4-hydroxy-3-chinainternational and hydrazides, pharmaceutical composition and method of treatment based on them

 

The invention relates to 4-hydroxy-3-chinainternational and hydrazides of General formula (I), where a represents a-CH2- or-NH-, a R1, R2, R3and R4such as defined in the claims. Also described pharmaceutical composition on the basis of these compounds and a method of treatment of infectious diseases caused by viruses of the herpes family. The technical result obtained new compounds possess valuable biological properties. 4 C. and 12 C.p. f-crystals, 1 PL.

Description text in facsimile form (see graphic material)

Claims

1. 4-hydroxy-3-chinainternational or hydrazide of the formula I

or its pharmaceutically acceptable salt,

where a is a

(a)- (CH2or

b) -NH-;

R1, R2, R3and R4represent independently from each other,

a) H,

b) halogen,

c) -CN,

d) -NO2,

e) aryl,

(f) heterocycle (het),

g) OR5,

h)1-12alkyl,

i)1-12alkyl, substituted one to three-CN, halogen, OR5,

-C(=O)R5, -COOR5, heterocycle (GE is 1,

k) -CH=CH-R12,

l) -(CH2)m-C(=O)R13,

m) -SR14,

n) -C(=S)R15,

o) -(CH2)m-SOiR13,

p) -NR7R8,

q) -NHSOiR13,

r) R1and R2taken together, represent a heterocycle

or

s) R2and R3taken together, represent a heterocycle

or4-6cycloalkyl;

R5represents a

a) H,

b) C1-8alkyl, optionally substituted one to three-HE, C1-4alkoxy, halogen,

c) aryl or

(d) heterocycle;

R6represents a

and-SO2With1-6alkyl;

R7and R8represent independently from each other,

a) H,

b) C1-8alkyl, optionally substituted with one to three

halogen, -CN, OR5, aryl, heterocycle, With3-6cycloalkyl, C1-6the quinil, C1-6alkenyl, -SR14or-NR16R17,

c) aryl,

(d) heterocycle,

(e) -(CH2)m-C(=O)OR5,

f) -(CH2)m-C(=O)R5;

R9represents a

(a) HE or

b) -OC1-8alkyl;

R10represents a

a) H,

b) -NR7R8,

c) C1-8alkyl, substituted by one or two halogen atoms, heterocycles, which are things like a

a)1-8alkyl, substituted one to three-CN, halogen, -COOR5, -SR5, -OR5, -NR7R8, -OC(=O)R10or

(C) -(CH2)m-heterocycle (het);

R12represents a

a) CN,

(b) (C1-8alkyl, substituted one to three-SR5, -OR5,

c) -C(=O)R5or

d) -COOR5;

R13represents a

a) C1-8alkyl,

b) C1-8alkyl, substituted with one to three aryl, -OR5,

c) a heterocycle,

d) aryl,

e) -NR7R8,

f) OR5,

q) halogen;

R14represents a

a) C1-8alkyl or

b) C1-8alkyl, substituted one to three, heterocycle, aryl, -OR5or-NR7R8;

R15represents a

a) -NH2or

b) -NHNH2;

R16and R17represent independently from each other,

a) H,

b) -C(=O)1-4alkyl;

aryl represents phenyl or naphthyl, optionally substituted by R18;

a heterocycle (het) is a 5-or 6-membered saturated or unsaturated heterocyclic ring having 1-3-heteroatom selected from the group consisting of nitrogen, oxygen and sulfur, where the heterocyclic ring is optionally condensed with benzoline a

a) halogen,

b) phenyl,

c) C1-8alkyl, substituted by one to three halogen atoms, -OR5,

d) OR5or

e) -SO2NH2;

M represents a sodium atom;

i = 1 or 2;

m = 0 or 1;

n = 2;

under the following conditions:

(a) when R2, R3and R4represent hydrogen, R1is a group other than methoxy,

(b) when R4represents CL, each of R2and R3represents hydrogen, R1is a group other than methyl,

(c) when R1represents hydrogen, each of R2and R4represents fluorine, and R3represents a heterocycle (het), heterocycle (het) is different from the substituted piperazinil,

(d) when R1and R3represent hydrogen, R2represents fluorine, R4is a group other than fluorine,

(e) when R2and R4represent hydrogen, R1represents fluorine, R3is a group other than fluorine,

(f) when R1and R3represents hydrogen, R2represents chlorine, R4is a group other than chlorine,

(g) when R1, R2and R3are R2is not cryptometrics,

(i) when R1, R2and R4represent hydrogen, R3is not triptoreline, and

(j) when R1, R2and R3represent hydrogen, R4is not morpholinium.

2. Connection on p. 1, where a represents a-CH2-.

3. Connection on p. 1, where R1, R2, R3and R4independently of one another represent a) halogen,

b) -CN-,

c) -NO2,

d) phenyl

e) heterocycle (het),

f) -OR5,

g) C1-6alkyl,

h) C1-6alkyl, substituted one to three-CN, halogen, OR5, -C(=O)R5, heterocycle, -COOR5, -OP(=O)(R9)2, -OPH(=O)R9

or-OC(=O)R10,

i) -CCR11,

j) -CH=CH-R12,

k) -C(=O)R13,

l) -SR14,

m) -SOiR13,

n) -NR7R8,

o) -NHSOiR13or

p) R1and R2taken together, represent a heterocycle;

R5represents a

a) H,

(b) (C1-4alkyl, optionally substituted by one to three groups-HE, halogen, C1-4alkoxy or

c) phenyl;

R7and R8represent independently from each other,

a) H,

(b) (C1-4Ala-C(=O)OR5or

(e) -(CH2)m-C(=O)R5;

R9represents (a) HE or

b) -OC1-8alkyl;

R10represents a

a) H,

b) -NR7R8or

c) C1-8alkyl, substituted by one or two atoms of halogen, heterocycle, -NR7R8or-C(=O)N(C1-4alkyl) (CH2)nS(=O)2O-M+;

R11represents a

a) C1-8alkyl, substituted by one to three halogen atoms, -CN, -OR5or-OC(=O)R10;

R12represents (a) C(=O)R5or

b) C1-4alkyl, substituted one to three-OR5,

R13represents a

a)1-4alkyl,

(b) (C1-4alkyl, substituted by one to three groups phenyl, -OR5;

c) phenyl,

e) -NR7R8or

f) OR5;

R14represents a

a) C1-4alkyl, optionally substituted by phenyl;

aryl represents phenyl optionally substituted by R18or naphthyl;

the heterocycle is pyrrolyl, morpholinyl, thiophenyl, thiazolyl, pyridinyl, thiadiazolyl or 2-oxo-oxazolyl, where the heterocycle optionally substituted R18,

R18represents a

a) halogen,

b) phenyl,

c1-4lcil, Deputy Prov.

i = 2;

m = 1;

n = 2.

4. Connection on p. 1, where

R1represents N;

R2, R3and R4independently from each other represent a

(a) fluorine,

b) a heterocycle,

c) -OR5,

d) C1-6alkyl, substituted with halogen, OR5, -C(=O)R5, -OP(=O) (R9)2, heterocycle, -OPH(=O)R9or-OC(=O)R10,

e) -CCR11,

f) -CH=CH-R12,

g) -C(=O)R13or

h) -NR7R8,

R5represents a

a) H, or

(b) (C1-4alkyl, optionally substituted-HE, halogen or

With1-4alkoxy;

R7and R8independently from each other represent a

a) H,

(b) (C1-4alkyl, optionally substituted by one or two atoms of halogen, -OR5or phenyl or

c) -C(=O)R5;

R9represents a

(a) HE or

b) -OS1-4alkyl;

R10represents a C1-8alkyl, substituted one or two of the following groups:

a) -C (=O) N (C1-4alkyl) (CH2)nS(=O)2O-M+,

b) halogen, or

c) -NR7R8;

R11represents a C1-4alkyl, substituted OR5or-OC(=O)R10;

R12represents a C1-4alkyl, predstavljaet morpholinyl or thiophenyl;

M is an atom of sodium and

n = 2.

5. Connection on p. 1, where

R1and R3independently from each other represent hydrogen;

R4represents a

a) H,

b) a fluorine or

c) -OR5;

R2represents a

a) thiophenyl,

b) C1-6alkyl, substituted OR5, -OP(=O)(OH)2, -ORN(=O)(OH) or-OC(=O)R10,

c) -CCR11or

d) -CH=CH-R12;

R5represents a

a) N or

(b) (C1-4alkyl, optionally substituted-HE or1-4alkoxy;

R10represents a C1-8alkyl, substituted one or two of the following groups:

a) -C (=O) N (C1-4alkyl) (CH2)2S (=O)2O-M+or

b) -NH2;

R11represents a C1-4alkyl, substituted OR5or-OC(=O)R10;

R12represents a C1-4alkyl, substituted OR5and

M represents a sodium atom.

6. The compound of the formula I

or its pharmaceutically acceptable salt,

where a is a

(a)- (CH2or

b) -NH-;

R1, R2, R3and R4represent independently from each other,

a) a heterocycle,

b)-OPH(=O)R9or-OC(=O)R10,

c)

d) -CH=CH-R12,

e) -C(=S)R15,

f) -NR7R8,

g) -NHSOiR13,

h) R1and R2taken together, represent a heterocycle or

R2and R3taken together, represent a heterocycle or

With4-6cycloalkyl;

R5represents a

a) H,

b) C1-8alkyl, optionally substituted one to three-HE,

C1-4alkoxy, halogen,

c) aryl or

(d) heterocycle;

R7and R8represent independently from each other,

a) H,

b) C1-8alkyl, optionally substituted one to three, halogen, -CN, OR5, aryl or heterocycle,

c) aryl,

(d) heterocycle,

(e) -(CH2)m-C(=O)OR5,

f) -(CH2)m-C(=O)OR5;

R9represents a

(a) HE or

b) -OS1-8alkyl;

R10represents a

a) H,

b) NR7R8,

C) C1-8alkyl, substituted by one or two atoms of halogen, heterocycle, -NR7R8or-C(=O)N(C1-4alkyl) (CH2)nS(=O)2O-M+;

R11represents a

a) C1-8alkyl, substituted one to three-CN, halogen, -COOR5, -SR5, -ORalkyl, substituted one to three, -SR5, -OR5,

b) -C(=O)R5or

c) -COOR5;

R13represents a

a) C1-8alkyl,

b) C1-4-alkyl, substituted by one to three aryl, -OR5,

c) a heterocycle,

d) aryl,

e) -NR7R8or

f) OR5;

R15represents a

a) -NH2or

b) -NHNH2;

aryl represents phenyl or naphthyl, optionally substituted by R18;

the heterocycle is a 5 - or 6-membered saturated or unsaturated heterocyclic ring having 1-3-heteroatom selected from the group consisting of nitrogen, oxygen and sulfur, and the heterocyclic ring is optionally condensed with a benzene ring and optionally substituted by an R18;

R18represents a

a) halogen,

b) phenyl,

c) C1-8alkyl, optionally substituted with one to three halogen atoms, -OR5;

d) OR5;

e) SO2NH2;

M represents a sodium atom;

i = 1 or 2;

m = 0;

n = 2;

provided that

(a) when R1represents hydrogen, each of R2and R4represents fluorine, and R3represents a heterocycle, the heterocycle is different from zamestnavatelia,

(c) when R1, R2, R3and R4independently represent-NR7R8, R7and R8are not hydrogen or alkyl,

(d) heterocycle is different from the cyclic amino group.

7. The method of treatment of infectious diseases caused by herpes viruses, such as herpes simplex virus (herpes simplex), herpes virus, the causative agent of chickenpox (varicella zoster), cytomegalovirus, Epstein-Barr, human herpes virus 8, which includes the introduction of required treatment to the patient an effective amount of the compounds of formula I.

8. The method according to p. 7, where the named herpes virus is a human cytomegalovirus.

9. The method according to p. 7, where the effective amount of the compounds under item 1 is administered orally, parenterally or topically.

10. The method according to p. 7, where the effective amount of the compounds on p. 1 represents 0.1 to 300 mg/kg body weight.

11. The method according to p. 7, where the effective amount of the compounds on p. 1 represents from about 1 to 30 mg/kg body weight.

12. Pharmaceutical composition having antiviral activity against viruses of the herpes family, which includes an effective amount of the compounds on p. 1 and pharmaceutically acceptable nose is olycarbonate;

(2) 7-amino-N-[(4-chlorophenyl)methyl]-4-hydroxy-3-chinainternational;

(3) N-[(4-chlorophenyl)methyl]-8-fluoro-4,6-dihydroxy-3-chinainternational;

(4) 6-bromo-N-[(4-chlorophenyl)methyl]-8-fluoro-3-chinainternational;

(5) N-[(4-chlorophenyl)methyl]-8-fluoro-4-hydroxy-6-iodine-3-chinainternational;

(6) N-[(4-chlorophenyl)methyl]-4-hydroxy-3-chinainternational;

(7) N-[(4-chlorophenyl)methyl]-4-hydroxy-7-methoxy-3-chinainternational;

(8) N-[(4-chlorophenyl)methyl]-4-hydroxy-5,7-bis(trifluoromethyl)-3-chinainternational;

(9) N-[(4-chlorophenyl)methyl]-7-fluoro-4-hydroxy-3-chinainternational;

(10) N-[(4-chlorophenyl)methyl]-6-fluoro-4-hydroxy-3-chinainternational;

(11) N-[(4-chlorophenyl)methyl]-4-hydroxy-7-methyl-3-chinainternational;

(12) N-[(4-chlorophenyl)methyl]-8-fluoro-4-hydroxy-3-chinainternational;

(13) N-[(4-chlorophenyl)methyl]-4-hydroxy-6-nitro-3-chinainternational;

(14) N-[(4-chlorophenyl)methyl]-5,6,7,8-titrator-4-hydroxy-3-chinainternational;

(15) N-[(4-chlorophenyl)methyl]-6,7,8-Cryptor-4-hydroxy-3-chinainternational;

(16) 6,7,8-Cryptor-4-hydroxy-3-quinoline-carboxylic acid 2-(4-chlorophenyl)hydrazide;

(17) N-[(4-chlorophenyl)methyl]-5,8-debtor-4-hydroxy-3-chinainternational;

(18) N-[(4-chlorophenyl)methyl]-7,8-debtor-4-hydroxy-3-chinainternational;

(19) 6-benzoyl-N-(4-Chlorobenzyl)-4-hydroc-chlorophenyl)methyl]-4-hydroxy-3-chinainternational;

(22) N-[(4-chlorophenyl)methyl]-4-hydroxy-6-methyl-3-chinainternational;

(23) N-[(4-chlorophenyl)methyl]-4-hydroxy-6-methoxy-3-chinainternational;

(24) N-[(4-chlorophenyl)methyl]-6-cyano-4-hydroxy-3-chinainternational;

(25) 7-(acetylamino)-N-[(4-chlorophenyl)methyl]-4-hydroxy-3-chinainternational;

(26) N-[(4-chlorophenyl)methyl]-4-hydroxy-7-[(methylsulphonyl)amino]-3-chinainternational;

(27) N-[(4-chlorophenyl)methyl]-7-(dimethylamino)-4-hydroxy-3-chinainternational;

(28) 6-amino-N-[(4-chlorophenyl)methyl]-4-hydroxy-3-chinainternational;

(29) N-[(4-chlorophenyl)methyl]-4-hydroxy-6-[(methylsulphonyl)amino]-3-chinainternational;

(30) N-[(4-chlorophenyl)methyl]-6-(dimethylamino)-4-hydroxy-3-chinainternational;

(31) 6-(acetylamino)-N-[(4-chlorophenyl)methyl]-4-hydroxy-3-chinainternational;

(32) N-[(4-chlorophenyl)methyl]-4-hydroxy-7-(1-pyrrolyl)-3-chinainternational;

(33) N-[(4-chlorophenyl)methyl]-4-hydroxy-7-[(phenylsulfonyl)amino]-3-chinainternational;

(34) N-[(4-chlorophenyl)methyl]-4-hydroxy-7-[[(phenylmethyl)sulfonyl]amino]-3-chinainternational;

(35) N-[(4-chlorophenyl)methyl]-7-[[(4-chlorophenyl)sulfonyl]amino]-4-hydroxy-3-chinainternational;

(36) 8-fluoro-4-hydroxy-3-quinoline-carboxylic acid 2-(4-chlorophenyl)hydrazide;

(37) N-[(4-chlorophenyl)methyl]-8-fluoro-4-hydroxy-6-methyl-3-Himmel]-4-hydroxy-6-iodine-3-chinainternational

(40) N-[(4-chlorophenyl)methyl]-6-(cyanomethyl)-4-hydroxy-3-chinainternational;

(41) N-[(4-chlorophenyl)methyl]-4,5-dihydroxy-3-chinainternational;

(42) 7,6-dichloro-N-[(4-chlorophenyl)methyl]-4-hydroxy-3-chinainternational;

(43) N-[(4-chlorophenyl)methyl]-4,6-dihydroxy-3-chinainternational;

(44) N-[(4-chlorophenyl)methyl]-4,8-dihydroxy-3-chinainternational;

(45) 8-chloro-N-[(4-chlorophenyl)methyl]-4-hydroxy-3-chinainternational;

(46) N-[(4-chlorophenyl)methyl]-4-hydroxy-6-[[(1-phenyl-1H-pyrazole-5-yl)amino]sulfonyl]-3-chinainternational;

(47) N-[(4-chlorophenyl)methyl]-8-cyano-4-hydroxy-3-chinainternational;

(48) N-[(4-chlorophenyl)methyl]-4-hydroxy-8-nitro-3-chinainternational;

(49) 7-amino-N-[(4-chlorophenyl)methyl]-4-hydroxy-8-methyl-3-chinainternational;

(50) N-[(4-chlorophenyl)methyl]-6-cyano-8-fluoro-4-hydroxy-3-chinainternational;

(51) 6-(aminoethoxymethyl)-N-[(4-chlorophenyl)methyl]-8-fluoro-4-hydroxy-3-chinainternational;

(52) N-[(4-chlorophenyl)methyl]-8-fluoro-4-hydroxy-6-(3-hydroxy-1-PROPYNYL)-3-chinainternational;

(53) 8-fluoro-4-hydroxy-6-iodine-3-quinoline-carboxylic acid 2-(4-chlorophenyl)hydrazide;

(54) 8-fluoro-4-hydroxy-6-methyl-3-quinoline-carboxylic acid 2-(4-chlorophenyl)hydrazide;

(55) N-((4-chlorophenyl)methyl)-7-chloro-4-hydroxy-3-chinainternational;

(56) N-((4-chlorophenyl)METI/p>(58) N-((4-chlorophenyl)methyl)-8-chloro-4-hydroxy-5-trifluoromethyl-3-chinainternational;

(59) N-((4-chlorophenyl)methyl)-6,8-dimethoxy-4-hydroxy-3-chinainternational;

(60) N-((4-chlorophenyl)methyl)-6,7-dimethoxy-4-hydroxy-3-chinainternational;

(61) N-((4-chlorophenyl)methyl)-4-hydroxy-5-methyl-3-chinainternational;

(62) N-[(4-chlorophenyl)methyl]-6-(1,1-dimethylethyl)-4-hydroxy-3-chinainternational;

(63) N-[(4-chlorophenyl)methyl]-7,8-dihydro-4-hydroxy-6N-cyclopent[g]quinoline-3-carboxamide;

(64) N-[(4-chlorophenyl)methyl]-1, 4-dihydro-8-(methylthio)-4-oxo-3-chinainternational;

(65) N-[(4-chlorophenyl)methyl]-9-hydroxytriazolam[5,4-f]-quinoline-8-carboxamide;

(66) 2-[(8-{[3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-4-hydroxy-6-chinoline)-2-PROPYNYL]oxy}-8-oxooctanoate) (methyl)amino]-1-econsultant sodium;

(67) 2-[(8-{[3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)-2-PROPYNYL]oxy}-8-oxooctanoate) (methyl)amino]-1-econsultant sodium;

(68) 2-[{8-[3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-4-hydroxy-6-chinoline)propoxy]-8-oxooctanoate}(methyl)amino]-1-econsultant sodium;

(69) N-(4-Chlorobenzyl)-4-hydroxy-7-{[(1-naphthylmethyl)amino]sulfonyl}-3-chinainternational;

(70) N-(4-Chlorobenzyl)-4-hydroxy-7-(methylsulfanyl)-3-chinainternational;

(71) N-[(4-chlorophenyl)methyl]-4-hydroxy-6-[(Hairdryer is l)propyl dihydrophosphate (approx. 269);

(73) N-[(4-chlorophenyl)methyl]-8-fluoro-4-hydroxy-6-(2-thiazolyl)-3-chinainternational (approx. 87);

(74) N-[(4-chlorophenyl)methyl]-8-fluoro-4-hydroxy-6-(2-thiophenyl)-3-chinainternational;

(75) N-((4-chlorophenyl)methyl)-4-hydroxy-5-trifluoromethyl-3-chinainternational;

(76) N-((4-chlorophenyl)methyl)-8-fluoro-4-hydroxy-6-(2-were)-3-chinainternational;

(77) N-((4-chlorophenyl)methyl)-6,7-debtor-4-hydroxy-8-(tetrahydro-2H-Piran-4-hydroxy)-3-chinainternational;

(78) N-((4-chlorophenyl)methyl)-6,7-debtor-4-hydroxy-8-methoxy-3-chinainternational;

(79) N-((4-chlorophenyl)methyl)-7,8-dimethoxy-6-fluoro-4-hydroxy-3-chinainternational;

(80) N-((4-chlorophenyl)methyl)-6,8-debtor-4-hydroxy-7-(4-(hydroxymethyl)-phenoxy)-3-chinainternational;

(81) N-((4-chlorophenyl)methyl)-6,8-debtor-4-hydroxy-7-methoxy-3-chinainternational;

(82) N-((4-chlorophenyl)methyl)-6,8-debtor-4-hydroxy-7-(2-(methoxy)ethoxy)-3-chinainternational;

(83) N-((4-chlorophenyl)methyl)-6,7-debtor-4-hydroxy-8-(2-(methoxy)ethoxy)-3-chinainternational;

(84) N-((4-chlorophenyl)methyl)-1,8-di(2-(methoxy)ethoxy)-6-fluoro-4-hydroxy-3-chinainternational;

(85) N-((4-chlorophenyl)methyl)-6,8-debtor-4-hydroxy-7-(1-methylethoxy)-3-chinainternational;

(86) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(1,3-thiazol-2-yl)-3-chinainternational;

(87) N-(4-chlorbenzyl)-6,8-DipTrace-3-chinainternational;

(89) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(2-pyridinyl)-3-chinainternational;

(90) N’-(4-chlorophenyl)-4-hydroxy-6-iodine-3-chinainternational;

(91) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-[2-(2-pyridinyl)ethinyl]-3-chinainternational;

(92) N-(4-chlorbenzyl)-6,8-debtor-4-hydroxy-7-[(2-methoxyethyl)amino]-3-chinainternational (approx.88);

(93) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(4-hydroxy-1-butynyl)-3-chinainternational;

(94) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-methoxy-1-PROPYNYL)-3-chinainternational;

(95) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-hydroxy-1-butynyl)-3-chinainternational;

(96) 6-(4-bromo-2-thienyl)-N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-3-chinainternational;

(97) N-(4-Chlorobenzyl)-8-fluoro-6-(hydrazinecarbothioamide)-4-hydroxy-3-chinainternational;

(98) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(4-hydroxybutyl)-3-chinainternational;

(99) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(5-methyl-1,3,4-thiadiazole-2-yl)-3-chinainternational;

(100) N-(4-Chlorobenzyl)-4-hydroxy-7-(3-hydroxy-1-PROPYNYL)-3-chinainternational;

(101) 7-(aminocarbonyl)-N-(4-Chlorobenzyl)-4-hydroxy-3-chinainternational;

(102) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-methoxypropyl)-3-chinainternational;

(103) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-[(Z)-4-hydroxy-1-butenyl]-3-chinainternational;

(104) N-hydroxy-3-methylbutyl)-3-chinainternational;

(106) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(5-hydroxy-1-pentenyl)-3-chinainternational;

(107) 6-{3-[benzyl(methyl)amino]propyl}-N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-3-chinainternational;

(108) methyl 3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinainternational;

(109) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-hydroxypropyl)-3-chinainternational;

(110) N-(4-Chlorobenzyl)-4-hydroxy-7-(3-hydroxypropyl)-3-chinainternational;

(111) ethyl (E)-3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)-2-propenoate;

(112) 2-[{8-[3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)propoxy]-8-oxooctanoate}(methyl)amino]-1-econsultant sodium;

(113) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)propanoic acid;

(114) 5-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)-4-pontenova acid;

(115) N-[(4-chlorophenyl)methyl]-9-hydroxy-3H-pyrazolo [4,3-f]quinoline-8-carboxamide;

(116) N-(4-Chlorobenzyl)-4-hydroxy-6-iodine-8-methoxy-3-chinainternational;

(117) N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-PROPYNYL)-8-methoxy-3-chinainternational;

(118) N-(4-Chlorobenzyl)-4-hydroxy-8-methoxy-6-(3-methoxy-1-PROPYNYL)-3-chinainternational;

(119) N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxypropyl)-8-methoxy-3-fineliner N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-PROPYNYL)-8-(triptoreline)-3-chinainternational;

(122) N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxypropyl)-8-(trifluoromethyl)-3-chinainternational;

(123) N-(4-Chlorobenzyl)-4-hydroxy-8-(2-hydroxyethoxy)-6-(3-hydroxypropyl)-3-chinainternational;

(124) N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1,1-dimethylpropyl)-3-chinainternational;

(125) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-[3-(methylthio)-1-PROPYNYL]-3-chinainternational;

(126) N-(4-Chlorobenzyl)-6-[3-(ethylthio)-1-PROPYNYL]-8-fluoro-4-hydroxy-3-chinainternational;

(127) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-[(Z)-3-(methylthio)-1-propenyl]-3-chinainternational;

(128) N-(4-Chlorobenzyl)-6-[(Z)-3-(ethylthio)-1-propenyl]-8-fluoro-4-hydroxy-3-chinainternational;

(129) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-[3-(methylthio)propyl]-3-chinainternational;

(130) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)-2-propenylboronic;

(131) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-hydroxybutyl)-3-chinainternational;

(132) N-(4-Chlorobenzyl)-6-[(E)-2-cyanoethyl]-8-fluoro-4-hydroxy-3-chinainternational;

(133) N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-PROPYNYL)-3-chinainternational;

(134) N-(4-Chlorobenzyl)-6-[(Z)-3-hydroxy-1-propenyl]-4-oxo-1,4-dihydro-3-chinainternational;

(135) N-(4-Chlorobenzyl)-6-[(E)-3-hydroxy-1-propenyl]-4-oxo-1,4-dihydro-3-chinainternational;

(136) N-(4-chlorobenz is hydroxy-3-chinainternational;

(138) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-oxopropyl)-3-chinainternational;

(139) N-(4-Chlorobenzyl)-4-hydroxy-7-(4-hydroxybutyl)-3-chinainternational;

(140) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(hydroxymethyl)-3-chinainternational;

(141) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)propyl methanesulfonate;

(142) N-(4-Chlorobenzyl)-8-fluoro-6-(3-fluoro-1-PROPYNYL)-4-hydroxy-3-chinainternational;

(143) N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxypropyl)-3-chinainternational;

(144) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)cut 2-bromoacetate;

(145) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)propyl 2-[(tert-butoxycarbonyl)-amino]-3-methylbutanoate;

(146) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)propyl 2-(4-morpholinyl)acetate;

(147) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)propyl 2-(dimethylamino)acetate;

(148) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)propyl 2-amino-3-methylbutanoate;

(149) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)-2-propenyl phenylcarbamate;

(150) N-(4-Chlorobenzyl)-4-hydroxy-6-propyl-3-chinainternational;

(151) N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-butynyl)-3-China benzyl)-8-fluoro-4-hydroxy-6-(5-hydroxyphenyl)-3-chinainternational;

(154) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)propyl 2,6-bis[(tert-butoxycarbonyl)amino]hexanoate;

(155) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)propyl 2,6-diaminohexanoic, salt triperoxonane acid;

(156) N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxybutyl)-3-chinainternational;

(157) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(4-morpholinylmethyl)-3-chinainternational;

(158) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)cut phenylcarbamate;

(159) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-oxobutyl)-3-chinainternational;

(160) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-4-hydroxy-6-chinoline)-2-propenyl 2,6-bis[(tert-butoxy-carbonyl)amino]hexanoate;

(161) salt triperoxonane acid 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-4-hydroxy-6-chinoline)-2-propenyl 2,6-diaminohexanoic;

(162) N-(4-Chlorobenzyl)-4-hydroxy-6-[(2-hydroxyethoxy)methyl]-3-chinainternational;

(163) N-(4-Chlorobenzyl)-4-hydroxy-6-{[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl}-3-chinainternational;

(164) methyl 3-{[(4-Chlorobenzyl)amino]carbonyl}-4-hydroxy-6-chinainternational;

(165) N-(4-Chlorobenzyl)-4-hydroxy-6-(hydroxymethyl)-3-chinainternational;

(166) 6-chloro-N-(4-Chlorobenzyl)-4-hydroxy-8-methyl-3-healingherbs is hydroxy-3-chinainternational;

(169) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(methylsulfanyl)-3-chinainternational;

(170) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-[(2-hydroxyethyl)sulfanyl]-3-chinainternational;

(171) 6-[(2-amino-ethyl)sulfanyl]-N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-3-chinainternational hydrobromide;

(172) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-{[(2-methoxyethoxy)methyl]sulfanyl}-3-chinainternational;

(173) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-{[2-(4-morpholinyl)ethyl]sulfanyl}-3-chinainternational;

(174) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(methylsulfinyl)-3-chinainternational;

(175) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(methylsulphonyl)-3-chinainternational;

(176) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-[(2-hydroxyethyl)sulfinil]-3-chinainternational;

(177) N-(4-Chlorobenzyl)-4-hydroxy-6-(2-thienyl)-3-chinainternational;

(178) N-(4-Chlorobenzyl)-4-hydroxy-6-(2-hydroxyethoxy)-3-chinainternational;

(179) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(4-morpholinylcarbonyl)-3-chinainternational;

(180) N3-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-N6-(2-hydroxyethyl)-3,6-chinainternational;

(181) N3-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-N6N~6~-dimethyl-3,6-chinainternational;

(182) N3-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-N6-(4-hydroxyphenethyl)-3,6-chinainternational)-8-fluoro-4-hydroxy-3,6-chinainternational;

(185) 6-amino-N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-3-chinainternational;

(186) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-{[(4-methoxyphenyl)sulfonyl]amino}-3-chinainternational;

(187) N-(4-Chlorobenzyl)-4-hydroxy-6-[(2-hydroxyethyl)amino]-3-chinainternational;

(188) N-(4-Chlorobenzyl)-6-[ethyl(2-hydroxyethyl)amino]-4-hydroxy-3-chinainternational;

(189) N-(4-Chlorobenzyl)-4-hydroxy-6-(2-oxo-1,3-oxazolidin-3-yl)-3-chinainternational;

(190) N-(4-Chlorobenzyl)-4-hydroxy-6-(4-morpholinylmethyl)-3-chinainternational;

(191) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-{[(1-naphthylmethyl)amino]sulfonyl}-3-chinainternational;

(192) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-{[2-(1H-indol-3-yl)ethyl]amino}sulfonyl)-3-chinainternational;

(193) N-(4-Chlorobenzyl)-8-fluoro-6-{[(2-furylmethyl)-amino]sulfonyl}-4-hydroxy-3-chinainternational;

(194) 6-{[bis(2-hydroxyethyl)amino]sulfonyl}-N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-3-chinainternational;

(195) ethyl 2-{[(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)sulfonyl]amino}acetate;

(196) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-{[(2-hydroxyethyl)amino]sulfonyl}-3-chinainternational;

(197) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(4-morpholinylcarbonyl)-3-chinainternational;

(198) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-{[(2-pyridinylmethyl)am olycarbonate;

(200) N-(4-Chlorobenzyl)-6-{[(cyclohexylmethyl)amino]sulfonyl}-8-fluoro-4-hydroxy-3-chinainternational;

(201) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-({[2-(1-methyl-2-pyrrolidinyl)ethyl]amino}sulfonyl)-3-chinainternational;

(202) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-({[2-(1-pyrrolidinyl)ethyl]amino}sulfonyl)-3-chinainternational;

(203) N-(4-Chlorobenzyl)-8-fluoro-6-{[(2-furylmethyl)-amino]sulfonyl}-4-hydroxy-3-chinainternational;

(204) N-(4-Chlorobenzyl)-6-({[3-(cyclohexylamino)-propyl]amino}sulfonyl)-8-fluoro-4-hydroxy-3-chinainternational;

(205) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-{[(1-naphthylmethyl)amino]sulfonyl}-3-chinainternational;

(206) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-({[2-(1H-imidazol-4-yl)ethyl]amino}sulfonyl)-3-chinainternational;

(207) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-{[(tetrahydro-2-furylmethyl)amino]sulfonyl}-3-chinainternational;

(208) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-{[(2-thienylmethyl)amino]sulfonyl}-3-chinainternational;

(209) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-({[2-(1H-indol-3-yl)ethyl]amino}sulfonyl)-3-chinainternational;

(210) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-({[2-(5-methoxy-1H-indol-3-yl)ethyl]amino}sulfonyl)-3-chinainternational;

(211) 6-{[(1,3-benzodioxol-5-ylmethyl)amino]sulfonyl}-N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-3-hinoeuma;

(213) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-({[3-(4-morpholinyl)propyl]amino}sulfonyl)-3-chinainternational;

(214) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-[({2-[(5-the nitro-2-pyridinyl)amino]ethyl}-amino)sulfonyl]-3-chinainternational;

(215) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-{[(2-pyridinylmethyl)amino]sulfonyl}-3-chinainternational;

(216) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-({[2-(2-pyridinyl)ethyl]amino}sulfonyl)-3-chinainternational;

(217) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-{[(3-pyridinylmethyl)amino]sulfonyl}-3-chinainternational;

(218) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-{[(4-pyridinylmethyl)amino]sulfonyl}-3-chinainternational;

(219) N-(4-Chlorobenzyl)-6-{[(4-Chlorobenzyl)amino]-sulfonyl}-8-fluoro-4-hydroxy-3-chinainternational;

(220) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-{[(4-methoxybenzyl)amino]sulfonyl}-3-chinainternational;

(221) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-[(neopentylene)sulfonyl]-3-chinainternational;

(222) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-{[(2-hydroxypropyl)amino]sulfonyl}-3-chinainternational;

(223) N-(4-Chlorobenzyl)-6{[(2,3-dihydroxypropyl)-amino]sulfonyl}-8-fluoro-4-hydroxy-3-chinainternational;

(224) N-(4-Chlorobenzyl)-6-{[(2,2-diphenylether)amino] sulfonyl}-8-fluoro-4-hydroxy-3-chinainternational;

(225) 11-{[(3-{[(4-chlorbenzyl)] amino}sulfonyl)-N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-3-chinainternational;

(227) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-({[2-(2-hydroxyethoxy)ethyl]amino}sulfonyl)-3-chinainternational;

(228) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-{[(2-gidroksistil)amino]sulfonyl}-3-chinainternational;

(229) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-[(phenethylamine)sulfonyl]-3-chinainternational;

(230) N-(4-Chlorobenzyl)-6-{[(4-chlorphenyl)amino]-sulfonyl}-8-fluoro-4-hydroxy-3-chinainternational;

(231) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-[(2-propylamino)sulfonyl]-3-chinainternational;

(232) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-[(isobutylamino)sulfonyl]-3-chinainternational;

(233) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-{[(3-phenylpropyl)amino]sulfonyl}-3-chinainternational;

(234) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-[(pentylamine)sulfonyl]-3-chinainternational;

(235) 6-({[3,5-bis(trifluoromethyl)benzyl]amino}-sulfonyl)-N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-3-chinainternational;

(236) N-(4-Chlorobenzyl)-6-({[2-(1-cyclohexen-1-yl)ethyl]amino}sulfonyl)-8-fluoro-4-hydroxy-3-chinainternational;

(237) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-({[2-(1-naphthylamine)ethyl]amino}sulfonyl)-3-chinainternational;

(238) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-[(methylamino)sulfonyl]-3-chinainternational;

(239) N-(4-Chlorobenzyl)-6-{[(cyanomethyl)amino]sulfonyl}-8-fluoro-4-hydrogencarbonate;

(241) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-{[(3-jobensis)amino]sulfonyl}-3-chinainternational;

(242) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-{[(2,2,2-triptorelin)amino]sulfonyl}-3-chinainternational;

(243) 6-{[(2-bromacil)amino]sulfonyl}-N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-3-chinainternational;

(244) N-(4-Chlorobenzyl)-6-{[(2-chloroethyl)amino]sulfonyl}-8-fluoro-4-hydroxy-3-chinainternational;

(245) N-(4-Chlorobenzyl)-6-{[(3,4-dihydroxyphenyl)amino]sulfonyl}-8-fluoro-4-hydroxy-3-chinainternational;

(246) N-(4-Chlorobenzyl)-6-({[2-(ethylsulfanyl)-ethyl]amino}sulfonyl)-8-fluoro-4-hydroxy-3-chinainternational;

(247) 6-{[(3-bromopropyl)amino]sulfonyl}-N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-3-chinainternational;

(248) 6-({[4-aminosulfonyl)benzyl]amino}sulfonyl)-N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-3-chinainternational;

(249) 6-[({2-[bis(2-hydroxyethyl)amino]ethyl}amino)sulfonyl]-N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-3-chinainternational;

(250) N-(4-Chlorobenzyl)-6-({[2-(ethylsulfanyl)-ethyl]amino}sulfonyl)-8-fluoro-4-hydroxy-3-chinainternational;

(251) N-(4-Chlorobenzyl)-6-{[(3,4-dimethylbenzyl)amino]sulfonyl}-8-fluoro-4-hydroxy-3-chinainternational;

(252) N-(4-Chlorobenzyl)-6-{[(cyclopropylmethyl)amino]sulfonyl}-8-fluoro-4-hydroxy-3-chinainternational;

(253) 6-{[(4-bromobenzyl)�({[2-(2-thienyl)ethyl]amino}sulfonyl)-3-chinainternational;

(255) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-{[(2-phenoxyethyl)amino]sulfonyl}-3-chinainternational;

(256) tert-butyl 2-{[(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)sulfonyl]amino}-acetate;

(257) tert-butyl 3-{[(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)sulfonyl]amino}propanoate;

(258) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-({[3-(triptoreline)benzyl]amino}sulfonyl)-3-chinainternational;

(259) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-{[(2-{[2-(hydroxymethyl)phenyl]sulfanyl}-benzyl)amino]sulfonyl}-3-chinainternational;

(260) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-({[4-(1,2,3-the thiadiazole-4-yl)benzyl]amino}sulfonyl)-3-chinainternational;

(261) N-(4-Chlorobenzyl)-6-{[(4-chloro-2-terbisil)-amino]sulfonyl}-8-fluoro-4-hydroxy-3-chinainternational;

(262) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-[({2-[(2-hydroxyethyl)sulfanyl]ethyl}-amino)sulfonyl]-3-chinainternational;

(263) 6-{[(2-amino-2-methylpropyl)amino]sulfonyl}-N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-3-chinainternational;

(264) 6-{[(2-amino-2-oxoethyl)amino]sulfonyl}-N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-3-chinainternational;

(265) 6-{[(4-aminobenzyl)amino]sulfonyl}-N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-3-chinainternational;

(266) di(tert-butyl)3-(3-{[(4-Chlorobenzyl)amino]-carbonyl}-8-propyla dihydrophosphate;

(268) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-4-hydroxy-6-chinoline)cut dihydrophosphate;

(269) tert-butyl-(3-{[(4-Chlorobenzyl)amino]carbonyl}-4-hydroxy-6-chinoline)propyl phosphonate;

(270) tert-butyl 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}8-fluoro-4-hydroxy-6-chinoline)propyl phosphonate;

(271) (E)-3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)-2-promonova acid or

(272) N-[(4-chlorophenyl)methyl]-4-hydroxy-7-iodine-3-chinainternational

14. Connection on p. 1, representing

(1) 7-amino-N-(4-Chlorobenzyl)-4-hydroxy-3-chinainternational;

(2) N-(4-Chlorobenzyl)-4-hydroxy-7-methoxy-3-chinainternational;

(3) N-(4-Chlorobenzyl)-7-fluoro-4-hydroxy-3-chinainternational;

(4) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-3-chinainternational;

(5) 6-chloro-N-(4-Chlorobenzyl)-4-hydroxy-3-chinainternational;

(6) N-(4-Chlorobenzyl)-4-hydroxy-6-methyl-3-chinainternational;

(7) N-(4-Chlorobenzyl)-4-hydroxy-6-methoxy-3-chinainternational;

(8) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-methyl-3-chinainternational;

(9) N-(4-Chlorobenzyl)-4-hydroxy-6-iodine-3-chinainternational;

(10) N-(4-Chlorobenzyl)-4-hydroxy-6-phenyl-3-chinainternational;

(11) N-(4-Chlorobenzyl)-4-hydroxy-6,8-dimethoxy-3-chinainternational;

(12) 6-(tert-butyl)-N-(4-Chlorobenzyl)-4-hydrox who yl)-9-hydroxy[1,3]thiazolo[5,4-f]quinoline-8-carboxamide;

(15) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-hydroxy-1-PROPYNYL)-3-chinainternational;

(16) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(1,3-thiazol-2-yl)-3-chinainternational;

(17) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(2-thienyl)-3-chinainternational;

(18) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-methoxy-1-PROPYNYL)-3-chinainternational;

(19) 6-(4-bromo-2-thienyl)-N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-3-chinainternational;

(20) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(4-hydroxybutyl)-3-chinainternational;

(21) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-[(Z)-4-hydroxy-1-butenyl]-3-chinainternational;

(22) N-(4-chlorbenzyl)-6,8-debtor-4-hydroxy-7-[4-(hydroxymethyl)phenoxy]-3-chinainternational;

(23) N-(4-chlorbenzyl)-6,8-debtor-4-hydroxy-7-methoxy-3-chinainternational;

(24) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(5-hydroxy-1-pentenyl)-3-chinainternational;

(25) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)-2-propenylboronic;

(26) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-hydroxypropyl)-3-chinainternational;

(27) N-(4-Chlorobenzyl)-4-hydroxy-7-(3-hydroxypropyl)-3-chinainternational;

(28) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-hydroxybutyl)-3-chinainternational;

(29) N-(4-Chlorobenzyl)-6-[(E)-2-cyanoethyl]-8-fluoro-4-hydroxy-3-chinainternational;

(30) N-(4-what-hydroxy-1-PROPYNYL)-3-chinainternational;

(32) N-(4-Chlorobenzyl)-4-hydroxy-8-methoxy-6-(3-methoxy-1-PROPYNYL)-3-chinainternational;

(33) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-[(Z)-3-hydroxy-1-PROPYNYL]-3-chinainternational;

(34) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-oxopropyl)-3-chinainternational;

(35) N-(4-Chlorobenzyl)-4-hydroxy-7-(4-hydroxybutyl)-3-chinainternational;

(36) N-(4-Chlorobenzyl)-4-hydroxy-6-iodine-8-methoxy-3-chinainternational;

(37) N-(4-Chlorobenzyl)-8-fluoro-6-(3-fluoro-1-PROPYNYL)-4-hydroxy-3-chinainternational;

(38) N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxypropyl)-3-chinainternational;

(39) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)cut 2-bromoacetate;

(40) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)propyl 2-[(tert-butoxycarbonyl)amino]-3-methylbutanoate;

(41) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)propyl 2-amino-3-methylbutanoate;

(42) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)-2-propenyl phenylcarbamate;

(43) N-((4-Chlorobenzyl)-4-hydroxy-6-propyl-3-chinainternational;

(44) N-((4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxypropyl)-8-methoxy-3-chinainternational;

(45) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(methylsulfanyl)-3-chinainternational;

(46) N-(4-Chlorobenzyl)-4-hydroxy-7{[(1l]-3-chinainternational;

(48) N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-PROPYNYL)-8-(triptoreline)-3-chinainternational;

(49) 2-[{8-[3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)propoxy]-8-oxooctanoate}(methyl)amino]-1-econsultant sodium;

(50) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)cut dihydrophosphate;

(51) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)propyl 2,6-bis[(tert-butoxycarbonyl)amino]hexanoate;

(52) tert-butyl 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)propyl phosphonate;

(53) 2-[(8-{[3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)-2-PROPYNYL]oxy}-8-oxooctanoate)(methyl)amino]-1-econsultant sodium;

(54) N-(4-Chlorobenzyl)-4-hydroxy-6-(2-hydroxyethoxy)-3-chinainternational;

(55) salt triperoxonane acid 3-(3-{[(4-Chlorobenzyl) amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)propyl 2,6-diaminohexanoic;

(56) N-(4-Chlorobenzyl)-4-hydroxy-6-[(2-hydroxyethyl)-amino]-3-chinainternational;

(57) N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxybutyl)-3-chinainternational;

(58) 2-[(8-{[3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-4-hydroxy-6-chinoline)-2-PROPYNYL]oxy}-8-oxooctanoate)(methyl)amino]-1-econsultant sodium;

(59) 2-[{8-[3-(3-{[(4-Chlorobenzyl)amino]carbon-Chlorobenzyl)amino]carbonyl}-4-hydroxy-6-chinoline)propyl phosphonate;

(61) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-4-hydroxy-6-chinoline)cut dihydrophosphate;

(62) N-(4-Chlorobenzyl)-4-hydroxy-8-(2-hydroxyethoxy)-6-(3-hydroxypropyl)-3-chinainternational;

(63) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(4-morpholinylmethyl)-3-chinainternational;

(64) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-oxobutyl)-3-chinainternational;

(65) N-(4-Chlorobenzyl)-4-hydroxy-6-(2-oxo-1,3-oxazolidin-3-yl)-3-chinainternational;

(66) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-4-hydroxy-6-chinoline)-2-propenyl 2,6-bis[(tert-butoxycarbonyl)amino]hexanoate;

(67) N-(4-Chlorobenzyl)-6-[(Z)-3-hydroxy-1-propenyl]-4-oxo-1,4-dihydro-3-chinainternational;

(68) N-(4-Chlorobenzyl)-6-[(E)-3-hydroxy-1-propenyl]-4-oxo-1,4-dihydro-3-chinainternational;

(69) Sol triperoxonane acid 3-(3-{[(4-Chlorobenzyl) amino]carbonyl}-4-hydroxy-6-chinoline)-2-propenyl 2,6-diaminohexanoic;

(70) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-4-hydroxy-6-chinoline)cut hydrophosphate;

(71) N-(4-Chlorobenzyl)-4-hydroxy-6-(2-thienyl)-3-chinainternational;

(72) N-(4-Chlorobenzyl)-4-hydroxy-6-[(2-hydroxyethoxy)methyl]-3-chinainternational;

(73) N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1,1-dimethylpropyl)-3-chinainternational;

(74) N-(4-Chlorobenzyl)-4-hydroxy-6-{[2-hydroxy-1-(hydroxymethyl)p>(76) methyl 3-{[(4-Chlorobenzyl)amino]carbonyl}-4-hydroxy-6-chinainternational or

(77) N-(4-Chlorobenzyl)-4-hydroxy-6-(4-morpholinylmethyl)-3-chinainternational.

15. Connection on p. 1, representing

(1) N-(4-Chlorobenzyl)-4-hydroxy-7-methoxy-3-chinainternational;

(2) N-(4-Chlorobenzyl)-7-fluoro-4-hydroxy-3-chinainternational;

(3) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-3-chinainternational;

(4) N-(4-Chlorobenzyl)-4-hydroxy-6-methoxy-3-chinainternational;

(5) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(2-thienyl)-3-chinainternational;

(6) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(4-hydroxybutyl)-3-chinainternational;

(7) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-[(Z)-4-hydroxy-1-butenyl]-3-chinainternational;

(8) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-hydroxypropyl)-3-chinainternational;

(9) N-(4-Chlorobenzyl)-4-hydroxy-7-(3-hydroxypropyl)-3-chinainternational;

(10) N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-PROPYNYL)-8-methoxy-3-chinainternational;

(11) N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-PROPYNYL)-3-chinainternational;

(12) N-(4-Chlorobenzyl)-4-hydroxy-8-methoxy-6-(3-methoxy-1-PROPYNYL)-3-chinainternational;

(13) N-(4-Chlorobenzyl)-4-hydroxy-7-(4-hydroxybutyl)-3-chinainternational;

(14) N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxypropyl)-3-China�6) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)propyl 2-amino-3-methylbutanoate;

(17) N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxypropyl)-8-methoxy-3-chinainternational;

(18) 2-[{8-[3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)propoxy]-8-oxooctanoate}(methyl)amino]-1-econsultant sodium;

(19) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)cut dihydrophosphate;

(20) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)propyl 2,6-bis[(tert-butoxycarbonyl)amino]hexanoate;

(21) tert-butyl 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)propyl phosphonate;

(22) salt triperoxonane acid 3-(3-{[(4-Chlorobenzyl) amino]carbonyl}-8-fluoro-4-hydroxy-6-chinoline)propyl 2,6-diaminohexanoic;

(23) N-(4-Chlorobenzyl)-4-hydroxy-6-[(2-hydroxyethyl)-amino]-3-chinainternational;

(24) N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxybutyl)-3-chinainternational;

(25) 2-[(8-{[3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-4-hydroxy-6-chinoline)-2-PROPYNYL]oxy}-8-oxooctanoate)(methyl)amino]-1-econsultant sodium;

(26) 2-[{8-[3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-4-hydroxy-6-chinoline)propoxy]-8-oxooctanoate}(methyl)-amino]-1-econsultant sodium;

(27) tert-butyl 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-4-hydroxy-6-chinoline)propyl phosphonate;

(28) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-4-hydro is-chinainternational;

(30) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(4-morpholinylmethyl)-3-chinainternational;

(31) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-4-hydroxy-6-chinoline)-2-propenyl 2,6-bis[(tert-butoxycarbonyl)amino]hexanoate;

(32) N-(4-Chlorobenzyl)-6-[(Z)-3-hydroxy-1-propenyl]-4-oxo-1,4-dihydro-3-chinainternational;

(33) N-(4-Chlorobenzyl)-6-[(E)-3-hydroxy-1-propenyl]-4-oxo-1,4-dihydro-3-chinainternational;

(34) salt triperoxonane acid 3-(3-{[(4-Harbin-ZIL)amino]carbonyl}-4-hydroxy-6-chinoline)-2-propenyl 2,6-diaminohexanoic;

(35) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-4-hydroxy-6-chinoline) cut hydrophosphate;

(36) N-(4-Chlorobenzyl)-4-hydroxy-6-(2-thienyl)-3-chinainternational;

(37) N-(4-Chlorobenzyl)-4-hydroxy-6-[(2-hydroxyethoxy)methyl]-3-chinainternational;

(38) N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1,1-dimethylpropyl)-3-chinainternational;

(39) methyl 3-{[(4-Chlorobenzyl)amino]carbonyl}-4-hydroxy-6-chinainternational or

(40) N-(4-Chlorobenzyl)-4-hydroxy-6-(4-morpholinylmethyl)-3-chinainternational.

16. Connection on p. 1, representing

(1) N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-hydroxypropyl)-3-chinainternational;

(2) N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-PROPYNYL)-8-methoxy-3-chinainternational;

(3) N-(4-Chlorobenzyl)-4-hydroc nonincorporated;

(5) N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxypropyl)-8-methoxy-3-chinainternational;

(6) 2-[(8-{[3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-4-hydroxy-6-chinoline)-2-PROPYNYL]oxy}-8-oxooctanoate)(methyl) amino]-1-econsultant sodium;

(7) 2-[{8-[3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-4-hydroxy-6-chinoline)propoxy]-8-oxooctanoate}(methyl)-amino]-1-econsultant sodium;

(8) 3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-4-hydroxy-6-chinoline)cut dihydrophosphate;

(9) N-(4-Chlorobenzyl)-6-[(Z)-3-hydroxy-1-propenyl]-4-oxo-1,4-dihydro-3-chinainternational;

(10) N-(4-Chlorobenzyl)-6-[(E)-3-hydroxy-1-propenyl]-4-oxo-1,4-dihydro-3-chinainternational;

(11) salt triperoxonane acid 3-(3-{[(4-chlorophenyl)amino]carbonyl}-4-hydroxy-6-chinoline)-2-propenyl 2,6-diaminohexanoic;

(12) 3-(3-{[(4-chlorophenyl)amino]carbonyl}-4-hydroxy-6-chinoline) cut hydrophosphate;

(13) N-(4-Chlorobenzyl)-4-hydroxy-6-(2-thienyl)-3-chinainternational;

(14) N-(4-Chlorobenzyl)-4-hydroxy-6-[(2-hydroxyethoxy)methyl]-3-chinainternational or

(15) N-(4-Chlorobenzyl)-4-hydroxy-6-(4-morpholinylmethyl)-3-chinainternational.

Priority points and attributes:

22.12.1997 on PP.1-16;

04.03.1998 on PP.1-16 varieties radicals.

 

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