IP Library › Granted Patent US 9,617,240
Granted Patent B2
US 9,617,240 · App. 14/774,517 · Granted Apr 11, 2017

Pyrazole derivative

Inventors: Asahi Kawana (Hino, JP); Chikashi Kanazawa (Hino, JP); Masayuki Tera (Takatsuki, JP); Yoshimasa Takahashi (Hino, JP); Mariko Imazeki (Tokyo, JP); Hiroyuki Takahashi (Hino, JP); Akira Tanokura (Hino, JP)
Assignee: Teijin Pharma Limited
C07D401/04C07D401/14C07D405/14C07D409/14
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Quick Facts
Patent No.
US 9,617,240
App. No.
14/774,517
Granted
Apr 11, 2017
Kind
B2
Abstract

Provided are a compound expressed by formula (I) or a pharmacologically permissible salt thereof, as well as a drug or drug composition that contains this compound as an active ingredient, having a xanthine oxidase inhibiting effect that is very useful for treating or preventing diseases that are contributed to by xanthine oxidase, such as gout, hyperuricemia, tumor lysis syndrome, urinary tract stones, hypertension, dyslipidemia, diabetes, cardiovascular disease such as heart failure and arterial sclerosis, renal disease such as diabetic near opacity and the like, respiratory disease such as chronic obstructive pulmonary disease and the like, autoimmune diseases such as inflammatory bowel disease, and the like. [In the formula, A, X, Y, Z, R, and R 1 have the meaning set forth in claim 1 ].

Claims (145)

1. A compound or a pharmaceutically acceptable salt thereof represented by the following formula (I)

wherein:

A represents a C 6-10 aryl group or a heteroaryl group, wherein the aryl group or heteroaryl group may be unsubstituted or substituted with 1 to 3 groups Q which are the same or different from one another and selected from the group consisting of a halogen atom, —CN, —NO 2 , a C 1-6 alkyl group, a C 3-7 cycloalkyl group, a C 1-6 halogenoalkyl group, a phenyl group, —CH 2 —O—R 2 , —O—R 2 , —O—C 1-6 halogenoalkyl, —O-benzyl, —O-phenyl, —O—CO—R 2 , —NR 3 R 4 , —NH—CO—R 2 , —CO 2 —R 2 , —CO—R 2 , —CO—NR 3 R 4 , —NH—SO 2 —R 2 , —CO-aryl, —S—R 2 , —SO 2 —C 1-6 alkyl, and —SO 2 -phenyl;

X, Y, and Z represent CR 5 or a nitrogen atom, wherein one of X, Y, and Z represents a nitrogen atom and the remaining two represent CR 5 ;

R represents a hydrogen atom or a C 1-6 alkyl group;

R 1 represents a hydrogen atom, an amino group, or a C 1-6 alkyl group;

R 2 represents a hydrogen atom or a C 1-6 alkyl group;

R 3 and R 4 are the same or different from each other and are a hydrogen atom or a C 1-6 alkyl group, where R 3 and R 4 may be taken together to form with the nitrogen atom to which they are attached a nitrogen-containing saturated monocyclic heterocycle; and

R 5 represents a hydrogen atom, a halogen atom, or a C 1-6 alkyl group.

2. The compound or a pharmaceutically acceptable salt thereof according to claim 1 , wherein X and Z represent CR 5 , and Y represents a nitrogen atom.

3. The compound or a pharmaceutically acceptable salt thereof according to claim 1 , wherein Y and Z represent CR 5 , and X represents a nitrogen atom.

4. The compound or a pharmaceutically acceptable salt thereof according to claim 1 , wherein X and Y represent CR 5 , and Z represents a nitrogen atom.

5. The compound or a pharmaceutically acceptable salt thereof according to claim 1 , wherein R 5 represents a hydrogen atom.

6. The compound or a pharmaceutically acceptable salt thereof according to claim 1 , wherein R and R 1 represent hydrogen atom.

7. The compound or a pharmaceutically acceptable salt thereof according to claim 1 , wherein A represents a C 6-10 aryl group which may be unsubstituted or substituted with 1 to 2 groups Q which are the same or different from one another and selected from the group consisting of a halogen atom, —CN, —NO 2 , a C 1-6 alkyl group, a C 3-7 cycloalkyl group, a C 1-6 halogenoalkyl group, a phenyl group, —CH 2 —O—R 2 , —O—R 2 , —O—C 1-6 halogenoalkyl, —O-benzyl, —O-phenyl, —O—CO—R 2 , —NR 3 R 4 , —NH—CO—R 2 , —CO 2 —R 2 , —CO—R 2 , —CO—NR 3 R 4 , —NH—SO 2 —R 2 , —CO-aryl, —S—R 2 , —SO 2 —C 1-6 alkyl, and —SO 2 -phenyl.

8. The compound or a pharmaceutically acceptable salt thereof according to claim 7 , wherein A represents a phenyl group which may be unsubstituted or substituted with 1 to 2 groups Q which are the same or different from one another and selected from the group consisting of a halogen atom, —CN, —NO 2 , a C 1-6 alkyl group, a C 3-7 cycloalkyl group, a C 1-6 halogenoalkyl group, a phenyl group, —CH 2 —O—R 2 , —O—R 2 , —O—C 1-6 halogenoalkyl, —O-benzyl, —O-phenyl, —O—CO—R 2 , —NR 3 R 4 , —NH—CO—R 2 , —CO 2 —R 2 , —CO—R 2 , —CO—NR 3 R 4 , —NH—SO 2 —R 2 , —CO-aryl, —S—R 2 , —SO 2 —C 1-6 alkyl, and —SO 2 -phenyl.

9. The compound or a pharmaceutically acceptable salt thereof according to any of claim 1 , wherein A represents a heteroaryl group which may be unsubstituted or substituted with 1 to 2 groups Q which are the same or different from one another and selected from the group consisting of a halogen atom, —CN, —NO 2 , a C 1-6 alkyl group, a C 3-7 cycloalkyl group, a C 1-6 halogenoalkyl group, a phenyl group, —CH 2 —O—R 2 , —O—R 2 , —O—C 1-6 halogenoalkyl, —O-benzyl, —O-phenyl, —O—CO—R 2 , —NR 3 R 4 , —NH—CO—R 2 , —CO 2 —R 2 , —CO—R 2 , —CO—NR 3 R 4 , —NH—SO 2 —R 2 , —CO-aryl, —S—R 2 , —SO 2 —C 1-6 alkyl, and —SO 2 -phenyl.

10. The compound or a pharmaceutically acceptable salt thereof according to claim 9 , wherein A represents a thienyl group which may be unsubstituted or substituted with 1 to 2 groups Q which are the same or different from one another and selected from the group consisting of a halogen atom, —CN, —NO 2 , a C 1-6 alkyl group, a C 3-7 cycloalkyl group, a C 1-6 halogenoalkyl group, a phenyl group, —CH 2 —O—R 2 , —O—R 2 , —O—C 1-6 halogenoalkyl, —O-benzyl, —O-phenyl, —O—CO—R 2 , —NR 3 R 4 , —NH—CO—R 2 , —CO 2 —R 2 , —CO—R 2 , —CO—NR 3 R 4 , —NH—SO 2 —R 2 , —CO-aryl, —S—R 2 , —SO 2 —C 1-6 alkyl, and —SO 2 -phenyl.

11. The compound or a pharmaceutically acceptable salt thereof according to claim 1 , wherein A is unsubstituted.

12. The compound or a pharmaceutically acceptable salt thereof according to claim 1 , wherein A is substituted with 1 to 3 groups Q which are the same or different from one another and selected from the group consisting of a halogen atom, a C 1-6 alkyl group, a C 3-7 cycloalkyl group, a C 1-6 halogenoalkyl group, a phenyl group, —O—R 2 , and —O—C 1-6 halogenoalkyl.

13. The compound or a pharmaceutically acceptable salt thereof according to claim 12 , wherein Q is selected from the group consisting of a halogen atom, a methyl group, and a methoxy group.

14. A compound selected from the following (1) to (107):

(1) 1-(4-cyano-5-phenylpyridin-2-yl)-1H-pyrazole-4-carboxylic acid;

(2) 1-[4-cyano-5-(4-methoxyphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(3) 1-[4-cyano-5-(2-ethoxyphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(4) 1-[4-cyano-5-(2-methylphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(5) 1-[4-cyano-5-(2-fluorophenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(6) 1-[4-cyano-5-(2-chlorophenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(7) 1-[4-cyano-5-(2-methoxyphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(8) 1-{4-cyano-5-[2-(trifluoromethyl)phenyl]pyridin-2-yl}-1H-pyrazole-4-carboxylic acid;

(9) 1-{4-cyano-5-[2-(trifluoromethoxy)phenyl]pyridin-2-yl}-1H-pyrazole-4-carboxylic acid;

(10) 1-[4-cyano-5-(3-methylphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(11) 1-[4-cyano-5-(3-fluorophenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(12) 1-[4-cyano-5-(3-chlorophenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(13) 1-[4-cyano-5-(3-methoxyphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(14) 1-[4-cyano-5-(4-methylphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(15) 1-[4-cyano-5-(4-chlorophenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(16) 1-[4-cyano-5-(4-hydroxyphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(17) 1-[4-cyano-5-(2-ethoxy-6-fluorophenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(18) 1-[4-cyano-5-(2-fluoro-6-methoxyphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(19) 1-[4-cyano-5-(2-fluoro-3-methoxyphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(20) 1-[4-cyano-5-(2,3-difluorophenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(21) 1-[4-cyano-5-(thiophen-3-yl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(22) 1-[4-cyano-5-(3-methylthiophen-2-yl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(23) 1-[4-cyano-5-(furan-3-yl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(24) 1-[4-cyano-5-(3-methoxypyridin-4-yl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(25) 1-[4-cyano-5-(pyridin-3-yl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(26) 1-(4-cyano-5-phenylpyridin-2-yl)-3-methyl-1H-pyrazole-4-carboxylic acid;

(27) 1-(4-cyano-5-phenylpyridin-2-yl)-3-(propan-2-yl)-1H-pyrazole-4-carboxylic acid;

(28) 1-(4-cyano-5-phenylpyridin-2-yl)-3,5-dimethyl-1H-pyrazole-4-carboxylic acid;

(29) 1-[4-cyano-5-(4-fluorophenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(30) 1-[4-cyano-5-(3-ethoxyphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(31) 1-[4-cyano-5-(3-propoxyphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(32) 1-[4-cyano-5-(2,4-difluorophenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(33) 1-[4-cyano-5-(2-fluoro-4-methylphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(34) 1-[4-cyano-5-(2-fluoro-5-methylphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(35) 1-[4-cyano-5-(2,5-difluorophenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(36) 1-[4-cyano-5-(2-fluoro-3-methylphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(37) 1-[4-cyano-5-(4-fluoro-3-methylphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(38) 1-[4-cyano-5-(2,3-dimethylphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(39) 1-[4-cyano-5-(3-fluoro-4-methylphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(40) 1-[4-cyano-5-(3-chloro-4-fluorophenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(41) 1-[4-cyano-5-(3-chloro-2-fluorophenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(42) 1-[5-(4-carboxyphenyl)-4-cyanopyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(43) 1-{4-cyano-5-[4-(trifluoromethyl)phenyl]pyridin-2-yl}-1H-pyrazole-4-carboxylic acid;

(44) 1-{4-cyano-5-[4-(trifluoromethoxy)phenyl]pyridin-2-yl}-1H-pyrazole-4-carboxylic acid;

(45) 1-{4-cyano-5-[3-(trifluoromethyl)phenyl]pyridin-2-yl}-1H-pyrazole-4-carboxylic acid;

(46) 1-{4-cyano-5-[3-(difluoromethoxy)phenyl]pyridin-2-yl}-1H-pyrazole-4-carboxylic acid;

(47) 1-{4-cyano-5-[4-(propane-2-yl)phenyl]pyridin-2-yl}-1H-pyrazole-4-carboxylic acid;

(48) 1-{4-cyano-5-[3-(propane-2-yl)phenyl]pyridin-2-yl}-1H-pyrazole-4-carboxylic acid;

(49) 1-[4-cyano-5-(4-fluoro-2-methylphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(50) 1-[4-cyano-5-(4-fluoro-2-methoxyphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(51) 1-[4-cyano-5-(4-chloro-3-methylphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(52) 1-{4-cyano-5-[(4-propan-2-yloxy)phenyl]pyridin-2-yl}-1H-pyrazole-4-carboxylic acid;

(53) 1-[5-(4-tert-butylphenyl)-4-cyanopyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(54) 1-[4-cyano-5-(4-phenoxyphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(55) 1-{4-cyano-5-[4-(methoxymethyl)phenyl]pyridin-2-yl}-1H-pyrazole-4-carboxylic acid;

(56) 1-{4-cyano-5-[3-(2-methylpropoxy)phenyl]pyridin-2-yl}-1H-pyrazole-4-carboxylic acid;

(57) 1-[4-cyano-5-(naphthalen-2-yl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(58) 1-[4-cyano-5-(4-methoxypyridin-3-yl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(59) 1-{4-cyano-5-[6-(dimethylamino)pyridin-3-yl]pyridin-2-yl}-1H-pyrazole-4-carboxylic acid;

(60) 1-[4-cyano-5-(5-fluoropyridin-3-yl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(61) 1-[5-(1-benzothiophen-3-yl)-4-cyanopyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(62) 1-[4-cyano-5-(pyridin-4-yl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(63) 1-{4-cyano-5-[4-(methylsulfanyl)phenyl]pyridin-2-yl}-1H-pyrazole-4-carboxylic acid;

(64) 1-{4-cyano-5-[4-(morpholin-4-yl)phenyl]pyridin-2-yl}-1H-pyrazole-4-carboxylic acid;

(65) 1-[4-cyano-5-(4-phenylphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(66) 1-{5-[4-(benzyloxy)phenyl]-4-cyanopyridin-2-yl}-1H-pyrazole-4-carboxylic acid;

(67) 1-{4-cyano-5-[3-(dimethylamino)phenyl]pyridin-2-yl}-1H-pyrazole-4-carboxylic acid;

(68) 1-[5-(4-aminophenyl)-4-cyanopyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(69) 1-[4-cyano-5-(4-methanesulfonamidophenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(70) 1-(4-cyano-5-{4-[(morpholin-4-yl)carbonyl]phenyl}pyridin-2-yl)-1H-pyrazole-4-carboxylic acid;

(71) 1-[5-(4-acetophenyl)-4-cyanopyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(72) 1-[4-cyano-5-(3-nitrophenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(73) 1-[5-(4-benzoylphenyl)-4-cyanopyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(74) 1-[4-cyano-5-(4-methanesulfonylphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(75) 1-(5-cyano-6-phenylpyridin-3-yl)-1H-pyrazole-4-carboxylic acid;

(76) 1-[5-cyano-6-(2-fluorophenyl)pyridin-3-yl]-1H-pyrazole-4-carboxylic acid;

(77) 1-[5-cyano-6-(2,4-difluorophenyl)pyridin-3-yl]-1H-pyrazole-4-carboxylic acid;

(78) 1-[5-cyano-6-(2-fluoro-4-methylphenyl)pyridin-3-yl]-1H-pyrazole-4-carboxylic acid;

(79) 1-[5-cyano-6-(2-fluoro-5-methylphenyl)pyridin-3-yl]-1H-pyrazole-4-carboxylic acid;

(80) 1-[5-cyano-6-(2,5-difluorophenyl)pyridin-3-yl]-1H-pyrazole-4-carboxylic acid;

(81) 1-[5-cyano-6-(2,3-difluorophenyl)pyridin-3-yl]-1H-pyrazole-4-carboxylic acid;

(82) 1-[5-cyano-6-(4-fluoro-3-methylphenyl)pyridin-3-yl]-1H-pyrazole-4-carboxylic acid;

(83) 1-[5-cyano-6-(3-fluoro-4-methylphenyl)pyridin-3-yl]-1H-pyrazole-4-carboxylic acid;

(84) 1-[5-cyano-6-(2-fluoro-5-methoxyphenyl)pyridin-3-yl]-1H-pyrazole-4-carboxylic acid;

(85) 1-(6-cyano-5-phenylpyridin-2-yl)-1H-pyrazole-4-carboxylic acid;

(86) 1-[6-cyano-5-(2-fluorophenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(87) 1-[6-cyano-5-(2-fluoro-4-methylphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(88) 1-[6-cyano-5-(2-fluoro-5-methylphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(89) 1-[6-cyano-5-(4-fluorophenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(90) 1-[6-cyano-5-(2,4-difluorophenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(91) 1-[6-cyano-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(92) 1-[6-cyano-5-(3-methylphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(93) 1-[6-cyano-5-(3-ethoxyphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(94) 1-[6-cyano-5-(4-fluoro-3-methylphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(95) 1-[6-cyano-5-(2,6-difluorophenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(96) 1-[6-cyano-5-(2-fluoro-6-methoxyphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(97) 3-amino-1-(4-cyano-5-phenylpyridin-2-yl)-1H-pyrazole-4-carboxylic acid;

(98) 3-amino-1-[4-cyano-5-(2-fluorophenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(99) 3-amino-1-[4-cyano-5-(4-fluorophenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(100) 3-amino-1-[4-cyano-5-(4-chlorophenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(101) 3-amino-1-[4-cyano-5-(3-methylphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(102) 3-amino-1-[4-cyano-5-(3-methoxyphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(103) 3-amino-1-[4-cyano-5-(2-fluoro-4-methylphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(104) 3-amino-1-[4-cyano-5-(2-fluoro-5-methylphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(105) 3-amino-1-[4-cyano-5-(2,4-difluorophenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid;

(106) 3-amino-1-[4-cyano-5-(4-fluoro-3-methylphenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid; and

(107) 3-amino-1-[4-cyano-5-(2-fluoro-5-methoxyphenyl)pyridine-2-yl]-1H-pyrazole-4-carboxylic acid;

or a pharmaceutically acceptable salt thereof.

15. A pharmaceutical composition comprising the compound according to claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

16. A xanthine oxidase inhibitor comprising the compound according to claim 1 , or a pharmaceutically acceptable salt thereof, as an active ingredient.

17. A therapeutic agent for gout, hyperuricemia, tumor lysis syndrome, urinary calculus, hypertension, dyslipidemia, diabetes, cardiovascular diseases such as arteriosclerosis or heart failure, renal diseases such as diabetic nephropathy, respiratory diseases such as chronic obstructive pulmonary disease, inflammatory bowel diseases, or autoimmune diseases, comprising the compound according to claim 1 , or a pharmaceutically acceptable salt thereof, as an active ingredient.

18. A therapeutic agent for gout or hyperuricemia, comprising the compound according to claim 1 , or a pharmaceutically acceptable salt thereof, as an active ingredient.

19. A compound represented by formula (II):

wherein:

A represents a C 6-10 aryl group or a heteroaryl group, wherein the aryl group or heteroaryl group may be unsubstituted or substituted with 1 to 3 groups Q which are the same or different from one another and selected from the group consisting of a halogen atom, —CN, —NO 2 , a C 1-6 alkyl group, a C 3-7 cycloalkyl group, a C 1-6 halogenoalkyl group, a phenyl group, —CH 2 —O—R 2 , —O—R 2 , —O—C 1-6 halogenoalkyl, —O-benzyl, —O-phenyl, —O—CO—R 2 , —NR 3 R 4 , —NH—CO—R 2 , —CO 2 —R 2 , —CO—R 2 , —CO—NR 3 R 4 , —NH—SO 2 —R 2 , —CO-aryl, —S—R 2 , —SO 2 —C 1-6 alkyl, and —SO 2 -phenyl;

X, Y, and Z represent CR 5 or a nitrogen atom, wherein one of X, Y, and Z represents a nitrogen atom and the remaining two represent CR 5 ;

R represents a hydrogen atom or a C 1-6 alkyl group;

R 1 represents a hydrogen atom, an amino group, or a C 1-6 alkyl group;

R 2 represents a hydrogen atom or a C 1-6 alkyl group;

R 3 and R 4 are the same or different from each other and are a hydrogen atom or a C 1-6 alkyl group, where R 3 and R 4 may be taken together to form with the nitrogen atom to which they are attached a nitrogen-containing saturated monocyclic heterocycle; and

R 5 represents a hydrogen atom, a halogen atom, or a C 1-6 alkyl group;

R 6 represents a protective group of a carboxyl group; and

W represents a halogen atom, a methanesulfonyloxy group, a p-toluenesulfonyloxy group, a trifluoromethanesulfonyloxy group, or a cyano group.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 26, 2018
From: TEIJIN PHARMA LIMITED
To: TEIJIN LIMITED
Reel/Frame 047322/0604 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 22, 2015
From: KAWANA, ASAHI; KANAZAWA, CHIKASHI; TERA, MASAYUKI; TAKAHASHI, YOSHIMASA; IMAZEKI, MARIKO; TAKAHASHI, HIROYUKI; TANOKURA, AKIRA
To: TEIJIN PHARMA LIMITED
Reel/Frame 036855/0682 →
Priority Claims (1)
JP 2013-072788 · Mar 29, 2013 · national
Continuity (1)
Related Publication 20160039784A1 · Feb 11, 2016