JP2010501589A5 - - Google Patents
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- 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
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- -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 (https=) | 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 (https=) |
| EP (2) | EP2527317A1 (https=) |
| JP (2) | JP5268912B2 (https=) |
| KR (1) | KR20090057038A (https=) |
| CN (1) | CN103833544A (https=) |
| AR (1) | AR062533A1 (https=) |
| AU (1) | AU2007286629A1 (https=) |
| BR (1) | BRPI0715839A2 (https=) |
| CA (1) | CA2661401A1 (https=) |
| CL (1) | CL2007002492A1 (https=) |
| EA (1) | EA200900344A1 (https=) |
| IL (1) | IL196989A0 (https=) |
| MX (1) | MX2009001687A (https=) |
| NO (1) | NO20090445L (https=) |
| TW (1) | TW200817353A (https=) |
| WO (1) | WO2008024892A2 (https=) |
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| RU2016108987A (ru) | 2009-08-18 | 2018-11-26 | Вентиркс Фармасьютикалз, Инк. | Замещенные бензоазепины в качестве модуляторов toll-подобного рецептора |
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-
2007
- 2007-08-22 US US11/843,015 patent/US7727978B2/en active Active
- 2007-08-23 MX MX2009001687A patent/MX2009001687A/es active IP Right Grant
- 2007-08-23 BR BRPI0715839-4A patent/BRPI0715839A2/pt not_active IP Right Cessation
- 2007-08-23 EP EP20120181050 patent/EP2527317A1/en not_active Withdrawn
- 2007-08-23 JP JP2009525773A patent/JP5268912B2/ja not_active Expired - Fee Related
- 2007-08-23 WO PCT/US2007/076593 patent/WO2008024892A2/en not_active Ceased
- 2007-08-23 CA CA002661401A patent/CA2661401A1/en not_active Abandoned
- 2007-08-23 AU AU2007286629A patent/AU2007286629A1/en not_active Abandoned
- 2007-08-23 EP EP07814376.5A patent/EP2054368B1/en active Active
- 2007-08-23 EA EA200900344A patent/EA200900344A1/ru unknown
- 2007-08-23 CN CN201410057480.5A patent/CN103833544A/zh active Pending
- 2007-08-23 KR KR1020097005903A patent/KR20090057038A/ko not_active Withdrawn
- 2007-08-24 CL CL2007002492A patent/CL2007002492A1/es unknown
- 2007-08-24 TW TW096131558A patent/TW200817353A/zh unknown
- 2007-08-24 AR ARP070103783A patent/AR062533A1/es not_active Application Discontinuation
-
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
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2013
- 2013-05-07 JP JP2013097499A patent/JP2013173783A/ja active Pending
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