GB1434871A - 10-piperazinyl-dibenzo-b,f-thiepin derivatives methods for their preparation and compositions containing them - Google Patents
10-piperazinyl-dibenzo-b,f-thiepin derivatives methods for their preparation and compositions containing themInfo
- Publication number
- GB1434871A GB1434871A GB1401774A GB1401774A GB1434871A GB 1434871 A GB1434871 A GB 1434871A GB 1401774 A GB1401774 A GB 1401774A GB 1401774 A GB1401774 A GB 1401774A GB 1434871 A GB1434871 A GB 1434871A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- compound
- reacting
- piperazinyl
- substituted
- 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
- 238000000034 method Methods 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 11
- 150000004885 piperazines Chemical class 0.000 abstract 5
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 abstract 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 abstract 3
- 125000004423 acyloxy group Chemical group 0.000 abstract 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 abstract 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 abstract 2
- CJNZAXGUTKBIHP-UHFFFAOYSA-N 2-iodobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1I CJNZAXGUTKBIHP-UHFFFAOYSA-N 0.000 abstract 1
- 101000653791 Bos taurus Protein S100-A12 Proteins 0.000 abstract 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- -1 carboxyl methyl group Chemical group 0.000 abstract 1
- 239000003874 central nervous system depressant Substances 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 239000012954 diazonium Substances 0.000 abstract 1
- 150000001989 diazonium salts Chemical class 0.000 abstract 1
- 238000011905 homologation Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 230000000701 neuroleptic effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D337/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D337/14—[b,f]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Abstract
1434871 Piperazinyl-dibenz[b,1]thiepin derivatives F HOFFMANN-LA ROCHE & CO AG 29 March 1974 [30 March 1973 16 Jan 1974] 14017/74 Heading C2C Novel compounds I and salts thereof in which n is 1 to 3, R is H or when n is 2 or 3, R is also OH or C 1-18 alkanoyloxy, one of R 1 and R 2 is H and the other is Cl, Me, MeO, MeS, Me 2 NSO 2 or CF 3 and one of R 3 and R 4 is H and the other is Me, MeO, MeS, Me 2 NSO 2 or CF 3 and the dotted line represents an optional bond are prepared by (1) reacting a compound II where Y is a leaving atom or group (preferably Cl) with an R-(CH 2 ) n -substituted piperazine to form a 10,11-dihydro derivative (2) reacting a compound IX with an R-(CH 2 ) n -substituted piperazine (3) reacting a compound V with ethylene oxide propylene oxide or a compound Y-(CH 2 ) n -R to form a 10,11-dihydro derivative (4) for compounds I in which R is C 1-18 alkanoyloxy, acylating the corresponding compound in which R is hydroxy or (5) for 10,11- dihydro derivatives hydrogenating the corresponding compound I containing the 10,11 double bond. Compounds IX (R 3 or R 4 =Mi or SMe) are prepared by diazotizing on R 1 or R 2 substituted anthranilic acid and reacting the diazonium salt with potassium iodide to form the corresponding 2-iodo-benzoic acid which is reacted in the presence of copper with an appropriately substituted thiophenol, converting the carboxyl group of the diphenyl ether to carboxyl methyl group by the Standard homologation procedure and cyclizing the acid under acidic conditions. Compounds IX are reduced to the alcohol which is chlorinated to form compounds V (Y = Cl). Compounds I are CNS depressants and have neuroleptic properties and form with a carrier a pharmaceutical composition which may be administered orally or parenterally. Reference has been directed by the Comptroller to Specification 1,369,525.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH460473A CH576469A5 (en) | 1973-03-30 | 1973-03-30 | Central-inhibitory and neuroleptic tricyclic cpds. - prepd. by reacting a 10-halo substd. dibenzothiepin with a substd. piperazine |
| CH56774 | 1974-01-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1434871A true GB1434871A (en) | 1976-05-05 |
Family
ID=25684979
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1401774A Expired GB1434871A (en) | 1973-03-30 | 1974-03-29 | 10-piperazinyl-dibenzo-b,f-thiepin derivatives methods for their preparation and compositions containing them |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS49135984A (en) |
| DE (1) | DE2412521A1 (en) |
| FR (1) | FR2223040B1 (en) |
| GB (1) | GB1434871A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS196893B1 (en) * | 1977-12-22 | 1980-04-30 | Miroslav Protiva | 3-fluor-10-piperazino-8-substituted 10,11-dihydro-dibenzothiepines |
-
1974
- 1974-03-15 DE DE19742412521 patent/DE2412521A1/en not_active Withdrawn
- 1974-03-29 JP JP3481274A patent/JPS49135984A/ja active Pending
- 1974-03-29 FR FR7411136A patent/FR2223040B1/fr not_active Expired
- 1974-03-29 GB GB1401774A patent/GB1434871A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS49135984A (en) | 1974-12-27 |
| FR2223040A1 (en) | 1974-10-25 |
| FR2223040B1 (en) | 1977-08-19 |
| DE2412521A1 (en) | 1974-10-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |