CA1059126A - Derives benzo(a)quinolisidine et procede pour leur preparation - Google Patents

Derives benzo(a)quinolisidine et procede pour leur preparation

Info

Publication number: CA1059126A
Authority: CA; Canada
Prior art keywords: formula; oxo; benzo; quinolisidine; hexahydro
Prior art date: 1975-09-11
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

Application number

CA240,991A

Other languages

English (en)

Inventor

Agoston David

Erzsebet Kanyo

Sandor Virag

Lajos Szabo

Istvan Toth

Laszlo Toke

Csaba Szantay

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Chinoin Private Co Ltd

Original Assignee

Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt

Priority date (The priority date 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 date listed.)

1975-09-11

Filing date

1975-12-03

Publication date

1979-07-24

1975-12-03 Application filed by Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt filed Critical Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt

1979-07-24 Application granted granted Critical

1979-07-24 Publication of CA1059126A publication Critical patent/CA1059126A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 52
230000008569 process Effects 0.000 title claims abstract description 39
238000002360 preparation method Methods 0.000 title claims abstract description 27
125000005605 benzo group Chemical group 0.000 title abstract description 9
150000001875 compounds Chemical class 0.000 claims abstract description 73
239000001257 hydrogen Substances 0.000 claims abstract description 23
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
-1 methylenedioxy group Chemical group 0.000 claims abstract description 16
150000003839 salts Chemical class 0.000 claims abstract description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
150000002431 hydrogen Chemical class 0.000 claims abstract description 11
150000001732 carboxylic acid derivatives Chemical group 0.000 claims abstract description 9
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 7
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 33
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 20
239000000126 substance Substances 0.000 claims description 16
125000004093 cyano group Chemical group *C#N 0.000 claims description 15
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
150000002081 enamines Chemical class 0.000 claims description 10
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
BLKRTGSUDRJCEH-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-5-oxohexanenitrile Chemical compound CN(C)CC(C(C)=O)CCC#N BLKRTGSUDRJCEH-UHFFFAOYSA-N 0.000 claims description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
238000005915 ammonolysis reaction Methods 0.000 claims description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 4
230000002140 halogenating effect Effects 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
XGHRSYWAZLGDDF-UHFFFAOYSA-N methyl 4-[(dimethylamino)methyl]-5-oxodecanoate Chemical compound CCCCCC(=O)C(CN(C)C)CCC(=O)OC XGHRSYWAZLGDDF-UHFFFAOYSA-N 0.000 claims description 4
125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 4
125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 4
239000003586 protic polar solvent Substances 0.000 claims description 4
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
MOYFDJUHGADBRF-UHFFFAOYSA-N 6,7-diethoxy-3,4-dihydroisoquinoline;hydrochloride Chemical compound Cl.C1CN=CC2=C1C=C(OCC)C(OCC)=C2 MOYFDJUHGADBRF-UHFFFAOYSA-N 0.000 claims description 3
125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 3
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
230000032050 esterification Effects 0.000 claims description 3
238000005886 esterification reaction Methods 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
150000003335 secondary amines Chemical class 0.000 claims description 3
KXWLFPPSOCSXPZ-UHFFFAOYSA-N 7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline Chemical compound C1CN=CC2=C1C=C1OCOC1=C2 KXWLFPPSOCSXPZ-UHFFFAOYSA-N 0.000 claims description 2
125000005250 alkyl acrylate group Chemical group 0.000 claims description 2
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 claims description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
238000010992 reflux Methods 0.000 claims description 2
239000002904 solvent Substances 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 2
QBKFLYWZRMHHRS-UHFFFAOYSA-N chloroform;1,4-dioxane Chemical compound ClC(Cl)Cl.C1COCCO1 QBKFLYWZRMHHRS-UHFFFAOYSA-N 0.000 claims 1
230000003301 hydrolyzing effect Effects 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
230000003110 anti-inflammatory effect Effects 0.000 abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
239000000203 mixture Substances 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 13
230000000694 effects Effects 0.000 description 11
229960002895 phenylbutazone Drugs 0.000 description 11
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 11
239000000243 solution Substances 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
206010030113 Oedema Diseases 0.000 description 8
125000003118 aryl group Chemical group 0.000 description 8
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 8
229960000905 indomethacin Drugs 0.000 description 8
230000005764 inhibitory process Effects 0.000 description 7
241001465754 Metazoa Species 0.000 description 6
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 5
230000001741 anti-phlogistic effect Effects 0.000 description 5
230000001754 anti-pyretic effect Effects 0.000 description 5
239000012153 distilled water Substances 0.000 description 5
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
230000000202 analgesic effect Effects 0.000 description 4
239000002260 anti-inflammatory agent Substances 0.000 description 4
229960001701 chloroform Drugs 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
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 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
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
238000009835 boiling Methods 0.000 description 3
238000006243 chemical reaction Methods 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
239000013078 crystal Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
230000003389 potentiating effect Effects 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
PQXVEYYRJHMTEV-UHFFFAOYSA-N 6,7-dimethoxy-3,4-dihydroisoquinolin-2-ium;chloride Chemical compound [Cl-].C1C[NH+]=CC2=C1C=C(OC)C(OC)=C2 PQXVEYYRJHMTEV-UHFFFAOYSA-N 0.000 description 2
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
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
208000025865 Ulcer Diseases 0.000 description 2
239000002253 acid Substances 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
230000003394 haemopoietic effect Effects 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
125000002560 nitrile group Chemical group 0.000 description 2
239000006187 pill Substances 0.000 description 2
229960001860 salicylate Drugs 0.000 description 2
239000000523 sample Substances 0.000 description 2
230000001624 sedative effect Effects 0.000 description 2
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
231100000397 ulcer Toxicity 0.000 description 2
NKSZCPBUWGZONP-UHFFFAOYSA-N 3,4-dihydroisoquinoline Chemical class C1=CC=C2C=NCCC2=C1 NKSZCPBUWGZONP-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
LKHHEMHSIKGIBO-UHFFFAOYSA-N 3-ethylpent-2-enoic acid Chemical compound CCC(CC)=CC(O)=O LKHHEMHSIKGIBO-UHFFFAOYSA-N 0.000 description 1
RTIDGRMONMNKDR-UHFFFAOYSA-N 7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline hydrochloride Chemical compound Cl.C1OC=2C=C3CCN=CC3=CC2O1 RTIDGRMONMNKDR-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-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
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
206010018691 Granuloma Diseases 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 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
229920002472 Starch Polymers 0.000 description 1
208000010513 Stupor Diseases 0.000 description 1
229960001138 acetylsalicylic acid Drugs 0.000 description 1
231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
238000011047 acute toxicity test Methods 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
239000002221 antipyretic Substances 0.000 description 1
229960004217 benzyl alcohol Drugs 0.000 description 1
125000000638 benzylaminocarbonyl group Chemical group C(C1=CC=CC=C1)NC(=O)* 0.000 description 1
230000036760 body temperature Effects 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
229960003563 calcium carbonate Drugs 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
229920001525 carrageenan Polymers 0.000 description 1
235000010418 carrageenan Nutrition 0.000 description 1
239000000969 carrier Substances 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000000839 emulsion Substances 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
230000000763 evoking effect Effects 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
235000014380 magnesium carbonate Nutrition 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
229960001708 magnesium carbonate Drugs 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229940057948 magnesium stearate Drugs 0.000 description 1
229960004815 meprobamate Drugs 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003208 petroleum Substances 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
239000002798 polar solvent Substances 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
229940032147 starch Drugs 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000003637 steroidlike Effects 0.000 description 1
231100000820 toxicity test Toxicity 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CA240,991A 1975-09-11 1975-12-03 Derives benzo(a)quinolisidine et procede pour leur preparation Expired CA1059126A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
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
CA1059126A true CA1059126A (fr)	1979-07-24

Family

ID=10994579

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA240,991A Expired CA1059126A (fr)	1975-09-11	1975-12-03	Derives benzo(a)quinolisidine et procede pour leur preparation

Country Status (3)

Country	Link
CA (1)	CA1059126A (fr)
HU (1)	HU174551B (fr)
SU (2)	SU655309A3 (fr)

1975
- 1975-09-11 HU HU75CI1603A patent/HU174551B/hu unknown
- 1975-12-03 CA CA240,991A patent/CA1059126A/fr not_active Expired
1976
- 1976-09-16 SU SU762398648A patent/SU655309A3/ru active
- 1976-11-05 SU SU762186408A patent/SU862821A3/ru active

Also Published As

Publication number	Publication date
SU862821A3 (ru)	1981-09-07
SU655309A3 (ru)	1979-03-30
HU174551B (hu)	1980-02-28

Publication	Publication Date	Title
CA1091247A (fr)	1980-12-09	Benzamides n-acyl-substituees, methode de preparation et medicaments les contenant
EP0025111B1 (fr)	1984-07-25	Dérivés 3-aminopropoxyaryliques, leur préparation et compositions pharmaceutiques les contenant
US4102886A (en)	1978-07-25	Process for the preparation of benzo(a)quinolizidine derivatives
US3752823A (en)	1973-08-14	N alkyl tetrahydrocarbazoles
US3123618A (en)	1964-03-03	Io-dihydroanthkacene-z
US4291039A (en)	1981-09-22	Tetrahydro β-carbolines having anti-hypertensive activity
US4209622A (en)	1980-06-24	3-(Ethoxycarbonyl-methyl)-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine
US2784199A (en)	1957-03-05	Endoxy isoindoline derivatives and salts thereof
US4208420A (en)	1980-06-17	New benzo [d] thiazole derivatives, process for their preparation and their therapeutic applications
US3458515A (en)	1969-07-29	Piperazine substituted pyrroles
US4029787A (en)	1977-06-14	Basically substituted 3-sulfamoylbenzoic acid derivatives and process for their preparation
US3647802A (en)	1972-03-07	2-amino-4-aryl-3 4-dihydroquinolines
US4101660A (en)	1978-07-18	2-Aminomethyl-5-phenyloxazoles and the pharmaceutically acceptable acid addition salts thereof
US4232160A (en)	1980-11-04	Isoquinoline propionamides exhibiting analgesic properties
US4013667A (en)	1977-03-22	2,2-Diaryl-3-(1-azabicyclo[2.2.2]oct-2-yl)propionamides and intermediates thereto
US2897195A (en)	1959-07-28	Nxyxc
FI63578C (fi)	1983-07-11	Analogifoerfarande foer framstaellning av nya farmakologiskt verksamma 1,3,4,14b-tetrahydro-2h 10h-pyrazino(1,2-a)pyrrolo(2,1-c)(1,4)bensodiazepiner
US4123541A (en)	1978-10-31	2-Aminomethyl-5-phenyloxazoles and the pharmaceutically acceptable salts thereof
US3328406A (en)	1967-06-27	Amide and piperazides of carbazole-9-glyoxylic acid
US3927015A (en)	1975-12-16	2-(3-Hydroxyaminomethyl-S-triazol-4-yl)benzophenones
US5098919A (en)	1992-03-24	Pyrrolo(2,1-b)thiazole derivatives
CA2055225A1 (fr)	1992-05-15	Composes, compositions pharmaceutiques les renfermant et procede pour les preparer
US3318902A (en)	1967-05-09	Substituted phenylacetic acid esters of hydroxyalkyl azaspiranes
US3812135A (en)	1974-05-21	Pyrroloindole and pyridoindole derivatives
US3950346A (en)	1976-04-13	Novel process for producing 2-ketoethylbenzomorphan derivatives and salts thereof