ES2554353T3 - Moduladores de transportadores del casete de unión a ATP - Google Patents
Moduladores de transportadores del casete de unión a ATP Download PDFInfo
- Publication number
- ES2554353T3 ES2554353T3 ES07755298.2T ES07755298T ES2554353T3 ES 2554353 T3 ES2554353 T3 ES 2554353T3 ES 07755298 T ES07755298 T ES 07755298T ES 2554353 T3 ES2554353 T3 ES 2554353T3
- Authority
- ES
- Spain
- Prior art keywords
- independently
- optionally substituted
- halogen
- aliphatic
- ring
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 abstract description 35
- 229910052736 halogen Inorganic materials 0.000 abstract description 29
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 26
- 150000002367 halogens Chemical class 0.000 abstract description 25
- -1 -OH Chemical group 0.000 abstract description 23
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 20
- 239000001257 hydrogen Substances 0.000 abstract description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 20
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 16
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 13
- 125000003118 aryl group Chemical group 0.000 abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 9
- 125000004429 atom Chemical group 0.000 abstract description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 7
- 125000005842 heteroatom Chemical group 0.000 abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract description 4
- 125000002950 monocyclic group Chemical group 0.000 abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 abstract description 3
- 125000005843 halogen group Chemical group 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000002619 bicyclic group Chemical group 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 9
- 150000002431 hydrogen Chemical group 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
- 125000001041 indolyl group Chemical group 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 125000002837 carbocyclic group Chemical group 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
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004043 oxo group Chemical group O=* 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 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
- 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
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 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
- 125000003368 amide group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([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
- 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
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