DE2311019A1 - Imidazolidinderivate - Google Patents
ImidazolidinderivateInfo
- Publication number
- DE2311019A1 DE2311019A1 DE19732311019 DE2311019A DE2311019A1 DE 2311019 A1 DE2311019 A1 DE 2311019A1 DE 19732311019 DE19732311019 DE 19732311019 DE 2311019 A DE2311019 A DE 2311019A DE 2311019 A1 DE2311019 A1 DE 2311019A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- carbon atoms
- hydrogen
- atom
- acid
- 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.)
- Pending
Links
- 150000002461 imidazolidines Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 28
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000003153 chemical reaction reagent Substances 0.000 claims description 10
- 229910052717 sulfur Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- -1 ethylene halide Chemical class 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 5
- 238000006482 condensation reaction Methods 0.000 claims description 5
- 230000003287 optical effect Effects 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 239000000935 antidepressant agent Substances 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- WXLCDTBTIVJDCE-UHFFFAOYSA-N 1,4-oxazepine Chemical compound O1C=CC=NC=C1 WXLCDTBTIVJDCE-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- CJKPKVLFYAXEBS-UHFFFAOYSA-N 2,3,6,7-tetrahydrooxazepine Chemical compound C1CC=CCNO1 CJKPKVLFYAXEBS-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000008098 formaldehyde solution Substances 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QPPOMEOQNLTFRU-UHFFFAOYSA-N 1,4-thiazepine Chemical compound S1C=CC=NC=C1 QPPOMEOQNLTFRU-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 230000001387 anti-histamine Effects 0.000 description 3
- 230000000794 anti-serotonin Effects 0.000 description 3
- 239000000739 antihistaminic agent Substances 0.000 description 3
- 239000003420 antiserotonin agent Substances 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-ZILXKATJSA-N (3R)-2,3-dihydroxybutanedioic acid Chemical compound OC([C@@H](O)C(O)=O)C(O)=O FEWJPZIEWOKRBE-ZILXKATJSA-N 0.000 description 1
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-PIKHSQJKSA-N (3s)-2,3-dihydroxybutanedioic acid Chemical compound OC(=O)C(O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-PIKHSQJKSA-N 0.000 description 1
- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 description 1
- POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical group C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- GRTOGORTSDXSFK-XJTZBENFSA-N ajmalicine Chemical compound C1=CC=C2C(CCN3C[C@@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 GRTOGORTSDXSFK-XJTZBENFSA-N 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- MGJURKDLIJVDEO-UHFFFAOYSA-N formaldehyde;hydrate Chemical compound O.O=C MGJURKDLIJVDEO-UHFFFAOYSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SFJGCXYXEFWEBK-UHFFFAOYSA-N oxazepine Chemical compound O1C=CC=CC=N1 SFJGCXYXEFWEBK-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient 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
- 239000006187 pill Substances 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7202963A NL7202963A (enrdf_load_stackoverflow) | 1972-03-07 | 1972-03-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2311019A1 true DE2311019A1 (de) | 1973-09-20 |
Family
ID=19815531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732311019 Pending DE2311019A1 (de) | 1972-03-07 | 1973-03-06 | Imidazolidinderivate |
Country Status (16)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0035749A1 (de) * | 1980-03-08 | 1981-09-16 | C.H. Boehringer Sohn | Heterocyclische Verbindungen, ihre Herstellung und diese Verbindungen enthaltende Arzneimittel |
| EP0073506A1 (de) * | 1981-09-02 | 1983-03-09 | Boehringer Ingelheim Kg | Heterocyclische Verbindungen, ihre Herstellung und Verwendung |
| DE3643991A1 (de) * | 1985-12-20 | 1987-06-25 | Egyt Gyogyszervegyeszeti Gyar | Optisch aktive 2-(chlor)-12-(3-(dimethylamino)-2-(methyl)-propyl)-12h-dibenzo(d,g)(1,3,6)dioxazocine sowie ihre saeureadditionssalze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL178593C (nl) * | 1974-01-31 | 1986-04-16 | Akzo Nv | Werkwijze ter bereiding van een farmaceutisch preparaat op basis van een tetracyclische verbinding en werkwijze voor de bereiding van de daarbij te gebruiken tetracyclische verbindingen. |
| NL7414038A (nl) * | 1974-10-28 | 1976-05-03 | Akzo Nv | Nieuwe tetracyclische pyrrolidino derivaten. |
| NL189199C (nl) * | 1975-04-05 | 1993-02-01 | Akzo Nv | Werkwijze ter bereiding van farmaceutische preparaten met werking op het centraal zenuwstelsel op basis van benz(aryl)azepinederivaten, de verkregen gevormde farmaceutische preparaten, alsmede werkwijze ter bereiding van de toe te passen benz(aryl)azepinederivaten. |
| JPS60500176A (ja) * | 1982-12-30 | 1985-02-07 | ビ−チヤム グル−プ ピ−エルシ− | 四環式化合物 |
| US4728735A (en) * | 1984-10-15 | 1988-03-01 | Merck & Co., Inc. | 10,11-dihydro-dibenzo-[b,f][1,4]-thiazepin derivatives |
| US5478934A (en) * | 1994-11-23 | 1995-12-26 | Yuan; Jun | Certain 1-substituted aminomethyl imidazole and pyrrole derivatives: novel dopamine receptor subtype specific ligands |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3435042A (en) * | 1965-03-30 | 1969-03-25 | Colgate Palmolive Co | Novel morphanthridine derivatives |
-
1972
- 1972-03-07 NL NL7202963A patent/NL7202963A/xx unknown
-
1973
- 1973-02-15 ZA ZA731086A patent/ZA731086B/xx unknown
- 1973-02-19 AU AU52303/73A patent/AU471800B2/en not_active Expired
- 1973-02-26 IE IE297/73A patent/IE37322B1/xx unknown
- 1973-03-01 GB GB1006173A patent/GB1421006A/en not_active Expired
- 1973-03-01 AR AR246878A patent/AR202388A1/es active
- 1973-03-02 US US337323A patent/US3860606A/en not_active Expired - Lifetime
- 1973-03-06 CH CH328773A patent/CH589083A5/xx not_active IP Right Cessation
- 1973-03-06 CA CA165,357A patent/CA1010032A/en not_active Expired
- 1973-03-06 BE BE128428A patent/BE796341A/xx unknown
- 1973-03-06 JP JP48026503A patent/JPS4899198A/ja active Pending
- 1973-03-06 HU HUAO353A patent/HU166348B/hu unknown
- 1973-03-06 ES ES412372A patent/ES412372A1/es not_active Expired
- 1973-03-06 DE DE19732311019 patent/DE2311019A1/de active Pending
- 1973-03-07 AT AT203073A patent/AT326667B/de not_active IP Right Cessation
- 1973-03-07 FR FR7308169A patent/FR2181796B1/fr not_active Expired
-
1974
- 1974-11-08 AR AR256461A patent/AR202429A1/es active
- 1974-11-08 AR AR256460A patent/AR203866A1/es active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0035749A1 (de) * | 1980-03-08 | 1981-09-16 | C.H. Boehringer Sohn | Heterocyclische Verbindungen, ihre Herstellung und diese Verbindungen enthaltende Arzneimittel |
| DK154299B (da) * | 1980-03-08 | 1988-10-31 | Boehringer Sohn Ingelheim | Analogifremgangsmaade til fremstilling af dibenzoimidazo-azepiner, -oxazepiner og -thiazepiner |
| EP0073506A1 (de) * | 1981-09-02 | 1983-03-09 | Boehringer Ingelheim Kg | Heterocyclische Verbindungen, ihre Herstellung und Verwendung |
| DE3643991A1 (de) * | 1985-12-20 | 1987-06-25 | Egyt Gyogyszervegyeszeti Gyar | Optisch aktive 2-(chlor)-12-(3-(dimethylamino)-2-(methyl)-propyl)-12h-dibenzo(d,g)(1,3,6)dioxazocine sowie ihre saeureadditionssalze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Also Published As
| Publication number | Publication date |
|---|---|
| IE37322L (en) | 1973-09-07 |
| ES412372A1 (es) | 1976-05-01 |
| FR2181796A1 (enrdf_load_stackoverflow) | 1973-12-07 |
| ATA203073A (de) | 1975-03-15 |
| AU5230373A (en) | 1974-08-22 |
| GB1421006A (en) | 1976-01-14 |
| FR2181796B1 (enrdf_load_stackoverflow) | 1976-10-22 |
| NL7202963A (enrdf_load_stackoverflow) | 1973-09-11 |
| AR202388A1 (es) | 1975-06-06 |
| HU166348B (enrdf_load_stackoverflow) | 1975-03-28 |
| IE37322B1 (en) | 1977-06-22 |
| CA1010032A (en) | 1977-05-10 |
| ZA731086B (en) | 1973-11-28 |
| AT326667B (de) | 1975-12-29 |
| AR202429A1 (es) | 1975-06-06 |
| US3860606A (en) | 1975-01-14 |
| AU471800B2 (en) | 1976-05-06 |
| BE796341A (nl) | 1973-09-06 |
| CH589083A5 (enrdf_load_stackoverflow) | 1977-06-30 |
| AR203866A1 (es) | 1975-10-31 |
| JPS4899198A (enrdf_load_stackoverflow) | 1973-12-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0035749B1 (de) | Heterocyclische Verbindungen, ihre Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| EP0572863A1 (de) | ZNS Pyrazinoindole | |
| DE2311019A1 (de) | Imidazolidinderivate | |
| DE1770756A1 (de) | Piperazinderivate und Verfahren zu deren Herstellung | |
| AT414125B (de) | Neue derivate des 4a,5,9,10,11,12-hexahydro- benzofuro(3a,3,2)(2) benzazepin, verfahren zu deren herstellung sowie deren verwendung zur herstellung von arzneimitteln | |
| DE2248477A1 (de) | Imidazolinverbindungen | |
| EP1265904A1 (de) | Neue positive allosterische ampa-rezeptor modulatoren (paarm), verfahren zu deren herstellung und deren verwendung als arzneimittel | |
| EP0008652A1 (de) | Neue Zwischenprodukte und deren Verwendung zur Herstellung von neuen Oxadiazolopyrimidinderivaten | |
| EP0534904A1 (de) | Imidazolylmethyl-Pyridine | |
| DD146186A5 (de) | Verfahren zur herstellung einer 4a,9b-hexahydro-ypsilon-verbindung | |
| DE2347727C2 (de) | Dibenzo-pyrimido-azepine, -oxazepine und- diazepine | |
| EP0064685A1 (de) | Dibenzo(de,g)chinolin-Derivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel | |
| EP0461574B1 (de) | 3,7-Diazabicyclo(3,3,1)-nonan-Verbindungen enthaltende Arzneimittel | |
| DE2841644C2 (enrdf_load_stackoverflow) | ||
| DE69328701T2 (de) | Diazabicycloderivate als 5-HT3-Antagonisten | |
| EP0266308B1 (de) | Indolo-pyrazino-benzodiazepin-Derivate | |
| CH638215A5 (de) | Oxadiazolopyrimidin-derivate. | |
| DE2601473A1 (de) | 2,3-dihydroergoline und verfahren zu ihrer herstellung | |
| DE2417063A1 (de) | Tricyclische sulfoximid-derivate | |
| DE2334782A1 (de) | 12-acyl-5,6,11,12-tetrahydrodibenzo eckige klammer auf b,f eckige klammer zu eckige klammer auf 1,4 eckige klammer zu diazocinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| DD220307A5 (de) | Verfahren zur herstellung von polycyclische carbonsaeureverbindungen | |
| DE69324794T2 (de) | Phenyl imidazolinon-derivate, verfahren zu ihrer herstellung und ihre verwendung als 5-ht3-rezeptor-antagonisten | |
| DE2716172A1 (de) | Bis-penicillanoyloxy-alkane | |
| DE2118339A1 (de) | Pipendinspiroverbindungen | |
| AT330782B (de) | Verfahren zur herstellung von neuen piperazinderivaten und ihren saureadditionssalzen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| OHJ | Non-payment of the annual fee |