DE2629877C2 - - Google Patents
Info
- Publication number
- DE2629877C2 DE2629877C2 DE2629877A DE2629877A DE2629877C2 DE 2629877 C2 DE2629877 C2 DE 2629877C2 DE 2629877 A DE2629877 A DE 2629877A DE 2629877 A DE2629877 A DE 2629877A DE 2629877 C2 DE2629877 C2 DE 2629877C2
- Authority
- DE
- Germany
- Prior art keywords
- pyrrolo
- dihydro
- benzazepine
- cyan
- mixture
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 20
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 18
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 9
- 235000019253 formic acid Nutrition 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 229910000838 Al alloy Inorganic materials 0.000 claims description 4
- 229910000990 Ni alloy Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 239000005022 packaging material Substances 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 28
- 239000000203 mixture Substances 0.000 description 26
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 14
- -1 Amino-propylidene Chemical group 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- JWBQFKXZFXSLAZ-UHFFFAOYSA-N 11-[3-(dimethylamino)propylidene]-5,6-dihydropyrrolo[1,2-c][3]benzazepine-2-carbaldehyde Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC(C=O)=CN21 JWBQFKXZFXSLAZ-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000000875 corresponding effect Effects 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 235000006408 oxalic acid Nutrition 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 230000011514 reflex Effects 0.000 description 6
- 208000007101 Muscle Cramp Diseases 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 208000013403 hyperactivity Diseases 0.000 description 5
- 239000003158 myorelaxant agent Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 208000005392 Spasm Diseases 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- QHACEJBZGFEEJE-UHFFFAOYSA-L bis(trifluoromethylsulfanyl)mercury Chemical compound [Hg+2].FC(F)(F)[S-].FC(F)(F)[S-] QHACEJBZGFEEJE-UHFFFAOYSA-L 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 210000003205 muscle Anatomy 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- WHASPLKNGUEKGD-UHFFFAOYSA-N 11-[3-(dimethylamino)propylidene]-5,6-dihydropyrrolo[1,2-c][3]benzazepine-2-carbonitrile Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC(C#N)=CN21 WHASPLKNGUEKGD-UHFFFAOYSA-N 0.000 description 3
- XDGFSERHJUTNJD-UHFFFAOYSA-N 11-oxo-5,6-dihydropyrrolo[1,2-c][3]benzazepine-2-carbonitrile Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC(C#N)=CN21 XDGFSERHJUTNJD-UHFFFAOYSA-N 0.000 description 3
- UVJURAVPWNZIFR-UHFFFAOYSA-N 11-oxopyrrolo[2,1-b][3]benzazepine-2-carbonitrile Chemical compound C1=CC2=CC=CC=C2C(=O)C2=CC(C#N)=CN21 UVJURAVPWNZIFR-UHFFFAOYSA-N 0.000 description 3
- MBSORYCFRFFVBR-UHFFFAOYSA-N 3-(5,6-dihydropyrrolo[1,2-c][3]benzazepin-11-ylidene)-n,n-dimethylpropan-1-amine Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CN21 MBSORYCFRFFVBR-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 208000008238 Muscle Spasticity Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- JURKNVYFZMSNLP-UHFFFAOYSA-N cyclobenzaprine Chemical compound C1=CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 JURKNVYFZMSNLP-UHFFFAOYSA-N 0.000 description 3
- 229960003572 cyclobenzaprine Drugs 0.000 description 3
- 239000003792 electrolyte Substances 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229940001470 psychoactive drug Drugs 0.000 description 3
- 239000004089 psychotropic agent Substances 0.000 description 3
- PLKKXWBJOVTVEU-UHFFFAOYSA-N pyrrolo[2,3-i][1]benzazepine Chemical class C1=CC=NC2=C3C=CN=C3C=CC2=C1 PLKKXWBJOVTVEU-UHFFFAOYSA-N 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000003204 tranquilizing agent Substances 0.000 description 3
- 230000002936 tranquilizing effect Effects 0.000 description 3
- VITRLXDSBBVNCZ-UHFFFAOYSA-K trichloroiron;hydrate Chemical compound O.Cl[Fe](Cl)Cl VITRLXDSBBVNCZ-UHFFFAOYSA-K 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- ZXBHYCRVSIUNAJ-UHFFFAOYSA-N 1-(2-phenylethyl)pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1CCC1=CC=CC=C1 ZXBHYCRVSIUNAJ-UHFFFAOYSA-N 0.000 description 2
- ONXFWZYTSMEDPR-UHFFFAOYSA-N 11-[3-(dimethylamino)propylidene]-5,6-dihydropyrrolo[1,2-c][3]benzazepine-9-carbonitrile Chemical compound C1CC2=CC=C(C#N)C=C2C(=CCCN(C)C)C2=CC=CN21 ONXFWZYTSMEDPR-UHFFFAOYSA-N 0.000 description 2
- UYRDUBJWJJTYLS-UHFFFAOYSA-N 11-[3-(dimethylamino)propylidene]pyrrolo[2,1-b][3]benzazepine-2-carbaldehyde Chemical compound C1=CC2=CC=CC=C2C(=CCCN(C)C)C2=CC(C=O)=CN21 UYRDUBJWJJTYLS-UHFFFAOYSA-N 0.000 description 2
- XCQXXBUHULPVSM-UHFFFAOYSA-N 11-oxo-5,6-dihydropyrrolo[1,2-c][3]benzazepine-2-carbaldehyde Chemical compound C1CN2C=C(C=O)C=C2C(=O)C2=CC=CC=C21 XCQXXBUHULPVSM-UHFFFAOYSA-N 0.000 description 2
- MGJXCBHTYYKMAT-UHFFFAOYSA-N 11-oxo-5,6-dihydropyrrolo[1,2-c][3]benzazepine-9-carbonitrile Chemical compound C1CC2=CC=C(C#N)C=C2C(=O)C2=CC=CN21 MGJXCBHTYYKMAT-UHFFFAOYSA-N 0.000 description 2
- SXBREWSWPDBVKH-UHFFFAOYSA-N 11-oxopyrrolo[2,1-b][3]benzazepine-2-carbaldehyde Chemical compound C1=CC2=CC=CC=C2C(=O)C2=CC(C=O)=CN21 SXBREWSWPDBVKH-UHFFFAOYSA-N 0.000 description 2
- HRDDEFFVLDBECG-UHFFFAOYSA-N 11-oxopyrrolo[2,1-b][3]benzazepine-9-carbonitrile Chemical compound C1=CC2=CC=C(C#N)C=C2C(=O)C2=CC=CN21 HRDDEFFVLDBECG-UHFFFAOYSA-N 0.000 description 2
- NFLTXPWUQFDVDF-UHFFFAOYSA-N 3-(9-bromopyrrolo[2,1-b][3]benzazepin-11-ylidene)-n,n-dimethylpropan-1-amine Chemical compound C1=CC2=CC=C(Br)C=C2C(=CCCN(C)C)C2=CC=CN21 NFLTXPWUQFDVDF-UHFFFAOYSA-N 0.000 description 2
- GLLXRIAKFJWCGR-UHFFFAOYSA-N 3-(9-iodo-5,6-dihydropyrrolo[1,2-c][3]benzazepin-11-ylidene)-n,n-dimethylpropan-1-amine Chemical compound C1CC2=CC=C(I)C=C2C(=CCCN(C)C)C2=CC=CN21 GLLXRIAKFJWCGR-UHFFFAOYSA-N 0.000 description 2
- KRBHNLFMZDOLGK-UHFFFAOYSA-N 4-cyano-1-(2-phenylethyl)pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC(C#N)=CN1CCC1=CC=CC=C1 KRBHNLFMZDOLGK-UHFFFAOYSA-N 0.000 description 2
- APSVCCUFSNKZRZ-UHFFFAOYSA-N 9-(trifluoromethylsulfanyl)-5,6-dihydropyrrolo[1,2-c][3]benzazepin-11-one Chemical compound C1CN2C=CC=C2C(=O)C2=CC(SC(F)(F)F)=CC=C21 APSVCCUFSNKZRZ-UHFFFAOYSA-N 0.000 description 2
- HTWDFTGTOXYBPX-UHFFFAOYSA-N 9-(trifluoromethylsulfanyl)pyrrolo[2,1-b][3]benzazepin-11-one Chemical compound C1=CN2C=CC=C2C(=O)C2=CC(SC(F)(F)F)=CC=C21 HTWDFTGTOXYBPX-UHFFFAOYSA-N 0.000 description 2
- BIADPAYAUCMUSO-UHFFFAOYSA-N 9-bromopyrrolo[2,1-b][3]benzazepin-11-one Chemical compound C1=CN2C=CC=C2C(=O)C2=CC(Br)=CC=C21 BIADPAYAUCMUSO-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 206010052904 Musculoskeletal stiffness Diseases 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 229910000389 calcium phosphate Inorganic materials 0.000 description 2
- 235000011010 calcium phosphates Nutrition 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- VONGYFFEWFJHNP-UHFFFAOYSA-N methyl 1h-pyrrole-2-carboxylate Chemical compound COC(=O)C1=CC=CN1 VONGYFFEWFJHNP-UHFFFAOYSA-N 0.000 description 2
- NRWRIGMKWMUEAK-UHFFFAOYSA-N methyl 4-cyano-1-(2-phenylethyl)pyrrole-2-carboxylate Chemical compound COC(=O)C1=CC(C#N)=CN1CCC1=CC=CC=C1 NRWRIGMKWMUEAK-UHFFFAOYSA-N 0.000 description 2
- YOJPRBSNULJGHK-UHFFFAOYSA-N n,n-dimethyl-3-[9-(trifluoromethylsulfanyl)-5,6-dihydropyrrolo[1,2-c][3]benzazepin-11-ylidene]propan-1-amine Chemical compound C1CC2=CC=C(SC(F)(F)F)C=C2C(=CCCN(C)C)C2=CC=CN21 YOJPRBSNULJGHK-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 210000002027 skeletal muscle Anatomy 0.000 description 2
- 229940125706 skeletal muscle relaxant agent Drugs 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 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 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- RLOSTJFTJFPCOV-UHFFFAOYSA-N 1-(2-chloro-2-phenylethyl)-4-cyanopyrrole-2-carbonyl chloride Chemical compound C=1C=CC=CC=1C(Cl)CN1C=C(C#N)C=C1C(Cl)=O RLOSTJFTJFPCOV-UHFFFAOYSA-N 0.000 description 1
- RPYDMZJAUBYFPR-UHFFFAOYSA-N 11-[3-(dimethylamino)propyl]-11-hydroxy-5,6-dihydropyrrolo[2,1-b][3]benzazepine-2-carbonitrile Chemical compound C1CC2=CC=CC=C2C(CCCN(C)C)(O)C2=CC(C#N)=CN21 RPYDMZJAUBYFPR-UHFFFAOYSA-N 0.000 description 1
- SKCHALNVVMXVIO-UHFFFAOYSA-N 11-[3-(dimethylamino)propyl]-11-hydroxypyrrolo[2,1-b][3]benzazepine-2-carbonitrile Chemical compound C1=CC2=CC=CC=C2C(CCCN(C)C)(O)C2=CC(C#N)=CN21 SKCHALNVVMXVIO-UHFFFAOYSA-N 0.000 description 1
- PWJLKYMVJVBEPD-UHFFFAOYSA-N 11-[3-(dimethylamino)propyl]-5,6-dihydropyrrolo[2,1-b][3]benzazepin-11-ol Chemical compound C1CC2=CC=CC=C2C(CCCN(C)C)(O)C2=CC=CN21 PWJLKYMVJVBEPD-UHFFFAOYSA-N 0.000 description 1
- RKHQFHXIWDYGPC-UHFFFAOYSA-N 11-[3-(dimethylamino)propylidene]-5,6-dihydropyrrolo[1,2-c][3]benzazepine-2-carbaldehyde;oxalic acid Chemical compound OC(=O)C(O)=O.C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC(C=O)=CN21 RKHQFHXIWDYGPC-UHFFFAOYSA-N 0.000 description 1
- BJIZXECRDHHTFL-UHFFFAOYSA-N 11-[3-(dimethylamino)propylidene]pyrrolo[2,1-b][3]benzazepine-2-carbonitrile Chemical compound C1=CC2=CC=CC=C2C(=CCCN(C)C)C2=CC(C#N)=CN21 BJIZXECRDHHTFL-UHFFFAOYSA-N 0.000 description 1
- ZVJHKYFQORNKRJ-UHFFFAOYSA-N 11h-pyrrolo[2,1-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2CC2=CC=CN21 ZVJHKYFQORNKRJ-UHFFFAOYSA-N 0.000 description 1
- UPQQXPKAYZYUKO-UHFFFAOYSA-N 2,2,2-trichloroacetamide Chemical compound OC(=N)C(Cl)(Cl)Cl UPQQXPKAYZYUKO-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
- YGLDQFWPUCURIP-UHFFFAOYSA-N 3h-3-benzazepine Chemical class C1=CNC=CC2=CC=CC=C21 YGLDQFWPUCURIP-UHFFFAOYSA-N 0.000 description 1
- SCHRRVXSPNLRMS-UHFFFAOYSA-N 3h-pyrrolo[2,1-b][3]benzazepine Chemical compound C1=CN2CC=CC2=CC2=CC=CC=C21 SCHRRVXSPNLRMS-UHFFFAOYSA-N 0.000 description 1
- IGAPMRZOLYQEJB-UHFFFAOYSA-N 4-cyano-1-(2-phenylethyl)pyrrole-2-carbonyl chloride Chemical compound ClC(=O)C1=CC(C#N)=CN1CCC1=CC=CC=C1 IGAPMRZOLYQEJB-UHFFFAOYSA-N 0.000 description 1
- WFEMZZIWWBHTKO-UHFFFAOYSA-N 5,6-dihydropyrrolo[1,2-c][3]benzazepin-11-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC=CN21 WFEMZZIWWBHTKO-UHFFFAOYSA-N 0.000 description 1
- BSNBDFRHEYCWQL-UHFFFAOYSA-N 6,11-dihydro-5H-pyrrolo[1,2-c][3]benzazepine Chemical compound C=1C=CN2C=1CC1=C(CC2)C=CC=C1 BSNBDFRHEYCWQL-UHFFFAOYSA-N 0.000 description 1
- WGMCAGDVZCLVAG-UHFFFAOYSA-N 9-iodo-5,6-dihydropyrrolo[1,2-c][3]benzazepin-11-one Chemical compound C1CN2C=CC=C2C(=O)C2=CC(I)=CC=C21 WGMCAGDVZCLVAG-UHFFFAOYSA-N 0.000 description 1
- 208000003174 Brain Neoplasms Diseases 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010049095 Decerebration Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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- 206010021118 Hypotonia Diseases 0.000 description 1
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- 208000021642 Muscular disease Diseases 0.000 description 1
- 201000002481 Myositis Diseases 0.000 description 1
- PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
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- 208000018737 Parkinson disease Diseases 0.000 description 1
- 208000008765 Sciatica Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- DRUIESSIVFYOMK-UHFFFAOYSA-N Trichloroacetonitrile Chemical compound ClC(Cl)(Cl)C#N DRUIESSIVFYOMK-UHFFFAOYSA-N 0.000 description 1
- 210000001361 achilles tendon Anatomy 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 1
- 229960000836 amitriptyline Drugs 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000002917 arthritic effect Effects 0.000 description 1
- 210000001841 basilar artery Anatomy 0.000 description 1
- 150000008038 benzoazepines Chemical class 0.000 description 1
- 208000029028 brain injury Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 210000003710 cerebral cortex Anatomy 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 206010008129 cerebral palsy Diseases 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- BCCLDZVXWYCMMP-UHFFFAOYSA-M copper(1+);trifluoromethanethiolate Chemical compound [Cu+].FC(F)(F)[S-] BCCLDZVXWYCMMP-UHFFFAOYSA-M 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- VXEAYBOGHINOKW-UHFFFAOYSA-N cyclobenzaprine hydrochloride Chemical compound Cl.C1=CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 VXEAYBOGHINOKW-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- QPJORFLSOJAUNL-UHFFFAOYSA-N dibenzo[a,d][7]annulene Chemical class C1=CC2=CC=CC=C2CC2=CC=CC=C21 QPJORFLSOJAUNL-UHFFFAOYSA-N 0.000 description 1
- 150000008508 dibenzocycloheptenes Chemical class 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 210000003746 feather Anatomy 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002496 iodine Chemical class 0.000 description 1
- 230000003447 ipsilateral effect Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000036244 malformation Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 210000001259 mesencephalon Anatomy 0.000 description 1
- KLLCRUMWQRYULP-UHFFFAOYSA-N methyl 4-cyano-1h-pyrrole-2-carboxylate Chemical compound COC(=O)C1=CC(C#N)=CN1 KLLCRUMWQRYULP-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- KDSZUONIFFXPON-UHFFFAOYSA-N n,n-dimethyl-3-[9-(trifluoromethylsulfanyl)pyrrolo[2,1-b][3]benzazepin-11-ylidene]propan-1-amine Chemical compound C1=CC2=CC=C(SC(F)(F)F)C=C2C(=CCCN(C)C)C2=CC=CN21 KDSZUONIFFXPON-UHFFFAOYSA-N 0.000 description 1
- WFBBCLFMSDMILA-UHFFFAOYSA-N n,n-dimethyl-3-pyrrolo[2,1-b][3]benzazepin-11-ylidenepropan-1-amine Chemical compound C1=CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CN21 WFBBCLFMSDMILA-UHFFFAOYSA-N 0.000 description 1
- 229960001158 nortriptyline Drugs 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000399 orthopedic effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 210000003455 parietal bone Anatomy 0.000 description 1
- 230000001936 parietal effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 210000004129 prosencephalon Anatomy 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 208000018198 spasticity Diseases 0.000 description 1
- 208000020431 spinal cord injury Diseases 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 210000003582 temporal bone Anatomy 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59243675A | 1975-07-02 | 1975-07-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2629877A1 DE2629877A1 (de) | 1977-01-20 |
| DE2629877C2 true DE2629877C2 (en:Method) | 1989-01-05 |
Family
ID=24370639
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762629877 Granted DE2629877A1 (de) | 1975-07-02 | 1976-07-02 | Pyrrolo eckige klammer auf 2,1-b eckige klammer zu eckige klammer auf 3 eckige klammer zu benzazepine |
| DE2661014A Expired DE2661014C2 (en:Method) | 1975-07-02 | 1976-07-02 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2661014A Expired DE2661014C2 (en:Method) | 1975-07-02 | 1976-07-02 |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS527996A (en:Method) |
| AU (1) | AU499122B2 (en:Method) |
| BE (1) | BE843678A (en:Method) |
| CA (1) | CA1092105A (en:Method) |
| CH (5) | CH626366A5 (en:Method) |
| CY (1) | CY1091A (en:Method) |
| DE (2) | DE2629877A1 (en:Method) |
| ES (1) | ES449432A1 (en:Method) |
| FR (1) | FR2315935A1 (en:Method) |
| GB (1) | GB1499047A (en:Method) |
| GR (1) | GR60851B (en:Method) |
| HK (1) | HK60580A (en:Method) |
| HU (1) | HU177866B (en:Method) |
| MY (1) | MY8100227A (en:Method) |
| NL (1) | NL188287C (en:Method) |
| PT (1) | PT65295B (en:Method) |
| SE (1) | SE424076B (en:Method) |
| ZA (1) | ZA763990B (en:Method) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4148903A (en) * | 1977-07-28 | 1979-04-10 | Merck & Co., Inc. | Antipsychotic, antiserotonin and antihistaminic pyrrolo[2,1-b][3]benzazepines |
| JPH0487401U (en:Method) * | 1990-12-06 | 1992-07-29 | ||
| US6271392B1 (en) | 1994-10-07 | 2001-08-07 | Rhone-Poulenc Inc. | Intermediates useful for the synthesis of 1-arylpyrrole pesticides |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3428677A (en) * | 1962-09-24 | 1969-02-18 | Merck & Co Inc | Chemical compounds and methods of preparing same |
| US3499037A (en) * | 1966-05-31 | 1970-03-03 | Merck & Co Inc | Preparation of trifluoromethyl substituted dibenzocycloheptenes |
-
1976
- 1976-06-30 PT PT65295A patent/PT65295B/pt unknown
- 1976-06-30 CA CA256,080A patent/CA1092105A/en not_active Expired
- 1976-06-30 FR FR7619897A patent/FR2315935A1/fr active Granted
- 1976-07-01 SE SE7607534A patent/SE424076B/xx not_active IP Right Cessation
- 1976-07-01 CH CH844376A patent/CH626366A5/de not_active IP Right Cessation
- 1976-07-01 ES ES449432A patent/ES449432A1/es not_active Expired
- 1976-07-01 GB GB27487/76A patent/GB1499047A/en not_active Expired
- 1976-07-01 AU AU15488/76A patent/AU499122B2/en not_active Expired
- 1976-07-01 BE BE168549A patent/BE843678A/xx not_active IP Right Cessation
- 1976-07-01 GR GR51162A patent/GR60851B/el unknown
- 1976-07-01 CY CY1091A patent/CY1091A/xx unknown
- 1976-07-02 ZA ZA00763990A patent/ZA763990B/xx unknown
- 1976-07-02 JP JP51077992A patent/JPS527996A/ja active Granted
- 1976-07-02 DE DE19762629877 patent/DE2629877A1/de active Granted
- 1976-07-02 HU HU76ME2001A patent/HU177866B/hu unknown
- 1976-07-02 DE DE2661014A patent/DE2661014C2/de not_active Expired
- 1976-07-02 NL NLAANVRAGE7607347,A patent/NL188287C/xx not_active IP Right Cessation
-
1980
- 1980-05-16 CH CH386280A patent/CH626618A5/de not_active IP Right Cessation
- 1980-05-16 CH CH386080A patent/CH626616A5/de not_active IP Right Cessation
- 1980-05-16 CH CH386180A patent/CH626617A5/de not_active IP Right Cessation
- 1980-05-16 CH CH385980A patent/CH626893A5/de not_active IP Right Cessation
- 1980-10-30 HK HK605/80A patent/HK60580A/xx unknown
-
1981
- 1981-12-30 MY MY227/81A patent/MY8100227A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CY1091A (en) | 1980-12-27 |
| SE7607534L (sv) | 1977-01-03 |
| JPS527996A (en) | 1977-01-21 |
| PT65295A (en) | 1976-07-01 |
| SE424076B (sv) | 1982-06-28 |
| NL188287C (nl) | 1992-05-18 |
| HU177866B (en) | 1982-01-28 |
| NL7607347A (nl) | 1977-01-04 |
| DE2661014A1 (en:Method) | 1985-07-04 |
| FR2315935B1 (en:Method) | 1978-11-17 |
| FR2315935A1 (fr) | 1977-01-28 |
| GR60851B (en) | 1978-08-31 |
| CA1092105A (en) | 1980-12-23 |
| ZA763990B (en) | 1978-02-22 |
| HK60580A (en) | 1980-11-07 |
| PT65295B (en) | 1978-05-10 |
| MY8100227A (en) | 1981-12-31 |
| DE2629877A1 (de) | 1977-01-20 |
| CH626893A5 (en) | 1981-12-15 |
| AU499122B2 (en) | 1979-04-05 |
| CH626616A5 (en) | 1981-11-30 |
| NL188287B (nl) | 1991-12-16 |
| AU1548876A (en) | 1978-01-05 |
| DE2661014C2 (en:Method) | 1989-01-05 |
| CH626618A5 (en) | 1981-11-30 |
| CH626617A5 (en) | 1981-11-30 |
| CH626366A5 (en) | 1981-11-13 |
| BE843678A (fr) | 1977-01-03 |
| JPH0132225B2 (en:Method) | 1989-06-29 |
| GB1499047A (en) | 1978-01-25 |
| ES449432A1 (es) | 1977-12-16 |
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