JP2004517069A - Ｔｇｆ阻害剤としてのピリジル置換トリアゾール類 - Google Patents
Ｔｇｆ阻害剤としてのピリジル置換トリアゾール類 Download PDFInfo
- Publication number
- JP2004517069A JP2004517069A JP2002543486A JP2002543486A JP2004517069A JP 2004517069 A JP2004517069 A JP 2004517069A JP 2002543486 A JP2002543486 A JP 2002543486A JP 2002543486 A JP2002543486 A JP 2002543486A JP 2004517069 A JP2004517069 A JP 2004517069A
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- JP
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- Prior art keywords
- alkyl
- triazol
- phenyl
- pharmaceutically acceptable
- 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.)
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- 150000003852 triazoles Chemical class 0.000 title abstract description 5
- 239000003112 inhibitor Substances 0.000 title description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 32
- -1 cyano, phenyl Chemical group 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 239000003814 drug Substances 0.000 claims abstract description 5
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 5
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
- 125000006574 non-aromatic ring group Chemical group 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 239000012453 solvate Substances 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 3
- 229910052799 carbon Inorganic materials 0.000 claims abstract 2
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- ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 claims description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
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- NOKBAPCRTWOCDK-UHFFFAOYSA-N 5-[5-(6-methylpyridin-2-yl)-2h-triazol-4-yl]-2,1,3-benzothiadiazole Chemical compound CC1=CC=CC(C2=C(N=NN2)C2=CC3=NSN=C3C=C2)=N1 NOKBAPCRTWOCDK-UHFFFAOYSA-N 0.000 claims description 4
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- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 4
- 230000004761 fibrosis Effects 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000007920 subcutaneous administration Methods 0.000 claims description 4
- BRLBQTSHXFZPGU-UHFFFAOYSA-N 1-methyl-6-[5-(6-methylpyridin-2-yl)-2h-triazol-4-yl]benzimidazole Chemical compound CC1=CC=CC(C=2C(=NNN=2)C=2C=C3N(C)C=NC3=CC=2)=N1 BRLBQTSHXFZPGU-UHFFFAOYSA-N 0.000 claims description 3
- QYUPKARFOVKNFD-UHFFFAOYSA-N 2-[5-(2,3-dihydro-1,4-benzodioxin-6-yl)-2h-triazol-4-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C=2C(=NNN=2)C=2C=C3OCCOC3=CC=2)=N1 QYUPKARFOVKNFD-UHFFFAOYSA-N 0.000 claims description 3
- WTNSSVMXBUHRHK-UHFFFAOYSA-N 2-[5-(2,3-dihydro-1-benzofuran-5-yl)-2h-triazol-4-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=NN2)C=2C=C3CCOC3=CC=2)=N1 WTNSSVMXBUHRHK-UHFFFAOYSA-N 0.000 claims description 3
- ITZNDPPKHRERBC-UHFFFAOYSA-N 2-[5-(3-chloro-4-methoxyphenyl)-2h-triazol-4-yl]-6-methylpyridine Chemical compound C1=C(Cl)C(OC)=CC=C1C1=NNN=C1C1=CC=CC(C)=N1 ITZNDPPKHRERBC-UHFFFAOYSA-N 0.000 claims description 3
- BCYKHYVRYKQRSW-UHFFFAOYSA-N 2-[5-(3-fluoro-4-methoxyphenyl)-2h-triazol-4-yl]-6-methylpyridine Chemical compound C1=C(F)C(OC)=CC=C1C1=NNN=C1C1=CC=CC(C)=N1 BCYKHYVRYKQRSW-UHFFFAOYSA-N 0.000 claims description 3
- YHQKEAUUFCYOAF-UHFFFAOYSA-N 2-[5-(4-methoxyphenyl)-2h-triazol-4-yl]-6-methylpyridine Chemical compound C1=CC(OC)=CC=C1C1=NNN=C1C1=CC=CC(C)=N1 YHQKEAUUFCYOAF-UHFFFAOYSA-N 0.000 claims description 3
- FSRXEKNOMXHHNF-UHFFFAOYSA-N 5-[2-ethyl-5-(6-methylpyridin-2-yl)triazol-4-yl]-2,1,3-benzothiadiazole Chemical compound N=1N(CC)N=C(C2=CC3=NSN=C3C=C2)C=1C1=CC=CC(C)=N1 FSRXEKNOMXHHNF-UHFFFAOYSA-N 0.000 claims description 3
- KBAQELPGKYWLTD-UHFFFAOYSA-N 6-[5-(6-methylpyridin-2-yl)-2h-triazol-4-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound CC1=CC=CC(C2=C(N=NN2)C2=CN3N=CN=C3C=C2)=N1 KBAQELPGKYWLTD-UHFFFAOYSA-N 0.000 claims description 3
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- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
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- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
- 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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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Ophthalmology & Optometry (AREA)
- Dermatology (AREA)
- Gastroenterology & Hepatology (AREA)
- Immunology (AREA)
- Vascular Medicine (AREA)
- Surgery (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0027987.7A GB0027987D0 (en) | 2000-11-16 | 2000-11-16 | Compounds |
| PCT/GB2001/005036 WO2002040476A1 (en) | 2000-11-16 | 2001-11-15 | Pyridyl-substituted triazoles as tgf inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004517069A true JP2004517069A (ja) | 2004-06-10 |
| JP2004517069A5 JP2004517069A5 (https=) | 2005-12-22 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002543486A Withdrawn JP2004517069A (ja) | 2000-11-16 | 2001-11-15 | Ｔｇｆ阻害剤としてのピリジル置換トリアゾール類 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20040152738A1 (https=) |
| EP (1) | EP1335916A1 (https=) |
| JP (1) | JP2004517069A (https=) |
| AU (1) | AU2002214163A1 (https=) |
| GB (1) | GB0027987D0 (https=) |
| WO (1) | WO2002040476A1 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005538996A (ja) * | 2002-07-31 | 2005-12-22 | スミスクライン・ビーチャム・コーポレイション | 化合物 |
| JP2013514305A (ja) * | 2009-12-17 | 2013-04-25 | エフ．ホフマン−ラ ロシュ アーゲー | エチニル誘導体 |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0127430D0 (en) * | 2001-11-15 | 2002-01-09 | Smithkline Beecham Corp | Compounds |
| GB0127433D0 (en) * | 2001-11-15 | 2002-01-09 | Smithkline Beecham Corp | Compounds |
| AR039241A1 (es) | 2002-04-04 | 2005-02-16 | Biogen Inc | Heteroarilos trisustituidos y metodos para su produccion y uso de los mismos |
| GB0217783D0 (en) * | 2002-07-31 | 2002-09-11 | Glaxo Group Ltd | Compounds |
| GB0217780D0 (en) * | 2002-07-31 | 2002-09-11 | Glaxo Group Ltd | Compounds |
| GB0217786D0 (en) * | 2002-07-31 | 2002-09-11 | Glaxo Group Ltd | Compounds |
| WO2004013135A1 (en) * | 2002-07-31 | 2004-02-12 | Smithkline Beecham Corporation | 2-phenylpyridin-4-yl derivatives as alk5 inhibitors |
| UA80295C2 (en) | 2002-09-06 | 2007-09-10 | Biogen Inc | Pyrazolopyridines and using the same |
| PL375973A1 (en) * | 2002-09-18 | 2005-12-12 | Pfizer Products Inc. | Novel isothiazole and isoxazole compounds as transforming growth factor (tgf) inhibitors |
| CA2497971A1 (en) | 2002-09-18 | 2004-04-01 | Pfizer Products Inc. | Triazole derivatives as transforming growth factor (tgf) inhibitors |
| MXPA05002332A (es) * | 2002-09-18 | 2005-06-08 | Pfizer Prod Inc | Nuevos compuestos de oxazol y tiazol como inhibidores del factor de crecimiento transformador (tgf). |
| HRP20050247A2 (en) | 2002-09-18 | 2005-10-31 | Pfizer Products Inc. | Pyrazole derivatives as transforming growth factor (tgf) inhibitors |
| JP4547271B2 (ja) * | 2002-09-18 | 2010-09-22 | ファイザー・プロダクツ・インク | トランスフォーミング増殖因子（ｔｇｆ）阻害剤としての新規イミダゾール化合物 |
| CA2513086A1 (en) * | 2002-12-19 | 2004-07-08 | Scios Inc. | Treatment of obesity and associated conditions with tgf-.beta. inhibitors |
| PA8595001A1 (es) | 2003-03-04 | 2004-09-28 | Pfizer Prod Inc | Nuevos compuestos heteroaromaticos condensados que son inhibidores del factor de crecimiento transforante (tgf) |
| GB0313915D0 (en) * | 2003-06-16 | 2003-07-23 | Smithkline Beecham Corp | Compounds |
| NZ549003A (en) * | 2004-03-05 | 2009-07-31 | Taisho Pharmaceutical Co Ltd | Thiazole derivative as an ALK5 inhibitor |
| JP5149177B2 (ja) | 2005-07-25 | 2013-02-20 | シンタ ファーマシューティカルズ コーポレーション | 増殖性疾患の治療のための、チューブリンポリマー化の１，２，３−トリアゾール系抑制剤 |
| WO2007070866A2 (en) * | 2005-12-16 | 2007-06-21 | Alcon, Inc. | Control of intraocular pressure using alk5 modulation agents |
| CA2874764C (en) | 2012-05-30 | 2022-11-01 | Cornell University | Generation of functional and durable endothelial cells from human amniotic fluid-derived cells |
| WO2014197421A1 (en) | 2013-06-05 | 2014-12-11 | Biotime, Inc. | Compositions and methods for induced tissue regeneration in mammalian species |
| US11078462B2 (en) | 2014-02-18 | 2021-08-03 | ReCyte Therapeutics, Inc. | Perivascular stromal cells from primate pluripotent stem cells |
| RU2688665C2 (ru) | 2014-04-22 | 2019-05-22 | Университет Базель | Новый способ получения производных триазина, пиримидина и пиридина |
| US10240127B2 (en) | 2014-07-03 | 2019-03-26 | ReCyte Therapeutics, Inc. | Exosomes from clonal progenitor cells |
| CA3202332A1 (en) | 2015-12-07 | 2017-06-15 | Agex Therapeutics, Inc. | Methods for the re-derivation of diverse pluripotent stem cell-derived brown fat cells |
| WO2022251359A1 (en) * | 2021-05-26 | 2022-12-01 | Theravance Biopharma R&D Ip, Llc | Bicyclic inhibitors of alk5 and methods of use |
| US12240830B2 (en) * | 2021-08-13 | 2025-03-04 | Bisichem Co., Ltd. | Fused ring heteroaryl compounds and use thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003525201A (ja) * | 1998-08-20 | 2003-08-26 | スミスクライン・ビーチャム・コーポレイション | 新規な置換トリアゾール化合物 |
-
2000
- 2000-11-16 GB GBGB0027987.7A patent/GB0027987D0/en not_active Ceased
-
2001
- 2001-11-15 JP JP2002543486A patent/JP2004517069A/ja not_active Withdrawn
- 2001-11-15 US US10/416,680 patent/US20040152738A1/en not_active Abandoned
- 2001-11-15 AU AU2002214163A patent/AU2002214163A1/en not_active Abandoned
- 2001-11-15 EP EP01982621A patent/EP1335916A1/en not_active Withdrawn
- 2001-11-15 WO PCT/GB2001/005036 patent/WO2002040476A1/en not_active Ceased
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005538996A (ja) * | 2002-07-31 | 2005-12-22 | スミスクライン・ビーチャム・コーポレイション | 化合物 |
| JP2013514305A (ja) * | 2009-12-17 | 2013-04-25 | エフ．ホフマン−ラ ロシュ アーゲー | エチニル誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002040476A1 (en) | 2002-05-23 |
| AU2002214163A1 (en) | 2002-05-27 |
| EP1335916A1 (en) | 2003-08-20 |
| US20040152738A1 (en) | 2004-08-05 |
| GB0027987D0 (en) | 2001-01-03 |
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