GB1148740A - 5,10-epoxy-5-(aminopropyl)-dibenzocycloheptenes - Google Patents
5,10-epoxy-5-(aminopropyl)-dibenzocycloheptenesInfo
- Publication number
- GB1148740A GB1148740A GB37077/66A GB3707766A GB1148740A GB 1148740 A GB1148740 A GB 1148740A GB 37077/66 A GB37077/66 A GB 37077/66A GB 3707766 A GB3707766 A GB 3707766A GB 1148740 A GB1148740 A GB 1148740A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- compounds
- formula
- preparation
- coo
- 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
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/02—Solvent extraction of solids
- B01D11/0203—Solvent extraction of solids with a supercritical fluid
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0403—Solvent extraction of solutions which are liquid with a supercritical fluid
- B01D11/0407—Solvent extraction of solutions which are liquid with a supercritical fluid the supercritical fluid acting as solvent for the solute
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
1,148,740. 5,10 - Epoxy - dibenzocycloheptenes. MERCK & CO. Inc. 18 Aug., 1966 [23 Aug., 1965], No. 37077/66. Addition to 1,074,081. Heading C2C. The invention comprises (1) novel compounds of the Formulµ (I), (II), (III), (IV) and (V) (wherein NR<SP>1</SP>R<SP>11</SP> is C 1-6 alkylamino, except in the amine oxides, di-(C 1-6 alkyl)-amino, or saturated heterocyclic amino of 5 or 6 ring atoms containing NH, N(C 1-4 alkyl), or O as the optional additional hetero atom or atoms; A is C 1-5 alkyl and Z is acyloxy of the formula R*.COO-, Q.COO- or C 6 H 5 (CH 2 ) n COO- where the benzene ring may be substituted by one, two or three halogen, CF 3 , C 1-5 alkyl or C 1-5 alkoxy substituents, R<SP>*</SP> is alkyl, Q is an unsaturated aliphatic hydrocarbon radical and n is zero, 1, 2 or 3; or A is H and Z is C 1-5 alkylsulphonylamino, C 6 H 5 (CH 2 ) n SO 2 NH- wherein the benzene ring may be substituted as defined above, or Q.COO- or C 6 H 5 (CH 2 ) n COO- as defined above; or, when NR<SP>1</SP>R<SP>11</SP> is monoalkylamino, A is H and Z is C 2-6 alkanoyloxy; or Z and A together are R*.COON=, Q.COON = or CH 6 (CH 2 ) n COON= as defined for similar radicals above, hydrazono or C 1-5 alkoxyimino; X and X<SP>1</SP> are H, halogen, C 1-6 alkyl, C 2-6 alkenyl, CF 3 , OH, C 1-4 alkoxy, SH, C 1-4 alkylthio, C 1-4 alkylsulphonyl or SONH 2 which may be mono- or di-(C 1-4 alkyl) substituted, more than one substituent being optionally present on each benzene ring; R<SP>111</SP> is C 1-6 alkyl; R is H, OH, oxo, hydroxyimino or NH 2 which may be mono-(C 1-6 alkyl) substituted, or R is OH and C 1-6 alkyl on the same carbon atom; R<SP>1</SP> in NR<SP>1</SP>.COOR<SP>6</SP> is C 1-6 alkyl; R<SP>6</SP> is alkyl, aralkyl or aryl; and Z<SP>0</SP> is OH, C 1-5 alkoxyimino, C 1-6 alkylamino, C 1-5 alkylsulphonylamino or C 6 H 5 - (CH 2 ) n SO 2 NH- (as above defined) and their acid-addition salts, and, where appropriate, N-oxides; (2) the novel 5-[3-(N-carbethoxy-N- methylamino) - propyl] - 10,11 - dihydro - 5,10- epoxy - 11 - hydroxy - 11 - methyl - 5H - dibenzo-[a,d]-cycloheptene; (3) certain novel epoxy-dibenzocycloheptenes falling within Claims 1 and 6 of Specification 1,074,081; (4) the preparation of compounds of the Formula (VI) by dealkylation of the corresponding dialkylamino compounds by reaction with a haloformate ester followed by hydrolysis; (5) the preparation of the 11-alkoxyimino compounds of Formula (I) by treatment of the corresponding 11-ketones with the appropriate alkoxyamine in an inert solvent, the starting materials being prepared by Oppenauer oxidation of the 11-ols; (6) the reduction of the 11- alkoxyimino products of (5) to the corresponding 11-amino compounds; (7) the preparation of the 11-acyloxy compounds of Formula (I) by acylation of the corresponding 11-ols; (8) the preparation of the 11-acyloxyimino compounds of the Formula (I) by acylation of the corresponding 11-hydroxyimino compounds, monoalkylamino starting materials in this and method (7) being used as their acid-addition salts; (9) the preparation of the 11-sulphonamido compounds of Formula (I) wherein NR<SP>1</SP>R<SP>11</SP> is not monoalkylamino from the corresponding 11-amino compounds and the appropriate sulphonyl halide or sulphonic anhydride; (10) dealkylation of the products of process (9) by the method of (4) to give the corresponding 3- monoalkylaminopropyl compounds; (11) the preparation of compounds of the Formula (I) wherein A is alkyl and Z is acyloxy by acylation of the corresponding 11-ols, the starting material being an acid-addition salt if NR<SP>1</SP>R<SP>11</SP> is monoalkylamino; and (12) the preparation of the 11-hydrazono compounds of Formula (I) by reaction of the corresponding 11-ketones with hydrazine. Products containing 2 dissimilar substituents on the 11-carbon atom may be resolved by conventional methods. The 5,10-epoxydibenzocycloheptenes of the invention, which are stated to be anti-depressants, may be made up into pharmaceutical compositions for oral or parenteral administration with suitable carriers.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US28696263A | 1963-06-11 | 1963-06-11 | |
US30663963A | 1963-09-04 | 1963-09-04 | |
US48190865A | 1965-08-23 | 1965-08-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1148740A true GB1148740A (en) | 1969-04-16 |
Family
ID=27403666
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1280/67A Expired GB1074086A (en) | 1963-06-11 | 1964-06-08 | Dibenzocycloheptene derivatives |
GB37077/66A Expired GB1148740A (en) | 1963-06-11 | 1966-08-18 | 5,10-epoxy-5-(aminopropyl)-dibenzocycloheptenes |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1280/67A Expired GB1074086A (en) | 1963-06-11 | 1964-06-08 | Dibenzocycloheptene derivatives |
Country Status (5)
Country | Link |
---|---|
US (1) | US3494935A (en) |
BE (1) | BE685858A (en) |
DE (1) | DE1543770A1 (en) |
GB (2) | GB1074086A (en) |
NL (1) | NL6611814A (en) |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE557002A (en) * | 1956-07-09 | |||
US3264342A (en) * | 1963-05-24 | 1966-08-02 | Geigy Chem Corp | Derivatives of 5h-dibenzo[a, d] cycloheptene |
US3258488A (en) * | 1963-08-12 | 1966-06-28 | Colgate Palmolive Co | Dibenzo[a, d]cycloheptene derivatives |
-
1964
- 1964-06-08 GB GB1280/67A patent/GB1074086A/en not_active Expired
-
1965
- 1965-08-23 US US481908A patent/US3494935A/en not_active Expired - Lifetime
-
1966
- 1966-08-18 GB GB37077/66A patent/GB1148740A/en not_active Expired
- 1966-08-22 NL NL6611814A patent/NL6611814A/xx unknown
- 1966-08-23 BE BE685858D patent/BE685858A/xx unknown
- 1966-08-23 DE DE19661543770 patent/DE1543770A1/en active Pending
Also Published As
Publication number | Publication date |
---|---|
BE685858A (en) | 1967-02-23 |
NL6611814A (en) | 1967-02-24 |
DE1543770A1 (en) | 1969-12-18 |
GB1074086A (en) | 1967-06-28 |
US3494935A (en) | 1970-02-10 |
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