JP2011527665A5 - - Google Patents
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- Publication number
- JP2011527665A5 JP2011527665A5 JP2011506436A JP2011506436A JP2011527665A5 JP 2011527665 A5 JP2011527665 A5 JP 2011527665A5 JP 2011506436 A JP2011506436 A JP 2011506436A JP 2011506436 A JP2011506436 A JP 2011506436A JP 2011527665 A5 JP2011527665 A5 JP 2011527665A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- piperidin
- trifluoromethyl
- carboxamide
- yloxy
- 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
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- 125000000217 alkyl group Chemical group 0.000 claims description 200
- 150000001875 compounds Chemical class 0.000 claims description 71
- -1 azepan-4-yl Chemical group 0.000 claims description 48
- 125000004122 cyclic group Chemical group 0.000 claims description 41
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 150000001204 N-oxides Chemical class 0.000 claims description 6
- 150000001721 carbon Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 6
- 239000000651 prodrug Substances 0.000 claims description 6
- 229940002612 prodrug Drugs 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- QFHBDWSBBWDESG-UHFFFAOYSA-N 2-[(4-fluorophenyl)methyl]-n-[1-(pyridin-3-ylmethyl)piperidin-4-yl]-3,4-dihydro-1h-isoquinoline-7-carboxamide Chemical compound C1=CC(F)=CC=C1CN1CC2=CC(C(=O)NC3CCN(CC=4C=NC=CC=4)CC3)=CC=C2CC1 QFHBDWSBBWDESG-UHFFFAOYSA-N 0.000 claims description 4
- MNMSQMPLOFCCAI-UHFFFAOYSA-N 2-[(4-fluorophenyl)methyl]-n-[1-[[4-(trifluoromethyl)phenyl]methyl]piperidin-4-yl]-3,4-dihydro-1h-isoquinoline-7-carboxamide Chemical compound C1=CC(F)=CC=C1CN1CC2=CC(C(=O)NC3CCN(CC=4C=CC(=CC=4)C(F)(F)F)CC3)=CC=C2CC1 MNMSQMPLOFCCAI-UHFFFAOYSA-N 0.000 claims description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
- 125000005605 benzo group Chemical group 0.000 claims description 4
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 4
- PECFFCAMVONDOD-UHFFFAOYSA-N n-[1-[(4-cyanophenyl)methyl]piperidin-4-yl]-2-[(4-fluorophenyl)methyl]-3,4-dihydro-1h-isoquinoline-7-carboxamide Chemical compound C1=CC(F)=CC=C1CN1CC2=CC(C(=O)NC3CCN(CC=4C=CC(=CC=4)C#N)CC3)=CC=C2CC1 PECFFCAMVONDOD-UHFFFAOYSA-N 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 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
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- GURNDTHBDGDGPI-UHFFFAOYSA-N 2-[(4-cyanophenyl)methyl]-n-[1-(pyridin-3-ylmethyl)piperidin-4-yl]-3,4-dihydro-1h-isoquinoline-7-carboxamide Chemical compound C=1C=C2CCN(CC=3C=CC(=CC=3)C#N)CC2=CC=1C(=O)NC(CC1)CCN1CC1=CC=CN=C1 GURNDTHBDGDGPI-UHFFFAOYSA-N 0.000 claims description 2
- SYODVRZVUGRYFT-UHFFFAOYSA-N 2-[(4-cyanophenyl)methyl]-n-[1-[(4-cyanophenyl)methyl]piperidin-4-yl]-3,4-dihydro-1h-isoquinoline-7-carboxamide Chemical compound C=1C=C2CCN(CC=3C=CC(=CC=3)C#N)CC2=CC=1C(=O)NC(CC1)CCN1CC1=CC=C(C#N)C=C1 SYODVRZVUGRYFT-UHFFFAOYSA-N 0.000 claims description 2
- POEQQIDCVAGZPC-UHFFFAOYSA-N 2-[(4-cyanophenyl)methyl]-n-[1-[[4-(trifluoromethyl)phenyl]methyl]piperidin-4-yl]-3,4-dihydro-1h-isoquinoline-7-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1CCC(NC(=O)C=2C=C3CN(CC=4C=CC(=CC=4)C#N)CCC3=CC=2)CC1 POEQQIDCVAGZPC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- IZODJALCKQEYNJ-UHFFFAOYSA-N 4-N-[1-[(4-cyanophenyl)methyl]piperidin-4-yl]benzene-1,4-dicarboxamide Chemical compound C(C1=CC=C(C(=O)N)C=C1)(=O)NC1CCN(CC1)CC1=CC=C(C=C1)C#N IZODJALCKQEYNJ-UHFFFAOYSA-N 0.000 claims description 2
- CVRCQOGRLOHSGK-UHFFFAOYSA-N 4-N-[1-[[4-(trifluoromethyl)phenyl]methyl]piperidin-4-yl]benzene-1,4-dicarboxamide Chemical compound C(C1=CC=C(C(=O)N)C=C1)(=O)NC1CCN(CC1)CC1=CC=C(C=C1)C(F)(F)F CVRCQOGRLOHSGK-UHFFFAOYSA-N 0.000 claims description 2
- XNNVNVVMALYLCH-UHFFFAOYSA-N 4-[2-[6-[1-[4-(trifluoromethyl)phenyl]piperidin-4-yl]oxy-1,3-benzoxazole-2-carbonyl]-2,5-diazabicyclo[2.2.1]heptane-5-carbonyl]benzonitrile Chemical compound C1=CC(C(F)(F)F)=CC=C1N1CCC(OC=2C=C3OC(=NC3=CC=2)C(=O)N2C3CC(N(C3)C(=O)C=3C=CC(=CC=3)C#N)C2)CC1 XNNVNVVMALYLCH-UHFFFAOYSA-N 0.000 claims description 2
- ZYGWRSOHCPOIBR-UHFFFAOYSA-N 4-[[2-[6-[1-[4-(trifluoromethyl)phenyl]piperidin-4-yl]oxy-1,3-benzoxazole-2-carbonyl]-2,5-diazabicyclo[2.2.1]heptan-5-yl]methyl]benzonitrile Chemical compound C1=CC(C(F)(F)F)=CC=C1N1CCC(OC=2C=C3OC(=NC3=CC=2)C(=O)N2C3CC(N(C3)CC=3C=CC(=CC=3)C#N)C2)CC1 ZYGWRSOHCPOIBR-UHFFFAOYSA-N 0.000 claims description 2
- 102100036009 5'-AMP-activated protein kinase catalytic subunit alpha-2 Human genes 0.000 claims description 2
- 101000783681 Homo sapiens 5'-AMP-activated protein kinase catalytic subunit alpha-2 Proteins 0.000 claims description 2
- ADVKAPHTRUEKKB-UHFFFAOYSA-N [5-(pyridin-4-ylmethyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-[6-[1-[4-(trifluoromethyl)phenyl]piperidin-4-yl]oxy-1,3-benzoxazol-2-yl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1N1CCC(OC=2C=C3OC(=NC3=CC=2)C(=O)N2C3CC(N(C3)CC=3C=CN=CC=3)C2)CC1 ADVKAPHTRUEKKB-UHFFFAOYSA-N 0.000 claims description 2
- 230000003213 activating effect Effects 0.000 claims description 2
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 2
- 230000037361 pathway Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 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
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 238000000338 in vitro Methods 0.000 claims 1
- 0 C*(C)c1ccccc1 Chemical compound C*(C)c1ccccc1 0.000 description 19
- 125000004093 cyano group Chemical group *C#N 0.000 description 13
- 125000001188 haloalkyl group Chemical group 0.000 description 9
- 125000003709 fluoroalkyl group Chemical group 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
Applications Claiming Priority (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4739908P | 2008-04-23 | 2008-04-23 | |
| US61/047,399 | 2008-04-23 | ||
| US4899708P | 2008-04-30 | 2008-04-30 | |
| US61/048,997 | 2008-04-30 | ||
| US5403508P | 2008-05-16 | 2008-05-16 | |
| US61/054,035 | 2008-05-16 | ||
| US5493408P | 2008-05-21 | 2008-05-21 | |
| US61/054,934 | 2008-05-21 | ||
| US5885408P | 2008-06-04 | 2008-06-04 | |
| US61/058,854 | 2008-06-04 | ||
| US7816608P | 2008-07-03 | 2008-07-03 | |
| US7820908P | 2008-07-03 | 2008-07-03 | |
| US7818008P | 2008-07-03 | 2008-07-03 | |
| US61/078,180 | 2008-07-03 | ||
| US61/078,209 | 2008-07-03 | ||
| US61/078,166 | 2008-07-03 | ||
| PCT/US2009/041448 WO2009132136A1 (en) | 2008-04-23 | 2009-04-22 | Carboxamide compounds for the treatment of metabolic disorders |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014184930A Division JP5964906B2 (ja) | 2008-04-23 | 2014-09-11 | 代謝障害の処置のためのカルボキサミド化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011527665A JP2011527665A (ja) | 2011-11-04 |
| JP2011527665A5 true JP2011527665A5 (enExample) | 2012-06-07 |
| JP5658138B2 JP5658138B2 (ja) | 2015-01-21 |
Family
ID=40756385
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011506436A Expired - Fee Related JP5658138B2 (ja) | 2008-04-23 | 2009-04-22 | 代謝障害の処置のためのカルボキサミド化合物 |
| JP2014184930A Expired - Fee Related JP5964906B2 (ja) | 2008-04-23 | 2014-09-11 | 代謝障害の処置のためのカルボキサミド化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014184930A Expired - Fee Related JP5964906B2 (ja) | 2008-04-23 | 2014-09-11 | 代謝障害の処置のためのカルボキサミド化合物 |
Country Status (15)
| Country | Link |
|---|---|
| US (6) | US8314107B2 (enExample) |
| EP (1) | EP2276761B1 (enExample) |
| JP (2) | JP5658138B2 (enExample) |
| KR (1) | KR101662333B1 (enExample) |
| CN (4) | CN106928211B (enExample) |
| AU (1) | AU2009240643B2 (enExample) |
| BR (1) | BRPI0911681B8 (enExample) |
| CA (1) | CA2722139C (enExample) |
| EA (1) | EA021119B1 (enExample) |
| ES (1) | ES2552549T3 (enExample) |
| IL (1) | IL208513A0 (enExample) |
| MX (1) | MX2010011288A (enExample) |
| NZ (1) | NZ588652A (enExample) |
| WO (1) | WO2009132136A1 (enExample) |
| ZA (1) | ZA201007127B (enExample) |
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| WO2008083124A1 (en) | 2006-12-28 | 2008-07-10 | Rigel Pharmaceuticals, Inc. | N-substituted-heterocycloalkyloxybenzamide compounds and methods of use |
| JP5544296B2 (ja) | 2007-11-16 | 2014-07-09 | ライジェル ファーマシューティカルズ， インコーポレイテッド | 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 |
| ES2553340T3 (es) * | 2007-12-12 | 2015-12-07 | Rigel Pharmaceuticals, Inc. | Compuestos de carboxamida, sulfonamida y amina para trastornos metabólicos |
| JP5658138B2 (ja) | 2008-04-23 | 2015-01-21 | ライジェル ファーマシューティカルズ， インコーポレイテッド | 代謝障害の処置のためのカルボキサミド化合物 |
| US8273900B2 (en) | 2008-08-07 | 2012-09-25 | Novartis Ag | Organic compounds |
| CN102365275B (zh) * | 2009-01-28 | 2014-09-24 | 里格尔药品股份有限公司 | 羧酰胺化合物及其使用方法 |
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| JPWO2011142359A1 (ja) * | 2010-05-10 | 2013-07-22 | 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 |
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| US20180183429A1 (en) * | 2016-12-28 | 2018-06-28 | Sirectifier Electronic Co., Ltd. | Integrated series schottky diode rectifier |
| JP7065589B2 (ja) | 2017-10-31 | 2022-05-12 | 株式会社明治 | ＩＬ－１β血清濃度低下用発酵乳、ＣＸＣＬ１血清濃度低下用発酵乳、癌に伴うＩＬ－１βの過度な血清濃度上昇の抑制用発酵乳、または、癌に伴うＣＸＣＬ１の過度な血清濃度上昇の抑制用発酵乳 |
| 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 |
| CN110372574A (zh) * | 2018-04-13 | 2019-10-25 | 中国药科大学 | 哌啶类ampk激动剂及其医药用途 |
| KR102364681B1 (ko) | 2020-04-10 | 2022-02-18 | 엘지전자 주식회사 | 디퓨저 및 이를 포함하는 헤어드라이어 |
| CN116323608A (zh) | 2020-05-19 | 2023-06-23 | 卡尔优普公司 | Ampk活化剂 |
| EP4172162A4 (en) | 2020-06-26 | 2024-08-07 | Kallyope, Inc. | AMPK ACTIVATORS |
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