Patents by Inventor Terence C. Smale

Terence C. Smale has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 4446146
    Abstract: The compounds 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 or ester thereof; R.sub.2 is a group of the sub-formula (a) or (b):--CR.sub.4 .dbd.C(R.sub.5) NH.CO.sub.n R.sub.6 (a)--CR.sub.7 .dbd.C(R.sub.8)R.sub.9 (b)wherein R.sub.4 is a hydrogen atom or a lower alkyl group; R.sub.5 is a hydrogen atom or a lower alkyl group; R.sub.6 is a lower alkyl, phenyl, fluorophenyl, chlorophenyl, bromophenyl or benzyl group; and n is 1 or 2; R.sub.7 is a hydrogen or a lower alkyl group; R.sub.8 is a hydrogen atom or a lower alkyl group; R.sub.9 is a hydrogen atom or a lower alkyl or phenyl group; R.sub.3 is a group of the sub-formula (c):CR.sub.10 R.sub.11 R.sub.12 (c)wherein R.sub.10 is a hydrogen atom or a hydroxyl or O.CO.R.sub.13 or O.CO.OR.sub.13 group where R.sub.13 is a lower alkyl, phenyl, benzyl, fluorobenzyl, chlorobenzyl, bromobenzyl, lower alkoxybenzyl or nitrobenzyl group; R.sub.11 is a hydrogen atom or a lower alkyl group; R.sub.
    Type: Grant
    Filed: July 20, 1979
    Date of Patent: May 1, 1984
    Assignee: Beecham Group Limited
    Inventors: Robert Southgate, Terence C. Smale, Roger J. Ponsford
  • Patent number: 4443599
    Abstract: There is provided a process for the preparation of an enantiomer of a compound of formula (I) which process comprises separation thereof from a mixture of diastereoisomers of a compound of the formula (I): ##STR1## wherein R is acetyl, .alpha.-hydroxyethyl or a protected derivative thereof, and R.sup.1 and R.sup.2 are substituted or unsubstituted hydrocarbon groups, or are joined so as to form a carbocyclic or heterocyclic ring; at least one of R.sup.1 and R.sup.2 containing a chiral center, such that the enantiomer can be separated thereby; and R.sup.3 and R.sup.4 are independently hydrogen or an organic group bonded via a carbon atom to the tetrahydro-oxazine ring, or R.sup.3 and R.sup.4 are joined so as to form together with the carbon atom to which they are attached an optionally substituted C.sub.3-7 cycloalkyl or optionally substituted heterocyclyl ring.The enantiomer is of use in the preparation of optically active carbapenem antibiotics.
    Type: Grant
    Filed: May 12, 1982
    Date of Patent: April 17, 1984
    Assignee: Beecham Group p.l.c.
    Inventor: Terence C. Smale
  • Patent number: 4431587
    Abstract: Compounds are described of the formula (II): ##STR1## wherein R.sub.1 is a group such that CO.sub.2 R.sub.1 is an ester group; A.sub.1 is a hydrogen atom; and A.sub.2 is a group CR.sub.2 R.sub.3 R.sub.4 wherein R.sub.2 is a hydrogen atom or a hydroxyl group; R.sub.3 is a hydrogen atom or a lower alkyl group; and R.sub.4 is a hydrogen atom or a lower alkyl group, a benzyl group, a phenyl group or is joined to R.sub.3 to form part of a C.sub.5-7 carboxylic ring or is a group of the formula CH(OH)R.sub.5 or CHX wherein R.sub.5 is a hydrogen atom or lower alkyl group and X is an oxygen atom or a CR.sub.6 R.sub.7 group where R.sub.6 is a hydrogen atom or a lower alkyl, phenyl, CN, CO.sub.2 R.sub.8 where R.sub.8 is a lower alkyl, phenyl or benzyl group and R.sub.7 is a hydrogen atom or a lower alkyl group or is joined to R.sub.6 to form part of a C.sub.5-7 carbocyclic ring. These compounds have been found to possess antibacterial properties. The preparation of these compounds is described.
    Type: Grant
    Filed: December 14, 1981
    Date of Patent: February 14, 1984
    Assignee: Beecham Group Limited
    Inventors: Kay H. Dickinson nee Berryman, Terence C. Smale, Robert Southgate
  • Patent number: 4428961
    Abstract: The present invention provides a compound of formula (I): ##STR1## wherein R.sup.1 is a group such that COOR.sup.1 is a carboxyic acid group or a salt or ester thereof;R.sup.3 is hydrogen or an organic radical;n is zero or 1;R.sup.4 and R.sup.5 are independently hydrogen or C.sub.1 -C.sub.3 alkyl;X is C.sub.1 -C.sub.6 alkylene optionally substituted by hydroxy or a carboxylic acid group or a salt or ester thereof;Y is an amino, or substituted amino, wherein the substituent is carboxylic acyl, C.sub.1 -C.sub.6 alkyl or a group .dbd.C(R.sup.14)NR.sup.15 R.sup.16 wherein R.sup.15 and or C.sub.1 -C.sub.6 alkyl and R.sup.14 is hydrogen or C.sub.1 -C.sub.6 alkyl, or a group --NR.sup.A R.sup.B wherein R.sup.A and R.sup.B are independently hydrogen or C.sub.1 -C.sub.6 alkyl.
    Type: Grant
    Filed: January 23, 1981
    Date of Patent: January 31, 1984
    Assignee: Beecham Group Limited
    Inventors: Robert Southgate, Terence C. Smale, Roger J. Ponsford
  • Patent number: 4405637
    Abstract: Compounds are described of the formula (II): ##STR1## wherein R.sub.1 is a group such that CO.sub.2 R.sub.1 is an ester group; A.sub.1 is a hydrogen atom; and A.sub.2 is a group CR.sub.2 R.sub.3 R.sub.4 wherein R.sub.2 is a hydrogen atom or a hydroxyl group; R.sub.3 is a hydrogen atom or a lower alkyl group; and R.sub.4 is a hydrogen atom or a lower alkyl group, a benzyl group, a phenyl group or is joined to R.sub.3 to form part of a C.sub.5-7 carboxylic ring or is a group of the formula CH(OH)R.sub.5 or CHX wherein R.sub.5 is a hydrogen atom or lower alkyl group and X is an oxygen atom or a CR.sub.6 R.sub.7 group where R.sub.6 is a hydrogen atom or a lower alkyl, phenyl, CN, CO.sub.2 R.sub.8 where R.sub.8 is a lower alkyl, phenyl or benzyl group and R.sub.7 is a hydrogen atom or a lower alkyl group or is joined to R.sub.6 to form part of a C.sub.5-7 carbocyclic ring. These compounds have been found to possess antibacterial properties. The preparation of these compounds is described.
    Type: Grant
    Filed: September 28, 1981
    Date of Patent: September 20, 1983
    Assignee: Beecham Group Limited
    Inventors: Kay H. Dickinson nee Berryman, Terence C. Smale, Robert Southgate
  • Patent number: 4350703
    Abstract: Compounds are described of the formula (II): ##STR1## wherein R.sub.1 is a group such that CO.sub.2 R.sub.1 is an ester group; A.sub.1 is a hydrogen atom; and A.sub.2 is a group CR.sub.2 R.sub.3 R.sub.4 wherein R.sub.2 is a hydrogen atom or a hydroxyl group; R.sub.3 is a hydrogen atom or a lower alkyl group; and R.sub.4 is a hydrogen atom or a lower alkyl group, a benzyl group, a phenyl group or is joined to R.sub.3 to form part of a C.sub.5-7 carboxylic ring or is a group of the formula CH(OH)R.sub.5 or CHX wherein R.sub.5 is a hydrogen atom or lower alkyl group and X is an oxygen atom or a CR.sub.6 R.sub.7 group where R.sub.6 is a hydrogen atom or a lower alkyl, phenyl, CN, CO.sub.2 R.sub.8 where R.sub.8 is a lower alkyl, phenyl or benzyl group and R.sub.7 is a hydrogen atom or a lower alkyl group or is joined to R.sub.6 to form part of a C.sub.5-7 carbocyclic ring. These compounds have been found to possess antibacterial properties. The preparation of these compounds is described.
    Type: Grant
    Filed: January 5, 1981
    Date of Patent: September 21, 1982
    Assignee: Beecham Group Limited
    Inventors: Kay H. Dickinson, Terence C. Smale, Robert Southgate
  • Patent number: 4347181
    Abstract: Compounds of the formula ##STR1## which are intermediates for producing antibacterial and .beta.-lactamase inhibiting compounds of the formula ##STR2## wherein R.sub.1 is alkyl of 1 to 6 carbon atoms, unsubstituted or substituted with hydroxy, amino, nitro, alkanoylamido of 1 to 6 carbon atoms, benzyloxycarbonylamido or p-nitrobenzyloxycarbonylamido; trityl; phenyl; or phenyl substituted by one or more members selected from the group consisting of halo, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, amino, alkanoylamido of 1 to 6 carbon atoms, benzyloxycarbonylamido or p-nitrobenzyloxycarbonylamido;R is alkyl of 1 to 6 carbon atoms, benzyl, p-nitrobenzyl, p-methoxybenzyl, phenacyl, p-bromophenacyl, 2,2,2-trichloroethyl, phthalidyl, phthalimidomethyl, .alpha.
    Type: Grant
    Filed: February 11, 1980
    Date of Patent: August 31, 1982
    Assignee: Beecham Group Limited
    Inventor: Terence C. Smale
  • Patent number: 4289696
    Abstract: The present invention provides a compound of formula (1): ##STR1## wherein G is hydrogen, alkyl, alkenyl, substituted alkyl or substituted alkenyl, R.sub.1 is alkyl or aryl, substituted alkyl or substituted aryl, and R is an organic group such that --CO.sub.2 R is an ester group. The compounds are useful as antibacterial and .beta.-lactamase inhibitory agents.
    Type: Grant
    Filed: February 11, 1980
    Date of Patent: September 15, 1981
    Assignee: Beecham Group Limited
    Inventor: Terence C. Smale
  • Patent number: 4223038
    Abstract: Compounds of the formula (I): ##STR1## wherein G is hydrogen, alkyl, alkenyl, substituted alkyl or substituted alkenyl, R.sub.1 is alkyl or aryl, substituted alkyl or substituted aryl, and R is an organic group such that --CO.sub.2 R is an ester group are produced. The compounds are useful as antibacterial and .beta.-lactamase inhibitory agents.
    Type: Grant
    Filed: October 30, 1978
    Date of Patent: September 16, 1980
    Assignee: Beecham Group Limited
    Inventor: Terence C. Smale