ES2580803T3 - Moduladores de transportadores del casete de unión a ATP - Google Patents
Moduladores de transportadores del casete de unión a ATP Download PDFInfo
- Publication number
- ES2580803T3 ES2580803T3 ES13167785.8T ES13167785T ES2580803T3 ES 2580803 T3 ES2580803 T3 ES 2580803T3 ES 13167785 T ES13167785 T ES 13167785T ES 2580803 T3 ES2580803 T3 ES 2580803T3
- Authority
- ES
- Spain
- Prior art keywords
- optionally substituted
- independently
- ring
- carboxylic acid
- aliphatic
- 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.)
- Active
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- 125000001931 aliphatic group Chemical group 0.000 abstract description 14
- 229910052736 halogen Inorganic materials 0.000 abstract description 11
- 150000002367 halogens Chemical class 0.000 abstract description 11
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 10
- 239000001257 hydrogen Substances 0.000 abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 6
- 125000004429 atom Chemical group 0.000 abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract description 6
- 125000003107 substituted aryl group Chemical group 0.000 abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 4
- -1 2- (tert-butyl) indole-5- yl Chemical group 0.000 abstract description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 208000007466 Male Infertility Diseases 0.000 abstract 1
- 208000035467 Pancreatic insufficiency Diseases 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HARUWJZORCBAAL-UHFFFAOYSA-N 6-(chloromethyl)-2,3-dihydro-1,4-benzodioxine Chemical compound O1CCOC2=CC(CCl)=CC=C21 HARUWJZORCBAAL-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- ZONLKONEGHMVBB-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzodioxin-6-yl)acetonitrile Chemical compound O1CCOC2=CC(CC#N)=CC=C21 ZONLKONEGHMVBB-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- BJHIKXHVCXFQLS-UHFFFAOYSA-N 1,3,4,5,6-pentahydroxyhexan-2-one Chemical compound OCC(O)C(O)C(O)C(=O)CO BJHIKXHVCXFQLS-UHFFFAOYSA-N 0.000 description 1
- NZZVDTIYQUASAT-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)cyclopropane-1-carboxylic acid Chemical compound C=1C=C2OCOC2=CC=1C1(C(=O)O)CC1 NZZVDTIYQUASAT-UHFFFAOYSA-N 0.000 description 1
- WDOQMVLDSMTVKP-UHFFFAOYSA-N 1-(1,3-dihydro-2-benzofuran-5-yl)cyclopropane-1-carboxylic acid Chemical compound C=1C=C2COCC2=CC=1C1(C(=O)O)CC1 WDOQMVLDSMTVKP-UHFFFAOYSA-N 0.000 description 1
- RRWKJVZZARHFPB-UHFFFAOYSA-N 1-(1-benzofuran-5-yl)cyclopropane-1-carboxylic acid Chemical compound C=1C=C2OC=CC2=CC=1C1(C(=O)O)CC1 RRWKJVZZARHFPB-UHFFFAOYSA-N 0.000 description 1
- HBLYKIRKVAVJLQ-UHFFFAOYSA-N 1-(1-benzofuran-6-yl)cyclopropane-1-carboxylic acid Chemical compound C=1C=C2C=COC2=CC=1C1(C(=O)O)CC1 HBLYKIRKVAVJLQ-UHFFFAOYSA-N 0.000 description 1
- YMTWFOQAQOMXRP-UHFFFAOYSA-N 1-(1-methylbenzimidazol-5-yl)cyclopropane-1-carboxylic acid Chemical compound C=1C=C2N(C)C=NC2=CC=1C1(C(O)=O)CC1 YMTWFOQAQOMXRP-UHFFFAOYSA-N 0.000 description 1
- PONCYYKNRUMPBJ-UHFFFAOYSA-N 1-(1-methylbenzotriazol-5-yl)cyclopropane-1-carboxylic acid Chemical compound C=1C=C2N(C)N=NC2=CC=1C1(C(O)=O)CC1 PONCYYKNRUMPBJ-UHFFFAOYSA-N 0.000 description 1
- UFFAEXWKGYYSSQ-UHFFFAOYSA-N 1-(1h-indol-5-yl)cyclopropane-1-carboxylic acid Chemical compound C=1C=C2NC=CC2=CC=1C1(C(=O)O)CC1 UFFAEXWKGYYSSQ-UHFFFAOYSA-N 0.000 description 1
- IELWGOUPQRHXLS-UHFFFAOYSA-N 1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropane-1-carboxylic acid Chemical compound C=1C=C2OC(F)(F)OC2=CC=1C1(C(=O)O)CC1 IELWGOUPQRHXLS-UHFFFAOYSA-N 0.000 description 1
- RKHLGXXHPSCJJL-UHFFFAOYSA-N 1-(2,2-dimethyl-1,3-benzodioxol-5-yl)cyclopropane-1-carboxylic acid Chemical compound C1=C2OC(C)(C)OC2=CC=C1C1(C(O)=O)CC1 RKHLGXXHPSCJJL-UHFFFAOYSA-N 0.000 description 1
- QVXPITFURMQHIV-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-6-yl)cyclopropane-1-carboxylic acid Chemical compound C=1C=C2OCCOC2=CC=1C1(C(=O)O)CC1 QVXPITFURMQHIV-UHFFFAOYSA-N 0.000 description 1
- UNYWNRTZUCJKPY-UHFFFAOYSA-N 1-(2,3-dihydro-1-benzofuran-5-yl)cyclopropane-1-carboxylic acid Chemical compound C=1C=C2OCCC2=CC=1C1(C(=O)O)CC1 UNYWNRTZUCJKPY-UHFFFAOYSA-N 0.000 description 1
- DDBSEHVRDVYHRQ-UHFFFAOYSA-N 1-(2,3-dihydro-1-benzofuran-6-yl)cyclopropane-1-carboxylic acid Chemical compound C=1C=C2CCOC2=CC=1C1(C(=O)O)CC1 DDBSEHVRDVYHRQ-UHFFFAOYSA-N 0.000 description 1
- CZPYUTXQDVNAFL-UHFFFAOYSA-N 1-(2-methoxyphenyl)cyclopropane-1-carboxylic acid Chemical compound COC1=CC=CC=C1C1(C(O)=O)CC1 CZPYUTXQDVNAFL-UHFFFAOYSA-N 0.000 description 1
- KNYGHQQOCHYYSP-UHFFFAOYSA-N 1-(2-methyl-3h-benzimidazol-5-yl)cyclopropane-1-carboxylic acid Chemical compound C=1C=C2NC(C)=NC2=CC=1C1(C(O)=O)CC1 KNYGHQQOCHYYSP-UHFFFAOYSA-N 0.000 description 1
- RHPXKWHEJOXWEH-UHFFFAOYSA-N 1-(2-oxo-3h-1,3-benzoxazol-5-yl)cyclopropane-1-carboxylic acid Chemical compound C=1C=C2OC(=O)NC2=CC=1C1(C(=O)O)CC1 RHPXKWHEJOXWEH-UHFFFAOYSA-N 0.000 description 1
- PGJOQLCGZQSXCU-UHFFFAOYSA-N 1-(2h-benzotriazol-5-yl)cyclopropane-1-carboxylic acid Chemical compound C=1C=C2NN=NC2=CC=1C1(C(=O)O)CC1 PGJOQLCGZQSXCU-UHFFFAOYSA-N 0.000 description 1
- YSWZECDCQZHATN-UHFFFAOYSA-N 1-(3,3-dimethyl-2h-1-benzofuran-5-yl)cyclopropane-1-carboxylic acid Chemical compound C1=C2C(C)(C)COC2=CC=C1C1(C(O)=O)CC1 YSWZECDCQZHATN-UHFFFAOYSA-N 0.000 description 1
- BYUXTEWDOBYESO-UHFFFAOYSA-N 1-(3,4-difluorophenyl)cyclopropane-1-carboxylic acid Chemical compound C=1C=C(F)C(F)=CC=1C1(C(=O)O)CC1 BYUXTEWDOBYESO-UHFFFAOYSA-N 0.000 description 1
- HLADYMRXHXVWDP-UHFFFAOYSA-N 1-(3,4-dihydro-2h-chromen-6-yl)cyclopropane-1-carboxylic acid Chemical compound C=1C=C2OCCCC2=CC=1C1(C(=O)O)CC1 HLADYMRXHXVWDP-UHFFFAOYSA-N 0.000 description 1
- GHJFLVNGRUWTLC-UHFFFAOYSA-N 1-(3,4-dihydroxyphenyl)cyclopropane-1-carboxylic acid Chemical compound C=1C=C(O)C(O)=CC=1C1(C(=O)O)CC1 GHJFLVNGRUWTLC-UHFFFAOYSA-N 0.000 description 1
- FELRPROQUKLRFC-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)cyclopropane-1-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC=C1C1(C(O)=O)CC1 FELRPROQUKLRFC-UHFFFAOYSA-N 0.000 description 1
- YAGVSCARZZXXKU-UHFFFAOYSA-N 1-(3-chloro-4-hydroxyphenyl)cyclopropane-1-carboxylic acid Chemical compound C=1C=C(O)C(Cl)=CC=1C1(C(=O)O)CC1 YAGVSCARZZXXKU-UHFFFAOYSA-N 0.000 description 1
- IJNNWPMZHGIFOW-UHFFFAOYSA-N 1-(3-chloro-4-methoxyphenyl)cyclopropane-1-carboxylic acid Chemical compound C1=C(Cl)C(OC)=CC=C1C1(C(O)=O)CC1 IJNNWPMZHGIFOW-UHFFFAOYSA-N 0.000 description 1
- JKIHCIJMQGMLOG-UHFFFAOYSA-N 1-(3-fluoro-4-methoxyphenyl)cyclopropane-1-carboxylic acid Chemical compound C1=C(F)C(OC)=CC=C1C1(C(O)=O)CC1 JKIHCIJMQGMLOG-UHFFFAOYSA-N 0.000 description 1
- DQALANWWCRLIPZ-UHFFFAOYSA-N 1-(3-hydroxy-4-methoxyphenyl)cyclopropane-1-carboxylic acid Chemical compound C1=C(O)C(OC)=CC=C1C1(C(O)=O)CC1 DQALANWWCRLIPZ-UHFFFAOYSA-N 0.000 description 1
- HNUPNADNJWDNFR-UHFFFAOYSA-N 1-(3-hydroxyphenyl)cyclopropane-1-carboxylic acid Chemical compound C=1C=CC(O)=CC=1C1(C(=O)O)CC1 HNUPNADNJWDNFR-UHFFFAOYSA-N 0.000 description 1
- OJHMCTKCWHHFRP-UHFFFAOYSA-N 1-(3-methoxy-4-phenylmethoxyphenyl)cyclopropane-1-carboxylic acid Chemical compound COC1=CC(C2(CC2)C(O)=O)=CC=C1OCC1=CC=CC=C1 OJHMCTKCWHHFRP-UHFFFAOYSA-N 0.000 description 1
- OKGXVHRWLUXELM-UHFFFAOYSA-N 1-(3-methoxyphenyl)cyclopropane-1-carboxylic acid Chemical compound COC1=CC=CC(C2(CC2)C(O)=O)=C1 OKGXVHRWLUXELM-UHFFFAOYSA-N 0.000 description 1
- WDHARPWQZYVRJH-UHFFFAOYSA-N 1-(3-methyl-1,2-benzoxazol-5-yl)cyclopropane-1-carboxylic acid Chemical compound C1=C2C(C)=NOC2=CC=C1C1(C(O)=O)CC1 WDHARPWQZYVRJH-UHFFFAOYSA-N 0.000 description 1
- HVCJDJBLQHCTFY-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)cyclopropane-1-carboxylic acid Chemical compound C=1C=C2NC=NC2=CC=1C1(C(=O)O)CC1 HVCJDJBLQHCTFY-UHFFFAOYSA-N 0.000 description 1
- QQYJLBPFNCLOMD-UHFFFAOYSA-N 1-(4-chloro-3-hydroxyphenyl)cyclopropane-1-carboxylic acid Chemical compound C=1C=C(Cl)C(O)=CC=1C1(C(=O)O)CC1 QQYJLBPFNCLOMD-UHFFFAOYSA-N 0.000 description 1
- HMAIOQOQPGCPKW-UHFFFAOYSA-N 1-(4-chloro-3-methoxyphenyl)cyclopropane-1-carboxylic acid Chemical compound C1=C(Cl)C(OC)=CC(C2(CC2)C(O)=O)=C1 HMAIOQOQPGCPKW-UHFFFAOYSA-N 0.000 description 1
- WTRVVRPSILRMNP-UHFFFAOYSA-N 1-(4-chloro-3-phenylmethoxyphenyl)cyclopropane-1-carboxylic acid Chemical compound C=1C=C(Cl)C(OCC=2C=CC=CC=2)=CC=1C1(C(=O)O)CC1 WTRVVRPSILRMNP-UHFFFAOYSA-N 0.000 description 1
- UPNXUJXIIZGXLQ-UHFFFAOYSA-N 1-(4-chlorophenyl)cyclohexane-1-carboxylic acid Chemical compound C=1C=C(Cl)C=CC=1C1(C(=O)O)CCCCC1 UPNXUJXIIZGXLQ-UHFFFAOYSA-N 0.000 description 1
- QJNFJEMGWIQMJT-UHFFFAOYSA-N 1-(4-chlorophenyl)cyclopentane-1-carboxylic acid Chemical compound C=1C=C(Cl)C=CC=1C1(C(=O)O)CCCC1 QJNFJEMGWIQMJT-UHFFFAOYSA-N 0.000 description 1
- YAHLWSGIQJATGG-UHFFFAOYSA-N 1-(4-chlorophenyl)cyclopropane-1-carboxylic acid Chemical compound C=1C=C(Cl)C=CC=1C1(C(=O)O)CC1 YAHLWSGIQJATGG-UHFFFAOYSA-N 0.000 description 1
- AOGCLMKYKRLDAB-UHFFFAOYSA-N 1-(4-hydroxy-4-methoxy-2,3-dihydrochromen-6-yl)cyclopropane-1-carboxylic acid Chemical compound C1=C2C(OC)(O)CCOC2=CC=C1C1(C(O)=O)CC1 AOGCLMKYKRLDAB-UHFFFAOYSA-N 0.000 description 1
- MBSAMXWFQMZRNE-UHFFFAOYSA-N 1-(4-methoxy-3-methylphenyl)cyclopropane-1-carboxylic acid Chemical compound C1=C(C)C(OC)=CC=C1C1(C(O)=O)CC1 MBSAMXWFQMZRNE-UHFFFAOYSA-N 0.000 description 1
- ZZXMORPBGYOROB-UHFFFAOYSA-N 1-(4-methoxy-3-phenylmethoxyphenyl)cyclopropane-1-carboxylic acid Chemical compound COC1=CC=C(C2(CC2)C(O)=O)C=C1OCC1=CC=CC=C1 ZZXMORPBGYOROB-UHFFFAOYSA-N 0.000 description 1
- JKJAJSWMKTWWJS-UHFFFAOYSA-N 1-(4-methoxyphenyl)cyclohexane-1-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1(C(O)=O)CCCCC1 JKJAJSWMKTWWJS-UHFFFAOYSA-N 0.000 description 1
- OMMROWIAJMZSLF-UHFFFAOYSA-N 1-(4-methoxyphenyl)cyclopentane-1-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1(C(O)=O)CCCC1 OMMROWIAJMZSLF-UHFFFAOYSA-N 0.000 description 1
- WCPFQQHADRJANG-UHFFFAOYSA-N 1-(4-methoxyphenyl)cyclopropane-1-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1(C(O)=O)CC1 WCPFQQHADRJANG-UHFFFAOYSA-N 0.000 description 1
- JONFWIWGPHCFLV-UHFFFAOYSA-N 1-(4-oxo-2,3-dihydrochromen-6-yl)cyclopropane-1-carboxylic acid Chemical compound C=1C=C2OCCC(=O)C2=CC=1C1(C(=O)O)CC1 JONFWIWGPHCFLV-UHFFFAOYSA-N 0.000 description 1
- CWIRUFZXQCNXLK-UHFFFAOYSA-N 1-(7-chloro-1,3-benzodioxol-5-yl)cyclopropane-1-carboxylic acid Chemical compound C=1C=2OCOC=2C(Cl)=CC=1C1(C(=O)O)CC1 CWIRUFZXQCNXLK-UHFFFAOYSA-N 0.000 description 1
- IREXTUHKNSCNHV-UHFFFAOYSA-N 1-(7-fluoro-1,3-benzodioxol-5-yl)cyclopropane-1-carboxylic acid Chemical compound C=1C=2OCOC=2C(F)=CC=1C1(C(=O)O)CC1 IREXTUHKNSCNHV-UHFFFAOYSA-N 0.000 description 1
- TVBHFGQXOHONQC-UHFFFAOYSA-N 1-(7-methoxy-1,3-benzodioxol-5-yl)cyclopropane-1-carboxylic acid Chemical compound C=1C=2OCOC=2C(OC)=CC=1C1(C(O)=O)CC1 TVBHFGQXOHONQC-UHFFFAOYSA-N 0.000 description 1
- HQBNLJOWTODEPR-UHFFFAOYSA-N 1-[3-(hydroxymethyl)-4-methoxyphenyl]cyclopropane-1-carboxylic acid Chemical compound C1=C(CO)C(OC)=CC=C1C1(C(O)=O)CC1 HQBNLJOWTODEPR-UHFFFAOYSA-N 0.000 description 1
- WLYQHMMKMYCFAP-UHFFFAOYSA-N 1-[4-(trifluoromethoxy)phenyl]cyclopropane-1-carboxylic acid Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C1(C(=O)O)CC1 WLYQHMMKMYCFAP-UHFFFAOYSA-N 0.000 description 1
- QXXHHHWXFHPNOS-UHFFFAOYSA-N 1-phenylcyclohexane-1-carboxylic acid Chemical compound C=1C=CC=CC=1C1(C(=O)O)CCCCC1 QXXHHHWXFHPNOS-UHFFFAOYSA-N 0.000 description 1
- RHPCYZLXNNRRMB-UHFFFAOYSA-N 1-phenylcyclopentane-1-carboxylic acid Chemical compound C=1C=CC=CC=1C1(C(=O)O)CCCC1 RHPCYZLXNNRRMB-UHFFFAOYSA-N 0.000 description 1
- IWWCCNVRNHTGLV-UHFFFAOYSA-N 1-phenylcyclopropane-1-carboxylic acid Chemical compound C=1C=CC=CC=1C1(C(=O)O)CC1 IWWCCNVRNHTGLV-UHFFFAOYSA-N 0.000 description 1
- MAKLRUMKFWTSAY-UHFFFAOYSA-N 1-spiro[1,3-benzodioxole-2,1'-cyclobutane]-5-ylcyclopropane-1-carboxylic acid Chemical compound C=1C=C2OC3(CCC3)OC2=CC=1C1(C(=O)O)CC1 MAKLRUMKFWTSAY-UHFFFAOYSA-N 0.000 description 1
- FFLHNBGNAWYMRH-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxin-6-ylmethanol Chemical compound O1CCOC2=CC(CO)=CC=C21 FFLHNBGNAWYMRH-UHFFFAOYSA-N 0.000 description 1
- HUAOQQIUUYXNFN-UHFFFAOYSA-N 4-(4-methoxyphenyl)oxane-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1(C(O)=O)CCOCC1 HUAOQQIUUYXNFN-UHFFFAOYSA-N 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- 229910006124 SOCl2 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
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| AU2005210474B2 (en) * | 2004-01-30 | 2011-07-07 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding cassette transporters |
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| US9012496B2 (en) | 2012-07-16 | 2015-04-21 | Vertex Pharmaceuticals Incorporated | Pharmaceutical compositions of (R)-1-(2,2-difluorobenzo[D][1,3]dioxol-5-yl)-N-(1-(2,3-dihydroxypropyl)-6-fluoro-2-(1-hydroxy-2-methylpropan-2-yl)-1H-indol-5-yl)cyclopropanecarboxamide and administration thereof |
| SMT201800590T1 (it) | 2012-11-02 | 2019-01-11 | Vertex Pharma | Composizioni farmaceutiche per il trattamento di malattie mediate da cftr |
| US20140221424A1 (en) | 2013-01-30 | 2014-08-07 | Vertex Pharmaceuticals Incorporated | Pharmaceutical compositions for use in the treatment of cystic fibrosis |
| AU2014302458A1 (en) | 2013-06-26 | 2015-12-24 | Proteostasis Therapeutics, Inc. | Methods of modulating CFTR activity |
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| TWI715523B (zh) | 2013-12-27 | 2021-01-11 | 日商中外製藥股份有限公司 | 含有托格列淨(Tofogliflozin)之固體製劑及其製造方法 |
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| SI3221692T1 (sl) | 2014-11-18 | 2021-11-30 | Vertex Pharmaceuticals Inc. | Postopek za izvajanje testov visoke prepustnosti z visoko zmogljivostno tekočinsko kromatografijo |
| MA41031A (fr) | 2014-11-26 | 2017-10-03 | Catabasis Pharmaceuticals Inc | Conjugués cystéamine-acide gras et leur utilisation comme activateurs de l'autophagie |
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