IL112011A - Crystalline 5-acetamdo-2,3,4,5-tetradeoxy-4-guanidino-d-glycero-d-galacto- non-enopyranosonic acid hydrates their preparation and pharmaceutical compositions containing them - Google Patents
Crystalline 5-acetamdo-2,3,4,5-tetradeoxy-4-guanidino-d-glycero-d-galacto- non-enopyranosonic acid hydrates their preparation and pharmaceutical compositions containing themInfo
- Publication number
- IL112011A IL112011A IL11201194A IL11201194A IL112011A IL 112011 A IL112011 A IL 112011A IL 11201194 A IL11201194 A IL 11201194A IL 11201194 A IL11201194 A IL 11201194A IL 112011 A IL112011 A IL 112011A
- Authority
- IL
- Israel
- Prior art keywords
- crystalline form
- guanidino
- glycero
- tetradeoxy
- hydrate
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 42
- 238000002360 preparation method Methods 0.000 title claims description 23
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 10
- 150000004677 hydrates Chemical class 0.000 title description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 62
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 49
- 239000013078 crystal Substances 0.000 claims description 37
- 239000000243 solution Substances 0.000 claims description 27
- 239000007864 aqueous solution Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 238000002425 crystallisation Methods 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 11
- 239000007900 aqueous suspension Substances 0.000 claims description 5
- 230000032683 aging Effects 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 2
- 150000002576 ketones Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 description 20
- 238000003828 vacuum filtration Methods 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- 239000000725 suspension Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 238000010899 nucleation Methods 0.000 description 5
- 239000002002 slurry Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000012512 characterization method Methods 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000003443 antiviral agent Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- SQVRNKJHWKZAKO-PFQGKNLYSA-N N-acetyl-beta-neuraminic acid Chemical class CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-PFQGKNLYSA-N 0.000 description 1
- 235000006629 Prosopis spicigera Nutrition 0.000 description 1
- 240000000037 Prosopis spicigera Species 0.000 description 1
- -1 acetone Chemical class 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 241000902900 cellular organisms Species 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- BQINXKOTJQCISL-GRCPKETISA-N keto-neuraminic acid Chemical class OC(=O)C(=O)C[C@H](O)[C@@H](N)[C@@H](O)[C@H](O)[C@H](O)CO BQINXKOTJQCISL-GRCPKETISA-N 0.000 description 1
- 238000004619 light microscopy Methods 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB939325841A GB9325841D0 (en) | 1993-12-17 | 1993-12-17 | Chemical compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL112011A0 IL112011A0 (en) | 1995-03-15 |
| IL112011A true IL112011A (en) | 1998-08-16 |
Family
ID=10746778
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL11201194A IL112011A (en) | 1993-12-17 | 1994-12-16 | Crystalline 5-acetamdo-2,3,4,5-tetradeoxy-4-guanidino-d-glycero-d-galacto- non-enopyranosonic acid hydrates their preparation and pharmaceutical compositions containing them |
Country Status (43)
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9325841D0 (en) * | 1993-12-17 | 1994-02-23 | Glaxo Group Ltd | Chemical compounds |
| MX9706496A (es) * | 1995-02-27 | 1997-11-29 | Gilead Sciences Inc | Nuevos inhibidores selectivos de las neuroaminidasas virales o bacterianas. |
| US5866601A (en) * | 1995-02-27 | 1999-02-02 | Gilead Sciences, Inc. | Carbocyclic compounds |
| US5763483A (en) * | 1995-12-29 | 1998-06-09 | Gilead Sciences, Inc. | Carbocyclic compounds |
| US6340702B1 (en) | 1996-07-22 | 2002-01-22 | Sankyo Company, Limited | Neuraminic acid derivatives, their preparation and their medical use |
| ATE211468T1 (de) * | 1996-07-22 | 2002-01-15 | Sankyo Co | Neuraminsäuredervate, ihre herstellung und medizinische verwendung |
| US6451766B1 (en) | 1996-07-22 | 2002-09-17 | Sankyo Company, Limited | Neuraminic acid derivatives, their preparation and their medical use |
| US5859284A (en) | 1996-08-23 | 1999-01-12 | Gilead Sciences, Inc. | Preparation of carbocyclic compounds |
| US6518438B2 (en) | 1996-08-23 | 2003-02-11 | Gilead Sciences, Inc. | Preparation of cyclohexene carboxylate derivatives |
| US5994377A (en) | 1996-10-21 | 1999-11-30 | Gilead Sciences, Inc. | Piperidine compounds |
| US5886213A (en) * | 1997-08-22 | 1999-03-23 | Gilead Sciences, Inc. | Preparation of carbocyclic compounds |
| TW477783B (en) * | 1997-12-12 | 2002-03-01 | Gilead Sciences Inc | Novel compounds useful as neuraminidase inhibitors and pharmaceutical compositions containing same |
| TWI291462B (en) * | 2000-04-25 | 2007-12-21 | Daiichi Sankyo Co Ltd | Hydrate crystal of neuraminic acid compound |
| US20080063722A1 (en) * | 2006-09-08 | 2008-03-13 | Advanced Inhalation Research, Inc. | Composition of a Spray-Dried Powder for Pulmonary Delivery of a Long Acting Neuraminidase Inhibitor (LANI) |
| CA2859296C (en) * | 2011-12-16 | 2016-10-11 | Daiichi Sankyo Company, Limited | Method for manufacturing neuraminic acid derivatives |
| CN109232677B (zh) * | 2018-10-18 | 2021-12-28 | 中国科学院合肥物质科学研究院 | 一种使n-乙酰神经氨酸水合物转化为n-乙酰神经氨酸的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU469694A1 (ru) * | 1972-12-22 | 1975-05-05 | Московский Ордена Трудового Красного Знамени Институт Тонкой Химической Технологии Им.М.В.Ломоносова | Способ получени 2-алкокси-6-алкил (арил)- -дигидропиранов |
| SK282950B6 (sk) * | 1990-04-24 | 2003-01-09 | Biota Scientific Management Pty Ltd | Deriváty alfa-D-neuramínovej kyseliny, spôsob ich prípravy, ich použitie a farmaceutické prípravky na ich báze |
| CA2081068C (en) * | 1991-10-23 | 2005-11-29 | Laurence Mark Von Itzstein | Antiviral 4-substituted-2-deoxy-2,3-didehydro-derivatives of .alpha.-d-neuraminic acid |
| GB9126725D0 (en) * | 1991-12-17 | 1992-02-12 | Glaxo Group Ltd | Process |
| US5639786A (en) | 1992-12-04 | 1997-06-17 | Biota Scientific Management, Pty., Ltd. | Antiviral 4-substituted-2-deoxy-2,3-didehydro-derivatives of α-D-neuraninic acid |
| GB9325841D0 (en) * | 1993-12-17 | 1994-02-23 | Glaxo Group Ltd | Chemical compounds |
-
1993
- 1993-12-17 GB GB939325841A patent/GB9325841D0/en active Pending
-
1994
- 1994-12-02 TW TW083111229A patent/TW452577B/zh not_active IP Right Cessation
- 1994-12-13 IS IS4240A patent/IS4240A/is unknown
- 1994-12-15 SI SI9430333T patent/SI0734382T1/xx unknown
- 1994-12-15 SV SV1994000076A patent/SV1994000076A/es active IP Right Grant
- 1994-12-15 ZA ZA9410003A patent/ZA9410003B/xx unknown
- 1994-12-15 EE EE9600135A patent/EE03353B1/xx unknown
- 1994-12-15 AP APAP/P/1994/000705A patent/AP541A/en active
- 1994-12-15 CN CN94194973A patent/CN1132829C/zh not_active Expired - Lifetime
- 1994-12-15 EP EP95904472A patent/EP0734382B1/en not_active Expired - Lifetime
- 1994-12-15 MY MYPI94003357A patent/MY116221A/en unknown
- 1994-12-15 AT AT95904472T patent/ATE199255T1/de active
- 1994-12-15 RU RU96115122A patent/RU2134690C1/ru active Protection Beyond IP Right Term
- 1994-12-15 ES ES95904472T patent/ES2155517T3/es not_active Expired - Lifetime
- 1994-12-15 MA MA23724A patent/MA23396A1/fr unknown
- 1994-12-15 SG SG1996007725A patent/SG46669A1/en unknown
- 1994-12-15 JP JP51653195A patent/JP3317972B2/ja not_active Expired - Lifetime
- 1994-12-15 PE PE1994257245A patent/PE31095A1/es not_active Application Discontinuation
- 1994-12-15 NZ NZ277789A patent/NZ277789A/en not_active IP Right Cessation
- 1994-12-15 CO CO94056728A patent/CO4340619A1/es unknown
- 1994-12-15 KR KR1019960703180A patent/KR100403256B1/ko not_active Expired - Lifetime
- 1994-12-15 AP APAP/P/1996/000810A patent/AP9600810A0/en unknown
- 1994-12-15 PL PL94315055A patent/PL186384B1/pl unknown
- 1994-12-15 SK SK785-96A patent/SK282972B6/sk not_active IP Right Cessation
- 1994-12-15 CA CA002177990A patent/CA2177990C/en not_active Expired - Lifetime
- 1994-12-15 DK DK95904472T patent/DK0734382T3/da active
- 1994-12-15 CN CNA2003101199989A patent/CN1502621A/zh active Pending
- 1994-12-15 DE DE69426726T patent/DE69426726T2/de not_active Expired - Lifetime
- 1994-12-15 CZ CZ19961693A patent/CZ289234B6/cs not_active IP Right Cessation
- 1994-12-15 HU HU9601642A patent/HU221971B1/hu active IP Right Grant
- 1994-12-15 RO RO96-01195A patent/RO114792B1/ro unknown
- 1994-12-15 UA UA96062328A patent/UA46723C2/uk unknown
- 1994-12-15 HR HR941001A patent/HRP941001B1/xx not_active IP Right Cessation
- 1994-12-15 WO PCT/EP1994/004154 patent/WO1995016680A1/en not_active Ceased
- 1994-12-15 PT PT95904472T patent/PT734382E/pt unknown
- 1994-12-15 EG EG79094A patent/EG20597A/xx active
- 1994-12-15 BR BR9408340A patent/BR9408340A/pt not_active Application Discontinuation
- 1994-12-16 IL IL11201194A patent/IL112011A/en not_active IP Right Cessation
- 1994-12-28 SA SA94150417A patent/SA94150417B1/ar unknown
-
1996
- 1996-06-13 FI FI962464A patent/FI120453B/fi not_active IP Right Cessation
- 1996-06-14 OA OA60842A patent/OA10325A/fr unknown
- 1996-06-14 NO NO19962545A patent/NO314759B1/no not_active IP Right Cessation
- 1996-07-08 BG BG100709A patent/BG63338B1/bg unknown
-
1997
- 1997-05-13 BR BRPP1100548-KB1A patent/BR1100548KB1/pt unknown
-
1999
- 1999-07-02 US US09/346,583 patent/US6294572B1/en not_active Expired - Lifetime
-
2000
- 2000-01-06 OA OA1200000004A patent/OA11275A/fr unknown
-
2001
- 2001-03-30 GR GR20010400531T patent/GR3035681T3/el unknown
- 2001-09-24 US US09/961,074 patent/US20020037865A1/en not_active Abandoned
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| ERR | Corrigendum |
Free format text: ADD NUMBER OF PATENT OF ADDITION 147990 |
|
| KB | Patent renewed | ||
| EXP | Patent expired |