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FR2456731A1 - Guanidino and amino benzoate(s) and phenyl sulphonate(s) - and related cpds. inhibit protease(s) and have bacteriostatic and fungistatic activity - Google Patents

Guanidino and amino benzoate(s) and phenyl sulphonate(s) - and related cpds. inhibit protease(s) and have bacteriostatic and fungistatic activity

Info

Publication number
FR2456731A1
FR2456731A1 FR7912395A FR7912395A FR2456731A1 FR 2456731 A1 FR2456731 A1 FR 2456731A1 FR 7912395 A FR7912395 A FR 7912395A FR 7912395 A FR7912395 A FR 7912395A FR 2456731 A1 FR2456731 A1 FR 2456731A1
Authority
FR
France
Prior art keywords
para
guanidino
substd
meta
cpds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
FR7912395A
Other languages
French (fr)
Inventor
Patrick Choay
Dominique Olliero
Edgar Sache
Camille Georges Wermuth
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Choay SA
Original Assignee
Choay SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Choay SA filed Critical Choay SA
Priority to FR7912395A priority Critical patent/FR2456731A1/en
Publication of FR2456731A1 publication Critical patent/FR2456731A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/26—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/18—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/22—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Peptides Or Proteins (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Substd.-arylamines and aryl-guanidines which inhibit protease (esp. serine-protease) activity and their enantiomers and acid addn. salts are new. Cpds have formula R1R2Ph-X-Y-Z (I), (where R1R2Ph-X- is known as the acylating part and -Y-2 as the acylated part of the molecule; R1 is opt. substd. guanidino (G) in position meta or para, primary amino in position meta or para, tert. amine having alkyl substituents in position para or nitro in position meta or para; R2 is alkoxy or when R1 is G then R2 may also be halo or alkyl in position meta or para according to whether the G gp. is meta or para; X is -CO- or -SO2-; Y is O, S or opt. substd. -NH-; Z is H (with the condition that when R1 is G it is in position 3 and that R2 is not halo in position 4), a cyclic group, esp. aryl (opt. substd. by guanidino, nitro or amino), a heterocyclic esp. opt. substd. pyrimidyl, morpholinyl or succinimide. R1 and R2 may also be H with the condition that they are not both H when Z does not contain a guanidino gp. Cpds. are protease inhibitors, which are particularly useful as inhibitors of serine proteases such as trypsin, plasmin and thrombin, bacteriostats and fungistats. (I) inhibit proteases by acylation of their active serine centre with the acylating part of the cpd., whilst the acylated part has excellent anticoagulant activity. The best bacteriostats have a lipophilic group on the non-acylating part and a meta- or para-guanidino gp. on the acylating part. Typical fungistats are diguanidines and cpds. have an ester gp. on the non-acylating part and a guanidino gp. on the acylating part. Activity tests are described.
FR7912395A 1979-05-16 1979-05-16 Guanidino and amino benzoate(s) and phenyl sulphonate(s) - and related cpds. inhibit protease(s) and have bacteriostatic and fungistatic activity Withdrawn FR2456731A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR7912395A FR2456731A1 (en) 1979-05-16 1979-05-16 Guanidino and amino benzoate(s) and phenyl sulphonate(s) - and related cpds. inhibit protease(s) and have bacteriostatic and fungistatic activity

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7912395A FR2456731A1 (en) 1979-05-16 1979-05-16 Guanidino and amino benzoate(s) and phenyl sulphonate(s) - and related cpds. inhibit protease(s) and have bacteriostatic and fungistatic activity

Publications (1)

Publication Number Publication Date
FR2456731A1 true FR2456731A1 (en) 1980-12-12

Family

ID=9225516

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7912395A Withdrawn FR2456731A1 (en) 1979-05-16 1979-05-16 Guanidino and amino benzoate(s) and phenyl sulphonate(s) - and related cpds. inhibit protease(s) and have bacteriostatic and fungistatic activity

Country Status (1)

Country Link
FR (1) FR2456731A1 (en)

Cited By (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62111963A (en) * 1985-11-12 1987-05-22 Ono Pharmaceut Co Ltd P-guanidinobenzoic acid thiophenyl ester derivative and pharmaceutical containing same
EP0229370A1 (en) * 1985-12-27 1987-07-22 Eisai Co., Ltd. Guanidinobenzoic ester derivative, a process for preparing same and pharmaceutical compositions containing same
EP0222608A3 (en) * 1985-11-12 1988-09-07 Ono Pharmaceutical Co., Ltd. Derivatives of p-guanidinobenzoic acid and pharmaceutical agents containing them as active ingredient
US4843094A (en) * 1985-11-12 1989-06-27 Ono Pharmaceutical Co., Ltd. Derivatives of p-guantidinobenzoic acid and pharmaceutical agents containing them as active ingredient
US4937370A (en) * 1987-06-02 1990-06-26 The Procter & Gamble Company Novel chromophores, sunscreen compositions and methods for preventing sunburn
US5138089A (en) * 1986-06-27 1992-08-11 The Procter & Gamble Company Chromophores, sunscreen compositions and methods for preventing sunburn
WO1992016503A1 (en) * 1991-03-25 1992-10-01 Boehringer Mannheim Gmbh New sulphonamides, process for preparing the same and medicaments containing these compounds
US5229107A (en) * 1986-06-27 1993-07-20 The Procter & Gamble Company Sunscreen agents, sunscreen compositions and methods for preventing sunburn
US5229106A (en) * 1986-06-27 1993-07-20 The Procter & Gamble Company Sunscreen agents, sunscreen compositions and method for preventing sunburn
US5230874A (en) * 1986-06-27 1993-07-27 The Procter & Gamble Company Sunscreen agents, sunscreen compositions and methods for preventing sunburn
US5243064A (en) * 1986-06-27 1993-09-07 The Procter & Gamble Company Chromophores, sunscreen compositions and methods for preventing sunburn
US5247084A (en) * 1985-11-12 1993-09-21 Ono Pharmaceutical Co., Ltd. Derivatives of p-guanidinobenzoic acid
US5352704A (en) * 1989-12-22 1994-10-04 Banyu Pharmaceutical Co., Ltd. Guanidinobenzene derivatives
WO1997036861A1 (en) * 1996-03-29 1997-10-09 G.D. Searle & Co. Meta-substituted phenylene sulphonamide derivatives
WO1997036858A1 (en) * 1996-03-29 1997-10-09 G.D. Searle & Co. Cyclopropyl alkanoic acid derivatives
FR2761061A1 (en) * 1997-03-20 1998-09-25 Synthelabo BENZENESULFONAMIDE DERIVATIVES, THEIR PREPARATION AND THERAPEUTIC USE THEREOF
WO2000017159A1 (en) * 1998-09-23 2000-03-30 Tularik Inc. Arylsulfonanilide ureas
JP3220225B2 (en) 1992-04-10 2001-10-22 小野薬品工業株式会社 Guanidinophenol derivatives
EP1285911A3 (en) * 1998-09-23 2003-03-26 Tularik Inc. Arylsulfonanilide ureas
WO2002070468A3 (en) * 2001-02-08 2003-09-04 Rotta Research Lab Novel benzamidine derivatives having anti-inflammatory and immunosuppressive activity
US6822001B2 (en) 2000-11-03 2004-11-23 Tularik Inc. Combination therapy using pentafluorobenzenesulfonamides and antineoplastic agents
WO2007143880A1 (en) * 2006-06-09 2007-12-21 Shanghai East Best Biopharmaceutical Enterprises Co., Ltd. Compounds for preventing and treating bacterial infection and its preparation and use
US7405227B2 (en) 2005-07-18 2008-07-29 Bipar Sciences, Inc. Treatment of cancer
US8048908B2 (en) 2006-07-13 2011-11-01 High Point Pharmaceuticals, Llc 11β-hydroxysteroid dehydrogenase type 1 active compounds
US8053431B2 (en) 2005-11-01 2011-11-08 High Point Pharmaceuticals, Llc Pharmaceutical use of substituted amides
US8053447B2 (en) 2006-04-07 2011-11-08 High Point Pharmaceuticals, Llc 11β-hydroxysteroid dehydrogenase type 1 active compounds
US8138342B2 (en) 2004-10-12 2012-03-20 High Point Pharmacueticals, LLC 11β-hydroxysteroid dehydrogenase type 1 active spiro compounds
US8143447B2 (en) 2006-09-05 2012-03-27 Bipar Sciences, Inc. Treatment of cancer
US8153798B2 (en) 2007-03-09 2012-04-10 High Point Pharmaceuticals, Llc Indole- and benzimidazole amides as hydroxysteroid dehydrogenase inhibitors
US8334305B2 (en) 2007-02-23 2012-12-18 High Point Pharmaceuticals, Llc N-adamantyl benzamides as inhibitors of 11-β-hydroxysteroid dehydrogenase
US8383820B2 (en) 2007-02-23 2013-02-26 High Point Pharmaceuticals, Llc N-adamantyl benzamides as inhibitors of 11-β-hydroxysteroid dehydrogenase
US8383683B2 (en) 2007-04-24 2013-02-26 High Point Pharmaceuticals, Llc Pharmaceutical use of substituted amides
GB2533925A (en) * 2014-12-31 2016-07-13 Univ Bath Antimicrobial compounds, compositions and methods
CN114805141A (en) * 2021-01-27 2022-07-29 中国科学院上海药物研究所 4-guanidinobenzoic acid aryl ester compound and application thereof in resisting SARS-CoV-2 virus
US11666888B2 (en) 2018-02-05 2023-06-06 Bio-Rad Laboratories, Inc. Chromatography resin having an anionic exchange-hydrophobic mixed mode ligand

Cited By (53)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5247084A (en) * 1985-11-12 1993-09-21 Ono Pharmaceutical Co., Ltd. Derivatives of p-guanidinobenzoic acid
EP0222608A3 (en) * 1985-11-12 1988-09-07 Ono Pharmaceutical Co., Ltd. Derivatives of p-guanidinobenzoic acid and pharmaceutical agents containing them as active ingredient
US4843094A (en) * 1985-11-12 1989-06-27 Ono Pharmaceutical Co., Ltd. Derivatives of p-guantidinobenzoic acid and pharmaceutical agents containing them as active ingredient
JPS62111963A (en) * 1985-11-12 1987-05-22 Ono Pharmaceut Co Ltd P-guanidinobenzoic acid thiophenyl ester derivative and pharmaceutical containing same
US5077428A (en) * 1985-11-12 1991-12-31 Ono Pharmaceutical Co., Ltd. Pharmacologically active derivatives of p-guanidinobenzoic acid
US5376655A (en) * 1985-11-12 1994-12-27 Ono Pharmaceutical Co., Ltd. Derivatives of p-guanidinobenzoic acid and pharmaceutical agents containing them as an active ingredient
EP0229370A1 (en) * 1985-12-27 1987-07-22 Eisai Co., Ltd. Guanidinobenzoic ester derivative, a process for preparing same and pharmaceutical compositions containing same
US4801603A (en) * 1985-12-27 1989-01-31 Eisai Co., Ltd. Guanidinobenzoic ester derivative
US4948808A (en) * 1985-12-27 1990-08-14 Eisai Co., Ltd. Guanidinobenzoic ester derivative
US5229106A (en) * 1986-06-27 1993-07-20 The Procter & Gamble Company Sunscreen agents, sunscreen compositions and method for preventing sunburn
US5210275A (en) * 1986-06-27 1993-05-11 The Procter & Gamble Company Chromophores, sunscreen compositions and methods for preventing sunburn
US5229107A (en) * 1986-06-27 1993-07-20 The Procter & Gamble Company Sunscreen agents, sunscreen compositions and methods for preventing sunburn
US5230874A (en) * 1986-06-27 1993-07-27 The Procter & Gamble Company Sunscreen agents, sunscreen compositions and methods for preventing sunburn
US5243064A (en) * 1986-06-27 1993-09-07 The Procter & Gamble Company Chromophores, sunscreen compositions and methods for preventing sunburn
US5138089A (en) * 1986-06-27 1992-08-11 The Procter & Gamble Company Chromophores, sunscreen compositions and methods for preventing sunburn
US4937370A (en) * 1987-06-02 1990-06-26 The Procter & Gamble Company Novel chromophores, sunscreen compositions and methods for preventing sunburn
US5352704A (en) * 1989-12-22 1994-10-04 Banyu Pharmaceutical Co., Ltd. Guanidinobenzene derivatives
WO1992016503A1 (en) * 1991-03-25 1992-10-01 Boehringer Mannheim Gmbh New sulphonamides, process for preparing the same and medicaments containing these compounds
JP3220225B2 (en) 1992-04-10 2001-10-22 小野薬品工業株式会社 Guanidinophenol derivatives
WO1997036861A1 (en) * 1996-03-29 1997-10-09 G.D. Searle & Co. Meta-substituted phenylene sulphonamide derivatives
WO1997036858A1 (en) * 1996-03-29 1997-10-09 G.D. Searle & Co. Cyclopropyl alkanoic acid derivatives
US5843906A (en) * 1996-03-29 1998-12-01 G. D. Searle & Co. Meta-substituted phenylene sulphonamide derivatives
US6677308B1 (en) 1996-03-29 2004-01-13 G. D. Searle & Co. Meta-substituted phenylene sulphonamide derivatives
FR2761061A1 (en) * 1997-03-20 1998-09-25 Synthelabo BENZENESULFONAMIDE DERIVATIVES, THEIR PREPARATION AND THERAPEUTIC USE THEREOF
WO1998042679A1 (en) * 1997-03-20 1998-10-01 Sanofi-Synthelabo Benzenesulphonamide derivatives, preparation and application thereof in therapy
EP1285911A3 (en) * 1998-09-23 2003-03-26 Tularik Inc. Arylsulfonanilide ureas
US6583165B2 (en) 1998-09-23 2003-06-24 Tularik Inc. Arylsulfonanilide ureas
WO2000017159A1 (en) * 1998-09-23 2000-03-30 Tularik Inc. Arylsulfonanilide ureas
US7060718B2 (en) 1998-09-23 2006-06-13 Amgen Inc. Arylsulfonanilide ureas
CN100335461C (en) * 1998-09-23 2007-09-05 图拉里克公司 Arylsulfonanilide ureas
US6214880B1 (en) 1998-09-23 2001-04-10 Tularik Inc. Arylsulfonanilide ureas
US6822001B2 (en) 2000-11-03 2004-11-23 Tularik Inc. Combination therapy using pentafluorobenzenesulfonamides and antineoplastic agents
US7560591B2 (en) 2001-02-08 2009-07-14 Rotta Research Laboratorium S.P.A. Benzamidine derivatives having anti-inflammatory and immunosuppressive activity
WO2002070468A3 (en) * 2001-02-08 2003-09-04 Rotta Research Lab Novel benzamidine derivatives having anti-inflammatory and immunosuppressive activity
US7202277B2 (en) 2001-02-08 2007-04-10 Rotta Research Laboratorium S.P.A. Benzamidine derivatives having anti-inflammatory and immunosuppressive activity
US8138342B2 (en) 2004-10-12 2012-03-20 High Point Pharmacueticals, LLC 11β-hydroxysteroid dehydrogenase type 1 active spiro compounds
US8377985B2 (en) 2005-07-18 2013-02-19 Bipar Sciences, Inc. Treatment of cancer
US7405227B2 (en) 2005-07-18 2008-07-29 Bipar Sciences, Inc. Treatment of cancer
US8053431B2 (en) 2005-11-01 2011-11-08 High Point Pharmaceuticals, Llc Pharmaceutical use of substituted amides
US8053447B2 (en) 2006-04-07 2011-11-08 High Point Pharmaceuticals, Llc 11β-hydroxysteroid dehydrogenase type 1 active compounds
WO2007143880A1 (en) * 2006-06-09 2007-12-21 Shanghai East Best Biopharmaceutical Enterprises Co., Ltd. Compounds for preventing and treating bacterial infection and its preparation and use
US8048908B2 (en) 2006-07-13 2011-11-01 High Point Pharmaceuticals, Llc 11β-hydroxysteroid dehydrogenase type 1 active compounds
US8143447B2 (en) 2006-09-05 2012-03-27 Bipar Sciences, Inc. Treatment of cancer
US8383820B2 (en) 2007-02-23 2013-02-26 High Point Pharmaceuticals, Llc N-adamantyl benzamides as inhibitors of 11-β-hydroxysteroid dehydrogenase
US8334305B2 (en) 2007-02-23 2012-12-18 High Point Pharmaceuticals, Llc N-adamantyl benzamides as inhibitors of 11-β-hydroxysteroid dehydrogenase
US8809540B2 (en) 2007-02-23 2014-08-19 High Point Pharmaceuticals, Llc N-adamantyl benzamides as inhibitors of 11-beta-hydroxysteroid dehydrogenase
US8153798B2 (en) 2007-03-09 2012-04-10 High Point Pharmaceuticals, Llc Indole- and benzimidazole amides as hydroxysteroid dehydrogenase inhibitors
US8383683B2 (en) 2007-04-24 2013-02-26 High Point Pharmaceuticals, Llc Pharmaceutical use of substituted amides
GB2533925A (en) * 2014-12-31 2016-07-13 Univ Bath Antimicrobial compounds, compositions and methods
WO2016108045A3 (en) * 2014-12-31 2016-09-15 Swansea University Antimicrobial compounds, compositions and methods
US11666888B2 (en) 2018-02-05 2023-06-06 Bio-Rad Laboratories, Inc. Chromatography resin having an anionic exchange-hydrophobic mixed mode ligand
US12194432B2 (en) 2018-02-05 2025-01-14 Bio-Rad Laboratories, Inc. Chromatography resin having an anionic exchange-hydrophobic mixed mode ligand
CN114805141A (en) * 2021-01-27 2022-07-29 中国科学院上海药物研究所 4-guanidinobenzoic acid aryl ester compound and application thereof in resisting SARS-CoV-2 virus

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