Patents by Inventor Stefan H. Unger
Stefan H. Unger 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).
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Patent number: 4792570Abstract: Compounds useful for treating inflammation, swelling and associated pain, represented by the formula: ##STR1## and the pharmaceutically acceptable acid addition salts thereof, wherein: a is an integer of 0-3;b is an integer of 0-2;n is an integer of 3-12;each X and each Y are independently -halo, --R.sup.1, -alkoxy, or -phenyl; andB is selected from the group consisting of:--NR.sup.1 R.sup.2, --NR.sup.1 (CH.sub.2 CH.sub.2 OH), ##STR2## in which R.sup.1 and R.sup.2 are independently H, alkyl or cycloalkyl;R.sup.3 is H, alkyl or --CH.sub.2 CH.sub.2 OH; andm is an integer of 3-8.Novel compounds are those wherein n is at least 6 if both a and b are 0.Type: GrantFiled: April 6, 1984Date of Patent: December 20, 1988Assignee: Syntex (U.S.A.) Inc.Inventors: Peter H. Nelson, James P. Dunn, Stefan H. Unger, Thomas R. Thieme
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Patent number: 4792551Abstract: Compounds useful for treating inflammation, pain and swelling, represented by the formula: ##STR1## and the pharmaceutically acceptable acid addition salts thereof, wherein: Y and Z are each independently halo, alkyl or alkoxy;l and m are each independently integers of 0-4;b is an integer of 2-12; andX is selected from the group consisting of:--NR.sup.1 R.sup.2, --NR.sup.1 (CH.sub.2 CH.sub.2 OH), ##STR2## in which R.sup.1 and R.sup.2 are independently H, alkyl or cycloalkyl;R.sup.3 is H, alkyl or CH.sub.2 CH.sub.2 OH; andn is an integer of 3-7.Type: GrantFiled: July 15, 1983Date of Patent: December 20, 1988Assignee: Syntex (U.S.A.) Inc.Inventors: Peter H. Nelson, Stefan H. Unger, Thomas R. Thieme
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Patent number: 4680300Abstract: A compound having the formula ##STR1## where Ar=naphthyl, biphenyl, or quinolinyl;X=oxygen or NH;Y=2 to 8;R.sub.1 =phenyl, substituted phenyl, hydrogen, lower alkyl; andR.sub.2 is the same or different from R.sub.3 and is alkyl, cycloalkyl, phenyl, substituted phenyl, thiazolyl; andthe pharmaceutically acceptable salts thereof.Compounds of this general formula are useful as anti-inflammatories, and as anti-psoriatic agents.Type: GrantFiled: January 10, 1985Date of Patent: July 14, 1987Assignee: Syntex (U.S.A.) Inc.Inventors: Peter Nelson, Stefan H. Unger
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Patent number: 4599331Abstract: This invention provides a method for inhibiting angiogenesis in mammals. A pharmaceutically acceptable formulation containing a compound of the formula ##STR1## where X.sub.1 X.sub.2 and X.sub.3 are H, C1, or F and X.sub.3 must be H if the substituent of R.sub.1 is .alpha.OH;R.sup.1 is chosen from the group consisting of hydroxyl and hydrogen;R.sub.2 is chosen from the group of alkyloxy or thioalkyls wherein said alkyls have less than 5 carbon atomsR.sub.3 is H or an alkyl having less than 6 carbon atoms, is administered to the mammal having undesirable angiogenesis.The wavy line at C-16 refers to either .alpha. or .beta..Type: GrantFiled: December 24, 1984Date of Patent: July 8, 1986Assignee: Syntex (U.S.A.) Inc.Inventors: Alain B. Schreiber, William J. Kowalski, Stefan H. Unger
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Patent number: 4560699Abstract: Novel 5-(4-vinyl- or 4-ethynylbenzoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids represented by the formula ##STR1## and the pharmaceutically acceptable, non-toxic alkyl esters and salts thereof, wherein R is vinyl or ethynyl, and Y is hydrogen, a lower alkyl group having from 1 to 6 carbon atoms, chloro or bromo.Type: GrantFiled: January 17, 1983Date of Patent: December 24, 1985Assignee: Syntex (U.S.A.) Inc.Inventors: Joseph M. Muchowski, Stefan H. Unger
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Patent number: 4536503Abstract: Compounds of the formula: ##STR1## and the pharmaceutically acceptable acid addition salts thereof, wherein; Y is halo, alkoxy, alkyl, or dialkylamino;a is 0, 1 or 2;b is an integer from 2-12 with the proviso that if b is 2 or 3 a cannot be 0; andX is selected from the group consisting of: --OH, OR.sup.1, --NH.sub.2, --NHR.sup.1, NR.sub.2.sup.1, ##STR2## and --NHCONHR.sup.2 in which each R.sup.1 is independently alkyl or cycloalkyl or in --NR.sub.2.sup.1, both R.sup.1 together are alkylene or form a piperazine ring optionally substituted at the ring N by alkyl or --CH.sub.2 CH.sub.2 OH; andR.sup.2 is alkyl, cycloalkyl, or optionally substituted phenyl;have antiinflammatory properties and are useful in the treatment of conditions characterized by inflammation and swelling.Type: GrantFiled: January 9, 1984Date of Patent: August 20, 1985Assignee: Syntex (U.S.A.) Inc.Inventors: Peter H. Nelson, Howard J. Ringold, Stefan H. Unger, Thomas R. Thieme
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Patent number: 4512990Abstract: Compounds of the formula: ##STR1## and the pharmaceutically acceptable acid addition salts thereof, wherein: Z is S;Y is halo, alkoxy, alkyl, or dialkylamino;a is 0, 1 or 2;b is an integer from 2-12 with the proviso that if b is 2 or 3, a cannot be 0, and with the further proviso that if X is OH, b cannot be 2-5 and with the further proviso that if X is --NH.sub.2, b cannot be 2-5; andX is selected from the group consisting of: --OH, OR.sup.1, --NH.sub.2, --NHR.sup.1, NR1/2, ##STR2## and --NHCONHR.sup.2 in which each R.sup.1 is independently alkyl or cycloalkyl or, in --NR1/2, both R.sup.1 s together are alkylene or form a piperazine ring optionally substituted at the ring N by alkyl or --CH.sub.2 CH.sub.2 OH; andR.sup.2 is alkyl, cycloalkyl, or optionally substituted phenyl;have antiinflammatory properties and are useful in the treatment of conditions characterized by inflammation and swelling.Type: GrantFiled: February 18, 1982Date of Patent: April 23, 1985Assignee: Syntex (U.S.A.), Inc.Inventors: Peter H. Nelson, Howard J. Ringold, Stefan H. Unger, Thomas R. Thieme
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Patent number: 4255432Abstract: Compounds of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are the same or different and are hydrogen, C.sub.1 to C.sub.6 alkyl, C.sub.6 to C.sub.12 carbocyclic aryl or aralkyl of 1 to 6 carbon atoms in the alkyl moiety and 6 to 12 carbon atoms in the carbocyclic aryl moiety;R.sup.4 and R.sup.5 are the same or different and are hydrogen or C.sub.1 to C.sub.6 alkyl; andR.sup.6 and R.sup.7 are the same or different and are hydrogen, C.sub.1 to C.sub.6 alkyl or C.sub.1 to C.sub.6 alkoxy. Methods for preparing these compounds are also disclosed. The compounds are useful as antihypertensives and as diuretics. They also function as antihistamines and as bronchodilating agents and are therefore effective in inhibiting the effects of allergic reactions. They are also of use in the treatment of migraine and in the treatment of vasospastic disorders.Type: GrantFiled: September 6, 1979Date of Patent: March 10, 1981Assignee: Syntex (U.S.A.) Inc.Inventors: Arthur F. Kluge, Arthur M. Strosberg, Stefan H. Unger
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Patent number: 4244961Abstract: Compounds of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are the same or different and are hydrogen, C.sub.1 to C.sub.6 alkyl, C.sub.6 to C.sub.14 carbocyclic aryl or aralkyl of 1 to 6 carbon atoms in the alkyl moiety and 6 to 12 carbon atoms in the carbocyclic aryl moiety and R.sup.4 is selected from the group having the formula ##STR2## where R is C.sub.1 to C.sub.8 alkyl, C.sub.1 to C.sub.8 alkoxy, halo, cyano, AlkNHC(O)-- or AlkC(O)NH-- and R' is Alk NHC(O) or Alk C(O)NH where Alk is C.sub.1 to C.sub.6 alkyl or the group 2-(endobicyclo[3.1.0]hexyl)ethyl. Methods for preparing the compounds are disclosed. The compounds are useful for the treatment of hypertension and cardiac disorders.Type: GrantFiled: October 26, 1978Date of Patent: January 13, 1981Assignee: Syntex (U.S.A.) Inc.Inventors: Arthur F. Kluge, Stefan H. Unger
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Patent number: 4177280Abstract: 1-Alkylamino-3-(4-[(endobicyclo[3.1.0]hex-6-yl)alkylure ido]-1-phenoxy)-2-propanol and substituted derivatives thereof; 1-alkylamino-3-(4-[(endobicyclo[3.1.0]hex-6-yl)-alkylcarbonylamino]-1-phen oxy)-2-propanol and substituted derivatives thereof; and 1-alkylamino-3-(4-[(endobicyclo-[3.1.0]hex-6-yl)alkoxycarbonylamino]-1-phe noxy)-2-propanol and substituted derivatives thereof as well as methods for preparing such compounds are disclosed. 5-(4-[(Endobicyclo[3.1.0]hex-6-yl)alkylureido]-1-phenoxy) methyl-3-alkyl-2-optionally substituted oxazolidine and derivatives thereof; 5-(4-[(endobicyclo[3.1.0]hex-6-yl alkylcarbonylamino]-1-phenoxy)methyl-3-alkyl-2-optionally substituted oxazolidine and derivatives thereof; and 5-(4-[(endobicyclo[3.1.0]hex-6-yl)alkoxycarbonylamino]-1-phenoxy)methyl-3- alkyl-2-optionally substituted oxazolidine and derivatives thereof and methods for preparing these compounds are also disclosed.Type: GrantFiled: July 3, 1978Date of Patent: December 4, 1979Assignee: Syntex (U.S.A.) Inc.Inventors: Karl G. Untch, Belig Berkoz, Stefan H. Unger
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Patent number: 4151297Abstract: 1-Alkylamino-3-(3- or 4-[2-(endobicyclo[3.1.0]-hex-6-yl)ethylaminocarbonyl]-1-phenoxy)-2-propano l and substituted derivatives thereof and methods for preparing such compounds are disclosed. 5-(3- Or 4-[2-(endobicyclo[3.1.0]hex-6-yl)ethylaminocarbonyl]-phenoxy)methyl 3-alkyl-2-optionally substituted oxazolidine and derivatives thereof, and methods for preparing such compounds are also disclosed. These compounds exhibit cardiovascular acitivity and are useful in the treatment of abnormal heart condition as well as hypertension in mammals. The former compounds are prepared by treatment of the corresponding 1,2-epoxy-3-(3- or 4-[2-(endobicyclo[3.1.0]hex-6-yl)-ethylaminocarbonyl]phenoxy)propane with the desired alkylamine or by base or acid hydrolysis of the corresponding 5-(3- or 4-[2-(endobicyclo[3.1.0]hex-6-yl)-ethylaminocarbonyl)-3-alkyl oxazolidine. The latter compounds are prepared from the corresponding 1-alkylamino-3-(3- or 4-[2-(endobicyclo[3.1.Type: GrantFiled: October 31, 1977Date of Patent: April 24, 1979Assignee: Syntex (U.S.A.) Inc.Inventors: Karl G. Untch, Stefan H. Unger, Brian Lewis
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Patent number: 4145443Abstract: 1-Alkylamino-3-(?2-(endobicyclo?3.1.0!-hex-6-yl)ethylaminocarbonyl!naphthyl oxy)-2-propanols and methods for preparing these compounds are disclosed. The compounds are useful in the treatment of hypertension and abnormal heart conditions in mammals. These compounds are prepared by the treatment of the corresponding 1,2-epoxy-3-?2-(endobicyclo?3.1.0!hex-6-yl)ethylaminocarbonyl!naphthyloxy) -propane with an alkylamine having the desired alkyl substituent or by base or acid hydrolysis of the corresponding 2-optionally substituted -3-alkyl-5-(?2-(endobicyclo?3.1.0!hex-6-yl)ethylaminocarbonyl!naphthyloxym ethyl)oxazolidine. These latter compounds can be prepared by condensing a hydroxy-substituted naphthalene with a 3-alkyl-5-tosyloxymethyloxazolidine such substituted or unsubstituted at the 2-position or alternatively, by treating the former aminopropanol compounds of the present invention with an aldehyde having the desired substituent.Type: GrantFiled: October 31, 1977Date of Patent: March 20, 1979Assignee: Syntex (U.S.A.) Inc.Inventors: Karl G. Untch, Stefan H. Unger
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Patent number: 4123550Abstract: 1-Alkylamino-3-([2-(endobicyclo[3.1.0]hex-6-yl)ethylaminocarbonyl]thienylox y)-2-propanols and methods for preparing these compounds are disclosed. The compounds are useful in the treatment of hypertension and abnormal heart conditions in mammals. These compounds are prepared by the treatment of the corresponding 1,2-epoxy-3-[2-(endobicyclo[3.1.0]hex-6-yl)ethylaminocarbonyl]heterocyclic aryloxy)propane with an alkylamine having the desired alkyl substituent or by base or acid hydrolysis of the corresponding 2-optionally substituted-3-alkyl-5-([2-(endobicyclo[3.1.0]hex-6-yl)ethylaminocarbonyl]h eterocyclic aryloxymethyl)oxazolidine. These latter compounds can be prepared by condensing a halo-substituted thiophene with a 3-alkyl-5-hydroxymethyloxazolidine such substituted or unsubstituted at the 2-position or alternatively, by treating the former aminopropanol compounds of the present invention with an aldehyde having the desired substituent.Type: GrantFiled: October 31, 1977Date of Patent: October 31, 1978Assignee: Syntex (U.S.A.) Inc.Inventors: Karl G. Untch, Stefan H. Unger, Brian Lewis
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Patent number: 4064258Abstract: 1-Alkylamino-3-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxy)-2-propanol; 5-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxymethylene-N-alkyloxazolid ine and/or 2-substituted oxazolidine derivatives thereof, and methods of making such compounds. The compounds exhibit cardiovascular activity and are useful in the treatment of abnormal heart conditions in mammals. The compounds are also useful in the treatment of hypertension in mammals. The 5-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazoli dines and derivatives are also intermediates for the 1-alkylamino-3-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxy)-2-propanol s. The 1-alkylamino-3-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxy)-2-propanol s can be prepared by base or acid hydrolysis of the corresponding 5-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazoli dine or derivative; or by treatment of the corresponding 3-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxy)-2,3-epoxypropane with the desired alkylamine.Type: GrantFiled: July 19, 1976Date of Patent: December 20, 1977Assignee: Syntex (U.S.A.) Inc.Inventors: Brian Lewis, Stefan H. Unger, Karl G. Untch
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Patent number: 4064257Abstract: 1-Alkylamino-3-(5-alkynylaminocarbonylthiazol-2-yloxy)-2-propanol; 5-(5-alkynylaminocarbonyl-thiazol-2-yloxymethylene)-N-alkyloxazolidine and/or 2-substituted oxazolidine derivatives thereof, and methods of making such compounds. The compounds exhibit cardiovascular activity and are useful in the treatment of abnormal heart conditions in mammals. The compounds are also useful in the treatment of hypertension in mammals. The 5-(5-alkynyl-aminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazolidines and derivatives are also intermediates for the 1-alkylamino-3-(5-alkynylaminocarbonylthiazol-2-yloxy)-2-propanols. The 1-alkylamino-3-(5-alkynylaminocarbonylthiazol-2-yloxy)-2-propanols can be prepared by base or acid hydrolysis of the corresponding 5-(5-alkynylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazolidine or derivative; or by treatment of the corresponding 3-(5-alkynylaminocarbonylthiazol-2-yloxy)-2,3-epoxypropane with the desired alkylamine.Type: GrantFiled: July 19, 1976Date of Patent: December 20, 1977Assignee: Syntex (U.S.A.) Inc.Inventors: Belig M. Berkoz, Brian Lewis, Stefan H. Unger
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Patent number: 4064259Abstract: 1-Alkylamino-3-(5-alkenylaminocarbonylthiazol-2-yloxy)-2-propanol; 5-(5-alkenylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazolidine and/or 2-substituted oxazolidine derivatives thereof, and methods of making such compounds. The compounds exhibit cardiovascular activity and are useful in the treatment of abnormal heart conditions in mammals. The compounds are also useful in the treatment of hypertension in mammals. The 5-(5-alkenylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazolidines and derivatives are also intermediates for the 1-alkylamino-3-(5-alkenylaminocarbonylthiazol-2-yloxy)-2-propanols. The 1-alkylamino-3-(5-alkenylaminocarbonylthiazol-2-yloxy)-2-propanols can be prepared by base or acid hydrolysis of the corresponding 5-(5-alkenylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazolidine or derivative; or by treatment of the corresponding 3-(5-alkenylaminocarbonylthiazol-2-yloxy)-2,3-epoxypropane with the desired alkylamine.Type: GrantFiled: July 19, 1976Date of Patent: December 20, 1977Assignee: Syntex (U.S.A.) Inc.Inventors: Belig M. Berkoz, Brian Lewis, Stefan H. Unger