GB1074082A - Dibenzocycloheptene compounds - Google Patents
Dibenzocycloheptene compoundsInfo
- Publication number
- GB1074082A GB1074082A GB28412/64A GB2841264A GB1074082A GB 1074082 A GB1074082 A GB 1074082A GB 28412/64 A GB28412/64 A GB 28412/64A GB 2841264 A GB2841264 A GB 2841264A GB 1074082 A GB1074082 A GB 1074082A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- formula
- formulae
- alkyl
- compound
- 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
- 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
-
- 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
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)
- Hydrogenated Pyridines (AREA)
Abstract
The invention comprises compounds of the formulae I, II, III, IV and V wherein each of R and R1 represents a C1- 6 alkyl radical or R and R1 are joined to represent, together with the N atom to which they are attached, a 1-piperidyl, 1 - pyrrolidinyl, 1 - morpholinyl or 1 - (C1- 4 alkyl) - 4 - piperazinyl ring, each of X and X1 represents a hydrogen or halogen atom or a C1- 6 alkyl, C2- 6 alkenyl, trifluoromethyl, hydroxyl, C1- 4 alkoxy, mercapto, C1- 4 alkylmercapto, C1- 4 alkylsulphonyl, sulphamoyl, C1- 4 alkylsulphamoyl or C2- 8 dialkylsulphamoyl radical, Ac represents an acyl radical and each of R11 and R111 represents a hydrogen atom or an alkyl, aryl or aralkyl group, and non-toxic salts of compounds of the Formulae I and II; the process wherein compounds of Formulae VI or VII are reacted with a Grignard reagent of the Formula HalMgCH2CH2CH2 NRR1, where Hal represents a halogen atom, the Grignard adducts hydrolysed and the resulting 5 - hydroxy - 5 - (3 - tertiary aminopropyl) derivatives dehydrated to give compounds of the Formulae III or V respectively which may be hydrolysed to give a compound of the Formula I; the preparation of compounds of the Formula I by treating compounds of the Formula VIII with osmium tetroxide in a dry, inert solvent and hydrolysing the resulting osmic esters; the preparation of compounds of the Formula II by reacting a compound of the Formula III or a compound of the Formula V, wherein each of R and R1 represents a C1- 6 alky radical, with a haloformate and hydrolysing the resulting urethane, or by reacting a compound of the Formula III, wherein each of R and R1 represents a C1- 6 alkyl group, with a cyanogen halide and hydrolysing the resulting product. <FORM:1074082/C2/1> <FORM:1074082/C2/2> <FORM:1074082/C2/3> <FORM:1074082/C2/4> <FORM:1074082/C2/5> <FORM:1074082/C2/6> <FORM:1074082/C2/7> <FORM:1074082/C2/8> Compounds of the Formula IV may be prepared by reacting a compound of the Formula III, wherein each of R and R1 represents a C1- 6 alkyl radical, with a haloformate or cyanogen halide and hydrolysing the resultant product in a basic medium. Therapeutic compositions with anti-depressant properties, in the forms of tablets, powders, sustained release pellets, solutions or suspensions for oral and parenteral application, comprise compounds of the Formulae I and II or their non-toxic salts, or compounds of the Formulae III, IV and V, with an inert pharmaceutical diluent, carrier or coating.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US296463A US3390179A (en) | 1963-07-22 | 1963-07-22 | Novel 10, 11-dihydro-10, 11-dihydroxy-(3-substituted aminopropylidene)-5h-dibenzo [a, d] cycloheptenes |
US4847870A | 1970-06-22 | 1970-06-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1074082A true GB1074082A (en) | 1967-06-28 |
Family
ID=26726156
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB35403/66A Expired GB1074084A (en) | 1963-07-22 | 1964-07-09 | Dibenzocycloheptene compounds |
GB28412/64A Expired GB1074082A (en) | 1963-07-22 | 1964-07-09 | Dibenzocycloheptene compounds |
GB35402/66A Expired GB1074083A (en) | 1963-07-22 | 1964-07-09 | Dibenzocycloheptene compounds |
GB35404/66A Expired GB1074085A (en) | 1963-07-22 | 1964-07-09 | Dibenzocycloheptene compounds |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB35403/66A Expired GB1074084A (en) | 1963-07-22 | 1964-07-09 | Dibenzocycloheptene compounds |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB35402/66A Expired GB1074083A (en) | 1963-07-22 | 1964-07-09 | Dibenzocycloheptene compounds |
GB35404/66A Expired GB1074085A (en) | 1963-07-22 | 1964-07-09 | Dibenzocycloheptene compounds |
Country Status (11)
Country | Link |
---|---|
US (2) | US3390179A (en) |
BE (1) | BE650800A (en) |
BR (1) | BR6460953D0 (en) |
CH (1) | CH494731A (en) |
DE (1) | DE1468339A1 (en) |
DK (3) | DK127723B (en) |
FR (2) | FR1572128A (en) |
GB (4) | GB1074084A (en) |
IL (2) | IL21665A (en) |
NL (1) | NL6408390A (en) |
SE (3) | SE332820B (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3905981A (en) * | 1973-10-12 | 1975-09-16 | Research Corp | N-dealkylation of tertiary amines |
US4089864A (en) * | 1974-03-25 | 1978-05-16 | Merck & Co., Inc. | 4-(10,11-Dihydro-cis and trans-10,11-dihydroxy-5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidines |
US3894032A (en) * | 1974-04-10 | 1975-07-08 | Merck & Co Inc | 10,11-Furo derivatives of cyproheptadine |
US4044143A (en) * | 1975-01-30 | 1977-08-23 | Merck & Co., Inc. | 10,11-Bis-(hydroxyalkyl) derivatives of cyproheptadine |
DE4232173A1 (en) * | 1992-09-25 | 1994-03-31 | Bayer Ag | 5-oxo-dibenzo (a, d) cyclohepta-1,4-diene |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3234279A (en) * | 1962-09-14 | 1966-02-08 | Merck & Co Inc | 5-(gamma-amino-propyl- and propylidene-) 5h-dibenzo[a, d]-10-hydroxy-10, 11-dihydrocycloheptenes and amine borane salts thereof |
-
1963
- 1963-07-22 US US296463A patent/US3390179A/en not_active Expired - Lifetime
-
1964
- 1964-07-02 SE SE09743/67A patent/SE332820B/xx unknown
- 1964-07-07 IL IL21665A patent/IL21665A/en unknown
- 1964-07-07 IL IL29677A patent/IL29677A/en unknown
- 1964-07-09 GB GB35403/66A patent/GB1074084A/en not_active Expired
- 1964-07-09 GB GB28412/64A patent/GB1074082A/en not_active Expired
- 1964-07-09 GB GB35402/66A patent/GB1074083A/en not_active Expired
- 1964-07-09 GB GB35404/66A patent/GB1074085A/en not_active Expired
- 1964-07-17 BR BR160953/64A patent/BR6460953D0/en unknown
- 1964-07-20 BE BE650800D patent/BE650800A/xx unknown
- 1964-07-21 DK DK362064AA patent/DK127723B/en unknown
- 1964-07-21 SE SE8875/64A patent/SE320963B/xx unknown
- 1964-07-21 CH CH953364A patent/CH494731A/en not_active IP Right Cessation
- 1964-07-21 DE DE19641468339 patent/DE1468339A1/en active Pending
- 1964-07-21 SE SE09742/67A patent/SE332819B/xx unknown
- 1964-07-21 FR FR1572128D patent/FR1572128A/fr not_active Expired
- 1964-07-22 NL NL6408390A patent/NL6408390A/xx unknown
- 1964-10-20 FR FR992062A patent/FR3905M/fr not_active Expired
-
1965
- 1965-07-09 DK DK351265AA patent/DK121856B/en unknown
- 1965-07-09 DK DK351165AA patent/DK121757B/en unknown
-
1970
- 1970-06-22 US US48478A patent/US3660389A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
US3660389A (en) | 1972-05-02 |
BE650800A (en) | 1965-01-20 |
CH494731A (en) | 1970-08-15 |
BR6460953D0 (en) | 1973-08-02 |
FR3905M (en) | 1966-02-07 |
DK121757B (en) | 1971-11-29 |
DK121856B (en) | 1971-12-13 |
SE332820B (en) | 1971-02-22 |
NL6408390A (en) | 1965-01-25 |
DK127723B (en) | 1973-12-24 |
US3390179A (en) | 1968-06-25 |
SE332819B (en) | 1971-02-22 |
SE320963B (en) | 1970-02-23 |
IL21665A (en) | 1969-01-29 |
GB1074083A (en) | 1967-06-28 |
GB1074085A (en) | 1967-06-28 |
DE1468339A1 (en) | 1968-12-19 |
FR1572128A (en) | 1969-06-27 |
GB1074084A (en) | 1967-06-28 |
IL29677A (en) | 1969-01-29 |
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