GB1274265A - Dibenzocycloheptene derivatives - Google Patents
Dibenzocycloheptene derivativesInfo
- Publication number
- GB1274265A GB1274265A GB28708/71A GB2870871A GB1274265A GB 1274265 A GB1274265 A GB 1274265A GB 28708/71 A GB28708/71 A GB 28708/71A GB 2870871 A GB2870871 A GB 2870871A GB 1274265 A GB1274265 A GB 1274265A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- methyl
- compound
- formula
- prepared
- 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
1,274,265. 1,5 - Disubstituted - dibenzocycloheptenes. F. HOFFMANN-LA ROCHE & CO. A.G. 1 May, 1969 [3 May, 1968], No. 28708/71. Divided out of 1,274,261. Heading C2C. Novel compounds of Formula I wherein the dotted bonds can be hydrogenated, R<SP>1</SP> represents a methyl or ketalized acetyl (as hereinafter defined) group and A represents an amino, N - hydroxy - N - methyl - amino or N- benzyl - N - methyl - amino group or, when an exocyclic single-bond is present in the 5-position, an N - methyl - N - acylamino or N - methyl- N-(esterified carboxyl) group; (the term " ketalized acetyl " group is used herein to mean an acetyl group ketalized with an alkanol or alkylene glycol containing up to 7 carbon atoms) are prepared by one of the following methods: Those derivatives which carry a 3-aminopropylidene chain in the 5-position can be prepared by replacing the keto group of a corresponding 5H - dibenzo[a,d]cyclohepten- 5 - one or 10,11- dihydro - 5H - dibenzo[a,d]cyclohepten - 5 - one by an ethylidene group (e.g. by means of a Grignard reaction), halogenating the product obtained, treating the resulting halide with a nitrile and reducing the nitrile obtained with lithium aluminium hydride. Where the nitrile carries a methyl group in the 1-position, the reduction can be carried out using catalytically activated hydrogen, there being obtained a derivative of Formula I in which R<SP>1</SP> represents a methyl group and in which a 3-aminopropyl group is present in the 5-position. Compounds of Formula I which carry a 3-amino-propyl or 3-aminopropylidene group in the 5-position are also prepared by treating a compound of the general formula wherein R<SP>1</SP> and the dotted bonds have the significance given earlier and Z represents a halogen atom or a substituted-sulfonyloxy group, with potassium phthalimide and reacting the product obtained with hydrazine. Compounds which carry a 3-aminopropyl group in the 5-position are prepared by reacting a compound of formula wherein R<SP>1</SP> and the dotted bonds have the significance given earlier and T represents an alkali metal atom, with acrylonitrile and then reducing the resulting nitrile. Compounds of Formula I which carry an N-hydroxy substituent on the chain at the 3-position are prepared as follows: 1 -(Methyl or ketalized acetyl)- 5H - dibenzo[a,d]cyclohepten-5-one or the corresponding 10,11-dihydro compound is reacted with a N-methyl-N-benzylaminopropyl magnesium halide. After hydrolysis of the resulting product (e.g. with saturated ammonium chloride solution), the 5-carbinol obtained is reacted with chloroformic acid ethyl ester. The resulting 5 - hydroxy - 5 - [3 - (N - methyl-N- carbethoxyamino)-propyl] compound is then hydrolysed in an alkaline medium. A decarboxylation thereby occurs and there is formed the corresponding 5-hydroxy-5-(3-methylaminopropyl) compound. Where such a compound carries a methyl group in the 1-position of the ring, it can be reduced to the corresponding 5-(3-methylaminopropyl) compound by treatment with catalytically activated hydrogen. Compounds of Formula I wherein A is N-benzyl- N-methylamino are prepared by reaction of N-methyl benzylamine with either of compounds of formulµ wherein A is an anion.
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 |
---|---|
GB1274265A true GB1274265A (en) | 1972-05-17 |
Family
ID=4312293
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB22175/69A Expired GB1274261A (en) | 1968-05-03 | 1969-05-01 | Dibenzocycloheptene derivatives and the manufacture thereof |
GB28708/71A Expired GB1274265A (en) | 1968-05-03 | 1969-05-01 | Dibenzocycloheptene derivatives |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB22175/69A Expired GB1274261A (en) | 1968-05-03 | 1969-05-01 | Dibenzocycloheptene derivatives and the manufacture thereof |
Country Status (16)
Country | Link |
---|---|
JP (1) | JPS4939675B1 (en) |
AT (9) | AT296958B (en) |
BE (1) | BE732328A (en) |
BR (1) | BR6908384D0 (en) |
CA (1) | CA972752A (en) |
CH (4) | CH513808A (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 |
---|---|---|---|---|
JPS5321654A (en) * | 1976-08-11 | 1978-02-28 | Matsushita Electric Works Ltd | Motor driven tooth brush |
JPS5321655A (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 |
US11517557B2 (en) | 2017-07-13 | 2022-12-06 | Tonix Pharmaceuticals Holding Corp. | Analogs of cyclobenzaprine and amitriptyline |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE630063A (en) * | 1962-03-23 |
-
1968
- 1968-05-03 CH CH1768570A patent/CH513808A/en not_active IP Right Cessation
- 1968-05-03 CH CH1768270A patent/CH513807A/en not_active IP Right Cessation
- 1968-05-03 CH CH661268A patent/CH501581A/en not_active IP Right Cessation
- 1968-05-03 CH CH1768070A patent/CH513806A/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 BR BR208384/69A patent/BR6908384D0/en unknown
- 1969-04-28 CA CA049,911A patent/CA972752A/en not_active Expired
- 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 IE IE611/69A patent/IE33452B1/en unknown
- 1969-05-01 GB GB28708/71A patent/GB1274265A/en not_active Expired
- 1969-05-02 AT AT1158870A patent/AT296958B/en not_active IP Right Cessation
- 1969-05-02 AT AT1158670A patent/AT294036B/en not_active IP Right Cessation
- 1969-05-02 JP JP44034472A patent/JPS4939675B1/ja active Pending
- 1969-05-02 AT AT1158770A patent/AT299153B/en not_active IP Right Cessation
- 1969-05-02 FR FR6914017A patent/FR2007772A1/fr not_active Withdrawn
- 1969-05-02 ES ES366688A patent/ES366688A1/en not_active Expired
- 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 AT AT1158470A patent/AT296957B/en not_active IP Right Cessation
- 1969-05-02 AT AT1158270A patent/AT296955B/en not_active IP Right Cessation
- 1969-05-02 AT AT1158970A patent/AT296959B/en not_active IP Right Cessation
- 1969-05-02 AT AT1158370A patent/AT296956B/en not_active IP Right Cessation
-
1973
- 1973-12-30 MY MY181/73A patent/MY7300181A/en unknown
Also Published As
Publication number | Publication date |
---|---|
SE365790B (en) | 1974-04-01 |
CH513807A (en) | 1971-10-15 |
ES366688A1 (en) | 1971-04-16 |
DE1922280A1 (en) | 1969-11-20 |
DE1922280B2 (en) | 1979-05-03 |
AT296958B (en) | 1972-03-10 |
AT296957B (en) | 1972-03-10 |
AT296955B (en) | 1972-03-10 |
AT296956B (en) | 1972-03-10 |
NL161439C (en) | 1980-02-15 |
NL6905705A (en) | 1969-11-05 |
IE33452B1 (en) | 1974-07-10 |
MY7300181A (en) | 1973-12-31 |
CH513808A (en) | 1971-10-15 |
IL32058A (en) | 1974-01-14 |
BR6908384D0 (en) | 1973-01-04 |
NO125628B (en) | 1972-10-09 |
CH513806A (en) | 1971-10-15 |
IL32058A0 (en) | 1969-06-25 |
FR2007772A1 (en) | 1970-01-09 |
BE732328A (en) | 1969-10-30 |
AT294036B (en) | 1971-11-10 |
CH501581A (en) | 1971-01-15 |
IE33452L (en) | 1969-11-03 |
AT296954B (en) | 1972-03-10 |
AT297679B (en) | 1972-04-10 |
CA972752A (en) | 1975-08-12 |
AT296959B (en) | 1972-03-10 |
DE1922280C3 (en) | 1980-01-17 |
JPS4939675B1 (en) | 1974-10-28 |
GB1274261A (en) | 1972-05-17 |
NL161439B (en) | 1979-09-17 |
AT299153B (en) | 1972-06-12 |
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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 |