UA112697C2 - Сполуки, які інгібують активність катехол-о-метилтрансферази - Google Patents

Сполуки, які інгібують активність катехол-о-метилтрансферази Download PDF

Info

Publication number: UA112697C2
Authority: UA; Ukraine
Prior art keywords: dihydroxy; alkyl; isophthalonitrile; aryl; dihydroxyisophthalonitrile
Prior art date: 2012-05-24

Application number

UAA201413852A

Other languages

English (en)

Ukrainian (uk)

Inventor

Марко Алмарк

Белл Девід Дін

Міка Кауппала

Анне Луйро

Тайна Паюнен

Ярмо Пюстюнен

Ейя Тіайнен

Матті Вайсмаа

Йозеф Мессінгер

Original Assignee

Оріон Корпорейшн

Priority date (The priority date 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 date listed.)

2012-05-24

Filing date

2013-05-23

Publication date

2016-10-10

2013-05-23 Application filed by Оріон Корпорейшн filed Critical Оріон Корпорейшн

2013-05-23 Priority claimed from PCT/FI2013/000026 external-priority patent/WO2013175053A1/fr

2016-10-10 Publication of UA112697C2 publication Critical patent/UA112697C2/uk

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 284
230000002401 inhibitory effect Effects 0.000 title abstract description 11
230000000694 effects Effects 0.000 title description 4
239000003543 catechol methyltransferase inhibitor Substances 0.000 claims abstract description 21
125000000217 alkyl group Chemical group 0.000 claims description 250
-1 aryl-5- Chemical group 0.000 claims description 247
125000003118 aryl group Chemical group 0.000 claims description 161
239000000203 mixture Substances 0.000 claims description 161
238000000034 method Methods 0.000 claims description 147
229910052736 halogen Inorganic materials 0.000 claims description 75
150000002367 halogens Chemical class 0.000 claims description 75
125000003342 alkenyl group Chemical group 0.000 claims description 69
125000003545 alkoxy group Chemical group 0.000 claims description 66
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 66
LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 claims description 61
125000001072 heteroaryl group Chemical group 0.000 claims description 58
125000000623 heterocyclic group Chemical group 0.000 claims description 51
125000001424 substituent group Chemical group 0.000 claims description 50
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 47
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 43
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 41
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 39
125000000304 alkynyl group Chemical group 0.000 claims description 32
WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 27
WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims description 27
229960004502 levodopa Drugs 0.000 claims description 27
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 25
238000002360 preparation method Methods 0.000 claims description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
229910052799 carbon Inorganic materials 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 17
125000004104 aryloxy group Chemical group 0.000 claims description 17
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 16
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 13
125000000392 cycloalkenyl group Chemical group 0.000 claims description 13
229940099362 Catechol O methyltransferase inhibitor Drugs 0.000 claims description 12
201000010099 disease Diseases 0.000 claims description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
125000004093 cyano group Chemical group *C#N 0.000 claims description 11
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 description 10
125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 10
150000002148 esters Chemical class 0.000 claims description 10
125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 8
208000018737 Parkinson disease Diseases 0.000 claims description 8
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
239000004480 active ingredient Substances 0.000 claims description 7
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 description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
NVGXGXGTZURLGS-UHFFFAOYSA-N methyl 2-(2,6-dicyano-3,4-dihydroxyphenyl)sulfanylbenzoate Chemical compound COC(=O)C1=CC=CC=C1SC1=C(C#N)C=C(O)C(O)=C1C#N NVGXGXGTZURLGS-UHFFFAOYSA-N 0.000 claims description 6
125000005504 styryl group Chemical group 0.000 claims description 6
ATQGWPGSDDWUHR-UHFFFAOYSA-N 2-(4-benzylpiperidin-1-yl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1N1CCC(CC=2C=CC=CC=2)CC1 ATQGWPGSDDWUHR-UHFFFAOYSA-N 0.000 claims description 5
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 description 5
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 description 5
LPPKZFJPKJTNGQ-UHFFFAOYSA-N 2-amino-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound NC1=C(C#N)C=C(O)C(O)=C1C#N LPPKZFJPKJTNGQ-UHFFFAOYSA-N 0.000 claims description 5
125000005553 heteroaryloxy group Chemical group 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
239000000126 substance Substances 0.000 claims description 5
238000002560 therapeutic procedure Methods 0.000 claims description 5
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 description 4
JCYAKULCZVKVNF-UHFFFAOYSA-N 2-(2,3-dihydro-1h-inden-5-yloxy)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1OC1=CC=C(CCC2)C2=C1 JCYAKULCZVKVNF-UHFFFAOYSA-N 0.000 claims description 4
KWMAWYUWCPKCGN-UHFFFAOYSA-N 2-(2,6-dimethylmorpholin-4-yl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound C1C(C)OC(C)CN1C1=C(C#N)C=C(O)C(O)=C1C#N KWMAWYUWCPKCGN-UHFFFAOYSA-N 0.000 claims description 4
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 description 4
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 description 4
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 description 4
JYFWOALMLSYDLK-UHFFFAOYSA-N 2-[(3-fluoro-4-methoxyphenyl)methyl]-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound C1=C(F)C(OC)=CC=C1CC1=C(C#N)C=C(O)C(O)=C1C#N JYFWOALMLSYDLK-UHFFFAOYSA-N 0.000 claims description 4
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 description 4
SWWZENHMWFZQSO-UHFFFAOYSA-N 2-[4-[(2,6-dicyano-3,4-dihydroxyphenyl)methyl]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1CC1=C(C#N)C=C(O)C(O)=C1C#N SWWZENHMWFZQSO-UHFFFAOYSA-N 0.000 claims description 4
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 description 4
XXMZBBKIBZJLFC-UHFFFAOYSA-N 4,5-dihydroxy-2-(2-methoxyethylamino)benzene-1,3-dicarbonitrile Chemical compound COCCNC1=C(C#N)C=C(O)C(O)=C1C#N XXMZBBKIBZJLFC-UHFFFAOYSA-N 0.000 claims description 4
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 description 4
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 description 4
IWXZIOQCOXSNIX-UHFFFAOYSA-N 4,5-dihydroxy-2-(3-methoxypropylamino)benzene-1,3-dicarbonitrile Chemical compound COCCCNC1=C(C#N)C=C(O)C(O)=C1C#N IWXZIOQCOXSNIX-UHFFFAOYSA-N 0.000 claims description 4
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 description 4
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 description 4
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 description 4
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 description 4
ZLWHCAKQHFZGHY-UHFFFAOYSA-N 4,5-dihydroxy-2-(pentan-3-ylamino)benzene-1,3-dicarbonitrile Chemical compound CCC(CC)NC1=C(C#N)C=C(O)C(O)=C1C#N ZLWHCAKQHFZGHY-UHFFFAOYSA-N 0.000 claims description 4
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 description 4
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 description 4
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 description 4
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 description 4
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 description 4
OZCJHLAFLUQOQH-UHFFFAOYSA-N 4,5-dihydroxy-2-[1-(2-methylpropyl)pyrazol-4-yl]benzene-1,3-dicarbonitrile Chemical compound C1=NN(CC(C)C)C=C1C1=C(C#N)C=C(O)C(O)=C1C#N OZCJHLAFLUQOQH-UHFFFAOYSA-N 0.000 claims description 4
PTORHPQDQRZXNR-UHFFFAOYSA-N 4,5-dihydroxy-2-morpholin-4-ylbenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1N1CCOCC1 PTORHPQDQRZXNR-UHFFFAOYSA-N 0.000 claims description 4
FXUXXZAZGWWMJW-UHFFFAOYSA-N 4,5-dihydroxy-2-naphthalen-1-ylbenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1C1=CC=CC2=CC=CC=C12 FXUXXZAZGWWMJW-UHFFFAOYSA-N 0.000 claims description 4
KLLUHZVGUJOLTB-UHFFFAOYSA-N 4,5-dihydroxy-2-naphthalen-2-ylbenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1C1=CC=C(C=CC=C2)C2=C1 KLLUHZVGUJOLTB-UHFFFAOYSA-N 0.000 claims description 4
YCQIYEZVWIPCLA-UHFFFAOYSA-N 4,5-dihydroxy-2-phenylbenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1C1=CC=CC=C1 YCQIYEZVWIPCLA-UHFFFAOYSA-N 0.000 claims description 4
ZHWWQVYDQHLZGC-UHFFFAOYSA-N 4,5-dihydroxy-2-pyridin-3-ylbenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1C1=CC=CN=C1 ZHWWQVYDQHLZGC-UHFFFAOYSA-N 0.000 claims description 4
ITYFACNLNDSSGE-UHFFFAOYSA-N 4-[(2,6-dicyano-3,4-dihydroxyphenyl)methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CC1=C(C#N)C=C(O)C(O)=C1C#N ITYFACNLNDSSGE-UHFFFAOYSA-N 0.000 claims description 4
241000124008 Mammalia Species 0.000 claims description 4
125000005605 benzo group Chemical group 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
229940126601 medicinal product Drugs 0.000 claims description 4
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 description 4
GILLLKMLIBNDKV-UHFFFAOYSA-N neluxicapone Chemical compound C1=CC(C)=CC=C1CC1=C(C#N)C=C(O)C(O)=C1C#N GILLLKMLIBNDKV-UHFFFAOYSA-N 0.000 claims description 4
AZPPQFUMOLVFQO-OWOJBTEDSA-N (e)-3-(2,6-dicyano-3,4-dihydroxyphenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=C(C#N)C=C(O)C(O)=C1C#N AZPPQFUMOLVFQO-OWOJBTEDSA-N 0.000 claims description 3
JNVAUAAKUTUYFG-UHFFFAOYSA-N 2-(1-benzylpyrazol-4-yl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1C1=CN(CC=2C=CC=CC=2)N=C1 JNVAUAAKUTUYFG-UHFFFAOYSA-N 0.000 claims description 3
MDSJHPWCTJPBNC-UHFFFAOYSA-N 2-(2,3-dihydro-1-benzofuran-5-yl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1C1=CC=C(OCC2)C2=C1 MDSJHPWCTJPBNC-UHFFFAOYSA-N 0.000 claims description 3
AAXSZTVSMNBKAZ-UHFFFAOYSA-N 2-(2,4-dimethylphenoxy)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound CC1=CC(C)=CC=C1OC1=C(C#N)C=C(O)C(O)=C1C#N AAXSZTVSMNBKAZ-UHFFFAOYSA-N 0.000 claims description 3
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 description 3
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 description 3
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 description 3
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 description 3
NLCKXTUFOUSQFD-UHFFFAOYSA-N 2-(3,3-dimethylbutyl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound CC(C)(C)CCC1=C(C#N)C=C(O)C(O)=C1C#N NLCKXTUFOUSQFD-UHFFFAOYSA-N 0.000 claims description 3
MGVOOKKXZPSLAJ-UHFFFAOYSA-N 2-(4-acetylphenoxy)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound C1=CC(C(=O)C)=CC=C1OC1=C(C#N)C=C(O)C(O)=C1C#N MGVOOKKXZPSLAJ-UHFFFAOYSA-N 0.000 claims description 3
XLJLSDNDRQXFBQ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1OC1=CC=C(Cl)C=C1 XLJLSDNDRQXFBQ-UHFFFAOYSA-N 0.000 claims description 3
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 description 3
FDINBDSSNJBBFU-UHFFFAOYSA-N 2-(4-cyanophenyl)sulfanyl-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1SC1=CC=C(C#N)C=C1 FDINBDSSNJBBFU-UHFFFAOYSA-N 0.000 claims description 3
KPRFXTSYAKPZMR-UHFFFAOYSA-N 2-(4-ethylphenoxy)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound C1=CC(CC)=CC=C1OC1=C(C#N)C=C(O)C(O)=C1C#N KPRFXTSYAKPZMR-UHFFFAOYSA-N 0.000 claims description 3
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 description 3
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 description 3
PLMNZRYKAFWFJM-UHFFFAOYSA-N 2-(cyclohexylamino)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1NC1CCCCC1 PLMNZRYKAFWFJM-UHFFFAOYSA-N 0.000 claims description 3
JYGNUCVLCNSQGM-UHFFFAOYSA-N 2-(cyclopenten-1-yl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1C1=CCCC1 JYGNUCVLCNSQGM-UHFFFAOYSA-N 0.000 claims description 3
QJDPPBBGFMCLAQ-UHFFFAOYSA-N 2-(hexylamino)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound CCCCCCNC1=C(C#N)C=C(O)C(O)=C1C#N QJDPPBBGFMCLAQ-UHFFFAOYSA-N 0.000 claims description 3
NJKROSXFJICDFP-UHFFFAOYSA-N 2-[(2,3-difluoro-4-methylphenyl)methyl]-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound FC1=C(F)C(C)=CC=C1CC1=C(C#N)C=C(O)C(O)=C1C#N NJKROSXFJICDFP-UHFFFAOYSA-N 0.000 claims description 3
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 description 3
SNDGQSGUAHTXNV-UHFFFAOYSA-N 2-[(3-fluoro-5-methylphenyl)methyl]-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound CC1=CC(F)=CC(CC=2C(=C(O)C(O)=CC=2C#N)C#N)=C1 SNDGQSGUAHTXNV-UHFFFAOYSA-N 0.000 claims description 3
ZFHOWJXZDWTILG-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1CC1=CC=C(Cl)C=C1 ZFHOWJXZDWTILG-UHFFFAOYSA-N 0.000 claims description 3
UCQGCXGTFUFNSH-UHFFFAOYSA-N 2-[(5-fluoro-2-methoxyphenyl)methyl]-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound FC=1C=CC(=C(CC2=C(C#N)C=C(C(=C2C#N)O)O)C1)OC UCQGCXGTFUFNSH-UHFFFAOYSA-N 0.000 claims description 3
GSJZJDDTPLAAPS-DUXPYHPUSA-N 2-[(e)-2-(2,4-difluorophenyl)ethenyl]-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1\C=C\C1=CC=C(F)C=C1F GSJZJDDTPLAAPS-DUXPYHPUSA-N 0.000 claims description 3
YRUGBQVTMXDQAA-VOTSOKGWSA-N 2-[(e)-2-cyclohexylethenyl]-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1\C=C\C1CCCCC1 YRUGBQVTMXDQAA-VOTSOKGWSA-N 0.000 claims description 3
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 description 3
GPVXNHTUDMIGHR-UHFFFAOYSA-N 2-[4-(2,6-dicyano-3,4-dihydroxyphenyl)pyrazol-1-yl]acetic acid Chemical compound C1=NN(CC(=O)O)C=C1C1=C(C#N)C=C(O)C(O)=C1C#N GPVXNHTUDMIGHR-UHFFFAOYSA-N 0.000 claims description 3
BCWBSGZFXLCYCF-UHFFFAOYSA-N 2-[4-(2,6-dicyano-3,4-dihydroxyphenyl)sulfanylphenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1SC1=C(C#N)C=C(O)C(O)=C1C#N BCWBSGZFXLCYCF-UHFFFAOYSA-N 0.000 claims description 3
FETZSDVHWKPZMR-UHFFFAOYSA-N 2-[4-[(2,6-dicyano-3,4-dihydroxyphenyl)methyl]phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1CC1=C(C#N)C=C(O)C(O)=C1C#N FETZSDVHWKPZMR-UHFFFAOYSA-N 0.000 claims description 3
RJSOWAFJGXXKOM-UHFFFAOYSA-N 3-(2,6-dicyano-3,4-dihydroxyphenyl)sulfanylbenzoic acid Chemical compound OC(=O)C1=CC=CC(SC=2C(=C(O)C(O)=CC=2C#N)C#N)=C1 RJSOWAFJGXXKOM-UHFFFAOYSA-N 0.000 claims description 3
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 description 3
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 description 3
UIVPKENTVBSTHA-UHFFFAOYSA-N 4,5-dihydroxy-2-(3-hydroxypropyl)benzene-1,3-dicarbonitrile Chemical compound OCCCC1=C(C#N)C=C(O)C(O)=C1C#N UIVPKENTVBSTHA-UHFFFAOYSA-N 0.000 claims description 3
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 description 3
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 description 3
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 description 3
DDWJTOPPONIOMV-UHFFFAOYSA-N 4,5-dihydroxy-2-(4-methylphenoxy)benzene-1,3-dicarbonitrile Chemical compound C1=CC(C)=CC=C1OC1=C(C#N)C=C(O)C(O)=C1C#N DDWJTOPPONIOMV-UHFFFAOYSA-N 0.000 claims description 3
NKQOTLMHPNGBSY-UHFFFAOYSA-N 4,5-dihydroxy-2-(4-phenoxyphenyl)sulfanylbenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1SC(C=C1)=CC=C1OC1=CC=CC=C1 NKQOTLMHPNGBSY-UHFFFAOYSA-N 0.000 claims description 3
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 description 3
YSEAMGZGKGDIAY-UHFFFAOYSA-N 4,5-dihydroxy-2-(naphthalen-1-ylmethyl)benzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1CC1=CC=CC2=CC=CC=C12 YSEAMGZGKGDIAY-UHFFFAOYSA-N 0.000 claims description 3
NMQBKAPWBOAJAZ-UHFFFAOYSA-N 4,5-dihydroxy-2-[(1-oxo-2,3-dihydroinden-5-yl)oxy]benzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1OC1=CC=C(C(=O)CC2)C2=C1 NMQBKAPWBOAJAZ-UHFFFAOYSA-N 0.000 claims description 3
KECFKNGOAQTSCS-UHFFFAOYSA-N 4,5-dihydroxy-2-[(2-hydroxyethylamino)methyl]benzene-1,3-dicarbonitrile;hydrochloride Chemical compound Cl.OCCNCC1=C(C#N)C=C(O)C(O)=C1C#N KECFKNGOAQTSCS-UHFFFAOYSA-N 0.000 claims description 3
JKYKGLVBLNQTKQ-UHFFFAOYSA-N 4,5-dihydroxy-2-[(4-hydroxyphenyl)methyl]benzene-1,3-dicarbonitrile Chemical compound C1=CC(O)=CC=C1CC1=C(C#N)C=C(O)C(O)=C1C#N JKYKGLVBLNQTKQ-UHFFFAOYSA-N 0.000 claims description 3
DTNYSBFWHMXEHV-UHFFFAOYSA-N 4,5-dihydroxy-2-[(4-phenylphenyl)methyl]benzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1CC1=CC=C(C=2C=CC=CC=2)C=C1 DTNYSBFWHMXEHV-UHFFFAOYSA-N 0.000 claims description 3
OEOPKWXIIGWVNC-QPJJXVBHSA-N 4,5-dihydroxy-2-[(e)-2-(4-methoxyphenyl)ethenyl]benzene-1,3-dicarbonitrile Chemical compound C1=CC(OC)=CC=C1\C=C\C1=C(C#N)C=C(O)C(O)=C1C#N OEOPKWXIIGWVNC-QPJJXVBHSA-N 0.000 claims description 3
FHADVGODXRGTPW-VOTSOKGWSA-N 4,5-dihydroxy-2-[(e)-2-(4-methylphenyl)ethenyl]benzene-1,3-dicarbonitrile Chemical compound C1=CC(C)=CC=C1\C=C\C1=C(C#N)C=C(O)C(O)=C1C#N FHADVGODXRGTPW-VOTSOKGWSA-N 0.000 claims description 3
IGNAPITUXFPXEQ-VOTSOKGWSA-N 4,5-dihydroxy-2-[(e)-2-phenylethenyl]benzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1\C=C\C1=CC=CC=C1 IGNAPITUXFPXEQ-VOTSOKGWSA-N 0.000 claims description 3
OFVRZKUBHGFREP-OWOJBTEDSA-N 4,5-dihydroxy-2-[(e)-2-thiophen-3-ylethenyl]benzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1\C=C\C1=CSC=C1 OFVRZKUBHGFREP-OWOJBTEDSA-N 0.000 claims description 3
MBDXPCNGMOBZPG-NSCUHMNNSA-N 4,5-dihydroxy-2-[(e)-3-methoxyprop-1-enyl]benzene-1,3-dicarbonitrile Chemical compound COC\C=C\C1=C(C#N)C=C(O)C(O)=C1C#N MBDXPCNGMOBZPG-NSCUHMNNSA-N 0.000 claims description 3
RMMXMAHLQIGUHU-UHFFFAOYSA-N 4,5-dihydroxy-2-[4-(morpholine-4-carbonyl)phenyl]sulfanylbenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1SC1=CC=C(C(=O)N2CCOCC2)C=C1 RMMXMAHLQIGUHU-UHFFFAOYSA-N 0.000 claims description 3
KQZMGWHXARCLLZ-UHFFFAOYSA-N 4,5-dihydroxy-2-[5-(morpholin-4-ylmethyl)thiophen-2-yl]benzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1C(S1)=CC=C1CN1CCOCC1 KQZMGWHXARCLLZ-UHFFFAOYSA-N 0.000 claims description 3
IIZLBAPQFHJOJT-UHFFFAOYSA-N 4,5-dihydroxy-2-[[4-(hydroxymethyl)phenyl]methyl]benzene-1,3-dicarbonitrile Chemical compound C1=CC(CO)=CC=C1CC1=C(C#N)C=C(O)C(O)=C1C#N IIZLBAPQFHJOJT-UHFFFAOYSA-N 0.000 claims description 3
ULCFWZSOQXHWRB-UHFFFAOYSA-N 4,5-dihydroxy-2-[[4-(trifluoromethyl)phenyl]methyl]benzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1CC1=CC=C(C(F)(F)F)C=C1 ULCFWZSOQXHWRB-UHFFFAOYSA-N 0.000 claims description 3
NAEBDSJMILVGHG-UHFFFAOYSA-N 4,5-dihydroxy-2-[[4-methyl-2-(trifluoromethyl)phenyl]methyl]benzene-1,3-dicarbonitrile Chemical compound FC(F)(F)C1=CC(C)=CC=C1CC1=C(C#N)C=C(O)C(O)=C1C#N NAEBDSJMILVGHG-UHFFFAOYSA-N 0.000 claims description 3
QVGHKFBFXXPKJF-UHFFFAOYSA-N 4,5-dihydroxy-2-methylbenzene-1,3-dicarbonitrile Chemical compound CC1=C(C#N)C=C(O)C(O)=C1C#N QVGHKFBFXXPKJF-UHFFFAOYSA-N 0.000 claims description 3
HFDKPKCXNXVXIE-UHFFFAOYSA-N 4,5-dihydroxy-2-phenylsulfanylbenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1SC1=CC=CC=C1 HFDKPKCXNXVXIE-UHFFFAOYSA-N 0.000 claims description 3
QNIHOSNRJIOCHP-UHFFFAOYSA-N 4,5-dihydroxy-2-prop-1-en-2-ylbenzene-1,3-dicarbonitrile Chemical compound CC(=C)C1=C(C#N)C=C(O)C(O)=C1C#N QNIHOSNRJIOCHP-UHFFFAOYSA-N 0.000 claims description 3
LXMNVAAXACBRNM-UHFFFAOYSA-N 4,5-dihydroxy-2-pyrrolidin-1-ylbenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1N1CCCC1 LXMNVAAXACBRNM-UHFFFAOYSA-N 0.000 claims description 3
PWKGBVNXLFYEHT-UHFFFAOYSA-N 4,5-dihydroxy-2-thiophen-2-ylbenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1C1=CC=CS1 PWKGBVNXLFYEHT-UHFFFAOYSA-N 0.000 claims description 3
WQEXLOKVICETBG-UHFFFAOYSA-N 4,5-dihydroxy-2-thiophen-3-ylbenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1C1=CSC=C1 WQEXLOKVICETBG-UHFFFAOYSA-N 0.000 claims description 3
KJDGITYGUGHUQW-UHFFFAOYSA-N 5-[(2,6-dicyano-3,4-dihydroxyphenyl)methyl]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(CC=2C(=C(O)C(O)=CC=2C#N)C#N)=C1 KJDGITYGUGHUQW-UHFFFAOYSA-N 0.000 claims description 3
XJYJIZALOHKHCH-UHFFFAOYSA-N C(C)C1=CC=C(C=NC2=C(C#N)C=C(C(=C2C#N)O)O)C=C1 Chemical compound C(C)C1=CC=C(C=NC2=C(C#N)C=C(C(=C2C#N)O)O)C=C1 XJYJIZALOHKHCH-UHFFFAOYSA-N 0.000 claims description 3
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 description 3
ZYRYSFOFIZDXMT-UHFFFAOYSA-N methyl 3-[4-(2,6-dicyano-3,4-dihydroxyphenyl)sulfanylphenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1SC1=C(C#N)C=C(O)C(O)=C1C#N ZYRYSFOFIZDXMT-UHFFFAOYSA-N 0.000 claims description 3
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 description 3
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 3
235000019260 propionic acid Nutrition 0.000 claims description 3
IVTMXOXVAHXCHI-YXLMWLKOSA-N (2s)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid;(2s)-3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic acid Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1.NN[C@@](C(O)=O)(C)CC1=CC=C(O)C(O)=C1 IVTMXOXVAHXCHI-YXLMWLKOSA-N 0.000 claims description 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 description 2
KTLVYXHOVCFXDF-UHFFFAOYSA-N 2-(3,6-dihydro-2h-pyran-4-yl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1C1=CCOCC1 KTLVYXHOVCFXDF-UHFFFAOYSA-N 0.000 claims description 2
DSWKCEZHYBGJGO-UHFFFAOYSA-N 2-(cyclohexen-1-yl)-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1C1=CCCCC1 DSWKCEZHYBGJGO-UHFFFAOYSA-N 0.000 claims description 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 description 2
LLLGDGTXDXKERE-UHFFFAOYSA-N 2-[(2-fluorophenyl)methyl]-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1CC1=CC=CC=C1F LLLGDGTXDXKERE-UHFFFAOYSA-N 0.000 claims description 2
OJSNFLKUMOUGDK-UHFFFAOYSA-N 2-[(4-chloro-2-methylphenyl)methyl]-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound CC1=CC(Cl)=CC=C1CC1=C(C#N)C=C(O)C(O)=C1C#N OJSNFLKUMOUGDK-UHFFFAOYSA-N 0.000 claims description 2
JXLWAUNELPYURD-UHFFFAOYSA-N 2-[(4-fluoro-3-methylphenyl)methyl]-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound C1=C(F)C(C)=CC(CC=2C(=C(O)C(O)=CC=2C#N)C#N)=C1 JXLWAUNELPYURD-UHFFFAOYSA-N 0.000 claims description 2
AKEDGFWTTNKSFN-UHFFFAOYSA-N 2-[(4-fluorophenyl)methyl]-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1CC1=CC=C(F)C=C1 AKEDGFWTTNKSFN-UHFFFAOYSA-N 0.000 claims description 2
OVECABHOCJNGHQ-XVNBXDOJSA-N 2-[(e)-3-cyclopentylprop-1-enyl]-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1\C=C\CC1CCCC1 OVECABHOCJNGHQ-XVNBXDOJSA-N 0.000 claims description 2
MDWWLIZJNHAPOY-UHFFFAOYSA-N 2-[5-(5-hexylthiophen-2-yl)thiophen-2-yl]-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound S1C(CCCCCC)=CC=C1C1=CC=C(C=2C(=C(O)C(O)=CC=2C#N)C#N)S1 MDWWLIZJNHAPOY-UHFFFAOYSA-N 0.000 claims description 2
NCWPQCRHFDKGJC-UHFFFAOYSA-N 2-benzyl-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1CC1=CC=CC=C1 NCWPQCRHFDKGJC-UHFFFAOYSA-N 0.000 claims description 2
VGJFSRWXUMEAEY-UHFFFAOYSA-N 2-ethyl-4,5-dihydroxybenzene-1,3-dicarbonitrile Chemical compound CCC1=C(C#N)C=C(O)C(O)=C1C#N VGJFSRWXUMEAEY-UHFFFAOYSA-N 0.000 claims description 2
QCWZNNAPANWGQS-UHFFFAOYSA-N 3-[(2,6-dicyano-3,4-dihydroxyphenyl)methyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(CC=2C(=C(O)C(O)=CC=2C#N)C#N)=C1 QCWZNNAPANWGQS-UHFFFAOYSA-N 0.000 claims description 2
XOWCAMJULXFLTN-UHFFFAOYSA-N 4,5-dihydroxy-2-(1-phenylethenyl)benzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1C(=C)C1=CC=CC=C1 XOWCAMJULXFLTN-UHFFFAOYSA-N 0.000 claims description 2
SXXUZWNWGYAHOI-UHFFFAOYSA-N 4,5-dihydroxy-2-(2-phenylethynyl)benzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1C#CC1=CC=CC=C1 SXXUZWNWGYAHOI-UHFFFAOYSA-N 0.000 claims description 2
CYIKRZYBRJSKDX-UHFFFAOYSA-N 4,5-dihydroxy-2-(3-methoxyprop-1-ynyl)benzene-1,3-dicarbonitrile Chemical compound COCC#CC1=C(C#N)C=C(O)C(O)=C1C#N CYIKRZYBRJSKDX-UHFFFAOYSA-N 0.000 claims description 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 description 2
QQQCVEAFIMUDRY-XBXARRHUSA-N 4,5-dihydroxy-2-[(e)-3-phenylprop-1-enyl]benzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1\C=C\CC1=CC=CC=C1 QQQCVEAFIMUDRY-XBXARRHUSA-N 0.000 claims description 2
MINUFASAKLTFEP-UHFFFAOYSA-N 4,5-dihydroxy-2-[3-(trifluoromethyl)phenyl]benzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1C1=CC=CC(C(F)(F)F)=C1 MINUFASAKLTFEP-UHFFFAOYSA-N 0.000 claims description 2
CQMMVRSUXFEWJG-UHFFFAOYSA-N 4,5-dihydroxy-2-[4-(trifluoromethyl)phenoxy]benzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1OC1=CC=C(C(F)(F)F)C=C1 CQMMVRSUXFEWJG-UHFFFAOYSA-N 0.000 claims description 2
VYUNPBBRKJRCKC-UHFFFAOYSA-N 4,5-dihydroxy-2-naphthalen-2-ylsulfanylbenzene-1,3-dicarbonitrile Chemical compound N#CC1=C(O)C(O)=CC(C#N)=C1SC1=CC=C(C=CC=C2)C2=C1 VYUNPBBRKJRCKC-UHFFFAOYSA-N 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 3
125000006554 (C4-C8) cycloalkenyl group Chemical group 0.000 claims 2
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229920006391 phthalonitrile polymer Polymers 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 description 1
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230000006920 protein precipitation Effects 0.000 description 1
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125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 1
GGOZGYRTNQBSSA-UHFFFAOYSA-N pyridine-2,3-diol Chemical class OC1=CC=CN=C1O GGOZGYRTNQBSSA-UHFFFAOYSA-N 0.000 description 1
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
230000009467 reduction Effects 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
238000005070 sampling Methods 0.000 description 1
230000035807 sensation Effects 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000004885 tandem mass spectrometry Methods 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
UITFWXLUFPGLDY-UHFFFAOYSA-N tert-butyl [2,4-dicyano-3-(2,6-dimethylmorpholin-4-yl)-6-methoxyphenyl] carbonate Chemical compound N#CC1=C(OC(=O)OC(C)(C)C)C(OC)=CC(C#N)=C1N1CC(C)OC(C)C1 UITFWXLUFPGLDY-UHFFFAOYSA-N 0.000 description 1
AZAHFPQXLTZXTA-UHFFFAOYSA-N tert-butyl [2,4-dicyano-3-(cyclohexylamino)-6-methoxyphenyl] carbonate Chemical compound N#CC1=C(OC(=O)OC(C)(C)C)C(OC)=CC(C#N)=C1NC1CCCCC1 AZAHFPQXLTZXTA-UHFFFAOYSA-N 0.000 description 1
AJDRXJKRJANNGW-UHFFFAOYSA-N tert-butyl [2,4-dicyano-6-methoxy-3-(2-methoxyethylamino)phenyl] carbonate Chemical compound COCCNC1=C(C#N)C=C(OC)C(OC(=O)OC(C)(C)C)=C1C#N AJDRXJKRJANNGW-UHFFFAOYSA-N 0.000 description 1
GHICQQQGVUZQAW-UHFFFAOYSA-N tert-butyl [2,4-dicyano-6-methoxy-3-(3-methoxypropylamino)phenyl] carbonate Chemical compound COCCCNC1=C(C#N)C=C(OC)C(OC(=O)OC(C)(C)C)=C1C#N GHICQQQGVUZQAW-UHFFFAOYSA-N 0.000 description 1
YYDFTIZJYGOLDX-UHFFFAOYSA-N tert-butyl [2,4-dicyano-6-methoxy-3-(pentan-3-ylamino)phenyl] carbonate Chemical compound CCC(CC)NC1=C(C#N)C=C(OC)C(OC(=O)OC(C)(C)C)=C1C#N YYDFTIZJYGOLDX-UHFFFAOYSA-N 0.000 description 1
XKXIQBVKMABYQJ-UHFFFAOYSA-M tert-butyl carbonate Chemical compound CC(C)(C)OC([O-])=O XKXIQBVKMABYQJ-UHFFFAOYSA-M 0.000 description 1
238000012360 testing method Methods 0.000 description 1
125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
LWNCDBSQZPDFOG-UHFFFAOYSA-N tributyl(2-methylprop-1-enyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C(C)C LWNCDBSQZPDFOG-UHFFFAOYSA-N 0.000 description 1
KCQJLTOSSVXOCC-UHFFFAOYSA-N tributyl(prop-1-ynyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C#CC KCQJLTOSSVXOCC-UHFFFAOYSA-N 0.000 description 1
YLGRTLMDMVAFNI-UHFFFAOYSA-N tributyl(prop-2-enyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)CC=C YLGRTLMDMVAFNI-UHFFFAOYSA-N 0.000 description 1
UKTDFYOZPFNQOQ-UHFFFAOYSA-N tributyl(thiophen-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CS1 UKTDFYOZPFNQOQ-UHFFFAOYSA-N 0.000 description 1
DINAKCGOEKXDTP-UHFFFAOYSA-N tributyl-(1-methylpyrrol-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CN1C DINAKCGOEKXDTP-UHFFFAOYSA-N 0.000 description 1
HKTFMFBUSSUPGJ-UHFFFAOYSA-N tributyl-(2-ethoxy-1,3-thiazol-5-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CN=C(OCC)S1 HKTFMFBUSSUPGJ-UHFFFAOYSA-N 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
235000012141 vanillin Nutrition 0.000 description 1
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

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Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

UAA201413852A 2012-05-24 2013-05-23 Сполуки, які інгібують активність катехол-о-метилтрансферази UA112697C2 (uk)

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US201261651217P	2012-05-24	2012-05-24
PCT/FI2013/000026 WO2013175053A1 (fr)	2012-05-24	2013-05-23	Composés inhibant l'activité de la catéchol o-méthyltransférase

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MA37561B1 (fr)	2016-09-30

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