JP2012502890A5 - - Google Patents
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- Publication number
- JP2012502890A5 JP2012502890A5 JP2011526518A JP2011526518A JP2012502890A5 JP 2012502890 A5 JP2012502890 A5 JP 2012502890A5 JP 2011526518 A JP2011526518 A JP 2011526518A JP 2011526518 A JP2011526518 A JP 2011526518A JP 2012502890 A5 JP2012502890 A5 JP 2012502890A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- pyrazolo
- pyridine
- chlorophenyl
- disease
- 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.)
- Granted
Links
- 208000027866 inflammatory disease Diseases 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 206010061218 Inflammation Diseases 0.000 claims 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 230000004054 inflammatory process Effects 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 206010047115 Vasculitis Diseases 0.000 claims 2
- 208000026278 immune system disease Diseases 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 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 1
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 1
- 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 1
- BCOHNJQZNDOYSC-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-1-(1-methylpiperidin-4-yl)pyrazolo[4,3-c]pyridine Chemical compound C1CN(C)CCC1N1C2=CC=NC=C2C(C=2C=C(Cl)C(Cl)=CC=2)=N1 BCOHNJQZNDOYSC-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 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 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 208000022309 Alcoholic Liver disease Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010003827 Autoimmune hepatitis Diseases 0.000 claims 1
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims 1
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims 1
- 206010007558 Cardiac failure chronic Diseases 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 206010012442 Dermatitis contact Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000003456 Juvenile Arthritis Diseases 0.000 claims 1
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims 1
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 1
- 206010039710 Scleroderma Diseases 0.000 claims 1
- 208000034189 Sclerosis Diseases 0.000 claims 1
- 206010040047 Sepsis Diseases 0.000 claims 1
- 206010051379 Systemic Inflammatory Response Syndrome Diseases 0.000 claims 1
- 201000009594 Systemic Scleroderma Diseases 0.000 claims 1
- 206010042953 Systemic sclerosis Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 201000004810 Vascular dementia Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 230000001363 autoimmune Effects 0.000 claims 1
- 208000018093 autoimmune cholangitis Diseases 0.000 claims 1
- 230000009787 cardiac fibrosis Effects 0.000 claims 1
- 208000003167 cholangitis Diseases 0.000 claims 1
- 208000019069 chronic childhood arthritis Diseases 0.000 claims 1
- 208000010247 contact dermatitis Diseases 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 230000003176 fibrotic effect Effects 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 1
- 230000000968 intestinal effect Effects 0.000 claims 1
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- 208000012947 ischemia reperfusion injury Diseases 0.000 claims 1
- 208000023589 ischemic disease Diseases 0.000 claims 1
- 201000002215 juvenile rheumatoid arthritis Diseases 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 230000007170 pathology Effects 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 230000002685 pulmonary effect Effects 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 201000004595 synovitis Diseases 0.000 claims 1
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 true JP2012502890A5 (enExample) | 2012-07-12 |
| JP5613671B2 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 (enExample) |
| EP (1) | EP2328895B1 (enExample) |
| JP (1) | JP5613671B2 (enExample) |
| WO (1) | WO2010031791A1 (enExample) |
Families Citing this family (17)
| 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 |
| GB201004311D0 (en) * | 2010-03-15 | 2010-04-28 | Proximagen Ltd | New enzyme inhibitor compounds |
| ES2549979T3 (es) * | 2010-05-26 | 2015-11-03 | Adverio Pharma Gmbh | El uso de estimuladores de la sGC, activadores de la sGC, solos y en combinaciones con inhibidores de la PDE5 para el tratamiento de esclerosis sistémica (EcS) |
| 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 |
| CN103889983B (zh) * | 2011-09-14 | 2015-12-09 | 普罗克西梅根有限公司 | 酶抑制剂化合物 |
| KR20150028999A (ko) | 2012-06-27 | 2015-03-17 | 에프. 호프만-라 로슈 아게 | 5-아자인다졸 화합물 및 이의 사용 방법 |
| GB201304526D0 (en) | 2013-03-13 | 2013-04-24 | Proximagen Ltd | New compounds |
| GB201304527D0 (en) | 2013-03-13 | 2013-04-24 | Proximagen Ltd | New compounds |
| CA2915163A1 (en) | 2013-06-12 | 2014-12-18 | 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 |
| GB201416446D0 (en) * | 2014-09-17 | 2014-10-29 | Proximagen Ltd | New enzyme inhibitor compounds |
| GB201416444D0 (en) * | 2014-09-17 | 2014-10-29 | Proximagen Ltd | New compounds |
| GB201507031D0 (en) * | 2015-04-24 | 2015-06-10 | Proximagen Ltd | New pharmaceutical salt forms |
| US20180360808A1 (en) | 2015-12-07 | 2018-12-20 | Benevolentai Cambridge Limited | Vap-1 inhibitors for treating pain |
| AU2017208998B2 (en) * | 2016-01-21 | 2021-07-15 | Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences | Bruton's tyrosine kinase inhibitors |
| EP3426637B1 (en) | 2016-03-11 | 2022-02-09 | Angel Pharmaceutical Co., Ltd. | Compounds and methods for modulating bruton's tyrosine kinase |
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 US US13/062,366 patent/US8633318B2/en not_active Expired - Fee Related
- 2009-09-16 EP EP09783092A patent/EP2328895B1/en not_active Not-in-force
- 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