GB1202579A - Pharmacologically active new isoquinoline derivative and process for preparing same - Google Patents
Pharmacologically active new isoquinoline derivative and process for preparing sameInfo
- Publication number
- GB1202579A GB1202579A GB5508867A GB5508867A GB1202579A GB 1202579 A GB1202579 A GB 1202579A GB 5508867 A GB5508867 A GB 5508867A GB 5508867 A GB5508867 A GB 5508867A GB 1202579 A GB1202579 A GB 1202579A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethoxyphenyl
- ethyl
- methyl
- dimethoxy
- imide
- 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
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- RUJBDQSFYCKFAA-UHFFFAOYSA-N Tofisopam Chemical compound N=1N=C(C)C(CC)C2=CC(OC)=C(OC)C=C2C=1C1=CC=C(OC)C(OC)=C1 RUJBDQSFYCKFAA-UHFFFAOYSA-N 0.000 abstract 2
- 150000003949 imides Chemical class 0.000 abstract 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 abstract 2
- 229940075930 picrate Drugs 0.000 abstract 2
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 abstract 2
- UVDYAKFPZXGKTI-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-4-ethyl-6,7-dimethoxy-3-methylisoquinoline Chemical compound C12=CC(OC)=C(OC)C=C2C(CC)=C(C)N=C1C1=CC=C(OC)C(OC)=C1 UVDYAKFPZXGKTI-UHFFFAOYSA-N 0.000 abstract 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- BGDCTHTZHFORBL-UHFFFAOYSA-N [1-(3,4-dimethoxyphenyl)-4-ethyl-6,7-dimethoxy-3-methylisochromen-1-yl]hydrazine Chemical compound N(N)C1(OC(=C(C2=C1C=C(C(=C2)OC)OC)CC)C)C2=CC(=C(C=C2)OC)OC BGDCTHTZHFORBL-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000010306 acid treatment Methods 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- 239000000796 flavoring agent Substances 0.000 abstract 1
- 235000013355 food flavoring agent Nutrition 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000004682 monohydrates Chemical class 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 abstract 1
- 239000003204 tranquilizing agent Substances 0.000 abstract 1
- 230000002936 tranquilizing effect Effects 0.000 abstract 1
Classifications
-
- 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
- C07D217/18—Aralkyl radicals
- C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/10—Quaternary compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/02—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,202,579. Isoquinoline N-imide derivative. EGYESULT GYOGYSZER - ES TAPSZERGYAR. 4 Dec., 1967 [9 Dec., 1966], No. 55088/67. Heading C2C. ,The invention comprises the compound of formula and its acid addition salts. The above compound is made by reacting (a) 3,4,3<SP>1</SP>,4<SP>1</SP> - tetramethoxy - 6 - (1 - acetylpropyl) - benzophenone with hydrazine or its hydrate, followed by acid treatment of the 1 - hydrazino - 1 - (3,4 - dimethoxyphenyl) - 3 - methyl - 4 - ethyl - 6,7 - dimethoxy - 1H - 2 - benzopyran (I) and/or 1 - (3,4 - dimethoxyphenyl) - 4 - methyl - 5 - ethyl - 7,8 - dimethoxy - 5H - 2,3 - benzodiazepine (II) so formed; (b) a 1 - (3,4 - dimethoxyphenyl) - 3 - methyl - 4 - ethyl - 6,7 - dimethoxy - isobenzopyrylium salt with hydrazine or its hydrate; or (c) 1 - (3,4 - dimethoxyphenyl) - 3 - methyl - 4 - ethyl - 6,7 - dimethoxyisoquinoline with a salt of H 2 NOSO 3 H in an alkaline medium. The imide and its salts formed in methods (a), (b) and (c) may be interconnected in the usual way. The monohydrate, hydrochloride and picrate of the imide, and the picrate of II are described. I may be converted to II by dehydration, e.g. by setting at 150‹ C. Tranquilizers comprise the above compound, which may be combined with carriers, binding, filling, surface active, and flavouring agents, and other (unspecified) active compounds.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI001000 | 1966-12-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1202579A true GB1202579A (en) | 1970-08-19 |
Family
ID=10994380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5508867A Expired GB1202579A (en) | 1966-12-09 | 1967-12-04 | Pharmacologically active new isoquinoline derivative and process for preparing same |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH583714A5 (en) |
| GB (1) | GB1202579A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE30014E (en) | 1966-12-09 | 1979-05-29 | Egyesult Gyogyazer-es Tapozergyar | 1-(3,4-Dimethoxy-phenyl)-4-methyl-5-ethyl-7,8-dimethoxy-5H-2,3-benzodiazepine |
| WO2009156776A1 (en) * | 2008-06-27 | 2009-12-30 | Egis Gyogyszergyar Nyilvanosan Müködö | Process for the preparation of high purity 1-(3,4-dimethoxy-phenyl)-5-ethyl-7,8-dimethoxy-4-methyl-5h-2,3-benzodiazepine |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU179018B (en) * | 1978-10-19 | 1982-08-28 | Gyogyszerkutato Intezet | Process for producing new 5h-2,3-benzodiazepine derivatives |
-
1967
- 1967-12-04 GB GB5508867A patent/GB1202579A/en not_active Expired
- 1967-12-08 CH CH341770A patent/CH583714A5/en not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE30014E (en) | 1966-12-09 | 1979-05-29 | Egyesult Gyogyazer-es Tapozergyar | 1-(3,4-Dimethoxy-phenyl)-4-methyl-5-ethyl-7,8-dimethoxy-5H-2,3-benzodiazepine |
| WO2009156776A1 (en) * | 2008-06-27 | 2009-12-30 | Egis Gyogyszergyar Nyilvanosan Müködö | Process for the preparation of high purity 1-(3,4-dimethoxy-phenyl)-5-ethyl-7,8-dimethoxy-4-methyl-5h-2,3-benzodiazepine |
Also Published As
| Publication number | Publication date |
|---|---|
| CH583714A5 (en) | 1977-01-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1327312A (en) | Hererocyclic compounds | |
| IE43312L (en) | Propanolamine derivatives | |
| GB1368416A (en) | Selectively herbicidal agents | |
| GB1202579A (en) | Pharmacologically active new isoquinoline derivative and process for preparing same | |
| ES388196A1 (en) | Imidazoline derivatives | |
| GB1394568A (en) | Diazepine derivatives and process for the production thereof | |
| GB1382916A (en) | Derivatives of 3-2-1-piperazinyl-ethyl- indoline | |
| GB1206088A (en) | New pyrazolodiazepinone compounds and methods for their production | |
| GB1394962A (en) | 1-ethylimidazoles their production and their medicinal use | |
| GB1114660A (en) | Tetrahydro-lsoquinolines | |
| ES319653A1 (en) | A procedure for the preparation of imidazole derivatives. (Machine-translation by Google Translate, not legally binding) | |
| GB1208195A (en) | Process for producing benzodiazepine derivatives | |
| GB1469226A (en) | Process for the preparation of 2-2-thienyl-ethylamine and derivatives thereof | |
| GB1397869A (en) | 1,8-naphthyridin derivatives | |
| GB1035777A (en) | Isoquinoline derivatives | |
| GB1319840A (en) | Substituted 5-amino imidazoles | |
| GB1284051A (en) | Process for the preparation of 3,4-dihydroisoquinoline derivatives | |
| GB1321691A (en) | Dihydro-3-piperidyl-2 3h-furanone derivatives | |
| GB1226530A (en) | ||
| GB1190022A (en) | Novel Hydraziyohimbanes | |
| GB1384523A (en) | Oxime derivatives and their preparation | |
| GB1339010A (en) | Tetrazolyl-anthraquinone derivatives | |
| GB1073521A (en) | Indole derivatives | |
| GB1409569A (en) | Amino derivatives of 2,2-diarylcyclopropane | |
| GB1251009A (en) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 429A | Application made for amendment of specification (sect. 29/1949) | ||
| 429H | Application (made) for amendment of specification now open to opposition (sect. 29/1949) | ||
| 429H | Application (made) for amendment of specification now open to opposition (sect. 29/1949) | ||
| 429G | Application made to the patents court ** appeal allowed (sect. 29/1949) | ||
| 429D | Case decided by the comptroller ** specification amended (sect. 29/1949) | ||
| SPA | Amended specification published | ||
| PE20 | Patent expired after termination of 20 years |