CA2691474A1 - Cyanoisoquinoleine - Google Patents
Cyanoisoquinoleine Download PDFInfo
- Publication number
- CA2691474A1 CA2691474A1 CA002691474A CA2691474A CA2691474A1 CA 2691474 A1 CA2691474 A1 CA 2691474A1 CA 002691474 A CA002691474 A CA 002691474A CA 2691474 A CA2691474 A CA 2691474A CA 2691474 A1 CA2691474 A1 CA 2691474A1
- Authority
- CA
- Canada
- Prior art keywords
- dimethoxy
- carbonitrile
- isoquinoline
- piperazin
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- HJHXYSBRTVFEDD-UHFFFAOYSA-N isoquinoline-1-carbonitrile Chemical compound C1=CC=C2C(C#N)=NC=CC2=C1 HJHXYSBRTVFEDD-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 96
- 238000000034 method Methods 0.000 claims abstract description 44
- 208000020016 psychiatric disease Diseases 0.000 claims abstract description 24
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- 239000003937 drug carrier Substances 0.000 claims abstract description 10
- 230000008569 process Effects 0.000 claims abstract description 8
- 101001072037 Homo sapiens cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Proteins 0.000 claims abstract description 3
- 102100036377 cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Human genes 0.000 claims abstract 2
- -1 6,7-Dimethoxy-1-[2-(4-methoxy-phenyl)-morpholin-4-yl]-isoquinoline-4-carbonitrile 6,7-Dimethoxy-1-(2-p-tolyl-morpholin-4-yl)-isoquinoline-4-carbonitrile Chemical compound 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 29
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 28
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 206010012289 Dementia Diseases 0.000 claims description 24
- 238000011282 treatment Methods 0.000 claims description 24
- 208000028017 Psychotic disease Diseases 0.000 claims description 21
- 206010013663 drug dependence Diseases 0.000 claims description 21
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims description 15
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- 150000002367 halogens Chemical class 0.000 claims description 15
- 229960003920 cocaine Drugs 0.000 claims description 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 14
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 12
- 239000003085 diluting agent Substances 0.000 claims description 12
- 208000022821 personality disease Diseases 0.000 claims description 12
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- 241000124008 Mammalia Species 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
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- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 201000006145 cocaine dependence Diseases 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 201000005040 opiate dependence Diseases 0.000 claims description 8
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 claims description 8
- 208000024254 Delusional disease Diseases 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
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- 229940124530 sulfonamide Drugs 0.000 claims description 7
- 150000003456 sulfonamides Chemical class 0.000 claims description 7
- VHPLRXAABSNXIW-UHFFFAOYSA-N 6,7-dimethoxy-1-[3-(3-methoxyphenyl)piperazin-1-yl]isoquinoline-4-carbonitrile Chemical compound COC1=CC=CC(C2NCCN(C2)C=2C3=CC(OC)=C(OC)C=C3C(C#N)=CN=2)=C1 VHPLRXAABSNXIW-UHFFFAOYSA-N 0.000 claims description 6
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- 208000005314 Multi-Infarct Dementia Diseases 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 208000022372 Reading disease Diseases 0.000 claims description 6
- 208000020186 Schizophreniform disease Diseases 0.000 claims description 6
- 208000011963 Substance-induced psychotic disease Diseases 0.000 claims description 6
- 231100000393 Substance-induced psychotic disorder Toxicity 0.000 claims description 6
- 201000004810 Vascular dementia Diseases 0.000 claims description 6
- 230000007000 age related cognitive decline Effects 0.000 claims description 6
- 230000001476 alcoholic effect Effects 0.000 claims description 6
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 6
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 claims description 6
- 230000002490 cerebral effect Effects 0.000 claims description 6
- 230000003001 depressive effect Effects 0.000 claims description 6
- 206010058319 dysgraphia Diseases 0.000 claims description 6
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- 239000000380 hallucinogen Substances 0.000 claims description 6
- 208000014674 injury Diseases 0.000 claims description 6
- 238000007917 intracranial administration Methods 0.000 claims description 6
- 201000003723 learning disability Diseases 0.000 claims description 6
- OXTKIDUJSSOMHD-UHFFFAOYSA-N n-[5-[4-(4-cyano-6,7-dimethoxyisoquinolin-1-yl)piperazin-2-yl]-2-methoxyphenyl]acetamide Chemical compound C1=C(NC(C)=O)C(OC)=CC=C1C1NCCN(C=2C3=CC(OC)=C(OC)C=C3C(C#N)=CN=2)C1 OXTKIDUJSSOMHD-UHFFFAOYSA-N 0.000 claims description 6
- 229940005483 opioid analgesics Drugs 0.000 claims description 6
- 229950010883 phencyclidine Drugs 0.000 claims description 6
- 208000022610 schizoaffective disease Diseases 0.000 claims description 6
- 230000008733 trauma Effects 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000003446 ligand Substances 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- SEESHWGGZOLEIR-UHFFFAOYSA-N 1-[2-(2-chlorophenyl)morpholin-4-yl]-6,7-dimethoxyisoquinoline-4-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=C(C#N)C=NC=1N(C1)CCOC1C1=CC=CC=C1Cl SEESHWGGZOLEIR-UHFFFAOYSA-N 0.000 claims description 2
- IPZYTQILGOUGNV-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)morpholin-4-yl]-6,7-dimethoxyisoquinoline-4-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=C(C#N)C=NC=1N(C1)CCOC1C1=CC=C(Cl)C=C1 IPZYTQILGOUGNV-UHFFFAOYSA-N 0.000 claims description 2
- NBLHJOQNQZTOKG-UHFFFAOYSA-N 1-[3-(1,3-benzodioxol-5-yl)piperazin-1-yl]-6,7-dimethoxy-3-methylisoquinoline-4-carbonitrile Chemical compound C1=C2OCOC2=CC(C2NCCN(C2)C2=C3C=C(C(=CC3=C(C#N)C(C)=N2)OC)OC)=C1 NBLHJOQNQZTOKG-UHFFFAOYSA-N 0.000 claims description 2
- USOGVMGOVDHEES-UHFFFAOYSA-N 1-[3-(1,3-benzodioxol-5-yl)piperazin-1-yl]-6,7-dimethoxyisoquinoline-4-carbonitrile Chemical compound C1=C2OCOC2=CC(C2NCCN(C2)C=2N=CC(=C3C=C(C(=CC3=2)OC)OC)C#N)=C1 USOGVMGOVDHEES-UHFFFAOYSA-N 0.000 claims description 2
- PATLSGNNAZAQCW-UHFFFAOYSA-N 1-[3-(2,4-dichloro-5-fluorophenyl)piperazin-1-yl]-6,7-dimethoxyisoquinoline-4-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=C(C#N)C=NC=1N(C1)CCNC1C1=CC(F)=C(Cl)C=C1Cl PATLSGNNAZAQCW-UHFFFAOYSA-N 0.000 claims description 2
- QTSZJTKDAGFGAQ-UHFFFAOYSA-N 1-[3-(2,4-dichlorophenyl)piperazin-1-yl]-6,7-dimethoxyisoquinoline-4-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=C(C#N)C=NC=1N(C1)CCNC1C1=CC=C(Cl)C=C1Cl QTSZJTKDAGFGAQ-UHFFFAOYSA-N 0.000 claims description 2
- NKZGRVLAMRNLEZ-UHFFFAOYSA-N 1-[3-(2,4-dimethoxyphenyl)piperazin-1-yl]-6,7-dimethoxyisoquinoline-4-carbonitrile Chemical compound COC1=CC(OC)=CC=C1C1NCCN(C=2C3=CC(OC)=C(OC)C=C3C(C#N)=CN=2)C1 NKZGRVLAMRNLEZ-UHFFFAOYSA-N 0.000 claims description 2
- IAEAVDNJKHJBBD-UHFFFAOYSA-N 1-[3-(2,5-dichlorophenyl)piperazin-1-yl]-6,7-dimethoxyisoquinoline-4-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=C(C#N)C=NC=1N(C1)CCNC1C1=CC(Cl)=CC=C1Cl IAEAVDNJKHJBBD-UHFFFAOYSA-N 0.000 claims description 2
- HPZXTEUKAGOOPV-UHFFFAOYSA-N 1-[3-(2,5-dimethoxyphenyl)piperazin-1-yl]-6,7-dimethoxy-3-methylisoquinoline-4-carbonitrile Chemical compound COC1=CC=C(OC)C(C2NCCN(C2)C=2C3=CC(OC)=C(OC)C=C3C(C#N)=C(C)N=2)=C1 HPZXTEUKAGOOPV-UHFFFAOYSA-N 0.000 claims description 2
- GBIQUSNZDHOOMK-UHFFFAOYSA-N 1-[3-(2,5-dimethoxyphenyl)piperazin-1-yl]-6,7-dimethoxyisoquinoline-4-carbonitrile Chemical compound COC1=CC=C(OC)C(C2NCCN(C2)C=2C3=CC(OC)=C(OC)C=C3C(C#N)=CN=2)=C1 GBIQUSNZDHOOMK-UHFFFAOYSA-N 0.000 claims description 2
- FIKAZIWYYSCGKV-UHFFFAOYSA-N 1-[3-(3,5-dimethoxyphenyl)piperazin-1-yl]-6,7-dimethoxy-3-methylisoquinoline-4-carbonitrile Chemical compound COC1=CC(OC)=CC(C2NCCN(C2)C=2C3=CC(OC)=C(OC)C=C3C(C#N)=C(C)N=2)=C1 FIKAZIWYYSCGKV-UHFFFAOYSA-N 0.000 claims description 2
- FVUQELSBIMKIFK-UHFFFAOYSA-N 1-[3-(3,5-dimethoxyphenyl)piperazin-1-yl]-6,7-dimethoxyisoquinoline-4-carbonitrile Chemical compound COC1=CC(OC)=CC(C2NCCN(C2)C=2C3=CC(OC)=C(OC)C=C3C(C#N)=CN=2)=C1 FVUQELSBIMKIFK-UHFFFAOYSA-N 0.000 claims description 2
- UKLRFPVJAQZCSS-UHFFFAOYSA-N 1-[3-(3-chloro-4-methoxyphenyl)piperazin-1-yl]-6,7-dimethoxyisoquinoline-4-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1C1NCCN(C=2C3=CC(OC)=C(OC)C=C3C(C#N)=CN=2)C1 UKLRFPVJAQZCSS-UHFFFAOYSA-N 0.000 claims description 2
- ZTBUUVPNBHHZKX-UHFFFAOYSA-N 1-[3-(3-chlorophenyl)piperazin-1-yl]-6,7-dimethoxyisoquinoline-4-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=C(C#N)C=NC=1N(C1)CCNC1C1=CC=CC(Cl)=C1 ZTBUUVPNBHHZKX-UHFFFAOYSA-N 0.000 claims description 2
- ZUJIIKNQQPOWPN-UHFFFAOYSA-N 1-[3-(3-fluoro-4-methoxyphenyl)piperazin-1-yl]-6,7-dimethoxyisoquinoline-4-carbonitrile Chemical compound C1=C(F)C(OC)=CC=C1C1NCCN(C=2C3=CC(OC)=C(OC)C=C3C(C#N)=CN=2)C1 ZUJIIKNQQPOWPN-UHFFFAOYSA-N 0.000 claims description 2
- IEGJKDQWJCSGIT-UHFFFAOYSA-N 1-[3-(4-bromophenyl)piperazin-1-yl]-6,7-dimethoxyisoquinoline-4-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=C(C#N)C=NC=1N(C1)CCNC1C1=CC=C(Br)C=C1 IEGJKDQWJCSGIT-UHFFFAOYSA-N 0.000 claims description 2
- TXTOIHWKTJDEPJ-UHFFFAOYSA-N 1-[3-(4-chlorophenyl)piperazin-1-yl]-6,7-dimethoxyisoquinoline-4-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=C(C#N)C=NC=1N(C1)CCNC1C1=CC=C(Cl)C=C1 TXTOIHWKTJDEPJ-UHFFFAOYSA-N 0.000 claims description 2
- CXHHDHQSCFBLIK-UHFFFAOYSA-N 1-[3-(4-ethoxyphenyl)piperazin-1-yl]-6,7-dimethoxyisoquinoline-4-carbonitrile Chemical compound C1=CC(OCC)=CC=C1C1NCCN(C=2C3=CC(OC)=C(OC)C=C3C(C#N)=CN=2)C1 CXHHDHQSCFBLIK-UHFFFAOYSA-N 0.000 claims description 2
- IXSFNICDTUOIHZ-UHFFFAOYSA-N 1-[3-(4-ethylphenyl)piperazin-1-yl]-6,7-dimethoxyisoquinoline-4-carbonitrile Chemical compound C1=CC(CC)=CC=C1C1NCCN(C=2C3=CC(OC)=C(OC)C=C3C(C#N)=CN=2)C1 IXSFNICDTUOIHZ-UHFFFAOYSA-N 0.000 claims description 2
- MIVATKKLJKUUNT-UHFFFAOYSA-N 1-[3-(4-fluorophenyl)piperazin-1-yl]-6,7-dimethoxyisoquinoline-4-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=C(C#N)C=NC=1N(C1)CCNC1C1=CC=C(F)C=C1 MIVATKKLJKUUNT-UHFFFAOYSA-N 0.000 claims description 2
- IEQSZXAIOGSYSD-UHFFFAOYSA-N 1-[3-[4-(dimethylamino)phenyl]piperazin-1-yl]-6,7-dimethoxy-3-methylisoquinoline-4-carbonitrile Chemical compound N1=C(C)C(C#N)=C2C=C(OC)C(OC)=CC2=C1N(C1)CCNC1C1=CC=C(N(C)C)C=C1 IEQSZXAIOGSYSD-UHFFFAOYSA-N 0.000 claims description 2
- DSEOZNSGJOIEFL-UHFFFAOYSA-N 1-[3-[4-(dimethylamino)phenyl]piperazin-1-yl]-6,7-dimethoxyisoquinoline-4-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=C(C#N)C=NC=1N(C1)CCNC1C1=CC=C(N(C)C)C=C1 DSEOZNSGJOIEFL-UHFFFAOYSA-N 0.000 claims description 2
- DNFOFZFKZDJFIP-UHFFFAOYSA-N 6,7-dimethoxy-1-(2-phenylthiomorpholin-4-yl)isoquinoline-4-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=C(C#N)C=NC=1N(C1)CCSC1C1=CC=CC=C1 DNFOFZFKZDJFIP-UHFFFAOYSA-N 0.000 claims description 2
- QWPUFFMWKXJJGC-UHFFFAOYSA-N 6,7-dimethoxy-1-(3-naphthalen-1-ylpiperazin-1-yl)isoquinoline-4-carbonitrile Chemical compound C1=CC=C2C(C3NCCN(C3)C=3N=CC(=C4C=C(C(=CC4=3)OC)OC)C#N)=CC=CC2=C1 QWPUFFMWKXJJGC-UHFFFAOYSA-N 0.000 claims description 2
- IPKJGWRGVXISIF-FQEVSTJZSA-N 6,7-dimethoxy-1-[(3r)-3-(4-methoxyphenyl)piperazin-1-yl]isoquinoline-4-carbonitrile Chemical compound C1=CC(OC)=CC=C1[C@H]1NCCN(C=2C3=CC(OC)=C(OC)C=C3C(C#N)=CN=2)C1 IPKJGWRGVXISIF-FQEVSTJZSA-N 0.000 claims description 2
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- HIUOSXISMBGZQC-UHFFFAOYSA-N 6,7-dimethoxy-1-[3-(3-nitrophenyl)piperazin-1-yl]isoquinoline-4-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=C(C#N)C=NC=1N(C1)CCNC1C1=CC=CC([N+]([O-])=O)=C1 HIUOSXISMBGZQC-UHFFFAOYSA-N 0.000 claims description 2
- TUWOQFPFWGMKHU-UHFFFAOYSA-N 6,7-dimethoxy-1-[3-(4-methoxy-2,6-dimethylphenyl)piperazin-1-yl]isoquinoline-4-carbonitrile Chemical compound CC1=CC(OC)=CC(C)=C1C1NCCN(C=2C3=CC(OC)=C(OC)C=C3C(C#N)=CN=2)C1 TUWOQFPFWGMKHU-UHFFFAOYSA-N 0.000 claims description 2
- OSGVJJJWYYMTID-UHFFFAOYSA-N 6,7-dimethoxy-1-[3-(4-methoxy-2-methylphenyl)piperazin-1-yl]isoquinoline-4-carbonitrile Chemical compound CC1=CC(OC)=CC=C1C1NCCN(C=2C3=CC(OC)=C(OC)C=C3C(C#N)=CN=2)C1 OSGVJJJWYYMTID-UHFFFAOYSA-N 0.000 claims description 2
- CORRHRAVMOTLIM-UHFFFAOYSA-N 6,7-dimethoxy-1-[3-(4-methoxy-3,5-dimethylphenyl)piperazin-1-yl]isoquinoline-4-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=C(C#N)C=NC=1N(C1)CCNC1C1=CC(C)=C(OC)C(C)=C1 CORRHRAVMOTLIM-UHFFFAOYSA-N 0.000 claims description 2
- UGKNKCASISPVFY-UHFFFAOYSA-N 6,7-dimethoxy-1-[3-(4-methoxyphenyl)piperazin-1-yl]-3-methylisoquinoline-4-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1NCCN(C=2C3=CC(OC)=C(OC)C=C3C(C#N)=C(C)N=2)C1 UGKNKCASISPVFY-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Psychiatry (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
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DKPA200701348 | 2007-09-19 | ||
DKPA200701348 | 2007-09-19 | ||
PCT/DK2008/050225 WO2009036766A1 (fr) | 2007-09-19 | 2008-09-18 | Cyanoisoquinoléine |
Publications (2)
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CA2691474A1 true CA2691474A1 (fr) | 2009-03-26 |
CA2691474C CA2691474C (fr) | 2013-09-10 |
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EP (1) | EP2203438A1 (fr) |
JP (1) | JP2010539195A (fr) |
CN (1) | CN101743239A (fr) |
AR (1) | AR068466A1 (fr) |
CA (1) | CA2691474C (fr) |
CL (1) | CL2008002809A1 (fr) |
TW (1) | TW200918519A (fr) |
WO (1) | WO2009036766A1 (fr) |
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US7858620B2 (en) * | 2007-09-19 | 2010-12-28 | H. Lundbeck A/S | Cyanoisoquinoline |
TW201215607A (en) * | 2010-07-02 | 2012-04-16 | Lundbeck & Co As H | Aryl-and heteroarylamid derivatives as PDE10A enzyme inhibitor |
BR112013021180A2 (pt) * | 2011-02-18 | 2019-09-24 | Allergan Inc | derivados de 6,7-dialcóxi-3-isoquinolinol substituído como inibidores de fosfodiesterase 10 (pde10a) |
US9938269B2 (en) | 2011-06-30 | 2018-04-10 | Abbvie Inc. | Inhibitor compounds of phosphodiesterase type 10A |
US20130116241A1 (en) | 2011-11-09 | 2013-05-09 | Abbvie Inc. | Novel inhibitor compounds of phosphodiesterase type 10a |
CA2852820A1 (fr) | 2011-11-09 | 2013-05-16 | AbbVie Deutschland GmbH & Co. KG | Carboxamides heterocycliques utiles comme inhibiteurs de la phosphodiesterase de type 10a |
UY34980A (es) | 2012-08-17 | 2014-03-31 | Abbvie Inc | Nuevos compuestos inhibidores de la fosfodiesterasa del tipo 10a |
KR20150056844A (ko) | 2012-09-17 | 2015-05-27 | 아비에 도이치란트 게엠베하 운트 콤파니 카게 | 포스포디에스테라제 타입 10a의 신규 억제제 화합물 |
WO2014071044A1 (fr) | 2012-11-01 | 2014-05-08 | Allergan, Inc. | Dérivés de 6,7-dialcoxy-3-isoquinoline substitués à titre d'inhibiteurs de phosphodiestérase 10 (pde10a) |
US9790203B2 (en) | 2012-11-26 | 2017-10-17 | Abbvie Inc. | Inhibitor compounds of phosphodiesterase type 10A |
US9200005B2 (en) | 2013-03-13 | 2015-12-01 | AbbVie Deutschland GmbH & Co. KG | Inhibitor compounds of phosphodiesterase type 10A |
MX2015012008A (es) | 2013-03-14 | 2016-04-15 | Abbvie Deutschland | Compuestos inhibidores novedosos de fosfodiesterasa tipo 10a. |
US9200016B2 (en) | 2013-12-05 | 2015-12-01 | Allergan, Inc. | Substituted 6, 7-dialkoxy-3-isoquinoline derivatives as inhibitors of phosphodiesterase 10 (PDE 10A) |
US20210379061A1 (en) | 2018-09-28 | 2021-12-09 | Takeda Pharmaceutical Company Limited | Balipodect for treating or preventing autism spectrum disorders |
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---|---|---|---|---|
US20060128695A1 (en) * | 2002-10-30 | 2006-06-15 | Neuro3D | Cyclic nucleotide phosphodiesterase inhibitors, preparation and uses |
UA86591C2 (ru) * | 2003-06-30 | 2009-05-12 | Алтана Фарма Аг | Пирролодигидроизохинолины как ингибиторы pde10, фармацевтическая композиция на их основе |
WO2005012485A2 (fr) * | 2003-07-31 | 2005-02-10 | Bayer Pharmaceuticals Corporation | Procedes pour traiter le diabete, et les troubles associes, au moyen d'inhibiteurs des pde10a |
CA2568929A1 (fr) * | 2004-06-07 | 2005-12-22 | Pfizer Products Inc. | Inhibition de la phosphodiesterase 10 dans le traitement des etats pathologiques associes a l'obesite et au syndrome metabolique |
US20060019975A1 (en) * | 2004-07-23 | 2006-01-26 | Pfizer Inc | Novel piperidyl derivatives of quinazoline and isoquinoline |
AU2007223801A1 (en) * | 2006-03-08 | 2007-09-13 | Amgen Inc. | Quinoline and isoquinoline derivatives as phosphodiesterase 10 inhibitors |
-
2008
- 2008-09-09 TW TW097134479A patent/TW200918519A/zh unknown
- 2008-09-17 AR ARP080104039A patent/AR068466A1/es unknown
- 2008-09-18 JP JP2010525197A patent/JP2010539195A/ja not_active Ceased
- 2008-09-18 CA CA2691474A patent/CA2691474C/fr not_active Expired - Fee Related
- 2008-09-18 EP EP08801401A patent/EP2203438A1/fr not_active Withdrawn
- 2008-09-18 CN CN200880021250A patent/CN101743239A/zh active Pending
- 2008-09-18 WO PCT/DK2008/050225 patent/WO2009036766A1/fr active Application Filing
- 2008-09-22 CL CL2008002809A patent/CL2008002809A1/es unknown
Also Published As
Publication number | Publication date |
---|---|
EP2203438A1 (fr) | 2010-07-07 |
WO2009036766A1 (fr) | 2009-03-26 |
CA2691474C (fr) | 2013-09-10 |
AR068466A1 (es) | 2009-11-18 |
JP2010539195A (ja) | 2010-12-16 |
CL2008002809A1 (es) | 2009-11-27 |
CN101743239A (zh) | 2010-06-16 |
TW200918519A (en) | 2009-05-01 |
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