GB1445127A - Benzocycloheptathiophene derivatives - Google Patents

Benzocycloheptathiophene derivatives

Info

Publication number
GB1445127A
GB1445127A GB4351573A GB4351573A GB1445127A GB 1445127 A GB1445127 A GB 1445127A GB 4351573 A GB4351573 A GB 4351573A GB 4351573 A GB4351573 A GB 4351573A GB 1445127 A GB1445127 A GB 1445127A
Authority
GB
United Kingdom
Prior art keywords
general formula
hydrogen atom
alkyl group
benzocycloheptathiophen
resulting
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
Application number
GB4351573A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sandoz AG
Original Assignee
Sandoz AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from CH1373872A external-priority patent/CH571516A5/en
Application filed by Sandoz AG filed Critical Sandoz AG
Publication of GB1445127A publication Critical patent/GB1445127A/en
Expired legal-status Critical Current

Links

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.
GB4351573A 1972-09-20 1973-09-17 Benzocycloheptathiophene derivatives Expired GB1445127A (en)

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 (1)

Publication Number Publication Date
GB1445127A true GB1445127A (en) 1976-08-04

Family

ID=27177046

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4351573A Expired GB1445127A (en) 1972-09-20 1973-09-17 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)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100331365A1 (en) * 2008-01-30 2010-12-30 Nippon Zoki Pharmaceutical Co., Ltd. Piperidine derivative
US8653285B2 (en) 2008-08-01 2014-02-18 Nippon Zoki Pharmaceutical Co., Ltd. Aminopropylidene derivative
TWI454470B (en) * 2009-07-28 2014-10-01 Nippon Zoki Pharmaceutical Co Method for producing thiabenzoazulene propionic acid derivatives

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5083989B2 (en) * 2008-11-20 2012-11-28 日本臓器製薬株式会社 Medicaments containing piperidine derivatives

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100331365A1 (en) * 2008-01-30 2010-12-30 Nippon Zoki Pharmaceutical Co., Ltd. Piperidine derivative
US8377967B2 (en) * 2008-01-30 2013-02-19 Nippon Zoki Pharmaceutical Co., Ltd. Piperidine derivative
US8653285B2 (en) 2008-08-01 2014-02-18 Nippon Zoki Pharmaceutical Co., Ltd. Aminopropylidene derivative
TWI454470B (en) * 2009-07-28 2014-10-01 Nippon Zoki Pharmaceutical Co Method for producing thiabenzoazulene propionic acid derivatives

Also Published As

Publication number Publication date
DK133677C (en) 1976-11-15
CA1011739A (en) 1977-06-07
HU166629B (en) 1975-04-28
DE2346747A1 (en) 1974-04-04
FR2199994A1 (en) 1974-04-19
IL43249A (en) 1978-06-15
NL7312684A (en) 1974-03-22
SE388858B (en) 1976-10-18
AU6047473A (en) 1975-03-20
IE38261B1 (en) 1978-02-01
IE38261L (en) 1974-03-20
ES418859A1 (en) 1976-06-01
IL43249A0 (en) 1973-11-28
DD107468A5 (en) 1974-08-05
PH9639A (en) 1976-01-26
JPS4969677A (en) 1974-07-05
DK133677B (en) 1976-06-28
FR2199994B1 (en) 1977-09-09

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee