JP2005527579A5 - - Google Patents
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- Publication number
- JP2005527579A5 JP2005527579A5 JP2003583332A JP2003583332A JP2005527579A5 JP 2005527579 A5 JP2005527579 A5 JP 2005527579A5 JP 2003583332 A JP2003583332 A JP 2003583332A JP 2003583332 A JP2003583332 A JP 2003583332A JP 2005527579 A5 JP2005527579 A5 JP 2005527579A5
- Authority
- JP
- Japan
- Prior art keywords
- tetrahydro
- benzazepine
- compound according
- methyl
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 66
- 125000000217 alkyl group Chemical group 0.000 claims 21
- 150000002367 halogens Chemical class 0.000 claims 19
- 229910052736 halogen Inorganic materials 0.000 claims 18
- 239000000203 mixture Substances 0.000 claims 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 14
- 238000000034 method Methods 0.000 claims 11
- 125000001424 substituent group Chemical group 0.000 claims 11
- 241000124008 Mammalia Species 0.000 claims 9
- 230000002265 prevention Effects 0.000 claims 9
- 208000008589 Obesity Diseases 0.000 claims 8
- 208000015114 central nervous system disease Diseases 0.000 claims 8
- 239000003814 drug Substances 0.000 claims 8
- 235000020824 obesity Nutrition 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 239000012453 solvate Substances 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 230000005856 abnormality Effects 0.000 claims 6
- 230000003542 behavioural effect Effects 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 4
- 229910052794 bromium Inorganic materials 0.000 claims 4
- 210000003169 central nervous system Anatomy 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- 230000006378 damage Effects 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 3
- 208000007848 Alcoholism Diseases 0.000 claims 3
- 208000000103 Anorexia Nervosa Diseases 0.000 claims 3
- 208000019901 Anxiety disease Diseases 0.000 claims 3
- 208000020925 Bipolar disease Diseases 0.000 claims 3
- 208000032841 Bulimia Diseases 0.000 claims 3
- 206010006550 Bulimia nervosa Diseases 0.000 claims 3
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims 3
- 206010012289 Dementia Diseases 0.000 claims 3
- 206010022773 Intracranial pressure increased Diseases 0.000 claims 3
- 208000019695 Migraine disease Diseases 0.000 claims 3
- 208000027626 Neurocognitive disease Diseases 0.000 claims 3
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 3
- 208000002193 Pain Diseases 0.000 claims 3
- 206010036618 Premenstrual syndrome Diseases 0.000 claims 3
- 208000028017 Psychotic disease Diseases 0.000 claims 3
- 201000001880 Sexual dysfunction Diseases 0.000 claims 3
- 206010041250 Social phobia Diseases 0.000 claims 3
- 102100026383 Vasopressin-neurophysin 2-copeptin Human genes 0.000 claims 3
- 238000013019 agitation Methods 0.000 claims 3
- 201000007930 alcohol dependence Diseases 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 208000025748 atypical depressive disease Diseases 0.000 claims 3
- 201000010064 diabetes insipidus Diseases 0.000 claims 3
- 206010015037 epilepsy Diseases 0.000 claims 3
- 230000001939 inductive effect Effects 0.000 claims 3
- 206010027175 memory impairment Diseases 0.000 claims 3
- 206010027599 migraine Diseases 0.000 claims 3
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims 3
- -1 n- propyl Chemical group 0.000 claims 3
- 208000022821 personality disease Diseases 0.000 claims 3
- 201000000484 premenstrual tension Diseases 0.000 claims 3
- 208000020016 psychiatric disease Diseases 0.000 claims 3
- 230000036186 satiety Effects 0.000 claims 3
- 235000019627 satiety Nutrition 0.000 claims 3
- 201000000980 schizophrenia Diseases 0.000 claims 3
- 231100000872 sexual dysfunction Toxicity 0.000 claims 3
- 201000002859 sleep apnea Diseases 0.000 claims 3
- 208000019116 sleep disease Diseases 0.000 claims 3
- 208000020685 sleep-wake disease Diseases 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 230000004584 weight gain Effects 0.000 claims 3
- 235000019786 weight gain Nutrition 0.000 claims 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- RYYXCFYKJMRFPZ-UHFFFAOYSA-N 5-ethyl-7-iodo-8-methoxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CCC1CNCCC2=CC(OC)=C(I)C=C12 RYYXCFYKJMRFPZ-UHFFFAOYSA-N 0.000 claims 2
- KTCVEIAEKPSBCJ-UHFFFAOYSA-N 7,8-dichloro-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CC1CNCCC2=CC(Cl)=C(Cl)C=C12 KTCVEIAEKPSBCJ-UHFFFAOYSA-N 0.000 claims 2
- 206010012335 Dependence Diseases 0.000 claims 2
- 208000012902 Nervous system disease Diseases 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 235000018823 dietary intake Nutrition 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 150000002460 imidazoles Chemical class 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 230000002458 infectious effect Effects 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 231100000331 toxic Toxicity 0.000 claims 2
- 230000002588 toxic effect Effects 0.000 claims 2
- PIFUPUQFKHPAJN-UHFFFAOYSA-N (7-bromo-8-methoxy-2,3,4,5-tetrahydro-1h-3-benzazepin-5-yl)methanol Chemical compound C1CNCC(CO)C2=C1C=C(OC)C(Br)=C2 PIFUPUQFKHPAJN-UHFFFAOYSA-N 0.000 claims 1
- MWVMYAWMFTVYED-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCCC2=CC=CC=C21 MWVMYAWMFTVYED-UHFFFAOYSA-N 0.000 claims 1
- VDDJHHQYKKCCIO-UHFFFAOYSA-N 5-ethyl-7-(trifluoromethyl)-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CCC1CNCCC2=CC=C(C(F)(F)F)C=C12 VDDJHHQYKKCCIO-UHFFFAOYSA-N 0.000 claims 1
- LGUJJJJNBBUBHT-UHFFFAOYSA-N 5-ethyl-7-iodo-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CCC1CNCCC2=CC=C(I)C=C12 LGUJJJJNBBUBHT-UHFFFAOYSA-N 0.000 claims 1
- GBYLNYMTYZRQLE-UHFFFAOYSA-N 5-methyl-7-(trifluoromethyl)-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CC1CNCCC2=CC=C(C(F)(F)F)C=C12 GBYLNYMTYZRQLE-UHFFFAOYSA-N 0.000 claims 1
- TTXLZSFANXGSGY-UHFFFAOYSA-N 7,8-dichloro-5-ethyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CCC1CNCCC2=CC(Cl)=C(Cl)C=C12 TTXLZSFANXGSGY-UHFFFAOYSA-N 0.000 claims 1
- ZVWYXVHPZNQTGP-UHFFFAOYSA-N 7-(2-chlorophenyl)-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1=C2C(C)CNCCC2=CC=C1C1=CC=CC=C1Cl ZVWYXVHPZNQTGP-UHFFFAOYSA-N 0.000 claims 1
- ZSPRCURTNKXTKN-UHFFFAOYSA-N 7-bromo-2,5-dimethyl-8-prop-2-enoxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CC1CNC(C)CC2=CC(OCC=C)=C(Br)C=C21 ZSPRCURTNKXTKN-UHFFFAOYSA-N 0.000 claims 1
- CJNIKSUHKLMLAY-UHFFFAOYSA-N 7-bromo-5-cyclopropyl-8-methoxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1=2C=C(Br)C(OC)=CC=2CCNCC1C1CC1 CJNIKSUHKLMLAY-UHFFFAOYSA-N 0.000 claims 1
- FZAXXXCRTZYHAH-UHFFFAOYSA-N 7-bromo-5-ethyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CCC1CNCCC2=CC=C(Br)C=C12 FZAXXXCRTZYHAH-UHFFFAOYSA-N 0.000 claims 1
- QSLHEIFNJPYBLS-UHFFFAOYSA-N 7-bromo-5-ethyl-8-methoxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CCC1CNCCC2=CC(OC)=C(Br)C=C12 QSLHEIFNJPYBLS-UHFFFAOYSA-N 0.000 claims 1
- UWFSZQMKPCCKFT-UHFFFAOYSA-N 7-bromo-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepin-8-ol Chemical compound CC1CNCCC2=CC(O)=C(Br)C=C12 UWFSZQMKPCCKFT-UHFFFAOYSA-N 0.000 claims 1
- KRBZRTWDEJCQIL-UHFFFAOYSA-N 7-bromo-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CC1CNCCC2=CC=C(Br)C=C12 KRBZRTWDEJCQIL-UHFFFAOYSA-N 0.000 claims 1
- BNEIDDXVFTVOOR-UHFFFAOYSA-N 7-bromo-5-methyl-8-phenylmethoxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound BrC=1C=C2C(C)CNCCC2=CC=1OCC1=CC=CC=C1 BNEIDDXVFTVOOR-UHFFFAOYSA-N 0.000 claims 1
- IYWYWVMPIJVOBD-UHFFFAOYSA-N 7-bromo-5-methyl-8-prop-2-enoxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CC1CNCCC2=CC(OCC=C)=C(Br)C=C12 IYWYWVMPIJVOBD-UHFFFAOYSA-N 0.000 claims 1
- OKANWZMGTYYNOW-UHFFFAOYSA-N 7-bromo-5-methyl-8-propan-2-yloxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCC(C)C2=C1C=C(OC(C)C)C(Br)=C2 OKANWZMGTYYNOW-UHFFFAOYSA-N 0.000 claims 1
- YJMJIRPWYQUXFC-UHFFFAOYSA-N 7-bromo-5-propan-2-yl-2,3,4,5-tetrahydro-1h-3-benzazepin-8-ol Chemical compound CC(C)C1CNCCC2=CC(O)=C(Br)C=C12 YJMJIRPWYQUXFC-UHFFFAOYSA-N 0.000 claims 1
- CABPILKLTHGNHC-UHFFFAOYSA-N 7-bromo-5-propan-2-yl-8-prop-2-enoxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CC(C)C1CNCCC2=CC(OCC=C)=C(Br)C=C12 CABPILKLTHGNHC-UHFFFAOYSA-N 0.000 claims 1
- LQGCCOADXMPGTL-UHFFFAOYSA-N 7-bromo-8-ethoxy-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCC(C)C2=C1C=C(OCC)C(Br)=C2 LQGCCOADXMPGTL-UHFFFAOYSA-N 0.000 claims 1
- XHRJDETZSGXGJN-UHFFFAOYSA-N 7-bromo-8-methoxy-2,5-dimethyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1C(C)NCC(C)C2=C1C=C(OC)C(Br)=C2 XHRJDETZSGXGJN-UHFFFAOYSA-N 0.000 claims 1
- TZUDPSHMYVSTRR-UHFFFAOYSA-N 7-bromo-8-methoxy-3,5-dimethyl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C1CN(C)CC(C)C2=C1C=C(OC)C(Br)=C2 TZUDPSHMYVSTRR-UHFFFAOYSA-N 0.000 claims 1
- HQQAIJWQKAFMGF-UHFFFAOYSA-N 7-bromo-8-methoxy-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCC(C)C2=C1C=C(OC)C(Br)=C2 HQQAIJWQKAFMGF-UHFFFAOYSA-N 0.000 claims 1
- XYDLVEIIQDOYDA-UHFFFAOYSA-N 7-bromo-8-methoxy-5-methyl-3-propyl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound CC1CN(CCC)CCC2=CC(OC)=C(Br)C=C21 XYDLVEIIQDOYDA-UHFFFAOYSA-N 0.000 claims 1
- IHRBUEKNYVJQIC-UHFFFAOYSA-N 7-bromo-8-methoxy-5-propan-2-yl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCC(C(C)C)C2=C1C=C(OC)C(Br)=C2 IHRBUEKNYVJQIC-UHFFFAOYSA-N 0.000 claims 1
- KVGYVFPNKGJTTP-UHFFFAOYSA-N 7-chloro-2,3,4,5-tetrahydro-1h-3-benzazepin-5-ol Chemical compound OC1CNCCC2=CC=C(Cl)C=C12 KVGYVFPNKGJTTP-UHFFFAOYSA-N 0.000 claims 1
- BPLNPUPEOXRWMZ-UHFFFAOYSA-N 7-chloro-3,5-dimethyl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound CC1CN(C)CCC2=CC=C(Cl)C=C12 BPLNPUPEOXRWMZ-UHFFFAOYSA-N 0.000 claims 1
- DNLSOPHLIKCIIV-UHFFFAOYSA-N 7-chloro-5-ethyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CCC1CNCCC2=CC=C(Cl)C=C12 DNLSOPHLIKCIIV-UHFFFAOYSA-N 0.000 claims 1
- OAJYPPWRJRZVRO-UHFFFAOYSA-N 7-chloro-5-ethyl-8-methoxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CCC1CNCCC2=CC(OC)=C(Cl)C=C12 OAJYPPWRJRZVRO-UHFFFAOYSA-N 0.000 claims 1
- XTTZERNUQAFMOF-UHFFFAOYSA-N 7-chloro-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CC1CNCCC2=CC=C(Cl)C=C12 XTTZERNUQAFMOF-UHFFFAOYSA-N 0.000 claims 1
- OSCDHVCJRHGBTH-UHFFFAOYSA-N 7-chloro-5-methyl-8-prop-2-enoxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CC1CNCCC2=CC(OCC=C)=C(Cl)C=C12 OSCDHVCJRHGBTH-UHFFFAOYSA-N 0.000 claims 1
- CKXNNAQKSQRYNX-UHFFFAOYSA-N 7-chloro-8-(2-fluorophenyl)-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound ClC=1C=C2C(C)CNCCC2=CC=1C1=CC=CC=C1F CKXNNAQKSQRYNX-UHFFFAOYSA-N 0.000 claims 1
- AELPHXGUKIVCSY-UHFFFAOYSA-N 7-chloro-8-fluoro-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CC1CNCCC2=CC(F)=C(Cl)C=C12 AELPHXGUKIVCSY-UHFFFAOYSA-N 0.000 claims 1
- SJJIKXOJEDKQRJ-UHFFFAOYSA-N 7-chloro-8-methoxy-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCC(C)C2=C1C=C(OC)C(Cl)=C2 SJJIKXOJEDKQRJ-UHFFFAOYSA-N 0.000 claims 1
- TXVNTTRQUFIPMP-UHFFFAOYSA-N 7-fluoro-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CC1CNCCC2=CC=C(F)C=C12 TXVNTTRQUFIPMP-UHFFFAOYSA-N 0.000 claims 1
- SAJLTUXRPKWFBP-UHFFFAOYSA-N 7-iodo-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepin-8-ol Chemical compound CC1CNCCC2=CC(O)=C(I)C=C12 SAJLTUXRPKWFBP-UHFFFAOYSA-N 0.000 claims 1
- MWDDRGPUDJHEAN-UHFFFAOYSA-N 7-iodo-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CC1CNCCC2=CC=C(I)C=C12 MWDDRGPUDJHEAN-UHFFFAOYSA-N 0.000 claims 1
- DCHHWZZHLKXNCB-UHFFFAOYSA-N 7-iodo-5-methyl-8-(trifluoromethoxy)-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CC1CNCCC2=CC(OC(F)(F)F)=C(I)C=C12 DCHHWZZHLKXNCB-UHFFFAOYSA-N 0.000 claims 1
- SONAPYLGIVLEEN-UHFFFAOYSA-N 7-iodo-5-methyl-8-prop-2-enoxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CC1CNCCC2=CC(OCC=C)=C(I)C=C12 SONAPYLGIVLEEN-UHFFFAOYSA-N 0.000 claims 1
- IIXFGYNBVWNWNL-UHFFFAOYSA-N 7-iodo-8-methoxy-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCC(C)C2=C1C=C(OC)C(I)=C2 IIXFGYNBVWNWNL-UHFFFAOYSA-N 0.000 claims 1
- RRUVWNUSSPWKJJ-UHFFFAOYSA-N 7-iodo-8-methoxy-5-methyl-3-propyl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound CC1CN(CCC)CCC2=CC(OC)=C(I)C=C21 RRUVWNUSSPWKJJ-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- HXIGMEDVVRGQPH-UHFFFAOYSA-N 8-methoxy-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine-7-carbonitrile Chemical compound C1CNCC(C)C2=C1C=C(OC)C(C#N)=C2 HXIGMEDVVRGQPH-UHFFFAOYSA-N 0.000 claims 1
- WBGUZBYKIJAQIY-UHFFFAOYSA-N 8-methoxy-5-methyl-7-(1,1,2,2,2-pentafluoroethyl)-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCC(C)C2=C1C=C(OC)C(C(F)(F)C(F)(F)F)=C2 WBGUZBYKIJAQIY-UHFFFAOYSA-N 0.000 claims 1
- VZPBGKYNLKOIBH-UHFFFAOYSA-N 8-methoxy-5-methyl-7-(trifluoromethyl)-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCC(C)C2=C1C=C(OC)C(C(F)(F)F)=C2 VZPBGKYNLKOIBH-UHFFFAOYSA-N 0.000 claims 1
- BOQDOEZEZODMKK-UHFFFAOYSA-N 8-methoxy-5-methyl-7-thiophen-2-yl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound COC1=CC=2CCNCC(C)C=2C=C1C1=CC=CS1 BOQDOEZEZODMKK-UHFFFAOYSA-N 0.000 claims 1
- 206010019233 Headaches Diseases 0.000 claims 1
- 201000009906 Meningitis Diseases 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- 230000032683 aging Effects 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 230000003247 decreasing effect Effects 0.000 claims 1
- 208000010643 digestive system disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 206010013663 drug dependence Diseases 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
- 206010014599 encephalitis Diseases 0.000 claims 1
- 235000012631 food intake Nutrition 0.000 claims 1
- 230000037406 food intake Effects 0.000 claims 1
- 230000005176 gastrointestinal motility Effects 0.000 claims 1
- 208000018685 gastrointestinal system disease Diseases 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 230000008733 trauma Effects 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37205802P | 2002-04-12 | 2002-04-12 | |
| US40549502P | 2002-08-23 | 2002-08-23 | |
| US43460702P | 2002-12-18 | 2002-12-18 | |
| US10/410,991 US6953787B2 (en) | 2002-04-12 | 2003-04-10 | 5HT2C receptor modulators |
| PCT/US2003/011076 WO2003086306A2 (en) | 2002-04-12 | 2003-04-11 | 5ht2c receptor modulators |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006058747A Division JP4191741B2 (ja) | 2002-04-12 | 2006-03-03 | ５ｈｔ２ｃレセプター修飾因子 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005527579A JP2005527579A (ja) | 2005-09-15 |
| JP2005527579A5 true JP2005527579A5 (enExample) | 2007-03-29 |
| JP4155926B2 JP4155926B2 (ja) | 2008-09-24 |
Family
ID=29255581
Family Applications (5)
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2003
- 2003-04-10 US US10/410,991 patent/US6953787B2/en not_active Expired - Lifetime
- 2003-04-11 KR KR1020047016198A patent/KR100812925B1/ko not_active Expired - Lifetime
- 2003-04-11 EP EP03718323A patent/EP1411881B9/en not_active Expired - Lifetime
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- 2003-04-11 CA CA002481723A patent/CA2481723C/en not_active Expired - Lifetime
- 2003-04-11 DE DE60300610T patent/DE60300610T2/de not_active Expired - Lifetime
- 2003-04-11 CN CN2009100001906A patent/CN101486677B/zh not_active Expired - Lifetime
- 2003-04-11 IL IL16416203A patent/IL164162A0/xx unknown
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- 2003-04-11 DK DK03718323T patent/DK1411881T3/da active
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- 2003-04-11 CN CNA2009100001925A patent/CN101486679A/zh active Pending
- 2003-04-11 MX MXPA04009965A patent/MXPA04009965A/es active IP Right Grant
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- 2003-04-11 BR BR122017023795A patent/BR122017023795B8/pt not_active IP Right Cessation
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- 2003-04-11 CN CNA200910000193XA patent/CN101485664A/zh not_active Withdrawn
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2004
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2008
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2014
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2016
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