GB1223524A - Improvements in the manufacture of penicillins and salts thereof - Google Patents

Improvements in the manufacture of penicillins and salts thereof

Info

Publication number
GB1223524A
GB1223524A GB2472969A GB2472969A GB1223524A GB 1223524 A GB1223524 A GB 1223524A GB 2472969 A GB2472969 A GB 2472969A GB 2472969 A GB2472969 A GB 2472969A GB 1223524 A GB1223524 A GB 1223524A
Authority
GB
United Kingdom
Prior art keywords
acid
stands
penicillins
formula
reacting
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
GB2472969A
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.)
LAAKETHDAS ORION Oy
Original Assignee
LAAKETHDAS ORION Oy
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 LAAKETHDAS ORION Oy filed Critical LAAKETHDAS ORION Oy
Publication of GB1223524A publication Critical patent/GB1223524A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D211/40—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D211/40—Oxygen atoms
    • C07D211/42—Oxygen atoms attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D309/06—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cephalosporin Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,223,524. Penicillins; xanthogen acids. LAAKETEHDAS ORION OY. 15 May, 1969 [20 May, 1968], No. 24729/69. Headings C2A and C2C. Novel penicillins of the general formula in which R stands for an alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aralkyl, alkoxyalkyl, aryloxyalkyl, alkylthioalkyl, aminoalkyl or a heterocyclic radical, R<SP>1</SP> stands for H or a methyl, phenyl or benzyl group and R<SP>2</SP> stands for H or a methyl group are prepared by reacting 6-APA or a salt thereof with a reactive derivative of an acid of formula and, if desired, converting the product to a salt with an inorganic or organic base. The acid reactants of Formula II are prepared by reacting a suitable potassium xanthogenate with a halogen carboxylic acid. The products may be purified by dissolving in sodium bicarbonate solution, extracting with ether and precipitating with acid.
GB2472969A 1968-05-20 1969-05-15 Improvements in the manufacture of penicillins and salts thereof Expired GB1223524A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FI141368A FI42085B (en) 1968-05-20 1968-05-20

Publications (1)

Publication Number Publication Date
GB1223524A true GB1223524A (en) 1971-02-24

Family

ID=8505597

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2472969A Expired GB1223524A (en) 1968-05-20 1969-05-15 Improvements in the manufacture of penicillins and salts thereof

Country Status (10)

Country Link
AT (1) AT283598B (en)
BE (1) BE733180A (en)
CH (1) CH518308A (en)
DE (1) DE1924760C3 (en)
ES (1) ES367403A1 (en)
FI (1) FI42085B (en)
FR (1) FR2009922A1 (en)
GB (1) GB1223524A (en)
NL (1) NL139749B (en)
SE (1) SE369526B (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004037780A1 (en) * 2002-10-23 2004-05-06 Noveon Ip Holdings Corp. S-(a, a’ -DISUBSTITUTED-a” -ACETIC ACID) SUBSTITUTED DITHIOCARBONATE DERIVATIVES FOR CONTROLLED RADICAL POLYMERIZATIONS, PROCESS AND POLYMERS MADE THEREFROM
US7205368B2 (en) * 2000-02-16 2007-04-17 Noveon, Inc. S-(α, α′-disubstituted-α′ ′-acetic acid) substituted dithiocarbonate derivatives for controlled radical polymerizations, process and polymers made therefrom
US7495050B2 (en) 2000-02-16 2009-02-24 Lubrizol Advanced Materials, Inc. Associative thickeners for aqueous systems
US7557235B2 (en) 2000-02-16 2009-07-07 Lubrizol Advanced Materials, Inc. Hydroxyl-terminated thiocarbonate containing compounds, polymers, and copolymers, and polyurethanes and urethane acrylics made therefrom
US7851582B2 (en) 2000-02-16 2010-12-14 Lubrizol Advanced Materials, Inc. S-(α, α′-disubstituted-α″-acetic acid)—substituted dithiocarbonate derivatives for controlled radical polymerizations, process and polymers made therefrom

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE788812A (en) * 1971-09-14 1973-03-14 Squibb & Sons Inc THIOACETYLATED PENICILLINS AND CEPHALOSPORINS, THEIR PREPARATION AND THERAPEUTIC USES
GB1506233A (en) * 1974-08-30 1978-04-05 Squibb & Sons Inc Cephalosporin derivatives

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB900666A (en) * 1960-05-13 1962-07-11 Beecham Res Lab Antibacterial agents

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7205368B2 (en) * 2000-02-16 2007-04-17 Noveon, Inc. S-(α, α′-disubstituted-α′ ′-acetic acid) substituted dithiocarbonate derivatives for controlled radical polymerizations, process and polymers made therefrom
US7335788B2 (en) 2000-02-16 2008-02-26 Lubrizol Advanced Materials, Inc. S-(α, α′-disubstituted-α″-acetic acid) substituted dithiocarbonate derivatives for controlled radical polymerizations, process and polymers made therefrom
US7495050B2 (en) 2000-02-16 2009-02-24 Lubrizol Advanced Materials, Inc. Associative thickeners for aqueous systems
US7557235B2 (en) 2000-02-16 2009-07-07 Lubrizol Advanced Materials, Inc. Hydroxyl-terminated thiocarbonate containing compounds, polymers, and copolymers, and polyurethanes and urethane acrylics made therefrom
US7851582B2 (en) 2000-02-16 2010-12-14 Lubrizol Advanced Materials, Inc. S-(α, α′-disubstituted-α″-acetic acid)—substituted dithiocarbonate derivatives for controlled radical polymerizations, process and polymers made therefrom
US8492576B2 (en) 2000-02-16 2013-07-23 Lubrizol Advanced Materials, Inc. Hydroxyl-terminated thiocarbonate containing compounds, polymers, and copolymers, and polyurethanes and urethane acrylics made therefrom
WO2004037780A1 (en) * 2002-10-23 2004-05-06 Noveon Ip Holdings Corp. S-(a, a’ -DISUBSTITUTED-a” -ACETIC ACID) SUBSTITUTED DITHIOCARBONATE DERIVATIVES FOR CONTROLLED RADICAL POLYMERIZATIONS, PROCESS AND POLYMERS MADE THEREFROM
JP2006503971A (en) * 2002-10-23 2006-02-02 ノベオン アイピー ホールディングス コーポレイション S-([alpha], [alpha] '-disubstituted- [alpha] "-acetic acid) -substituted dithiocarbonate derivatives for controlled radical polymerization, process and polymers prepared therefrom

Also Published As

Publication number Publication date
FI42085B (en) 1970-02-02
ES367403A1 (en) 1971-04-01
CH518308A (en) 1972-01-31
BE733180A (en) 1969-11-03
AT283598B (en) 1970-08-10
DE1924760A1 (en) 1969-11-27
NL139749B (en) 1973-09-17
DE1924760C3 (en) 1975-04-24
FR2009922A1 (en) 1970-02-13
NL6907604A (en) 1969-11-24
DE1924760B2 (en) 1974-09-12
SE369526B (en) 1974-09-02

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