JP2003508515A5 - - Google Patents
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- Publication number
- JP2003508515A5 JP2003508515A5 JP2001521703A JP2001521703A JP2003508515A5 JP 2003508515 A5 JP2003508515 A5 JP 2003508515A5 JP 2001521703 A JP2001521703 A JP 2001521703A JP 2001521703 A JP2001521703 A JP 2001521703A JP 2003508515 A5 JP2003508515 A5 JP 2003508515A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- hydroxy
- formula
- alkyl
- compound
- 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.)
- Pending
Links
- 125000000217 alkyl group Chemical group 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 17
- -1 chloro, fluoro, bromo, methyl Chemical group 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 12
- 238000001727 in vivo Methods 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 150000002829 nitrogen Chemical group 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 125000006163 5-membered heteroaryl group Chemical group 0.000 description 2
- 125000005330 8 membered heterocyclic group Chemical group 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- QIVNIXITRYBVFC-LLVKDONJSA-N (2r)-n-(2-chloro-3-methylsulfanyl-4-methylsulfonylphenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound CSC1=C(Cl)C(NC(=O)[C@@](C)(O)C(F)(F)F)=CC=C1S(C)(=O)=O QIVNIXITRYBVFC-LLVKDONJSA-N 0.000 description 1
- DLTGWXUOKOEXOM-MRXNPFEDSA-N (2r)-n-(2-chloro-3-morpholin-4-yl-4-propan-2-ylsulfonylphenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound CC(C)S(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1N1CCOCC1 DLTGWXUOKOEXOM-MRXNPFEDSA-N 0.000 description 1
- NZNZUJLCMIBXOV-GFCCVEGCSA-N (2r)-n-(2-chloro-4-ethylsulfonyl-3-methylsulfanylphenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound CCS(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1SC NZNZUJLCMIBXOV-GFCCVEGCSA-N 0.000 description 1
- RYDLOPNOJOTIDO-CQSZACIVSA-N (2r)-n-(2-chloro-4-methylsulfonyl-3-morpholin-4-ylphenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound FC(F)(F)[C@@](O)(C)C(=O)NC1=CC=C(S(C)(=O)=O)C(N2CCOCC2)=C1Cl RYDLOPNOJOTIDO-CQSZACIVSA-N 0.000 description 1
- XBEQNLUGGXWRPT-MRXNPFEDSA-N (2r)-n-[2-chloro-3-(1-oxo-1,4-thiazinan-4-yl)-4-propan-2-ylsulfonylphenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound CC(C)S(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1N1CCS(=O)CC1 XBEQNLUGGXWRPT-MRXNPFEDSA-N 0.000 description 1
- YVFKGEVOGBEGBA-OAHLLOKOSA-N (2r)-n-[2-chloro-4-ethylsulfonyl-3-(1-oxo-1,4-thiazinan-4-yl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound CCS(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1N1CCS(=O)CC1 YVFKGEVOGBEGBA-OAHLLOKOSA-N 0.000 description 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- 0 CC(*)(C(F)(F)F)C(Nc1cc(*)c(C)c(*)c1*)=O Chemical compound CC(*)(C(F)(F)F)C(Nc1cc(*)c(C)c(*)c1*)=O 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 208000018262 Peripheral vascular disease Diseases 0.000 description 1
- 125000006241 alcohol protecting group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9920814.2 | 1999-09-04 | ||
| GBGB9920814.2A GB9920814D0 (en) | 1999-09-04 | 1999-09-04 | Chemical compounds |
| GB0006641.5 | 2000-03-21 | ||
| GB0006641A GB0006641D0 (en) | 2000-03-21 | 2000-03-21 | Chemical compounds |
| PCT/GB2000/003314 WO2001017956A1 (en) | 1999-09-04 | 2000-08-30 | Substituted n-phenyl 2-hydroxy-2-methyl-3,3,3-trifluoropropanamide derivatives which elevate pyruvate dehydrogenase activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003508515A JP2003508515A (ja) | 2003-03-04 |
| JP2003508515A5 true JP2003508515A5 (https=) | 2007-10-04 |
Family
ID=26243905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001521703A Pending JP2003508515A (ja) | 1999-09-04 | 2000-08-30 | ピルビン酸デヒドロゲナーゼ活性を高める置換ｎ−フェニル−２−ヒドロキシ−２−メチル−３，３，３−トリフルオロプロパンアミド誘導体 |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US6689909B1 (https=) |
| EP (1) | EP1214296B1 (https=) |
| JP (1) | JP2003508515A (https=) |
| KR (1) | KR100692232B1 (https=) |
| CN (1) | CN1235877C (https=) |
| AR (1) | AR035163A1 (https=) |
| AT (1) | ATE262507T1 (https=) |
| AU (1) | AU760061B2 (https=) |
| BG (1) | BG65099B1 (https=) |
| BR (1) | BR0013694A (https=) |
| CA (1) | CA2381581A1 (https=) |
| CO (1) | CO5190690A1 (https=) |
| CZ (1) | CZ2002773A3 (https=) |
| DE (1) | DE60009319T2 (https=) |
| DK (1) | DK1214296T3 (https=) |
| EE (1) | EE05080B1 (https=) |
| ES (1) | ES2216940T3 (https=) |
| HK (1) | HK1045496B (https=) |
| HU (1) | HUP0202725A3 (https=) |
| IL (2) | IL148111A0 (https=) |
| IS (1) | IS2069B (https=) |
| MX (1) | MXPA02002319A (https=) |
| MY (1) | MY127036A (https=) |
| NO (1) | NO20021040L (https=) |
| NZ (1) | NZ517147A (https=) |
| PL (1) | PL353887A1 (https=) |
| PT (1) | PT1214296E (https=) |
| RU (1) | RU2255085C2 (https=) |
| SK (1) | SK286774B6 (https=) |
| TR (1) | TR200200550T2 (https=) |
| TW (1) | TW577867B (https=) |
| WO (1) | WO2001017956A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6878712B1 (en) | 1999-09-04 | 2005-04-12 | Astrazeneca Ab | Amides as inhibitors for pyruvate dehydrogenase |
| GB0012012D0 (en) * | 2000-05-19 | 2000-07-05 | Astrazeneca Ab | Chemical compound |
| GB0120471D0 (en) * | 2001-08-23 | 2001-10-17 | Astrazeneca Ab | Chemical compounds |
| KR100927304B1 (ko) * | 2001-12-27 | 2009-11-18 | 다이이찌 세이야꾸 가부시기가이샤 | β-아밀로이드 단백 생산·분비 저해제 |
| US9388164B2 (en) | 2011-05-03 | 2016-07-12 | Agios Pharmaceuticals, Inc | Methods of using pyruvate kinase activators |
| EA032007B1 (ru) | 2012-11-08 | 2019-03-29 | Аджиос Фармасьютикалз, Инк. | Терапевтические соединения и композиции и их использование в качестве модуляторов пк-m2 |
| WO2014139144A1 (en) | 2013-03-15 | 2014-09-18 | Agios Pharmaceuticals, Inc. | Therapeutic compounds and compositions |
| TWI796353B (zh) | 2017-08-15 | 2023-03-21 | 美商阿吉歐斯製藥公司 | 丙酮酸激酶調節劑及其用途 |
| CN109096186B (zh) * | 2018-09-29 | 2020-08-04 | 中南大学 | 一种2-芳磺酰基喹啉衍生物的合成方法 |
| AU2022337617A1 (en) * | 2021-09-01 | 2024-04-18 | Japan Tobacco Inc. | Nitrogen-containing tricyclic compound and pharmaceutical use thereof |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0002309B1 (en) | 1977-10-12 | 1982-12-01 | Imperial Chemical Industries Plc | Acylanilides, process for their manufacture and pharmaceutical and veterinary compositions containing them |
| US4191775A (en) | 1977-12-15 | 1980-03-04 | Imperial Chemical Industries Limited | Amide derivatives |
| NZ197008A (en) | 1980-05-22 | 1984-10-19 | Ici Ltd | Acylanilide derivatives and pharmaceutical compositions |
| AU8961382A (en) | 1981-11-06 | 1983-05-12 | Imperial Chemical Industries Plc | Amide derivatives |
| US4537618A (en) | 1982-05-26 | 1985-08-27 | Ciba Geigy Corporation | N-phenylsulfonyl-N'-pyrimidinylureas |
| ATE28864T1 (de) | 1982-07-23 | 1987-08-15 | Ici Plc | Amide-derivate. |
| GB8617653D0 (en) | 1986-07-18 | 1986-08-28 | Ici Plc | Amide derivatives |
| GB8617652D0 (en) | 1986-07-18 | 1986-08-28 | Ici Plc | Acylanilide derivatives |
| GB9116069D0 (en) * | 1991-07-25 | 1991-09-11 | Ici Plc | Therapeutic amides |
| GB9214120D0 (en) * | 1991-07-25 | 1992-08-12 | Ici Plc | Therapeutic amides |
| EP0539329A1 (de) | 1991-10-25 | 1993-04-28 | Ciba-Geigy Ag | Acetylen-Verbindungen, verwendbar als Leukotrien-Antagonisten |
| SE9103397D0 (sv) | 1991-11-18 | 1991-11-18 | Kabi Pharmacia Ab | Nya substituerade salicylsyror |
| IL105558A (en) | 1992-05-18 | 1998-04-05 | Zeneca Ltd | Tertiary carbinols having potassium channel activity, process for their preparation and pharmaceutical compositions containing them |
| GB9305295D0 (en) * | 1993-03-15 | 1993-05-05 | Zeneca Ltd | Therapeutic compounds |
| GB9309716D0 (en) | 1993-05-12 | 1993-06-23 | Zeneca Ltd | Heterocyclic derivatives |
| GB9310069D0 (en) | 1993-05-17 | 1993-06-30 | Zeneca Ltd | Heterocyclic compounds |
| GB9310095D0 (en) | 1993-05-17 | 1993-06-30 | Zeneca Ltd | Therapeutic compounds |
| GB2278054A (en) * | 1993-05-18 | 1994-11-23 | Zeneca Ltd | Compounds for the treatment of urinary incontinence |
| GB9505082D0 (en) | 1995-03-14 | 1995-05-03 | Zeneca Ltd | Medicament |
| GB9607458D0 (en) | 1996-04-10 | 1996-06-12 | Zeneca Ltd | Enzymatic process for stereoselective preparation of therapeutic amides |
| GB9804648D0 (en) | 1998-03-06 | 1998-04-29 | Zeneca Ltd | Chemical compounds |
| GB9805520D0 (en) * | 1998-03-17 | 1998-05-13 | Zeneca Ltd | Chemical compounds |
| GB9811427D0 (en) | 1998-05-29 | 1998-07-22 | Zeneca Ltd | Chemical compounds |
-
2000
- 2000-08-30 CA CA002381581A patent/CA2381581A1/en not_active Abandoned
- 2000-08-30 PL PL00353887A patent/PL353887A1/xx not_active Application Discontinuation
- 2000-08-30 SK SK300-2002A patent/SK286774B6/sk not_active IP Right Cessation
- 2000-08-30 AU AU68543/00A patent/AU760061B2/en not_active Ceased
- 2000-08-30 KR KR1020027002841A patent/KR100692232B1/ko not_active Expired - Fee Related
- 2000-08-30 BR BR0013694-8A patent/BR0013694A/pt not_active Application Discontinuation
- 2000-08-30 EP EP00956672A patent/EP1214296B1/en not_active Expired - Lifetime
- 2000-08-30 MY MYPI20004037 patent/MY127036A/en unknown
- 2000-08-30 WO PCT/GB2000/003314 patent/WO2001017956A1/en not_active Ceased
- 2000-08-30 US US10/069,994 patent/US6689909B1/en not_active Expired - Fee Related
- 2000-08-30 IL IL14811100A patent/IL148111A0/xx active IP Right Grant
- 2000-08-30 DK DK00956672T patent/DK1214296T3/da active
- 2000-08-30 EE EEP200200113A patent/EE05080B1/xx not_active IP Right Cessation
- 2000-08-30 PT PT00956672T patent/PT1214296E/pt unknown
- 2000-08-30 CN CNB008152446A patent/CN1235877C/zh not_active Expired - Fee Related
- 2000-08-30 JP JP2001521703A patent/JP2003508515A/ja active Pending
- 2000-08-30 ES ES00956672T patent/ES2216940T3/es not_active Expired - Lifetime
- 2000-08-30 TR TR2002/00550T patent/TR200200550T2/xx unknown
- 2000-08-30 HU HU0202725A patent/HUP0202725A3/hu unknown
- 2000-08-30 HK HK02107004.7A patent/HK1045496B/en not_active IP Right Cessation
- 2000-08-30 AT AT00956672T patent/ATE262507T1/de not_active IP Right Cessation
- 2000-08-30 NZ NZ517147A patent/NZ517147A/en unknown
- 2000-08-30 MX MXPA02002319A patent/MXPA02002319A/es active IP Right Grant
- 2000-08-30 RU RU2002108508/04A patent/RU2255085C2/ru not_active IP Right Cessation
- 2000-08-30 CZ CZ2002773A patent/CZ2002773A3/cs unknown
- 2000-08-30 DE DE60009319T patent/DE60009319T2/de not_active Expired - Fee Related
- 2000-09-01 CO CO00065992A patent/CO5190690A1/es not_active Application Discontinuation
- 2000-09-04 AR ARP000104623A patent/AR035163A1/es unknown
- 2000-09-04 TW TW089118053A patent/TW577867B/zh not_active IP Right Cessation
-
2002
- 2002-02-11 IL IL148111A patent/IL148111A/en not_active IP Right Cessation
- 2002-02-26 IS IS6285A patent/IS2069B/xx unknown
- 2002-03-01 NO NO20021040A patent/NO20021040L/no not_active Application Discontinuation
- 2002-03-14 BG BG106520A patent/BG65099B1/bg unknown
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