JP2006520808A5 - - Google Patents
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- Publication number
- JP2006520808A5 JP2006520808A5 JP2006507668A JP2006507668A JP2006520808A5 JP 2006520808 A5 JP2006520808 A5 JP 2006520808A5 JP 2006507668 A JP2006507668 A JP 2006507668A JP 2006507668 A JP2006507668 A JP 2006507668A JP 2006520808 A5 JP2006520808 A5 JP 2006520808A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- isopentylcyclohexanecarbonylamino
- dimethylthiopropionate
- transfer protein
- ethylbutyl
- 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
- 239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 claims 16
- 229940125881 cholesteryl ester transfer protein inhibitor Drugs 0.000 claims 16
- YZQLWPMZQVHJED-UHFFFAOYSA-N 2-methylpropanethioic acid S-[2-[[[1-(2-ethylbutyl)cyclohexyl]-oxomethyl]amino]phenyl] ester Chemical compound C=1C=CC=C(SC(=O)C(C)C)C=1NC(=O)C1(CC(CC)CC)CCCCC1 YZQLWPMZQVHJED-UHFFFAOYSA-N 0.000 claims 7
- 239000003814 drug Substances 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 6
- 208000024172 Cardiovascular disease Diseases 0.000 claims 4
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 239000000654 additive Substances 0.000 claims 3
- 230000000996 additive effect Effects 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- OVRLABAFXJPIMU-UHFFFAOYSA-N 1-(2-ethylbutyl)-n-(2-sulfanylphenyl)cyclohexane-1-carboxamide Chemical compound C=1C=CC=C(S)C=1NC(=O)C1(CC(CC)CC)CCCCC1 OVRLABAFXJPIMU-UHFFFAOYSA-N 0.000 claims 2
- -1 1-isopentylcyclohexanecarbonylamino Chemical group 0.000 claims 2
- KEWSCDNULKOKTG-UHFFFAOYSA-N 4-cyano-4-ethylsulfanylcarbothioylsulfanylpentanoic acid Chemical compound CCSC(=S)SC(C)(C#N)CCC(O)=O KEWSCDNULKOKTG-UHFFFAOYSA-N 0.000 claims 2
- 206010002383 Angina Pectoris Diseases 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 108010061846 Cholesterol Ester Transfer Proteins Proteins 0.000 claims 2
- 102000012336 Cholesterol Ester Transfer Proteins Human genes 0.000 claims 2
- 102100037637 Cholesteryl ester transfer protein Human genes 0.000 claims 2
- 101000880514 Homo sapiens Cholesteryl ester transfer protein Proteins 0.000 claims 2
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 208000018262 Peripheral vascular disease Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 239000008280 blood Substances 0.000 claims 2
- 210000004369 blood Anatomy 0.000 claims 2
- 208000029078 coronary artery disease Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 238000001727 in vivo Methods 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- 230000036470 plasma concentration Effects 0.000 claims 2
- 238000002203 pretreatment Methods 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 230000004952 protein activity Effects 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims 1
- INKBUBAEIMNSIG-UHFFFAOYSA-N 1-(2-methylpropyl)-n-(2-sulfanylphenyl)cyclohexane-1-carboxamide Chemical compound C=1C=CC=C(S)C=1NC(=O)C1(CC(C)C)CCCCC1 INKBUBAEIMNSIG-UHFFFAOYSA-N 0.000 claims 1
- OBWOWYBSZTURFB-UHFFFAOYSA-N 1-(3-methylbutyl)-n-(2-sulfanylphenyl)cyclohexane-1-carboxamide Chemical compound C=1C=CC=C(S)C=1NC(=O)C1(CCC(C)C)CCCCC1 OBWOWYBSZTURFB-UHFFFAOYSA-N 0.000 claims 1
- WSDMOYWCWHLBPX-UHFFFAOYSA-N 1-(3-methylbutyl)-n-(2-sulfanylphenyl)cyclopentane-1-carboxamide Chemical compound C=1C=CC=C(S)C=1NC(=O)C1(CCC(C)C)CCCC1 WSDMOYWCWHLBPX-UHFFFAOYSA-N 0.000 claims 1
- QSHCOFDJVJBWJU-UHFFFAOYSA-N 1-(3-methylbutyl)-n-(4-methyl-2-sulfanylphenyl)cyclohexane-1-carboxamide Chemical compound C=1C=C(C)C=C(S)C=1NC(=O)C1(CCC(C)C)CCCCC1 QSHCOFDJVJBWJU-UHFFFAOYSA-N 0.000 claims 1
- ZUBAYESAZFWZPL-UHFFFAOYSA-N 1-(3-methylbutyl)-n-(5-methyl-2-sulfanylphenyl)cyclohexane-1-carboxamide Chemical compound C=1C(C)=CC=C(S)C=1NC(=O)C1(CCC(C)C)CCCCC1 ZUBAYESAZFWZPL-UHFFFAOYSA-N 0.000 claims 1
- RPOWLQXTRJDTQA-UHFFFAOYSA-N 1-butyl-n-(2-sulfanylphenyl)cyclohexane-1-carboxamide Chemical compound C=1C=CC=C(S)C=1NC(=O)C1(CCCC)CCCCC1 RPOWLQXTRJDTQA-UHFFFAOYSA-N 0.000 claims 1
- HNJZDNMUVSELCB-UHFFFAOYSA-N 1-ethyl-n-(2-sulfanylphenyl)cyclohexane-1-carboxamide Chemical compound C=1C=CC=C(S)C=1NC(=O)C1(CC)CCCCC1 HNJZDNMUVSELCB-UHFFFAOYSA-N 0.000 claims 1
- BEZLZUVKRNXSDY-UHFFFAOYSA-N 1-methyl-n-(2-phenylsulfanylcarbonylsulfanylphenyl)cyclohexane-1-carboxamide Chemical compound C=1C=CC=C(SC(=O)SC=2C=CC=CC=2)C=1NC(=O)C1(C)CCCCC1 BEZLZUVKRNXSDY-UHFFFAOYSA-N 0.000 claims 1
- LRWUYINHKRXNQH-UHFFFAOYSA-N 1-methyl-n-(2-sulfanylphenyl)cyclohexane-1-carboxamide Chemical compound C=1C=CC=C(S)C=1NC(=O)C1(C)CCCCC1 LRWUYINHKRXNQH-UHFFFAOYSA-N 0.000 claims 1
- YOTSORLUOLPCCV-UHFFFAOYSA-N 1-propan-2-yl-n-(2-sulfanylphenyl)cyclohexane-1-carboxamide Chemical compound C=1C=CC=C(S)C=1NC(=O)C1(C(C)C)CCCCC1 YOTSORLUOLPCCV-UHFFFAOYSA-N 0.000 claims 1
- GIBQUYMCEXFBRU-UHFFFAOYSA-N 1-propyl-n-(2-sulfanylphenyl)cyclohexane-1-carboxamide Chemical compound C=1C=CC=C(S)C=1NC(=O)C1(CCC)CCCCC1 GIBQUYMCEXFBRU-UHFFFAOYSA-N 0.000 claims 1
- JHSXHKMJBWOMRU-UHFFFAOYSA-N 2,2-dimethylpropanethioic s-acid Chemical compound CC(C)(C)C(S)=O JHSXHKMJBWOMRU-UHFFFAOYSA-N 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- ZYSULIBJXPPZRD-UHFFFAOYSA-N 6-[2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl]sulfanyl-6-oxohexanoic acid Chemical compound C=1C=CC=C(SC(=O)CCCCC(O)=O)C=1NC(=O)C1(CCC(C)C)CCCCC1 ZYSULIBJXPPZRD-UHFFFAOYSA-N 0.000 claims 1
- 208000032928 Dyslipidaemia Diseases 0.000 claims 1
- 208000037487 Endotoxemia Diseases 0.000 claims 1
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 1
- 208000000563 Hyperlipoproteinemia Type II Diseases 0.000 claims 1
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 1
- 102100024640 Low-density lipoprotein receptor Human genes 0.000 claims 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical group C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 206010045261 Type IIa hyperlipidaemia Diseases 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000005110 aryl thio group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- UIJGNTRUPZPVNG-UHFFFAOYSA-N benzenecarbothioic s-acid Chemical compound SC(=O)C1=CC=CC=C1 UIJGNTRUPZPVNG-UHFFFAOYSA-N 0.000 claims 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 1
- 229960000913 crospovidone Drugs 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 1
- 201000001386 familial hypercholesterolemia Diseases 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 208000006575 hypertriglyceridemia Diseases 0.000 claims 1
- LRXMNFMNMFWCOJ-UHFFFAOYSA-N methyl [2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl]sulfanylformate Chemical compound COC(=O)SC1=CC=CC=C1NC(=O)C1(CCC(C)C)CCCCC1 LRXMNFMNMFWCOJ-UHFFFAOYSA-N 0.000 claims 1
- 208000031225 myocardial ischemia Diseases 0.000 claims 1
- GHSLUZCHSFWKRE-UHFFFAOYSA-N n-(4,5-dichloro-2-sulfanylphenyl)-1-(3-methylbutyl)cyclohexane-1-carboxamide Chemical compound C=1C(Cl)=C(Cl)C=C(S)C=1NC(=O)C1(CCC(C)C)CCCCC1 GHSLUZCHSFWKRE-UHFFFAOYSA-N 0.000 claims 1
- LHNSUEDKNSIQML-UHFFFAOYSA-N n-(4,5-dichloro-2-sulfanylphenyl)-1-(3-methylbutyl)cyclopentane-1-carboxamide Chemical compound C=1C(Cl)=C(Cl)C=C(S)C=1NC(=O)C1(CCC(C)C)CCCC1 LHNSUEDKNSIQML-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 claims 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 229940121649 protein inhibitor Drugs 0.000 claims 1
- 239000012268 protein inhibitor Substances 0.000 claims 1
- 208000037803 restenosis Diseases 0.000 claims 1
- WBCRBXAFIQXPJQ-UHFFFAOYSA-N s-[2-[(1-methylcyclohexanecarbonyl)amino]phenyl] 2,2-dimethylpropanethioate Chemical compound CC(C)(C)C(=O)SC1=CC=CC=C1NC(=O)C1(C)CCCCC1 WBCRBXAFIQXPJQ-UHFFFAOYSA-N 0.000 claims 1
- CUFAKTNZJHSRMF-UHFFFAOYSA-N s-[2-[[1-(2-ethylbutyl)cyclohexanecarbonyl]amino]phenyl] 1-acetylpiperidine-4-carbothioate Chemical compound C=1C=CC=C(SC(=O)C2CCN(CC2)C(C)=O)C=1NC(=O)C1(CC(CC)CC)CCCCC1 CUFAKTNZJHSRMF-UHFFFAOYSA-N 0.000 claims 1
- MJLUTSZKWAWVAY-UHFFFAOYSA-N s-[2-[[1-(2-ethylbutyl)cyclohexanecarbonyl]amino]phenyl] 2,2-dimethylpropanethioate Chemical compound C=1C=CC=C(SC(=O)C(C)(C)C)C=1NC(=O)C1(CC(CC)CC)CCCCC1 MJLUTSZKWAWVAY-UHFFFAOYSA-N 0.000 claims 1
- CVANHIYHWIDBGC-UHFFFAOYSA-N s-[2-[[1-(2-ethylbutyl)cyclohexanecarbonyl]amino]phenyl] 2-(4-chlorophenoxy)ethanethioate Chemical compound C=1C=CC=C(SC(=O)COC=2C=CC(Cl)=CC=2)C=1NC(=O)C1(CC(CC)CC)CCCCC1 CVANHIYHWIDBGC-UHFFFAOYSA-N 0.000 claims 1
- AFVJGCXNVCMGBC-UHFFFAOYSA-N s-[2-[[1-(2-ethylbutyl)cyclohexanecarbonyl]amino]phenyl] 2-methoxyethanethioate Chemical compound C=1C=CC=C(SC(=O)COC)C=1NC(=O)C1(CC(CC)CC)CCCCC1 AFVJGCXNVCMGBC-UHFFFAOYSA-N 0.000 claims 1
- CCSJXVJLCREWRO-UHFFFAOYSA-N s-[2-[[1-(2-ethylbutyl)cyclohexanecarbonyl]amino]phenyl] ethanethioate Chemical compound C=1C=CC=C(SC(C)=O)C=1NC(=O)C1(CC(CC)CC)CCCCC1 CCSJXVJLCREWRO-UHFFFAOYSA-N 0.000 claims 1
- MJGXFBMXAVDVQR-UHFFFAOYSA-N s-[2-[[1-(2-methylpropyl)cyclohexanecarbonyl]amino]phenyl] 1-acetylpiperidine-4-carbothioate Chemical compound C=1C=CC=C(SC(=O)C2CCN(CC2)C(C)=O)C=1NC(=O)C1(CC(C)C)CCCCC1 MJGXFBMXAVDVQR-UHFFFAOYSA-N 0.000 claims 1
- AVHJWJNTHBRPPL-UHFFFAOYSA-N s-[2-[[1-(2-methylpropyl)cyclohexanecarbonyl]amino]phenyl] 2-(4-chlorophenoxy)ethanethioate Chemical compound C=1C=CC=C(SC(=O)COC=2C=CC(Cl)=CC=2)C=1NC(=O)C1(CC(C)C)CCCCC1 AVHJWJNTHBRPPL-UHFFFAOYSA-N 0.000 claims 1
- ZKLYDYIGXBYRKG-UHFFFAOYSA-N s-[2-[[1-(2-methylpropyl)cyclohexanecarbonyl]amino]phenyl] 2-methylpropanethioate Chemical compound C=1C=CC=C(SC(=O)C(C)C)C=1NC(=O)C1(CC(C)C)CCCCC1 ZKLYDYIGXBYRKG-UHFFFAOYSA-N 0.000 claims 1
- ZSWAVFZBRNIUBU-UHFFFAOYSA-N s-[2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]-4-(trifluoromethyl)phenyl] 2,2-dimethylpropanethioate Chemical compound C=1C(C(F)(F)F)=CC=C(SC(=O)C(C)(C)C)C=1NC(=O)C1(CCC(C)C)CCCCC1 ZSWAVFZBRNIUBU-UHFFFAOYSA-N 0.000 claims 1
- LJSAHYCOQKCCQZ-UHFFFAOYSA-N s-[2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]-4-nitrophenyl] 2,2-dimethylpropanethioate Chemical compound C=1C([N+]([O-])=O)=CC=C(SC(=O)C(C)(C)C)C=1NC(=O)C1(CCC(C)C)CCCCC1 LJSAHYCOQKCCQZ-UHFFFAOYSA-N 0.000 claims 1
- WIDPRMXSHTWZFE-UHFFFAOYSA-N s-[2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl] 2,2-dimethylpropanethioate Chemical compound C=1C=CC=C(SC(=O)C(C)(C)C)C=1NC(=O)C1(CCC(C)C)CCCCC1 WIDPRMXSHTWZFE-UHFFFAOYSA-N 0.000 claims 1
- FXIULSQKMBPEOI-UHFFFAOYSA-N s-[2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl] 2-(4-chlorophenoxy)ethanethioate Chemical compound C=1C=CC=C(SC(=O)COC=2C=CC(Cl)=CC=2)C=1NC(=O)C1(CCC(C)C)CCCCC1 FXIULSQKMBPEOI-UHFFFAOYSA-N 0.000 claims 1
- HYSIQIZWVLUQLT-UHFFFAOYSA-N s-[2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl] 2-acetamido-3-phenylpropanethioate Chemical compound C=1C=CC=C(SC(=O)C(CC=2C=CC=CC=2)NC(C)=O)C=1NC(=O)C1(CCC(C)C)CCCCC1 HYSIQIZWVLUQLT-UHFFFAOYSA-N 0.000 claims 1
- OTMSDUWIKWKOJA-UHFFFAOYSA-N s-[2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl] 2-acetamido-5-amino-5-oxopentanethioate Chemical compound C=1C=CC=C(SC(=O)C(CCC(N)=O)NC(C)=O)C=1NC(=O)C1(CCC(C)C)CCCCC1 OTMSDUWIKWKOJA-UHFFFAOYSA-N 0.000 claims 1
- SSAIZJDBBXDECD-UHFFFAOYSA-N s-[2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl] 2-chloroethanethioate Chemical compound C=1C=CC=C(SC(=O)CCl)C=1NC(=O)C1(CCC(C)C)CCCCC1 SSAIZJDBBXDECD-UHFFFAOYSA-N 0.000 claims 1
- MXLMXGUKFHEMNV-UHFFFAOYSA-N s-[2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl] 2-hydroxy-2-methylpropanethioate Chemical compound C=1C=CC=C(SC(=O)C(C)(C)O)C=1NC(=O)C1(CCC(C)C)CCCCC1 MXLMXGUKFHEMNV-UHFFFAOYSA-N 0.000 claims 1
- CVPUOEPURYNJKD-UHFFFAOYSA-N s-[2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl] 2-methoxyethanethioate Chemical compound COCC(=O)SC1=CC=CC=C1NC(=O)C1(CCC(C)C)CCCCC1 CVPUOEPURYNJKD-UHFFFAOYSA-N 0.000 claims 1
- XHVJBTXLUDEYRF-UHFFFAOYSA-N s-[2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl] 2-methylpropanethioate Chemical compound C=1C=CC=C(SC(=O)C(C)C)C=1NC(=O)C1(CCC(C)C)CCCCC1 XHVJBTXLUDEYRF-UHFFFAOYSA-N 0.000 claims 1
- FRZSEBDDONUPPE-UHFFFAOYSA-N s-[2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl] 2-phenoxyethanethioate Chemical compound C=1C=CC=C(SC(=O)COC=2C=CC=CC=2)C=1NC(=O)C1(CCC(C)C)CCCCC1 FRZSEBDDONUPPE-UHFFFAOYSA-N 0.000 claims 1
- PAUVZWIHHQXRET-UHFFFAOYSA-N s-[2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl] benzenecarbothioate Chemical compound C=1C=CC=C(SC(=O)C=2C=CC=CC=2)C=1NC(=O)C1(CCC(C)C)CCCCC1 PAUVZWIHHQXRET-UHFFFAOYSA-N 0.000 claims 1
- OYMZRBRXYBINJS-UHFFFAOYSA-N s-[2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl] cyclohexanecarbothioate Chemical compound C=1C=CC=C(SC(=O)C2CCCCC2)C=1NC(=O)C1(CCC(C)C)CCCCC1 OYMZRBRXYBINJS-UHFFFAOYSA-N 0.000 claims 1
- UEQKYAQEIJRSJL-UHFFFAOYSA-N s-[2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl] cyclopropanecarbothioate Chemical compound C=1C=CC=C(SC(=O)C2CC2)C=1NC(=O)C1(CCC(C)C)CCCCC1 UEQKYAQEIJRSJL-UHFFFAOYSA-N 0.000 claims 1
- JDXPRSNPJGKLDY-UHFFFAOYSA-N s-[2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl] ethanethioate Chemical compound C=1C=CC=C(SC(C)=O)C=1NC(=O)C1(CCC(C)C)CCCCC1 JDXPRSNPJGKLDY-UHFFFAOYSA-N 0.000 claims 1
- HWBRDPQUXXEYBF-UHFFFAOYSA-N s-[2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl] n-phenylcarbamothioate Chemical compound C=1C=CC=C(SC(=O)NC=2C=CC=CC=2)C=1NC(=O)C1(CCC(C)C)CCCCC1 HWBRDPQUXXEYBF-UHFFFAOYSA-N 0.000 claims 1
- ZWIFWJMAXNUTID-UHFFFAOYSA-N s-[2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl] propanethioate Chemical compound CCC(=O)SC1=CC=CC=C1NC(=O)C1(CCC(C)C)CCCCC1 ZWIFWJMAXNUTID-UHFFFAOYSA-N 0.000 claims 1
- IUOPLRYKLPOZOU-UHFFFAOYSA-N s-[2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl] pyridine-3-carbothioate Chemical compound C=1C=CC=C(SC(=O)C=2C=NC=CC=2)C=1NC(=O)C1(CCC(C)C)CCCCC1 IUOPLRYKLPOZOU-UHFFFAOYSA-N 0.000 claims 1
- JFCOHMGXJCIKPZ-UHFFFAOYSA-N s-[4,5-dichloro-2-[(1-cyclopropylcyclohexanecarbonyl)amino]phenyl] 2,2-dimethylpropanethioate Chemical compound CC(C)(C)C(=O)SC1=CC(Cl)=C(Cl)C=C1NC(=O)C1(C2CC2)CCCCC1 JFCOHMGXJCIKPZ-UHFFFAOYSA-N 0.000 claims 1
- OLXQLAYHYKQVRD-UHFFFAOYSA-N s-[4,5-dichloro-2-[(1-pentylcyclohexanecarbonyl)amino]phenyl] 2,2-dimethylpropanethioate Chemical compound C=1C(Cl)=C(Cl)C=C(SC(=O)C(C)(C)C)C=1NC(=O)C1(CCCCC)CCCCC1 OLXQLAYHYKQVRD-UHFFFAOYSA-N 0.000 claims 1
- ITEBOTJVVWYIQA-UHFFFAOYSA-N s-[4,5-dichloro-2-[(1-propan-2-ylcyclohexanecarbonyl)amino]phenyl] 2,2-dimethylpropanethioate Chemical compound C=1C(Cl)=C(Cl)C=C(SC(=O)C(C)(C)C)C=1NC(=O)C1(C(C)C)CCCCC1 ITEBOTJVVWYIQA-UHFFFAOYSA-N 0.000 claims 1
- LRLVDOHJDUBITP-UHFFFAOYSA-N s-[4,5-dichloro-2-[[1-(3-methylbutyl)cyclobutanecarbonyl]amino]phenyl] 2,2-dimethylpropanethioate Chemical compound C=1C(Cl)=C(Cl)C=C(SC(=O)C(C)(C)C)C=1NC(=O)C1(CCC(C)C)CCC1 LRLVDOHJDUBITP-UHFFFAOYSA-N 0.000 claims 1
- MPTSSPNHRTXQBL-UHFFFAOYSA-N s-[4,5-dichloro-2-[[1-(3-methylbutyl)cycloheptanecarbonyl]amino]phenyl] 2,2-dimethylpropanethioate Chemical compound C=1C(Cl)=C(Cl)C=C(SC(=O)C(C)(C)C)C=1NC(=O)C1(CCC(C)C)CCCCCC1 MPTSSPNHRTXQBL-UHFFFAOYSA-N 0.000 claims 1
- LSJSNHMUBPMISY-UHFFFAOYSA-N s-[4,5-dichloro-2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl] 2,2-dimethylpropanethioate Chemical compound C=1C(Cl)=C(Cl)C=C(SC(=O)C(C)(C)C)C=1NC(=O)C1(CCC(C)C)CCCCC1 LSJSNHMUBPMISY-UHFFFAOYSA-N 0.000 claims 1
- BFYLHKTYMPKXHG-UHFFFAOYSA-N s-[4,5-dichloro-2-[[1-(3-methylbutyl)cyclopentanecarbonyl]amino]phenyl] 2,2-dimethylpropanethioate Chemical compound C=1C(Cl)=C(Cl)C=C(SC(=O)C(C)(C)C)C=1NC(=O)C1(CCC(C)C)CCCC1 BFYLHKTYMPKXHG-UHFFFAOYSA-N 0.000 claims 1
- NOPRLOFLORGLJY-UHFFFAOYSA-N s-[4,5-dichloro-2-[[1-(cyclohexylmethyl)cyclohexanecarbonyl]amino]phenyl] 2,2-dimethylpropanethioate Chemical compound CC(C)(C)C(=O)SC1=CC(Cl)=C(Cl)C=C1NC(=O)C1(CC2CCCCC2)CCCCC1 NOPRLOFLORGLJY-UHFFFAOYSA-N 0.000 claims 1
- MSFCBUDDVRTHPO-UHFFFAOYSA-N s-[4,5-dichloro-2-[[1-(cyclopropylmethyl)cyclohexanecarbonyl]amino]phenyl] 2,2-dimethylpropanethioate Chemical compound CC(C)(C)C(=O)SC1=CC(Cl)=C(Cl)C=C1NC(=O)C1(CC2CC2)CCCCC1 MSFCBUDDVRTHPO-UHFFFAOYSA-N 0.000 claims 1
- IAJQFWNTMVVJFU-UHFFFAOYSA-N s-[4,5-difluoro-2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl] 2,2-dimethylpropanethioate Chemical compound C=1C(F)=C(F)C=C(SC(=O)C(C)(C)C)C=1NC(=O)C1(CCC(C)C)CCCCC1 IAJQFWNTMVVJFU-UHFFFAOYSA-N 0.000 claims 1
- TURBPAKUUPDMHO-UHFFFAOYSA-N s-[4-chloro-2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl] 2,2-dimethylpropanethioate Chemical compound C=1C(Cl)=CC=C(SC(=O)C(C)(C)C)C=1NC(=O)C1(CCC(C)C)CCCCC1 TURBPAKUUPDMHO-UHFFFAOYSA-N 0.000 claims 1
- GQAZVPMGDGAFBJ-UHFFFAOYSA-N s-[4-cyano-2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl] 2,2-dimethylpropanethioate Chemical compound C=1C(C#N)=CC=C(SC(=O)C(C)(C)C)C=1NC(=O)C1(CCC(C)C)CCCCC1 GQAZVPMGDGAFBJ-UHFFFAOYSA-N 0.000 claims 1
- XIKSVWQUCOSSBL-UHFFFAOYSA-N s-[4-methyl-2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl] ethanethioate Chemical compound C=1C(C)=CC=C(SC(C)=O)C=1NC(=O)C1(CCC(C)C)CCCCC1 XIKSVWQUCOSSBL-UHFFFAOYSA-N 0.000 claims 1
- PPLIUJAXWQFCOC-UHFFFAOYSA-N s-[5-chloro-2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl] 2,2-dimethylpropanethioate Chemical compound C=1C=C(Cl)C=C(SC(=O)C(C)(C)C)C=1NC(=O)C1(CCC(C)C)CCCCC1 PPLIUJAXWQFCOC-UHFFFAOYSA-N 0.000 claims 1
- FEENFRZHDJHJGY-UHFFFAOYSA-N s-[5-fluoro-2-[[1-(3-methylbutyl)cyclohexanecarbonyl]amino]phenyl] 2,2-dimethylpropanethioate Chemical compound C=1C=C(F)C=C(SC(=O)C(C)(C)C)C=1NC(=O)C1(CCC(C)C)CCCCC1 FEENFRZHDJHJGY-UHFFFAOYSA-N 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
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| US8022058B2 (en) | 2000-05-10 | 2011-09-20 | The Trustees Of Columbia University In The City Of New York | Agents for preventing and treating disorders involving modulation of the RyR receptors |
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| AU2004220548A1 (en) | 2003-03-07 | 2004-09-23 | The Trustees Of Columbia University, In The City Of New York | Type 1 ryanodine receptor-based methods |
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2004
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- 2004-03-17 NZ NZ542852A patent/NZ542852A/en not_active IP Right Cessation
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- 2004-03-17 PL PL04721345T patent/PL1603553T3/pl unknown
- 2004-03-17 BR BRPI0408466A patent/BRPI0408466B8/pt not_active IP Right Cessation
- 2004-03-17 JP JP2006507668A patent/JP5546715B2/ja not_active Expired - Lifetime
- 2004-03-17 US US10/802,220 patent/US20040225018A1/en not_active Abandoned
- 2004-03-17 EP EP10179280A patent/EP2289507A1/en not_active Withdrawn
- 2004-03-17 SI SI200431822T patent/SI1603553T1/sl unknown
- 2004-03-17 KR KR1020057017449A patent/KR100857759B1/ko not_active Expired - Lifetime
- 2004-03-17 AU AU2004222434A patent/AU2004222434B2/en not_active Expired
- 2004-03-17 ES ES04721345T patent/ES2377121T3/es not_active Expired - Lifetime
- 2004-03-17 EP EP04721345A patent/EP1603553B9/en not_active Expired - Lifetime
- 2004-03-17 DK DK04721345.9T patent/DK1603553T3/da active
- 2004-03-17 MX MXPA05009848A patent/MXPA05009848A/es active IP Right Grant
- 2004-03-17 CA CA002519432A patent/CA2519432C/en not_active Expired - Fee Related
- 2004-03-17 KR KR1020087000175A patent/KR20080008440A/ko not_active Withdrawn
-
2005
- 2005-09-08 IL IL170749A patent/IL170749A/en active IP Right Grant
- 2005-10-14 NO NO20054740A patent/NO336891B1/no not_active IP Right Cessation
- 2005-10-14 CO CO05105279A patent/CO5640101A2/es not_active Application Discontinuation
-
2010
- 2010-11-10 JP JP2010252215A patent/JP2011052006A/ja active Pending
-
2012
- 2012-02-06 CY CY20121100126T patent/CY1112324T1/el unknown
-
2013
- 2013-07-26 US US13/951,909 patent/US20140243414A1/en not_active Abandoned
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