GB1449159A - Benzoisoindoline derivatives - Google Patents
Benzoisoindoline derivativesInfo
- Publication number
- GB1449159A GB1449159A GB4547773A GB4547773A GB1449159A GB 1449159 A GB1449159 A GB 1449159A GB 4547773 A GB4547773 A GB 4547773A GB 4547773 A GB4547773 A GB 4547773A GB 1449159 A GB1449159 A GB 1449159A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- compounds
- reduction
- cinnamyl
- dioxo
- 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
- DPUGFWNCMIJEIS-UHFFFAOYSA-N 2,3-dihydro-1h-benzo[e]isoindole Chemical class C1=CC2=CC=CC=C2C2=C1CNC2 DPUGFWNCMIJEIS-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- VINVRAXYMYQZQY-UHFFFAOYSA-N 4-hydroxy-4-phenyl-5,5a,6,7-tetrahydro-3aH-benzo[e]isoindole-1,3-dione Chemical compound O=C1NC(C2C(CC3C(=C12)C=CCC3)(C3=CC=CC=C3)O)=O VINVRAXYMYQZQY-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 238000006345 epimerization reaction Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000005059 halophenyl group Chemical group 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000000203 mixture 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
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/62—Naphtho [c] pyrroles; Hydrogenated naphtho [c] pyrroles
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
1449159 Benzisoindoline derivatives SANDOZ Ltd 28 Sept 1973 [29 Sept 1972 3 Aug 1973] 45477/73 Heading C2C The invention comprises compounds of formula and their acid addition salts, wherein R is H, alkenyl or alkynyl, or alkyl optionally substituted by OH cycloalkyl, Ph (possibly monohalogen, alkyl or alkoxy substituted) or COZ: Z is OH, alkyl, alkoxy, Ph or halophenyl; R 1 , R 2 are each H, halogen or alkyl; and either X=Y=H and rings B and C are in cis-configuration, or X-Y forms an additional bond. In examples, these compounds are prepared by (a) epimerization, (b) N-substitution, (c) reduction or hydrolysis of an N-acyl analogue (A), (d) hydrogenolysis of an N-benzyl compound, (e) reduction of the compound in which X-Y forms a bond, (f) reduction of the 1,3- dioxo analogue (itself derived by dehydrating the tetrahydro - 1,3 - dioxo - 4 - hydroxy - 4- phenylbenzoisoindoline. Compounds (A) may be prepared by cyclizing (e.g.) an appropriate N,N - bis - cinnamyl- or N - cinnamyl - N- phenylpropynyl derivative of CF 3 CONH 2 . Therapeutic compositions, preferably administered orally, comprise compounds of the above formula, which have antidepressant and analgesic activity.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1425072A CH590231A5 (en) | 1972-09-29 | 1972-09-29 | Benzo(f)isoindoline derivs - with antidepressant and analgesic activity |
| CH1130573A CH605748A5 (en) | 1973-08-03 | 1973-08-03 | Benzo(f)isoindoline derivs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1449159A true GB1449159A (en) | 1976-09-15 |
Family
ID=25708104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4547773A Expired GB1449159A (en) | 1972-09-29 | 1973-09-28 | Benzoisoindoline derivatives |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS602304B2 (en) |
| AT (1) | AT339891B (en) |
| CA (1) | CA1008865A (en) |
| DD (2) | DD118630A5 (en) |
| DE (1) | DE2348593A1 (en) |
| DK (1) | DK136420B (en) |
| ES (4) | ES419195A1 (en) |
| FI (1) | FI57748C (en) |
| FR (1) | FR2201092B1 (en) |
| GB (1) | GB1449159A (en) |
| HK (1) | HK380A (en) |
| IE (1) | IE39474B1 (en) |
| IL (1) | IL43333A (en) |
| MY (1) | MY8000220A (en) |
| NL (1) | NL7313111A (en) |
| PH (1) | PH12933A (en) |
| SE (1) | SE394110B (en) |
| SU (1) | SU707521A3 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0000154B1 (en) * | 1977-06-28 | 1981-07-29 | Sandoz Ag | New benz(f)isoindolines, their preparation and medicaments containing them |
| FR2791345B1 (en) * | 1999-03-26 | 2001-05-04 | Adir | NOVEL BENZO [3,4] CYCLOBUTA [1,2-C] PYRROLE DERIVATIVES, THEIR PREPARATION PROCESS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE792374A (en) * | 1971-12-08 | 1973-06-06 | Allen & Hanburys Ltd | NEW DERIVATIVES OF ISOINDOLINE |
-
1973
- 1973-09-20 DK DK516373AA patent/DK136420B/en not_active IP Right Cessation
- 1973-09-20 FI FI2934/73A patent/FI57748C/en active
- 1973-09-21 SE SE7312916A patent/SE394110B/en unknown
- 1973-09-24 NL NL7313111A patent/NL7313111A/xx not_active Application Discontinuation
- 1973-09-26 DD DD187137*A patent/DD118630A5/xx unknown
- 1973-09-26 DD DD173691A patent/DD114604A5/xx unknown
- 1973-09-26 IL IL43333A patent/IL43333A/en unknown
- 1973-09-27 DE DE19732348593 patent/DE2348593A1/en not_active Withdrawn
- 1973-09-27 IE IE1730/73A patent/IE39474B1/en unknown
- 1973-09-28 FR FR7334863A patent/FR2201092B1/fr not_active Expired
- 1973-09-28 CA CA182,178A patent/CA1008865A/en not_active Expired
- 1973-09-28 GB GB4547773A patent/GB1449159A/en not_active Expired
- 1973-09-28 JP JP48108577A patent/JPS602304B2/en not_active Expired
- 1973-09-28 AT AT833873A patent/AT339891B/en not_active IP Right Cessation
- 1973-09-29 ES ES419195A patent/ES419195A1/en not_active Expired
- 1973-10-01 PH PH15069A patent/PH12933A/en unknown
-
1975
- 1975-12-16 ES ES443519A patent/ES443519A1/en not_active Expired
- 1975-12-16 ES ES443518A patent/ES443518A1/en not_active Expired
- 1975-12-16 ES ES443517A patent/ES443517A1/en not_active Expired
-
1976
- 1976-10-28 SU SU762415454A patent/SU707521A3/en active
-
1980
- 1980-01-03 HK HK3/80A patent/HK380A/en unknown
- 1980-12-30 MY MY220/80A patent/MY8000220A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE394110B (en) | 1977-06-06 |
| FI57748B (en) | 1980-06-30 |
| ES443519A1 (en) | 1977-08-16 |
| PH12933A (en) | 1979-10-17 |
| DK136420C (en) | 1978-03-13 |
| DD118630A5 (en) | 1976-03-12 |
| ES443518A1 (en) | 1977-08-01 |
| NL7313111A (en) | 1974-04-02 |
| DD114604A5 (en) | 1975-08-12 |
| ATA833873A (en) | 1977-02-15 |
| JPS602304B2 (en) | 1985-01-21 |
| FR2201092B1 (en) | 1977-09-09 |
| IL43333A0 (en) | 1973-11-28 |
| FR2201092A1 (en) | 1974-04-26 |
| AU6085273A (en) | 1975-04-10 |
| ES419195A1 (en) | 1976-12-16 |
| ES443517A1 (en) | 1977-08-16 |
| DE2348593A1 (en) | 1974-04-11 |
| IE39474B1 (en) | 1978-10-25 |
| HK380A (en) | 1980-01-11 |
| CA1008865A (en) | 1977-04-19 |
| DK136420B (en) | 1977-10-10 |
| IE39474L (en) | 1974-03-29 |
| AT339891B (en) | 1977-11-10 |
| JPS4970960A (en) | 1974-07-09 |
| SU707521A3 (en) | 1979-12-30 |
| FI57748C (en) | 1980-10-10 |
| IL43333A (en) | 1978-10-31 |
| MY8000220A (en) | 1980-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 48R | Reference inserted (sect. 8/1949) | ||
| SP | Amendment (slips) printed | ||
| PCNP | Patent ceased through non-payment of renewal fee |