JP5752689B2 - フィロウイルス疾患を治療するイミノ糖および方法 - Google Patents
フィロウイルス疾患を治療するイミノ糖および方法 Download PDFInfo
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- JP5752689B2 JP5752689B2 JP2012528004A JP2012528004A JP5752689B2 JP 5752689 B2 JP5752689 B2 JP 5752689B2 JP 2012528004 A JP2012528004 A JP 2012528004A JP 2012528004 A JP2012528004 A JP 2012528004A JP 5752689 B2 JP5752689 B2 JP 5752689B2
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- 239000011664 nicotinic acid Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 229950010765 pivalate Drugs 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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- 230000002250 progressing effect Effects 0.000 description 1
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- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000013595 supernatant sample Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
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- 239000003826 tablet Substances 0.000 description 1
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- 238000004448 titration Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000014599 transmission of virus Effects 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
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| US27225309P | 2009-09-04 | 2009-09-04 | |
| US61/272,253 | 2009-09-04 | ||
| US28250710P | 2010-02-22 | 2010-02-22 | |
| US61/282,507 | 2010-02-22 | ||
| PCT/US2010/047493 WO2011028779A1 (en) | 2009-09-04 | 2010-09-01 | Iminosugars and methods of treating filoviral diseases |
Publications (3)
| Publication Number | Publication Date |
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| JP2013503881A JP2013503881A (ja) | 2013-02-04 |
| JP2013503881A5 JP2013503881A5 (https=) | 2013-10-03 |
| JP5752689B2 true JP5752689B2 (ja) | 2015-07-22 |
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| EP (1) | EP2473046B1 (https=) |
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| KR (1) | KR20120081990A (https=) |
| CN (2) | CN105748476A (https=) |
| CA (1) | CA2772813A1 (https=) |
| ES (1) | ES2527623T3 (https=) |
| WO (1) | WO2011028779A1 (https=) |
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| EP2398321B1 (en) | 2009-02-23 | 2015-11-25 | United Therapeutics Corporation | Iminosugars and methods of treating viral diseases |
| WO2013148791A1 (en) | 2012-03-28 | 2013-10-03 | Institute For Hepatitis And Virus Research | Novel alkylated imino sugars exhibiting glucosidase inhibition and their method of use |
| KR20150035767A (ko) | 2012-06-06 | 2015-04-07 | 유니터 바이롤로지, 엘엘씨 | 신규 이미노당 및 그의 용도 |
| CN106102464A (zh) * | 2013-05-02 | 2016-11-09 | 牛津大学之校长及学者 | 采用亚氨基糖的糖脂抑制 |
| JP6456393B2 (ja) | 2013-09-16 | 2019-01-23 | エマージェント バイロロジー エルエルシー | デオキシノジリマイシン誘導体およびその使用方法 |
| EP3200826B1 (en) * | 2014-09-30 | 2021-04-21 | Vecht-lifshitz, Susan Eve | Pharmaceutical compositions for treating ebola virus disease |
| BR112017008898B1 (pt) | 2014-11-05 | 2022-11-29 | Emergent Virology Llc | Compostos de iminoaçúcares, suas composições farmacêuticas e usos dos mesmos para tratar doenças virais |
| CN109628647A (zh) * | 2019-02-02 | 2019-04-16 | 广州市妇女儿童医疗中心 | 抗病毒药物筛选方法及其应用 |
Family Cites Families (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1555654A (en) * | 1977-06-25 | 1979-11-14 | Exxon Research Engineering Co | Agricultural burner apparatus |
| NO154918C (no) * | 1977-08-27 | 1987-01-14 | Bayer Ag | Analogifremgangsmaate til fremstilling av terapeutisk aktive derivater av 3,4,5-trihydroksypiperidin. |
| DE2834122A1 (de) | 1978-08-03 | 1980-02-14 | Bayer Ag | Verfahren zur herstellung von 6-amino-6-desoxy-l-sorbose |
| DE2839309A1 (de) * | 1978-09-09 | 1980-03-27 | Bayer Ag | 3,4,5-trihydroxypiperidin-derivate |
| DE2853573A1 (de) | 1978-12-12 | 1980-07-03 | Bayer Ag | Herstellung von n-substituierten derivaten des l-desoxynojirimycins |
| DE3038901A1 (de) * | 1980-10-15 | 1982-05-06 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von n-substituierten derivaten des 1-desoxynojirimycins |
| DE3611841A1 (de) * | 1986-04-09 | 1987-10-15 | Bayer Ag | Verfahren zur herstellung von 1-desoxynojirimycin und dessen n-derivaten |
| US5043273A (en) * | 1989-08-17 | 1991-08-27 | Monsanto Company | Phosphorylated glycosidase inhibitor prodrugs |
| US5103008A (en) * | 1989-08-17 | 1992-04-07 | Monsanto Company | Compound, N-butyl-deoxynojirimycin-6-phosphate |
| US4994572A (en) * | 1989-10-12 | 1991-02-19 | Monsanto Company | Synthesis of nojirimycin derivatives |
| US5030638A (en) * | 1990-02-26 | 1991-07-09 | G. D. Searle & Co. | Method of antiviral enhancement |
| US5200523A (en) * | 1990-10-10 | 1993-04-06 | Monsanto Company | Synthesis of nojirimycin derivatives |
| ZA931934B (en) | 1992-03-18 | 1993-03-18 | Us Bioscience | Compostitions of N-(phosphonoacetyl)-L-aspartic acid and methods of their use as broad spectrum antivirals |
| US5206251A (en) * | 1992-04-01 | 1993-04-27 | G. D. Searle & Co. | 2- and 3- amino and azido derivatives of 1,5-iminosugars |
| US5399567A (en) * | 1993-05-13 | 1995-03-21 | Monsanto Company | Method of treating cholera |
| AU1876095A (en) | 1994-02-25 | 1995-09-11 | G.D. Searle & Co. | Use of 1-deoxynojirimycin and its derivatives for treating mammals infected with respiratory syncytial virus |
| KR20010033028A (ko) | 1997-12-11 | 2001-04-25 | 더 챈슬러 마스터즈 앤드 스칼라스 오브 더 유니버시티 오브 옥스포드 | 막-관련 바이러스 복제의 억제 |
| US6689759B1 (en) | 1998-02-12 | 2004-02-10 | G. D. Searle & Co. | Methods of Treating hepatitis virus infections with N-substituted-1,5-dideoxy-1,5-imino-d-glucitol compounds in combination therapy |
| US6610703B1 (en) * | 1998-12-10 | 2003-08-26 | G.D. Searle & Co. | Method for treatment of glycolipid storage diseases |
| GB9828474D0 (en) * | 1998-12-24 | 1999-02-17 | British Aerospace | Surface topology inspection |
| ATE402701T1 (de) * | 1999-02-12 | 2008-08-15 | United Therapeutics Corp | N-(8,8,8-trifluorooctyl)-1,5-dideoxy-1,5-imino- - glucitol zur behandlung von hepatitis-virus- infektionen |
| GB0100889D0 (en) * | 2001-01-12 | 2001-02-21 | Oxford Glycosciences Uk Ltd | Compounds |
| EP1196190B1 (en) * | 1999-07-26 | 2003-03-19 | G.D. SEARLE & CO. | Use of long-chain n-alkyl derivatives of deoxynojirimycin and a glucocerebrosidase enzyme for the manufacture of a medicament for the treatment of glycolipid storage diseases |
| US7256005B2 (en) * | 1999-08-10 | 2007-08-14 | The Chancellor, Masters And Scholars Of The University Of Oxford | Methods for identifying iminosugar derivatives that inhibit HCV p7 ion channel activity |
| EP2857036B1 (en) * | 2003-01-31 | 2016-12-21 | Mount Sinai School of Medicine of New York University | Combination therapy for treating protein deficiency disorders |
| US7446098B2 (en) * | 2003-02-18 | 2008-11-04 | Mount Sinai School Of Medicine Of New York University | Combination therapy for treating protein deficiencies |
| US20050256168A1 (en) * | 2004-04-28 | 2005-11-17 | Block Timothy M | Compositions for oral administration for the treatment of interferon-responsive disorders |
| US7524829B2 (en) * | 2004-11-01 | 2009-04-28 | Avi Biopharma, Inc. | Antisense antiviral compounds and methods for treating a filovirus infection |
| GB0501352D0 (en) * | 2005-01-21 | 2005-03-02 | Slingsby Jason H | Use of glycosylation modulators in combination with membrane fusion inhibitors for treatment of infections caused by viruses bearing glycosylated envelope |
| CA2601797A1 (en) * | 2005-03-16 | 2006-09-21 | University Of Oxford | Mannose immunogens for hiv-1 |
| EP3782655A1 (en) * | 2005-05-17 | 2021-02-24 | Amicus Therapeutics, Inc. | A method for the treatment of pompe disease using 1-deoxynojirimycin and derivatives |
| KR20080031474A (ko) * | 2005-07-27 | 2008-04-08 | 유니버시티 오브 플로리다 리서치 파운데이션, 아이엔씨. | 안구 질환의 치료를 위한 열충격의 사용 |
| US20100004156A1 (en) * | 2005-07-27 | 2010-01-07 | Shalesh Kaushal | Small Compounds That Correct Protein Misfolding and Uses Thereof |
| US20070244184A1 (en) * | 2006-01-09 | 2007-10-18 | Simon Fraser University | Glycosidase inhibitors and methods of synthesizing same |
| DE602007008870D1 (de) * | 2006-04-24 | 2010-10-14 | Amc Amsterdam | Verbessertes verfahren zur behandlung von cystischer fibrose |
| CN104876855A (zh) * | 2006-05-24 | 2015-09-02 | 联合治疗公司 | 脱氧吉瑞霉素和d-阿拉伯胶素醇类似物及使用方法 |
| JP2009545621A (ja) | 2006-08-02 | 2009-12-24 | ユナイテッド セラピューティクス コーポレーション | ウィルス感染症のリポソーム処置 |
| KR20090057035A (ko) * | 2006-08-21 | 2009-06-03 | 유나이티드 세러퓨틱스 코오포레이션 | 바이러스 감염의 치료를 위한 병용 요법 |
| KR20100127842A (ko) * | 2008-03-26 | 2010-12-06 | 유니버시티 오브 옥스퍼드 | 소포체 표적화 리포좀 |
| WO2010027996A1 (en) * | 2008-09-02 | 2010-03-11 | Institute For Hepatitis And Virus Research | Novel imino sugar derivatives demonstrate potent antiviral activity and reduced toxicity |
| US8703744B2 (en) * | 2009-03-27 | 2014-04-22 | The Chancellor, Masters And Scholars Of The University Of Oxford | Cholesterol level lowering liposomes |
-
2010
- 2010-09-01 CA CA2772813A patent/CA2772813A1/en not_active Abandoned
- 2010-09-01 KR KR1020127007711A patent/KR20120081990A/ko not_active Ceased
- 2010-09-01 US US12/873,708 patent/US20110065754A1/en not_active Abandoned
- 2010-09-01 WO PCT/US2010/047493 patent/WO2011028779A1/en not_active Ceased
- 2010-09-01 ES ES10814412.2T patent/ES2527623T3/es active Active
- 2010-09-01 JP JP2012528004A patent/JP5752689B2/ja not_active Expired - Fee Related
- 2010-09-01 CN CN201610084994.9A patent/CN105748476A/zh active Pending
- 2010-09-01 CN CN2010800483990A patent/CN102595895A/zh active Pending
- 2010-09-01 EP EP10814412.2A patent/EP2473046B1/en not_active Not-in-force
Also Published As
| Publication number | Publication date |
|---|---|
| JP2013503881A (ja) | 2013-02-04 |
| KR20120081990A (ko) | 2012-07-20 |
| EP2473046A1 (en) | 2012-07-11 |
| ES2527623T3 (es) | 2015-01-27 |
| EP2473046B1 (en) | 2014-10-22 |
| US20110065754A1 (en) | 2011-03-17 |
| CN105748476A (zh) | 2016-07-13 |
| CA2772813A1 (en) | 2011-03-10 |
| EP2473046A4 (en) | 2013-04-24 |
| WO2011028779A1 (en) | 2011-03-10 |
| CN102595895A (zh) | 2012-07-18 |
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