GB1153186A - Penicillanic Acid Derivatives - Google Patents

Penicillanic Acid Derivatives

Info

Publication number
GB1153186A
GB1153186A GB2800266A GB2800266A GB1153186A GB 1153186 A GB1153186 A GB 1153186A GB 2800266 A GB2800266 A GB 2800266A GB 2800266 A GB2800266 A GB 2800266A GB 1153186 A GB1153186 A GB 1153186A
Authority
GB
United Kingdom
Prior art keywords
alkyl
formula
compound
penicillanate
carboxamido
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
GB2800266A
Inventor
Takayuki Naito
Susumu Nakagawa
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.)
Bristol Banyu Research Institute Ltd
Original Assignee
Bristol Banyu Research Institute 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
Application filed by Bristol Banyu Research Institute Ltd filed Critical Bristol Banyu Research Institute Ltd
Publication of GB1153186A publication Critical patent/GB1153186A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
    • C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
    • C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
    • 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
    • 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/194—Radicals derived from thio- or thiono carboxylic acids
    • 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

Abstract

1,153,186. Penicillanic acid derivatives; 5 - alkyl - 3 - arylisothiazole - 4 - carboxylic acids. BRISTOL-BANYU RESEARCH INSTITUTE Ltd. 22 June, 1966 [23 June, 1965], No. 28002/66. Headings C2A and C2C. Antibacterially active penicillanic acid derivatives have the Formula I wherein R<SP>1</SP> represents H, Cl, CF 3 ; R<SP>2</SP> is H, Cl, CF 3 , F, methylsulphonyl, NO 2 , C 1 to C 10 alkyl or C 1 to C 10 alkoxy; and R<SP>3</SP> is C 1 to C 10 alkyl. Pharmaceutically acceptable salts thereof include the alkali and alkaline earth metal, ammonium and amine salts e.g. N-ethylpiperidine salt. The penicillins are prepared by reacting 6-aminopenicillanic acid or a salt thereof with an acid chloride, or functional equivalent thereof, having the Formula II wherein R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> have the above meanings. Typical compounds are sodium 6-[5-methyl-3- (2<SP>1</SP>,6<SP>1</SP> - dichlorophenyl) isothiazole - 4 - carboxamido] penicillanate, sodium 6 - [5- methyl - 3 - (2<SP>1</SP> - chlorophenyl) - isothiazole - 4- carboxamido] penicillanate and sodium [5- methyl - 3 - (2<SP>1</SP>,6<SP>1</SP> - di - trifluoromethyl - phenyl)- 4-carboxamido] penicillanate. 5 - Alkyl - 3 - arylisothiazole - 4 - carboxylic acids corresponding to the acid chlorides of Formula II above, are prepared by the following reaction schemes: (A) Alternatively, the compound III of scheme (A) may be converted to compound IV by the following steps Compound I of scheme (A) is treated with BuLi and RI to form which is treated with CuCn to form compound II of scheme A; wherein AR represents: and R<SP>1</SP> and R<SP>2</SP> have the above meanings. 2,-6 Dichlorobenzonitrile is prepared by Pharmaceutical compositions comprise a penicillin of Formula I above and a carrier. They may be used for the treatment of mastitis in cattle or as a nutritional supplement e.g. when mixed with an animal feed. Reference has been directed by the Comptroller to Specification 1,059,303.
GB2800266A 1965-06-23 1966-06-22 Penicillanic Acid Derivatives Expired GB1153186A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US46641465A 1965-06-23 1965-06-23

Publications (1)

Publication Number Publication Date
GB1153186A true GB1153186A (en) 1969-05-29

Family

ID=23851659

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2800266A Expired GB1153186A (en) 1965-06-23 1966-06-22 Penicillanic Acid Derivatives

Country Status (14)

Country Link
AT (1) AT267059B (en)
BE (1) BE681505A (en)
BR (1) BR6680644D0 (en)
CH (1) CH468408A (en)
CS (1) CS155141B2 (en)
DK (1) DK135426B (en)
ES (1) ES327383A1 (en)
FI (1) FI48597C (en)
FR (1) FR5871M (en)
GB (1) GB1153186A (en)
IL (1) IL25756A (en)
NL (2) NL6608094A (en)
NO (1) NO135827C (en)
SE (1) SE356055B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4544752A (en) * 1980-09-22 1985-10-01 Eli Lilly And Company 3-Aryl-5-isothiazolecarboxylic acids and related compounds used to lower uric acid levels

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4544752A (en) * 1980-09-22 1985-10-01 Eli Lilly And Company 3-Aryl-5-isothiazolecarboxylic acids and related compounds used to lower uric acid levels

Also Published As

Publication number Publication date
NL6608094A (en) 1966-12-27
DE1670091A1 (en) 1970-07-16
AT267059B (en) 1968-12-10
BR6680644D0 (en) 1973-11-29
BE681505A (en) 1966-11-24
FR5871M (en) 1968-03-11
NO135827C (en) 1977-06-08
FI48597C (en) 1974-11-11
FI48597B (en) 1974-07-31
CH468408A (en) 1969-02-15
DK135426B (en) 1977-04-25
NL131487C (en)
ES327383A1 (en) 1967-07-16
NO135827B (en) 1977-02-28
IL25756A (en) 1970-06-17
DE1670091B2 (en) 1975-06-26
CS155141B2 (en) 1974-05-30
DK135426C (en) 1977-10-10
SE356055B (en) 1973-05-14

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees