JP2008520206A5 - - Google Patents
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- Publication number
- JP2008520206A5 JP2008520206A5 JP2007541425A JP2007541425A JP2008520206A5 JP 2008520206 A5 JP2008520206 A5 JP 2008520206A5 JP 2007541425 A JP2007541425 A JP 2007541425A JP 2007541425 A JP2007541425 A JP 2007541425A JP 2008520206 A5 JP2008520206 A5 JP 2008520206A5
- Authority
- JP
- Japan
- Prior art keywords
- lipase
- process according
- unsubstituted
- protecting group
- mixture
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims 13
- 102000004882 Lipase Human genes 0.000 claims 6
- 108090001060 Lipase Proteins 0.000 claims 6
- 239000004367 Lipase Substances 0.000 claims 6
- 235000019421 lipase Nutrition 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 125000003367 polycyclic group Chemical group 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 150000003952 β-lactams Chemical class 0.000 claims 2
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims 1
- QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical group NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 1
- 241001661345 Moesziomyces antarcticus Species 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-N carbamothioic s-acid Chemical group NC(S)=O GNVMUORYQLCPJZ-UHFFFAOYSA-N 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 229940125904 compound 1 Drugs 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 claims 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62840104P | 2004-11-15 | 2004-11-15 | |
| US60/628,401 | 2004-11-15 | ||
| PCT/US2005/041276 WO2006055528A2 (en) | 2004-11-15 | 2005-11-15 | Process for the preparation of an optically acitive n-carbamate protected beta-lactam by optical resolution employing a candida antarctica lipase |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008520206A JP2008520206A (ja) | 2008-06-19 |
| JP2008520206A5 true JP2008520206A5 (https=) | 2009-01-08 |
| JP4738416B2 JP4738416B2 (ja) | 2011-08-03 |
Family
ID=36190809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007541425A Expired - Fee Related JP4738416B2 (ja) | 2004-11-15 | 2005-11-15 | Ｃａｎｄｉｄａａｎｔａｒｃｔｉｃａリパーゼを使用した光学分割による光学活性Ｎ−カルバメート保護化β−ラクタムを調製するためのプロセス |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7459301B2 (https=) |
| EP (1) | EP1812581B1 (https=) |
| JP (1) | JP4738416B2 (https=) |
| AT (1) | ATE421996T1 (https=) |
| CA (1) | CA2580151C (https=) |
| DE (1) | DE602005012597D1 (https=) |
| DK (1) | DK1812581T3 (https=) |
| ES (1) | ES2320364T3 (https=) |
| PT (1) | PT1812581E (https=) |
| WO (1) | WO2006055528A2 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7754714B2 (en) * | 2004-05-18 | 2010-07-13 | Rigel Pharmaceuticals, Inc. | Cycloalkyl substituted pyrimidinediamine compounds and their uses |
| GB2420559B (en) * | 2004-11-15 | 2008-08-06 | Rigel Pharmaceuticals Inc | Stereoisomerically enriched 3-aminocarbonyl bicycloheptene pyrimidinediamine compounds and their uses |
| WO2007070872A1 (en) | 2005-12-15 | 2007-06-21 | Rigel Pharmaceuticals, Inc. | Kinase inhibitors and their uses |
| HU227663B1 (en) * | 2007-07-09 | 2011-10-28 | Univ Szegedi | Resolution process |
| RU2535032C2 (ru) | 2008-12-22 | 2014-12-10 | Милленниум Фармасьютикалз, Инк. | Сочетание ингибиторов аврора киназы и анти-cd 20 антител |
| EP2489663A1 (en) | 2011-02-16 | 2012-08-22 | Almirall, S.A. | Compounds as syk kinase inhibitors |
| EP3076963A4 (en) | 2013-12-06 | 2017-09-13 | Millennium Pharmaceuticals, Inc. | Combination of aurora kinase inhibitors and anti-cd30 antibodies |
| WO2017015316A1 (en) | 2015-07-21 | 2017-01-26 | Millennium Pharmaceuticals, Inc. | Administration of aurora kinase inhibitor and chemotherapeutic agents |
| WO2019195658A1 (en) | 2018-04-05 | 2019-10-10 | Dana-Farber Cancer Institute, Inc. | Sting levels as a biomarker for cancer immunotherapy |
| CN111194304B (zh) * | 2018-04-18 | 2022-09-27 | 宜昌东阳光长江药业股份有限公司 | 一种桥环化合物的制备方法 |
| US20220305048A1 (en) | 2019-08-26 | 2022-09-29 | Dana-Farber Cancer Institute, Inc. | Use of heparin to promote type 1 interferon signaling |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE258605T1 (de) | 1998-07-09 | 2004-02-15 | Lonza Ag | Verfahren zur herstellung von (1r,4s)-2- azabicyclo 2.2.1 hept-5-en-3-on-derivaten |
-
2005
- 2005-11-15 AT AT05826088T patent/ATE421996T1/de active
- 2005-11-15 EP EP05826088A patent/EP1812581B1/en not_active Expired - Lifetime
- 2005-11-15 DE DE602005012597T patent/DE602005012597D1/de not_active Expired - Lifetime
- 2005-11-15 ES ES05826088T patent/ES2320364T3/es not_active Expired - Lifetime
- 2005-11-15 DK DK05826088T patent/DK1812581T3/da active
- 2005-11-15 JP JP2007541425A patent/JP4738416B2/ja not_active Expired - Fee Related
- 2005-11-15 US US11/281,186 patent/US7459301B2/en active Active
- 2005-11-15 WO PCT/US2005/041276 patent/WO2006055528A2/en not_active Ceased
- 2005-11-15 PT PT05826088T patent/PT1812581E/pt unknown
- 2005-11-15 CA CA2580151A patent/CA2580151C/en not_active Expired - Fee Related
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