JP5613671B2 - 新規化合物ｉｉ - Google Patents
新規化合物ｉｉ Download PDFInfo
- Publication number
- JP5613671B2 JP5613671B2 JP2011526518A JP2011526518A JP5613671B2 JP 5613671 B2 JP5613671 B2 JP 5613671B2 JP 2011526518 A JP2011526518 A JP 2011526518A JP 2011526518 A JP2011526518 A JP 2011526518A JP 5613671 B2 JP5613671 B2 JP 5613671B2
- Authority
- JP
- Japan
- Prior art keywords
- pyrazolo
- pyridine
- chlorophenyl
- alkyl
- mmol
- 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.)
- Expired - Fee Related
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- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 70
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 201000010099 disease Diseases 0.000 claims description 18
- 208000027866 inflammatory disease Diseases 0.000 claims description 12
- 230000004054 inflammatory process Effects 0.000 claims description 12
- 206010061218 Inflammation Diseases 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 230000002265 prevention Effects 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 206010047115 Vasculitis Diseases 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 208000026278 immune system disease Diseases 0.000 claims description 6
- 230000002757 inflammatory effect Effects 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- LZKOUGJOPWLART-UHFFFAOYSA-N 2-[4-[3-(4-chlorophenyl)pyrazolo[4,3-c]pyridin-1-yl]piperidin-1-yl]acetonitrile Chemical compound C1=CC(Cl)=CC=C1C(C1=CN=CC=C11)=NN1C1CCN(CC#N)CC1 LZKOUGJOPWLART-UHFFFAOYSA-N 0.000 claims description 4
- XPVUPBSNQJEXEH-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-(1-ethylpiperidin-4-yl)pyrazolo[4,3-c]pyridine Chemical compound C1CN(CC)CCC1N1C2=CC=NC=C2C(C=2C=CC(Cl)=CC=2)=N1 XPVUPBSNQJEXEH-UHFFFAOYSA-N 0.000 claims description 4
- MLQIYLMUBRUWBG-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-(1-methylpiperidin-4-yl)pyrazolo[4,3-c]pyridine Chemical compound C1CN(C)CCC1N1C2=CC=NC=C2C(C=2C=CC(Cl)=CC=2)=N1 MLQIYLMUBRUWBG-UHFFFAOYSA-N 0.000 claims description 4
- FIHUDPNQLJSABX-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-(1-methylsulfonylpiperidin-4-yl)pyrazolo[4,3-c]pyridine Chemical compound C1CN(S(=O)(=O)C)CCC1N1C2=CC=NC=C2C(C=2C=CC(Cl)=CC=2)=N1 FIHUDPNQLJSABX-UHFFFAOYSA-N 0.000 claims description 4
- IAFTWMRWSLCWEK-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-(1-propan-2-ylpiperidin-4-yl)pyrazolo[4,3-c]pyridine Chemical compound C1CN(C(C)C)CCC1N1C2=CC=NC=C2C(C=2C=CC(Cl)=CC=2)=N1 IAFTWMRWSLCWEK-UHFFFAOYSA-N 0.000 claims description 4
- OVLPQYMQAFDTQU-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-(oxan-4-ylmethyl)pyrazolo[4,3-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C(C1=CN=CC=C11)=NN1CC1CCOCC1 OVLPQYMQAFDTQU-UHFFFAOYSA-N 0.000 claims description 4
- UZSPJWMTOLNNKX-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-(oxolan-3-ylmethyl)pyrazolo[4,3-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C(C1=CN=CC=C11)=NN1CC1COCC1 UZSPJWMTOLNNKX-UHFFFAOYSA-N 0.000 claims description 4
- LLMRQVSOOAHDJW-CYBMUJFWSA-N 3-(4-chlorophenyl)-1-[(3r)-oxolan-3-yl]pyrazolo[4,3-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C(C1=CN=CC=C11)=NN1[C@H]1COCC1 LLMRQVSOOAHDJW-CYBMUJFWSA-N 0.000 claims description 4
- LLMRQVSOOAHDJW-ZDUSSCGKSA-N 3-(4-chlorophenyl)-1-[(3s)-oxolan-3-yl]pyrazolo[4,3-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C(C1=CN=CC=C11)=NN1[C@@H]1COCC1 LLMRQVSOOAHDJW-ZDUSSCGKSA-N 0.000 claims description 4
- KXOGGAVFFAFNKX-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-[1-(2-methoxyethyl)piperidin-4-yl]pyrazolo[4,3-c]pyridine Chemical compound C1CN(CCOC)CCC1N1C2=CC=NC=C2C(C=2C=CC(Cl)=CC=2)=N1 KXOGGAVFFAFNKX-UHFFFAOYSA-N 0.000 claims description 4
- HNIFHTYFMMNOHW-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-piperidin-3-ylpyrazolo[4,3-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C(C1=CN=CC=C11)=NN1C1CNCCC1 HNIFHTYFMMNOHW-UHFFFAOYSA-N 0.000 claims description 4
- PWYGCQOJSRMOEA-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-(oxan-4-yl)pyrazolo[4,3-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1=C2C=NC=CC2=NN1C1CCOCC1 PWYGCQOJSRMOEA-UHFFFAOYSA-N 0.000 claims description 4
- SVZNMZJVEAKFLC-UHFFFAOYSA-N 3-(4-fluorophenyl)-1-(1-methylpiperidin-4-yl)pyrazolo[4,3-c]pyridine Chemical compound C1CN(C)CCC1N1C2=CC=NC=C2C(C=2C=CC(F)=CC=2)=N1 SVZNMZJVEAKFLC-UHFFFAOYSA-N 0.000 claims description 4
- ILLQLEAXIUKHGR-UHFFFAOYSA-N 3-(4-fluorophenyl)-1-(oxan-4-yl)pyrazolo[4,3-c]pyridine Chemical compound C1=CC(F)=CC=C1C(C1=CN=CC=C11)=NN1C1CCOCC1 ILLQLEAXIUKHGR-UHFFFAOYSA-N 0.000 claims description 4
- LUJBRNLFLGPZAM-UHFFFAOYSA-N 3-(4-methylphenyl)-1-(oxan-4-yl)pyrazolo[4,3-c]pyridine Chemical compound C1=CC(C)=CC=C1C(C1=CN=CC=C11)=NN1C1CCOCC1 LUJBRNLFLGPZAM-UHFFFAOYSA-N 0.000 claims description 4
- CPQJEVUJWCHUBM-UHFFFAOYSA-N 4-[1-(oxan-4-yl)pyrazolo[4,3-c]pyridin-3-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C(C1=CN=CC=C11)=NN1C1CCOCC1 CPQJEVUJWCHUBM-UHFFFAOYSA-N 0.000 claims description 4
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- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- XXTMZVKFFDHZOE-UHFFFAOYSA-N 1-[4-[3-(4-chlorophenyl)pyrazolo[4,3-c]pyridin-1-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1N1C2=CC=NC=C2C(C=2C=CC(Cl)=CC=2)=N1 XXTMZVKFFDHZOE-UHFFFAOYSA-N 0.000 claims description 3
- BHGICOLLCKBACN-UHFFFAOYSA-N 3-(4-fluorophenyl)-1-piperidin-4-ylpyrazolo[4,3-c]pyridine Chemical compound C1=CC(F)=CC=C1C(C1=CN=CC=C11)=NN1C1CCNCC1 BHGICOLLCKBACN-UHFFFAOYSA-N 0.000 claims description 3
- 206010003246 arthritis Diseases 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims description 3
- 230000007170 pathology Effects 0.000 claims description 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 2
- 208000022309 Alcoholic Liver disease Diseases 0.000 claims description 2
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 206010003827 Autoimmune hepatitis Diseases 0.000 claims description 2
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims description 2
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims description 2
- 206010007558 Cardiac failure chronic Diseases 0.000 claims description 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 2
- 208000011231 Crohn disease Diseases 0.000 claims description 2
- 206010012442 Dermatitis contact Diseases 0.000 claims description 2
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
- 208000003456 Juvenile Arthritis Diseases 0.000 claims description 2
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims description 2
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims description 2
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 2
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 2
- 206010063837 Reperfusion injury Diseases 0.000 claims description 2
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- 206010039710 Scleroderma Diseases 0.000 claims description 2
- 206010040047 Sepsis Diseases 0.000 claims description 2
- 206010051379 Systemic Inflammatory Response Syndrome Diseases 0.000 claims description 2
- 201000009594 Systemic Scleroderma Diseases 0.000 claims description 2
- 206010042953 Systemic sclerosis Diseases 0.000 claims description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 2
- 201000004810 Vascular dementia Diseases 0.000 claims description 2
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- 230000001363 autoimmune Effects 0.000 claims description 2
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- 230000009787 cardiac fibrosis Effects 0.000 claims description 2
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- 208000010247 contact dermatitis Diseases 0.000 claims description 2
- 230000003176 fibrotic effect Effects 0.000 claims description 2
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 2
- 230000000968 intestinal effect Effects 0.000 claims description 2
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 2
- 208000012947 ischemia reperfusion injury Diseases 0.000 claims description 2
- 208000023589 ischemic disease Diseases 0.000 claims description 2
- 201000002215 juvenile rheumatoid arthritis Diseases 0.000 claims description 2
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- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
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- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 156
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 40
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- 239000000543 intermediate Substances 0.000 description 25
- 238000004007 reversed phase HPLC Methods 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 18
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- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 13
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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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
- Heart & Thoracic Surgery (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Psychiatry (AREA)
- Communicable Diseases (AREA)
- Obesity (AREA)
- Gastroenterology & Hepatology (AREA)
- Emergency Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0801980 | 2008-09-16 | ||
| SE0801980-4 | 2008-09-16 | ||
| US10672708P | 2008-10-20 | 2008-10-20 | |
| US61/106,727 | 2008-10-20 | ||
| PCT/EP2009/062018 WO2010031791A1 (en) | 2008-09-16 | 2009-09-16 | New compounds ii |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012502890A JP2012502890A (ja) | 2012-02-02 |
| JP2012502890A5 JP2012502890A5 (OSRAM) | 2012-07-12 |
| JP5613671B2 true JP5613671B2 (ja) | 2014-10-29 |
Family
ID=41226934
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011526518A Expired - Fee Related JP5613671B2 (ja) | 2008-09-16 | 2009-09-16 | 新規化合物ｉｉ |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US8633318B2 (OSRAM) |
| EP (1) | EP2328895B1 (OSRAM) |
| JP (1) | JP5613671B2 (OSRAM) |
| WO (1) | WO2010031791A1 (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0699173B2 (ja) | 1990-03-30 | 1994-12-07 | 工業技術院長 | 押出成形用強化セメント組成物 |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201004311D0 (en) * | 2010-03-15 | 2010-04-28 | Proximagen Ltd | New enzyme inhibitor compounds |
| CN103038232B (zh) | 2010-05-26 | 2016-01-20 | 阿德弗里奥药品有限责任公司 | 单独的和与PDE5抑制剂相组合的sGC刺激剂、sGC活化剂用于治疗系统性硬化症(SSc)的用途 |
| FI20115234A0 (fi) | 2011-03-08 | 2011-03-08 | Biotie Therapies Corp | Uusia pyridatsinoni- ja pyridoniyhdisteitä |
| GB201115853D0 (en) * | 2011-09-14 | 2011-10-26 | Proximagen Ltd | New enzyme inhibitor compounds |
| US9150574B2 (en) | 2011-09-14 | 2015-10-06 | Proximagen Limited | Enzyme inhibitor compounds |
| CA2871388A1 (en) | 2012-06-27 | 2014-01-03 | F. Hoffmann-La Roche Ag | 5-azaindazole compounds and methods of use |
| GB201304526D0 (en) | 2013-03-13 | 2013-04-24 | Proximagen Ltd | New compounds |
| GB201304527D0 (en) | 2013-03-13 | 2013-04-24 | Proximagen Ltd | New compounds |
| US20160113893A1 (en) | 2013-06-12 | 2016-04-28 | Proximagen Limited | New therapeutic uses of enzyme inhibitors |
| WO2015189534A1 (en) | 2014-06-12 | 2015-12-17 | Proximagen Limited | Vap-1 inhibitors for treating muscular dystrophy |
| GB201416444D0 (en) * | 2014-09-17 | 2014-10-29 | Proximagen Ltd | New compounds |
| GB201416446D0 (en) * | 2014-09-17 | 2014-10-29 | Proximagen Ltd | New enzyme inhibitor compounds |
| GB201507031D0 (en) * | 2015-04-24 | 2015-06-10 | Proximagen Ltd | New pharmaceutical salt forms |
| CA3007768A1 (en) | 2015-12-07 | 2017-06-15 | Benevolentai Cambridge Limited | Vap-1 inhibitors for treating pain |
| CA3009669C (en) | 2016-01-21 | 2023-08-08 | Zibo Biopolar Changsheng Pharmaceutical Co. Ltd. | Bruton's tyrosine kinase inhibitors |
| PL3426637T3 (pl) | 2016-03-11 | 2022-05-30 | Angel Pharmaceutical Co., Ltd. | Związki i sposoby modulowania kinazy tyrozynowej brutona |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5264576A (en) * | 1992-10-22 | 1993-11-23 | Hoechst-Roussel Pharmaceuticals Incorporated | Pyrazolo[4,3-c]pyridines which are intermediates |
| AU2002214505A1 (en) * | 2000-11-09 | 2002-05-21 | Biovitrum Ab | New use of 4, 5, 6, 7-tetrahydroimidazo-(4,5-c)pyridine derivatives |
-
2009
- 2009-09-16 EP EP09783092A patent/EP2328895B1/en not_active Not-in-force
- 2009-09-16 US US13/062,366 patent/US8633318B2/en not_active Expired - Fee Related
- 2009-09-16 WO PCT/EP2009/062018 patent/WO2010031791A1/en not_active Ceased
- 2009-09-16 JP JP2011526518A patent/JP5613671B2/ja not_active Expired - Fee Related
-
2013
- 2013-12-13 US US14/105,517 patent/US20140107150A1/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0699173B2 (ja) | 1990-03-30 | 1994-12-07 | 工業技術院長 | 押出成形用強化セメント組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20110195992A1 (en) | 2011-08-11 |
| EP2328895B1 (en) | 2013-03-27 |
| US8633318B2 (en) | 2014-01-21 |
| EP2328895A1 (en) | 2011-06-08 |
| WO2010031791A1 (en) | 2010-03-25 |
| JP2012502890A (ja) | 2012-02-02 |
| US20140107150A1 (en) | 2014-04-17 |
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