ES366688A1 - Dibenzocycloheptene derivatives and the manufacture thereof - Google Patents
Dibenzocycloheptene derivatives and the manufacture thereofInfo
- Publication number
- ES366688A1 ES366688A1 ES366688A ES366688A ES366688A1 ES 366688 A1 ES366688 A1 ES 366688A1 ES 366688 A ES366688 A ES 366688A ES 366688 A ES366688 A ES 366688A ES 366688 A1 ES366688 A1 ES 366688A1
- Authority
- ES
- Spain
- 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)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
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 formul[mu] where R1 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 formul[mu] 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 formul[mu] 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.
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 |
|---|---|
| ES366688A1 true ES366688A1 (en) | 1971-04-16 |
Family
ID=4312293
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES366688A Expired ES366688A1 (en) | 1968-05-03 | 1969-05-02 | Dibenzocycloheptene derivatives and the manufacture thereof |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS4939675B1 (en) |
| AT (9) | AT299153B (en) |
| BE (1) | BE732328A (en) |
| BR (1) | BR6908384D0 (en) |
| CA (1) | CA972752A (en) |
| CH (4) | CH501581A (en) |
| DE (1) | DE1922280C3 (en) |
| ES (1) | ES366688A1 (en) |
| FR (1) | FR2007772A1 (en) |
| GB (2) | GB1274261A (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) |
Families Citing this family (4)
| 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 |
| JP2020526592A (en) * | 2017-07-13 | 2020-08-31 | トニックス ファーマシューティカルズ ホールディング コーポレーション | Cyclobenzaprine analogs and amitryptylene analogs |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL290533A (en) * | 1962-03-23 |
-
1968
- 1968-05-03 CH CH661268A patent/CH501581A/en not_active IP Right Cessation
- 1968-05-03 CH CH1768570A patent/CH513808A/en not_active IP Right Cessation
- 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
- 1968-06-28 NO NO2577/68A patent/NO125628B/no unknown
- 1968-06-28 SE SE08965/68A patent/SE365790B/xx 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 GB22175/69A patent/GB1274261A/en not_active Expired
- 1969-05-01 GB GB28708/71A patent/GB1274265A/en not_active Expired
- 1969-05-01 IE IE611/69A patent/IE33452B1/en unknown
- 1969-05-02 AT AT1158770A patent/AT299153B/en not_active IP Right Cessation
- 1969-05-02 AT AT1158370A patent/AT296956B/en not_active IP Right Cessation
- 1969-05-02 AT AT1158670A patent/AT294036B/en not_active IP Right Cessation
- 1969-05-02 AT AT1158870A patent/AT296958B/en not_active IP Right Cessation
- 1969-05-02 AT AT425469A patent/AT296954B/en not_active IP Right Cessation
- 1969-05-02 ES ES366688A patent/ES366688A1/en not_active Expired
- 1969-05-02 AT AT1158270A patent/AT296955B/en not_active IP Right Cessation
- 1969-05-02 JP JP44034472A patent/JPS4939675B1/ja active Pending
- 1969-05-02 AT AT1158970A patent/AT296959B/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 AT1158570A patent/AT297679B/en active
-
1973
- 1973-12-30 MY MY181/73A patent/MY7300181A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT296959B (en) | 1972-03-10 |
| SE365790B (en) | 1974-04-01 |
| CH501581A (en) | 1971-01-15 |
| BR6908384D0 (en) | 1973-01-04 |
| MY7300181A (en) | 1973-12-31 |
| IL32058A (en) | 1974-01-14 |
| BE732328A (en) | 1969-10-30 |
| AT297679B (en) | 1972-04-10 |
| DE1922280C3 (en) | 1980-01-17 |
| GB1274265A (en) | 1972-05-17 |
| CH513806A (en) | 1971-10-15 |
| CH513808A (en) | 1971-10-15 |
| NL6905705A (en) | 1969-11-05 |
| CH513807A (en) | 1971-10-15 |
| NL161439B (en) | 1979-09-17 |
| FR2007772A1 (en) | 1970-01-09 |
| IE33452L (en) | 1969-11-03 |
| AT296954B (en) | 1972-03-10 |
| DE1922280A1 (en) | 1969-11-20 |
| AT294036B (en) | 1971-11-10 |
| CA972752A (en) | 1975-08-12 |
| AT299153B (en) | 1972-06-12 |
| NO125628B (en) | 1972-10-09 |
| IL32058A0 (en) | 1969-06-25 |
| DE1922280B2 (en) | 1979-05-03 |
| GB1274261A (en) | 1972-05-17 |
| NL161439C (en) | 1980-02-15 |
| AT296958B (en) | 1972-03-10 |
| IE33452B1 (en) | 1974-07-10 |
| AT296956B (en) | 1972-03-10 |
| JPS4939675B1 (en) | 1974-10-28 |
| AT296957B (en) | 1972-03-10 |
| AT296955B (en) | 1972-03-10 |
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