CH626615A5 - - Google Patents
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- CH626615A5 CH626615A5 CH1369275A CH1369275A CH626615A5 CH 626615 A5 CH626615 A5 CH 626615A5 CH 1369275 A CH1369275 A CH 1369275A CH 1369275 A CH1369275 A CH 1369275A CH 626615 A5 CH626615 A5 CH 626615A5
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- CH
- Switzerland
- Prior art keywords
- group
- compounds
- formula
- hydrogen
- general formula
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 45
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 21
- -1 methylenedioxy group Chemical group 0.000 claims description 17
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- RHVCCFKUACIGSM-UHFFFAOYSA-N 2,3,4,6,7,11b-hexahydro-1h-benzo[a]quinolizine Chemical class C1CC2=CC=CC=C2C2N1CCCC2 RHVCCFKUACIGSM-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 7
- 150000002081 enamines Chemical class 0.000 claims description 7
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 239000003586 protic polar solvent Substances 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims 4
- 238000009835 boiling Methods 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000004185 ester group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- NKSZCPBUWGZONP-UHFFFAOYSA-N 3,4-dihydroisoquinoline Chemical class C1=CC=C2C=NCCC2=C1 NKSZCPBUWGZONP-UHFFFAOYSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 238000005915 ammonolysis reaction Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 15
- 229960002895 phenylbutazone Drugs 0.000 description 12
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 10
- 239000000155 melt Substances 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- WSOLXOBNHSHKFH-UHFFFAOYSA-N 3-(9,10-diethoxy-2-oxo-1,3,4,6,7,11b-hexahydrobenzo[a]quinolizin-3-yl)propanenitrile Chemical compound C1CN2CC(CCC#N)C(=O)CC2C2=C1C=C(OCC)C(OCC)=C2 WSOLXOBNHSHKFH-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- QLSCNQCATINUIJ-UHFFFAOYSA-N 3-(9,10-dimethoxy-2-oxo-1,3,4,6,7,11b-hexahydrobenzo[a]quinolizin-3-yl)propanenitrile Chemical compound C1CN2CC(CCC#N)C(=O)CC2C2=C1C=C(OC)C(OC)=C2 QLSCNQCATINUIJ-UHFFFAOYSA-N 0.000 description 6
- 206010030113 Oedema Diseases 0.000 description 6
- 229960000905 indomethacin Drugs 0.000 description 6
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000001754 anti-pyretic effect Effects 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 230000001562 ulcerogenic effect Effects 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229940076279 serotonin Drugs 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 229960000212 aminophenazone Drugs 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000001624 sedative effect Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 231100001274 therapeutic index Toxicity 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- INOGRTKGRNICER-UHFFFAOYSA-N [Cl-].C1CCC[NH+]2CCCCC12 Chemical compound [Cl-].C1CCC[NH+]2CCCCC12 INOGRTKGRNICER-UHFFFAOYSA-N 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000000638 benzylaminocarbonyl group Chemical group C(C1=CC=CC=C1)NC(=O)* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- LJPZHJUSICYOIX-UHFFFAOYSA-N quinolizidine Chemical compound C1CCCC2CCCCN21 LJPZHJUSICYOIX-UHFFFAOYSA-N 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 230000004617 sleep duration Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229960004025 sodium salicylate Drugs 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
Classifications
-
- 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
- C07D491/12—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 three hetero rings
- C07D491/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
- C07D455/06—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine containing benzo [a] quinolizine ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU74CI00001514A HU172466B (hu) | 1974-10-23 | 1974-10-23 | Sposob poluchenija proizvodnykh benzo/a/khinolizidina s ingibitirujuhhim dejstviem protiv vospalenija |
| HU75CI1603A HU174551B (hu) | 1975-09-11 | 1975-09-11 | Sposob poluchenija proizvodnykh benzo-skobka-a-skobka zakrytakinazolizidina s antiflogistichnojj aktivnost'ju |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH626615A5 true CH626615A5 (en, 2012) | 1981-11-30 |
Family
ID=26318402
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1369275A CH626615A5 (en, 2012) | 1974-10-23 | 1975-10-22 | |
| CH320081A CH628894A5 (de) | 1974-10-23 | 1981-05-15 | Verfahren zum herstellen von neuen benzo(a) chinolizidin-derivaten. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH320081A CH628894A5 (de) | 1974-10-23 | 1981-05-15 | Verfahren zum herstellen von neuen benzo(a) chinolizidin-derivaten. |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US4102886A (en, 2012) |
| AT (1) | AT352730B (en, 2012) |
| CH (2) | CH626615A5 (en, 2012) |
| DD (1) | DD123666A1 (en, 2012) |
| DE (1) | DE2547287A1 (en, 2012) |
| DK (1) | DK475975A (en, 2012) |
| FI (1) | FI752952A7 (en, 2012) |
| FR (1) | FR2289193A1 (en, 2012) |
| GB (1) | GB1521320A (en, 2012) |
| NL (1) | NL7512415A (en, 2012) |
| NO (1) | NO144529C (en, 2012) |
| YU (2) | YU264675A (en, 2012) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU264675A (en) * | 1974-10-23 | 1982-05-31 | Chinoin Gyogyszer Es Vegyeszet | Process for obtaining benzo (a)-quinolizidine derivatives |
| HU175890B (en) * | 1977-06-15 | 1980-11-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing new 1,2,3,4,6,7-hexahydro-11-b-alpha-benzo-square bracket-a-square brecket closed-quinolyzine derivatives |
| US4992446A (en) * | 1989-09-05 | 1991-02-12 | G. D. Searle & Co. | Tricyclic quinolizine amides |
| GB2410947B (en) * | 2004-02-11 | 2008-09-17 | Cambridge Lab Ltd | Pharmaceutical compounds |
| GB0514501D0 (en) * | 2005-07-14 | 2005-08-24 | Cambridge Lab Ireland Ltd | Pharmaceutical compounds |
| GB0516168D0 (en) * | 2005-08-05 | 2005-09-14 | Cambridge Lab Ireland Ltd | Pharmaceutical compounds |
| GB0810857D0 (en) * | 2008-06-13 | 2008-07-23 | Cambridge Lab Ireland Ltd | Pharmaceutical compounds |
| GB2462611A (en) * | 2008-08-12 | 2010-02-17 | Cambridge Lab | Pharmaceutical composition comprising tetrabenazine |
| US20110053866A1 (en) * | 2008-08-12 | 2011-03-03 | Biovail Laboratories International (Barbados) S.R.L. | Pharmaceutical compositions |
| GB2463451A (en) | 2008-09-08 | 2010-03-17 | Cambridge Lab | 3, 11b cis-dihydrotetrabenazine compounds for use in the treatment of dementia |
| GB2463283A (en) * | 2008-09-08 | 2010-03-10 | Cambridge Lab | 3,11b-cis-dihydrotetrabenazine for use in treating asthma |
| GB2463452A (en) * | 2008-09-08 | 2010-03-17 | Cambridge Lab | Desmethyl derivatives of tetrabenazine and pharmaceutical compositions thereof |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2830992A (en) * | 1958-04-15 | Quinolizine derivatives | ||
| US2830993A (en) * | 1958-04-15 | Quinolizine derivatives | ||
| US3095419A (en) * | 1963-06-25 | Process for preparing z-oxo-j- | ||
| US2843591A (en) * | 1958-07-15 | Method for preparing same | ||
| US3123609A (en) * | 1964-03-03 | Benzo | ||
| US3635986A (en) * | 1969-12-22 | 1972-01-18 | Miles Lab | 2-substituted amino-hexahydrobenzo(a)quinolizines |
| US3634431A (en) * | 1969-12-22 | 1972-01-11 | Miles Lab | Acylated and alkylated derivatives of 2-aminohexahydrobenzo(a)quinolizines |
| YU264675A (en) * | 1974-10-23 | 1982-05-31 | Chinoin Gyogyszer Es Vegyeszet | Process for obtaining benzo (a)-quinolizidine derivatives |
| DE2757113A1 (de) * | 1977-12-21 | 1979-06-28 | Siegfried Ag | Imidazolylvinylaether und verfahren zu ihrer herstellung |
-
1975
- 1975-10-20 YU YU02646/75A patent/YU264675A/xx unknown
- 1975-10-21 GB GB43206/75A patent/GB1521320A/en not_active Expired
- 1975-10-21 US US05/624,470 patent/US4102886A/en not_active Expired - Lifetime
- 1975-10-22 DE DE19752547287 patent/DE2547287A1/de not_active Withdrawn
- 1975-10-22 NO NO753544A patent/NO144529C/no unknown
- 1975-10-22 FI FI752952A patent/FI752952A7/fi not_active Application Discontinuation
- 1975-10-22 CH CH1369275A patent/CH626615A5/de not_active IP Right Cessation
- 1975-10-22 DD DD188991A patent/DD123666A1/xx unknown
- 1975-10-22 DK DK475975A patent/DK475975A/da not_active Application Discontinuation
- 1975-10-23 FR FR7532428A patent/FR2289193A1/fr active Granted
- 1975-10-23 NL NL7512415A patent/NL7512415A/xx not_active Application Discontinuation
- 1975-10-23 AT AT808075A patent/AT352730B/de not_active IP Right Cessation
-
1976
- 1976-11-24 US US05/744,608 patent/US4342871A/en not_active Expired - Lifetime
-
1981
- 1981-05-15 CH CH320081A patent/CH628894A5/de not_active IP Right Cessation
- 1981-07-30 YU YU01877/81A patent/YU187781A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO144529C (no) | 1981-09-16 |
| FR2289193B1 (en, 2012) | 1980-05-30 |
| AU8593275A (en) | 1977-04-28 |
| US4102886A (en) | 1978-07-25 |
| YU187781A (en) | 1983-01-21 |
| YU264675A (en) | 1982-05-31 |
| NO144529B (no) | 1981-06-09 |
| US4342871A (en) | 1982-08-03 |
| DE2547287A1 (de) | 1976-04-29 |
| DK475975A (da) | 1976-04-24 |
| NO753544L (en, 2012) | 1976-04-26 |
| DD123666A1 (en, 2012) | 1977-01-12 |
| FI752952A7 (en, 2012) | 1976-04-24 |
| ATA808075A (de) | 1979-03-15 |
| AT352730B (de) | 1979-10-10 |
| CH628894A5 (de) | 1982-03-31 |
| FR2289193A1 (fr) | 1976-05-28 |
| GB1521320A (en) | 1978-08-16 |
| NL7512415A (nl) | 1976-04-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |