JP2016500115A5 - - Google Patents
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- Publication number
- JP2016500115A5 JP2016500115A5 JP2015544335A JP2015544335A JP2016500115A5 JP 2016500115 A5 JP2016500115 A5 JP 2016500115A5 JP 2015544335 A JP2015544335 A JP 2015544335A JP 2015544335 A JP2015544335 A JP 2015544335A JP 2016500115 A5 JP2016500115 A5 JP 2016500115A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- selenazole
- formic acid
- cyano
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 23
- FICQFRCPSFCFBY-UHFFFAOYSA-N 2-[bis(methylsulfanyl)methylidene]propanedinitrile Chemical compound CSC(SC)=C(C#N)C#N FICQFRCPSFCFBY-UHFFFAOYSA-N 0.000 claims description 14
- -1 R b is H Chemical group 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- OZQRSDCVZYGMMZ-UHFFFAOYSA-N 2-[3-cyano-4-(cyclopropylmethoxy)phenyl]-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound [se]1C(C(O)=O)=C(C)N=C1C(C=C1C#N)=CC=C1OCC1CC1 OZQRSDCVZYGMMZ-UHFFFAOYSA-N 0.000 claims description 4
- XWQZGBSSSNZOIO-UHFFFAOYSA-N 2-(3-cyano-4-cyclohexylsulfanylphenyl)-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound C(#N)C=1C=C(C=CC1SC1CCCCC1)C=1[Se]C(=C(N1)C)C(=O)O XWQZGBSSSNZOIO-UHFFFAOYSA-N 0.000 claims description 2
- AIVRMJQFXVTQFW-UHFFFAOYSA-N 2-(3-cyano-4-ethoxyphenyl)-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound C1=C(C#N)C(OCC)=CC=C1C1=NC(C)=C(C(O)=O)[se]1 AIVRMJQFXVTQFW-UHFFFAOYSA-N 0.000 claims description 2
- VWRYHVIUYDSFOD-UHFFFAOYSA-N 2-(3-cyano-4-naphthalen-1-ylphenyl)-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound [se]1C(C(O)=O)=C(C)N=C1C1=CC=C(C=2C3=CC=CC=C3C=CC=2)C(C#N)=C1 VWRYHVIUYDSFOD-UHFFFAOYSA-N 0.000 claims description 2
- VWPQHAKPTFXZFI-UHFFFAOYSA-N 2-(3-cyano-4-phenylmethoxyphenyl)-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound [se]1C(C(O)=O)=C(C)N=C1C(C=C1C#N)=CC=C1OCC1=CC=CC=C1 VWPQHAKPTFXZFI-UHFFFAOYSA-N 0.000 claims description 2
- ZEOSJTLLZKNHCC-UHFFFAOYSA-N 2-(3-cyano-4-propan-2-yloxyphenyl)-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1C1=NC(C)=C(C(O)=O)[se]1 ZEOSJTLLZKNHCC-UHFFFAOYSA-N 0.000 claims description 2
- JXWZPOXVTBYQLO-UHFFFAOYSA-N 2-(3-cyano-4-propan-2-ylsulfanylphenyl)-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound C1=C(C#N)C(SC(C)C)=CC=C1C1=NC(C)=C(C(O)=O)[se]1 JXWZPOXVTBYQLO-UHFFFAOYSA-N 0.000 claims description 2
- LFAFXFBGJIKZDF-UHFFFAOYSA-N 2-(3-cyano-4-pyridin-2-ylsulfanylphenyl)-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound [se]1C(C(O)=O)=C(C)N=C1C(C=C1C#N)=CC=C1SC1=CC=CC=N1 LFAFXFBGJIKZDF-UHFFFAOYSA-N 0.000 claims description 2
- ISFYDGWZVFOSLF-UHFFFAOYSA-N 2-(4-benzylsulfanyl-3-cyanophenyl)-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound [se]1C(C(O)=O)=C(C)N=C1C(C=C1C#N)=CC=C1SCC1=CC=CC=C1 ISFYDGWZVFOSLF-UHFFFAOYSA-N 0.000 claims description 2
- GBYPWHXCDNXFQE-UHFFFAOYSA-N 2-(4-tert-butylsulfanyl-3-cyanophenyl)-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound [se]1C(C(O)=O)=C(C)N=C1C1=CC=C(SC(C)(C)C)C(C#N)=C1 GBYPWHXCDNXFQE-UHFFFAOYSA-N 0.000 claims description 2
- OIWASTVUDYNHDQ-UHFFFAOYSA-N 2-(6-cyano-1-pyridin-3-ylcyclohexa-2,4-dien-1-yl)-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound C(#N)C1C=CC=CC1(C=1C=NC=CC=1)C=1[Se]C(=C(N=1)C)C(=O)O OIWASTVUDYNHDQ-UHFFFAOYSA-N 0.000 claims description 2
- TVBIEBOKMSVPMT-UHFFFAOYSA-N 2-(6-cyano-1-pyridin-4-ylcyclohexa-2,4-dien-1-yl)-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound CC1=C([Se]C(=N1)C2(C=CC=CC2C#N)C3=CC=NC=C3)C(=O)O TVBIEBOKMSVPMT-UHFFFAOYSA-N 0.000 claims description 2
- BHAKKGAABUFYHN-UHFFFAOYSA-N 2-[3-bromo-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound C1=C(Br)C(OCC(C)C)=CC=C1C1=NC(C)=C(C(O)=O)[se]1 BHAKKGAABUFYHN-UHFFFAOYSA-N 0.000 claims description 2
- VOAFBCREWROANP-UHFFFAOYSA-N 2-[3-bromo-4-(phenylcarbamoyl)phenyl]-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound [se]1C(C(O)=O)=C(C)N=C1C(C=C1Br)=CC=C1C(=O)NC1=CC=CC=C1 VOAFBCREWROANP-UHFFFAOYSA-N 0.000 claims description 2
- WJFJPFIOFQKRCF-UHFFFAOYSA-N 2-[3-cyano-4-(2-methylpropylsulfanyl)phenyl]-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound C1=C(C#N)C(SCC(C)C)=CC=C1C1=NC(C)=C(C(O)=O)[se]1 WJFJPFIOFQKRCF-UHFFFAOYSA-N 0.000 claims description 2
- VGMHPKSVFAHOHY-UHFFFAOYSA-N 2-[3-cyano-4-(3-methylbutoxy)phenyl]-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound C1=C(C#N)C(OCCC(C)C)=CC=C1C1=NC(C)=C(C(O)=O)[se]1 VGMHPKSVFAHOHY-UHFFFAOYSA-N 0.000 claims description 2
- HLFHKDUVCDXMNB-UHFFFAOYSA-N 2-[3-cyano-4-(4-methylpiperazin-1-yl)phenyl]-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound C1CN(C)CCN1C1=CC=C(C=2[se]C(=C(C)N=2)C(O)=O)C=C1C#N HLFHKDUVCDXMNB-UHFFFAOYSA-N 0.000 claims description 2
- UGFYBXZHOBOTIB-UHFFFAOYSA-N 2-[3-cyano-4-(cyclohexylmethoxy)phenyl]-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound [se]1C(C(O)=O)=C(C)N=C1C(C=C1C#N)=CC=C1OCC1CCCCC1 UGFYBXZHOBOTIB-UHFFFAOYSA-N 0.000 claims description 2
- GYLQJSKRAQHYCO-UHFFFAOYSA-N 2-[3-cyano-4-(dimethylamino)phenyl]-4-methyl-1,3-selenazole-5-carboxylic acid Chemical compound C1=C(C#N)C(N(C)C)=CC=C1C1=NC(C)=C(C(O)=O)[se]1 GYLQJSKRAQHYCO-UHFFFAOYSA-N 0.000 claims description 2
- MFFJRDFTNYKHRZ-UHFFFAOYSA-N 4-methyl-2-[3-(trifluoromethyl)phenyl]-1,3-selenazole-5-carboxylic acid Chemical compound [se]1C(C(O)=O)=C(C)N=C1C1=CC=CC(C(F)(F)F)=C1 MFFJRDFTNYKHRZ-UHFFFAOYSA-N 0.000 claims description 2
- XXYPCAUGDJXHHD-UHFFFAOYSA-N 4-methyl-2-[4-(2-methylpropoxy)-3-(trifluoromethyl)phenyl]-1,3-selenazole-5-carboxylic acid Chemical compound C1=C(C(F)(F)F)C(OCC(C)C)=CC=C1C1=NC(C)=C(C(O)=O)[se]1 XXYPCAUGDJXHHD-UHFFFAOYSA-N 0.000 claims description 2
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 11
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 125000004193 piperazinyl group Chemical class 0.000 claims 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- 229940123769 Xanthine oxidase inhibitor Drugs 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- AWHNUHMUCGRKRA-UHFFFAOYSA-N benzylsulfonylmethylbenzene Chemical group C=1C=CC=CC=1CS(=O)(=O)CC1=CC=CC=C1 AWHNUHMUCGRKRA-UHFFFAOYSA-N 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 2
- 239000003064 xanthine oxidase inhibitor Substances 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- UVMPOFNVOXGNFV-UHFFFAOYSA-N 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-(hydroxymethyl)-1,3-selenazole-5-carboxylic acid Chemical compound C1=C(C#N)C(OCC(C)C)=CC=C1C1=NC(CO)=C(C(O)=O)[se]1 UVMPOFNVOXGNFV-UHFFFAOYSA-N 0.000 claims 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical class CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 claims 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 1
- 201000005569 Gout Diseases 0.000 claims 1
- 201000001431 Hyperuricemia Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 208000033679 diabetic kidney disease Diseases 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- USVVENVKYJZFMW-ONEGZZNKSA-N (e)-carboxyiminocarbamic acid Chemical compound OC(=O)\N=N\C(O)=O USVVENVKYJZFMW-ONEGZZNKSA-N 0.000 description 1
- 0 Cc1c(*)nc(-c2ccccc2)[s]1 Chemical compound Cc1c(*)nc(-c2ccccc2)[s]1 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical compound OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210504310.8 | 2012-11-30 | ||
| CN201210504310.8A CN103848798B (zh) | 2012-11-30 | 2012-11-30 | 2-芳基硒唑化合物及其药物组合物 |
| PCT/CN2013/087736 WO2014082548A1 (zh) | 2012-11-30 | 2013-11-24 | 2-芳基硒唑化合物及其药物组合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016500115A JP2016500115A (ja) | 2016-01-07 |
| JP2016500115A5 true JP2016500115A5 (OSRAM) | 2017-05-18 |
| JP6143877B2 JP6143877B2 (ja) | 2017-06-07 |
Family
ID=50827179
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015544335A Expired - Fee Related JP6143877B2 (ja) | 2012-11-30 | 2013-11-24 | ２−アリールセレナゾール化合物及びその薬剤組成物 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9802907B2 (OSRAM) |
| EP (1) | EP2927219B1 (OSRAM) |
| JP (1) | JP6143877B2 (OSRAM) |
| CN (1) | CN103848798B (OSRAM) |
| WO (1) | WO2014082548A1 (OSRAM) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103936693B (zh) * | 2013-01-22 | 2016-06-15 | 沈阳药科大学 | 2-(3-氰基-4-取代苯基)-4-甲基-1,3-硒唑-5-甲酸及其酯类化合物和制备方法 |
| CN108358866B (zh) * | 2017-01-12 | 2021-03-23 | 江西同和药业股份有限公司 | 一种非布司他中间体的制备方法及其在制备非布司他中的应用 |
| CN111662239B (zh) * | 2019-03-06 | 2023-07-28 | 中国医学科学院药物研究所 | 1,2,4-三唑类化合物及其制法和药物用途 |
| CN113354616B (zh) * | 2020-03-05 | 2024-03-26 | 中国医学科学院药物研究所 | 二芳基-1,2,4-三唑类化合物及其制法和药物用途 |
| WO2022083687A1 (zh) * | 2020-10-21 | 2022-04-28 | 南京明德新药研发有限公司 | 硒杂环类化合物及其应用 |
| WO2023202706A1 (zh) * | 2022-04-21 | 2023-10-26 | 南京明德新药研发有限公司 | 硒杂环类化合物的盐型和晶型及其应用 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2725886B2 (ja) * | 1990-11-30 | 1998-03-11 | 帝人株式会社 | ２―アリールチアゾール誘導体及びその医薬組成物 |
| JP3113110B2 (ja) | 1993-01-19 | 2000-11-27 | 帝人株式会社 | イソキサゾールおよびイソチアゾール誘導体 |
| CA2190993C (en) | 1995-04-07 | 2004-06-01 | Mikio Ota | Protective agent for organ or tissue |
| ID21775A (id) | 1996-10-25 | 1999-07-22 | Yoshitomi Pharmaceutical | Senyawa-senyawa 1-fenilpirazol dan penggunaan farmasinya |
| JPH10310578A (ja) | 1996-11-13 | 1998-11-24 | Yoshitomi Pharmaceut Ind Ltd | ３−フェニルピラゾール化合物 |
| JP2002105067A (ja) * | 2000-09-28 | 2002-04-10 | Teijin Ltd | ２−フェニルチアゾール誘導体、およびそれを有効成分とする医薬組成物 |
| EP1757610B1 (en) | 2004-06-14 | 2011-06-08 | Nippon Chemiphar Co., Ltd. | Condensed pyrimidine derivative and xanthine oxidase inhibitor |
| JPWO2006022375A1 (ja) | 2004-08-27 | 2008-05-08 | アステラス製薬株式会社 | ２−フェニルチオフェン誘導体 |
| EP1783116B1 (en) | 2004-08-27 | 2009-08-26 | Astellas Pharma Inc. | 2-phenylpyridine derivative |
| WO2007043457A1 (ja) * | 2005-10-07 | 2007-04-19 | Astellas Pharma Inc. | トリアリールカルボン酸誘導体 |
| CA2789458A1 (en) * | 2010-02-25 | 2011-09-01 | Heonjoong Kang | Selenalzole derivative having ligand which activates peroxisome proliferator activated receptor (ppar), preparing method thereof and usage of the chemical compounds |
| CN103130744B (zh) * | 2012-08-28 | 2014-10-15 | 沈阳药科大学 | 一种硒唑甲酸类化合物及其制备方法和用途 |
-
2012
- 2012-11-30 CN CN201210504310.8A patent/CN103848798B/zh active Active
-
2013
- 2013-11-24 EP EP13858539.3A patent/EP2927219B1/en not_active Not-in-force
- 2013-11-24 JP JP2015544335A patent/JP6143877B2/ja not_active Expired - Fee Related
- 2013-11-24 WO PCT/CN2013/087736 patent/WO2014082548A1/zh not_active Ceased
- 2013-11-24 US US14/648,664 patent/US9802907B2/en not_active Expired - Fee Related
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