DE69315079T2 - Beta-aminoalkyl und beta-n-peptidylaminoalkylborsäure - Google Patents
Beta-aminoalkyl und beta-n-peptidylaminoalkylborsäureInfo
- Publication number
- DE69315079T2 DE69315079T2 DE69315079T DE69315079T DE69315079T2 DE 69315079 T2 DE69315079 T2 DE 69315079T2 DE 69315079 T DE69315079 T DE 69315079T DE 69315079 T DE69315079 T DE 69315079T DE 69315079 T2 DE69315079 T2 DE 69315079T2
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- acid
- 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.)
- Expired - Fee Related
Links
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- 125000003118 aryl group Chemical group 0.000 claims abstract description 17
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- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 108010020132 microbial serine proteinases Proteins 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- QEALYLRSRQDCRA-UHFFFAOYSA-N myristamide Chemical compound CCCCCCCCCCCCCC(N)=O QEALYLRSRQDCRA-UHFFFAOYSA-N 0.000 description 1
- TYRGLVWXHJRKMT-QMMMGPOBSA-N n-benzyloxycarbonyl-l-serine-betalactone Chemical compound OC(=O)[C@H](C)NC(=O)OCC1=CC=CC=C1 TYRGLVWXHJRKMT-QMMMGPOBSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical class OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- FATBGEAMYMYZAF-UHFFFAOYSA-N oleicacidamide-heptaglycolether Natural products CCCCCCCCC=CCCCCCCCC(N)=O FATBGEAMYMYZAF-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 125000005541 phosphonamide group Chemical group 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001444 polymaleic acid Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 150000004804 polysaccharides Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000004023 quaternary phosphonium compounds Chemical class 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000002461 renin inhibitor Substances 0.000 description 1
- 229940086526 renin-inhibitors Drugs 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229940071207 sesquicarbonate Drugs 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229940045919 sodium polymetaphosphate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910000031 sodium sesquicarbonate Inorganic materials 0.000 description 1
- 235000018341 sodium sesquicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229940037312 stearamide Drugs 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- DIORMHZUUKOISG-UHFFFAOYSA-N sulfoformic acid Chemical compound OC(=O)S(O)(=O)=O DIORMHZUUKOISG-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003457 sulfones Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical group ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 108010075550 termamyl Proteins 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000004026 tertiary sulfonium compounds Chemical class 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical group NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- WCTAGTRAWPDFQO-UHFFFAOYSA-K trisodium;hydrogen carbonate;carbonate Chemical compound [Na+].[Na+].[Na+].OC([O-])=O.[O-]C([O-])=O WCTAGTRAWPDFQO-UHFFFAOYSA-K 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 229910009111 xH2 O Inorganic materials 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Detergent Compositions (AREA)
- Peptides Or Proteins (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/931,809 US5442100A (en) | 1992-08-14 | 1992-08-14 | β-aminoalkyl and β-N-peptidylaminoalkyl boronic acids |
| PCT/US1993/007276 WO1994004542A1 (en) | 1992-08-14 | 1993-08-03 | β-AMINOALKYL AND β-N-PEPTIDYLAMINOALKYL BORONIC ACIDS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69315079D1 DE69315079D1 (de) | 1997-12-11 |
| DE69315079T2 true DE69315079T2 (de) | 1998-06-04 |
Family
ID=25461390
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69315079T Expired - Fee Related DE69315079T2 (de) | 1992-08-14 | 1993-08-03 | Beta-aminoalkyl und beta-n-peptidylaminoalkylborsäure |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US5442100A (enExample) |
| EP (1) | EP0655067B1 (enExample) |
| JP (1) | JPH08500113A (enExample) |
| CN (1) | CN1047596C (enExample) |
| AT (1) | ATE159945T1 (enExample) |
| AU (1) | AU4799793A (enExample) |
| DE (1) | DE69315079T2 (enExample) |
| MX (1) | MX9304970A (enExample) |
| TW (1) | TW251274B (enExample) |
| WO (1) | WO1994004542A1 (enExample) |
Families Citing this family (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE149563T1 (de) * | 1992-08-14 | 1997-03-15 | Procter & Gamble | Alpha-aminoborsäurehaltige flüssige waschmittel |
| AU7121394A (en) * | 1993-07-09 | 1995-02-06 | Borax Consolidated Ltd | 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 |
| EP0830473A4 (en) | 1995-06-05 | 1999-01-07 | Creative Prod Resource Inc | CHEMICAL CLEANING KIT FOR USE IN DRYER |
| US5658651A (en) | 1995-09-29 | 1997-08-19 | Creative Products Resource, Inc. | Fabric treatment and softener system for in-dryer use |
| 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 |
| WO1996041859A1 (en) * | 1995-06-13 | 1996-12-27 | Novo Nordisk A/S | 4-substituted-phenyl-boronic acids as enzyme stabilizers |
| IL146923A0 (en) * | 1999-06-14 | 2002-08-14 | Wisconsin Alumni Res Found | Oligomers and polymers of cyclic imino carboxylic acids |
| CN101014691A (zh) * | 2004-09-08 | 2007-08-08 | 宝洁公司 | 具有改善的气味的衣物处理组合物 |
| ES2568784T5 (es) * | 2008-01-04 | 2023-09-13 | Procter & Gamble | Una composición detergente para lavado de ropa que comprende glicosil hidrolasa |
| US20090209447A1 (en) * | 2008-02-15 | 2009-08-20 | Michelle Meek | Cleaning compositions |
| CN102057030B (zh) | 2008-06-06 | 2016-05-11 | 宝洁公司 | 包含家族44木葡聚糖酶变体的洗涤剂组合物 |
| BR122014008753A2 (pt) | 2008-06-17 | 2015-12-29 | Millennium Pharm Inc | compostos de éster boronato e composições farmacêuticas dos mesmos |
| 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 |
| BR112012000520A2 (pt) | 2009-07-09 | 2016-02-16 | Procter & Gamble | composição catalítica detergente para lavagem de roupa que compreende teores relativamente baixos de eletrólito solúvel em água |
| US8933131B2 (en) | 2010-01-12 | 2015-01-13 | The Procter & Gamble Company | Intermediates and surfactants useful in household cleaning and personal care compositions, and methods of making the same |
| CA2792767C (en) | 2010-03-12 | 2014-07-08 | The Procter & Gamble Company | Ph tuneable amido-gellant for use in consumer product compositions |
| US8207107B2 (en) | 2010-03-12 | 2012-06-26 | The Procter & Gamble Company | Di-amido gellant for use in consumer product compositions |
| EP2603514B1 (en) | 2010-08-10 | 2018-07-18 | Rempex Pharmaceuticals, Inc. | Cyclic boronic acid ester derivatives and therapeutic uses thereof |
| WO2012138423A1 (en) | 2011-02-17 | 2012-10-11 | The Procter & Gamble Company | Compositions comprising mixtures of c10-c13 alkylphenyl sulfonates |
| MX2013009546A (es) | 2011-02-17 | 2013-11-22 | Procter & Gamble | Alquilfenil sulfonatos lineales de base biologica. |
| 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 |
| EP2802593A1 (en) * | 2012-01-09 | 2014-11-19 | The University of Tromsoe | Therapeutic boron-containing compounds |
| EP2716644B1 (en) | 2012-10-03 | 2017-04-05 | The Procter and Gamble Company | A stable enzyme stabilizer premix |
| JP2016509594A (ja) | 2013-01-04 | 2016-03-31 | レンペックス・ファーマシューティカルズ・インコーポレイテッド | ボロン酸誘導体及びその治療的使用 |
| US9241947B2 (en) | 2013-01-04 | 2016-01-26 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| 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 |
| JP7020778B2 (ja) | 2013-05-03 | 2022-02-16 | ノボザイムス アクティーゼルスカブ | 洗剤酵素のマイクロカプセル化 |
| US9687497B1 (en) | 2014-05-05 | 2017-06-27 | Rempex Pharmaceuticals, Inc. | Salts and polymorphs of cyclic boronic acid ester derivatives and therapeutic uses thereof |
| RS59488B1 (sr) | 2014-05-05 | 2019-12-31 | Rempex Pharmaceuticals Inc | Sinteza boronatnih soli i njihove upotrebe |
| MX2016015093A (es) | 2014-05-19 | 2017-03-27 | Rempex Pharmaceuticals Inc | Derivados de acido boronico y sus usos terapeuticos. |
| CN106659761A (zh) | 2014-05-20 | 2017-05-10 | 千年药物公司 | 初级癌症疗法后使用的含硼蛋白酶体抑制剂 |
| EA201692301A1 (ru) | 2014-07-01 | 2017-06-30 | Ремпекс Фармасьютикалз, Инк. | Производные бороновой кислоты и их терапевтическое применение |
| WO2016001319A1 (en) | 2014-07-03 | 2016-01-07 | Novozymes A/S | Improved stabilization of non-protease enzyme |
| US10662205B2 (en) | 2014-11-18 | 2020-05-26 | Qpex Biopharma, Inc. | Cyclic boronic acid ester derivatives and therapeutic uses thereof |
| WO2016097352A1 (en) | 2014-12-19 | 2016-06-23 | Novozymes A/S | Protease variants and polynucleotides encoding same |
| WO2016100043A1 (en) | 2014-12-19 | 2016-06-23 | Rempex Pharmaceuticals, Inc. | Apparatus and continuous flow process for production of boronic acid derivatives |
| US20180051041A1 (en) | 2015-03-17 | 2018-02-22 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| CN114292829A (zh) | 2015-07-06 | 2022-04-08 | 诺维信公司 | 脂肪酶变体以及编码它们的多核苷酸 |
| BR112018007474A2 (pt) | 2015-10-14 | 2018-10-30 | Novozymes A/S | ?limpeza de membranas de filtração de água? |
| EP3478693B1 (en) | 2016-06-30 | 2021-07-21 | Qpex Biopharma, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| US11078445B2 (en) | 2017-05-05 | 2021-08-03 | Novozymes A/S | Compositions comprising lipase and sulfite |
| CN111108183A (zh) | 2017-06-30 | 2020-05-05 | 诺维信公司 | 酶浆液组合物 |
| JP7377545B2 (ja) | 2017-10-11 | 2023-11-10 | キューペックス バイオファーマ， インコーポレイテッド | ボロン酸誘導体およびその合成 |
| WO2019086528A1 (en) | 2017-11-01 | 2019-05-09 | Novozymes A/S | Polypeptides and compositions comprising such polypeptides |
| EP4379029A1 (en) | 2017-11-01 | 2024-06-05 | Novozymes A/S | Polypeptides and compositions comprising such polypeptides |
| EP3765185B1 (en) | 2018-03-13 | 2023-07-19 | Novozymes A/S | Microencapsulation using amino sugar oligomers |
| CA3097127A1 (en) | 2018-04-20 | 2019-10-24 | Qpex Biopharma, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| EP3647397A1 (en) | 2018-10-31 | 2020-05-06 | Henkel AG & Co. KGaA | Cleaning compositions containing dispersins iv |
| ES2981999T3 (es) | 2018-10-31 | 2024-10-14 | Henkel Ag & Co Kgaa | Composiciones limpiadoras que contienen dispersinas V |
| JP7381740B2 (ja) | 2019-11-27 | 2023-11-15 | ザ プロクター アンド ギャンブル カンパニー | 液体洗濯洗剤組成物 |
| WO2021123307A2 (en) | 2019-12-20 | 2021-06-24 | Novozymes A/S | Polypeptides having proteolytic activity and use thereof |
| US20240301328A1 (en) | 2021-03-12 | 2024-09-12 | Novozymes A/S | Polypeptide variants |
| WO2024131880A2 (en) | 2022-12-23 | 2024-06-27 | Novozymes A/S | Detergent composition comprising catalase and amylase |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2872479A (en) * | 1955-06-30 | 1959-02-03 | Callery Chemical Co | Preparation of organoboron compounds |
| US3912595A (en) * | 1974-02-25 | 1975-10-14 | Us Health | Method of purifying enzymes using boronic acids covalently bonded to an insoluble support |
| IT1129814B (it) * | 1980-07-02 | 1986-06-11 | Unilever Nv | Composizione detergente enzimatica liquida |
| US4462922A (en) * | 1981-11-19 | 1984-07-31 | Lever Brothers Company | Enzymatic liquid detergent composition |
| GB8311314D0 (en) * | 1983-04-26 | 1983-06-02 | Unilever Plc | Aqueous enzyme-containing compositions |
| US4652394A (en) * | 1983-05-31 | 1987-03-24 | Colgate Palmolive Co. | Built single phase liquid anionic detergent compositions containing stabilized enzymes |
| DE3413571A1 (de) * | 1984-04-11 | 1985-10-24 | Hoechst Ag, 6230 Frankfurt | Verwendung von kristallinen schichtfoermigen natriumsilikaten zur wasserenthaertung und verfahren zur wasserenthaertung |
| US4537707A (en) * | 1984-05-14 | 1985-08-27 | The Procter & Gamble Company | Liquid detergents containing boric acid and formate to stabilize enzymes |
| US4566985A (en) * | 1984-09-19 | 1986-01-28 | Applied Biochemists, Inc. | Method of cleaning using liquid compositions comprising stabilized mixtures of enzymes |
| US4747977A (en) * | 1984-11-09 | 1988-05-31 | The Procter & Gamble Company | Ethanol-free liquid laundry detergent compositions |
| US4842769A (en) * | 1985-07-26 | 1989-06-27 | Colgate-Palmolive Co. | Stabilized fabric softening built detergent composition containing enzymes |
| US4900475A (en) * | 1985-07-26 | 1990-02-13 | Colgate-Palmolive Co. | Stabilized built liquid detergent composition containing enzyme |
| US4933287A (en) * | 1985-08-09 | 1990-06-12 | Gist-Brocades N.V. | Novel lipolytic enzymes and their use in detergent compositions |
| EG18543A (en) * | 1986-02-20 | 1993-07-30 | Albright & Wilson | Protected enzyme systems |
| US4842758A (en) * | 1986-10-31 | 1989-06-27 | Colgate-Palmolive Company | Stabilized enzyme system for use in aqueous liquid built detergent compositions |
| US4704233A (en) * | 1986-11-10 | 1987-11-03 | The Procter & Gamble Company | Detergent compositions containing ethylenediamine-N,N'-disuccinic acid |
| US5187157A (en) * | 1987-06-05 | 1993-02-16 | Du Pont Merck Pharmaceutical Company | Peptide boronic acid inhibitors of trypsin-like proteases |
| DK571587D0 (da) * | 1987-11-02 | 1987-11-02 | Novo Industri As | Enzymatisk detergentsammensaetning |
| EP0315574A3 (de) * | 1987-11-05 | 1990-08-22 | Hoechst Aktiengesellschaft | Renin-Inhibitoren |
| GB8810822D0 (en) * | 1988-05-06 | 1988-06-08 | Unilever Plc | Liquid detergent compositions |
| US4963655A (en) * | 1988-05-27 | 1990-10-16 | Mayo Foundation For Medical Education And Research | Boron analogs of amino acid/peptide protease inhibitors |
| US5039446A (en) * | 1988-07-01 | 1991-08-13 | Genencor International, Inc. | Liquid detergent with stabilized enzyme |
| DE3840452A1 (de) * | 1988-12-01 | 1990-06-07 | Hoechst Ag | (beta)-amino-boronsaeure-derivate |
| CA2006527A1 (en) * | 1988-12-30 | 1990-06-30 | Martin S. Cardinali | Enzymatic liquid detergent compositions |
| US4959179A (en) * | 1989-01-30 | 1990-09-25 | Lever Brothers Company | Stabilized enzymes liquid detergent composition containing lipase and protease |
| US4908150A (en) * | 1989-02-02 | 1990-03-13 | Lever Brothers Company | Stabilized lipolytic enzyme-containing liquid detergent composition |
| EP0385401A1 (en) * | 1989-02-27 | 1990-09-05 | Occidental Chemical Corporation | Unique Microbial lipases with activity at temperatures and pHs suitable for use in detergents |
| ATE188990T1 (de) * | 1989-05-15 | 2000-02-15 | Clorox Co | Wäschewaschverfahren |
| EP0450702A3 (en) * | 1990-04-06 | 1993-06-02 | Unilever N.V. | Process for preparing liquid enzymatic detergent compositions |
| EP0478050A1 (en) * | 1990-09-24 | 1992-04-01 | Unilever N.V. | Detergent composition |
| DK0486073T3 (da) * | 1990-11-14 | 1996-12-09 | Procter & Gamble | Væskeformig detergentsammensætning, der indeholder lipase og protease |
-
1992
- 1992-08-14 US US07/931,809 patent/US5442100A/en not_active Expired - Fee Related
-
1993
- 1993-08-03 JP JP6506312A patent/JPH08500113A/ja active Pending
- 1993-08-03 EP EP93918597A patent/EP0655067B1/en not_active Expired - Lifetime
- 1993-08-03 AT AT93918597T patent/ATE159945T1/de not_active IP Right Cessation
- 1993-08-03 WO PCT/US1993/007276 patent/WO1994004542A1/en not_active Ceased
- 1993-08-03 AU AU47997/93A patent/AU4799793A/en not_active Abandoned
- 1993-08-03 DE DE69315079T patent/DE69315079T2/de not_active Expired - Fee Related
- 1993-08-14 CN CN93117839A patent/CN1047596C/zh not_active Expired - Fee Related
- 1993-08-16 MX MX9304970A patent/MX9304970A/es not_active IP Right Cessation
- 1993-10-13 TW TW082108452A patent/TW251274B/zh active
-
1995
- 1995-05-04 US US08/434,901 patent/US5488157A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ATE159945T1 (de) | 1997-11-15 |
| US5442100A (en) | 1995-08-15 |
| TW251274B (enExample) | 1995-07-11 |
| CN1090850A (zh) | 1994-08-17 |
| AU4799793A (en) | 1994-03-15 |
| WO1994004542A1 (en) | 1994-03-03 |
| DE69315079D1 (de) | 1997-12-11 |
| US5488157A (en) | 1996-01-30 |
| CN1047596C (zh) | 1999-12-22 |
| MX9304970A (es) | 1994-05-31 |
| EP0655067B1 (en) | 1997-11-05 |
| JPH08500113A (ja) | 1996-01-09 |
| EP0655067A1 (en) | 1995-05-31 |
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| 8339 | Ceased/non-payment of the annual fee |