GB1392542A - Diazepine derivatives - Google Patents

Diazepine derivatives

Info

Publication number
GB1392542A
GB1392542A GB2236972A GB2236972A GB1392542A GB 1392542 A GB1392542 A GB 1392542A GB 2236972 A GB2236972 A GB 2236972A GB 2236972 A GB2236972 A GB 2236972A GB 1392542 A GB1392542 A GB 1392542A
Authority
GB
United Kingdom
Prior art keywords
general formula
group
hydrogen atom
benzoyl
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
GB2236972A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche 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
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB1392542A publication Critical patent/GB1392542A/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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen 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
    • C07D333/02—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

Landscapes

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

Abstract

1392542 1,3 - Dihydro - 5 - phenyl - 2H- thieno[2,3-e][1,4]diazepin- 2 - ones F HOFFMANN-LA ROCHE & CO AG 12 May 1972 [14 May 1971] 22369/72 Heading C2C Novel 1,3 - dihydro - 5 - phenyl - 2H - thieno- [2,3-e][1,4]diazepin- 2 - ones of the general formula wherein R 1 is a halogen atom or nitro group, R 2 is a hydrogen atom or -CH 2 X group, in which X is a hydrogen atom or an alkyl, alkenyl or cycloalkyl group containing at most 4 carbon atoms, a hydroxymethyl or methoxy group or a dialkylaminomethyl group of at most 5 carbon atoms, and R 3 is an o-halo-, o-trifluoromethyl- or o,o<SP>1</SP> - dihalo - phenyl group or, when R 1 is a halogen atom, an onitrophenyl group, and their salts are prepared (a) by halogenating or nitrating a 1,3 - dihydro - 5 - phenyl - 2H- thieno- [2,3-e][1,4]diazepin- 2 - one of the general formula above wherein R 1 is a hydrogen atom and R 3 may be an o-nitrophenyl group in the case of halogenation, at the 7-position; (b) by cyclizing a 2-aminoacetylamino-3-benzoylthiophene of the general formula and (c) when R 2 is a -CH 2 X group, by substituting the corresponding compound in which R 2 is a hydrogen atom with the desired group at the 1-position; followed optionally by salification of the product. 1,3 - Dihydro - 5 - phenyl - 2H - thieno[2,3-e]- [1,4]diazepin - 2 - ones of the first general formula above wherein R 1 is a hydrogen atom, and R 3 is an o-halophenyl, o-trifluoromethylphenyl, o,o<SP>1</SP>-dihalophenyl or onitrophenyl group, which are novel provided that whenR 2 is a hydrogen atom or -CH 2 X, in which X is a hydrogen atom or a C 1-3 alkyl group, R 3 is not an o-halophenyl or o-trifluoromethylphenyl group, are prepared (d) when R<SP>2</SP> is a -CH 2 X group, by a process analogous to (c) above; and (e) by a process analogous to (b) above. 2 - Aminoacetylamino - 3 - benzoyl - thiophenes of the second general formula above wherein R 1 is a hydrogen or halogen atom or a nitro group are prepared (f) when R 2 is a hydrogen atom, by reacting a 2-chloroacetylamino-3-benzoyl-thiophene of the general formula with sodium iodide and reacting the resulting 2- iodo - acetylamino - 3 - benzoyl - thiophene of the general formula with ammonia; and (g) when R 1 is a hydrogen atom and R 2 is a -CH 2 X group, by reacting a phenacyl cyanide of the general formula R 3 COCH 2 CN with 2,5-dihydroxy- 1 ,4-dithiane, acetylating the resulting 2-amino-3-benzoylthiophene of the general formula substituting the resulting 2-acetylamino-3-benzoyl - thiophene of the general formula at the nitrogen atom with a-CH 2 X group, acid hydrolysing the resulting 2-acetyl-amino-3-benzoyl-thiophene of the general formula and reacting the resulting 2-amino-3-benzoylthiophene with carbobenzoxyglycyl chloride in the presence of a base, followed by treatment with HBr in glacial acetic acid. 2 - Chloroacetylamino - 3 - benzoyl - thiophenes of the third general formula above are prepared (h) when R 1 is a halogen atom or nitro group, by halogenating or nitrating the corresponding compound in which R 1 is a hydrogen atom; and (i) when R 1 is a hydrogen atom, by chloroacetylating a 2-amino-3-benzoyl-thiophene of the sixth general formula above. Phenacyl cyanides of the fifth general formula above are prepared (j) by treating a benzonitrile of the general formula R 3 -CN with acetonitrile and sodium and hydrolysing the resulting imine of the general formula or (k) by brominating an acetophenone of the general formula R 3 COCH 3 and treating the resulting phenacyl bromide with aqueous-alcoholic potassium cyanide. Pharmaceutical compositions having musclerelaxant and sedative activity comprise, as active ingredient, a 1,3-dihydro-5-phenyl-2H- thieno[2,3-e][1,4]diazepin-2-one of the first general formula above wherein R 1 is a halogen atom or nitro group of a pharmaceutically utilizable acid addition salt thereof, in association with a compatible pharmaceutical carrier. Reference has been directed by the Comptroller to Specification 1,291,684.
GB2236972A 1971-05-14 1972-05-12 Diazepine derivatives Expired GB1392542A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH720371 1971-05-14

Publications (1)

Publication Number Publication Date
GB1392542A true GB1392542A (en) 1975-04-30

Family

ID=4321476

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2236972A Expired GB1392542A (en) 1971-05-14 1972-05-12 Diazepine derivatives

Country Status (12)

Country Link
AT (1) AT318621B (en)
AU (1) AU4179572A (en)
BE (1) BE783236A (en)
BG (1) BG20372A3 (en)
BR (1) BR7203013D0 (en)
DE (1) DE2221623A1 (en)
FR (1) FR2137838B1 (en)
GB (1) GB1392542A (en)
IL (1) IL39322A0 (en)
LU (1) LU65349A1 (en)
NL (1) NL7205730A (en)
ZA (1) ZA722874B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10116378C2 (en) * 2001-04-04 2003-05-28 Boehringer Ingelheim Pharma Process for the preparation of 6-aryl-4H-s-triazolo [3,4-c] thieno [2,3-e] -1,4-diazepines

Also Published As

Publication number Publication date
FR2137838B1 (en) 1975-06-20
BE783236A (en) 1972-11-10
DE2221623A1 (en) 1972-11-30
AU4179572A (en) 1973-11-08
IL39322A0 (en) 1972-06-28
ZA722874B (en) 1973-02-28
BR7203013D0 (en) 1973-07-17
BG20372A3 (en) 1975-11-05
NL7205730A (en) 1972-11-16
AT318621B (en) 1974-11-11
LU65349A1 (en) 1973-11-23
FR2137838A1 (en) 1972-12-29

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees