JP2004509857A5 - - Google Patents
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- Publication number
- JP2004509857A5 JP2004509857A5 JP2002515891A JP2002515891A JP2004509857A5 JP 2004509857 A5 JP2004509857 A5 JP 2004509857A5 JP 2002515891 A JP2002515891 A JP 2002515891A JP 2002515891 A JP2002515891 A JP 2002515891A JP 2004509857 A5 JP2004509857 A5 JP 2004509857A5
- Authority
- JP
- Japan
- Prior art keywords
- dimethylethyl
- oxazolyl
- thiazolyl
- thio
- methyl
- 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.)
- Withdrawn
Links
- 150000003839 salts Chemical class 0.000 description 12
- 239000012453 solvate Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 125000000547 substituted alkyl group Chemical group 0.000 description 5
- 239000003937 drug carrier Substances 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- USAKOZCUIYTREA-LLVKDONJSA-N (3r)-n-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]piperidine-3-carboxamide Chemical compound O1C(C(C)(C)C)=CN=C1CSC(S1)=CN=C1NC(=O)[C@H]1CNCCC1 USAKOZCUIYTREA-LLVKDONJSA-N 0.000 description 2
- 0 C*(C)c1cnc(CSc2cnc(NC(C3CN(*)CCC3)=O)[s]2)[o]1 Chemical compound C*(C)c1cnc(CSc2cnc(NC(C3CN(*)CCC3)=O)[s]2)[o]1 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- OUSFTKFNBAZUKL-UHFFFAOYSA-N N-(5-{[(5-tert-butyl-1,3-oxazol-2-yl)methyl]sulfanyl}-1,3-thiazol-2-yl)piperidine-4-carboxamide Chemical compound O1C(C(C)(C)C)=CN=C1CSC(S1)=CN=C1NC(=O)C1CCNCC1 OUSFTKFNBAZUKL-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 2
- USAKOZCUIYTREA-UHFFFAOYSA-N n-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]piperidine-3-carboxamide Chemical compound O1C(C(C)(C)C)=CN=C1CSC(S1)=CN=C1NC(=O)C1CNCCC1 USAKOZCUIYTREA-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- USAKOZCUIYTREA-NSHDSACASA-N (3s)-n-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]piperidine-3-carboxamide Chemical compound O1C(C(C)(C)C)=CN=C1CSC(S1)=CN=C1NC(=O)[C@@H]1CNCCC1 USAKOZCUIYTREA-NSHDSACASA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- -1 dihydrochloride Chemical compound 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LURBGHNXFQSPMM-UHFFFAOYSA-N n-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]-1-(2,3-dihydroxypropyl)piperidine-4-carboxamide Chemical compound O1C(C(C)(C)C)=CN=C1CSC(S1)=CN=C1NC(=O)C1CCN(CC(O)CO)CC1 LURBGHNXFQSPMM-UHFFFAOYSA-N 0.000 description 1
- NASKBLMGBFRGIF-UHFFFAOYSA-N n-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]-1-(2-hydroxyethyl)piperidine-4-carboxamide Chemical compound O1C(C(C)(C)C)=CN=C1CSC(S1)=CN=C1NC(=O)C1CCN(CCO)CC1 NASKBLMGBFRGIF-UHFFFAOYSA-N 0.000 description 1
- BMJRSDXYHRHHKI-UHFFFAOYSA-N n-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]-1-cyclopropylpiperidine-4-carboxamide Chemical compound O1C(C(C)(C)C)=CN=C1CSC(S1)=CN=C1NC(=O)C1CCN(C2CC2)CC1 BMJRSDXYHRHHKI-UHFFFAOYSA-N 0.000 description 1
- JJJVIPYJUNRQTI-UHFFFAOYSA-N n-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]-1-propan-2-ylpiperidine-4-carboxamide Chemical compound C1CN(C(C)C)CCC1C(=O)NC(S1)=NC=C1SCC1=NC=C(C(C)(C)C)O1 JJJVIPYJUNRQTI-UHFFFAOYSA-N 0.000 description 1
- IYLMWEFXWOERFM-UHFFFAOYSA-N n-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]cyclohexanecarboxamide Chemical compound O1C(C(C)(C)C)=CN=C1CSC(S1)=CN=C1NC(=O)C1CCCCC1 IYLMWEFXWOERFM-UHFFFAOYSA-N 0.000 description 1
- 230000023603 positive regulation of transcription initiation, DNA-dependent Effects 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US61662700A | 2000-07-26 | 2000-07-26 | |
US09/727,957 US6515004B1 (en) | 1999-12-15 | 2000-12-01 | N-[5-[[[5-alkyl-2-oxazolyl]methyl]thio]-2-thiazolyl]-carboxamide inhibitors of cyclin dependent kinases |
US09/746,060 US6414156B2 (en) | 1998-10-21 | 2000-12-22 | Process for preparing azacycloalkanoylaminothiazoles |
PCT/US2001/015081 WO2002010162A1 (en) | 2000-07-26 | 2001-05-09 | N-[5-[[[5-alkyl-2-oxazolyl]methyl]thio]-2-thiazolyl] carboxamide inhibitors of cyclin dependent kinases |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2004509857A JP2004509857A (ja) | 2004-04-02 |
JP2004509857A5 true JP2004509857A5 (ru) | 2008-06-19 |
Family
ID=27417184
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2002515891A Withdrawn JP2004509857A (ja) | 2000-07-26 | 2001-05-09 | サイクリン依存性キナーゼのn−[5−[[[5−アルキル−2−オキサゾリル]メチル]チオ]−2−チアゾリル]カルボキサミドインヒビター |
Country Status (26)
Country | Link |
---|---|
EP (1) | EP1303513A1 (ru) |
JP (1) | JP2004509857A (ru) |
KR (1) | KR20030016429A (ru) |
CN (1) | CN100457753C (ru) |
AR (1) | AR030563A1 (ru) |
AU (1) | AU2001259704A1 (ru) |
BG (1) | BG65132B1 (ru) |
BR (1) | BR0112674A (ru) |
CA (1) | CA2417254A1 (ru) |
CZ (1) | CZ2003237A3 (ru) |
EE (1) | EE200300041A (ru) |
EG (1) | EG24409A (ru) |
GE (1) | GEP20043367B (ru) |
HR (1) | HRP20030116A2 (ru) |
HU (1) | HUP0303698A2 (ru) |
IL (2) | IL153591A0 (ru) |
LV (1) | LV13037B (ru) |
MX (1) | MXPA03000774A (ru) |
MY (1) | MY129635A (ru) |
NO (1) | NO20030394L (ru) |
PL (1) | PL365170A1 (ru) |
SI (1) | SI21099A (ru) |
SK (1) | SK18392002A3 (ru) |
TW (1) | TWI302533B (ru) |
WO (1) | WO2002010162A1 (ru) |
YU (1) | YU4903A (ru) |
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6414156B2 (en) | 1998-10-21 | 2002-07-02 | Bristol-Myers Squibb Company | Process for preparing azacycloalkanoylaminothiazoles |
EP2311818B1 (en) * | 2002-02-28 | 2013-01-16 | Novartis AG | Combination of a 5-phenylthiazole compound as PI3 kinase inhibitor with an antiinflammatory, bronchodilatory or antihistamine drug |
PE20030968A1 (es) | 2002-02-28 | 2004-01-12 | Novartis Ag | Derivados de 5-feniltiazol como inhibidores de cinasas |
US7084271B2 (en) | 2002-09-04 | 2006-08-01 | Schering Corporation | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
US8580782B2 (en) | 2002-09-04 | 2013-11-12 | Merck Sharp & Dohme Corp. | Substituted pyrazolo[1,5-a]pyrimidines as cyclin dependent kinase inhibitors |
RU2380369C9 (ru) | 2002-09-04 | 2011-07-10 | Шеринг Корпорейшн | Новые пиразолопиримидины как ингибиторы циклин-зависимой киназы |
US8673924B2 (en) | 2002-09-04 | 2014-03-18 | Merck Sharp & Dohme Corp. | Substituted pyrazolo[1,5-a]pyrimidines as cyclin dependent kinase inhibitors |
CA2499874A1 (en) | 2002-09-23 | 2004-04-01 | Schering Corporation | Novel imidazopyrazines as cyclin dependent kinase inhibitors |
WO2004026877A1 (en) | 2002-09-23 | 2004-04-01 | Schering Corporation | Imidazopyrazines as cyclin dependent kinase inhibitors |
GB0320197D0 (en) | 2003-08-28 | 2003-10-01 | Novartis Ag | Organic compounds |
EP1555264A1 (en) * | 2004-01-15 | 2005-07-20 | Sireen AG | Five-membered heterocyclic compounds as inhibitors of SRC family protein kinase. |
DE102005008310A1 (de) * | 2005-02-17 | 2006-08-24 | Schering Ag | Verwendung von CDKII Inhibitoren zur Fertilitätskontrolle |
EP1928865A1 (en) | 2005-08-17 | 2008-06-11 | Schering Corporation | Novel high affinity thiophene-based and furan-based kinase ligands |
ATE478852T1 (de) | 2005-09-09 | 2010-09-15 | Schering Corp | Neue 4-cyano-, 4-amino-, und 4- aminomethylderivative von pyrazoloä1,5- aüpyridinen, pyrazoloä1,5-cüpyrimidinen und 2h- indazolverbindungen und 5-cyano-, 5-amino- und 5- aminomethylderivative von imidazoä1,2-aüpyridinen,und imidazoä1,5-aüpyrazinverbindungen als inhibitoren der cyclinabhänggen kinase |
WO2007041712A1 (en) | 2005-10-06 | 2007-04-12 | Schering Corporation | Pyrazolopyrimidines as protein kinase inhibitors |
JP2009539846A (ja) * | 2006-06-06 | 2009-11-19 | ブリストル−ミエルス スクイッブ カンパニー | N−[5−[[[5−(1,1−ジメチルエチル)−2−オキサゾリル]メチル]チオ]−2−チアゾリル]−4−ピペリジンカルボキサミドの結晶形 |
US20090175852A1 (en) | 2006-06-06 | 2009-07-09 | Schering Corporation | Imidazopyrazines as protein kinase inhibitors |
US9206142B2 (en) | 2006-10-31 | 2015-12-08 | Merck Sharp & Dohme Corp. | Anilinopiperazine derivatives and methods of use thereof |
AR063531A1 (es) | 2006-10-31 | 2009-01-28 | Schering Corp | Derivados de anilinopiperazina y composicion farmaceutica |
EP2409700A1 (en) | 2007-05-08 | 2012-01-25 | Schering Corporation | Methods of treatment using intravenous formulations comprising temozolomide |
TW200922564A (en) | 2007-09-10 | 2009-06-01 | Curis Inc | CDK inhibitors containing a zinc binding moiety |
WO2010075542A1 (en) | 2008-12-23 | 2010-07-01 | Curis, Inc. | Cdk inhibitors |
EP2470183B1 (en) | 2009-08-26 | 2015-09-16 | Merck Sharp & Dohme Corp. | Heterocyclic amide compounds as protein kinase inhibitors |
WO2013148775A1 (en) | 2012-03-30 | 2013-10-03 | Merck Sharp & Dohme Corp. | Predictive biomarker useful for cancer therapy mediated by a cdk inhibitor |
EP3078671A4 (en) * | 2013-12-04 | 2017-05-31 | Hangzhou Minsheng Institutes for Pharma Research Co., Ltd. | Gemcitabine derivative, composition containing the derivative and pharmaceutical use of the derivative |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6262096B1 (en) * | 1997-11-12 | 2001-07-17 | Bristol-Myers Squibb Company | Aminothiazole inhibitors of cyclin dependent kinases |
US6040321A (en) * | 1997-11-12 | 2000-03-21 | Bristol-Myers Squibb Company | Aminothiazole inhibitors of cyclin dependent kinases |
CA2332325A1 (en) * | 1998-06-18 | 1999-12-23 | Bristol-Myers Squibb Company | Carbon substituted aminothiazole inhibitors of cyclin dependent kinases |
US6414156B2 (en) * | 1998-10-21 | 2002-07-02 | Bristol-Myers Squibb Company | Process for preparing azacycloalkanoylaminothiazoles |
MY125768A (en) * | 1999-12-15 | 2006-08-30 | Bristol Myers Squibb Co | N-[5-[[[5-alkyl-2-oxazolyl]methyl]thio]-2-thiazolyl]-carboxamide inhibitors of cyclin dependent kinases |
-
2001
- 2001-05-09 SI SI200120051A patent/SI21099A/sl not_active IP Right Cessation
- 2001-05-09 BR BR0112674-1A patent/BR0112674A/pt not_active Application Discontinuation
- 2001-05-09 WO PCT/US2001/015081 patent/WO2002010162A1/en not_active Application Discontinuation
- 2001-05-09 HU HU0303698A patent/HUP0303698A2/hu unknown
- 2001-05-09 CN CNB018133673A patent/CN100457753C/zh not_active Expired - Fee Related
- 2001-05-09 AU AU2001259704A patent/AU2001259704A1/en not_active Abandoned
- 2001-05-09 JP JP2002515891A patent/JP2004509857A/ja not_active Withdrawn
- 2001-05-09 CZ CZ2003237A patent/CZ2003237A3/cs unknown
- 2001-05-09 EE EEP200300041A patent/EE200300041A/xx unknown
- 2001-05-09 EP EP01933266A patent/EP1303513A1/en not_active Withdrawn
- 2001-05-09 GE GE5063A patent/GEP20043367B/en unknown
- 2001-05-09 KR KR10-2003-7001141A patent/KR20030016429A/ko not_active Application Discontinuation
- 2001-05-09 IL IL15359101A patent/IL153591A0/xx unknown
- 2001-05-09 YU YU4903A patent/YU4903A/sh unknown
- 2001-05-09 MX MXPA03000774A patent/MXPA03000774A/es unknown
- 2001-05-09 PL PL01365170A patent/PL365170A1/xx not_active Application Discontinuation
- 2001-05-09 SK SK1839-2002A patent/SK18392002A3/sk unknown
- 2001-05-09 CA CA002417254A patent/CA2417254A1/en not_active Abandoned
- 2001-05-16 TW TW090111741A patent/TWI302533B/zh not_active IP Right Cessation
- 2001-05-22 MY MYPI20012414A patent/MY129635A/en unknown
- 2001-05-23 EG EG20010550A patent/EG24409A/xx active
- 2001-05-24 AR ARP010102516A patent/AR030563A1/es unknown
-
2002
- 2002-12-23 IL IL153591A patent/IL153591A/en not_active IP Right Cessation
-
2003
- 2003-01-16 BG BG107468A patent/BG65132B1/bg unknown
- 2003-01-24 NO NO20030394A patent/NO20030394L/no not_active Application Discontinuation
- 2003-02-19 HR HR20030116A patent/HRP20030116A2/hr not_active Application Discontinuation
- 2003-02-26 LV LVP-03-24A patent/LV13037B/en unknown
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