GB1274261A - Dibenzocycloheptene derivatives and the manufacture thereof - Google Patents
Dibenzocycloheptene derivatives and the manufacture thereofInfo
- Publication number
- GB1274261A GB1274261A GB22175/69A GB2217569A GB1274261A GB 1274261 A GB1274261 A GB 1274261A GB 22175/69 A GB22175/69 A GB 22175/69A GB 2217569 A GB2217569 A GB 2217569A GB 1274261 A GB1274261 A GB 1274261A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- group
- formula
- compounds
- methyl
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
- C07C65/38—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups having unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/33—Polycyclic acids
- C07C63/331—Polycyclic acids with all carboxyl groups bound to non-condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/30—Ortho- or ortho- and peri-condensed systems containing three rings containing seven-membered rings
- C07C2603/32—Dibenzocycloheptenes; Hydrogenated dibenzocycloheptenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Abstract
1,274,261. 1,5 - Disubstituted - dibenzocycloheptenes. F. HOFFMANN-LA ROCHE & CO. A.G. 1 May, 1969 [3 May, 1968], No. 22175/69. Heading C2C. Novel compounds of Formula I in which R 1 represents a hydrogen atom or a methyl group, R represents a methyl or acetyl group and the dotted bonds can be hydrogenated, N-oxides of compounds of Formula I in which R 1 represents a methyl group, geometric and optical isomers of said compounds, and N-oxides and acid addition salts of said compounds, N-oxides and isomers; with the exception of 1-methyl-5-(3-methylaminopropylidene) - 5H - dibenzo - [a,d] - cycloheptene and 1 - acetyl - 5 - (3 - methylaminopropyl)-5H- dibenzo 10,11-dihydrocycloheptene, are prepared by one of the following methods: (a) reduction of a compound of formula (b) dehydration of one of the compounds of formulµ where R<SP>1</SP> is methyl or a ketalized acetyl group, (c) reacting a compound of formula wherein W represents a halogen atom, with a 3-dimethylaminopropyl magnesium halide, (d) treating a compound of one of the general formulµ wherein Z represents a halogen atom or a substituted sulfonyloxy group and A represents the anion of an acid, with methylamine, dimethylamine or dimethylhydroxylamine, (e) methylating a primary amine of the general formula wherein E represents an amino group or an N-hydroxy-N-methyl group, (f) debenzylating a compound of the general formula (g) heating a compound of either of formulµ wherein P 1 represents a hydrogen atom or a hydroxyl group and P 2 represents a hydrogen atom or P 1 and P 2 together represent an additional bond, Q represents the residue of an aldehyde and B represents the anion of an acid, (h) reacting a compound of the general formula wherein T is an alkali metal atom with a compound of formula L.CH 2 .CH 2 .CH 2 N(CH 3 ) 2 , wherein L is a halogen atom or a substituted sulphonyloxy group, and (i) hydrolytically cleaving a compound of formula wherein D represents an acyl or esterified carboxyl group, whereupon, in any desired sequence and if desired, a resulting compound in which R 1 represents a hydrogen atom is methylated, if desired, a compound in which R 1 represents a methyl group is oxidized or converted into a compound in which R 1 represents a hydrogen atom by demethylation, if desired, an unsaturated product obtained is hydrogenated, if desired, a 10,11-dihydro compound obtained is dehydrogenated, if necessary, a ketal obtained is deketalized, if desired, the geometric and/or optical isomers are isolated from an isomer mixture obtained and, if desired, a base obtained is converted into an acid addition salt. 1 - Methyl - 5 - chloro - 5H - dibenzo[a,d]cycloheptene and the 10,11-dihydro-compound are prepared by the action of thionyl chloride on the corresponding 5-hydroxy-compounds which are obtained by reduction of the 5-keto compounds. Pharmaceutical compositions in conventional forms for oral or parenteral administration and having antidepressant, adrenolytic, anihistamine and local anaesthetic activity comprise an above novel compound and a carrier therefor.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB28707/71A GB1274264A (en) | 1968-05-03 | 1969-05-01 | Dibenzocycloheptene derivatives |
| GB28706/71A GB1274263A (en) | 1968-05-03 | 1969-05-01 | Dibenzocycloheptene derivatives |
| GB28709/71A GB1274266A (en) | 1968-05-03 | 1969-05-01 | Dibenzocycloheptene derivatives |
| GB28705/71A GB1274262A (en) | 1968-05-03 | 1969-05-01 | Dibenzocycloheptene derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH661268A CH501581A (en) | 1968-05-03 | 1968-05-03 | Process for the preparation of tricyclic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1274261A true GB1274261A (en) | 1972-05-17 |
Family
ID=4312293
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28708/71A Expired GB1274265A (en) | 1968-05-03 | 1969-05-01 | Dibenzocycloheptene derivatives |
| GB22175/69A Expired GB1274261A (en) | 1968-05-03 | 1969-05-01 | Dibenzocycloheptene derivatives and the manufacture thereof |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28708/71A Expired GB1274265A (en) | 1968-05-03 | 1969-05-01 | Dibenzocycloheptene derivatives |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS4939675B1 (en) |
| AT (9) | AT296955B (en) |
| BE (1) | BE732328A (en) |
| BR (1) | BR6908384D0 (en) |
| CA (1) | CA972752A (en) |
| CH (4) | CH513806A (en) |
| DE (1) | DE1922280C3 (en) |
| ES (1) | ES366688A1 (en) |
| FR (1) | FR2007772A1 (en) |
| GB (2) | GB1274265A (en) |
| IE (1) | IE33452B1 (en) |
| IL (1) | IL32058A (en) |
| MY (1) | MY7300181A (en) |
| NL (1) | NL161439C (en) |
| NO (1) | NO125628B (en) |
| SE (1) | SE365790B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110996932A (en) * | 2017-07-13 | 2020-04-10 | 托尼克斯医药控股公司 | Cyclobenzaprine and amitriptyline analogs |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5321655A (en) * | 1976-08-11 | 1978-02-28 | Matsushita Electric Works Ltd | Motor driven tooth brush |
| JPS5321654A (en) * | 1976-08-11 | 1978-02-28 | Matsushita Electric Works Ltd | Motor driven tooth brush |
| CA1160219A (en) * | 1981-01-16 | 1984-01-10 | Werner Aschwanden | Cycloheptene derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE630063A (en) * | 1962-03-23 |
-
1968
- 1968-05-03 CH CH1768070A patent/CH513806A/en not_active IP Right Cessation
- 1968-05-03 CH CH1768270A patent/CH513807A/en not_active IP Right Cessation
- 1968-05-03 CH CH1768570A patent/CH513808A/en not_active IP Right Cessation
- 1968-05-03 CH CH661268A patent/CH501581A/en not_active IP Right Cessation
- 1968-06-28 SE SE08965/68A patent/SE365790B/xx unknown
- 1968-06-28 NO NO2577/68A patent/NO125628B/no unknown
-
1969
- 1969-04-14 NL NL6905705.A patent/NL161439C/en active
- 1969-04-22 IL IL32058A patent/IL32058A/en unknown
- 1969-04-28 CA CA049,911A patent/CA972752A/en not_active Expired
- 1969-04-28 BR BR208384/69A patent/BR6908384D0/en unknown
- 1969-04-30 BE BE732328D patent/BE732328A/xx unknown
- 1969-04-30 DE DE1922280A patent/DE1922280C3/en not_active Expired
- 1969-05-01 GB GB28708/71A patent/GB1274265A/en not_active Expired
- 1969-05-01 GB GB22175/69A patent/GB1274261A/en not_active Expired
- 1969-05-01 IE IE611/69A patent/IE33452B1/en unknown
- 1969-05-02 AT AT1158270A patent/AT296955B/en not_active IP Right Cessation
- 1969-05-02 AT AT1158870A patent/AT296958B/en not_active IP Right Cessation
- 1969-05-02 AT AT1158370A patent/AT296956B/en not_active IP Right Cessation
- 1969-05-02 AT AT1158470A patent/AT296957B/en not_active IP Right Cessation
- 1969-05-02 FR FR6914017A patent/FR2007772A1/fr not_active Withdrawn
- 1969-05-02 AT AT1158970A patent/AT296959B/en not_active IP Right Cessation
- 1969-05-02 ES ES366688A patent/ES366688A1/en not_active Expired
- 1969-05-02 AT AT1158770A patent/AT299153B/en not_active IP Right Cessation
- 1969-05-02 AT AT1158570A patent/AT297679B/en active
- 1969-05-02 AT AT425469A patent/AT296954B/en not_active IP Right Cessation
- 1969-05-02 JP JP44034472A patent/JPS4939675B1/ja active Pending
- 1969-05-02 AT AT1158670A patent/AT294036B/en not_active IP Right Cessation
-
1973
- 1973-12-30 MY MY181/73A patent/MY7300181A/en unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110996932A (en) * | 2017-07-13 | 2020-04-10 | 托尼克斯医药控股公司 | Cyclobenzaprine and amitriptyline analogs |
| EP3651751A4 (en) * | 2017-07-13 | 2021-03-31 | Tonix Pharmaceuticals Holding Corp. | CYCLOBENZAPRINE ANALOGA AND AMITRYPTILES |
| US11517557B2 (en) | 2017-07-13 | 2022-12-06 | Tonix Pharmaceuticals Holding Corp. | Analogs of cyclobenzaprine and amitriptyline |
| US12156864B2 (en) | 2017-07-13 | 2024-12-03 | TONIX Pharmaceuticals Holding Corp | Analogs of cyclobenzaprine and amitryptilene |
Also Published As
| Publication number | Publication date |
|---|---|
| AT296958B (en) | 1972-03-10 |
| AT296959B (en) | 1972-03-10 |
| IL32058A0 (en) | 1969-06-25 |
| IE33452B1 (en) | 1974-07-10 |
| DE1922280A1 (en) | 1969-11-20 |
| ES366688A1 (en) | 1971-04-16 |
| BE732328A (en) | 1969-10-30 |
| NO125628B (en) | 1972-10-09 |
| GB1274265A (en) | 1972-05-17 |
| MY7300181A (en) | 1973-12-31 |
| NL161439B (en) | 1979-09-17 |
| AT294036B (en) | 1971-11-10 |
| SE365790B (en) | 1974-04-01 |
| AT296956B (en) | 1972-03-10 |
| JPS4939675B1 (en) | 1974-10-28 |
| NL6905705A (en) | 1969-11-05 |
| NL161439C (en) | 1980-02-15 |
| IL32058A (en) | 1974-01-14 |
| BR6908384D0 (en) | 1973-01-04 |
| AT296955B (en) | 1972-03-10 |
| AT297679B (en) | 1972-04-10 |
| IE33452L (en) | 1969-11-03 |
| CH513807A (en) | 1971-10-15 |
| AT296957B (en) | 1972-03-10 |
| FR2007772A1 (en) | 1970-01-09 |
| DE1922280B2 (en) | 1979-05-03 |
| DE1922280C3 (en) | 1980-01-17 |
| CH513808A (en) | 1971-10-15 |
| CH501581A (en) | 1971-01-15 |
| AT296954B (en) | 1972-03-10 |
| AT299153B (en) | 1972-06-12 |
| CH513806A (en) | 1971-10-15 |
| CA972752A (en) | 1975-08-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |