WO1994004542A1 - β-AMINOALKYL AND β-N-PEPTIDYLAMINOALKYL BORONIC ACIDS - Google Patents

β-AMINOALKYL AND β-N-PEPTIDYLAMINOALKYL BORONIC ACIDS Download PDF

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Publication number
WO1994004542A1
WO1994004542A1 PCT/US1993/007276 US9307276W WO9404542A1 WO 1994004542 A1 WO1994004542 A1 WO 1994004542A1 US 9307276 W US9307276 W US 9307276W WO 9404542 A1 WO9404542 A1 WO 9404542A1
Authority
WO
WIPO (PCT)
Prior art keywords
acid
alkyl
group
compound
aryl
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.)
Ceased
Application number
PCT/US1993/007276
Other languages
English (en)
French (fr)
Inventor
David William Bjorkquist
Rajan Keshav Panandiker
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.)
Procter and Gamble Co
Original Assignee
Procter and Gamble Co
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 Procter and Gamble Co filed Critical Procter and Gamble Co
Priority to JP6506312A priority Critical patent/JPH08500113A/ja
Priority to DE69315079T priority patent/DE69315079T2/de
Priority to EP93918597A priority patent/EP0655067B1/en
Priority to AU47997/93A priority patent/AU4799793A/en
Publication of WO1994004542A1 publication Critical patent/WO1994004542A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/38—Products with no well-defined composition, e.g. natural products
    • C11D3/386—Preparations containing enzymes, e.g. protease or amylase
    • C11D3/38663—Stabilised liquid enzyme compositions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Definitions

  • Another preferred compound has the same formula as the above, except that Y is 0
  • composition of matter having serine protease reversible inhibition properties comprising the compound described herein and serine protease (described below).
  • Citrate builders e.g., citric acid and soluble salts thereof (particularly sodium salt), are polycarboxylate builders of particular importance for heavy duty liquid detergent formulations, but can also be used in granular compositions.
  • diethylcyanophosphonate (1.09 g, 6.7 mmoles) is added slowly. The reaction is stirred overnight. After removing the volatiles under reduced pressure, the residue is dissolved in ethyl acetate (30 ml) and extracted with one portion (15 ml) of 2N HCl in a separatory funnel. The funnel is shaken for 12 minutes until compound (13) precipitates and is suspended in the aqueous layer. Compound (13) is collected by filtration and dried under vacuum.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Detergent Compositions (AREA)
  • Peptides Or Proteins (AREA)
  • Saccharide Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
PCT/US1993/007276 1992-08-14 1993-08-03 β-AMINOALKYL AND β-N-PEPTIDYLAMINOALKYL BORONIC ACIDS Ceased WO1994004542A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP6506312A JPH08500113A (ja) 1992-08-14 1993-08-03 β‐アミノアルキルおよびβ‐Ｎ‐ペプチジルアミノアルキルボロニン酸
DE69315079T DE69315079T2 (de) 1992-08-14 1993-08-03 Beta-aminoalkyl und beta-n-peptidylaminoalkylborsäure
EP93918597A EP0655067B1 (en) 1992-08-14 1993-08-03 Beta-aminoalkyl and beta-n-peptidylaminoalkyl boronic acids
AU47997/93A AU4799793A (en) 1992-08-14 1993-08-03 Beta -aminoalkyl and beta -n-peptidylaminoalkyl boronic acids

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US07/931,809 1992-08-14
US07/931,809 US5442100A (en) 1992-08-14 1992-08-14 β-aminoalkyl and β-N-peptidylaminoalkyl boronic acids

Publications (1)

Publication Number Publication Date
WO1994004542A1 true WO1994004542A1 (en) 1994-03-03

Family

ID=25461390

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1993/007276 Ceased WO1994004542A1 (en) 1992-08-14 1993-08-03 β-AMINOALKYL AND β-N-PEPTIDYLAMINOALKYL BORONIC ACIDS

Country Status (10)

Country Link
US (2) US5442100A (2)
EP (1) EP0655067B1 (2)
JP (1) JPH08500113A (2)
CN (1) CN1047596C (2)
AT (1) ATE159945T1 (2)
AU (1) AU4799793A (2)
DE (1) DE69315079T2 (2)
MX (1) MX9304970A (2)
TW (1) TW251274B (2)
WO (1) WO1994004542A1 (2)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011088089A1 (en) 2010-01-12 2011-07-21 The Procter & Gamble Company Intermediates and surfactants useful in household cleaning and personal care compositions, and methods of making the same
WO2012112828A1 (en) 2011-02-17 2012-08-23 The Procter & Gamble Company Bio-based linear alkylphenyl sulfonates
WO2012138423A1 (en) 2011-02-17 2012-10-11 The Procter & Gamble Company Compositions comprising mixtures of c10-c13 alkylphenyl sulfonates
WO2013104897A1 (en) * 2012-01-09 2013-07-18 University of Tromsø Therapeutic boron-containing compounds
US10526351B2 (en) 2008-06-17 2020-01-07 Millennium Pharmaceuticals, Inc. Boronate ester compounds and pharmaceutical compositions thereof
US11241448B2 (en) 2014-05-20 2022-02-08 Millennium Pharmaceuticals, Inc. Methods for cancer therapy

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EP0583536B1 (en) * 1992-08-14 1997-03-05 The Procter & Gamble Company Liquid detergents containing an alpha-amino boronic acid
WO1995002046A1 (en) * 1993-07-09 1995-01-19 Novo Nordisk A/S Boronic acid or borinic acid derivatives as enzyme stabilizers
US5834415A (en) * 1994-04-26 1998-11-10 Novo Nordisk A/S Naphthalene boronic acids
DE4422433A1 (de) * 1994-06-28 1996-01-04 Cognis Bio Umwelt Mehrenzymgranulat
US5731439A (en) * 1995-03-24 1998-03-24 The Dupont Merck Pharmaceutical Company Piperidine containing aminobornic acids
US6086634A (en) 1995-06-05 2000-07-11 Custom Cleaner, Inc. Dry-cleaning compositions containing polysulfonic acid
US6036727A (en) 1995-06-05 2000-03-14 Creative Products Resource, Inc. Anhydrous dry-cleaning compositions containing polysulfonic acid, and dry-cleaning kits for delicate fabrics
WO1996039556A1 (en) 1995-06-05 1996-12-12 Creative Products Resource, Inc. Dry-cleaning kit for in-dryer use
US5658651A (en) 1995-09-29 1997-08-19 Creative Products Resource, Inc. Fabric treatment and softener system for in-dryer use
DE69621131T2 (de) * 1995-06-13 2002-11-28 Novozymes A/S, Bagsvaerd 4-substituierte-phenylboronsäuren als enzymstabilisatoren
CA2374580C (en) * 1999-06-14 2009-12-15 Wisconsin Alumni Research Foundation Oligomers and polymers of cyclic imino carboxylic acids
BRPI0515062A (pt) * 2004-09-08 2008-07-01 Procter & Gamble composições para tratamento de roupas para lavar com odor aprimorado
CA2709704C (en) 2008-01-04 2013-08-06 The Procter & Gamble Company A laundry detergent composition comprising glycosyl hydrolase
US20090209447A1 (en) * 2008-02-15 2009-08-20 Michelle Meek Cleaning compositions
PL3404088T3 (pl) 2008-06-06 2025-04-28 The Procter & Gamble Company Kompozycja detergentu zawierająca odmianę z grupy 44 ksyloglukanazy
WO2011005730A1 (en) 2009-07-09 2011-01-13 The Procter & Gamble Company A catalytic laundry detergent composition comprising relatively low levels of water-soluble electrolyte
BR112012000531A2 (pt) 2009-07-09 2019-09-24 Procter & Gamble composição detergente para lavagem de roupas catalítica que compreende teores relativamente baixos de eletrólito solúvel em água
MX2012010572A (es) 2010-03-12 2012-10-09 Procter & Gamble Gelificante diamido para utilizar en composiciones de productos de consumo.
US8222197B2 (en) 2010-03-12 2012-07-17 The Procter & Gamble Company Liquid detergent compositions comprising pH tuneable amido-gellants, and processes for making
RS60310B1 (sr) 2010-08-10 2020-07-31 Rempex Pharmaceuticals Inc Ciklični derivati estra boronske kiseline, postupak za pripremu injihove terapeutske upotrebe
EP2737043B1 (en) 2011-07-25 2017-01-04 The Procter and Gamble Company Detergents having acceptable color
US20130303427A1 (en) 2011-09-13 2013-11-14 Susana Fernandez Prieto MICROCAPSULE COMPOSITIONS COMPRISING pH TUNEABLE DI-AMIDO GELLANTS
EP2716644B1 (en) 2012-10-03 2017-04-05 The Procter and Gamble Company A stable enzyme stabilizer premix
US9241947B2 (en) 2013-01-04 2016-01-26 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
KR20150103269A (ko) 2013-01-04 2015-09-09 렘펙스 파머수티클스 인코퍼레이티드 보론산 유도체 및 그의 치료적 용도
CN105189724A (zh) 2013-03-14 2015-12-23 诺维信公司 含有酶和抑制剂的水溶性膜
WO2014177709A1 (en) 2013-05-03 2014-11-06 Novozymes A/S Microencapsulation of detergent enzymes
EP3139930B1 (en) 2014-05-05 2024-08-14 Melinta Therapeutics, Inc. Salts and polymorphs of cyclic boronic acid ester derivatives and therapeutic uses thereof
SI3140310T1 (sl) 2014-05-05 2020-01-31 Rempex Pharmaceuticals, Inc. Sinteza boronatnih soli in njihova uporaba
WO2015179308A1 (en) 2014-05-19 2015-11-26 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
EA201692301A1 (ru) 2014-07-01 2017-06-30 Ремпекс Фармасьютикалз, Инк. Производные бороновой кислоты и их терапевтическое применение
CN106471110A (zh) 2014-07-03 2017-03-01 诺维信公司 改进的非蛋白酶类酶稳定化
WO2016081297A1 (en) 2014-11-18 2016-05-26 Rempex Pharmaceuticals, Inc. Cyclic boronic acid ester derivatives and therapeutic uses thereof
EP3233869B1 (en) 2014-12-19 2019-09-25 Rempex Pharmaceuticals, Inc. Apparatus and continuous flow process for production of boronic acid derivatives
US10400230B2 (en) 2014-12-19 2019-09-03 Novozymes A/S Protease variants and polynucleotides encoding same
US20180051041A1 (en) 2015-03-17 2018-02-22 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
EP3950939A3 (en) 2015-07-06 2022-06-08 Novozymes A/S Lipase variants and polynucleotides encoding same
JP2018531783A (ja) 2015-10-14 2018-11-01 ノボザイムス アクティーゼルスカブ 水濾過膜の洗浄
ES2894251T3 (es) 2016-06-30 2022-02-14 Qpex Biopharma Inc Derivados de ácido borónico y usos terapéuticos de los mismos
WO2018202846A1 (en) 2017-05-05 2018-11-08 Novozymes A/S Compositions comprising lipase and sulfite
EP3645692B1 (en) 2017-06-30 2025-12-31 Novozymes A/S ENZYMATIC SUSPENSION COMPOSITION
MX2020003495A (es) 2017-10-11 2020-09-18 Qpex Biopharma Inc Derivados de acido boronico y sintesis de los mismos.
EP3704240A1 (en) 2017-11-01 2020-09-09 Novozymes A/S Polypeptides and compositions comprising such polypeptides
WO2019086530A1 (en) 2017-11-01 2019-05-09 Novozymes A/S Polypeptides and compositions comprising such polypeptides
US20210002588A1 (en) 2018-03-13 2021-01-07 Novozymes A/S Microencapsulation Using Amino Sugar Oligomers
US12016868B2 (en) 2018-04-20 2024-06-25 Qpex Biopharma, Inc. Boronic acid derivatives and therapeutic uses thereof
EP3647398B1 (en) 2018-10-31 2024-05-15 Henkel AG & Co. KGaA Cleaning compositions containing dispersins v
EP3647397A1 (en) 2018-10-31 2020-05-06 Henkel AG & Co. KGaA Cleaning compositions containing dispersins iv
CA3154440A1 (en) 2019-11-27 2021-06-03 Phillip Kyle Vinson Improved alkylbenzenesulfonate surfactants
US20220411773A1 (en) 2019-12-20 2022-12-29 Novozymes A/S Polypeptides having proteolytic activity and use thereof
BR112022022367A2 (pt) 2020-05-05 2023-01-10 Qpex Biopharma Inc Derivados e síntese de ácido borônico, formas polimórficas e usos terapêuticos dos mesmos
EP4305146A1 (en) 2021-03-12 2024-01-17 Novozymes A/S Polypeptide variants
CN120344647A (zh) 2022-12-23 2025-07-18 诺维信公司 包含过氧化氢酶和淀粉酶的洗涤剂组合物

Citations (1)

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Publication number Priority date Publication date Assignee Title
EP0371467A2 (de) * 1988-12-01 1990-06-06 Hoechst Aktiengesellschaft Beta-Amino-Boronsäure-Derivate

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10526351B2 (en) 2008-06-17 2020-01-07 Millennium Pharmaceuticals, Inc. Boronate ester compounds and pharmaceutical compositions thereof
US10604538B2 (en) 2008-06-17 2020-03-31 Millenium Pharmaceuticals, Inc. Boronate ester compounds and pharmaceutical compositions thereof
US11485746B2 (en) 2008-06-17 2022-11-01 Millennium Pharmaceuticals, Inc. Boronate ester compounds and pharmaceutical compositions thereof
WO2011088089A1 (en) 2010-01-12 2011-07-21 The Procter & Gamble Company Intermediates and surfactants useful in household cleaning and personal care compositions, and methods of making the same
WO2012112828A1 (en) 2011-02-17 2012-08-23 The Procter & Gamble Company Bio-based linear alkylphenyl sulfonates
WO2012138423A1 (en) 2011-02-17 2012-10-11 The Procter & Gamble Company Compositions comprising mixtures of c10-c13 alkylphenyl sulfonates
WO2013104897A1 (en) * 2012-01-09 2013-07-18 University of Tromsø Therapeutic boron-containing compounds
US11241448B2 (en) 2014-05-20 2022-02-08 Millennium Pharmaceuticals, Inc. Methods for cancer therapy

Also Published As

Publication number Publication date
EP0655067A1 (en) 1995-05-31
ATE159945T1 (de) 1997-11-15
MX9304970A (es) 1994-05-31
CN1090850A (zh) 1994-08-17
JPH08500113A (ja) 1996-01-09
US5488157A (en) 1996-01-30
DE69315079D1 (de) 1997-12-11
US5442100A (en) 1995-08-15
DE69315079T2 (de) 1998-06-04
AU4799793A (en) 1994-03-15
TW251274B (2) 1995-07-11
EP0655067B1 (en) 1997-11-05
CN1047596C (zh) 1999-12-22

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