公开(公告)号：US4438101A

公开(公告)日：1984-03-20

申请号：US944808

申请日：1978-09-22

Applicant: Roger J. Ponsford ,  Thomas T. Howarth

Inventor： Roger J. Ponsford ,  Thomas T. Howarth

IPC: C07D503/06 ,  A61K31/42 ,  A61K31/424 ,  A61K31/43 ,  A61K31/545 ,  A61P31/04 ,  C07D503/00 ,  C07D503/22 ,  A61K35/00

CPC classification number: A61K31/545 ,  A61K31/43 ,  C07D503/00

Abstract: The compounds of the formula (II): ##STR1## and salts and esters thereof wherein R.sub.1 is an inert organic group of up to 14 carbon atoms and R.sub.2 is an inert organic group of up to 16 carbon atoms, the group NR.sub.1 R.sub.2 containing up to 22 carbon atoms, are antibacterial agents able to enhance the effectiveness of penicillins and cephalosporins against certain .beta.-lactamase producing bacteria.

Abstract translation: 式（II）化合物：其中R 1为至多14个碳原子的惰性有机基团，R 2为至多16个碳原子的惰性有机基团，NR1R2基团 含有多达22个碳原子的抗菌剂是能够增强青霉素和头孢菌素对某些β-内酰胺酶生产菌的有效性的抗菌剂。

公开(公告)号：US4609495A

公开(公告)日：1986-09-02

申请号：US278564

申请日：1981-06-29

Applicant: Roger J. Ponsford ,  Thomas T. Howarth

Inventor： Roger J. Ponsford ,  Thomas T. Howarth

IPC: A61K31/42 ,  A61K31/43 ,  A61K31/545 ,  C07D503/00 ,  C07D498/04

CPC classification number: A61K31/42 ,  A61K31/43 ,  A61K31/545 ,  C07D503/00

Abstract: The compounds of the formula (II): ##STR1## and salts and esters thereof wherein R is an inert organic group of up to 18 carbon atoms and are able to inhibit the action of various bacterial .beta.-lactamases. Thus when a compound of the formula (II) or its salt or ester is used together with a penicillin or cephalosporin, the effectiveness of that penicillin or cephalosporin can be considerably enhanced. These novel synergysts can be prepared by etherification of an ester of clavulanic acid followed if desired by deesterification. The novel synergysts also possess antibacterial activity.

Abstract translation: 式（II）的化合物：其中R是具有至多18个碳原子的惰性有机基团并能够抑制各种细菌β-内酰胺酶的作用的盐和酯。 因此，当将式（II）化合物或其盐或酯与青霉素或头孢菌素一起使用时，可以显着提高该青霉素或头孢菌素的有效性。 这些新型协同增效剂可以通过使用克拉维酸的酯化来制备，如果需要，通过酯化作用。 新型增效剂也具有抗菌活性。

公开(公告)号：US4548815A

公开(公告)日：1985-10-22

申请号：US538767

申请日：1983-10-03

Applicant: Roger J. Ponsford ,  Thomas T. Howarth

Inventor： Roger J. Ponsford ,  Thomas T. Howarth

IPC: A61K31/42 ,  A61K31/43 ,  A61K31/545 ,  C07D503/00 ,  A61K35/00

CPC classification number: A61K31/42 ,  A61K31/43 ,  A61K31/545 ,  C07D503/00

Abstract: The compounds of the formula (II): ##STR1## and salts and esters thereof wherein R is an inert ogranic group of up to 18 carbon atoms and are able to inhibit the action of various bacterial .beta.-lactamases. Thus when a compound of the formula (II) or its salt or ester is used together with a penicillin or cephalosporin, the effectiveness of that penicillin or cephalosporin can be considerably enhanced. These novel synergysts can be prepared by etherification of an ester of clavulanic acid followed if desired by deesterification. The novel synergysts also possess antibacterial activity.

Abstract translation: 式（II）的化合物：其中R是具有至多18个碳原子的惰性极性基团并且能够抑制各种细菌β-内酰胺酶的作用的盐和酯。 因此，当将式（II）化合物或其盐或酯与青霉素或头孢菌素一起使用时，可以显着提高该青霉素或头孢菌素的有效性。 这些新型协同增效剂可以通过使用克拉维酸的酯化来制备，如果需要，通过酯化作用。 新型增效剂也具有抗菌活性。

公开(公告)号：US4228174A

公开(公告)日：1980-10-14

申请号：US8421

申请日：1979-02-01

Applicant: Roger J. Ponsford ,  Thomas T. Howarth

Inventor： Roger J. Ponsford ,  Thomas T. Howarth

IPC: A61K31/42 ,  A61P31/04 ,  C07D503/00 ,  C07D498/04

CPC classification number: C07D503/00

Abstract: The compounds of the formula (II): ##STR1## and salts and esters thereof wherein R is an inert organic group of up to 18 carbon atoms and are able to inhibit the action of various bacterial .beta.-lactamases. Thus when a compound of the formula (II) or its salt or ester is used together with a penicillin or cephalosporin, the effectiveness of that penicillin or cephalosporin can be considerably enhanced. These novel synergysts can be prepared by etherification of an ester of clavulanic acid followed if desired by de-esterification. The novel synergysts also possess antibacterial activity.

Abstract translation: 式（II）的化合物：其中R是具有至多18个碳原子的惰性有机基团并能够抑制各种细菌β-内酰胺酶的作用的盐和酯。 因此，当将式（II）化合物或其盐或酯与青霉素或头孢菌素一起使用时，可以显着提高该青霉素或头孢菌素的有效性。 如果需要，通过脱酯化可以通过使克拉维酸的酯化来制备这些新颖的增效剂。 新型增效剂也具有抗菌活性。

公开(公告)号：US4382084A

公开(公告)日：1983-05-03

申请号：US129188

申请日：1980-03-10

Applicant: Roger J. Ponsford ,  Thomas T. Howarth

Inventor： Roger J. Ponsford ,  Thomas T. Howarth

IPC: C07D503/06 ,  A61K31/42 ,  A61K31/424 ,  A61K31/43 ,  A61K31/545 ,  A61P31/04 ,  C07D503/00 ,  C07D503/22 ,  A61K35/00

CPC classification number: A61K31/545 ,  A61K31/43 ,  C07D503/00

Abstract: The compounds of the formula (II): ##STR1## and salts and esters theereof wherein R.sub.1 is an inert organic group of up to 14 carbon atoms and R.sub.2 is an inert organic group of up to 16 carbon atoms, the group NR.sub.1 R.sub.2 containing up to 22 carbon atoms, are antibacterial agents able to enhance the effectiveness of penicillins and cephalosporins against certain .beta.-lactamase producing bacteria.

Abstract translation: 式（II）的化合物：其中R 1为至多14个碳原子的惰性有机基团，R 2为至多16个碳原子的惰性有机基团，其中R 1为NR 1 R 2 含有多达22个碳原子的抗菌剂是能够增强青霉素和头孢菌素对某些β-内酰胺酶生产菌的有效性的抗菌剂。

公开(公告)号：US4256638A

公开(公告)日：1981-03-17

申请号：US942156

申请日：1978-09-14

Applicant: Roger J. Ponsford ,  Thomas T. Howarth

Inventor： Roger J. Ponsford ,  Thomas T. Howarth

IPC: C07D503/06 ,  A61K31/42 ,  A61K31/424 ,  A61K31/43 ,  A61K31/545 ,  A61P31/04 ,  C07D503/00 ,  C07D503/22 ,  C07D498/04 ,  C07B29/00

CPC classification number: A61K31/545 ,  A61K31/43 ,  C07D503/00

Abstract: The compounds of the formula (II): ##STR1## and salts and esters thereof wherein R.sub.1 is an inert organic group of up to 14 carbon atoms and R.sub.2 is an inert organic group of up to 16 carbon atoms, the group NR.sub.1 R.sub.2 containing up to 22 carbon atoms, are antibacterial agents able to enhance the effectiveness of penicillins and cephalosporins against certain .beta.-lactamase producing bacteria.

Abstract translation: 式（II）化合物：其中R 1为至多14个碳原子的惰性有机基团，R 2为至多16个碳原子的惰性有机基团，NR1R2基团 含有多达22个碳原子的抗菌剂是能够增强青霉素和头孢菌素对某些β-内酰胺酶生产菌的有效性的抗菌剂。

公开(公告)号：US4138403A

公开(公告)日：1979-02-06

申请号：US708343

申请日：1976-07-26

Applicant: Thomas T. Howarth ,  Allan G. Brown ,  David F. Corbett ,  Roger J. Ponsford

Inventor： Thomas T. Howarth ,  Allan G. Brown ,  David F. Corbett ,  Roger J. Ponsford

IPC: A61K31/42 ,  A61P31/04 ,  C07D205/08 ,  C07D205/09 ,  C07D263/16 ,  C07D503/00 ,  C07F7/18 ,  C07D498/04

CPC classification number: C07D263/16 ,  C07D205/08 ,  C07D205/09 ,  C07D503/00 ,  C07F7/1852

Abstract: Compounds of the formula ##STR1## and salts and esters thereof wherein R.sub.1 is hydrogen, alkyl of 1 to 4 carbon atoms, phenyl, alkenyl of 2 to 4 carbon atoms, alkynyl of 2 to 4 carbon atoms, acyl of 1 to 4 carbon atoms, a carboxylic acid group or ester thereof of 1 to 7 carbon atoms, or alkyl of 1 to 4 carbon atoms substituted by 1 or 2 halogen atoms, hydroxyl, substituted hydroxyl, amino, protected amino, substituted thio of 1 to 7 carbon atoms, substituted sulphinyl of 1 to 7 carbon atoms, substituted sulphonyl of 1 to 7 carbon atoms, or by a carboxylic acid group or ester thereof of 1 to 7 carbon atoms;R.sub.2 is hydrogen or alkyl of 1 to 4 carbon atoms, or is joined to R.sub.1 to form a cycloalkyl group of 3 to 6 carbon atoms;R.sub.3 is hydrogen, chlorine or bromine; andR.sub.4 is hydrogen, halogen, azido or amino; provided that when R.sub.4 is azido, R.sub.3 is hydrogen and R.sub.1 is methyl,R.sub.2 is not methyl, and that when R.sub.2 R.sub.3 and R.sub.4 are hydrogen andR.sub.1 is hydroxyethyl or an acyl derivative thereof, the compound does not have the (2R, 3S, 5R) stereochemistry; inhibit certain .beta.-lactamate enzymes and are useful in antiseptic and disinfectant solutions.

Abstract translation: 式（I）的化合物及其盐和酯，其中R 1是氢，1至4个碳原子的烷基，苯基，2至4个碳原子的烯基，2至4个碳原子的炔基，1至 4个碳原子，1至7个碳原子的羧酸基团或其酯，或被1或2个卤素原子取代的1至4个碳原子的烷基，羟基，取代的羟基，氨基，保护的氨基，取代的硫代1至7个 碳原子，1至7个碳原子的取代亚磺酰基，1至7个碳原子的取代磺酰基，或其1至7个碳原子的羧酸基或其酯; R2是氢或1〜4个碳原子的烷基，或者与R1连接，形成3〜6个碳原子的环烷基; R3是氢，氯或溴; R4是氢，卤素，叠氮基或氨基; 条件是当R 4是叠氮基时，R 3是氢，R 1是甲基，R 2不是甲基，当R 2 + L，R 3和R 4是氢并且R 1是羟乙基或其酰基衍生物时，该化合物不具有 ，3S，5R）立体化学; 抑制某些β-乳酸酶，并且可用于消毒和消毒溶液。

公开(公告)号：US4505894A

公开(公告)日：1985-03-19

申请号：US412591

申请日：1982-08-30

Applicant: Roger J. Ponsford

Inventor： Roger J. Ponsford

IPC: C07D503/08 ,  A61K31/42 ,  A61K31/424 ,  A61K31/43 ,  A61K31/545 ,  A61P31/04 ,  C07D503/00 ,  C07D503/20 ,  A61K35/00

CPC classification number: A61K31/43 ,  A61K31/545 ,  C07D503/00

Abstract: Compounds of the formula ##STR1## wherein X is S, SO or SO.sub.2 and R is an inert hydrocarbon of up to 20 carbon atoms which will not lead to rapid degradation of the above compound unsubstituted or substituted and A is a group such and CO.sub.2 A represents a carboxylic acid group or a salt or ester thereof, are useful for their antibacterial activity and for their .beta.-lactamase inhibitory activity.

Abstract translation: 式中，X为S，SO或SO 2的化合物，R为至多20个碳原子的惰性烃，其不会导致上述未被取代或取代的化合物的快速降解，A是这样的基团，而CO 2 A表示 羧酸基团或其盐或酯可用于其抗菌活性和β-内酰胺酶抑制活性。

公开(公告)号：US4263314A

公开(公告)日：1981-04-21

申请号：US4891

申请日：1979-01-19

Applicant: Roger J. Ponsford ,  Robert Southgate ,  Patricia M. Roberts

Inventor： Roger J. Ponsford ,  Robert Southgate ,  Patricia M. Roberts

IPC: C07D477/04 ,  C07D477/20 ,  A61K31/40 ,  C07D487/04

CPC classification number: C07D477/20 ,  C07D477/04

Abstract: The present invention provides the antibacterial agents of the formula (II): ##STR1## wherein R.sub.1 is a group such that CO.sub.2 R.sub.1 is a carboxylic acid group or a salt thereof or is a group of the formula CO.sub.2 R.sub.1.sup.1 wherein R.sub.1.sup.1 is a group such that CO.sub.2 R.sub.1.sup.1 is an ester group, R.sub.2 is a hydrogen atom or a lower alkyl group; R.sub.3 is a hydrogen atom or a lower alkyl group; and R.sub.4 is a phenyl group or a phenyl group substituted by one or two groups selected from fluorine, chlorine, OR.sub.5, NH.CO.R.sub.5, NH.CO.sub.2 R.sub.5 or CO.sub.2 R.sub.5 where R.sub.5 is a lower alkyl or benzyl group.A process for their preparation and their use in pharmaceutical compositions is also described.

Abstract translation: 本发明提供式（II）的抗菌剂：其中R 1是CO 2 R 1是羧酸基或其盐的基团，或者是式CO 2 R 11的基团，其中R 11是这样的基团，使得CO 2 R 11 是酯基，R2是氢原子或低级烷基; R3是氢原子或低级烷基; R 4是苯基或被一个或两个选自氟，氯，OR 5，NH.CO.R 5，NH.CO 2 R 5或CO 2 R 5的基团取代的苯基，其中R 5是低级烷基或苄基。 还描述了其制备方法及其在药物组合物中的应用。

公开(公告)号：US4704385A

公开(公告)日：1987-11-03

申请号：US835346

申请日：1986-03-03

Applicant: Roger J. Ponsford ,  Michael J. Pearson ,  Stephen C. Finch

Inventor： Roger J. Ponsford ,  Michael J. Pearson ,  Stephen C. Finch

IPC: C07D205/08 ,  A61K31/395 ,  A61K31/397 ,  A61K31/425 ,  A61P31/04 ,  C07D205/085 ,  C07D403/04 ,  C07D403/12 ,  C07D409/12 ,  C07D417/12 ,  C07F7/10 ,  C07F7/18 ,  C07F9/568 ,  C07D401/12

CPC classification number: C07D403/04 ,  C07D205/085 ,  C07D403/12 ,  C07D409/12 ,  C07D417/12 ,  C07F7/10 ,  C07F9/5683

Abstract: A monocyclic .beta.-lactam antibiotic having a formamido substituent at the 3S-position, including compounds of the formula (I): ##STR1## and salts thereof wherein R is --SO.sub.3 H; --PO(OH)Y wherein Y is C.sub.1-6 alkoxy, hydroxy, aryloxy, C.sub.1-6 alkyl or aryl; ##STR2## wherein Z represents C.sub.1-6 alkyl or aryl; ##STR3## wherein Z.sup.1 and Z.sup.2 may be the same or different and each represents hydrogen, C.sub.1-6 alkyl, aryl, amino or C.sub.1-6 alkoxy, or Z.sup.1 and Z.sup.2 together form the residue of a heterocyclic ring; --OSO.sub.3 H; or ##STR4## where X is hydrogen or hydroxy; R.sup.1 is an amino, protected amino or carboxylic acylamino group, and R.sup.2 and R.sup.3 are independently selected from hydrogen or a hydrocarbon group of 1 to 18 carbon atoms.