CA2144342C - Synthesis of n-acetyl neuraminic acid derivatives - Google Patents
Synthesis of n-acetyl neuraminic acid derivatives Download PDFInfo
- Publication number
- CA2144342C CA2144342C CA002144342A CA2144342A CA2144342C CA 2144342 C CA2144342 C CA 2144342C CA 002144342 A CA002144342 A CA 002144342A CA 2144342 A CA2144342 A CA 2144342A CA 2144342 C CA2144342 C CA 2144342C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- galacto
- acetamido
- glycero
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 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 title description 3
- 230000015572 biosynthetic process Effects 0.000 title description 2
- 238000003786 synthesis reaction Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 18
- 239000002253 acid Substances 0.000 claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 239000012736 aqueous medium Substances 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- -1 hydrochloric Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000004684 trihydrates Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003828 vacuum filtration 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Glass Compositions (AREA)
- Iron Core Of Rotating Electric Machines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929220327A GB9220327D0 (en) | 1992-09-25 | 1992-09-25 | Process |
| GB9220327.2 | 1992-09-25 | ||
| PCT/EP1993/002575 WO1994007886A1 (en) | 1992-09-25 | 1993-09-23 | Synthesis of n-acetyl neuraminic acid derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2144342A1 CA2144342A1 (en) | 1994-04-14 |
| CA2144342C true CA2144342C (en) | 2000-05-16 |
Family
ID=10722539
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002144342A Expired - Lifetime CA2144342C (en) | 1992-09-25 | 1993-09-23 | Synthesis of n-acetyl neuraminic acid derivatives |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP0662967B1 (en, 2012) |
| CN (1) | CN1041416C (en, 2012) |
| AT (1) | ATE162188T1 (en, 2012) |
| AU (1) | AU672634B2 (en, 2012) |
| CA (1) | CA2144342C (en, 2012) |
| CY (1) | CY2110B1 (en, 2012) |
| DE (1) | DE69316382T2 (en, 2012) |
| DK (1) | DK0662967T3 (en, 2012) |
| ES (1) | ES2112433T3 (en, 2012) |
| FI (1) | FI112224B (en, 2012) |
| GB (1) | GB9220327D0 (en, 2012) |
| GR (1) | GR3026298T3 (en, 2012) |
| IL (1) | IL107069A (en, 2012) |
| IS (1) | IS4071A (en, 2012) |
| MX (1) | MX9305902A (en, 2012) |
| NO (1) | NO308743B1 (en, 2012) |
| PL (1) | PL174446B1 (en, 2012) |
| SG (1) | SG50642A1 (en, 2012) |
| TW (1) | TW282464B (en, 2012) |
| WO (1) | WO1994007886A1 (en, 2012) |
| ZA (1) | ZA937032B (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3300365B2 (ja) * | 1995-02-27 | 2002-07-08 | ギリアード サイエンシーズ，インコーポレイテッド | ウイルスまたは細菌ノイラミニダーゼの新規な選択的インヒビター |
| 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 |
| US6518438B2 (en) | 1996-08-23 | 2003-02-11 | Gilead Sciences, Inc. | Preparation of cyclohexene carboxylate derivatives |
| US5859284A (en) * | 1996-08-23 | 1999-01-12 | Gilead Sciences, Inc. | Preparation of carbocyclic compounds |
| 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 |
| DE10230780A1 (de) * | 2002-07-09 | 2004-02-05 | Degussa Ag | Verfahren zur Herstellung von 1-Methylcyclopropylguanidin bzw. dessen Salzen |
| CA2744793A1 (en) | 2008-11-28 | 2010-06-03 | Cipla Limited | Process for preparing zanamivir and intermediates for use in the process |
| US20140073804A1 (en) | 2011-02-24 | 2014-03-13 | Ganpat Dan Shimbhu CHARAN | Process for the preparation of zanamivir |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ288492B6 (en) * | 1990-04-24 | 2001-06-13 | Biota Scient Management | Derivatives of alpha-D-neuraminic acid, process of their preparation, their use and pharmaceutical preparations based thereon |
| 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 |
-
1992
- 1992-09-25 GB GB929220327A patent/GB9220327D0/en active Pending
-
1993
- 1993-09-17 TW TW082107635A patent/TW282464B/zh not_active IP Right Cessation
- 1993-09-20 IS IS4071A patent/IS4071A/is unknown
- 1993-09-22 IL IL107069A patent/IL107069A/en not_active IP Right Cessation
- 1993-09-23 DE DE69316382T patent/DE69316382T2/de not_active Expired - Lifetime
- 1993-09-23 CA CA002144342A patent/CA2144342C/en not_active Expired - Lifetime
- 1993-09-23 PL PL93308203A patent/PL174446B1/pl unknown
- 1993-09-23 EP EP93921840A patent/EP0662967B1/en not_active Expired - Lifetime
- 1993-09-23 AU AU51088/93A patent/AU672634B2/en not_active Expired
- 1993-09-23 ZA ZA937032A patent/ZA937032B/xx unknown
- 1993-09-23 DK DK93921840T patent/DK0662967T3/da active
- 1993-09-23 ES ES93921840T patent/ES2112433T3/es not_active Expired - Lifetime
- 1993-09-23 SG SG1996007544A patent/SG50642A1/en unknown
- 1993-09-23 AT AT93921840T patent/ATE162188T1/de active
- 1993-09-23 WO PCT/EP1993/002575 patent/WO1994007886A1/en active IP Right Grant
- 1993-09-24 CN CN93118291A patent/CN1041416C/zh not_active Expired - Lifetime
- 1993-09-24 MX MX9305902A patent/MX9305902A/es unknown
-
1995
- 1995-03-23 FI FI951378A patent/FI112224B/fi not_active IP Right Cessation
- 1995-03-24 NO NO951136A patent/NO308743B1/no not_active IP Right Cessation
-
1998
- 1998-03-06 GR GR980400469T patent/GR3026298T3/el unknown
- 1998-09-10 CY CY9800026A patent/CY2110B1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX9305902A (es) | 1994-05-31 |
| PL308203A1 (en) | 1995-07-24 |
| ES2112433T3 (es) | 1998-04-01 |
| AU672634B2 (en) | 1996-10-10 |
| WO1994007886A1 (en) | 1994-04-14 |
| IL107069A (en) | 1998-01-04 |
| ZA937032B (en) | 1994-05-16 |
| DE69316382D1 (de) | 1998-02-19 |
| ATE162188T1 (de) | 1998-01-15 |
| TW282464B (en, 2012) | 1996-08-01 |
| NO951136D0 (no) | 1995-03-24 |
| GR3026298T3 (en) | 1998-06-30 |
| CN1041416C (zh) | 1998-12-30 |
| GB9220327D0 (en) | 1992-11-11 |
| EP0662967B1 (en) | 1998-01-14 |
| IS4071A (is) | 1994-03-26 |
| FI951378L (fi) | 1995-03-23 |
| DK0662967T3 (da) | 1998-09-14 |
| SG50642A1 (en) | 1999-04-27 |
| FI951378A0 (fi) | 1995-03-23 |
| NO308743B1 (no) | 2000-10-23 |
| NO951136L (no) | 1995-05-08 |
| IL107069A0 (en) | 1993-12-28 |
| CA2144342A1 (en) | 1994-04-14 |
| EP0662967A1 (en) | 1995-07-19 |
| PL174446B1 (pl) | 1998-07-31 |
| CN1099389A (zh) | 1995-03-01 |
| CY2110B1 (en) | 2002-04-26 |
| FI112224B (fi) | 2003-11-14 |
| AU5108893A (en) | 1994-04-26 |
| DE69316382T2 (de) | 1998-07-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |