JP2011503210A5 - - Google Patents
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- Publication number
- JP2011503210A5 JP2011503210A5 JP2010534263A JP2010534263A JP2011503210A5 JP 2011503210 A5 JP2011503210 A5 JP 2011503210A5 JP 2010534263 A JP2010534263 A JP 2010534263A JP 2010534263 A JP2010534263 A JP 2010534263A JP 2011503210 A5 JP2011503210 A5 JP 2011503210A5
- Authority
- JP
- Japan
- Prior art keywords
- piperidin
- yloxy
- alkyl
- phenyl
- trifluoromethyl
- 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 hydrate Chemical class 0.000 claims description 257
- 150000001875 compounds Chemical class 0.000 claims description 123
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 22
- 125000004122 cyclic group Chemical group 0.000 claims description 19
- 150000001204 N-oxides Chemical class 0.000 claims description 17
- 239000000651 prodrug Substances 0.000 claims description 17
- 229940002612 prodrug Drugs 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 239000012453 solvate Substances 0.000 claims description 17
- 125000001188 haloalkyl group Chemical group 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 7
- 125000005605 benzo group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 150000003857 carboxamides Chemical class 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- MCLGXPUTSWJSRB-UHFFFAOYSA-N 1-(pyridin-4-ylmethyl)-n-[5-[1-[4-(trifluoromethyl)phenyl]piperidin-4-yl]oxy-2,3-dihydro-1h-inden-1-yl]piperidin-4-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1N1CCC(OC=2C=C3CCC(C3=CC=2)NC2CCN(CC=3C=CN=CC=3)CC2)CC1 MCLGXPUTSWJSRB-UHFFFAOYSA-N 0.000 claims description 2
- IIYPLRFMIACDPN-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]-n-[5-[1-[4-(trifluoromethyl)phenyl]piperidin-4-yl]oxy-2,3-dihydro-1h-inden-1-yl]piperidin-4-amine Chemical compound C1=CC(F)=CC=C1CN1CCC(NC2C3=CC=C(OC4CCN(CC4)C=4C=CC(=CC=4)C(F)(F)F)C=C3CC2)CC1 IIYPLRFMIACDPN-UHFFFAOYSA-N 0.000 claims description 2
- 102100036009 5'-AMP-activated protein kinase catalytic subunit alpha-2 Human genes 0.000 claims description 2
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- GCWSPRDNKSEPKJ-UHFFFAOYSA-N CC1C=CC(=CN1C2CCN(CC2)CC3=CN(C=N3)C(C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)OC7CCN(CC7)C8=CC=C(C=C8)C(F)(F)F Chemical compound CC1C=CC(=CN1C2CCN(CC2)CC3=CN(C=N3)C(C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)OC7CCN(CC7)C8=CC=C(C=C8)C(F)(F)F GCWSPRDNKSEPKJ-UHFFFAOYSA-N 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 2
- 101000783681 Homo sapiens 5'-AMP-activated protein kinase catalytic subunit alpha-2 Proteins 0.000 claims description 2
- AVRWEULSKHQETA-UHFFFAOYSA-N Thiophene-2 Chemical compound S1C=2CCCCCC=2C(C(=O)OC)=C1NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F AVRWEULSKHQETA-UHFFFAOYSA-N 0.000 claims description 2
- 230000003213 activating effect Effects 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims description 2
- ZTFZEMAQQLKFEQ-UHFFFAOYSA-N n-[1-(pyridin-4-ylmethyl)piperidin-4-yl]-6-[1-[4-(trifluoromethyl)phenyl]piperidin-4-yl]oxypyridine-2-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1N1CCC(OC=2N=C(C=CC=2)C(=O)NC2CCN(CC=3C=CN=CC=3)CC2)CC1 ZTFZEMAQQLKFEQ-UHFFFAOYSA-N 0.000 claims description 2
- JGGUDZHAKXSMBF-UHFFFAOYSA-N n-[5-[1-[4-(trifluoromethyl)phenyl]piperidin-4-yl]oxy-2,3-dihydro-1h-inden-1-yl]piperidin-4-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1N1CCC(OC=2C=C3CCC(C3=CC=2)NC2CCNCC2)CC1 JGGUDZHAKXSMBF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 230000037361 pathway Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- KXNHURZRBCWTFV-UHFFFAOYSA-N tert-butyl 4-[[5-[1-[4-(trifluoromethyl)phenyl]piperidin-4-yl]oxy-2,3-dihydro-1h-inden-1-yl]amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1C2=CC=C(OC3CCN(CC3)C=3C=CC(=CC=3)C(F)(F)F)C=C2CC1 KXNHURZRBCWTFV-UHFFFAOYSA-N 0.000 claims description 2
- RTJCPJPIPFHECW-UHFFFAOYSA-N tert-butyl 4-[[6-[1-[4-(trifluoromethyl)phenyl]piperidin-4-yl]oxypyridin-3-yl]sulfonylamino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NS(=O)(=O)C(C=N1)=CC=C1OC1CCN(C=2C=CC(=CC=2)C(F)(F)F)CC1 RTJCPJPIPFHECW-UHFFFAOYSA-N 0.000 claims description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- DFWJSMFBORLYJK-UHFFFAOYSA-N O=C(C1=CC(C=CC=C2)=C2S1)NOC(CC1)CCN1C1=CC=C(C(F)(F)F)C=C1 Chemical compound O=C(C1=CC(C=CC=C2)=C2S1)NOC(CC1)CCN1C1=CC=C(C(F)(F)F)C=C1 DFWJSMFBORLYJK-UHFFFAOYSA-N 0.000 claims 1
- NKFLEFWUYAUDJV-UHFFFAOYSA-N pyridine-3-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CN=C1 NKFLEFWUYAUDJV-UHFFFAOYSA-N 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 9
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- BYHWWOPUEYHTSB-UHFFFAOYSA-N 4-[[4-[[5-[1-[4-(trifluoromethyl)phenyl]piperidin-4-yl]oxy-2,3-dihydro-1h-inden-1-yl]amino]piperidin-1-yl]methyl]benzonitrile Chemical compound C1=CC(C(F)(F)F)=CC=C1N1CCC(OC=2C=C3CCC(C3=CC=2)NC2CCN(CC=3C=CC(=CC=3)C#N)CC2)CC1 BYHWWOPUEYHTSB-UHFFFAOYSA-N 0.000 description 1
- 229920002527 Glycogen Polymers 0.000 description 1
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000004190 glucose uptake Effects 0.000 description 1
- 229940096919 glycogen Drugs 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US98872107P | 2007-11-16 | 2007-11-16 | |
| US60/988,721 | 2007-11-16 | ||
| US99055807P | 2007-11-27 | 2007-11-27 | |
| US99055407P | 2007-11-27 | 2007-11-27 | |
| US60/990,554 | 2007-11-27 | ||
| US60/990,558 | 2007-11-27 | ||
| US99118907P | 2007-11-29 | 2007-11-29 | |
| US60/991,189 | 2007-11-29 | ||
| US1392407P | 2007-12-14 | 2007-12-14 | |
| US61/013,924 | 2007-12-14 | ||
| PCT/US2008/083801 WO2009065131A1 (en) | 2007-11-16 | 2008-11-17 | Carboxamide, sulfonamide and amine compounds for metabolic disorders |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011503210A JP2011503210A (ja) | 2011-01-27 |
| JP2011503210A5 true JP2011503210A5 (enExample) | 2012-12-20 |
| JP5544296B2 JP5544296B2 (ja) | 2014-07-09 |
Family
ID=40352415
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010534263A Expired - Fee Related JP5544296B2 (ja) | 2007-11-16 | 2008-11-17 | 代謝障害のためのカルボキサミド、スルホンアミド、およびアミン化合物 |
Country Status (15)
| Country | Link |
|---|---|
| US (3) | US8119809B2 (enExample) |
| EP (1) | EP2231600B1 (enExample) |
| JP (1) | JP5544296B2 (enExample) |
| KR (1) | KR101573091B1 (enExample) |
| CN (1) | CN101910131B (enExample) |
| AU (3) | AU2008322426C1 (enExample) |
| BR (1) | BRPI0820171B8 (enExample) |
| CA (1) | CA2705947C (enExample) |
| EA (1) | EA019509B1 (enExample) |
| ES (1) | ES2552733T3 (enExample) |
| IL (1) | IL205624A (enExample) |
| MX (2) | MX382569B (enExample) |
| NZ (1) | NZ585298A (enExample) |
| WO (1) | WO2009065131A1 (enExample) |
| ZA (1) | ZA201003412B (enExample) |
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| US20160214967A1 (en) * | 2013-09-30 | 2016-07-28 | The University Of Tokyo | Activator of adiponectin receptor |
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| EP3959205B1 (en) * | 2019-04-26 | 2025-11-12 | Merck Sharp & Dohme LLC | Process for the preparation of intermediates useful for making (2s,5r)-7-oxo-n-piperidin-4-yl-6-(sulfoxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide |
| CN116322663A (zh) | 2020-09-30 | 2023-06-23 | 比奥维拉迪维治疗股份有限公司 | Ampk激活剂及其使用方法 |
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-
2008
- 2008-11-17 EP EP08848677.4A patent/EP2231600B1/en not_active Not-in-force
- 2008-11-17 KR KR1020107013166A patent/KR101573091B1/ko not_active Expired - Fee Related
- 2008-11-17 US US12/272,581 patent/US8119809B2/en active Active
- 2008-11-17 CN CN200880124960.1A patent/CN101910131B/zh not_active Expired - Fee Related
- 2008-11-17 CA CA2705947A patent/CA2705947C/en active Active
- 2008-11-17 WO PCT/US2008/083801 patent/WO2009065131A1/en not_active Ceased
- 2008-11-17 NZ NZ585298A patent/NZ585298A/xx not_active IP Right Cessation
- 2008-11-17 MX MX2014005186A patent/MX382569B/es unknown
- 2008-11-17 ES ES08848677.4T patent/ES2552733T3/es active Active
- 2008-11-17 BR BRPI0820171A patent/BRPI0820171B8/pt not_active IP Right Cessation
- 2008-11-17 EA EA201070619A patent/EA019509B1/ru not_active IP Right Cessation
- 2008-11-17 AU AU2008322426A patent/AU2008322426C1/en not_active Ceased
- 2008-11-17 MX MX2010005298A patent/MX2010005298A/es active IP Right Grant
- 2008-11-17 JP JP2010534263A patent/JP5544296B2/ja not_active Expired - Fee Related
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2010
- 2010-05-09 IL IL205624A patent/IL205624A/en active IP Right Grant
- 2010-05-14 ZA ZA2010/03412A patent/ZA201003412B/en unknown
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- 2012-01-11 US US13/348,380 patent/US8569340B2/en not_active Expired - Fee Related
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- 2013-10-14 US US14/053,325 patent/US9174964B2/en active Active
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