GB1122212A - Process for the preparation of substituted piperidine derivatives - Google Patents
Process for the preparation of substituted piperidine derivativesInfo
- Publication number
- GB1122212A GB1122212A GB3485665A GB3485665A GB1122212A GB 1122212 A GB1122212 A GB 1122212A GB 3485665 A GB3485665 A GB 3485665A GB 3485665 A GB3485665 A GB 3485665A GB 1122212 A GB1122212 A GB 1122212A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethoxy
- tetrahydro
- isoquinolyl
- acid
- benzoyl
- 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
- 238000000034 method Methods 0.000 title abstract 2
- 150000003053 piperidines Chemical class 0.000 title 1
- -1 methylenedioxy group Chemical group 0.000 abstract 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 8
- NSLJVQUDZCZJLK-UHFFFAOYSA-N 6,7-dimethoxy-3,4-dihydroisoquinoline Chemical compound C1CN=CC2=C1C=C(OC)C(OC)=C2 NSLJVQUDZCZJLK-UHFFFAOYSA-N 0.000 abstract 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000003118 aryl group Chemical group 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 abstract 3
- 239000000047 product Substances 0.000 abstract 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 abstract 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- IGCLBXMPDYBWJC-UHFFFAOYSA-N 1-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)-4-phenylbutan-2-one Chemical compound O=C(CC1NCCC2=CC(=C(C=C12)OC)OC)CCC1=CC=CC=C1 IGCLBXMPDYBWJC-UHFFFAOYSA-N 0.000 abstract 1
- TYMMLFUYTPWHOL-UHFFFAOYSA-N 2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)-1-(4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C=C1)C(CC1NCCC2=CC(=C(C=C12)OC)OC)=O TYMMLFUYTPWHOL-UHFFFAOYSA-N 0.000 abstract 1
- OXTNCQMOKLOUAM-UHFFFAOYSA-N 3-Oxoglutaric acid Chemical compound OC(=O)CC(=O)CC(O)=O OXTNCQMOKLOUAM-UHFFFAOYSA-N 0.000 abstract 1
- MFEILWXBDBCWKF-UHFFFAOYSA-N 3-phenylpropanoyl chloride Chemical compound ClC(=O)CCC1=CC=CC=C1 MFEILWXBDBCWKF-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 230000003569 amebicidal effect Effects 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- XHZKIWBUQAONBR-UHFFFAOYSA-N benzyl 6,7-dimethoxy-1-(2-oxopropyl)-3,4-dihydro-1H-isoquinoline-2-carboxylate Chemical compound C(=O)(OCC1=CC=CC=C1)N1C(C2=CC(=C(C=C2CC1)OC)OC)CC(=O)C XHZKIWBUQAONBR-UHFFFAOYSA-N 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 239000006071 cream Substances 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 239000007937 lozenge Substances 0.000 abstract 1
- MIOOVIILBQHHNK-UHFFFAOYSA-N methyl 3-cyclohexyl-3-oxopropanoate Chemical compound COC(=O)CC(=O)C1CCCCC1 MIOOVIILBQHHNK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002674 ointment Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 230000002035 prolonged effect Effects 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
- 239000012279 sodium borohydride Substances 0.000 abstract 1
- UOULCEYHQNCFFH-UHFFFAOYSA-M sodium;hydroxymethanesulfonate Chemical compound [Na+].OCS([O-])(=O)=O UOULCEYHQNCFFH-UHFFFAOYSA-M 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
-
- 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
- C07D455/02—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing not further condensed quinolizine ring 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
-
- 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
- C07D455/08—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 having an isoquinolyl-1, a substituted isoquinolyl-1 or an alkylenedioxyisoquinolyl-1 radical linked through only one carbon atom, attached in position 2, e.g. emetine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Compounds of the general formula <FORM:1122212/C2/1> some of which are stated to be novel, where R1 is alkyl, cycloalkyl, aryl or aralkyl of up to 11 carbon atoms in which the aromatic ring, when present, is optionally substituted by 1, 2 or 3 methoxy radicals or alkyl radicals or a methylenedioxy group, or is the radical <FORM:1122212/C2/2> R2 is alkyl, aryl or aralkyl of up to 8 C atoms where the aromatic ring, when present, is optionally substituted by 1, 2 or 3 Cl atoms, methoxy or alkyl groups or a methylenedioxy group; R3 and R4, same or different, are -(CH3)3- or -(CH3)4- which may be substituted by one or more C1- 6 alkyl radicals and/ or phenyl radicals, or the radical <FORM:1122212/C2/3> which latter is optionally substituted in the phenyl ring by 1, 2 or 3 alkyl or methoxy radicals, or a methylenedioxy group; R5 is H, acyl up to 9 C atoms, carbobenzoxy, carbalkoxy, alkyl or aralkyl radical containing up to 9 carbon atoms, and acid addition salts thereof are prepared by condensing a cyclic b -amino ketone of the formula <FORM:1122212/C2/4> where R6 is C1- 11 alkyl, cycloalkyl, aryl or aralkyl, in which the aromatic ring is optionally substituted by 1, 2 or 3 methoxy or C1- 2 alkyl radicals or a methylenedioxy group or is the radical <FORM:1122212/C2/5> where R7 is C1- 9 acyl or a carbobenzoxy o lower carbalkoxy radical or an acid addition salt thereof, with an aldehyde of the formula O=CH-CH2R2 in the presence of water and/or a water-miscible organic solvent to obtain a mixture of a compound of the first general formula above where R1 is R6 and a corresponding pyridinium salt of the formula <FORM:1122212/C2/6> where X(-) is an anion, reducing the mixed reaction products and, if desired, separating the resulting desired product into its diastereoisomeric forms and/or converting it into an acid addition salt. The reduction is advantageously carried out with sodium borohydride in methanol. 1 - (N - benzoyl - 1,2,3,4 - tetrahydro - 6,7-dimethoxy - isoquinolyl - 1) - 2 - (1,2,3,4 - tetrahydro - 6,7 - dimethoxy - isoquinolyl - 1) - acetone is prepared by treating g -(1,2,3,4-tetrahydro-6,7 - dimethoxyisoquinolyl - 1) - b - oxobutyric acid with benzoyl chloride and reacting the resulting corresponding N - benzoyl compound with 3,4 - dihydro - 6,7 - dimethoxy - isoquinoline (the product may be further benzoylated to 1,3 - bis - (N - benzoyl - 1,2,3,4 - tetrahydro-6,7-dimethoxy - isoquinolyl - 1) - acetone; perchlorate salts of all those compounds are mentioned. 1 - (N - carbobenzoxy - 1,2,3,4 - tetrahydro-6,7-dimethoxy - isoquinolyl - 1) - 3 - (1 - 1,2,3,4-tetrahydro - 6,7 - dimethoxy - isoquinolyl - 1)-acetone is prepared by reacting g -(1,2,3,4-tetrahydro-6,7 - dimethoxy - isoquinolyl - 1) - b - oxobutyric acid with carbobenzoxychloride; the resulting corresponding N-carbobenzoxy compound loses CO2 on prolonged standing to form N-carbobenzoxy - 1 - acetonyl - 6,7 - dimethoxy - 1,2,3,4-tetrahydroisoquinoline and reacting this compound with 3,4 - dihydro - 6,7 - dimethoxy - isoquinoline (the product may be further reacted with carbobenzoxy chloride to form 1,3-bis-(N-carbobenzoxy - 6,7 - dimethoxy - 1,2,3,4 - tetrahydro - isoquinolyl - 1) - acetone which is also obtainable by direct reaction between 1,3-bis-(6,7 - dimethoxy - 1,2,3,4 - tetrahydro - isoquinolyl-1)-acetone and carbobenzoxy chloride). 1 - (N - benzoyl - 1,2,3,4 - tetrahydro - 6,7-methylenedioxy - isoquinolyl - 1) - 3 - (1,2,3,4-tetrahydro - 6,7 - methylenedioxy - isoquinolyl-1)-acetone is prepared by reacting acetone dicarboxylic acid and 6,7-methylenedioxy-3,4-dihydro-isoquinoline to form g (1,2,3,4-tetrahydro - 6,7 - methylenedioxy - isoquinolyl - 1)-b -oxobutyric acid which on standing loses CO2 to form bis - (6,7 - methylenedioxy - 1,2,3,4-tetrahydro - isoquinolyl - 1) - acetone, reacting this compound with benzoyl chloride and reacting the resulting corresponding N-benzoyl compound with 6,7 - methylenedioxy - 3,4 - dihydroisoquinoline. Cyclohexyl - (6,7 - dimethoxy - 1,2,3,4 - tetrahydro - isoquinolyl - 1 - methyl) - ketone is prepared by reacting hexahydrobenzoic acid chloride with sodium acetoacetic ester, acid cleaving the resulting hexahydro-benzoyl-acetoacetic ester with sodium methylate in methanol to form hexahydrobenzoyl acetic acid methyl ester, saponifying this ester to the corresponding free carboxylic acid, and reacting this acid with 3,4 - dihydro - 6,7 - dimethoxy - isoquinoline. 1 - (2 - oxo - 4 - phenylbutyl) - 6,7 - dimethoxy-1,2,3, 4 - tetrahydroisoquinoline is prepared from hydrocinnamic acid chloride by a similar method. 3 - (2 - Benzoyl - 6,7 - dimethoxy - 1,2,3,4-tetrahydroisoquinolyl - 1) - acetone is prepared by reacting a -tripiperideine and the N-benzoyl compound of g - (6,7 - dimethoxy - 1,2,3,4-tetrahydro - isoquinolyl - 1) - b - oxobutyric acid and allowing the mixture to stand. 1 - (2 - p - Methoxyphenyl - 2 - oxo - ethyl)-6,7-dimethoxy - 1,2,3,4 - tetrahydroisoquinoline is prepared by saponification of p-methoxybenzoyl ethyl acetate with alkali at room temperature and condensation of the resulting b -keto acid. Pharmaceutical compositions having e.g. amoebicidal or trichomonadocidal activity comprise a compound of the first general formula above or a pharmaceutically acceptable salt thereof together with an inert physiologically acceptable carrier. They may be administered parenterally or enterally and may be formulated as solutions, suspensions, emulsions, implantates, tablets, lozenges, creams or ointments.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM0062148 | 1964-08-19 | ||
| DEM0062274 | 1964-09-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1122212A true GB1122212A (en) | 1968-07-31 |
Family
ID=25987592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3485665A Expired GB1122212A (en) | 1964-08-19 | 1965-08-13 | Process for the preparation of substituted piperidine derivatives |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH461496A (en) |
| DE (2) | DE1470084A1 (en) |
| GB (1) | GB1122212A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002010135A1 (en) * | 2000-08-01 | 2002-02-07 | Ono Pharmaceutical Co., Ltd. | 3,4-dihydroisoquinoline derivative compounds and drugs containing these compounds as the active ingredient |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ191763A (en) * | 1978-10-13 | 1984-05-31 | Hoffmann La Roche | 7-beta-phenyl-quinolidines, intermediates and pharmaceutical compositions |
| GB8615785D0 (en) * | 1986-06-27 | 1986-08-06 | Beecham Group Plc | Compounds |
-
1964
- 1964-08-19 DE DE19641470084 patent/DE1470084A1/en active Pending
- 1964-09-01 DE DE19641470091 patent/DE1470091A1/en active Pending
-
1965
- 1965-07-28 CH CH1053965A patent/CH461496A/en unknown
- 1965-08-13 GB GB3485665A patent/GB1122212A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002010135A1 (en) * | 2000-08-01 | 2002-02-07 | Ono Pharmaceutical Co., Ltd. | 3,4-dihydroisoquinoline derivative compounds and drugs containing these compounds as the active ingredient |
| US6956033B2 (en) | 2000-08-01 | 2005-10-18 | Ono Pharmaceutical Co., Ltd. | 3,4-dihydroisoquinoline derivative compound and a pharmaceutical agent comprising it as active ingredient |
| JP4982937B2 (en) * | 2000-08-01 | 2012-07-25 | 小野薬品工業株式会社 | 3,4-Dihydroisoquinoline derivative compound and drug containing the compound as an active ingredient |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1470084A1 (en) | 1969-05-29 |
| CH461496A (en) | 1968-08-31 |
| DE1470091A1 (en) | 1969-05-08 |
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