JP2007523152A - キナゾリンおよびイソキノリンのテトラヒドロイソキノリニル誘導体 - Google Patents
キナゾリンおよびイソキノリンのテトラヒドロイソキノリニル誘導体 Download PDFInfo
- Publication number
- JP2007523152A JP2007523152A JP2006553698A JP2006553698A JP2007523152A JP 2007523152 A JP2007523152 A JP 2007523152A JP 2006553698 A JP2006553698 A JP 2006553698A JP 2006553698 A JP2006553698 A JP 2006553698A JP 2007523152 A JP2007523152 A JP 2007523152A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- disorder
- compound
- isoquinolin
- mammal
- 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.)
- Abandoned
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- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 title description 11
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 92
- 238000000034 method Methods 0.000 claims abstract description 80
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 58
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 241000124008 Mammalia Species 0.000 claims description 54
- 208000035475 disorder Diseases 0.000 claims description 54
- 229910052736 halogen Inorganic materials 0.000 claims description 47
- 150000002367 halogens Chemical class 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 38
- 125000003342 alkenyl group Chemical group 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- -1 4-methoxy-1,3-dioxa-7,9-diaza-cyclopenta [a] naphthalen-6-yl Chemical group 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 125000000304 alkynyl group Chemical group 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 201000000980 schizophrenia Diseases 0.000 claims description 17
- 206010012289 Dementia Diseases 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- 230000036651 mood Effects 0.000 claims description 13
- 230000004770 neurodegeneration Effects 0.000 claims description 13
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 12
- 208000019901 Anxiety disease Diseases 0.000 claims description 12
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 12
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 12
- 208000024891 symptom Diseases 0.000 claims description 12
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 12
- 208000028017 Psychotic disease Diseases 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 208000020016 psychiatric disease Diseases 0.000 claims description 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
- 208000023105 Huntington disease Diseases 0.000 claims description 10
- 208000018737 Parkinson disease Diseases 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 206010013663 drug dependence Diseases 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 9
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 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 8
- 239000002581 neurotoxin Substances 0.000 claims description 8
- 231100000618 neurotoxin Toxicity 0.000 claims description 8
- 101710138657 Neurotoxin Proteins 0.000 claims description 7
- 230000007278 cognition impairment Effects 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 208000019906 panic disease Diseases 0.000 claims description 7
- 208000011117 substance-related disease Diseases 0.000 claims description 7
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims description 6
- 208000020401 Depressive disease Diseases 0.000 claims description 6
- 208000019022 Mood disease Diseases 0.000 claims description 6
- 208000027099 Paranoid disease Diseases 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 208000024714 major depressive disease Diseases 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 230000000698 schizophrenic effect Effects 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 208000016285 Movement disease Diseases 0.000 claims description 5
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- 239000000651 prodrug Substances 0.000 claims description 5
- 229940002612 prodrug Drugs 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims description 4
- 206010065040 AIDS dementia complex Diseases 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 208000027534 Emotional disease Diseases 0.000 claims description 4
- 206010061216 Infarction Diseases 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- 206010034912 Phobia Diseases 0.000 claims description 4
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229940025084 amphetamine Drugs 0.000 claims description 4
- 229960003920 cocaine Drugs 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 230000007574 infarction Effects 0.000 claims description 4
- CXPWLJYVNZFQPX-UHFFFAOYSA-N n-[2-(6,7-dimethoxyquinazolin-4-yl)-3,4-dihydro-1h-isoquinolin-7-yl]-4-propan-2-ylbenzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(CC1=C2)CCC1=CC=C2NS(=O)(=O)C1=CC=C(C(C)C)C=C1 CXPWLJYVNZFQPX-UHFFFAOYSA-N 0.000 claims description 4
- DJNSJXYEAWGFBL-UHFFFAOYSA-N n-[2-(6,7-dimethoxyquinazolin-4-yl)-3,4-dihydro-1h-isoquinolin-7-yl]acetamide Chemical compound C1CC2=CC=C(NC(C)=O)C=C2CN1C1=C(C=C(C(OC)=C2)OC)C2=NC=N1 DJNSJXYEAWGFBL-UHFFFAOYSA-N 0.000 claims description 4
- 208000022821 personality disease Diseases 0.000 claims description 4
- 231100000572 poisoning Toxicity 0.000 claims description 4
- 230000000607 poisoning effect Effects 0.000 claims description 4
- 208000028173 post-traumatic stress disease Diseases 0.000 claims description 4
- YWQUEJLVFCBHRP-UHFFFAOYSA-N 1-(3,4-dihydro-1h-isoquinolin-2-yl)-6,7-dimethoxyisoquinoline Chemical group C1CC2=CC=CC=C2CN1C1=C(C=C(C(OC)=C2)OC)C2=CC=N1 YWQUEJLVFCBHRP-UHFFFAOYSA-N 0.000 claims description 3
- YXJKFOSZPDJMPY-UHFFFAOYSA-N 2-(6,7-dimethoxyquinazolin-4-yl)-3,4-dihydro-1h-isoquinolin-7-amine Chemical compound C1CC2=CC=C(N)C=C2CN1C1=C(C=C(C(OC)=C2)OC)C2=NC=N1 YXJKFOSZPDJMPY-UHFFFAOYSA-N 0.000 claims description 3
- WFTBEXYCSPIJSL-UHFFFAOYSA-N 3-chloro-n-[2-(6,7-dimethoxyquinazolin-4-yl)-3,4-dihydro-1h-isoquinolin-7-yl]benzamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(CC1=C2)CCC1=CC=C2NC(=O)C1=CC=CC(Cl)=C1 WFTBEXYCSPIJSL-UHFFFAOYSA-N 0.000 claims description 3
- WGDYPQLFKDSLSE-UHFFFAOYSA-N 4-(3,4-dihydro-1h-isoquinolin-2-yl)-6-ethoxy-7-methoxyquinazoline Chemical compound C1CC2=CC=CC=C2CN1C1=C2C=C(OCC)C(OC)=CC2=NC=N1 WGDYPQLFKDSLSE-UHFFFAOYSA-N 0.000 claims description 3
- BJVLSVOQWNJBLR-UHFFFAOYSA-N 4-chloro-n-[2-(6,7-dimethoxyquinazolin-4-yl)-3,4-dihydro-1h-isoquinolin-7-yl]benzamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(CC1=C2)CCC1=CC=C2NC(=O)C1=CC=C(Cl)C=C1 BJVLSVOQWNJBLR-UHFFFAOYSA-N 0.000 claims description 3
- DPHDZOLFXPCYMD-UHFFFAOYSA-N 4-chloro-n-[2-(6,7-dimethoxyquinazolin-4-yl)-3,4-dihydro-1h-isoquinolin-7-yl]benzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(CC1=C2)CCC1=CC=C2NS(=O)(=O)C1=CC=C(Cl)C=C1 DPHDZOLFXPCYMD-UHFFFAOYSA-N 0.000 claims description 3
- IKLHKJWPKXTFLB-UHFFFAOYSA-N 4-tert-butyl-n-[2-(6,7-dimethoxyquinazolin-4-yl)-3,4-dihydro-1h-isoquinolin-7-yl]benzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(CC1=C2)CCC1=CC=C2NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 IKLHKJWPKXTFLB-UHFFFAOYSA-N 0.000 claims description 3
- XOFGGFSZAJCEEW-UHFFFAOYSA-N 6,7-dimethoxy-4-[8-(4-methylpiperazin-1-yl)sulfonyl-3,4-dihydro-1h-isoquinolin-2-yl]quinazoline Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(CC1=2)CCC1=CC=CC=2S(=O)(=O)N1CCN(C)CC1 XOFGGFSZAJCEEW-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 208000024254 Delusional disease Diseases 0.000 claims description 3
- 206010026749 Mania Diseases 0.000 claims description 3
- 208000006011 Stroke Diseases 0.000 claims description 3
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 3
- 208000016620 Tourette disease Diseases 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 230000006999 cognitive decline Effects 0.000 claims description 3
- JPMVVTJYSRIFCD-UHFFFAOYSA-N n-[2-(6,7-dimethoxyquinazolin-4-yl)-3,4-dihydro-1h-isoquinolin-7-yl]-2,2-dimethylpropanamide Chemical compound C1CC2=CC=C(NC(=O)C(C)(C)C)C=C2CN1C1=C(C=C(C(OC)=C2)OC)C2=NC=N1 JPMVVTJYSRIFCD-UHFFFAOYSA-N 0.000 claims description 3
- FXIZAJLEYNNCEH-UHFFFAOYSA-N n-[2-(6,7-dimethoxyquinazolin-4-yl)-3,4-dihydro-1h-isoquinolin-7-yl]-2,5-dimethylbenzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(CC1=C2)CCC1=CC=C2NS(=O)(=O)C1=CC(C)=CC=C1C FXIZAJLEYNNCEH-UHFFFAOYSA-N 0.000 claims description 3
- UNHAZXCFRHBBNS-UHFFFAOYSA-N n-[2-(6,7-dimethoxyquinazolin-4-yl)-3,4-dihydro-1h-isoquinolin-7-yl]-3,4-dimethoxybenzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)NC1=CC=C(CCN(C2)C=3C4=CC(OC)=C(OC)C=C4N=CN=3)C2=C1 UNHAZXCFRHBBNS-UHFFFAOYSA-N 0.000 claims description 3
- TVHUSEDNEWKNSP-UHFFFAOYSA-N n-[2-(6,7-dimethoxyquinazolin-4-yl)-3,4-dihydro-1h-isoquinolin-7-yl]-4-(trifluoromethyl)benzenesulfonamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(CC1=C2)CCC1=CC=C2NS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 TVHUSEDNEWKNSP-UHFFFAOYSA-N 0.000 claims description 3
- UHMAUBJIUGTYTC-UHFFFAOYSA-N n-[2-(6,7-dimethoxyquinazolin-4-yl)-3,4-dihydro-1h-isoquinolin-7-yl]-4-ethylbenzamide Chemical compound C1=CC(CC)=CC=C1C(=O)NC1=CC=C(CCN(C2)C=3C4=CC(OC)=C(OC)C=C4N=CN=3)C2=C1 UHMAUBJIUGTYTC-UHFFFAOYSA-N 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 201000001119 neuropathy Diseases 0.000 claims description 3
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 208000002851 paranoid schizophrenia Diseases 0.000 claims description 3
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 208000016686 tic disease Diseases 0.000 claims description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical group CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 2
- UOIXJDLUBZGOMK-UHFFFAOYSA-N 4-(3,4-dihydro-1h-isoquinolin-2-yl)-7-methoxyquinazoline Chemical compound C1CC2=CC=CC=C2CN1C1=NC=NC2=CC(OC)=CC=C21 UOIXJDLUBZGOMK-UHFFFAOYSA-N 0.000 claims description 2
- RMPQATFCEFDGQT-UHFFFAOYSA-N 4-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)-6-ethoxy-7-methoxyquinazoline Chemical compound C1CC2=CC(OC)=C(OC)C=C2CN1C1=C2C=C(OCC)C(OC)=CC2=NC=N1 RMPQATFCEFDGQT-UHFFFAOYSA-N 0.000 claims description 2
- UMYIWEUVVJGISG-UHFFFAOYSA-N 4-(6,7-dimethoxy-3-methyl-3,4-dihydro-1h-isoquinolin-2-yl)-6-ethoxy-7-methoxyquinazoline Chemical compound C1C2=CC(OC)=C(OC)C=C2CC(C)N1C1=C2C=C(OCC)C(OC)=CC2=NC=N1 UMYIWEUVVJGISG-UHFFFAOYSA-N 0.000 claims description 2
- QGOJEVQLSMJIOU-UHFFFAOYSA-N 4-(7,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)-6-ethoxy-7-methoxyquinazoline Chemical compound C1CC2=CC=C(OC)C(OC)=C2CN1C1=C2C=C(OCC)C(OC)=CC2=NC=N1 QGOJEVQLSMJIOU-UHFFFAOYSA-N 0.000 claims description 2
- MUOKUOYNTHTOBU-UHFFFAOYSA-N 4-[[2-(6,7-dimethoxyquinazolin-4-yl)-3,4-dihydro-1h-isoquinolin-8-yl]sulfonyl]morpholine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(CC1=2)CCC1=CC=CC=2S(=O)(=O)N1CCOCC1 MUOKUOYNTHTOBU-UHFFFAOYSA-N 0.000 claims description 2
- VZEYVFSYLMBPOE-UHFFFAOYSA-N 6,7,8-trimethoxy-4-[8-(4-methylpiperazin-1-yl)sulfonyl-3,4-dihydro-1h-isoquinolin-2-yl]quinazoline Chemical compound N1=CN=C2C(OC)=C(OC)C(OC)=CC2=C1N(CC1=2)CCC1=CC=CC=2S(=O)(=O)N1CCN(C)CC1 VZEYVFSYLMBPOE-UHFFFAOYSA-N 0.000 claims description 2
- ZTOPTNRJJLNDJG-UHFFFAOYSA-N 6,7-dimethoxy-4-(3-propyl-3,4-dihydro-1h-isoquinolin-2-yl)quinazoline Chemical compound COC1=C(OC)C=C2C(N3CC4=CC=CC=C4CC3CCC)=NC=NC2=C1 ZTOPTNRJJLNDJG-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- VZFRNCSOCOPNDB-OXYNIABMSA-N isodomoic acid D Natural products CC(C=C/C=C(/C)C1CNC(C1CC(=O)O)C(=O)O)C(=O)O VZFRNCSOCOPNDB-OXYNIABMSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- YFMJTLUPSMCTOQ-UHFFFAOYSA-N isoquinoline-5-sulfonic acid Chemical compound N1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 YFMJTLUPSMCTOQ-UHFFFAOYSA-N 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
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- SLUVGWPCXBWFGG-UHFFFAOYSA-N n-[2-(6,7-dimethoxyquinazolin-4-yl)-3,4-dihydro-1h-isoquinolin-7-yl]-4-methoxybenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC1=CC=C(CCN(C2)C=3C4=CC(OC)=C(OC)C=C4N=CN=3)C2=C1 SLUVGWPCXBWFGG-UHFFFAOYSA-N 0.000 description 1
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- 125000000962 organic group Chemical group 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical class C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
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- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 102000020233 phosphotransferase Human genes 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
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- 125000000168 pyrrolyl group Chemical group 0.000 description 1
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- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
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- 230000002441 reversible effect Effects 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
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- 238000000844 transformation Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
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- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- ZJVTYKZWDWVIFD-UHFFFAOYSA-N zinc;hydrochloride Chemical compound Cl.[Zn] ZJVTYKZWDWVIFD-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Addiction (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54556504P | 2004-02-18 | 2004-02-18 | |
| PCT/IB2005/000307 WO2005082883A2 (en) | 2004-02-18 | 2005-02-07 | Tetrahydroisoquinolinyl derivatives of quinazoline and isoquinoline |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007523152A true JP2007523152A (ja) | 2007-08-16 |
| JP2007523152A5 JP2007523152A5 (https=) | 2008-03-13 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006553698A Abandoned JP2007523152A (ja) | 2004-02-18 | 2005-02-07 | キナゾリンおよびイソキノリンのテトラヒドロイソキノリニル誘導体 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7268142B2 (https=) |
| EP (1) | EP1723134A2 (https=) |
| JP (1) | JP2007523152A (https=) |
| AR (1) | AR047682A1 (https=) |
| BR (1) | BRPI0507839A (https=) |
| CA (1) | CA2556413A1 (https=) |
| DO (1) | DOP2005000022A (https=) |
| GT (1) | GT200500027A (https=) |
| NL (1) | NL1028321C2 (https=) |
| PA (1) | PA8624101A1 (https=) |
| PE (1) | PE20050694A1 (https=) |
| TW (1) | TW200528446A (https=) |
| UY (1) | UY28750A1 (https=) |
| WO (1) | WO2005082883A2 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2018502900A (ja) * | 2014-10-22 | 2018-02-01 | ザ ボード オブ リージェンツ オブ ザ ユニバーシティー オブ テキサス システム | ジスコイジンドメイン受容体１を標的化する小分子阻害剤およびその使用 |
| JP2023507185A (ja) * | 2019-12-18 | 2023-02-21 | シーエイチディーアイ ファウンデーション，インコーポレーテッド | ハンチンチンタンパク質をイメージングするための化合物及びプローブ |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ552397A (en) | 2004-07-15 | 2011-04-29 | Amr Technology Inc | Aryl-and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| MX2008002207A (es) * | 2005-08-16 | 2008-03-27 | Memory Pharm Corp | Inhibidores de fosfodiesterasa 10. |
| WO2007096743A1 (en) * | 2006-02-23 | 2007-08-30 | Pfizer Products Inc. | Substituted quinazolines as pde10 inhibitors |
| US20070287707A1 (en) * | 2006-02-28 | 2007-12-13 | Arrington Mark P | Phosphodiesterase 10 inhibitors |
| US20090099175A1 (en) * | 2006-03-01 | 2009-04-16 | Arrington Mark P | Phosphodiesterase 10 inhibitors |
| US20070265258A1 (en) * | 2006-03-06 | 2007-11-15 | Ruiping Liu | Quinazoline derivatives as phosphodiesterase 10 inhibitors |
| WO2007103554A1 (en) * | 2006-03-08 | 2007-09-13 | Amgen Inc. | Quinoline and isoquinoline derivatives as phosphodiesterase 10 inhibitors |
| ES2392553T3 (es) | 2006-07-10 | 2012-12-11 | H. Lundbeck A/S | Derivados (3-aril-piperazina-1-ilo) de 6,7-dialcoxiquinazolina, 6,7-dialcoxiftalazina y 6,7-dialcoxiisoquinolina |
| US7786139B2 (en) | 2006-11-21 | 2010-08-31 | Omeros Corporation | PDE10 inhibitors and related compositions and methods |
| EP2142517A2 (en) * | 2007-05-18 | 2010-01-13 | Wyeth | Quinazoline compounds |
| US7858620B2 (en) | 2007-09-19 | 2010-12-28 | H. Lundbeck A/S | Cyanoisoquinoline |
| US9156812B2 (en) | 2008-06-04 | 2015-10-13 | Bristol-Myers Squibb Company | Crystalline form of 6-[(4S)-2-methyl-4-(2-naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine |
| US8133897B2 (en) | 2008-06-20 | 2012-03-13 | H. Lundbeck A/S | Phenylimidazole derivatives as PDE10A enzyme inhibitors |
| TWI501965B (zh) * | 2008-06-20 | 2015-10-01 | Lundbeck & Co As H | 作為ｐｄｅ１０ａ酵素抑制劑之新穎苯基咪唑衍生物 |
| AU2010247735B2 (en) | 2009-05-12 | 2015-07-16 | Albany Molecular Research, Inc. | Crystalline forms of (S)-7-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)- 1,2,3,4-tetrahydroisoquinoline and use thereof |
| AU2010247763B2 (en) * | 2009-05-12 | 2015-12-24 | Albany Molecular Research, Inc. | 7-([1,2,4,]triazolo[1,5,-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4- tetrahydroisoquinoline and use thereof |
| WO2010132437A1 (en) | 2009-05-12 | 2010-11-18 | Albany Molecular Research, Inc. | Aryl, heteroaryl, and heterocycle substituted tetrahydroisoquinolines and use thereof |
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| US20030032579A1 (en) * | 2001-04-20 | 2003-02-13 | Pfizer Inc. | Therapeutic use of selective PDE10 inhibitors |
| PE20030008A1 (es) * | 2001-06-19 | 2003-01-22 | Bristol Myers Squibb Co | Inhibidores duales de pde 7 y pde 4 |
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2005
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- 2005-02-07 BR BRPI0507839-3A patent/BRPI0507839A/pt not_active IP Right Cessation
- 2005-02-07 WO PCT/IB2005/000307 patent/WO2005082883A2/en not_active Ceased
- 2005-02-07 JP JP2006553698A patent/JP2007523152A/ja not_active Abandoned
- 2005-02-07 CA CA002556413A patent/CA2556413A1/en not_active Abandoned
- 2005-02-15 PE PE2005000175A patent/PE20050694A1/es not_active Application Discontinuation
- 2005-02-16 DO DO2005000022A patent/DOP2005000022A/es unknown
- 2005-02-16 UY UY28750A patent/UY28750A1/es not_active Application Discontinuation
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- 2005-02-17 AR ARP050100564A patent/AR047682A1/es unknown
- 2005-02-17 TW TW094104654A patent/TW200528446A/zh unknown
- 2005-02-17 NL NL1028321A patent/NL1028321C2/nl not_active IP Right Cessation
- 2005-02-18 PA PA20058624101A patent/PA8624101A1/es unknown
- 2005-02-18 US US11/062,133 patent/US7268142B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2018502900A (ja) * | 2014-10-22 | 2018-02-01 | ザ ボード オブ リージェンツ オブ ザ ユニバーシティー オブ テキサス システム | ジスコイジンドメイン受容体１を標的化する小分子阻害剤およびその使用 |
| JP2023507185A (ja) * | 2019-12-18 | 2023-02-21 | シーエイチディーアイ ファウンデーション，インコーポレーテッド | ハンチンチンタンパク質をイメージングするための化合物及びプローブ |
| JP7720847B2 (ja) | 2019-12-18 | 2025-08-08 | シーエイチディーアイ ファウンデーション，インコーポレーテッド | ハンチンチンタンパク質をイメージングするための化合物及びプローブ |
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| WO2005082883A3 (en) | 2007-04-26 |
| DOP2005000022A (es) | 2005-08-30 |
| TW200528446A (en) | 2005-09-01 |
| AR047682A1 (es) | 2006-02-01 |
| WO2005082883A2 (en) | 2005-09-09 |
| PA8624101A1 (es) | 2005-11-25 |
| PE20050694A1 (es) | 2005-10-04 |
| CA2556413A1 (en) | 2005-09-09 |
| EP1723134A2 (en) | 2006-11-22 |
| NL1028321A1 (nl) | 2005-08-19 |
| US7268142B2 (en) | 2007-09-11 |
| BRPI0507839A (pt) | 2007-05-08 |
| GT200500027A (es) | 2005-10-24 |
| UY28750A1 (es) | 2005-09-30 |
| NL1028321C2 (nl) | 2006-05-23 |
| US20050182079A1 (en) | 2005-08-18 |
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