Bicyclo Ring System Which Is 1-oxa-4-aza-bicyclo(3.2.0)hep-tane (including Unsaturated) Patents (Class 540/347)
  • Patent number: 10231970
    Abstract: A method of synthesizing a heteropolycycle, the method involving: reacting a bisepoxide with a first heteroatom nucleophile, to obtain a mixture comprising a diol compound; and further processing, to obtain the heteropolycycle with at least two heteroatoms within its polycyclic backbone, wherein each nitrogen within the polycyclic backbone of the heteropolycycle is introduced into the polycyclic backbone via an amine nucleophile.
    Type: Grant
    Filed: September 30, 2015
    Date of Patent: March 19, 2019
    Assignee: NV Heterocycles
    Inventor: Derek Alton Lightner
  • Patent number: 8802387
    Abstract: The present invention relates to compounds for and a method of detecting beta-lactamase activity in a sample. The sample is contacted with a nanoparticulate tag. The nanoparticulate tag comprises a metal or a combination of metals, or it comprises a nanotube of a metal, boron nitride and/or carbon. The respective metal is capable of forming one of a covalent bond, a coordinative bond and a non-covalent interaction with a thio or a seleno group. The sample is contacted with a compound of one of general formulas (I)-(III) and (VII)-(IX). At least one beta-lactam moiety of the compound is cleaved by the beta-lactamase activity in the sample. As a result a cleavage moiety Z-A-Z, Z-A-Z—R15, Z-A-Z—R16, Z-A-Z—R17, Z-A-Z—R18 or Z-G-N(R8)R9 is released that is immobilised on the surface of the nanoparticulate tag by a covalent bond via a Z atom. The presence of beta-lactamase activity is determined based on the presence of the cleavage moiety immobilized onto the surface of the nanoparticulate tag.
    Type: Grant
    Filed: April 30, 2008
    Date of Patent: August 12, 2014
    Assignee: Nanyang Technological University
    Inventors: Bengang Xing, Xianfeng Huang, Tingting Jiang, Rongrong Liu
  • Patent number: 7812014
    Abstract: The present invention provides a compound of formula I wherein one of A and B is hydrogen and the other an optionally substituted fused bicyclic heteroaryl group as defined herein; X is O; R5 is H, C1-C6 alkyl, C5-C6 cycloalkyl, or CHR3OCOC1-C6 alkyl; and R3 is hydrogen, C1-C6 alkyl, C5-C6 cycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl; or a pharmaceutically acceptable salt thereof; and pharmaceutical compositions and the use thereof for the treatment of bacterial infection or disease in a patient in need thereof.
    Type: Grant
    Filed: August 21, 2008
    Date of Patent: October 12, 2010
    Assignee: Wyeth LLC
    Inventors: Aranapakam Mudumbai Venkatesan, Tarek Suhayl Mansour, Takao Abe, Itsuki Yamamura, Tsuyoshi Takasaki, Atul Agarwal, Osvaldo Dos Santos, Fuk-Wah Sum, Yang-I Lin
  • Publication number: 20100228015
    Abstract: This invention relates to novel homotopic prodrugs and medicaments and methods for their preparation, testing and use. In one embodiment, the homotopic prodrug has the general formula wherein is a biologically-active moiety comprising a carboxylic acid functional group, and Rb is a homotopically-symmetrical alcohol bonded to the biologically-active moiety through the carboxylic acid functional group to form an ester linkage, as well as optical isomers, enantiomers, pharmaceutically acceptable salts, biohydrolyzable amides, esters, and imides thereof and combinations thereof.
    Type: Application
    Filed: April 23, 2010
    Publication date: September 9, 2010
    Inventors: Mitchell A. deLong, Jill M. McFadden, Susan M. Royalty, Eric J. Toone, Jeffrey D. Yingling
  • Patent number: 7691842
    Abstract: The present invention provides a compound of formula I, pharmaceutical compositions and the use thereof for the treatment of bacterial infection or disease in a patient in need thereof, wherein one of A and B denotes hydrogen and the other an optionally substituted fused tricyclic heteroaryl group; and X is O.
    Type: Grant
    Filed: August 7, 2008
    Date of Patent: April 6, 2010
    Assignee: Wyeth LLC
    Inventors: Aranapakam Mudumbai Venkatesan, Tarek Suhayl Mansour, Takao Abe, Ado Mihira, Atul Agarwal, Hideki Ushirogochi, Yansong Gu, Satoshi Tamai, Fuk-Wah Sum
  • Publication number: 20090275065
    Abstract: The present invention relates to compounds for and a method of detecting beta-lactamase activity in a sample. The sample is contacted with a nanoparticulate tag. The nanoparticulate tag comprises a metal or a combination of metals, or it comprises a nanotube of a metal, boron nitride and/or carbon. The respective metal is capable of forming one of a covalent bond, a coordinative bond and a non-covalent interaction with a thio or a seleno group. The sample is contacted with a compound of one of general formulas (I)-(III) and (VII)-(IX). At least one beta-lactam moiety of the compound is cleaved by the beta-lactamase activity in the sample. As a result a cleavage moiety Z-A-Z, Z-A-Z-R15, Z-A-Z-R16, Z-A-Z-R17, Z-A-Z-R18 or Z-G-N(R8)R9 is released that is immobilised on the surface of the nanoparticulate tag by a covalent bond via a Z atom. The presence of beta-lactamase activity is determined based on the presence of the cleavage moiety immobilized onto the surface of the nanoparticulate tag.
    Type: Application
    Filed: April 30, 2008
    Publication date: November 5, 2009
    Inventors: Bengang XING, Xianfeng Huang, Tingting Jiang, Rongrong Liu
  • Publication number: 20080318921
    Abstract: The present invention provides a compound of formula I, pharmaceutical compositions and the use thereof for the treatment of bacterial infection or disease in a patient in need thereof.
    Type: Application
    Filed: August 7, 2008
    Publication date: December 25, 2008
    Applicant: Wyeth
    Inventors: Aranapakam Mudumbai Venkatesan, Tarek Suhayl Mansour, Takao Abe, Ado Mihira, Atul Agarwal, Hideki Ushirogochi, Yansong Gu, Satoshi Tamai, Fuk-Wah Sum
  • Publication number: 20080312203
    Abstract: The present invention provides a compound of formula I wherein one of A and B is hydrogen and the other an optionally substituted fused bicyclic heteroaryl group; and X is O, pharmaceutical compositions and the use thereof for the treatment of bacterial infection or disease in a patient in need thereof.
    Type: Application
    Filed: August 21, 2008
    Publication date: December 18, 2008
    Applicant: Wyeth
    Inventors: Aranapakam Mudumbai Venkatesan, Tarek Suhayl Mansour, Takao Abe, Itsuki Yamamura, Tsuyoshi Takasaki, Atul Agarwal, Osvaldo Dos Santos, Fuk-Wah Sum, Yang-I Lin
  • Patent number: 7459551
    Abstract: The present invention provides a method for preparing a ?-lactam compound of the following Formula (3), which comprises the step of reacting a compound of the following Formula (1) with a trialkyl phosphite represented by the formula (R5O)3P (wherein R5 represents an ethyl group, etc.) in an amount of 2 to 5 moles per mole of the compound and the step of heating the resulting reaction mixture in a diluent, wherein said method is characterized by having the step of completely removing unreacted trialkyl phosphite from the reaction mixture prior to the step of heating. (wherein X represents S, etc., Y represents N, etc., n represents 0 or 1, R1 represents an optionally substituted alkyl group containing 1 to 10 carbon atoms, etc., R2 and R3 each represent an optionally substituted alkyl or heterocyclic group, etc., and R4 represents an alkenyloxy group containing 1 to 6 carbon atoms, etc., provided that R1 and R2 may together form a ?-lactam ring, etc.
    Type: Grant
    Filed: March 26, 2003
    Date of Patent: December 2, 2008
    Assignee: Asubio Pharma Co., Ltd.
    Inventor: Akira Kaneko
  • Patent number: 7247622
    Abstract: An oxapenem compound which is, or is capable of forming, a zwitterion of formula wherein R is a C1-C8 branched or straight chain alkyl group which is substituted by a protonated nitrogen base. The compounds find particular use as high bioavailability ?-lactamase inhibitors.
    Type: Grant
    Filed: October 11, 2001
    Date of Patent: July 24, 2007
    Assignee: Amura Limited
    Inventors: Hans Rudolf Pfaendler, Iain Nelson Simpson
  • Patent number: 7018997
    Abstract: The present invention provides a compound of formula I, pharmaceutical compositions and the use thereof for the treatment of bacterial infection or disease in a patient in need thereof. wherein one of A and B denotes hydrogen and the other an optionally substituted fused tricyclic heteroaryl group; and X is S.
    Type: Grant
    Filed: May 1, 2003
    Date of Patent: March 28, 2006
    Assignee: Wyeth
    Inventors: Aranapakam Mudumbai Venkatesan, Tarek Suhayl Mansour, Takao Abe, Ado Mihira, Atul Agarwal, Hideki Ushirogochi, Yansong Gu, Satoshi Tamai, Fuk-Wah Sum
  • Publication number: 20040259856
    Abstract: The present invention is based on the discovery that certain fermentation products of the marine actinomycete strains CNB392 and CNB476 are effective inhibitors of hyperproliferative mammalian cells. The CNB392 and CNB476 strains lie within the family Micromonosporaceae, and the generic epithet Salinospora has been proposed for this obligate marine group. The reaction products produced by this strain are classified as salinosporamides, and are particularly advantageous in treating neoplastic disorders due to their low molecular weight, low IC50 values, high pharmaceutical potency, and selectivity for cancer cells over fungi.
    Type: Application
    Filed: April 30, 2004
    Publication date: December 23, 2004
    Applicant: The Regents of the University of California
    Inventors: William Fenical, Paul Jensen, Tracy Mincer, Robert H.R. Feling
  • Publication number: 20040138196
    Abstract: The present invention is based on the discovery that certain fermentation products of the marine actinomycete strains CNB392 and CNB476 are effective inhibitors of hyperproliferative mammalian cells. The CNB392 and CNB476 strains lie within the family Micromonosporaceae, and the generic epithet Salinospora has been proposed for this obligate marine group. The reaction products produced by this strain are classified as salinosporamides, and are particularly advantageous in treating neoplastic disorders due to their low molecular weight, low IC50 values, high pharmaceutical potency, and selectivity for cancer cells over fungi.
    Type: Application
    Filed: June 20, 2003
    Publication date: July 15, 2004
    Inventors: William Fenical, Paul Jensen, Tracy Mincer, Robert H.R. Feling
  • Publication number: 20040043978
    Abstract: The present invention provides a compound of formula I, pharmaceutical compositions and the use thereof for the treatment of bacterial infection or disease in a patient in need thereof.
    Type: Application
    Filed: May 1, 2003
    Publication date: March 4, 2004
    Applicant: Wyeth
    Inventors: Aranapakam Mudumbai Venkatesan, Tarek Suhayl Mansour, Takao Abe, Ado Mihira, Atul Agarwal, Hideki Ushirogochi, Yansong Gu, Satoshi Tamai, Fuk-Wah Sum
  • Publication number: 20030203886
    Abstract: Use of the 2-amino-2,4,4-trimethylpentane salt of clavulanic acid as an intermediate in the production of pharmaceutically acceptable salts of clavulanic acid.
    Type: Application
    Filed: May 13, 2003
    Publication date: October 30, 2003
    Inventors: Franz Krenmueller, Harald Summer
  • Publication number: 20030166923
    Abstract: A compound of formula (I): 1
    Type: Application
    Filed: December 19, 2002
    Publication date: September 4, 2003
    Applicant: SmithKline Beecham p.l.c.
    Inventors: Eric Hunt, Steven Coulton, Jeremy David Hinks, Stephen Frederick Moss, Stephen Christopher Martin Fell, Alfred John Eglington, George Burton
  • Publication number: 20030149016
    Abstract: Disclosed is a novel carbapenem derivative having a substituted imidazo[5,1-b]thiazole group at the 2-position on the, carbapenem ring have high anti-microbial activities against &bgr;-lactamase producing bacteria, MRSA, resistant-Pseudomonas aeruginosa, PRSP, enterococci, and influenza, and high stabilities to DHP-1.
    Type: Application
    Filed: August 14, 2002
    Publication date: August 7, 2003
    Inventors: Yuko Kano, Toshiro Sasaki, Yumiko Sambongi, Kiyoshi Tanabe, Yoshihisa Akiyama, Hideo Kitagawa, Takahisa Maruyama, Hiromasa Takizawa, Takashi Ando, Kazuhiro Aihara, Kunio Atsumi, Katsuyoshi Iwamatsu, Takashi Ida
  • Publication number: 20030119085
    Abstract: Substrates for &bgr;-lactamase of the general formula I 1
    Type: Application
    Filed: October 24, 2002
    Publication date: June 26, 2003
    Applicant: The Regents of the University of California
    Inventors: Roger Y. Tsien, Gregor Zlokarnik
  • Publication number: 20030027809
    Abstract: An objective of the present invention is to provide carbapenem derivatives which have potent antibiotic activity against MRSA, PRSP, Influenzavirus, and &bgr;-lactamase-producing bacteria and are stable against DHP-1.
    Type: Application
    Filed: July 25, 2002
    Publication date: February 6, 2003
    Inventors: Yuko Kano, Takahisa Maruyama, Yumiko Sambongi, Kazuhiro Aihara, Kunio Atsumi, Kastuyoshi Iwamatsu, Takashi Ida
  • Publication number: 20030022881
    Abstract: An objective of the present invention is to provide carbapenem derivatives which have potent antibiotic activity against MRSA, PRSP, Influenzavirus, and &bgr;-lactamase-producing bacteria and are stable against DHP-1.
    Type: Application
    Filed: July 25, 2002
    Publication date: January 30, 2003
    Inventors: Yuko Kano, Takahisa Maruyama, Yasuo Yamamoto, Eiki Shitara, Toshiro Sasaki, Kazuhiro Aihara, Kunio Atsumi, Katsuyoshi Iwamatsu, Takashi Ida
  • Publication number: 20030004337
    Abstract: Lactams, libraries of lactams, and an efficient method of synthesizing a lactam, including a &ggr;-lactam, in which an a-diazoacetamide of the general structure (I) is reacted under conditions promoting intramolecular C-H insertion, for example in the presence of a rhodium salt such as Rh2(OAc)4, 1
    Type: Application
    Filed: May 4, 2001
    Publication date: January 2, 2003
    Inventors: Kyung Woon Jung, Cheol Hwan Yoon
  • Patent number: 6495539
    Abstract: Compounds of the formula and the salts, esters and amides thereof wherein Z is S, SO, SO2 or O; each of R1, R2 and R3 is independently H or substituted or unsubstituted alkyl (1-10C), substituted or unsubstituted alkenyl, substituted or unsubstituted acyl (2-11C), substituted or unsubstituted aryl (6-14C), substituted or unsubstituted arylcarbonyl (7-15C), substituted or unsubstituted arylalkyl (7-15C), substituted or unsubstituted pyridyl wherein substituents on any alkyl, alkenyl, or acyl moiety are selected from the group consisting of halo, and RO, wherein R is H or alkyl (1-6C), and substituents on any aryl or pyridyl moiety are selected from the group consisting of halo, and RO, where R is H or alkyl (1-6C), —CN and —CF3; with the proviso that R1 is not H and R1 and R3 are not identical and with the proviso that in formula (1), the B ring may contain one double bond that is located between positions 2 and 3, and in formula (2), the B ring may contain one double bond tha
    Type: Grant
    Filed: February 19, 1999
    Date of Patent: December 17, 2002
    Assignee: Washington University
    Inventors: Scott J. Hultgren, Fredrik Almqvist, Gabriel Soto
  • Publication number: 20020004595
    Abstract: A new crystalline form of potassium clavulanate is disclosed. Also disclosed are a process for producing the new crystalline form of potassium clavulanate, pharmaceutical compositions containing it and methods of treating bacterial infections.
    Type: Application
    Filed: July 19, 2001
    Publication date: January 10, 2002
    Applicant: SmithKline Beecham Corporation
    Inventors: Paul Gerard Butterly, Gilroy John Keohane, Esin Fatma Kosal
  • Publication number: 20010036940
    Abstract: Use of the 2-amino-2,4,4-trimethylpentane salt of clavulanic acid as an intermediate in the production of pharmaceutically acceptable salts of clavulanic acid.
    Type: Application
    Filed: June 26, 2001
    Publication date: November 1, 2001
    Inventors: Franz Krenmueller, Harald Summer
  • Publication number: 20010025104
    Abstract: ? Provided is a process for purification of clavulanic acid or a pharmaceutically acceptable salt or ester thereof, including adding an additional solvent to a solution of clavulanic acid in water immiscible solvent; contacting the solution with an amine; isolating the amine salt of the clavulanic acid formed; and converting the amine into clavulanic acid or a pharmaceutically acceptable salt or ester thereof.
    Type: Application
    Filed: December 14, 2000
    Publication date: September 27, 2001
    Applicant: Lek Pharmaceutical & Chemical Co. DD.
    Inventor: Egidij Capuder
  • Patent number: 6255479
    Abstract: A method for preparing an &agr;-oxolactam comprising, reacting a corresponding &agr;-diazolactam with an oxygen donor, in the presence of a transition metal catalyst, to yield the corresponding &agr;-oxolactam.
    Type: Grant
    Filed: December 29, 1998
    Date of Patent: July 3, 2001
    Assignee: Research Corporation Technologies, Inc.
    Inventors: John D. Buynak, Akireddy Srinivasa Rao
  • Patent number: 5998612
    Abstract: A method of preparing intermediates for carbapenem antibiotics characterized by treating a N-deprotected acetoxy conpound of the formula: ##STR1## in the presence of a Lewis acid or a silylating agent to yeild an intermediate; and cyclizing the intermediate in the presence of rhodium (II) acetate to form a bicyclic ketoester.
    Type: Grant
    Filed: June 12, 1992
    Date of Patent: December 7, 1999
    Inventors: Paul J. Reider, Edward J. J. Grabowski
  • Patent number: 5994342
    Abstract: 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: Grant
    Filed: April 4, 1997
    Date of Patent: November 30, 1999
    Assignees: 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
  • Patent number: 5905076
    Abstract: Novel 6-substituted amino-4-oxa-1-azabicyclo?3,2,0!heptan-7-one compounds, as well as the pharmaceutically acceptable salts thereof and diastereoisomers thereof, of formula I, ##STR1## are disclosed, which exhibit excellent cysteine protease inhibitory activity and may be used for treatment of different diseases such as muscular dystrophy, arthritis, myocardial infarction, Alzheimer's disease, bacterial infection, common cold, osteroporosis and cancer metastasis.
    Type: Grant
    Filed: April 8, 1997
    Date of Patent: May 18, 1999
    Assignee: National Research Council of Canada
    Inventors: Rajeshwar Singh, Nian E. Zhou, Degi Guo, Alan Cameron, Jadwiga Kaleta, Enrico Purisima, Robert Menard, Ronald George Micetich
  • Patent number: 5703231
    Abstract: The present invention provides a process for making a compound having a structure according to Formula (I) ##STR1## wherein A.sup.1, A.sup.2 and A.sup.3 are independently carbon or nitrogen and R.sup.1, R.sup.3, R.sup.4 and R.sup.6 are known quinolone substituents; and wherein one of R.sup.1, R.sup.3 or R.sup.6 may be a lactam-containing moiety;or a protected form, salt, pharmaceutically-acceptable salt, biohydrolyzable ester, or solvate thereof;the process comprising reacting one or more organosilicon compounds with a compound having a structure according to Formula (II) ##STR2## wherein A.sup.1, A.sup.2 and A.sup.3, R.sup.1, R.sup.3, R.sup.4 and R.sup.6 as described above; wherein one of R.sup.1, R.sup.3 or R.sup.6 may be a lactam-containing moiety; and X is a leaving group;or a protected form, salt, biohydrolyzable ester, or solvate thereof.
    Type: Grant
    Filed: November 14, 1996
    Date of Patent: December 30, 1997
    Assignee: The Procter & Gamble Company
    Inventors: Jared Lynn Randall, Jane Ellen Godlewski
  • Patent number: 5679789
    Abstract: Potassium clavulanate exists in a novel crystalline habit, namely in the form of rosettes, having improved processing properties. The novel form may, for example, be obtained by crystallization or recrystallization using inverse precipitation, preferably at 8.degree.-15.degree. C.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: October 21, 1997
    Assignee: Beecham Group, p.l.c.
    Inventors: Dennis Edward Clark, Shaukat Hussain Malik, Paul Gerard Butterly, Clive Elton Badman, Jeffrey David Haseler
  • Patent number: 5288861
    Abstract: Potassium clavulanate exists in a novel crystalline habit, namely in the form of rosettes, having improved processing properties. The novel form may, for example, be obtained by crystallization or recrystallization using inverse precipitation, preferably at 8.degree.-15.degree. C.
    Type: Grant
    Filed: November 18, 1992
    Date of Patent: February 22, 1994
    Assignee: Beecham Group plc
    Inventors: Dennis E. Clark, Shaukat H. Malik, Paul G. Butterly, Clive E. Badman, Jeffrey D. Haseler
  • Patent number: 5260438
    Abstract: A method for removing tri-substituted silyl group from .beta.-lactam compound having a tri-substituted silyl group-protecting hydroxy group, which comprises treating with an acid and a fluoride selected from alkali metal fluoride, alkaline earth metal fluoride and hydrogenfluoride of organic or inorganic amine, by which the tri-substituted silyl group can be easily and effectively removed under moderate conditions so that the desired compound can be obtained in high yield at low cost.
    Type: Grant
    Filed: April 27, 1993
    Date of Patent: November 9, 1993
    Assignee: Tanabe Seiyaku Co., Ltd.
    Inventors: Hiroshi Horikawa, Kazuhiko Kondo, Tameo Iwasaki
  • Patent number: 5096899
    Abstract: Compounds of the structural formulae ##STR1## and their pharmaceutically acceptable salts, esters and amide derivatives, in which R.sup.1 and R.sup.2, independently of one another, denote hydrogen or pharmaceutically acceptable groups which have 1 to 10 carbon atoms and are bonded to the remaining part of the molecule via carbon-carbon single bonds, and in which R.sup.3, R.sup.4 and R.sup.5, independently of one another, denote pharmaceutically acceptable groups which have 1 to 10 carbon atoms and are bonded to the remaining part of the molecule via carbon-carbon single bonds, are useful antibiotics.The trisubstitution by three groups R.sup.3, R.sup.4 and R.sup.5, which are bonded via carbon-carbon single bonds, results in a noticeable increase in the hydrolysis stability and thus also in the antibacterial action of axapenemcarboxylic acids.
    Type: Grant
    Filed: August 24, 1990
    Date of Patent: March 17, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans R. Pfaendler, Wolfram Hendel
  • Patent number: 5055573
    Type: Grant
    Filed: August 24, 1990
    Date of Patent: October 8, 1991
    Assignee: Merck & Co., Inc.
    Inventors: Lovji D. Cama, Burton G. Christensen
  • Patent number: 4877783
    Abstract: .beta.-Lactam antibiotics having an .alpha.-formamido substituent on the carbon atom adjacent to the carbonyl group of the .beta.-lactam ring and in particular bicyclic compounds having the partial structure: ##STR1## Intermediates and processes for the preparation of the compounds are further disclosed.
    Type: Grant
    Filed: January 24, 1985
    Date of Patent: October 31, 1989
    Assignee: Beecham Group p.l.c.
    Inventor: Peter H. Milner
  • Patent number: 4804658
    Abstract: This invention relates to novel imidazopyridine derivatives useful in the treatment of diseases or disorders mediated by platelet-activating factor. This invention further relates to pharmaceutical compositions of such imidazopyridine derivatives.
    Type: Grant
    Filed: September 15, 1986
    Date of Patent: February 14, 1989
    Assignee: G. D. Searle & Co.
    Inventors: Paul W. Manley, Roderick A. Porter
  • Patent number: 4654331
    Abstract: The (5-R-2-oxo-1,3-dioxolen-4-yl)methyl moiety: ##STR1## wherein R is loweralkyl of 1-6 carbon atoms, especially methyl or t-butyl; when utilized as an ester on a pharmaceutical having a carboxylic acid functionality, enhances oral absorption of the pharmaceutical. This effect is applicable to a broad range of pharmaceutically active substances, including antibiotics, and antihypertensives as well as other classes of therapeutic agents.
    Type: Grant
    Filed: August 23, 1984
    Date of Patent: March 31, 1987
    Assignee: Merck & Co., Inc.
    Inventor: Burton G. Christensen