JP2001031631A5 - - Google Patents
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- JP2001031631A5 JP2001031631A5 JP2000171482A JP2000171482A JP2001031631A5 JP 2001031631 A5 JP2001031631 A5 JP 2001031631A5 JP 2000171482 A JP2000171482 A JP 2000171482A JP 2000171482 A JP2000171482 A JP 2000171482A JP 2001031631 A5 JP2001031631 A5 JP 2001031631A5
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- 238000000034 method Methods 0.000 description 36
- 125000000217 alkyl group Chemical group 0.000 description 18
- 125000003342 alkenyl group Chemical group 0.000 description 16
- 125000003277 amino group Chemical group 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 15
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- 125000000304 alkynyl group Chemical group 0.000 description 12
- -1 1-ethyl-propoxy Chemical group 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 125000000623 heterocyclic group Chemical group 0.000 description 9
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 8
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- 125000002837 carbocyclic group Chemical group 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 125000000547 substituted alkyl group Chemical group 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical group NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 4
- 239000002262 Schiff base Substances 0.000 description 4
- 150000004753 Schiff bases Chemical class 0.000 description 4
- KOOADCGQJDGAGA-UHFFFAOYSA-N [amino(dimethyl)silyl]methane Chemical compound C[Si](C)(C)N KOOADCGQJDGAGA-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 238000006317 isomerization reaction Methods 0.000 description 4
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 4
- 150000003141 primary amines Chemical class 0.000 description 4
- 0 *C(CCC1)C1=C Chemical compound *C(CCC1)C1=C 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- JGZKUKYUQJUUNE-UHFFFAOYSA-L magnesium;ethoxyethane;dibromide Chemical group [Mg+2].[Br-].[Br-].CCOCC JGZKUKYUQJUUNE-UHFFFAOYSA-L 0.000 description 2
- 238000007248 oxidative elimination reaction Methods 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- CHBMQUIYXCYDEO-MBLYYGPHSA-N CS(O)(=O)=O.CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@@H]([C@H](N)C1)S(C)(=O)=O Chemical compound CS(O)(=O)=O.CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@@H]([C@H](N)C1)S(C)(=O)=O CHBMQUIYXCYDEO-MBLYYGPHSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- XSLCXXFBDZXUTP-MGPQQGTHSA-N ethyl (3r,4r,5r)-5-formamido-4-hydroxy-3-pentan-3-yloxycyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](O)[C@H](NC=O)C1 XSLCXXFBDZXUTP-MGPQQGTHSA-N 0.000 description 1
- XMTYZVODESWUIS-RBSFLKMASA-N ethyl (3r,4r,5r)-5-formamido-4-methylsulfonyl-3-pentan-3-yloxycyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](S(C)(=O)=O)[C@H](NC=O)C1 XMTYZVODESWUIS-RBSFLKMASA-N 0.000 description 1
- YAYJVAVBLBKVLR-RCCFBDPRSA-N ethyl (3r,4r,5s)-4-acetamido-3-pentan-3-yloxy-5-(prop-2-enylamino)cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](NCC=C)C1 YAYJVAVBLBKVLR-RCCFBDPRSA-N 0.000 description 1
- MVOFDZANDCBTOQ-OAGGEKHMSA-N ethyl (3r,4s,5r)-4-hydroxy-3-pentan-3-yloxy-5-(prop-2-enylamino)cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@@H](O)[C@H](NCC=C)C1 MVOFDZANDCBTOQ-OAGGEKHMSA-N 0.000 description 1
- CXXAIYHLQXMRAX-UPJWGTAASA-N ethyl (3r,4s,5r)-5-amino-4-hydroxy-3-pentan-3-yloxycyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@@H](O)[C@H](N)C1 CXXAIYHLQXMRAX-UPJWGTAASA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- VSZGPKBBMSAYNT-RRFJBIMHSA-N oseltamivir Chemical compound CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1 VSZGPKBBMSAYNT-RRFJBIMHSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99111418.2 | 1999-06-11 | ||
| EP99111418 | 1999-06-11 | ||
| EP00103588 | 2000-02-21 | ||
| EP00103588.0 | 2000-02-21 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2001031631A JP2001031631A (ja) | 2001-02-06 |
| JP2001031631A5 true JP2001031631A5 (enExample) | 2007-07-12 |
| JP4656696B2 JP4656696B2 (ja) | 2011-03-23 |
Family
ID=26070572
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000171482A Expired - Fee Related JP4656696B2 (ja) | 1999-06-11 | 2000-06-08 | ノイラミニダーゼ阻害剤の調製方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US6437171B1 (enExample) |
| EP (1) | EP1059283B1 (enExample) |
| JP (1) | JP4656696B2 (enExample) |
| KR (1) | KR100679780B1 (enExample) |
| CN (1) | CN1191230C (enExample) |
| AT (1) | ATE241589T1 (enExample) |
| CA (1) | CA2310714C (enExample) |
| DE (1) | DE60002949T2 (enExample) |
| DK (1) | DK1059283T3 (enExample) |
| ES (1) | ES2198244T3 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1059283B1 (en) * | 1999-06-11 | 2003-05-28 | F. Hoffmann-La Roche Ag | Process for preparing neuraminidase inhibitor ro-64-0796 |
| JP2001131144A (ja) * | 1999-11-02 | 2001-05-15 | Sagami Chem Res Center | ７−アザビシクロ［４．１．０］ヘプト−３−エン−３−カルボン酸エステル類の製造方法 |
| US6518048B2 (en) * | 2000-04-10 | 2003-02-11 | Hoffmann-La Roche Inc. | Stereo-specific synthesis of shimikic acid derivatives with improved efficiency |
| GB0202563D0 (en) * | 2002-02-04 | 2002-03-20 | Glaxo Group Ltd | Process |
| US7122684B2 (en) * | 2003-03-13 | 2006-10-17 | Roche Colorado Corporation | Process for preparing 1,2-diamino compounds |
| US7875730B2 (en) | 2004-02-23 | 2011-01-25 | Cadila Healthcare Ltd. | Process for manufacture of racemic Carvedilol |
| JP4682204B2 (ja) * | 2004-09-02 | 2011-05-11 | エフ．ホフマン−ラ ロシュ アーゲー | ４，５−ジアミノシキミ酸の製造方法 |
| KR100819759B1 (ko) * | 2005-12-01 | 2008-04-07 | (주)파인켐 | 아자이드 화합물의 폭발성을 제거한 공정을 이용한 1,2-다이아미노 화합물 또는 이의 부가염 제조 방법 |
| WO2008028057A2 (en) * | 2006-08-30 | 2008-03-06 | President And Fellows Of Harvard College | Shikimic acid-derived compounds for inhibition and detection of aurora a-associated tumors |
| JP5698128B2 (ja) * | 2009-06-09 | 2015-04-08 | 国立大学法人 岡山大学 | ジヒドロキシヘキセン酸エステル及びその製造方法 |
| JP4496351B1 (ja) * | 2009-09-01 | 2010-07-07 | 国立大学法人 岡山大学 | １，３−ジオキソラン化合物及びその製造方法 |
| CN113024396B (zh) * | 2019-12-25 | 2024-01-30 | 上海奥博生物医药股份有限公司 | 一种奥司他韦的制备方法及其中间体 |
| CN111153818B (zh) * | 2020-03-13 | 2023-03-28 | 遂成药业股份有限公司 | 一种制备抗病毒药物达菲中间体叔丁胺衍生物i的方法 |
| CN111499536B (zh) * | 2020-05-06 | 2022-10-18 | 湖南欧亚药业有限公司 | 一种奥司他韦的制备方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1593775A1 (de) * | 1967-04-13 | 1971-03-25 | Basf Ag | Verfahren zur Herstellung von 1,2-Diaminen |
| JPS57144247A (en) * | 1981-03-02 | 1982-09-06 | Lion Corp | Preparation of n-substituted amino-alcohol compound |
| JPH04368356A (ja) * | 1991-06-12 | 1992-12-21 | Nitto Denko Corp | Ｎ，ｎ−ジメチル−３−アミノ−２−メチル−２−プロパノールの製造方法。 |
| US5866601A (en) | 1995-02-27 | 1999-02-02 | Gilead Sciences, Inc. | Carbocyclic compounds |
| SI9620042A (sl) | 1995-02-27 | 1998-12-31 | Gilead Sciences, Inc. | Novi selektivni inhibitorji virusnih ali bakterijskih neuraminidaz |
| US5763483A (en) | 1995-12-29 | 1998-06-09 | Gilead Sciences, Inc. | Carbocyclic compounds |
| JP3622983B2 (ja) * | 1996-08-23 | 2005-02-23 | ギリアード サイエンシーズ， インコーポレイテッド | シクロヘキセンカルボキシレート誘導体の調製 |
| 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 |
| JPH10251190A (ja) * | 1997-03-11 | 1998-09-22 | Sumitomo Chem Co Ltd | 芳香族ケトン化合物、その製造方法およびその中間体 |
| US5886213A (en) | 1997-08-22 | 1999-03-23 | Gilead Sciences, Inc. | Preparation of carbocyclic compounds |
| JP2001516739A (ja) * | 1997-09-17 | 2001-10-02 | ギリアード サイエンシーズ， インコーポレイテッド | ６員環を含む化合物、それらの調製プロセス、および医薬としてのそれらの使用 |
| JP3075558B2 (ja) * | 1998-01-16 | 2000-08-14 | 日本たばこ産業株式会社 | 光学活性アミノアルコール類の製造方法 |
| EP1059283B1 (en) * | 1999-06-11 | 2003-05-28 | F. Hoffmann-La Roche Ag | Process for preparing neuraminidase inhibitor ro-64-0796 |
-
2000
- 2000-06-03 EP EP00111787A patent/EP1059283B1/en not_active Expired - Lifetime
- 2000-06-03 DK DK00111787T patent/DK1059283T3/da active
- 2000-06-03 ES ES00111787T patent/ES2198244T3/es not_active Expired - Lifetime
- 2000-06-03 DE DE60002949T patent/DE60002949T2/de not_active Expired - Lifetime
- 2000-06-03 AT AT00111787T patent/ATE241589T1/de active
- 2000-06-06 CA CA002310714A patent/CA2310714C/en not_active Expired - Lifetime
- 2000-06-08 US US09/590,317 patent/US6437171B1/en not_active Expired - Lifetime
- 2000-06-08 JP JP2000171482A patent/JP4656696B2/ja not_active Expired - Fee Related
- 2000-06-09 CN CNB001181394A patent/CN1191230C/zh not_active Expired - Fee Related
- 2000-06-09 KR KR1020000031535A patent/KR100679780B1/ko not_active Expired - Fee Related
-
2002
- 2002-02-22 US US10/081,345 patent/US6939986B2/en not_active Expired - Lifetime
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