JP2015522547A5 - - Google Patents
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- Publication number
- JP2015522547A5 JP2015522547A5 JP2015513234A JP2015513234A JP2015522547A5 JP 2015522547 A5 JP2015522547 A5 JP 2015522547A5 JP 2015513234 A JP2015513234 A JP 2015513234A JP 2015513234 A JP2015513234 A JP 2015513234A JP 2015522547 A5 JP2015522547 A5 JP 2015522547A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydroxy
- alkyl
- isophthalonitrile
- dihydroxyisophthalonitrile
- aryl
- 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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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 65
- 125000003118 aryl group Chemical group 0.000 claims 46
- 125000001424 substituent group Chemical group 0.000 claims 25
- 150000001875 compounds Chemical class 0.000 claims 24
- 229910052736 halogen Inorganic materials 0.000 claims 24
- 150000002367 halogens Chemical class 0.000 claims 24
- 125000001072 heteroaryl group Chemical group 0.000 claims 24
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 21
- 125000000623 heterocyclic group Chemical group 0.000 claims 18
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 16
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 12
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000004104 aryloxy group Chemical group 0.000 claims 8
- -1 -S- Chemical group 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- SXUJYFUQEBCEQC-UHFFFAOYSA-N 4,5-dihydroxy-2-(4-methylphenyl)sulfinylbenzene-1,3-dicarbonitrile Chemical compound C1=CC(C)=CC=C1S(=O)C1=C(C#N)C=C(O)C(O)=C1C#N SXUJYFUQEBCEQC-UHFFFAOYSA-N 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- WRMOTBFQPWIWKJ-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1C1=CC2=CC=CC=C2O1 WRMOTBFQPWIWKJ-UHFFFAOYSA-N 0.000 claims 2
- YKDPOHVWOHYLFW-UHFFFAOYSA-N 2-(1-benzothiophen-2-yl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1C1=CC2=CC=CC=C2S1 YKDPOHVWOHYLFW-UHFFFAOYSA-N 0.000 claims 2
- MPEVAWSDBABWDV-UHFFFAOYSA-N 2-(2,4-dimethylphenyl)sulfanyl-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound CC1=CC(C)=CC=C1SC1=C(C#N)C=C(O)C(O)=C1C#N MPEVAWSDBABWDV-UHFFFAOYSA-N 0.000 claims 2
- HHTCYPAGVGJZAR-UHFFFAOYSA-N 2-(2,5-dimethylphenyl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound CC1=CC=C(C)C(C=2C(=C(O)C(O)=CC=2C#N)C#N)=C1 HHTCYPAGVGJZAR-UHFFFAOYSA-N 0.000 claims 2
- WCSUOXUOVLTKFD-UHFFFAOYSA-N 2-(2,5-dimethylthiophen-3-yl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound S1C(C)=CC(C=2C(=C(O)C(O)=CC=2C#N)C#N)=C1C WCSUOXUOVLTKFD-UHFFFAOYSA-N 0.000 claims 2
- GUMRAWQGDJOCLN-UHFFFAOYSA-N 2-(2,6-dicyano-3,4-dihydroxyphenyl)sulfanylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1SC1=C(C#N)C=C(O)C(O)=C1C#N GUMRAWQGDJOCLN-UHFFFAOYSA-N 0.000 claims 2
- RQQJDTMYWQXCNQ-UHFFFAOYSA-N 2-(2-chlorophenyl)sulfanyl-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1SC1=CC=CC=C1Cl RQQJDTMYWQXCNQ-UHFFFAOYSA-N 0.000 claims 2
- VBVOXCKLGZPDIW-UHFFFAOYSA-N 2-(2-ethoxy-1,3-thiazol-5-yl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound S1C(OCC)=NC=C1C1=C(C#N)C=C(O)C(O)=C1C#N VBVOXCKLGZPDIW-UHFFFAOYSA-N 0.000 claims 2
- RWUFYJBSUZEBLN-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1C1=CC=C(Cl)C(Cl)=C1 RWUFYJBSUZEBLN-UHFFFAOYSA-N 0.000 claims 2
- UGCSIICSBLXZFL-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1C1=CC=C(F)C(F)=C1 UGCSIICSBLXZFL-UHFFFAOYSA-N 0.000 claims 2
- QSHGDZHDJOMOIU-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1=C(C#N)C=C(O)C(O)=C1C#N QSHGDZHDJOMOIU-UHFFFAOYSA-N 0.000 claims 2
- XFJOIGJXNNVKFE-UHFFFAOYSA-N 2-(3,4-dimethylphenyl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound C1=C(C)C(C)=CC=C1C1=C(C#N)C=C(O)C(O)=C1C#N XFJOIGJXNNVKFE-UHFFFAOYSA-N 0.000 claims 2
- GXFCKWUXFROWPF-UHFFFAOYSA-N 2-(3,5-dimethylphenyl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound CC1=CC(C)=CC(C=2C(=C(O)C(O)=CC=2C#N)C#N)=C1 GXFCKWUXFROWPF-UHFFFAOYSA-N 0.000 claims 2
- SZRJMCZAWDMSEA-UHFFFAOYSA-N 2-(3-ethylphenyl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound CCC1=CC=CC(C=2C(=C(O)C(O)=CC=2C#N)C#N)=C1 SZRJMCZAWDMSEA-UHFFFAOYSA-N 0.000 claims 2
- PCUKLZNWLBIGHE-UHFFFAOYSA-N 2-(4-butylphenyl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound C1=CC(CCCC)=CC=C1C1=C(C#N)C=C(O)C(O)=C1C#N PCUKLZNWLBIGHE-UHFFFAOYSA-N 0.000 claims 2
- RFKFRZAEKGALJP-UHFFFAOYSA-N 2-(4-chloro-3-methylphenyl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound C1=C(Cl)C(C)=CC(C=2C(=C(O)C(O)=CC=2C#N)C#N)=C1 RFKFRZAEKGALJP-UHFFFAOYSA-N 0.000 claims 2
- DKGRKPDYWCUMBQ-UHFFFAOYSA-N 2-(4-chlorophenyl)sulfanyl-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1SC1=CC=C(Cl)C=C1 DKGRKPDYWCUMBQ-UHFFFAOYSA-N 0.000 claims 2
- NVBUXBHSTROYDV-UHFFFAOYSA-N 2-(4-ethylphenyl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound C1=CC(CC)=CC=C1C1=C(C#N)C=C(O)C(O)=C1C#N NVBUXBHSTROYDV-UHFFFAOYSA-N 0.000 claims 2
- LOHMAVGXJJXBGV-UHFFFAOYSA-N 2-(4-ethylphenyl)sulfanyl-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound C1=CC(CC)=CC=C1SC1=C(C#N)C=C(O)C(O)=C1C#N LOHMAVGXJJXBGV-UHFFFAOYSA-N 0.000 claims 2
- BSOFKRUNZCXJRX-UHFFFAOYSA-N 2-(4-fluoro-3-methoxyphenyl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound C1=C(F)C(OC)=CC(C=2C(=C(O)C(O)=CC=2C#N)C#N)=C1 BSOFKRUNZCXJRX-UHFFFAOYSA-N 0.000 claims 2
- RDCVFQWVSNFOLH-UHFFFAOYSA-N 2-(4-fluoro-3-methylphenyl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound C1=C(F)C(C)=CC(C=2C(=C(O)C(O)=CC=2C#N)C#N)=C1 RDCVFQWVSNFOLH-UHFFFAOYSA-N 0.000 claims 2
- QIULYBCFZUXEPS-UHFFFAOYSA-N 2-(4-fluorophenyl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1C1=CC=C(F)C=C1 QIULYBCFZUXEPS-UHFFFAOYSA-N 0.000 claims 2
- NHHKCAWXIXGNOW-UHFFFAOYSA-N 2-(4-fluorophenyl)sulfanyl-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1SC1=CC=C(F)C=C1 NHHKCAWXIXGNOW-UHFFFAOYSA-N 0.000 claims 2
- SRZHYRHIYFKYLH-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=C(C#N)C=C(O)C(O)=C1C#N SRZHYRHIYFKYLH-UHFFFAOYSA-N 0.000 claims 2
- DKSOVKLVBAGNQC-UHFFFAOYSA-N 2-(5-chlorothiophen-2-yl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1C1=CC=C(Cl)S1 DKSOVKLVBAGNQC-UHFFFAOYSA-N 0.000 claims 2
- PLEOKVGZUMCJKC-UHFFFAOYSA-N 2-(5-hexylthiophen-2-yl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound S1C(CCCCCC)=CC=C1C1=C(C#N)C=C(O)C(O)=C1C#N PLEOKVGZUMCJKC-UHFFFAOYSA-N 0.000 claims 2
- NPABYYWAQONFLO-UHFFFAOYSA-N 2-(furan-2-yl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1C1=CC=CO1 NPABYYWAQONFLO-UHFFFAOYSA-N 0.000 claims 2
- MMFIBCTVFPKPJD-UHFFFAOYSA-N 2-(furan-3-yl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1C1=COC=C1 MMFIBCTVFPKPJD-UHFFFAOYSA-N 0.000 claims 2
- VOWBPQBYOYIQEV-UHFFFAOYSA-N 2-[(2,4-dimethylphenyl)methyl]-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound CC1=CC(C)=CC=C1CC1=C(C#N)C=C(O)C(O)=C1C#N VOWBPQBYOYIQEV-UHFFFAOYSA-N 0.000 claims 2
- XGZDAQYWZXEJCB-UHFFFAOYSA-N 2-[(2,5-dimethylphenyl)methyl]-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound CC1=CC=C(C)C(CC=2C(=C(O)C(O)=CC=2C#N)C#N)=C1 XGZDAQYWZXEJCB-UHFFFAOYSA-N 0.000 claims 2
- OBKCNPNICXSFAK-UHFFFAOYSA-N 2-[(2-ethylphenyl)methyl]-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound CCC1=CC=CC=C1CC1=C(C#N)C=C(O)C(O)=C1C#N OBKCNPNICXSFAK-UHFFFAOYSA-N 0.000 claims 2
- YIDXRBPZRUZWHU-UHFFFAOYSA-N 2-[(3,5-dimethylphenyl)methyl]-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound CC1=CC(C)=CC(CC=2C(=C(O)C(O)=CC=2C#N)C#N)=C1 YIDXRBPZRUZWHU-UHFFFAOYSA-N 0.000 claims 2
- HGPBRWOEDRSNRY-UHFFFAOYSA-N 2-[(4-ethylphenyl)methyl]-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound C1=CC(CC)=CC=C1CC1=C(C#N)C=C(O)C(O)=C1C#N HGPBRWOEDRSNRY-UHFFFAOYSA-N 0.000 claims 2
- LFMXNUUAZFKXEP-SNAWJCMRSA-N 2-[(e)-3,3-dimethylbut-1-enyl]-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound CC(C)(C)\C=C\C1=C(C#N)C=C(O)C(O)=C1C#N LFMXNUUAZFKXEP-SNAWJCMRSA-N 0.000 claims 2
- JZVZBANAUAQMBF-NSCUHMNNSA-N 2-[(e)-but-2-enyl]-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound C\C=C\CC1=C(C#N)C=C(O)C(O)=C1C#N JZVZBANAUAQMBF-NSCUHMNNSA-N 0.000 claims 2
- JZVZBANAUAQMBF-IHWYPQMZSA-N 2-[(z)-but-2-enyl]-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound C\C=C/CC1=C(C#N)C=C(O)C(O)=C1C#N JZVZBANAUAQMBF-IHWYPQMZSA-N 0.000 claims 2
- TVFOPAUFPBSFEC-UHFFFAOYSA-N 2-ethenyl-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound OC1=CC(C#N)=C(C=C)C(C#N)=C1O TVFOPAUFPBSFEC-UHFFFAOYSA-N 0.000 claims 2
- FDVYQEWGHNXPQN-UHFFFAOYSA-N 4,5-dihydroxy-2-(1-methylpyrazol-4-yl)benzene-1,3-dicarbonitrile Chemical compound C1=NN(C)C=C1C1=C(C#N)C=C(O)C(O)=C1C#N FDVYQEWGHNXPQN-UHFFFAOYSA-N 0.000 claims 2
- FJEPAFDSYTUQJJ-UHFFFAOYSA-N 4,5-dihydroxy-2-(1-methylpyrrol-2-yl)benzene-1,3-dicarbonitrile Chemical compound CN1C=CC=C1C1=C(C#N)C=C(O)C(O)=C1C#N FJEPAFDSYTUQJJ-UHFFFAOYSA-N 0.000 claims 2
- CYXVKRQIYRKTOD-UHFFFAOYSA-N 4,5-dihydroxy-2-(2-methylphenyl)benzene-1,3-dicarbonitrile Chemical compound CC1=CC=CC=C1C1=C(C#N)C=C(O)C(O)=C1C#N CYXVKRQIYRKTOD-UHFFFAOYSA-N 0.000 claims 2
- NMPOFAAWTFMFRB-UHFFFAOYSA-N 4,5-dihydroxy-2-(2-methylphenyl)sulfanylbenzene-1,3-dicarbonitrile Chemical compound CC1=CC=CC=C1SC1=C(C#N)C=C(O)C(O)=C1C#N NMPOFAAWTFMFRB-UHFFFAOYSA-N 0.000 claims 2
- ZHDDULHIXMCHLM-UHFFFAOYSA-N 4,5-dihydroxy-2-(2-methylprop-1-enyl)benzene-1,3-dicarbonitrile Chemical compound CC(C)=CC1=C(C#N)C=C(O)C(O)=C1C#N ZHDDULHIXMCHLM-UHFFFAOYSA-N 0.000 claims 2
- SWZWUSBUTUQWBQ-UHFFFAOYSA-N 4,5-dihydroxy-2-(3-methoxyphenyl)sulfanylbenzene-1,3-dicarbonitrile Chemical compound COC1=CC=CC(SC=2C(=C(O)C(O)=CC=2C#N)C#N)=C1 SWZWUSBUTUQWBQ-UHFFFAOYSA-N 0.000 claims 2
- KEZOIYLMIKHTQA-UHFFFAOYSA-N 4,5-dihydroxy-2-(3-methylbut-2-en-2-yl)benzene-1,3-dicarbonitrile Chemical compound CC(C)=C(C)C1=C(C#N)C=C(O)C(O)=C1C#N KEZOIYLMIKHTQA-UHFFFAOYSA-N 0.000 claims 2
- HUFIIRWHGASLHT-UHFFFAOYSA-N 4,5-dihydroxy-2-(3-methylbut-2-enyl)benzene-1,3-dicarbonitrile Chemical compound CC(C)=CCC1=C(C#N)C=C(O)C(O)=C1C#N HUFIIRWHGASLHT-UHFFFAOYSA-N 0.000 claims 2
- AQNROFGRTLAZAI-UHFFFAOYSA-N 4,5-dihydroxy-2-(3-methylphenyl)benzene-1,3-dicarbonitrile Chemical compound CC1=CC=CC(C=2C(=C(O)C(O)=CC=2C#N)C#N)=C1 AQNROFGRTLAZAI-UHFFFAOYSA-N 0.000 claims 2
- CAVPFONTRDCUGS-UHFFFAOYSA-N 4,5-dihydroxy-2-(3-propan-2-ylphenyl)benzene-1,3-dicarbonitrile Chemical compound CC(C)C1=CC=CC(C=2C(=C(O)C(O)=CC=2C#N)C#N)=C1 CAVPFONTRDCUGS-UHFFFAOYSA-N 0.000 claims 2
- JZOQFUKEYDHTFG-UHFFFAOYSA-N 4,5-dihydroxy-2-(4-methoxyphenyl)benzene-1,3-dicarbonitrile Chemical compound C1=CC(OC)=CC=C1C1=C(C#N)C=C(O)C(O)=C1C#N JZOQFUKEYDHTFG-UHFFFAOYSA-N 0.000 claims 2
- JHEPHGSZFOETLK-UHFFFAOYSA-N 4,5-dihydroxy-2-(4-methoxyphenyl)sulfanylbenzene-1,3-dicarbonitrile Chemical compound C1=CC(OC)=CC=C1SC1=C(C#N)C=C(O)C(O)=C1C#N JHEPHGSZFOETLK-UHFFFAOYSA-N 0.000 claims 2
- BQXLCRWMXPKFMF-UHFFFAOYSA-N 4,5-dihydroxy-2-(4-methylphenyl)benzene-1,3-dicarbonitrile Chemical compound C1=CC(C)=CC=C1C1=C(C#N)C=C(O)C(O)=C1C#N BQXLCRWMXPKFMF-UHFFFAOYSA-N 0.000 claims 2
- WCXWHLMVDZMSPC-UHFFFAOYSA-N 4,5-dihydroxy-2-(4-methylphenyl)sulfanylbenzene-1,3-dicarbonitrile Chemical compound C1=CC(C)=CC=C1SC1=C(C#N)C=C(O)C(O)=C1C#N WCXWHLMVDZMSPC-UHFFFAOYSA-N 0.000 claims 2
- GGSUVYHOFWUALH-UHFFFAOYSA-N 4,5-dihydroxy-2-(4-propan-2-yloxyphenyl)benzene-1,3-dicarbonitrile Chemical compound C1=CC(OC(C)C)=CC=C1C1=C(C#N)C=C(O)C(O)=C1C#N GGSUVYHOFWUALH-UHFFFAOYSA-N 0.000 claims 2
- YZZDCXAWHMAVRI-UHFFFAOYSA-N 4,5-dihydroxy-2-(4-propan-2-ylphenyl)benzene-1,3-dicarbonitrile Chemical compound C1=CC(C(C)C)=CC=C1C1=C(C#N)C=C(O)C(O)=C1C#N YZZDCXAWHMAVRI-UHFFFAOYSA-N 0.000 claims 2
- GSCCDWDNRSLBEE-UHFFFAOYSA-N 4,5-dihydroxy-2-(4-propoxyphenyl)benzene-1,3-dicarbonitrile Chemical compound C1=CC(OCCC)=CC=C1C1=C(C#N)C=C(O)C(O)=C1C#N GSCCDWDNRSLBEE-UHFFFAOYSA-N 0.000 claims 2
- SWNSRZVRUTWKEZ-UHFFFAOYSA-N 4,5-dihydroxy-2-(4-propylphenyl)benzene-1,3-dicarbonitrile Chemical compound C1=CC(CCC)=CC=C1C1=C(C#N)C=C(O)C(O)=C1C#N SWNSRZVRUTWKEZ-UHFFFAOYSA-N 0.000 claims 2
- NMEHNHVRERXEJE-UHFFFAOYSA-N 4,5-dihydroxy-2-(5-methylfuran-2-yl)benzene-1,3-dicarbonitrile Chemical compound O1C(C)=CC=C1C1=C(C#N)C=C(O)C(O)=C1C#N NMEHNHVRERXEJE-UHFFFAOYSA-N 0.000 claims 2
- WFNFTDSNHAEWBV-UHFFFAOYSA-N 4,5-dihydroxy-2-(5-methylthiophen-2-yl)benzene-1,3-dicarbonitrile Chemical compound S1C(C)=CC=C1C1=C(C#N)C=C(O)C(O)=C1C#N WFNFTDSNHAEWBV-UHFFFAOYSA-N 0.000 claims 2
- POUIMLDGRWLNLE-UHFFFAOYSA-N 4,5-dihydroxy-2-(6-methoxynaphthalen-2-yl)benzene-1,3-dicarbonitrile Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C1=C(C#N)C=C(O)C(O)=C1C#N POUIMLDGRWLNLE-UHFFFAOYSA-N 0.000 claims 2
- OZTILRVPXKVVQE-UHFFFAOYSA-N 4,5-dihydroxy-2-[(2-methoxyphenyl)methyl]benzene-1,3-dicarbonitrile Chemical compound COC1=CC=CC=C1CC1=C(C#N)C=C(O)C(O)=C1C#N OZTILRVPXKVVQE-UHFFFAOYSA-N 0.000 claims 2
- XVSRJMZDHREXNY-UHFFFAOYSA-N 4,5-dihydroxy-2-[(2-methylphenyl)methyl]benzene-1,3-dicarbonitrile Chemical compound CC1=CC=CC=C1CC1=C(C#N)C=C(O)C(O)=C1C#N XVSRJMZDHREXNY-UHFFFAOYSA-N 0.000 claims 2
- VFDRCKGFBHUFPP-UHFFFAOYSA-N 4,5-dihydroxy-2-[(3-methylphenyl)methyl]benzene-1,3-dicarbonitrile Chemical compound CC1=CC=CC(CC=2C(=C(O)C(O)=CC=2C#N)C#N)=C1 VFDRCKGFBHUFPP-UHFFFAOYSA-N 0.000 claims 2
- IOLDKKZEBHKDQD-UHFFFAOYSA-N 4,5-dihydroxy-2-[(4-propan-2-ylphenyl)methyl]benzene-1,3-dicarbonitrile Chemical compound C1=CC(C(C)C)=CC=C1CC1=C(C#N)C=C(O)C(O)=C1C#N IOLDKKZEBHKDQD-UHFFFAOYSA-N 0.000 claims 2
- UUNRAXZKEKDTSE-UHFFFAOYSA-N 4,5-dihydroxy-2-[(6-methoxynaphthalen-2-yl)methyl]benzene-1,3-dicarbonitrile Chemical compound C1=CC2=CC(OC)=CC=C2C=C1CC1=C(C#N)C=C(O)C(O)=C1C#N UUNRAXZKEKDTSE-UHFFFAOYSA-N 0.000 claims 2
- HRHNAYJLXAFBMP-HWKANZROSA-N 4,5-dihydroxy-2-[(e)-4-methylpent-1-enyl]benzene-1,3-dicarbonitrile Chemical compound CC(C)C\C=C\C1=C(C#N)C=C(O)C(O)=C1C#N HRHNAYJLXAFBMP-HWKANZROSA-N 0.000 claims 2
- ZFLAHUUYMWKZOM-SNAWJCMRSA-N 4,5-dihydroxy-2-[(e)-pent-1-enyl]benzene-1,3-dicarbonitrile Chemical compound CCC\C=C\C1=C(C#N)C=C(O)C(O)=C1C#N ZFLAHUUYMWKZOM-SNAWJCMRSA-N 0.000 claims 2
- QIGOCKONENVPEX-NSCUHMNNSA-N 4,5-dihydroxy-2-[(e)-prop-1-enyl]benzene-1,3-dicarbonitrile Chemical compound C\C=C\C1=C(C#N)C=C(O)C(O)=C1C#N QIGOCKONENVPEX-NSCUHMNNSA-N 0.000 claims 2
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- PXYHPLGIONSYQK-UHFFFAOYSA-N methyl 2-[4-[(2,6-dicyano-3,4-dihydroxyphenyl)methyl]phenyl]acetate Chemical compound C1=CC(CC(=O)OC)=CC=C1CC1=C(C#N)C=C(O)C(O)=C1C#N PXYHPLGIONSYQK-UHFFFAOYSA-N 0.000 claims 1
- MJWBSLVERYPSDX-UHFFFAOYSA-N methyl 4-(2,6-dicyano-3,4-dihydroxyphenoxy)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1OC1=C(C#N)C=C(O)C(O)=C1C#N MJWBSLVERYPSDX-UHFFFAOYSA-N 0.000 claims 1
- FGMPRFUGRGZDTN-UHFFFAOYSA-N methyl 4-(2,6-dicyano-3,4-dihydroxyphenyl)sulfanylbenzoate Chemical compound C1=CC(C(=O)OC)=CC=C1SC1=C(C#N)C=C(O)C(O)=C1C#N FGMPRFUGRGZDTN-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims 1
- AZGMRSGNXXIFKL-UHFFFAOYSA-N n-butyl-4-(2,6-dicyano-3,4-dihydroxyphenyl)benzamide Chemical compound C1=CC(C(=O)NCCCC)=CC=C1C1=C(C#N)C=C(O)C(O)=C1C#N AZGMRSGNXXIFKL-UHFFFAOYSA-N 0.000 claims 1
- WNFXXRRZFZIRMN-UHFFFAOYSA-N n-cyclohexyl-3-(2,6-dicyano-3,4-dihydroxyphenyl)benzamide Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1C1=CC=CC(C(=O)NC2CCCCC2)=C1 WNFXXRRZFZIRMN-UHFFFAOYSA-N 0.000 claims 1
- PMGQQMXBUNZOHS-UHFFFAOYSA-N n-cyclohexyl-4-(2,6-dicyano-3,4-dihydroxyphenyl)benzamide Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1C1=CC=C(C(=O)NC2CCCCC2)C=C1 PMGQQMXBUNZOHS-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- VHIJIGMENODJCM-UHFFFAOYSA-N tert-butyl 3-(2,6-dicyano-3,4-dihydroxyphenyl)benzoate Chemical compound CC(C)(C)OC(=O)C1=CC=CC(C=2C(=C(O)C(O)=CC=2C#N)C#N)=C1 VHIJIGMENODJCM-UHFFFAOYSA-N 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
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| EP3590940B1 (en) | 2012-09-25 | 2021-06-09 | F. Hoffmann-La Roche AG | Hexahydropyrrolo[3,4-c]pyrrole derivatives and related compounds as autotaxin (atx) inhibitors and as inhibitors of the lysophosphatidic acid (lpa) production for treating e.g. renal diseases |
| AR095079A1 (es) | 2013-03-12 | 2015-09-16 | Hoffmann La Roche | Derivados de octahidro-pirrolo[3,4-c]-pirrol y piridina-fenilo |
| NO3074400T3 (enExample) | 2013-11-26 | 2018-04-14 | ||
| MA39792B1 (fr) | 2014-03-26 | 2019-12-31 | Hoffmann La Roche | Composés bicycliques en tant qu'inhibiteurs de production d'autotaxine (atx) et d'acide lysophosphatidique (lpa) |
| EP3122751B1 (en) | 2014-03-26 | 2019-10-30 | F.Hoffmann-La Roche Ag | Condensed [1,4]diazepine compounds as autotaxin (atx) and lysophosphatidic acid (lpa) production inhibitors |
| MA41898A (fr) | 2015-04-10 | 2018-02-13 | Hoffmann La Roche | Dérivés de quinazolinone bicyclique |
| MX387736B (es) | 2015-09-04 | 2025-03-18 | Hoffmann La Roche | Derivados de fenoximetilo. |
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