公开(公告)号：US3749711A

公开(公告)日：1973-07-31

申请号：US3749711D

申请日：1970-09-18

Applicant: HOECHST AG

Inventor： SCHORR M ,  SCHRINNER E ,  SCHUTZE E

IPC: C07D233/22 ,  C07D499/00 ,  C07D499/44 ,  C07D499/48 ,  C07D99/16

CPC classification number: C07D499/00 ,  C07D233/22

Abstract: ANTIBIOTICALLY ACTIVE ACYLAMINOPENICILLANIC ACIDS OF THE GENERAL FORMULA I

6-(R1-N=C(-N(-R2)(-R3))-A-B-CH2-CO-NH-),2-(HOOC-),3,3-

DI(CH3-)PENAM

IN WHICH R1, R2 AND R3 REPRESENT HYDROGEN OR LOWER ALKYL GROUPS, R1 AND R2 MAY FORM TOGETHER AN ALKYLENE GROUP WHICH MAY BE SUBSTITUTED, A REPRESENTS A PHENYLENE OR THIENYLENE GROUP WHICH MAY BE SUBSTITUTED AND B REPRESENTS OXYGEN OR A CHEMICAL BOND, AND THE PHYSIOLOGICALLY TOLERATED SALTS THEREOF, PHARMACEUTICAL PREPARATIONS CONTAINING THESE COMPOUNDS AND PROCESS FOR THE PREPARATION OF SUCH COMPOUNDS AND PREPARATIONS.

公开(公告)号：FR2070094A1

公开(公告)日：1971-09-10

申请号：FR7035001

申请日：1970-09-28

Applicant: HOECHST AG ,  HOECHST AG

Inventor： SCHORR M ,  SCHRINNER E ,  SCHUTZE E

IPC: C07D499/00 ,  C07D499/44 ,  C07D499/48 ,  C07D233/22 ,  A61K21/00 ,  C07D99/00

公开(公告)号：SE375097B

公开(公告)日：1975-04-07

申请号：SE1307070

申请日：1970-09-25

Applicant: HOECHST AG

Inventor： SCHORR M ,  SCHRINNER E ,  SCHUTZE E

IPC: C07D233/22 ,  C07D499/00 ,  C07D499/44 ,  C07D499/48 ,  C07D99/16

Abstract: 1285790 Acylaminopenicillins FARBWERKE HOECHST AG 28 Sept 1970 [27 Sept 1969 (2)] 46107/70 Headings C2A andC2C Novel acylaminopenicillanic acids of Formula I wherein R 1 and R 2 are the same or different and are hydrogen or C 1 to C 5 alkyl or together form an optionally substituted alkylene group linking the nitrogen atoms, R 3 is hydrogen or C 1 to C 5 alkyl, A is an optionally substituted phenylene or thienylene group and B is oxygen or a chemical bond, and salts thereof, are prepared by reacting 6-aminopenicillanic acid or a salt thereof with a carboxylic acid of Formula II wherein R 1 , R 2 , R 3 , A and B are as defined above or an N-acylating derivative or salt thereof. The groups R1, R 2 and R 3 preferably contain a total of not more than 6 carbon atoms. When R 1 and R 2 form an alkylene group, this may be substituted, e.g. by C 1 to C 5 alkyl groups which may be closed into a ring and this ring may include a hetero atom. A is preferably 1,4-phenylene or 2,5-thienylene and may be substituted, e.g. by alkyl, alkoxy and/or halogen. The reaction may be carried out in water, preferably together with a water-miscible solvent, at pH 6-9 and at ambient temperature or below; an acid-acceptor, e.g. NaHC0 3 or triethylamine, is preferably present in the medium. The product may be isolated by simply lyophilizing the reaction mixture to give the penicillin in the form of a crude mixture with salts (e.g. NaCl) formed as by-products, which may be used therapeutically without purification providing the salts are non-toxic. It is purified by re-crystallization from concentrated aqueous solution. The acid chlorides of 4-amidinophenylacetic acid, 4-amidmophenoxyacetic acid and 4-(2- imidazolinyl)-phenoxyacetic acid as their hydrochloride salts are prepared by reacting the acid with thionyl chloride. Pharmaceutical compositions having antibacterial activity against gram-positive and gramnegative bacteria comprise an acylaminopenicillanic acid of Formula I as defined above or a physiologically tolerable salt thereof together with a pharmaceutical carrier.

公开(公告)号：BR6915194D0

公开(公告)日：1973-02-13

申请号：BR21519469

申请日：1969-12-16

Applicant: HOECHST AG

Inventor： SCHOR M ,  SCHRINNER E ,  SCHUTZE E

IPC: C07D499/00 ,  C07D499/60 ,  C07D99/16

公开(公告)号：CH566310A5

公开(公告)日：1975-09-15

申请号：CH1422270

申请日：1970-09-25

Applicant: HOECHST AG

Inventor： SCHORR M ,  SCHRINNER E ,  SCHUTZE E

IPC: C07D233/22 ,  C07D499/00 ,  C07D499/44 ,  C07D499/48

Abstract: 1285790 Acylaminopenicillins FARBWERKE HOECHST AG 28 Sept 1970 [27 Sept 1969 (2)] 46107/70 Headings C2A andC2C Novel acylaminopenicillanic acids of Formula I wherein R 1 and R 2 are the same or different and are hydrogen or C 1 to C 5 alkyl or together form an optionally substituted alkylene group linking the nitrogen atoms, R 3 is hydrogen or C 1 to C 5 alkyl, A is an optionally substituted phenylene or thienylene group and B is oxygen or a chemical bond, and salts thereof, are prepared by reacting 6-aminopenicillanic acid or a salt thereof with a carboxylic acid of Formula II wherein R 1 , R 2 , R 3 , A and B are as defined above or an N-acylating derivative or salt thereof. The groups R1, R 2 and R 3 preferably contain a total of not more than 6 carbon atoms. When R 1 and R 2 form an alkylene group, this may be substituted, e.g. by C 1 to C 5 alkyl groups which may be closed into a ring and this ring may include a hetero atom. A is preferably 1,4-phenylene or 2,5-thienylene and may be substituted, e.g. by alkyl, alkoxy and/or halogen. The reaction may be carried out in water, preferably together with a water-miscible solvent, at pH 6-9 and at ambient temperature or below; an acid-acceptor, e.g. NaHC0 3 or triethylamine, is preferably present in the medium. The product may be isolated by simply lyophilizing the reaction mixture to give the penicillin in the form of a crude mixture with salts (e.g. NaCl) formed as by-products, which may be used therapeutically without purification providing the salts are non-toxic. It is purified by re-crystallization from concentrated aqueous solution. The acid chlorides of 4-amidinophenylacetic acid, 4-amidmophenoxyacetic acid and 4-(2- imidazolinyl)-phenoxyacetic acid as their hydrochloride salts are prepared by reacting the acid with thionyl chloride. Pharmaceutical compositions having antibacterial activity against gram-positive and gramnegative bacteria comprise an acylaminopenicillanic acid of Formula I as defined above or a physiologically tolerable salt thereof together with a pharmaceutical carrier.

公开(公告)号：FR2070094B1

公开(公告)日：1974-04-12

申请号：FR7035001

申请日：1970-09-28

Applicant: HOECHST AG

Inventor： SCHORR M ,  SCHRINNER E ,  SCHUTZE E

IPC: C07D233/22 ,  C07D499/00 ,  C07D499/44 ,  C07D499/48 ,  A61K21/00 ,  C07D99/00

Abstract: 1285790 Acylaminopenicillins FARBWERKE HOECHST AG 28 Sept 1970 [27 Sept 1969 (2)] 46107/70 Headings C2A andC2C Novel acylaminopenicillanic acids of Formula I wherein R 1 and R 2 are the same or different and are hydrogen or C 1 to C 5 alkyl or together form an optionally substituted alkylene group linking the nitrogen atoms, R 3 is hydrogen or C 1 to C 5 alkyl, A is an optionally substituted phenylene or thienylene group and B is oxygen or a chemical bond, and salts thereof, are prepared by reacting 6-aminopenicillanic acid or a salt thereof with a carboxylic acid of Formula II wherein R 1 , R 2 , R 3 , A and B are as defined above or an N-acylating derivative or salt thereof. The groups R1, R 2 and R 3 preferably contain a total of not more than 6 carbon atoms. When R 1 and R 2 form an alkylene group, this may be substituted, e.g. by C 1 to C 5 alkyl groups which may be closed into a ring and this ring may include a hetero atom. A is preferably 1,4-phenylene or 2,5-thienylene and may be substituted, e.g. by alkyl, alkoxy and/or halogen. The reaction may be carried out in water, preferably together with a water-miscible solvent, at pH 6-9 and at ambient temperature or below; an acid-acceptor, e.g. NaHC0 3 or triethylamine, is preferably present in the medium. The product may be isolated by simply lyophilizing the reaction mixture to give the penicillin in the form of a crude mixture with salts (e.g. NaCl) formed as by-products, which may be used therapeutically without purification providing the salts are non-toxic. It is purified by re-crystallization from concentrated aqueous solution. The acid chlorides of 4-amidinophenylacetic acid, 4-amidmophenoxyacetic acid and 4-(2- imidazolinyl)-phenoxyacetic acid as their hydrochloride salts are prepared by reacting the acid with thionyl chloride. Pharmaceutical compositions having antibacterial activity against gram-positive and gramnegative bacteria comprise an acylaminopenicillanic acid of Formula I as defined above or a physiologically tolerable salt thereof together with a pharmaceutical carrier.

公开(公告)号：BR6915127D0

公开(公告)日：1973-03-08

申请号：BR21512769

申请日：1969-12-15

Applicant: HOECHST AG

Inventor： SCHORR M ,  SCHRINNER E ,  SCHUTZE E

IPC: C07D499/00 ,  C07D499/46 ,  C07D99/16

公开(公告)号：GB1285790A

公开(公告)日：1972-08-16

申请号：GB4610770

申请日：1970-09-28

Applicant: HOECHST AG

Inventor： SCHORR M ,  SCHRINNER E ,  SCHUTZE E

IPC: C07D233/22 ,  C07D499/00 ,  C07D499/44 ,  C07D499/48

Abstract: 1285790 Acylaminopenicillins FARBWERKE HOECHST AG 28 Sept 1970 [27 Sept 1969 (2)] 46107/70 Headings C2A andC2C Novel acylaminopenicillanic acids of Formula I wherein R 1 and R 2 are the same or different and are hydrogen or C 1 to C 5 alkyl or together form an optionally substituted alkylene group linking the nitrogen atoms, R 3 is hydrogen or C 1 to C 5 alkyl, A is an optionally substituted phenylene or thienylene group and B is oxygen or a chemical bond, and salts thereof, are prepared by reacting 6-aminopenicillanic acid or a salt thereof with a carboxylic acid of Formula II wherein R 1 , R 2 , R 3 , A and B are as defined above or an N-acylating derivative or salt thereof. The groups R1, R 2 and R 3 preferably contain a total of not more than 6 carbon atoms. When R 1 and R 2 form an alkylene group, this may be substituted, e.g. by C 1 to C 5 alkyl groups which may be closed into a ring and this ring may include a hetero atom. A is preferably 1,4-phenylene or 2,5-thienylene and may be substituted, e.g. by alkyl, alkoxy and/or halogen. The reaction may be carried out in water, preferably together with a water-miscible solvent, at pH 6-9 and at ambient temperature or below; an acid-acceptor, e.g. NaHC0 3 or triethylamine, is preferably present in the medium. The product may be isolated by simply lyophilizing the reaction mixture to give the penicillin in the form of a crude mixture with salts (e.g. NaCl) formed as by-products, which may be used therapeutically without purification providing the salts are non-toxic. It is purified by re-crystallization from concentrated aqueous solution. The acid chlorides of 4-amidinophenylacetic acid, 4-amidmophenoxyacetic acid and 4-(2- imidazolinyl)-phenoxyacetic acid as their hydrochloride salts are prepared by reacting the acid with thionyl chloride. Pharmaceutical compositions having antibacterial activity against gram-positive and gramnegative bacteria comprise an acylaminopenicillanic acid of Formula I as defined above or a physiologically tolerable salt thereof together with a pharmaceutical carrier.

公开(公告)号：IE34536B1

公开(公告)日：1975-06-11

申请号：IE121270

申请日：1970-09-18

Applicant: HOECHST AG

Inventor： SCHORR M ,  SCHRINNER E ,  SCHUTZE E

IPC: C07D233/22 ,  C07D499/00 ,  C07D499/44 ,  C07D499/48 ,  C07D99/14 ,  C07D99/22 ,  A61K21/00

Abstract: 1285790 Acylaminopenicillins FARBWERKE HOECHST AG 28 Sept 1970 [27 Sept 1969 (2)] 46107/70 Headings C2A andC2C Novel acylaminopenicillanic acids of Formula I wherein R 1 and R 2 are the same or different and are hydrogen or C 1 to C 5 alkyl or together form an optionally substituted alkylene group linking the nitrogen atoms, R 3 is hydrogen or C 1 to C 5 alkyl, A is an optionally substituted phenylene or thienylene group and B is oxygen or a chemical bond, and salts thereof, are prepared by reacting 6-aminopenicillanic acid or a salt thereof with a carboxylic acid of Formula II wherein R 1 , R 2 , R 3 , A and B are as defined above or an N-acylating derivative or salt thereof. The groups R1, R 2 and R 3 preferably contain a total of not more than 6 carbon atoms. When R 1 and R 2 form an alkylene group, this may be substituted, e.g. by C 1 to C 5 alkyl groups which may be closed into a ring and this ring may include a hetero atom. A is preferably 1,4-phenylene or 2,5-thienylene and may be substituted, e.g. by alkyl, alkoxy and/or halogen. The reaction may be carried out in water, preferably together with a water-miscible solvent, at pH 6-9 and at ambient temperature or below; an acid-acceptor, e.g. NaHC0 3 or triethylamine, is preferably present in the medium. The product may be isolated by simply lyophilizing the reaction mixture to give the penicillin in the form of a crude mixture with salts (e.g. NaCl) formed as by-products, which may be used therapeutically without purification providing the salts are non-toxic. It is purified by re-crystallization from concentrated aqueous solution. The acid chlorides of 4-amidinophenylacetic acid, 4-amidmophenoxyacetic acid and 4-(2- imidazolinyl)-phenoxyacetic acid as their hydrochloride salts are prepared by reacting the acid with thionyl chloride. Pharmaceutical compositions having antibacterial activity against gram-positive and gramnegative bacteria comprise an acylaminopenicillanic acid of Formula I as defined above or a physiologically tolerable salt thereof together with a pharmaceutical carrier.

公开(公告)号：NL7013978A

公开(公告)日：1971-03-30

申请号：NL7013978

申请日：1970-09-22

Applicant: HOECHST AG

Inventor： SCHORR M ,  SCHRINNER E ,  SCHUTZE E

IPC: C07D233/22 ,  C07D499/00 ,  C07D499/44 ,  C07D499/48 ,  C07D99/16 ,  A61K27/00

Abstract: 1285790 Acylaminopenicillins FARBWERKE HOECHST AG 28 Sept 1970 [27 Sept 1969 (2)] 46107/70 Headings C2A andC2C Novel acylaminopenicillanic acids of Formula I wherein R 1 and R 2 are the same or different and are hydrogen or C 1 to C 5 alkyl or together form an optionally substituted alkylene group linking the nitrogen atoms, R 3 is hydrogen or C 1 to C 5 alkyl, A is an optionally substituted phenylene or thienylene group and B is oxygen or a chemical bond, and salts thereof, are prepared by reacting 6-aminopenicillanic acid or a salt thereof with a carboxylic acid of Formula II wherein R 1 , R 2 , R 3 , A and B are as defined above or an N-acylating derivative or salt thereof. The groups R1, R 2 and R 3 preferably contain a total of not more than 6 carbon atoms. When R 1 and R 2 form an alkylene group, this may be substituted, e.g. by C 1 to C 5 alkyl groups which may be closed into a ring and this ring may include a hetero atom. A is preferably 1,4-phenylene or 2,5-thienylene and may be substituted, e.g. by alkyl, alkoxy and/or halogen. The reaction may be carried out in water, preferably together with a water-miscible solvent, at pH 6-9 and at ambient temperature or below; an acid-acceptor, e.g. NaHC0 3 or triethylamine, is preferably present in the medium. The product may be isolated by simply lyophilizing the reaction mixture to give the penicillin in the form of a crude mixture with salts (e.g. NaCl) formed as by-products, which may be used therapeutically without purification providing the salts are non-toxic. It is purified by re-crystallization from concentrated aqueous solution. The acid chlorides of 4-amidinophenylacetic acid, 4-amidmophenoxyacetic acid and 4-(2- imidazolinyl)-phenoxyacetic acid as their hydrochloride salts are prepared by reacting the acid with thionyl chloride. Pharmaceutical compositions having antibacterial activity against gram-positive and gramnegative bacteria comprise an acylaminopenicillanic acid of Formula I as defined above or a physiologically tolerable salt thereof together with a pharmaceutical carrier.