KR20000076151A - 옥시알킬렌 포스페이트 화합물 및 이의 용도 - Google Patents
옥시알킬렌 포스페이트 화합물 및 이의 용도 Download PDFInfo
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- KR20000076151A KR20000076151A KR1019997008242A KR19997008242A KR20000076151A KR 20000076151 A KR20000076151 A KR 20000076151A KR 1019997008242 A KR1019997008242 A KR 1019997008242A KR 19997008242 A KR19997008242 A KR 19997008242A KR 20000076151 A KR20000076151 A KR 20000076151A
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- alkyl
- alkenyl
- alkynyl
- heteroaryl
- aryl
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- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 201000009410 rhabdomyosarcoma Diseases 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
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- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 230000008684 selective degradation Effects 0.000 description 1
- 239000008299 semisolid dosage form Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- MFBOGIVSZKQAPD-UHFFFAOYSA-M sodium butyrate Chemical compound [Na+].CCCC([O-])=O MFBOGIVSZKQAPD-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- 208000001608 teratocarcinoma Diseases 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/113—Esters of phosphoric acids with unsaturated acyclic alcohols
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/814,386 US6030961A (en) | 1997-03-11 | 1997-03-11 | Oxyalkylene phosphate compounds and uses thereof |
| US8/814,386 | 1997-03-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20000076151A true KR20000076151A (ko) | 2000-12-26 |
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| EP (1) | EP0986391A4 (enExample) |
| JP (1) | JP2001514665A (enExample) |
| KR (1) | KR20000076151A (enExample) |
| AU (1) | AU6459798A (enExample) |
| CA (1) | CA2283162A1 (enExample) |
| IL (1) | IL131742A (enExample) |
| WO (1) | WO1998040080A1 (enExample) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2686899B1 (fr) * | 1992-01-31 | 1995-09-01 | Rhone Poulenc Rorer Sa | Nouveaux polypeptides biologiquement actifs, leur preparation et compositions pharmaceutiques les contenant. |
| AU696167B2 (en) * | 1993-10-29 | 1998-09-03 | Trustees Of Boston University | Physiologically stable compositions of butyric acid, and butyric acid salts and derivatives as anti-neoplastic agents |
| US6124495A (en) | 1997-03-11 | 2000-09-26 | Beacon Laboratories, Inc. | Unsaturated oxyalkylene esters and uses thereof |
| US6822267B1 (en) * | 1997-08-20 | 2004-11-23 | Advantest Corporation | Signal transmission circuit, CMOS semiconductor device, and circuit board |
| AU774861B2 (en) * | 1998-02-11 | 2004-07-08 | Douglas V Faller | Compositions and methods for the treatment of cystic fibrosis |
| AU2001266557A1 (en) * | 2000-04-12 | 2001-10-23 | Human Genome Sciences, Inc. | Albumin fusion proteins |
| US20050100991A1 (en) * | 2001-04-12 | 2005-05-12 | Human Genome Sciences, Inc. | Albumin fusion proteins |
| US20020120008A1 (en) * | 2000-06-29 | 2002-08-29 | Seymour Benzer | Life extension of drosophila by a drug treatment |
| IL137672A0 (en) * | 2000-08-03 | 2001-10-31 | Dpharm Ltd | Derivatives of branched-chain lipophilic molecules and uses thereof |
| WO2002028828A1 (en) * | 2000-10-05 | 2002-04-11 | Temple University - Of The Commonwealth System Of Higher Education | Substituted (e)-styryl benzylsulfones for treating proliferative disorders |
| AUPR059400A0 (en) * | 2000-10-06 | 2000-11-02 | Bar-Ilan University | Formaldehyde-releasing prodrugs |
| AU2002214649A1 (en) * | 2000-10-16 | 2002-04-29 | Neopharm, Inc. | Liposomal formulation of mitoxantrone |
| AU2002310122A1 (en) * | 2001-05-25 | 2002-12-09 | Human Genome Sciences, Inc. | Chemokine beta-1 fusion proteins |
| RU2298414C2 (ru) | 2001-08-21 | 2007-05-10 | Астеллас Фарма Инк. | Медицинское применение ингибитора гистоновой дезацетилазы и способ оценки его противоопухолевого действия |
| JP4638148B2 (ja) | 2001-10-16 | 2011-02-23 | スローン − ケタリング・インスティテュート・フォー・キャンサー・リサーチ | 神経変性疾患および脳の癌の処置 |
| AU2002348474A1 (en) * | 2001-10-18 | 2003-04-28 | The Salk Institute For Biological Studies | Methods of using deacetylase inhibitors to promote cell differentiation and regeneration |
| JP5424521B2 (ja) * | 2001-12-21 | 2014-02-26 | ヒューマン ジノーム サイエンシーズ， インコーポレイテッド | アルブミン融合タンパク質 |
| AU2002364587A1 (en) * | 2001-12-21 | 2003-07-30 | Human Genome Sciences, Inc. | Albumin fusion proteins |
| EP2266552A3 (en) | 2002-03-04 | 2011-03-02 | Merck HDAC Research, LLC | Methods of inducing terminal differentiation |
| US7456219B2 (en) | 2002-03-04 | 2008-11-25 | Merck Hdac Research, Llc | Polymorphs of suberoylanilide hydroxamic acid |
| US7148257B2 (en) | 2002-03-04 | 2006-12-12 | Merck Hdac Research, Llc | Methods of treating mesothelioma with suberoylanilide hydroxamic acid |
| US7154002B1 (en) | 2002-10-08 | 2006-12-26 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| US7250514B1 (en) | 2002-10-21 | 2007-07-31 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| CA2513213C (en) | 2003-01-22 | 2013-07-30 | Human Genome Sciences, Inc. | Albumin fusion proteins |
| US7169801B2 (en) | 2003-03-17 | 2007-01-30 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| CA2535806C (en) | 2003-08-26 | 2009-02-17 | Aton Pharma, Inc. | The use of hdac inhibitors for the treatment of cancer |
| AU2004270150C1 (en) | 2003-08-29 | 2011-07-14 | Merck Hdac Research, Llc | Combination methods of treating cancer |
| US20050159470A1 (en) * | 2003-12-19 | 2005-07-21 | Syrrx, Inc. | Histone deacetylase inhibitors |
| US20050137234A1 (en) * | 2003-12-19 | 2005-06-23 | Syrrx, Inc. | Histone deacetylase inhibitors |
| WO2005087216A2 (de) * | 2004-03-12 | 2005-09-22 | Eberhard-Karls-Universität Tübingen | Behandlung von anämischen zuständen durch inhibierung der erythrozytenapoptose |
| US7642275B2 (en) * | 2004-12-16 | 2010-01-05 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| US7642253B2 (en) * | 2005-05-11 | 2010-01-05 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| TWI365068B (en) | 2005-05-20 | 2012-06-01 | Merck Sharp & Dohme | Formulations of suberoylanilide hydroxamic acid and methods for producing same |
| AU2006270322A1 (en) * | 2005-07-14 | 2007-01-25 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| EP1976835A2 (en) * | 2006-01-13 | 2008-10-08 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| EP2049139A4 (en) | 2006-04-24 | 2009-06-24 | Gloucester Pharmaceuticals Inc | TREATMENT OF TUMORS EXPRESSING RAS |
| US8957027B2 (en) | 2006-06-08 | 2015-02-17 | Celgene Corporation | Deacetylase inhibitor therapy |
| MX2009006969A (es) | 2006-12-29 | 2010-04-07 | Gloucester Pharmaceuticals | Purificacion de romidepsina. |
| WO2010105112A1 (en) * | 2009-03-11 | 2010-09-16 | Hemaquest Pharmaceuticals, Inc. | Detection of short-chain fatty acids in biological samples |
| US20110086869A1 (en) | 2009-09-24 | 2011-04-14 | The Trustees Of Boston University | Methods for treating viral disorders |
| CN102802412A (zh) | 2009-12-08 | 2012-11-28 | 海玛奎斯特医药公司 | 用于治疗红细胞病症的方法及低剂量方案 |
| US20110245154A1 (en) | 2010-03-11 | 2011-10-06 | Hemaquest Pharmaceuticals, Inc. | Methods and Compositions for Treating Viral or Virally-Induced Conditions |
| MY185130A (en) | 2010-07-12 | 2021-04-30 | Celgene Corp | Romidepsin solid forms and uses thereof |
| US8859502B2 (en) | 2010-09-13 | 2014-10-14 | Celgene Corporation | Therapy for MLL-rearranged leukemia |
| AU2013202506B2 (en) | 2012-09-07 | 2015-06-18 | Celgene Corporation | Resistance biomarkers for hdac inhibitors |
| AU2013202507B9 (en) | 2012-11-14 | 2015-08-13 | Celgene Corporation | Inhibition of drug resistant cancer cells |
| NZ630311A (en) | 2013-12-27 | 2016-03-31 | Celgene Corp | Romidepsin formulations and uses thereof |
| GB2567093A (en) | 2016-07-15 | 2019-04-03 | Viracta Therapeutics Inc | Histone deacetylase inhibitors for use in immunotherapy |
| EP3976198A4 (en) | 2019-05-31 | 2023-07-19 | Viracta Subsidiary, Inc. | METHODS OF TREATING VIRUS-ASSOCIATED CANCERS WITH HISTONE DEACETYLASE INHIBITORS |
Family Cites Families (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2940855A (en) * | 1957-11-27 | 1960-06-14 | Eastman Kodak Co | Sensitization of photographic emulsions |
| US3219630A (en) * | 1961-08-25 | 1965-11-23 | Tenneco Chem | Production of branched chain polyoxymethylene polycarboxylates |
| US3293220A (en) * | 1962-10-11 | 1966-12-20 | Toyo Rayon Co Ltd | Process for heat stabilization of polyoxymethylene |
| FR1386096A (fr) * | 1963-03-26 | 1965-01-15 | Heyden Newport Chemical Corp | Perfectionnements apportés aux procédés pour la production de dicarboxylates de méthylène |
| US3336262A (en) * | 1965-11-05 | 1967-08-15 | Tenneco Chem | Branched chain polyoxymethylene polycarboxylates |
| FR1540418A (fr) * | 1966-07-21 | 1968-09-27 | Asahi Chemical Ind | Procédé pour la préparation d'aldéhydes et d'anhydrides d'acides |
| US3574714A (en) * | 1967-02-22 | 1971-04-13 | Sumitomo Chemical Co | Alpha,alpha-diacyloxy-2,3,4,5,6-pentachlorotoluene derivatives |
| GB1220447A (en) * | 1967-04-19 | 1971-01-27 | Wyeth John & Brother Ltd | Salicylic acid derivatives |
| US3720706A (en) * | 1972-01-24 | 1973-03-13 | Chevron Res | Methylene and oxymethylene bis-ester production |
| US3812176A (en) * | 1972-01-24 | 1974-05-21 | Chevron Res | Methylene and oxymethylene bis-ester production |
| CA1012885A (en) * | 1972-06-28 | 1977-06-28 | Chevron Research And Technology Company | Fungus and mold control |
| US3931412A (en) * | 1972-06-28 | 1976-01-06 | Chevron Research Company | Fungus and bacteria control with di-carboxylic acid esters |
| DE2417143C2 (de) * | 1974-04-09 | 1982-04-15 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von (Thio) Phosphor(Phosphon)säureestern |
| US4123552A (en) * | 1974-05-09 | 1978-10-31 | Chevron Research Company | Compositions for preserving crops and animal feedstuffs |
| US4012526A (en) * | 1974-05-09 | 1977-03-15 | Chevron Research Company | Oxymethylene di-carboxylic acid esters as anti-fungal agents and animal growth promoters |
| US4105681A (en) * | 1975-08-01 | 1978-08-08 | Hoffmann-La Roche Inc. | 9-phenyl 5,6-dimethyl-nona-2,4,6,8-tetraeonic acid compounds |
| US4215215A (en) * | 1975-08-01 | 1980-07-29 | Hoffmann-La Roche Inc. | 9-Phenyl-nonate traene compounds |
| US4198416A (en) * | 1976-09-30 | 1980-04-15 | Meiji Seika Kaisha, Ltd. | 5-Alkoxy-picolinic esters and anti-hypertensive composition containing 5-alkoxy-picolinic esters |
| DE3175184D1 (en) * | 1980-12-26 | 1986-09-25 | Ss Pharmaceutical Co | 2,3-butanediol diester derivatives, process for producing the same, and an antiulcer drug containing the same |
| JPS5815912A (ja) * | 1981-07-22 | 1983-01-29 | Ss Pharmaceut Co Ltd | 消炎鎮痛剤 |
| GB2126082A (en) * | 1982-08-12 | 1984-03-21 | Heinrich Schulze | Pharmaceutical preparations having analgetic and cytostatic activity |
| CA1201127A (en) * | 1982-09-10 | 1986-02-25 | Katsuhiro Uchida | Biphenylylpropionic acid derivative, process for preparing the same and pharmaceutical composition containing the same |
| US4816570A (en) * | 1982-11-30 | 1989-03-28 | The Board Of Regents Of The University Of Texas System | Biologically reversible phosphate and phosphonate protective groups |
| US5196567A (en) * | 1983-02-19 | 1993-03-23 | Kaken Pharmaceutical Co., Ltd. | Biphenylylpropionic acid derivative, process for preparing the same and pharmaceutical composition containing the same |
| GB8310080D0 (en) * | 1983-04-14 | 1983-05-18 | Interox Chemicals Ltd | Bleach composition |
| GB8310081D0 (en) * | 1983-04-14 | 1983-05-18 | Interox Chemicals Ltd | Peroxygen compounds |
| JPS601122A (ja) * | 1983-06-20 | 1985-01-07 | Green Cross Corp:The | ビフエニリルプロピオン酸誘導体脂肪乳剤 |
| US4760057A (en) * | 1983-06-23 | 1988-07-26 | Merck & Co., Inc. | (Acyloxyalkoxy)carbonyl derivatives as bioreversible prodrug moieties for primary and secondary amine functions in drugs |
| IT1213182B (it) * | 1984-06-25 | 1989-12-14 | Simes | Derivati di composti a struttura catecolamminica. |
| US4916230A (en) * | 1984-07-02 | 1990-04-10 | Merck & Co., Inc. | Process for preparing novel N-(acyloxy-alkoxy)carbonyl derivatives useful as bioreversible prodrug moieties for primary and secondary amine functions in drugs |
| US4968788A (en) * | 1986-04-04 | 1990-11-06 | Board Of Regents, The University Of Texas System | Biologically reversible phosphate and phosphonate protective gruops |
| DK498487A (da) * | 1986-10-06 | 1988-04-07 | Hoffmann La Roche | Hidtil ukendte retinoider |
| US5025029A (en) * | 1986-10-10 | 1991-06-18 | Children's Hospital Medical Center Of Northern California | Method for augmenting fetal hemoglobin |
| JPS63101348A (ja) * | 1986-10-20 | 1988-05-06 | Idemitsu Kosan Co Ltd | １，１−ジエステルの製造方法 |
| US4885311A (en) * | 1987-06-29 | 1989-12-05 | Molecular Design International | Topical transretinoids for treatment of acne and skin diseases |
| US5200553A (en) * | 1987-07-30 | 1993-04-06 | Kupat Holim Health Insurance Institution Of The General Federation Of Labor | Biologically active carboxylic acid esters |
| FR2633929B2 (fr) * | 1987-09-25 | 1995-05-24 | Picardie Universite | Derives non toxiques de l'acide n-butyrique, presentant des actions therapeutiques retardees |
| SG86966A1 (en) * | 1988-11-29 | 2002-03-19 | Childrens Hosp Medical Center | Medicament for augmenting fetal hemoglobin |
| CA2037150C (en) * | 1990-03-27 | 1999-12-28 | Guenter Gross | Retinoids |
| US5216004A (en) * | 1990-09-13 | 1993-06-01 | Children's Hospital Medical Center Of North California | Method for preventing malaria |
| AU3972193A (en) * | 1992-04-07 | 1993-11-08 | Scripps Research Institute, The | Method for inducing tolerance to an antigen using butyrate |
| US5569675A (en) * | 1994-03-07 | 1996-10-29 | Bar Ilan University | Methods of using carboxylic acid esters to increase fetal-hemoglobin levels |
| US5710176A (en) * | 1994-09-16 | 1998-01-20 | Bar-Ilan University | Retinoyloxy (substituted) methyl butyrates useful for the treatment of cancer and other proliferative diseases |
-
1997
- 1997-03-11 US US08/814,386 patent/US6030961A/en not_active Expired - Lifetime
-
1998
- 1998-03-11 EP EP98910333A patent/EP0986391A4/en not_active Withdrawn
- 1998-03-11 WO PCT/US1998/004834 patent/WO1998040080A1/en not_active Ceased
- 1998-03-11 JP JP53979398A patent/JP2001514665A/ja not_active Ceased
- 1998-03-11 IL IL13174298A patent/IL131742A/xx not_active IP Right Cessation
- 1998-03-11 KR KR1019997008242A patent/KR20000076151A/ko not_active Withdrawn
- 1998-03-11 AU AU64597/98A patent/AU6459798A/en not_active Abandoned
- 1998-03-11 CA CA002283162A patent/CA2283162A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU6459798A (en) | 1998-09-29 |
| WO1998040080A9 (en) | 1999-06-10 |
| US6030961A (en) | 2000-02-29 |
| WO1998040080A1 (en) | 1998-09-17 |
| CA2283162A1 (en) | 1998-09-17 |
| EP0986391A1 (en) | 2000-03-22 |
| IL131742A0 (en) | 2001-03-19 |
| IL131742A (en) | 2005-11-20 |
| JP2001514665A (ja) | 2001-09-11 |
| EP0986391A4 (en) | 2000-11-29 |
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| Date | Code | Title | Description |
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| PA0105 | International application |
Patent event date: 19990910 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |