Patents Assigned to Ayerst, McKenna & Harrison Limited
  • Patent number: 4405625
    Abstract: A method is disclosed for lowering blood glucose levels in a diabetic mammal by administering an effective amount of 1,3-dioxo-1H-benz[de]isoquinoline-2(3H)-acetic acid.
    Type: Grant
    Filed: June 4, 1979
    Date of Patent: September 20, 1983
    Assignee: Ayerst, McKenna and Harrison Limited
    Inventor: Wilbur Lippmann
  • Patent number: 4189490
    Abstract: Compounds of formula I ##STR1## in which R.sup.1 is hydrogen, halogen, nitro, trifluoromethyl, lower alkyl or lower alkoxy; R.sup.2 is hydrogen or lower alkyl; R.sup.3 is hydroxy, 1H-tetrazol-5-yl or COOR.sup.4 wherein R.sup.4 is hydrogen or lower alkyl, and X is O, S, SO or SO.sub.2, are disclosed. The compounds of formula I are useful for treating allergic conditions. Methods for the preparation and use of the compounds are disclosed.
    Type: Grant
    Filed: January 29, 1979
    Date of Patent: February 19, 1980
    Assignee: Ayerst McKenna & Harrison Limited
    Inventors: Adolf H. Philipp, Ivo L. Jirkovsky
  • Patent number: 4183955
    Abstract: Tropone derivatives characterized by having a derivative of oxamic acid at positions 2 and or 5 are disclosed. In addition, the tropone nucleus can be optionally further substituted. The foregoing compounds are useful for preventing or treating allergic conditions in a mammal. Methods for the preparation and use of said compounds are disclosed.
    Type: Grant
    Filed: August 31, 1978
    Date of Patent: January 15, 1980
    Assignee: Ayerst. McKenna & Harrison Limited
    Inventors: Jehan F. Bagli, Tibor Bogri
  • Patent number: 4171443
    Abstract: 10b-Azafluoranthene derivatives characterized by having a 1,2,3,3a,5,6-hexahydro-4-oxa(or thia)-10b-azafluoranthene nucleus having an alkanamine substituent at position 3 or 3a are disclosed. The nucleus is optionally further substituted on the aromatic ring. The derivatives are useful antidepressant agents, and methods for their preparation and use are also disclosed.
    Type: Grant
    Filed: May 8, 1978
    Date of Patent: October 16, 1979
    Assignee: Ayerst, McKenna & Harrison Limited
    Inventors: Andre A. Asselin, Leslie G. Humber
  • Patent number: 4170653
    Abstract: Disclosed herein are compounds of the formula ##STR1## in which Ar is phenyl or 1-naphthyl; R.sup.1 is hydrogen or lower alkyl; and R.sup.2 and R.sup.3 together with the nitrogen atom to which they are joined form a heterocyclic amine radical selected from the group consisting of 1-pyrrolidinyl, piperidino, morpholino and 4-(lower alkyl)-1-piperazinyl. The compounds are antidepressant agents and methods for their preparation and use also are disclosed.
    Type: Grant
    Filed: September 1, 1977
    Date of Patent: October 9, 1979
    Assignee: Ayerst McKenna and Harrison Limited
    Inventors: Jean-Marie Ferland, Real Laliberte, Wilbur Lippmann, Thomas A. Pugsley
  • Patent number: 4161608
    Abstract: A process for preparing 11-deoxyprostaglandin E.sub.1, E.sub.2 and E.sub.3 and analogs thereof is realized by treating an appropriate di(lower)alkyl 3-(optionally substituted)-2-formylcyclopropane-1,1-dicarboxylate with an ylid prepared from a Wittig reagent of formula (AlkO).sub.2 POCH.sub.2 CO--(c)-CH.sub.3 in which Alk is an alkyl containing one to three carbon atoms and (c) is either (CH.sub.2).sub.q wherein q is an integer from 1 to 6 or cis CH.sub.2 CH.dbd.CH(CH.sub.2).sub.r wherein r is an integer from 0 to 3 to obtain the corresponding compound of formula: ##STR1## in which R.sup.2 is hydrogen, lower alkyl or CH.sub.2 OR.sup.3 wherein R.sup.3 is lower alkanoyl, R.sup.4 is lower alkyl and (c) is as defined herein. The latter compound is reduced with an alkali metal borohydride to yield the corresponding alcohol derivative. Condensation of this alcohol derivative or preferably its corresponding tetrahydropyran-2-yl ether derivative with a triester of formula CH(COOR.sup.6).sub.2 --(a)-(CH.sub.
    Type: Grant
    Filed: January 27, 1978
    Date of Patent: July 17, 1979
    Assignee: Ayerst, McKenna and Harrison Limited
    Inventors: Nedumparambil A. Abraham, Jehan F. Bagli, Tibor Bogri
  • Patent number: 4152457
    Abstract: Tropone derivatives substituted with an amino-, thio- or oxy-derivative of oxalic acid or acetic acid are disclosed. In addition, the tropone nucleus can be optionally further substituted. The foregoing compounds are useful for preventing or treating allergic conditions in a mammal. Methods for the preparation and use of the compounds are disclosed.
    Type: Grant
    Filed: October 11, 1977
    Date of Patent: May 1, 1979
    Assignee: Ayerst, McKenna and Harrison Limited
    Inventors: Jehan F. Bagli, Tibor Bogri
  • Patent number: 4152456
    Abstract: Tropone derivatives substituted with an amino-, thio- or oxy-derivative of oxalic acid or acetic acid are disclosed. In addition, the tropone nucleus can be optionally further substituted. The foregoing compounds are useful for preventing or treating allergic conditions in a mammal. Methods for the preparation and use of the compounds are disclosed.
    Type: Grant
    Filed: October 7, 1977
    Date of Patent: May 1, 1979
    Assignee: Ayerst, McKenna and Harrison Limited
    Inventors: Jehan F. Bagli, Tibor Bogri
  • Patent number: 4140779
    Abstract: Disclosed herein are compounds of the formula ##STR1## in which Ar is l-naphthyl; R.sup.1 and R.sup.2 are either the same or different selected from the group consisting of hydrogen or lower alkyl, or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are joined form a heterocyclic amine radical selected from the group consisting of 1-pyrrolidinyl, piperidine, morpholine and 4-(lower alkyl)-1-piperazinyl; and R.sup.3 and R.sup.4 are either the same or different selected from the group consisting of hydrogen or lower alkyl, or R.sup.3 and R.sup.4 together with the nitrogen to which they are joined represent a heterocyclic amine radical selected from the group consisting of 1-pyrrolidinyl, piperidino, morpholino and 4-(lower alkyl)-1-piperazinyl; or a therapeutically acceptable acid addition salt thereof. The compounds are antidepressant agents and methods for their preparation and use also are disclosed.
    Type: Grant
    Filed: May 19, 1976
    Date of Patent: February 20, 1979
    Assignee: Ayerst, McKenna and Harrison Limited
    Inventors: Jean-Marie Ferland, Real R. Laliberte, Wilbur Lippmann, Thomas A. Pugsley
  • Patent number: 4130649
    Abstract: Cyclohepta[b]pyridine-2-carboxylic acid derivatives characterized by having a 4,7-dihydro-4,7-dioxo-1H-cyclohepta-[b]pyridine nucleus substituted at position 2 with a carboxylic acid or carboxylic acid ester are disclosed. In addition, the nucleus can be optionally further substituted at positions 1, 5,6 and 8. The foregoing compounds are useful for preventing or treating allergic conditions in a mammal. Methods for the preparation and use of the compounds are disclosed.
    Type: Grant
    Filed: April 21, 1977
    Date of Patent: December 19, 1978
    Assignee: Ayerst, McKenna & Harrison Limited
    Inventors: Jehan F. Bagli, Tibor Bogri
  • Patent number: 4125625
    Abstract: Tropone derivatives characterized by having a derivative of oxamic acid at positions 2 and or 5 are disclosed. In addition, the tropone nucleus can be optionally further substituted. The foregoing compounds are useful for preventing or treating allergic conditions in a mammal. Methods for the preparation and use of said compounds are disclosed.
    Type: Grant
    Filed: May 31, 1977
    Date of Patent: November 14, 1978
    Assignee: Ayerst, McKenna & Harrison Limited
    Inventors: Jehan F. Bagli, Tibor Bogri
  • Patent number: 4118511
    Abstract: Disclosed herein are compounds of the formula ##STR1## in which Ar is phenyl or 1-naphthyl; R.sup.1 is hydrogen or lower alkyl; and R.sup.2 and R.sup.3 are either the same or different selected from the group consisting of hydrogen or lower alkyl; with the proviso that when R.sup.1 is lower alkyl then R.sup.2 is the same lower alkyl. The compounds are antidepressant agents and methods for their preparation and use also are disclosed.
    Type: Grant
    Filed: November 18, 1977
    Date of Patent: October 3, 1978
    Assignee: Ayerst, McKenna & Harrison Limited
    Inventors: Jean-Marie Ferland, Real Laliberte, Wilbur Lippmann, Thomas A. Pugsley
  • Patent number: 4118380
    Abstract: Compounds of the formula 1 or 1a ##STR1##HSCH.sub.2 CH.sub.2 CO-A-Phe-Phe-Trp-Lys-Thr-Phe-Thr-Ser-NHCH.sub.2 CH.sub.2 SH (1a)in which A is Gly-Asn or Lys-Gly, or therapeutically acceptable salts thereof are disclosed. The compounds of formulae 1 and 1a are useful for the management of diabetes and the treatment of acromegaly in mammals. Compositions and methods for their use also are disclosed.
    Type: Grant
    Filed: July 25, 1977
    Date of Patent: October 3, 1978
    Assignee: Ayerst, McKenna & Harrison Limited
    Inventors: Hans U. Immer, Nedumparambil A. Abraham
  • Patent number: 4118394
    Abstract: Pyranoindole and thiopyranoindole derivatives characterized by having an amino(lower)alkyl radical attached to either or both the 1 and 9 position of a pyrano[3,4-b]indole or thiopyrano[3,4-b]indone nucleus are disclosed. The amino portion of the amino(lower)alkyl radical may be further substituted with one or two lower alkyl groups or incorporated into a heterocyclic amine radical. The derivatives having the amino(lower)alkyl radical only at position 1 are further substituted at position 1 and may be optionally substituted at positions 3, 4, 5, 6, 7, 8, and 9. The derivatives having the amino(lower)alkyl radical only at position 9 possess two substituents at position 1 and may be optionally substituted at position 3, 4, 5, 6, 7, and 8. The derivatives having an amino(lower)alkyl radical at both positions 1 and 9 are further substituted at position 1 and may be optionally substituted at positions 3, 4, 5, 6, 7 and 8.
    Type: Grant
    Filed: August 8, 1977
    Date of Patent: October 3, 1978
    Assignee: Ayerst, McKenna & Harrison Limited
    Inventors: Christopher A. Demerson, Leslie G. Humber, Andre A. Asselin, Ivo Jirkovsky, Thomas A. Dobson
  • Patent number: 4118495
    Abstract: A method is disclosed for preventing or decreasing the secretion or availability of excessive amounts of glucagon in a human having abnormally increased levels of glucagon by administering an effective amount of 1,3-dioxo-1H-benz[de]isoquinoline-2(3H)-acetic acid.
    Type: Grant
    Filed: July 25, 1977
    Date of Patent: October 3, 1978
    Assignee: Ayerst, McKenna & Harrison Limited
    Inventor: Wilbur Lippmann
  • Patent number: 4110468
    Abstract: Tropone derivatives substituted with an amino-, thio- or oxy-derivative of oxalic acid or acetic acid are disclosed. In addition, the tropone nucleus can be optionally further substituted. The foregoing compounds are useful for preventing or treating allergic conditions in a mammal. Methods for the preparation and use of the compounds are disclosed.
    Type: Grant
    Filed: October 7, 1977
    Date of Patent: August 29, 1978
    Assignee: Ayerst, McKenna & Harrison Limited
    Inventors: Jehan F. Bagli, Tibor Bogri
  • Patent number: 4108997
    Abstract: [2]Benzopyrano[4,3-b]pyridine derivatives characterized by having a 2,3,4,4a,6,10b-hexahydro-1H-[2]benzopyrano[4,3-b]pyridine nucleus bearing substituents at positions 1,6,8 and 9 are disclosed. The derivatives are useful diuretic agents. Methods for their preparation and use also are disclosed.
    Type: Grant
    Filed: December 20, 1976
    Date of Patent: August 22, 1978
    Assignee: Ayerst, McKenna & Harrison Limited
    Inventors: Jean A. Gauthier, Leslie G. Humber, Clara Revesz
  • Patent number: 4100343
    Abstract: A process for preparing 11-deoxyprostaglandin E.sub.1, E.sub.2 and E.sub.3 and analogs thereof is realized by treating an appropriate di(lower)alkyl 3-(optionally substituted)-2-formylcyclopropane-1,1-dicarboxylate with an ylid prepared from a Wittig reagent of formula (AlkO).sub.2 POCH.sub.2 CO-(c)-CH.sub.3 in which Alk is an alkyl containing one to three carbon atoms and (c) is either (CH.sub.2).sub.q wherein q is an integer from 1 to 6 or cis CH.sub.2 CH.dbd.CH(CH.sub.2).sub.r wherein r is an integer from 0 to 3 to obtain the corresponding compound of formula: ##STR1## in which R.sup.2 is hydrogen, lower akyl or CH.sub.2 OR.sup.3 wherein R.sup.3 is lower alkanoyl, R.sup.4 is lower alkyl and (c) is as defined herein. The latter compound is reduced with an alkali metal borohydride to yield the corresponding alcohol derivative. Condensation of this alcohol derivative or preferably its corresponding tetrahydropyran-2-yl ether derivative with a triester of formula CH(COOR.sup.6).sub.2 -(a)-(CH.sub.
    Type: Grant
    Filed: November 11, 1976
    Date of Patent: July 11, 1978
    Assignee: Ayerst, McKenna & Harrison Limited
    Inventors: Nedumparambil A. Abraham, Jehan F. Bagli, Tibor Bogri
  • Patent number: 4081530
    Abstract: Compounds of the formula 1 or 1a ##STR1## wherein R.sup.1 is H--, H--Gly or H--Leu and R.sup.2 is H or COOH and pharmaceutically acceptable salts thereof, are disclosed. The compounds of formulae 1 and 1a are useful for the management of diabetes and the treatment of acromegaly. Methods for their use are also disclosed.
    Type: Grant
    Filed: June 4, 1975
    Date of Patent: March 28, 1978
    Assignee: Ayerst, McKenna & Harrison Limited
    Inventors: Hans U. Immer, Verner R. Nelson, Kazimir Sestanj
  • Patent number: 4056538
    Abstract: Pyranoindole and thiopyranoindole derivatives characterized by having an amino(lower)alkyl radical attached to either or both the 1 and 9 position of a pyrano[ 3,4-b]indole or thiopyrano[3,4-b]indole nucleus are disclosed. The amino position of the amino(lower)alkyl radical may be further substituted with one or two lower alkyl groups or incorporated into a heterocyclic amine radical. The derivatives having the amino(lower)alkyl radical only at position 1 are further substituted at position 1 and may be optionally substituted at positions 3, 4, 5, 6, 7, 8, and 9. The derivatives having the amino(lower)alkyl radical only at position 9 posses two substituents at position 1 and may be optionally substituted at position 3, 4, 5, 6, 7, and 8. The derivatives having an amino(lower)alkyl radical at both positions 1 and 9 are further substituted at position 1 and may be optionally substituted at positions 3, 4, 5, 6, 7 and 8.
    Type: Grant
    Filed: October 18, 1976
    Date of Patent: November 1, 1977
    Assignee: Ayerst, McKenna & Harrison Limited
    Inventors: Christopher A. Demerson, Leslie G. Humber, Andre A. Asselin, Ivo Jirkovsky, Thomas A. Dobson