NO312675B1 - Fremgangsmåte for fremstilling av N-acetyl- neuraminsyrederivater - Google Patents
Fremgangsmåte for fremstilling av N-acetyl- neuraminsyrederivater Download PDFInfo
- Publication number
- NO312675B1 NO312675B1 NO19955124A NO955124A NO312675B1 NO 312675 B1 NO312675 B1 NO 312675B1 NO 19955124 A NO19955124 A NO 19955124A NO 955124 A NO955124 A NO 955124A NO 312675 B1 NO312675 B1 NO 312675B1
- Authority
- NO
- Norway
- Prior art keywords
- catalyst
- compound
- formula
- formic acid
- palladium
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 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 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 18
- 235000019253 formic acid Nutrition 0.000 claims abstract description 18
- 238000007327 hydrogenolysis reaction Methods 0.000 claims abstract description 5
- 230000003197 catalytic effect Effects 0.000 claims abstract description 4
- 230000007062 hydrolysis Effects 0.000 claims abstract description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 29
- 239000003054 catalyst Substances 0.000 claims description 26
- 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 claims description 14
- 229910052763 palladium Inorganic materials 0.000 claims description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical group [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- 239000011981 lindlar catalyst Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims 1
- 239000003610 charcoal Substances 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 2
- 125000002252 acyl group Chemical group 0.000 abstract description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- -1 peracetyl NANA methyl ester Chemical class 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 150000004682 monohydrates Chemical class 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 241000712461 unidentified influenza virus Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- 230000009385 viral infection Effects 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
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Steroid Compounds (AREA)
- Iron Core Of Rotating Electric Machines (AREA)
- Glass Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB939312531A GB9312531D0 (en) | 1993-06-17 | 1993-06-17 | Process |
| PCT/EP1994/001940 WO1995000503A1 (en) | 1993-06-17 | 1994-06-15 | Process for the preparation of n-acetyl neuraminic acid derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO955124L NO955124L (no) | 1995-12-15 |
| NO955124D0 NO955124D0 (no) | 1995-12-15 |
| NO312675B1 true NO312675B1 (no) | 2002-06-17 |
Family
ID=10737336
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19955124A NO312675B1 (no) | 1993-06-17 | 1995-12-15 | Fremgangsmåte for fremstilling av N-acetyl- neuraminsyrederivater |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5597933A (es) |
| EP (1) | EP0705256B1 (es) |
| JP (1) | JP3298644B2 (es) |
| CN (1) | CN1061343C (es) |
| AT (1) | ATE172198T1 (es) |
| AU (1) | AU687825B2 (es) |
| CA (1) | CA2165329C (es) |
| CY (1) | CY2184B1 (es) |
| DE (1) | DE69413974T2 (es) |
| DK (1) | DK0705256T3 (es) |
| ES (1) | ES2125463T3 (es) |
| FI (1) | FI111941B (es) |
| GB (1) | GB9312531D0 (es) |
| HK (1) | HK1011995A1 (es) |
| HU (1) | HU213451B (es) |
| NO (1) | NO312675B1 (es) |
| SG (1) | SG48162A1 (es) |
| WO (1) | WO1995000503A1 (es) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI9620042A (sl) | 1995-02-27 | 1998-12-31 | Gilead Sciences, Inc. | Novi selektivni inhibitorji virusnih ali bakterijskih neuraminidaz |
| 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 |
| 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 |
| US20040053999A1 (en) * | 1997-09-17 | 2004-03-18 | Bischofberger Norbert W. | Novel compounds and methods for synthesis and therapy |
| TW480247B (en) * | 1997-12-12 | 2002-03-21 | Gilead Sciences Inc | Novel compounds useful as neuraminidase inhibitors and pharmaceutical compositions containing same |
| US7636596B2 (en) * | 2002-12-20 | 2009-12-22 | Medtronic, Inc. | Organ access device and method |
| KR101142052B1 (ko) | 2010-02-18 | 2012-07-19 | 한미약품 주식회사 | 자나미비어의 제조방법 |
| CN101962375B (zh) * | 2010-09-21 | 2012-05-23 | 仙居县圃瑞药业有限公司 | 扎那米韦中间体叠氮还原工艺方法 |
| TW201625247A (zh) | 2014-05-12 | 2016-07-16 | 葛蘭素史密斯克藍智慧財產權有限公司 | 用於治療傳染性疾病之醫藥組合物 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AP249A (en) * | 1990-04-24 | 1993-03-17 | Biota Scient Management Pty Ltd | Anti-viral compounds. |
| GB9126725D0 (en) * | 1991-12-17 | 1992-02-12 | Glaxo Group Ltd | Process |
-
1993
- 1993-06-17 GB GB939312531A patent/GB9312531D0/en active Pending
-
1994
- 1994-06-15 DE DE69413974T patent/DE69413974T2/de not_active Expired - Lifetime
- 1994-06-15 AU AU70006/94A patent/AU687825B2/en not_active Expired
- 1994-06-15 HU HU9503599A patent/HU213451B/hu unknown
- 1994-06-15 SG SG1996007494A patent/SG48162A1/en unknown
- 1994-06-15 EP EP94918871A patent/EP0705256B1/en not_active Expired - Lifetime
- 1994-06-15 US US08/549,820 patent/US5597933A/en not_active Expired - Lifetime
- 1994-06-15 CA CA002165329A patent/CA2165329C/en not_active Expired - Lifetime
- 1994-06-15 AT AT94918871T patent/ATE172198T1/de active
- 1994-06-15 JP JP50240795A patent/JP3298644B2/ja not_active Expired - Lifetime
- 1994-06-15 DK DK94918871T patent/DK0705256T3/da active
- 1994-06-15 CN CN94192472A patent/CN1061343C/zh not_active Expired - Lifetime
- 1994-06-15 ES ES94918871T patent/ES2125463T3/es not_active Expired - Lifetime
- 1994-06-15 WO PCT/EP1994/001940 patent/WO1995000503A1/en active IP Right Grant
-
1995
- 1995-12-14 FI FI955993A patent/FI111941B/fi not_active IP Right Cessation
- 1995-12-15 NO NO19955124A patent/NO312675B1/no not_active IP Right Cessation
-
1998
- 1998-12-14 HK HK98113326A patent/HK1011995A1/xx not_active IP Right Cessation
-
1999
- 1999-01-14 CY CY9900002A patent/CY2184B1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US5597933A (en) | 1997-01-28 |
| FI955993A (fi) | 1995-12-14 |
| JPH08511550A (ja) | 1996-12-03 |
| WO1995000503A1 (en) | 1995-01-05 |
| ES2125463T3 (es) | 1999-03-01 |
| DE69413974D1 (de) | 1998-11-19 |
| EP0705256A1 (en) | 1996-04-10 |
| GB9312531D0 (en) | 1993-08-04 |
| CA2165329C (en) | 2002-08-20 |
| DE69413974T2 (de) | 1999-03-11 |
| HU9503599D0 (en) | 1996-02-28 |
| CY2184B1 (en) | 2002-11-08 |
| HUT73561A (en) | 1996-08-28 |
| CN1125441A (zh) | 1996-06-26 |
| EP0705256B1 (en) | 1998-10-14 |
| JP3298644B2 (ja) | 2002-07-02 |
| HK1011995A1 (en) | 1999-07-23 |
| HU213451B (en) | 1997-06-30 |
| DK0705256T3 (da) | 1999-06-23 |
| NO955124L (no) | 1995-12-15 |
| AU7000694A (en) | 1995-01-17 |
| FI111941B (fi) | 2003-10-15 |
| FI955993A0 (fi) | 1995-12-14 |
| ATE172198T1 (de) | 1998-10-15 |
| CA2165329A1 (en) | 1995-01-05 |
| AU687825B2 (en) | 1998-03-05 |
| NO955124D0 (no) | 1995-12-15 |
| SG48162A1 (en) | 1998-04-17 |
| CN1061343C (zh) | 2001-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |