GB1180615A - Novel Substituted Hexahydroazepino-(4,5-b) Indoles - Google Patents
Novel Substituted Hexahydroazepino-(4,5-b) IndolesInfo
- Publication number
- GB1180615A GB1180615A GB1757867A GB1757867A GB1180615A GB 1180615 A GB1180615 A GB 1180615A GB 1757867 A GB1757867 A GB 1757867A GB 1757867 A GB1757867 A GB 1757867A GB 1180615 A GB1180615 A GB 1180615A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- pharmaceutically acceptable
- acid addition
- addition salts
- active
- 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
- BHDUGUXLCPXVMZ-UHFFFAOYSA-N 1,2,3,4,5,5a-hexahydroazepino[4,5-b]indole Chemical class C1CNCCC2N=C(C=CC=C3)C3=C21 BHDUGUXLCPXVMZ-UHFFFAOYSA-N 0.000 title 1
- 150000003839 salts Chemical class 0.000 abstract 3
- 239000004480 active ingredient Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 230000002363 herbicidal effect Effects 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 150000002475 indoles Chemical class 0.000 abstract 1
- 239000003701 inert diluent Substances 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 229940125723 sedative agent Drugs 0.000 abstract 1
- 239000000932 sedative agent Substances 0.000 abstract 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 abstract 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D223/08—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D223/12—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1,180,615. Pharmaceutical and herbicidal compositions. UPJOHN CO. 17 April, 1967 [10 May, 1966], No. 17578/68. Headings A5B and A5E. [Also in Division C2] Pharmaceutical compositions, suitable for oral administration, comprise as active ingredients novel azepino [4, 5-6] indole derivatives of the formula in which R and R<SP>1</SP>, which may be the same or different, are H, C 1-3 alkyl, C 1-3 alkoxy, fluorine, bromine or iodine, R 1 is C 1-3 alkyl and R 2 is methyl, ethyl, propyl or benzyl, or pharmaceutically acceptable acid addition salts thereof together with pharmaceutically acceptable carriers. The above compounds are active tranquilisers and sedatives and act as antidepressants and as a norexigenic agents. Herbicidal compositions comprise as the active ingredient a trichloroacetic acid addition salts of the above novel compounds together with an inert diluent. The fluosilicate salts are useful as moth-proofing agents.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54888066A | 1966-05-10 | 1966-05-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1180615A true GB1180615A (en) | 1970-02-04 |
Family
ID=24190763
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4488369A Expired GB1180616A (en) | 1966-05-10 | 1967-04-17 | Improvements in or relating to Hexahydroazepine Compounds and the Manufacture thereof |
| GB1757867A Expired GB1180615A (en) | 1966-05-10 | 1967-04-17 | Novel Substituted Hexahydroazepino-(4,5-b) Indoles |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4488369A Expired GB1180616A (en) | 1966-05-10 | 1967-04-17 | Improvements in or relating to Hexahydroazepine Compounds and the Manufacture thereof |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE698268A (en) |
| CH (1) | CH506543A (en) |
| DE (1) | DE1695943A1 (en) |
| ES (1) | ES340258A1 (en) |
| FR (1) | FR6699M (en) |
| GB (2) | GB1180616A (en) |
| GR (1) | GR35044B (en) |
| IL (2) | IL27776A (en) |
| NL (1) | NL6706513A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002024701A3 (en) * | 2000-09-20 | 2002-06-13 | Upjohn Co | Substituted azepino[4,5b)indole derivatives |
| US7485634B2 (en) | 2002-05-24 | 2009-02-03 | Exelixis, Inc. | Azepinoindole and pyridoindole derivatives as pharmaceutical agents |
| US7595311B2 (en) | 2002-05-24 | 2009-09-29 | Exelixis, Inc. | Azepinoindole derivatives as pharmaceutical agents |
| US11905295B2 (en) | 2021-11-17 | 2024-02-20 | Terran Biosciences Inc. | Solid forms of tabernanthalog monofumarate salt for treating neurological disorders and/or psychiatric disorders |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2029828B (en) * | 1978-08-24 | 1983-04-27 | Omnium Chimique Sa | Vincadifformine derivatives |
| FR2663935A1 (en) * | 1990-06-27 | 1992-01-03 | Adir | NOVEL 1,2,3,4,5,6-HEXAHYDROAZEPINO [4,5-B] INDOLES AND 1,2,3,4-TETRAHYDROBETHACARBOLINES, PROCESSES FOR PREPARING THEM AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| MY122278A (en) | 1999-07-19 | 2006-04-29 | Upjohn Co | 1,2,3,4,5,6-hexahydroazepino[4,5-b]indoles containing arylsulfones at the 9-position |
| US7030109B2 (en) | 1999-07-19 | 2006-04-18 | Pharmacia & Upjohn Company | 1,2,3,4,5,6-Hexahydroazepino[4,5-b]indoles containing arylsulfones at the 9-position |
| WO2002004456A1 (en) * | 2000-07-06 | 2002-01-17 | Pharmacia & Upjohn Company | SUBSTITUTED 2,3,7,8,9,10,11,12-OCTAHYDROAZEPINO[4,5-b]PYRANO[3,2-e]INDOLES |
| JP4679517B2 (en) * | 2003-07-23 | 2011-04-27 | エグゼリクシス， インコーポレイテッド | Azepine derivatives as drugs |
-
1967
- 1967-04-10 GR GR670135044A patent/GR35044B/en unknown
- 1967-04-11 IL IL2777667A patent/IL27776A/en unknown
- 1967-04-11 IL IL3680167A patent/IL36801A/en unknown
- 1967-04-17 GB GB4488369A patent/GB1180616A/en not_active Expired
- 1967-04-17 GB GB1757867A patent/GB1180615A/en not_active Expired
- 1967-05-05 CH CH637567A patent/CH506543A/en not_active IP Right Cessation
- 1967-05-08 ES ES340258A patent/ES340258A1/en not_active Expired
- 1967-05-09 DE DE19671695943 patent/DE1695943A1/en active Pending
- 1967-05-10 NL NL6706513A patent/NL6706513A/xx unknown
- 1967-05-10 BE BE698268D patent/BE698268A/xx unknown
- 1967-08-08 FR FR117261A patent/FR6699M/fr not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002024701A3 (en) * | 2000-09-20 | 2002-06-13 | Upjohn Co | Substituted azepino[4,5b)indole derivatives |
| US6583135B2 (en) | 2000-09-20 | 2003-06-24 | Pharmacia & Upjohn Company | Substituted azepino[4,5b]indole derivatives |
| US6828314B2 (en) | 2000-09-20 | 2004-12-07 | Pfizer | Substituted azepino[4,5b]indoline derivatives |
| US6903090B2 (en) | 2000-09-20 | 2005-06-07 | Pfizer | Substituted azepino[4,5b]indole derivatives |
| US7485634B2 (en) | 2002-05-24 | 2009-02-03 | Exelixis, Inc. | Azepinoindole and pyridoindole derivatives as pharmaceutical agents |
| US7595311B2 (en) | 2002-05-24 | 2009-09-29 | Exelixis, Inc. | Azepinoindole derivatives as pharmaceutical agents |
| AU2003243328B2 (en) * | 2002-05-24 | 2010-05-20 | X-Ceptor Therapeutics, Inc. | Azepinoindole and pyridoindole derivatives as pharmaceutical agents |
| AU2003243328C1 (en) * | 2002-05-24 | 2010-10-21 | X-Ceptor Therapeutics, Inc. | Azepinoindole and pyridoindole derivatives as pharmaceutical agents |
| US11905295B2 (en) | 2021-11-17 | 2024-02-20 | Terran Biosciences Inc. | Solid forms of tabernanthalog monofumarate salt for treating neurological disorders and/or psychiatric disorders |
Also Published As
| Publication number | Publication date |
|---|---|
| ES340258A1 (en) | 1968-06-01 |
| GR35044B (en) | 1968-07-31 |
| FR6699M (en) | 1969-02-10 |
| GB1180616A (en) | 1970-02-04 |
| BE698268A (en) | 1967-11-10 |
| DE1695943A1 (en) | 1971-05-13 |
| CH506543A (en) | 1971-04-30 |
| IL27776A (en) | 1971-11-29 |
| NL6706513A (en) | 1967-11-13 |
| IL36801A (en) | 1971-11-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1172034A (en) | Substituted 3-Ureidopyrrolidines | |
| FI872864A0 (en) | Process for the preparation of pharmaceutically active benzimidazole derivatives | |
| BG60102B2 (en) | Method for preparing of 5-fluoro-2[[(4-cyclopropylmethoxy-2-pyridyl)methyl]thionyl]-1h-ben zimidazole | |
| FI870421A0 (en) | Analogous method for the preparation of 5,6-dihydro-2- (substituted phenyl) -1,2,4-triazine-3,5 (2H, 4H) -dione derivatives having protozoal activity | |
| RU94046044A (en) | NEW 7β-SUBSTITUTED 4-AZA-5a-CHOLESTAN-ONES AS INHIBITORS OF 5a-REDUCTASE, PHARMACEUTICAL COMPOSITION BASED ON THEREOF, METHOD OF ITS PREPARING | |
| GB1180615A (en) | Novel Substituted Hexahydroazepino-(4,5-b) Indoles | |
| GB1388358A (en) | Taste-improving formulations of oral penicillins | |
| ATE92036T1 (en) | CARDIOVASCULAR ACTIVE CONNECTIONS. | |
| AU1891683A (en) | Substituted 1-phenyl-isoquinoline anti-arrythmic agents | |
| GB1185522A (en) | 00,5-(Iminomethano)-10,11-Dihydro-5H-Dibenzo [a,d]Cycloheptene and Derivatives | |
| GB1188846A (en) | Thiazole Derivatives | |
| SE8107524L (en) | Heterocyclic Associations | |
| GB1160597A (en) | Novel Isoxazolo[5,4-6]Pyridines and the Preparation Thereof | |
| GB1177145A (en) | Heterocyclic Allylic Amines | |
| DK0524696T3 (en) | Oral preparations containing dapiprazole | |
| FR1602627A (en) | 3 omega-subst alkyl indoles | |
| CS548987A2 (en) | Process for preparing new tetracycline derivatives of indole | |
| GB1420976A (en) | Pharmaceutical compositions for use in the treatment of certain respiratory diseases or conditions in prematurely born children | |
| IE39639L (en) | Preparation of n-substituted cycloserine derivatives. | |
| GB1215152A (en) | Biguanide derivatives and pharmaceutical preparations containing them | |
| AU7506591A (en) | A therapeutic agent for dysuria comprising alpha-phenyl-alpha-pyridylalkanoic acid derivatives | |
| NO823682L (en) | PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVE PYRIDAZINONIMINE DERIVATIVES. | |
| GB1321368A (en) | Organo-phosphorus compounds useful for the control of helminths in warm-blooded animals | |
| ATE92037T1 (en) | CARDIOVASCULAR ACTIVE CONNECTIONS. | |
| IE33893L (en) | Insecticidal agents; substituted benzene derivatives |