GB1112601A - 9,10-dihydro-4h-benzo[4,5] cyclohepta [1,2-b] thiophene derivatives and their production - Google Patents

9,10-dihydro-4h-benzo[4,5] cyclohepta [1,2-b] thiophene derivatives and their production

Info

Publication number
GB1112601A
GB1112601A GB32955/65A GB3295565A GB1112601A GB 1112601 A GB1112601 A GB 1112601A GB 32955/65 A GB32955/65 A GB 32955/65A GB 3295565 A GB3295565 A GB 3295565A GB 1112601 A GB1112601 A GB 1112601A
Authority
GB
United Kingdom
Prior art keywords
alkyl
compounds
coor5
hydrogen
together form
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
GB32955/65A
Inventor
Ernst Jucker
Anton Ebnother
Jean-Michel Bastian
Erwin Rissi
Andre Stoll
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 CH1046764A external-priority patent/CH444185A/en
Priority claimed from CH1046864A external-priority patent/CH444186A/en
Priority claimed from CH806465A external-priority patent/CH473139A/en
Application filed by Sandoz AG filed Critical Sandoz AG
Publication of GB1112601A publication Critical patent/GB1112601A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/78Heterocyclic 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
    • C07D333/80Seven-membered rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention comprises compounds of the formula <FORM:1112601/C2/1> and acid addition salts thereof, in which (i) R1 is H or CH3, R2 is H, R3 is C1- 4 alkyl and R14 is C1- 4 alkyl; or (ii) R1 is H or CH3, R2 is H and R3 and R14 with the nitrogen atom form a piperidino, pyrrolidino or 4-(C1- 4 alkyl)-piperazino radical; or (iii) R1 with R3 forms a -(CH2)2- or -(CH2)3 - radical, R2 is H and R14 is H or C1- 4 alkyl; or (iv) R1 and R3 together form a -(CH2)3- or -(CH2)4-radical and R14 is H or C1- 4 alkyl; X and Y are hydrogen atoms or together form a second bond and in the case where X and Y are hydrogen R14 may also be a group -COOR5, in which R5 is a C1- 4 alkyl or C7- 10 aralkyl group; and comprises also processes for preparing these compounds by (a) for the preparation of compounds wherein X and Y are hydrogen, heating the corresponding compound wherein X and Y together form a second bond or X represents OH and Y represents H with hydrogen iodide and red phosphorus, or (b) for the preparation of compounds wherein R14 is H or COOR5, reacting a compound wherein R14 is CH3 with a chloroformic ester Cl.COOR5 and if desired, hydrolysing the resulting compound wherein R14 is COOR5. Compounds of the above formula wherein X and Y together form a second bond are made by reacting 9,10-di-hydro - 4H - benzo - [4,5] - cyclohepta - [1,2-b]-thiopen-4-one with a Grignard compound of the formula Hal-Mg-CH2.CHR1.CHR2.NR3R4 to give an intermediate product of the above formula wherein X is OH and Y is H which is then treated to split off water, e.g. with hydrogen chloride and glacial acetic acid. Pharmaceutical preparations having pharmacodynamic properties comprise the above compounds of the invention and a carrier, preferably in a form adapted to the enteral or parenteral administration of 15-300 mg. per day.
GB32955/65A 1964-08-11 1965-08-02 9,10-dihydro-4h-benzo[4,5] cyclohepta [1,2-b] thiophene derivatives and their production Expired GB1112601A (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
CH1046764A CH444185A (en) 1964-08-11 1964-08-11 Process for the preparation of new thiophene derivatives
CH1046864A CH444186A (en) 1964-08-11 1964-08-11 Process for the preparation of new thiophene derivatives
CH806465A CH473139A (en) 1965-06-09 1965-06-09 Process for the preparation of new 9,10-dihydro-4H-benzo (4,5) cyclohepta (1,2-b) thiophene derivatives
CH806265 1965-06-09
CH806365A CH473823A (en) 1964-08-11 1965-06-09 Process for the preparation of new 4H-Benzo (4,5) cyclohepta (1,2-b) thiophene derivatives
CH1519265 1965-11-03

Publications (1)

Publication Number Publication Date
GB1112601A true GB1112601A (en) 1968-05-08

Family

ID=27543810

Family Applications (1)

Application Number Title Priority Date Filing Date
GB32955/65A Expired GB1112601A (en) 1964-08-11 1965-08-02 9,10-dihydro-4h-benzo[4,5] cyclohepta [1,2-b] thiophene derivatives and their production

Country Status (8)

Country Link
BE (1) BE668053A (en)
CH (1) CH473823A (en)
DE (1) DE1250449B (en)
FR (1) FR4866M (en)
GB (1) GB1112601A (en)
NL (1) NL6510328A (en)
NO (3) NO115027B (en)
SE (3) SE326453B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4775691A (en) * 1985-12-09 1988-10-04 Sandoz Ltd. 4H-benzo[4,5]cyclohepta[1,2-b]thiophene derivatives

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4775691A (en) * 1985-12-09 1988-10-04 Sandoz Ltd. 4H-benzo[4,5]cyclohepta[1,2-b]thiophene derivatives

Also Published As

Publication number Publication date
NO115025B (en) 1968-07-08
FR4866M (en) 1967-02-27
DE1250449B (en) 1967-09-21
CH473823A (en) 1969-06-15
NL6510328A (en) 1966-02-14
SE326454B (en) 1970-07-27
NO115027B (en) 1968-07-08
SE326453B (en) 1970-07-27
BE668053A (en) 1966-02-09
SE326197B (en) 1970-07-20
NO115026B (en) 1968-07-08

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