HRP20050246A2 - Novel isothiazole and isoxazole compounds as transforming growth factor (tgf) inhibitors - Google Patents
Novel isothiazole and isoxazole compounds as transforming growth factor (tgf) inhibitors Download PDFInfo
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- HRP20050246A2 HRP20050246A2 HR20050246A HRP20050246A HRP20050246A2 HR P20050246 A2 HRP20050246 A2 HR P20050246A2 HR 20050246 A HR20050246 A HR 20050246A HR P20050246 A HRP20050246 A HR P20050246A HR P20050246 A2 HRP20050246 A2 HR P20050246A2
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- alkyl
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- phenyl
- amino
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- 102000009618 Transforming Growth Factors Human genes 0.000 title description 16
- 108010009583 Transforming Growth Factors Proteins 0.000 title description 16
- 239000003112 inhibitor Substances 0.000 title description 8
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 title description 4
- 150000002545 isoxazoles Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 140
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 77
- -1 cyano, nitro, carbamoyl Chemical group 0.000 claims description 60
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 22
- 239000000651 prodrug Substances 0.000 claims description 21
- 229940002612 prodrug Drugs 0.000 claims description 21
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 20
- 201000010099 disease Diseases 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 241001465754 Metazoa Species 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
- 125000000172 C5-C10 aryl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 5
- 125000003368 amide group Chemical group 0.000 claims description 5
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- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
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- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 3
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- 201000011510 cancer Diseases 0.000 claims description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
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- 125000001475 halogen functional group Chemical group 0.000 claims 1
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 5
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- 108091000080 Phosphotransferase Proteins 0.000 description 5
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- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- 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
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
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- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
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- A—HUMAN NECESSITIES
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- 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
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Obesity (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Oncology (AREA)
- Gastroenterology & Hepatology (AREA)
- Cardiology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41213102P | 2002-09-18 | 2002-09-18 | |
| US48458003P | 2003-07-02 | 2003-07-02 | |
| PCT/IB2003/004005 WO2004026865A1 (en) | 2002-09-18 | 2003-09-12 | Novel isothiazole and isoxazole compounds as transforming growth factor (tgf) inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20050246A2 true HRP20050246A2 (en) | 2005-10-31 |
Family
ID=32033584
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20050246A HRP20050246A2 (en) | 2002-09-18 | 2005-03-16 | Novel isothiazole and isoxazole compounds as transforming growth factor (tgf) inhibitors |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US7030125B2 (xx) |
| EP (1) | EP1542995A1 (xx) |
| JP (1) | JP2006506443A (xx) |
| KR (1) | KR20050057441A (xx) |
| CN (1) | CN1681809A (xx) |
| AP (1) | AP2005003262A0 (xx) |
| AR (1) | AR041275A1 (xx) |
| AU (1) | AU2003263431A1 (xx) |
| BR (1) | BR0314286A (xx) |
| CA (1) | CA2499332A1 (xx) |
| CO (1) | CO5550458A2 (xx) |
| EA (1) | EA200500286A1 (xx) |
| EC (1) | ECSP055685A (xx) |
| HR (1) | HRP20050246A2 (xx) |
| IS (1) | IS7695A (xx) |
| MA (1) | MA27444A1 (xx) |
| MX (1) | MXPA05002378A (xx) |
| NO (1) | NO20051852L (xx) |
| OA (1) | OA12925A (xx) |
| PA (1) | PA8583101A1 (xx) |
| PE (1) | PE20050076A1 (xx) |
| PL (1) | PL375973A1 (xx) |
| TW (1) | TW200410954A (xx) |
| UY (1) | UY27983A1 (xx) |
| WO (1) | WO2004026865A1 (xx) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| TW200417547A (en) | 2002-07-31 | 2004-09-16 | Smithkline Beecham Corp | Compounds |
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- 2003-09-12 PL PL03375973A patent/PL375973A1/xx not_active Application Discontinuation
- 2003-09-12 KR KR1020057004662A patent/KR20050057441A/ko not_active Application Discontinuation
- 2003-09-12 JP JP2004568905A patent/JP2006506443A/ja not_active Withdrawn
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- 2003-09-12 WO PCT/IB2003/004005 patent/WO2004026865A1/en active Application Filing
- 2003-09-12 CN CNA038222043A patent/CN1681809A/zh active Pending
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- 2003-09-12 MX MXPA05002378A patent/MXPA05002378A/es active IP Right Grant
- 2003-09-12 BR BR0314286-8A patent/BR0314286A/pt not_active IP Right Cessation
- 2003-09-12 AU AU2003263431A patent/AU2003263431A1/en not_active Abandoned
- 2003-09-12 OA OA1200500074A patent/OA12925A/en unknown
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- 2003-09-17 US US10/667,167 patent/US7030125B2/en not_active Expired - Fee Related
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| US20040116473A1 (en) | 2004-06-17 |
| AP2005003262A0 (en) | 2005-03-31 |
| TW200410954A (en) | 2004-07-01 |
| CO5550458A2 (es) | 2005-08-31 |
| AR041275A1 (es) | 2005-05-11 |
| AU2003263431A1 (en) | 2004-04-08 |
| IS7695A (is) | 2005-02-14 |
| JP2006506443A (ja) | 2006-02-23 |
| CN1681809A (zh) | 2005-10-12 |
| KR20050057441A (ko) | 2005-06-16 |
| MXPA05002378A (es) | 2005-05-23 |
| ECSP055685A (es) | 2005-05-30 |
| EP1542995A1 (en) | 2005-06-22 |
| US7030125B2 (en) | 2006-04-18 |
| EA200500286A1 (ru) | 2005-08-25 |
| NO20051852L (no) | 2005-06-16 |
| MA27444A1 (fr) | 2005-07-01 |
| PE20050076A1 (es) | 2005-03-26 |
| WO2004026865A1 (en) | 2004-04-01 |
| BR0314286A (pt) | 2005-08-02 |
| PA8583101A1 (es) | 2004-04-23 |
| UY27983A1 (es) | 2004-04-30 |
| PL375973A1 (en) | 2005-12-12 |
| OA12925A (en) | 2006-10-13 |
| CA2499332A1 (en) | 2004-04-01 |
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