GB1359304A - 5-substituted-5h-dibenzo a,d cycloheptene derivatives - Google Patents
5-substituted-5h-dibenzo a,d cycloheptene derivativesInfo
- Publication number
- GB1359304A GB1359304A GB2480971A GB2480971A GB1359304A GB 1359304 A GB1359304 A GB 1359304A GB 2480971 A GB2480971 A GB 2480971A GB 2480971 A GB2480971 A GB 2480971A GB 1359304 A GB1359304 A GB 1359304A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- prepared
- compounds
- compound
- alkyl
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/36—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
- C07D303/10—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals in which the oxirane rings are condensed with a carbocyclic ring system having three or more relevant rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1359304 Dibenzocycloheptene derivatives SANDOZ Ltd 19 April 1971 [26 March 1970] 24809/71 Addition to 1311004 Heading C2C The invention comprises novel compounds of Formula I: (in which Z is -CH=CH- or -CH 2 -CH 2 -, R is H, NH 2 or C 1-4 alkyl and each of R 1 and R 2 is H, F, Cl, Br or C 1-3 alkoxy, provided that when R 1 and R 2 are both H, then R is C 1-4 alkyl) and acid addition salts thereof. Compounds of the Formula Ia: (in which R<SP>1</SP>, R<SP>1</SP> 1 and R<SP>1</SP> 2 are the same as R, R 1 and R 2 , except that when R<SP>1</SP> is C 1-4 alkyl, each of R<SP>1</SP> 1 and R<SP>1</SP> 2 is other than H) are prepared by reacting a compound of Formula II: with a compound of formula R<SP>1</SP>NH 2 . Compounds of Formula Ib: (in which each of R<SP>11</SP> 1 and R<SP>11</SP> 2 is H, F, Cl, Br or C 1-3 alkoxy, provided that at least one is other than H) are prepared by catalytically hydrogenating a compound of Formula Ic: Compounds of Formula Id: (in which R<SP>11</SP> is H or C 1-4 alkyl, provided that when R 1 and R 2 are both H, R<SP>11</SP> is C 1-4 alkyl) are prepared by subjecting a compound of Formula IV: to alkaline hydrolysis. Compounds of Formula IV are prepared by cyclizing a corresponding 5-hydroxy-dibenzo- [a, d] cyclohepten-5-acetic acid hydrazide or its 10,11-dihydro derivative, and optionally alkylating the resulting compound IV in which R<SP>11</SP> is H. 5 - Hydroxy - dibenzo[a, d]cyclohepten-5-acetic acid hydrazide is prepared by reacting 5-hydroxydibenzo[a, d]cyclohepten-5-acetic acid ethyl ester (itself prepared from dibenzo[a, d]cyclohepten- 5-one by the Reformatsky reaction) with hydrazine. Compounds of Formula II are prepared by reacting an appropriate dibenzocyclohepten-5- one or 10,11-dihydro derivative thereof with dimethylsulphonium methylide. Pharmaceutical compositions having anticonvulsant activity for oral or parenteral administration comprise a compound I, or a pharmaceutically acceptable acid addition salt thereof, together with a pharmaceutical carrier. Reference has been directed by the Comptroller to Specification 1,250,270.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US023077A US3911017A (en) | 1969-04-04 | 1970-03-26 | 5-Aminomethyl-5H-dibenzo{8 a,d{9 cycloheptenes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1359304A true GB1359304A (en) | 1974-07-10 |
Family
ID=21812997
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5092673A Expired GB1359305A (en) | 1970-03-26 | 1971-04-19 | 5-substituted-5h-dibenzo a,d cycloheptene derivatives |
| GB2480971A Expired GB1359304A (en) | 1970-03-26 | 1971-04-19 | 5-substituted-5h-dibenzo a,d cycloheptene derivatives |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5092673A Expired GB1359305A (en) | 1970-03-26 | 1971-04-19 | 5-substituted-5h-dibenzo a,d cycloheptene derivatives |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE764851R (en) |
| CH (5) | CH539647A (en) |
| DE (1) | DE2114092A1 (en) |
| ES (1) | ES389533A1 (en) |
| FR (3) | FR2085744B2 (en) |
| GB (2) | GB1359305A (en) |
-
1971
- 1971-03-15 CH CH809673A patent/CH539647A/en not_active IP Right Cessation
- 1971-03-15 CH CH1110273A patent/CH545276A/en not_active IP Right Cessation
- 1971-03-15 CH CH809573A patent/CH539646A/en not_active IP Right Cessation
- 1971-03-15 CH CH809473A patent/CH540224A/en not_active IP Right Cessation
- 1971-03-15 CH CH809373A patent/CH539603A/en not_active IP Right Cessation
- 1971-03-24 DE DE19712114092 patent/DE2114092A1/en active Pending
- 1971-03-24 ES ES389533A patent/ES389533A1/en not_active Expired
- 1971-03-25 BE BE764851A patent/BE764851R/en active
- 1971-03-25 FR FR7110584A patent/FR2085744B2/fr not_active Expired
- 1971-04-19 GB GB5092673A patent/GB1359305A/en not_active Expired
- 1971-04-19 GB GB2480971A patent/GB1359304A/en not_active Expired
-
1973
- 1973-03-13 FR FR7308839A patent/FR2201887B2/fr not_active Expired
- 1973-07-26 FR FR7327432A patent/FR2190471B2/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES389533A1 (en) | 1974-03-16 |
| CH539646A (en) | 1973-09-14 |
| DE2114092A1 (en) | 1971-10-28 |
| GB1359305A (en) | 1974-07-10 |
| FR2190471B2 (en) | 1976-07-02 |
| CH539603A (en) | 1973-09-14 |
| BE764851R (en) | 1971-09-27 |
| CH545276A (en) | 1974-01-31 |
| FR2201887B2 (en) | 1976-04-09 |
| FR2201887A2 (en) | 1974-05-03 |
| FR2085744B2 (en) | 1975-10-31 |
| FR2190471A2 (en) | 1974-02-01 |
| CH540224A (en) | 1973-09-28 |
| FR2085744A2 (en) | 1971-12-31 |
| CH539647A (en) | 1973-09-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |