IE38261L - Benzocycloheptathiophene derivatives. - Google Patents
Benzocycloheptathiophene derivatives.Info
- Publication number
- IE38261L IE38261L IE731667A IE166773A IE38261L IE 38261 L IE38261 L IE 38261L IE 731667 A IE731667 A IE 731667A IE 166773 A IE166773 A IE 166773A IE 38261 L IE38261 L IE 38261L
- Authority
- IE
- Ireland
- Prior art keywords
- general formula
- hydrogen atom
- alkyl group
- benzocycloheptathiophen
- resulting
- Prior art date
Links
- 150000008617 benzocycloheptathiophenes Chemical class 0.000 title abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 4
- KOMODKOORXGLLK-UHFFFAOYSA-N 2H-cyclohepta[e][1]benzothiol-4-ol Chemical compound C=1CSC=2C1C1=CC=CC=CC1=CC2O KOMODKOORXGLLK-UHFFFAOYSA-N 0.000 abstract 3
- 230000003301 hydrolyzing effect Effects 0.000 abstract 3
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 3
- 239000000047 product Substances 0.000 abstract 3
- JWHDENUPJBYDPO-UHFFFAOYSA-N 2h-cyclohepta[e][1]benzothiole Chemical compound C1=CC=CC=C2C3=CCSC3=CC=C21 JWHDENUPJBYDPO-UHFFFAOYSA-N 0.000 abstract 2
- 239000007818 Grignard reagent Substances 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- GJYHOYAPCGHYBS-UHFFFAOYSA-N cyclohepta[e][1]benzothiol-4-one Chemical compound C1=CSC2=C1C1=CC=CC=CC1=CC2=O GJYHOYAPCGHYBS-UHFFFAOYSA-N 0.000 abstract 2
- 150000004795 grignard reagents Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000001078 anti-cholinergic effect Effects 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
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000008024 pharmaceutical diluent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
- C07D333/80—Seven-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
1445127 Benzocycloheptathiophenes SANDOZ Ltd 17 Sept 1973 [20 Sept 1972 (2) 27 Sept 1972] 43515/73 Heading C2C Novel benzocycloheptathiophenes of the general formula wherein R 1 is a hydrogen or chlorine atom in the 6- or 7-position, R 2 is a C 1-4 alkyl group, R 3 is a hydrogen atom or C 1-4 alkyl group, R 4 is a hydrogen atom or hydroxyl group and R 5 is a hydrogen atom or, when R 4 is a hydroxyl group, a C 1-4 alkyl group, or R 4 and R 5 together form an oxygen atom, and A is an ethylene or vinylene group, and acid addition salts thereof are prepared (a) when R 4 and R 5 together form an oxygen atom, by acylating a benzocycloheptathiophene of the general formula (b) when R 4 is a hydroxyl group and R 5 is a hydrogen atom, by reducing the product of (a); (c) when R 4 is a hydroxyl group and each of R 3 and R 5 is a C 1-4 alkyl group, by reacting the corresponding compound in which R 4 and R 5 together form an oxygen atom with a compound of the general formula wherein RI 5 is a C 1-4 alkyl group and Z is Li or -MgX (X is Cl, Br or I) and hydrolysing the reaction product; (d) when each of R 4 and R 5 is a hydrogen atom, by reducing the product of (a); and (e) when each of R 4 and R 5 is a hydrogen atom, by dehydrating a 4-hydroxybenzocycloheptathiophene of the general formula followed optionally by salification of the product. 4 - Hydroxybenzocycloheptathiophenes of the fourth general formula above are prepared by chloroalkylating a benzocycloheptathiophen-4- one of the general formula reducing the resulting 2-chloroalkyl-benzocycloheptathiophen-4-one of the general formula reacting the resulting 2-alkyl-benzocycloheptathiophen-4-one of the general formula with a Grignard reagent of the general formula and hydrolysing the resulting complex. Benzocycloheptathiophenes of the second general formula above are prepared by reacting a benzocycloheptathiophen-4-one and a Grignard reagent of the fifth and eighth general formula above, hydrolysing the resulting complex and dehydrating the resulting 4- hydroxybenzocycloheptathiophene. Pharmaceutical compositions having antidepressant, analgesic and anti-cholinergic activity comprise as active ingredient, a benzocycloheptathiophene of the first general formula above or a pharmaceutically acceptable acid addition salt thereof, in association with a pharmaceutical carrier or diluent.
[GB1445127A]
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1373872A CH571516A5 (en) | 1972-09-20 | 1972-09-20 | Benzo(4,5) cyclohepta(1,2-b)thiphophenes - neuroleptics, CNS sedatives, analgesics and anticholinergics |
| CH1373972 | 1972-09-20 | ||
| CH1409572 | 1972-09-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE38261L true IE38261L (en) | 1974-03-20 |
| IE38261B1 IE38261B1 (en) | 1978-02-01 |
Family
ID=27177046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1667/73A IE38261B1 (en) | 1972-09-20 | 1973-09-18 | Benzocycloheptathiophene derivatives |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS4969677A (en) |
| CA (1) | CA1011739A (en) |
| DD (1) | DD107468A5 (en) |
| DE (1) | DE2346747A1 (en) |
| DK (1) | DK133677B (en) |
| ES (1) | ES418859A1 (en) |
| FR (1) | FR2199994B1 (en) |
| GB (1) | GB1445127A (en) |
| HU (1) | HU166629B (en) |
| IE (1) | IE38261B1 (en) |
| IL (1) | IL43249A (en) |
| NL (1) | NL7312684A (en) |
| PH (1) | PH9639A (en) |
| SE (1) | SE388858B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5096500B2 (en) * | 2008-01-30 | 2012-12-12 | 日本臓器製薬株式会社 | Piperidine derivatives |
| KR101375680B1 (en) | 2008-08-01 | 2014-03-19 | 니폰 조키 세야쿠 가부시키가이샤 | Aminopropylidene derivative |
| JP5083989B2 (en) * | 2008-11-20 | 2012-11-28 | 日本臓器製薬株式会社 | Medicaments containing piperidine derivatives |
| WO2011013632A1 (en) * | 2009-07-28 | 2011-02-03 | 日本臓器製薬株式会社 | Method for producing thiabenzoazulene propionic acid derivative |
-
1973
- 1973-09-11 SE SE7312362A patent/SE388858B/en unknown
- 1973-09-12 DK DK501473AA patent/DK133677B/en unknown
- 1973-09-14 NL NL7312684A patent/NL7312684A/xx not_active Application Discontinuation
- 1973-09-17 CA CA181,183A patent/CA1011739A/en not_active Expired
- 1973-09-17 JP JP48103965A patent/JPS4969677A/ja active Pending
- 1973-09-17 GB GB4351573A patent/GB1445127A/en not_active Expired
- 1973-09-17 DE DE19732346747 patent/DE2346747A1/en active Pending
- 1973-09-18 IE IE1667/73A patent/IE38261B1/en unknown
- 1973-09-18 HU HUSA2532A patent/HU166629B/hu unknown
- 1973-09-18 DD DD173667A patent/DD107468A5/xx unknown
- 1973-09-18 IL IL43249A patent/IL43249A/en unknown
- 1973-09-18 ES ES418859A patent/ES418859A1/en not_active Expired
- 1973-09-19 PH PH15037*UA patent/PH9639A/en unknown
- 1973-09-20 FR FR7333761A patent/FR2199994B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2346747A1 (en) | 1974-04-04 |
| GB1445127A (en) | 1976-08-04 |
| FR2199994B1 (en) | 1977-09-09 |
| IE38261B1 (en) | 1978-02-01 |
| JPS4969677A (en) | 1974-07-05 |
| CA1011739A (en) | 1977-06-07 |
| PH9639A (en) | 1976-01-26 |
| IL43249A (en) | 1978-06-15 |
| ES418859A1 (en) | 1976-06-01 |
| DK133677C (en) | 1976-11-15 |
| AU6047473A (en) | 1975-03-20 |
| DD107468A5 (en) | 1974-08-05 |
| HU166629B (en) | 1975-04-28 |
| SE388858B (en) | 1976-10-18 |
| IL43249A0 (en) | 1973-11-28 |
| FR2199994A1 (en) | 1974-04-19 |
| NL7312684A (en) | 1974-03-22 |
| DK133677B (en) | 1976-06-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1511463A (en) | 1-acylamino methyl-1,2,3,4-tetrahydroisoquinolines | |
| IE33862B1 (en) | Thiepin and oxepin derivatives,processes for their production and medicaments containing same | |
| IE38261B1 (en) | Benzocycloheptathiophene derivatives | |
| GB1456627A (en) | Pyridobenzodiazepinones | |
| IE34314L (en) | Dibenzodioxocine derivatives | |
| GB1394504A (en) | 1,2-bis-4-phenyl-1-piperazinyl-ethane derivatives | |
| GB1252329A (en) | ||
| IE32223B1 (en) | Novel carboxylic acids,processes for their production and compositions containing the same | |
| IE41562L (en) | Indolinone and fluorenone derivatives | |
| GB1181469A (en) | Novel Benzothiopyrano Indazole Compounds and Means of Producing the Same | |
| GB1473971A (en) | 3-hydroxy-5,6-benzomorphinan derivatives | |
| GB1503447A (en) | Dl-and 8r-9-fluoro-prostadienoic acid derivatives and process | |
| IE33870B1 (en) | Benzobenzofuranooxepine compounds and process for preparing the same | |
| IE35223L (en) | Bis-basic ethers of 2, 6- and 2, 7-dihydroxy-anthraquinones | |
| IE35137B1 (en) | New n-methyl-imidazole derivatives processes for their manufacture and their use as medicines | |
| GB1252487A (en) | ||
| GB1489784A (en) | Pharmaceutically active substituted keto-acid derivatives | |
| GB1440670A (en) | Lactam derivatives | |
| GB1397697A (en) | Phenoxyalicyclic carboxylic acid derivatives methods of making them and compositions containing them | |
| GB1496710A (en) | Furotriazines | |
| GB1389540A (en) | Derivatives of alpha-aminocephalosporins | |
| GB1412168A (en) | Penicillins and production thereof | |
| GB1425911A (en) | Phenylacetic acid derivatives, process for their preparation and therapeutic composition containing same | |
| GB1478400A (en) | Derivatives of dinitro-2,2,bithiophene and application thereof | |
| IE38218B1 (en) | Substituted formylazapentadienenitriles and a method for producing them |