ES2524361T3 - Iminoazúcares para su uso en el tratamiento de enfermedades por bunyavirus y togavirus - Google Patents
Iminoazúcares para su uso en el tratamiento de enfermedades por bunyavirus y togavirus Download PDFInfo
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- ES2524361T3 ES2524361T3 ES10786885.3T ES10786885T ES2524361T3 ES 2524361 T3 ES2524361 T3 ES 2524361T3 ES 10786885 T ES10786885 T ES 10786885T ES 2524361 T3 ES2524361 T3 ES 2524361T3
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- RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000012678 infectious agent Substances 0.000 description 1
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- 238000002347 injection Methods 0.000 description 1
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- 238000001361 intraarterial administration Methods 0.000 description 1
- 238000007913 intrathecal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000034217 membrane fusion Effects 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 229960001512 miglustat Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
- PGSADBUBUOPOJS-UHFFFAOYSA-N neutral red Chemical compound Cl.C1=C(C)C(N)=CC2=NC3=CC(N(C)C)=CC=C3N=C21 PGSADBUBUOPOJS-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000002245 particle Substances 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
- 239000012071 phase Substances 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
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 230000001850 reproductive effect Effects 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
- 239000000126 substance Substances 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000013595 supernatant sample Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 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
- 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
- 210000002845 virion Anatomy 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
Classifications
-
- 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
- A61K31/33—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
- 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
-
- 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
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18661409P | 2009-06-12 | 2009-06-12 | |
| US186614P | 2009-06-12 | ||
| PCT/US2010/038247 WO2010144759A1 (en) | 2009-06-12 | 2010-06-11 | Iminosugars and methods of treating bunyaviral and togaviral diseases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2524361T3 true ES2524361T3 (es) | 2014-12-05 |
Family
ID=43306958
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10786885.3T Active ES2524361T3 (es) | 2009-06-12 | 2010-06-11 | Iminoazúcares para su uso en el tratamiento de enfermedades por bunyavirus y togavirus |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US8426445B2 (https=) |
| EP (1) | EP2440205B1 (https=) |
| JP (1) | JP5634510B2 (https=) |
| KR (1) | KR101463661B1 (https=) |
| CN (1) | CN102639133B (https=) |
| CA (1) | CA2765086C (https=) |
| ES (1) | ES2524361T3 (https=) |
| WO (1) | WO2010144759A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2753195C (en) | 2009-02-23 | 2015-06-02 | United Therapeutics Corporation | Iminosugars and methods of treating viral diseases |
| CN102639133B (zh) * | 2009-06-12 | 2015-03-11 | 联合治疗公司 | 亚氨基糖和治疗布尼亚病毒性疾病以及披膜病毒性疾病的方法 |
| IN2014MN02539A (https=) | 2012-06-06 | 2015-07-24 | Unither Virology Llc | |
| CN102875450B (zh) * | 2012-10-25 | 2015-04-08 | 上海丝绸集团股份有限公司 | 一种从桑叶中提取制备1-脱氧野尻霉素的工艺方法 |
| KR20150128899A (ko) | 2013-03-15 | 2015-11-18 | 유니터 바이롤로지, 엘엘씨 | 항박테리아 화합물 |
| KR20160055916A (ko) | 2013-09-16 | 2016-05-18 | 이머전트 바이롤로지 엘엘씨 | 데옥시노지리마이신 유도체 및 그의 이용 방법 |
| CN104357583B (zh) * | 2014-10-31 | 2016-11-09 | 中国检验检疫科学研究院 | 巴马哈森林病毒的实时荧光rt-pcr检测试剂盒和方法 |
| CA2966893C (en) * | 2014-11-05 | 2023-10-24 | Emergent Virology Llc | Iminosugars |
| CN114732822B (zh) * | 2019-03-13 | 2023-06-30 | 中国人民解放军军事科学院军事医学研究院 | 氨基葡萄糖及其衍生物作为抗病毒药物的应用 |
Family Cites Families (46)
| 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 |
| 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 |
| WO1995022975A1 (en) | 1994-02-25 | 1995-08-31 | G.D. Searle & Co. | Use of 1-deoxynojirimycin and its derivatives for treating mammals infected with respiratory syncytial virus |
| BR9813508A (pt) * | 1997-12-11 | 2000-10-03 | Univ Oxford | Inibição de replicação viral associada com membrana |
| EP1714676A3 (en) | 1998-02-12 | 2006-11-15 | G.D. Searle LLC. | Use of N-substituted-1,5-dideoxy-1,5-imino-D-glucitol compounds for treating hepatitis virus infections |
| US6809083B1 (en) | 1998-02-12 | 2004-10-26 | Richard A. Mueller | Use of N-substituted-1, 5-dideoxy-1, 5-imino-D-glucitol compounds for treating hepatitis virus infections |
| 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 |
| JP2002536407A (ja) * | 1999-02-12 | 2002-10-29 | ジー・ディー・サール・アンド・カンパニー | 肝炎ウィルス感染の治療のための置換−１，５−ジデオキシ−１，５−イミノ−ｄ−グルシトール化合物の使用 |
| GB0100889D0 (en) * | 2001-01-12 | 2001-02-21 | Oxford Glycosciences Uk Ltd | Compounds |
| ATE234626T1 (de) * | 1999-07-26 | 2003-04-15 | Searle & Co | Verwendung von langkettigen n-alkyl derivaten von deoxynojirimycin mit glucocerebrosidase enzyme zur herstellung eines medikaments zur behandlung von mit glykolipiden akkumulation zusammenhängenden krankheiten |
| 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 |
| PT2441467E (pt) * | 2003-01-31 | 2015-10-12 | Sinai School Medicine | Terapia combinada para o tratamento de transtornos associados a uma deficiência proteica |
| US7446098B2 (en) | 2003-02-18 | 2008-11-04 | Mount Sinai School Of Medicine Of New York University | Combination therapy for treating protein deficiencies |
| US7135575B2 (en) * | 2003-03-03 | 2006-11-14 | Array Biopharma, Inc. | P38 inhibitors and methods of use thereof |
| US20060211752A1 (en) | 2004-03-16 | 2006-09-21 | Kohn Leonard D | Use of phenylmethimazoles, methimazole derivatives, and tautomeric cyclic thiones for the treatment of autoimmune/inflammatory diseases associated with toll-like receptor overexpression |
| 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 |
| KR20080056688A (ko) * | 2005-03-16 | 2008-06-23 | 유니버시티 오브 옥스퍼드 | Ｈｉｖ－ｉ용 만노스 면역원 |
| EP2932982B1 (en) * | 2005-05-17 | 2018-10-03 | 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 |
| AU2006272497B2 (en) | 2005-07-27 | 2012-07-19 | University Of Florida Research Foundation, Inc. | 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 |
| AU2007241622A1 (en) * | 2006-04-24 | 2007-11-01 | Academisch Medisch Centrum | Improved treatment of cystic fibrosis |
| US8975280B2 (en) * | 2006-05-24 | 2015-03-10 | The Chancellor, Masters And Scholars Of The University Of Oxford | Deoxynojirimycin and D-arabinitol analogs and methods of using |
| 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 |
| US20080131398A1 (en) * | 2006-08-21 | 2008-06-05 | United Therapeutics Corporation | Combination therapy for treatment of viral infections |
| WO2008068548A1 (en) | 2006-12-08 | 2008-06-12 | Institut Necker | Use of inhibitors of the glycosylation process for the prevention and treatment of genetic diseases |
| US20090252785A1 (en) * | 2008-03-26 | 2009-10-08 | University Of Oxford | Endoplasmic reticulum targeting liposomes |
| 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 |
| KR20120059447A (ko) * | 2009-03-27 | 2012-06-08 | 더 챈슬러 마스터즈 앤드 스칼라스 오브 더 유니버시티 오브 옥스포드 | 콜레스테롤 수준 저하 리포좀 |
| CN102639133B (zh) * | 2009-06-12 | 2015-03-11 | 联合治疗公司 | 亚氨基糖和治疗布尼亚病毒性疾病以及披膜病毒性疾病的方法 |
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2010
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- 2010-06-11 ES ES10786885.3T patent/ES2524361T3/es active Active
- 2010-06-11 KR KR1020127000433A patent/KR101463661B1/ko not_active Expired - Fee Related
- 2010-06-11 JP JP2012515167A patent/JP5634510B2/ja not_active Expired - Fee Related
- 2010-06-11 US US12/813,882 patent/US8426445B2/en not_active Expired - Fee Related
- 2010-06-11 EP EP10786885.3A patent/EP2440205B1/en not_active Not-in-force
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2013
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2440205A1 (en) | 2012-04-18 |
| CA2765086C (en) | 2015-12-15 |
| US8748460B2 (en) | 2014-06-10 |
| US8426445B2 (en) | 2013-04-23 |
| US20130150405A1 (en) | 2013-06-13 |
| JP5634510B2 (ja) | 2014-12-03 |
| KR20120038960A (ko) | 2012-04-24 |
| EP2440205B1 (en) | 2014-08-27 |
| WO2010144759A1 (en) | 2010-12-16 |
| US20100317696A1 (en) | 2010-12-16 |
| EP2440205A4 (en) | 2013-04-24 |
| CN102639133A (zh) | 2012-08-15 |
| KR101463661B1 (ko) | 2014-11-19 |
| CN102639133B (zh) | 2015-03-11 |
| JP2012530061A (ja) | 2012-11-29 |
| CA2765086A1 (en) | 2010-12-16 |
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