Patents Assigned to Ayerst, McKenna and Harrison Limited
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Patent number: 4405625Abstract: 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: GrantFiled: June 4, 1979Date of Patent: September 20, 1983Assignee: Ayerst, McKenna and Harrison LimitedInventor: Wilbur Lippmann
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Patent number: 4189490Abstract: 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: GrantFiled: January 29, 1979Date of Patent: February 19, 1980Assignee: Ayerst McKenna & Harrison LimitedInventors: Adolf H. Philipp, Ivo L. Jirkovsky
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Patent number: 4183955Abstract: 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: GrantFiled: August 31, 1978Date of Patent: January 15, 1980Assignee: Ayerst. McKenna & Harrison LimitedInventors: Jehan F. Bagli, Tibor Bogri
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Patent number: 4171443Abstract: 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: GrantFiled: May 8, 1978Date of Patent: October 16, 1979Assignee: Ayerst, McKenna & Harrison LimitedInventors: Andre A. Asselin, Leslie G. Humber
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Patent number: 4170653Abstract: 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: GrantFiled: September 1, 1977Date of Patent: October 9, 1979Assignee: Ayerst McKenna and Harrison LimitedInventors: Jean-Marie Ferland, Real Laliberte, Wilbur Lippmann, Thomas A. Pugsley
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Patent number: 4161608Abstract: 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: GrantFiled: January 27, 1978Date of Patent: July 17, 1979Assignee: Ayerst, McKenna and Harrison LimitedInventors: Nedumparambil A. Abraham, Jehan F. Bagli, Tibor Bogri
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Patent number: 4152457Abstract: 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: GrantFiled: October 11, 1977Date of Patent: May 1, 1979Assignee: Ayerst, McKenna and Harrison LimitedInventors: Jehan F. Bagli, Tibor Bogri
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Patent number: 4152456Abstract: 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: GrantFiled: October 7, 1977Date of Patent: May 1, 1979Assignee: Ayerst, McKenna and Harrison LimitedInventors: Jehan F. Bagli, Tibor Bogri
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Patent number: 4140779Abstract: 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: GrantFiled: May 19, 1976Date of Patent: February 20, 1979Assignee: Ayerst, McKenna and Harrison LimitedInventors: Jean-Marie Ferland, Real R. Laliberte, Wilbur Lippmann, Thomas A. Pugsley
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Patent number: 4130649Abstract: 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: GrantFiled: April 21, 1977Date of Patent: December 19, 1978Assignee: Ayerst, McKenna & Harrison LimitedInventors: Jehan F. Bagli, Tibor Bogri
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Patent number: 4125625Abstract: 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: GrantFiled: May 31, 1977Date of Patent: November 14, 1978Assignee: Ayerst, McKenna & Harrison LimitedInventors: Jehan F. Bagli, Tibor Bogri
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Patent number: 4118394Abstract: 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: GrantFiled: August 8, 1977Date of Patent: October 3, 1978Assignee: Ayerst, McKenna & Harrison LimitedInventors: Christopher A. Demerson, Leslie G. Humber, Andre A. Asselin, Ivo Jirkovsky, Thomas A. Dobson
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Patent number: 4118511Abstract: 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: GrantFiled: November 18, 1977Date of Patent: October 3, 1978Assignee: Ayerst, McKenna & Harrison LimitedInventors: Jean-Marie Ferland, Real Laliberte, Wilbur Lippmann, Thomas A. Pugsley
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Patent number: 4118495Abstract: 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: GrantFiled: July 25, 1977Date of Patent: October 3, 1978Assignee: Ayerst, McKenna & Harrison LimitedInventor: Wilbur Lippmann
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Patent number: 4118380Abstract: 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: GrantFiled: July 25, 1977Date of Patent: October 3, 1978Assignee: Ayerst, McKenna & Harrison LimitedInventors: Hans U. Immer, Nedumparambil A. Abraham
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Patent number: 4110468Abstract: 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: GrantFiled: October 7, 1977Date of Patent: August 29, 1978Assignee: Ayerst, McKenna & Harrison LimitedInventors: Jehan F. Bagli, Tibor Bogri
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Patent number: 4108997Abstract: [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: GrantFiled: December 20, 1976Date of Patent: August 22, 1978Assignee: Ayerst, McKenna & Harrison LimitedInventors: Jean A. Gauthier, Leslie G. Humber, Clara Revesz
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Patent number: 4100343Abstract: 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: GrantFiled: November 11, 1976Date of Patent: July 11, 1978Assignee: Ayerst, McKenna & Harrison LimitedInventors: Nedumparambil A. Abraham, Jehan F. Bagli, Tibor Bogri
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Patent number: 4081530Abstract: 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: GrantFiled: June 4, 1975Date of Patent: March 28, 1978Assignee: Ayerst, McKenna & Harrison LimitedInventors: Hans U. Immer, Verner R. Nelson, Kazimir Sestanj
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Patent number: 4056538Abstract: 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: GrantFiled: October 18, 1976Date of Patent: November 1, 1977Assignee: Ayerst, McKenna & Harrison LimitedInventors: Christopher A. Demerson, Leslie G. Humber, Andre A. Asselin, Ivo Jirkovsky, Thomas A. Dobson