JP2017509676A5 - - Google Patents
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- Publication number
- JP2017509676A5 JP2017509676A5 JP2016560674A JP2016560674A JP2017509676A5 JP 2017509676 A5 JP2017509676 A5 JP 2017509676A5 JP 2016560674 A JP2016560674 A JP 2016560674A JP 2016560674 A JP2016560674 A JP 2016560674A JP 2017509676 A5 JP2017509676 A5 JP 2017509676A5
- Authority
- JP
- Japan
- Prior art keywords
- carboxamide
- pyridine
- cyclopropylmethoxy
- oxadiazol
- cyclopropyl
- 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
- -1 halophenylalkyl Chemical group 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 22
- 208000020016 psychiatric disease Diseases 0.000 claims description 18
- 206010003246 arthritis Diseases 0.000 claims description 16
- 208000028017 Psychotic disease Diseases 0.000 claims description 15
- 206010061218 Inflammation Diseases 0.000 claims description 10
- 206010028980 Neoplasm Diseases 0.000 claims description 10
- 206010014599 encephalitis Diseases 0.000 claims description 10
- 230000004054 inflammatory process Effects 0.000 claims description 10
- 201000004792 malaria Diseases 0.000 claims description 10
- 208000001132 Osteoporosis Diseases 0.000 claims description 9
- 208000002193 Pain Diseases 0.000 claims description 9
- 208000006673 asthma Diseases 0.000 claims description 9
- 208000026278 immune system disease Diseases 0.000 claims description 9
- 208000004296 neuralgia Diseases 0.000 claims description 9
- 208000021722 neuropathic pain Diseases 0.000 claims description 9
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 8
- 206010020751 Hypersensitivity Diseases 0.000 claims description 7
- 230000000172 allergic effect Effects 0.000 claims description 7
- 230000007815 allergy Effects 0.000 claims description 7
- 208000010668 atopic eczema Diseases 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 5
- 208000026935 allergic disease Diseases 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 230000000069 prophylactic effect Effects 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 16
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000005059 halophenyl group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 2
- LZPWAYBEOJRFAX-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2$l^{2}-dioxaborolane Chemical group CC1(C)O[B]OC1(C)C LZPWAYBEOJRFAX-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical group FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 claims 2
- 229910052763 palladium Inorganic materials 0.000 claims 2
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical group CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 claims 1
- FACJIODPNQMPJQ-UHFFFAOYSA-N 4-[5-cyclopropyl-6-(cyclopropylmethoxy)pyridine-2-carbonyl]thiomorpholine-3-carboxamide Chemical compound NC(=O)C1CSCCN1C(=O)C(N=C1OCC2CC2)=CC=C1C1CC1 FACJIODPNQMPJQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- GHBIFWJMGJLPJL-UHFFFAOYSA-N C1(CC1)COC1=C(C=CC(=N1)C(=O)NC12CC3(CC(CC(C1)C3)C2)O)N2CC(C2)(F)F Chemical compound C1(CC1)COC1=C(C=CC(=N1)C(=O)NC12CC3(CC(CC(C1)C3)C2)O)N2CC(C2)(F)F GHBIFWJMGJLPJL-UHFFFAOYSA-N 0.000 claims 1
- GANJOZPBMGPBDY-UHFFFAOYSA-N CC(C)(CC1=NC(=NO1)C1=CC=CC=C1)NC(=O)C1=NC(OCC(F)(F)F)=CC=C1 Chemical compound CC(C)(CC1=NC(=NO1)C1=CC=CC=C1)NC(=O)C1=NC(OCC(F)(F)F)=CC=C1 GANJOZPBMGPBDY-UHFFFAOYSA-N 0.000 claims 1
- QETRMUBQKBPDKU-UHFFFAOYSA-N CC(C)(CC1=NN=C(O1)C1=CC=CC=C1)NC(=O)C1=NC(OCC(F)(F)F)=CC=C1 Chemical compound CC(C)(CC1=NN=C(O1)C1=CC=CC=C1)NC(=O)C1=NC(OCC(F)(F)F)=CC=C1 QETRMUBQKBPDKU-UHFFFAOYSA-N 0.000 claims 1
- NXTDMSXSJGPTNM-UHFFFAOYSA-N COCCOCC(C)(C)C1=NOC(NC(=O)C2=NC(OCC3CC3)=C(C=C2)N2CC(F)(F)C2)=C1 Chemical compound COCCOCC(C)(C)C1=NOC(NC(=O)C2=NC(OCC3CC3)=C(C=C2)N2CC(F)(F)C2)=C1 NXTDMSXSJGPTNM-UHFFFAOYSA-N 0.000 claims 1
- BWMGKSFFMRANBX-UHFFFAOYSA-N N-[3-(1-azido-2-methylpropan-2-yl)-1,2-oxazol-5-yl]-5-cyclopropyl-6-(cyclopropylmethoxy)pyrazine-2-carboxamide Chemical compound CC(C)(CN=[N+]=[N-])C1=NOC(NC(=O)C2=CN=C(C3CC3)C(OCC3CC3)=N2)=C1 BWMGKSFFMRANBX-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
- 125000005620 boronic acid group Chemical group 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000007822 coupling agent Substances 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- STUHQDIOZQUPGP-UHFFFAOYSA-N morpholin-4-ium-4-carboxylate Chemical compound OC(=O)N1CCOCC1 STUHQDIOZQUPGP-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
- 102000009135 CB2 Cannabinoid Receptor Human genes 0.000 description 3
- 108010073376 CB2 Cannabinoid Receptor Proteins 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002621 endocannabinoid Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 239000002469 receptor inverse agonist Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14163555.7 | 2014-04-04 | ||
| EP14163555 | 2014-04-04 | ||
| PCT/EP2015/057151 WO2015150440A1 (en) | 2014-04-04 | 2015-04-01 | Pyridine-2-amides useful as cb2 agonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017509676A JP2017509676A (ja) | 2017-04-06 |
| JP2017509676A5 true JP2017509676A5 (enExample) | 2019-05-16 |
| JP6654574B2 JP6654574B2 (ja) | 2020-02-26 |
Family
ID=50424143
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016560674A Expired - Fee Related JP6654574B2 (ja) | 2014-04-04 | 2015-04-01 | Ｃｂ２アゴニストとして有用なピリジン−２−アミド |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US20160376262A1 (enExample) |
| EP (1) | EP3126359A1 (enExample) |
| JP (1) | JP6654574B2 (enExample) |
| KR (1) | KR20160142365A (enExample) |
| CN (1) | CN106132958A (enExample) |
| AR (1) | AR099933A1 (enExample) |
| AU (1) | AU2015239539A1 (enExample) |
| CA (1) | CA2943013A1 (enExample) |
| CL (1) | CL2016002483A1 (enExample) |
| CR (1) | CR20160448A (enExample) |
| EA (1) | EA030116B1 (enExample) |
| IL (1) | IL247817A0 (enExample) |
| MA (1) | MA39843A (enExample) |
| MX (1) | MX2016012689A (enExample) |
| PE (1) | PE20161370A1 (enExample) |
| PH (1) | PH12016501865A1 (enExample) |
| SG (2) | SG11201608108SA (enExample) |
| TW (1) | TW201623276A (enExample) |
| WO (1) | WO2015150440A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MA38404B1 (fr) | 2013-03-26 | 2017-09-29 | Hoffmann La Roche | Nouveaux dérivés de pyridine |
| MA39837B1 (fr) | 2014-04-04 | 2020-05-29 | H Lundbeck As | Quinazoline-thf-amines halogénées en tant qu'inhibiteurs de la pde1 |
| MY195889A (en) * | 2015-12-09 | 2023-02-27 | Hoffmann La Roche | Phenyl Derivatives as Cannabinoid Receptor 2 Agonists |
| JP2019513700A (ja) | 2016-03-16 | 2019-05-30 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 殺有害生物剤及び植物保護剤としてのｎ−（シアノベンジル）−６−（シクロプロピル−カルボニルアミノ）−４−（フェニル）−ピリジン−２−カルボキサミド誘導体及び関連する化合物 |
| WO2018234284A1 (en) | 2017-06-20 | 2018-12-27 | F. Hoffmann-La Roche Ag | Pyridine derivatives |
| CN116640118B (zh) | 2018-06-27 | 2025-12-19 | 豪夫迈·罗氏有限公司 | 放射性标记的大麻素受体2配体 |
| CN119161323A (zh) * | 2018-06-27 | 2024-12-20 | 豪夫迈·罗氏有限公司 | 作为大麻素受体2的抑制剂的新型吡啶和吡嗪化合物 |
| CN112119068A (zh) | 2018-06-27 | 2020-12-22 | 豪夫迈·罗氏有限公司 | 作为大麻素受体2的抑制剂的新型氮杂环丁烷-取代的吡啶和吡嗪化合物 |
| WO2020002270A1 (en) | 2018-06-27 | 2020-01-02 | F. Hoffmann-La Roche Ag | Pyridine and pyrazine derivatives as preferential cannabinoid 2 agonists |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2601575A1 (en) | 2005-03-31 | 2006-10-05 | Schering Corporation | Spirocyclic thrombin receptor antagonists |
| FR2887550A1 (fr) | 2005-06-24 | 2006-12-29 | Sanofi Aventis Sa | Derives de 1-benzylpyrazole-3-acetamide, leur preparation et leur application en therapeutique |
| EP2155747B1 (en) * | 2007-05-10 | 2012-10-24 | GE Healthcare Limited | Imidazol (1,2-a)pyridines and related compounds with activity at cannabinoid cb2 receptors |
| EP2311443A1 (en) | 2009-10-15 | 2011-04-20 | Rheinische Friedrich-Wilhelms-Universität | Pharmaceutical composition containing cannabinoid-receptor 2 antagonists |
| WO2012031817A1 (en) * | 2010-09-09 | 2012-03-15 | F. Hoffmann-La Roche Ag | Determination of abca1 protein levels in cells |
| US9321727B2 (en) * | 2011-06-10 | 2016-04-26 | Hoffmann-La Roche Inc. | Pyridine derivatives as agonists of the CB2 receptor |
| US9403808B2 (en) * | 2011-10-28 | 2016-08-02 | Hoffmann-La Roche Inc. | Pyrazine derivatives |
| RS55951B1 (sr) * | 2012-12-07 | 2017-09-29 | Hoffmann La Roche | Derivati pirazina kao agonisti cb2 receptora |
| PL2928868T3 (pl) * | 2012-12-07 | 2017-12-29 | F.Hoffmann-La Roche Ag | Pirydyno-2-amidy użyteczne jako agoniści cb2 |
-
2015
- 2015-04-01 MX MX2016012689A patent/MX2016012689A/es unknown
- 2015-04-01 CA CA2943013A patent/CA2943013A1/en not_active Abandoned
- 2015-04-01 WO PCT/EP2015/057151 patent/WO2015150440A1/en not_active Ceased
- 2015-04-01 CN CN201580017199.1A patent/CN106132958A/zh active Pending
- 2015-04-01 PE PE2016001656A patent/PE20161370A1/es unknown
- 2015-04-01 EP EP15713492.5A patent/EP3126359A1/en not_active Withdrawn
- 2015-04-01 CR CR20160448A patent/CR20160448A/es unknown
- 2015-04-01 AR ARP150100985A patent/AR099933A1/es unknown
- 2015-04-01 MA MA039843A patent/MA39843A/fr unknown
- 2015-04-01 SG SG11201608108SA patent/SG11201608108SA/en unknown
- 2015-04-01 AU AU2015239539A patent/AU2015239539A1/en not_active Abandoned
- 2015-04-01 SG SG10201809066TA patent/SG10201809066TA/en unknown
- 2015-04-01 KR KR1020167030780A patent/KR20160142365A/ko not_active Withdrawn
- 2015-04-01 EA EA201691983A patent/EA030116B1/ru not_active IP Right Cessation
- 2015-04-01 JP JP2016560674A patent/JP6654574B2/ja not_active Expired - Fee Related
- 2015-04-02 TW TW104111026A patent/TW201623276A/zh unknown
-
2016
- 2016-09-09 US US15/260,826 patent/US20160376262A1/en not_active Abandoned
- 2016-09-14 IL IL247817A patent/IL247817A0/en unknown
- 2016-09-22 PH PH12016501865A patent/PH12016501865A1/en unknown
- 2016-09-30 CL CL2016002483A patent/CL2016002483A1/es unknown
-
2018
- 2018-07-24 US US16/044,320 patent/US20180327396A1/en not_active Abandoned