JP2010514788A5 - - Google Patents
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- Publication number
- JP2010514788A5 JP2010514788A5 JP2009544239A JP2009544239A JP2010514788A5 JP 2010514788 A5 JP2010514788 A5 JP 2010514788A5 JP 2009544239 A JP2009544239 A JP 2009544239A JP 2009544239 A JP2009544239 A JP 2009544239A JP 2010514788 A5 JP2010514788 A5 JP 2010514788A5
- Authority
- JP
- Japan
- Prior art keywords
- piperidin
- yloxy
- benzamide
- benzylpiperidin
- alkyl
- 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 171
- 150000001875 compounds Chemical class 0.000 claims description 163
- 125000000217 alkyl group Chemical group 0.000 claims description 92
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 38
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
- 125000001475 halogen functional group Chemical group 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 21
- 239000012453 solvate Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 15
- 239000000651 prodrug Substances 0.000 claims description 15
- 229940002612 prodrug Drugs 0.000 claims description 15
- 150000001204 N-oxides Chemical class 0.000 claims description 12
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 150000007942 carboxylates Chemical class 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 150000003857 carboxamides Chemical class 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 4
- OPZIJNBWFXUVDG-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-3-chloro-4-[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]oxybenzamide Chemical compound C1=CC(OC)=CC=C1CN1CCC(OC=2C(=CC(=CC=2)C(=O)NC2CCN(CC=3C=CC=CC=3)CC2)Cl)CC1 OPZIJNBWFXUVDG-UHFFFAOYSA-N 0.000 claims description 4
- SJIZCVQALKMPCJ-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-4-(1-benzylpiperidin-4-yl)oxy-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NC2CCN(CC=3C=CC=CC=3)CC2)=CC=C1OC(CC1)CCN1CC1=CC=CC=C1 SJIZCVQALKMPCJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 4
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 4
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 150000004677 hydrates Chemical class 0.000 claims description 3
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 2
- PYPFAWVKBZFLFU-UHFFFAOYSA-N 4-[[4-[[3-fluoro-4-[1-[4-(trifluoromethyl)phenyl]piperidin-4-yl]oxybenzoyl]amino]piperidin-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1CCC(NC(=O)C=2C=C(F)C(OC3CCN(CC3)C=3C=CC(=CC=3)C(F)(F)F)=CC=2)CC1 PYPFAWVKBZFLFU-UHFFFAOYSA-N 0.000 claims description 2
- 102100036009 5'-AMP-activated protein kinase catalytic subunit alpha-2 Human genes 0.000 claims description 2
- 229920002527 Glycogen Polymers 0.000 claims description 2
- 101000783681 Homo sapiens 5'-AMP-activated protein kinase catalytic subunit alpha-2 Proteins 0.000 claims description 2
- 230000003213 activating effect Effects 0.000 claims description 2
- 125000003725 azepanyl group Chemical group 0.000 claims description 2
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 2
- 125000002393 azetidinyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 230000004190 glucose uptake Effects 0.000 claims description 2
- 229940096919 glycogen Drugs 0.000 claims description 2
- 229940095102 methyl benzoate Drugs 0.000 claims description 2
- OSEGNJLBTIAZAR-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-4-(1-benzylpiperidin-4-yl)oxy-3-chlorobenzamide Chemical compound ClC1=CC(C(=O)NC2CCN(CC=3C=CC=CC=3)CC2)=CC=C1OC(CC1)CCN1CC1=CC=CC=C1 OSEGNJLBTIAZAR-UHFFFAOYSA-N 0.000 claims description 2
- ZSSQHQZDGFFADT-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-4-[1-[(3,4-dichlorophenyl)methyl]piperidin-4-yl]oxy-3-fluorobenzamide Chemical compound FC1=CC(C(=O)NC2CCN(CC=3C=CC=CC=3)CC2)=CC=C1OC(CC1)CCN1CC1=CC=C(Cl)C(Cl)=C1 ZSSQHQZDGFFADT-UHFFFAOYSA-N 0.000 claims description 2
- VTAPBBBNOFCMJE-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-4-[1-[(3,4-difluorophenyl)methyl]piperidin-4-yl]oxy-3-fluorobenzamide Chemical compound C1=C(F)C(F)=CC=C1CN1CCC(OC=2C(=CC(=CC=2)C(=O)NC2CCN(CC=3C=CC=CC=3)CC2)F)CC1 VTAPBBBNOFCMJE-UHFFFAOYSA-N 0.000 claims description 2
- WPVQGPSAFVQBTQ-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-4-[1-[(4-chlorophenyl)methyl]piperidin-4-yl]oxy-3-fluorobenzamide Chemical compound FC1=CC(C(=O)NC2CCN(CC=3C=CC=CC=3)CC2)=CC=C1OC(CC1)CCN1CC1=CC=C(Cl)C=C1 WPVQGPSAFVQBTQ-UHFFFAOYSA-N 0.000 claims description 2
- FEMJUIILXCLATR-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-4-[1-[(4-cyanophenyl)methyl]piperidin-4-yl]oxy-3-fluorobenzamide Chemical compound FC1=CC(C(=O)NC2CCN(CC=3C=CC=CC=3)CC2)=CC=C1OC(CC1)CCN1CC1=CC=C(C#N)C=C1 FEMJUIILXCLATR-UHFFFAOYSA-N 0.000 claims description 2
- RSVKHYKCXSKQMH-UHFFFAOYSA-N n-[1-[(4-chlorophenyl)methyl]piperidin-4-yl]-4-[1-(4-cyanophenyl)piperidin-4-yl]oxy-3-fluorobenzamide Chemical compound FC1=CC(C(=O)NC2CCN(CC=3C=CC(Cl)=CC=3)CC2)=CC=C1OC(CC1)CCN1C1=CC=C(C#N)C=C1 RSVKHYKCXSKQMH-UHFFFAOYSA-N 0.000 claims description 2
- FTQQFCXRUSWUMF-UHFFFAOYSA-N n-[1-[(4-chlorophenyl)methyl]piperidin-4-yl]-4-[1-[(3,4-dichlorophenyl)methyl]piperidin-4-yl]oxy-3-fluorobenzamide Chemical compound FC1=CC(C(=O)NC2CCN(CC=3C=CC(Cl)=CC=3)CC2)=CC=C1OC(CC1)CCN1CC1=CC=C(Cl)C(Cl)=C1 FTQQFCXRUSWUMF-UHFFFAOYSA-N 0.000 claims description 2
- UIOUEJIAZRRPMS-UHFFFAOYSA-N n-[1-[(4-chlorophenyl)methyl]piperidin-4-yl]-4-[1-[(3,4-difluorophenyl)methyl]piperidin-4-yl]oxy-3-fluorobenzamide Chemical compound C1=C(F)C(F)=CC=C1CN1CCC(OC=2C(=CC(=CC=2)C(=O)NC2CCN(CC=3C=CC(Cl)=CC=3)CC2)F)CC1 UIOUEJIAZRRPMS-UHFFFAOYSA-N 0.000 claims description 2
- QFKXALBARODOIK-UHFFFAOYSA-N n-[1-[(4-chlorophenyl)methyl]piperidin-4-yl]-4-[1-[(4-chlorophenyl)methyl]piperidin-4-yl]oxy-3-fluorobenzamide Chemical compound FC1=CC(C(=O)NC2CCN(CC=3C=CC(Cl)=CC=3)CC2)=CC=C1OC(CC1)CCN1CC1=CC=C(Cl)C=C1 QFKXALBARODOIK-UHFFFAOYSA-N 0.000 claims description 2
- WHGMTCQFUXQDID-UHFFFAOYSA-N n-[1-[(4-chlorophenyl)methyl]piperidin-4-yl]-4-[1-[(4-cyanophenyl)methyl]piperidin-4-yl]oxy-3-fluorobenzamide Chemical compound FC1=CC(C(=O)NC2CCN(CC=3C=CC(Cl)=CC=3)CC2)=CC=C1OC(CC1)CCN1CC1=CC=C(C#N)C=C1 WHGMTCQFUXQDID-UHFFFAOYSA-N 0.000 claims description 2
- OESUCOSKWSDWGA-UHFFFAOYSA-N n-[1-[(4-cyanophenyl)methyl]piperidin-4-yl]-4-[1-(4-cyanophenyl)piperidin-4-yl]oxy-3-fluorobenzamide Chemical compound FC1=CC(C(=O)NC2CCN(CC=3C=CC(=CC=3)C#N)CC2)=CC=C1OC(CC1)CCN1C1=CC=C(C#N)C=C1 OESUCOSKWSDWGA-UHFFFAOYSA-N 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 230000037361 pathway Effects 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 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
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 3
- 125000006187 phenyl benzyl group Chemical group 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 0 CC*(C1)CN(*)*CC(C)C*1OC(C=C1)=CC(C)(C)C=C1C(N(*)*)=O Chemical compound CC*(C1)CN(*)*CC(C)C*1OC(C=C1)=CC(C)(C)C=C1C(N(*)*)=O 0.000 description 35
- 238000000034 method Methods 0.000 description 13
- 125000003709 fluoroalkyl group Chemical group 0.000 description 12
- 238000006467 substitution reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88231206P | 2006-12-28 | 2006-12-28 | |
| US60/882,312 | 2006-12-28 | ||
| US98871907P | 2007-11-16 | 2007-11-16 | |
| US60/988,719 | 2007-11-16 | ||
| PCT/US2007/088742 WO2008083124A1 (en) | 2006-12-28 | 2007-12-21 | N-substituted-heterocycloalkyloxybenzamide compounds and methods of use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010514788A JP2010514788A (ja) | 2010-05-06 |
| JP2010514788A5 true JP2010514788A5 (OSRAM) | 2012-01-26 |
| JP5650404B2 JP5650404B2 (ja) | 2015-01-07 |
Family
ID=39204919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009544239A Expired - Fee Related JP5650404B2 (ja) | 2006-12-28 | 2007-12-21 | Ｎ−置換−ヘテロシクロアルキルオキシベンズアミド化合物およびその使用方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US8012955B2 (OSRAM) |
| EP (1) | EP2079694B1 (OSRAM) |
| JP (1) | JP5650404B2 (OSRAM) |
| CA (1) | CA2674237C (OSRAM) |
| ES (1) | ES2627221T3 (OSRAM) |
| WO (1) | WO2008083124A1 (OSRAM) |
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| AU2009240643B2 (en) | 2008-04-23 | 2014-03-06 | Rigel Pharmaceuticals, Inc. | Carboxamide compounds for the treatment of metabolic disorders |
| WO2010088392A1 (en) * | 2009-01-28 | 2010-08-05 | Rigel Pharmaceuticals, Inc. | Carboxamide compounds and methods for using the same |
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| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2011123681A1 (en) | 2010-03-31 | 2011-10-06 | Rigel Pharmaceuticals, Inc. | Methods for using carboxamide, sulfonamide and amine compounds |
| WO2011142359A1 (ja) * | 2010-05-10 | 2011-11-17 | 日産化学工業株式会社 | スピロ化合物及びアディポネクチン受容体活性化薬 |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
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| US8697911B2 (en) | 2010-07-07 | 2014-04-15 | Boehringer Ingelheim International Gmbh | Rho kinase inhibitors |
| US9079880B2 (en) | 2010-07-07 | 2015-07-14 | Boehringer Ingelheim International Gmbh | Rho kinase inhibitors |
| PT2598483T (pt) * | 2010-07-29 | 2020-10-12 | Rigel Pharmaceuticals Inc | Compostos heterocíclicos de ativação de ampk e métodos de utilização dos mesmos |
| WO2012054367A1 (en) | 2010-10-19 | 2012-04-26 | Boehringer Ingelheim International Gmbh | Rho kinase inhibitors |
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| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
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| CN105102448B (zh) | 2013-02-28 | 2018-03-06 | 百时美施贵宝公司 | 作为rock1和rock2抑制剂的苯基吡唑衍生物 |
| AR094929A1 (es) | 2013-02-28 | 2015-09-09 | Bristol Myers Squibb Co | Derivados de fenilpirazol como inhibidores potentes de rock1 y rock2 |
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| JP6664632B2 (ja) * | 2013-09-30 | 2020-03-13 | 国立大学法人 東京大学 | アディポネクチン受容体活性化化合物 |
| US10059667B2 (en) | 2014-02-06 | 2018-08-28 | Merck Sharp & Dohme Corp. | Antidiabetic compounds |
| US9832291B2 (en) | 2015-01-12 | 2017-11-28 | Cisco Technology, Inc. | Auto-configurable transport stack |
| CN104803914B (zh) * | 2015-03-05 | 2017-11-14 | 成都理工大学 | 作为Rho激酶抑制剂的六氢氮杂卓氧基苯甲酰胺类化合物 |
| CN110372638B (zh) * | 2018-04-13 | 2023-09-22 | 中国药科大学 | 哌嗪类ampk激动剂及其医药用途 |
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-
2007
- 2007-12-21 EP EP07855342.7A patent/EP2079694B1/en not_active Not-in-force
- 2007-12-21 US US11/963,742 patent/US8012955B2/en active Active
- 2007-12-21 ES ES07855342.7T patent/ES2627221T3/es active Active
- 2007-12-21 CA CA2674237A patent/CA2674237C/en active Active
- 2007-12-21 WO PCT/US2007/088742 patent/WO2008083124A1/en not_active Ceased
- 2007-12-21 JP JP2009544239A patent/JP5650404B2/ja not_active Expired - Fee Related
-
2011
- 2011-07-18 US US13/185,030 patent/US8697727B2/en active Active
-
2014
- 2014-02-25 US US14/189,638 patent/US9181220B2/en active Active
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