WO1999024416A1 - Aminothiazole inhibitors of cyclin dependent kinases - Google Patents
Aminothiazole inhibitors of cyclin dependent kinases Download PDFInfo
- Publication number
- WO1999024416A1 WO1999024416A1 PCT/US1998/023197 US9823197W WO9924416A1 WO 1999024416 A1 WO1999024416 A1 WO 1999024416A1 US 9823197 W US9823197 W US 9823197W WO 9924416 A1 WO9924416 A1 WO 9924416A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- aryl
- cycloalkyl
- heteroaryl
- heterocycloalkyl
- Prior art date
Links
- XPFCKQIEMRMHHK-UHFFFAOYSA-N CC(C)c1cnc(C(F)Sc2cnc(NC(C)=O)[s]2)[o]1 Chemical compound CC(C)c1cnc(C(F)Sc2cnc(NC(C)=O)[s]2)[o]1 XPFCKQIEMRMHHK-UHFFFAOYSA-N 0.000 description 1
- 0 CC1=NC(*)=C(*)*1 Chemical compound CC1=NC(*)=C(*)*1 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/54—Nitrogen and either oxygen or sulfur atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Definitions
- R 4 is hydrogen, alkyl, cycloalkyl, aryl, cycloalkylalkyl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl, heterocycloalkylalkyl; or CO-alkyl, CO-cycloalkyl, CO-aryl, CO-alkyl-cyclo alkyl, CO-alkyl-aryl, CO-heteroaryl, CO-alkyl-heteroaryl, CO-heterocycloalkyl, CO-alkyl-heterocycloalkyl; or CONH-alkyl, CONH-cycloalkyl, CONH-aryl, CONH-alkyl-cycloalkyl, CONH-alkyl-aryl, CONH-heteroaryl, CONH-alkyl-heteroaryl, CONH-heterocycloalkyl, CONH-heterocycloalkyl, CONH-heterocycloalky
- the intermediate (IV) is then reduced to a thiol (V) using reducing agents such as dithiothreitol (DTT), sodium borohydride, zinc or other known reducing agents.
- DTT dithiothreitol
- Compound (V) is then reacted with alkyl, aryl or heteroaryl halides, such as R 3 (CR-R 2 ) n -L, where L is a leaving group such as a halogen, in the presence of a base such as potassium carbonate to obtain compounds of formula I.
- the steps of reducing the thiocyanothiazole intermediate (IV) to the thiol (V), and the reaction of the reduced thiol (V) to provide compounds of formula I where X is S may be carried out sequentially without purification.
- the reaction was incubated at 30°C for 1 hour and then stopped by the addition of cold trichloroacetic acid (TCA) to a final concentration of 15% and incubated on ice for 20 minutes.
- TCA cold trichloroacetic acid
- the reaction was harvested onto GF/C unifilter plates (Packard) using a Packard Filtermate Universal harvester, and the filters were counted on a Packard
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Immunology (AREA)
- Oncology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Molecular Biology (AREA)
- AIDS & HIV (AREA)
- Urology & Nephrology (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
Description
Claims
Priority Applications (14)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE69838515T DE69838515T2 (en) | 1997-11-12 | 1998-11-02 | AMINOTHIAZOLE FOR INHIBITING CYCLINE-DEPENDENT KINASES |
CA002309551A CA2309551C (en) | 1997-11-12 | 1998-11-02 | Aminothiazole inhibitors of cyclin dependent kinases |
KR10-2003-7004561A KR20030036862A (en) | 1997-11-12 | 1998-11-02 | Composition for inhibiting cyclin dependent kinases |
PL340540A PL204642B1 (en) | 1997-11-12 | 1998-11-02 | Aminothiazolic inhibitors of cyclin-dependent kinases |
HU0004559A HUP0004559A3 (en) | 1997-11-12 | 1998-11-02 | Aminothiazole inhibitors of cyclin dependent kinases, pharmaceutical compositions containing them and their use |
JP2000520430A JP4344084B2 (en) | 1997-11-12 | 1998-11-02 | Aminothiazole inhibitors of cyclin-dependent kinases |
NZ503828A NZ503828A (en) | 1997-11-12 | 1998-11-02 | Aminothiazole inhibitors of cyclin dependent kinases |
BR9814124-4A BR9814124A (en) | 1997-11-12 | 1998-11-02 | Aminothiazole inhibitors of cyclin-dependent kinases |
EP98956431A EP1042307B1 (en) | 1997-11-12 | 1998-11-02 | Aminothiazole inhibitors of cyclin dependent kinases |
AU12955/99A AU730607B2 (en) | 1997-11-12 | 1998-11-02 | Aminothiazole inhibitors of cyclin dependent kinases |
DK98956431T DK1042307T3 (en) | 1997-11-12 | 1998-11-02 | Aminothiazoline inhibitors of cyclin-dependent kinases |
IL13558998A IL135589A (en) | 1997-11-12 | 1998-11-02 | Aminothiazole derivatives and pharmaceutical compositions containing the same |
NO20002153A NO316773B1 (en) | 1997-11-12 | 2000-04-27 | Aminothiazole inhibitors for cyclin-dependent kinases, pharmaceutical composition and use thereof |
HK00107675A HK1029109A1 (en) | 1995-11-12 | 2000-11-30 | Aminothiazole inhibitors of cyclin dependent kinases |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US6519597P | 1997-11-12 | 1997-11-12 | |
US60/065,195 | 1997-11-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1999024416A1 true WO1999024416A1 (en) | 1999-05-20 |
Family
ID=22060972
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1998/023197 WO1999024416A1 (en) | 1995-11-12 | 1998-11-02 | Aminothiazole inhibitors of cyclin dependent kinases |
Country Status (32)
Country | Link |
---|---|
US (1) | US6040321A (en) |
EP (1) | EP1042307B1 (en) |
JP (1) | JP4344084B2 (en) |
KR (2) | KR20030036862A (en) |
CN (1) | CN1160343C (en) |
AR (1) | AR017182A1 (en) |
AT (1) | ATE374771T1 (en) |
AU (1) | AU730607B2 (en) |
BR (1) | BR9814124A (en) |
CA (1) | CA2309551C (en) |
CO (1) | CO4990957A1 (en) |
CY (1) | CY1107509T1 (en) |
CZ (1) | CZ297907B6 (en) |
DE (1) | DE69838515T2 (en) |
DK (1) | DK1042307T3 (en) |
EG (1) | EG24028A (en) |
ES (1) | ES2296347T3 (en) |
HU (1) | HUP0004559A3 (en) |
ID (1) | ID23983A (en) |
IL (1) | IL135589A (en) |
MY (1) | MY120779A (en) |
NO (1) | NO316773B1 (en) |
NZ (1) | NZ503828A (en) |
PE (1) | PE131699A1 (en) |
PL (1) | PL204642B1 (en) |
PT (1) | PT1042307E (en) |
RU (1) | RU2211839C2 (en) |
TR (1) | TR200001344T2 (en) |
TW (1) | TW593292B (en) |
UY (1) | UY25239A1 (en) |
WO (1) | WO1999024416A1 (en) |
ZA (1) | ZA9810332B (en) |
Cited By (67)
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WO2000075120A1 (en) * | 1999-06-04 | 2000-12-14 | Agouron Pharmaceuticals, Inc. | Diaminothiazoles and their use for inhibiting protein kinases |
WO2001007411A1 (en) * | 1999-07-26 | 2001-02-01 | Banyu Pharmaceutical Co., Ltd. | Biarylurea derivatives |
WO2001014353A1 (en) * | 1999-08-12 | 2001-03-01 | Pharmacia Italia, S.P.A. | Arylmethyl-carbonylamino-thiazole derivatives and their use as antitumor agents |
US6214852B1 (en) | 1998-10-21 | 2001-04-10 | Bristol-Myers Squibb Company | N-[5-[[[5-alkyl-2-oxazolyl]methyl]thio]-2-thiazolyl]-carboxamide inhibitors of cyclin dependent kinases |
WO2001044217A1 (en) * | 1999-12-15 | 2001-06-21 | Bristol-Myers Squibb Co. | Aminothiazole inhibitors of cyclin dependent kinases |
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WO2001056567A1 (en) * | 2000-02-04 | 2001-08-09 | Novo Nordisk A/S | 2,4-diaminothiazole derivatives and their use as glycogen synthase kinase-3 (gsk-3) inhibitors |
WO2001058852A2 (en) * | 2000-02-11 | 2001-08-16 | Dompé S.p.A. | (r)-2-aryl-propionamides, useful in the inhibition of il-8-induced chemiotaxis of neutrophils |
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WO2001095856A2 (en) * | 2000-06-15 | 2001-12-20 | Chaconne Nsi Co., Ltd. | Urea derivative useful as an anti-cancer agent and process for preparing same |
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US6720346B2 (en) | 2001-07-06 | 2004-04-13 | Agouron Pharmaceuticals, Inc. | Thiazole benzamide derivatives and pharmaceutical compositions for inhibiting cell proliferation |
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