Patents Assigned to SynPhar Laboratories, Inc.
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Patent number: 6153616Abstract: A compound of formula I, or an optical isomer or pharmaceutically acceptable salt thereof, ##STR1## is disclosed as well as a pharmaceutical composition and a method of treating or preventing a fungal infection using the compound.Type: GrantFiled: January 16, 1998Date of Patent: November 28, 2000Assignees: Synphar Laboratories, Inc., Taiho Pharmaceuticals Co., Ltd.Inventors: Mohsen Daneshtalab, Yadagiri Bathini, Dai Nguyen, Inderjit Sidhu, Mark Abel, Chan Ha, Sameeh Salama, Jehangir Khan, Ronald Micetich, Tetsuo Furukawa, Norio Unemi
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Patent number: 6133485Abstract: The asymmetric production of pure diastereomeric (2R,3R), (2R,3S), (2S,3R) and (2S,3S)-2-aryl-1-substituted butan-2,3-diols from the derivatives of lactic acid.Type: GrantFiled: April 15, 1998Date of Patent: October 17, 2000Assignees: Synphar Laboratories, Inc., Taiho Pharmaceuticals Co., Ltd.Inventors: Inder Pal Singh, Inderjit Sidhu, Bhupinder Palak, Ronald G. Micetich
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Patent number: 5994340Abstract: New 2-oxo-1-azetidine sulfonic acid derivatives with an aminoalkyl substituted "anti" (E-isomer) oxyimino group in the acylamino substituent at the 3 position of the monobactam ring. These compounds are potent inhibitors of bacterial .beta.-lactamases. These compounds can be used in combination with .beta.-lactam antibiotics to increase the effectiveness of the .beta.-lactam antibiotics in fighting infection caused by .beta.-lactamase producing bacteria.Type: GrantFiled: August 29, 1997Date of Patent: November 30, 1999Assignee: SynPhar Laboratories, Inc.Inventors: Samarendra N. Maiti, Oludotun A. Phillips, Eduardo L. Setti, Andhe V. Narender Reddy, Ronald G. Micetich, Fusahiro Higashitani, Chieko Kunugita, Koichi Nishida, Tatsuya Uji
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Patent number: 5994342Abstract: The present invention is based on the discovery that certain 3-(substituted methyl)-4-oxa-1-azabicyclo[3.2.0]heptan-7-one derivatives of formula I or a pharmaceutically acceptable salt thereof are useful as antitumor agents against sensitive and resistant tumor cells. ##STR1## Wherein X is NH or O, and R is defined in the specification.Type: GrantFiled: April 4, 1997Date of Patent: November 30, 1999Assignees: Taiho Pharmaceutical Co., Ltd., Synphar Laboratories Inc.Inventors: Rajeshwar Singh, Tomohiro Yamashita, Charles Fiakpui, George Thomas, Chan Ha, Hiroshi Matsumoto, Toshio Otani, Shinji Oie, Ronald Micetich
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Patent number: 5986108Abstract: Disclosed herein are azetidin-2-one compounds which exhibit excellent cysteine proteinase inhibitory activity. The compounds are 4-substituted-3-{1 or 2 amino acid residue}-azetidin-2-ones of forumula I ##STR1## wherein AAR is a 1 or 2 acid residue, and R.sub.1 and R.sub.2 are as defined herein. The compounds can be used in the treatment of various diseases such as muscular dystrophy, bone resorption disorders, myocardial infarction and cancer metastasis.Type: GrantFiled: September 8, 1997Date of Patent: November 16, 1999Assignee: Synphar Laboratories, Inc.Inventors: Rajeshwar Singh, Nian En Zhou, Deqi Guo, Ronald G. Micetich
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Patent number: 5959123Abstract: The present invention is based on the discovery that certain 3,4-disubstituted-azetidin-2-one derivatives exhibit excellent cysteine proteinase inhibitory activity which can be used for treatment of different diseases such as muscular dystrophy, myocardial infarction, bone resorption, arthritis, cancer metastasis, pulmonary emphysema, septic shock, cerebral ischemia, memory function, Alzheimer and cataract, malaria, glomerular basement membrane degradation, bacterial infection, inflammatory diseases, parasitic infections, and viral infections. In accordance to the present invention, there is provided a 3,4-disubstituted-azetidin-2-one derivatives of formula I, wherein R.sub.1, R.sub.2 and R.sub.3 are as defined herein, or a pharmaceutically acceptable salt thereof.Type: GrantFiled: September 22, 1997Date of Patent: September 28, 1999Assignee: Synphar Laboratories, Inc.Inventors: Rajeshwar Singh, Nian E. Zhou, Deqi Guo, Ronald G. Micetich
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Patent number: 5888998Abstract: A compound of formula (I) ##STR1## wherein R.sub.1 is selected from the group consisting of 2-thienyl, 2-furyl, 2-pyrrolyl, 1-methyl-2-pyrrolyl, 2-amino-1-thiazolyl and 5-isothiazolyl;R.sub.2 is selected from the group consisting of: ##STR2## and M is hydrogen or a pharmaceutically acceptable cation; wherein the oxyimino fragment (.dbd.N--OR.sub.2) in formula (I) is in the `anti` orientation.Type: GrantFiled: April 24, 1997Date of Patent: March 30, 1999Assignees: Synphar Laboratories, Inc., Taiho Pharmaceutical Co., Ltd.Inventors: Samarendra N. Maiti, Eduardo L. Setti, Oludotun A. Phillips, Andhe V. Narender Reddy, Ronald G. Micetich, Rajeshwar Singh, Fusahiro Higashitani, Chieko Kunugita, Koichi Nishida, Tatsuya Uji
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Patent number: 5652234Abstract: The present invention relates to the use of 3-(7-oxo-1-aza-4-oxabicyclo[3.2.0]hept-3-yl)alanine derivatives of formula (I) or a pharmaceutically acceptable salt thereof, as antitumor agents. ##STR1## Wherein R is: hydrogen or COOR.sub.2 wherein R.sub.2 is C.sub.1 -C.sub.3 alkyl group which may be substituted with aryl group.Wherein R.sub.1 is:hydrogen or C.sub.1 -C.sub.3 alkyl group which may be substituted with one or two aryl groups.Type: GrantFiled: October 6, 1995Date of Patent: July 29, 1997Assignees: Taiho Pharmaceutical Co., Limited, SynPhar Laboratories, Inc.Inventors: Rajeshwar Singh, Tomohiro Yamashita, Charles Fiakpui, George Thomas, Chan Ha, Hiroshi Matsumoto, Toshio Otani, Shinji Oie, Ronald Micetich
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Patent number: 5616606Abstract: Oligopeptide antiretroviral agents are represented by formula (I), wherein A is a moiety bearing a positive charge and of a size which avoids steric inhibition of binding of said compound to nucleic acid sequences associated with the cellular activity of retroviruses; R.sub.1 is a moiety derived from a dicarboxylic acid; Hew is a five-membered heterocyclic moiety; y and z are independently 0, 1, 2 or 3; and x is 0 or 1. These compounds exhibit antiretroviral activity, especially against Human Immunodeficiency Virus (HIV).Type: GrantFiled: August 2, 1995Date of Patent: April 1, 1997Assignees: Synphar Laboratories, Inc., Taiho Pharmaceutical Co., Ltd.Inventors: J. William Lown, Ronald G. Micetich
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Patent number: 5561126Abstract: The present invention relates to the use of 4-oxa-1-azabicyclo [3,2,0] heptan-7-one derivatives of formula (I) or a pharmaceutically acceptable salt thereof, as antitumor agents. ##STR1## Wherein R is --OCOR.sub.1 group wherein R.sub.1 is hydrogen atom, a C.sub.1-9 alkyl group which may be substituted by either one or two substituents selected together from halogen atom, hydroxy, carboxy group or (3RS,5SR)-(4-oxo-1-azabicyclo[3,2,0]heptan-7-one-3-yl) methyloxycarbonyl, a C.sub.2-17 alkenyl group, which may be substituted by carboxy group or (3RS,5SR)-(4-oxa-1-azabicyclo [3,2,0]heptan-7-one-3-yl)methyloxycarbonyl, A C.sub.2-4 alkynyl group, a C.sub.3-6 cycloalkyl group which may be substituted by carboxy group or phenyl group which may have 1, 2 or 3 substituents selected from the group consisting of cyano group, halogen atom, C.sub.1-6 alkoxy group which may be substituted by carboxy group, C.sub.1-6 alkyl group, amino group or hydroxy group.--OR.sub.2 wherein R.sub.Type: GrantFiled: March 16, 1995Date of Patent: October 1, 1996Assignees: Taiho Pharmaceutical Co., Ltd., Synphar Laboratories, Inc.Inventors: Toshio Otani, Shinji Oie, Hiroshi Matsumoto, Mark Tempest, Ronald Micetich, Rajeshwar Singh, Tomohiro Yamashita
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Patent number: 5530134Abstract: A process for the synthesis of compounds of the formulas Ia and Ib below, wherein R.sub.1, R.sub.2, and R.sub.3, which are the same or different, are each selected from hydrogen and C.sub.1 -C.sub.4 alkyl, including the compound Anabaseine (Ia, wherein R.sub.1 =R.sub.2 R.sub.3 =H) (3,4,5,6-tetrahydro-2', 3'-bipyridine), the process comprising reacting sodium salt of .delta.-valerolactone with substituted ethyl nicotinate derivative to produce the Claisen product sodium 3-nicotinoyl-2-tetrahydropyranone enolate derivative, heating the sodium 3-nicotinoyl-2-tetrahydropyranone enolate derivative with concentrated HCl to produce 3-(5-chloro-1-pentanone-1-yl) pyridine derivative, dissolving the 3-(5-chloro-1-pentanone-1-yl) pyridine derivative in ethanol and then heating the 3-(5-chloro-1-pentanone-1-yl) pyridine derivative in ethanol with ethanolic ammonia solution in a sealed container to produce the compound Ia.Type: GrantFiled: September 6, 1994Date of Patent: June 25, 1996Assignee: Synphar Laboratories Inc.Inventors: Mohsen Daneshtalab, Dai Nguyen, Inderjit Sidhu, Ronald G. Micetich
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Patent number: 5502068Abstract: The invention is directed to novel cyclopropylpyrroloindole-oligopeptide compounds which are useful as anticancer agents. The novel cyclopropylpyrroloindole-oligopeptide compounds have the following general structure: ##STR1## wherein, Het.sup.1 and Het.sup.2 are individually selected from the group consisting of pyrrole, imidazole, triazole, thiophene, furan, thiazole, oxazole and pyrazole,R is selected from the group consisting of a valence bond; a C.sub.1 -C.sub.6 alkyl; a C.sub.2 -C.sub.6 alkenyl; a C.sub.2 -C.sub.6 alkynyl; and an ortho, meta or para linked aromatic group,A is selected from the group consisting of a C.sub.1 -C.sub.6 alkyl group; an amidine or derivative thereof; a guanidine; a secondary, tertiary or quaternary ammonium salt; and a sulfonium salt,n is 0 to 3, andm is 0 to 3.Type: GrantFiled: January 31, 1995Date of Patent: March 26, 1996Assignee: Synphar Laboratories, Inc.Inventors: J. William Lown, Yuqiang Wang, Weide Luo
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Patent number: 5478947Abstract: A high purity triazole is obtained by the reaction of a hydrazide of the general formula II and glyoxal followed by the treatment of the intermediate of general formula IV with ammonia. The total process is done in one pot and does not require the isolation of the intermediate IV. The triazole (I) is isolated by distillation. Synthesis of various N.sub.1 -substituted triazoles is also described following the same procedure.Type: GrantFiled: July 29, 1994Date of Patent: December 26, 1995Assignee: SynPhar Laboratories, Inc.Inventors: Inder P. Singh, Paul Spevak, Bhupinder Palak, Samuel Amedjo, Ronald J. Micetich
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Patent number: 5446037Abstract: This invention relates to 2-[(substituted)methylene]cephalosporin sulfones and in particular 2-[(heteroaryl substituted)methylene]cephalosporin sulfones which are effective elastase inhibitors as well as effective thrombin inhibitors and therefore are useful as anti-inflammatory, anti-degenerative and anti-thrombin agents.Type: GrantFiled: December 13, 1993Date of Patent: August 29, 1995Assignee: Synphar Laboratories, Inc.Inventors: Samarendra Maiti, Charles Fiakpui, A. V. N. Reddy, David Czajkowski, Paul Spevak, Harninder Atwal, Ronald G. Micetich
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Patent number: 5439904Abstract: 2-spiro (2'-spirocycloalkyl) cyclopropyl cephalosporin sulfone compounds, methods of treating patients for elastase inhibition, and processes for preparing such compounds.Type: GrantFiled: December 7, 1993Date of Patent: August 8, 1995Assignee: Synphar Laboratories, Inc.Inventors: Samarendra N. Maiti, Charles Y. Fiakpui, Andhe V. N. Reddy, David P. Czajkowski, Ronald G. Micetich
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Patent number: 5342846Abstract: Substituted quinoline compounds and intermediates thereto, processes for producing those compounds and intermediates, pharmaceutical compositions using those compounds, methods for treating bacterial infections using those compounds, and methods for disinfecting using those compounds.Type: GrantFiled: July 14, 1992Date of Patent: August 30, 1994Assignee: SynPhar Laboratories, Inc.Inventors: Rajeshwar Singh, Rakhshandeh Fathi-Afshar, Inder P. Singh, George Thomas, Thomas R. Doerksen, Maya P. Singh, Ronald G. Micetich
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Patent number: 5264429Abstract: Derivatives of 2-spirocyclopropyl cephalosporin sulfone of the structural formula I ##STR1## are provided which are useful as potent elastase inhibitors.Type: GrantFiled: August 20, 1991Date of Patent: November 23, 1993Assignee: SynPhar Laboratories, Inc.Inventors: Samarendra N. Maiti, David Czajkowski, Paul Spevak, Kazuo Adachi, Ronald G. Micetich
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Patent number: 5264430Abstract: Derivatives of 2-spirocyclopropyl cephalosporin sulfone of the structural formula I ##STR1## are provided which are useful as potent elastase inhibitors.Type: GrantFiled: April 8, 1991Date of Patent: November 23, 1993Assignee: SynPhar Laboratories, Inc.Inventors: Samarendra N. Maiti, David Czajkowski, Paul Spevak, Kazuo Adachi, Ronald G. Micetich
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Patent number: 5120750Abstract: A 1,4-dihydropyridine derivative of the formula I: ##STR1## is provided in which: A is an azole moiety;R is a C.sub.1 -C.sub.4 alkyl group;X is --CH.sub.2 --, --S--, --SO-- or --SO.sub.2 --;n is 5, 6, 7 or 8; andPh is a phenyl group substituted once or twice by NO.sub.2, CF.sub.3 or Cl groups.Type: GrantFiled: April 11, 1990Date of Patent: June 9, 1992Assignee: SynPhar Laboratories, Inc.Inventors: Mohsen Daneshtalab, Dai Q. Nguyen, Ronald G. Micetich