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GB1291684A - THIENO[2,3-e][1,4]DIAZEPIN-2-ONES AND PHARMACEUTICAL PREPARATIONS THEREOF - Google Patents

THIENO[2,3-e][1,4]DIAZEPIN-2-ONES AND PHARMACEUTICAL PREPARATIONS THEREOF

Info

Publication number
GB1291684A
GB1291684A GB21598/71A GB2159871A GB1291684A GB 1291684 A GB1291684 A GB 1291684A GB 21598/71 A GB21598/71 A GB 21598/71A GB 2159871 A GB2159871 A GB 2159871A GB 1291684 A GB1291684 A GB 1291684A
Authority
GB
United Kingdom
Prior art keywords
general formula
benzoylthiophene
reaction
diazepin
thieno
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
GB21598/71A
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.)
Mitsubishi Tanabe Pharma Corp
Original Assignee
Yoshitomi Pharmaceutical Industries Ltd
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 JP45015819A external-priority patent/JPS4910955B1/ja
Priority claimed from JP45019403A external-priority patent/JPS4940000B1/ja
Priority claimed from JP45056154A external-priority patent/JPS4932549B1/ja
Priority claimed from JP45067442A external-priority patent/JPS4940238B1/ja
Application filed by Yoshitomi Pharmaceutical Industries Ltd filed Critical Yoshitomi Pharmaceutical Industries Ltd
Publication of GB1291684A publication Critical patent/GB1291684A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • 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
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/36—Nitrogen atoms
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

1291684 5 - Phenyl -1,2 - dihydro - 3H-thieno- [2,3 - e][1,4] diazepin - 2 - ones YOSHITOMI PHARMACEUTICAL INDUSTRIES Ltd 19 April 1971 [17 Feb 1970 23 Feb 1970 7 March 1970 25 June 1970 31 July 1970] 21598/71 Heading C2C Novel 5 - phenyl - 1,2 - dihydro - 3H-thieno- [2,3 - e][1,4] - diazepin - 2 - ones of the general formula wherein each of R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> is a hydrogen atom or C 1-4 alkyl group, or R<SP>1</SP> and R<SP>2</SP> together form a tri- or penta-methylene group, and R is a hydrogen or halogen atom or a trifluoromethyl or C 1-4 alkoxy group, but R is not a hydrogen atom when each of R<SP>1</SP> and R<SP>2</SP> is a hydrogen atom or C 1-4 alkyl group; and pharmaceutically acceptable acid addition salts thereof are prepared (a) by intramolecular condensation of a 2 - aminoacetamido - 3 - benzoylthiophene of the general formula or an acid addition salt thereof; (b) by reaction of a 2-azidoacetamido-3-benzoylthiophene of the general formula with hydrazine; (c) by reaction of a 2-amino-3- benzoylthiophene of the general formula with an alkyl glycinate of the general formula H 2 NCH 2 COOR<SP>4</SP>, wherein R<SP>4</SP> is a C 1-4 alkyl group, or an acid addition salt thereof; and (d) when R<SP>3</SP> is a C 1-4 alkyl group, by reaction of the corresponding compound in which R<SP>3</SP> is a hydrogen atom with a compound of the general formula R<SP>3</SP>X, wherein X is a reactive atom or group; followed optionally by salification of the product. 2 - Aminoacetamido - 3 - benzoylthiophenes of the second general formula above are prepared (i) by reaction of a 2-amino-3-benzoylthiophene of the fourth general formula above with N- benzyloxycarbonylglycyl chloride and reaction of the resulting 2-benzyloxycarbonylaminoacetamido-3-benzoylthiophene of the general formula with hydrogen bromide in acetic acid; (ii) by reaction of a 2-iodoacetamido-3-benzoylthiophene of the general formula with ammonia; and (iii) by reaction of a 2-azidoacetamido-3-benzoylthiophene of the third general formula above with hydrogen bromide in acetic acid. 2 - Azidoacetamido - 3 - benzoylthiophenes of the third general formula above are prepared by reaction of a 2-iodoacetamido-3-benzoylthiophene of the eighth general formula above with sodium azide. Pharmaceutical compositions having activities in narcosis-potentiation, suppression of fighting behaviour and anticonvulsant effect comprise, as active ingredient, a 5-phenyl-1,2-dihydro- 3H - thieno[2,3-e][1,4]diazepin- 2 - one of the first general formula above or a pharmaceutically acceptable acid addition salt thereof, together with a carrier.
GB21598/71A 1970-02-17 1971-04-19 THIENO[2,3-e][1,4]DIAZEPIN-2-ONES AND PHARMACEUTICAL PREPARATIONS THEREOF Expired GB1291684A (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
JP1407070 1970-02-17
JP45015819A JPS4910955B1 (en) 1970-02-23 1970-02-23
JP45019403A JPS4940000B1 (en) 1970-03-07 1970-03-07
JP45056154A JPS4932549B1 (en) 1970-06-25 1970-06-25
JP45067442A JPS4940238B1 (en) 1970-07-31 1970-07-31

Publications (1)

Publication Number Publication Date
GB1291684A true GB1291684A (en) 1972-10-04

Family

ID=27519583

Family Applications (1)

Application Number Title Priority Date Filing Date
GB21598/71A Expired GB1291684A (en) 1970-02-17 1971-04-19 THIENO[2,3-e][1,4]DIAZEPIN-2-ONES AND PHARMACEUTICAL PREPARATIONS THEREOF

Country Status (9)

Country Link
US (1) US3849405A (en)
BE (1) BE763014A (en)
CA (1) CA927388A (en)
CH (1) CH568322A5 (en)
DE (1) DE2107356C3 (en)
FR (1) FR2081520B1 (en)
GB (1) GB1291684A (en)
NL (1) NL175723C (en)
SE (1) SE367415B (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1340227A (en) * 1970-09-03 1973-12-12 Yoshitomi Pharmaceutical 5-pyridyl-thieno-2,3-e 1,4-diazepin 2-one derivatives their production and pharmaceutical compositions containing them
JPS5418280B2 (en) * 1971-10-30 1979-07-06
GB1387783A (en) * 1972-08-08 1975-03-19 Yoshitomi Pharmaceutical Thiophene derivatives, method for their preparation and pharmaceutical composition thereof
ES412186A1 (en) * 1973-02-28 1976-01-01 Made Labor Sa Process for preparing derivatives of thienodiazepinone
FR2385721A1 (en) * 1977-03-31 1978-10-27 Hexachimie CYCLOPROPYL-6 DIHYDRO-1,3 METHYL-1 PHENYL-5 OXO-2 2 H-THIENO (2,3-E) DIAZEPINE, ITS PREPARATION PROCESS AND ITS THERAPEUTIC APPLICATION
EP0348523A4 (en) * 1987-12-22 1991-10-09 Yoshitomi Pharmaceutical Industries, Ltd. Thienodiazepine compounds and their medicinal use
EP2935284A4 (en) * 2012-12-21 2016-04-27 Abbvie Inc Heterocyclic nuclear hormone receptor modulators

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH540247A (en) * 1967-04-21 1973-09-28 Ciba Geigy Ag Process for the preparation of heterocyclic compounds containing asthylene double bonds
GB1256548A (en) * 1968-12-10 1971-12-08

Also Published As

Publication number Publication date
CA927388A (en) 1973-05-29
CH568322A5 (en) 1975-10-31
US3849405A (en) 1974-11-19
DE2107356A1 (en) 1971-08-26
DE2107356C3 (en) 1978-05-03
FR2081520B1 (en) 1974-08-30
FR2081520A1 (en) 1971-12-03
BE763014A (en) 1971-07-16
DE2107356B2 (en) 1977-09-22
NL7102066A (en) 1971-08-19
SE367415B (en) 1974-05-27
NL175723B (en) 1984-07-16
NL175723C (en) 1984-12-17

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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