Patents Assigned to John Wyeth & Brother Limited
  • Patent number: 4608379
    Abstract: Compounds containing a cation of formula Ia ##STR1## and a pharmaceutically acceptable anion are anti-fungal agents. In formula Ia and Ib R.sub.1 is alkyl of at least 3 carbon atoms or aralkyl; R.sub.2 and R.sub.5 are hydrogen, lower alkyl, lower alkoxy, halogen or nitro; R.sub.6 and R.sub.7, when separate, are lower alkyl or aryl(lower)alkyl or, when joined together, are --(CH.sub.2).sub.2 --A--(CH.sub.2).sub.2 -- (where A is --(CH.sub.2).sub.n --, O, S or NR.sub.8 where n is O, 1 or 2 and R.sub.8 is lower alkyl) or a mono- or di-(lower alkyl) substitution product thereof.
    Type: Grant
    Filed: September 5, 1984
    Date of Patent: August 26, 1986
    Assignee: John Wyeth & Brother Limited
    Inventor: John T. A. Boyle
  • Patent number: 4604398
    Abstract: The invention concerns benzoquinolizines of general formula ##STR1## or their pharmaceutically acceptable acid addition salts. In the formula R.sup.1 and R.sup.2 which may be the same or different each represent hydrogen, lower alkyl, lower alkoxy or halogen, R.sup.3 represents lower alkyl and R.sup.4 is lower alkoxy or lower alkoxy carbonyl. The compounds possess .alpha..sub.2 -adrenoceptor antagonistic activity in warm blooded animals.
    Type: Grant
    Filed: June 13, 1985
    Date of Patent: August 5, 1986
    Assignee: John Wyeth & Brother Limited
    Inventor: Terence J. Ward
  • Patent number: 4578480
    Abstract: The invention relates to the preparation of 1-bromo-2-D-alkylpropanoyl-L-proline derivatives and analogous compounds which are useful as chemical intermediates to angiotensin converting enzyme (ACE) inhibitors and to the stereospecific synthesis of such ACE inhibitors having the formula: ##STR1## wherein R.sup.1 is lower alkyl and R.sup.4 and R.sup.5 are both hydrogen or together with the carbons to which they are attached represent a benzene ring optionally substituted by defined substituents. Intermediates of formula ##STR2## are also disclosed wherein R.sup.1, R.sup.4, R.sup.5 are as defined above and B.sup.+ is a cation.
    Type: Grant
    Filed: May 10, 1982
    Date of Patent: March 25, 1986
    Assignee: John Wyeth & Brother Limited
    Inventor: Roger Crossley
  • Patent number: 4550114
    Abstract: The invention concerns benzoquinolizines of general formula ##STR1## and their pharmaceutically acceptable acid addition salts. In the formula R.sup.1 and R.sup.2 which may be the same or different each represent hydrogen, lower alkyl, lower alkoxy or halogen, R.sup.3 represents hydrogen or lower alkyl and R.sup.4 represents a heterocyclic radical attached to the SO.sub.2 group through a carbon atom of the heterocyclic ring. The compounds possess .alpha..sub.2 -adrenoceptor antagonistic activity in warm blooded animals.
    Type: Grant
    Filed: January 3, 1984
    Date of Patent: October 29, 1985
    Assignee: John Wyeth & Brother limited
    Inventor: John F. White
  • Patent number: 4546187
    Abstract: The invention concerns novel compounds of formula IX--A--S--Y (I)wherein X is a radical selected from imidazolyl, pyridyl, quinolyl, tetrahydropyridyl or piperidyl any of which may be substituted and Y is any of the above radicals or a pyridinium radical, A is alkylene of 1-6 carbon atoms. Most of the compounds are anti-ulcer agents but some have anti-hypertensive activity, e.g. where X is quinolyl. Methods of treating ulcers and anti-ulcer compositions are also described.
    Type: Grant
    Filed: June 23, 1983
    Date of Patent: October 8, 1985
    Assignee: John Wyeth & Brother Limited
    Inventors: Roger Crossley, Kay H. Dickinson
  • Patent number: 4539406
    Abstract: An improved process for preparing fused carbocyclic ring derivatives of pyridine especially 5,6,7,8-tetrahydroquinoline 8-nitriles, amides and thioamides is described. The nitriles and thioamides are anti-ulcer and/or anti-secretory agents. Typically a compound of formula A ##STR1## wherein M is sodium, potassium, lithium or MgHal where Hal is chlorine, bromine or iodine, is reacted with a silyl compound R.sub.x.sup.a Si(NCY).sub.4-x III, wherein R.sup.a is selected from electron donating substituents, e.g. alkoxy or dialkylamino, and hydrocarbon substituents e.g. alkyl, at least one R.sup.a being an electron donating substituent, Y is oxygen or sulphur, x has a value from 1 to 3, then subjecting the product to hydrolysis or alcoholysis to obtain the corresponding nitrile, amide or thioamide, provided that when a nitrile is desired the molar ratio of compound III to compound A is at least 2:1 and x is 3 and Y is S. The products may be isolated as acid addition salts.
    Type: Grant
    Filed: June 21, 1983
    Date of Patent: September 3, 1985
    Assignee: John Wyeth & Brother Limited
    Inventor: Roger Crossley
  • Patent number: 4532253
    Abstract: The invention concerns pharmaceutical compositions containing a novel oxazole derivative, calcium oxaprozin. The formulations may be for oral or other use. The oral formulations are more palatable than those containing oxaprozin itself.
    Type: Grant
    Filed: July 11, 1984
    Date of Patent: July 30, 1985
    Assignee: John Wyeth & Brother Limited
    Inventor: Ahmed S. Mughal
  • Patent number: 4529798
    Abstract: Fused carbocyclic ring derivatives of pyridine which contain a nitrile or thioamide group on the carbocyclic ring e.g. 8-cyano or thiocarboxamido-5,6,7,8-tetrahydroquinolines are prepared by a process in which a sodium, potassium, lithium or magnesium halide derivative of the pyridine compound is treated with a compound RaRbNCN wherein Ra and Rb are the same or different and represent alkyl, cycloalkyl, or aralkyl, or Ra and Rb are joined to form a heterocyclic ring with the nitrogen, and the product is treated with a proton source to obtain the nitrile which is optionally treated with a sulphurizing agent to form the thioamide. The nitriles or thioamides may be isolated as their acid addition salts.
    Type: Grant
    Filed: December 2, 1981
    Date of Patent: July 16, 1985
    Assignee: John Wyeth & Brother Limited
    Inventor: Robin G. Shephard
  • Patent number: 4526970
    Abstract: An improved process for preparing tetrahydroquinolines and related compounds especially 5,6,7,8-tetrahydroquinoline-8-nitriles, amides and thioamides is described. The nitriles and thioamides are anti-ulcer and/or anti-secretory agents. Typically a compound of formula A ##STR1## where M is sodium, potassium, lithium or MgHal where Hal is chlorine, bromine or iodine, is reacted, e.g., in an ether solvent, with a silyl compound R.sub.x.sup.a Si(NCY).sub.4-x (III) wherein R.sup.a is alkyl, cycloalkyl, aralkyl, or aryl, at least one group R.sup.a being a branched chain alkyl, cycloalkyl, aryl or branched chain aralkyl, Y is oxygen or sulphur, x has a value from 1 to 3, then subjecting the product to hydrolysis or alcoholysis, to obtain the corresponding nitrile, amide or thioamide, provided that when a nitrile is desired the molar ratio of compound III to compound A is at least 2:1 and x is 3 and Y is S. The products may be obtained as acid addition salts.Compound A may contain various substituents, e.g.
    Type: Grant
    Filed: June 21, 1983
    Date of Patent: July 2, 1985
    Assignee: John Wyeth & Brother Limited
    Inventor: Robin G. Shepherd
  • Patent number: 4526967
    Abstract: The invention concerns benzoquinolizines of general formula ##STR1## and their pharmaceutically acceptable acid addition salts. In formula (I), R represents hydrogen or lower alkyl, R.sup.1 and R.sup.2 which may be the same or different each represent hydrogen, lower alkyl, lower alkoxy or halogen, R.sup.3 and R.sup.4 which may be the same or different each represents lower alkyl, halo(lower)alkyl or aryl and A represents a lower alkylene group having 1 to 3 carbon atoms in the chain between the two N atoms. The compounds possess .alpha..sub.2 -adrenoceptor antagonistic activity in warm blooded animals.
    Type: Grant
    Filed: March 19, 1984
    Date of Patent: July 2, 1985
    Assignee: John Wyeth & Brother Limited
    Inventor: Terence J. Ward
  • Patent number: 4524060
    Abstract: The invention provides a sustained release pharmaceutical composition comprising a mixture of micronized indoramin or a pharmaceutically acceptable salt thereof, a water-channelling agent, a wetting agent and a disintegrant, the mixture being in the form of a non-compressed pellet and having an enteric coat or a sustained release coat permeable to gastrointestinal juices. Sustained release capsules are also provided comprising a plurality of the aforementioned pellets.
    Type: Grant
    Filed: October 28, 1983
    Date of Patent: June 18, 1985
    Assignee: John Wyeth & Brother Limited
    Inventors: Ahmed S. Mughal, David S. Holmes
  • Patent number: 4506082
    Abstract: The invention relates to the preparation of 1-bromo-2-D-alkylphopanoyl-L-proline derivatives and analogous compounds which are useful as chemical intermediates to angiotensin converting enzyme (ACE) inhibitors and to the stereospecific synthesis of such ACE inhibitors having the formula: ##STR1## wherein R.sup.1 is lower alkyl and R.sup.4 and R.sup.5 are both hydrogen or together with the carbons to which they are attached represent a benzene ring optionally substituted by defined substituents. Intermediates of formula ##STR2## are also disclosed wherein R.sup.1, R.sup.4, R.sup.5 are as defined above and B.sup.+ is a cation.
    Type: Grant
    Filed: May 10, 1982
    Date of Patent: March 19, 1985
    Assignee: John Wyeth & Brother Limited
    Inventor: Roger Crossley
  • Patent number: 4481200
    Abstract: The invention concerns benzoquinolizines of formula ##STR1## and their pharmaceutically acceptable acid addition salts. In the formula R.sup.1 and R.sup.2 which may be the same or different each represent hydrogen, lower alkyl, lower alkoxy or halogen, R.sup.3 represents methyl or ethyl, A represents a direct bond between the S and N atoms or a lower alkylene group having 1 to 3 carbon atoms in the chain between the S and N atoms, R.sup.4 and R.sup.5 each independently represent hydrogen, lower alkyl, aryl or aryl(lower)alkyl or together with the nitrogen atom to which they are attached represent a five or six membered heterocyclic ring. The compounds possess .alpha..sub.2 -adrenoceptor antagonistic activity and can be incorporated into pharmaceutical compositions.
    Type: Grant
    Filed: March 3, 1983
    Date of Patent: November 6, 1984
    Assignee: John Wyeth & Brother, Limited
    Inventors: Terence J. Ward, John F. White
  • Patent number: 4473572
    Abstract: The invention concerns benzoquinolizines of formula ##STR1## and their pharmaceutically acceptable acid addition salts. In the formula, R.sup.1 and R.sup.2 which may be the same or different, each represent hydrogen, lower alkyl, lower alkoxy or halogen, R.sup.3 represents methyl or ethyl and R.sup.4 represents halo(lower)alkyl. The compounds possess .alpha..sub.2 -adrenoceptor antagonistic activity and can be incorporated into pharmaceutical compositions.
    Type: Grant
    Filed: March 3, 1983
    Date of Patent: September 25, 1984
    Assignee: John Wyeth & Brother, Limited
    Inventor: Terence J. Ward
  • Patent number: 4467091
    Abstract: Novel N-(4-pyridyl)acetamide derivatives having the formula ##STR1## [where R.sup.1 and R.sup.2 are aryl or heteroarly (optionally linked together by a lower alkylene bridge) or one of R.sup.1 and R.sup.2 is aryl or heteroaryl and the other of R.sup.1 and R.sup.2 is lower alkyl or ar(lower)alkyl, R.sup.3 and R.sup.4 are each hydrogen or lower alkyl] and their nontoxic acid addition salts are described. They are chemical intermediates for the preparation of 4-pyridinamine derivatives having the formula ##STR2## which show CNS activity and may be used as antidepressant drugs.
    Type: Grant
    Filed: January 28, 1983
    Date of Patent: August 21, 1984
    Assignee: John Wyeth & Brother Limited
    Inventors: Edwin T. Edington, Alan C. White
  • Patent number: 4466963
    Abstract: Pharmaceutical compositions containing meptazinol or a pharmaceutically acceptable acid addition salt thereof and ibuprofen or a pharmaceutically acceptable salt thereof are useful in treating pain in mammals.
    Type: Grant
    Filed: July 5, 1983
    Date of Patent: August 21, 1984
    Assignee: John Wyeth & Brother Limited
    Inventors: John F. Cavalla, Roger J. Stephens
  • Patent number: 4465838
    Abstract: The invention concerns a new anti-inflammatory agent calcium oxaprozin, its preparation and use in pharmaceutical formulations. Calcium oxaprozin is more palatable than oxaprozin itself.
    Type: Grant
    Filed: April 26, 1982
    Date of Patent: August 14, 1984
    Assignee: John Wyeth & Brother Limited
    Inventor: Ahmed S. Mughal
  • Patent number: 4463177
    Abstract: m-Hydroxyphenyl substituted compounds of formula ##STR1## where R is an organic radical and R.sup.1 is hydroen or an organic radical are prepared by dehydrohalogenating a compound of formula ##STR2## (where X is chlorine or bromine, and R and R.sup.1 have the above meanings). Preferred novel starting materials of formula (II) are of the formula ##STR3## (where R.sup.1 and X are as above, n is 2,3 or 4, R.sup.2 is hydrogen or lower alkyl and R.sup.3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, cycloalkyl(lower)alkyl or aryl(lower)alkyl).
    Type: Grant
    Filed: November 26, 1982
    Date of Patent: July 31, 1984
    Assignee: John Wyeth & Brother Limited
    Inventor: Robin G. Shepherd
  • Patent number: 4454139
    Abstract: The invention concerns benzoquinolizines of formula ##STR1## and their acid addition salts. In the formula R.sup.7 is lower alkyl or a phenyl or naphthyl radical optionally substituted with specified substituents and R.sup.8 is methyl or ethyl. The compounds possess high .alpha..sub.2 (presynaptic) adrenoceptor antagonistic activity and a good .alpha..sub.2 /.alpha..sub.1 antagonistic selectivity.
    Type: Grant
    Filed: September 9, 1982
    Date of Patent: June 12, 1984
    Assignee: John Wyeth & Brother, Limited
    Inventors: Terence J. Ward, John L. Archibald
  • Patent number: 4447604
    Abstract: Thiazolotriazine derivatives having the formula I ##STR1## their pharmaceutically acceptable salts, pharmaceutically acceptable triazolotriazinium compounds containing the cation having formula II ##STR2## and their zwitterionic forms and pharmaceutically acceptable acid addition salts [where A is hydroxy whilst B is hydrogen or A and B together represent a direct bond; R.sup.1 is aryl; R.sup.2 and R.sup.3 are independently lower alkyl or ar(lower)alkyl] are novel compounds useful as anti-cancer agents.
    Type: Grant
    Filed: April 1, 1982
    Date of Patent: May 8, 1984
    Assignee: John Wyeth & Brother Limited
    Inventors: John L. Archibald, John T. A. Boyle