Triheterocyclic compounds and pharmaceutical agent comprising thereof as active component

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to triheterocyclic compound of the formula (I): wherein X represents carbon atom; Y represents carbon or nitrogen atom; W represents carbon or nitrogen atom; U represents -CR2, and Z represents -CR2 or nitrogen atom; ring A represents (C5-C6)-cycloalkyl ring or 5-membered heterocyclic ring comprising one nitrogen, oxygen or sulfur atom; R1 represents alkyl, alkenyl, alkynyl, -NR4R5, -OR6 and others; R3 represents phenyl ring substituted with 1-3 substitutes or pyridyl or 1,3-dioxoindanyl ring substituted with 1-2 substitutes, and its pharmaceutically acceptable salts and pharmaceutical composition containing thereof as an active component. Also, invention relates to derivatives of pyrazolopyrimidine and derivatives of pyrrolopyrimidine. Compounds of the formula (I) show antagonistic activity with respect to corticotropin-releasing factor receptors. The compound can be used in treatment and/or prophylaxis of depression, anxiety state, disorders in food intake, post-traumatic stress, ulcerous disease, irritable bowel syndrome, Alzheimer's disease, abuse in drugs using or alcoholic syndrome dependence.

EFFECT: valuable medicinal properties of compounds and pharmaceutical agent.

7 cl, 1 dwg, 24 ex

 

The technical field

The present invention relates to three-heterocyclic compounds of the formula (I):

where all the symbols have the meanings defined hereinafter, which can be used as pharmaceuticals, and pharmaceutical preparation containing as active ingredient.

The level of technology

Corticotropinreleasing factor (was made the KRF CRF) is a peptide containing 41 amino acid residue, and it was isolated in 1981 from sheep hypothalamus. An assumption was made that was made the KRF is released from the hypothalamus and regulates the secretion of adrenocorticotropic hormone (ACTH, ACTH) from the pituitary [Science, 218, 377-379 (1982)].

Biological action begins with the binding was made the KRF with the receptor was made the KRF, which is located on the membranous surface of ACTH-producing cells in the anterior pituitary. Identified two subtypes of receptors was made the KRF, and each of them are distributed in various brain areas. For example, many 1 receptors are distributed in the pituitary, hypothalamus, cerebral cortex, and many 2 receptors are distributed in the septal part of the brain, paraventrikulyarnoe nuclei of the hypothalamus. In addition, the receptors can also be distributed in peripheral organs such as the heart, gastrointestinal tra is those lung, brain substance of adrenal glands, spleen, liver, kidney, prostate gland. More specifically, the receptor 1 is in the intestine or spleen, the receptor 2 is in the stomach, and in particular the receptor 2β is in the heart and skeletal muscle.

ACTH, which is released due to the stimulation was made the KRF, stimulates the secretion of cortisol from the adrenal cortex and refers to the system action for reproductive, growth, gastrointestinal function, inflammation, immune system, nervous system, etc. Therefore, it is believed, was made the KRF plays the role of regulator of these functions.

It is reported that in the brain of patients with depression and diseases associated with anxiety state is allocated the excess was made the KRF [Science, 226, 1342-1343 (1984); Neuroscience and Behavioral Reviews, 22, 635-651 (1998); J. Endocrinol, 160, 1-12 (1999)].

In addition, it is reported communication was made the KRF with various diseases, such as impaired food intake [Science, 273, 1561-1564 (1996)], inflammation [Endocrinology, 137, 5747-5750 (1996)], irritable bowel syndrome [Am.J.Physiol., 253, G582-G586 (1987)], drug addiction [Psychopharmacology, 137, 184-190 (1998)] and ischemia [Soc Neurosci Abstr. (Nov. 4-9, New Orleans), 807.5 (2000)].

On the other hand, was made the KRF closely associated with stress. For example, the introduction was made the KRF in the brain causes the same behavioral and endocrine response, which takes place the animal in causing stress conditions, Nature, 297, 331, (1982)].

As mentioned above, attention is drawn to was made the KRF and Central nervous system disorders, neuropsychiatric disorders or diseases of peripheral organs.

Thus, receptor inhibition was made the KRF, as it is useful in the case of diseases caused by abnormal secretion was made the KRF, for example, in the case of various diseases, including diseases caused by stress. For example, suppose that it can be used for the prevention and/or treatment of depression, single episode depression, recurrent depression, postpartum depression, depression, caused by poor treatment of child anxiety, disorders associated with fear (e.g., panic, specific phobia, fear of ruin, social phobia, obsessive compulsive disorder), emotional disorders, bipolar disorder, post traumatic stress disorder, peptic ulcer, diarrhea, constipation, syndrome level becomes too low, colon cancer, inflammatory bowel disease (ulcerative colitis, Crohn's disease), stress-related disorders gastrointestinal tract, nervous vomiting, disorders of food intake (for example, loss of appetite, bulimia nervous), obesity, stress-related sleep disturbance, pain, muscle fibers induced sleep disturbance caused by the article is the ECCA suppression of the immune system, stress headaches, stress-induced fever, caused by stress, pain, post-operative stress, rheumatoid arthritis, osteoarthritis, osteoporosis, psoriasis, thyroid dysfunction, uveitis, asthma, induced inappropriate Antidiarrhoeal hormone disorders, pain, inflammation, allergic diseases, wounds of the head, spinal cord injury, ischemic neuronal damage, toxic neural damage, disease, Cushing disease, stroke, spasm, muscle spasm, epilepsy, ischemia, Parkinson's disease, Huntington's disease, urinary incontinence, Alzheimer's disease, senile dementia in medical literature type, multi-infarct dementia, amyotrophic lateral sclerosis, hypoglycemia, cardiovascular or associated with heart disease (hypertension, tachycardia, congestive heart failure), addiction to the excessive use of drugs or alcohol syndrome.

On the other hand, the following known compounds with antagonistic activity was made the KRF.

(1) In the description of the publication WO 97/29109 compound of formula (A):

where

R1Arepresents NR4AR5Aor or5A;

R2Arepresents alkyl, alkoxy, alkylthio;

R3A represents H, alkyl, alkylsulfonyl, alkylsulfate or alkylthio;

R4Arepresents H, alkyl, mono - or di(cycloalkyl)methyl, cycloalkyl, alkenyl, hydroxyalkyl, alkylcarboxylic or alkyloxyalkyl;

R5Arepresents alkyl, mono - or di(cycloalkyl)methyl, Ar1A-CH2alkenyl, alkyloxyalkyl, hydroxyalkyl, thienylmethyl, furylmethyl, alkylthiomethyl, morpholinyl and others;

or R4Aand R5Atogether with the nitrogen atom to which they are attached, can form pyrrolidinyl, piperidinyl, homopiperazine or morpholinyl, optionally substituted alkyl, alkyloxyalkyl;

ArAndrepresents phenyl, phenyl, substituted by 1, 2 or 3 substituents, independently from each other selected from halogen, alkyl, trifloromethyl, hydroxy and others; pyridinyl, pyridinyl, substituted by 1, 2 or 3 substituents, independently from each other selected from halogen, alkyl, trifloromethyl, hydroxy,

described as a receptor antagonist was made the KRF.

(2) In the description of the publication WO 98/03510 compound of formula (I):

where

AndInrepresents N or CRIn;

ZBrepresents N or CR2B;

ArBselected from phenyl, naphthyl, pyridyl, pyrimidinyl, teinila, furanyl, teinila, benzothiazyl, benzofuranyl and others, each of zamestitelya Boptionally substituted by 1-5 substituents R4B;

RBrepresents H, alkyl, alkenyl, quinil, cycloalkyl, cycloalkenyl, halogen, cyano or halogenated;

R1Brepresents H, alkyl, alkenyl, quinil, halogen, cyano or halogenated, hydroxyalkyl and others;

R2Brepresents H, alkyl, alkenyl, quinil, cycloalkyl, cycloalkenyl, hydroxyalkyl and others;

R3Brepresents N, OR7B, SH, S(O)nR13B, COR7B, CO2R7B, OC(O)R13B, NR8BCOR7B, N(COR7B)2, NR8BCONR6BR7B, NR8BCO2R13B, NR6BR7B, alkyl, alkenyl, quinil, cycloalkyl, cycloalkenyl and others;

R4Brepresents alkyl, alkenyl, quinil, cycloalkyl, cycloalkenyl, NO2, halogen, cyano, halogenated, NR6BR7B, NR8BCOR7Band others,

described as a receptor antagonist was made the KRF.

(3) In the description of the publication WO 98/08847 compound of formula (C):

where the dotted lines indicate optional double bonds;

AndWithrepresents nitrogen or CR7C;

InWithrepresents NR1CR2C, CR1CR2CR10CC(=CR2CR11CR1C, NHCR1CR2CR10COCR1CR2CR10CSCR1CR2CR10C2CR10COther1C, CR2CR10COR1C, CR2CR10CSR1Cor COR2C;

JCand KCeach independently from each other represents a nitrogen or carbon, and both are not astami;

DCand ECeach independently from each other selected from nitrogen, CR4C, C=O, C=S, sulfur, oxygen, CR4CR6Cand NR8C;

GWithrepresents a nitrogen or carbon;

the ring containing DCEC, GWith, KCand JCcan be a saturated or unsaturated 5-membered ring and optionally substituted with one or two double bonds, and optionally may contain one to three heteroatoms in the ring, and optionally can have one or two group C=O or C=S;

R1Crepresents alkyl, optionally substituted by one or two substituents, independently of one another selected from hydroxy, fluorine, chlorine, bromine, iodine, O-alkyl, CF3With(=O)O-alkyl, OC(=O)alkyl, and others;

R2Crepresents alkyl, which optionally contains from one to three double or triple links, aryl or arylalkyl, cycloalkyl, cycloalkenyl and others;

R3Crepresents H, alkyl, O-alkyl, chlorine, fluorine, bromine, iodine, alkylene-O-alkyl, alkylen HE or S-alkyl;

R4Crepresents H, alkyl, fluorine, chlorine, bromine, iodine, hydrox is, cyano, amino, alkylene-HE, CF3and others;

R5Crepresents phenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and each group contains from one to four substituents R13Cwhere from one to three of these substituents can be independently from each other selected from fluorine, chlorine, alkyl and O-alkyl, and one of these substituents can be selected from bromine, iodine, formyl, HE, alkylen-HE, alkylene-O-alkyl, cyano, CF3, nitro, amino, alkylamino, dialkylamino and others,

described as a receptor antagonist was made the KRF.

Description of the invention

The present invention relates to three-heterocyclic compounds. More specifically, the present invention relates (1) to compounds of formula (I):

where each of X and Y independently from each other represents a carbon or nitrogen, and both of them are simultaneously astami;

W represents a carbon or nitrogen;

U and Z each independently from each other represents CR2, NR13, nitrogen, oxygen, sulfur, C=O or C=S;

R2represents a

(i) hydrogen,

(ii) C1-8-alkyl,

(iii) C2-8-alkenyl,

(iv) C2-8-quinil,

(v) halogen,(vi) CF3,

(vii) cyano,

(viii) nitro,

(ix) NR9R10where each of the substituents R9and R10independently from each other represents:

i) hydrogen,

(ii) C1-4-alkyl,

(iii) C3-10 mono - or bi-carbocyclic ring,

(iv) a 3-10 membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, or

(v) C1-4-alkyl, substituted C3-10 mono - or bi-carbocyclic ring or a 3 to 10-membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom,

(x) OR11where R11represents:

(i) hydrogen,

(ii) C1-4-alkyl,

(iii) C5-6-carbocyclic ring,

(iv) a 5 - or 6-membered heterocyclic ring containing 1-2 nitrogen atom and 1 oxygen atom and/or 1 sulfur atom, or

(v) C1-4-alkyl, substituted C5-6-carbocyclic ring or a 5 - or 6-membered heterocyclic ring containing 1-2 nitrogen atom and 1 oxygen atom and/or 1 sulfur atom,

(xi) SH,

(xii) S(O)nR12where n is 0, 1 or 2, R12represents:

(i) C1-4-alkyl,

(ii) C5-6-carbocyclic ring,

(iii) a 5 - or 6-membered heterocyclic ring containing 1-2 nitrogen atom and 1 oxygen atom and/or 1 sulfur atom, or

(iv) C1-4-alkyl, substituted C5-6-carbocyclic ring or a 5 - or 6-membered heterocyclic ring containing 1-2 nitrogen atom and 1 oxygen atom and/or 1 sulfur atom,

(xiii) COR11,

(xiv) COOR11,

(xv) CONR9R10,

(xvi) C3-10 mono - or bi-carbocyclic ring,

(xvii) 3-10-the Lenna mono - or bi-heterocyclic ring, containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, or

(xviii) C1-4-alkyl, substituted by 1-2 substituents selected from halogen, CF3, OCF3, cyano, nitro, NR9R10, OR11, =N-OR11, SH, S(O)nR12, COR11, COOR11, CONR9R10, C3-10 mono - or bi-carbocyclic ring, and 3-10 membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom,

R13represents a

(i) hydrogen,

(ii) C1-4-alkyl,

(iii) C2-4-alkenyl,

(iv) C2-4-quinil,

(v) C3-10 mono - or bi-carbocyclic ring,

(vi) 3-10 membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, or

(vii) C1-4-alkyl, substituted C3-10 mono - or bi-carbocyclic ring or a 3 to 10-membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom,

----represents a single or double bond,

is a C4-6-carbocyclic ring, or a 4-6-membered heterocyclic ring containing at least one atom of nitrogen, oxygen and sulfur, and these rings are unsubstituted or substituted by 1-3 substituents selected from C1-4-alkyl, C1-4-alkoxy, halogen and CF3,

R1represents a

(i) C1-8-alkyl, is which is unsubstituted or substituted by 1-5 substituents R 14;

(ii) C2-8-alkenyl, which is unsubstituted or substituted by 1-5 substituents R14;

(iii) C2-8-quinil, which is unsubstituted or substituted by 1-5 substituents R14;

(iv) NR4R5where each of the substituents R4and R5independently from each other represents a

(i) hydrogen,

(ii) C1-15-alkyl, which is unsubstituted or substituted by 1-5 substituents R17;

(iii) C2-15-alkenyl, which is unsubstituted or substituted by 1-5 substituents R17;

(iv) C2-15-quinil, which is unsubstituted or substituted by 1-5 substituents R17;

(v) C3-15 mono - or bi-carbocyclic ring which is unsubstituted or substituted by 1-5 substituents R18;

(vi) 3-15 membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, which is unsubstituted or substituted by 1-5 substituents R18;

(v) OR6where substituent R6represents a

(i) hydrogen,

(ii) C1-10-alkyl,

(iii) C2-10-alkenyl,

(iv) C2-10-quinil,

(v) C3-15 mono - or bi-carbocyclic ring which is unsubstituted or substituted by 1-5 substituents R18;

(vi) 3-15 membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, which is unsubstituted or substituted is 1-5 substituents R 18;

(vii) C1-4-alkyl, substituted by 1-2 substituents selected from halogen, CF3, OCF3, cyano, nitro, NR9R10, OR11, =N-OR11, SH, S(O)nR12, COR11, COOR11, CONR9R10, C3-10 mono - or bi-carbocyclic ring which is unsubstituted or substituted by 1-5 substituents R18, and 3-10 membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, which is unsubstituted or substituted by 1-5 substituents R18;

(vi) SH,

(vii) S(O)nR7where n takes the values indicated above, R7represents:

(i) C1-8-alkyl,

(ii) C3-10 mono - or bi-carbocyclic ring which is unsubstituted or substituted by 1-5 substituents R18;

(iii) 3-10 membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, which is unsubstituted or substituted by 1-5 substituents R18;

(iv) C1-4-alkyl, substituted C3-10 mono - or bi-carbocyclic ring which is unsubstituted or substituted by 1-5 substituents R18or 3-10-membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, which is unsubstituted or substituted by 1-5 substituents R18;

(viii) COR6,

(ix) COOR 6,

(x) CONR4R5,

(xi) NR8COR6awhere R6arepresents:

(i) hydrogen,

(ii) C1-10-alkyl,

(iii) C2-10-alkenyl,

(iv) C2-10-quinil or

(v) C1-4-alkyl, substituted by 1-2 substituents selected from halogen, CF3, OCF3, cyano, nitro, NR9R10, OR11a, =N-OR11, SH, S(O)nR12, COR11, COOR11and CONR9R10,

(xii) NR8COOR6where R6has the above meaning, R8represents:

(i) hydrogen,

(ii) C1-8-alkyl,

(iii) C2-8-alkenyl,

(iv) C2-8-quinil,

(v) C3-10 mono - or bi-carbocyclic ring which is unsubstituted or substituted by 1-5 substituents R18;

(vi) 3-10 membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, which is unsubstituted or substituted by 1-5 substituents R18; or

(vii) C1-4-alkyl, substituted by 1-2 substituents selected from halogen, CF3, OCF3, cyano, nitro, NR9R10, OR11, =N-OR11, SH, S(O)nR12, COR11, COOR11, CONR9R10, C3-10 mono - or bi-carbocyclic ring which is unsubstituted or substituted by 1-5 substituents R18, and 3-10 membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, which is is unsubstituted or substituted by 1-5 substituents R 18;

(xiii) NR8CONR4R5,

(xiv) C3-15 mono - or bi-carbocyclic ring which is unsubstituted or substituted by 1-5 substituents R15; or

(xv) 3-15 membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, which is unsubstituted or substituted by 1-5 substituents R15,

R11arepresents (i) hydrogen, (ii) C1-4-alkyl or (iii) C1-4-alkyl, substituted C5-6 carbocyclic ring or 5 - or 6-membered heterocyclic ring containing 1-2 nitrogen atom and 1 oxygen atom and/or 1 sulfur atom,

R14represents (a) halogen, (b) CF3(c) OCF3, (d) cyano, (e) nitro, (f) NR4R5(g) OR6, (h) =N-OR6(j) SH, (k) S(O)nR7, (l) COR6(m) COOR6(n) CONR4R5, (o) NR8COR6(p) NR8COOR6(q) NR8CONR4R5, (r) C3-15 mono - or bi-carbocyclic ring which is unsubstituted or substituted by 1-5 substituents R15or (s) 3-15 membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, which is unsubstituted or substituted by 1-5 substituents R15;

R15represents (a) C1-8-alkyl, (b) C2-8-alkenyl, (C) C2-8-quinil, (d) C1-4-alkoxy(C1-4)-alkyl, (e) halogen, (f) CF3(g) OCF3, (h) cyano, (j) neither the ro (k) NR4R5, (l) OR6(m) SH (n) S(O)nR7, (o) COR6(p) COOR6(q) CONR4R5, (r) NR8COR6, (s) NR8COOR6, (t) NR8CONR4R5, (u) C3-10 mono - or bi-carbocyclic ring which is unsubstituted or substituted by 1-5 substituents R20(v) 3-10 membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, which is unsubstituted or substituted by 1-5 substituents R20or (w) C1-4-alkyl, substituted by 1-2 substituents selected from halogen, CF3, OCF3, cyano, nitro, NR4R5, OR6, =N-OR6, SH, S(O)nR7, COR6, COOR6, CONR4R5, NR8COR6, NR8COOR6, NR8CONR4R5, C3-10 mono - or bi-carbocyclic ring which is unsubstituted or substituted by 1-5 substituents R20, and 3-10 membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, which is unsubstituted or substituted by 1-5 substituents R20;

R17represents (a) halogen, (b) CF3(c) OCF3, (d) cyano, (e) nitro, (f) NR9R10(g) OR11a, (h) =N-OR11(j) SH, (k) S(O)nR12, (l) COR11(m) COOR11(n) CONR9R10, (o) NR8COR11(p) NR8COOR11(q) NRsup> 8CONR9R10, (r) C3-15 mono - or bi-carbocyclic ring which is unsubstituted or substituted by 1-5 substituents R18aor (s) 3-15 membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, which is unsubstituted or substituted by 1-5 substituents R18a;

R18represents (a) C1-4-alkyl, (b) C2-4-alkenyl, (C) C2-4-quinil, (d) halogen, (e) CF3and (f) OCF3, (g) cyano, (h) nitro, (j) SH, (k) S(O)nR12, (l) NR9R10, (m) OR11(n) COR11, (o) COOR11(p) CONR9R10(q) C5-6-carbocyclic ring, (r) 5 - or 6-membered heterocyclic ring containing 1-2 nitrogen atom and 1 oxygen atom and/or 1 sulfur atom, or (s) C1-4-alkyl, substituted C5-6 carbocyclic ring or 5 - or 6-membered heterocyclic ring containing 1-2 nitrogen atom and 1 oxygen atom and/or 1 sulfur atom,

R18arepresents (a) C1-4-alkyl, (b) C2-4-alkenyl, (C) C2-4-quinil, (d) halogen, (e) CF3and (f) OCF3, (g) cyano, (h) nitro, (j) SH, (k) S(O)nR12, (l) NR9R10, (m) OR11a(n) COR11, (o) COOR11or (p) CONR9R10,

R19represents a C1-4-alkyl, C1-4-alkoxy, halogen, CF3, OCF3, cyano, nitro, amino, NH(C1-4-alkyl) or N(C1-4-alkyl)2,

R3represents (i) a C5-10 mono - or bi-carbocyclization, substituted by 1-5 substituents R16or (ii) a 5-10 membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, substituted by 1-5 substituents R16,

R16represents a

(a) C1-8-alkyl,

(b) C2-8-alkenyl,

(C) C2-8-quinil,

(d) halogen,

(e) CF3,

(f) OCF3,

(g) cyano,

(h) nitro,

(j) NR9R10,

(k) OR11,

(l) SH,

(m) S(O)nR12except phenylthio,(n) COR11,

(o) COOR11,

(p) CONR9R10,

(q) NR8COR11,

(r) NR8COOR11,

(s) NR8CONR9R10,

(t) C3-10 mono - or bi-carbocyclic ring,

(u) 3-10 membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom,

(v) C1-4-alkyl, substituted by 1 to 2 substituents selected from halogen, CF3, OCF3, cyano, nitro, NR9R10, OR11, =N-OR11, SH, S(O)nR12, COR11, COOR11, CONR9R10, NR8COR11, NR8COOR11, NR8CONR9R10, C3-10 mono - or bi-carbocyclic ring, and 3-10 membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom,

provided that, (1) when X and W are carbon atoms, Y and Z are ashtami, U is from the battle of CR 4and R1is a OR6Deputy R3is not phenyl, substituted 1 atom of halogen, phenyl, substituted 1-trifluoromethyl, and phenyl substituted by trifluoromethyl and nitro, and (2) when X, Y and Z are carbon atoms, and U and W are ashtami, Deputy R3represents a C5-10 mono - or bi-carbocyclic ring, substituted by 1-5 substituents R16;

their pharmaceutically acceptable salt, or hydrate,

(2) manner of receiving them and

(3) to pharmaceutical compositions containing them as a receptor antagonist was made the KRF.

In the description of C1-4-alkyl means methyl, ethyl, propyl, butyl and isomeric groups.

In the description of C1-8-alkyl means methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl and their isomeric groups.

In the description of C1-15-alkyl means methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl and their isomeric groups.

In the description of C1-4-alkoxy means methoxy, ethoxy, propoxy, butoxy and their isomeric groups.

In the description of the C2-4-alkenyl means vinyl, propenyl, butenyl and their isomeric groups.

In the description C2-8-alkenyl means ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl containing 1-3 double bonds, and their isomeric groups. For example, vinyl, propenyl, butenyl, pentenyl, hexenyl, hexadienyl, GE is Tennille, heptadienyl, octenyl, octadienal.

In the description C2-15-alkenyl means ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl containing 1-3 double bonds, and their isomeric groups. For example, vinyl, propenyl, butenyl, pentenyl, hexenyl, hexadienyl, heptenyl, heptadienyl, octenyl, octadienal, nonanal, nonadienal, decenyl, decadienal, undecenyl, dodecenyl, tridecanol, tetradecanol, pentadecanol.

In the description of the C2-4-quinil means ethinyl, PROPYNYL, butynyl and their isomeric groups.

In the description C2-8-quinil means ethyl, propyl, butyl, hexyl, heptyl, octyl containing 1-3 triple bond, and their isomeric groups. For example, ethinyl, PROPYNYL, butynyl, pentenyl, hexenyl, hexadienyl, heptenyl, heptadienyl, octenyl, octadienal.

In the description C2-15-quinil means ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl containing 1-3 triple bond, and their isomeric groups. For example, ethinyl, PROPYNYL, butynyl, pentenyl, hexenyl, hexadienyl, heptenyl, heptadienyl, octenyl, octadienal, nonini, decenyl, undecenyl, dodecenyl, tridecanol, pentadecanol.

In the description halogen represents fluorine, chlorine, bromine and iodine.

In the description of C1-4-alkoxy(C1-4)alkyl means methyl, ethyl, propyl, butyl and isomeric groups who, substituted with one methoxy, ethoxy, propoxy, butoxy and their isomeric groups.

In the description of the C4-6-carbocyclic ring represents a C4-6-carbocyclic aryl or partially or fully saturated version. For example, CYCLOBUTANE, cyclopentane, cyclohexane, cyclopentene, cyclohexene, cyclopentadiene, cyclohexadiene, benzene.

In the description C5-6-carbocyclic ring represents a C5-6-carbocyclic aryl or partially or fully saturated version. For example, a cyclopentane, cyclohexane, cyclopentene, cyclohexene, cyclopentadiene, cyclohexadiene, benzene.

In the description C3-10 mono - or bi-carbocyclic ring is a C3-10 mono-or bi-carbocyclic aryl or partially or fully saturated version. For example, cyclopropane, CYCLOBUTANE, cyclopentane, cyclohexane, Cycloheptane, cyclopentene, cyclohexene, cyclopentadiene, cyclohexadiene, benzene, pentalene, inden, naphthalene, azulene, perhydroanthracene, indan, palikonda, tetrahydronaphthalen, peridontal, perpetraitor.

In the description C3-15 mono - or bi-carbocyclic ring is a C3-15 mono - or bi-carbocyclic aryl or partially or fully saturated version, or bridge bi-carbocyclic ring. For example, cyclopropane, CYCLOBUTANE, cyclopentane, cyclohexane, Cycloheptane, cyclopentene, clohexane, cyclopentadiene, cyclohexadiene, benzene, pentalene, inden, naphthalene, azulene, geptalen, perhydroanthracene, indan, palikonda, tetrahydronaphthalen, peridontal, pergerson, perheravintolan, bicyclo[3.1.1]heptane.

In the description C5-10 mono - or bi-carbocyclic ring represents a C5-10 mono - or bi-carbocyclic aryl or partially or fully saturated version. For example, a cyclopentane, cyclohexane, Cycloheptane, cyclopentene, cyclohexene, cycloheptene, cyclopentadiene, cyclohexadiene, cycloheptadiene, benzene, pentalene, inden, naphthalene, azulene, perhydroanthracene, indan, palikonda, tetrahydronaphthalen, peridontal, perpetraitor.

In the description 4-6-membered heterocyclic ring containing at least one atom of nitrogen, oxygen and sulfur, is a 4-6-membered heterocyclic aryl containing at least one atom of nitrogen, oxygen and sulfur or partially or completely saturated version. For example, azetidine, pyrrolidine, pyrrolin, pyrrole, tetrahydrofuran, dihydrofuran, furan, tetrahydrothiophene, dihydrothiophene, thiophene, piperidine, dihydropyridines, pyridine, tetrahydropyran, dihydropyran, Piran, tetrahydrothiopyran, dihydrothiophene, thiopyran.

In the description of the 5 - or 6-membered heterocyclic ring containing 1-2 nitrogen atom and 1 oxygen atom and/or 1 sulfur atom, p is ecstasy a 5 - or 6-membered heterocyclic aryl, containing 1-2 nitrogen atom and 1 oxygen atom and/or 1 sulfur atom, or partially or fully saturated version. For example, pyrrole, imidazole, pyrazole, pyridine, pyrazin, pyrimidine, pyridazine, furan, Piran, thiophene, tiain (thiopyran), oxazol, isoxazol, thiazole, isothiazol, pyrrolin, pyrrolidine, piperidine, imidazoline, imidazolidine, pyrazoline, pyrazolidine, piperazine, targetability, targetability, dihydrofuran, tetrahydrofuran, tetrahydropyran, dihydrothiophene, tetrahydrothiophene, tetrahydrothieno, morpholine, thiomorpholine.

In the description 3-10-membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, is a 3-10-membered mono - or bi-heterocyclic aryl containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, or partially or fully saturated version. 3-10-membered mono - or bi-heterocyclic aryl containing 1-4-atom of nitrogen, 1-2 of oxygen and/or 1-2 sulfur atom, a represents, for example, pyrrole, imidazole, pyrazole, thiazole, tetrazole, pyridine, pyrazin, pyrimidine, pyridazine, azepine, diazepine, furan, Piran, oxepin, thiophene, tiain (thiopyran), tiepin, oxazol, isoxazol, oxadiazol, oxazin, oxadiazon, oxazepine, oxadiazon, thiazole, isothiazol, thiadiazole, teasin, thiadiazin, diazepin, thiadiazin, indole, isoindole endolysin, benzofuran from benzofuran, benzothiophen, isobenzofuran, indazole, quinoline, isoquinoline, hemolysin, phthalazine, naphthiridine, cinoxacin, hinzelin, cinnolin, benzoxazol, benzoxadiazole, benzothiazole, benzimidazole, benzofuran, benzothiadiazole, benzotriazole.

The above partially or fully saturated 3-10 membered mono - or bi-heterocyclic aryl containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, a represents, for example, aziridine, azatin, azetidin, pyrrolin, pyrrolidin, imidazolin, imidazolidin, pyrazoline, pyrazolidine, triazoline, thiazolidin, tetrazolyl, tetrazolium, piperidine, piperazine, dihydropyridines, tetrahydropyridine, dihydropyridine, tetrahydropyridine, dihydropyrimidin, tetrahydropyrimidin, targetability, dihydropyridin, tetrahydropyridine, targetability, dehydroacetic, tetrahydroazepine, peligrosa, dihydrovitamin, tetrahydroazepine, targetrotation, oxiran oxetan, dihydrofuran, tetrahydrofuran, dihydropyran, tetrahydropyran, dehydroacetic, tetrahydroazepine, perhydroxyl, thiran, tieton, dihydrothiophene, tetrahydrothiophene, dehydration (dihydrothiophene), tetrahydrate (tetrahydrothiopyran), dihydrothiophene, tetrahydrothiophene, pengertian, oxazoline (dihydrooxazolo), oxazolidin (tetrahydrooxazolo), dihydroisoxazole, tetrahydrooxazolo, oxadiazol is n (dihydroimidazole), oxadiazolidine (tetrahydrooxazolo), thiazolin (dihydrothiazolo), thiazolidin (tetrahydrothieno), dihydroisoxazole, tetrahydrocortisol, morpholine, thiomorpholine, indolin, isoindoline, dihydrobenzofuran, perhydroanthracene, dihydroisobenzofuran, peligrosamente, dihydrobenzofuran, targetobjecttype, dihydroisobenzofuran, peligrosamente, dihydroindol, peritoneal, dihydroquinoline, tetrahydroquinoline, perhydroxyl, dihydroisoquinoline, tetrahydroisoquinoline, perhydrosqualene, dihydrophenazine, tetrahydrophthalate, PermitRootLogin, dihydronaphthalene, tetrahydronaphthalene, perhydroanthracene, dihydroquinoxaline, tetrahydroquinoxalin, perhydrophenanthrene, dihydroquinazolin, tetrahydroquinazolin, perhydrophenanthrene, dihydroindole, tetrahydroindole, permitiendoles, dihydroisoxazole, perhydroanthracene, dihydrobenzofuran, perhydroanthracene, dehydrobenzperidol, perhydroanthracene, dioxolane, dioxane, dioxazine, dioksiinien, chroman, isochroman.

In the description 3-15 membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, represents a 3-15 membered mono - or bi-heterocyclic aryl containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, or partially or completely saturated vari the NT. For example, 3-15 membered mono - or bi-heterocyclic aryl containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, a is a pyrrole, imidazole, pyrazole, triazole, tetrazole, pyridine, pyrazin, pyrimidine, pyridazine, azepine, diazepine, furan, Piran, oxepin, thiophene, tiain (thiopyran), tiepin, oxazol, isoxazol, oxadiazol, oxazin, oxadiazon, oxazepine, oxadiazon, thiazole, isothiazol, thiadiazole, teasin, thiadiazin, diazepin, thiadiazin, indole, isoindole, indolizine benzofuran, isobenzofuran, benzothiophene, isobenzofuran, indazole, quinoline, isoquinoline, hemolysin, phthalazine, naphthiridine, cinoxacin, hinzelin, cinnolin, benzoxazol, benzoxadiazole, benzthiazole, benzimidazole, benzazepin, benzodiazepine, benzotriazol, benzoxazepin, benzodiazepin, benzodiazepin, benzothiadiazole, benzothiadiazepine, benzofurazan.

The above partially or fully saturated 3-15 membered mono - or bi-heterocyclic aryl containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, a represents, for example, aziridine, azatin, azetidin, pyrrolin, pyrrolidin, imidazolin, imidazolidin, pyrazoline, pyrazolidine, triazoline, thiazolidin, tetrazolyl, tetrazolium, piperidine, piperazine, dihydropyridines, tetrahydropyridine, dihydropyridine, tetrahydropyridine, dihydropyrimidin, tetrahydropyrimidin, pergidae is imidan, dihydropyridin, tetrahydropyridine, targetability, dehydroacetic, tetrahydroazepine, peligrosa, dihydrovitamin, tetrahydroazepine, targetrotation, oxiran, oxetan, dihydrofuran, tetrahydrofuran, dihydropyran, tetrahydropyran, dehydroacetic, tetrahydroazepine, perhydroxyl, thiran, tieton, dihydrothiophene, tetrahydrothiophene, dehydration (dihydrothiophene), tetrahydrate (tetrahydrothiopyran), dihydrothiophene, tetrahydrothiophene, pengertian, oxazoline (dihydrooxazolo), oxazolidin (tetrahydrooxazolo), dihydroisoxazole, tetrahydrooxazolo, oxadiazolyl (dihydroimidazole), oxadiazolidine (tetrahydrooxazolo), thiazolin (dihydrothiazolo), thiazolidin (tetrahydrothieno), dihydroisoxazole, tetrahydrocortisol, morpholine, thiomorpholine, indolin, isoindoline, dihydrobenzofuran, perhydroanthracene, dihydroisobenzofuran, peligrosamente, dihydrobenzofuran, targetobjecttype, dihydroisobenzofuran, peligrosamente, dihydroindol, peritoneal, dihydroquinoline, tetrahydroquinoline, perhydroxyl, dihydroisoquinoline, tetrahydroisoquinoline, perhydrosqualene, dihydrophenazine, tetrahydrophthalate, PermitRootLogin, dihydronaphthalene, tetrahydronaphthalene, perhydroanthracene, dihydroquinoxaline, tetrahydroquinoxalin, perhydrophenanthrene, DigiTech is Natolin, tetrahydroquinazolin, perhydrophenanthrene, dihydroindole, tetrahydroindole, permitiendoles, dihydroisoxazole, perhydroanthracene, dihydrobenzofuran, perhydroanthracene, dehydrobenzperidol, peligrosidad, digitalisation, tetrahydrobenzene, dihydrobenzofuran, tetrahydrolipstatin, dihydroisoxazole, tetrahydrobenzaldehyde, dioxolane, dioxane, dioxazine, dioksiinien, chroman, isochroman.

In the description 5-10-membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, represents a 5-10 membered mono - or bi-heterocyclic aryl containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, or partially or fully saturated version. For example, a 5-10 membered mono - or bi-heterocyclic aryl containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, a is a pyrrole, imidazole, pyrazole, triazole, tetrazole, pyridine, pyrazin, pyrimidine, pyridazine, azepine, diazepine, furan, Piran, oxepin, thiophene, tiain (thiopyran), tiepin, oxazol, isoxazol, oxadiazol, oxazin, oxadiazon, oxazepine, oxadiazon, thiazole, isothiazol, thiadiazole, teasin, thiadiazin, diazepin, thiadiazin, indole, isoindole, indolizine benzofuran, isobenzofuran, benzothiophene, isobenzofuran, indazole, quinoline, isoquinoline, hemolysin, ft is Latin, the naphthiridine, cinoxacin, hinzelin, cinnolin, benzoxazol, benzoxadiazole, benzthiazole, benzimidazole, benzofuran, benzothiadiazole, benzotriazole.

The above partially or fully saturated 5-to 10-membered mono - or bi-heterocyclic aryl containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, a represents, for example, pyrrolin, pyrrolidin, imidazolin, imidazolidin, pyrazoline, pyrazolidine, triazoline, thiazolidin, tetrazolyl, tetrazolium, piperidine, piperazine, dihydropyridines, tetrahydropyridine, dihydropyridine, tetrahydropyridine, dihydropyrimidin, tetrahydropyrimidin, targetability, dihydropyridin, tetrahydropyridine, targetability, dehydroacetic, tetrahydroazepine, peligrosa, dihydrovitamin, tetrahydroazepine, targetrotation, oxiran, oxetan, dihydrofuran, tetrahydrofuran, dihydropyran, tetrahydropyran, dehydroacetic, tetrahydroazepine, perhydroxyl, thiran, tieton, dihydrothiophene, tetrahydrothiophene, dehydration (dihydrothiophene), tetrahydrate (tetrahydrothiopyran), dihydrothiophene, tetrahydrothiophene, pengertian, oxazoline (dihydrooxazolo), oxazolidin (tetrahydrooxazolo), dihydroisoxazole, tetrahydrooxazolo, oxadiazolyl (dihydroimidazole), oxadiazolidine (tetrahydrooxazolo), thiazolin (dihydrothiazolo), thiazolidin (tetrahydro the thiazole), dihydrothiazolo, tetrahydrocortisol, morpholine, thiomorpholine, indolin, isoindoline, dihydrobenzofuran, perhydroanthracene, dihydroisobenzofuran, peligrosamente, dihydrobenzofuran, targetobjecttype, dihydroisobenzofuran, peligrosamente, dihydroindol, peritoneal, dihydroquinoline, tetrahydroquinoline, perhydroxyl, dihydroisoquinoline, tetrahydroisoquinoline, perhydrosqualene, dihydrophenazine, tetrahydrophthalate, PermitRootLogin, dihydronaphthalene, tetrahydronaphthalene, perhydroanthracene, dihydroquinoxaline, tetrahydroquinoxalin, perhydrophenanthrene, dihydroquinazolin, tetrahydroquinazolin, perhydrophenanthrene, dihydroindole, tetrahydroindole, permitiendoles, dihydroisoxazole, perhydroanthracene, dihydrobenzofuran, perhydroanthracene, dehydrobenzperidol, perhydroanthracene, dioxolane, dioxane, dioxazine, dioksiinien, chroman, isochroman.

In the compound of formula (I) of the present invention the radical

is saturated, partially saturated or unsaturated 5-membered carbocyclic ring or heterocyclic ring. In the ring, X and Y can represent all combinations, where X is a carbon and Y is nitrogen, X is a nitrogen and Y is carbon, and the AC is X, and Y represent carbon atoms. Specifically, preferred are the following combinations:

(i) X represents carbon, Y is nitrogen, each of U and Z is carbon or nitrogen and W is a carbon;

(ii) X represents nitrogen, Y is carbon, each of U and Z is carbon or nitrogen and W is a carbon;

(iii) each of X and Y is carbon, each of U and W is carbon or nitrogen, and Z represents carbon,

(iv) each of X and Y is carbon, U represents nitrogen and Z represents oxygen or sulfur, U represents oxygen or sulfur, Z is a nitrogen and W is a carbon; or

(v) each of X and Y is carbon, each of Z and W is nitrogen and U is a C=O or C=s

The preferred combination is:

(i-1) each of X, U and W is carbon, and each of Y and Z is nitrogen;

(i-2) each of X, Z and W is carbon, and each of Y and U is nitrogen;

(i-3) each of X, Z, U and W is carbon and Y is nitrogen;

(ii-1) each of X, Z and U is nitrogen, and each of Y and W is carbon;

(ii-2) each of X and Z is nitrogen, and each of Y, U and W is carbon;

(ii-3) each of X and U is nitrogen, and each of Y, Z and W is carbon;

(ii-4) X represents nitrogen, and each of Y, Z, U and W is carbon;

(iii-1) each of X, Y and Z is carbon, and each of U and W is nitrogen;

(iii-2) each of X, Y, Z, and U is carbon, and W represents nitrogen;

(iv-1) each of X, Y, and W is carbon, Z represents oxygen and U represents nitrogen;

(iv-2) each of X, Y, and W is carbon, Z represents sulfur, and U represents nitrogen;

(iv-3) each of X, Y, and W is carbon, Z is a nitrogen and U represents oxygen;

(iv-4) each of X, Y, and W is carbon, Z is a nitrogen and U represents sulfur;

(v-1) each of X and Y is carbon, each of Z and W is a nitrogen, and U represents C=O; or

(v-2) each of X and Y is carbon, each of Z and W is a nitrogen and U is a C=S.

Of the compounds of formula (I) of the present invention the following compounds of formula (I-i)-(I-xxvi) are presented as examples of specific compounds.

Of the compounds of formula (I-i)-(I-xxvi) the following compounds are preferred.

In the compound of formula (I) of the present invention C4-6 carbocyclic ring, or a 4-6-membered Goethe is acyclically ring, containing at least one atom of nitrogen, oxygen and sulfur, represented by the formula:

is a C4-6 carbocyclic aryl or partially or fully saturated version or a 4-6-membered heterocyclic aryl containing at least one atom of nitrogen, oxygen and sulfur or partially or completely saturated option.

The following radicals are preferred as ring And:

where G represents O, S or NH; Rxrepresents a C1-4-alkyl, C1-4-alkoxy, halogen or CF3; m is 0-3.

In the compound of formula (I) of the present invention, the preferred substituent R1represents:

(i) C1-8-alkyl, which is unsubstituted or substituted by 1-5 substituents R14;

(ii) C2-8-alkenyl, which is unsubstituted or substituted by 1-5 substituents R14;

(iii) C2-8-quinil, which is unsubstituted or substituted by 1-5 substituents R14;

(iv) NR4R5;

(v) OR6;

(vi) C3-15 mono - or bi-carbocyclic ring which is unsubstituted or substituted by 1-5 substituents R15; or

(vii) 3-15 membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, which is unsubstituted or substituted by 1-5 what zamestitelyami R 15.

The preferred combination of R4and R5in NR4R5in the above preferred substituent R1represents:

(a) R4represents (i) hydrogen, and R5represents (ii) C1-15-alkyl, which is unsubstituted or substituted by 1-5 substituents R17; (iii) C2-15-alkenyl, which is unsubstituted or substituted by 1-5 substituents R17, (iv) C2-15-quinil, which is unsubstituted or substituted by 1-5 substituents R17; (v) C3-15 mono - or bi-carbocyclic ring which is unsubstituted or substituted by 1-5 substituents R18; or (vi) 3-15 membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, which is unsubstituted or substituted by 1-5 substituents R18; or

(b) R4represents (ii) C1-15-alkyl, which is unsubstituted or substituted by 1-5 substituents R17; (iii) C2-15-alkenyl, which is unsubstituted or substituted by 1-5 substituents R17; (iv) C2-15-quinil, which is unsubstituted or substituted by 1-5 substituents R17; or (v-1) C3-6 mono-carbocyclic ring, and R5represents (ii) C1-15-alkyl, which is unsubstituted or substituted by 1-5 substituents R17; (iii) C2-15-alkenyl, which is unsubstituted or substituted by 1-5 replace the s R 17; (iv) C2-15-quinil, which is unsubstituted or substituted by 1-5 substituents R17; (v) C3-15 mono - or bi-carbocyclic ring which is unsubstituted or substituted by 1-5 substituents R18; or (vi) 3-15 membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, which is unsubstituted or substituted by 1-5 substituents R18.

Preferably, 3-15 membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, which is unsubstituted or substituted by 1-5 substituents R15in the above preferred R1connected through the nitrogen in the ring. It represents a group:

which is unsubstituted or substituted by 1-5 substituents R15and this group represents a 3-15 membered mono - or bi-heterocyclic ring necessarily containing one nitrogen, and, in addition, optionally containing one atom of nitrogen, oxygen, or sulfur. Specifically, we are talking about the following heterocyclic rings, which are unsubstituted or substituted by 1-5 substituents R15.

Specific compounds of the present invention are compounds described in the examples below, and their pharmaceutical is acceptable salt.

Unless otherwise noted, the invention encompasses all isomers. For example, alkyl, alkoxy, alkenyl and quinil include linear and branched isomers. Isomers, based on the double bond, cycle, condensed cycle (E, Z, CIS, TRANS)isomers that exist due to the presence of asymmetric(s) atom(s) carbon (R-configuration, S-configuration, αconfiguration β-configuration, enantiomers, diastereoisomers), optically active compounds having optical rotation (D, L, d, l-configuration), polar compounds obtained by chromatographic separation (high-polar compound, less polar compound), equilibrium compounds, the mixture existing in the free ratio, racemic mixtures are included in the invention.

[Sol]

The compound of the present invention of formula (I) can be converted to the corresponding pharmaceutically acceptable salt by known methods. In the present invention, pharmaceutically acceptable salts are salts of alkali metals, salts of alkaline-earth metals, ammonium salts, salts of amines, acid additive salt.

Non-toxic and water-soluble salts are preferred. Suitable salts are alkali metal salts, such as potassium, sodium, salts of alkaline-earth metals such as calcium, magnesium; ammonium salts f is rmaceuticals acceptable organic amines, such as Tetramethylammonium, triethylamine, methylamine, dimethylamine, cyclopentylamine, benzylamine, phenethylamine, piperidine, monoethanolamine, diethanolamine, Tris(hydroxymethyl)methylaminomethyl, lysine, arginine, N-methyl-D-glucamine. Salt of an alkali metal is preferred.

Non-toxic and water-soluble acid additive salts are preferred. Suitable acid additive salts are salts of inorganic acids such as hydrochloride, hydrobromide, sulfate, phosphate, nitrate; salts of organic acids such as acetate, triptorelin, lactate, tartrate, oxalate, fumarate, maleate, citrate, benzoate, methanesulfonate, aconsultant, bansilalpet, toluensulfonate, isethionate, glucuronate, gluconate.

The compound of formula (I) of the present invention and salts thereof can be converted into the corresponding hydrates in the usual way.

Obtaining the compounds of the present invention

The present compound of the formula (I) can be obtained, for example, in the following ways :

(A) From compounds of formula (I), the compound in which R1is a HE, and R2and R3are not HE, cyano, =N-OR11or the group that contains IT, cyano or =N-OR11then there is the connection of the formula (I-A):

where each of the substituents ZaUaand R3-aand out the same values as Z, U and R3provided that they are not HE, cyano, =N-OR11or the group that contains IT, cyano or =N-OR11; other symbols have the above meanings;

can be obtained by reacting the compounds of formula (II-1):

where all symbols are defined above;

with the compound of the formula (III-1)

where ring Aarepresents a saturated or partially saturated C4-6 carbocyclic ring, or a 4-6-membered heterocyclic ring, Et represents ethyl, and the other symbols have the above meanings;

or sequentially exposing the oxidation reaction.

The above reaction of the compound of formula (II) and compounds of formula (III) are known and carried out, for example, in an organic solvent (e.g. acetic acid) at temperatures from room temperature up to the boiling temperature under reflux.

The oxidation reaction is known, and is performed, for example, in an organic solvent (e.g., diphenyl ether) using a catalyst based on a metal (e.g. palladium on charcoal, palladium, palladium hydroxide, palladium acetate, palladium mobile), when 0˜250°C.

(B) From compounds of formula (I), the compound in which R1is not HE, cyano, =N-OR6or a group containing cyano and is =N-OR 11and C3-10 mono - or bi-carbocyclic ring, 3-10-membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, R2and R3are not HE, cyano, =N-OR11or the group that contains IT, cyano or =N-OR11then there is the connection of the formula (I):

where substituent R1-ahas the same meaning as R1provided that it is not HE, cyano, =N-OR6or a group containing cyano or =N-OR11and C3-10 mono - or bi-carbocyclic ring, or 3-10-membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom; and other symbols have the above meanings;

can be obtained by the coupling of compounds of formula (IV)

where X is a halogen, and other symbols have the above meanings;

with the compound of the formula (V-1)

where R1-abhas the same meaning as R1provided that it is not HE, cyano, =N-OR6or a group containing cyano or =N-OR11and C3-10 mono - or bi-carbocyclic ring, 3-10-membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom;

or sequentially exposing the reactions is oxidation, or

with the compound of the formula (V-2)

where R1-acrepresents a C3-10 mono - or bi-carbocyclic ring, 3-10-membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom;

or sequentially exposing the oxidation reaction.

The above reaction of the compound of formula (IV) and compounds of formula (V-1) is known, and is performed, for example, in an organic solvent (for example, isopropyl alcohol, toluene, ethanol, tetrahydrofuran) or without a solvent, optionally in the presence of a base (e.g. sodium hydroxide, ethoxide sodium) at 0˜200°C.

The above reaction of the compound of formula (IV) and compounds of formula (V-2)is known to hold, for example, in an organic solvent (for example, in dimethoxyethane, dimethylformamide) in the presence of a catalyst (e.g. palladium acetate) using a phosphine compound (such as triphenylphosphine) at a temperature of from 20°With up to approximately the boiling temperature under reflux.

The oxidation reaction is conducted according to the above-described method.

On the other hand, from compounds of the formula (I-B), the compound in which R1-arepresents a C1-4-alkyl, substituted by 1-2 substituents OR6or CONR4R5, i.e. the compound (I-B-1)

where R1-a-1represents alkyl substituted by 1-2 substituents OR6or CONR4R5and other symbols have the above meanings;

can be obtained by reduction of compounds of formula (I-b-2):

where R1-a-2represents alkyl substituted by 1-2 substituents COOR6and other symbols have the above meanings;

or after exercise recovery, by reacting the compounds of formula (VI):

where R6-a-2represents (i) C1-10-alkyl, (ii) C2-10-alkenyl, (iii) C2-10-quinil, (iv) C3-15 mono - or bi-carbocyclic ring which is substituted by 1-5 substituents R18or is unsubstituted, (v) 3-15 membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, which is substituted by 1-5 substituents R18or is unsubstituted, or (vi) C1-4-alkyl, substituted by 1-2 groups selected from C3-10 mono - or bi-carbocyclic ring which is substituted by 1-5 substituents R18or is unsubstituted, and 3-10 membered mono - or bi-heterocyclic ring containing 1-4 nitrogen atom, 1-2 oxygen atoms and/or 1-2 sulfur atom, which is substituted by 1-5 substituents R18or is unsubstituted;

connection fo the formula (VII):

where all the symbols have the above values.

The reaction of recovery, as it is known, is carried out in an organic solvent (e.g. diethyl ether, methylene chloride, toluene), using a reducing agent (for example, diisopropylaminoethyl) at -78˜50°C.

The reaction of the compound (VI) and compounds after reduction reaction of the compounds of formula (I-B-2) is known, and is performed, for example, in an organic solvent (e.g. dimethylformamide), using a base (e.g. sodium hydride) at 0˜50°C.

The reaction of the compound (VII) and connection after you restore the compounds of formula (I-B-2) is known, and is performed, for example, in an organic solvent (e.g. methanol, ethanol, isopropanol), when 0˜100°C.

On the other hand, from compounds of the formula (I-B), the compound in which R1represents NR4R5and the substituents R4and R5each independently from each other represents a C1-15-alkyl, which is substituted by 1-5 substituents R17or is unsubstituted, and the substituents R2and R3are not HE, cyano, =N-OR11or the group that contains IT, cyano or =N-OR11, i.e. the compound (I-B-3):

where the substituents R4b-3and R5b-3each independently researched the mo from each other represents a C1-15-alkyl, which is substituted by 1-5 substituents R17or is unsubstituted, and other symbols have the above meanings;

can be obtained in accordance with the following scheme (1):

In scheme (1), the substituent R4b-6represents a C1-14-alkyl, which is substituted by 1-5 substituents R17or is unsubstituted substituent R5b-4represents a C1-14-alkyl, which is substituted by 1-5 substituents R17or is unsubstituted, and other symbols have the above values.

The amidation reaction is known, and is performed, for example, in an organic solvent (e.g. chloroform, methylene chloride, diethyl ether, tetrahydrofuran) or without a solvent, using acylhomoserine (for example, oxanilide or thionyl chloride, etc. at temperatures between -20°s to ˜ boiling point under reflux, and then the obtained gelegenheid acid may be subjected to interaction with the amine in an organic solvent (e.g. chloroform, methylene chloride, diethyl ether, tetrahydrofuran) in the presence of tertiary amine (e.g. pyridine, triethylamine, of dimethylaniline, dimethylaminopyridine) at 0-40°C. the Reaction can be conducted in an atmosphere of inert gas (e.g. argon, nitrogen) to prevent water to receive the deposits of the preferred result.

Response and recovery are known, and it is conducted, for example, in an organic solvent (e.g. tetrahydrofuran) using a reducing agent (for example, borane-dimethyl sulfide, lithium aluminum hydride) at a temperature of from 0°s to ˜ the boiling temperature under reflux.

The compound of the formula (I-B-7) can be obtained by the coupling of compounds of formula (II-2):

where all the symbols have the above meanings;

with the compound of the formula (III-2):

where all the symbols have the above meanings;

or sequentially exposing the oxidation reaction.

The above reaction of the compound of the formula (II-2) and the compounds of formula (III-2) is known, and is performed, for example, in an organic solvent (e.g. benzene, toluene) using an acid (e.g. p-toluensulfonate acid or its hydrate) at a temperature of from room temperature up to the boiling temperature under reflux, and then in an organic solvent (e.g. tetrahydrofuran) using a base (for example, Isopropylamine lithium) at a temperature of from -10 to ˜50°C.

(C) From compounds of formula (I) compound in which at least one of the substituents R2and R3is a HE or a group, soderjamoe, that is, the compound of formula (I-C):

where each of the substituents ZCUCand R3-Chas the same meaning as Z, U and R3provided that at least one of them is a HE or a group containing IT, and the other symbols have the meanings previously defined;

can also be obtained by demethylation of compounds in which at least one of the substituents R2and R3represents a methoxy or a group containing methoxy, in the compound of the formula (I-B), i.e. the compounds of formula (I-B-8):

where each of the substituents Zb-8Ub-8and R3-b-8has the same meaning as Z, U and R3provided that at least one of them represents a methoxy or a group containing methoxy, and the other symbols have the above values.

The demethylation reaction is known, and is performed, for example, in an organic solvent (e.g. methylene chloride, ethyl acetate, chloroform) using a Lewis acid (for example, tribromide boron) at -80˜80°C.

(D) From compounds of formula (I) compound in which at least one of the substituents R1, R2and R3represents a group containing =N-OR6or =N-OR11then there is the connection of the formula (I-D):

where each of the substituents R1-d, ZdUdand R3-dhas the same meaning as R1, Z, U and R3provided that at least one of them represents a group containing =N-OR6or =N-OR11and other symbols have the above meanings;

can be obtained

(1) deacetylating compounds in which at least one substituent R1, R2and R3represents a group containing a-CH(O-C1-4-alkyl)2in the compound of the formula (I-B), i.e. the compounds of formula (I-B-9):

where each of the substituents R1-b-9, Zb-9Ub-9and R3-b-9has the same meaning as R1, Z, U and R3provided that at least one of them represents a group containing a-CH(OS-1-4-alkyl)2and other symbols have the above meanings;

then the reaction of formation of the oxime, or

(2) the oxidation reaction of the compounds in which R1-arepresents a group containing IT in the compound of formula (I) or the compound of formula (I-C), i.e. the compounds of formula (I-B-10):

where each of the substituents R1-b-10, Zb-10Ub-10and R3-b-10has the same meaning as R1, Z, U and R3provided that R1-b-10HE is a sludge which, at least one of the substituents Zb-10Ub-10and R3-b-10is a group that contains IT, and the other symbols have the above meanings;

and then the formation of the oxime.

The reaction deacetylases known, and it is conducted, for example, in an organic solvent (for example, acetic acid, dioxane) using an acid (e.g. hydrochloric acid, sulfuric acid) at 0˜100°C.

The oxidation reaction is known, and is performed, for example, in an organic solvent (e.g. methylene chloride) or without solvent in the presence of a base (e.g. triethylamine, diisopropylethylamine) using dimethyl sulfoxide and complex of sulfur trioxide and pyridine, dicyclohexylcarbodiimide or oxalicacid at 0˜50°C.

The reaction of formation of the oxime, as it is known, is carried out, for example, in an organic solvent (e.g. pyridine) using H2N-O-R6or H2N-O-R11when 0˜50°C.

(E) From compounds of formula (I) compound in which at least one of the substituents R1, R2and R3represents cyano or a group containing cyano, i.e. the compound of formula (I-E):

where each of the substituents R1 nd, ZeUeand R3has the same values, that is R 1, Z, U and R3provided that at least one of the substituents R1 nd, ZeUeand R3represents cyano or the group that contains the cyano and the other symbols have the above meanings;

can be obtained by the reaction of dehydration of compounds in which at least one of the substituents R1, R2and R3represents a group containing =N-OH in the compound of the formula (I-D), i.e. the compound (I-D-1):

where each of the substituents R1-d-1, Zd-1Ud-1and R3-d-1has the same meaning as R1, Z, U and R3provided that at least one of the substituents R1-d-1, Zd-1Ud-1and R3-d-1represents a group containing =N-OH, and the other symbols have the above values.

The dehydration reaction is known, and is performed, for example, in an organic solvent (e.g. methylene chloride) in the presence of a base (e.g. triethylamine, diisopropylethylamine) using anhydrous triftormetilfullerenov acid or trichloromethylmercapto at 0˜50°C.

The compound of formula (IV) can be obtained by reaction of halogenation of compounds of formula (I-A).

The compounds of formula (II), (III), (V), (VI) and (VII) can be known by themselves or can be obtained well-known venture is the event. For example, the compound of formula (II):

where substituent R2-ahas the same meaning as R2provided that it is not HE, cyano, =N-OR11or the group that contains IT, cyano or =N-OR11and the substituent R3-ahas the above values;

can be obtained by the coupling of compounds of formula (VIII):

where all the symbols have the above meanings;

with hydrazine. In addition, among the compounds of the formula (III) ethyl ether, Cyclopentanone-2-carboxylic acid is commercially available. Among the compounds of formula (VI) 1-cyano-1-(2-methyl-4-methoxyphenyl)propane-2-it is described in the publication Bioorganic & Med. Chem., 8, 181-189 (2000).

And starting materials, and reagents in the present invention can be known by themselves or can be obtained by known methods.

In each reaction in the present description, the reaction products can be purified by conventional methods of purification, for example by distillation at atmospheric or reduced pressure, high performance liquid chromatography, thin-layer chromatography or column chromatography using silica gel or magnesium silicate; or by washing or recrystallization. Cleaning can be performed after each reaction or after a series of reactions.

Brief description of drawings

In Fig. 1 presents a graph of time spent in open transitions, rats, which came into force on 1, 3, 10 and 30 mg/kg of the compounds of the present invention.

In Fig. 2 shows a graph of the number of inputs into the open transitions rats, which came into force on 1, 3, 10 and 30 mg/kg of the compounds of the present invention.

The pharmacological activity

The compound of the present invention of formula (I) has, for example, antagonistic activity for receptors was made the KRF, and the effect of the compounds of the present invention is confirmed by the following tests.

(1) Assessing binding

[preparation of cell membranes]

After cultivation before reaching the merge cell line expressing human receptors CRF (line expressing cells: cells Cho-K1)cells are harvested with a scraper. The collected cells are washed twice with PBS, pre-suspending in buffer to assess binding (Tris-HCl (50 mm, pH 7.0), EDTU (2 mm, pH 8.0), MgCl2(10 mm), cooled by ice. Suspended cells are homogenized in the homogenizer Downs, and centrifuged at 10,000 g to collect the membrane fraction. The membrane fraction of the collected cells re-suspended in a small amount of buffer to assess the binding, and then diluted with the specified buffer to 1 mg/ml thus Obtained membrane faction is used to assess the binding.

[Evaluation link]

Fifty μl of [125I] h/R was made the KRF brought to 0.5 nm using a buffer to assess the binding, add in covered with silicone tube 1.5 ml tube, add 1 ál of compounds diluted in the appropriate number of times DMSO (to determine total binding) or with a solution of h/R was made the KRF (100 μm, for determination of nonspecific binding, respectively. Sample preparation the membrane fraction of 50 ál each added to the tubes to initiate the reaction (final concentration of [125I] h/R was made the KRF: 0,25 nm), then the mixture was incubated for 2 h at room temperature. At the end of the reaction tube is subjected to centrifugation at 15000 g to collect the membrane fraction. The supernatant discarded and the pellet washed twice in chilled PBS(-)containing 0.01% of Triton X-100. The magnitude of the radioactivity of the respective tubes is measured using γ-counter.

Specific binding is determined by subtracting a value of nonspecific binding from each variable binding.

The results show that the inventive compounds have a high affinity to the receptor CRF (IC50: < 1 μm).

(2) Measurement of activity to reduce anxiety using cascade plus-maze

Two transitions (indoor and outdoor) of the same width and length (50 cm·10 cm), which is s closed in the right corner with the formation of the plus-maze, rises to a height of 50 cm above ground level. Closed transition has a wall 40 see the Light at both ends of the open transition remain at constant brightness. Thirty minutes after administration of different doses of the tested compounds (5 ml/kg) male SD rats placed in the center of the plus-maze. The time spent in the open transitions and the number of entries in the corresponding transitions are measured over a 5 minute period. Staff, defining indicators, in the course of the experiment is located at fixed locations.

The results obtained are shown in Fig. 1 and 2. The graphs show that the time spent in the open transitions are extended considerably, and the number of entries into the open transitions increases significantly with the introduction of 3 and 10 mg/kg compound of example 2(78) of the present invention, i.e. the connection is active, the overwhelming anxiety.

[Toxicity]

The toxicity of the compounds of the present invention is very low, that is, it confirms the fact that these compounds are safe for use as medicaments.

Industrial application

[Application in pharmaceuticals]

Because they have antagonistic activity against receptors was made the KRF, the compounds of the present invention of formula (I) can be used for the prevention and/or cured what I diseases, caused by excessive secretion was made the KRF, such as depression, single episode depression, recurrent depression, postpartum depression, depression, caused by poor treatment of child anxiety, disorders associated with fear (e.g., panic, specific phobia, fear of ruin, social phobia, obsessive compulsive disorder), emotional disorders, bipolar disorder, post traumatic stress disorder, peptic ulcer, diarrhea, constipation, syndrome level becomes too low, colon cancer, inflammatory bowel disease (ulcerative colitis, Crohn's disease), stress-related disorder of the gastrointestinal tract, nervous vomiting, disorders of food intake (for example, loss of appetite, bulimia nervous), obesity, caused from stress, sleep disorders, pain, muscle fibers caused by sleep disorders, stress-induced suppression of the immune system caused by stress headaches, stress-induced fever, caused by stress, pain, post-operative stress, rheumatoid arthritis, osteoarthritis, osteoporosis, psoriasis, thyroid dysfunction, uveitis, asthma, induced inappropriate Antidiarrhoeal hormone disorders, pain, inflammation, allergic diseases, wounds of the head, spinal cord injury, ischemic narodnog the damage toxic neural damage, disease, Cushing's (Cushing), of an apoplectic fit, spasm, muscle spasm, epilepsy, ischemia, Parkinson's disease, Huntington's disease, urinary incontinence, Alzheimer's disease, senile dementia in medical literature type, multi-infarct dementia, amyotrophic lateral sclerosis, hypoglycemia, cardiovascular or associated with heart disease (hypertension, tachycardia, congestive heart failure), addiction to the excessive use of drugs or alcohol syndrome.

For the purposes of the above, the compounds of formula (I) of the present invention, their nontoxic salts, acid additive salts or hydrates can usually be introduced systemically or locally, usually by oral or parenteral administration.

Dose that must be entered, determined, for example, the age, body weight, symptom, the desired therapeutic effect, the route of administration and duration of treatment, etc. For adult human dose based on patient time usually ranges from 1 mg to 1000 mg by oral administration, up to several times a day, and from 0.1 to 100 mg when administered parenterally, preferably intravenously, up to several times per day or by continuous injection into a vein over 1 to 24 hours in the den is.

As mentioned above, the dose that should be used depend on various conditions. Therefore, there are cases in which can be used doses lower or higher than the above defined intervals.

Compounds of the present invention can be introduced in the form of, for example, solid compositions, liquid compositions or other compositions for oral administration, solutions for injection, liquid, ointments or suppositories for parenteral administration.

Solid compositions for oral administration include compressed tablets, pellets, capsules, dispersible powders and granules. Capsules include hard capsules and soft capsules.

In such solid forms one or more active compounds can be mixed with carriers such as lactose, mannitol, glucose, microcrystalline cellulose, starch; binders such as hydroxypropylcellulose, polyvinylpyrrolidone or metasilicates magnesium; dispersing agents such as calcipala cellulose; lubricating agents such as magnesium stearate; stabilizing agents and solution adjuvants, such as glutamic acid or aspartic acid; and prepared in accordance with methods well known in normal pharmaceutical practice. If desirable the, the solid form may be covered by finishes such as sugar, gelatin, phthalate of hydroxypropylcellulose or hydroxypropylmethylcellulose; or can be covered by two or more films. And, in addition, the coating can include a Department within the capsules of the ability to absorb materials such as gelatin.

Liquid forms for oral administration include pharmaceutically acceptable solutions, suspensions and emulsions, syrups and elixirs. In such forms one or more active compounds may be dissolved, suspended or emulsified in the diluent normally used in this field, such as purified water, ethanol or their mixture. In addition, such liquid formulations may include some additives, such as wetting agents, suspendresume agents, emulsifying agents, sweetening agents, corrective agents, flavoring agents, preservative or buffer agent.

Solutions for injection for parenteral administration include sterile aqueous solutions, suspensions, emulsions and solid form, which is dissolved or suspended in the solvent(s) for injection immediately before use. In solutions for injection one or more active compounds may be dissolved, suspended or emulsified in a solvent(s). Solvents can include di is fillerbunny water for injection, physiological saline, vegetable oil, propylene glycol, polyethylene glycol, an alcohol, e.g. ethanol, or a mixture. Solutions for injection may include some additives, such as stabilizing agents, solution adjuvants, such as glutamic acid, aspartic acid or POLYSORBATE 80 (registered trade mark); suspendresume agents, emulsifying agents, soothing agent, a buffer agent, a preservative. They can be sterilized in the final stage or can be cooked and balanced in accordance with the methods of sterilization. They can also be prepared in the form of sterile solid dosage forms, such as dried by freezing of products that can be dissolved in sterile water or some other sterile diluent for injection immediately before use.

Other forms for parenteral administration include liquids for external use, ointments and undermydesk liquid ointments, inhalations, sprays, candles and uterine rings for vaginal insertion, which contain one or more active compounds and can be prepared by methods in themselves known. Sprays can include additional substances other than diluents, such as stabilizing agents, such as sodium sulfate; isotonic buffer and the coefficients, such as sodium chloride, sodium citrate or citric acid. For the preparation of such sprays may be used the method described in U.S. patent No. 2868691 or 3095355.

The best way of carrying out the invention

The following reference examples and examples illustrate but do not limit the present invention.

When chromatographic separation and TLC solvents in parentheses show exhibiting or eluting solvents, and used the ratio of solvents are three-dimensional.

These NMR listed with indication used in the measurement of the solvent (in parentheses).

Reference example 1

2-Methyl-4-methoxyphenylacetonitrile

In an argon atmosphere a mixture of N-bromosuccinimide (17.8 g) and 2,2'-azobisisobutyronitrile (494 mg) are added to a solution of 1,2-dimethyl-4-methoxybenzene (13,6 g) in carbon tetrachloride (200 ml). The mixture is refluxed for 6.5 hours. The reaction mixture was cooled in an ice bath. The insoluble substance is filtered off and washed with carbon tetrachloride. The combined filtrate is concentrated. The residue is dissolved in N,N-dimethylformamide (100 ml), and to the mixture is added sodium cyanide (9,86 g). The mixture is stirred over night at room temperature. The reaction mixture was poured into water and the mixture extracted with diethyl ether. About the organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated. The residue is purified column chromatography on silica gel (ethyl acetate:n-hexane = 1:6 to 1:4)will be specified in the header connection (11,78 g)having the following physical properties.

TLC: Rf= 0,20 (n-hexane:ethyl acetate = 9:1).

NMR (300 MHz, CDCl3): δ from 7.24 (d, J=8.0 Hz, 1H), 6,78-6,72 (m, 2H), 3,79 (s, 3H), of 3.60 (s, 2H), 2,32 (s, 3H).

Reference example 2

1-Cyano-1-(2-methyl-4-methoxyphenyl)propane-2-he

In an argon atmosphere to a solution of the compound obtained in reference example 1 (11,7 g)in ethyl acetate (60 ml), add on parts sodium metal (2.3 g). The mixture is stirred for 2 hours at 50°C. To the reaction mixture are added ethyl acetate and the mixture is refluxed for 2.5 hours and then stirred overnight at room temperature. Precipitated precipitated substance is filtered off and washed with diethyl ether. The resulting crystals are dissolved in water (300 ml). The solution is brought to pH 4 by adding 2 N. hydrochloric acid and extracted with ethyl acetate. The organic layer is dried over anhydrous sodium sulfate and concentrated receive specified in the header connection (12,06 g), which has the following physical properties.

TLC: Rf= 0,45 (n-hexane:ethyl acetate = 1:1).

Reference example 3

2-Chloro-4-methoxybutanol Isleta

A solution of 3-chloro-4-bromoanisole (2.14 g) in anhydrous tetrahydrofuran (10 ml) cooled to -78°C. To the solution is added dropwise to 1.56 M n-utility in hexane (6.5 ml) and the mixture is stirred for 30 min. the reaction mixture is added dropwise triisopropylsilyl (2.3 ml) and the mixture is stirred 2 h at -78°C. To the reaction mixture is added saturated aqueous solution of ammonium chloride and the mixture extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated. The obtained solid is washed with tert.-butylmethylamine ether (4 ml), filtered and dried, get mentioned in the title compound (681 mg) having the following physical properties.

TLC: Rf= 0,55 (methylene chloride:methanol = 19:1).

NMR (300 MHz, CDCl3): δ 7,22 (d, J=8,4 Hz, 1H), 6,93 (d, J=2.4 Hz, 1H), 6,86 (DD, J=8,4, 2.4 Hz, 1H), 3,79 (s, 3H).

Reference example 4

4-(2-chloro-4-methoxyphenyl)-5-methylisoxazol

To a suspension of the compound obtained in reference example 3 (644 mg), 4-iodine-5-methylisoxazole (658 mg) and sodium bicarbonate (791 mg) in a mixture of dimethoxyethane (2.5 ml) and water (2.5 ml) is added tetrakis(triphenylphosphine)palladium (36 mg). The mixture is stirred for 16 h at 80°C. To the reaction mixture, which is cooled to room temperature is, add water and ethyl acetate. The insoluble substance is filtered off. The organic layer separated from the filtrate, washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated. The residue is purified column chromatography on silica gel (n-hexane:ethyl acetate = 19:1 to 15:1)get mentioned in the title compound (637 mg) having the following physical properties.

TLC: Rf= 0,44 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 8,29 (users, 1H), 7,16 (d, J=8,4 Hz, 1H),? 7.04 baby mortality (d, J=2.4 Hz, 1H), 6.87 in (DD, J=8,4, 2.4 Hz, 1H), 3,84 (s, 3H), 2,41 (users, 3H).

Reference example 5

1-Cyano-1-(2-chloro-4-methoxyphenyl)propane-2-he

To a solution of the compound obtained in reference example 4 (623 mg)in methanol (2.8 ml) is added 1.5 M sodium methoxide in methanol (2.8 ml) and the mixture is stirred for 4 hours. The reaction mixture was diluted with water and washed with hexane/tert.-butyl methyl ether (10 ml, 1:1). The aqueous layer was brought to pH 5 by adding 4 n hydrochloric acid (1 ml) and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrate, get mentioned in the title compound (497 mg) having the following physical properties.

TLC: R f= 0,13 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,38 (d, J=8,4 Hz, 1H), 7,00 (d, J=2.4 Hz, 1H), 6.89 in (DD, J=8,4, 2.4 Hz, 1H), 5,11 (s, 1H), 3,83 (s, 3H), to 2.29 (s, 3H).

Reference example 6

5-Amino-3-methyl-4-(2-methyl-4-methoxyphenyl)pyrazole

To a solution of the compound obtained in reference example 2 (8,63 g)in toluene (200 ml) is added acetic acid (8.0 ml) and hydrazine monohydrate (4.5 ml). The mixture is refluxed for 5.5 hours and stirred at room temperature overnight. The reaction mixture was concentrated. To the residue add 6 N. hydrochloric acid and the solution extracted with a mixture of ethyl acetate/n-hexane (30 ml/30 ml). The aqueous layer was acidified by adding concentrated aqueous ammonia, and extracted with ethyl acetate. The organic layer is dried over anhydrous sodium sulfate and concentrated receive specified in the header connection (scored 8.38 g) with the following physical properties.

TLC: Rf= 0,30 (chloroform:methanol = 9:1).

NMR (300 MHz, CDCl3): δ was 7.08 (d, J=8.0 Hz, 1H), at 6.84 (d, J=2.5 Hz, 1H), 6,77 (DD, J=8,0, 2.5 Hz, 1H), 4,10 (users, 3H), 3,83 (s, 3H), of 2.18 (s, 3H), 2,07 (s, 3H).

Example 1

8-Hydroxy-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

To a solution of the compound obtained in reference example 6 (500 mg)in acetic acid (3 ml) is added ethyl-cyclopen is anon-2-carboxylate (0,40 ml). The mixture is refluxed 3 hours. Then the reaction mixture is cooled to room temperature, to the mixture is added diethyl ether/n-hexane (10 ml; 2:1). Precipitated precipitated crystals are filtered and the crystals washed with a mixture of diethyl ether/n-hexane (10 ml; 2:1), dried, get mentioned in the title compound (480 mg) having the following physical properties.

TLC: Rf= 0,47 (chloroform:methanol = 9:1).

NMR (300 MHz, DMSO-d6): δ 11,90 (users, 1H), 7,10 (d, J=8.0 Hz, 1H), 6,93 (d, J=3.0 Hz, 1H), 6,83 (DD, J=3,0, 8.0 Hz, 1H), of 3.78 (s, 3H), of 2.81 (t, J=7.5 Hz, 2H), 2,66 (t, J=7.5 Hz, 2H), 2,07 (s, 3H), of 2.05 (s, 3H), 2,03 (m, 2H).

Reference example 7

8-Chloro-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

To a suspension of the compound obtained in example 1 (400 mg)in toluene (4 ml) is added phosphorus oxychloride (0,60 ml) and diethylaniline (0.25 ml). The mixture is refluxed for 1 hour. The reaction mixture is cooled and poured into cold aqueous sodium bicarbonate solution. The mixture is stirred for 10 minutes to destroy excess phosphorus oxychloride. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated. The residue is purified column chromatography on silica gel (ethyl acetate:n-hexa is = 1:3 to 1:2), get listed in the title compound (411 mg) having the following physical data.

TLC: Rf= 0,52 (n-hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ to 7.15 (d, J=8.5 Hz, 1H), to 6.88 (d, J=2.5 Hz, 1H), for 6.81 (DD, J=8,5, 2.5 Hz, 1H), 3,83 (s, 3H), 3,09-3,00 (m, 4H), 2.40 a (s, 3H), of 2.23 (m, 2H), of 2.15 (s, 3H).

Example 2

8-(3-Pentylamine)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

A mixture of the compound obtained in reference example 7 (150 mg)and 3-pentylamine (0.6 ml) is stirred for 1 hour at 140°C. the Reaction mixture is cooled and purified column chromatography on silica gel (ethyl acetate:n-hexane = 1:3), get mentioned in the title compound (169 mg) having the following physical properties.

TLC: Rf= 0,57 (n-hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ to 7.15 (d, J=8.5 Hz, 1H), 6,85 (d, J=3.0 Hz, 1H), 6,78 (DD, J=8,5, 3.0 Hz, 1H), 6,21 (d, J=10.5 Hz, 1H), 3,82 (s, 3H), 3,81 (m, 1H), is 3.08 (t, J=7,0 Hz, 2H), 2,89 (t, J=8.0 Hz, 2H), 2,30 (s, 3H), are 2.19 (s, 3H), and 2.14 (m, 2H), 1.69 in (m, 4H), of 1.02 (m, 6H).

Examples 2(1)-2(365)

The following compounds are obtained using the appropriate connection instead of 1,2-dimethyl-4-methoxybenzene, by the same method as in the series of reactions of reference example 1 → reference example 2 → reference example 6 → example 1 using the appropriate connection instead of ethyl Cyclopentanone-2-carboxylate → reference the example 7 → example 2 using a corresponding compound instead of 3 pentylamine or using the compounds obtained in reference example 5, or the corresponding compound by the same method as in the series of reactions of reference example 6 → example 1 → reference example 7 → example 2, or sequentially with known way to salt connection.

Example 2(1)

8-(N-Ethyl-N-n-butylamino)-2-methoxymethyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,43 (n-hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,22 (d, J=8.7 Hz, 1H), at 6.84 (d, J=2.7 Hz, 1H), 6,77 (DD, J=8,7, 2.7 Hz, 1H), 4,49 (m, 2H), 3,81 (s, 3H), 3,67 (sq, J=7.2 Hz, 2H), 3,61 (t, J=7.2 Hz, 2H), 3.33 and (s, 3H), of 2.97 (t, J=7.2 Hz, 2H), only 2.91 (t, J=7.8 Hz, 2H), 2,19 (s, 3H), 2.13 in (m, 2H), 1.55V (m, 2H), 1,35 (m, 2H), 1,17 (t, J=7.2 Hz, 3H), of 0.89 (t, J=7.2 Hz, 3H).

Example 2(2)

8-(N-Propyl-N-(2-hydroxyethyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,80 (n-hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,14 (d, J=8,4 Hz, 1H), 6,86 (d, J=2.7 Hz, 1H), 6,79 (DD, J=8,4, 2.7 Hz, 1H), 3,90 (t, J=4,8 Hz, 2H), 3,83 (s, 3H), of 3.64 (m, 2H), 3.43 points (m, 2H), 2,98 (t, J=7.2 Hz, 2H), 2,92 (t, J=7.8 Hz, 2H), 2,31 (s, 3H), 2,17 (s, 3H), of 2.15 (m, 2H), 1,58 (m, 2H), of 0.95 (t, J=7.2 Hz, 3H).

Example 2(3)

8-(3-Pentylamine)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrothieno[3,4-d]is irazola[1,5-a]pyrimidine

TLC: Rfor = 0.51 (n-hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.15 (d, J=8.5 Hz, 1H), 6,86 (d, J=2.5 Hz, 1H), 6,79 (DD, J=8,5, 2.5 Hz, 1H), 6,44 (d, J=10.0 Hz, 1H), 4,32 (users, 2H), 4,14 (users, 2H), 3,82 (s, 3H), 3,76 (m, 1H), 2,32 (s, 3H), of 2.18 (s, 3H), 1,84-of 1.57 (m, 4H), of 1.03 (t, J=7.0 Hz, 6H).

Example 2(4)

9-(3-Pentylamine)-6-methyl-5-(2-methyl-4-methoxyphenyl)-2,3-dihydrothieno[3,2-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,40 (n-hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.15 (d, J=8.5 Hz, 1H), 6,85 (d, J=3.0 Hz, 1H), 6,79 (DD, J=8,5, 3.0 Hz, 1H), 6,17 (d, J=10.0 Hz, 1H), 3,99 (m, 1H), 3,82 (s, 3H), 3,36-3,20 (m, 4H), of 2.30 (s, 3H), of 2.18 (s, 3H), 1,82-of 1.56 (m, 4H), of 1.03 (t, J=7.5 Hz, 6H).

Example 2(5)

8-(3-Pentylamine)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,33 (n-hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.15 (d, J=8.5 Hz, 1H), 6,86 (d, J=2.5 Hz, 1H), 6,79 (DD, J=8,5, 2.5 Hz, 1H), 6,32 (d, J=10.0 Hz, 1H), from 5.29 (s, 2H), 4,90 (users, 2H), 3,82 (s, 3H), 3,24 (m, 1H), 2,33 (s, 3H), of 2.18 (s, 3H), 1,84-of 1.56 (m, 4H), of 1.02 (t, J=7.5 Hz, 6H).

Example 2(6)

9-(3-Pentylamine)-6-methyl-5-(2-methyl-4-methoxyphenyl)-2,3-dihydrofuro[3,2-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,43 (n-hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,31 (users, 1H), 7,12 (d, J=8,4 Hz, 1H), 6.89 in (d, J=2.7 Hz, 1H), PC 6.82 (DD, J=8,4, 2.7 Hz, 1H), amounts to 4.76 (t, J=9.0 Hz, 2H), 4,30 (m, 1H), 3,83 (s, 3H), 3,74 (t, J=9.0 Hz, 2H),2,34 (s, 3H), 2,19 (s, 3H), 1,90 is 1.70 (m, 4H), was 1.04 (m, 6H).

Example 2(7)

The hydrochloride of 9-(3-pentylamine)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,6,7,8-tetrahydropyrazolo[3,2-b]hintline

TLC: Rf= 0,45 (n-hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 13,04 (users, 1H), to $ 7.91 (users, 1H), 7,15 (d, J=8.5 Hz, 1H), of 6.96 (d, J=2.5 Hz, 1H), 6.87 in (DD, J=8,5, 2.5 Hz, 1H), 5,65 (users, 1H), 3,79 (s, 3H), of 2.75 (m, 2H), 2,58 (m, 2H), 2,19 (s, 3H), of 2.05 (s, 3H), 1,88-of 1.64 (m, 8H), of 0.91 (t, J=7.5 Hz, 6H).

Example 2(8)

6-Methyl-5-(2-methyl-4-methoxyphenyl)-9-[(2S,4R)-4-methoxy-2-methoxypiperidine-1-yl]-2,3-dihydrofuro[3,2-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,24 (n-hexane:ethyl acetate = 1:1).

NMR (300 MHz, DMSO-d6): δ to 7.09 (d, J=7.5 Hz, 1H), make 6.90 (d, J=2.4 Hz, 1H), for 6.81 (DD, J=7,5, 2.4 Hz, 1H), 5,07 (users, 1H), of 4.66 (dt, J=9,0, 9.0 Hz, 1H), 4,56 (dt, J=9,0, 9.0 Hz, 1H), 4,24 (DD, J=12,6, 3.6 Hz, 1H), 4,05 (users, 1H), of 3.85 (d, J=12,6 Hz, 1H), of 3.77 (s, 3H), 3,42 (DD, J=10,2, 3,9 Hz, 1H), 3,33 (DD, J=10,2, 5,l Hz, 1H), up 3.22 (DD, J=9,0, 9,0 Hz, 2H), 3,21 (s, 3H), 3,18 (s, 3H), of 2.18 (s, 3H), 2,07 (s, 3H), 2,30-of 1.95 (m, 2H).

Example 2(9)

9-(3-Pentylamine)-6-methyl-5-(2-methyl-4-methoxyphenyl)-2,3-dihydropyrrolo[3,2-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,37 (n-hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,16 (d, J=8,4 Hz, 1H), 6,85 (d, J=2.7 Hz, 1H), 6,78 (DD, J=2.7, and an 8.4 Hz, 1H), 5,86 (d, J=10.5 Hz, 1H), 4,07 (m, 1H), 3,82 (s, 3H), to 3.58 (t, J=8,1 Hz, 2H), 3,06 (t, J=8,1 Hz, 2H), 2,30 (s, 3H), are 2.19 (s, 3H), 1,52-to 1.82 (m, 4H), 1,01 (m, 6H).

Example 2(10)

Hydrochloride of 2-methyl-3-(2-methyl-4-methoxyphenyl)-8-[(2S,4R)-4-methoxy-2-methoxypiperidine-1-yl]-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,30 (n-hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,15 and 7,07 (d, J=8,4 Hz, two conformational isomers, 1H), 6.89 in and 6,87 (d, J=2.7 Hz, two conformational isomers, 1H), 6.83 and to 6.80 (DD, J=8,4, 2.7 GHz, two conformational isomers, 1H), 5,65 (users, 1H), 4,32-4,10 (m, 3H), 3,82 (s, 3H), 3,50 is 3.40 (m, 4H), 3,367 and 3,361 (s, two conformational isomers, 3H), 3,29, and of 3.28 (s, two conformational isomers, 3H), 3,23-to 2.99 (m, 2H), 2,42 (m, 1H), 2,30-2,10 (m, 3H), 2,245 and 2,240 (with two conformational isomers, 3H), 2.22 and 2,14 (with two conformational isomers, 3H).

Example 2(11)

Hydrochloride of 2-methyl-3-(2-methyl-4-methoxyphenyl)-8-[(2S,4R)-4-methoxy-2-methoxypiperidine-1-yl]-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,22 (n-hexane:ethyl acetate = 1:1).

NMR (300 MHz, DMSO-d6) δ7,10 (users, 1H), 6.89 in (d, J=2.4 Hz, 1H), for 6.81 (DD, J=8,1, 2.4 Hz, 1H), 5,33 (d, J=10,8 Hz, 1H), 5.25-inch (users, 1H), 5,15 (d, J=10,8 Hz, 1H), around 4.85 (d, J=14.4 Hz, 1H), and 4.75 (d, J=14.4 Hz, 1H), 4,10-of 3.85 (m, 3H), of 3.77 (s, 3H), 3,39 (DD, J=9,9, 4.5 Hz, 1H), or 3.28 (DD, J=9,9, 5,l Hz, 1H), up 3.22 (s, 3H), 3.15 in (s, 3H), of 2.25 (m, 1H), of 2.21 (s, 3H), 2,15-2,00 (m, 4H).

Example 2(12)

6-Methyl-5-(2-methyl-4-methoxyphenyl)-9-[(2S,4R)-4-methoxy-2-methoxypiperidine-1-yl]-2,3-dihydropyrrolo[3,2-d]pyrazolo[1,5-a]pyrimidine

<> TLC: Rf= 0,43 (chloroform:methanol = 20:1).

NMR (300 MHz, CDCl3): δ7,16 (d, J=8,4 Hz, 1H), 6,86 (d, J=2.7 Hz, 1H), 6,79 (DD, J=2.7, and an 8.4 Hz, 1H), 4,71 (m, 1H), 4,20 (m, 1H), 4,06 (m, 1H), 3,82 (s, 3H), of 3.60 (t, J=7.8 Hz, 2H), 3,54 (m, 1H), 3,48 (DD, J=4,5, 9,6 Hz, 1H), 3,39 (m, 1H), 3,34 (s, 3H), of 3.28 (s, 3H), to 3.09 (m, 2H), 2,24-to 2.40 (m, 4H), to 2.18 (s, 3H), 2,01 (m, 1H).

Example 2(13)

8 Isopropylamino-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,34 (n-hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.15 (d, J=8,4 Hz, 1H), 6,86 (d, J=2.7 Hz, 1H), 6,79 (DD, J=8,4, 2.7 Hz, 1H), to 6.39 (d, J=9.6 Hz, 1H), 5,32 (s, 2H), 4,90 (s, 2H), 3,82 (s, 3H), 3,74 (m, 1H), 2,32 (s, 3H), of 2.16 (s, 3H), 1,41 (d, J=6.6 Hz, 6H).

Example 2(14)

8-[(2S)-1,1-Diethoxybutane-2-yl]amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,26 (n-hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.15 (d, J=8,1 Hz, 1H), 6,86 (d, J=2.4 Hz, 1H), 6,79 (DD, J=8,1, 2.4 Hz, 1H), 6,57 (userd, J=ll,l Hz, 1H), are 5.36 (d, J=9.9 Hz, 1H), 5,26 (d, J=9.9 Hz, 1H), 4,90 (s, 2H), 4,33 (d, J=3,9 Hz, 1H)that is 3.82 (s, 3H), 3,50 (s, 3H), of 3.48 (s, 3H), 3,39 (m, 1H), 2,32 (s, 3H), 2,17 (s, 3H), of 1.88 (m, 1H), 1,68 (m, 1H), 1.04 million (users, 3H).

Example 2(15)

8-[(2S)-1,1-Diethoxybutane-2-yl]amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,30 (n-hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.15 (d, J=8,1 Hz, 1H), 6,85 (q, j =3.0 Hz, 1H), 6,77 (DD, J=8,1, 3.0 Hz, 1H), 6,47 (userd, J=11.8 Hz, 1H), 4,34 (users, 1H), 4,01 (m, 1H), 3,81 (s, 3H), 3,49 (C, 6N), 3,19-3,00 (m, 2H), 2,89 (t, J=7.8 Hz, 2H), 2,30 (s, 3H), of 2.18 (s, 3H), 2.13 in (m, 2H), 1,86 (m, 1H), 1,65 (m, 1H), 1.04 million (users, 3H).

Example 2(16)

8-(1,3-Dimethoxypropane-2-yl)amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,42 (n-hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,14 (d, J=8,1 Hz, 1H), 6.87 in (userd, J=8,1 Hz, 1H), 6,85 (d, J=2.4 Hz, 1H), 6,79 (DD, J=8,1, 2.4 Hz, 1H), 5,33 (s, 2H), 4,89 (s, 2H), 3,81 (s, 3H), of 3.75 (m, 1H), 3,62 (d, J=4.8 Hz, 4H), 3,42 (s, 6H), of 2.33 (s, 3H), of 2.16 (s, 3H).

Example 2(17)

8-Bis(2-methoxyethyl)amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,24 (n-hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDC13): δ to 7.15 (d, J=8,1 Hz, 1H), 6.87 in (d, J=2.7 Hz, 1H), 6,79 (DD, J=8,1, 2.7 Hz, 1H), 5,22 (s, 2H), 4,89 (s, 2H), 3,88 (t, J=6.0 Hz, 4H), 3,82 (s, 3H), 3,55 (t, J=6.0 Hz, 4H), 3,30 (s, 6H), of 2.33 (s, 3H), of 2.16 (s, 3H).

Example 2(18)

8-(1,3-Dimethoxypropane-2-yl)amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,53 (n-hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,01 (d, J=8,4 Hz, 1H), 6,72 (d, J=2.7 Hz, 1H), only 6.64 (DD, J=8,4, 2.7 Hz, 1H), 6,60 (d, J=9.9 Hz, 1H), 4,14 (m, 1H), 3,69 (s, 3H), 3,50 (d, J=5.4 Hz, 4H), 3,30 (s, 6H), to 2.99 (t, J=7.2 Hz, 2H)that was 2.76 (t, J=7.8 Hz, 2H), 2,18 (s, 3H), 2,04 (s, 3H), a 2.01 (m, 2H).

Example 2(19)

8-Bis(3-methoxyethyl)amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,41 (n-hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ to 7.15 (d, J=8,4 Hz, 1H), 6,86 (d, J=2.7 Hz, 1H), 6,78 (DD, J=8,4, 2.7 Hz, 1H), 3,88 (t, J=5.7 Hz, 4H), 3,82 (s, 3H), 3,52 (t, J=5.7 Hz, 4H), 3,30 (s, 6H), of 3.00 (t, J=6.9 Hz, 2H), only 2.91 (t, J=7,8 Hz, 2H), 2,32 (s, 3H), of 2.18 (s, 3H), and 2.14 (m, 2H).

Example 2(20)

Hydrochloride (5RS)-8-(3-pentylamine)-2,5-dimethyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,44 (n-hexane:ethyl acetate = 2:1).

NMR (300 MHz, DMSO-d6): δ 8,71 (users, 1H), 7,15 (d, J=8.5 Hz, 1H), 6,93 (d, J=2.5 Hz, 1H), 6,85 (DD, J=8,5, 2.5 Hz, 1H), 5,70 (users, 1H), 5.25-inch (DD, J=10,0, 2.0 Hz, 1H), 5,17 (d, J=10.0 Hz, 1H), 5,11 (m, 1H), 3,79 (s, 3H), 3,26 (m, 1H), and 2.26 (s, 3H), 2,10 (s, 3H), 1,83-of 1.57 (m, 4H), of 1.41 (d, J=5.5 Hz, 3H), 0,93-of 0.83 (m, 6H).

Example 2(21)

8-(3-Pentylamine)-2-methyl-3-(2,4-dichlorophenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,50 (n-hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,50 (d, J=2.0 Hz, 1H), 7,35 (d, J=8.5 Hz, 1H), 7,29 (DD, J=8,5, 2.0 Hz, 1H), 6,23 (d, J=10.5 Hz, 1H), 3,81 (m, 1H), 3,09 (t, J=7.5 Hz, 2H), only 2.91 (t, J=7.5 Hz, 2H), 2,34 (s, 3H), of 2.15 (m, 2H), 1,82-of 1.55 (m, 4H), 1,01 (t, J=7.5 Hz, 6H).

Example 2(22)

8-(3-Pentylamine)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydropyrrolo[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,48 (chloroform:methanol = 10:1).

NMR (300 MHz, CDCl3): δ 7,16 (d, J=8,1H, 1H), 6,86 (d, J=2.7 Hz, 1H), 6,79 (DD, J=2,7, 8,1 Hz, 1H), 6,29 (d, J=10,2 Hz, 1H), 4,43 (s, 2H), 4,10 (s, 2H), 3,82 (s, 3H), 3,49 (m, 1H), 2,32 (s, 3H), of 2.18 (s, 3H), 1.55V-of 1.84 (m, 4H), of 1.02 (m, 6H).

Example 2(23)

8 Diethylamino-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,67 (n-hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,16 (d, J=8,4 Hz, 1H), 6,86 (d, J=2.7 Hz, 1H), 6,79 (DD, J=8,4, 2.7 Hz, 1H), 3,82 (s, 3H), 3,66 (sq, J=7.2 Hz, 4H), to 2.99 (t, J=7.5 Hz, 2H), only 2.91 (t, J=7.5 Hz, 2H), 2,33 (s, 3H), 2,19 (s, 3H)by 2.13 (m, 2H), of 1.18 (t, J=7.2 Hz, 6H).

Example 2(24)

8-(N-Ethyl-N-n-butylamino)-2-methyl-3-(2,4-dichlorophenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,78 (n-hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,17 (d, J=8,4 Hz, 1H), 6,86 (d, J=3.0 Hz, 1H), 6,79 (DD, J=8,4, 3.0 Hz, 1H), 3,82 (s, 3H), 3,70 of 3.56 (m, 4H), of 2.97 (t, J=6.9 Hz, 2H), only 2.91 (t, J=7.7 Hz, 2H), 2,33 (s, 3H), 2,19 (s, 3H), 2,13 (m, 2H), 1.55V (m, 2H), 1,32 (m, 2H), 1,17 (t, J=7.2 Hz, 3H), of 0.90 (t, J=7.2 Hz, 3H).

Example 2(25)

8 Dicyclopentadiene-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,40 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ to 7.15 (d, J=8,1 Hz, 1H), 6,85 (d, J=2.7 Hz, 1H), 6,78 (DD, J=8,1, 2.7 Hz, 1H), 6,36 (d, J=10,2 Hz, 1H), 3,82 (s, 3H), 3,41 (m, 1H), 3,01 (t, J=7.2 Hz, 2H), 2,87 (t, J=8,1 G is, 2H), 2,31 (s, 3H), 2,19 (s, 3H), 2,10 (m, 2H), 1,20-1,08 (m, 2H), 0,66-0,32 (m, 8H).

Example 2(26)

8-(N-Propyl-N-(2-hydroxyethyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,26 (n-hexane:ethyl acetate = 1:2).

NMR (300 MHz, CDCl3): δ 7,14 (d, J=8,4 Hz, 1H), 6.87 in (d, J=2.7 Hz, 1H), 6,80 (DD, J=8,4, 2.7 Hz, 1H), 6,54 (users, 1H), total of 5.21 (s, 2H), 4,89 (s, 2H), 3.96 points (ushort, J=4,8 Hz, 2H), 3,83 (s, 3H), 3,80 (m, 2H), 3,29 (t, J=7.5 Hz, 2H), 2,33 (s, 3H), 2,17 (s, 3H), and 1.63 (m, 2H), and 1.00 (t, J=7.5 Hz, 3H).

Example 2(27)

8-(3-Pentylamine)-2-methoxymethyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,27 (n-hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,19 (d, J=8.5 Hz, 1H), 6,85 (d, J=2.5 Hz, 1H), 6,78 (DD, J=8,5, 2.5 Hz, 1H), 6,32 (d, J=10.5 Hz, 1H), 4,54-and 4.40 (m, 2H), 3,82 (s, 3H), 3,81 (m, 1H), 3,37 (s, 3H), 3,10 (t, J=7,0 Hz, 2H), 2.91 in (t, J=8.0 Hz, 2H), measuring 2.20 (s, 3H), and 2.14 (m, 2H), 1,80-of 1.53 (m, 4H), 1,08-of 0.94 (m, 6H).

Example 2(28)

8-(3-Pentylamine)-2-methyl-3-(1,3-dioksiinien-5-yl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,61 (n-hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,22 (d, J=1.5 Hz, 1H), 7,10 (DD, J=1.5 and 8.1 Hz, 1H), 6.89 in (d, J=8,1 Hz, 1H), 6,20 (userd, J=10.5 Hz, 1H), 5,96 (s, 2H), 3,80 (m, 1H), is 3.08 (t, J=7.5 Hz, 2H), equal to 2.94 (t, J=8,1 Hz, 2H), 2,52 (s, 3H), of 2.15 (m, 2H), 1,51 and 1.80 (m, 4H), and 1.00 (t, J=7.5 Hz, 6H).

Example 2(29)

8-(3-Pentylamine)-2-methyl-3-(3,4-acid)-6,dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,56 (n-hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,29 (d, J=2.1 Hz, 1H), 7,19 (DD, J=2,1, 8,1 Hz, 1H), of 6.96 (d, J=8,1 Hz, 1H), 6,20 (userd, J=10.5 Hz, 1H), 3,93 (s, 3H), 3,91 (s, 3H), 3,80 (m, 1H), 3,09 (t, J=7.2 Hz, 2H), equal to 2.94 (t, J=7.5 Hz, 2H), to 2.55 (s, 3H), of 2.16 (m, 2H), 1,53-of 1.81 (m, 4H), and 1.00 (t, J=7.2 Hz, 6H).

Example 2(30)

8 Cyclopropylamino-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,33 (n-hexane:ethyl acetate = 3:2).

NMR (300 MHz, CDCl3): δ 7,14 (d, J=8,1 Hz, 1H), 6,86 (d, J=2.7 Hz, 1H), 6,79 (DD, J=8,1, 2.7 Hz, 1H), 6,62 (users, 1H), 5,54 (users, 2H), 4,91 (users, 2H), 3,82 (s, 3H), 2,89 (m, 1H), 2,30 (s, 3H), of 2.15 (s, 3H), 0,98-0,84 (m, 4H).

Example 2(31)

8-(3-Pentylamine)-2-cyclobutyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,62 (benzene:ethyl acetate = 5:1).

NMR (300 MHz, CDCl3): δ to 7.09 (d, J=8,1 Hz, 1H), 6,83 (d, J=2.7 Hz, 1H), 6.75 in (DD, J=8,1, 2.7 Hz, 1H), 6.35mm (d, J=10.5 Hz, 1H), 3,82 (s, 3H), 3,81 (m, 1H), 3,53 (m, 1H), is 3.08 (t, J=7.5 Hz, 2H), 2,88 (t, J=7.8 Hz, 2H)that is 2.41 (m, 2H), 2,28-to 2.06 (m, 4H), of 2.15 (s, 3H), 2,01 is 1.58 (m, 6H), of 1.05 (t, J=7.5 Hz, 3H), of 1.02 (t, J=7.8 Hz, 3H).

Example 2(32)

8-(3-Pentylamine)-2-ethyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,59 (benzene:ethyl acetate = 5:1).

NMR (300 MHz, CDCl3): δ to 7.15 (d, J=8,1 Hz, 1H), 6,85 (d, J=2.7 Hz, 1H), 6,77 (the d, J=8,1, 2.7 Hz, 1H), 6,27 (d, J=10.5 Hz, 1H), 3,82 (s, 3H), 3,80 (m, 1H), is 3.08 (t, J=7.5 Hz, 2H), 2,89 (t, J=7.8 Hz, 2H), to 2.67 (m, 2H), 2,17 (s, 3H), 2.13 in (m, 2H), 1,81-of 1.52 (m, 4H), of 1.16 (t, J=7.2 Hz, 3H), was 1.04 (t, J=7.5 Hz, 3H), 1,01 (t, J=7.8 Hz, 3H).

Example 2(33)

Hydrochloride 8-(3-pentylamine)-2-isopropyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,60 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,28 (m, 1H), to 7.09 (d, J=8,4 Hz, 1H), make 6.90 (d, J=2.4 Hz, 1H), for 6.81 (DD, J=8,4, 2.4 Hz, 1H), 3,99 (m, 1H), 3,84 (s, 3H), 3,49 (m, 2H), 3,12 (t, J=7.2 Hz, 2H), 2,99 (m, 1H), 2,28 (m, 2H), 2,20 (s, 3H), of 1.85 (m, 2H), 1,74 (m, 2H), 1,24 (d, J=6.9 Hz, 3H), 1,19 (d, J=7.2 Hz, 3H), of 1.08 (t, J=7.5 Hz, 3H), of 1.06 (t, J=7.5 Hz, 3H).

Example 2(34)

Hydrochloride 8-(2-ethylbutylamine)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,55 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,46 (m, 1H), 7,11 (d, J=8,4 Hz, 1H), 6.89 in (d, J=2.4 Hz, 1H), PC 6.82 (DD, J=8,4, 2.4 Hz, 1H), 3,83 (s, 3H), 3,74 (t, J=6.0 Hz, 2H), 3,49 (t, J=7.8 Hz, 2H), 3,21 (t, J=7.5 Hz, 2H), 2,28 (s, 3H), and 2.26 (m, 2H), 2,19 (s, 3H), by 1.68 (m, 1H), 1,53 (m, 4H), and 1.00 (t, J=7.5 Hz, 6H).

Example 2(35)

Hydrochloride 8-(3-pentylamine)-2-methylthiomethyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,31 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,31 (userd, J=10,8 Hz, 1H), 7,16 (d, J=8,4 Hz, 1H), 6.89 in (d, J=2.4 Hz, 1H), 6,80 DD, J=an 8.4, 2.4 Hz, 1H), 4.00 points (users, 1H), 3,83 (s, 3H), 3,70 (d, J=13.5 Hz, 1H), 3,60 (d, J=13.5 Hz, 1H), 3,50 (m, 2H), 3,14 (t, J=7.2 Hz, 2H), to 2.29 (m, 2H), 2,32 (s, 3H), 2,04 (s, 3H), 1,95-of 1.65 (m, 4H), 1,07 (t, J=7.2 Hz, 3H), of 1.05 (t, J=7.5 Hz, 3H).

Example 2(36)

8-(N-Methyl-N-cyclopropylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,16 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,14 (d, J=8,1 Hz, 1H), 6,86 (d, J=2.7 Hz, 1H), 6,79 (DD, J=8,1, 2.7 Hz, 1H), 5,47 (users, 2H), 4,90 (users, 2H), 3,82 (s, 3H), of 3.45 (s, 3H), 2,80 (m, 1H), 2,33 (s, 3H), of 2.16 (s, 3H), from 0.84 (d, J=6,0 Hz, 4H).

Example 2(37)

8-(3-Pentylamine)-2-methyl-3-(2,4-dimetilfenil)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,50 (benzene:ethyl acetate = 10:1).

NMR (300 MHz, CDCl3): δ 7,13 (d, J=7.5 Hz, 1H), 7,11 (users, 1H), 7,03 (m, 1H), 6,21 (d, J=10,8 Hz, 1H), 3,80 (m, 1H), is 3.08 (t, J=6.9 Hz, 2H), 2,89 (t, J=7.5 Hz, 2H), 2,34 (s, 3H), 2,31 (s, 3H), of 2.18 (s, 3H), 2.13 and (m, 2H), 1.56 to to 1.82 (m, 4H), of 1.02 (m, 6H).

Example 2(38)

Hydrochloride 8-(3-pentylamine)-2-methyl-3-(2,5-dimetilfenil)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,54 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,31 (userd, J=10,2 Hz, 1H), 7,24 (d, J=7.5 Hz, 1H), 7,15 (userd, J=1,2, 7.5 Hz, 1H), 7,01 (users, 1H), 3,99 (m, 1H), 3,49 (t, J=7.5 Hz, 2H), 3,14 (t, J=6.9 Hz, 2H), 2,35 (s, 3H), 2,32 (s, 3H), to 2.29 (m, 2H), 2,18 (s, 3H), 1,64-of 1.94 (m, 4H), of 1.07 (t, J=7.5 Hz, 3H), of 1.06 (t, J=7.2 Hz, 3H).

Example 2(9)

8 Cyclobutylamine-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,36 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,14 (d, J=8.7 Hz, 1H), 6,85 (d, J=2.7 Hz, 1H), 6,77 (DD, J=8,7, 2.7 Hz, 1H), 6,50 (userd, J=8,4 Hz, 1H), 4,46 (m, 1H), 3,81 (s, 3H), of 3.12 (t, J=7.2 Hz, 2H), 2,88 (t, J=7.8 Hz, 2H), 2,43 (m, 2H)that is 2.30 (s, 3H), 2,23-of 2.08 (m, 4H), of 2.16 (s, 3H), 1,90 is 1.70 (m, 2H).

Example 2(40)

Hydrochloride, 8-(N-ethyl-N-cyclobutylamine)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,38 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ for 7.12 (d, J=8.7 Hz, 1H), 6.89 in (d, J=2.7 Hz, 1H), PC 6.82 (DD, J=8,7, 2.7 Hz, 1H), 4,74 (m, 1H), 3,99 (m, 2H), 3,83 (s, 3H), of 3.48 (t, J=7.5 Hz, 2H), 2,98 (t, J=7.5 Hz, 2H), 2,20-2,10 (m, 6H), 2,30 (s, 3H), 2,17 (s, 3H), 1,90 is 1.70 (m, 2H), 1,16 (t, J=7.2 Hz, 3H).

Example 2(41)

8-(Propane-1,3-diol-2-yl)amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,44 (chloroform:methanol = 9:1).

NMR (300 MHz, CDCl3): δ 7,17 (d, J=8,1 Hz, 1H), 6,86 (d, J=2.7 Hz, 1H), 6,79 (DD, J=8,1, 2.7 Hz, 1H), 6.73 x (d, J=10,2 Hz, 1H), 4,12 (m, 1H), 3,98-a 3.83 (m, 4H), 3,82 (s, 3H), 3,05 (t, J=7.2 Hz, 2H), 2,87 (t, J=8,1 Hz, 2H), 2,30 (s, 3H), of 2.16 (s, 3H), 2,11 (m, 2H).

Example 2(42)

8-(3-Pentylamine)-2-(2-furyl)-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,33 (n-hexane:ethyl acetate = 4:1).

NMR (300 MHz, CDCl3): δ 7,47 (m, 1H), 7,21 (d, J=8,1 Hz, 1H), 6.87 in (d, J=2.7 Hz, 1H), for 6.81 (DD, J=8,1, 2.7 Hz, 1H), 6,38-6,30 (m, 2H), equal to 6.05 (m, 1H), 3,84 (s, 3H), 3,82 (m, 1H), 3,11 (t, J=7.2 Hz, 2H), only 2.91 (t, J=7,8 Hz, 2H), 2,15 (m, 2H), 2,10 (s, 3H), of 1.70 (m, 4H), was 1.04 (t, J=7.2 Hz, 3H), 1,01 (t, J=7.2 Hz, 3H).

Example 2(43)

Hydrochloride 8-(3-pentylamine)-2-phenyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,41 (n-hexane:ethyl acetate = 4:1).

NMR (300 MHz, CDCl3): δ to 7.59-rate of 7.54 (m, 2H), 7,45-7,19 (m, 5H), 6,88-PC 6.82 (m, 2H), Android 4.04 (m, 1H), 3,85 (s, 3H), 3,55 (t, J=7.8 Hz, 2H), 3,17 (t, J=7.8 Hz, 2H), 2,32 (m, 2H), 2.05 is (s, 3H), 1,97-of 1.55 (m, 4H), 1,10 (t, J=to 6.9 Hz, 3H), of 1.07 (t, J=7.2 Hz, 3H).

Example 2(44)

8-(2-Dimethylaminoethyl)amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,30 (methylene chloride:methanol = 19:1).

NMR (300 MHz, CDCl3): δ to 7.15 (d, J=8,4 Hz, 1H), 6,85 (d, J=2.7 Hz, 1H), 6,77 (DD, J=8,4, 2.7 Hz, 1H), of 6.71 (t, J=5.7 Hz, 1H), 3,82 (s, 3H), of 3.75 (dt, J=5,7, and 6.3 Hz, 2H), 3,19 (t, J=7.5 Hz, 2H), 2,88 (t, J=7.5 Hz, 2H), 2,63 (t, J=6.3 Hz, 2H), 2,33 (s, 6H), 2,31 (s, 3H), 2,17 (s, 3H), 2,12 (m, 2H).

Example 2(45)

The dihydrochloride 8-(N-methyl-N-(2-dimethylaminoethyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,46 (methylene chloride:methanol = 9:1).

NMR (300 MHz, pyridine-d5 0.5 ml + CDCl30.1 ml): δ 7,42 (d, J=8,4 Hz, 1H),? 7.04 baby mortality (d, J=2.7 Hz, 1H), of 6.96 (DD, J=8,4, 2.7 Hz, 1H), 4,21 (t, J=7.5 Hz, 2H), 3,85 (t, J=7.5 Hz, 2H, in), 3.75 (s, 3H), 3,14 (s, 3H), of 3.00 (s, 6H), 2,90 (t, J=7.5 Hz, 2H), 2,80 (t, J=7.5 HZ, 2H), 2,41 (s, 3H), of 2.36 (s, 3H), 1,90 (m, 2H).

Example 2(46)

8-(N-Ethyl-N-(2-dimethylaminoethyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,46 (methylene chloride:methanol = 9:1).

NMR (300 MHz, CDCl3): δ to 7.15 (d, J=8,4 Hz, 1H), 6,85 (d, J=2.7 Hz, 1H), 6,78 (DD, J=8,4, 2.7 Hz, 1H), 3,82 (s, 3H), 3,80 (t, J=7.2 Hz, 2H), 3,64 (sq, J=7.2 Hz, 2H), 2,99 (t, J=7.5 Hz, 2H), 2,90 (t, J=7.5 Hz, 2H), 2,56 (t, J=7.2 Hz, 2H), 2,31 (s, 3H), of 2.25 (s, 6H), 2,17 (s, 3H), 2,12 (m, 2H), 1,17 (t, J=7.2 Hz, 3H).

Example 2(47)

Hydrochloride 8-(4-heptylamine)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,50 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,27 (userd, J=9.6 Hz, 1H), 7,11 (d, J=8,4 Hz, 1H), to 6.88 (d, J=2.7 Hz, 1H), for 6.81 (DD, J=8,4, 2.7 Hz, 1H), 4,12 (m, 1H), 3,82 (s, 3H), 3,49 (t, J=7.5 Hz, 2H), 3,11 (t, J=7.5 Hz, 2H), 2,32-of 2.20 (m, 2H), 2,28 (s, 3H), of 2.20 (s, 3H), 1,82 is 1.60 (m, 4H), 1.60-to of 1.36 (m, 4H), 0,99 (t, J=7.2 Hz, 3H), and 0.98 (t, J=7.2 Hz, 3H).

Example 2(48)

Hydrochloride 8-(2-butylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,40 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ of 7.36 (userd, J=9.9 Hz, 1 is), 7,12 and 7,11 (d, J=8,4 Hz, two conformational isomers, 1H), to 6.88 (d, J=2.7 Hz, 1H), for 6.81 (DD, J=8,4, 2.7 Hz, 1H), 4,18 (m, 1H), 3,83 (s, 3H), of 3.48 (t, J=7.5 Hz, 2H), and 3.16 (t, J=7.5 Hz, 2H), 2,40-of 2.20 (m, 2H), 2,28 (s, 3H), 2,19 and 2,18 (with two conformational isomers, 3H), of 1.80 (m, 2H), to 1.48 and 1.47 (d, J=6,6 Hz, two conformational isomers, 3H), of 1.09 and 1.08 (t, J=7.2 Hz, two conformational isomers, 3H).

Example 2(49)

Hydrochloride, 8-(N-propyl-N-cyclopropylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,42 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,13 (m, 1H), 6,88 (users, 1H), PC 6.82 (m, 1H), 3,88 (m, 2H), 3,83 (users, 3H), of 3.77 (users, 2H), 3,37 (m, 2H), 3,06 (m, 2H), to 2.29 (s, 3H), 2,24 (m, 2H), 2,19 (s, 3H), at 1.73 (m, 2H), 1,12 (m, 1H), 0,96 (m, 3H), and 0.62 (m, 2H), 0.26 per users, 2H).

Example 2(50)

Hydrochloride 8-(3-pentylamine)-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,46 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, DMSO-d6): δ a 9.25 (m, 1H), 8,31 (s, 1H), 7.23 percent (d, J=8,1 Hz, 1H), 6,95 (d, J=2.4 Hz, 1H), 6,86 (DD, J=2,4, 8,1 Hz, 1H), 3,99 (m, 1H), of 3.78 (s, 3H), 3.15 in (m, 2H), to 3.02 (t, J=7.8 Hz, 2H), measuring 2.20 (s, 3H), 2,18 (m, 2H), 1.60-to a 1.88 (m, 4H), to 0.89 (t, J=7.5 Hz, 6H).

Example 2(51)

Hydrochloride 8-[(2R)-1-methoxybutan-2-yl]amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,21 (n-hexane:utilized the t = 3:1).

NMR (300 MHz, CDCl3): δ 7,63 (userd, J=8,4 Hz, 1H), to 7.09 (d, J=8.7 Hz, 1H), 6.87 in (d, J=2.7 Hz, 1H), 6,79 (DD, J=8,7, 2.7 Hz, 1H), 4,19 (m, 1H), 3,81 (s, 3H), 3,65-of 3.53 (m, 2H), 3.45 points (t, J=8,1 Hz, 2H), 3.43 points and 3,41 (with two conformational isomer, 3H), 3,26-a 3.01 (m, 2H), 2,30-of 2.20 (m, 2H), 2,28 (s, 3H), of 2.18 (s, 3H), 1,96 is 1.58 (m, 2H), only 1.08 and 1.07 (t, J=7.5 Hz, two conformational isomers, 3H).

Example 2(52)

Hydrochloride 8-[(2S)-1-methoxybutan-2-yl]amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,21 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ to 7.59 (userd, J=10,2 Hz, 1H), 7,11 (d, J=8,4 Hz, 1H), to 6.88 (d, J=2.4 Hz, 1H), for 6.81 (DD, J=8,4, 2.7 Hz, 1H), 4,19 (m, 1H), 3,83 (s, 3H), 3,66-of 3.53 (m, 2H), 3,48 (t, J=8,1 Hz, 2H), 3,44 and 3,42 (with two conformational isomer, 3H), 3,26-to 3.02 (m, 2H), 2,30-of 2.20 (m, 2H), to 2.29 (s, 3H), of 2.20 (s, 3H), 1,98 was 1.69 (m, 2H), of 1.09 and 1.08 (t, J=7.5 Hz, two conformational isomers, 3H).

Example 2(53)

8 Cyclopentylamine-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,30 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ to 7.15 (d, J=8.7 Hz, 1H), at 6.84 (d, J=2.7 Hz, 1H), 6,77 (DD, J=8,7, 2.7 Hz, 1H), 6,34 (userd, J=9.0 Hz, 1H), to 4.38 (m, 1H), 3,82 (s, 3H), 3.15 in (t, J=7.2 Hz, 2H), 2,89 (t, J=7.8 Hz, 2H), 2,30 (s, 3H), 2,17 (s, 3H), 2,18 is 2.00 (m, 4H), 1,95-of 1.65 (m, 6H).

Example 2(54)

8-(3-Pentylamine)-2-methyl-3-(2,4-differenl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,57 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ to 7.50 (DDD, J=6,6, 8,4, and 8.4 Hz, 1H), 6,86-of 6.99 (m, 2H), 6,23 (d, J=10,8 Hz, 1H), 3,80 (m, 1H), 3,09 (t, J=7.2 Hz, 2H), 2,92 (t, J=8,l Hz, 2H), 2,39 (d, J=1.5 Hz, 3H), of 2.15 (m, 2H), 1,53-of 1.81 (m, 4H), 1,01 (t, J=7.2 Hz, 6H).

Example 2(55)

Hydrochloride 8-(3-pentylamine)-2-trifluoromethyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,42 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,33 (userd, J=10,2 Hz, 1H), 7,13 (d, J=8.7 Hz, 1H), 6.89 in (d, J=2.4 Hz, 1H), for 6.81 (DD, J=2,4, and 8.7 Hz, 1H), Android 4.04 (m, 1H), 3,83 (s, 3H), of 3.56 (m, 2H), 3,20 (m, 2H), 2,33 (m, 2H), 2,19 (s, 3H), 1.70 to 2,22 (m, 4H), of 1.08 (m, 6H).

Example 2(56)

Hydrochloride, 8-(N-ethyl-N-(2-methoxyethyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,20 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,11 (d, J=8,4 Hz, 1H), 6.89 in (d, J=2.7 Hz, 1H), PC 6.82 (DD, J=8,4, 2.7 Hz, 1H), 4,34-4,17 (m, 2H), 3,91 (sq, J=7.2 Hz, 2H), 3,83 (s, 3H), 3,68 (t, J=5,1 Hz, 2H), 3,47 (t, J=7.8 Hz, 2H), 3,32 (s, 3H), 3,06 (t, J=7.2 Hz, 2H), 2,28 (s, 3H), 2,30-of 2.20 (m, 2H), 2,18 (s, 3H), of 1.38 (t, J=7.2 Hz, 3H).

Example 2(57)

8 Cyclohexylamino-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,30 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ to 7.15 (d, J=8,1 Hz, 1H), at 6.84 (d, J=2.7 Hz, 1H), 6,77 (DD, J=8,1, 2.7 G is, 1H), 6,34 (userd, J=9.6 Hz, 1H), 3,81 (s, 3H), 3,80 (m, 1H), 3,10 (t, J=7.2 Hz, 2H), 2,88 (t, J=7.8 Hz, 2H), 2,30 (s, 3H), 2,17 (s, 3H), 2,18 is 2.00 (m, 4H), 1,90 and 1.80 (m, 2H), 1,75-to 1.60 (m, 1H), 1,50-1,20 (m, 5H).

Example 2(58)

Hydrochloride, 8-(N-propyl-N-(3-pentyl)amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,43 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,14 (d, J=8,l Hz, 1H), 6.89 in (d, J=2.7 Hz, 1H), PC 6.82 (DD, J=8,1, 2.7 Hz, 1H), 4,20 (m, 1H), 3,83 (s, 3H), of 3.60 (m, 2H), 3,38 (t, J=7.5 Hz, 2H), 2,97 (t, J=7.5 Hz, 2H), 2,30-of 2.15 (m, 2H), of 2.27 (s, 3H), of 2.20 (s, 3H), 2.00 in to 1.70 (m, 4H), of 1.42 (m, 2H), and 0.98 (t, J=7.5 Hz, 6H), of 0.90 (t, J=7.5 Hz, 3H).

Example 2(59)

8-(3-Pentylamine)-2-methyl-3-(4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,57 (n-hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ of 7.60 (d, J=9.0 Hz, 2H), 6,99 (d, J=9.0 Hz, 2H), 6,10 (userd, J=10.5 Hz, 1H), 3,84 (s, 3H), 3,81 (m, 1H), is 3.08 (t, J=7.2 Hz, 2H), equal to 2.94 (t, J=7.8 Hz, 2H), 2,53 (s, 3H), of 2.15 (m, 2H), 1,53-to 1.82 (m, 4H), and 1.00 (t, J=7.2 Hz, 6H).

Example 2(60)

8-(3-Pentylamine)-2-isopropyl-3-(4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,54 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ of 7.48 (d, J=8.7 Hz, 2H), 6,97 (d, J=8.7 Hz, 2H), 6,29 (userd, J=10.5 Hz, 1H), 3,84 (s, 3H), 3,80 (m, 1H), 3,32 (Sept., J=6,9 Hz, 1H), of 3.07 (t, J=7.2 Hz, 2H), only 2.91 (t, J=7.5 Hz, 2H), 2.13 in (m, 2H), 1,63 of-1.83 (m, 4H), of 1.33 (d, J=6.9 Hz, 6H), is 1.01 (t, J=7.5 Hz, 6H).

Example 2(61)

8-tert.-Butylamino-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,35 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,15 (userd, J=8.7 Hz, 1H), 6,97 (users, 1H), 6,85 (d, J=2.7 Hz, 1H), 6,78 (DD, J=8,7, 2.7 Hz, 1H), 3,81 (s, 3H), 3.15 in (t, J=7.2 Hz, 2H), only 2.91 (t, J=7.5 Hz, 2H), 2,30 (s, 3H), of 2.18 (s, 3H), 2,11 (m, 2H), 1.57 in (s, 9H).

Example 2(62)

Hydrochloride 8-(3-pentylamine)-3-(2,4,6-trimetilfenil)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,58 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ to $ 7.91 (s, 1H), 7,39 (userd, J=10,2 Hz, 1H), 6,99 (s, 2H), a 4.03 (m, 1H), 3,52 (t, J=7.8 Hz, 2H), 3,17 (t, J=7.2 Hz, 2H), 2,32 (s, 3H), 2,31 (m, 2H), 2.13 and (s, 6H), 1,67 is 1.96 (m, 4H), of 1.07 (t, J=7,5 Hz, 6H).

Example 2(63)

Hydrochloride 8-(1-cyclobutylmethyl)amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,28 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, pyridine-d50.5 ml + CDC130.1 ml): δ 7,46 (d, J=8,1 Hz, 1H), 7,06 (d, J=2.7 Hz, 1H), 6,97 (DD, J=8,1, 2.7 Hz, 1H), 6,80 (d, J=10,2 Hz, 1H), 3.96 points (m, 1H), 3,74 (s, 3H), of 2.97 (DDD, J=14,1, to 7.2, 7.2 Hz, 2H), 2,86 (t, J=7.5 Hz, 2H), 2,50-of 2.36 (m, 1H), 2,47 (s, 3H), 2,39 (s, 3H), 2.05 is-of 1.65 (m, 8H)and 1.15 (d, J=6.3 Hz, 3H).

Example 2(64)

8-(3-Pentylamine)-2-methyl-3-(2,3-dimethyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,37 (benzene:ethyl acetate = 10:1).

NMR (300 MHz, CDCl3): δ was 7.08 (d, J=8,1 Hz, 1H), 6,78 (d, J=8,1 Hz, 1H), 6,21 (d, J=10,8 Hz, 1H), 3,84 (s, 3H), 3,81 (m, 1H), is 3.08 (t, J=6.6 Hz, 2H), 2,88 (t, J=8,1 Hz, 2H), to 2.29 (s, 3H), of 2.21 (s, 3H), 2.13 in (m, 2H), 2,10 (s, 3H), 1.56 to to 1.82 (m, 4H), of 1.03 (t, J=7.5 Hz, 3H), 1,01 (t, J=6.9 Hz, 3H).

Example 2(65)

8-(3-Pentylamine)-2-methyl-3-(2,5-dimethyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,43 (benzene:ethyl acetate = 10:1).

NMR (300 MHz, CDCl3): δ 6,99 (s, 1H), 6,76 (s, 1H), 6,20 (d, J=10.5 Hz, 1H), 3,84 (s, 3H), 3,82 (m, 1H), is 3.08 (t, J=6.9 Hz, 2H), 2,89 (t, J=7.2 Hz, 2H), 2,31 (s, 3H), 2,19 (s, 3H), 2,17 (s, 3H), and 2.14 (m, 2H), 1,54-of 1.80 (m, 4H), 1,01 (m, 6H).

Example 2(66)

8-(N-(2,2,2-Triptorelin)-N-cyclopropylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,62 (n-hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,17 (d, J=8,1 Hz, 1H), 6.87 in (d, J=2.7 Hz, 1H), 6,80 (DD, J=8,1, 2.7 Hz, 1H), with 4.64 (sq, J=9.6 Hz, 2H), 3,82 (s, 3H), 3,41 (d, J=6.6 Hz, 2H), 2,98 (t, J=6.9 Hz, 2H), equal to 2.94 (t, J=7.5 Hz, 2H), 2,34 (s, 3H), 2.21 are of 2.09 (m, 2H), 2,18 (s, 3H), of 1.03 (m, 1H), or 0.57 (m, 2H), 0,21 (m, 2H).

Example 2(67)8-(2,2,2-Triptorelin)amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,22 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,14 (d, J=8,1 Hz, 1H), 6,85 (d, J=2.7 Hz, 1H), 6,78 (DD, J=8,1, 2.7 Hz, 1H), 6.75 in (IRT, J=7.8 Hz, 1H), 4,22 (DQC., J=7,8, and 7.8 Hz, 2H), 3,82 (s, 3H), of 3.12 (t, J=7.5 Hz, 2H), 2,92 (t, J=7.8 Hz, 2H), 2,31 (s, 3H), 2,23-of 2.09 (m, 2H), 2,17 (s, 3H).

Example 2(68)

Hydrochloride 8-[(2R)-1-methoxybutan-2-yl]amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,25 (n-hexane:ethyl acetate = 2:1).

NMR (300 MHz, pyridine-d50.5 ml + CDC130.1 ml): δ 7,39 (d, J=8,1 Hz, 1H), 7,37 (userd, J=9,3 Hz, 1H), 7,03 (d, J=2.7 Hz, 1H), 6,95 (DD, J=8,1, 2.7 Hz, 1H), the 5.45 (d, J=9.9 Hz, 1H), 5,35 (d, J=9.9 Hz, 1H), 4,98 (users, 2H), 3,74 (s, 3H), 3,63-3,48 (m, 3H), 3,26 (s, 3H), 2,41 (s, 3H), of 2.34 (s, 3H), 1,82 is 1.60 (m, 2H), 0,97 (t, J=7.5 Hz, 3H).

Example 2(69)

Hydrochloride 8-[(2R)-1-methoxybutan-2-yl]amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-2,3-dihydrofuro[3,2-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,29 (n-hexane:ethyl acetate = 2:1).

NMR (300 MHz, pyridine-d50.5 ml + CDC130.1 ml): δ 7,40 (d, J=8,4 Hz, 1H), 7,03 (users, 1H), 6,95 (DD, J=8,4, 2.4 Hz, 1H), 6,80 (userd, J=9,3 Hz, 1H), 4,47 (m, 1H), 4,47 (t, J=8,4 Hz, 2H), 3,74 (s, 3H), of 3.56 (d, J=4,8 Hz, 2H), or 3.28 (s, 3H), 3,12 (t, J=8,4 Hz, 2H), 2,43 (s, 3H), of 2.35 (s, 3H), 1,87 of 1.46 (m, 2H), and 1.00 (t, J=7.5 Hz, 3H).

Example 2(70)

Hydrochloride 8-(3-pentylamine)-3-(2,6-dimethyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,33 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ of 7.90 (s, 1H), 7,39 (userd, J=10,2 Hz, 1H), 6,72 (s, 2H), was 4.02 (m, 1H), 3,81 (s, 3H), 3,53 (t, J=7.8 Hz, 2H), 3,7 (t, J=6,9 Hz, 2H), 2,32 (m, 2H), and 2.14 (s, 6H), 1,66 is 1.96 (m, 4H), of 1.08 (t, J=7.2 Hz, 6H).

Example 2(71)

Hydrochloride 8-(3-pentylamine)-3-(4,6-dimethyl-2-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,33 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ to 7.99 (s, 1H), 7,37 (userd, J=10,8 Hz, 1H), 6.75 in (s, 1H), 6,70 (s, 1H), 4,01 (m, 1H), 3,85 (s, 3H), of 3.57 (t, J=7.8 Hz, 2H), and 3.16 (t, J=7.2 Hz, 2H), a 2.36 (s, 3H), 2,31 (m, 2H), of 2.23 (s, 3H), 1,63-of 1.92 (m, 4H), of 1.06 (t, J=7.2 Hz, 6H).

Example 2(72)

8-(3-Pentylamine)-2-methyl-3-(2,6-dimethyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,33 (benzene:ethyl acetate = 10:1).

NMR (300 MHz, CDCl3): δ of 6.68 (s, 2H), 6,21 (d, J=10.5 Hz, 1H), 3,81 (m, 1H), 3,80 (s, 3H), to 3.09 (t, J=7.2 Hz, 2H), 2,88 (t, J=7.8 Hz, 2H), 2,19 (s, 3H), 2.13 in (m, 2H), 2,04 (s, 6H), 1,55 of-1.83 (m, 4H), of 1.03 (t, J=7,5 Hz, 6H).

Example 2(73)

8-(3-Pentylamine)-2-methyl-3-(4,6-dimethyl-2-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,33 (benzene:ethyl acetate = 10:1).

NMR (300 MHz, CDCl3): δ to 6.75 (m, 1H), 6,62 (s, 1H), 6,21 (d, J=10.5 Hz, 1H), 3,80 (m, 1H), 3,71 (s, 3H), 3,06 (m, 2H), 2,87 (m, 2H), 2,34 (s, 3H), 2,24 (s, 3H), 2,12 (m, 2H), 2,09 (s, 3H), 1,53 and 1.80 (m, 4H), of 1.03 (t, J=7.2 Hz, 3H), and 1.00 (t, J=7.5 Hz, 3H).

Example 2(74)

Hydrochloride 8-(3-methylpentan-3-yl)amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,36 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 8,01 (users, 1H), 7,12 (d, J=8,1 Hz, 1H), 6.89 in (d, J=2.7 Hz, 1H), PC 6.82 (DD, J=8,1, 2.7 Hz, 1H), 3,83 (s, 3H), 3,52 (t, J=7.8 Hz, 2H), and 3.16 (t, J=7.2 Hz, 2H), 2,28 (s, 3H), 2,24 (m, 2H), measuring 2.20 (s, 3H), 2.00 in of 1.85 (m, 4H), of 1.55 (s, 3H), of 1.03 (t, J=7.5 Hz, 6H).

Example 2(75)

8-(3-Pentylamine)-2-methyl-3-(5-chloro-1,3-dioksiinien-6-yl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,44 (benzene:ethyl acetate = 10:1).

NMR (300 MHz, CDCl3): δ of 6.96 (s, 1H), 6,85 (s, 1H), 6.22 per (userd, J=10.5 Hz, 1H), of 5.99 (s, 2H), 3,80 (m, 1H), is 3.08 (t, J=7.2 Hz, 2H), only 2.91 (t, J=7.8 Hz, 2H), 2,34 (s, 3H), of 2.16 (m,2H), 1,53-of 1.81 (m, 4H), 1,01 (t, J=7,2 Hz, 6H).

Example 2(76)

Hydrochloride, 8-(N-ethyl-N-benzylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,43 (n-hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,26-the 7.43 (m, 5H), 7,13 (d, J=8,4 Hz, 1H), 6.89 in (d, J=2.7 Hz, 1H), 6,83 (DD, J=2.7, and an 8.4 Hz, 1H), total of 5.21 (s, 2H), a 3.87 (sq, J=6,9 Hz, 2H), 3,83 (s, 3H), 3,47 (t, J=7.2 Hz, 2H), 3,03 (t, J=7.2 Hz, 2H), to 2.29 (s, 3H), 2,22 (m, 2H), 2,19 (s, 3H), of 1.39 (t, J=6.9 Hz, 3H).

Example 2(77)

Hydrochloride 8-(3-pentylamine)-2-methyl-3-(2-chloro-4-trifloromethyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,52 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, pyridine-d5(0.5 ml), CDCl3(0.1 ml)): δ 7,71 (d, J=8,4 Hz, 1H), EUR 7.57 (m, 1H), 7,28 (who, 1H), 6,77 (d, J=10.5 Hz, 1H), 3,74 (m, 1H), 2.95 points (t, J=7.5 Hz, 2H), 2,85 (t, J=7.8 Hz, 2H), 2,46 (s, 3H), of 1.98 (m, 2H), 1,64 is 1.48 (m, 4H), to 0.92 (t, J=7.5 Hz, 6H).

Example 2(78)

Hydrochloride 8-(3-pentylamine)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,20 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, pyridine-d5(0.5 ml), CDCl3(0.1 ml)): δ to 7.59 (d, J=8,4 Hz, 1H), 7,24 (d, J=2.4 Hz, lH), 6,98 (DD, J=8,4, 2.4 Hz, 1H), 6,78 (d, J=10.5 Hz, 1H), 3,74 (m, 1H), 3,69 (s, 3H), equal to 2.94 (t, J=7.2 Hz, 2H), 2,85 (t, J=7.8 Hz, 2H), of 2.51 (s, 3H), a 1.96 (m, 2H), 1,64 is 1.48 (m, 4H), of 0.91 (t, J=7.5 Hz, 6H).

Example 2(79)

Hydrochloride, 8-(N-benzyl-N-(2-methoxyethyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,24 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,34-7,44 (m, 3H), 7,27-7,34 (m, 2H), 7,13 (d, J=8,4 Hz, 1H), make 6.90 (d, J=2.7 Hz, 1H), 6,83 (DD, J=2.7, and an 8.4 Hz, 1H), 5,11 (s, 2H), 4,14 (t, J=4,8 Hz, 2H), of 3.84 (s, 3H), of 3.64 (t, J=4,8 Hz, 2H), to 3.49 (t, J=7.8 Hz, 2H), 3,29 (s, 3H), of 3.07 (t, J=7.2 Hz, 2H), 2,31 (s, 3H), of 2.23 (m, 2H), 2,19 (s, 3H).

Example 2(80)

8-(1,2,5,6-Tetrahydropyridine)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,30 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ to 7.15 (d, J=8,1 Hz, 1H), 6,85 (d, J=2.7 Hz, 1H), 6,78 (DD, J=2,7, 8,1 Hz, CDCl3), 5,97 (m, 1H), of 5.83 (m, 1H), 4,21 (m, 2H), 3,85 (m, 2H), 3,82 (s, 3H), of 3.07 (t, J=7.2 Hz, 2H), 2,89 (t, J=7.5 Hz, 2H), 2,41 (m, 2H), 2,32 (s, 3H), of 2.16 (s, 3H), 2,11 (m, 2H).

Example 2(81)

Hydrochloride 8-(3-pentylamine)-2-methyl-3-(2-methoxy-4,5-dimetilfenil)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,29 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,29 (userd, J=10,2 Hz, 1H),? 7.04 baby mortality (s, 1H), 6,83 (s, 1H), 3,95 (m, 1H), 3,90 (s, 3H), of 3.56 (t, J=7.8 Hz, 2H), 3,12 (t, J=7.5 Hz, 2H), 2,42 (s, 3H), 2,31(s, 3H), 2,28 (m, 2H), 2,24 (s, 3H), 1,90-of 1.62 (m, 4H), was 1.04 (t, J=7.5 Hz, 6N).

Example 2(82)

8-(1,2,3,4-Tetrahydroisoquinoline-2-yl)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,24 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7.23 percent-to 7.18 (m, 3H), 7,16 (d, J=8,4 Hz, 1H), 7,11 (m, 1H), 6,86 (d, J=2.4 Hz, 1H), 6,79 (DD, J=8,4, 2.4 Hz, 1H), a 4.86 (s, 2H), 4.09 to (t, J=5.7 Hz, 2H), 3,82 (s, 3H), is 3.08 (t, J=5.7 Hz, 2H), 2,97 (t, J=7.2 Hz, 2H), 2,89 (t, J=7.8 Hz, 2H), 2,33 (s, 3H), 2,17 (s, 3H), of 2.08 (m, 2H).

Example 2(83)

8 Phenylamino-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,35 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 8,01 (user., 1H), 7,45-7,38 (m, 2H), 7,33-7,17 (m, 4H), 6.87 in (d, J=2.4 Hz, 1H), 6,80 (DD, J=8,1, 2.4 Hz, 1H), 3,83 (s, 3H), 2,89 (t, J=7.8 Hz, 2H), 2,35 (s, 3H), 2,30 (t, J=7.5 Hz, 2H), of 2.21 (s, 3H), 2,02-1,90 (m, 2H).

Example 2(84)

8-(2-Were)amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]feast Medin

TLC: Rf= 0,37 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,76 (user., 1H), 7,32-7,17 (m, 5H), 6.87 in (d, J=2.4 Hz, 1H), 6,80 (DD, J=8,4, 2.4 Hz, 1H), 3,83 (s, 3H), 2,85 (t, J=7.5 Hz, 2H), a 2.36 (s, 6H), 2,22 (s, 3H), 2,13 (t, J=7.5 Hz, 2H), 1,96-of 1.85 (m, 2H).

Example 2(85)

8-(3-Were)amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,38 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ of 7.96 (user., 1H), 7,32-7,26 (m, 1H), 7,19 (d, J=8,4 Hz, 1H), 7,12-7,01 (m, 3H), 6.87 in (d, J=2.7 Hz, 1H), 6,80 (DD, J=8,4, 2.7 Hz, 1H), 3,83 (s, 3H), 2,88 (t, J=7.8 Hz, 2H), 2.40 a (s, 3H), of 2.35 (s, 3H), 2,31 (t, J=6,9 Hz, 2H), of 2.21 (s, 3H), 2,02 is 1.91 (m, 2H).

Example 2(86)

8-(4-Were)amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,33 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,93 (user., 1H), 7.23 percent-7,11 (m, 5H), 6.87 in (d, J=2.7 Hz, 1H), 6,80 (DD, J=8,4, 2.7 Hz, 1H), 3,83 (s, 3H), of 2.86 (t, J=7.5 Hz, 2H), 2.40 a (s, 3H), of 2.35 (s, 3H), to 2.29 (t, J=7.5 Hz, 2H), of 2.21 (s, 3H), 2.00 in a 1.88 (m, 2H).

Example 2(87)

8-(N-Phenyl-N-propylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,48 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,31-7,24 (m, 2H), 7,21 (d, J=8,4 Hz, 1H), 6,99-6,87 (m, 4H), for 6.81 (DD, J=8,4, 2.7 Hz, 1H), 4,15-4,07 (m, 2H), of 3.84 (s, 3H), of 2.92 (t, J=7.5 Hz, 2H), a 2.36 (s, 3H), 31st (t, J=7.5 Hz, 2H), 2,22 (s, 3H), 2.05 is-of 1.94 (m, 2H), 1,82 by 1.68 (m, 2H), of 0.96 (t, J=7.2 Hz, 3H).

Example 2(88)

8-(N-Benzyl-N-propylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,63 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,33-7,21 (m, 5H), 7,19 (d, J=8,4 Hz, 1H), 6.87 in (d, J=2.7 Hz, 1H), 6,80 (DD, J=8,4, 2.7 Hz, 1H), a 4.86 (s, 2H), 3,83 (s, 3H), 3,42-to 3.34 (m, 2H), 2,88 (t, J=7.8 Hz, 2H), of 2.81 (t, J=7,l Hz, 2H,), a 2.36 (s, 3H), of 2.20 (s, 3H), 2,11-to 1.98 (m, 2H), 1,67-and 1.54 (m, 2H), from 0.88 (t, J=7.5 Hz, 3H).

Example 2(89)

Hydrochloride, 8-(N,N-diallylamine)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,46 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,11 (d, J=8,4 Hz, 1H), 6.89 in (d, J=2.7 Hz, 1H), PC 6.82 (DD, J=2.7, and an 8.4 Hz, 1H), 6,03 (m, 2H), of 5.40 (d, J=10.5 Hz, 2H), 5,35 (d, J=18 Hz, 2H), 4,49 (d, J=6.0 Hz, 4H), 3,83 (s, 3H), 3,47 (t, J=7,8 Hz, 2H), is 3.08 (t, J=7.2 Hz, 2H), 2,28 (s, 3H), of 2.23 (m, 2H), 2,18 (s, 3H).

Example 2(90)

8-(3-Pentylamine)-2-methyl-3-(2-methyl-4-dimethylaminophenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,17 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,11 (d, J=8,1 Hz, 1H), 6,70 (d, J=2.7 Hz, 1H), only 6.64 (DD, J=8,1, 2.7 Hz, 1H), to 6.19 (d, J=10,2 Hz, 1H), 3,80 (m, 1H), is 3.08 (t, J=7.5 Hz, 2H), 2.95 and (C, 6N), 2,89 (t, J=7.5 Hz, 2H), 2,32 (s, 3H), to 2.18 (s, 3H), 2,18-of 2.08 (m, 2H), 1,80-of 1.56 (m, 4H), 1,01 (users, 6N).

Example 2(91)

Hydrochloride 8-(1-phenylpropyl the Mino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,45 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,83 (d, J=8.7 Hz, 1H), 7,27-of 7.48 (m, 5H), 7,12 (d, J=8,4 Hz, 1H), to 6.88 (m, 1H), for 6.81 (DD, J=2.7, and an 8.4 Hz, 1H), 5,10 (m, 1H), 3,82 (s, 3H), 3,41 (m, 2H), and 3.16 (m, 1H), and 2.83 (m, 1H), 2,32 (s, 3H), are 2.19 2.20 (s, total 3H), 2,12 (m, 4H), of 1.12 and 1.01 (t, J=7.2 Hz, total 3H).

Example 2(92)

Hydrochloride, 8-(N-(2-phenylethyl)-N-propylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,35 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7.23 percent-7,05 (m, 6H), of 6.90 (d, J=2.4 Hz, 1H), 6,83 (DD, J=8,4, 2.4 Hz, 1H), 4,33 (t, J=6.6 Hz, 2H), of 3.84 (s, 3H), 3,71 (t, J=6.9 Hz, 2H), 3,37 (t, J=7.5 Hz, 2H), 2,98 (t, J=7.2 Hz, 2H), 2,77 (t, J=7.5 Hz, 2H), 2,32 (s, 3H), of 2.20 (s, 3H), 2,20-to 2.06 (m, 2H), 1,81 by 1.68 (m, 2H), 0,97 (t, J=7.5 Hz, 3H).

Example 2(93)

8-(N-(3-Phenylpropyl)-N-propylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,40 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,26-7,05 (m, 6H), 6,86 (d, J=2.7 Hz, 1H), 6,79 (DD, J=8,4, 2.7 Hz, 1H), 3,83 (s, 3H), 3,66-of 3.53 (m, 4H), 2,88 (t, J=7.5 Hz, 2H), 2,87 (t, J=7.5 Hz, 2H), 2,62 (t, J=7.8 Hz, 2H), 2,32 (s, 3H), are 2.19 (s, 3H), 2,15-2,04 (m, 2H), 1,95 of-1.83 (m, 2H), 1,61-1,49 (m, 2H), from 0.88 (t, J=7.2 Hz, 3H).

Example 2(94)

8-(N-(4-Phenylbutyl)-N-propylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf=0,48 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,25-7,05 (m, 6H), 6,86 (d, J=2.7 Hz, 1H), 6,78 (DD, J=8,1, 2.7 Hz, 1H), 3,83 (s, 3H), 3,63 (t, J=6.6 Hz, 2H), 3,57-to 3.49 (m, 2H), 2,90 (t, J=7.5 Hz, 2H), 2,88 (t, J=7.5 Hz, 2H), 2.57 m (t, J=6,9 Hz, 2H), 2,32 (s, 3H), 2,19 (s, 3H), 2,15-2,05 (m, 2H), 1,66-1,49 (m, 6H), to 0.88 (t, J=7.5 Hz, 3H).

Example 2(95)

Hydrochloride 8-(1-phenyl-2-butyl)amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,41 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, DMSO-d6): δ 9,24 (m, 1H),? 7.04 baby mortality-7,30 (m, 6H), 6,95 (users, 1H), 6,86 (DD, J=2.7, and an 8.4 Hz, 1H), 4,20 (users, 1H), of 3.78 (s, 3H), 2,87-3,17 (m, 3H), 2,64-2,87 (m, 3H), and 2.26 (s, 3H), 1,82-to 2.18 (m, 5H), 1,63-to 1.82 (m, 2H), 0,93 (ushort, J=6,9 Hz, 3H).

Example 2(96)

Hydrochloride 8-(1-phenyl-3-pentyl)amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,43 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, DMSO-d6): δ 8,53 (m, 1H), 7,09-7,28 (m, 6H), of 6.96 (d, J=3.0 Hz, 1H), 6,85 (DD, J=3.0 a, and 8.4 Hz, 1H), 4,10 (m, 1H), 3,82 (s, 3H), 2,89-to 3.02 (m, 3H), 2,68-to 2.85 (m, 3H), of 2.25 (s, 3H), 2.00 in 2,22 (m, 7H), to 1.79 (m, 2H), with 0.93 (t, J=7.5 Hz, 3H).

Example 2(97)

Hydrochloride, 8-(N-(4-were)-N-propylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,43 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,27 (d, J=8.1 Hz, 2H), 7,13-7,22 (m, 3H), of 6.90 (d, J=2.4 Hz, 1H), at 6.84 (DD, J=2,4, and 8.7 Hz, 1H), 4,46 (m, 2H), 3,84 (who, 3H), the 3.35 (m, 2H), 2,43 (s, 3H), 2,31 (s, 3H), 2,22 (s, 3H), 1.77 in-of 1.97 (m, 6H), and 0.98 (t, J=7.5 Hz, 3H).

Example 2(98)

Hydrochloride, 8-(N-(4-were)methyl-N-propylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,45 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,11-7,21 (m, 5H), of 6.90 (d, J=2.7 Hz, 1H), 6,83 (DD, J=2.7, and 8.7 Hz, 1H), 5,13 (s, 2H), of 3.84 (s, 3H), and 3.72 (t, J=7.5 Hz, 2H), 3,48 (t, J=8,1 Hz, 2H), 3,01 (t, J=6.9 Hz, 2H), a 2.36 (s, 3H), 2,29 (s, 3H), 2,22 (m, 2H), 2,19 (s, 3H), 1.77 in (m, 2H), were 0.94 (t, J=7.5 Hz, 3H).

Example 2(99)

Hydrochloride, 8-(N-(3-were)-N-propylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,41 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ of 7.36 (m, 1H), 7,06-7,24 (m, 4H), 6,91 (d, J=2.4 Hz, 1H), at 6.84 (DD, J=2,4, 8,1 Hz, 1H), 4,46 (m, 2H), of 3.84 (s, 3H), 3,36 (m, 2H), 2,42 (s, 3H), 2,32 (s, 3H), of 2.23 (s, 3H), 1.77 in is 2.00 (m, 6H), 0,99 (t, J=7.2 Hz, 3H).

Example 2(100)

Hydrochloride, 8-(N-(4-methoxyphenyl)methyl-N-propylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,26 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ to 7.18 (d, J=8.7 Hz, 2H), 7,13 (d, J=8,4 Hz, 1H), make 6.90(d, J=8.7 Hz, 2H), make 6.90 (d, J=3.0 Hz, 1H), 6,83 (DD, J=3.0 a, and 8.4 Hz, 1H), 5,10 (s, 2H), of 3.84 (s, 3H), 3,82 (s, 3H), 3,70 (t, J=7.5 Hz, 2H), to 3.49 (t, J=8,1 Hz, 2H), 3,01 (t, J=6.9 Hz, 2H), 2,30 (s, 3H), 2,22 (m, 2H), 2,19 (s, 3H), of 1.75 (m, 2H), 0,93 (who, J=7.2 Hz, 3H).

Example 2(101)

Hydrochloride, 8-(N-(4-chlorophenyl)methyl-N-propylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,26 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,37 (d, J=8.7 Hz, 2H), 7,24 (d, J=8.7 Hz, 2H), 7,12 (d, J=8,4 Hz, 1H), make 6.90 (d, J=2.7 Hz, 1H), 6,83 (DD, J=2.7, and an 8.4 Hz, 1H), further 5.15 (s, 2H), 3,83 (s, 3H), 3,68 (m, 2H), 3,50 (t, J=7.8 Hz, 2H), to 3.02 (t, J=7.2 Hz, 2H), to 2.29 (s, 3H), of 2.25 (m, 2H), 2,19 (s, 3H), of 1.74 (m, 2H), of 0.93 (t, J=7.2 Hz, 3H).

Example 2(102)

Hydrochloride, 8-(N-(2-were)-N-propylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,46 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,27 was 7.45 (m, 4H), 7,16 (d, J=8,4 Hz, 1H), make 6.90 (d, J=2.4 Hz, 1H), at 6.84 (DD, J=2,4, and 8.4 Hz, 1H), 4.53-in (m, 1H), 4,37 (m, 1H), 3,84 (s, 3H), 3,34 (m, 2H), 2,31 (s, 3H), of 2.23 (s, 3H), 2,10 (s, 3H), 1,50-2,07 (m, 6H), of 0.97 (t, J=7.5 Hz, 3H).

Example 2(103)

Hydrochloride, 8-((3S)-3-methoxymethyl-1,2,3,4-tetrahydroisoquinoline-2-yl)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,56 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,30-7,05 (m, 5H), 6.90 to to 6.75 (m, 2H), 5,48 (m, 1H), to 5.03 (d, J=15.6 Hz, 1H), 4.72 in (DD, J=15,6, 3,9 Hz, 1H), 3,82 (s, 3H), 3.33 and and of 3.32 (s, 3H), a 3.87 was 3.05 (m, 7H), 2,82 (d, J=15.6 Hz, 1H), 2.40 a is 2.10 (m, 2H), to 2.29 (s, 3H), 2,25 and are 2.11 (s, 3H).

Example 2(104)

The dihydrochloride 8-(3-Pentti is amino)-2-methyl-3-(2-dimethylamino-4-methylpyridin-5-yl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,42 (chloroform:methanol = 20:1).

NMR (300 MHz, CDCl3): δ 8,01 (s, 1H), 7,32 (d, J=10,2 Hz, 1H), 6,85 (s, 1H), 4.00 points (m, 1H), 3,41 (s, 6H), 3,40 (m, 2H), 3,17 (m, 2H), is 2.37 (s, 3H), 2,33 (m, 2H), 2,32 (s, 3H), 1,65-of 1.95 (m, 4H), of 1.07 (t, J=7.5 Hz, 3H), was 1.06 (t, J=7.2 Hz, 3H).

Example 2(105)

Hydrochloride, 8-((2S)-1-methoxy-3-phenyl-2-propyl)amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,26 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.77 (m, 1H), 7,25 was 7.36 (m, 3H), 7,16-of 7.23 (m, 2H), 7,11 (m, 1H), to 6.88 (m, 1H), 6,80 (m, 1H), of 4.44 (m, 1H), 3,82 (s, 3H), 3,53-3,68 (m, 2H), 3,47 and 3.46 (s, 3H), 3,38 (m, 2H), 3,11 (t, J=7.2 Hz, 2H), is 3.08 (m, 1H), 2,81 (m, 1H), 2,31 (s, 3H), of 2.20 and 2.17 (s, 3H), of 2.15 (m, 2H).

Example 2(106)

Hydrochloride, 8-(N-(4-methylthiophenyl)methyl-N-propylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,50 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.25 (d, J=8,4 Hz, 2H), 7,18 (d, J=8,4 Hz, 2H), 7,13 (d, J=8,1 Hz, 1H), make 6.90 (d, J=2.4 Hz, 1H), 6,83 (DD, J=2,4, 8,1 Hz, 1H), 5,13 (s, 2H), of 3.84 (s, 3H), 3,70 (m, 2H), 3,50 (t, J=7.8 Hz, 2H), a 3.01 (t, J=6.9 Hz, 2H), 2,50 (s, 3H), to 2.29 (s, 3H), of 2.23 (m, 2H), 2,19 (s, 3H), of 1.75 (m, 2H), of 0.93 (t, J=7.5 Hz, 3H).

Example 2(107)

The dihydrochloride 8-(4-phenylpiperazin-1-yl)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,30 hexane:ethyl acetate = 2:1).

NMR (300 MHz, DMSO-d6): δ 7,30-7,38 (m, 2H), 7,21-7,29 (m, 2H), 7,12 (d, J=8,4 Hz, 1H), 7,00 (userd, J=6,9 Hz, 1H), 6,95 (d, J=2.7 Hz, 1H), 6,86 (DD, J=2.7, and an 8.4 Hz, 1H), 4,22 (users, 4H), 3,79 (s, 3H), 3,53 (users, 4H), 3,14 (m, 2H,), of 2.97 (t, J=7.8 Hz, 2H), of 2.21 (s, 3H), of 2.15 (m, 2H), 2.06 to (s, 3H).

Example 2(108)

8-(4-(2-Chlorophenyl)piperazine-1-yl)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,38 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,41 (DD, J=1.5 and 7.8 Hz, 1H), 7,28 (m, 1H), 7,16 (d, J=8,1 Hz, 1H), 7,15 (d, J=8.7 Hz, 1H), 7,03 (m, 1H), 6,86 (d, J=2.7 Hz, 1H), 6,79 (DD, J=2,7, 8,1 Hz, 1H), 3,90 (m, 4H), 3,82 (s, 3H), 3.33 and (t, J=4,8H, 4H), and 3.16 (t, J=7.5 Hz, 2H), only 2.91 (t, J=7.8 Hz, 2H), 2,33 (s, 3H), 2,17 (s, 3H), and 2.14 (m, 2H).

Example 2(109)

Hydrochloride, 8-(N,N-dibutylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,57 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ for 7.12 (d, J=7.8 Hz, 1H), 6.89 in (d, J=2.4 Hz, 1H), PC 6.82 (DD, J=2,4, and 7.8 Hz, 1H), 3,90 (t, J=7.5 Hz, 4H), 3,83 (s, 3H), of 3.48 (m, 2H), to 3.02 (m, 2H), and 2.27 (s, 3H), of 2.25 (m, 2H), 2,19 (s, 3H), 1,71 (m, 4H), to 1.38 (m, 4H), of 0.97 (t, J=6.9 Hz, 6H).

Example 2(110)

Hydrochloride, 8-(N-methyl-N-butylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,36 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,10 (d, J=8,1 Hz, 1H), to 6.88 (d, J=3.0 Hz, 1H), for 6.81 (DD, J=3,0, 8,1 Hz, 1H), 3,9 (m, 2H), 3,83 (s, 3H), 3,51 (s, 3H), of 3.45 (t, J=8,1 Hz, 2H), 3,12 (t, J=6.9 Hz, 2H), and 2.26 (s, 3H), of 2.23 (m, 2H), 2,18 (s, 3H), of 1.85 (m, 2H), 1,40 (m, 2H), 0,99 (t, J=7.2 Hz, 3H).

Example 2(111)

Hydrochloride, 8-(N-(4-were)methyl-N-butylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,53 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,10-7,21 (m, 5H), 6.89 in (d, J=2.4 Hz, 1H), 6,83 (DD, J=2,4, 8,1 Hz, 1H), 5,13 (s, 2H), 3,83 (s, 3H), of 3.77 (t, J=7.2 Hz, 2H), 3,48 (t, J=7.8 Hz, 2H), 3,01 (t, J=6.9 Hz, 2H), a 2.36 (s, 3H), 2,29 (s, 3H), of 2.21 (m, 2H), 2,19 (s, 3H), at 1.73 (m, 2H), of 1.34 (m, 2H), of 0.93 (t, J=7.2 Hz, 3H).

Example 2(112)

Hydrochloride, 8-(N-(4-were)methyl-N-(2-methoxyethyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,23 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,25-7,05 (m, 5H), 6,98-of 6.78 (m, 2H), is 5.06 (s, 2H), 4,22-a 4.03 (m, 2H), of 3.84 (s, 3H), 3.75 to to 3.58 (m, 2H), to 3.58-to 3.38 (m, 2H), 3,30 (s, 3H), 3,20-2,90 (m, 2H), a 2.36 (s, 3H), of 2.30 (s, 3H), of 2.21 (m, 2H,), are 2.19 (s, 3H).

Example 2(113)

Hydrochloride, 8-(N-cyclopropyl-N-(4-were)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,35 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,25-to 6.95 (m, 5H), 6,95-of 6.73 (m, 2H), 5.40 to-5,15 (m, 2H), 3,83 (s, 3H), 3,65-3,30 (m, 2H), 3,30-2,95 (m, 2H), 2,35 (s, 3H), 2,31 (s, 3H), 2,30-2,10 (m, 3H), 2,19 (s, 3H), 1,10-0,80 (m, 4H).

Note the R 2(114)

Hydrochloride, 8-(N-cyclopropylmethyl-N-(4-were)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,37 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,30-7,00 (m, 5H), 7,00 to 6.75 (m, 2H), 5,24 (s, 2H), of 3.84 (s, 3H), 3,80-of 3.60 (m, 2H), 3,60-to 3.35 (m, 2H), 3,20-2,90 (m, 2H), 2,34 (s, 3H), to 2.29 (s, 3H), 2,22 (s, 2H), 2,11 (s, 3H), 1,38-of 1.05 (m, 1H), of 0.75 and 0.50 (m, 2H), 0,35-0,10 (m, 2H).

Example 2(115)

8-(N,N-Dipropylamino-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,59 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,17 (d, J=8,4 Hz, 1H), 6,86 (d, J=2.4 Hz, 1H), 6,79 (DD, J=2,4, and 8.4 Hz, 1H), 3,82 (s, 3H), of 3.56 (m, 4H), 2.95 points (t, J=7.2 Hz, 2H), 2,90 (t, J=7.8 Hz, 2H), 2,33 (s, 3H), 2,19 (s, 3H), 2.13 and (m, 2H), 1,58 (m, 4H), to 0.89 (t, J=7.5 Hz, 6H).

Example 2(116)

Hydrochloride, 8-(N-(4-were)methyl-N-(2-butynyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,47 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,33 (d, J=8,l Hz, 2H), 7,19 (d, J=8.1 Hz, 2H), 7,11 (d, J=8.7 Hz, 1H), 6.89 in (d, J=2.7 Hz, 1H), PC 6.82 (DD, J=2.7, and 8.7 Hz, 1H), 5,27 (d, J=to 15.0 Hz, 1H), 5,24 (d, J=to 15.0 Hz, 1H), to 4.41 (m, 2H), a 3.83 (s, 3H), 3,51 (t, J=7.5 Hz, 2H), up 3.22 (t, J=6.9 Hz, 2H), is 2.37 (s, 3H), of 2.28 (s, 3H), of 2.25 (m, 2H), 2,17 (s, 3H), 1.91 a (t, J=2,4 Hz, 3H).

Example 2(117)

8-(N-propyl-N-(2-butynyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-is ihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,55 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,16 (d, J=8,1 Hz, 1H), 6,86 (d, J=2.7 Hz, 1H), 6,79 (DD, J=2,7, 8,1 Hz, 1H), and 4.40 (m, 2H), 3,82 (s, 3H), 3,55 (m, 2H), 3,11 (t, J=7.2 Hz, 2H), only 2.91 (t, J=7.8 Hz, 2H), 2,32 (s, 3H), 2,18 (s, 3H), 2.13 in (m, 2H), 1,81 (t, J=2,4 Hz, 3H), of 1.66 (m, 2H), of 0.95 (t, J=7.5 Hz, 3H).

Example 2(118)

Hydrochloride 8-(5-nonylamine)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,58 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,33 (userd, J=10.5 Hz, 1H), 7,12 (d, J=8.7 Hz, 1H), to 6.88 (d, J=2.7 Hz, 1H), for 6.81 (DD, J=2.7, and 8.7 Hz, 1H), 4,10 (m, 1H), 3,83 (s, 3H), 3,49 (t, J=8,1 Hz, 2H), 3,12 (t, J=6.6 Hz, 2H), to 2.29 (s, 3H), and 2.27 (m, 2H), measuring 2.20 (s, 3H), 1.61 of-a 1.88 (m, 4H), 1.30 and of 1.53 (m, 8H), were 0.94 (m, 6H).

Example 2(119)

Hydrochloride, 8-(N-cyclopentyl-N-(4-were)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,38 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CD3OD): δ 7,20-6,98 (m, 5H), 6,93 (d, J=2.4 Hz, 1H), 6,85 (DD, J=8,6, and 2.4 Hz, 1H), 5,20 (d, J=16.5 Hz, 1H), 5,09 (d, J=16.5 Hz, 1H), 5,02-4,70 (m, 1H), 3,81 (s, 3H), 3,17 (t, J=7.2 Hz, 2H), 2,98 (t, J=7,8 Hz, 2H), to 2.29 (s, 3H), 2,22 (s, 3H), of 1.98 (s, 3H), 2.40 a is 1.60 (m, 10H).

Example 2(120)

8-(N-Cyclopropylmethyl-N-(4-methylthiophenyl)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf = 0,85 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,28-7,16 (m, 5H), 6.87 in (d, J=3.0 Hz, 1H), 6,79 (DD, J=3.0 a, and 8.4 Hz, 1H), 4,89 (s, 2H), 3,83 (s, 3H), 3,38 (d, J=6,9 Hz, 2H), 2,96 (t, J=7.2 Hz, 2H), 2,89 (t, J=7.2 Hz, 2H), 2,47 (s, 3H), 2,36 (s, 3H), 2,19 (s, 3H), of 2.09 (Quint., J=7.2 Hz, 2H), 1,10-of 0.95 (m, 1H), 0,52 at 0.42 (m, 2H), 0,10-0,05 (m, 2H).

Example 2(121)

8-(N-(4-Forfinal)methyl-N-propylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,87 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,28-7,16 (m, 3H), 7.03 is-to 6.95 (m, 2H), 6.87 in (d, J=2.4 Hz, 1H), 6,79 (DD, J=2,4, and 8.4 Hz, 1H), 4,80 (s, 2H), 3,83 (s, 3H), 3,40-of 3.32 (m, 2H), 2,89 (t, J=7.5 Hz, 2H), of 2.81 (t, J=7.5 Hz, 2H), 2,36 (, 3H), of 2.20 (s, 3H), 2,07 (Quint., J=7.5 Hz, 2H), 1,62 of 1.50 (m, 2H), from 0.88 (t, J=7.2 Hz, 3H).

Example 2(122)

8-(N-Cyclobutyl-N-(4-were)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,48 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,19 (d, J=8,4 Hz, 1H), 7,02 (d, J=7.5 Hz, 2H), 6.89 in (d, J=7.5 Hz, 2H), 6.87 in (d, J=8.0 Hz, 1H), 6,80 (DD, J=8,4, 3.0 Hz, 1H), 4,90-4,70 (m, 2H), 4,08 (m, 1H), 3,83 (s, 3H), 2,84 (t, J=7.5 Hz, 2H), 2,61 (m, 2H), 2,39 (s, 3H), of 2.30 (s, 3H), 2,19 (s, 3H), 2,20-to 2.06 (m, 4H), to 1.96 (m, 2H), 1,80-to 1.60 (m, 2H).

Example 2(123)

8-(N-Ethyl-N-(4-were)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,69 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,19 (d, J=8,1 Hz, 1H), 7,14-7,06 (m, 4H), 6.87 in (d, J=2.7 Hz, 1H), 6,80 (DD, J=2,7, 8,1 Hz, 1H), to 4.81 (s, 2H), a 3.87 (s, 3H), 3,47 (sq, J=6,9 Hz, 2H), 2,88 (t, J=7.8 Hz, 2H), 2,81 (ushort, J=7.8 Hz, 2H), a 2.36 (s, 3H), of 2.33 (s, 3H), of 2.20 (s, 3H), 2,04 (Quint., J=7.8 Hz, 2H), of 1.18 (t, J=6.9 Hz, 3H).

Example 2(124)

8-(N-Propyl-N-(4-triptoreline)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,79 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ EUR 7.57 (userd, J=8,1 Hz, 2H), 7,44 (userd, J=8,1 Hz, 2H), 7,18 (d, J=8.7 Hz, 1H), 6.87 in (d, J=2.4 Hz, 1H), 6,79 (DD, J=2,4, and 8.7 Hz, 1H), 4,91 (s, 2H), 3,83 (s, 3H), 3,49-of 3.25 (m, 2H), 2,90 (t, J=7.8 Hz, 2H), 2,87 (t, J=7.8 Hz, 2H), 2,35 (s, 3H), 2,19 (s, 3H), 2,18 is 2.00 (m, 2H), 1,62 of 1.50 (m, 2H), from 0.88 (t, J=7.5 Hz, 3H).

Example 2(125)

8-(N-Propyl-N-(tetrahydrofuran-2-yl)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,31 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,16 (d, J=8,1 Hz, 1H), 6,86 (d, J=2.7 Hz, 1H), 6,78 (DD, J=2,7, 8,1 Hz, 1H), 3,84-4,06 (m, 2H), 3,82 (s, 3H), 3,64-of 3.80 (m, 3H), 3,50-to 3.64 (m, 2H), 2,99 (t, J=7.2 Hz, 2H), only 2.91 (t, J=8,1 Hz, 2H,), 2,32 (s, 3H), 2,19 (s, 3H), 2.13 in (m, 2H), 1,74 is 2.00 (m, 3H), 1,42-of 1.65 (m, 3H), of 0.89 (t, J=7.5 Hz, 3H).

Example 2(126)

8-(N-Butyl-N-(2-methoxyethyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,30 (hexane:ethyl acetate = 2:).

NMR (300 MHz, CDCl3): δ 7,16 (d, J=8,4 Hz, 1H), 6,86 (d, J=2.7 Hz, 1H), 6,79 (DD, J=2.7, and an 8.4 Hz, 1H), 3,92 (t, J=5.7 Hz, 2H), 3,82 (s, 3H), of 3.57 (m, 2H), 3,50 (t, J=5.7 Hz, 2H), or 3.28 (s, 3H), 2,98 (t, J=7.8 Hz, 2H), only 2.91 (t, J=7.8 Hz, 2H), 2,32 (s, 3H), of 2.18 (s, 3H), 2.13 in (m, 2H), 1.55V (m, 2H), 1,33 (m, 2H), of 0.90 (t, J=7.2 Hz, 3H).

Example 2(127)

8-(N-Propyl-N-(cyclopropylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,45 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,16 (d, J=8,1 Hz, 1H), 6,85 (d, J=2.7 Hz, 1H), 6,78 (DD, J=8,1, 2.7 Hz, 1H), 3,85 (m, 2H), 3,82 (s, 3H), 3,19 (t, J=7.5 Hz, 2H), of 3.07 (m, 1H), 2,92 (t, J=7.5 Hz, 2H), 2,31 (s, 3H), 2,18 (s, 3H), 2,12 (m, 2H), 1,62 (m, 2H), 0,89 (t, J=7.2 Hz, 3H), 0,80 was 0.68 (m, 4H).

Example 2(128)

8-(N-Cyclobutylmethyl-N-(2-methoxyethyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,57 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,17 (d, J=8,4 Hz, 1H), 6,86 (d, J=2.7 Hz, 1H), 6,78 (DD, J=2.7, and an 8.4 Hz, 1H), 3,82 (s, 3H), 3,82 (t, J=6.0 Hz, 2H), 3,64 (d, J=7.5 Hz, 2H), 3,49 (t, J=6.0 Hz, 2H), or 3.28 (s, 3H), 2,96 (t, J=7.2 Hz, 2H), only 2.91 (t, J=7.8 Hz, 2H), 2,62-of 2.50 (m, 1H), 2,32 (s, 3H), of 2.18 (s, 3H), 2,20-2,05 (m, 2H), 2.06 to was 1.58 (m, 6H).

Example 2(129)

Hydrochloride 8-(3-etoxycarbonyl)-1,2,5,6-tetrahydropyridine)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,27 (hexane:ethyl acetate = 2:1).

NMR (300 M is C, CDCl3): δ 7,27 (m, 1H), to 7.09 (d, J=8,1 Hz, 1H), to 6.88 (d, J=2.7 Hz, 1H), for 6.81 (DD, J=2,7, 8,1 Hz, 1H), to 4.62 (m, 2H), 4,27 (sq, J=6,9 Hz, 2H), 4,20 (t, J=5.7 Hz, 2H), 3,83 (s, 3H), 3,47 (t, J=7.2 Hz, 2H), and 3.16 (t, J=6.0 Hz, 2H), 2,85 (m, 2H), and 2.27 (s, 3H), and 2.26 (m, 2H), 2,17 (s, 3H), of 1.34 (t, J=6.9 HZ, 3H).

Example 2(130)

8-(N-Cyclopropylmethyl-N-(4-were)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,68 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,21 (d, J=7.8 Hz, 2H), 7,16 (d, J=7.8 Hz, 2H), 7,13 (d, J=8,4 Hz, 1H), make 6.90 (d, J=2.7 Hz, 1H), 6,83 (DD, J=2.7, and an 8.4 Hz, 1H), 5,41 (users, 2H), 5,27 (m, 2H), 5,22 (users, 2H), 3,83 (s, 3H), 3,74 (m, 2H), is 2.37 (s, 3H), 2,31 (s, 3H), of 2.20 (s, 3H), 1,24 (m, 1H), 0.67 and (m, 2H), 0,24 (m, 2H).

Example 2(131)

8-(3-(3-Methyl-1,2,4-oxadiazol-5-yl)-1,2,5,6-tetrahydropyridine)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,18 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,29 (m, 1H), 7,15 (d, J=8.7 Hz, 1H), 6,86 (d, J=2.7 Hz, 1H), 6,79 (DD, J=2.7, and 8.7 Hz, 1H), 4,57 (m, 2H), 3,94 (m, 2H), 3,82 (s, 3H), to 3.09 (t, J=7.5 Hz, 2H), only 2.91 (t, J=7.8 Hz, 2H), 2,71 (m, 2H), 2,42 (s, 3H), 2,32 (s, 3H), 2,17 (s, 3H), and 2.14 (m, 2H).

Example 2(132)

8-(4-Heptylamine)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf=0,48 (hexane:ethyl acetate=2:1).

NMR (300 MHz, CDCl3): δ 7,37 (d, J=8.7 Hz, 1H), 7,07 (d, J=2.4 Hz, 1H), 6,97 (DD, =2,4, to 8.7 Hz, 1H), 4,13 (m, 1H), 3,85 (s, 3H), 3,35-3,66 (m, 2H), 3,13 (t, J=7.5 Hz, 2H), 2,34 (s, 3H), to 2.29 (m, 2H), 1.60-to of 1.84 (m, 4H), 1,34 is 1.60 (m, 4H), and 1.00 (t, J=7.2 Hz, 3H), 0,99 (t, J=7.5 Hz, 3H).

Example 2(133)

8-(N-Cyclopropylmethyl-N-(2-butynyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TCX: Rf=0,73 (hexane:ethyl acetate=1:1).

NMR (300 MHz, CDCl3): δ 7,16 (d, J=8,1 Hz, 1H), 6,86 (d, J=2.7 Hz, 1H), 6,78 (DD, J=8,1, 2.7 Hz, 1H), 4,54 (users, 2H), 3,82 (s, 3H), 3,53 (d, J=6,9 Hz, 2H), 3,13 (t, J=7.2 Hz, 2H), only 2.91 (t, J=7.8 Hz, 2H), 2,33 (s, 3H), 2,17 (s, 3H), 2,17-of 2.08 (m, 2H), 1,81 (t, J=2.7 Hz, 3H), 1,20-of 1.16 (m, 1H), 0.60 and 0.52 in (m, 2H), of 0.36 to 0.28 (m, 2H).

Example 2(134)

8-(N-(2-Methoxyethyl)-N-(2-butynyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TCX: Rf=0,13 (hexane:ethyl acetate=3:1).

NMR (300 MHz, CDCl3): δ to 7.15 (d, J=8,4 Hz, 1H), 6,86 (d, J=2.7 Hz, 1H), 6,79 (DD, J=8,4, 2.7 Hz, 1H), of 4.44-4,39 (m, 2H), 3,92 (t, J=6.0 Hz, 2H), 3,82 (s, 3H), of 3.65 (t, J=6.0 Hz, 2H), 3,34 (s, 3H), of 3.13 (t, J=7.2 Hz, 2H), only 2.91 (t, J=7.8 Hz, 2H), 2,32 (s, 3H), 2,17 (s, 3H), 2,17-of 2.08 (m, 2H), 1,81 (t, J=2.7 Hz, 3H).

Example 2(135)

8-(2-Butylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,80 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ to 7.15 (d, J=8,4 Hz, 1H), 6,85 (d, J=2.4 Hz, 1H), 6,78 (DD, J=8,4, 2.4 Hz, 1H), 6,53 (t, J=6,9 Hz, 1H), 4,36-4,30 (m, 2H), 3,82 (s, 3H), of 3.25 (t, J=7.2 Hz, 2H, 2,90 (t, J=7.8 Hz, 2H), 2,31 (s, 3H), of 2.18 (s, 3H), 2,20-of 2.08 (m, 2H)and 1.83 (t, J=2.1 Hz, 3H).

Example 2(136)

8-(4-(4-Chlorophenyl)-1,2,5,6-tetrahydropyridine)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,10 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,42-7,30 (m, 4H), 7,16 (d, J=8,1 Hz, 1H), 6,86 (d, J=2.4 Hz, 1H), 6,79 (DD, J=8,1, 2.4 Hz, 1H), 6.22 per 6,18 (m, 1H), 4,50-4,32 (m, 2H), 4,10-3,90 (m, 2H), 3,82 (s, 3H), 3,10 (t, J=6.9 Hz, 2H), 2.91 in (t, J=7.5 Hz, 2H), 2,82-2,69 (m, 2H), 2,33 (s, 3H), 2,17 (s, 3H), 2,17-of 2.08 (m, 2H).

Example 2(137)

Hydrochloride, 8-(N-cyclopropylmethyl-N-(4-were)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,53 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ of 7.36 (d, J=8,4 Hz, 1H), 7,18 (d, J=8.1 Hz, 2H), 7,15 (d, J=8.1 Hz, 2H), was 7.08 (d, J=2.7 Hz, 1H), 6,97 (DD, J=8,4, 2.7 Hz, 1H), 5.25-inch (d, J=15,9 Hz, 1H), total of 5.21 (d, J=15,9 Hz, 1H), 3,85 (s, 3H), 3,70 (m, 2H), 3,36-3,62 (m, 2H), of 3.07 (t, J=7.2 Hz, 2H), a 2.36 (s, 3H), of 2.35 (s, 3H), of 2.23 (m, 2H), 1,23 (m, 1H), 0,63 (m, 2H), 0,18 (m, 2H).

Example 2(138)

8-(N-Propyl-N-(4-triptoreline)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TCX: Rf=0,55 (hexane:ethyl acetate=3:1).

NMR (300 MHz, CDCl3): δ 7,32 (userd, J=8.7 Hz, 2H), 7,18 (d, J=8,4 Hz, 1H), 7,15 (userd, J=8.7 Hz, 2H), 6.87 in (d, J=2.7 Hz, 1H), 6,80 (DD, J=8,4, 2.7 Hz, 1H), 4,84 (s, 2H), 3,83 (s, 3H) 3,41-to 3.35 (m, 2H), 2,89 (t, J=7.5 Hz, 2H), and 2.83 (t, J=7.8 Hz, 2H), a 2.36 (s, 3H), 2,19 (s, 3H), 2,19-2,00 (m, 2H), 1,66-and 1.54 (m, 2H), from 0.88 (t, J=7.5 Hz, 3H).

Example 2(139)

8-(N-(2-Butynyl)-N-cyclopropylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo [1,5-a]pyrimidine

TCX: Rf=0,40 (hexane:ethyl acetate=3:1).

NMR (300 MHz, CDCl3): δ 7,29 (d, J=8.7 Hz, 1H), 7,05 (d, J=2.4 Hz, 1H), to 6.88 (DD, J=8,7, 2.4 Hz, 1H), 4,54 (sq, J=2.1 Hz, 2H), 3,83 (s, 3H), 3,52 (d, J=6.6 Hz, 2H), 3,13 (t, J=7.5 Hz, 2H), 2,92 (t, J=7.5 Hz, 2H), 2,37 (s, 3H), 2.13 and (Quint., J=7.5 Hz, 2H), 1,81 (t, J=2.1 Hz, 3H), 1,16-1,02 (m, 1H), 0.60 and 0.52 in (m, 2H), 0,32-0,26 (m, 2H).

Example 2(140)

Hydrochloride, 8-(N-propyl-N-(3-were)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,52 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,27 (m, 1H), 7,15 (m, 1H), 7,13 (d, J=8,1 Hz, 1H), 7,05 (m, 2H), make 6.90 (d, J=2.7 Hz, 1H), 6,83 (DD, J=2,7, 8,1 Hz, 1H), 5,14 (s, 2H), 3,83 (s, 3H), 3,74 (m, 2H), 3,49 (t, J=7.2 Hz, 2H), 3,02 (t, J=6.9 Hz, 2H), a 2.36 (s, 3H), to 2.29 (s, 3H), 2,22 (m, 2H), measuring 2.20 (s, 3H), 1.77 in (m, 2H), were 0.94 (t, J=7.2 Hz, 3H).

Example 2(141)

Hydrochloride, 8-(N-propyl-N-(2-were)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,52 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,18-7,30 (m, 4H), 7,13 (d, J=8,1 Hz, 1H), make 6.90 (d, J=2.4 Hz, 1H), 6,83 (DD, J=2,4, 8,1 Hz, 1H), 5,13 (s, 2H), 3,83 (s, 3H), and 78 (m, 2H), 3,49 (t, J=6.9 Hz, 2H), 3,00 (t, J=6.9 Hz, 2H), 2,28 (s, 3H), 2,24 (s, 3H), of 2.21 (m, 2H), 2,19 (s, 3H), 1,79 (m, 2H), were 0.94 (t, J=7.2 Hz, 3H).

Example 2(142)

Hydrochloride 8-(3-pentylamine)-2-methyl-3-(2-chloro-4-ethoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,49 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,34 (d, J=8.7 Hz, 1H), 7,06 (d, J=2.4 Hz, 1H), 6,95 (DD, J=2,4, and 8.7 Hz, 1H), 4,07 (m, 2H), 3,99 (m, 1H), 3,34-the 3.65 (m, 2H), 3,13 (t, J=7.8 Hz, 2H), 2,35 (s, 3H), to 2.29 (m, 2H), 1,62-of 1.93 (m, 4H), to 1.42 (t, J=6.9 Hz, 3H), of 1.06 (t, J=7.5 Hz, 3H), of 1.05 (t, J=7.2 Hz, 3H).

Example 2(143)

Hydrochloride 8-(3-pentylamine)-2-methyl-3-(2-chloro-4-ethoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,40 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,52 (userd, J=10,2 Hz, 1H), 7,32 (d, J=8,4 Hz, 1H), 7,07 (d, J=2.4 Hz, 1H), 6,95 (DD, J=2,4, and 8.4 Hz, 1H), 5,49 (d, J=16.5 Hz, 1H), 5,39 (d, J=16.5 Hz, 1H), 5,28 (users, 2H), 4,07 (m, 2H), 3,40 (m, 1H)that is 2.40 (s, 3H), 1,68-to 1.98 (m, 4H), USD 1.43 (t, J=6.9 Hz, 3H), of 1.07 (t, J=7.2 Hz, 3H), of 1.06 (t, J=7.2 Hz, 3H).

Example 2(144)

Hydrochloride, 8-(N-methyl-N-hexylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,09 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,11 (d, J=8,4 Hz, 1H), 6.89 in (d, J=2.4 Hz, 1H), PC 6.82 (DD, J=8,4, 2.4 Hz, 1H), 4,01-3,95 (m, 2H), 3,83 (s, 3H), 3,51 (s, 3H), 3,51-of 3.42 (m, 2H), 3,18-of 3.06 (m, 2H), and 2.26 (s, 3H), 2.26 and-to 2.18 (m, 2H), to 2.18 (s, 3H), 1,96 and 1.80 (m, 2H), 1,44-1,25 (m, 6H), 0,90 (IRT, J=6.6 Hz, 3H).

Example 2(145)

Hydrochloride, 8-(N-methyl-N-(3-pentyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,47 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,11 (d, J=8,4 Hz, 1H), 6.89 in (d, J=2.7 Hz, 1H), PC 6.82 (m, 1H), 4,55 (m, 1H), 3,83 (s, 3H), of 3.46 (t, J=7.8 Hz, 2H), 3.27 to (s, 3H), 3,10 (t, J=6.9 Hz, 2H), and 2.26 (s, 3H), of 2.45 (m, 2H), 2,19 (s, 3H), 1,76-to 1.98 (m, 4H), 1,01 (t, J=7.2 Hz, 6H).

Example 2(146)

Hydrochloride, 8-(N-methyl-N-(4-heptyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rfor = 0.51 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,11 (d, J=8,4 Hz, 1H), 6.89 in (d, J=3.0 Hz, 1H), PC 6.82 (DD, J=3.0 a, and 8.4 Hz, 1H), 4,80 (m, 1H), 3,83 (s, 3H), 3,47 (t, J=7.5 Hz, 2H), 3.27 to (s, 3H), to 3.09 (t, J=7.5 Hz, 2H, in), 2.25 (s, 3H), 2,24 (m, 2H), 2,19 (s, 3H), 1,64-of 1.94 (m, 4H), 1,28 is 1.58 (m, 4H), of 0.97 (t, J=7.2 Hz, 6H).

Example 2(147)

Hydrochloride, 8-(N-cyclopropyl-N-(4-were)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,54 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,34 (d, J=8,4 Hz, 1H), 7,11 (d, J=7.8 Hz, 2H), to 7.09 (d, J=2.4 Hz, 1H), 7,02 (d, J=7.8 Hz, 2H), 6,94 (DD, J=2,4, and 8.4 Hz, 1H), 5,18-and 5.30 (m, 4H), of 5.15 (s, 2H), 3,85 (s, 3H), to 2.67 (m, 1H), 2,41 (s, 3H), of 2.33 (s, 3H), of 0.85 to 1.00 (m, 4H).

Example 2(148)

Hydrochloride, 8-(N-cyclopropylmethyl-N-(4-were)methylamino)-2-methyl-3-(2-chloro-4-ethoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,58 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ to 7.35 (d, J=8,4 Hz, 1H), 7,19 (d, J=8.1 Hz, 2H), 7,17 (d, J=8.1 Hz, 2H), was 7.08 (d, J=2.7 Hz, 1H), of 6.96 (DD, J=2.7, and an 8.4 Hz, 1H), 5,10-5,50 (m, 6H), 3,85 (s, 3H), of 3.69 (m, 2H), is 2.37 (s, 3H), 2,36 (s, 3H), 1,21 (m, 1H), 0,65 (m, 2H), 0,22 (m, 2H).

Example 2(149)

8-(N-Cyclobutyl-N-propylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,45 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,17 (d, J=8,1 Hz, 1H), 6,86 (d, J=2.7 Hz, 1H), 6,78 (DD, J=8,1, 2.7 Hz, 1H), 4,35 (Quint., J=7.5 Hz, 1H), 3,82 (s, 3H), 3,69-3,10 (m, 2H), equal to 2.94 (t, J=6.9 Hz, 2H), 2,90 (t, J=7.8 Hz, 2H), 2,33 (s, 3H), 2,22-2,02 (m, 9H), 1,78 is 1.58 (m, 2H), 1.39 in (Sextus., J=7.8 Hz, 2H), from 0.84 (t, J=7.8 Hz, 3H).

Example 2(150)

The dihydrochloride 8-(N-isobutyl-N-(2-dimethylaminoethyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,63 (ethyl acetate:acetic acid:water= 3:1:1).

NMR (300 MHz, DMSO-d6): δ 7,11 (d, J=8,4 Hz, 1H), 6,91 (d, J=2.7 Hz, 1H), PC 6.82 (DD, J=8,4, 2.7 Hz, 1H), 4,08-3,98 (m, 2H), of 3.78 (s, 3H), 3,50-of 3.42 (m, 2H), 3,42-of 3.32 (m, 2H), 3,01 (ushort, J=6,9 Hz, 2H), 2,87 (ushort, J=7.8 Hz, 2H,), and 2.79 (s, 3H), 2,77 (s, 3H), of 2.25 (s, 3H), 2,18 is 2.00 (m, 2H), 2,08 (s, 3H), 1,80-of 1.64 (m, 1H), or 0.83 (d, J=6.6 Hz, 6H).

Example 2(151)

8-(N-Propyl-N-(4-forfinal)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,34 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,31 (d, J=8.7 Hz, 1H), 7,28-7,24 (m, 2H), was 7.08 (d, J=3.0 Hz, 1H), 7,05-6,97 (m, 2H), 6.90 to (DD, J=8,7, 3.0 Hz, 1H), 5,09 (s, 2H), 4,91 (s, 2H), 4,89 (s, 2H), of 3.84 (s, 3H), 3.33 and-of 3.27 (m, 2H), 2.40 a (s, 3H), 1,63 (Sextus., J=7.8 Hz, 2H), 0,39 (t, J=7.8 Hz, 3H).

Example 2(152)

8-(N-Propyl-N-(4-forfinal)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,36 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ to 7.32 (d, J=8,4 Hz, 1H), 7,28-7,20 (m, 2H), 7,07 (d, J=2.7 Hz, 1H), 7,02-6,94 (m, 2H), 6.89 in (DD, J=8,4, 2.7 Hz, 1H), 4,80 (s, 2H), of 3.84 (s, 3H), 3,36 (ushort, J=7.5 Hz, 2H), 2,90 (t, J=7.5 Hz, 2H), 2,82 (t, J=7.5 Hz, 2H), 2,39 (s, 3H), 2,07 (Quint., J=7.5 Hz, 2H), 1,68 is 1.48 (m, 2H), 0,87 (t, J=7.5 Hz, 3H).

Example 2(153)

Hydrochloride, 8-(N-cyclopropylmethyl-N-(4-methylthiophenyl)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,67 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ to 7.35 (d, J=8,4 Hz, 1H), 7,27 (d, J=8,4 Hz, 2H), 7,22 (d, J=8,4 Hz, 2H), to 7.09 (d, J=2.7 Hz, 1H), 6,97 (DD, J=2.7, and an 8.4 Hz, 1H), 5,48 (d, J=16.5 Hz, 1H), lower than the 5.37 (d, J=16.5 Hz, 1H), 5,33 (d, J=15,9 Hz, 1H), 5,24 (s, 2H), 5,24 (d, J=15,9 Hz, 1H), 3,85 (s, 3H), of 3.69 (m, 2H), 2,50 (s, 3H), of 2.36 (s, 3H), 1,19 (m, 1H), 0.69 (m, 2H), 0,24 (m, 2H).

Example 2(154)

Hydrochloride, 8-(N,N-dipropylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

T is X: R f= 0,69 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,33 (d, J=8.7 Hz, 1H), was 7.08 (d, J=2.4 Hz, 1H), of 6.96 (DD, J=2,4, and 8.7 Hz, 1H), 5,48 (TD, J=1,8, is 16.8 Hz, 1H), are 5.36 (dt, J=1,8, is 16.8 Hz, 1H), total of 5.21 (t, J=1.8 Hz, 2H), 3,85 (m, 4H), 3,85 (s, 3H), 2,35 (s, 3H)and 1.83 (m, 4H), of 1.02 (t, J=7.2 Hz, 6H).

Example 2(155)

Hydrochloride, 8-(N,N-dibutylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,74 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,34 (d, J=8,4 Hz, 1H), was 7.08 (d, J=2.4 Hz, 1H), of 6.96 (DD, J=2,4, and 8.4 Hz, 1H), vs. 5.47 (d, J=16.5 Hz, 1H), are 5.36 (d, J=16.5 Hz, 1H), total of 5.21 (s, 2H), 3,88 (m, 4H), 3,85 (s, 3H), of 2.34 (s, 3H), 1,79 (m, 4H), of 1.42 (m, 4H), and 1.00 (t, J=7.2 Hz, 6H).

Example 2(156)

8-(N-Cyclopropylmethyl-N-(4-forfinal)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,27 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,33-7,26 (m, 3H), 7,06 (d, J=2.7 Hz, 1H), 7,01-to 6.95 (m, 2H), to 6.88 (DD, J=8,4, 2.7 Hz, 1H), 4,88 (s, 2H), of 3.84 (s, 3H), 3,38 (d, J=6,9 Hz, 2H), 2,96 (t, J=7.2 Hz, 2H), only 2.91 (t, J=7.2 Hz, 2H), 2,39 (s, 3H), 2,10 (Quint., J=7.2 Hz, 2H), 1,10-0,98 (m, 1H), 0,49 at 0.42 (m, 2H), 0.08 to 0,02 (m, 2H).

Example 2(157)

Hydrochloride, 8-(N-propyl-N-(4-were)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,43 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,33 (d, J=8.7 Hz, 1H), 7,19 (d, J=8,l Hz, 2H), 7,13 (who, J=8.1 Hz, 2H), was 7.08 (d, J=2.7 Hz, 1H), 6,95 (DD, J=2,7, 8,1 Hz, 1H), 5,28 (m, 2H), 5,13 (m, 2H), 5,08 (m, 2H), 3,85 (s, 3H), of 3.64 (m, 2H), is 2.37 (s, 3H), of 2.36 (s, 3H), of 1.80 (m, 2H), of 0.95 (t, J=7.5 Hz, 3H).

Example 2(158)

The dihydrochloride 8-(3-pentylamine)-2-methyl-3-(3-chloro-5-triptorelin-2-yl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,19 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 8,91 (s, 1H), 8,12 (s, 1H), 3,99 (m, 1H), 3,50 (m, 2H), 3.15 in (m, 2H), 2,47 (s, 3H), 2,32 (m, 2H), 1,94-of 1.64 (m, 4H), 1.06 a (ushort, J=6.9 Hz, 6H).

Example 2(159)

Hydrochloride, 8-(N-butyl-N-propylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,21 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,34 (d, J=8,1 Hz, 1H), was 7.08 (d, J=2.4 Hz, 1H), of 6.96 (DD, J=8,1, 2.4 Hz, 1H), 5,47 and 5.35 (Rth, J=16.5 Hz, 2H), total of 5.21 (users, 2H), 4,00-3,75 (m) and 3.85 (s) total 7H, was 2.34 (s, 3H), 1,90 is 1.75 (m, 4H), 1,42 (Sextus., J=7.2 Hz, 2H), of 1.05 and 0.98 (m, 6H).

Example 2(160)

Hydrochloride, 8-(N-butyl-N-propylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,33 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ for 7.12 (d, J=8.7 Hz, 1H), 6.89 in (d, J=2.4 Hz, 1H), PC 6.82 (DD, J=8,7, 2.4 Hz, 1H), 3.95 to 3,80 (m) and 3,83 (C) total 7H, of 3.48 (t, J=7.5 Hz, 2H), to 3.02 (t, J=7.5 Hz, 2H), 2,30-2,18 (m) and of 2.27 (s) total 5H, 2,19 (s, 3H), 1,80-of 1.65 (m, 4H), 1,38 (Sextus., J=7.2 Hz, 2H), of 0.96 (t, J=7.2 Hz, 6H).

Example 2(161)

Guide klorid 8-(4-heptylamine)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,54 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,52 (d, J=10,2 Hz, 1H), 7,34 (d, J=8.7 Hz, 1H), was 7.08 (d, J=2.4 Hz, 1H), 6,97 (DD, J=2,4, and 8.7 Hz, 1H), 5,49 (userd, J=16,8 Hz, 1H), 5,39 (d, J=16,8 Hz, 1H), 5,28 (m, 2H), 3,85 (s, 3H), 3,53 (m, 1H), 2,39 (s, 3H), of 1.75 (m, 4H), of 1.47 (m, 4H), and 1.00 (t, J=7.2 Hz, 6H).

Example 2(162)

Hydrochloride, 8-(N-butyl-N-ethylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,48 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,33 (d, J=8.7 Hz, 1H), was 7.08 (d, J=2.4 Hz, 1H), of 6.96 (DD, J=2,4, and 8.7 Hz, 1H), 5,46 (m, 1H), 5,35 (m, 1H), 5,23 (t, J=1.5 Hz, 2H), 3,80-4,00 (m, 4H), 3,85 (s, 3H), of 2.34 (s, 3H), of 1.80 (m, 2H), of 1.46 (t, J=7.2 Hz, 3H), of 1.44 (m, 2H), 1,01 (t, J=7.2 Hz, 3H).

Example 2(163)

8-(N-Cyclopropyl-N-(4-forfinal)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,80 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ to 7.32 (d, J=8,4 Hz, 1H), 7,17-to 7.09 (m, 2H), 7,07 (d, J=2.7 Hz, 1H), of 6.96-6,93 (m, 2H), 6.90 to (DD, J=8,4, 2.7 Hz, 1H), free 5.01 (s, 2H), of 3.84 (s, 3H), 2,97-of 2.86 (m, 4H), to 2.75 (m, 1H), 2,39 (s, 3H), 2,03 (m, 2H), 0,80 was 0.68 (m, 4H).

Example 2(164)

8-(N-Propyl-N-(2-forfinal)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,85 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,24 for 7.12 (m, 2H), 7,19 (d, J=8,1 Hz, 1H), 7,06-6,97 (m, 2H), 6.87 in (d, J=2.7 Hz, 1H), 6,80 (DD, J=8,1, 2.7 Hz, 1H), 5,00 to 4.92 (m, 2H), 3,83 (s, 3H), 3,42-to 3.36 (m, 2H), 2,86 (t, J=7.5 Hz, 2H), 2,75 (t, J=7.5 Hz, 2H), is 2.37 (s, 3H), 2,19 (s, 3H), 2,02 (Quint., J=7.5 Hz, 2H), 1,68 of 1.46 (m, 2H), of 0.90 (t, J=7.2 Hz, 3H).

Example 2(165)

8-(N-Propyl-N-(3-forfinal)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,86 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,30-7,22 (m, 1H), 7,18 (d, J=8,4 Hz, 1H), 7,08-7,01 (m, 2H), 6,98-of 6.90 (m, 1H), 6.87 in (d, J=2.4 Hz, 1H), 6,80 (DD, J=8,4, 2.4 Hz, 1H), around 4.85 (s, 2H), 3,83 (s, 3H), 3,42-to 3.36 (m, 2H), 2,89 (t, J=7.5 Hz, 2H), 2,86 (t, J=7.5 Hz, 2H), a 2.36 (s, 3H), 2,19 (s, 3H), of 2.09 (Quint., J=7.5 Hz, 2H), 1,68-of 1.52 (m, 2H), from 0.88 (t, J=7.5 Hz, 3H).

Example 2(166)

8 Dicyclopentadiene-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,39 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,29 (d, J=8.7 Hz, 1H), 7,06 (d, J=2.4 Hz, 1H), 6.89 in (DD, J=2,4, and 8.7 Hz, 1H), 6.48 in (userd, J=9.9 Hz, 1H), 5,22 (users, 2H), 4,89 (users, 2H), 3,83 (s, 3H), 2,87 (m, 1H), is 2.37 (s, 3H)and 1.15 (m, 2H), and 0.61 (m, 4H), 0,42 (m, 4H).

Example 2(167)

8 Dicyclopentadiene-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,40 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,29 (d, J=8,4 Hz, 1H),? 7.04 baby mortality (d, J=2.4 Hz, 1H), 6.87 in (DD, J=2,4, and 8.4 Hz, 1H), 6,37 (userd, J=9.9 Hz, 1H), 3,82 (s, 3H), 3,40 (m, 1H),3,01 (t, J=6,9 Hz, 2H), 2,88 (t, J=7.8 Hz, 2H), 2,35 (s, 3H), 2,11 (m, 2H), 1.14 in (m, 2H), from 0.50 to 0.66 (m, 4H), 0,35-0,50 (m, 4H).

Example 2(168)

Hydrochloride, 8-(N-butyl-N-propylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,52 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,40-7,30 (m, 1H), was 7.08 (s, 1H), 7,00-of 6.90 (m, 1H), 4,00-3,80 (m) and 3.85 (s) total 7H, 3,65-3,30 (m, 2H), 3,10-2,95 (m, 2H), 2.40 a-2,20 (m) and 2,33 (s) total 5H, 1,80-of 1.65 (m, 4H), 1,43-of 1.30 (m, 2H), 0,97 (t, J=6,6 Hz, 6H).

Example 2(169)

8-(N-Cyclopropylmethyl-N-propylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,54 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,31 (d, J=8,4 Hz, 1H), 7,05 (d, J=2.7 Hz, 1H), to 6.88 (DD, J=8,4, 2.7 Hz, 1H), 3,83 (s, 3H), 3,64-to 3.58 (m, 2H), 3,53 (d, J=6,9 Hz, 2H), 3,01 (t, J=7.2 Hz, 2H), 2,92 (t, J=7.2 Hz, 2H), a 2.36 (s, 3H), and 2.14 (Quint., J=7.2 Hz, 2H), 1,65-of 1.55 (m, 2H), 1,05-of 0.90 (m, 1H), of 0.91 (t, J=7.5 Hz, 3H), from 0.50 to 0.40 (m, 2H), 0,15-0,05 (m, 2H).

Example 2(170)

8-(N-Cyclopropylmethyl-N-propylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,42 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,30 (d, J=8,4 Hz, 1H), 7,07 (d, J=2.7 Hz, 1H), 6.89 in (DD, J=8,4, 2.7 Hz, 1H), 5,23 (s, 2H), 4,91 (s, 2H), 3,83 (s, 3H), 3,65-to 3.50 (m, 4H), of 2.38 (s, 3H), and 1.63 (Quint., J=7.2 Hz, 2H), 1,10-0,98 (m, 1H), were 0.94 (t, J=7.2 Hz, 3H), 0.56 to 0,46 (m, 2H), 0,15 (DD, J=10,8, 5,l Hz, 2H).

Note the R 2(171)

Hydrochloride, 8-(N-(2-butynyl)-N-propylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,44 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,34 (d, J=8.7 Hz, 1H), was 7.08 (d, J=1.8 Hz, 1H), of 6.96 (userd, J=8.7 Hz, 1H), 4,56 (d, J=2.1 Hz, 2H), 4,05-3,80 (m) and 3.85 (s) total 5H, 3,65-3,30 (m, 2H), 3.25 to 3,10 (m, 2H), 2.40 a-2,20 (m) and 2,33 (s) total 5H, 1,95-1,80 (m) and 1,89 (s) total 5H, a 1.01 (t, J=7.2 Hz, 3H).

Example 2(172)

8-(N-(2-Butynyl)-N-propylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,36 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,28 (d, J=8.7 Hz, 1H), 7,07 (d, J=2.7 Hz, 1H), 6.90 to (DD, J=8,7, 2.7 Hz, 1H), 5,32 (s, 2H), 4,91 (s, 2H), 4,45 (sq, J=2.1 Hz, 2H), of 3.84 (s, 3H), 3,55 is-3.45 (m, 2H), of 2.38 (s, 3H), equal to 1.82 (t, J=2,1 Hz, 3H), 1,72 (Sextus., J=7.2 Hz, 2H), and 0.98 (t, J=7.2 Hz, 3H).

Example 2(173)

Hydrochloride, 8-(N-butyl)-N-(2-methoxyethyl)amino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,34 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.35 (d, J=7.8 Hz, 1H), was 7.08 (d, J=2.1 Hz, 1H), 6,97 (userd, J=7.8 Hz, 1H), 4,30-4,18 (m, 2H), 3,90-of 3.78 (m) and 3.85 (s) total 5H, 3,70-3,30 (m) to 3.64 (m) total 4H, 3,30 (s, 3H), is 3.08 are 2.98 (m, 2H), 2.40 a-2,18 (m and 2,33 (s) total 5H, 1,80-of 1.65 (m, 2H), 1,43-of 1.35 (m, 2H), of 0.96 (t, J=7.2 Hz, 3H).

Example 2(174)

Hydrochloride, 8-(N-butyl-N-(2-methoxyethyl)amino)-2-methyl-3-(2-CHL is R-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,39 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,40-7,30 (m, 1H), 7,08 (users, 1H), 7,05-to 6.95 (m, 1H), ceiling of 5.60 to 5.35 (m, 2H), and 5.30-of 5.15 (m, 2H), 4,40-4,20 (m, 2H), 3,90-3,70 (m) and 3.85 (s) total 7H, the 3.35 (s, 3H), of 2.35 (s, 3H), 1.85 to to 1.70 (m, 2H), 1,50-to 1.38 (m, 2H), 0,99 (t, J=6.9 Hz, 3H).

Example 2(175)

8-(N-Propyl-N-(4-triptoreline)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,42 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,39-7,33 (m, 2H), 7,31 (d, J=8,4 Hz, 1H), 7,21-to 7.15 (m, 2H), was 7.08 (d, J=2.4 Hz, 1H), 6,91 (DD, J=8,4, 2.4 Hz, 1H), 5,12 (s, 2H), 4.95 points (s, 2H), 4,90 (s, 2H), of 3.84 (s, 3H), 3,36 of 3.28 (m, 2H), 2.40 a (s, 3H), 1.70 to and 1.54 (m, 2H), 0,89 (t, J=7.5 Hz, 3H).

Example 2(176)

8-(N-Cyclopropylmethyl-N-(4-forfinal)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,28 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,33-7,26 (m, 2H), 7,18 (d, J=8,4 Hz, 1H), 7.03 is-6,94 (m, 2H), 6.87 in (d, J=2.7 Hz, 1H), 6,80 (DD, J=8,4, 2.7 Hz, 1H), 4,88 (s, 2H), 3,83 (s, 3H), 3,38 (d, J=6,9 Hz, 2H), 2.95 points (t, J=6.9 Hz, 2H), 2,89 (t, J=6.9 Hz, 2H), a 2.36 (s, 3H), 2,19 (s, 3H), of 2.09 (Quint., J=6,9 Hz, 2H), 1,01 (m, 1H), 0,58 at 0.42 (m, 2H), 0,20-0,01 (m, 2H).

Example 2(177)

8-(3-Pentylamine)-2-methyl-3-(3,5-dichloropyridine-2-yl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,38 (hexane:ethyl acetate = 3:1).

YAM who (300 MHz, CDCl3): δ 8,58 (d, J=2,l Hz, 1H), 7,81 (d, J=2,l Hz, 1H), 6,24 (userd, J=ll,l Hz, 1H), 3,80 (m, 1H), is 3.08 (t, J=7.5 Hz, 2H), 2,93 (t, J=7.5 Hz, 2H), 2,41 (s, 3H), of 2.15 (Quint., J=7.5 Hz, 2H), 1,80-of 1.52 (m, 4H), and 1.00 (t, J=7.5 Hz, 6H).

Example 2(178)

Hydrochloride, 8-(N-butyl-N-ethylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,61 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.35 (d, J=8,4 Hz, 1H), 7,07 (d, J=2.7 Hz, 1H), of 6.96 (DD, J=2.7, and an 8.4 Hz, 1H), 3,94 (m, 4H), 3,85 (s, 3H), 3,30-3,62 (m, 2H), 3,05 (m, 2H), 2,32 (s, 3H), of 2.25 (m, 2H), 1,74 (m, 2H), 1,32 is 1.48 (m, 5H), and 0.98 (t, J=7.8 Hz, 3H).

Example 2(179)

Hydrochloride, 8-(N-cyclopropylmethyl-N-(4-triptoreline)-methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,54 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ the 7.65 (d, J=8,4 Hz, 2H), 7,47 (d, J=8,4 Hz, 2H), 7,13 (d, J=8.7 Hz, 1H), make 6.90 (d, J=2.4 Hz, 1H), 6,83 (DD, J=2,4, and 8.7 Hz, 1H), lower than the 5.37 (s, 2H), 3,83 (s, 3H), 3,66 (m, 2H), 3,52 (t, J=7.5 Hz, 2H), 3,11 (t, J=7.2 Hz, 2H), to 2.29 (s, 3H), and 2.27 (m, 2H), 2,19 (s, 3H), 1.14 in (m, 1H), 0,65 (m, 2H), 0,17 (m, 2H).

Example 2(180)

Hydrochloride 8-(3-pentylamine)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,40 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,52 (userd, J=10,2 Hz, 1H), 7,35 (d, J=8.7 Hz, 1H), was 7.08 (d, J=2.7 Hz, 1H), of 6.96 (DD, J=2.7, and 8.7 Hz, 1H), 5,50 (d, J=16.5 Hz, 1H), of 5.39 (d, J=16.5 Hz, 1H), from 5.29 (s, 2H), 3,85 (s, 3H), 3,39 (m, 1H), 2.40 a (s, 3H), 1,68-to 1.98 (m, 4H), of 1.06 (m, 6H).

Example 2(181)

8-(N-Cyclopropylmethyl-N-(4-forfinal)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,28 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,34-7,28 (m, 2H), 7,30 (d, J=8,4 Hz, 1H), was 7.08 (d, J=2.7 Hz, 1H), 7,05-6,98 (m, 2H), 6,901 (DD, J=8,4, 2.7 Hz, 1H), total of 5.21 (s, 2H), is 4.93 (s, 2H), 4,90 (s, 2H), of 3.84 (s, 3H), 3,38 (d, J=6,9 Hz, 2H,), is 2.40 (s, 3H), 1,08-0,94 (m, 1H), 0.56 to 0,48 (m, 2H), 0.14 to 0.06 to (m, 2H).

Example 2(182)

The dihydrochloride 8-(N-benzyl-N-(2-dimethylaminoethyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,60 (ethyl acetate:acetic acid:water= 3:1:1).

NMR (300 MHz, CD3OD): δ 7,45-to 7.32 (m, 5H), 7,18 (d, J=8,4 Hz, 1H), 6,98 (d, J=2.7 Hz, 1H), 6.90 to (DD, J=8,4, 2.7 Hz, 1H), 5,20 (s, 2H), and 4.40 (m, 2H), of 3.84 (s, 3H), of 3.75 (m, 2H), and 3.16 (m, 2H), 3,06 (m, 2H), 2,96 (s, 6H), to 2.35 (s, 3H), 2,38-to 2.18 (m, 2H), 2,11 (s, 3H).

Example 2(183)

The dihydrochloride 8-(N-benzyl-N-(2-dimethylaminoethyl)amino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,80 (ethyl acetate:acetic acid:water= 3:1:1).

NMR (300 MHz, CD3OD): δ 7,60-7,30 (m, 6H), 7,19 (d, J=2.4 Hz, 1H), 7,08-7,02 (m, 1H), 5,13 (s, 2H), 4,96 (s, 2H), 4,94 (s, 2H), 4,40-4,24 (m, 2H), a 3.87 (s, 3H), 3,76 (m, 1H), of 3.56 (m, 1H), 2,99 (s, 3H), 2,98 (s, 3H), is 2.44 (s, 3H).

Note the R 2(184)

The dihydrochloride 8-(N-benzyl-N-(2-dimethylaminoethyl)amino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,27 (chloroform:methanol = 9:1).

NMR (300 MHz, CD3OD): δ 7,46-7,26 (m, 6H), 7,20 (d, J=2,l Hz, 1H), 7,08-7,02 (m, 1H), 5,11 (users, 2H), 4,34-4,20 (m, 2H), a 3.87 (s, 3H), 3,76-to 3.64 (m, 2H), 3,34-2,86 (m) and 2,96 (C) total 10H, is 2.41 (s, 3H), 2.26 and is 2.10 (m, 2H).

Example 2(185)

Hydrochloride, 8-(N-(2-butynyl)-N-ethylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,36 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,10 (d, J=8,4 Hz, 1H), to 6.88 (d, J=2.7 Hz, 1H), PC 6.82 (DD, J=2.7, and an 8.4 Hz, 1H), 4,55 (sq, J=2.1 Hz, 2H), 4,08 (m, 2H), 3,83 (s, 3H), of 3.48 (t, J=7.5 Hz, 2H), up 3.22 (t, J=6.9 Hz, 2H), 2,28 (s, 3H), of 2.24 (m, 2H), 2,17 (s, 3H), 1,90 (t, J=2.1 Hz, 3H), 1,47 (t, J=7.2 Hz, 3H).

Example 2(186)

Hydrochloride, 8-(N-(2-butynyl)-N-ethylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,26 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.32 (d, J=8,4 Hz, 1H), was 7.08 (d, J=2.4 Hz, 1H), 6,95 (DD, J=2,4, and 8.4 Hz, 1H), 5,41 (s, 2H), are 5.36 (m, 2H), 4,46 (m, 2H), 4,08 (m, 2H), 3,85 (s, 3H), of 2.36 (s, 3H), 1,89 (t, J=2.7 Hz, 3H)and 1.51 (t, J=7.2 Hz, 3H).

Example 2(187)

Hydrochloride, 8-(N-(2-butynyl)-N-ethylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,32 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,34 (d, J=8,4 Hz, 1H), 7,07 (d, J=2.7 Hz, 1H), of 6.96 (DD, J=2.7, and an 8.4 Hz, 1H), 4,54 (m, 2H), 4.09 to (m, 2H), 3,85 (s, 3H), 3,35-to 3.64 (m, 2H), up 3.22 (t, J=7.2 Hz, 2H), 2,34 (s, 3H), and 2.26 (m, 2H), 1,90 (t, J=2,4 Hz, 3H), 1,47 (t, J=7.2 Hz, 3H).

Example 2(188)

8-(N,N-Dipropylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,40 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,30 (d, J=8,4 Hz, 1H), 7,05 (d, J=2.7 Hz, 1H), to 6.88 (DD, J=2.7, and an 8.4 Hz, 1H), 3,83 (s, 3H), of 3.56 (m, 4H), 2.95 points (t, J=7.2 Hz, 2H), only 2.91 (t, J=8,1 Hz, 2H), a 2.36 (s, 3H), 2.13 in (m, 2H), 1,58 (m, 4H), to 0.89 (t, J=7.2 Hz, 6H).

Example 2(189)

8-(N-(2-Butynyl)-N-cyclopropylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,50 (toluene:acetone = 5:1).

NMR (300 MHz, CDCl3): δ 7,28 (d, J=8,4 Hz, 1H), 7,07 (d, J=2.7 Hz, 1H), 6.90 to (DD, J=8,4, 2.7 Hz, 1H), to 5.35 (s, 2H), 4,91 (s, 2H), 4,56 (m, 2H), 3,83 (s, 3H), 3,50 (m, 2H), 2,39 (s, 3H), equal to 1.82 (t, J=2,4 Hz, 3H), 1,15 (m, 1H), of 0.64 to 0.56 (m, 2H), range 0.38 to 0.28 (m, 2H).

Example 2(190)

8-(N-Propyl-N-(4-cyanophenyl)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,22 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,60 (userd, J=8,1 Hz, 2H), 7,47 (userd, J=8,1 Hz, 2H), 7,17 (d, J=8.7 Hz, 1H), 6.87 in (d, J=2.7 Hz, 1H), 6,79 (DD, J=8,7, 2.7 Hz, 1H), 4,90 (s, 2H) a 3.83 (s, 3H), 3,39 (m, 2H), 2,94-2,82 (m, 4H), of 2.34 (s, 3H), of 2.18 (s, 3H), 2,11 (m, 2H), 1,59 (m, 2H), from 0.88 (t, J=7.2 Hz, 3H).

Example 2(191)

8-(N-(Cyclopropyl)-N-(4-methylthiophenyl)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,20 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ to 7.32 (d, J=8,4 Hz, 1H), 7,19-7,13 (m, 2H), was 7.08 (d, J=2.7 Hz, 1H), 7,06-7,01 (m, 2H), 6,91 (DD, J=8,4, 2.7 Hz, 1H), 5,20 (s, 2H), further 5.15 (s, 2H), 4,91 (s, 2H), of 3.84 (s, 3H), of 2.56 (m, 1H), 2,46 (, 3H), 2,41 (s, 3H), 0.95 to-0,88 (m, 4H).

Example 2(192)

8-(N-Propyl-N-(4-methylthiophenyl)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,25 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,31 (d, J=8.7 Hz, 1H), 7,20 (s, 4H), was 7.08 (d, J=2.7 Hz, 1H), 6.90 to (DD, J=8,7, 2.7 Hz, 1H), 5,10 (s, 2H), 4,90 (s, 2H), 4,89 (s, 2H), of 3.84 (s, 3H), 3,34 (m, 2H), 2,48 (s, 3H), 2.40 a (s, 3H), 1,70 of 1.50 (m, 2H), 0,89 (t, J=7.5 Hz, 3H).

Example 2(193)

8-(N-(Cyclopropyl)-N-(4-forfinal)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,19 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ to 7.32 (d, J=8,4 Hz, 1H), 7,14? 7.04 baby mortality (m, 3H), 7,02-6,94 (m, 2H), 6,92 (DD, J=8,4, 2.4 Hz, 1H), 5,19 (s, 2H), 5,16 (s, 2H), 4,91 (s, 2H), of 3.84 (s, 3H), by 2.55 (m, 1H), 2,41 (s, 3H), 0,90-0,76 (m, 4H).

Example 2(194)

8-(N-Propyl-N-(3-forfinal)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d[1,5-a]pyrimidine

TLC: Rf= 0,48 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,33 (d, J=8,4 Hz, 1H), 7,26-to 7.15 (m, 2H), 7,07 (d, J=2.4 Hz, 1H), 7,05-6,98 (m, 2H), 6.89 in (DD, J=8,4, 2.4 Hz, 1H), 4,94 (s, 2H), of 3.84 (s, 3H), 3,39 (m, 2H), 2,88 (t, J=7.5 Hz, 2H), 2,77 (t, J=7.5 Hz, 2H), 2.40 a (s, 3H), 2,04 (Quint., J=7.5 Hz, 2H), and 1.63 (m, 2H), of 0.90 (t, J=7.5 Hz, 3H).

Example 2(195)

8-(N-Propyl-N-(3-forfinal)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,46 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ to 7.32 (d, J=8,4 Hz, 1H), 7,28-7,16 (m, 2H), was 7.08 (d, J=2.4 Hz, 1H), 7,07-of 6.99 (m, 2H), 6,91 (DD, J=8,4, 2.4 Hz, 1H), 5,07 (s, 2H), 5,04 (s, 2H), 4,88 (s, 2H), of 3.84 (s, 3H), of 3.13 (m, 2H), 2,41 (, 3H), 1,68 (Sextus., J=7.5 Hz, 2H), of 0.93 (t, J=7.5 Hz, 3H).

Example 2(196)

8 Dipropylamino-2-methyl-3-(2,5-dichlorophenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,64 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,41 (d, J=8.7 Hz, 1H), 7,40 (d, J=2.4 Hz, 1H), 7.23 percent (DD, J=8,7, 2.4 Hz, 1H), 3,60-to 3.52 (m, 4H), 2,96 (t, J=7,8 Hz) and 2.93 (t, J=7,8 Hz) total 4H, is 2.37 (s, 3H), of 2.15 (Quint., J=7.8 Hz, 2H), 1,65 of 1.50 (m, 4H), to 0.89 (t, J=7.2 Hz, 6H).

Example 2(197)

8 Dipropylamino-2-methyl-3-(2,4-dichlorophenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,57 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,51 (d, J=2.4 Hz, 1H), 7,35 (d, J=8,1 Hz, 1H), 7,29 (DD, J=8,1, 2.4 Hz,1H), the 3.65-to 3.50 (m, 4H), 2,96 (t, J=7.2 Hz) and of 2.92 (t, J=7.2 Hz) total 4H, a 2.36 (s, 3H), and 2.14 (Quint., J=7.2 Hz, 2H), 1,63-of 1.45 (m, 4H), to 0.89 (t, J=7.5 Hz, 6H).

Example 2(198)

8 Dipropylamino-2-methyl-3-(4-were)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,58 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,58 (d, J=7.8 Hz, 2H), 7,24 (d, J=7.8 Hz, 2H), 3,60-to 3.52 (m, 4H), 3.00 and-2,90 (m, 4H), of 2.56 (s, 3H), is 2.37 (s, 3H), and 2.14 (Quint., J=7.5 Hz, 2H), 1,64 is 1.48 (m, 4H), of 0.87 (t, J=7.2 Hz, 6H).

Example 2(199)

8 Dipropylamino-2-methyl-3-(3-were)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,61 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,50 (C) and 7,47 (d, J=7.5 Hz) total 2H, to 7.32 (t, J=7.5 Hz, 1H), 7,06 (t, J=7.5 Hz, 1H), 3,60-to 3.52 (m, 4H), 2,96 (t, J=7.8 Hz, 4H), 2.57 m (s, 3H), 2,41 (s, 3H), of 2.15 (Quint., J=7.8 Hz, 2H), 1,64-of 1.45 (m, 4H), to 0.88 (t, J=7.2 Hz, 6H).

Example 2(200)

8 Dipropylamino-2-methyl-3-(2-were)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,56 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,35-7,20 (m, 4H), 3,62-of 3.54 (m, 4H), 2,96 (t, J=7.2 Hz) and 2,90 (t, J=7.2 Hz) total 4H, of 2.34 (s, 3H), 2,22 (s, 3H), 2.13 and (Quint., J=7.2 Hz, 2H), 1,63 of 1.50 (m, 4H), to 0.89 (t, J=7.5 Hz, 6H).

Example 2(201)

8-(N-Propyl-N-(benzo[d]-1,3-dioxolane-5-yl)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

f= 0,31 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ to 7.18 (d, J=8,1 Hz, 1H), 6.87 in (d, J=2.7 Hz, 1H), 6,77-6,83 (m, 2H), 6,67 to 6.75 (m, 2H), 5,94 (s, 2H), 4,74 (s, 2H), 3,83 (s, 3H), 3,37 (m, 2H), 2,89 (t, J=7.8 Hz, 2H), 2,85 (t, J=7.5 Hz, 2H), of 2.35 (s, 3H), of 2.20 (s, 3H), of 2.08 (m, 2H), 1,58 (m, 2H), from 0.88 (t, J=7.2 Hz, 3H).

Example 2(202)

Hydrochloride, 8-(N-propyl-N-(benzo[d]-1,3-dioxolane-5-yl)-methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,38 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ of 7.36 (d, J=8,4 Hz, 1H), was 7.08 (d, J=2.7 Hz, 1H), 6,97 (DD, J=8,4, 2.7 Hz, 1H), 6,70-PC 6.82 (m, 3H), 6,00 (s, 2H), 5,07 (s, 2H), 3,85 (s, 3H), 3,71 (m, 2H), 3,36-to 3.64 (m, 2H), 3,03 (t, J=7.4 Hz, 2H,), to 2.35 (s, 3H), 2,24 (m, 2H), 1,74 (m, 2H), of 0.93 (t, J=7.5 Hz, 3H).

Example 2(203)

8-(3-Pentylamine)-2-methyl-3-(2-were)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,39 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,30-to 7.18 (m, 4H), 6,23 (d, J=10.5 Hz, 1H), 3,90 of 3.75 (m, 1H), 3,09 (t, J=7.2 Hz, 2H), 2,90 (t, J=7.2 Hz, 2H), 2,32 (s, 3H), 2,22 (s, 3H), and 2.14 (Quint., J=7.2 Hz, 2H), 1,80 is 1.58 (m, 4H), 1,08-to 0.96 (m, 6H).

Example 2(204)8-(3-Pentylamine)-2-methyl-3-(3-were)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,45 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ to 7.50 (s, 1H), 7,46 (d, J=7.8 Hz, 1H), 7,31 (t, J=7.8 Hz, 1H), 7,05 (d, J=7.8 Hz, 1H), 6,21 (d, J=10,8 Hz, 1H), 3,86-3,74 (m, 1H), is 3.08 (t, J=7.2 Hz, 2H), 2.95 points (t,J=7.2 Hz, 2H), by 2.55 (s, 3H), 2,41 (s, 3H), of 2.15 (Quint., J=7.2 Hz, 2H), 1,82-of 1.55 (m, 4H), 1,01 (t, J=7.5 Hz, 6H).

Example 2(205)

8-(3-Pentylamine)-2-methyl-3-(4-were)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,47 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ EUR 7.57 (d, J=7.8 Hz, 2H), 7,24 (d, J=7.8 Hz, 2H), 6,20 (10,5 Hz, 1H), 3,83 of 3.75 (m, 1H), is 3.08 (t, J=7.2 Hz, 2H), equal to 2.94 (t, J=7.2 Hz, 2H), by 2.55 (s, 3H), is 2.37 (s, 3H), of 2.15 (Quint., J=7.2 Hz, 2H), 1,80-of 1.52 (m, 4H), and 1.00 (t, J=7.2 Hz, 6H).

Example 2(206)

Hydrochloride 8-(3-pentylamine)-2-methyl-3-(2-methylthio-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,10 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,26-7,16 (m, 1H), 6,83 (m, 1H), 6,84-6,76 (m, 1H), 3,97 (m, 1H), 3,86 (s, 3H), of 3.48 (m, 2H), 3,12 (m, 2H), 2,44 (s, 3H), of 2.33 (s, 3H), 2,28 (m, 2H), 1,95-of 1.44 (m, 4H), 1,11-0,99 (m, 6H).

Example 2(207)

Hydrochloride, 8-(N-propyl-N-(benzo[d]-1,3-dioxolane-5-yl)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,40 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,34 (d, J=8.7 Hz, 1H), was 7.08 (d, J=2.7 Hz, 1H), 6,95 (DD, J=2.7, and 8.7 Hz, 1H), 6,78-6,83 (m, 2H), 6,72 (m, 1H), of 5.99 (s, 2H), 5,28 (m, 2H), 5,16 (s, 2H), 5,04 (m, 2H), 3,85 (s, 3H), of 3.60 (m, 2H,), of 2.38 (s, 3H), 1.77 in (m, 2H), of 0.95 (t, J=7.2 Hz, 3H).

Example 2(208)

Hydrochloride, 8-(N-benzyl-N-cyclopropylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-Cyclops the NTA[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,58 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,25-the 7.43 (m, 5H), 7,13 (d, J=7.8 Hz, 1H), make 6.90 (d, J=2.4 Hz, 1H), 6,83 (DD, J=2,4, and 7.8 Hz, 1H), 5,28 (s, 2H), of 3.84 (s, 3H), of 3.69 (m, 2H), 3,48 (t, J=8,1 Hz, 2H), of 3.07 (t, J=7.2 Hz, 2H), 2,30 (s, 3H), 2,24 (m, 2H), 2,19 (s, 3H), of 1.16 (m, 1H), 0,63 (m, 2H), 0,18 (m, 2H).

Example 2(209)

Hydrochloride, 8-(N-benzyl-N-cyclopropylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,56 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,25-the 7.43 (m, 6H), to 7.09 (d, J=2.7 Hz, 1H), of 6.96 (DD, J=2.7, and an 8.4 Hz, 1H), 5,27 (m, 2H), 3,85 (s, 3H), 3,68 (m, 2H), 3,48 (m, 2H), of 3.07 (t, J=6.9 Hz, 2H), 2,35 (s, 3H), of 2.23 (m, 2H), 1,16 (m, 1H), of 0.64 (m, 2H), 0,18 (m, 2H).

Example 2(210)

Hydrochloride, 8-(N-benzyl-N-cyclopropylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,47 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,26 was 7.45 (m, 6H), to 7.09 (d, J=2.4 Hz, 1H), of 6.96 (DD, J=2,4, 8,1 Hz, 1H), are 5.36 (m, 2H), 5,28 (m, 2H), 5,23 (s, 2H), 3,85 (s, 3H), of 3.69 (m, 2H), is 2.37 (s, 3H), 1,21 (m, 1H), 0,66 (m, 2H), 0,22 (m, 2H).

Example 2(211)

8-(N-Butyl-N-(2-butynyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,38 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,16 (d, J=8,4 Hz, 1H), 6,86 (d, J=2.7 Hz, 1H), 6,79 (DD, J=,4, 2.7 Hz, 1H), 4,40 (users, 2H), 3,82 (s, 3H)and 3.59 (m, 2H), 3,11 (t, J=7.2 Hz, 2H), only 2.91 (t, J=7.8 Hz, 2H), 2,32 (s, 3H), of 2.18 (s, 3H), 2.13 in (m, 2H), 1,81 (t, J=2,l Hz, 3H), and 1.63 (m, 2H), 1,38 (m, 2H), of 0.94 (t, J=7.5 Hz, 3H).

Example 2(212)

Hydrochloride 8-(3-pentylamine)-2-methyl-3-(2-methyl-4-forfinal)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,44 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, DMSO-d6): δ 7,34-7,24 (m, 2H), 7,20-7,10 (m, 1H), 4,03-of 3.85 (m, 1H), 3,14 (ushort, J=8,l Hz, 2H), 2.95 and (ushort, J=8,1 Hz, 2H, in), 2.25 (s, 3H), 2,25-2,10 (m) and 2.12 (C) total 5H, 1,85-to 1.60 (m, 4H), 0,95-of 0.85 (m, 6H).

Example 2(213)

Hydrochloride 8-(3-pentylamine)-2-methyl-3-(2,5-dichlorophenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,46 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, DMSO-d6): δ to 7.68 (d, J=8,4 Hz, 1H), 7,62-7,55 (m) and to 7.59 (C) total 2H, a 4.03-of 3.85 (m, 1H), 3,14 (ushort, J=7.8 Hz, 2H), 2,96 (ushort, J=7.8 Hz, 2H), 2,32 (s, 3H), 2,25-2,10 (m, 2H), 1.85 to to 1.60 (m, 4H), to 0.89 (t, J=7.5 Hz, 6H).

Example 2(214)

Hydrochloride 8-(3-pentylamine)-2-methyl-3-(2,4-acid)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,43 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, DMSO-d6): δ from 7.24 (d, J=8,1 Hz, 1H), of 6.71 (d, J=2.4 Hz, 1H), 6,66 (DD, J=8,1, 2.4 Hz, 1H), 4,05-of 3.85 (m, 1H), 3,85 (s, 3H), 3,74 (s, H), 3.15 in (ushort, J=8,l Hz, 2H), 2,99 (ushort, J=8,l Hz, 2H), 2,33(s, 3H in ), 2.25-2,10 (m, 2H), 1.85 to to 1.63 (m, 4H), to 0.89 (t, J=7.5 Hz, 6H).

Example 2(215)

Hydrochloride 8-(3-p is tramino)-2-methyl-3-(2-fluoro-4-were)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,43 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, DMSO-d6): δ 9,20-9,00 (m, 1H), 7,39 (t, J=7.8 Hz, 1H), 7,22 (d, J=ll,l Hz, 1H), 7,17 (d, J=7.8 Hz, 1H), 4,05-of 3.60 (m, 1H, overlapped with water, DMSO-d6), 3,14 (ushort, J=7.8 Hz, 2H), 2,99 (ushort, J=7.8 Hz, 2H), 2.40 a (s, 3H), is 2.37 (s, 3H), 2,18 (Quint., J=7.8 Hz, 2H), 1,83 is 1.60 (m, 4H), to 0.89 (t, J=7.5 Hz, 6H).

Example 2(216)

8-(N-Butyl-N-(2-butynyl)amino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,80 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,29 (d, J=8.7 Hz, 1H), 7,06 (d, J=2.4 Hz, 1H), to 6.88 (DD, J=8,7, 2.4 Hz, 1H), 4,39 (sq, J=2,l Hz, 2H), 3,83 (s, 3H)and 3.59 (m, 2H), 3,11 (t, J=7.5 Hz, 2H), 2,93 (t, J=7.5 Hz, 2H), a 2.36 (s, 3H), and 2.14 (Quint., J=7.5 Hz, 2H), 1,81 (t, J=2,l Hz, 3H), 1,68-and 1.54 (m, 2H), 1.39 in (Sextus., J=7.5 Hz, 2H), were 0.94 (t, J=7.5 Hz, 3H).

Example 2(217)

8-(N-Butyl-N-(2-butynyl)amino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,78 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,28 (d, J=8.7 Hz, 1H), 7,07 (d, J=2.7 Hz, 1H), 6.89 in (DD, J=8,7, 2.7 Hz, 1H), 5,33 (s, 2H), 4,91 (s, 2H), of 4.44 (sq, J=2.4 Hz, 2H), 3,83 (s, 3H), of 3.54 (m, 2H), of 2.38 (s, 3H), equal to 1.82 (t, J=2.4 Hz, 3H), 1,74-to 1.61 (m, 2H), 1,41 (Sextus., J=7.5 Hz, 2H), of 0.96 (t, J=7.5 Hz, 3H).

Example 2(218)

Hydrochloride 8-(3-methyl-2-butylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,36 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,45 (userd, J=10,2 Hz, 1H), 7,11 (DD, J=4.2, and an 8.4 Hz, 1H), 6.89 in (d, J=2.4 Hz, 1H), PC 6.82 (DD, J=2,4, and 8.4 Hz, 1H), 4,07 (m, 1H), 3,83 (s, 3H), 3,49 (m, 2H), 3.15 in (t, J=6.9 Hz, 2H), to 2.29 (m, 2H), 2,28 (, 3H), 2.20 2,19 (s, total 3H), 1,99 (m, 1H), of 1.42 and 1.41 (d, J=6,6 Hz, total 3H), of 1.05 to 1.14 (m, 6H).

Example 2(219)

Hydrochloride 8-(1-cyclohexylethylamine)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,36 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,42 (userd, J=10.5 Hz, 1H), 7,11 and 7.10 (d, J=8.1 Hz, total 1H), to 6.88 (d, J=2.7 Hz, 1H), for 6.81 (DD, J=2,7, 8,1 Hz, 1H), a 4.03 (m, 1H), 3,82 (s, 3H), of 3.48 (m, 2H), 3,12 (t, J=7.5 Hz, 2H), 2,28 (m, 2H), 2,28 (s, 3H), of 2.20 and 2.18 (s, total 3H), 1,52-of 1.95 (m, 6H), of 1.41 and 1.40 (d, J=6,6 Hz, total 3H), of 1.01 to 1.37 (m, 5H).

Example 2(220)

Hydrochloride 8-(2-pentylamine)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,36 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,34 (userd, J=9.6 Hz, 1H), 7,11 and 7.10 (d, J=8.7 Hz, total 1H), 6.89 in (d, J=2.7 Hz, 1H), for 6.81 (DD, J=2.7, and 8.7 Hz, 1H), 4,25 (m, 1H), 3,83 (s, 3H), 3,49 (m, 2H), and 3.16 (t, J=6.9 Hz, 2H), to 2.29 (m, 2H), 2,28 (s, 3H), 2.20 2,19 (s, total 3H), 1,70-1,80 (m, 2H), 1,44 is 1.58 (m, 2H), 1,47, and of 1.46 (d, J=6,6 Hz, total 3H), 1,01 (m, 3H).

Example 2(221)

Hydrochloride 8-(2-heptylamine)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,43 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,32 (userd, J=10,2 Hz, 1H), 7,12 and 7,11 (d, J=8,4 Hz, total 1H), 6.89 in (d, J=2.7 Hz, 1H), PC 6.82 (DD, J=2.7, and an 8.4 Hz, 1H), 4,22 (m, 1H), 3,83 (s, 3H), 3,50 (m, 2H), 3.15 in (t, J=6.9 Hz, 2H), to 2.29 (m, 2H), 2,28 (s, 3H), 2.20 2,19 (s, total 3H), 1,71-of 1.81 (m, 2H), 1.30 and of 1.55 (m, 9H), to 0.92 (m, 3H).

Example 2(222)

Hydrochloride 8-(1-methoxy-2-propylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,30 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,66 (userd, J=8,4 Hz, 1H), 7,11 and 7.10 (d, J=8.7 Hz, total 1H), to 6.88 (d, J=2.7 Hz, 1H), 6,80 (DD, J=2.7, and 8.7 Hz, 1H), 4,46 (m, 1H), 3,82 (s, 3H), of 3.64 (DD, J=3,9, 9.9 Hz, 1H), 3,42-to 3.58 (m, 3H), of 3.46 and 3.45 (with only 3H), 3,23 (m, 1H), 3,11 (m, 1H), to 2.29 (m, 2H), to 2.29 (s, 3H), are 2.19 and 2.18 (s, only, 3H), 1,49 (d, J=6.6 Hz, 3H).

Example 2(223)

Hydrochloride 8-(2-octylamine)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,60 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,33 (userd, J=10,2 Hz, 1H), 7,12 and 7,11 (d, J=8.1 Hz, total 1H), 6.89 in (d, J=2.7 Hz, 1H), PC 6.82 (DD, J=2,7, 8,1 Hz, 1H), 4,23 (m, 1H), 3,83 (s, 3H), 3,50 (ushort, J=7.2 Hz, 2H), 3.15 in (t, J=6.6 Hz, 2H), 2,29 (m, 2H), 2,28 (s, 3H), 2.20 2,19 (s, total 3H), of 1.75 (m, 2H), 1.46 and a 1.45 (d, J=6.3 Hz, total 3H), 1,26-of 1.45 (m, 8H), of 0.90 (m, 3H).

Example 2(224)

8-(1,2,3,4-Tetrahydronaphthalen-1-yl)amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]Piri is one

TLC: Rf= 0,16 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,44 (m, 1H), 7,27-7,14 (m, 4H), 6,85 (d, J=2.7 Hz, 1H), 6,78 (DD, J=8,1, 2.7 Hz, 1H), 6,69 (userd, J=9.9 Hz, 1H), 5,22 (m, 1H), 3,82 (s, 3H), 3,24-is 3.08 (m, 2H), 3.00 and was 2.76 (m, 4H), and 2.26 (s, 3H), 2,24-to 1.82 (m, 6H), of 2.20 (s, 3H).

Example 2(225)

8-((1S,2S,3S,5R)-2,6,6-trimethylbicyclo[3.1.1]-3-heptyl)amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,25 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,16 (d, J=8,1 Hz, 1H), 6,85 (d, J=2.4 Hz, 1H), 6,78 (DD, J=8,1, 2.4 Hz, 1H), 6.35mm (userd, J=10,8 Hz, 1H), or 4.31 (m, 1H), 3,82 (s, 3H), 3,22-of 3.06 (m, 2H), only 2.91 (t, J=8,1 Hz, 2H), 2,62 is 2.46 (m, 2H), 2,31 (s, 3H), 2,19 (s, 3H), 2,19-to 1.82 (m, 6H), of 1.29 (s, 3H), 1,20 (d, J=6.0 Hz, 3H), 1,11-1,08 (m, 1H), 1,09 (s, 3H).

Example 2(226)

Hydrochloride 8-(3-pentylamine)-2-methyl-3-(2-methyl-4-chlorophenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,41 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,38-to 7.32 (m, 2H), 7,26-7,10 (m, 2H), 4.04 the-3,90 (m, 1H), 3,60-3,30 (m, 2H), 3,13 (t, J=6.6 Hz, 2H), 2,39 (s, 3H), of 2.35 (s, 3H), 2,28 (Quint., J=6,6 Hz, 2H), 1,92-of 1.40 (m, 4H), of 1.06 (t, J=7.2 Hz, 6H).

Example 2(227)

Hydrochloride 8-(3-pentylamine)-2-methyl-3-(2,5-acid)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,52 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,32-7,24 (m, 1H), 7,00-6,9 (m, 2H), 6,85 (d, J=2.4 Hz, 1H), 4,05-3,95 (m, 1H), 3,90 (s, 3H), of 3.84 (s, 3H), of 3.56 (t, J=7.8 Hz, 2H), 3,12 (t, J=7.8 Hz, 2H), 2,43 (s, 3H), to 2.29 (Quint., J=7.8 Hz, 2H), 1,90-of 1.40 (m, 4H), of 1.05 (t, J=7.5 Hz, 6H).

Example 2(228)

Hydrochloride 8-(3-pentylamine)-2-methyl-3-(2-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,24 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,41 (t, J=8,1 Hz, 1H), 7,34-7,24 (m, 2H), 7,10-7,02 (m, 2H), 4,03-3,90 (m, 1H), 3,94 (s, 3H), of 3.56 (t, J=7.5 Hz, 2H), 3,12 (t, J=7.5 Hz, 2H), 2,43 (s, 3H), 2,36-of 2.20 (m, 2H), 1,90-of 1.40 (m, 4H), of 1.05 (t, J=7.5 Hz, 6H).

Example 2(229)

Hydrochloride 8 Dicyclopentadiene-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,46 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,87 (m, 1H), 7,11 (d, J=8.7 Hz, 1H), 6.89 in (d, J=2.7 Hz, 1H), PC 6.82 (DD, J=2.7, and 8.7 Hz, 1H), lower than the 5.37 (s, 2H), 5,19 (m, 2H), 3,83 (s, 3H), 2,90 (m, 1H), a 2.36 (s, 3H), of 2.20 (s, 3H), 1.26 in (m, 2H), 0,66-of 0.85 (m, 4H), 0,47 (m, 4H).

Example 2(230)

Hydrochloride, 8-(N-butyl-N-ethylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,49 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,10 (d, J=8.7 Hz, 1H), 6.89 in (d, J=2.7 Hz, 1H), PC 6.82 (DD, J=2.7, and 8.7 Hz, 1H), of 5.40 (s, 2H), 5,23 (s, 2H), 3,85-4,00 (m, 4H), 3,83 (s, 3H), to 2.29 (s, 3H), 2,19 (s, 3H), equal to 1.82 (m, 2H), 1,46 (t, J=6,9 Hz, 3H), of 1.44 (m, 2H), of 1.02 (t, J=6.9 Hz, 3H).

Example 2(231)

Hydrochloride, 8-(N-butyl-N-propylamino-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,54 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,10 (d, J=8,4 Hz, 1H), 6.89 in (d, J=2.4 Hz, 1H), PC 6.82 (DD, J=2,4, and 8.4 Hz, 1H), of 5.40 (s, 2H), total of 5.21 (s, 2H), a 3.87 (m, 4H), 3,83 (s, 3H), to 2.29 (s, 3H), 2,19 (s, 3H), equal to 1.82 (m, 4H), of 1.42 (m, 2H), of 1.02 (t, J=7.2 Hz, 3H), and 1.00 (t, J=7.2 Hz, 3H).

Example 2(232)

Hydrochloride, 8-(N,N-dipropylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rfor = 0.51 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,10 (d, J=8,4 Hz, 1H), 6.89 in (d, J=3.0 Hz, 1H), PC 6.82 (DD, J=3.0 a, and 8.4 Hz, 1H), 5,39 (users, 2H), total of 5.21 (users, 2H), 3,85 (m, 4H), 3,83 (s, 3H), to 2.29 (s, 3H), 2,19 (s, 3H)and 1.83 (m, 4H), of 1.02 (t, J=7,2 Hz, 6H).

Example 2(233)

Hydrochloride, 8-(N-ethyl-N-(4-hydroxybutyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,29 (hexane:ethyl acetate = 1:2).

NMR (300 MHz, CDCl3): δ 7,10 (d, J=8,4 Hz, 1H), 6.87 in (d, J=3.0 Hz, 1H), 6,79 (DD, J=3.0 a, and 8.4 Hz, 1H), a 3.87-4,01 (m, 4H), 3,82 (s, 3H), of 3.65 (t, J=6.0 Hz, 2H), 3,38 (t, J=7.5 Hz, 2H), 3,06 (t, J=7.2 Hz, 2H), and 2.27 (s, 3H), 2,24 (m, 2H), 2,17 (s, 3H), of 1.86 (m, 2H), 1.61 of (m, 2H), 1,38(t, J=7.2 Hz, 3H).

Example 2(234)

Hydrochloride, 8-bis(2-methoxyethyl)amino-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,35 (hexane:ethyl acetate = 1:2).

NMR (300 MHz, CDCl3): δ 7,33 (d, J=8,4 Hz, 1H), was 7.08 (d, J=2.4 to the C, 1H), of 6.96 (DD, J=2,4, and 8.4 Hz, 1H), 5.40 to (m, 1H), 5,33 (m, 1H), 5.25 in (m, 2H), 4,15 (m, 4H), 3,85 (s, 3H), 3,71 (t, J=5,l Hz, 4H), to 3.35 (s, 6H), to 2.35 (s, 3H).

Example 2(235)

Hydrochloride 8-(3-pentylamine)-2-methyl-3-(2-methoxy-5-isopropylphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,36 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ of 7.23 (DD, J=8,4, 2,l Hz, 1H), 7,12 (d, J=2.1 Hz, 1H), 6,98 (d, J=8,4 Hz, 1H), 4,00-3,85 (m) 3,91 (C) total 4H, to 3.58-3,30 (m, 2H), 3,11 (t, J=6.9 Hz, 2H), 2,92 (m, 1H), 2,43 (s, 3H), 2,35-2,20 (m, 2H), 1,90 of 1.50 (m, 4H), of 1.26 (d, J=6.9 Hz, 6H), was 1.04 (t, J=7.5 Hz, 6H).

Example 2(236)

Hydrochloride 8-(3-pentylamine)-2-methyl-3-(2-methoxy-5-forfinal)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,26 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,20-to 6.95 (m, 4H), 4.04 the-3,80 (m) 3,91 (C) total 4H, 3,52 is 3.40 (m, 2H), 3,12 (t, J=7.2 Hz, 2H), 2,43 (s, 3H), and 2.27 (Quint., J=7.2 Hz, 2H), 1,90-of 1.40 (m, 4H), of 1.05 (t, J=7.5 Hz, 6H).

Example 2(237)

Hydrochloride, 8-(N-butyl-N-(4-forfinal)methylamino)-2-methyl-3-(2-chloro-5-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,40 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,44-7,20 (m, 3H), 7,14-of 6.90 (m, 4H), 5,03 (users, 2H), 3,85 (s, 3H), 3,62 (m, 2H), 3,29 (m, 2H), 2,96 (m, 2H), is 2.37 (s, 3H), 2,19 (m, 2H), 1,65 (m, 2H), 1,32 (m, 2H), 0,90 (m, 3H).

Example 2(238)

Hydrochloride, 8-(N-butyl-N-(4-forfinal)methylamino)-2-methyl-3-(2-chloro-4-methods Setenil)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,20 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,40-7,26 (m, 3H), 7,12 (userd, J=7.8 Hz, 2H), to 7.09 (d, J=2,l Hz, 1H), 6,99-6,92 (m, 1H), 5.40 to (m, 2H), and 5.30-5,08 (m, 4H), 3,85 (s, 3H), 3,70 (m, 2H), is 2.37 (s, 3H), of 1.76 (m, 2H), 1,36 (m, 2H), were 0.94 (t, J=7.5 Hz, 3H).

Example 2(239)

Hydrochloride, 8-(N-butyl-N-(4-forfinal)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,28 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,29 (m, 2H), 7.18 in? 7.04 baby mortality (m, 3H), 6.89 in (d, J=2.1 Hz, 1H), 6,85-of 6.78 (m, 1H), 5,23 (m, 2H), 5,15 (m, 2H), 5,11 (m, 2H), 3,83 (s, 3H), to 3.58 (m, 2H), 2,33 (s, 3H), of 2.20 (s, 3H), 1,71 (m, 2H), 1,35 (m, 2H), 0,95-0,84 (m, 3H).

Example 2(240)

Hydrochloride 8-(3-pentylamine)-2-methyl-3-(2-methoxy-5-chlorophenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,26 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,33 (DD, J=9,0, 3.0 Hz, 1H), 7,25-7,05 (m) and 7,22 (d, J=3.0 Hz) total 2H, 6,98 (d, J=9.0 Hz, 1H), 4,03-3,85 (m) 3,93 (C) total 4H, 3,55 is 3.40 (m, 2H), 3,13 (t, J=7.2 Hz, 2H), 2,43 (s, 3H), 2,28 (Quint., J=7.2 Hz, 2H), 1,90-of 1.40 (m, 4H), of 1.05 (t, J=7.5 Hz, 6H).

Example 2(241)

Hydrochloride, 8-(N-ethyl-N-(2-butyryl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,37 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,10 (d, J=8,4 Hz, 1H), 6.89 in (d, J=2.7 Hz, 1H), PC 6.82 (DD, J=,7, and 8.4 Hz, 1H), 5,41 (s, 4H), 4,48 (m, 2H), 4,14 (m, 2H), 3,83 (s, 3H), 2,31 (s, 3H), of 2.18 (s, 3H), 1,90 (t, J=2,4 Hz, 3H), and 1.54 (t, J=7.2 Hz, 3H).

Example 2(242)

Hydrochloride, 8-(N-propyl-N-(2-butyryl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,47 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,10 (d, J=8,1 Hz, 1H), 6.89 in (d, J=2.7 Hz, 1H), PC 6.82 (DD, J=2,7, 8,1 Hz, 1H), 5,41 (m, 2H), 5,39 (m, 2H), 5,42 (m, 2H), 3,98 (m, 2H), 3,83 (s, 3H), 2,31 (s, 3H), of 2.18 (s, 3H), of 1.94 (m, 2H), 1, 89 (t, J=2.7 Hz, 3H), of 1.05 (t, J=7.2 Hz, 3H).

Example 2(243)

Hydrochloride, 8-(N-propyl-N-(4-methylthiophenyl)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,45 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,27 (d, J=8,4 Hz, 2H), 7,20 (d, J=8,4 Hz, 2H), 7,12 (d, J=8,4 Hz, 1H), make 6.90 (d, J=2.7 Hz, 1H), 6,83 (DD, J=2.7, and an 8.4 Hz, 1H), of 5.40 (s, 2H), 5,11-of 5.26 (m, 4H), of 3.84 (s, 3H), 3,70 (m, 2H), 2,50 (s, 3H), 2,31 (s, 3H), of 2.20 (s, 3H), of 1.84 (m, 2H), 0,97 (t, J=7.2 Hz, 3H).

Example 2(244)

Hydrochloride, 8-(N-propyl-N-(benzo[d]-1,3-dioxolane-5-yl)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,45 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,13 (d, J=8,1 Hz, 1H), make 6.90 (d, J=2.7 Hz, 1H), 6,83 (DD, J=2,7, 8,1 Hz, 1H), PC 6.82 (d, J=7.5 Hz, 1H), 6,78 (d, J=1.5 Hz, 1H), 6.73 x (DD, J=1.5 and 7.5 Hz, 1H), 6,01 (s, 2H), of 5.39 (s, 2H), 5,17 (s, 2H), 5,11 (m, 2H), of 3.84 (s, 3H), of 3.69 (m, 2H), 2,32 (s, 3), of 2.21 (s, 3H), of 1.81 (m, 2H), of 0.96 (t, J=7.2 Hz, 3H).

Example 2(245)

Hydrochloride, 8-(N-benzyl-N-cyclopropylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,47 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,34-7,46 (m, 3H), 7,26-7,33 (m, 2H), 7,13 (d, J=8.7 Hz, 1H), make 6.90 (d, J=2.7 Hz, 1H), at 6.84 (DD, J=2.7, and 8.7 Hz, 1H), 5,42 (s, 2H), 5,33 (m, 2H), 5,24 (s, 2H), of 3.84 (s, 3H), of 3.73 (m, 2H), 2,31 (, 3H), of 2.20 (s, 3H), 1,24 (m, 1H), 0.69 (m, 2H), 0,24 (m, 2H).

Example 2(246)

Hydrochloride, 8-(N-cyclopropylmethyl)-N-(4-triptoreline)-methylamino)-2-methyl-3-(2-chloro-5-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,48 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,62 (userd, J=7.8 Hz, 2H), of 7.48 (userd, J=7.8 Hz, 2H), 7,34 (userd, J=8,1 Hz, 1H), was 7.08 (d, J=2.4 Hz, 1H), 6.90 to-to 6.88 (m, 1H), 5,19 (users, 2H), 3,85 (s, 3H), of 3.54 (m, 2H), 3,36-3,14 (m, 2H), 3,14 are 2.98 (m, 2H,), a 2.36 (s, 3H), 2,22 (m, 2H), 1,12-0,98 (m, 1H), 0,64-0,52 (m, 2H), of 0.18 to 0.08 (m, 2H).

Example 2(247)

Hydrochloride, 8-(N-cyclopropylmethyl)-N-(4-triptoreline)-methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,42 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,65 (userd, J=7.5 Hz, 2H), 7,49 (userd, J=7.5 Hz, 2H), 7,33 (d, J=8,4 Hz, 1H), was 7.08 (d, J=2.4 Hz, 1H), 6,95 (DD, J=8,4, 2.4 Hz, 1H), 5,35-by 5.18 (m, 6H), 3,85 (s, 3H), of 3.54 (d, J=6.6 Hz, 2H), a 2.36 (s, 3H), 1,11 (m, 1H, to 0.72 to 0.60 (m, 2H)and 0.22 to 0.14 (m, 2H).

Example 2(248)

Hydrochloride, 8-(N-cyclopropylmethyl)-N-(4-triptoreline)-methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,42 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.68 (d, J=7.8 Hz, 2H), 7,49 (d, J=7.8 Hz, 2H), 7,12 (d, J=8,4 Hz, 1H), make 6.90 (d, J=2.7 Hz, 1H), 6,83 (DD, J=8,4, 2.7 Hz, 1H), 5,42 (m, 2H), 5,38 (s, 2H), 5,27 (s, 2H), 3,83 (s, 3H), 3,61 (m, 2H), 2,30 (s, 3H), 2,19 (s, 3H)and 1.15 (m, 1H), 0.74 and-0,66 (m, 2H), 0,26-0,18 (m, 2H).

Example 2(249)

Hydrochloride, 8-(N-propyl-N-(4-cyanophenyl)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,29 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,66 (userd, J=7.8 Hz, 2H), 7,49 (userd, J=7.8 Hz, 2H), 7,15 (d, J=8,4 Hz, 1H), to 6.88 (d, J=2.7 Hz, 1H), for 6.81 (DD, J=8,4, 2.7 Hz, 1H), 5,15 (users, 2H), 5,09 (users, 2H), 5,01 (users, 2H), 3,83 (s, 3H), 3,37 (m, 2H), 2,33 (s, 3H), of 2.18 (s, 3H), 1,74 is 1.60 (m, 2H), of 0.91 (t, J=6.9 Hz, 3H).

Example 2(250)

Hydrochloride, 8-(N-cyclopropyl-N-(4-forfinal)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,40 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.32 (d, J=8,4 Hz, 1H), 7,16-7,07 (m, 3H), 7,02-6,94 (m, 2H), 6,92 (DD, J=8,4, 3.0 Hz, 1H), 5,20 (s, 2H), by 5.18 (s, 2H), 4,94 (s, 2H), of 3.84 (s, 3H), of 2.56 (m, 1H), 2,41 (s, 3H), 0,89-of 0.79 (m, 4H).

Example 2(251)

Hydrochloride, 8-(N-t is chlorophyl-N-(4-forfinal)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,44 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,19-was 7.08 (m, 3H),? 7.04 baby mortality-of 6.96 (m, 2H), to 6.88 (d, J=2.7 Hz, 1H), PC 6.82 (DD, J=8,4, 2.7 Hz, 1H), 5,28-by 5.18 (m, 4H), to 5.00 (s, 2H), 3,83 (s, 3H), 2,60 (m, 1H), of 2.38 (s, 3H), of 2.18 (s, 3H), 0,90-0,80 (m, 4H).

Example 2(252)

Hydrochloride, 8-(N-cyclopropylmethyl-N-(4-forfinal)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,49 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ of 7.36-7,29 (m, 2H), 7,15-7,05 (m, 3H), of 6.90 (d, J=2.7 Hz, 1H), at 6.84 (DD, J=8,1, 2.7 Hz, 1H), of 5.39 (s, 2H), 5,32-5,20 (m, 4H), of 3.84 (s, 3H), 3,62 (m, 2H), 2,32 (s, 3H), of 2.20 (s, 3H), 1,20-1,08 (m, 1H), 0,72-of 0.62 (m, 2H), and 0.28 to 0.18 (m, 2H).

Example 2(253)

Hydrochloride, 8-(N-propyl-N-(2-methoxyethyl)amino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,35 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,34 (d, J=8.7 Hz, 1H), was 7.08 (d, J=2.4 Hz, 1H), 6,97 (DD, J=8,7, 2.4 Hz, 1H), 5,48 (d, J=16,8 Hz, 1H), are 5.36 (d, J=16,8 Hz, 1H), 5,23 (s, 2H), to 4.38-4,22 (m, 2H), 3,85 (s, 3H), 3,78-3,66 (m, 4H), to 3.34 (s, 3H), of 2.35 (s, 3H), 1,81 (Sextus., J=7.5 Hz, 2H), 1,01 (t, J=7.5 Hz, 3H).

Example 2(254)

Hydrochloride, 8-(N-propyl)-N-(2-methoxyethyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,33 (hexane:ethyl acetate = 2:1)AMR (300 MHz, CDCl3): δ 7,11 (d, J=8,4 Hz, 1H), 689 (d, J=2.4 Hz, 1H), 6,83 (DD, J=8,4, 2.4 Hz, 1H) 5,41 (s, 2H), with 5.22 (s, 2H), 4,30 (m, 2H), 3,83 (s, 3H), 3,80-of 3.60 (m, 4H), to 3.34 (s, 3H), of 2.30 (s, 3H), 2,19 (s, 3H), 1,81 (Sextus., J=7.5 Hz, 2H), 1,01 (t, J=7.5 Hz, 3H).

Example 2(255)

Hydrochloride 8-(3-pentylamine)-2-methyl-3-(2-methyl-4-cyanophenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,45 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ the 7.65 (s, 1H), EUR 7.57 (d, J=7.8 Hz, 1H), 7,34 (d, J=7.8 Hz, 1H), 7.24 to was 7.08 (m, 1H), 4,06-3,88 (m, 1H), 3,41 (ushort, J=7.2 Hz, 2H), 3.15 in (t, J=7.2 Hz, 2H), 2.40 a-2,20 (m) and 2,30 (C) total 8H, 1,90-of 1.40 (m, 4H), was 1.06 (t, J=6.6 Hz, 6H).

Example 2(256)

Hydrochloride, 8-(N-propyl-N-(2-methoxyethyl)amino)-2-methyl-3-(2-chloro-5-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,46 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,34 (userd, J=8,4 Hz, 1H), was 7.08 (d, J=2.4 Hz, 1H), 6,99-6,91 (m, 1H), 4,20 (m, 2H), 3,85 (s, 3H), of 3.75 (m, 2H), 3,62 (m, 2H), 3,52-3,30 (m, 2H), 3,30 (s, 3H), 3,03 (m, 2H), 2,33 (s, 3H), 2,24 (m, 2H), 1,72 (m, 2H), of 0.96 (t, J=7.5 Hz, 3H).

Example 2(257)

Hydrochloride, 8-(N-ethyl-N-(4-methylthiophenyl)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,42 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,40-7,30 (m, 1H), 7,30-7,16 (m, 4H), was 7.08 (d, J=2.4 Hz, 1H), 6,99-6,92 (m, 1H), 5,11 (users, 2H), 3,85 (s, 3H), of 3.78 (m, 2H), 3,42 (m, 2H), 3,00 (m, 2H), 2,50 (s, 3H), of 2.35 (s, 3H), of 2.21 (m, 2H), of 1.34 (m, 3H).

The use of the 2(258)

Hydrochloride, 8-(N-ethyl-N-(4-methylthiophenyl)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,35 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.35 (d, J=8.7 Hz, 1H), 7,28 (userd, J=8,1 Hz, 2H), 7,21 (userd, J=8,1 Hz, 2H), to 7.09 (d, J=2.7 Hz, 1H), 6,97 (DD, J=8,7, 2.7 Hz, 1H), 5,48 at 5.27 (m, 2H), 5,27-of 5.06 (m, 4H), 3,85 (s, 3H), 3,88-of 3.78 (m, 2H,), of 2.50 (s, 3H), of 2.36 (s, 3H), of 1.42 (t, J=6.9 Hz, 3H).

Example 2(259)

Hydrochloride, 8-(N-ethyl-N-(4-methylthiophenyl)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,40 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,28 (userd, J=8,4 Hz, 2H), 7,22 (userd, J=8,4 Hz, 2H), 7,13 (d, J=8,4 Hz, 1H), make 6.90 (d, J=2.7 Hz, 1H), at 6.84 (DD, J=8,4, 2.7 Hz, 1H), 5.40 to (users, 2H), 5,22-5,08 (m, 4H), 3,86 (m, 2H), of 3.84 (s, 3H), 2,50 (s, 3H), 2,31 (c, 3H), of 2.20 (s, 3H), USD 1.43 (t, J=6.6 Hz, 3H).

Example 2(260)

Hydrochloride 8-(3-pentylamine)-2-methyl-3-(4-methylthiophenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,46 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,52 (d, J=8,4 Hz, 2H), 7,39 (d, J=8,4 Hz, 2H), 7,31 (d, J=10.5 Hz, 1H), 4,06-3,90 (m, 1H), 3,60 (t, J=7.8 Hz, 2H), 3,13 (t, J=7.8 Hz, 2H), 2,52 (s, 3H), 2.49 USD (s, 3H), 2,30 (Quint., J=7.8 Hz, 2H), 1,94-of 1.64 (m, 4H), of 1.05 (t, J=7.2 Hz, 6H).

Example 2(261)

Hydrochloride, 8-(N-butyl-N-(2-methoxyethyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,61 (hexane:ethyl acetate = 1:2).

NMR (300 MHz, CDCl3): δ 7,11 (d, J=8,4 Hz, 1H), 6.89 in (d, J=2.4 Hz, 1H), PC 6.82 (DD, J=8,4, 2.4 Hz, 1H), of 5.40 (s, 2H), with 5.22 (s, 2H), 4,29 (m, 2H), 3,83 (s, 3H), of 3.78 (m, 2H), and 3.72 (t, J=5,1 Hz, 2H), 3,34 (s, 3H), 2,30 (s, 3H), 2,19 (s, 3H), 1.77 in (Quint., J=7.5 Hz, 2H), 1,42 (Sextus., J=7.5 Hz, 2H), and 1.00 (t, J=7.5 Hz, 3H).

Example 2(262)

Hydrochloride 8-(3-pentylamine)-2-methyl-3-(4-dimethylaminophenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,57 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,72 (d, J=7.8 Hz, 2H), 7,60-7,40 (m, 2H), 6,88 to 6.75 (m, 1H), 3,98-of 3.85 (m, 1H), 3,35-of 3.25 (m, 2H), 3,15-3,05 (m) and of 3.13 (C) total 8H, 2,52 (s, 3H), 2,25 (Quint., J=7.8 Hz, 2H), 1.85 to to 1.60 (m, 4H), of 1.03 (t, J=7.5 Hz, 6H)Primer 2(263)

Hydrochloride, 8-(N-cyclopropylmethyl-N-propylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,55 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.15 (d, J=8,4 Hz, 1H), to 6.88 (d, J=2.4 Hz, 1H), for 6.81 (DD, J=8,4, 2.4 Hz, 1H), 5,24 (s, 2H), 5,04 (s, 2H), 3,83 (s, 3H), 3,69-3,63 (m, 4H), of 2.33 (s, 3H), of 2.18 (s, 3H), 1.70 to (Sextus., J=7.5 Hz, 2H), 1,07 (m, 1H), of 0.96 (t, J=7.5 Hz, 3H), of 0.56 (m, 2H), 0,20 (m, 2H).

Example 2(264)

8-(N-Propyl-N-(5-methylfuran-2-yl)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,47 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,31 (d, J=8,4 Hz, 1H), was 7.08 (d, J=2.7 Hz, 1H), 6.90 to (DD, J=2.7, and an 8.4 Hz, 1H), 6,02 (d, J=3.0 Hz, 1H), 5,86 (m, 1H), to 5.08 (s, 2H), 4,91 (s, 2H), 4,90 (s, 2H), of 3.84 (s, 3H), 3,26 (m, 2H), 2, 41 (s, 3H), of 2.23 (s, 3H), of 1.66 (m, 2H), were 0.94 (t, J=7.2 Hz, 3H).

Example 2(265)

8-(N-Propyl-N-(5-methylfuran-2-yl)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,49 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.18 (d, J=8,1 Hz, 1H), to 6.88 (d, J=2.4 Hz, 1H), for 6.81 (d, J=2,4, 8,1 Hz, 1H), 6,01 (d, J=3.0 Hz, 1H), 5,86 (m, 1H), 5,07 (s, 2H), 4,91 (s, 2H), 4,88 (s, 2H), 3,83 (s, 3H), of 3.25 (m, 2H), 2,37 (s, 3H), 2,22 (s, 3H), of 2.18 (s, 3H), 1,67 (m, 2H), were 0.94 (t, J=7.5 Hz, 3H).

Example 2(266)

Hydrochloride, 8-(N-cyclopropylmethyl-N-(2-methoxyethyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,29 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,16 (d, J=8,1 Hz, 1H), 6,86 (d, J=2.4 Hz, 1H), 6,80 (DD, J=8,1, 2.4 Hz, 1H), 5.25 in (s, 2H), 4,90 (s, 2H), of 4.05 (t, J=5.4 Hz, 2H), 3,83 (s, 3H), of 3.56 (t, J=5.4 Hz, 2H), 3,48 (d, J=6,9 Hz, 2H), 3,29 (s, 3H), of 2.34 (s, 3H), 2,17 (s, 3H), 1.04 million (m, 1H), 0,56 (m, 2H), 0,22 (m, 2H).

Example 2(267)

Hydrochloride, 8-(N-propyl-N-(4-triptoreline)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro-[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rfor = 0.51 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ of 7.36 (userd, J=8,1 Hz, 2H), 7,18 (userd, J=8,1 Hz, 2H), 7,17 (d, J=8,4 Hz, 1H), to 6.88 (d, J2,4 Hz, 1H), for 6.81 (DD, J=8,4, 2.4 Hz, 1H), 5,13 (users, 2H), equal to 4.97 (users, 2H), 4.92 in (users, 2H), 3,83 (s, 3H), 3,34 (m, 2H), a 2.36 (s, 3H), of 2.18 (s, 3H), of 1.64 (m, 2H), of 0.90 (t, J=7.2 Hz, 3H).

Example 2(268)

Hydrochloride, 8-(N-propyl-N-(4-forfinal)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,53 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,32-7,22 (m, 2H), 7,17 (userd, J=8.7 Hz, 1H), 7,02 (m, 2H), to 6.88 (d, J=2.4 Hz, 1H), 6,82 (userd, J=8.7 Hz, 1H), 5,11 (users, 2H), 4.95 points (users, 4H), 3,83 (s, 3H), 3,34 (m, 2H), a 2.36 (s, 3H), 2,19 (s, 3H), of 1.65 (m, 2H), of 0.90 (t, J=6.9 Hz, 3H).

Example 2(269)

Hydrochloride 8-(3-pentylamine)-2-methyl-3-(2-chloro-4-methylthiophenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,64 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,40-7,34 (m, 2H), 7,33-7,24 (m, 2H), 3,99 (m, 1H), 3,66-to 3.35 (m, 2H), 3,13 (t, J=7.5 Hz, 2H), 2,52 (s, 3H), of 2.35 (s, 3H), 2,30 (m, 2H), 1,94-of 1.64 (m, 4H), of 1.10 to 1.00 (m,6H).

Example 2(270)

Hydrochloride, 8-(N-cyclopropylmethyl-N-(2-butynyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,52 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,14 (d, J=8,1 Hz, 1H), to 6.88 (d, J=2.7 Hz, 1H), for 6.81 (DD, J=8,1, 2.7 Hz, 1H), lower than the 5.37 (s, 2H), of 5.05 (s, 2H), 4,58 (s, 2H), 3,83 (s, 3H), 3,62 (m, 2H), 2,35 (s, 3H), 2,17 (s, 3H), of 1.84 (s, 3H), of 1.20 (m, 1H), 0,63 (m, 2H), 0,36 (m, 2H).

Example 2(271)

Hydrochloride, 8-(N-(2-Metacity the)-N-(2-butynyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,29 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,13 (d, J=8,1 Hz, 1H), 6.87 in (d, J=2.4 Hz, 1H), for 6.81 (DD, J=8,1, 2.4 Hz, 1H), of 5.39 (s, 2H), is 5.06 (s, 2H), 4,42 (s, 2H), 4,06 (m, 2H), 3,83 (s, 3H), 3,81 (m, 2H), 3,37 (s, 3H), of 2.33 (s, 3H), 2,17 (s, 3H), of 1.85 (s, 3H).

Example 2(272)

Hydrochloride, 8-(N-(2-methoxyethyl)-N-(2-butynyl)amino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,39 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,28 (d, J=8,4 Hz, 1H), 7,06 (d, J=2.4 Hz, 1H), 6.89 in (DD, J=8,4, 2.4 Hz, 1H), lower than the 5.37 (s, 2H), 4.92 in (s, 2H), 4,36 (m, 2H), 3,95 (t, J=5.4 Hz, 2H), 3,83 (s, 3H), 3,76 (t, J=5.4 Hz, 2H), 3,36 (s, 3H), is 2.37 (s, 3H)and 1.83 (s, 3H).

Example 2(273)

Hydrochloride, 8-(N-(2-methoxyethyl)-N-(2-butynyl)amino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,44 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.32 (d, J=8,4 Hz, 1H), 7,06 (d, J=2.7 Hz, 1H), 6,93 (DD, J=8,4, 2.7 Hz, 1H), 4.53-in (m, 2H), 4,18 (m, 2H), of 3.84 (s, 3H), 3,81 (t, J=4,8 Hz, 2H), on 3.36 (s, 3H), 3,30 (m, 2H), 3,20 (t, J=7.2 Hz, 2H), 2,34 (s, 3H), 2,22 (Quint., J=7.2 Hz, 2H), 1,86 (t, J=2,4 Hz, 3H).

Example 2(274)

8-(N-Propyl-N-(5-methylfuran-2-yl)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,53 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.32 (d, J=8,4 Hz, 1H), 7,06 (d, J=2.7 Hz, 1H), 6.89 in (DD, J=2.7, and an 8.4 Hz, 1H), of 5.99 (d, J=3.0 Hz, 1H), to 5.85 (DD, J=1,6, 3.0 Hz, 1H), 4,78 (s, 2H), of 3.84 (s, 3H), at 3.35 (m, 2H), 2,90 (t, J=7.5 Hz, 2H), of 2.81 (t, J=7.2 Hz, 2H 2,39 (s, 3H), 2,22 (m, 3H), 2,07 (m, 2H), 1,62 (m, 2H), of 0.91 (t, J=7.5 Hz, 3H).

Example 2(275)

Hydrochloride, 8-(N-benzyl-N-cyclopropylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,49 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,42-7,30 (m, 4H), 7,25-to 7.15 (m, 2H), to 7.09 (d, J=2.4 Hz, 1H), 7,00-6,94 (m, 1H), 5,39 (d, J=14,7 Hz, 1H), 5,27 (d, J=14,7 Hz, 1H), 3,85 (s, 3H), 3,70-of 3.32 (m, 2H), 3,12 (m, 2H), 2,96 (m, 1H), 2,37 (s, 3H), of 2.21 (m, 2H), 1,20 to 0.92 (m, 4H).

Example 2(276)

Hydrochloride, 8-(N-benzyl-N-cyclopropylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,42 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.32 (d, J=8,4 Hz, 1H), 7,30-7,26 (m, 3H), 7,15-to 7.09 (m, 2H), was 7.08 (d, J=2.4 Hz, 1H), 6,91 (DD, J=8,4, 2.4 Hz, 1H), 5,20 (s, 2H), 5,19 (s, 2H), 4,91 (s, 2H), of 3.84 (s, 3H), of 2.56 (m, 1H), 2,41 (, 3H), 0,92-0,78 (m, 4H).

Example 2(277)

Hydrochloride, 8-(N-benzyl-N-cyclopropylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,40 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,33-7,19 (m, 3H), 7,19 (d, J=8,1 Hz, 1H), 7,14-was 7.08 (m, 2H), to 6.88 (d, J=2.7 Hz, 1H), PC 6.82 (DD, J=8,1, 2.7 Hz, 1H), 5,32-5,12 (m, 2H), 5,19 (s, 2H), 4,89 (s, 2H), 3,83 (s, 3H), 2.57 m (m, 1H), 2,38 (s, 3H), 2,1 (s, 3H), 0,92-0,78 (m, 4H).

Example 2(278)

Hydrochloride, 8-(N-cyclopropylmethyl-N-(2-methoxyethyl)amino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,30 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,33 (d, J=8,4 Hz, 1H), was 7.08 (d, J=2.4 Hz, 1H), 6,94 (DD, J=8,4, 2.4 Hz, 1H), and 5.30 (m) and 5,27 (C) total 4H, 4,32 (m, 2H), of 3.84 (s, 3H), 3.72 points-to 3.67 (m, 4H), and 3.31 (s, 3H), of 2.36 (s, 3H), 1,11 (m, 1H), of 0.71 (m, 2H), 0,36 (m, 2H).

Example 2(279)

Hydrochloride, 8-(N-cyclopropylmethyl-N-(2-methoxyethyl)amino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,33 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,34 (d, J=8,4 Hz, 1H), was 7.08 (d, J=2.4 Hz, 1H), 6,95 (DD, J=8,4, 2.4 Hz, 1H), 4,30 (m, 2H), 3,85 (s, 3H), 3,71 (d, J=6.6 Hz, 2H), to 3.64 (t, J=5,l Hz, 2H), 3,41 (m, 2H), 3,29 (s, 3H), 3,07 (t, J=7.2 Hz, 2H), 2,34 (s, 3H), 2,24 (Quint., J=7.2 Hz, 2H), 1,09 (m, 1H), 0,65 (m, 2H), 0.31 in (m, 2H).

Example 2(280)

8-(3-Pentylamine)-2-methyl-3-(2-chloro-4-bromophenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,61 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ the 7.65 (d, J=2.1 Hz, 1H), 7,44 (DD, J=2,1, 8,1 Hz, 1H), 7,28 (d, J=8,1 Hz, 1H), 6,23 (userd, J=10.5 Hz, 1H), 3,81 (m, 1H), 3,09 (t, J=7.2 Hz, 2H), 2,90 (t, J=7.8 Hz, 2H), 2,34 (s, 3H), of 2.15 (m, 2H), 1,60-to 1.82 (m, 4H), 1,01 (t, J=7.5 Hz, 6H).

Example 2(281)

8-(3-Pentylamine)-2-methyl-3-(2,5-dichloro-4-methoxyphenyl)-6,7-dihydro-5H-is clopant[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,65 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,40 (s, 1H), 7,06 (s, 1H), 6.22 per (userd, J=10.5 Hz, 1H), 3,92 (s, 3H), 3,81 (m, 1H), is 3.08 (t, J=6.9 Hz, 2H), only 2.91 (t, J=7.8 Hz, 1H), 2,33 (s, 3H), of 2.15 (m, 2H), 1,58-to 1.82 (m, 4H), 1,01 (t, J=7,5 Hz, 6H).

Example 2(282)

8-(3-Pentylamine)-2-methyl-3-(2,5-dichloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,61 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,39 (s, 1H), 7,07 (s, 1H), 6,34 (userd, J=10.5 Hz, 1H), from 5.29 (m, 2H), is 4.93 (m, 2H), 3,93 (s, 3H), 3,24 (m, 1H), a 2.36 (s, 3H), 1,67-of 1.84 (m, 4H), of 1.02 (t, J=7.2 Hz, 6H).

Example 2(283)

Hydrochloride, 8-(N-cyclopropyl-N-(4-cyanophenyl)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,26 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.61 (d, J=7.8 Hz, 2H), 7,33 (d, J=7.8 Hz, 2H), 7,30 (d, J=8.7 Hz, 1H), was 7.08 (d, J=2.7 Hz, 1H), 6,91 (DD, J=8,7, 2.7 Hz, 1H), 5,27 (s, 2H, in), 5.25 (s, 2H), is 4.93 (s, 2H), of 3.84 (s, 3H), 2,58 (m, 1H), 2.40 a (s, 3H), 0,84 (m, 4H).

Example 2(284)

Hydrochloride, 8-(N-cyclopropyl-N-(4-cyanophenyl)methylamino-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,24 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.61 (d, J=7.8 Hz, 2H), 7,33 (d, J=7.8 Hz, 2H), 7,17 (d, J=8,1 Hz, 1H), to 6.88 (d, J=2.7 Hz, 1H), PC 6.82 (DD, J=8,1, 2.7 Hz, 1H), 5.40 to-5,20 (m, 2H, in), 5.25 (s, 2H, 4,91 (s, 2H), 3,83 (s, 3H), 2,58 (m, 1H), a 2.36 (s, 3H), 2,17 (s, 3H), 0,84 (m, 4H).

Example 2(285)

Hydrochloride 8 dibutylamino-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,66 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.35 (d, J=8,4 Hz, 1H), 7,07 (d, J=2.1 Hz, 1H), 6,94 (DD, J=8,4, and 2.1 Hz, 1H), 3,84 (s and m, total 7H), to 3.35 (m, 2H), 3,01 (t, J=7.5 Hz, 2H), 2,33 (s, 3H), 2,22 (Quint., J=7.5 Hz, 2H), rate of 1.67 (Quint., J=7.5 Hz, 4H), 1,36 (Sextus., J=7.5 Hz, 2H), of 0.95 (t, J=7.5 Hz, 6H).

Example 2(286)

Hydrochloride 8 dibutylamino-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,63 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,11 (d, J=8,4 Hz, 1H), 6.89 in (d, J=2.4 Hz, 1H), 6,83 (DD, J=8,4, 2.4 Hz, 1H), 5,43 (s, 2H), total of 5.21 (s, 2H), 3,88 (m, 4H), 3,83 (s, 3H), to 2.29 (s, 3H), of 2.20 (s, 3H), of 1.78 (Quint., J=7.5 Hz, 4H), 1,42 (Sextus., J=7.5 Hz, 4H), and 1.00 (t, J=7.5 Hz, 6H).

Example 2(287)

Hydrochloride, 8-bis(methoxyethyl)amino-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,26 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.35 (d, J=9.0 Hz, 1H), was 7.08 (d, J=2.7 Hz, 1H), of 6.96 (DD, J=9,0, 2.7 Hz, 1H), 4,15 (m, 4H), 3,85 (s, 3H), of 3.64 (t, J=5.4 Hz, 4H), 3,53 (m, 1H), of 3.45 (m, 1H), and 3.31 (s, 6H), was 3.05 (t, J=7.2 Hz, 2H), 2,34 (s, 3H), 2,22 (Quint., J=7.2 Hz, 2H).

Example 2(288)

Hydrochloride, 8-(N-ethyl-N-cyclopropylamino)-2-methyl--(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,49 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,31 (d, J=7.8 Hz, 1H), 7,07 (d, J=2.1 Hz, 1H), 6,92 (m, 1H), 5,28 (s, 2H), 5,11 (s, 2H), of 3.84 (s, 3H), 3,81 (m, 2H), 3,69 (m, 2H), is 2.37 (s, 3H), of 1.33 (s, 3H), of 1.09 (m, 1H), 0,60 (m, 2H), 0,24 (m, 2H).

Example 2(289)

Hydrochloride, 8-(N-ethyl-N-cyclopropylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,50 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ for 7.12 (m, 1H), 6.89 in (s, 1H), PC 6.82 (m, 1H), 5,38 (m, 2H), 5,31 (m, 2H), 3,99 (m, 2H), 3,83 (s and m, total 5H), 2,31(s, 3H), of 2.20 (s, 3H), of 1.44 (m, 3H), 1,19 (m, 1H), 0,72 (m, 2H), 0,36 (m, 2H).

Example 2(290)

Hydrochloride, 8-(N-ethyl-N-cyclopropylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rfor = 0.51 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,31 (d, J=8,4 Hz, 1H), 7,06 (d, J=2.4 Hz, 1H), 6.89 in (DD, J=8,4, 2.4 Hz, 1H), 3,84 (s, 3H), of 3.77 (sq, J=7.2 Hz, 2H)and 3.59 (d, J=6.6 Hz, 2H), 3.04 from (t, J=7.5 Hz, 4H), of 2.36 (s, 3H), 2,16 (Quint., J=7.5 Hz, 2H), 1,23 (t, J=7.2 Hz, 3H), of 1.03 (m, 1H), and 0.50 (m, 2H), and 0.15 (m, 2H).

Example 2(291)

Hydrochloride, 8-(N-cyclopropyl-N-(4-cyanophenyl)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,29 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, DMSO-d6): δ 7,83-7,76 (m, 2H), 7,54-of 7.48 (who, 2H), 7,30 (DD, J=8,7, 1.2 Hz, 1H), 7,16 (m, 1H), 7,02-of 6.96 (m, 1H), 5,12 (m, 2H), 3,82 (s, 3H), 3,06 (m, 2H), 2,94-2,78 (m, 3H), of 2.25 (s, 3H), of 2.05 (m, 2H), 0,79 to 0.70 (m, 2H), and 0.61 (m, 2H).

Example 2(292)

Hydrochloride, 8-(N-cyclopropylmethyl-N-(4-cyanophenyl)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,37 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,69 (userd, J=7.2 Hz, 2H), 7,49 (userd, J=7.2 Hz, 2H), 7,34 (userd, J=8,4 Hz, 1H), to 7.09 (d, J=2,l Hz, 1H), of 6.96 (m, 1H), 5,33 (m, 2H), 3,85 (s, 3H), of 3.60 (m, 2H), 3,48 (m, 2H), 3,10 (m, 2H), 2,33 (s, 3H), 2,28 (m, 2H), 1,18-1,02 (m, 1H), 0.70 to EUR 0.58 (m, 2H), 0,22 one-0.10 (m, 2H).

Example 2(293)

Hydrochloride, 8-(N-cyclopropylmethyl-N-(4-cyanophenyl)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,21 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.68 (d, J=8.1 Hz, 2H), 7,52 (d, J=8.1 Hz, 2H), 7,31 (d, J=8.7 Hz, 1H), was 7.08 (d, J=2.4 Hz, 1H), 6,94 (DD, J=8,7, 2.4 Hz, 1H), 5,26 (m, 4H), 5,14 (s, 2H), of 3.84 (s, 3H), of 3.45 (d, J=6.6 Hz, 2H), a 2.36 (s, 3H), of 1.05 (m, 1H), 0,68-of 0.56 (m, 2H), only 0.18 to 0.10(m, 2H).

Example 2(294)

Hydrochloride, 8-(N-cyclopropylmethyl-N-(4-cyanophenyl)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,37 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,66 (d, J=7.8 Hz, 2H), 7,52 (d, J=7.8 Hz, 2H), 7,15 (d, J=8,l Hz, 1H), to 6.88 (d, J=2.4 Hz, 1H), PC 6.82 (DD, J=8,1,2,4 Hz, 1H), a 5.25 (s, 2H), 5,13 (s, 2H), 5,00 (s, 2H), 3,83 (s, 3H), 3,41 (d, J=6.6 Hz, 2H), 2,34 (s, 3H), of 2.18 (s, 3H), of 1.02 (m, 1H), 0.60 and 0.52 in (m, 2H), 0.12 to 0.06 to (m, 2H).

Example 2(295)

8-(N-Propyl-N-(thiophene-3-yl)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,48 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,31 (d, J=8.7 Hz, 1H), 7,28 (m, 1H), 7,13 (m, 1H), was 7.08 (d, J=2.4 Hz, 1H), 6,98 (DD, J=0,9, 4.8 Hz, 1H), 6.90 to (DD, J=2,4, and 8.7 Hz, 1H), to 5.08 (s, 2H), 4,96 (s, 2H), 4,89 (s, 2H), of 3.84 (s, 3H), of 3.32 (m, 2H), 2,41 (s, 3H), of 1.64 (m, 2H), of 0.90 (t, J=7.5 Hz, 3H).

Example 2(296)

8-(N-Propyl-N-(5-methylthiophene-2-yl)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,50 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,31 (d, J=8.7 Hz, 1H), 7,07 (d, J=2.4 Hz, 1H), 6.90 to (DD, J=2,4, and 8.7 Hz, 1H), 6,66 (d, J=3.3 Hz, 1H), 6,56 (m, 1H), 5,02-5,17 (m, 4H), of 4.90 (s, 2H), of 3.84 (s, 3H), of 3.27 (m, 2H), 2,44 (s, 3H), to 2.42 (s, 3H), of 1.64 (m, 2H), to 0.92 (t, J=7.5 Hz, 3H).

Example 2(297)

Hydrochloride, 8-(N-butyl-N-cyclopropylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,61 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,31 (d, J=8.7 Hz, 1H), 7,06 (d, J=2.1 Hz, 1H), 6.89 in (DD, J=8,7, and 2.1 Hz, 1H), 3,83 (s, 3H), of 3.69 (t, J=7.2 Hz, 2H), of 3.56 (d, J=7.2 Hz, 2H), to 3.02 (m, 4H), of 2.36 (s, 3H), of 2.15 (Quint., J=7.2 Hz, 2H), 1,58 (Quint., J=7.5 Hz, 2H), 1,34 (Sextus., J=7.5 Hz, 2H), 1,02 (m, 1H), of 0.91(t, J=7.5 Hz, 3H), of 0.48 (m, 2H), 0,13 (m, 2H).

Example 2(298)

Hydrochloride, 8-(N-butyl-N-cyclopropylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,40 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.32 (d, J=8,4 Hz, 1H), 7,07 (d, J=2.1 Hz, 1H), 6,93 (DD, J=8,4, and 2.1 Hz, 1H), 5.25 in (s, 2H), 5,17 (s, 2H), of 3.84 (s, 3H), of 3.77 (m, 2H), 3,71 (m, 2H), is 2.37 (s, 3H), of 1.70 (Quint., J=7.2 Hz, 2H), 1.39 in (Sextus., J=7.2 Hz, 2H), 1,10 (m, 1H), of 0.96 (t, J=7.2 Hz, 3H), and 0.62 (m, 2H), and 0.25 (m, 2H).

Example 2(299)

Hydrochloride, 8-(N-butyl-N-cyclopropylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,45 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.15 (d, J=8.7 Hz, 1H), to 6.88 (d, J=2.1 Hz, 1H), for 6.81 (DD, J=8,7, 2,l Hz, 1H), 5.25 in (s, 2H), 5,13 (s, 2H), 3,83 (s, 3H), of 3.75 (m, 2H), 3,70 (m, 2H), 2,33 (s, 3H), of 2.18 (s, 3H), 1.69 in (m, 2H,), 1,39 (Sextus., J=7.5 Hz, 2H), 1,09 (m, 1H), of 0.96 (t, J=7.5 Hz, 3H), of 0.60 (m, 2H), 0,23 (m, 2H).

Example 2(300)

8-(N-Propyl-N-(thiophene-3-yl)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,48 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,28 (DD, J=2.7, and 5,l Hz, 1H), 7,18 (d, J=8.7 Hz, 1H), 7,13 (m, 1H), 6,97 (DD, J=1,5, 5,1 Hz, 1H), to 6.88 (d, J=3.0 Hz, 1H), for 6.81 (DD, J=3,0, to 8.7 Hz, 1H), 5,07 (s, 2H), 4,96 (s, 2H), 4,87 (c, 2H), 3,83 (s, 3H), and 3.31 (m, 2H), is 2.37 (s, 3H), 2,19 (s, 3H), of 1.64 (m, 2H), of 0.91 (t, J=7.2 Hz, 3H).

Example 2(301)

TLC: Rf= 0,47 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.18 (d, J=8,4 Hz, 1H), to 6.88 (d, J=3.0 Hz, 1H), for 6.81 (DD, J=3.0 a, and 8.4 Hz, 1H), 6,65 (d, J=3.3 Hz, 1H), 6,55 (m, 1H), 5,11 (s, 4H), 4,88 (s, 2H), 3,83 (s, 3H), of 3.27 (m, 2H), 2,43 (s, 3H), 2,38 (s, 3H), 2,19 (s, 3H), of 1.65 (m, 2H), to 0.92 (t, J=7.5 Hz, 3H).

Example 2(302)

Hydrochloride 8-(3-pentylamine)-2-methyl-3-(2-chloro-4-ethoxycarbonylphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,56 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 8,21 (d, J=1.5 Hz, 1H), 8,08 (DD, J=1.5 and 7.8 Hz, 1H), 7,56 (d, J=7.8 Hz, 1H), 7,30 (userd, J=10,8 Hz, 1H), to 4.38 (sq, J=6,9 Hz, 2H), 4.00 points (m, 1H), 3,34-to 3.64 (m, 2H), 3.15 in (t, J=6.9 Hz, 2H), 2,35 (s, 3H), 2,31 (m, 2H), 1,65 is 1.96 (m, 4H), of 1.41 (t, J=6.9 Hz, 3H), of 1.07 (t, J=7.5 Hz, 3H), of 1.06 (t, J=7.5 Hz, 3H).

Example 2(303)

Hydrochloride, 8-(N-propyl-N-(2-forfinal)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,52 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,35 (m, 2H), 7,10-6,92 (m, 5H), 5,16 (m, 2H), 3,85 (s, 3H), 3,70 (m, 2H), 3,60-to 3.34 (m, 2H), 3,03 (m, 2H), 2,35 (s, 3H), and 2.26 (m, 2H), of 1.75 (m, 2H), were 0.94 (m, 3H).

Example 2(304)

Hydrochloride, 8-(N-propyl-N-(2-forfinal)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,45 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ of 7.48-,33 (m, 2H), 7,13? 7.04 baby mortality (m, 4H), 6,97 (DD, J=8,4, 2.4 Hz, 1H), 5,50-of 5.15 (m, 4H), to 5.17 (s, 2H), 3,85 (s, 3H), 3,74-of 3.60 (m, 2H), is 2.37 (s, 3H), 1,82 (Sextus., J=7.2 Hz, 2H), 0,97 (t, J=7.2 Hz, 3H).

Example 2(305)

Hydrochloride, 8-(N-propyl-N-(2-forfinal)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,55 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ of 7.36-7,26 (m, 1H), 7,16 (d, J=8.7 Hz, 1H), 7,09-of 6.96 (m, 3H), to 6.88 (d, J=2.7 Hz, 1H), PC 6.82 (DD, J=8,7, 2.7 Hz, 1H), 5,13 (s, 2H), to 5.03 (s, 2H), 5,02 (s, 2H), 3,83 (s, 3H), 3,41 (m, 2H), 2,35 (, 3H), 2,19 (s, 3H), 1.69 in (Sextus., J=7.2 Hz, 2H), to 0.92 (t, J=7.2 Hz, 3H).

Example 2(306)

8-(N-Propyl-N-(5-methylthiophene-2-yl)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,57 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.32 (d, J=8,4 Hz, 1H), 7,06 (d, J=2.7 Hz, 1H), 6.89 in (DD, J=2.7, and an 8.4 Hz, 1H), only 6.64 (d, J=3.3 Hz, 1H), 6,54 (m, 1H), 4,96 (s, 2H), of 3.84 (s, 3H), 3,38 (m, 2H), 2,90 (t, J=7.5 Hz, 2H), 2,86 (t, J=7.2 Hz, 2H), 2,43 (s, 3H), 2.40 a (s, 3H), of 2.08 (m, 2H), 1.61 of (m, 2H), of 0.90 (t, J=7.5 Hz, 3H).

Example 2(307)

8-(N-Propyl-N-(thiophene-3-yl)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,53 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.32 (d, J=8.7 Hz, 1H), 7,25 (m, 1H), 7,11 (m, 1H), 7,07 (d, J=2.7 Hz, 1H), 6,95 (DD, J=1,5, 5,l Hz, 1H), 6.89 in (DD, J=2.7, and 8.7 Hz, 1H), around 4.85 (s, 2H), of 3.84 (s, 3H), 3,39 (m, 2H), 2,90 (t,J=7.5 Hz, 2H), of 2.81 (t, J=7.2 Hz, 2H), 2,39 (s, 3H), 2,07 (m, 2H), 1,60 (m, 2H), 0,89 (t, J=7.2 Hz, 3H).

Example 2(308)

8-(N-Ethyl-N-propylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,58 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,30 (d, J=8,4 Hz, 1H), 7,06 (d, J=2.7 Hz, 1H), to 6.88 (DD, J=8,4, 2.7 Hz, 1H), 3,83 (s, 3H), 3,66 (sq, J=6,9 Hz, 2H), 3,60-to 3.50 (m, 2H), 3,02-2,84 (m, 4H), is 2.37 (s, 3H), 2,20-2,04 (m, 2H), 1,64-1,52 (m, 2H), 1,17 (t, J=6.9 Hz, 3H), of 0.90 (t, J=6.9 Hz, 3H).

Example 2(309)

8-(N-Ethyl-N-propylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,55 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,16 (d, J=8.7 Hz, 1H), 6.87 in (d, J=2.7 Hz, 1H), 6,80 (DD, J=8,7, 2.7 Hz, 1H), 5,20 (s, 2H), 4,89 (s, 2H), 3,82 (s, 3H), 3,67 (sq, J=7.2 Hz, 2H), 3,60-of 3.48 (m, 2H), 2,34 (s, 3H), of 2.18 (s, 3H), 1,72-of 1.56 (m, 2H), 1,23 (t, J=7.2 Hz, 3H), of 0.93 (t, J=7.2 Hz, 3H).

Example 2(310)

8-(N-Ethyl-N-propylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rfor = 0.51 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,29 (d, J=8.7 Hz, 1H), 7,06 (d, J=2.7 Hz, 1H), 6.89 in (DD, J=8,7, 2.7 Hz, 1H), 5,19 (s, 2H), 4,90 (s, 2H), 3,83 (s, 3H), 3,67 (sq, J=7.2 Hz, 2H), 3,60-of 3.48 (m, 2H), of 2.38 (s, 3H), 1.70 to 1,50 (m, 2H,), 1,24 (t, J=7.2 Hz, 3H), of 0.93 (t, J=7.2 Hz, 3H).

Example 2(311)

8-(3-Pentylamine)-2-methyl-3-(2-chloro-4-carbamoylmethyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]feast Medin

TLC: Rf= 0,53 (methylene chloride:ethyl acetate = 10:1).

NMR (300 MHz, CDCl3): δ of 7.96 (d, J=1.8 Hz, 1H), of 7.70 (DD, J=8,1, 1.8 Hz, 1H), 7,50 (d, J=8,1 Hz, 1H), of 6.26 (d, J=10.5 Hz, 1H), 3,82 (m, 1H), 3,14 was 3.05 (m, 2H), only 2.91 (t, J=7.8 Hz, 2H), a 2.36 (s, 3H), 2,22 is 2.10 (m, 2H), 1,85 of 1.50 (m, 4H), of 1.02 (t, J=7.5 Hz, 6H).

Example 2(312)

8-(3-Pentylamine)-2-methyl-3-(2-chloro-4-(N-methylcarbamoyl)-phenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,55 (methylene chloride:ethyl acetate = 10:1).

NMR (300 MHz, CDCl3): δ 7,89 (d, J=1.8 Hz, 1H), to 7.64 (DD, J=7,8, 1.8 Hz, 1H), 7,45 (d, J=7.8 Hz, 1H), 6.42 per (users, 1H), of 6.26 (d, J=10,2 Hz, 1H), 3,82 (m, 1H), 3,14 was 3.05 (m, 2H), 3,01 (d, J=4.5 Hz, 3H), only 2.91 (t, J=7.8 Hz, 2H), 2,35 (s, 3H), 2,22-of 2.09 (m, 2H), 1,82-of 1.55 (m, 4H), of 1.02(t, J=7.5 Hz, 6H).

Example 2(313)

8-(3-Pentylamine)-2-methyl-3-(2-chloro-4-(N,N-dimethylcarbamoyl)phenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,65 (methylene chloride:ethyl acetate = 10:1).

NMR (300 MHz, CDCl3): δ 7,56 (d, J=1.5 Hz, 1H), 7,46 (d, J=7.8 Hz, 1H), was 7.36 (DD, J=7,8, 1.5 Hz, 1H), of 6.26 (d, J=9.9 Hz, 1H), 3,82 (m, 1H), 3,17-to 3.02 (m, 8H), of 2.92 (t, J=7.8 Hz, 2H), 2,34 (s, 3H), 2.21 are to 2.06 (m, 2H), 1,85-of 1.42 (m, 4H), of 1.02 (t, J=7.5 Hz, 6H).

Example 2(314)

8-(3-Pentylamine)-2-methyl-3-(2,6-dimethyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,29 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 6,69 (s, 2H), 6,32 (d, J=10.8 G is, 1H), from 5.29 (s, 2H), 4,88 (s, 2H), 3,80 (s, 3H), 3,30-3,18 (m, 1H), 2,22 (s, 3H), 2,04 (s, 6H), 1,83-of 1.55 (m, 4H), of 1.03 (t, J=7.2 Hz, 6H).

Example 2(315)

8-(N-Ethyl-N-(4-forfinal)methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,49 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,30-7,22 (m, 2H), 7,18 (d, J=8,1 Hz, 1H), 7,06-6,94 (m, 2H), to 6.88 (d, J=2.7 Hz, 1H), for 6.81 (DD, J=8,1, 2.7 Hz, 1H), 5,09 (s, 2H), 4,96-4,80 (m, 4H), 3,83 (s, 3H), 3,41 (sq, J=7.2 Hz, 2H), 2,37 (, 3H), of 2.18 (s, 3H), of 1.23 (t, J=7.2 Hz, 3H).

Example 2(316)

8-(N-Ethyl-N-(4-forfinal)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,42 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.32 (d, J=8,4 Hz, 1H), 7,26-7,22 (m, 2H), 7,07 (d, J=2.4 Hz, 1H),? 7.04 baby mortality-6,94 (m, 2H), 6.90 to (DD, J=8,4, 2.4 Hz, 1H), to 4.81 (s, 2H), of 3.84 (s, 3H), 3,47 (sq, J=7.2 Hz, 2H), 2,90 (t, J=7.2 Hz, 2H), 2,82 (t, J=7.2 Hz, 2H), 2.40 a (s, 3H), 2,16-to 1.98 (m, 2H), of 1.18 (t, J=7.2 Hz, 3H).

Example 2(317)

8-(N-Ethyl-N-(4-forfinal)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,46 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,31 (d, J=8,1 Hz, 1H), 7,30-7,24 (m, 2H), was 7.08 (d, J=2.7 Hz, 1H), 7,06-6,94 (m, 2H), 6,91 (DD, J=8,1, 2.7 Hz, 1H), 5,10 (s, 2H), 4,90 (s, 2H), 4,89 (s, 2H), of 3.84 (s, 3H), 3,42 (sq, J=7.2 Hz, 2H,), is 2.40 (s, 3H), 1,22 (t, J=7.2 Hz, 3H).

Example 2(318)

8-(3-Pentylamine)-2-methyl-3-(2-chloro-4,6-DiMeo Setenil)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,26 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 6.67 (d, J=2.7 Hz, 1H), 6,45 (d, J=2.7 Hz, 1H), 6,23 (d, J=10,8 Hz, 1H), 3,82 (s, 3H), 3,80 (m, 1H), 3,70 (s, 3H), of 3.07 (m, 2H), 2,90 (m, 2H, in), 2.25 (s, 3H), 2.13 in (m, 2H), 1,52 and 1.80 (m, 4H), of 1.02 (t, J=7.2 Hz, 3H), 1,01 (t, J=7.2 Hz, 3H).

Example 2(319)

8-(3-Pentylamine)-2-methyl-3-(2-chloro-4,6-acid)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,22 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ of 6.68 (d, J=2.7 Hz, 1H), 6,47 (d, J=2.7 Hz, 1H), 6,34 (d, J=10,8 Hz, 1H), 5,28 (s, 2H), 4.92 in (d, J=13.5 Hz, 1H), 4,90 (d, J=13.5 Hz, 1H), 3,83 (s, 3H), 3,71 (s, 3H), 3,23 (m, 1H), 2,28 (s, 3H), 1,53-to 1.82 (m, 4H), of 1.02 (t, J=7.5 Hz, 3H), 1,01 (t, J=7.5 Hz, 3H).

Example 2(320)

8-(3-Pentylamine)-2-methyl-3-(2-chloro-4-AMINOPHENYL)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,22 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,16 (d, J=8,4 Hz, 1H), PC 6.82 (d, J=2,l Hz, 1H), 6,63 (DD, J=8,4, 2,l Hz, 1H), 6,21 (d, J=10,2 Hz, 1H), a 3.87-3,62 (m, 3H), 3,12-3,03 (m, 2H), 2.95 and-of 2.86 (m, 2H), 2,34 (s, 3H), 2,20-2,07 (m, 2H), 1.85 to 1,50 (m, 4H), 1,01 (t, J=7.5 Hz, 6H).

Example 2(321)

8-(4-Heptylamine)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,48 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.15 (d, J=8.7 Hz, 1H), 6,86 (d, J=2.7 Hz, 1H), 6,79 (DD, J=8,7, 2.7 Hz, 1H), 6,32 (d, J=10,8 Hz, 1H), from 5.29 (s, 2H), 4,90 (s, 2H), 3,82 (s, 3H), 3,40(m, 1H), 2,32 (s, 3H), of 2.18 (s, 3H), 1,78-to 1.38 (m, 8H), of 0.95 (t, J=7.2 Hz, 6H).

Example 2(322)

8-(3-Pentylamine)-2-methyl-3-(2-chloro-4-methylaminophenol)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,45 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ to 7.18 (d, J=8,4 Hz, 1H), 6.73 x (d, J=2.4 Hz, 1H), 6,56 (DD, J=8,4, 2.4 Hz, 1H), 6,21 (d, J=10.5 Hz, 1H), 3,88-3,70 (m, 2H), 3,12-to 3.02 (m, 2H), 2.95 and is 2.80 (m, 2H), 2,85 (s, 3H), of 2.34 (s, 3H), 2,20-2,05 (m, 2H), 1,80 of 1.50 (m, 4H), 1,01 (t, J=7.2 Hz, 6H).

Example 2(323)

8-(3-Pentylamine)-2-methyl-3-(2-formyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,26 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 9,85 (s, 1H), 7,55 (d, J=2.7 Hz, 1H), 7,38 (d, J=8,4 Hz, 1H), 7,22 (DD, J=8,4, 2.7 Hz, 1H), 6,23 (d, J=9.6 Hz, 1H), 3,93-3,74 (m) and the 3.89 (C) total 4H, to 3.09 (t, J=7.5 Hz, 2H), 2,88 (t, J=7.5 Hz, 2H), 2,39 (s, 3H), and 2.14 (Quint., J=7.5 Hz, 2H), 1,83 of 1.50 (m, 4H), of 1.02 (t, J=7.5 Hz, 6H).

Example 2(324)

8-(3-Pentylamine)-2-methyl-3-(2-cyano-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,54 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,46 (d, J=9.0 Hz, 1H), 7,24 (d, J=2.4 Hz, 1H), 7,18 (DD, J=9,0, 2.4 Hz, 1H), 6,24 (d, J=10.5 Hz, 1H), 3,88-to 3.73 (m) and 3,86 (C) total 4H, to 3.09 (t, J=7.2 Hz, 2H), 2,92 (t, J=7.2 Hz, 2H), 2,43 (s, 3H), of 2.15 (Quint., J=7.2 Hz, 2H), 1,80 of 1.50 (m, 4H), of 1.02 (t, J=7.2 Hz, 6H).

Example 2(325)

8-(3-Pentylamine)-2-methyl-3-(2-ethyl-4-methoxyphenyl)-6,7-dihydro-5H-CEC is openta[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,30 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ for 7.12 (d, J=8,4 Hz, 1H), to 6.88 (d, J=2.4 Hz, 1H), 6,77 (DD, J=8,4, 2.4 Hz, 1H), 6,21 (d, J=10.5 Hz, 1H), 3,83 of 3.75 (m) and 3,83 (C) total 4H, is 3.08 (t, J=7.2 Hz, 2H), 2,88 (t, J=7.2 Hz, 2H), 2,52 (sq, J=7,8 Hz, 2H), 2,28 (s, 3H), 2.13 and (Quint., J=7.2 Hz, 2H), 1,83 of 1.50 (m, 4H), 1,10-to 0.98 (m, 9H).

Example 2(326)

Hydrochloride 8-(4-heptylamine)-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rfor = 0.51 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ to 8.20 (s, 1H), 7,65 (d, J=8,4 Hz, 1H), 7,38 (d, J=10,2 Hz, 1H), 7,08-6,97 (m, 2H), 4,15 (m, 1H), 3,84 (s, 3H), 3,61 (m, 2H), and 3.16 (m, 2H), 2,33 (m, 2H), 1,88 is 1.60 (m, 4H), 1.60-to of 1.35 (m, 4H), 0,99 (t, J=7.5 Hz, 6H).

Example 2(327)

8-(N,N-Dipropylamino)-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,54 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 8,32 (s, 1H), 7,78 (d, J=8.7 Hz, 1H), 7,03 (d, J=2.7 Hz, 1H), 6,91 (DD, J=8,7, 2.7 Hz, 1H), 3,83 (s, 3H), of 3.57 (m, 4H), of 2.97 (m, 4H), 2,17 (m, 2H), 1,66 of 1.50 (m, 4H), to 0.88 (t, J=7.5 Hz, 6H).

Example 2(328)

8-(N,N-Dipropylamino)-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,58 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 8,35 (s, 1H), 7,72 (d, J=9.0 Hz, 1H),? 7.04 baby mortality (d, J=2.4 Hz, 1H), 6,91 (DD, J=9,0, 2.4 Hz, 1H), 5,20 (s, 2H), 4,94 (s, 2H), 3,82 (s, 3H), of 3.57 (t, J=7.5 Hz, 4H), 1,72 of 1.46 (m, 4), of 0.90 (t, J=7.2 Hz, 6H).

Example 2(329)

8-(N-Cyclopropylmethyl-N-propylamino)-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,60 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ of 8.37 (s, 1H), 7,73 (d, J=8,4 Hz, 1H), 7,05 (d, J=2.7 Hz, 1H), 6,92 (DD, J=8,4, 2.7 Hz, 1H), 5.25 in (s, 2H), 4,96 (s, 2H), 3,83 (s, 3H), 3,64-to 3.50 (m, 4H), 1,72-of 1.56 (m, 2H), 1.04 million (m, 1H), 0,93 (t, J=7.5 Hz, 3H), of 0.58 to 0.44 (m, 2H), of 0.20 to 0.08 (m, 2H).

Example 2(330)

8-(N-Benzyl-N-cyclopropylamino)-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,52 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 8,42 (s, 1H), 7,74 (d, J=8,4 Hz, 1H), 7,38-7,20 (m, 5H), 7,06 (d, J=2.7 Hz, 1H), 6,93 (DD, J=8,4, 2.7 Hz, 1H), 5.25 in (s, 2H), 4,96 (s, 2H), 4.95 points (s, 2H), of 3.84 (s, 3H), 3.43 points (d, J=6.6 Hz, 2H), the 1.04 (m, 1H), 0,58-0,46 (m, 2H), 0,16-0,04 (m, 2H).

Example 2(331)

8-(N-Cyclopropylmethyl-N-(4-were)methylamino)-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,56 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 8,42 (s, 1H), of 7.75 (d, J=8,4 Hz, 1H), 7,19 (d, J=7.8 Hz, 2H), 7,13 (d, J=7.8 Hz, 2H), 7,06 (d, J=2.4 Hz, 1H), 6,93 (DD, J=8,4, 2.4 Hz, 1H), 5,24 (s, 2H), 4.95 points (s, 2H), 4,91 (s, 2H), 3,84 (s, 3H), 3,42 (d, J=6.3 Hz, 2H), 2,33 (s, 3H), 1.04 million (m, 1H), 0,58-0,46 (m, 2H), 0,18-0,04 (m, 2H).

Example 2(332)

8-(N-Propyl-N-(2-butynyl)methylamino)-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,41 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ of 8.37 (s, 1H), 7,71 (d, J=8.7 Hz, 1H), 7,05 (d, J=2.7 Hz, 1H), 6,92 (DD, J=8,7, 2.7 Hz, 1H), of 5.34 (s, 2H), equal to 4.97 (s, 2H), of 4.44 (sq, J=2.4 Hz, 2H), 3,83 (s, 3H), 3,52 (m, 2H), equal to 1.82 (t, J=2.4 Hz, 3H), 1,80-of 1.62 (m, 2H), and 0.98 (t, J=7.2 Hz, 3H).

Example 2(333)

Hydrochloride 8-(3-pentylamine)-2-methyl-3-(2-methoxycarbonyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,26 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ of 7.70 (d, J=2.7 Hz, 1H), 7,34 (d, J=8,4 Hz, 1H), 7,30-7,16 (m) and 7,19 (DD, J=8,4, 2.7 Hz) total 2H, a 4.03-3,83 (m) and the 3.89 (C) total 4H, of 3.77 (s, 3H), 3,54-to 3.36 (m, 2H), 3,11 (t, J=7.5 Hz, 2H), 2,33-2,00 (m) and 2,25 (C) total 4H, 1,90 is 1.58 (m, 4H), of 1.05 (t, J=7.5 Hz, 6H).

Example 2(334)

8-(N-Butyl-N-cyclopropylamino)-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,45 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ of 8.37 (s, 1H), 7,74 (d, J=9.0 Hz, 1H), 7,05 (d, J=2.7 Hz, 1H), 6,91 (DD, J=9,0, 2.7 Hz, 1H), 5.25 in (s, 2H), 4,96 (s, 2H), 3,83 (s, 3H), 3,66-to 3.52 (m, 4H), 1,66 is 1.48 (m, 2H), 1,44-1,22 (m, 2H), 1.04 million (m, 1H), of 0.91 (t, J=7.2 Hz, 3H), 0.60 and of 0.44 (m, 2H)and 0.22 to 0.08 (m, 2H).

Example 2(335)

8-(3-Pentyl)-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,57 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 8,32 (s, 1H), 7,74 (d, J=8.7 Hz, 1H),? 7.04 baby mortality (d, J=2.7 Hz, 1H), 6,91 (DD, J=8,7, 2.7 Hz, 1H), 6.42 per (d, J=108 Hz, 1H), 5,31 (s, 2H), equal to 4.97 (s, 2H), 3,83 (s, 3H), of 3.28 (m, 1H), 1,84-and 1.54 (m, 4H), 1,01 (t, J=7.2 Hz, 6H).

Example 2(336)

8-(N-Cyclopropylmethyl-N-(4-forfinal)methylamino)-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,41 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 8.41 (s, 1H), 7,74 (d, J=9.0 Hz, 1H), 7,38-7,24 (m, 2H), 7,12-of 6.96 (m, 3H), 6,92 (DD, J=9,0, 2.7 Hz, 1H), 5.25 in (s, 2H), 4.95 points (s, 2H), 4,91 (s, 2H), of 3.84 (s, 3H), 3,39 (d, J=6,9 Hz, 2H), 1,02 (m, 1H), 0,60 to 0.44 (m, 2H), 0,16-0,02 (m, 2H).

Example 2(337)

8-(N-Cyclopropyl-N-(2-forfinal)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,41 (toluene:ethyl acetate = 10:1).

NMR (300 MHz, CDCl3): δ to 7.32 (d, J=8,4 Hz, 1H), 7.23 percent (m, 1H), 7,13-6,97 (m, 3H), 7,06 (d, J=2.7 Hz, 1H), 6.89 in (DD, J=8,4, 2.7 Hz, 1H), 5,15 (users, 2H), of 3.84 (s, 3H), 2,98-of 2.86 (m, 4H), and 2.83 (m, 1H), 2.40 a (s, 3H), 2,02 (m, 2H), 0,84-0,72 (m, 4H).

Example 2(338)

8-(N-Cyclopropylmethyl-N-(2-forfinal)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,49 (toluene:ethyl acetate = 10:1).

NMR (300 MHz, CDCl3): δ to 7.32 (d, J=8.7 Hz, 1H), 7,35-7,16 (m, 2H), 7,06 (d, J=2.4 Hz, 1H), 7,08-6,97 (m, 2H), 6.89 in (DD, J=8.7 Hz, 2.4 Hz, 1H), 5,02 (s, 2H), of 3.84 (s, 3H), 3,41 (d, J=6,9 Hz, 2H), 2,98-2,84 (m, 4H), 2.40 a (s, 3H), 2,07 (m, 2H), of 1.05 (m, 1H), 0,48 (m, 2H), 0,10 (m, 2H).

Example 2(339)

8-(N-Cyclopropylmethyl-N-propylamino)-3-(2-chloro-4-m is toxigenic)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,76 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 8,32 (s, 1H), 7,78 (d, J=8.7 Hz, 1H), 7,03 (d, J=2.7 Hz, 1H), 6,91 (DD, J=8,7, 2.7 Hz, 1H), 3,83 (s, 3H), 3,68-to 3.58 (m, 2H), 3,52 (d, J=6,9 Hz, 2H), 3,06-2,90 (m, 4H), 2.26 and-of 2.08 (m, 2H), 1,66-1,46 (m, 2H), 1,01 (m, 1H), from 0.90 (t, J=7.2 Hz, 3H), 0,52 at 0.42 (m, 2H), 0,16-0,04 (m, 2H).

Example 2(340)

8-(N-Propyl-N-(4-were)methylamino)-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,61 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ of 8.37 (s, 1H), 7,79 (d, J=9.0 Hz, 1H), 7.18 in-7,07 (m, 4H),? 7.04 baby mortality (d, J=2.7 Hz, 1H), 6,92 (DD, J=9,0, 2.7 Hz, 1H), 4,79 (s, 2H), 3,83 (s, 3H), 3.45 points-to 3.36 (m, 2H), 2,96 (t, J=7.8 Hz, 2H), 2,89 (t, J=7.8 Hz, 2H), 2,32 (s, 3H), 2,20-2,04 (m, 2H), 1,66 of 1.46 (m, 2H), 0,87 (t, J=7.2 Hz, 3H).

Example 2(341)

8-(N-Benzyl-N-cyclopropylamino)-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,67 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ scored 8.38 (s, 1H), 7,79 (d, J=8.7 Hz, 1H), 7,38-to 7.18 (m, 5H), 7,05 (d, J=2.4 Hz, 1H), 6,92 (DD, J=8,7, 2.4 Hz, 1H), 4.92 in (s, 2H), 3,83 (s, 3H), 3,40 (d, J=6,9 Hz, 2H), 3,01 (t, J=7.2 Hz, 2H), 2,97 (t, J=7.8 Hz, 2H), 2,22-to 2.06 (m, 2H), 1,02 (m, 1H), 0,54 at 0.42 (m, 2H), 0.12 and 0.02 for (m, 2H).

Example 2(342)

8-(N-Cyclopropylmethyl-N-(4-were)methylamino)-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,71 (hexane:ethyl acetate 2:1).

NMR (300 MHz, CDCl3): δ of 8.37 (s, 1H), 7,79 (d, J=8,4 Hz, 1H), 7,20 (d, J=8.1 Hz, 2H), 7,11 (d, J=8.1 Hz, 2H), 7,05 (d, J=2.7 Hz, 1H), 6,92 (DD, J=8,4, 2.7 Hz, 1H), 4,88 (s, 2H), 3,83 (s, 3H), 3,39 (d, J=6.6 Hz, 2H), a 3.01 (t, J=7.2 Hz, 2H), 2,97 (t, J=7.8 Hz, 2H), 2,32 (s, 3H), 2,22-to 2.06 (m, 2H), 1,02 (m, 1H), 0,54 at 0.42 (m, 2H), 0.14 to 0,02 (m, 2H).

Example 2(343)

8-(N-Propyl-N-(4-forfinal)methylamino)-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,54 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ of 8.37 (s, 1H), 7,79 (d, J=8.7 Hz, 1H), 7,30-7,22 (m, 2H), 7,05 (d, J=2.4 Hz, 1H),? 7.04 baby mortality-of 6.96 (m, 2H), 6,92 (DD, J=8,7, 2.4 Hz, 1H), 4,78 (s, 2H), 3,83 (s, PS), of 3.46-to 3.34 (m, 2H), 2,97 (t, J=7,8 Hz, 2H), 2,89 (t, J=7.2 Hz, 2H), 2,20-2,04 (m, 2H), 1,66 is 1.48 (m, 2H), 0,87 (t, J=7.5 Hz, 3H).

Example 2(344)

8 Dicyclopentadiene-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,58 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ of 8.28 (s, 1H), 7,78 (d, J=8.7 Hz, 1H), 7,03 (d, J=2.4 Hz, 1H), 6,91 (DD, J=8,7, 2.4 Hz, 1H), 6.42 per (d, J=9.6 Hz, 1H), 3,82 (s, 3H), 3,44 (m, 1H), 3,10-3,00 (m, 2H), 2,98-is 2.88 (m, 2H), 2,22-to 2.06 (m, 2H), 1,20 was 1.06 (m, 2H), 0,68-of 0.48 (m, 4H), 0,48-0,34 (m, 4H).

Example 2(345)

8-(4-Heptylamine)-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,54 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 8,32 (s, 1H), 7,74 (d, J=8.7 Hz, 1H),? 7.04 baby mortality (d, J=2.7 Hz, 1H), 6,92 (DD, J=8,7, 2.7 Hz, 1H), 6.42 per (d, J=10,8 Hz, 1H), 5,32 (s, H), equal to 4.97 (s, 2H), 3,83 (s, 3H), 3,42 (m, 1H), 1,78-of 1.26 (m, 8H), of 0.95 (t, J=7.2 Hz, 6H).

Example 2(346)

8-(N-Propyl-N-(4-were)methylamino)-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,53 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 8.41 (s, 1H), of 7.75 (d, J=8.7 Hz, 1H), 7,16-was 7.08 (m, 4H), 7,06 (d, J=2.4 Hz, 1H), 6,92 (DD, J=8,7, 2.4 Hz, 1H), 5,14 (s, 2H), 4.95 points (s, 2H), 4,88 (s, 2H), of 3.84 (s, 3H), 3,42 of 3.28 (m, 2H), 2,33 (, 3H), 1,72 of 1.50 (m, 2H), 0,89 (t, J=7.5 Hz, 3H).

Example 2(347)

8-(N-Propyl-N-(4-forfinal)methylamino)-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,50 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 8.41 (s, 1H), 7,74 (d, J=8,4 Hz, 1H), 7,32-to 7.18 (m, 2H), 7,08-6,97 (m, 3H), 6,93 (DD, J=8,4, 2.4 Hz, 1H), further 5.15 (s, 2H), 4.95 points (s, 2H), 4,88 (s, 2H), of 3.84 (s, 3H), 3,40-3,26 (m, 2H), 1.70 to to 1.48 (m, 2H), 0,89 (t, J=7.2 Hz, 3H).

Example 2(348)

8 Dicyclopentadiene-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,47 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ with 8.33 (s, 1H), 7,73 (d, J=8.7 Hz, 1H),? 7.04 baby mortality (d, J=2.7 Hz, 1H), (DD, J=8,7, 2.7 Hz, 1H), 6,55 (d, J=9.6 Hz, 1H), 5.25 in (s, 2H), 4,94 (s, 2H), 3,83 (s, 3H), of 2.92 (m, 1H), 1,22 was 1.06 (m, 2H), 0.70 to-to 0.48 (m, 4H), 0,48-0,30 (m, 4H).

Example 2(349)

8-(N-Cyclopropylmethyl-N-(4-triptoreline)methylamino)-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,42 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 8.41 (s, 1H), 7,73 (d, J=8,4 Hz, 1H), 7,60 (d, J=8.1 Hz, 2H), 7,50 (d, J=8.1 Hz, 2H), 7,06 (d, J=2.7 Hz, 1H), 6,93 (DD, J=8,4, 2.7 Hz, 1H), 5,27 (s, 2H), 5,02 (s, 2H), 4,96 (s, 2H), 3,84 (s, 3H), 3,40 (d, J=6.6 Hz, 2H), 1,02 (m, 1H), 0,60-0,46 (m, 2H), 0,16-0,04 (m, 2H).

Example 2(350)

8-(N-Cyclopropyl-N-(4-were)methylamino)-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,60 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ at 8.36 (s, 1H), 7,80 (d, J=8,4 Hz, 1H), 7,12-6,99 (m, 5H), 6,93 (DD, J=8,4, 2.7 Hz, 1H), 4,96 (s, 2H), 3,83 (s, 3H), of 2.97 (t, J=7.8 Hz, 2H), equal to 2.94 (t, J=7.5 Hz, 2H), 2,78 (m, 1H), 2,32 (s, 3H), 2,16 is 2.00 (m, 2H), of 0.82 and 0.68 (m, 4H).

Example 2(351)

8-(N-Cyclopropylmethyl-N-(4-triptoreline)methylamino)-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,55 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ of 8.37 (s, 1H), 7,78 (d, J=8.7 Hz, 1H), 7,58 (d, J=8.1 Hz, 2H), 7,49 (d, J=8.1 Hz, 2H), 7,05 (d, J=2.7 Hz, 1H), 6,92 (DD, J=8,7, 2.7 Hz, 1H), equal to 4.97 (s, 2H), 3,83 (s, 3H), 3,39 (d, J=6.6 Hz, 2H), totaling 3.04 (t, J=7.2 Hz, 2H), 2,99 (t, J=7.8 Hz, 2H), 2,18 (m, 2H), 1,01 (m, 1H), 0.56 to 0,42 (m, 2H), 0.14 to 0,02 (m, 2H).

Example 2(352)

8-(3-Pentylamine)-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,53 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ of 8.27 (s, 1H), 7,79 (d, J=8.7 Hz, H), 7,03 (d, J=2.4 Hz, 1H), 6,91 (DD, J=8,7, 2.4 Hz, 1H), 6,30 (d, J=10,2 Hz, 1H), 3,82 (s, 3H), 3,82 (m, 1H), 3,11 (t, J=7.2 Hz, 2H), 2,96 (t, J=7.8 Hz, 2H), 2,24-of 2.08 (m, 2H), 1,84-of 1.52 (m, 4H), 1,01 (t, J=7.5 Hz, 6H).

Example 2(353)

8-(N-Cyclopropylmethyl-N-(4-forfinal)methylamino)-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,46 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ of 8.37 (s, 1H), 7,78 (d, J=8.7 Hz, 1H), 7,38-7,24 (m, 2H), 7,05 (d, J=2.7 Hz, 1H), 7,05-6,93 (m, 2H), 6,92 (DD, J=8,7, 2.7 Hz, 1H), to 4.87 (s, 2H), 3,83 (s, 3H), 3,37 (d, J=6,9 Hz, 2H), 3,01 (t, J=7.5 Hz, 2H), 2,97 (t, J=7.5 Hz, 2H), 2,22-to 2.06 (m, 2H), and 1.00 (m, 1H), 0,54-0,40 (m, 2H), 0.12 and 0.02 for (m, 2H).

Example 2(354)

8-(3-Pentylamine)-2-methyl-3-(2-(1-methyl-1-hydroxyethyl)-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,50 (hexane:ethyl acetate = 1:2).

NMR (300 MHz, CDCl3): δ of 7.23 (d, J=2.7 Hz, 1H), 7,03 (d, J=8.7 Hz, 1H), 6,83 (DD, J=8,7, 2.7 Hz, 1H), of 6.26 (d, J=10,2 Hz, 1H), 5,00-is 4.85 (m, 1H), 3,85 of 3.75 (m) 3,84 (C) total 4H, a 3.06 (t, J=6.9 Hz, 2H), 2,85 (t, J=6,9 Hz, 2H), to 2.29 (s, 3H), 2,11 (Quint., J=7.5 Hz, 2H), 1,80-1,50 (m) 1,64 (C) total 7H, of 1.30 (s, 3H), of 1.03 (t, J=7,2 Hz) and 1.00 (t, J=7.2 Hz) total 6H.

Example 2(355)

8-(N-Propyl-N-(4-triptoreline)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,52 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.32 (d, J=9.0 Hz, 2H), 7,32 (d, J=8,4 G is, 1H), 7,15 (d, J=9.0 Hz, 2H), 7,07 (d, J=2.7 Hz, 1H), 6.89 in (DD, J=8,4, 2.7 Hz, 1H), 4,84 (s, 2H), of 3.84 (s, 3H), 3,44-of 3.32 (m, 2H), only 2.91 (t, J=7.5 Hz, 2H), 2,84 (t, J=7.8 Hz, 2H), 2,39 (s, 3H), 2.06 to 1,98 (m, 2H), 1,66 is 1.48 (m, 2H), from 0.88 (t, J=7.2 Hz, 3H).

Example 2(356)

8-(3-Hexylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,44 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,30 (d, J=8.7 Hz, 1H), 7,05 (d, J=2.4 Hz, 1H), to 6.88 (DD, J=8,7, 2.4 Hz, 1H), from 6.22 (d, J=10,8 Hz, 1H), 3,84 (m, 1H), 3,83 (s, 3H), is 3.08 (t, J=7.5 Hz, 2H), 2,90 (t, J=7.8 Hz, 2H), 2,34 (s, 3H), 2,20-2,04 (m, 2H), 1,80-of 1.32 (m, 6H), and 1.00 (t, J=6.9 Hz, 3H), of 0.95 (t, J=6.9 Hz, 3H).

Example 2(357)

8-(3-Pentylamine)-2-methyl-3-(2-methoxy-4-methylpyridin-5-yl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,23 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 8,00 (s, 1H), 6,69 (s, 1H), 6,23 (d, J=10.5 Hz, 1H), 3,94 (s, 3H), 3,82 (m, 1H), is 3.08 (t, J=7.5 Hz, 2H), 2,89 (t, J=7.8 Hz, 2H), 2,32 (s, 3H), 2,20-to 2.06 (m, 2H), 2,18 (s, 3H), 1,82-and 1.54 (m, 4H), of 1.02 (t, J=7.2 Hz, 6H).

Example 2(358)

Hydrochloride, 8-(N-butyl-N-cyclopropylamino)-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,61 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ of 8.27 (s, 1H), 7,71 (d, J=8,4 Hz, 1H),? 7.04 baby mortality (d, J=2.4 Hz, 1H), 6,94 (m, 1H), 3,90-3,70 (m, 2H), 3,83 (s, 3H), of 3.64 (d, J=6.6 Hz, 2H), 3,30-of 3.12 (m, 2H), 3,12-2,96 (m, 2H), 2,32-2,12 (m, 2H), 1,68 of 1.50 (m, 2H), 1,46 is 1.20 (m, 2H), 1.06 a (m, 1H), 0,91 (who, J=7.2 Hz, 3H), 0,62-0,46 (m, 2H), 0.24 to 0.10 is (m, 2H).

Example 2(359)

Hydrochloride, 8-(N-cyclopropyl-N-(4-were)methylamino)-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,49 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 8,42 (s, 1H), 7,76 (d, J=8.7 Hz, 1H), to 7.09 (d, J=8.1 Hz, 2H), 7,06 (d, J=2.7 Hz, 1H), 6,99 (d, J=8.1 Hz, 2H), 6,93 (DD, J=8,7, 2.7 Hz, 1H), 5,19 (s, 2H), 5,11 (s, 2H), 4,96 (s, 2H), 3,84 (s, 3H), 2,58 (m, 1H), 2,32 (s, 3H), 0,86-0,76 (m, 4H).

Example 2(360)

8-(N-Propyl-N-(4-were)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,74 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.32 (d, J=8.7 Hz, 1H), 7,16-7,06 (m, 4H), 7,07 (d, J=3.0 Hz, 1H), 6.89 in (DD, J=8,7, 3.0 Hz, 1H), 4,80 (s, 2H), of 3.84 (s, 3H), 3,42-3,30 (m, 2H), 2,89 (t, J=7.8 Hz, 2H), 2,82 (t, J=7.2 Hz, 2H), 2,39 (s, 3H), of 2.33 (s, 3H), 2,04-to 1.98 (m, 2H), 1.70 to to 1.48 (m, 2H), 0,87 (t, J=7.2 Hz, 3H).

Example 2(361)

8-(N-Propyl-N-(4-cyanophenyl)methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,38 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.64 (d, J=8.1 Hz, 2H), 7,50 (d, J=8.1 Hz, 2H), 7,30 (d, J=8,4 Hz, 1H), was 7.08 (d, J=2.7 Hz, 1H), make 6.90 (d, J=8,4, 2.7 Hz, 1H), 5,14 (s, 2H), free 5.01 (s, 2H), 4,91 (s, 2H), of 3.84 (s, 3H), 3,36-3,22 (m, 2H), of 2.38 (s, 3H), 1.70 to 1,50 (m, 2H), 0,89 (t, J=7.2 Hz, 3H).

Example 2(362)

8-(N-Propyl-N-(4-cyanophenyl)methylamino)-2-methyl-3-(2-chloro-4-IU is oxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,46 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.61 (d, J=7.8 Hz, 2H), 7,47 (d, J=7.8 Hz, 2H), 7,31 (d, J=8,4 Hz, 1H), 7,07 (d, J=2.7 Hz, 1H), 6.89 in (DD, J=8,4, 2.7 Hz, 1H), 4,90 (s, 2H), of 3.84 (s, 3H), 3,44-of 3.32 (m, 2H), 2,92 (t, J=7.8 Hz, 2H), 2,88 (t, J=7.5 Hz, 2H), of 2.38 (s, 3H), 2,20-2,02 (m, 2H), 1,66 of 1.46 (m, 2H), from 0.88 (t, J=7.2 Hz, 3H).

Example 2(363)

8-(N-Cyclopropylmethyl-N-methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,30 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,30 (d, J=8,4 Hz, 1H), 7,05 (d, J=3.0 Hz, 1H), to 6.88 (DD, J=8,4, 3.0 Hz, 1H), 3,83 (s, 3H), 3,61 (d, J=6,9 Hz, 2H), 3,30 (s, 3H), of 3.12 (t, J=7.2 Hz, 2H), 2,92 (t, J=7.5 Hz, 2H), a 2.36 (s, 3H), 2,20-to 2.06 (m, 2H), 1,09 (m, 1H), 0,60-0,46 (m, 2H), were 0.24 and 0.12 (m, 2H).

Example 2(364)

8-(N-Cyclopropylmethyl-N-methylamino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,22 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,16 (d, J=8,4 Hz, 1H), 6.87 in (d, J=3.0 Hz, 1H), 6,80 (DD, J=8,4, 3.0 Hz, 1H), to 5.35 (s, 2H), 4,89 (s, 2H), 3,83 (s, 3H), and 3.72 (DD, J=6,9, 1.5 Hz, 2H), 3.27 to (s, 3H), of 2.34 (s, 3H), of 2.15 (s, 3H), 1,10 (m, 1H), 0.60 and of 0.48 (m, 2H), were 0.24 to 0.14 (m, 2H).

Example 2(365)

8-(N-Cyclopropylmethyl-N-methylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,18 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3: δ 7,29 (d, J=8.7 Hz, 1H), 7,06 (d, J=2.7 Hz, 1H), to 6.88 (DD, J=8,7, 2.7 Hz, 1H), to 5.35 (s, 2H), 4,91 (s, 2H), 3,83 (s, 3H), 3,71 (d, J=6,9 Hz, 2H), 3.27 to (s, 3H), of 2.38 (s, 3H), 1,10 (m, 1H), 0,62-0,50 (m, 2H), of 0.26 to 0.16 (m, 2H).

Example 2(366)

8-(4-Heptylamine)-3-(2,6-dimethyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,55 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,80 (s, 1H), 6,83 (s, 2H), 6,27 (d, J=ll,l Hz, 1H), 3,98 (m, 1H), 3,80 (s, 3H), 3,11 (t, J=7.5 Hz, 2H), only 2.91 (t, J=7.8 Hz, 2H), 2,22-2,04 (m, 2H), 2.13 and (s, 6H), 1,76-of 1.30 (m, 8H), is 0.96 (t, J=7.2 Hz, 6H).

Example 2(367)

8 Dipropylamino-3-(2,6-dimethyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,54 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,86 (s, 1H), 6,69 (s, 2H), 3,80 (s, 3H), 3,64-of 3.46 (m, 4H), 2,98 (t, J=7.2 Hz, 2H), 2,92 (t, J=7.5 Hz, 2H), 2,22 is 2.00 (m, 2H), 2,12 (s, 6H), 1,68 is 1.48 (m, 4H), to 0.89 (t, J=7.5 Hz, 6H).

Example 2(368)

8-(N-Cyclopropylmethyl-N-propylamino)-3-(2,6-dimethyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rfor = 0.51 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,86 (s, 1H), 6,69 (s, 2H), 3,80 (s, 3H), 3,68-to 3.58 (m, 2H), 3,54 (d, J=6.6 Hz, 2H), 3,03 (t, J=7.5 Hz, 2H), 2,93 (t, J=7.5 Hz, 2H), 2,04 is 2.00 (m, 2H), 2,12 (s, 6H), 1,68 of 1.50 (m, 2H), 1,02 (m, 1H), of 0.91 (t, J=7.5 Hz, 3H), 0,54-0,40 (m, 2H), 0,18-0,04 (m, 2H).

Example 2(369)

8-(N-Benzyl-N-cyclopropylamino)-3-(2,6-dimethyl-4-methoxyphenyl)-6,7-dihydro-5H-CEC is openta[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,49 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.93 (s, 1H), 7,42-was 7.08 (m, 5H), 6,70 (s, 2H), 4,94 (s, 2H), 3,81 (s, 3H), 3,41 (d, J=6.6 Hz, 2H), to 3.02 (t, J=7.5 Hz, 2H), 2,92 (t, J=7.8 Hz, 2H), 2,22-2,04 (m, 2H), 2.13 and (s, 6H), of 1.03 (m, 1H), 0,54 is 0.38 (m, 2H), 0,12-0,01 (m, 2H).

Example 2(370)

8-(N-Cyclopropylmethyl-N-(4-methylphenylethyl)amino)-3-(2,6-dimethyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,53 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ a 7.92 (s, 1H), 7,21 (d, J=8.1 Hz, 2H), 7,11 (d, J=8.1 Hz, 2H), 6,70 (s, 2H), 4,89 (s, 2H), 3,81 (s, 3H), 3,40 (d, J=6,9 Hz, 2H), to 3.02 (t, J=7.2 Hz, 2H), 2,92 (t, J=7.5 Hz, 2H), 2,32 (s, 3H), 2,22-2,04 (m, 2H), 2.13 and (s, 6H), of 1.03 (m, 1H), 0,54-0,40 (m, 2H), 0,10-0,01 (m, 2H).

Example 2(371)

8-(N-Propyl-N-(4-performer)amino)amino-3-(2,6-dimethyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,46 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ a 7.92 (s, 1H), was 7.36-7.18 in (m, 2H), 7,06-to 6.88 (m, 2H), 6,70 (s, 2H), 4,80 (s, 2H), 3,81 (s, 3H), 3.46 in-of 3.32 (m, 2H), 3.00 and is 2.80 (m, 4H), 2,22 is 2.00 (m, 2H), 2.13 and (s, 6H), 1.70 to to 1.48 (m, 2H), from 0.88 (t, J=7.2 Hz, 3H).

Example 2(372)

8 Dicyclopentadiene-3-(2,6-dimethyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,45 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,81 (s, 1H), of 6.68 (s, 2H), 6,40 (d, J=9.9 Hz, 1H), 3,80 (s, 3H), 3,6 (m, 1H), 3,05 (t, J=7.5 Hz, 2H), 2,89 (t, J=7.8 Hz, 2H), 2,22-2,02 (m, 2H), 2.13 and (s, 6H), 1,20 was 1.06 (m, 2H), 0,68-0,36 (m, 8H).

Example 2(373)

8-(N-Butyl-N-cyclopropylamino)-3-(2,6-dimethyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,61 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,87 (s, 1H), 6,69 (s, 2H), 3,80 (s, 3H), 3,76-of 3.60 (m, 2H), 3,53 (d, J=6,9 Hz, 2H), 3,03 (t, J=7.2 Hz, 2H), 2,93 (t, J=7.5 Hz, 2H), 2,22 is 2.00 (m, 2H), 2,12 (s, 6H), 1,64 of 1.46 (m, 2H), 1,42-1,22 (m, 2H), 1,02 (m, 1H), from 0.90 (t, J=7.2 Hz, 3H), 0.56 to 0,38 (m, 2H), 0.18 to 0,02 (m, 2H).

Example 2(374)

8-(N-Cyclopropylmethyl-N-(4-forfinal)methylamino)-3-(2,6-dimethyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rfor = 0.51 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ a 7.92 (s, 1H), 7,38-7,26 (m, 2H), 7,06-6,94 (m, 2H), of 6.71 (s, 2H), 4,89 (s, 2H), 3,81 (s, 3H), 3,39 (d, J=6.6 Hz, 2H), to 3.02 (t, J=7.2 Hz, 2H), 2,93 (t, J=7.2 Hz, 2H), 2,22 is 2.00 (m, 2H), 2,13 (, 6H), 1,01 (m, 1H), 0,54-0,40 (m, 2H), 0,10-0,01 (m, 2H).

Example 3

8-(N-Ethyl-N-n-butylamino)-2-hydroxymethyl-3-(2-methyl-4-hydroxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

To a solution of the compound obtained in example 2(1) (506 mg)in methylene chloride (14 ml), cooled to -78°add 1M solution tribromide boron in methylene chloride (12 ml). The mixture is stirred for 30 min at -78°and then for 5 min at -30°C. the Reaction is th mixture was poured into saturated aqueous sodium bicarbonate solution and the resulting solution was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated. The residue is purified column chromatography on silica gel (n-hexane:ethyl acetate = 1:1 to 2:3)will be specified in the title compound (303 mg)having the following physical properties.

TLC: Rf= 0,14 (n-hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 9,41 (users, 1H), make 6.90 (d, J=9.0 Hz, 1H), 6.42 per (m, 2H), 4,71 (users, 2H), 3,70 (sq, J=7.5 Hz, 2H), to 3.64 (t, J=7.5 Hz, 2H), 3,01 (t, J=7.8 Hz, 4H), 2,39 (users, 1H), 2,18 (m, 2H), a 2.01 (s, 3H), 1,58 (m, 2N), of 1.35 (m, 2H), 1,21 (t, J=7.5 Hz, 3H), of 0.91 (t, J=7.5 Hz, 3H).

Example 4

8-(N-Ethyl-N-n-butylamino)-2-hydroxymethyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

To a solution of the compound obtained in example 3 (985 mg)in methylene chloride (10 ml), cooled to 0°add sodium hydride (95 mg; 63,1%dispersion in oil). The mixture is stirred for 30 minutes To the reaction mixture add methyliodide (of 0.18 ml) and the resulting mixture is stirred for 2 hours at 0°C. To the reaction mixture is added saturated aqueous solution of ammonium chloride and the resulting solution was extracted with ethyl acetate. The organic layer was washed with 1M aqueous sodium hydroxide solution and then with saturated aqueous solution, dried over anhydrous sodium sulfate and concentrated. The residue cleaned the Ute column chromatography on silica gel (toluene:ethyl acetate = 5:1 to 4:1 and 7:2), get listed in the title compound (947 mg)having the following physical properties.

TLC: Rf= 0,35 (n-hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,19 (d, J=8,4 Hz, 1H), 6,85 (d, J=2.7 Hz, 1H), 6,78 (DD, J=8,4, 2.7 Hz, 1H), 4,73 (d, J=5.7 Hz, 2H), 3,82 (s, 3H), 3,65 (sq, J=7.2 Hz, 2H)and 3.59 (t, J=7.2 Hz, 2H), 2,98 (t, J=6.9 Hz, 2H), 2,92 (t, J=7.8 Hz, 2H), 2,35 (m, 1H), 2,19 (s, 3H), of 2.15 (m, 2H), 1.55V (m, 2H), 1,35 (m, 2H), of 1.18 (t, J=7.2 Hz, 3H), of 0.90 (t, J=7.2 Hz, 3H).

Example 5

8-(N-Propyl-N-(2-methoxymethyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

To a solution of the compound obtained in example 2(2) (186 mg)in dimethylsulfoxide (5 ml), add triethylamine (0,39 ml) and a complex of sulfur trioxide and pyridine (225 mg). The mixture is stirred for 2 hours at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated. To a solution of the residue in pyridine (5 ml) was added the hydrochloride of o-methylhydroxylamine (28 mg). The mixture is stirred for 15 hours at room temperature. The reaction mixture was concentrated and diluted with ethyl acetate. The diluted solution was washed with saturated aqueous sodium bicarbonate and then saturated aqueous sodium chloride, dried over anhydrous sulfa what Ohm sodium and concentrate. The residue is purified column chromatography on silica gel (n-hexane:ethyl acetate = 4:1 to 3:1)get mentioned in the title compound (16 mg)having the following physical properties.

TLC: Rf= 0,78 (n-hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3):

main isomer

δ EUR 7.57 (t, J=5.7 Hz, 1H), 7,15(d, J=8,4 Hz, 1H), 6,86 (d, J=2.4 Hz, 1H), 6,79 (DD, J=8,4, 2.4 Hz, 1H), 4,35 (d, J=6.0 Hz, 2H), 3,86 (s, 3H), 3,82 (s, 3H), 3,49 (t, J=7.8 Hz, 2H), 2,99 (t, J=7.2 Hz, 2H), only 2.91 (t, J=7.5 Hz, 2H), 2,32 (s, 3H), of 2.18 (s, 3H), and 2.14 (m, 2H), 1,58 (m, 2H), of 0.90 (t, J=7.2 Hz, 3H)

side-isomer

δ to 7.15 (d, J=8,4 Hz, 1H), 6,95 (t, J=3,9 Hz, 1H), 6,86 (d, J=2.4 Hz, 1H), 6,79 (DD, J=8,4, 2.4 Hz, 1H), 4,47 (d, J=4,2 Hz, 2H), 3,90 (s, 3H), 3,82 (s, 3H), of 3.54 (t, J=7.8 Hz, 2H), 2,99 (t, J=7.2 Hz, 2H), only 2.91 (t, J=7.5 Hz, 2H), 2,32 (s, 3H), of 2.18 (s, 3H), and 2.14 (m, 2H), 1,58 (m, 2H), to 0.92 (t, J=7.2 Hz, 3H).

Examples 5(1)-5(2)

The following connections receive according to the method of example 5 using the compound obtained in example 2(26), or compounds obtained in example 4, and hydroxylamine hydrochloride instead of hydrochloride of o-methylhydroxylamine.

Example 5(1)

Hydrochloride, 8-(N-propyl-N-(2-methoxymethyl)amino)-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,22 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, pyridine-d50.5 ml + CDC130.1 ml):

main isomer

δ 7,87 (t, J=5.4 Hz, 1H), 7,38 (d, J=8,4 Hz, 1H), 7,03 (d, J=2.7 Hz, 1H), 6,95 (DD, J=8,4, 2.7 Hz, 1H), 5,27 (s, 2H),equal to 4.97 (s, 2H), 4,59 (d, J=5.4 Hz, 2H), 3,86 (s, 3H), 3,74 (s, 3H), 3,38 (t, J=7.5 Hz, 2H), 2,44 (s, 3H), 2,31 (s, 3H), 1,65 of 1.50 (m, 2H), 0,81 (t, J=7.5 Hz, 3H)

side-isomer

δ 7,38 (d, J=8,4 Hz, 1H), 7,31 (t, J=4,2 Hz, 1H), 7,03 (d, J=2.7 Hz, 1H), 6,95 (DD, J=8,4, 2.7 Hz, 1H), 5.25 in (s, 2H), 4.95 points (s, 2H), 4,71 (d, J=4,2 Hz, 2H), 3,92 (s, 3H), 3,74 (s, 3H), 3.43 points (t, J=7.2 Hz, 2H), 2,43 (s, 3H), 2,31 (s, 3H), 1,65 of 1.50 (m, 2H), from 0.84 (t, J=7.2 Hz, 3H).

Example 5(2)

8-(N-Ethyl-N-n-butylamino)-2-gidroksilaminami-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,19 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ of 8.15 (s, 1H), of 7.96 (users; 1H), 7,18 (d, J=8,1 Hz, 1H), 6,85 (d, J=2.7 Hz, 1H), 6,79 (DD, J=8,1, 2.7 Hz, 1H), 3,82 (s, 3H), 3,67 (sq, J=7.2 Hz, 2H), 3,61 (t, J=7.5 Hz, 2H), 2,99 (t, J=7.2 Hz, 2H), of 2.92 (t, J=7.8 Hz, 2H), 2,18 (s, 3H), of 2.16 (m, 2H), 1.55V (m, 2H), 1,33 (m, 2H), of 1.18 (t, J=7.2 Hz, 3H), of 0.89 (t, J=7.5 Hz, 3H).

Example 6

8-[(2S)-1-Hydroxylaminopurine-2-yl]amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

To a solution of the compound obtained in example 2(15) (290 mg)in acetic acid (4 ml) is added 1M hydrochloric acid (1.4 ml), and the mixture is stirred for 1 hour at 80°C. the Reaction mixture was poured into saturated aqueous sodium bicarbonate solution (100 ml) in an ice bath, the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sulfate on the model and concentrate. Hydroxylamine hydrochloride (52 mg) are added to a solution of the residue in pyridine (3 ml) and the mixture is stirred for 15 hours at room temperature. The reaction mixture was concentrated and diluted with ethyl acetate. The diluted solution was washed with saturated aqueous sodium bicarbonate and then saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated. The residue is purified column chromatography on silica gel (n-hexane:ethyl acetate = 1:1)get mentioned in the title compound (143 mg)having the following physical properties for mixture of isomers.

TLC: Rf= 0,32 (n-hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDC13):

main isomer

δ 7,80 (users, 1H), 7,47 (d, J=6.0 Hz, 1H), 7,14 (d, J=8,4 Hz, 1H), at 6.84 (d, J=2.7 Hz, 1H), 6,78 (DD, J=8,4, 2.7 Hz, 1H), 6,53 (d, J=9.6 Hz, 1H), 4,60 (m, 1H), 3,82 (s, 3H), 3.25 to about 3.00 (m, 2H), 2,88 (t, J=7.5 Hz, 2H), 2,31 (s, 3H), 2,17 (s, 3H), 2,10 (m, 2H), 1,90 (m, 2H), 1,11 (t, J=7.2 Hz, 3H)

side-isomer

6 charged 8.52 (users, 1H), 7,14 (d, J=8,4 Hz, 1H), at 6.84 (d, J=2.7 Hz, 1H), 6,80 (m, 1H), 6,78 (DD, J=8,4, 2.7 Hz, 1H), 6,44 (d, J=9.6 Hz, 1H), 5,23 (m, 1H), 3,82 (s, 3H), 3.25 to about 3.00 (m, 2H), 2,88 (t, J=7.5 Hz, 2H), 2,31 (s, 3H), 2,17 (s, 3H), 2,10 (m, 2H), 1,90 (m, 2H), 1,11 (t, J=7.2 Hz, 3H).

Example 6(1)

8-[(2S)-1-Methoxyaminomethyl-2-yl]amino-2-methyl-3-(2-methyl-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

Specified in the title compound (128 mg)having the following physical and the definition of property, get the technique similar to the method of example 5 using the compound obtained in example 2(14) (365 mg), and hydrochloride of o-methylhydroxylamine instead of hydroxylamine hydrochloride.

TLC: Rf= 0,20 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDC13):

main isomer

δ of 7.36 (d, J=6.0 Hz, 1H), 7,14 (d, J=8,4 Hz, 1H), 6,86 (d, J=2.7 Hz, 1H), 6,79 (DD, J=8,4, 2.7 Hz, 1H), 6,60 (d, J=9.9 Hz, 1H), vs. 5.47 (d, J=10.5 Hz, 1H), 5,31 (d, J=10.5 Hz, 1H), 4,89 (s, 2H), 4,07 (m, 1H), 3,86 (s, 3H), 3,82 (s, 3H), of 2.33 (s, 3H), of 2.16 (s, 3H), 1,96-to 1.87 (m, 2H), 1,10 (t, J=7.5 Hz, 3H)

side-isomer

δ 7,14 (d, J=8,4 Hz, 1H), 6,86 (d, J=2.7 Hz, 1H), 6,79 (DD, J=8,4, 2.7 Hz, 1H), 6,76 (m, 1H), 6,53 (d, J=9.9 Hz, 1H), and 5.30 (m, 2H), 4,89 (s, 2H), 4.72 in (m, 1H), 3.96 points (s, 3H), 3,82 (s, 3H), of 2.33 (s, 3H), of 2.16 (s, 3H), 1,96-to 1.87 (m, 2H), 1,10 (t, J=7.5 Hz, 3H).

Example 7

8-[(1S)-1-Cyanopropionic]-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

To a solution of the compound obtained in example 6 (137 mg)in methylene chloride (1 ml), cooled to -78°With, add triethylamine (0,32 ml) and the anhydride triftormetilfullerenov acid (13 ml). The mixture is stirred for 2 hours at room temperature. To the reaction mixture is added saturated aqueous sodium bicarbonate solution and the resulting solution was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrate the Ute. The residue is purified column chromatography on silica gel (n-hexane:ethyl acetate = 3:1 to 2:1)receive specified in the title compound (100 mg)having the following physical properties.

TLC: Rf= 0,27 (n-hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.15 (d, J=8,1 Hz, 1H), 6,86 (d, J=2.7 Hz, 1H), 6,79 (DD, J=8,1, 2.7 Hz, 1H), 6,50 (d, J=9.6 Hz, 1H), 4,78 (m, 1H), 3,82 (s, 3H), of 3.33 (DDD, J=14,4, 7,5, 6.3 Hz, 1H), 3,11 (DDD, J=14,4, 8,1, 6.3 Hz, 1H), with 2.93 (m, 2H), 2,31 (s, 3H), 2,25-2,10 (m, 7H), of 1.29 (t, J=7.5 Hz, 3H).

Example 7(1)

8-(N-Ethyl-N-n-butylamino)-2-cyano-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

Specified in the title compound (195 mg)having the following physical properties, get the technique similar to the method of example 7, using the compound obtained in example 5(2)(211 mg).

TLC: Rf= 0,34 (n-hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,28 (d, J=8,4 Hz, 1H), to 6.88 (d, J=2.7 Hz, 1H), 6,83 (DD, J=8,4, 2.7 Hz, 1H), 3,83 (s, 3H), 3,65 (sq, J=6,9 Hz, 2H), to 3.58 (t, J=7.5 Hz, 2H), 3,00 (t, J=7.2 Hz, 2H), 2,96 (t, J=7.8 Hz, 2H), 2,29 (s, 3H), 2,18 (m, 2H), 1.57 in (m, 2H), 1,33 (m, 2H), 1,20 (t, J=6.9 Hz, 3H), of 0.91 (t, J=7.2 Hz, 3H).

Example 8

9-(3-Pentylamine)-6-methyl-5-(2-methyl-4-methoxyphenyl)furo[3,2-d]pyrazolo[1,5-a]pyrimidine

To a solution of the compound obtained in example 2(6) (215 mg)in diphenyl ether (3 ml) is added 10%palladium on coal (150 mg) and the mixture paramesh who live within 4 hours at 250° C. After cooling the reaction mixture to room temperature it was diluted with methanol (10 ml). The diluted solution was filtered through celite (registered trade mark). The filtrate is concentrated, and the residue is purified column chromatography on silica gel (n-hexane:acetone = 9:1)get mentioned in the title compound (150 mg)having the following physical properties.

TLC: Rf= 0,42 (n-hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDC13): b 7,76 (d, J=2.4 Hz, 1H), 7,20 (d, J=8,1 Hz, 1H), to 6.88 (d, J=2.7 Hz, 1H), 6,80 (DD, J=8,1, 2.7 Hz, 1H), 6,78 (d, J=2.4 Hz, 1H), 6,28 (userd, J=10,2 Hz, 1H), 4,30 (m, 1H), 3,83 (s, 3H), is 2.37 (s, 3H), 2,21 (s, 3H), 1,92-of 1.65 (m, 4H), of 1.05 (m, 6H).

Example 9

8-(3-Pentyloxy)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

In a solution of sodium hydride (92.0 mg; 60% in oil) in toluene is added dropwise 3-pentanol (202 mg) and the mixture is stirred for 2 min at 80°C. To this mixture is added the compound obtained in reference example 7 (250 mg)and the resulting mixture is stirred for 5 hours. To the reaction mixture are added water and ethyl acetate and stirred. The organic layer is separated. Then the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated. The residue is purified column chromatography is and silica gel (hexane:ethyl acetate = 5:1), get listed in the title compound (128 mg)having the following physical properties.

TLC: Rf= 0,58 (toluene:ethyl acetate = 5:1).

NMR (300 MHz, CDCl3): δ 7,16 (d, J=8,4 Hz, 1H), 6,86 (d, J=2.4 Hz, 1H), 6,79 (DD, J=8,4, 2.4 Hz, 1H), of 5.05 (Quint., J=6.0 Hz, 1H), 3,82 (s, 3H), 3,05 (t, J=7.5 Hz, 2H), equal to 2.94 (t, J=7.5 Hz, 2H), 2,34 (s, 3H), 2,22 is 2.10 (m, 2H), 2,16 (s, 3H), 1,92-of 1.78 (m, 4H), of 1.05 (t, J=7.5 Hz, 6H).

Examples 9(1)-9(5)

The following compounds are obtained according to the method similar to the method of example 9, using the appropriate connection.

Example 9(1)

8-(3-Pentyloxy)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,50 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,29 (d, J=8,4 Hz, 1H), 7,06 (d, J=2.4 Hz, 1H), 6.89 in (DD, J=8,4, 2.4 Hz, 1H), 5,06 (Quint., J=6.0 Hz, 1H), 3,83 (s, 3H), 3,05 (t, J=7.2 Hz, 2H), 2.95 points (t, J=7.2 Hz, 2H), of 2.38 (s, 3H), 2,16 (Quint., J=7.2 Hz, 2H), 1,94-of 1.74 (m, 4H), was 1.04 (t, J=7.5 Hz, 6H).

Example 9(2)

8-(3-Pentyloxy)-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,25 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,28 (d, J=8,4 Hz, 1H), 7,07 (d, J=2.7 Hz, 1H), 6.90 to (DD, J=8,4, 2.7 Hz, 1H), from 5.29 (s, 2H), is 4.93 (s, 2H), 4,56 (m, 1H), 3,84 (s, 3H), 2,41 (s, 3H), 1,99 and 1.80 (m, 4H), of 1.05 (t, J=7.5 Hz, 6H).

Example 9(3)

8-(4-Heptyloxy)-2-methyl-3-(2-chloro-5-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,85 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,29 (d, J=8.7 Hz, 1H), 7,06 (d, J=2.7 Hz, 1H), 6.89 in (DD, J=8,7, 2.7 Hz, 1H), 5,22 (Quint., J=6.0 Hz, 1H), 3,83 (s, 3H), 3,05 (t, J=7.5 Hz, 2H), 2.95 points (t, J=7.5 Hz, 2H), is 2.37 (s, 3H), 2, 16 (Quint., J=7.5 Hz, 2H), 1,90-of 1.66 (m, 4H), 1,58-of 1.42 (m, 4H), of 0.95 (t, J=7.2 Hz, 6H).

Example 9(4)

8 Isopropoxy-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,36 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,29 (d, J=8,4 Hz, 1H), 7,06 (d, J=2.4 Hz, 1H), 6.89 in (DD, J=8,4, 2.4 Hz, 1H), 5,43 (Sept., J=6.3 Hz, 1H), 3,83 (s, 3H), 3,06 (t, J=7.5 Hz, 2H), 2,96 (t, J=7.5 Hz, 2H), of 2.38 (s, 3H), 2,16 (Quint., J=7.5 Hz, 2H)and 1.51 (d, J=6.3 Hz, 6H).

Example 9(5)

8-(1,6-Heptadien-4-yl)oxy-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,58 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,29 (d, J=8,4 Hz, 1H), 7,06 (d, J=2.7 Hz, 1H), 6.89 in (DD, J=8,4, 2.7 Hz, 1H), 5,90 (DDT, J=17.1 to, to 10.2, 6.9 Hz, 2H), 5,34 (Quint., J=6.3 Hz, 1H), 5,17 (m, 2H), 5,11 (DD, m, 2H), 3,83 (s, 3H), 3,01 (t, J=7.5 Hz, 2H), 2.95 points (t, J=7.5 Hz, 2H), 2,70-of 2.50 (m, 4H), of 2.38 (s, 3H), of 2.15 (Quint., J=7.5 Hz, 2H).

Example 10

Hydrochloride 8-(3-pentylthio)-2-methyl-3-(2-chloro-5-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

3-Acetylthiophene (252 mg) and the compound obtained in reference example 7 (300 mg)are added to a solution guide is IDA sodium (68,9 mg; 60% in oil) in ethanol (17 ml) at 0°C. After stirring the mixture for 1 hour, the reaction mixture was concentrated. To the residue is added water and ethyl acetate and stirred. The organic layer is separated. Then the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated. The residue is purified column chromatography on silica gel (hexane:ethyl acetate = 5:1), to a purified substance is added a mixture of 4 G. hydrochloric acid and ethyl acetate (0.2 ml), the solution stirred for 10 min and concentrated receive specified in the header connection (271,1 mg) having the following physical properties.

TLC: Rf= 0,57 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ 7,29 (d, J=8.7 Hz, 1H), 7,07 (d, J=2.4 Hz, 1H), 6.89 in (DD, J=8,7, 2.4 Hz, 1H), 4,27 (Quint., J=6.3 Hz, 1H), 3,84 (s, 3H), 3,05 (t, J=7.5 Hz, 2H), 3,00 (t, J=7.5 Hz, 2H), 2.40 a (s, 3H), 2,17 (Quint., J=7.5 Hz, 2H), 1,72-of 1.64 (m, 4H), of 1.02 (t, J=7.5 Hz, 6H).

Example 11

8-(4-Were)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

To the compound obtained in reference example 7 (300 mg), dimethoxyethane (3 ml) is added 4-methylphenylimino acid (131 mg), palladium acetate (11 mg), triphenylphosphine (48 mg) and saturated aqueous solution of sodium carbonate (2 ml)and the mixture is boiled fix refrigerator for 5 hours. After cooling to room temperature the reaction mixture was diluted with ethyl acetate. The diluted solution was washed with saturated aqueous sodium chloride and water, dried over anhydrous magnesium sulfate and concentrated. The residue is purified column chromatography on silica gel (hexane:ethyl acetate = 5:1)get mentioned in the title compound (222 mg) having the following physical properties.

TLC: Rf= 0,41 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,72 (d, J=8.1 Hz, 2H), was 7.36 (d, J=8.1 Hz, 2H), 7,19 (d, J=8,4 Hz, 1H), to 6.88 (d, J=2.7 Hz, 1H), for 6.81 (DD, J=2.7, and an 8.4 Hz, 1H), 3,84 (s, 3H), 3,01 (t, J=7.5 Hz, 2H), equal to 2.94 (t, J=6.6 Hz, 2H), 2, 45 (s, 3H), of 2.30 (s, 3H), of 2.20 (s, 3H), and 2.14 (m, 2H).

Example 11(1)-11(5)

These compounds get the technique similar to the method of example 11, using the appropriate connection.

Example 11(1)

Hydrochloride 8-(2,4-Dichlorophenyl)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,38 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, DMSO-d6): δ to $ 7.91 (d, J=1.8 Hz, 1H), of 7.70 (d, J=8,4 Hz, 1H), to 7.64 (DD, J=1,8, and 8.4 Hz, 1H), 7,11 (userd, J=8,1 Hz, 1H), make 6.90 (d, J=2.7 Hz, 1H), for 6.81 (DD, J=2.7, and an 8.4 Hz, 1H), of 3.77 (s, 3H), equal to 2.94 (m, 2H), 2,68 (m, 2H), and 2.14 (s, 3H), 2,12 (m, 2H), 2,09 (s, 3H).

Example 11(2)

8-(3-Triptoreline)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,27 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 8,08 (users, 1H), 8,06 (userd, J=8,1 Hz, 1H), 7,79 (userd, J=7.8 Hz, 1H), 7,70 (.d, J=8,1, 7.8 Hz, 1H), 7,19 (d, J=8,1 Hz, 1H), 6.89 in (d, J=2.7 Hz, 1H), PC 6.82 (DD, J=8,1, 2.7 Hz, 1H), 3,84(8, 3H), 3.04 from (t, J=7.5 Hz, 2H), equal to 2.94 (t, J=7.5 Hz, 2H), 2,31 (s, 3H), of 2.20 (s, 3H), 2,18 (m, 2H).

Example 11(3)

Hydrochloride 8-(4-methoxyphenyl)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,23 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ a 7.92 (d, J=9.0 Hz, 2H), 7,16 (d, J=9.0 Hz, 2H), 7,16 (d, J=9.0 Hz, 1H), 6,92 (d, J=2.7 Hz, 1H), 6,86 (DD, J=9,0, 2.7 Hz, 1H), 3,95 (s, 3H), 3,85 (s, 3H), 3,61 (t, J=7.5 Hz, 2H), to 3.09 (t, J=7.5 Hz, 2H), of 2.38 (s, 3H), 2,30 (m, 2H), measuring 2.20 (s, 3H).

Example 11(4)

8-(3,5-Dichlorophenyl)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,50 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ of 7.69 (d, J=1.8 Hz, 2H), 7,52 (t, J=1.8 Hz, 1H), 7,17 (d, J=8,4 Hz, 1H), to 6.88 (d, J=2.7 Hz, 1H), PC 6.82 (DD, J=2.7, and an 8.4 Hz, 1H), 3,84 (s, 3H), to 3.02 (t, J=7.5 Hz, 2H), 2,93 (t, J=6.9 Hz, 2H), 2,32 (s, 3H), 2,19 (s, 3H), 2,17 (m, 2H).

Example 11(5)

8-(2-Were)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,38 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,34-of 7.48 (m, 4H), 7,20 (m, 1H), 6.89 in (d, J=2.7 Hz, 1H), PC 6.82 (DD, J=2,7, 8,1 G is, 1H), 3,84 (s, 3H), 3.04 from (m, 2H), 2,81 (m, 1H), 2,62 (m, 1H), and 2.27 (s, 3H), of 2.20 (m, 3H), 2,17 (s, 3H), of 2.15 (m, 2H).

Example 12

8-Bis(etoxycarbonyl)methyl-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

To a suspension of sodium hydride (210 mg, 63.1% in oil) in tetrahydrofuran add diethylmalonate (880 mg) and the mixture is stirred for 30 min at room temperature. The compound obtained in reference example 7 (820 mg), is added to the reaction mixture and the resulting mixture is refluxed 4 hours. To the reaction mixture is added saturated aqueous solution of ammonium chloride (10 ml) and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated. The residue is purified column chromatography on silica gel (hexane:ethyl acetate = 8:1 to 7:1)get mentioned in the title compound (1.10 g) with the following physical properties.

TLC: Rf= 0,48 (hexane:ethyl acetate = 2:1).

NMR (300 MHz, CDCl3): δ to 7.15 (d, J=8,1 Hz, 1H), 6.87 in (d, J=3.0 Hz, 1H), 6,80 (DD, J=8,1, 3.0 Hz, 1H), 6,02 (s, 1H), 4,32 (m, 4H), 3,82 (s, 3H), 2,96 (t, J=7.8 Hz, 2H), only 2.91 (t, J=7.8 Hz, 2H), 2,32 (s, 3H), 2.21 are 2,09 (m, 2H), 2,17 (s, 3H), 1,32 (t, J=7.2 Hz, 6N).

Examples 12(1)-12(4)

These compounds get the technique similar to the method of example 12, using the appropriate connection.

Example 12(1)

8-(1-Dimethylamino-1,3-dioxo-2-butyl)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,55 (ethyl acetate).

NMR (300 MHz, CDCl3): δ 7,14 (d, J=8,1 Hz, 1H), 6.87 in (d, J=1.8 Hz, 1H), 6,83-6,74 (m, 1H), 6,29 (s, 1H), 3,83 (s, 3H), 3,05 (s, 3H), 3,05-2,60 (m, 6H), is 2.41 (s, 3H), of 2.30 (s, 3H), 2,16 (users, 6H).

Example 12(2)

8-(2,4-Dioxo-3-pentyl)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,34 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 16,93 (s, 1H), 7,19 (d, J=8,4 Hz, 1H), 6.89 in (d, J=3.0 Hz, 1H), 6,83 (DD, J=8,4, 3.0 Hz, 1H), 3,84 (s, 3H), 3.04 from (t, J=7.2 Hz, 2H), of 2.81 (t, J=7.2 Hz, 2H), 2,33 (s, 3H), 2,20 (Quint., J=7.2 Hz, 2H), 2,18 (s, 3H), of 1.95 (s, 6H).

Example 12(3)

8-Bis(etoxycarbonyl)methyl-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,18 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,28 (d, J=8,4 Hz, 1H), 7,07 (d, J=2.4 Hz, 1H), 6.89 in (DD, J=8,4, 2.4 Hz, 1H), 6,02 (s, 1H), 4,40-4,20 (m, 4H), of 3.84 (s, 3H), 2,98 (t, J=7.5 Hz, 2H), 2,92 (t, J=7.5 Hz, 2H), 2,35 (s, 3H), 2,17 (Quint., J=7.5 Hz, 2H), 1,31 (t, J=7.2 Hz, 6H).

Example 12(4)

8-Bis(etoxycarbonyl)methyl-2-methyl-3-(2-chloro-4-methoxyphenyl)-5,7-dihydrofuro[3,4-d]pyrazolo[1,5-a]pyrimidine

TLC: Rf= 0,28 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3

Example 13

8-(1,3-Hydroxy-2-propyl)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

In an argon atmosphere 1M diisopropylaminoethyl (3,94 ml in hexane) is added dropwise into a solution of the compound obtained in example 12 (355 mg)in anhydrous diethyl ether (7 ml) at -78°C. the Mixture is heated to 0°C and stirred for 4.5 hours. To the mixture are added dropwise methanol and then heated to room temperature. To the reaction mixture add 1 N. hydrochloric acid and the mixture extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated. The residue is purified column chromatography on silica gel (hexane:ethyl acetate = 3:1)get mentioned in the title compound (260 mg) having the following physical properties.

TLC: Rf= 0,50 (chloroform:methanol = 9:1).

NMR (300 MHz, CDCl3): δ 7,13 (userd, J=8.7 Hz, 1H), 6.87 in (s, 1H), 6,80 (userd, J=8.7 Hz, 1H), equal to 4.97 (m, 1H), 4,90 (m, 1H), 4,24 (m, 2H), 4,13 (m, 2H), 3,83 (s, 3H)and 3.59 (m, 1H), 2,98 (ushort, J=7.2 Hz, 4H), 2,31 (s, 3H), 2,28-2,00 (m, 5H).

Example 14

8-(1,3-Dimethoxy-2-propyl)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

A solution of the compound obtained in example 13 (120 mg) in DMF (2 ml)is added dropwise into a solution of sodium hydride (26,0 mg; 60% in oil) in DMF at 0°C. To the mixture is added dropwise methyliodide (81,0 μl) and then stirred for 1 hour. To the reaction mixture are added water and ethyl acetate, the organic layer separated. Then the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated after adding benzene (5 ml). The residue is purified column chromatography on silica gel (hexane:ethyl acetate = 3:1)receive specified in the header connection (58,7 mg) having the following physical properties.

TLC: Rf= 0,80 (ethyl acetate).

NMR (300 MHz, CDCl3): δ to 7.15 (d, J=8,4 Hz, 1H), 6,86 (d, J=2.4 Hz, 1H), 6,79 (DD, J=8,4, 2.4 Hz, 1H), 4,28-4,16 (m, 1H), 4,14-4,06 (m, 2H), 3.96 points-3,86 (m, 2H), 3,83 (s, 3H), at 3.35 (s, 6H), 3,06 (t, J=7.5 Hz, 2H), 2,94 (t, J=7.5 Hz, 2H), 2,31 (s, 3H), 2,17 (s, 3H), 2,17-of 2.08 (m, 2H).

Example 15

8-(N,N-Dimethylcarbamoyl)-2-methyl-3-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine

To a solution of the compound obtained in example 12 (410 mg)in methanol (1 ml) at 24°add 50%aqueous solution of dimethylamine (491 mg) and the mixture is stirred for 20 hours at 90°C. the Reaction mixture is cooled at room temperature is e, to the mixture are added water and ethyl acetate and stirred. The organic layer is separated. Then the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated. The residue is purified column chromatography on silica gel (hexane:ethyl acetate = 5:1)receive specified in the header connection (102,7 mg) having the following physical properties.

TLC: Rf= 0,55 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,16 (d, J=8,4 Hz, 1H), 6.87 in (d, J=2.7 Hz, 1H), 6,80 (DD, J=8,4, 2.7 Hz, 1H), 3,83 (s, 3H), of 3.27 (d, J=1.2 Hz, 1H), 3.04 from-to 2.94 (m, 5H), of 2.72 (s, 3H), of 2.36 (s, 3H), 2,24 is 2.10 (m, 8H).

Reference example 8

2-Chloro-4-methoxybenzaldehyde

To a suspension of sodium hydride (2.6 g; 62.6% in oil) in dimethylformamide (80 ml) is added dropwise over 15 min a solution of 2-chloro-4-hydroxybenzaldehyde (10.0 g) in dimethylformamide (50 ml). The mixture is stirred for 30 minutes In the reaction mixture for 10 min at 0°With added dropwise methyliodide (4,2 ml) and stirred for 1 hour. The reaction mixture was poured into water and extracted with a mixture of hexane/ethyl acetate (1:1). The organic layer is washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrate, get mentioned in the title compound (10.7 g) with the following physical is Kimi data.

TLC: Rf= 0,61 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 10,33 (d, J=0.6 Hz, 1H), of 7.90 (d, J=9.0 Hz, 1H), 6,94 (d, J=2.4 Hz, 1H), 6.89 in (DDD, J=9,0, the 2.4, 0.6 Hz, 1H), with 3.89 (s, 3H).

Reference example 9

1-(2,2-Dibromoethenyl)-2-chloro-4-methoxybenzoyl

To a solution of the compound obtained in reference example 8 (5.0 g) in methylene chloride add tetrabromide carbon (10.7 g). To the mixture are added in several portions triphenylphosphine (16,9 g), maintaining the internal temperature of 5°s or less. The mixture is stirred 30 min at 0°C. Suspension of the reaction mixture in hexane (500 ml) was poured into a silica gel (30 g) and then filtered. The silica gel was washed with hexane/ethyl acetate (10:1). The filtrate and washings are combined and concentrated. The residue is purified column chromatography on silica gel (hexane:ethyl acetate = 10:1)get mentioned in the title compound (6.6 g) with the following physical properties.

TLC: Rf= 0,82 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ a 7.62 (d, J=9.0 Hz, 1H), 7,51 (s, 1H), 6,94 (d, J=2,l Hz, 1H), 6,83 (DD, J=9,0, 2,l Hz, 1H), 3,81 (s, 3H).

Reference example 10

1-(1-PROPYNYL)-2-chloro-5-methoxybenzo

To a solution of the compound obtained in reference example 9 (1.98 g)in tetrahydrofuran (20 ml) at -78°add 1.57 M solution of n-utility in hexane (8.2 ml). The mixture is stirred for 30 min and 1 cha is at 0° C. the Reaction mixture was cooled to -78°add methyliodide ones (0.46 ml) and stirred for 1 hour at 0°C. the Reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated. The residue is purified column chromatography on silica gel (hexane:ethyl acetate = 10:1)receive specified in the header connection (0,89 g) with the following physical properties.

TLC: Rf= 0,69 (hexane:ethyl acetate = 5:1).

NMR (300 MHz, CDCl3): δ 7,34 (d, J=8.7 Hz, 1H), 6,91 (d, J=2.7 Hz, 1H), 6.73 x (d, J=8.7 Hz, 2.7 Hz, 1H), 3,79 (s, 3H), 2,10 (s, 3H).

Reference example 11

5-Bis(trimethylsilyl)amino-2-cyano-3-methyl-4-(2-chloro-4-methoxyphenyl)pyrrol

In the atmosphere of argon diisobutylaluminium (13,8 ml) are added to a Nickel chloride (832 g), which was dried by heating for 30 min, and then the mixture is stirred for 15 minutes After the color change of the mixture on black to the reaction mixture for 25 minutes add the compound obtained in referential example 10 (11.6 g), trimethylsilylacetamide (46 ml). The mixture is heated and hexane is distilled off. The solution is stirred for 2.5 hours at 130°C. the Reaction mixture is cooled to room temperature and diluted with methylene chloride. A diluted solution of purified column chromatography on silica gel (Gex is n:ethyl acetate = 10:1), get listed in the title compound (9.5 g) with the following physical data, and 2-bis(trimethylsilyl)amino-5-cyano-3-methyl-(4-(2-chloro-4-methoxyphenyl)pyrrole (5,2 g) as a by-product.

TLC: Rf= 0,34 (hexane:ethyl acetate = 10:1).

NMR (300 MHz, CDCl3): δ 7,76 (users, 1H), 7,10 (d, J=8,4 Hz, 1H), 7,00 (d, J=2.7 Hz, 1H), PC 6.82 (DD, J=8,4, 2.7 Hz, 1H), 3,83 (s, 3H), of 2.06 (s, 3H), of 0.14 (s, 9H), -0,14 (s, 9H).

Reference example 12

5-Amino-2-cyano-3-methyl-4-(2-chloro-4-methoxyphenyl)pyrrol

To a solution of the compound obtained in reference example 11 (6,27 g)in methanol (50 ml) is added at room temperature 1 N. aqueous sodium hydroxide solution (15,4 ml). The mixture is refluxed for 1.5 hour. After cooling to room temperature the reaction mixture was poured into aqueous sodium carbonate solution and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated receive specified in the header connection (4,78 g) having the following physical data.

TLC: Rf= 0,20 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 8,61 (users, 1H), 7,14 (d, J=8.7 Hz, 1H), 7,03 (d, J=2.4 Hz, 1H), 6,86 (DD, J=8,7, 2.4 Hz, 1H), 3,83 (s, 3H), 3,71 (users, 2H), 2,04 (s, 3H).

Example 16

1-Cyano-2-methyl-8-hydroxy-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[,2-a]pyrimidine

Specified in the title compound (1.35 g) are obtained by the method similar to the method of example 1 using the compound obtained in reference example 12 (4.15 g).

TLC: Rf= 0,15 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, DMSO-d6): δ 12,25 (users, 1H), 7,31 (d, J=7.8 Hz, 1H), 7,20 (d, J=2.7 Hz, 1H), 7,02 (DD, J=7,8, 2.7 Hz, 1H), 3,83 (s, 3H), and 2.83 (m, 2H), 2,66 (m, 2H), 2.06 to (s, 3H), 2,03 (m, 2H).

Example 17

1-Cyano-2-methyl-8-(3-pentylamine)-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,2-a]pyrimidine

Specified in the title compound (112 mg) are obtained by the method similar to the method of example 2, using 1-cyano-2-methyl-8-chloro-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrrolo[1,2-a]pyrimidine (180 mg)obtained by the method similar to the method of reference example 7, using the compound obtained in reference example 16.

TLC: Rf= 0,36 (toluene:ethyl acetate = 9:1).

NMR (300 MHz, CDCl3): δ to 7.25 (d, J=8,4 Hz, 1H), 7,05 (d, J=2.4 Hz, 1H), to 6.88 (DD, J=8,4, 2.4 Hz, 1H), 5,94 (d, J=9.0 Hz, 1H), 3,83 (s, 3H), 3,82 (m, 1H), 3.04 from (m, 2H), 2,87 (m, 2H), to 2.29 (s, 3H), 2,11(m, 2H), 1,82-to 1.60 (m, 4H), was 1.04 (t, J=7.5 Hz, 3H), of 1.03 (t, J=7.5 Hz, 3H).

Example 17(1)

1-Cyano-2-methyl-8-dipropylamino-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[d]pyrazolo[1,2-a]pyrimidine

Specified in the header is connected to the e, having the following physical properties, get the technique similar to the technique of a series of reactions of reference example 8 → reference example 9 → reference example 10 → reference example 11 → reference example 12 → example 16 → example 17, using the appropriate connection.

TLC: Rf= 0,39 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,26 (d, J=8,1 Hz, 1H), 7,06 (d, J=2.4 Hz, 1H), 6.89 in (DD, J=8,1, 2.4 Hz, 1H), 3,84 (s, 3H), 3,35-3,13 (m, 4H), 3.00 and is 2.80 (m, 4H), 2,32 (s, 3H), and 2.14 (m, 2H), 1,81-to 1.38 (m, 4H), of 0.91 (t, J=7.5 Hz,, 6H).

Reference example 13

5-Amino-4-cyano-2,3-dimethyl-1-(2-methyl-4-methoxyphenyl)pyrrol

To a solution of 2-methyl-4-methoxyaniline (10 g) in toluene (120 ml) add acetoin and hydrate p-toluenesulfonic acid (44 mg). The mixture is refluxed 2 hours. After cooling to room temperature, to the reaction mixture add malononitrile (4.6 ml) and refluxed for 12 hours. The cooled reaction mixture is concentrated. The residue is diluted with ether and filtered receive specified in the title compound (5.73 g) with the following physical properties.

TLC: Rf= 0,65 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,07 (d, J=8,4 Hz, 1H), 6.87 in (d, J=3.0 Hz, 1H), PC 6.82 (DD, J=3.0 a, and 8.4 Hz, 1H), 3,84 (s, 3H), 3,71 (users, 2H), 2.06 to (s, 3H), of 1.99 (s, 3H), at 1.73 (s, 3H).

Example 18

2,3-Dimethyl-4-amino-1-(2-methyl-4-methoxyphenyl)-6,7-di is Idro-5H-cyclopent[f]pyrrolo[2,3-b]pyridine

To a solution of the compound obtained in reference example 13 (4.0 g)in benzene (40 ml) was added Cyclopentanone (1,46 ml) and the hydrate p-toluenesulfonic acid (40 mg). The mixture is refluxed and dehydration within 12 hours. The insoluble substance is filtered through celite and the filtrate concentrated. In an argon atmosphere add 2M diisopropylamide lithium (15,7 ml in THF) to a solution of the residue in anhydrous tetrahydrofuran (80 ml) at 0°and then the mixture is heated to room temperature and stirred for 5 days. To the reaction mixture, water is added and the mixture extracted with ethyl acetate. The extract is washed successively with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated. The residue is purified column chromatography on silica gel (ethyl acetate), get mentioned in the title compound (2.85 g) having the following physical data.

TLC: Rfor = 0.51 (chloroform:methanol = 10:1).

NMR (300 MHz, CDCl3): δ 7,10 (d, J=8,4 Hz, 1H), 6,85 (d, J=3.0 Hz, 1H), 6,80(DD, J=3.0 a, and 8.4 Hz, 1H), or 4.31 (s, 2H), 3,83 (s, 3H), 2,90 (m, 2H), 2,74 (m, 2H), 2,48 (s, 3H), 2,10 (m, 2H), of 1.97 (s, 3H), 1,90 (s, 3H).

Example 19

2,3-Dimethyl-4-ethylcarbodiimide-1-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[f]pyrrolo[2,3-b]pyridine

To a solution of the compound obtained in example 18 (600 mg), TG is (60 ml), add triethylamine (520 μl) and propionitrile (180 μl). The mixture is stirred for 2 hours. The reaction mixture was diluted with ethyl acetate, the diluted solution was washed with saturated aqueous sodium bicarbonate and then saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated. The residue was washed with hexane, and get mentioned in the title compound (451 mg), which has the following physical properties.

TLC: Rf= 0,60 (chloroform:methanol = 10:1).

NMR (300 MHz, CDCl3): δ 7,30 (m, 1H), was 7.08 (d, J=8,4 Hz, 1H), 6.87 in (d, J=2.7 Hz, 1H), 6,83 (DD, J=2.7, and an 8.4 Hz, 1H), 3,84 (s, 3H), 2,98 (t, J=7.2 Hz, 2H), 2,87 (m, 2H), of 2.51 (m, 2H), is 2.37 (s, 3H), of 2.09 (m, 2H), 2,02 (s, 3H), of 1.88 (s, 3H), of 1.33 (m, 3H).

Example 20

2,3-Dimethyl-4-propylamino-1-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[f]pyrrolo[2,3-b]pyridine

To a solution of the compound obtained in example 19 (451 mg)in THF (5.0 ml) is added 2M complex of borane and dimethyl sulfide (4.8 ml; in THF) and the mixture is refluxed 5 hours. To the reaction mixture is added methanol and then refluxed 2 hours. After cooling, the reaction mixture was diluted with ethyl acetate. The diluted solution was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated. The residue is purified column chromatography on silica gel (hexane:ethyl acetate = 1:1)receive specified in is the head of the compound (268 mg), which has the following physical properties.

TLC: Rf= 0,47 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ to 7.09 (d, J=8.7 Hz, 1H), 6,85 (d, J=2.7 Hz, 1H), 6,80 (DD, J=2.7, and 8.7 Hz, 1H), 3,83 (s, 3H), 3.43 points (m, 2H), 3,05 (m, 2H), 2,84 (m, 2H), 2,48 (s, 3H), 2,04 (m, 2H), of 1.97 (s, 3H), 1,90 (s, 3H), of 1.65 (m, 2H), of 1.02 (t, J=7.5 Hz, 3H).

Example 21

2,3-Dimethyl-4-(N-ethylcarbazole-N-propylamino)-1-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[f]pyrrolo[2,3-b]pyridine

In the atmosphere of argon added triethylamine (360 μl) and propionitrile (134 μl) to a solution of the compound obtained in example 20 (234 mg)in methylene chloride (3.0 ml) at 0aboutC. the Mixture is stirred for 1 hour. The reaction mixture was diluted with ethyl acetate, and the diluted solution was washed with saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated. The residue is purified column chromatography on silica gel (hexane:ethyl acetate = 2:1)receive specified in the title compound (242 mg), which has the following physical properties.

TLC: Rf= 0,57 (hexane:ethyl acetate = 1:1).

NMR (300 MHz, CDCl3): δ 7,11 (m, 1H), make 6.90 (d, J=2.4 Hz, 1H), 6,85 (DD, J=2,4, and 8.4 Hz, 1H), 3,92 (m, 1H), 3,86 (s, 3H), 3,42 (m, 1H), 3,01 (t, J=7.8 Hz, 2H), 2,87 (m, 2H), measuring 2.20 (s, 3H), 1,94-of 2.20 (m, 4H), to 2.06 (s, 3H), 1.92 and 1,90 (s, total 3H), and 1.63 (m, 2H), 0,99-1,10 (m, 3H), 0,85-of 0.94 (m, 3H).

Example 22

2,3-Dimethyl-4-dipropyl the Mino-1-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[f]pyrrolo[2,3-b]pyridine

Specified in the title compound (182 mg)having the following physical properties, get the technique similar to the method of example 20, using the compound obtained in example 21 (242 mg).

TLC: Rf= 0,45 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,10 (d, J=8,4 Hz, 1H), 6.87 in (d, J=2.7 Hz, 1H), for 6.81 (DD, J=8,4, 2.7 Hz, 1H), 3,84 (s, 3H), 3,17 (m, 4H), 2.95 points (t, J=7.5 Hz, 2H), 2,88 (t, J=7.5 Hz, 2H), 2,44 (s, 3H), of 2.05 (m, 2H), 2,01 (s, 3H), of 1.92 (s, 3H), of 1.52 (m, 4H), of 0.85 (t, J=7.2 Hz, 6H).

Example 22(1)

2,3-Dimethyl-4-(N-ethyl-N-pentylamine)-1-(2-methyl-4-methoxyphenyl)-6,7-dihydro-5H-cyclopent[f]pyrrolo[2,3-b]pyridine

Specified in the title compound having the following physical properties, get the technique similar to the technique of a series of reactions of example 19 → example 20 → example 21 → example 22, using the compound obtained in example 18, and the corresponding connection.

TLC: Rf= 0,41 (hexane:ethyl acetate = 3:1).

NMR (300 MHz, CDCl3): δ 7,10 (d, J=8,4 Hz, 1H), 6,86 (d, J=2.7 Hz, 1H), for 6.81 (DD, J=8,4, 2.7 Hz, 1H), 3,84 (s, 3H), 3.27 to (sq, J=6,9 Hz, 2H), 3,18 (m, 2H), 2.95 points (t, J=7.2 Hz, 2H), 2,88 (t, J=7.8 Hz, 2H), 2,44 (s, 3H)that was 2.05 (m, 2H), from 2.00 (s, 3H), 1.91 a (s, 3H), 1,50 (m, 2H), 1,38 is 1.20 (m, 4H), of 1.05 (t, J=6.9 Hz, 3H), 0,86 (t, J=6.9 Hz, 3H).

Sample preparation

Sample preparation 1

The following components are mixed in the usual way and pressed to obtain 100 tablets each to the x contains 50 mg of active ingredient.

8-(3-Pentylamine)-2-methyl-3-(2-methyl-4-methoxyphenyl)-
6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine5.0 g
Calcium salt of carboxymethylcellulose
(dispersing agent)0.2 g
Magnesium stearate (lubricating agent)0.1 g
Microcrystalline cellulose4.7 grams

Example product 2

The following components are mixed in the usual way. The solution is sterilized in the usual way, put in portions of 5 ml in ampoules and dried by freezing, obtain 100 ampoules each containing 20 mg of the active ingredient.

8-(3-Pentylamine)-2-methyl-3-(2-methyl-4-methoxyphenyl)-
6,7-dihydro-5H-cyclopent[d]pyrazolo[1,5-a]pyrimidine2.0 g
Mannitol20 g
Distilled water500 ml

1. The compound of formula (I)

where X represents a carbon and Y is carbon or nitrogen;

W represents a carbon or nitrogen;

U represents CR2The Z represents CR 2or nitrogen,

R2represents a

(i) hydrogen,

(ii) C1-8-alkyl,

(iii) CF3,

(iv) cyano,

(v) OR11in which R11represents a

(i) hydrogen,

(ii)1-4-alkyl,

(vi) SR12where R12represents a C1-4alkyl

(vii)3-6-cycloalkyl ring,

(viii) phenyl ring

(ix) foreline ring,

(x)1-4-alkyl, substituted by substituents selected from OR11, SR12or =N-OR11,represents a single or double bond,

represents a C5-6-cycloalkyl ring or 5-membered heterocyclic ring containing one nitrogen atom, oxygen or sulfur, and such rings are unsubstituted or substituted C1-4-alkyl,

R1represents a

(i) C1-8-alkyl, which is unsubstituted or substituted by 1-2 substituents R14;

(ii) NR4R5where each of the substituents R4and R5independently from each other represents a

(i) hydrogen,

(ii) C1-15-alkyl, which is unsubstituted or substituted by 1-2 substituents R17;

(iii)2-15alkenyl;

(iv)2-15

(v)3-10-mono - or bi-carbocyclic ring which is unsubstituted or substituted by 1-3 substituents R18;

(iii) OR6in which R6represents a

(i) hydrogen,

(ii) C1-10-alkyl,

(iii)2-10alkenyl,

or R1represents a

(iv) SR7in which R7represents C1-8-alkyl,

(v) NR8COR6awhere R6arepresents a C1-10-alkyl, and

R8represents a

(i) hydrogen,

(ii) C1-8-alkyl;

(vi) a phenyl ring which is unsubstituted or substituted by 1-2 substituents R15;

(vii)5-10membered mono - or biheterocyclic ring containing 1-2 nitrogen atom,

which is substituted R15;

R11arepresents (i) hydrogen or (ii) C1-4-alkyl,

R14represents (a) OR6(b) COR6, (C) COOR6, (d) CONR4R5where R4and R5each independently represents hydrogen or C1-8alkyl;

R15represents (a) C1-8-alkyl, (b) (C1-4-alkoxy(C1-4)-alkyl, (C) halogen, (d) CF3(e) OCF3, (f) cyano, (g) OR6, (h) COR6(j) COOR6, (k) a phenyl ring which is unsubstituted or substituted what alogena, (1)1,2,4-oxadiazolyl, substituted C1-4the alkyl (m)1-4alkyl, substituted OR6;

R17represents (a) CF3, (b) cyano, (C) NR9R10, (d) OR11a, (e) =N-OR11and (f) SR12(g) COR11, (h)3-6cycloalkyl or phenyl ring which is unsubstituted or substituted R18aor (j) a mono - or biheterocyclic ring selected from tetrahydrofuranyl, furil, teinila, and benzodioxane, which is unsubstituted or substituted With1-4by alkyl;

R18represents a C1-4-alkyl,

R18arepresents (a)1-4-alkyl, (b) halogen, (C) CF3, (d) OCF3, (e) cyano, (f) SR12(g)OR11a,

R3represents (i) a phenyl ring substituted by 1-3 substituents R16or (ii) peregrinae or 1,3-dioxindole ring, substituted with 1-2 R16,

R16represents a

(a)1-8-alkyl,

(b) halogen,

(c) CF3,

(d) OCF3,

(e) cyano,

(f) NR9R10where R9and R10independently from each other represent

(i) hydrogen,

(ii)1-4alkyl,

(g) OR11,

(k) COOR11,

(h) S(O)nR12where n is from 0 to 2, with the exception of phenylthio,

(i) COR11,

(k) CONR9R10,

(m)1-4-alkyl, substituted by 1-2 substituents OR11;

provided that when each of X and W is carbon, each of Y and Z is nitrogen, U represents CR2and R1is a OR6, R3is not phenyl, substituted 1 atom of halogen, phenyl, substituted 1-trifluoromethyl.

or its pharmaceutically acceptable salts or hydrates.

2. The compound according to claim 1, where W represents a carbon, each of Y and Z represents nitrogen, its pharmaceutically acceptable salt or hydrate.

3. The compound according to claim 1, where W represents a carbon, Y is nitrogen, its pharmaceutically acceptable salt or hydrate.

4. The compound according to claim 1, where Y is a carbon, W is a nitrogen, its pharmaceutically acceptable salt or hydrate.

5. The compound of the formula (I-i)

where all the symbols have the meanings defined in claim 1, according to claim 1, its pharmaceutically acceptable salt or hydrate.

6. The compound of the formula (I-ii)

where all the symbols have the meanings defined in claim 1, according to claim 1, its pharmaceutically acceptable salt or hydrate.

7. The compound according to claim 1, represents:

(59) 8-(3-pentylamine)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5 is-cyclopent[d]pyrazolo[1,5-a]pyrimidine;

8. Pharmaceutical composition for treatment and/or prevention of diseases caused by excessive secretion of corticotropinreleasing factor, namely depression, single episode depression, recurrent depression, postpartum depression, depression, caused by poor treatment of child anxiety, disorders associated with fear (for example panic, specific phobia, fear of ruin, social phobia, obsessive compulsive disorder), emotional disorders, bipolar disorder, post traumatic stress disorder, peptic ulcer, diarrhea, constipation, irritable bowel syndrome, inflammatory bowel disease (ulcerative colitis, Crohn's disease), caused stress disorders of the gastrointestinal tract, nervous vomiting, disorders of food intake (such as loss of appetite, bulimia nervous), obesity, stress-related sleep disturbance, pain, muscle fibers caused by sleep disorders, stress-induced suppression of the immune system caused by stress headaches, stress-induced fever, caused by stress, pain, post-operative stress, rheumatoid arthritis, osteoarthritis, osteoporosis, psoriasis, thyroid dysfunction, uveitis, asthma, induced inappropriate Antidiarrhoeal hormone disorders, the Oli, inflammation, allergic diseases, wounds of the head, spinal cord injury, ischemic neuronal damage, toxic neural damage, disease, Cushing (Gushing), of an apoplectic fit, spasm, muscle spasm, epilepsy, ischemia, Parkinson's disease, Huntington's disease, urinary incontinence, Alzheimer's disease, senile dementia in medical literature type, multi-infarct dementia, amyotrophic lateral sclerosis, hypoglycemia, cardiovascular or associated with heart disease (hypertension, tachycardia, congestive heart failure), addiction to the excessive use of drugs or alcohol syndrome, which includes a compound of formula (I) claim 1, its pharmaceutically acceptable salt or hydrate as an active ingredient.



 

Same patents:

FIELD: organic chemistry, biochemistry, medicine, pharmacy.

SUBSTANCE: invention describes a compound of the general formula (I) or (II) wherein R1 represents hydrogen atom; R2 is taken among the group consisting of aryl and heteroaryl; R3 is taken among the group consisting of halogen atom, nitro-, cyano-group, (C1-C6)-alkyl, (C1-C6)-alkoxy-group, trifluoromethyl, trifluoromethoxy-group, -NH2, -NH-(C1-C6)-alkyl and -N-(C1-C6)-alkyl)2; b is a whole number from 0 to 4; R4 is taken independently among the group consisting of halogen atom, hydroxy-, carboxy-, oxo-group, (C1-C6)-alkyl, (C1-C6)-alkoxy-group, (C1-C6)-alkoxycarbonyl, phenyl (wherein phenyl group can be substituted optionally with one-three substitutes taken independently among RD), phenylsulfonyl, heteroaryl (wherein heteroaryl can be substituted optionally with one-three substitutes taken independently among RD), heterocycloalkyl, -NH2, -NHRA, -N-(RA)2,

wherein each RD is taken independently among halogen atom, hydroxy-, carboxy-, oxo-group, (C1-C4)-alkyl, (C1-C4)-alkylthio, hydroxy-(C1-C4)-alkyl, (C1-C4)-alkoxy-group, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylcarbonyl, trifluoromethyl, trifluoromethoxy-group, -NH2. -NHRA, -N-(RA)2, -C(O)N(RA)2, -SO2N(RA)2, acetylamino-, nitro-, cyano-group, formyl, (C1-C6)-alkylsulfonyl, carboxy-(C1-C6)-alkyl and aralkyl; c = 0; a means a whole number from 0 to 1; Y is taken among the group consisting of a residue -(C1-C)-alkyl, -C(O)-, -(C2-C6)-alkenyl)-carbonyl, -carbonyl-(C1-C6)-alkyl)-, -C(S)-, -C(O)NH-(C1-C6)_alkyl), -C(O)-(C3-C7)-cycloalkyl)- and (C3-C7)-cycloalkyl)-C(O)-; represents phenyl;

is taken among the group consisting of phenyl, heteroaryl and cycloalkyl under condition that when R1 represents hydrogen atom, R3 represents hydrogen atom, b = 0, c = 1, Y represents -CH2-, represents phenyl and represents phenyl then R2 is not trimethoxyphenyl, and its pharmaceutically acceptable salts. Also, invention describes a pharmaceutical composition designated for inhibition of activity of phosphodiesterase comprising a pharmaceutically acceptable vehicle and compound by cl. 1, method for preparing pharmaceutical composition, methods for treatment of sexual dysfunction by using compound by cl. 1 or pharmaceutical composition, method for increasing the concentration of cGMP in penis tissue and method for treatment of state when inhibition of activity of phosphodiesterase shows the favorable effect. Invention provides preparing novel compounds possessing useful biological properties.

EFFECT: valuable medicinal and biochemical properties of compounds and composition.

17 cl, 7 tbl, 98 ex

FIELD: organic chemistry, biochemistry, pharmacy.

SUBSTANCE: invention relates to new anellated carbamoyl azaheterocycles of the general formula (1)

or (2) possessing the inhibitory effect on protein kinase activity, a focused library comprising these compounds, and pharmaceutical composition based on thereof. In the general formula (1) or (2) R1 represents hydrogen atom or optionally substituted (C1-C6)-alkyl; R2 and R3 represent independently of one another hydrogen atom, inert substitute, optionally substituted (C1-C6)-alkyl, optionally substituted (C3-C8)-cycloalkyl, optionally substituted phenyl, optionally substituted aryl, optionally substituted heterocyclyl; R4 represents optionally substituted (C1-C6)-alkyl, optionally substituted (C3-C8)-cycloalkyl, optionally substituted phenyl, optionally substituted aryl, optionally substituted heterocyclyl; A and B in common with carbon and nitrogen atoms joined to the form an optionally substituted and optionally condensed azaheterocycle; D and F in common with carbon atoms joined form an optionally substituted and optionally condensed phenyl or aryl, optionally substituted and optionally condensed azaheterocycle. K and L in common with carbon and nitrogen atoms joined to them form an optionally substituted azaheterocycle. Also, invention related to methods for preparing compounds of the general formulae (1) or (2).

EFFECT: improved preparing methods.

10 cl, 2 sch, 25 tbl, 7 ex

FIELD: organic chemistry, chemical technology, pharmacy.

SUBSTANCE: invention relates to new biologically active derivatives of pyridothienodiazepine. Invention describes derivatives of pyridothienodiazepine of the general formula (I):

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EFFECT: improved preparing method, valuable medicinal properties of compounds.

17 cl, 70 ex

The invention relates to new 3-substituted derivatives 3,4,5,6,7,8-hexahydropyrazino[4', 3': 4,5] -thieno[2,3-d] pyrimidine of the General formula I and their physiologically acceptable salts with selective action of antagonists 5HT1Band 5HT1Aand has inhibiting effect of reuse of serotonin

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The invention relates to novel condensed isoindoline formula I

< / BR>
where ring b and F are independently from each other represent a 6-membered carbocyclic ring; R1means H, C1-C4alkyl; AND1and2pairs are selected from the group including =O, N, -OR", where R" denotes N;1and2pairwise mean =O; X in all positions independently from each other selected from the group: a) unsubstituted WITH1-C3alkylen, b) -S-; R3, R4, R5, R6independently from each other selected from the group comprising H1-C4alkyl; compounds 1 can be used for inhibiting protein kinase C (PKC) and inhibit the activity of tyrosine kinase (trk)

--carboline" target="_blank">

The invention relates to bellrowan-carbolines, formula I, where R3denotes-CO-R1or group (a); R1- C1-C6alkoxy; R2- N2C1-C4alkyl, C1-C4alkoxy - C1-C2alkyl; And -- 5-6-membered unsaturated cycle, in which 1-2 carbon atoms may be replaced by N, O and/or S, which may be substituted with one R5or R6; R5and R6identical or different, denote H, C1-C6alkyl, NR7R8C1-C6alkyl which may be substituted by hydroxyl or C1-C4alkoxyl, phenyl, 5-6-membered heteroaryl residue, which contains one or two atoms of N, O or S, and phenyl and heteroaryl residue may be substituted C1-C4the alkyl, C1-C4alkoxyl, halogen, or R5and R6together,- CH2)nwhere n = 4; R7and R8- H, C1-C4alkyl, acyl, as well as their isomers, tautomers and salts

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FIELD: organic chemistry of heterocyclic compounds, biology, medicine, pharmacy.

SUBSTANCE: invention relates to new substituted pyrido[4',3':5,6]pyrano[2,3-d]pyrimidines of the general formula (1): or (2): or their pharmaceutically acceptable salts, N-oxides or hydrate possessing physiologically active properties, in particular, eliciting ability to induce apoptosis in tumor cells causing their death. In the general formula (1) or (2) X represents sulfur or oxygen atom; Y represents sulfur atom, group -SO, group -SO2, group -NH or group -NR6; R1 represents aryl, substituted aryl, heteroaryl; R2 and R5 represent hydrogen atom, alkyl, allyl, substituted benzyl, group -CH2-C(O)R3, group -CH2-C(O)NR3R4 wherein R3, R4 and R6 represent inert substitute. Also, invention relates to new combinatory libraries for search compound-leaders and candidates for medicinal compounds preparing by screening the combinatory libraries.

EFFECT: valuable medicinal properties of compounds.

9 cl, 1 tbl, 9 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to a new substance eliciting an antiviral and antibacterial activity that is based on derivatives of 2,8-dithioxo-1H-pyrano[2,3-d;6,5-d']dipyrimidine and their 10-aza-analogues. This substance comprises derivative of indicated group of the general formula: A1*M: wherein X is taken among the group: oxygen atom (O), NH, N-alkyl; R1 is taken among the group: hydrogen atom (H), OH, chlorine atom (Cl), O-alkyl, NH2, NH-alkyl, NH-Ar, N-(alkyl)2, SH, S-alkyl; R2 is taken among the group: unsubstituted or substituted phenyl, naphthyl, thienyl; R3 is taken among the group: hydrogen atom (H), chlorine atom (Cl), O-alkyl, NH2, NH-alkyl, S-dihydroxypyrimidinyl; M is absent or taken among the group: cation Na, K, Li, ammonium or any other pharmacologically acceptable cation; or complex of pharmacologically acceptable cation (see above) with anion of one of derivatives of A1 (variants R1-R3 are given above). Invention provides preparing new compounds eliciting an antiviral and antibacterial activity.

EFFECT: valuable medicinal properties of substance.

17 cl, 7 tbl, 16 ex

The invention relates to a method for producing a condensed polycyclic alkaloids of General formula I, including new, including phase cyclization of azometynoylid General formula II, where a is optionally substituted aryl, Z is oxygen, n = 1, Y is optionally substituted aryl, W and X together with the nitrogen atoms and the carbon to which they are attached, form a saturated or unsaturated nitrogen-containing heterocyclic group, possibly substituted and possibly condensed with aryl, carbocyclic or heterocyclic group

The invention relates to novel condensed pyrrolo (2,3-C)carbazole-6-Onam represented by the General formulas (I) and (II)

The invention relates to new derivatives of 5H-pyrano[2,3-d:6,5-d']dipyrimidine General formula I possess anti-microbial, antiviral and immunomodulatory effects

The invention relates to a new process for the preparation of 9-amino-20/S/-camptothecin formula /I/

< / BR>
which is a well-known anti-cancer agent: Wani, etc

The invention relates to the field of macrolides

FIELD: organic chemistry, medicine.

SUBSTANCE: invention relates to derivatives of imidazo[1,5-a]pyrimido[5,4-d][1]benzazepine of the formula (I): , wherein R1 means halogen atom or (lower)alkyl; R2 means hydrogen atom, (lower)alkyl, (C3-C7)-cycloalkyl, -(CH2)m-phenyl wherein phenyl ring can be substituted with (lower)alkoxy-group or it means -(CH2)m-indolyl; R3 means -C(O)O-(lower)alkyl, -C(O)OH or five-membered heteroaromatic group comprising nitrogen and oxygen atoms as heteroatoms and wherein rings can be substituted with (lower)alkyl or (C3-C7)-cycloalkyl; n means 0, 1 or 2; m means 0, 1 or 2, and their pharmaceutically acceptable acid-additive salts. Compounds of this class elicit the high degree and selectivity to binding sites of GABA A α5-receptor and can be used in treatment of the conception enhancer or disorders of cognitive ability similar with Alzheimer's disease.

EFFECT: valuable medicinal properties of derivatives.

10 cl, 6 sch, 41 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention describes derivatives of benzodiazepine of the general formula (I): wherein R1 represents hydrogen, halogen atom, (C1-C7)-alkyl, hydroxy- or (C1-C7)-alkylthio-group; R2 represents -C(O)O-(C1-C7)-alkyl, 1,2,4-oxadiazole-3-yl or 1,2,4-oxadiazole-5-yl wherein their cyclic fragments are substituted with (C3-C7)-cycloalkyl; R3 represents hydrogen atom (C1-C7)-alkyl, -(CH2)n-(C3-C7)-cycloalkyl, -(CH2)n-halogen, -(CH2)n-pyridine-4-yl or -(CH2)n-phenyl wherein phenyl ring can be substituted with one or some substitutes chosen from the group comprising (C1-C7)-alkoxy-group, halogen atom, -SO2CH3, phenyl, -OCF3, nitro-group, -CF3, -NR2, or it means -(CH)n-indolyl optionally substituted with (C1-C7)-alkyl or (C1-C7)-alkoxy-group, or means pyrrolidinyl-5-oxo-group, -C(O)-NR2, -(CH2)n-OH, -(CH2)n-NR2 or -(CH2)n-benzo[1,3]dioxol; R represents hydrogen atom or (C1-C7)-alkyl; n = 0, 1, 2 or 3, and its pharmaceutically acceptable acid-additive salts with exception for the following compounds: 9H-imidazo[1,5-a][1,2,4]triazolo[3,4-d][1,4]benzodiazepine-10-carboxylic acid ethyl ester. 10-(3-cyclopropyl-1,2,4-oxadiazole-5-yl)-9H-imidazo[1,5-a][1,2,4]triazolo[4,3-d][1,4]benzodiazepine, 3-fluoro-9H-imidazo[1,5-a][1,2,4]triazolo[4,3-d]benzodiazepine-10-carboxylic acid ethyl ester, 10-(3-cyclopropyl-1,2,4-oxadiazole-5-yl)-3-fluoro-9H-imidazo[1,5-a][1,2,4]triazolo[4,3-d][1,4]benzodiazepine, 3-chloro-9H-imidazo[1,5-a][1,2,4]triazolo[4,3-d][1,4]benzodiazepine-10-carboxylic acid ethyl ester, 3-chloro-1-(3-cyclopropyl-1,2,4-oxadiazole-5-yl)-9H-imidazo[1,5-a][1,2,4]triazolo[4,3-d][1,4]benzodiazepine and 3-methyl-9H-imidazo[1,5-a][1,2,4]triazolo[3,4-d][1,4]benzodiazepine-10-carboxylic acid ethyl ester. Also, invention relates to pharmaceutical composition comprising both new and above enumerated and excluded compounds. New compounds possess ability for selective binding with α5-subunit of gamma-aminobutyric acid receptor A and can be used in treatment, for example, Alzheimer's diseases.

EFFECT: valuable medicinal properties of compounds and pharmaceutical composition.

13 cl, 1 tbl, 67 ex

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