JP2010536750A5 - - Google Patents
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- JP2010536750A5 JP2010536750A5 JP2010521002A JP2010521002A JP2010536750A5 JP 2010536750 A5 JP2010536750 A5 JP 2010536750A5 JP 2010521002 A JP2010521002 A JP 2010521002A JP 2010521002 A JP2010521002 A JP 2010521002A JP 2010536750 A5 JP2010536750 A5 JP 2010536750A5
- Authority
- JP
- Japan
- Prior art keywords
- azabicyclo
- trimethyl
- octane
- sulfonyl
- ester
- 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- Withdrawn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 description 28
- 150000002148 esters Chemical class 0.000 claims description 18
- 229940002612 prodrug Drugs 0.000 claims description 18
- 239000000651 prodrug Substances 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000012453 solvate Substances 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 208000008589 Obesity Diseases 0.000 claims description 14
- 235000020824 obesity Nutrition 0.000 claims description 14
- 239000003112 inhibitor Substances 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 11
- -1 sulfonylamino, substituted carbonylamino Chemical group 0.000 claims description 10
- 102000004277 11-beta-hydroxysteroid dehydrogenases Human genes 0.000 claims description 8
- 108090000874 11-beta-hydroxysteroid dehydrogenases Proteins 0.000 claims description 8
- 102000012336 Cholesterol Ester Transfer Proteins Human genes 0.000 claims description 8
- 108010061846 Cholesterol Ester Transfer Proteins Proteins 0.000 claims description 8
- 102100030643 Hydroxycarboxylic acid receptor 2 Human genes 0.000 claims description 8
- 101710125793 Hydroxycarboxylic acid receptor 2 Proteins 0.000 claims description 8
- 102000007330 LDL Lipoproteins Human genes 0.000 claims description 8
- 108010007622 LDL Lipoproteins Proteins 0.000 claims description 8
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 8
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 229940124597 therapeutic agent Drugs 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 6
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
- 229940122502 Cholesterol absorption inhibitor Drugs 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 4
- 229940125922 IBAT inhibitor Drugs 0.000 claims description 4
- 206010022489 Insulin Resistance Diseases 0.000 claims description 4
- 206010033645 Pancreatitis Diseases 0.000 claims description 4
- 239000012190 activator Substances 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 4
- 239000000556 agonist Substances 0.000 claims description 4
- 239000000883 anti-obesity agent Substances 0.000 claims description 4
- 239000003472 antidiabetic agent Substances 0.000 claims description 4
- 229940125708 antidiabetic agent Drugs 0.000 claims description 4
- 229940125710 antiobesity agent Drugs 0.000 claims description 4
- 239000003613 bile acid Substances 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 235000012000 cholesterol Nutrition 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 4
- 235000021323 fish oil Nutrition 0.000 claims description 4
- 150000002632 lipids Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 235000002378 plant sterols Nutrition 0.000 claims description 4
- FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical class C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 claims description 4
- 239000002516 radical scavenger Substances 0.000 claims description 4
- 239000003981 vehicle Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- WVBTUIPJSOKKNR-UHFFFAOYSA-N 1-[2-[[4-[5-[(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)sulfonyl]thiophen-2-yl]pyrimidin-2-yl]amino]ethyl]imidazolidin-2-one Chemical compound C1C(C)(C)CC(C)(C2)CC1N2S(=O)(=O)C(S1)=CC=C1C(N=1)=CC=NC=1NCCN1CCNC1=O WVBTUIPJSOKKNR-UHFFFAOYSA-N 0.000 claims description 2
- KAFKJWKZTUZLKI-UHFFFAOYSA-N 1-[4-[(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)sulfonyl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)N1C(CC(C)(C)C2)CC2(C)C1 KAFKJWKZTUZLKI-UHFFFAOYSA-N 0.000 claims description 2
- GZRZZESETIUWLM-UHFFFAOYSA-N 2,2,2-trifluoro-1-[8-[(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)sulfonyl]-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound C1CN(C(=O)C(F)(F)F)CC2=C1C=CC=C2S(=O)(=O)N(C1)C2CC1(C)CC(C)(C)C2 GZRZZESETIUWLM-UHFFFAOYSA-N 0.000 claims description 2
- ZBVVLPXPDHRGOE-UHFFFAOYSA-N 3,3,5-trimethyl-7-(2,3,5,6-tetramethylphenyl)sulfonyl-7-azabicyclo[3.2.1]octane Chemical compound CC1=CC(C)=C(C)C(S(=O)(=O)N2C3CC(CC(C)(C)C3)(C)C2)=C1C ZBVVLPXPDHRGOE-UHFFFAOYSA-N 0.000 claims description 2
- JABJHRXQRZQLCF-UHFFFAOYSA-N 3,3,5-trimethyl-7-(2-nitrophenyl)sulfonyl-7-azabicyclo[3.2.1]octane Chemical compound C1C(C)(C)CC(C)(C2)CC1N2S(=O)(=O)C1=CC=CC=C1[N+]([O-])=O JABJHRXQRZQLCF-UHFFFAOYSA-N 0.000 claims description 2
- YYUJIFQDKZTFLM-UHFFFAOYSA-N 3,3,5-trimethyl-7-(3-nitrophenyl)sulfonyl-7-azabicyclo[3.2.1]octane Chemical compound C1C(C)(C)CC(C)(C2)CC1N2S(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 YYUJIFQDKZTFLM-UHFFFAOYSA-N 0.000 claims description 2
- MARHYADBQYWBAV-UHFFFAOYSA-N 3,3,5-trimethyl-7-[2-(trifluoromethyl)phenyl]sulfonyl-7-azabicyclo[3.2.1]octane Chemical compound C1C(C)(C)CC(C)(C2)CC1N2S(=O)(=O)C1=CC=CC=C1C(F)(F)F MARHYADBQYWBAV-UHFFFAOYSA-N 0.000 claims description 2
- ZBSYCERXWWNIEZ-UHFFFAOYSA-N 3-[(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)sulfonyl]benzoic acid Chemical compound C1C(C)(C)CC(C)(C2)CC1N2S(=O)(=O)C1=CC=CC(C(O)=O)=C1 ZBSYCERXWWNIEZ-UHFFFAOYSA-N 0.000 claims description 2
- URKTVVCTXQBKEG-ZBEGNZNMSA-N 3-[[(1s,5r)-3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl]sulfonyl]-2h-pyrazolo[3,4-b]pyridine Chemical compound C1=CC=C2C(S(=O)(=O)N3C[C@]4(C[C@@]3(CC(C)(C)C4)[H])C)=NNC2=N1 URKTVVCTXQBKEG-ZBEGNZNMSA-N 0.000 claims description 2
- ZFKKFYFTGRHWSA-UHFFFAOYSA-N 4-[(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)sulfonyl]aniline Chemical compound C1C(C)(C)CC(C)(C2)CC1N2S(=O)(=O)C1=CC=C(N)C=C1 ZFKKFYFTGRHWSA-UHFFFAOYSA-N 0.000 claims description 2
- HTLNNHARPMAHKG-UHFFFAOYSA-N 4-[(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)sulfonyl]benzoic acid Chemical compound C1C(C)(C)CC(C)(C2)CC1N2S(=O)(=O)C1=CC=C(C(O)=O)C=C1 HTLNNHARPMAHKG-UHFFFAOYSA-N 0.000 claims description 2
- COLVNLJTOAVVDM-UHFFFAOYSA-N 5-[2-ethoxy-5-[(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)sulfonyl]phenyl]-1-methyl-3-propyl-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound C1C(CC(C)(C)C2)(C)CC2N1S(=O)(=O)C1=CC=C(OCC)C(C=2NC3=C(C(N=2)=O)N(C)N=C3CCC)=C1 COLVNLJTOAVVDM-UHFFFAOYSA-N 0.000 claims description 2
- PGGQZJRCVBXLJZ-UHFFFAOYSA-N 5-phenyl-2-[4-[(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)sulfonyl]phenyl]-1,3-oxazole Chemical compound C1C(C)(C)CC(C)(C2)CC1N2S(=O)(=O)C(C=C1)=CC=C1C(O1)=NC=C1C1=CC=CC=C1 PGGQZJRCVBXLJZ-UHFFFAOYSA-N 0.000 claims description 2
- MDJRECKUZREDLA-UHFFFAOYSA-N 6-(5-tert-butyl-2-methylphenyl)sulfonyl-6-azabicyclo[3.2.1]octane Chemical compound CC1=CC=C(C(C)(C)C)C=C1S(=O)(=O)N1C(CCC2)CC2C1 MDJRECKUZREDLA-UHFFFAOYSA-N 0.000 claims description 2
- UFIYWUYYLFQPKA-UHFFFAOYSA-N 6-[(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)sulfonyl]-1h-benzo[cd]indol-2-one Chemical compound N1C(=O)C2=CC=CC3=C2C1=CC=C3S(=O)(=O)N(C1)C2CC1(C)CC(C)(C)C2 UFIYWUYYLFQPKA-UHFFFAOYSA-N 0.000 claims description 2
- NBPPYFOIQNMSKM-UHFFFAOYSA-N 6-[(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)sulfonyl]-3h-1,3-benzoxazol-2-one Chemical compound C1=C2NC(=O)OC2=CC(S(=O)(=O)N2C3CC(CC(C)(C)C3)(C2)C)=C1 NBPPYFOIQNMSKM-UHFFFAOYSA-N 0.000 claims description 2
- FDDWLPBXZBOSPT-UHFFFAOYSA-N 7-(2,3-dichlorophenyl)sulfonyl-3,3,5-trimethyl-7-azabicyclo[3.2.1]octane Chemical compound C1C(C)(C)CC(C)(C2)CC1N2S(=O)(=O)C1=CC=CC(Cl)=C1Cl FDDWLPBXZBOSPT-UHFFFAOYSA-N 0.000 claims description 2
- PODWDIABNHWHEZ-UHFFFAOYSA-N 7-(2,4-difluorophenyl)sulfonyl-3,3,5-trimethyl-7-azabicyclo[3.2.1]octane Chemical compound C1C(C)(C)CC(C)(C2)CC1N2S(=O)(=O)C1=CC=C(F)C=C1F PODWDIABNHWHEZ-UHFFFAOYSA-N 0.000 claims description 2
- IEGRNONCHQMKBV-UHFFFAOYSA-N 7-(2,5-dibromophenyl)sulfonyl-3,3,5-trimethyl-7-azabicyclo[3.2.1]octane Chemical compound C1C(C)(C)CC(C)(C2)CC1N2S(=O)(=O)C1=CC(Br)=CC=C1Br IEGRNONCHQMKBV-UHFFFAOYSA-N 0.000 claims description 2
- WLVYFAQQCDUZRS-UHFFFAOYSA-N 7-(2,5-dichlorophenyl)sulfonyl-3,3,5-trimethyl-7-azabicyclo[3.2.1]octane Chemical compound C1C(C)(C)CC(C)(C2)CC1N2S(=O)(=O)C1=CC(Cl)=CC=C1Cl WLVYFAQQCDUZRS-UHFFFAOYSA-N 0.000 claims description 2
- DBBDJJUNLNFEII-UHFFFAOYSA-N 7-(2,5-dimethylphenyl)sulfonyl-3,3,5-trimethyl-7-azabicyclo[3.2.1]octane Chemical compound CC1=CC=C(C)C(S(=O)(=O)N2C3CC(CC(C)(C)C3)(C)C2)=C1 DBBDJJUNLNFEII-UHFFFAOYSA-N 0.000 claims description 2
- YEKYRGXRVHQYEW-UHFFFAOYSA-N 7-(3,4-difluorophenyl)sulfonyl-3,3,5-trimethyl-7-azabicyclo[3.2.1]octane Chemical compound C1C(C)(C)CC(C)(C2)CC1N2S(=O)(=O)C1=CC=C(F)C(F)=C1 YEKYRGXRVHQYEW-UHFFFAOYSA-N 0.000 claims description 2
- PIGNSXKZJHBQPT-UHFFFAOYSA-N 7-(4-ethoxyphenyl)sulfonyl-3,3,5-trimethyl-7-azabicyclo[3.2.1]octane Chemical compound C1=CC(OCC)=CC=C1S(=O)(=O)N1C(CC(C)(C)C2)CC2(C)C1 PIGNSXKZJHBQPT-UHFFFAOYSA-N 0.000 claims description 2
- TZVKMTAZWTZMBU-UHFFFAOYSA-N 7-(4-methoxyphenyl)sulfonyl-3,3,5-trimethyl-7-azabicyclo[3.2.1]octane Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C(CC(C)(C)C2)CC2(C)C1 TZVKMTAZWTZMBU-UHFFFAOYSA-N 0.000 claims description 2
- MTUPOGYWPRWVBX-UHFFFAOYSA-N 7-(4-tert-butylphenyl)sulfonyl-3,3,5-trimethyl-7-azabicyclo[3.2.1]octane Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)N1C(CC(C)(C)C2)CC2(C)C1 MTUPOGYWPRWVBX-UHFFFAOYSA-N 0.000 claims description 2
- LVJFNVMUGQXPEV-UHFFFAOYSA-N 7-(5-bromo-2-ethoxyphenyl)sulfonyl-3,3,5-trimethyl-7-azabicyclo[3.2.1]octane Chemical compound CCOC1=CC=C(Br)C=C1S(=O)(=O)N1C(CC(C)(C)C2)CC2(C)C1 LVJFNVMUGQXPEV-UHFFFAOYSA-N 0.000 claims description 2
- LIEUBWALQMYYLL-UHFFFAOYSA-N 7-(5-bromo-6-chloropyridin-3-yl)sulfonyl-3,3,5-trimethyl-7-azabicyclo[3.2.1]octane Chemical compound C1C(C)(C)CC(C)(C2)CC1N2S(=O)(=O)C1=CN=C(Cl)C(Br)=C1 LIEUBWALQMYYLL-UHFFFAOYSA-N 0.000 claims description 2
- FPUKGFSQJNYRDN-UHFFFAOYSA-N 7-(benzenesulfonyl)-3,3,5-trimethyl-7-azabicyclo[3.2.1]octane Chemical compound C1C(C)(C)CC(C)(C2)CC1N2S(=O)(=O)C1=CC=CC=C1 FPUKGFSQJNYRDN-UHFFFAOYSA-N 0.000 claims description 2
- NQDOMBRQXKSSNQ-UHFFFAOYSA-N 7-benzylsulfonyl-3,3,5-trimethyl-7-azabicyclo[3.2.1]octane Chemical compound C1C(C)(C)CC(C)(C2)CC1N2S(=O)(=O)CC1=CC=CC=C1 NQDOMBRQXKSSNQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- SZTRMKDLPQXMSX-UHFFFAOYSA-N methyl 3-[(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)sulfonyl]benzoate Chemical compound COC(=O)C1=CC=CC(S(=O)(=O)N2C3CC(CC(C)(C)C3)(C)C2)=C1 SZTRMKDLPQXMSX-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000005504 styryl group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- SBJAAFMZXQXSCV-UHFFFAOYSA-N 3-[(3,3,5-trimethyl-7-azabicyclo[3.2.1]octan-7-yl)sulfonyl]aniline Chemical compound C1C(C)(C)CC(C)(C2)CC1N2S(=O)(=O)C1=CC=CC(N)=C1 SBJAAFMZXQXSCV-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 description 13
- 0 CC(c(cc1)ccc1S(N1C(C2)CC(C)(C)CC2(C)C1)(=*)=O)O Chemical compound CC(c(cc1)ccc1S(N1C(C2)CC(C)(C)CC2(C)C1)(=*)=O)O 0.000 description 12
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| US95598507P | 2007-08-15 | 2007-08-15 | |
| PCT/US2008/009609 WO2009023181A1 (en) | 2007-08-15 | 2008-08-12 | 6-SUBSTITUTED SULFONYL AZABICYCLO[3.2.1]OCTANES USEFUL TO INHIBIT 11β-HYDROXYSTEROID DEHYDROGENASE TYPE-1 |
Publications (2)
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| JP2010536750A JP2010536750A (ja) | 2010-12-02 |
| JP2010536750A5 true JP2010536750A5 (enExample) | 2011-06-23 |
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| MX (1) | MX2010001825A (enExample) |
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|---|---|---|---|---|
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| 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 |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, 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 |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| 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 |
| JPWO2019026575A1 (ja) * | 2017-08-04 | 2020-06-18 | 国立大学法人東海国立大学機構 | 花成時期調節剤、農薬組成物及び植物の花成時期の調節方法 |
| EP4157263A4 (en) * | 2020-05-26 | 2024-09-11 | The Regents Of The University Of Michigan | Mitochondrial targeting compounds for the treatment of associated diseases |
| CN111743898A (zh) * | 2020-06-11 | 2020-10-09 | 温州医科大学附属第二医院、温州医科大学附属育英儿童医院 | 11β-HSD1抑制剂在应激环境下保护神经干细胞的应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| IL154306A0 (en) | 2003-02-05 | 2003-09-17 | Rimonyx Pharmaceuticals Ltd | Pharmaceutical compositions comprising thieno [2,3-c] pyridine derivatives and use thereof |
| JP2009515984A (ja) * | 2005-11-15 | 2009-04-16 | バーテックス ファーマシューティカルズ インコーポレイテッド | キナーゼ阻害剤として有用なアザインダゾール |
| ES2584188T3 (es) * | 2007-05-10 | 2016-09-26 | Avalon Pharmaceuticals | Derivados de fluoreno, antraceno, xanteno, dibenzosuberona y acridina y usos de los mismos |
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2008
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- 2008-08-12 EP EP08795217.2A patent/EP2188293B1/en active Active
- 2008-08-12 CA CA2696288A patent/CA2696288A1/en not_active Abandoned
- 2008-08-12 MX MX2010001825A patent/MX2010001825A/es not_active Application Discontinuation
- 2008-08-12 JP JP2010521002A patent/JP2010536750A/ja not_active Withdrawn
- 2008-08-12 WO PCT/US2008/009609 patent/WO2009023181A1/en not_active Ceased
- 2008-08-12 US US12/672,817 patent/US8466149B2/en active Active
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