GB1017696A - Substituted 5h-dibenzo[a, d]cycloheptenes and 10,11-dihydro-5h-dibenzo[a, d]cycloheptenes - Google Patents
Substituted 5h-dibenzo[a, d]cycloheptenes and 10,11-dihydro-5h-dibenzo[a, d]cycloheptenesInfo
- Publication number
- GB1017696A GB1017696A GB3514262A GB3514262A GB1017696A GB 1017696 A GB1017696 A GB 1017696A GB 3514262 A GB3514262 A GB 3514262A GB 3514262 A GB3514262 A GB 3514262A GB 1017696 A GB1017696 A GB 1017696A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dibenzo
- cyclohepten
- dihydro
- compound
- radical
- 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
- QPJORFLSOJAUNL-UHFFFAOYSA-N dibenzo[a,d][7]annulene Chemical class C1=CC2=CC=CC=C2CC2=CC=CC=C21 QPJORFLSOJAUNL-UHFFFAOYSA-N 0.000 title abstract 4
- PJQCANLCUDUPRF-UHFFFAOYSA-N dibenzocycloheptene Chemical class C1CC2=CC=CC=C2CC2=CC=CC=C12 PJQCANLCUDUPRF-UHFFFAOYSA-N 0.000 title 1
- -1 C1-C4 alkyl radical Chemical class 0.000 abstract 17
- 150000001875 compounds Chemical class 0.000 abstract 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- 150000003254 radicals Chemical class 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 3
- 239000011777 magnesium Substances 0.000 abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract 3
- 229910052700 potassium Inorganic materials 0.000 abstract 3
- 239000011591 potassium Substances 0.000 abstract 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical group [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 229910052744 lithium Inorganic materials 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 2
- VBMVFJIFEVLDGP-UHFFFAOYSA-N n,n-dimethyl-11-oxo-5,6-dihydrodibenzo[3,1-[7]annulene-2-sulfonamide Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC(S(=O)(=O)N(C)C)=CC=C21 VBMVFJIFEVLDGP-UHFFFAOYSA-N 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- UKFHUHRZOQDUCI-UHFFFAOYSA-N 11-chloro-2-methylsulfanyl-11h-dibenzo[1,3-e:1',2'-f][7]annulene Chemical compound C1=CC2=CC=CC=C2C(Cl)C2=CC(SC)=CC=C21 UKFHUHRZOQDUCI-UHFFFAOYSA-N 0.000 abstract 1
- VIEXKWPWUNNTBM-UHFFFAOYSA-N 11-chloro-n,n-dimethyl-11h-dibenzo[1,3-e:1',2'-f][7]annulene-2-sulfonamide Chemical compound C1=CC2=CC=CC=C2C(Cl)C2=CC(S(=O)(=O)N(C)C)=CC=C21 VIEXKWPWUNNTBM-UHFFFAOYSA-N 0.000 abstract 1
- MPRGNTGIUDDLEC-UHFFFAOYSA-N 11-hydroxy-n,n-dimethyl-11h-dibenzo[1,3-e:1',2'-f][7]annulene-2-sulfonamide Chemical compound C1=CC2=CC=CC=C2C(O)C2=CC(S(=O)(=O)N(C)C)=CC=C21 MPRGNTGIUDDLEC-UHFFFAOYSA-N 0.000 abstract 1
- JOMFDSUEDLXEFK-UHFFFAOYSA-N 11-hydroxy-n,n-dimethyl-6,11-dihydro-5h-dibenzo[1,3-e:1',2'-f][7]annulene-2-sulfonamide Chemical compound C1CC2=CC=CC=C2C(O)C2=CC(S(=O)(=O)N(C)C)=CC=C21 JOMFDSUEDLXEFK-UHFFFAOYSA-N 0.000 abstract 1
- SFHGZGMYSAGHBK-UHFFFAOYSA-N 2-bromo-11-oxo-5,6-dihydrodibenzo[3,1-b:3',1'-f][7]annulene-9-sulfonyl fluoride Chemical compound C1CC2=CC=C(Br)C=C2C(=O)C2=CC(S(=O)(=O)F)=CC=C21 SFHGZGMYSAGHBK-UHFFFAOYSA-N 0.000 abstract 1
- HYKKSGGCBKGVQG-UHFFFAOYSA-N 2-bromo-5,6-dihydrodibenzo[3,1-[7]annulen-11-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC(Br)=CC=C21 HYKKSGGCBKGVQG-UHFFFAOYSA-N 0.000 abstract 1
- LJYSMPGOLKZAQW-UHFFFAOYSA-N 2-bromo-n,n-dimethyl-11-oxo-5,6-dihydrodibenzo[3,1-b:3',1'-f][7]annulene-9-sulfonamide Chemical compound C1CC2=CC=C(Br)C=C2C(=O)C2=CC(S(=O)(=O)N(C)C)=CC=C21 LJYSMPGOLKZAQW-UHFFFAOYSA-N 0.000 abstract 1
- RYMQWZPAZBQXMX-UHFFFAOYSA-N 2-bromodibenzo[1,3-e:1',2'-f][7]annulen-11-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=CC(Br)=CC=C21 RYMQWZPAZBQXMX-UHFFFAOYSA-N 0.000 abstract 1
- WPIBDMOGKGFVSK-UHFFFAOYSA-N 2-chloro-N,N-dimethyltricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaene-5-sulfonamide Chemical compound ClC1C2=C(CCC3=C1C=C(C=C3)S(N(C)C)(=O)=O)C=CC=C2 WPIBDMOGKGFVSK-UHFFFAOYSA-N 0.000 abstract 1
- MEMVQJUQGICZAP-UHFFFAOYSA-N 2-methylsulfanyl-11h-dibenzo[1,3-e:1',2'-f][7]annulen-11-ol Chemical compound C1=CC2=CC=CC=C2C(O)C2=CC(SC)=CC=C21 MEMVQJUQGICZAP-UHFFFAOYSA-N 0.000 abstract 1
- LWCXUOXJODMQNH-UHFFFAOYSA-N 2-methylsulfanyldibenzo[1,3-e:1',2'-f][7]annulen-11-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=CC(SC)=CC=C21 LWCXUOXJODMQNH-UHFFFAOYSA-N 0.000 abstract 1
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 239000007900 aqueous suspension Substances 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 abstract 1
- 229940045803 cuprous chloride Drugs 0.000 abstract 1
- 150000008282 halocarbons Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/02—Lithium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises substituted 5H-dibenzo[a,d]cycloheptene and their 10,11-dihydro derivatives which compounds have the general formulae <FORM:1017696/C2/1> wherein Z represents -CH2CH2CH2- or -CCCH2-which may be further substituted by a C1-C4 alkyl radical, each of R and R1 represents a C1-C6 alkyl radical or a cycloalkyl, phenyl or benzyl radical provided that when R and R1 are other than alkyl radicals the total number of carbon atoms in R and R1 does not exceed 9 and provided further that when Z is the radical -CH2CH2CH2-which radical may by further substituted by a C1-C4 alkyl radical and R and R1 are both alkyl radicals they are linked together through a nitrogen atom to form a 1-lower alkyl-4-piperazinyl radical, and when Z is the radical -CCH2-which radical may be further substituted with a C1-C4 alkyl radical, R and R1 may be linked together through a carbon, nitrogen or oxygen atom to form a 1-piperidyl, 4-morpholinyl, 1-pyrrolidyl or 1 - (C1- 4 alkyl) - 4 - piperazinyl ring, and each of X and X1 represents a hydrogen or a halogen atom or a C1- 4 alkoxy, C1- 4 alkylmercapto, C1- 4 alkylsulphonyl or C2- 8 dialkylsulphamoyl group and acid addition salts thereof; and a process for the preparation of compounds of the above general formulae wherein Z represents -CH2CH2CH2- or -CCCH2-which may be further substituted by a C1-C4 alkyl radical, and each of R and R1 is a C1-C6 alkyl radical or a cycloalkyl, phenyl or benzyl radical provided that when R and R1 are other than alkyl radicals the total number of carbon atoms in R and R1 does not exceed 9 and provided further that when R and R1 are both alkyl radicals, they may be linked together through carbon, nitrogen or oxygen atoms to form a 1-piperidyl, 4-morpholinyl, 1-pyrrolidyl or 1-C1- 4 alkyl-4-piperazinyl ring, by reacting the required 5-halo-substituted 5H-dibenzo[a,d]cycloheptene or 10,11-dihydro derivative thereof with the required organo-metal compound of the formula <FORM:1017696/C2/2> wherein Y represents lithium or Hal-Mg. Acid addition salts of the compound defined above are also mentioned. Pharmaceutical compositions useful as anti-depressants contain as the active ingredients the substituted 5H-dibenzo[a,d]cycloheptenes and their 10,11-dihydro derivatives defined above. The compositions may be administered in the form of powders, capsules, tablets, elixirs, solutions or aqueous suspensions. 5 - Chloro - 3 - methylmercapto - 5H - dibenzo[a,d]cycloheptene is prepared by reacting methyl mercaptan and cuprous chloride, reacting the resulting cuprous methyl mercaptide with 3-bromo - 5H - dibenzo[a,d]cyclohepten - 5 - one to form 3 - methylmercapto - 5H - dibenzo[a,d]-cyclohepten-5-one, reducing this compound with potassium borohydride to form 3-methyl-mercapto - 5H - dibenzo[a,d]cyclohepten - 5 - ol, treating this compound with hydrogen chloride to form the desired corresponding 5-chloro compound. 5 - Chloro - 3 - dimethylsulphamoyl - 5H - dibenzo[a,d]cyclohepten is prepared by reacting 3 - bromo - 10,11 - dihydro - 5H - dibenzo[a,d]-cyclohepten-5-one with fluosulphonic acid to form 3 - bromo - 7 - fluorosulphonyl - 10,11 - dihydro - 5H - dibenzo[a,d]cyclohepten - 5 - one, treating this compound with dimethylamine to form 3 - bromo - 7 - dimethylsulphamoyl - 10,11 -dihydro - 5H - dibenzo[a,d]cyclohepten - 5 - one, hydrogenating this compound in the presence of palladium on charcoal to form 3-dimethylsulphamoyl - 10,11 - dihydro - 5H - dibenzo[a,d]-cyclohepten-5-one, treating this compound with N-bromosuccinimide and benzoyl peroxide to form 3 - dimethylsulphamoyl - 5H - dibenzo[a,d]-cyclohepten-3-one, reducing this compound with potassium borohydride to form 3-dimethylsulphamoyl - 5H - dibenzo[a,d]cyclohepten - 5 - ol, and treating this compound with hydrogen chloride to form the desired 5-chloro compound. 5 - Chloro - 3 - dimethylsulphamoyl - 10,11 -dihydro - 5H - dibenzo[a,d]cycloheptene is prepared by reducing 3-dimethylsulphamoyl-10,11-dihydro - 5H - dibenzo[a,d]cyclohepten-5-one with potassium borohydride and treating the resulting 3 - dimethylsulphamoyl - 10,11 - dihydro - 5H - dibenzo[a,d]cyclohepten - 5 - ol with hydrogen chloride. Organo-metal compounds of the general formula <FORM:1017696/C2/3> wherein Y represents lithium or Hal-Mg in which Hal is a halogen, preferably chlorine or bromine, and R, R1 and Z have the significance indicated in the first paragraph above, are prepared by the usual methods from magnesium and the required organo-halides, and from phenyl-lithium and the required substituted hydrocarbon. Reference has been directed by the Comptroller to Specifications 858,188 and 975,465.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14022261A | 1961-09-25 | 1961-09-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1017696A true GB1017696A (en) | 1966-01-19 |
Family
ID=22490268
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3514262A Expired GB1017696A (en) | 1961-09-25 | 1962-09-14 | Substituted 5h-dibenzo[a, d]cycloheptenes and 10,11-dihydro-5h-dibenzo[a, d]cycloheptenes |
Country Status (2)
| Country | Link |
|---|---|
| AT (1) | AT244323B (en) |
| GB (1) | GB1017696A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0056617A2 (en) * | 1981-01-16 | 1982-07-28 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Cycloheptene derivatives, process and intermediates for their preparation, and pharmceuticals containing them |
| EP0056616A2 (en) * | 1981-01-16 | 1982-07-28 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Cycloheptene derivatives, process for their preparation, and pharmaceuticals containing them |
-
1962
- 1962-09-14 GB GB3514262A patent/GB1017696A/en not_active Expired
- 1962-09-18 AT AT742362A patent/AT244323B/en active
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0056617A2 (en) * | 1981-01-16 | 1982-07-28 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Cycloheptene derivatives, process and intermediates for their preparation, and pharmceuticals containing them |
| EP0056616A2 (en) * | 1981-01-16 | 1982-07-28 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Cycloheptene derivatives, process for their preparation, and pharmaceuticals containing them |
| EP0056616A3 (en) * | 1981-01-16 | 1982-10-27 | F. Hoffmann-La Roche & Co. Aktiengesellschaft | Cycloheptene derivatives, process and intermediates for their preparation, and pharmaceuticals containing them |
| EP0056617A3 (en) * | 1981-01-16 | 1982-11-17 | F. Hoffmann-La Roche & Co. Aktiengesellschaft | Cycloheptene derivatives, process and intermediates for their preparation, and pharmceuticals containing them |
| US4513002A (en) * | 1981-01-16 | 1985-04-23 | Hoffmann-La Roche Inc. | Cycloheptene derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| AT244323B (en) | 1965-12-27 |
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