JP2012512252A5 - - Google Patents
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- Publication number
- JP2012512252A5 JP2012512252A5 JP2011542339A JP2011542339A JP2012512252A5 JP 2012512252 A5 JP2012512252 A5 JP 2012512252A5 JP 2011542339 A JP2011542339 A JP 2011542339A JP 2011542339 A JP2011542339 A JP 2011542339A JP 2012512252 A5 JP2012512252 A5 JP 2012512252A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- trifluoromethyl
- piperidine
- carboxylic acid
- oxazole
- 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.)
- Withdrawn
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- 150000001875 compounds Chemical class 0.000 claims 47
- 150000003839 salts Chemical class 0.000 claims 36
- -1 alkyl oxadiazole Chemical compound 0.000 claims 33
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 23
- PYCFLCQAJFEELT-UHFFFAOYSA-N 2-phenyl-5-(trifluoromethyl)-1,3-oxazole-4-carboxylic acid Chemical compound O1C(C(F)(F)F)=C(C(=O)O)N=C1C1=CC=CC=C1 PYCFLCQAJFEELT-UHFFFAOYSA-N 0.000 claims 12
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 12
- 125000005907 alkyl ester group Chemical group 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 239000005711 Benzoic acid Substances 0.000 claims 8
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 8
- TVEAZHOLMPKUGM-UHFFFAOYSA-N 2-piperidinobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1N1CCCCC1 TVEAZHOLMPKUGM-UHFFFAOYSA-N 0.000 claims 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical compound ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 claims 6
- ZYLZQIMSYNAILC-UHFFFAOYSA-N 2-piperazin-1-ylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1N1CCNCC1 ZYLZQIMSYNAILC-UHFFFAOYSA-N 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- ASMNZIPDDLMPLY-UHFFFAOYSA-N piperidine;pyridine-2-carboxylic acid Chemical compound C1CCNCC1.OC(=O)C1=CC=CC=N1 ASMNZIPDDLMPLY-UHFFFAOYSA-N 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- SDSDAIQLQREBIR-UHFFFAOYSA-N 1-pyridin-2-yl-3-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound N1=C(C(F)(F)F)C(C(=O)O)=CN1C1=CC=CC=N1 SDSDAIQLQREBIR-UHFFFAOYSA-N 0.000 claims 2
- PFFPTUQGAMYZNZ-UHFFFAOYSA-N 2-[2-(trifluoromethoxy)phenyl]-5-(trifluoromethyl)-1,3-oxazole-4-carboxylic acid Chemical compound O1C(C(F)(F)F)=C(C(=O)O)N=C1C1=CC=CC=C1OC(F)(F)F PFFPTUQGAMYZNZ-UHFFFAOYSA-N 0.000 claims 2
- HJVZMZHBCNRXCD-UHFFFAOYSA-N 2-[4-[5-[[2-phenyl-5-(trifluoromethyl)-1,3-oxazole-4-carbonyl]amino]pyridin-2-yl]piperazin-1-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1N1CCN(C=2N=CC(NC(=O)C3=C(OC(=N3)C=3C=CC=CC=3)C(F)(F)F)=CC=2)CC1 HJVZMZHBCNRXCD-UHFFFAOYSA-N 0.000 claims 2
- NYBJNMCQXDPCBM-UHFFFAOYSA-N 2-phenyl-5-(trifluoromethyl)-n-[6-[4-[2-(trifluoromethyl)phenyl]piperazin-1-yl]pyridin-3-yl]-1,3-oxazole-4-carboxamide Chemical compound FC(F)(F)C=1OC(C=2C=CC=CC=2)=NC=1C(=O)NC(C=N1)=CC=C1N(CC1)CCN1C1=CC=CC=C1C(F)(F)F NYBJNMCQXDPCBM-UHFFFAOYSA-N 0.000 claims 2
- YKQYRBWQTCQQKC-UHFFFAOYSA-N 2-phenyl-5-(trifluoromethyl)-n-[6-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]pyridin-3-yl]-1,3-oxazole-4-carboxamide Chemical compound FC(F)(F)C=1OC(C=2C=CC=CC=2)=NC=1C(=O)NC(C=N1)=CC=C1N(CC1)CCN1C1=CC=CC(C(F)(F)F)=C1 YKQYRBWQTCQQKC-UHFFFAOYSA-N 0.000 claims 2
- BQXSMDFVQCAVID-UHFFFAOYSA-N 2-phenyl-5-(trifluoromethyl)-n-[6-[4-[3-(trifluoromethyl)phenyl]piperidin-1-yl]pyridin-3-yl]-1,3-oxazole-4-carboxamide Chemical compound FC(F)(F)C=1OC(C=2C=CC=CC=2)=NC=1C(=O)NC(C=N1)=CC=C1N(CC1)CCC1C1=CC=CC(C(F)(F)F)=C1 BQXSMDFVQCAVID-UHFFFAOYSA-N 0.000 claims 2
- KPUNYFDILYXQRE-UHFFFAOYSA-N 2-phenyl-5-(trifluoromethyl)-n-[6-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]pyridin-3-yl]-1,3-oxazole-4-carboxamide Chemical compound FC(F)(F)C=1OC(C=2C=CC=CC=2)=NC=1C(=O)NC(C=N1)=CC=C1N(CC1)CCN1C1=CC=C(C(F)(F)F)C=C1 KPUNYFDILYXQRE-UHFFFAOYSA-N 0.000 claims 2
- SQUFJMKDTYFVQO-UHFFFAOYSA-N 2-phenyl-n-[6-(4-phenylpiperazin-1-yl)pyridin-3-yl]-5-(trifluoromethyl)-1,3-oxazole-4-carboxamide Chemical compound FC(F)(F)C=1OC(C=2C=CC=CC=2)=NC=1C(=O)NC(C=N1)=CC=C1N(CC1)CCN1C1=CC=CC=C1 SQUFJMKDTYFVQO-UHFFFAOYSA-N 0.000 claims 2
- FUYFSLADZIFBCQ-UHFFFAOYSA-N 2-phenyl-n-[6-(4-pyrimidin-2-ylpiperazin-1-yl)pyridin-3-yl]-5-(trifluoromethyl)-1,3-oxazole-4-carboxamide Chemical compound FC(F)(F)C=1OC(C=2C=CC=CC=2)=NC=1C(=O)NC(C=N1)=CC=C1N(CC1)CCN1C1=NC=CC=N1 FUYFSLADZIFBCQ-UHFFFAOYSA-N 0.000 claims 2
- FAVATDBDOUESNH-UHFFFAOYSA-N 3-[4-[4-[[2-phenyl-5-(trifluoromethyl)-1,3-oxazole-4-carbonyl]amino]phenyl]piperidin-1-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(N2CCC(CC2)C=2C=CC(NC(=O)C3=C(OC(=N3)C=3C=CC=CC=3)C(F)(F)F)=CC=2)=C1 FAVATDBDOUESNH-UHFFFAOYSA-N 0.000 claims 2
- CFEGXHNBQVTVKM-UHFFFAOYSA-N 3-[4-[5-[[2-phenyl-5-(trifluoromethyl)-1,3-oxazole-4-carbonyl]amino]pyridin-2-yl]piperazin-1-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(N2CCN(CC2)C=2N=CC(NC(=O)C3=C(OC(=N3)C=3C=CC=CC=3)C(F)(F)F)=CC=2)=C1 CFEGXHNBQVTVKM-UHFFFAOYSA-N 0.000 claims 2
- DLNNSFUQXKGREA-UHFFFAOYSA-N 4-[4-[4-[[2-phenyl-5-(trifluoromethyl)-1,3-oxazole-4-carbonyl]amino]phenyl]piperidin-1-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N1CCC(C=2C=CC(NC(=O)C3=C(OC(=N3)C=3C=CC=CC=3)C(F)(F)F)=CC=2)CC1 DLNNSFUQXKGREA-UHFFFAOYSA-N 0.000 claims 2
- BNJMIAOVJXCRCF-UHFFFAOYSA-N 4-[4-[5-[[2-phenyl-5-(trifluoromethyl)-1,3-oxazole-4-carbonyl]amino]pyridin-2-yl]piperazin-1-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N1CCN(C=2N=CC(NC(=O)C3=C(OC(=N3)C=3C=CC=CC=3)C(F)(F)F)=CC=2)CC1 BNJMIAOVJXCRCF-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- FCNWTYAGSIIHRL-UHFFFAOYSA-N ethyl 4-[4-[5-[[1-pyridin-2-yl-3-(trifluoromethyl)pyrazole-4-carbonyl]amino]pyridin-2-yl]piperazin-1-yl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N1CCN(C=2N=CC(NC(=O)C=3C(=NN(C=3)C=3N=CC=CC=3)C(F)(F)F)=CC=2)CC1 FCNWTYAGSIIHRL-UHFFFAOYSA-N 0.000 claims 2
- UZLFMMXJPRIDRZ-UHFFFAOYSA-N ethyl 4-[4-[5-[[2-phenyl-5-(trifluoromethyl)-1,3-oxazole-4-carbonyl]amino]pyridin-2-yl]piperazin-1-yl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N1CCN(C=2N=CC(NC(=O)C3=C(OC(=N3)C=3C=CC=CC=3)C(F)(F)F)=CC=2)CC1 UZLFMMXJPRIDRZ-UHFFFAOYSA-N 0.000 claims 2
- IRSVYBIJXNKBRG-UHFFFAOYSA-N n-[6-[4-(2-methoxyphenyl)piperazin-1-yl]pyridin-3-yl]-2-phenyl-5-(trifluoromethyl)-1,3-oxazole-4-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(C=2N=CC(NC(=O)C3=C(OC(=N3)C=3C=CC=CC=3)C(F)(F)F)=CC=2)CC1 IRSVYBIJXNKBRG-UHFFFAOYSA-N 0.000 claims 2
- BHYRDXWTCLJNDQ-UHFFFAOYSA-N n-[6-[4-(3-methoxyphenyl)piperazin-1-yl]pyridin-3-yl]-2-phenyl-5-(trifluoromethyl)-1,3-oxazole-4-carboxamide Chemical compound COC1=CC=CC(N2CCN(CC2)C=2N=CC(NC(=O)C3=C(OC(=N3)C=3C=CC=CC=3)C(F)(F)F)=CC=2)=C1 BHYRDXWTCLJNDQ-UHFFFAOYSA-N 0.000 claims 2
- YSKBWIRXFWWGIJ-UHFFFAOYSA-N n-[6-[4-(4-fluorophenyl)piperazin-1-yl]pyridin-3-yl]-1-pyridin-2-yl-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1CCN(C=2N=CC(NC(=O)C=3C(=NN(C=3)C=3N=CC=CC=3)C(F)(F)F)=CC=2)CC1 YSKBWIRXFWWGIJ-UHFFFAOYSA-N 0.000 claims 2
- VJVRORHYESEGSV-UHFFFAOYSA-N n-[6-[4-(4-methoxyphenyl)piperazin-1-yl]pyridin-3-yl]-2-phenyl-5-(trifluoromethyl)-1,3-oxazole-4-carboxamide Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2N=CC(NC(=O)C3=C(OC(=N3)C=3C=CC=CC=3)C(F)(F)F)=CC=2)CC1 VJVRORHYESEGSV-UHFFFAOYSA-N 0.000 claims 2
- DFWAKSFJIHBKMB-UHFFFAOYSA-N n-[6-[4-hydroxy-4-[3-(trifluoromethyl)phenyl]piperidin-1-yl]pyridin-3-yl]-2-phenyl-5-(trifluoromethyl)-1,3-oxazole-4-carboxamide Chemical compound C1CC(O)(C=2C=C(C=CC=2)C(F)(F)F)CCN1C(N=C1)=CC=C1NC(=O)C(=C(O1)C(F)(F)F)N=C1C1=CC=CC=C1 DFWAKSFJIHBKMB-UHFFFAOYSA-N 0.000 claims 2
- WEYVCQFUGFRXOM-UHFFFAOYSA-N perazine Chemical compound C1CN(C)CCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 WEYVCQFUGFRXOM-UHFFFAOYSA-N 0.000 claims 2
- 229960002195 perazine Drugs 0.000 claims 2
- RVFVPPONXUZVTJ-UHFFFAOYSA-N piperazine;pyrimidine Chemical compound C1CNCCN1.C1=CN=CN=C1 RVFVPPONXUZVTJ-UHFFFAOYSA-N 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- BIDJDZNQEXQRQK-UHFFFAOYSA-N 2-phenyl-n-[2-[4-(3-propan-2-yl-1,2,4-oxadiazol-5-yl)piperidin-1-yl]pyrimidin-5-yl]-5-(trifluoromethyl)-1,3-oxazole-4-carboxamide Chemical compound CC(C)C1=NOC(C2CCN(CC2)C=2N=CC(NC(=O)C3=C(OC(=N3)C=3C=CC=CC=3)C(F)(F)F)=CN=2)=N1 BIDJDZNQEXQRQK-UHFFFAOYSA-N 0.000 claims 1
- ZFUJGWSHPNBAAF-UHFFFAOYSA-N 2-phenyl-n-[4-[4-(3-propan-2-yl-1,2,4-oxadiazol-5-yl)piperidin-1-yl]phenyl]-5-(trifluoromethyl)-1,3-oxazole-4-carboxamide Chemical compound CC(C)C1=NOC(C2CCN(CC2)C=2C=CC(NC(=O)C3=C(OC(=N3)C=3C=CC=CC=3)C(F)(F)F)=CC=2)=N1 ZFUJGWSHPNBAAF-UHFFFAOYSA-N 0.000 claims 1
- JZTAYPMFFRPCGR-UHFFFAOYSA-N 2-phenyl-n-[6-[3-(3-propan-2-yl-1,2,4-oxadiazol-5-yl)pyrrolidin-1-yl]pyridin-3-yl]-5-(trifluoromethyl)-1,3-oxazole-4-carboxamide Chemical compound CC(C)C1=NOC(C2CN(CC2)C=2N=CC(NC(=O)C3=C(OC(=N3)C=3C=CC=CC=3)C(F)(F)F)=CC=2)=N1 JZTAYPMFFRPCGR-UHFFFAOYSA-N 0.000 claims 1
- YSSGWMIUYKMVDU-QFIPXVFZSA-N 4-[(3s)-3-[4-[[2-phenyl-5-(trifluoromethyl)-1,3-oxazole-4-carbonyl]amino]phenoxy]pyrrolidin-1-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N1C[C@@H](OC=2C=CC(NC(=O)C3=C(OC(=N3)C=3C=CC=CC=3)C(F)(F)F)=CC=2)CC1 YSSGWMIUYKMVDU-QFIPXVFZSA-N 0.000 claims 1
- YSSGWMIUYKMVDU-UHFFFAOYSA-N 4-[3-[4-[[2-phenyl-5-(trifluoromethyl)-1,3-oxazole-4-carbonyl]amino]phenoxy]pyrrolidin-1-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N1CC(OC=2C=CC(NC(=O)C3=C(OC(=N3)C=3C=CC=CC=3)C(F)(F)F)=CC=2)CC1 YSSGWMIUYKMVDU-UHFFFAOYSA-N 0.000 claims 1
- PJGWDEIXVQQGHQ-UHFFFAOYSA-N 4-[4-[4-[(5-ethyl-2-phenyl-1,3-oxazole-4-carbonyl)amino]phenyl]piperidin-1-yl]benzoic acid Chemical compound CCC=1OC(C=2C=CC=CC=2)=NC=1C(=O)NC(C=C1)=CC=C1C(CC1)CCN1C1=CC=C(C(O)=O)C=C1 PJGWDEIXVQQGHQ-UHFFFAOYSA-N 0.000 claims 1
- GCGZHOKMJIEQDC-UHFFFAOYSA-N 4-cyclopropyloxadiazole;piperidine Chemical compound C1CCNCC1.C1CC1C1=CON=N1 GCGZHOKMJIEQDC-UHFFFAOYSA-N 0.000 claims 1
- RUTXQXPVSKGUCH-UHFFFAOYSA-N 4-propyloxadiazole Chemical compound CCCC1=CON=N1 RUTXQXPVSKGUCH-UHFFFAOYSA-N 0.000 claims 1
- PZLZNPDGRCCEHL-UHFFFAOYSA-N 6-[4-[4-[(4-phenylthiophene-2-carbonyl)amino]phenyl]piperidin-1-yl]pyridine-3-carboxylic acid Chemical compound N1=CC(C(=O)O)=CC=C1N1CCC(C=2C=CC(NC(=O)C=3SC=C(C=3)C=3C=CC=CC=3)=CC=2)CC1 PZLZNPDGRCCEHL-UHFFFAOYSA-N 0.000 claims 1
- JTRIRWFHXCNJRC-UHFFFAOYSA-N 6-[4-[4-[[2-phenyl-5-(trifluoromethyl)-1,3-oxazole-4-carbonyl]amino]phenyl]piperidin-1-yl]pyridine-3-carboxylic acid Chemical compound N1=CC(C(=O)O)=CC=C1N1CCC(C=2C=CC(NC(=O)C3=C(OC(=N3)C=3C=CC=CC=3)C(F)(F)F)=CC=2)CC1 JTRIRWFHXCNJRC-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 229910052739 hydrogen Chemical group 0.000 claims 1
- 239000001257 hydrogen Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- WHWPJUQTGCHISO-UHFFFAOYSA-N O=C(c1ccc[s]1)Nc1ccccc1 Chemical compound O=C(c1ccc[s]1)Nc1ccccc1 WHWPJUQTGCHISO-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13815708P | 2008-12-17 | 2008-12-17 | |
| US61/138,157 | 2008-12-17 | ||
| PCT/US2009/068048 WO2010077861A1 (en) | 2008-12-17 | 2009-12-15 | Inhibitors of diacylglycerol aclytransferase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012512252A JP2012512252A (ja) | 2012-05-31 |
| JP2012512252A5 true JP2012512252A5 (https=) | 2013-02-07 |
Family
ID=42241316
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011542339A Withdrawn JP2012512252A (ja) | 2008-12-17 | 2009-12-15 | ジアシルグリセロールアシルトランスフェラーゼの阻害剤 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8211914B2 (https=) |
| EP (1) | EP2378878A4 (https=) |
| JP (1) | JP2012512252A (https=) |
| CN (1) | CN102245024A (https=) |
| AU (1) | AU2009333333A1 (https=) |
| CA (1) | CA2745445A1 (https=) |
| IL (1) | IL213164A0 (https=) |
| WO (1) | WO2010077861A1 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8115011B2 (en) * | 2007-05-22 | 2012-02-14 | Madrigal Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| US8153644B2 (en) * | 2007-05-22 | 2012-04-10 | Madrigal Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| US8211884B2 (en) * | 2008-08-06 | 2012-07-03 | Madrigal Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| US8324385B2 (en) * | 2008-10-30 | 2012-12-04 | Madrigal Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| JP2012512252A (ja) | 2008-12-17 | 2012-05-31 | ブイアイエイ・ファーマシューティカルズ・インコーポレーテッド | ジアシルグリセロールアシルトランスフェラーゼの阻害剤 |
| WO2012173219A1 (ja) * | 2011-06-17 | 2012-12-20 | 第一三共株式会社 | 新規ビアリールエーテル誘導体 |
| RU2014141046A (ru) | 2012-04-13 | 2016-04-27 | Мицубиси Танабе Фарма Корпорейшн | Амидопиридиновое производное и его применение |
| CR20170077A (es) | 2014-08-04 | 2017-06-26 | Nuevolution As | Derivados de heterociclilo opcionalmente condensados de pirimidina útiles para el tratamiento de enfermedades inflamatorias, metabólicas, oncológicas y autoinmunitarias |
| AR109179A1 (es) | 2016-08-19 | 2018-11-07 | Pfizer | Inhibidores de diacilglicerol aciltransferasa 2 |
| UY38994A (es) | 2019-12-20 | 2021-07-30 | Nuevolution As | Compuestos activos frente a receptores nucleares |
| MX2022007265A (es) | 2019-12-20 | 2022-09-09 | Nuevolution As | Compuestos activos frente a receptores nucleares. |
| AU2021245397A1 (en) | 2020-03-31 | 2022-10-20 | Nuevolution A/S | Compounds active towards nuclear receptors |
| WO2021198956A1 (en) | 2020-03-31 | 2021-10-07 | Nuevolution A/S | Compounds active towards nuclear receptors |
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| US3250771A (en) * | 1962-12-17 | 1966-05-10 | Geigy Chem Corp | 5-monocarbocyclic aryl-n-lower alkyl-2-pyrrolidine carboxylic acid, esters, amides and derivatives thereof |
| DE2337461A1 (de) * | 1973-07-24 | 1975-02-06 | Boehringer Mannheim Gmbh | Neue indolderivate und verfahren zu deren herstellung |
| US4066654A (en) * | 1975-04-16 | 1978-01-03 | G. D. Searle & Co. | 1-triarylalkyl-4-phenyl-4-piperidine carboxylic acids and derivatives |
| US6495558B1 (en) * | 1999-01-22 | 2002-12-17 | Amgen Inc. | Kinase inhibitors |
| MXPA01008142A (es) | 1999-02-10 | 2003-07-21 | Welfide Corp | Compuestos de amida, y uso medicinal de los mismos. |
| US6756374B2 (en) * | 2001-01-22 | 2004-06-29 | Hoffmann-La Roche Inc. | Diaminothiazoles having antiproliferative activity |
| AU2002333456B2 (en) | 2001-08-31 | 2008-07-17 | Sanofi-Aventis Deutschland Gmbh | Diaryl cycloalkyl derivatives, method for producing the same and the use thereof as PPAR activators |
| AU2003261935A1 (en) | 2002-09-06 | 2004-03-29 | Takeda Pharmaceutical Company Limited | Furan or thiophene derivative and medicinal use thereof |
| RU2342388C2 (ru) * | 2002-11-22 | 2008-12-27 | Джапан Тобакко Инк. | Конденсированные бициклические азотсодержащие гетероциклы, обладающие dgat ингибирующим действием |
| DE10308353A1 (de) * | 2003-02-27 | 2004-12-02 | Aventis Pharma Deutschland Gmbh | Diarylcycloalkylderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US7148246B2 (en) * | 2003-02-27 | 2006-12-12 | Sanofi-Aventis Deutschland Gmbh | Cycloalkyl derivatives having bioisosteric carboxylic acid groups, processes for their preparation and their use as pharmaceuticals |
| AU2006210056A1 (en) * | 2005-02-07 | 2006-08-10 | F. Hoffmann-La Roche Ag | Inhibitors of diacylglycerol acyltransferase (DGAT) |
| AU2006258917A1 (en) | 2005-06-11 | 2006-12-21 | Astrazeneca Ab | Oxadiazole derivatives as DGAT inhibitors |
| CN101316844A (zh) * | 2005-11-28 | 2008-12-03 | 霍夫曼-拉罗奇有限公司 | 二酰甘油酰基转移酶(dgat)抑制剂 |
| KR20080063865A (ko) | 2005-11-28 | 2008-07-07 | 에프. 호프만-라 로슈 아게 | 다이아실글리세롤 아실전이효소(ｄｇａｔ)의 저해제 |
| US8115011B2 (en) * | 2007-05-22 | 2012-02-14 | Madrigal Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| US20090099201A1 (en) * | 2007-05-22 | 2009-04-16 | David Robert Bolin | Diacylglycerol Acyltransferase Inhibitors |
| US8153644B2 (en) * | 2007-05-22 | 2012-04-10 | Madrigal Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| US8058299B2 (en) * | 2007-05-22 | 2011-11-15 | Via Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| BRPI0811947A2 (pt) | 2007-05-22 | 2014-11-11 | Via Pharmaceuticals Inc | Composto, processo para a preparação de um composto, composição farmacêutica, uso de um composto e método de tratamento de obesidade, diabetes do tipo ii, dislipidemia ou síndrome metabólica |
| US8211884B2 (en) | 2008-08-06 | 2012-07-03 | Madrigal Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| US20110224193A1 (en) * | 2008-11-19 | 2011-09-15 | Merck Sharp & Dohme Corp | Inhibitors of diacylglycerol acyltransferase |
| AU2009322774A1 (en) * | 2008-12-03 | 2011-06-30 | Via Pharmaceuticals, Inc | Inhibitors of diacylglycerol acyltransferase |
| JP2012512252A (ja) | 2008-12-17 | 2012-05-31 | ブイアイエイ・ファーマシューティカルズ・インコーポレーテッド | ジアシルグリセロールアシルトランスフェラーゼの阻害剤 |
-
2009
- 2009-12-15 JP JP2011542339A patent/JP2012512252A/ja not_active Withdrawn
- 2009-12-15 WO PCT/US2009/068048 patent/WO2010077861A1/en not_active Ceased
- 2009-12-15 US US12/638,244 patent/US8211914B2/en not_active Expired - Fee Related
- 2009-12-15 EP EP09836834A patent/EP2378878A4/en not_active Withdrawn
- 2009-12-15 AU AU2009333333A patent/AU2009333333A1/en not_active Abandoned
- 2009-12-15 CN CN2009801505265A patent/CN102245024A/zh active Pending
- 2009-12-15 CA CA2745445A patent/CA2745445A1/en not_active Abandoned
-
2011
- 2011-05-26 IL IL213164A patent/IL213164A0/en unknown
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