Patents by Inventor Karl G. Untch
Karl G. Untch 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: 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: 4172949Abstract: Compounds of the formula ##STR1## wherein R is hydrogen or methyl; R.sup.1 is hydrogen, C.sub.1 to C.sub.8 linear or branched alkyl or C.sub.1 to C.sub.8 linear or branched alkanoyl; X is oxygen or sulfur; R.sup.2 is selected from the group hydrogen, C.sub.1 to C.sub.18 linear or branched alkyl and the radicals --(CH.sub.2).sub.n --NR.sup.3 R.sup.4, --CH.sub.2 --CH(OH)--CH.sub.2 --OH or a ketal thereof formed from the aldehyde or ketone R.sup.5 R.sup.6 CO, wherein R.sup.3 and R.sup.4 are each independently C.sub.1 to C.sub.6 linear or branched alkyl or R.sup.3 and R.sup.4 taken together with the nitrogen atom of the first radical are attached to form a 5- or 6-membered heterocyclic ring, R.sup.5 and R.sup.6 are each independently hydrogen, C.sub.1 to C.sub.6 linear or branched alkyl, phenyl or benzyl or R.sup.5 and R.sup.Type: GrantFiled: June 28, 1978Date of Patent: October 30, 1979Assignee: Syntex (U.S.A.) Inc.Inventors: James P. Dunn, Peter H. Nelson, Karl G. Untch
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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: 4131746Abstract: (dl)-13-Substituted sulfinyl-prostaglandin-like [(dl)-2.alpha.-substituted-3.beta.-(1.alpha.-substituted sulfinyl-trans-2-alkenyl)-1-oxygenated cyclopentane and (dl)-2.alpha.-substituted-3.beta.-(1.alpha.-substituted sulfinyl-trans-2-alkenyl)-4-oxygenated-1-oxygenated cyclopentane] compounds exhibit prostaglandin-like biological properties and are also useful intermediates in the preparation of known prostaglandins.Type: GrantFiled: January 7, 1977Date of Patent: December 26, 1978Assignee: Syntex (USA) Inc.Inventors: Karl G. Untch, Gilbert J. Stork
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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: 4112114Abstract: Esters of 2-substituted-5-oxo-5H-dibenzo[a,d]cycloheptenes represented by the following formula: ##STR1## where R' is --CH.sub.2 --CH.dbd.CH.sub.2, --CH.sub.2 --CH(OH)--CH.sub.2 OH, ##STR2## where Y is either O or S, or ##STR3## where R.sup.4 and R.sup.5 are independently hydrogen, alkyl having 1 to 6 carbon atoms, phenyl, or benzyl, or together R.sup.4 and R.sup.5 form an alkylene bridge having 4, 5 or 6 carbon atoms; one of R.sup.2 and R.sup.3 is hydrogen and the other is hydrogen, methyl, or ethyl, or together R.sup.2 and R.sup.3 are methylene. The compounds have anti-inflammatory, analgesic, and antipyretic activities and, accordingly, are useful in the treatment of inflammation, pain and/or pyrexia.Type: GrantFiled: September 2, 1977Date of Patent: September 5, 1978Assignee: Syntex (U.S.A.) Inc.Inventors: Peter H. Nelson, Karl G. Untch
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Patent number: 4100174Abstract: 2-(5H-Dibenzo[a,d]cyclohepten-5-on-2-yl) acetic, propionic and butyric acids, are prepared from glycidonitrile intermediates.Type: GrantFiled: December 6, 1976Date of Patent: July 11, 1978Assignee: Syntex (U.S.A.) Inc.Inventors: Peter H. Nelson, Karl G. Untch
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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: 4059611Abstract: 2-(5H-Dibenzo[a,d]cyclohepten-5-on-2-yl) acetic, propionic and butyric acid, and esters and salts thereof, are prepared by oxidation of non-ketonic intermediates.Type: GrantFiled: July 6, 1976Date of Patent: November 22, 1977Assignee: Syntex (U.S.A.) Inc.Inventors: Peter H. Nelson, Karl G. Untch
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Patent number: 4054579Abstract: 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)acetic, propionic and butyric acids, and esters and salts thereof, are prepared by solvolysis of nitrile or amide intermediates, or of ketal-protected nitrile, amide, acid, ester or salt intermediates.Type: GrantFiled: June 21, 1976Date of Patent: October 18, 1977Assignee: Syntex (U.S.A.) Inc.Inventors: Peter H. Nelson, Karl G. Untch, James P. Dunn
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Patent number: 4051260Abstract: 2-Substituted-5-oxo-5H-dibenzo[a,d]cycloheptenes represented by the following formula: ##STR1## where one of R.sup.2 and R.sup.3 is hydrogen, and the other is hydrogen, methyl, or ethyl, or together R.sup.2 and R.sup.3 are methylene; and R' and R.sup.4 are alkoxy, or together R' and R.sup.4 are .dbd.O, .dbd.NOH, .dbd.NNHCONH.sub.2, or alkylenedioxy of the formula --O--CH.sub.2 --(CR.sup.5.sub.2).sub.n --CH.sub.2 --O-- where n.sub.5 is O-2, R.sup.5 is hydrogen or methyl when n is 1, and R.sup.5 is hydrogen when n is 2, or one of R' and R.sup.4 is --OH and the other is (SO.sub.3 Y) where Y is sodium or potassium. The compounds have anti-inflammatory, analgesic and anti-pyretic activities and, accordingly, are useful in the treatment of inflammation, pain and pyrexia.Type: GrantFiled: April 8, 1976Date of Patent: September 27, 1977Assignee: Syntex (U.S.A.) Inc.Inventors: Peter H. Nelson, Karl G. Untch
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Patent number: 4049697Abstract: (dl)-13-Substituted sulfinyl-prostaglandin-like [(dl)-2.alpha.-substituted-3.beta.-(1.alpha.-substituted sulfinyl-trans-2-alkenyl)-1-oxygenated cyclopentane and (dl)-2.alpha.-substituted-3.beta.-(1.alpha.-substituted sulfinyl-trans-2-alkenyl)-4-oxygenated-1-oxygenated cyclopentane] compounds exhibit prostaglandin-like biological properties and are also useful intermediates in the preparation of known prostaglandins.Type: GrantFiled: April 5, 1976Date of Patent: September 20, 1977Assignee: Syntex (U.S.A.) Inc.Inventors: Karl G. Untch, Gilbert J. Stork
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Patent number: 4046801Abstract: 13-Cis prostaglandin derivatives; cis-octenol ether copper.sup.(I) lithium reagents and methods of making such reagents and using the reagents to prepare the 13-cis prostaglandin derivatives. The 13-cis prostaglandin derivatives exhibit prostaglandin-like pharmacological properties and are further useful as intermediates for the corresponding prostaglandin isomers having the normal 13-trans configuration.Type: GrantFiled: December 9, 1974Date of Patent: September 6, 1977Assignee: Syntex (U.S.A.) Inc.Inventors: Arthur F. Kluge, Karl G. Untch, John H. Fried
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Patent number: 4041173Abstract: A compound selected from the group of compounds represented by the formula ##STR1## R is hydrogen, alkyl having 1 to 12 carbon atoms, or ##STR2## where n is an integer of 2 to 4 inclusive and R.sup.4 and R.sup.5 are independently lower alkyl of 1 to 6 carbon atoms inclusive or together R.sup.4 and R.sup.5 and the nitrogen atom to which they are attached form a heterocyclic ring having 5 to 6 total ring atoms;R.sup.1 is at the 7, 8 or 9 position and is halogen, hydroxy, lower alkoxy of 1 to 6 carbon atoms inclusive, or lower alkyl of 1 to 4 carbons atoms, inclusive;The dotted lines may be an additional, optional bond between the carbon atoms at the 10- and 11 positions; andThe pharmaceutically acceptable salts thereof. The compounds are used pharmaceutically to treat allergic reactions and autoimmune diseases.Type: GrantFiled: October 6, 1975Date of Patent: August 9, 1977Assignee: Syntex (U.S.A.) Inc.Inventors: Peter H. Nelson, Karl G. Untch
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Patent number: 4038299Abstract: 2-Substituted-5-oxo-5H-dibenzo [a,d] cycloheptenes represented by the following formula: ##STR1## where one of R.sup.2 and R.sup.3 is hydrogen, and the other is hydrogen, methyl, or ethyl, or together R.sup.2 and R.sup.3 are methylene; the dotted line represents an optional, additional bond between the carbon atoms at the 10- and 11-positions; and the pharmaceutically acceptable esters and ethers thereof. The compounds have anti-inflammatory, analgesic, and antipyretic activities and, accordingly, are useful in the treatment of inflammation, pain and pyrexia.Type: GrantFiled: March 8, 1976Date of Patent: July 26, 1977Assignee: Syntex (U.S.A.) Inc.Inventors: Peter H. Nelson, Karl G. Untch
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Patent number: 4035509Abstract: 2-Substituted-5-oxo-5H-dibenzo[a,d]cycloheptenes represented by the following formula: ##STR1## where R' is hydrogen, alkyl having 1 to 12 carbon atoms, or ##STR2## where n is an integer from 2 to 4, inclusive, and R.sup.4 and R.sup.5 are independently lower alkyl having 1 to 6 carbon atoms or together R.sup.4 and R.sup.5 and the nitrogen atom to which they are attached form a heterocyclic ring having 5 or 6 total ring atoms; and the pharmaceutically acceptable salts thereof. The compounds are useful in the treatment of auto-immune diseases and allergic reactions.Type: GrantFiled: March 31, 1975Date of Patent: July 12, 1977Assignee: Syntex (U.S.A.) Inc.Inventors: Peter H. Nelson, Karl G. Untch
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Patent number: 4033978Abstract: 3-Carboxy-5-substituted-thiacycl[2.2.2]azines of the formula: ##STR1## wherein R is phenyl or phenyl monosubstituted in the meta or para position with fluoro, chloro, lower alkyl of from 1 to 4 carbon atoms or lower alkoxy of from 1 to 4 carbon atoms, and the pharmaceutically acceptable salts thereof.These compounds are useful as anticomplimentary agents, specifically for the treatment of inflammatory conditions, auto-immune diseases, allergic reactions and vascular diseases.Type: GrantFiled: August 15, 1975Date of Patent: July 5, 1977Assignee: Syntex (U.S.A.) Inc.Inventors: Karl G. Untch, John O. Gardner
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Patent number: 4020094Abstract: 2-Substituted-5-oxo-5H-dibenzo[a,d]cycloheptenes represented by the following formula: ##STR1## where R' is hydrogen, alkyl having 1 to 12 carbon atoms, or ##STR2## where n is an integer from 2 to 4, inclusive, and R.sup.4 and R.sup.5 are independently lower alkyl having 1 to 6 carbon atoms or together R.sup.4 and R.sup.5 and the nitrogen atom to which they are attached form a heterocyclic ring having 5 or 6 total ring atoms; one of R.sup.2 and R.sup.3 is hydrogen and the other is hydrogen, methyl, or ethyl, or together R.sup.2 and R.sup.3 are methylene; and the pharmaceutically acceptable salts thereof. The compounds have anti-inflammatory, analgesic, and antipyretic activities and, accordingly, are useful in the treatment of inflammation, pain and/or pyrexia.Type: GrantFiled: March 24, 1975Date of Patent: April 26, 1977Assignee: Syntex (U.S.A.) Inc.Inventors: Peter H. Nelson, Karl G. Untch
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Patent number: 4011241Abstract: 2-(5H-Dibenzo[a,d]cyclohepten-5-on-2-yl)acetic, propionic and butyric acids, are prepared from glycidonitrile intermediates. The acid products exhibit anti-inflamatory, analgesic and anti-pyretic activity.Type: GrantFiled: September 8, 1975Date of Patent: March 8, 1977Assignee: Syntex (U.S.A.) Inc.Inventors: Peter H. Nelson, Karl G. Untch