NO322205B1 - Tricykliske forbindelser, deres fremstilling og anvendelse samt preparater inneholdende forbindelsene - Google Patents
Tricykliske forbindelser, deres fremstilling og anvendelse samt preparater inneholdende forbindelsene Download PDFInfo
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- NO322205B1 NO322205B1 NO19983970A NO983970A NO322205B1 NO 322205 B1 NO322205 B1 NO 322205B1 NO 19983970 A NO19983970 A NO 19983970A NO 983970 A NO983970 A NO 983970A NO 322205 B1 NO322205 B1 NO 322205B1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 487
- 238000002360 preparation method Methods 0.000 title claims description 41
- 150000003839 salts Chemical class 0.000 claims abstract description 48
- 125000001424 substituent group Chemical group 0.000 claims abstract description 38
- 125000005843 halogen group Chemical group 0.000 claims abstract description 30
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 25
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 19
- 125000003277 amino group Chemical group 0.000 claims abstract description 18
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims abstract description 18
- 125000000623 heterocyclic group Chemical class 0.000 claims abstract description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 7
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- -1 cyano, hydroxy Chemical group 0.000 claims description 158
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 112
- 238000000034 method Methods 0.000 claims description 109
- 239000003795 chemical substances by application Substances 0.000 claims description 41
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
- 230000009467 reduction Effects 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 22
- 238000007363 ring formation reaction Methods 0.000 claims description 15
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 14
- YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 claims description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 14
- DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 claims description 14
- 229960003987 melatonin Drugs 0.000 claims description 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 8
- 102000001419 Melatonin receptor Human genes 0.000 claims description 8
- 108050009605 Melatonin receptor Proteins 0.000 claims description 8
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
- 230000001105 regulatory effect Effects 0.000 claims description 6
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 6
- 230000029936 alkylation Effects 0.000 claims description 5
- 238000005804 alkylation reaction Methods 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 230000027455 binding Effects 0.000 claims description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 3
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims description 3
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 3
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
- 230000008454 sleep-wake cycle Effects 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims description 2
- 230000009471 action Effects 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 2
- 230000027288 circadian rhythm Effects 0.000 claims description 2
- 230000006806 disease prevention Effects 0.000 claims description 2
- 235000019256 formaldehyde Nutrition 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- SDSGISCYQWUIMI-UHFFFAOYSA-N n-[2-(2,6,7,8-tetrahydro-1h-cyclopenta[e][1]benzofuran-8-yl)ethyl]acetamide Chemical group C1=C2OCCC2=C2C(CCNC(=O)C)CCC2=C1 SDSGISCYQWUIMI-UHFFFAOYSA-N 0.000 claims description 2
- FCRJFCVXPXEUPT-UHFFFAOYSA-N n-[2-(7-phenyl-2,6-dihydro-1h-cyclopenta[e][1]benzofuran-8-yl)ethyl]propanamide Chemical compound C1C2=CC=C3OCCC3=C2C(CCNC(=O)CC)=C1C1=CC=CC=C1 FCRJFCVXPXEUPT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 2
- 208000019116 sleep disease Diseases 0.000 claims description 2
- 125000000213 sulfino group Chemical group [H]OS(*)=O 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 229940124597 therapeutic agent Drugs 0.000 claims description 2
- RYYNBBSULBXPJL-BJMVGYQFSA-N (2e)-2-(1,2,6,7-tetrahydrocyclopenta[e][1]benzofuran-8-ylidene)ethanamine Chemical group C1=C2OCCC2=C2C(=C/CN)/CCC2=C1 RYYNBBSULBXPJL-BJMVGYQFSA-N 0.000 claims 1
- BFNUHWYOQCGTCA-UHFFFAOYSA-N 2-(2,6,7,8-tetrahydro-1h-cyclopenta[e][1]benzofuran-8-yl)ethanamine Chemical group C1=C2OCCC2=C2C(CCN)CCC2=C1 BFNUHWYOQCGTCA-UHFFFAOYSA-N 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 64
- 229930195733 hydrocarbon Natural products 0.000 abstract description 60
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 356
- 239000002904 solvent Substances 0.000 description 244
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 186
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 186
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 171
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 159
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 149
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 135
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 134
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 126
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 116
- 239000011541 reaction mixture Substances 0.000 description 108
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 93
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 90
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 88
- 239000000203 mixture Substances 0.000 description 88
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 87
- 239000002585 base Substances 0.000 description 87
- 150000001408 amides Chemical class 0.000 description 85
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 82
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 82
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 78
- 230000035484 reaction time Effects 0.000 description 70
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 69
- 150000002170 ethers Chemical class 0.000 description 63
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 61
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 60
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 59
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 58
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 58
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 58
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 56
- 238000004587 chromatography analysis Methods 0.000 description 56
- 238000004821 distillation Methods 0.000 description 56
- 238000001953 recrystallisation Methods 0.000 description 56
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 52
- 150000001298 alcohols Chemical class 0.000 description 50
- 229910052751 metal Inorganic materials 0.000 description 50
- 239000002184 metal Substances 0.000 description 50
- 239000000047 product Substances 0.000 description 50
- 239000012043 crude product Substances 0.000 description 48
- 238000000926 separation method Methods 0.000 description 47
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 46
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 46
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 45
- 239000002253 acid Substances 0.000 description 45
- 150000003462 sulfoxides Chemical class 0.000 description 44
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 43
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 43
- 150000008282 halocarbons Chemical class 0.000 description 43
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 43
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 42
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 42
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 41
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 40
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 40
- 239000003054 catalyst Substances 0.000 description 39
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- 150000002148 esters Chemical group 0.000 description 31
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 30
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 30
- 229910000027 potassium carbonate Inorganic materials 0.000 description 29
- 229910000029 sodium carbonate Inorganic materials 0.000 description 29
- 239000000126 substance Substances 0.000 description 29
- 229940093915 gynecological organic acid Drugs 0.000 description 28
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 28
- 150000007524 organic acids Chemical class 0.000 description 28
- 235000005985 organic acids Nutrition 0.000 description 28
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 27
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 27
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 26
- 230000002378 acidificating effect Effects 0.000 description 26
- 150000004703 alkoxides Chemical class 0.000 description 26
- 150000002825 nitriles Chemical class 0.000 description 26
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 26
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 26
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 24
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 24
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 23
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 22
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 22
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 22
- 150000008046 alkali metal hydrides Chemical class 0.000 description 22
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 22
- 150000007529 inorganic bases Chemical class 0.000 description 22
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 22
- 229910000105 potassium hydride Inorganic materials 0.000 description 22
- 238000006722 reduction reaction Methods 0.000 description 22
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 22
- 239000012312 sodium hydride Substances 0.000 description 22
- 229910000104 sodium hydride Inorganic materials 0.000 description 22
- 239000002841 Lewis acid Substances 0.000 description 21
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 21
- 150000001447 alkali salts Chemical class 0.000 description 21
- 150000004982 aromatic amines Chemical class 0.000 description 21
- 238000007796 conventional method Methods 0.000 description 21
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 21
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 21
- 150000007517 lewis acids Chemical class 0.000 description 21
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 21
- 150000003512 tertiary amines Chemical class 0.000 description 21
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 21
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 21
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 20
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 18
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 18
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 18
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 18
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 18
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 18
- 238000006798 ring closing metathesis reaction Methods 0.000 description 18
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 18
- 239000002168 alkylating agent Substances 0.000 description 17
- 229910052987 metal hydride Inorganic materials 0.000 description 17
- 150000004681 metal hydrides Chemical class 0.000 description 17
- 229940100198 alkylating agent Drugs 0.000 description 16
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 16
- 229910000024 caesium carbonate Inorganic materials 0.000 description 16
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 16
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 15
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 15
- 230000002140 halogenating effect Effects 0.000 description 15
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 14
- 235000019253 formic acid Nutrition 0.000 description 14
- 229930195734 saturated hydrocarbon Natural products 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 13
- 229910017052 cobalt Inorganic materials 0.000 description 13
- 239000010941 cobalt Substances 0.000 description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
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- 238000000638 solvent extraction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- RODHHGZKXKDCJK-UHFFFAOYSA-J tetrachlorotitanium;2,2,2-trifluoroacetic acid Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Ti+4].OC(=O)C(F)(F)F RODHHGZKXKDCJK-UHFFFAOYSA-J 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/16—Masculine contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
-
- 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
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
-
- 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
-
- 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
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Diabetes (AREA)
- Gynecology & Obstetrics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrane Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5149196 | 1996-03-08 | ||
| JP18366796 | 1996-07-12 | ||
| JP2918597 | 1997-02-13 | ||
| PCT/JP1997/000677 WO1997032871A1 (en) | 1996-03-08 | 1997-03-05 | Tricyclic compounds, their production and use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO983970L NO983970L (no) | 1998-08-28 |
| NO983970D0 NO983970D0 (no) | 1998-08-28 |
| NO322205B1 true NO322205B1 (no) | 2006-08-28 |
Family
ID=27286462
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19983970A NO322205B1 (no) | 1996-03-08 | 1998-08-28 | Tricykliske forbindelser, deres fremstilling og anvendelse samt preparater inneholdende forbindelsene |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6218429B1 (cs) |
| EP (2) | EP0885210B2 (cs) |
| JP (1) | JP4358917B2 (cs) |
| KR (1) | KR100494214B1 (cs) |
| CN (3) | CN100443480C (cs) |
| AT (1) | ATE219071T1 (cs) |
| CA (1) | CA2241666C (cs) |
| CZ (1) | CZ291626B6 (cs) |
| DE (1) | DE69713294T3 (cs) |
| DK (1) | DK0885210T5 (cs) |
| ES (1) | ES2175350T5 (cs) |
| HU (1) | HU224220B1 (cs) |
| NO (1) | NO322205B1 (cs) |
| NZ (1) | NZ330656A (cs) |
| PL (1) | PL188093B1 (cs) |
| PT (1) | PT885210E (cs) |
| SK (1) | SK283970B6 (cs) |
| TW (1) | TW562803B (cs) |
| WO (1) | WO1997032871A1 (cs) |
Families Citing this family (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2773798B1 (fr) * | 1998-01-16 | 2001-02-02 | Adir | Nouveaux composes tricycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| CN1206996C (zh) * | 1998-06-09 | 2005-06-22 | 武田药品工业株式会社 | 用于治疗或预防睡眠障碍的药物组合物 |
| AU6595000A (en) | 1999-08-20 | 2001-03-19 | Takeda Chemical Industries Ltd. | Dihydrobenzofuran derivatives, process for the preparation thereof and agents |
| CA2381468C (en) * | 1999-08-20 | 2013-05-28 | Yasuyuki Suzuki | Percutaneous absorption preparations containing melatonin receptor agonist for percutaneous treatment of sleep disorders |
| JP4721495B2 (ja) * | 1999-08-20 | 2011-07-13 | 武田薬品工業株式会社 | ジヒドロベンゾフラン誘導体、その製造法及び剤 |
| JP4632499B2 (ja) * | 1999-08-26 | 2011-02-16 | 武田薬品工業株式会社 | 鼻粘膜付着マトリックス |
| CA2383716C (en) * | 1999-09-08 | 2011-11-01 | Aventis Cropscience Uk Limited | Methods for reducing the phytotoxicity of herbicides using pre-treatment with antidotes |
| AU2002214306A1 (en) * | 2000-11-17 | 2002-05-27 | Takeda Chemical Industries Ltd. | Pharmaceutical preparation containing talc/barium sulfate |
| ATE469644T1 (de) * | 2000-11-17 | 2010-06-15 | Takeda Pharmaceutical | Pharmazeutische zubereitung enthaltend n-ä2-(1,6, 7,8-tetrahydro-2h-indenoä5,4 büfuran-8- yl)ethylüpropionamid ummantelt mit einer copolyvidon-enthaltenden, polyäthylenglykolfreien umhüllung |
| US6800648B2 (en) * | 2001-04-26 | 2004-10-05 | Wyeth | Antipsychotic aminomethyl derivatives of 7,8-dihydro-3H-1,6,9-trioxa-3-AZA-cyclopenta[a]naphthalen-2-one |
| IL149377A (en) * | 2002-04-28 | 2012-10-31 | Neurim Pharma 1991 | Pharmaceutical formulation comprising melatonin for the potentiation of the effect of hypnotic compounds |
| TWI400220B (zh) * | 2004-09-13 | 2013-07-01 | Takeda Pharmaceutical | 光活性胺衍生物的製法 |
| TW200626137A (en) * | 2004-12-13 | 2006-08-01 | Takeda Pharmaceuticals Co | Preventive or therapeutic agent for sleep disorder |
| NZ561677A (en) * | 2005-04-04 | 2011-02-25 | Takeda Pharmaceutical | (S)-N-[2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]propionamide, and its use for treating depression and anxiety neurosis |
| AU2006260201B2 (en) * | 2005-06-22 | 2011-10-20 | Takeda Pharmaceutical Company Limited | Tablet containing hardly soluble active ingredient |
| BRPI0614701A2 (pt) | 2005-07-29 | 2011-04-12 | Vanda Pharmaceuticals Inc | usos de um composto para melhorar a vigìlia e composições farmacêuticas |
| PE20080122A1 (es) * | 2006-03-20 | 2008-04-24 | Takeda Pharmaceutical | Agente profilactico o terapeutico para el sindrome de colon irritable |
| AR061478A1 (es) * | 2006-06-19 | 2008-08-27 | Takeda Pharmaceutical | Compuesto triciclico y composicion farmaceutica |
| JP5227806B2 (ja) * | 2006-12-08 | 2013-07-03 | 武田薬品工業株式会社 | 三環性化合物およびその医薬用途 |
| WO2008083204A2 (en) * | 2006-12-28 | 2008-07-10 | Braincells, Inc. | Modulation of neurogenesis by melatoninergic ligands |
| AU2007342806A1 (en) | 2006-12-28 | 2008-07-17 | Takeda Pharmaceutical Company Limited | Tricyclic compound and pharmaceutical use thereof |
| EP2139845A1 (en) * | 2007-02-26 | 2010-01-06 | Teva Pharmaceutical Industries Ltd. | Intermediates and processes for the synthesis of ramelteon |
| AU2008246719A1 (en) | 2007-04-26 | 2008-11-13 | Takeda Pharmaceutical Company Limited | Bicyclic compound and pharmaceutical use thereof |
| US8084630B2 (en) | 2007-05-31 | 2011-12-27 | Teva Pharmaceutical Industries Ltd. | Process for the synthesis of ramelteon and its intermediates |
| WO2009060318A2 (en) * | 2007-07-12 | 2009-05-14 | Teva Pharmaceutical Industries Ltd. | Polymorphic forms of ramelteon and processes for preparation thereof |
| ES2324849A1 (es) * | 2007-10-25 | 2009-08-17 | Ferrer Internacional, S.A. | Compuestos de indano. |
| US7470814B1 (en) * | 2007-10-31 | 2008-12-30 | Ferrer Internacional, S.A. | Process for the preparation of substituted 7-allyl-6-hydroxy-indanes |
| WO2009056993A2 (en) * | 2007-11-01 | 2009-05-07 | Teva Pharmaceutical Industries Ltd. | A process for the synthesis of ramelteon and its intermediates |
| CA2713598C (en) * | 2008-01-31 | 2016-07-05 | Takeda Pharmaceutical Company Limited | Prophylactic or therapeutic agent for attention deficit/hyperactivity disorder |
| US8871807B2 (en) | 2008-03-28 | 2014-10-28 | Ecolab Usa Inc. | Detergents capable of cleaning, bleaching, sanitizing and/or disinfecting textiles including sulfoperoxycarboxylic acids |
| US12203056B2 (en) | 2008-03-28 | 2025-01-21 | Ecolab Usa Inc. | Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents |
| US8809392B2 (en) | 2008-03-28 | 2014-08-19 | Ecolab Usa Inc. | Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents |
| AU2009230713C1 (en) | 2008-03-28 | 2018-08-02 | Ecolab Inc. | Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents |
| UY32016A (es) | 2008-07-30 | 2010-01-29 | Ferrer Int | Compuesto de 1,6-dihidro-2h-3-oxa-6-aza-as-indaceno |
| US20100152468A1 (en) * | 2008-10-16 | 2010-06-17 | Teva Pharmaceutical Industries Ltd. | Process for the synthesis of ramelteon and its intermediates |
| EP2344468A4 (en) * | 2008-11-14 | 2012-08-01 | Watson Pharma Private Ltd | PROCESS FOR PREPARING RAMELTÉON |
| WO2010074753A1 (en) | 2008-12-23 | 2010-07-01 | Map Pharmaceuticals, Inc. | Inhalation devices and related methods for administration of sedative hypnotic compounds |
| EP2396309A1 (en) | 2009-02-12 | 2011-12-21 | LEK Pharmaceuticals d.d. | Synthesis of (s)-n-ý2-(1,6,7,8-tetrahydro-2h-indeno-ý5,4-b¨furan-8-yl)ethyl¨propionamide |
| EP2406242B1 (en) * | 2009-03-10 | 2013-06-05 | Industriale Chimica S.R.L. | Process for the preparation of ramelteon |
| EP2243775A1 (en) | 2009-04-07 | 2010-10-27 | LEK Pharmaceuticals d.d. | Synthesis of 1-(2,3-Dihydrobenzofuran-4-YL)ethanone as intermediate in the preparation of ramelteon |
| EP2483258A1 (en) * | 2009-09-29 | 2012-08-08 | Lonza Ltd. | Process for preparing 1,2,6,7-tetrahydro-8h-indeno[5,4-b]furan-8-one |
| CA2777782C (en) * | 2009-10-15 | 2016-06-28 | Children's Medical Center Corporation | Sepiapterin reductase inhibitors for the treatment of pain |
| WO2012035303A2 (en) | 2010-09-17 | 2012-03-22 | Cipla Limited Et Al | A novel process for synthesis of ramelteon, and key intermediates for the synthesis of ramelteon |
| CN102321056B (zh) * | 2011-07-29 | 2014-05-14 | 宁波人健药业集团股份有限公司 | 一种合成雷美替胺的方法 |
| CN102391220A (zh) * | 2011-10-10 | 2012-03-28 | 四川大学 | 三环乙醇类化合物及其制备方法和用途 |
| US9321664B2 (en) | 2011-12-20 | 2016-04-26 | Ecolab Usa Inc. | Stable percarboxylic acid compositions and uses thereof |
| CA2867565C (en) | 2012-03-30 | 2021-01-19 | Victor KEASLER | Use of peracetic acid/hydrogen peroxide and peroxide-reducing agents for treatment of drilling fluids, frac fluids, flowback water and disposal water |
| AR091699A1 (es) | 2012-07-10 | 2015-02-25 | Astellas Pharma Inc | Derivado de indol carboxamida |
| WO2014010603A1 (ja) | 2012-07-10 | 2014-01-16 | アステラス製薬株式会社 | 腹圧性尿失禁又は混合型尿失禁の治療又は予防用医薬組成物、及び該医薬組成物に含有される化合物のスクリーニング方法 |
| CN103724357B (zh) * | 2012-10-11 | 2016-06-08 | 中国药科大学 | 一种3,4-二氢吡喃并[3,2-b]吲哚-2-酮类化合物的合成方法 |
| CN102924410A (zh) * | 2012-10-29 | 2013-02-13 | 华润赛科药业有限责任公司 | 一种雷美替胺的制备方法及其中间体 |
| US20140256811A1 (en) | 2013-03-05 | 2014-09-11 | Ecolab Usa Inc. | Efficient stabilizer in controlling self accelerated decomposition temperature of peroxycarboxylic acid compositions with mineral acids |
| US8822719B1 (en) | 2013-03-05 | 2014-09-02 | Ecolab Usa Inc. | Peroxycarboxylic acid compositions suitable for inline optical or conductivity monitoring |
| US10165774B2 (en) | 2013-03-05 | 2019-01-01 | Ecolab Usa Inc. | Defoamer useful in a peracid composition with anionic surfactants |
| WO2015108039A1 (ja) | 2014-01-14 | 2015-07-23 | アステラス製薬株式会社 | インドール化合物 |
| CN108697689B (zh) | 2016-01-08 | 2022-04-26 | 武田药品工业株式会社 | 自闭症谱系障碍的预防或治疗剂 |
| ES2987503T3 (es) | 2016-01-08 | 2024-11-15 | Takeda Pharmaceuticals Co | Compuestos que tienen afinidad por el receptor de melatonina como agente profiláctico o terapéutico para el delirio confusional |
| US12096768B2 (en) | 2019-08-07 | 2024-09-24 | Ecolab Usa Inc. | Polymeric and solid-supported chelators for stabilization of peracid-containing compositions |
| CN110776485B (zh) * | 2019-11-22 | 2022-09-30 | 山东邹平大展新材料有限公司 | 一种雷美替胺杂质的制备方法 |
| WO2023059546A1 (en) * | 2021-10-04 | 2023-04-13 | Psilosterics, Llc | Serotonin receptor agonists and methods of making and using the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2680366B1 (fr) * | 1991-08-13 | 1995-01-20 | Adir | Nouveaux derives d'arylethylamines, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2681862B1 (fr) | 1991-09-27 | 1993-11-12 | Adir Cie | Nouvelles (benzocycloalkyl)alkylamines, leur procede de preparation, et les compositions pharmaceutiques qui les contiennent. |
| FR2713636B1 (fr) | 1993-12-07 | 1996-01-05 | Adir | Nouveaux dérivés naphtaléniques, leur procédé de préparation, et les compositions pharmaceutiques qui les contiennent. |
| GB9326192D0 (en) * | 1993-12-22 | 1994-02-23 | Glaxo Group Ltd | Chemical compounds |
| GB9407919D0 (en) * | 1994-04-21 | 1994-06-15 | Glaxo Group Ltd | Chemical compounds |
| FR2725985B1 (fr) † | 1994-10-21 | 1996-11-15 | Adir | Nouveaux composes tricycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US5661186A (en) | 1995-02-24 | 1997-08-26 | Bristol-Myers Squibb Co. | Tetralinyl-and indanyl-ethylamides |
-
1997
- 1997-03-05 PL PL97328726A patent/PL188093B1/pl unknown
- 1997-03-05 DK DK97905450T patent/DK0885210T5/da active
- 1997-03-05 WO PCT/JP1997/000677 patent/WO1997032871A1/en active IP Right Grant
- 1997-03-05 DE DE69713294T patent/DE69713294T3/de not_active Expired - Lifetime
- 1997-03-05 HU HU9900616A patent/HU224220B1/hu active IP Right Grant
- 1997-03-05 ES ES97905450T patent/ES2175350T5/es not_active Expired - Lifetime
- 1997-03-05 NZ NZ330656A patent/NZ330656A/xx not_active IP Right Cessation
- 1997-03-05 CN CNB971927006A patent/CN100443480C/zh not_active Expired - Lifetime
- 1997-03-05 CA CA002241666A patent/CA2241666C/en not_active Expired - Lifetime
- 1997-03-05 SK SK1150-98A patent/SK283970B6/sk not_active IP Right Cessation
- 1997-03-05 KR KR10-1998-0707080A patent/KR100494214B1/ko not_active Expired - Lifetime
- 1997-03-05 PT PT97905450T patent/PT885210E/pt unknown
- 1997-03-05 CN CNA200610100063XA patent/CN1900067A/zh active Pending
- 1997-03-05 EP EP97905450A patent/EP0885210B2/en not_active Expired - Lifetime
- 1997-03-05 AT AT97905450T patent/ATE219071T1/de active
- 1997-03-05 CZ CZ19982775A patent/CZ291626B6/cs not_active IP Right Cessation
- 1997-03-05 CN CNB2005100916061A patent/CN100441574C/zh not_active Expired - Lifetime
- 1997-03-05 EP EP04027766A patent/EP1550655A1/en not_active Withdrawn
- 1997-03-06 TW TW086102717A patent/TW562803B/zh not_active IP Right Cessation
-
1998
- 1998-08-28 NO NO19983970A patent/NO322205B1/no not_active IP Right Cessation
- 1998-09-22 JP JP26811098A patent/JP4358917B2/ja not_active Expired - Lifetime
-
1999
- 1999-05-10 US US09/309,519 patent/US6218429B1/en not_active Expired - Lifetime
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| Date | Code | Title | Description |
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| MK1K | Patent expired |