GB1271018A - Novel derivatives of thiazine carboxylic acid and processes for their preparation - Google Patents

Novel derivatives of thiazine carboxylic acid and processes for their preparation

Info

Publication number
GB1271018A
GB1271018A GB47790/71A GB4779071A GB1271018A GB 1271018 A GB1271018 A GB 1271018A GB 47790/71 A GB47790/71 A GB 47790/71A GB 4779071 A GB4779071 A GB 4779071A GB 1271018 A GB1271018 A GB 1271018A
Authority
GB
United Kingdom
Prior art keywords
thiazine
aminomethyl
lactams
dihydro
carboxylic acids
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
GB47790/71A
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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 Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB1271018A publication Critical patent/GB1271018A/en
Expired legal-status Critical Current

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Classifications

    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01H—ELECTRIC SWITCHES; RELAYS; SELECTORS; EMERGENCY PROTECTIVE DEVICES
    • H01H9/00—Details of switching devices, not covered by groups H01H1/00 - H01H7/00
    • H01H9/18—Distinguishing marks on switches, e.g. for indicating switch location in the dark; Adaptation of switches to receive distinguishing marks
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
    • C07D207/36—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/38—2-Pyrrolones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/02—Preparation
    • C07D501/08—Preparation by forming the ring or condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
    • C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
    • C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
    • C07D501/42—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by an araliphatic carboxylic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F21—LIGHTING
    • F21V—FUNCTIONAL FEATURES OR DETAILS OF LIGHTING DEVICES OR SYSTEMS THEREOF; STRUCTURAL COMBINATIONS OF LIGHTING DEVICES WITH OTHER ARTICLES, NOT OTHERWISE PROVIDED FOR
    • F21V17/00—Fastening of component parts of lighting devices, e.g. shades, globes, refractors, reflectors, filters, screens, grids or protective cages
    • F21V17/10—Fastening of component parts of lighting devices, e.g. shades, globes, refractors, reflectors, filters, screens, grids or protective cages characterised by specific fastening means or way of fastening
    • F21V17/16—Fastening of component parts of lighting devices, e.g. shades, globes, refractors, reflectors, filters, screens, grids or protective cages characterised by specific fastening means or way of fastening by deformation of parts; Snap action mounting
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01H—ELECTRIC SWITCHES; RELAYS; SELECTORS; EMERGENCY PROTECTIVE DEVICES
    • H01H13/00—Switches having rectilinearly-movable operating part or parts adapted for pushing or pulling in one direction only, e.g. push-button switch
    • H01H13/50—Switches having rectilinearly-movable operating part or parts adapted for pushing or pulling in one direction only, e.g. push-button switch having a single operating member
    • H01H13/52—Switches having rectilinearly-movable operating part or parts adapted for pushing or pulling in one direction only, e.g. push-button switch having a single operating member the contact returning to its original state immediately upon removal of operating force, e.g. bell-push switch

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Theoretical Computer Science (AREA)
  • Biotechnology (AREA)
  • Molecular Biology (AREA)
  • General Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Cephalosporin Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,271,018. Pyrrolo - thiazine derivatives. ROUSSEL-UCLAF. 27 June, 1969 [27 June, 1968], No. 47790/71. Divided out of 1,271,013. Heading C2C. The invention comprises novel threo or erythro (or mixtures thereof) pyrrolo-thiazine derivatives of the formulµ in which R<SP>1</SP> is H or unsubstituted or substituted aryl, R is alkyl or aralkyl and Y is imido or acylamino, and the preparation thereof. The γ- lactams of 2-(α-R-oxycarbonyl-α-γ-methyl)-5- aminomethyl - 2,3 - dihydro - 1,3 - thiazine - 4- carboxylic acids (VIII) are obtained by reacting the corresponding 1-R<SP>1</SP>-2,3-dioxo-4-mercaptomethylpyrrolidines with enamines of the formula The γ-lactams of 2-(α-R-oxycarbonyl-α-aminomethyl) - 5 - aminomethyl - 2,3 - dihydro - 1,3- thiazine-4-carboxylic acids (VIIIa) are prepared by reacting compounds of Formula VIII above with hydrazine or subjecting said compounds to acid hydrolysis or hydrogenolysis. Hydrolysis of the resulting compounds gives the γ- lactams of 2 - (α - carboxy - α - aminomethyl)- 5 - aminomethyl - 2,3 - dihydro - 1,3 - thiazine- 4-carboxylic acids (IX) which on reaction with a tritylation agent give the γ-lactams of 2-(α- carboxy - α - tritylaminomethyl) - 5 - aminomethyl - 2,3 - dihydro - 1,3 - thiazine - 4 - carboxylic acids (IXa). The three isomers of the latter compound may be obtained by isomerization of the erythro isomers by treatment with alkaline reagents.
GB47790/71A 1968-06-27 1969-06-27 Novel derivatives of thiazine carboxylic acid and processes for their preparation Expired GB1271018A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR156898 1968-06-27

Publications (1)

Publication Number Publication Date
GB1271018A true GB1271018A (en) 1972-04-19

Family

ID=8651750

Family Applications (5)

Application Number Title Priority Date Filing Date
GB47787/71A Expired GB1271015A (en) 1968-06-27 1969-06-27 Novel pyrrolidine carboxylic acids, esters thereof and processes for their preparation
GB47789/71A Expired GB1271017A (en) 1968-06-27 1969-06-27 Novel pyrrolidine derivatives, and processes for their preparation
GB32567/69A Expired GB1271013A (en) 1968-06-27 1969-06-27 Novel cephalosporin derivatives, and processes for their preparation
GB47788/71A Expired GB1271016A (en) 1968-06-27 1969-06-27 Novel pyrrolidine derivatives, and processes for their preparation
GB47790/71A Expired GB1271018A (en) 1968-06-27 1969-06-27 Novel derivatives of thiazine carboxylic acid and processes for their preparation

Family Applications Before (4)

Application Number Title Priority Date Filing Date
GB47787/71A Expired GB1271015A (en) 1968-06-27 1969-06-27 Novel pyrrolidine carboxylic acids, esters thereof and processes for their preparation
GB47789/71A Expired GB1271017A (en) 1968-06-27 1969-06-27 Novel pyrrolidine derivatives, and processes for their preparation
GB32567/69A Expired GB1271013A (en) 1968-06-27 1969-06-27 Novel cephalosporin derivatives, and processes for their preparation
GB47788/71A Expired GB1271016A (en) 1968-06-27 1969-06-27 Novel pyrrolidine derivatives, and processes for their preparation

Country Status (14)

Country Link
JP (2) JPS4934999B1 (en)
AT (2) AT293614B (en)
BE (1) BE735127A (en)
BR (3) BR6910252D0 (en)
CH (3) CH515276A (en)
DE (4) DE1932498A1 (en)
ES (2) ES368820A1 (en)
FR (1) FR1584569A (en)
GB (5) GB1271015A (en)
HU (1) HU162644B (en)
IL (1) IL32379A (en)
NL (2) NL142691B (en)
PL (1) PL79142B1 (en)
SU (2) SU495841A3 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0277215A1 (en) * 1986-08-19 1988-08-10 Horst Forschner Do-it-yourself garments and set of components of do-it-yourself garments
EA013864B1 (en) * 2008-08-29 2010-08-30 Лимонова, Анастасия Викторовна Method of enhancement antimicrobal activity of cephalosporin antibiotics

Also Published As

Publication number Publication date
CH522635A (en) 1972-05-15
SU495841A3 (en) 1975-12-15
FR1584569A (en) 1969-12-26
BR6910252D0 (en) 1973-02-08
IL32379A (en) 1973-10-25
DE1966203B2 (en) 1980-02-07
IL32379A0 (en) 1969-08-27
DE1966204A1 (en) 1971-10-21
JPS5028440B1 (en) 1975-09-16
GB1271013A (en) 1972-04-19
GB1271015A (en) 1972-04-19
DE1967030A1 (en) 1976-07-29
DE1967030C3 (en) 1978-08-03
DE1932504A1 (en) 1970-01-15
BR6910250D0 (en) 1973-02-08
PL79142B1 (en) 1975-06-30
SU384232A3 (en) 1973-05-23
DE1966203A1 (en) 1972-01-27
NL6909850A (en) 1969-12-30
CH515276A (en) 1971-11-15
GB1271017A (en) 1972-04-19
BR6910251D0 (en) 1973-02-08
DE1932498A1 (en) 1970-02-26
CH513206A (en) 1971-09-30
DE1932504B2 (en) 1977-03-17
JPS4934999B1 (en) 1974-09-19
NL142691B (en) 1974-07-15
AT293615B (en) 1971-10-25
ES368820A1 (en) 1971-05-16
NL142415B (en) 1974-06-17
ES395175A2 (en) 1974-01-16
AT293614B (en) 1971-10-25
DE1967030B2 (en) 1977-11-24
DE1966203C3 (en) 1980-10-09
NL6909849A (en) 1969-12-30
HU162644B (en) 1973-03-28
GB1271016A (en) 1972-04-19
BE735127A (en) 1969-12-29

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