Patents by Inventor Harold C. Kluender
Harold C. Kluender 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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Preparation and use of 1,5,6,7-tetrahydropyrrolo[3,2-c]pyridine derivatives for treatment of obesity
Patent number: 7071207Abstract: This invention relates to 1,5,6,7-tetrahydropyrrolo[3,2-c]pyridine derivatives which have been found to suppress appetite and induce weight loss. The invention also provides methods for synthesis of the compounds, pharmaceutical compositions comprising the compounds, and methods of using such compositions for inducing weight loss and treating obesity and obesity-related disorders.Type: GrantFiled: September 24, 2002Date of Patent: July 4, 2006Assignee: Bayer Pharmaceuticals CorporationInventors: Roger A. Smith, Stephen J. O'Connor, Wai C. Wong, Soongyu Choi, Harold C. Kluender, Jianmei Fan, Zhonghua Zhang, Rico C. Lavoie, Brent L. Podlogar -
Publication number: 20040267028Abstract: This invention relates to pyrrole derivatives which have been found to suppress appetite and induce weight loss. The invention also provides methods for synthesis of the compounds, pharmaceutical compositions comprising the compounds, and methods of using such compositions for inducing weight loss and treating obesity and obesity-related disorders.Type: ApplicationFiled: March 5, 2004Publication date: December 30, 2004Inventors: Roger A Smith, Harold C. Kluender, Ning Su, Rico C. Lavoie, Jianmei Fan
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Patent number: 5266713Abstract: Aryl alkenoic acid derivatives, and physiologically acceptable salts thereof, are provided which are potent leukotriene antagonists and may be used for the treatment of circulatory diseases and preferably for respiratory diseases such as asthma. The derivatives have a general formula I ##STR1## in which X is --S--,W is CH.dbd.CH;o is 1 to 4;n is 2 to 6;m is 0 to 2;T and Z, same or different, represent oxygen or a direct bond;R.sup.2 and R.sup.3, represent hydrogen, or fluorine;A represents carboxyl, CO.sub.2 R.sub.4.sup.4, wherein R.sup.4 is lower alkylR is ##STR2## wherein Y represents carboxyl, CO.sub.2 R.sup.4, wherein R.sup.4 is lower alkylR.sup.7 and R.sup.8, same or different, represent H or lower alkyl;R.sup.9 represents --OH, --O-alkyl, NH.sub.2 or a NHCH.sub.2 CO.sub.2 H group; andR.sup.10 R3 is H.Type: GrantFiled: August 12, 1992Date of Patent: November 30, 1993Assignee: Miles Inc.Inventors: Trevor S. Abram, Peter Norman, Stephen R. Tudhope, Harold C. Kluender, Robert N. Schut, Heinrich Meier, Ulrich Rosentreter
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Patent number: 5221760Abstract: An alkenoic acid derivative of the formula ##STR1## in which X and Y are identical or different and represent sulfur, sulfoxide, sulfone, an alkylene chain, --SCH.sub.2 --, or oxygen or a direct bond,W represents --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --,o represents a number 1 to 5,A and B are identical or different and represent carboxyl, carboxymethylene, tetrazolyl or tetrazolylmethylene, or --CO.sub.2 R.sup.9 or --CH.sub.2 CO.sub.2 R.sup.9 or --CONR.sup.10 R.sup.11 or nitrilen represents a number 1 to 10,m represents a number 0 to 7,T and Z are identical or different and represent oxygen or a direct bond andR.sup.2, R.sup.3, R.sup.8 are identical or different and represent hydrogen, alkyl, alkoxy, halogen, trifluoromethyl, trifluoromethoxy, cyano or nitro andR.sup.9 is lower alkyl and R.sup.10 and R.sup.11 are hydrogen, lower alkyl, alkylsulfonyl or arylsulfonyl or together are an alkylene chain to form a ringand pharmaceutically acceptable salts thereof.Type: GrantFiled: June 1, 1992Date of Patent: June 22, 1993Assignee: Bayer AktiengesellschaftInventors: Ulrich Rosentreter, Harold C. Kluender, Trevor S. Abram, Peter Norman, Steven R. Tudhope
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Patent number: 5159097Abstract: An alkenoic acid derivative of the formula ##STR1## in which X and Y are identical or different and represent sulfur, sulfoxide, sulfone, an alkylene chain, --SCH.sub.2 --, or oxygen or a direct bond,W represents --CH.dbd.CH--or --CH.sub.2 --CH.sub.2 --,o represents a number 1 to 5,A and B are identical or different and represent carboxyl, carboxymethylene, tetrazolyl or tetrazolylmethylene, or --CO.sub.2 R.sup.9 or --CH.sub.2 CO.sub.2 R.sup.9 or --CONR.sup.10 R.sup.11 or nitrilen represents a number 1 to 10,m represents a number 0 to 7,T and Z are identical or different and represent oxygen or a direct bond andR.sup.2, R.sup.3, R.sup.8 are identical or different and represent hydrogen, alkyl, alkoxy, halogen, trifluoromethyl, trifluoromethoxy, cyano or nitro andR.sup.9 is lower alkyl and R.sup.10 and R.sup.11 are hydrogen, lower alkyl, alkylsulfonyl or arylsulfonyl or together are an alkylene chain to form a ringand pharmaceutically acceptable salts thereof.Type: GrantFiled: November 26, 1990Date of Patent: October 27, 1992Assignee: Bayer AktiengesellschaftInventors: Ulrich Rosentreter, Harold C. Kluender, Trevor S. Abram, Peter Norman, Steven R. Tudhope
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Patent number: 5041638Abstract: An alkenoic acid derivative of the formula ##STR1## in which X and Y are identical or different and represent sulfur, sulfoxide, sulfone, an alkylene chain, --SCH.sub.2 --, or oxygen or a direct bond,W represents --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --,o represents a number 1 to 5,A and B are identical or different and represent carboxyl, carboxymethylene, tetrazolyl or tetrazolylmethylene, or --CO.sub.2 R.sup.9 or --CH.sub.2 CO.sub.2 R.sup.9 or --CONR.sup.10 R.sup.11 or nitrilen represents a number 1 to 10,m represents a number 0 to 7,T and Z are identical or different and represent oxygen or a direct bond andR.sup.2, R.sup.3, R.sup.8 are identical or different and represent hydrogen, alkyl, alkoxy, halogen, trifluoromethyl, trifluoromethoxy, cyano or nitro andR.sup.9 is lower alkyl and R.sup.10 and R.sup.11 are hydrogen, lower alkyl, alkylsulfonyl or arylsulfonyl or together are an alkylene chain to form a ringand pharmaceutically acceptable salts thereof.Type: GrantFiled: May 9, 1989Date of Patent: August 20, 1991Assignee: Bayer AktiengesellschaftInventors: Ulrich Rosentreter, Harold C. Kluender, Trevor S. Abram, Peter Norman, Steven R. Tudhope
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Patent number: 4833157Abstract: A therapeutic method for inhibiting gastric secretion in an individual for whom such therapy is indicated is disclosed. The method comprises administering to such an individual an effective inhibitory amount of certain derivatives of 15-deoxy-16-hydroxy-prostaglandin E.sub.1 esters.Type: GrantFiled: January 4, 1988Date of Patent: May 23, 1989Assignee: Miles Inc.Inventors: Harold C. Kluender, Warren D. Woessner, William G. Biddlecom
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Patent number: 4742080Abstract: A therapeutic method for producing bronchodilation in an individual for whom such therapy is indicated is disclosed. The method comprises administering to said individual an effective bronchodilation amount of certain derivatives of 15-deoxy-16-hydroxy-prostaglandin E.sub.1 esters.Type: GrantFiled: March 15, 1985Date of Patent: May 3, 1988Assignee: Miles Laboratories, Inc.Inventors: Harold C. Kluender, Warren D. Woesner, William G. Biddlecom
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Patent number: 4543421Abstract: An improved method for the preparation of prostaglandin analogs which comprises preparation of two equivalents of an alkyl or alkenyl lithium reagent in an aprotic solvent mixture such as pentane or hexane and tetrahydrofuran, conversion of said reagent by addition of 1 equivalent of copper (I) cyanide to a copper reagent, conversion of said copper reagent to the blocked prostaglandin analog by the addition of a 2-alkylcyclopent-2-en-1-one reagent and quenching of the resultant reaction mixture with aprotic media or an active acylating agent and finally optionally deblocking the resultant product is disclosed. This method is an improvement over previous methods in that more modest temperatures and less hazardous and/or less complex reagents are used and in that for some analogs the method is shorter than previous methods.Type: GrantFiled: May 11, 1983Date of Patent: September 24, 1985Assignee: Miles Laboratories, Inc.Inventors: Paul F. Corey, Harold C. Kluender
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Patent number: 4415592Abstract: Analogues of PGE.sub.1 having the structural formula, ##STR1## in which J is R-hydroxymethylene or S-hydroxymethylene; R.sub.1 is hydrogen; R.sub.2 is hydrogen or together with R.sub.4 is a methylene chain of 2 to 3 carbon atoms such that a cycloalkyl of 5 to 6 carbon atoms inclusive is formed; R.sub.3 is hydrogen or methyl, or together with R.sub.4 is a methylene or a lower alkylated methylene chain of 2 to 5 carbon atoms such that a cycloalkyl or a lower alkylated cycloalkyl of 4 to 7 carbon atoms inclusive is formed, or together with R.sub.4 is bicycloalkyl or bicycloalkenyl moiety having the formula: ##STR2## such that a bicycloalkyl or bicycloalkenyl compound is formed, wherein m and n are integers having a value from 0 to 3, p is an integer having a value from 0 to 4 and q is an integer having a value of from 1 to 4 and wherein the double bond of such bicycloalkenyl is in the m, n, p, or q bridge; R.sub.4 is hydrogen or methyl or together with R.sub.2 or R.sub.Type: GrantFiled: March 12, 1982Date of Patent: November 15, 1983Assignee: Miles Laboratories, Inc.Inventors: Harold C. Kluender, Warren D. Woessner, William G. Biddlecom
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Patent number: 4336404Abstract: Disclosed are 1-acyloxy-15-deoxy-16-hydroxy prostaglandin E.sub.1 analogs characterized by the formula: ##STR1## Compounds corresponding to the foregoing formula in which R.sub.1 can be H or methyl and R.sub.2 can be C(CH.sub.3).sub.2 (CH.sub.2).sub.2 CH.sub.3 or (CH.sub.2).sub.3 CH.sub.3 are variously useful as inhibitors of gastric secretion and as bronchodilators.Type: GrantFiled: May 29, 1980Date of Patent: June 22, 1982Assignee: Miles Laboratories, Inc.Inventors: William G. Biddlecom, Harold C. Kluender, Warren D. Woessner
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Patent number: 4331688Abstract: Analogues of PGE.sub.1 having the structural formula, ##STR1## in which J is R-hydroxymethylene or S-hydroxymethylene; R.sub.1 is hydrogen; R.sub.2 is hydrogen or together with R.sub.4 is a methylene chain of 2 to 3 carbon atoms such that a cycloalkyl of 5 to 6 carbon atoms inclusive is formed; R.sub.3 is hydrogen or methyl, or together with R.sub.4 is a methylene or a lower alkylated methylene chain of 2 to 5 carbon atoms such that a cycloalkyl or a lower alkylated cycloalkyl of 4 to 7 carbon atoms inclusive is formed, or together with R.sub.4 is bicycloalkyl or bicycloalkenyl moiety having the formula: ##STR2## such that a bicycloalkyl or bicycloalkenyl compound is formed, wherein m and n are integers having a value from 0 to 3, p is an integer having a value from 0 to 4 and q is an integer having a value of from 1 to 4 and wherein the double bond of such bicycloalkenyl is in the m, n, p, or q bridge; R.sub.4 is hydrogen or methyl or together with R.sub.2 or R.sub.Type: GrantFiled: December 12, 1980Date of Patent: May 25, 1982Assignee: Miles Laboratories, Inc.Inventors: Harold C. Kluender, Warren D. Woessner, William G. Biddlecom
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Patent number: 4275224Abstract: Analogues of PGE.sub.1 having the structural formula, ##STR1## in which J is R-hydroxymethylene or S-hydroxymethylene; R.sub.1 is hydrogen; R.sub.2 is hydrogen or together with R.sub.4 is a methylene chain of 2 to 3 carbon atoms such that a cycloalkyl of 5 to 6 carbon atoms inclusive is formed; R.sub.3 is hydrogen or methyl, or together with R.sub.4 is a methylene or a lower alkylated methylene chain of 2 to 5 carbon atoms such that a cycloalkyl or a lower alkylated cycloalkyl of 4 to 7 carbon atoms inclusive is formed, or together with R.sub.4 is bicycloalkyl or bicycloalkenyl moiety having the formula: ##STR2## such that a bicycloalkyl or bicycloalkenyl compound is formed, wherein m and n are integers having a value from 0 to 3, p is an integer having a value from 0 to 4 and q is an integer having a value of from 1 to 4 and wherein the double bond of such bicycloalkenyl is in the m, n, p, or q bridge; R.sub.4 is hydrogen or methyl or together with R.sub.2 or R.sub.Type: GrantFiled: December 26, 1978Date of Patent: June 23, 1981Assignee: Miles Laboratories, Inc.Inventors: Harold C. Kluender, Warren D. Woessner, William G. Biddlecom
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Patent number: 4220795Abstract: Novel C15 cyclobutyl analogs or derivatives of prostaglandins of the E-, A- and F-classes are useful modifiers of smooth muscle activity. The compounds have valuable pharmacological properties such as platelet antiaggregating agents, gastric antisecretory agents and brochodilating agents.Type: GrantFiled: August 14, 1978Date of Patent: September 2, 1980Assignee: Miles Laboratories, Inc.Inventors: Harold C. Kluender, Henry C. Arndt
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Patent number: 4171331Abstract: Disclosed are trans 1 & 2-di(loweralkyl)phosphono; 1 & 2-chloro, bromo and iodo; 1 & 2-thio and 1 & 2-amino analogues of E.sub.1, A.sub.1, F.sub.1.alpha., F.sub.1.beta., 11 deoxy E.sub.1, 11 deoxy F.sub.1.beta., and 11 deoxy F.sub.1.alpha. prostaglandins.The prostaglandins of this invention are variously useful as antithrombic agents, bronchodilators such as in the treatment of asthma, inhibitors of gastric secretion and as antihypertensive agents. Certain of the prostaglandins disclosed herein are useful as precursors for prostaglandins having one or more of the foregoing utilities.Type: GrantFiled: June 5, 1978Date of Patent: October 16, 1979Assignee: Miles Laboratories, Inc.Inventors: William G. Biddlecom, Harold C. Kluender, Warren D. Woessner
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Patent number: 4159998Abstract: Disclosed is an improved process for the preparation of 2-(7-hydroxyalkyl)-4R, 4S or 4RS -hydroxy-cyclopent-2-enone corresponding to the formula ##STR1## wherein m is an integer from 2 to 4. The compounds prepared by this process are useful as precursors in the preparation of carbinol PGE.sub.1 analogues having utility as bronchodilators and inhibitors of gastric secretion.Type: GrantFiled: September 11, 1978Date of Patent: July 3, 1979Assignee: Miles Laboratories, Inc.Inventor: Harold C. Kluender
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Patent number: 4158018Abstract: Disclosed are trans, 3-oxa carbinol analogs of prostaglandin E.sub.1 represented by the formula: ##STR1## wherein R is n-alkyl of 4-6 carbon atoms, cycloalkyl of 5 to 7 carbon atoms or 1,1-dimethylalkyl of 6 to 8 carbon atoms. Particular compounds corresponding to the above formula are variously useful as antithrombotic agents due to their ability to inhibit platelet aggregation, bronchodilators, inhibitors of gastric secretion and anti-hypertensive agents.Type: GrantFiled: September 12, 1978Date of Patent: June 12, 1979Assignee: Miles Laboratories, Inc.Inventor: Harold C. Kluender
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Patent number: 4149017Abstract: Useful intermediates in the preparation of bicycloalkyl analogues or derivatives of prostaglandins are represented by the formula ##STR1## wherein: X is an iodo or bromo radical;A is an acid-labile hydroxyl-protecting group;G is an integer having a value of from 0 to 10; andB is selected for the class of bicycloalkyl radicals of the formula: ##STR2## WHERE M AND P ARE INTEGERS HAVING A VALUE OF FROM 1 TO 4; N IS AN INTEGER HAVING A VALUE OF FROM 0 TO 4 SUCH THAT THE SUM OF M, N AND P IS GREATER THAN OR EQUAL TO 3 AND THE POINT OF ATTACHMENT OF THE ALKYL CHAIN (CH.sub.2).sub.g to the bicycloalkyl radical is in the (CH.sub.2).sub.m bridge or in the bridgehead position.Type: GrantFiled: July 25, 1977Date of Patent: April 10, 1979Assignee: Miles Laboratories, Inc.Inventors: Warren D. Woessner, Charles J. Sih, Harold C. Kluender, Henry C. Arndt, William G. Biddlecom
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Patent number: 4132738Abstract: Analogues of PGE.sub.1 having the structural formula, ##STR1## in which J is R-hydroxymethylene or S-hydroxymethylene; R.sub.1 is hydrogen; R.sub.2 is hydrogen or together with R.sub.4 is a methylene chain of 2 to 3 carbon atoms such that a cycloalkyl of 5 to 6 carbon atoms inclusive is formed; R.sub.3 is hydrogen or methyl, or together with R.sub.4 is a methylene or a lower alkylated methylene chain of 2 to 5 carbon atoms such that a cycloalkyl or a lower alkylated cycloalkyl of 4 to 7 carbon atoms inclusive is formed, or together with R.sub.4 is bicycloalkyl or bicycloalkenyl moiety having the formula: ##STR2## SUCH THAT A BICYCLOALKYL OR BICYCLOALKENYL COMPOUND IS FORMED, WHEREIN M AND N ARE INTEGERS HAVING A VALUE FROM 0 TO 3, P IS AN INTEGER HAVING A VALUE FROM 0 TO 4 AND Q IS AN INTEGER HAVING A VALUE OF FROM 1 TO 4 AND WHEREIN THE DOUBLE BOND OF SUCH BICYCLOALKENYL IS IN THE M, N, P, OR Q BRIDGE; R.sub.4 is hydrogen or methyl or together with R.sub.2 or R.sub.Type: GrantFiled: February 23, 1978Date of Patent: January 2, 1979Assignee: Miles Laboratories, Inc.Inventors: Harold C. Kluender, Warren D. Woessner, William G. Biddlecom
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Patent number: 4127727Abstract: Depentyl analogues of prostaglandins A, E, and F having no C-16 to C-20 carbon atoms. The analogues correspond to the formula ##STR1## wherein: L is methylene, ethylene, or trimethylene;K is ethylene or cis-vinylene;M is carbonyl, .alpha.-hydroxymethylene, or .beta.-hydroxymethylene;N is methylene or methine, provided that N is methine only if P is methine and M is carbonyl;P is methylene, ethylene, .alpha.-hydroxymethylene or methine, provided that P is methine only if N is methine; and,R is carboxyl; hydroxymethylene, alkoxycarbonyl, the alkyl portion of said alkoxycarbonyl being a lower alkyl, or a pharmacologically acceptable non-toxic carboxy salt.The analogues are prepared by first converting a trans-1-iodo-3-alkoxy-1-propene to the corresponding lithio compound. This lithio compound then combines with the hexamethylphosphorous triamide complex of copper (I) pentyne to give an alkenylcopper species.Type: GrantFiled: April 14, 1977Date of Patent: November 28, 1978Assignee: Miles Laboratories, Inc.Inventor: Harold C. Kluender