CA2849114C - Sialic acid analogs - Google Patents
Sialic acid analogs Download PDFInfo
- Publication number
- CA2849114C CA2849114C CA2849114A CA2849114A CA2849114C CA 2849114 C CA2849114 C CA 2849114C CA 2849114 A CA2849114 A CA 2849114A CA 2849114 A CA2849114 A CA 2849114A CA 2849114 C CA2849114 C CA 2849114C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- sialic acid
- structural formula
- group
- hydrogen
- Prior art date
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
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- WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 description 1
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
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- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
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- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000003553 thiiranes Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 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
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/02—Acyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/10—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to heterocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/02—Acyclic radicals
- C07H7/027—Keto-aldonic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Physical Education & Sports Medicine (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161550610P | 2011-10-24 | 2011-10-24 | |
| US61/550,610 | 2011-10-24 | ||
| PCT/US2012/061737 WO2013063149A1 (en) | 2011-10-24 | 2012-10-24 | Sialic acid analogs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2849114A1 CA2849114A1 (en) | 2013-05-02 |
| CA2849114C true CA2849114C (en) | 2020-12-15 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2849114A Active CA2849114C (en) | 2011-10-24 | 2012-10-24 | Sialic acid analogs |
Country Status (13)
| Country | Link |
|---|---|
| US (5) | US8840926B2 (enExample) |
| EP (1) | EP2771348B1 (enExample) |
| JP (1) | JP6196224B2 (enExample) |
| KR (1) | KR102049214B1 (enExample) |
| CN (1) | CN103974965B (enExample) |
| AU (1) | AU2012328874B2 (enExample) |
| BR (1) | BR112014009760B1 (enExample) |
| CA (1) | CA2849114C (enExample) |
| ES (1) | ES2807890T3 (enExample) |
| HK (1) | HK1201067A1 (enExample) |
| IL (1) | IL231714B (enExample) |
| MX (1) | MX347541B (enExample) |
| WO (1) | WO2013063149A1 (enExample) |
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| US9241896B2 (en) | 2008-12-19 | 2016-01-26 | Ultragenyx Pharmaceutical Inc. | Methods and formulations for treating sialic acid deficiencies |
| CA2805222A1 (en) | 2010-07-13 | 2012-01-19 | Ultragenyx Pharmaceutical Inc. | Methods and formulations for treating sialic acid deficiencies |
| ES2807890T3 (es) | 2011-10-24 | 2021-02-24 | Ultragenyx Pharmaceutical Inc | Análogos de ácido siálico |
| CA2862836A1 (en) * | 2012-01-18 | 2013-07-25 | Ultragenyx Pharmaceutical Inc. | Methods and formulations for treating sialic acid deficiencies |
| TW201720803A (zh) | 2015-09-14 | 2017-06-16 | 超基因克斯製藥公司 | 唾液酸或其鹽或溶劑合物之晶型 |
| WO2024173797A1 (en) * | 2023-02-17 | 2024-08-22 | Ultragenyx Pharmaceutical Inc. | Crystalline forms of sialic acid derivatives and methods for their use |
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| JPS6168418A (ja) | 1984-09-11 | 1986-04-08 | Kanto Ishi Pharma Co Ltd | 去痰薬 |
| JPS63139193A (ja) * | 1986-11-28 | 1988-06-10 | Mect Corp | シアル酸誘導体１，７−ラクトン |
| US6156544A (en) | 1993-06-09 | 2000-12-05 | Glaxo Group Limited | Process for the preparation of N-acetylneuraminic acid |
| EP0820305A2 (en) | 1995-04-04 | 1998-01-28 | Wound Healing of Oklahoma | Cancer treatment by photodynamic therapy, in combination with an immunoadjuvant |
| US5624677A (en) | 1995-06-13 | 1997-04-29 | Pentech Pharmaceuticals, Inc. | Controlled release of drugs delivered by sublingual or buccal administration |
| EP1070725B9 (en) | 1998-04-10 | 2011-02-23 | Mitsubishi Chemical Corporation | Solid dispersion containing sialic acid derivative |
| KR20030006721A (ko) | 2001-07-14 | 2003-01-23 | 삼성전자 주식회사 | 리소그라피 시스템 및 이를 이용한 레티클 표면의 파티클제거방법 |
| ATE503498T1 (de) | 2002-06-21 | 2011-04-15 | Novo Nordisk Healthcare Ag | Pegylierte glykoformen von faktor vii |
| US7238677B2 (en) | 2003-03-28 | 2007-07-03 | Kimberly-Clark Worldwide, Inc. | Prevention of urogenital infections |
| JP2007517776A (ja) * | 2003-12-09 | 2007-07-05 | スフェリックス， インコーポレイテッド | カテコール官能基を有する生体接着性ポリマー |
| KR101202607B1 (ko) | 2005-03-03 | 2012-11-20 | 마나테크 인코포레이티드 | 영양 보조제의 조절된 방출을 위한 방법 및 조성물 |
| US20100226855A1 (en) * | 2006-03-02 | 2010-09-09 | Spherics, Inc. | Rate-Controlled Oral Dosage Formulations |
| WO2008027557A2 (en) * | 2006-08-31 | 2008-03-06 | Spherics, Inc. | Topiramate compositions and methods of enhancing its bioavailability |
| CA2680842C (en) | 2007-05-31 | 2015-11-24 | Government Of The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services National Institutes Of Health | N-acetyl mannosamine or derivatives thereof for use in treating a kidney disorder in a mammal |
| US20090081249A1 (en) | 2007-08-27 | 2009-03-26 | Massachusetts Institute Of Technology | Bi-Functional Polymer-Attached Inhibitors of Influenza Virus |
| US8524772B2 (en) | 2008-05-09 | 2013-09-03 | Tiara Pharmaceuticals, Inc. | Controlled release of N-acetylcysteine (NAC) for reduction of systemic and/or vascular inflammation |
| KR101116864B1 (ko) | 2008-08-01 | 2012-02-29 | 주식회사 베네비오 | 고지혈증, 지방간 또는 비만의 예방 또는 치료용 조성물 |
| US20100160363A1 (en) | 2008-12-19 | 2010-06-24 | Aaipharma Services Corp. | Extended-release pharmaceutical formulations |
| US9241896B2 (en) | 2008-12-19 | 2016-01-26 | Ultragenyx Pharmaceutical Inc. | Methods and formulations for treating sialic acid deficiencies |
| US20100159001A1 (en) | 2008-12-19 | 2010-06-24 | Cardinal John R | Extended-Release Pharmaceutical Formulations |
| JP5626734B2 (ja) | 2009-05-15 | 2014-11-19 | 公益財団法人ヒューマンサイエンス振興財団 | Ｇｎｅタンパク質の機能低下に起因する疾患の治療用医薬剤、食品組成物 |
| CA2805222A1 (en) | 2010-07-13 | 2012-01-19 | Ultragenyx Pharmaceutical Inc. | Methods and formulations for treating sialic acid deficiencies |
| ES2807890T3 (es) | 2011-10-24 | 2021-02-24 | Ultragenyx Pharmaceutical Inc | Análogos de ácido siálico |
| CA2862836A1 (en) | 2012-01-18 | 2013-07-25 | Ultragenyx Pharmaceutical Inc. | Methods and formulations for treating sialic acid deficiencies |
| KR102646509B1 (ko) | 2015-01-28 | 2024-03-11 | 교와 핫꼬 바이오 가부시키가이샤 | N-아세틸노이라민산암모늄염·무수화물의 결정 및 그 제조 방법 |
| TW201720803A (zh) | 2015-09-14 | 2017-06-16 | 超基因克斯製藥公司 | 唾液酸或其鹽或溶劑合物之晶型 |
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| ES2807890T3 (es) | 2021-02-24 |
| MX347541B (es) | 2017-04-28 |
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| BR112014009760B1 (pt) | 2022-11-29 |
| US10065981B2 (en) | 2018-09-04 |
| JP6196224B2 (ja) | 2017-09-13 |
| IL231714A0 (en) | 2014-05-28 |
| US10457701B2 (en) | 2019-10-29 |
| EP2771348B1 (en) | 2020-05-20 |
| BR112014009760A8 (pt) | 2018-01-16 |
| JP2014530882A (ja) | 2014-11-20 |
| IL231714B (en) | 2018-10-31 |
| CN103974965B (zh) | 2019-09-24 |
| US20130122094A1 (en) | 2013-05-16 |
| KR20140084277A (ko) | 2014-07-04 |
| US20190127409A1 (en) | 2019-05-02 |
| BR112014009760A2 (pt) | 2017-04-18 |
| KR102049214B1 (ko) | 2019-11-28 |
| AU2012328874B2 (en) | 2017-08-31 |
| EP2771348A1 (en) | 2014-09-03 |
| US20160297846A1 (en) | 2016-10-13 |
| US8840926B2 (en) | 2014-09-23 |
| AU2012328874A1 (en) | 2014-04-10 |
| US10889607B2 (en) | 2021-01-12 |
| HK1201067A1 (en) | 2015-08-21 |
| US20200131215A1 (en) | 2020-04-30 |
| US9221858B2 (en) | 2015-12-29 |
| MX2014004928A (es) | 2014-11-10 |
| EP2771348A4 (en) | 2015-09-09 |
| CN103974965A (zh) | 2014-08-06 |
| US20150038693A1 (en) | 2015-02-05 |
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