GB2004872A - Dibenzocycloheptenimines - Google Patents
DibenzocyclohepteniminesInfo
- Publication number
- GB2004872A GB2004872A GB7837284A GB7837284A GB2004872A GB 2004872 A GB2004872 A GB 2004872A GB 7837284 A GB7837284 A GB 7837284A GB 7837284 A GB7837284 A GB 7837284A GB 2004872 A GB2004872 A GB 2004872A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenylalkyl
- cycloalkylalkyl
- alkenyl
- alkyl
- dialkylaminoalkyl
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/112—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- C07D295/116—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings with the doubly bound oxygen or sulfur atoms directly attached to a carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
This invention provides 5-substituted- 10,11-dihydro-5H-dibenzo[a, d]cyclohepten-5,10-imines and their salts, methods of preparing such compounds and pharmaceutical compositions containing them. The free-base forms have the formula <IMAGE> where R is hydrogen; alkyl, alkenyl, phenylalkyl, halophenylalkyl, alkylphenylalkyl, cycloalkyl, cycloalkylalkyl or dialkylaminoalkyl, R<1> is hydrogen, alkyl, alkenyl, phenylalkyl, cycloalkyl or cycloalkylalkyl, CH2R<2> is alkyl, alkenyl, phenylalkyl, cycloalkylalkyl, dialkylaminoalkyl or hydroxyalkyl, and R<3> and R<4> are H, halogen, alkoxy, CF3S-, -CN, -COOH or -OH and are useful as antianxiety agents, muscle relaxants and in the treatment of extrapyramidal disorders such as in Parkinson's disease.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83463977A | 1977-09-19 | 1977-09-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2004872A true GB2004872A (en) | 1979-04-11 |
| GB2004872B GB2004872B (en) | 1982-04-15 |
Family
ID=25267426
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8037685A Expired GB2061947B (en) | 1977-09-19 | 1978-09-19 | Dibenzocycloheptenimines |
| GB7837284A Expired GB2004872B (en) | 1977-09-19 | 1978-09-19 | Chemical compounds and their production and use |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8037685A Expired GB2061947B (en) | 1977-09-19 | 1978-09-19 | Dibenzocycloheptenimines |
Country Status (33)
| Country | Link |
|---|---|
| JP (1) | JPS5463100A (en) |
| AR (1) | AR231544A1 (en) |
| AT (1) | AT370103B (en) |
| AU (1) | AU520178B2 (en) |
| BE (1) | BE870562A (en) |
| CA (1) | CA1129850A (en) |
| CH (1) | CH637954A5 (en) |
| CY (1) | CY1283A (en) |
| DE (1) | DE2840786A1 (en) |
| DK (1) | DK153843C (en) |
| ES (7) | ES473492A1 (en) |
| FI (1) | FI65618C (en) |
| FR (1) | FR2403334A1 (en) |
| GB (2) | GB2061947B (en) |
| GR (1) | GR65703B (en) |
| HK (1) | HK30885A (en) |
| HU (1) | HU180868B (en) |
| IE (1) | IE47355B1 (en) |
| IL (1) | IL55521A0 (en) |
| IT (1) | IT1113279B (en) |
| KE (1) | KE3501A (en) |
| LU (1) | LU80262A1 (en) |
| NL (1) | NL191488C (en) |
| NO (1) | NO151861C (en) |
| NZ (1) | NZ188361A (en) |
| PH (1) | PH15920A (en) |
| PL (3) | PL121605B1 (en) |
| PT (1) | PT68544A (en) |
| SE (1) | SE437520B (en) |
| SG (1) | SG9585G (en) |
| SU (2) | SU895288A3 (en) |
| YU (1) | YU41432B (en) |
| ZA (1) | ZA785291B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4477668A (en) * | 1982-04-07 | 1984-10-16 | Merck & Co., Inc. | Process for 5-methyl-10,11-dihydro-5H-dibenzo[a,d]-cyclohepten-5,10-imine |
| EP0303512A1 (en) * | 1987-08-13 | 1989-02-15 | Merck Sharp & Dohme Ltd. | Substituted dibenzocycloheptenimines |
| WO1996032390A1 (en) * | 1995-04-11 | 1996-10-17 | Neurogen Corporation | PREPARATION OF CHIRAL 5-AMINOCARBONYL-5H-DIBENZO-[a,d]CYCLOHEPTEN-5,10-IMINES BY OPTICAL RESOLUTION |
| US5739337A (en) * | 1996-03-08 | 1998-04-14 | Neurogen Corporation | Process for preparing dibenzo-1-carboxamido-1,4-azabicyclo 3.2.1!octanes |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4232158A (en) * | 1979-06-04 | 1980-11-04 | Merck & Co., Inc. | 10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imines |
| ES2843724T3 (en) | 2015-11-30 | 2021-07-20 | Inst Nat Sante Rech Med | NMDAR antagonists for the treatment of tumor angiogenesis |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE794904A (en) * | 1972-02-04 | 1973-08-02 | Roussel Uclaf | NEW DIBENZOCYCLOHEPTENE DERIVATIVES AND THEIR PREPARATION |
| BE829075A (en) * | 1974-05-15 | 1975-11-14 | 9,10-DIHYDROANTHRACEN-9,10-IMINES SUBSTITUTES AND THEIR HETEROCYCLIC ANALOGUES (AZA) |
-
1978
- 1978-08-28 NL NL7808847A patent/NL191488C/en not_active IP Right Cessation
- 1978-08-31 SE SE7809187A patent/SE437520B/en not_active IP Right Cessation
- 1978-09-01 FI FI782680A patent/FI65618C/en not_active IP Right Cessation
- 1978-09-04 NO NO783017A patent/NO151861C/en unknown
- 1978-09-04 DK DK389978A patent/DK153843C/en not_active IP Right Cessation
- 1978-09-06 PH PH21575A patent/PH15920A/en unknown
- 1978-09-06 IL IL7855521A patent/IL55521A0/en not_active IP Right Cessation
- 1978-09-06 NZ NZ188361A patent/NZ188361A/en unknown
- 1978-09-08 GR GR57185A patent/GR65703B/en unknown
- 1978-09-08 AU AU39668/78A patent/AU520178B2/en not_active Expired
- 1978-09-12 PT PT68544A patent/PT68544A/en unknown
- 1978-09-13 CA CA311,197A patent/CA1129850A/en not_active Expired
- 1978-09-14 AR AR273708A patent/AR231544A1/en active
- 1978-09-15 IE IE1866/78A patent/IE47355B1/en not_active IP Right Cessation
- 1978-09-15 CH CH969078A patent/CH637954A5/en not_active IP Right Cessation
- 1978-09-15 FR FR7826533A patent/FR2403334A1/en active Granted
- 1978-09-15 AT AT0669778A patent/AT370103B/en not_active IP Right Cessation
- 1978-09-16 PL PL1978225938A patent/PL121605B1/en unknown
- 1978-09-16 PL PL1978209632A patent/PL112834B1/en unknown
- 1978-09-16 PL PL1978217435A patent/PL118478B1/en unknown
- 1978-09-18 BE BE190553A patent/BE870562A/en not_active IP Right Cessation
- 1978-09-18 HU HU78ME2204A patent/HU180868B/en not_active IP Right Cessation
- 1978-09-18 ZA ZA785291A patent/ZA785291B/en unknown
- 1978-09-18 SU SU782665603A patent/SU895288A3/en active
- 1978-09-18 IT IT51126/78A patent/IT1113279B/en active
- 1978-09-18 YU YU2196/78A patent/YU41432B/en unknown
- 1978-09-19 CY CY1283A patent/CY1283A/en unknown
- 1978-09-19 JP JP11420078A patent/JPS5463100A/en active Granted
- 1978-09-19 DE DE19782840786 patent/DE2840786A1/en active Granted
- 1978-09-19 LU LU80262A patent/LU80262A1/en unknown
- 1978-09-19 ES ES473492A patent/ES473492A1/en not_active Expired
- 1978-09-19 GB GB8037685A patent/GB2061947B/en not_active Expired
- 1978-09-19 GB GB7837284A patent/GB2004872B/en not_active Expired
-
1979
- 1979-08-09 ES ES483283A patent/ES483283A1/en not_active Expired
- 1979-08-09 ES ES483288A patent/ES483288A1/en not_active Expired
- 1979-08-09 ES ES483287A patent/ES483287A1/en not_active Expired
- 1979-08-09 ES ES483284A patent/ES483284A1/en not_active Expired
- 1979-08-09 ES ES483286A patent/ES483286A1/en not_active Expired
- 1979-08-09 ES ES483285A patent/ES483285A1/en not_active Expired
- 1979-11-02 SU SU792834514A patent/SU915800A3/en active
-
1985
- 1985-02-05 KE KE3501A patent/KE3501A/en unknown
- 1985-02-07 SG SG95/85A patent/SG9585G/en unknown
- 1985-04-18 HK HK308/85A patent/HK30885A/en not_active IP Right Cessation
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4477668A (en) * | 1982-04-07 | 1984-10-16 | Merck & Co., Inc. | Process for 5-methyl-10,11-dihydro-5H-dibenzo[a,d]-cyclohepten-5,10-imine |
| EP0303512A1 (en) * | 1987-08-13 | 1989-02-15 | Merck Sharp & Dohme Ltd. | Substituted dibenzocycloheptenimines |
| WO1996032390A1 (en) * | 1995-04-11 | 1996-10-17 | Neurogen Corporation | PREPARATION OF CHIRAL 5-AMINOCARBONYL-5H-DIBENZO-[a,d]CYCLOHEPTEN-5,10-IMINES BY OPTICAL RESOLUTION |
| US5686614A (en) * | 1995-04-11 | 1997-11-11 | Neurogen Corporation | Preparation of chiral 5-aminocarbonyl-5H-dibenzo a,d!cyclohepten-5,10-imines by optical resolution |
| US5739337A (en) * | 1996-03-08 | 1998-04-14 | Neurogen Corporation | Process for preparing dibenzo-1-carboxamido-1,4-azabicyclo 3.2.1!octanes |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PE20 | Patent expired after termination of 20 years |
Effective date: 19980918 |