JP2010501589A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2010501589A5 JP2010501589A5 JP2009525773A JP2009525773A JP2010501589A5 JP 2010501589 A5 JP2010501589 A5 JP 2010501589A5 JP 2009525773 A JP2009525773 A JP 2009525773A JP 2009525773 A JP2009525773 A JP 2009525773A JP 2010501589 A5 JP2010501589 A5 JP 2010501589A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- heterocyclyl
- cycloalkyl
- arylalkyl
- 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 —C (═O) OH Chemical group 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 32
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims 184
- 125000003118 aryl group Chemical group 0.000 claims 167
- 125000000623 heterocyclic group Chemical group 0.000 claims 143
- 125000000753 cycloalkyl group Chemical group 0.000 claims 136
- 125000003710 aryl alkyl group Chemical group 0.000 claims 90
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 83
- 229910052717 sulfur Inorganic materials 0.000 claims 73
- 229910052739 hydrogen Inorganic materials 0.000 claims 72
- 239000001257 hydrogen Substances 0.000 claims 72
- 125000005843 halogen group Chemical group 0.000 claims 60
- 125000005842 heteroatom Chemical group 0.000 claims 59
- 150000002431 hydrogen Chemical class 0.000 claims 57
- 125000003342 alkenyl group Chemical group 0.000 claims 56
- 229910052760 oxygen Inorganic materials 0.000 claims 53
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 40
- 125000001188 haloalkyl group Chemical group 0.000 claims 40
- 125000000304 alkynyl group Chemical group 0.000 claims 36
- 125000004122 cyclic group Chemical group 0.000 claims 32
- 229910052799 carbon Inorganic materials 0.000 claims 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 10
- 125000003367 polycyclic group Chemical group 0.000 claims 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 8
- 230000008602 contraction Effects 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000003831 tetrazolyl group Chemical group 0.000 claims 7
- 239000003814 drug Substances 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 4
- 208000028698 Cognitive impairment Diseases 0.000 claims 3
- 208000032928 Dyslipidaemia Diseases 0.000 claims 3
- 208000010412 Glaucoma Diseases 0.000 claims 3
- 206010020772 Hypertension Diseases 0.000 claims 3
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 3
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 3
- 208000008589 Obesity Diseases 0.000 claims 3
- 208000010067 Pituitary ACTH Hypersecretion Diseases 0.000 claims 3
- 208000020627 Pituitary-dependent Cushing syndrome Diseases 0.000 claims 3
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 3
- 208000010877 cognitive disease Diseases 0.000 claims 3
- 206010012601 diabetes mellitus Diseases 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 201000001421 hyperglycemia Diseases 0.000 claims 3
- 235000020824 obesity Nutrition 0.000 claims 3
- 201000008482 osteoarthritis Diseases 0.000 claims 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 229940124597 therapeutic agent Drugs 0.000 claims 3
- 241000235648 Pichia Species 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims 1
- 101001110310 Lentilactobacillus kefiri NADP-dependent (R)-specific alcohol dehydrogenase Proteins 0.000 claims 1
- 241000223252 Rhodotorula Species 0.000 claims 1
- 244000005700 microbiome Species 0.000 claims 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- 238000002953 preparative HPLC Methods 0.000 description 3
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 3
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- 229910004373 HOAc Inorganic materials 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- IYKFYARMMIESOX-UHFFFAOYSA-N adamantanone Chemical compound C1C(C2)CC3CC1C(=O)C2C3 IYKFYARMMIESOX-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
- NOFZMNUYEFQMBS-UHFFFAOYSA-N 1-(1,3-dimethylimidazolidin-2-yl)oxybenzotriazole Chemical compound CN1CCN(C)C1ON1C2=CC=CC=C2N=N1 NOFZMNUYEFQMBS-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical group C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- SIYYOHROEIZBBC-UHFFFAOYSA-N 5-(2-adamantylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione Chemical compound O=C1OC(C)(C)OC(=O)C1=C1C(C2)CC3CC2CC1C3 SIYYOHROEIZBBC-UHFFFAOYSA-N 0.000 description 1
- YNODJRWOUJABGN-UHFFFAOYSA-N 5-[[2-(4-fluorophenyl)-2-adamantyl]methyl]-2h-tetrazole Chemical compound C1=CC(F)=CC=C1C1(CC=2NN=NN=2)C(C2)CC3CC2CC1C3 YNODJRWOUJABGN-UHFFFAOYSA-N 0.000 description 1
- BGVLOJBYTSTMBP-UHFFFAOYSA-N 6-chloro-3-methoxy-1,2-benzoxazole Chemical compound ClC1=CC=C2C(OC)=NOC2=C1 BGVLOJBYTSTMBP-UHFFFAOYSA-N 0.000 description 1
- YMDMRRBISDUMPR-UHFFFAOYSA-N C=CCOC1(C2C(C3)CC1CC3C2)C(CC1)=CC=C1F Chemical compound C=CCOC1(C2C(C3)CC1CC3C2)C(CC1)=CC=C1F YMDMRRBISDUMPR-UHFFFAOYSA-N 0.000 description 1
- ZUEQEVQHLOKSDX-UHFFFAOYSA-N CCCCCCCCC(C)C(C(=O)O)C(=O)O Chemical compound CCCCCCCCC(C)C(C(=O)O)C(=O)O ZUEQEVQHLOKSDX-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- JISSSAVHYKGFHT-UHFFFAOYSA-N NC(CC1(C2CC(C3)CC1CC3C2)c(cc1)ccc1F)=O Chemical compound NC(CC1(C2CC(C3)CC1CC3C2)c(cc1)ccc1F)=O JISSSAVHYKGFHT-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- OJFKUJDRGJSAQB-UHFFFAOYSA-N TAK-632 Chemical compound C1=C(NC(=O)CC=2C=C(C=CC=2)C(F)(F)F)C(F)=CC=C1OC(C(=C1S2)C#N)=CC=C1N=C2NC(=O)C1CC1 OJFKUJDRGJSAQB-UHFFFAOYSA-N 0.000 description 1
- 239000012317 TBTU Substances 0.000 description 1
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- UNGMXQVELCJRIH-UHFFFAOYSA-N adamantane-2-carboxylic acid Chemical compound C1C(C2)CC3CC1C(C(=O)O)C2C3 UNGMXQVELCJRIH-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- BWBZTXSPTHTBBM-UHFFFAOYSA-L bis(3-methylimidazol-3-ium-1-yl)methanone;trifluoromethanesulfonate Chemical group [O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.CN1C=C[N+](C(=O)[N+]2=CN(C)C=C2)=C1 BWBZTXSPTHTBBM-UHFFFAOYSA-L 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- BRKADVNLTRCLOW-UHFFFAOYSA-M magnesium;fluorobenzene;bromide Chemical compound [Mg+2].[Br-].FC1=CC=[C-]C=C1 BRKADVNLTRCLOW-UHFFFAOYSA-M 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LVSJDHGRKAEGLX-UHFFFAOYSA-N oxolane;2,2,2-trifluoroacetic acid Chemical compound C1CCOC1.OC(=O)C(F)(F)F LVSJDHGRKAEGLX-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- LUYQYZLEHLTPBH-UHFFFAOYSA-N perfluorobutanesulfonyl fluoride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O LUYQYZLEHLTPBH-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LQUPKVMEAATBSL-UHFFFAOYSA-L zinc;2,3,4-trichlorophenolate Chemical compound [Zn+2].[O-]C1=CC=C(Cl)C(Cl)=C1Cl.[O-]C1=CC=C(Cl)C(Cl)=C1Cl LQUPKVMEAATBSL-UHFFFAOYSA-L 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84007106P | 2006-08-24 | 2006-08-24 | |
| US60/840,071 | 2006-08-24 | ||
| US11/843,015 US7727978B2 (en) | 2006-08-24 | 2007-08-22 | Cyclic 11-beta hydroxysteroid dehydrogenase type I inhibitors |
| US11/843,015 | 2007-08-22 | ||
| PCT/US2007/076593 WO2008024892A2 (en) | 2006-08-24 | 2007-08-23 | Cyclic 11-beta hydroxysteroid dehydrogenase type i inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013097499A Division JP2013173783A (ja) | 2006-08-24 | 2013-05-07 | 環状１１−βヒドロキシステロイドデヒドロゲナーゼＩ型阻害剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010501589A JP2010501589A (ja) | 2010-01-21 |
| JP2010501589A5 true JP2010501589A5 (enExample) | 2010-11-04 |
| JP5268912B2 JP5268912B2 (ja) | 2013-08-21 |
Family
ID=38896814
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009525773A Expired - Fee Related JP5268912B2 (ja) | 2006-08-24 | 2007-08-23 | 環状１１−βヒドロキシステロイドデヒドロゲナーゼＩ型阻害剤 |
| JP2013097499A Pending JP2013173783A (ja) | 2006-08-24 | 2013-05-07 | 環状１１−βヒドロキシステロイドデヒドロゲナーゼＩ型阻害剤 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013097499A Pending JP2013173783A (ja) | 2006-08-24 | 2013-05-07 | 環状１１−βヒドロキシステロイドデヒドロゲナーゼＩ型阻害剤 |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US7727978B2 (enExample) |
| EP (2) | EP2054368B1 (enExample) |
| JP (2) | JP5268912B2 (enExample) |
| KR (1) | KR20090057038A (enExample) |
| CN (1) | CN103833544A (enExample) |
| AR (1) | AR062533A1 (enExample) |
| AU (1) | AU2007286629A1 (enExample) |
| BR (1) | BRPI0715839A2 (enExample) |
| CA (1) | CA2661401A1 (enExample) |
| CL (1) | CL2007002492A1 (enExample) |
| EA (1) | EA200900344A1 (enExample) |
| IL (1) | IL196989A0 (enExample) |
| MX (1) | MX2009001687A (enExample) |
| NO (1) | NO20090445L (enExample) |
| TW (1) | TW200817353A (enExample) |
| WO (1) | WO2008024892A2 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7727978B2 (en) * | 2006-08-24 | 2010-06-01 | Bristol-Myers Squibb Company | Cyclic 11-beta hydroxysteroid dehydrogenase type I inhibitors |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US8119658B2 (en) | 2007-10-01 | 2012-02-21 | Bristol-Myers Squibb Company | Triazolopyridine 11-beta hydroxysteroid dehydrogenase type I inhibitors |
| JP5746612B2 (ja) * | 2008-03-19 | 2015-07-08 | オーリムメッド・ファルマ・インコーポレーテッド | 中枢神経系疾患および障害の治療に有効な新規化合物 |
| US20210130285A1 (en) | 2008-03-19 | 2021-05-06 | Aurimmed Pharma, Inc. | Novel compounds advantageous in the treatment of central nervous system diseases and disorders |
| GB0811643D0 (en) | 2008-06-25 | 2008-07-30 | Cancer Rec Tech Ltd | New therapeutic agents |
| JP5600104B2 (ja) | 2008-08-01 | 2014-10-01 | ベンティアールエックス ファーマシューティカルズ， インコーポレイテッド | Ｔｏｌｌ様受容体アゴニスト処方物およびその使用 |
| WO2010054215A1 (en) | 2008-11-06 | 2010-05-14 | Ventirx Pharmaceuticals, Inc. | Methods of synthesis of benzazepine derivatives |
| EP2243479A3 (en) | 2009-04-20 | 2011-01-19 | Abbott Laboratories | Novel amide and amidine derivates and uses thereof |
| PL2467377T3 (pl) | 2009-08-18 | 2017-10-31 | Ventirx Pharmaceuticals Inc | Podstawione benzoazepiny jako modulatory receptora toll-podobnego |
| RU2580320C2 (ru) | 2009-08-18 | 2016-04-10 | Вентиркс Фармасьютикалз, Инк. | Замещенные бензоазепины в качестве модуляторов toll-подобного рецептора |
| WO2011068927A2 (en) * | 2009-12-04 | 2011-06-09 | Abbott Laboratories | 11-β-HYDROXYSTEROID DEHYDROGENASE TYPE 1 (11B-HSD1) INHIBITORS AND USES THEREOF |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8933024B2 (en) | 2010-06-18 | 2015-01-13 | Sanofi | Azolopyridin-3-one derivatives as inhibitors of lipases and phospholipases |
| 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 |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| 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 |
| 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 |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013094761A1 (ja) | 2011-12-23 | 2013-06-27 | Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 | 新規s1p受容体調整薬 |
| WO2015061272A1 (en) | 2013-10-22 | 2015-04-30 | Bristol-Myers Squibb Company | Isotopically labeled triazolopyridine 11-beta hydroxysteroid dehydrogenase type i inhibitors |
| GB201517217D0 (en) | 2015-09-29 | 2015-11-11 | Astex Therapeutics Ltd And Cancer Res Technology Ltd | Pharmaceutical compounds |
| GB201517216D0 (en) | 2015-09-29 | 2015-11-11 | Cancer Res Technology Ltd And Astex Therapeutics Ltd | Pharmaceutical compounds |
| WO2017127306A1 (en) | 2016-01-18 | 2017-07-27 | Arisan Therapeutics | Adamatane derivatives for the treatment of filovirus infection |
| GB201704966D0 (en) | 2017-03-28 | 2017-05-10 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| GB201704965D0 (en) | 2017-03-28 | 2017-05-10 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| WO2019018185A1 (en) | 2017-07-15 | 2019-01-24 | Arisan Therapeutics Inc. | ENANTIOMERICALLY PURE ADAMATANE DERIVATIVES FOR THE TREATMENT OF FILOVIRUS INFECTIONS |
Family Cites Families (89)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE558071A (enExample) | 1956-06-16 | |||
| US3674836A (en) | 1968-05-21 | 1972-07-04 | Parke Davis & Co | 2,2-dimethyl-{11 -aryloxy-alkanoic acids and salts and esters thereof |
| US4027009A (en) | 1973-06-11 | 1977-05-31 | Merck & Co., Inc. | Compositions and methods for depressing blood serum cholesterol |
| JPS5612114B2 (enExample) | 1974-06-07 | 1981-03-18 | ||
| US4231938A (en) | 1979-06-15 | 1980-11-04 | Merck & Co., Inc. | Hypocholesteremic fermentation products and process of preparation |
| MX7065E (es) | 1980-06-06 | 1987-04-10 | Sankyo Co | Un procedimiento microbiologico para preparar derivados de ml-236b |
| US4450171A (en) | 1980-08-05 | 1984-05-22 | Merck & Co., Inc. | Antihypercholesterolemic compounds |
| US4448784A (en) | 1982-04-12 | 1984-05-15 | Hoechst-Roussel Pharmaceuticals, Inc. | 1-(Aminoalkylphenyl and aminoalkylbenzyl)-indoles and indolines and analgesic method of use thereof |
| US5354772A (en) | 1982-11-22 | 1994-10-11 | Sandoz Pharm. Corp. | Indole analogs of mevalonolactone and derivatives thereof |
| FR2547814B1 (fr) | 1983-06-22 | 1985-10-18 | Sanofi Sa | Derives de l'acide bicyclo (3.2.1.) octane carboxylique, leur procede de preparation et leur application therapeutique |
| US4691051A (en) | 1985-01-04 | 1987-09-01 | Pennwalt Corporation | Adamantyl phenyl β-alanines |
| US4681893A (en) | 1986-05-30 | 1987-07-21 | Warner-Lambert Company | Trans-6-[2-(3- or 4-carboxamido-substituted pyrrol-1-yl)alkyl]-4-hydroxypyran-2-one inhibitors of cholesterol synthesis |
| US4759923A (en) | 1987-06-25 | 1988-07-26 | Hercules Incorporated | Process for lowering serum cholesterol using poly(diallylmethylamine) derivatives |
| JP2569746B2 (ja) | 1987-08-20 | 1997-01-08 | 日産化学工業株式会社 | キノリン系メバロノラクトン類 |
| NO177005C (no) | 1988-01-20 | 1995-07-05 | Bayer Ag | Analogifremgangsmåte for fremstilling av substituerte pyridiner, samt mellomprodukter til bruk ved fremstillingen |
| FI94339C (fi) | 1989-07-21 | 1995-08-25 | Warner Lambert Co | Menetelmä farmaseuttisesti käyttökelpoisen /R-(R*,R*)/-2-(4-fluorifenyyli)- , -dihydroksi-5-(1-metyylietyyli)-3-fenyyli-4-/(fenyyliamino)karbonyyli/-1H-pyrroli-1-heptaanihapon ja sen farmaseuttisesti hyväksyttävien suolojen valmistamiseksi |
| US5177080A (en) | 1990-12-14 | 1993-01-05 | Bayer Aktiengesellschaft | Substituted pyridyl-dihydroxy-heptenoic acid and its salts |
| AU1893492A (en) | 1991-04-17 | 1992-11-17 | Merck & Co., Inc. | Pharmaceutical combination for the treatment of benign prostatic hyperplasia comtaining a 5 alpha-reductase inhibitor |
| JP2648897B2 (ja) | 1991-07-01 | 1997-09-03 | 塩野義製薬株式会社 | ピリミジン誘導体 |
| US5595872A (en) | 1992-03-06 | 1997-01-21 | Bristol-Myers Squibb Company | Nucleic acids encoding microsomal trigyceride transfer protein |
| US5594016A (en) | 1992-12-28 | 1997-01-14 | Mitsubishi Chemical Corporation | Naphthalene derivatives |
| JP3254219B2 (ja) | 1993-01-19 | 2002-02-04 | ワーナー−ランバート・コンパニー | 安定な経口用のｃｉ−９８１製剤およびその製法 |
| US5739135A (en) | 1993-09-03 | 1998-04-14 | Bristol-Myers Squibb Company | Inhibitors of microsomal triglyceride transfer protein and method |
| IL111175A0 (en) | 1993-10-07 | 1994-12-29 | Du Pont Merck Pharma | Electrophilic peptide analogs as inhibitors of trypsin-like serine proteases and pharmaceutical compositions containing them |
| US5776983A (en) | 1993-12-21 | 1998-07-07 | Bristol-Myers Squibb Company | Catecholamine surrogates useful as β3 agonists |
| US5488064A (en) | 1994-05-02 | 1996-01-30 | Bristol-Myers Squibb Company | Benzo 1,3 dioxole derivatives |
| US5385929A (en) | 1994-05-04 | 1995-01-31 | Warner-Lambert Company | [(Hydroxyphenylamino) carbonyl] pyrroles |
| FR2723317B1 (fr) | 1994-08-04 | 1996-10-31 | Sanofi Sa | Utilisation d'antagonistes de la neurotensine pour la preparation de medicaments diuretiques |
| US5612359A (en) | 1994-08-26 | 1997-03-18 | Bristol-Myers Squibb Company | Substituted biphenyl isoxazole sulfonamides |
| US5491134A (en) | 1994-09-16 | 1996-02-13 | Bristol-Myers Squibb Company | Sulfonic, phosphonic or phosphiniic acid β3 agonist derivatives |
| US5541204A (en) | 1994-12-02 | 1996-07-30 | Bristol-Myers Squibb Company | Aryloxypropanolamine β 3 adrenergic agonists |
| US5620997A (en) | 1995-05-31 | 1997-04-15 | Warner-Lambert Company | Isothiazolones |
| WO1997012613A1 (en) | 1995-10-05 | 1997-04-10 | Warner-Lambert Company | Method for treating and preventing inflammation and atherosclerosis |
| DE69636677D1 (de) | 1995-12-13 | 2006-12-14 | Univ California | Kristalle der mit einem Ligand komplexierten Ligandenbindedomäne des Schilddrüsenhormonrezeptors |
| SK282848B6 (sk) | 1996-03-14 | 2002-12-03 | Warner-Lambert Company | Premostené cyklické aminokyseliny, farmaceutická kompozícia obsahujúca tieto aminokyseliny |
| US5770615A (en) | 1996-04-04 | 1998-06-23 | Bristol-Myers Squibb Company | Catecholamine surrogates useful as β3 agonists |
| US5962440A (en) | 1996-05-09 | 1999-10-05 | Bristol-Myers Squibb Company | Cyclic phosphonate ester inhibitors of microsomal triglyceride transfer protein and method |
| US5885983A (en) | 1996-05-10 | 1999-03-23 | Bristol-Myers Squibb Company | Inhibitors of microsomal triglyceride transfer protein and method |
| US5827875A (en) | 1996-05-10 | 1998-10-27 | Bristol-Myers Squibb Company | Inhibitors of microsomal triglyceride transfer protein and method |
| DZ2285A1 (fr) | 1996-08-08 | 2002-12-25 | Smithkline Beecham Corp | Inhibiteurs de protéase de la cystéine. |
| GB9624611D0 (en) | 1996-11-26 | 1997-01-15 | Zeneca Ltd | Bicyclic amine compounds |
| US5760246A (en) | 1996-12-17 | 1998-06-02 | Biller; Scott A. | Conformationally restricted aromatic inhibitors of microsomal triglyceride transfer protein and method |
| TW536540B (en) | 1997-01-30 | 2003-06-11 | Bristol Myers Squibb Co | Endothelin antagonists: N-[[2'-[[(4,5-dimethyl-3-isoxazolyl)amino]sulfonyl]-4-(2-oxazolyl)[1,1'-biphenyl]-2-yl]methyl]-N,3,3-trimethylbutanamide and N-(4,5-dimethyl-3-isoxazolyl)-2'-[(3,3-dimethyl-2-oxo-1-pyrrolidinyl)methyl]-4'-(2-oxazolyl)[1,1'-biphe |
| EP0971881A1 (en) | 1997-03-28 | 2000-01-19 | AstraZeneca AB | Process for the preparation of n-(3-hydroxy-succinyl)-amino acid derivatives |
| GB9713739D0 (en) | 1997-06-27 | 1997-09-03 | Karobio Ab | Thyroid receptor ligands |
| CA2298813A1 (en) | 1997-08-28 | 1999-03-04 | Merck & Co., Inc. | Pyrrolidine and piperidine modulators of chemokine receptor activity |
| UA57811C2 (uk) | 1997-11-21 | 2003-07-15 | Пфайзер Продактс Інк. | Фармацевтична композиція, що містить інгібітор альдозоредуктази та інгібітор глікогенфосфорилази (варіанти), комплект, який її включає, та способи лікування ссавців зі станом інсулінорезистентності |
| WO1999031075A1 (en) | 1997-12-16 | 1999-06-24 | Warner-Lambert Company | 1-substituted-1-aminomethyl-cycloalkane derivatives (=gabapentin analogues), their preparation and their use in the treatment of neurological disorders |
| HUP0100082A3 (en) | 1998-01-26 | 2001-12-28 | Abbott Gmbh & Co Kg | Thrombin inhibitor, peptide derivatives, pharmaceutical compositions comprising thereof and their use |
| YU46200A (sh) | 1998-02-27 | 2003-02-28 | Pfizer Products Inc. | N-(supstituisani peto-članog di-ili triaza dinezasićenog prstena)karbonil/guanidin derivati za tretiranje ishemije |
| PT1094816E (pt) | 1998-07-06 | 2009-03-10 | Bristol Myers Squibb Co | Sulfonamidas bifenílicas duplamente antagonistas receptores de angiotensina e endotelina |
| GB9828442D0 (en) | 1998-12-24 | 1999-02-17 | Karobio Ab | Novel thyroid receptor ligands and method II |
| HUP9900445A2 (hu) * | 1999-02-24 | 2001-06-28 | EGIS Gyógyszergyár Rt. | Eljárás (1R,2S,4R)-(-)-N,N-(dimetilamino-etoxi)-2-fenil-1,7,7-trimetil-biciklo[2.2.1]heptán előállítására és ennek köztiterméke |
| US6548529B1 (en) | 1999-04-05 | 2003-04-15 | Bristol-Myers Squibb Company | Heterocyclic containing biphenyl aP2 inhibitors and method |
| TW200528436A (en) | 1999-09-22 | 2005-09-01 | Bristol Myers Squibb Co | Substituted acid derivatives useful as antiodiabetic and antiobesity agents and method |
| PH12000002657B1 (en) | 1999-10-12 | 2006-02-21 | Bristol Myers Squibb Co | C-aryl glucoside SGLT2 inhibitors |
| WO2001060818A1 (en) | 2000-02-14 | 2001-08-23 | Tularik Inc. | Lxr modulators |
| US6620829B2 (en) * | 2000-10-17 | 2003-09-16 | Warner-Lambert Company | Method of treating noninflammatory cartilage damage |
| US7112593B2 (en) | 2001-03-27 | 2006-09-26 | Eisai Co., Ltd. | N-aryl-substituted cyclic amine derivative and medicine containing the same as active ingredient |
| JP4776810B2 (ja) | 2001-05-30 | 2011-09-21 | 日本曹達株式会社 | α位トリ置換酢酸の製造方法 |
| MXPA03011566A (es) * | 2001-06-11 | 2004-10-28 | Xenoport Inc | Formas de dosificacion de profarmacos de analogos de gaba administrados oralmente que tienen toxicidad reducida. |
| US20030114460A1 (en) | 2001-12-14 | 2003-06-19 | Allergan Sales, Inc. | Pharmaceutical conjugates with enhanced pharmacokinetic characteristics |
| EP1469841A1 (en) | 2002-01-31 | 2004-10-27 | Warner-Lambert Company | Alpha 2 delta ligands to treat tinnitus |
| AU2003207717B9 (en) | 2002-02-01 | 2009-05-07 | Merck & Co., Inc. | 11-beta-hydroxysteroid dehydrogenase 1 inhibitors useful for the treatment of diabetes, obesity and dyslipidemia |
| TW200401635A (en) * | 2002-07-23 | 2004-02-01 | Yamanouchi Pharma Co Ltd | 2-Cyano-4-fluoropyrrolidine derivative or salt thereof |
| JP4012016B2 (ja) * | 2002-08-29 | 2007-11-21 | キヤノン株式会社 | 画像処理装置、画像処理方法、記憶媒体、及びプログラム |
| US20040209858A1 (en) | 2002-10-22 | 2004-10-21 | Bennani Youssef L. | Cycloalkylamides and their therapeutic applications |
| WO2004056744A1 (en) | 2002-12-23 | 2004-07-08 | Janssen Pharmaceutica N.V. | Adamantyl acetamides as hydroxysteroid dehydrogenase inhibitors |
| TW200503994A (en) | 2003-01-24 | 2005-02-01 | Novartis Ag | Organic compounds |
| US7135575B2 (en) * | 2003-03-03 | 2006-11-14 | Array Biopharma, Inc. | P38 inhibitors and methods of use thereof |
| US7700583B2 (en) | 2003-04-11 | 2010-04-20 | High Point Pharmaceuticals, Llc | 11β-hydroxysteroid dehydrogenase type 1 active compounds |
| ATE482747T1 (de) | 2003-04-11 | 2010-10-15 | High Point Pharmaceuticals Llc | Neue amide derivate und deren pharmazeutische verwendungen |
| EP1615667A2 (en) | 2003-04-11 | 2006-01-18 | Novo Nordisk A/S | Combinations of an 11-beta-hydroxysteroid dehydrogenase type 1 inhibitor and a glucocorticoid receptor agonist |
| US20060094699A1 (en) | 2003-04-11 | 2006-05-04 | Kampen Gita Camilla T | Combination therapy using an 11beta-hydroxysteroid dehydrogenase type 1 inhibitor and a glucocorticoid receptor agonist to minimize the side effects associated with glucocorticoid receptor agonist therapy |
| US7501405B2 (en) | 2003-04-11 | 2009-03-10 | High Point Pharmaceuticals, Llc | Combination therapy using an 11β-hydroxysteroid dehydrogenase type 1 inhibitor and an antihypertensive agent for the treatment of metabolic syndrome and related diseases and disorders |
| WO2004089416A2 (en) | 2003-04-11 | 2004-10-21 | Novo Nordisk A/S | Combination of an 11beta-hydroxysteroid dehydrogenase type 1 inhibitor and an antihypertensive agent |
| TW200528440A (en) * | 2003-10-31 | 2005-09-01 | Fujisawa Pharmaceutical Co | 2-cyanopyrrolidinecarboxamide compound |
| JPWO2005097738A1 (ja) * | 2004-04-06 | 2008-02-28 | 大日本住友製薬株式会社 | 新規スルホンアミド誘導体 |
| US7880001B2 (en) | 2004-04-29 | 2011-02-01 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase Type 1 enzyme |
| EP1841723A1 (en) | 2004-12-31 | 2007-10-10 | Universität Dortmund | Decaline derived compounds as pharmaceutically active agents |
| US20060148871A1 (en) | 2005-01-05 | 2006-07-06 | Rohde Jeffrey J | Metabolic stabilization of substituted adamantane |
| KR101496190B1 (ko) | 2005-01-05 | 2015-02-26 | 애브비 인코포레이티드 | 11-베타-하이드록시스테로이드 데하이드로게나제 타입 1 효소의 억제제로서의 아다만틸 유도체 |
| KR101302627B1 (ko) | 2005-01-05 | 2013-09-10 | 아비에 인코포레이티드 | 11-베타-하이드록시스테로이드 데하이드로게나제 타입 1 효소의 억제제 |
| WO2007038452A1 (en) | 2005-09-28 | 2007-04-05 | Merck & Co., Inc. | Process for synthesizing 1,2,4-triazoles |
| JP5036722B2 (ja) | 2005-10-20 | 2012-09-26 | メルク・シャープ・エンド・ドーム・コーポレイション | １１−ベータ−ヒドロキシステロイドデヒドロゲナーゼ−１阻害剤としてのトリアゾール誘導体 |
| EP1801098A1 (en) | 2005-12-16 | 2007-06-27 | Merck Sante | 2-Adamantylurea derivatives as selective 11B-HSD1 inhibitors |
| PE20080403A1 (es) | 2006-07-14 | 2008-04-25 | Amgen Inc | Derivados heterociclicos fusionados y metodos de uso |
| US8217177B2 (en) | 2006-07-14 | 2012-07-10 | Amgen Inc. | Fused heterocyclic derivatives and methods of use |
| US7727978B2 (en) * | 2006-08-24 | 2010-06-01 | Bristol-Myers Squibb Company | Cyclic 11-beta hydroxysteroid dehydrogenase type I inhibitors |
-
2007
- 2007-08-22 US US11/843,015 patent/US7727978B2/en active Active
- 2007-08-23 KR KR1020097005903A patent/KR20090057038A/ko not_active Withdrawn
- 2007-08-23 BR BRPI0715839-4A patent/BRPI0715839A2/pt not_active IP Right Cessation
- 2007-08-23 MX MX2009001687A patent/MX2009001687A/es active IP Right Grant
- 2007-08-23 EA EA200900344A patent/EA200900344A1/ru unknown
- 2007-08-23 CA CA002661401A patent/CA2661401A1/en not_active Abandoned
- 2007-08-23 EP EP07814376.5A patent/EP2054368B1/en active Active
- 2007-08-23 CN CN201410057480.5A patent/CN103833544A/zh active Pending
- 2007-08-23 WO PCT/US2007/076593 patent/WO2008024892A2/en not_active Ceased
- 2007-08-23 EP EP20120181050 patent/EP2527317A1/en not_active Withdrawn
- 2007-08-23 AU AU2007286629A patent/AU2007286629A1/en not_active Abandoned
- 2007-08-23 JP JP2009525773A patent/JP5268912B2/ja not_active Expired - Fee Related
- 2007-08-24 AR ARP070103783A patent/AR062533A1/es not_active Application Discontinuation
- 2007-08-24 TW TW096131558A patent/TW200817353A/zh unknown
- 2007-08-24 CL CL2007002492A patent/CL2007002492A1/es unknown
-
2009
- 2009-01-29 NO NO20090445A patent/NO20090445L/no not_active Application Discontinuation
- 2009-02-11 IL IL196989A patent/IL196989A0/en unknown
-
2010
- 2010-04-14 US US12/759,867 patent/US8299054B2/en active Active
-
2013
- 2013-05-07 JP JP2013097499A patent/JP2013173783A/ja active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US9718779B2 (en) | Intermediate and polymorphs of 1-(4-methoxypheny1)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5,6,7-tetra hydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide and process thereof | |
| US8648189B2 (en) | Method for the preparation of rivoraxaban | |
| JP5586632B2 (ja) | ５員の複素環式化合物のアザスピラニル−アルキルカルバメートの誘導体、この調製およびこの治療的使用 | |
| US7119116B2 (en) | Derivatives of dioxane-2-alkyl carbamates, preparation thereof and application thereof in therapeutics | |
| US10358423B2 (en) | Processes for the preparation of 4-alkoxy-3-(acyl or alkyl)oxypicolinamdes | |
| US20090023918A1 (en) | Process for preparing 3-acylaminobenzofuran-2-carboxylic acid derivative | |
| JP4617292B2 (ja) | アリールアルキルカルバメート誘導体の製造およびそれらの治療用途 | |
| KR20110034020A (ko) | 알킬 티아졸 카르바메이트 유도체, 그의 제조법, 및 ｆａａｈ 효소 억제제로서의 그의 용도 | |
| WO2022232948A1 (en) | Processes for the preparation of the enantiomers of 3,4-methylenedioxymethamphetamine (mdma) and n-methyl-1,3-benzodioxolylbutanamine (mbdb) | |
| KR20120014202A (ko) | ５-원 헤테로시클릭 화합물 시클로펜타［ｃ］피롤릴알킬카르바메이트 유도체, 그의 제조법 및 그의 치료 용도 | |
| AU625664B2 (en) | 3,4-Dehydropiperidine derivatives having psychotropic activity | |
| JP2002544207A (ja) | ２，２−ジメチル−１，３−ジオキサン中間体の塩及びその製法 | |
| WO2016045586A1 (zh) | 苯并恶唑并恶嗪酮类化合物的制备方法及其中间体和晶型 | |
| US20190276430A1 (en) | 4-((6-(2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-mercapto-1h-1,2,4-triazol-1-yl)propyl)pyridin-3-yl)oxy)benzonitrile and processes of preparation | |
| KR20190036549A (ko) | 피라졸-아미드 화합물의 제조 방법 | |
| JP2012511514A (ja) | レニン阻害剤としての３，４−置換ピペリジン誘導体 | |
| CN1305995A (zh) | 制备1,4－二氢吡啶化合物的方法 | |
| CA1334416C (en) | 4-phenyl-4-¬n-(phenyl)amido|piperidine derivatives and pharmaceutical compositions and method employing such compounds | |
| US12215114B2 (en) | Processes and intermediates for producing diazaspiro lactam compounds | |
| JP6884857B2 (ja) | フェニルアラニン類化合物の製造方法 | |
| KR101166280B1 (ko) | 시탈로프램 및 에난티오머의 제조 방법 | |
| ES2216482T3 (es) | Derivado de 5-(2,2-difluoro-1,3-benzodioxol-5-il)ciclopentenopiridina sustituido. | |
| JP5728027B2 (ja) | ピロール誘導体及びその製造方法 | |
| CN101137646A (zh) | Ccr5受体拮抗剂的合成 | |
| JP2007524705A (ja) | ヘテロアリール−アルキルカーバメート誘導体、それらの製造方法、及び、ｆａａｈ酵素インヒビターとしてのそれらの使用 |