RU2009110254A - Производные 2-(пиразин-2-ил)тиазола и 2-(1н-пиразол-3-ил)тиразола и связанные с ним соединения в качестве ингибиторов стеароил-соа десатуразы для лечения метаболических, сердечно-сосудистых и других нарушений - Google Patents
Производные 2-(пиразин-2-ил)тиазола и 2-(1н-пиразол-3-ил)тиразола и связанные с ним соединения в качестве ингибиторов стеароил-соа десатуразы для лечения метаболических, сердечно-сосудистых и других нарушений Download PDFInfo
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- RU2009110254A RU2009110254A RU2009110254/04A RU2009110254A RU2009110254A RU 2009110254 A RU2009110254 A RU 2009110254A RU 2009110254/04 A RU2009110254/04 A RU 2009110254/04A RU 2009110254 A RU2009110254 A RU 2009110254A RU 2009110254 A RU2009110254 A RU 2009110254A
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- RU
- Russia
- Prior art keywords
- carboxylic acid
- pyrazol
- methylthiazole
- alkyl
- aryl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract 18
- 150000007979 thiazole derivatives Chemical class 0.000 title 1
- 125000003118 aryl group Chemical group 0.000 claims abstract 51
- 125000000217 alkyl group Chemical group 0.000 claims abstract 50
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 40
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 40
- 239000001257 hydrogen Substances 0.000 claims abstract 40
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 37
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract 36
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 36
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 34
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 24
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract 20
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 19
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract 16
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims abstract 16
- 125000002947 alkylene group Chemical group 0.000 claims abstract 15
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- 229910052717 sulfur Inorganic materials 0.000 claims abstract 3
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- CYNQYUQKILVCSY-HXUWFJFHSA-N n-benzyl-2-[1-[(2s)-2-hydroxy-2-phenylethyl]pyrazol-3-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(C[C@@H](O)C=3C=CC=CC=3)C=C2)SC=1C(=O)NCC1=CC=CC=C1 CYNQYUQKILVCSY-HXUWFJFHSA-N 0.000 claims 1
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- HDSGUOKYJJDUFO-UHFFFAOYSA-N n-benzyl-2-[5-[2-(4-fluorophenyl)ethyl]pyrazin-2-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=CC(CCC=3C=CC(F)=CC=3)=NC=2)SC=1C(=O)NCC1=CC=CC=C1 HDSGUOKYJJDUFO-UHFFFAOYSA-N 0.000 claims 1
- JYLRTPHRXNYQKP-UHFFFAOYSA-N n-benzyl-2-[6-(dimethylamino)pyrazin-2-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CN(C)C1=CN=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=CC=CC=2)=N1 JYLRTPHRXNYQKP-UHFFFAOYSA-N 0.000 claims 1
- DUPJSRQEIOJXIB-FMIVXFBMSA-N n-benzyl-2-[6-[(e)-2-(4-fluorophenyl)ethenyl]pyrazin-2-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(\C=C\C=3C=CC(F)=CC=3)C=NC=2)SC=1C(=O)NCC1=CC=CC=C1 DUPJSRQEIOJXIB-FMIVXFBMSA-N 0.000 claims 1
- CGLGLWNFCHPFKN-UHFFFAOYSA-N n-benzyl-2-[6-[2-(4-fluorophenoxy)ethyl-methylamino]pyrazin-2-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C=1N=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=CC=CC=2)=NC=1N(C)CCOC1=CC=C(F)C=C1 CGLGLWNFCHPFKN-UHFFFAOYSA-N 0.000 claims 1
- AEVBIYNSSLOWIE-UHFFFAOYSA-N n-benzyl-2-[6-[2-(4-fluorophenyl)ethyl]pyrazin-2-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(CCC=3C=CC(F)=CC=3)C=NC=2)SC=1C(=O)NCC1=CC=CC=C1 AEVBIYNSSLOWIE-UHFFFAOYSA-N 0.000 claims 1
- NHASVGLGVMODRE-UHFFFAOYSA-N n-benzyl-2-[6-[2-(4-fluorophenyl)ethylamino]pyrazin-2-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(NCCC=3C=CC(F)=CC=3)C=NC=2)SC=1C(=O)NCC1=CC=CC=C1 NHASVGLGVMODRE-UHFFFAOYSA-N 0.000 claims 1
- MBALKBRJRNEXCS-UHFFFAOYSA-N n-benzyl-4-methyl-2-(1h-pyrazol-5-yl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2NN=CC=2)SC=1C(=O)NCC1=CC=CC=C1 MBALKBRJRNEXCS-UHFFFAOYSA-N 0.000 claims 1
- KPNNJUWSPXKUQZ-UHFFFAOYSA-N n-benzyl-4-methyl-2-[1-(2-phenoxyethyl)pyrazol-3-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCOC=3C=CC=CC=3)C=C2)SC=1C(=O)NCC1=CC=CC=C1 KPNNJUWSPXKUQZ-UHFFFAOYSA-N 0.000 claims 1
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- HDFQZRAJGYXLEJ-UHFFFAOYSA-N n-benzyl-4-methyl-2-[1-(2-pyridin-2-ylethyl)pyrazol-3-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCC=3N=CC=CC=3)C=C2)SC=1C(=O)NCC1=CC=CC=C1 HDFQZRAJGYXLEJ-UHFFFAOYSA-N 0.000 claims 1
- VQJKYGUXJPUYEY-UHFFFAOYSA-N n-benzyl-4-methyl-2-[1-(3-methylbutyl)pyrazol-3-yl]-1,3-thiazole-5-carboxamide Chemical compound CC(C)CCN1C=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=CC=CC=2)=N1 VQJKYGUXJPUYEY-UHFFFAOYSA-N 0.000 claims 1
- WPQXFAXZKZFIOX-UHFFFAOYSA-N n-benzyl-4-methyl-2-[1-(3-phenylpropyl)pyrazol-3-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCCC=3C=CC=CC=3)C=C2)SC=1C(=O)NCC1=CC=CC=C1 WPQXFAXZKZFIOX-UHFFFAOYSA-N 0.000 claims 1
- AXGKNLBSHYSJBH-KRWDZBQOSA-N n-benzyl-4-methyl-2-[1-[(2r)-2-phenylpropyl]pyrazol-3-yl]-1,3-thiazole-5-carboxamide Chemical compound C([C@H](C)C=1C=CC=CC=1)N(N=1)C=CC=1C(S1)=NC(C)=C1C(=O)NCC1=CC=CC=C1 AXGKNLBSHYSJBH-KRWDZBQOSA-N 0.000 claims 1
- AXGKNLBSHYSJBH-QGZVFWFLSA-N n-benzyl-4-methyl-2-[1-[(2s)-2-phenylpropyl]pyrazol-3-yl]-1,3-thiazole-5-carboxamide Chemical compound C([C@@H](C)C=1C=CC=CC=1)N(N=1)C=CC=1C(S1)=NC(C)=C1C(=O)NCC1=CC=CC=C1 AXGKNLBSHYSJBH-QGZVFWFLSA-N 0.000 claims 1
- UHZOCHGUMDRKFR-UHFFFAOYSA-N n-benzyl-4-methyl-2-[5-(3-phenylpropyl)pyrazin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=CC(CCCC=3C=CC=CC=3)=NC=2)SC=1C(=O)NCC1=CC=CC=C1 UHZOCHGUMDRKFR-UHFFFAOYSA-N 0.000 claims 1
- GTMQESWOUJKROP-UHFFFAOYSA-N n-benzyl-4-methyl-2-[6-(2-phenylethyl)pyrazin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(CCC=3C=CC=CC=3)C=NC=2)SC=1C(=O)NCC1=CC=CC=C1 GTMQESWOUJKROP-UHFFFAOYSA-N 0.000 claims 1
- KQYPATXQBASHAJ-UHFFFAOYSA-N n-benzyl-4-methyl-2-[6-(3-phenylpropyl)pyrazin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(CCCC=3C=CC=CC=3)C=NC=2)SC=1C(=O)NCC1=CC=CC=C1 KQYPATXQBASHAJ-UHFFFAOYSA-N 0.000 claims 1
- WCUJIXRJEZFGKN-FMIVXFBMSA-N n-benzyl-4-methyl-2-[6-[(e)-2-[4-(trifluoromethyl)phenyl]ethenyl]pyrazin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(\C=C\C=3C=CC(=CC=3)C(F)(F)F)C=NC=2)SC=1C(=O)NCC1=CC=CC=C1 WCUJIXRJEZFGKN-FMIVXFBMSA-N 0.000 claims 1
- MPLHKNJNLFDAOB-OUKQBFOZSA-N n-benzyl-4-methyl-2-[6-[(e)-2-phenylethenyl]pyrazin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(\C=C\C=3C=CC=CC=3)C=NC=2)SC=1C(=O)NCC1=CC=CC=C1 MPLHKNJNLFDAOB-OUKQBFOZSA-N 0.000 claims 1
- OOQMPRBWXAJUFF-UHFFFAOYSA-N n-benzyl-4-methyl-2-[6-[2-[4-(trifluoromethyl)phenyl]ethyl]pyrazin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(CCC=3C=CC(=CC=3)C(F)(F)F)C=NC=2)SC=1C(=O)NCC1=CC=CC=C1 OOQMPRBWXAJUFF-UHFFFAOYSA-N 0.000 claims 1
- 229960003512 nicotinic acid Drugs 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 230000028327 secretion Effects 0.000 claims 1
- 239000004059 squalene synthase inhibitor Substances 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- GGNIKGLUPSHSBV-UHFFFAOYSA-N thiazole-5-carboxamide Chemical compound NC(=O)C1=CN=CS1 GGNIKGLUPSHSBV-UHFFFAOYSA-N 0.000 claims 1
- 201000005665 thrombophilia Diseases 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 0 Cc1n[n](**)*(C)c1 Chemical compound Cc1n[n](**)*(C)c1 0.000 description 1
Classifications
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- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
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- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
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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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Dermatology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Physical Education & Sports Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Nutrition Science (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82342506P | 2006-08-24 | 2006-08-24 | |
| US60/823,425 | 2006-08-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2009110254A true RU2009110254A (ru) | 2010-09-27 |
Family
ID=38951374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2009110254/04A RU2009110254A (ru) | 2006-08-24 | 2007-08-22 | Производные 2-(пиразин-2-ил)тиазола и 2-(1н-пиразол-3-ил)тиразола и связанные с ним соединения в качестве ингибиторов стеароил-соа десатуразы для лечения метаболических, сердечно-сосудистых и других нарушений |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8314138B2 (https=) |
| EP (1) | EP2086970B1 (https=) |
| JP (1) | JP2010501567A (https=) |
| KR (1) | KR20090040478A (https=) |
| CN (1) | CN101506203B (https=) |
| AU (1) | AU2007288245A1 (https=) |
| BR (1) | BRPI0719122A2 (https=) |
| CA (1) | CA2661017A1 (https=) |
| MX (1) | MX2009002019A (https=) |
| RU (1) | RU2009110254A (https=) |
| WO (1) | WO2008024390A2 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2762557C1 (ru) * | 2018-04-26 | 2021-12-21 | Пфайзер Инк. | Производные 2-аминопиридина или 2-аминопиримидина в качестве циклинзависимых ингибиторов киназы |
| RU2790006C2 (ru) * | 2018-04-26 | 2023-02-14 | Пфайзер Инк. | Производные 2-аминопиридина или 2-аминопиримидина в качестве циклинзависимых ингибиторов киназы |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2009001634A (es) | 2006-08-15 | 2009-02-25 | Novartis Ag | Compuestos heterociclicos adecuados para el tratamiento de enfermedades relacionadas con el nivel elevado de lipidos. |
| WO2008074835A1 (en) | 2006-12-20 | 2008-06-26 | Novartis Ag | 2-substituted 5-membered heterocycles as scd inhibitors |
| WO2008128335A1 (en) * | 2007-04-20 | 2008-10-30 | Merck Frosst Canada Ltd. | Novel heteroaromatic compounds as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| WO2009073973A1 (en) * | 2007-12-11 | 2009-06-18 | Merck Frosst Canada Ltd. | Novel heteroaromatic compounds as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| WO2009103739A1 (en) * | 2008-02-20 | 2009-08-27 | Novartis Ag | Heterocyclic inhibitors of stearoyl-coa desaturase |
| GB0810913D0 (en) * | 2008-06-13 | 2008-07-23 | Smithkline Beecham Corp | Comppounds |
| US20110184027A1 (en) * | 2008-09-25 | 2011-07-28 | Glenmark Pharmaceuticals S.A. | Tissue selective stearoyl-coa desaturase 1 inhibitors and cell based screening assay for their identification |
| DE102008057344A1 (de) | 2008-11-14 | 2010-05-20 | Bayer Schering Pharma Aktiengesellschaft | Aminoalkyl-substituierte Aryl-Verbindungen und ihre Verwendung |
| DE102009041241A1 (de) | 2009-09-11 | 2011-08-04 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Substituierte Aryl-Verbindungen und ihre Verwendung |
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- 2007-08-22 BR BRPI0719122-7A patent/BRPI0719122A2/pt not_active Application Discontinuation
- 2007-08-22 JP JP2009525617A patent/JP2010501567A/ja active Pending
- 2007-08-22 AU AU2007288245A patent/AU2007288245A1/en not_active Abandoned
- 2007-08-22 EP EP07811474.1A patent/EP2086970B1/en not_active Not-in-force
- 2007-08-22 KR KR1020097005864A patent/KR20090040478A/ko not_active Withdrawn
- 2007-08-22 CN CN200780031571XA patent/CN101506203B/zh not_active Expired - Fee Related
- 2007-08-22 RU RU2009110254/04A patent/RU2009110254A/ru not_active Application Discontinuation
- 2007-08-22 US US12/438,654 patent/US8314138B2/en not_active Expired - Fee Related
- 2007-08-22 CA CA002661017A patent/CA2661017A1/en not_active Abandoned
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| Publication number | Priority date | Publication date | Assignee | Title |
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| RU2762557C1 (ru) * | 2018-04-26 | 2021-12-21 | Пфайзер Инк. | Производные 2-аминопиридина или 2-аминопиримидина в качестве циклинзависимых ингибиторов киназы |
| US11220494B2 (en) | 2018-04-26 | 2022-01-11 | Pfizer Inc. | Cyclin dependent kinase inhibitors |
| RU2790006C2 (ru) * | 2018-04-26 | 2023-02-14 | Пфайзер Инк. | Производные 2-аминопиридина или 2-аминопиримидина в качестве циклинзависимых ингибиторов киназы |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2007288245A1 (en) | 2008-02-28 |
| EP2086970B1 (en) | 2014-02-26 |
| CN101506203B (zh) | 2013-10-16 |
| US8314138B2 (en) | 2012-11-20 |
| MX2009002019A (es) | 2009-03-09 |
| EP2086970A2 (en) | 2009-08-12 |
| WO2008024390A3 (en) | 2008-04-17 |
| KR20090040478A (ko) | 2009-04-24 |
| CA2661017A1 (en) | 2008-02-28 |
| WO2008024390A2 (en) | 2008-02-28 |
| BRPI0719122A2 (pt) | 2013-12-10 |
| JP2010501567A (ja) | 2010-01-21 |
| CN101506203A (zh) | 2009-08-12 |
| US20100239520A1 (en) | 2010-09-23 |
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