JP5485142B2 - 鏡像異性体に富化したn−カルボン酸無水物の調製方法 - Google Patents
鏡像異性体に富化したn−カルボン酸無水物の調製方法 Download PDFInfo
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- 238000000034 method Methods 0.000 title claims description 24
- 238000002360 preparation method Methods 0.000 title description 13
- 150000001875 compounds Chemical class 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 22
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 238000001953 recrystallisation Methods 0.000 claims description 6
- 238000000859 sublimation Methods 0.000 claims description 6
- 230000008022 sublimation Effects 0.000 claims description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000003208 petroleum Substances 0.000 claims description 5
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims description 4
- 235000008206 alpha-amino acids Nutrition 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 238000010981 drying operation Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- -1 (D) -N-methylalanine carboxylic acid anhydrides Chemical class 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- GDFAOVXKHJXLEI-VKHMYHEASA-N N-methyl-L-alanine Chemical compound C[NH2+][C@@H](C)C([O-])=O GDFAOVXKHJXLEI-VKHMYHEASA-N 0.000 description 4
- 235000001014 amino acid Nutrition 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- WTFJJYYGWFKOQH-VKHMYHEASA-N (4s)-3,4-dimethyl-1,3-oxazolidine-2,5-dione Chemical compound C[C@@H]1N(C)C(=O)OC1=O WTFJJYYGWFKOQH-VKHMYHEASA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- GDFAOVXKHJXLEI-GSVOUGTGSA-N (2r)-2-(methylamino)propanoic acid Chemical compound CN[C@H](C)C(O)=O GDFAOVXKHJXLEI-GSVOUGTGSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000006345 epimerization reaction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 230000035479 physiological effects, processes and functions Effects 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 238000012916 structural analysis Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- WTFJJYYGWFKOQH-GSVOUGTGSA-N (4r)-3,4-dimethyl-1,3-oxazolidine-2,5-dione Chemical compound C[C@H]1N(C)C(=O)OC1=O WTFJJYYGWFKOQH-GSVOUGTGSA-N 0.000 description 1
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- 0 **([C@@](*)C(O1)=O)C1=O Chemical compound **([C@@](*)C(O1)=O)C1=O 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 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 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- LMUVIOBZBRHXMY-BYPYZUCNSA-N C[C@@H](C(O)=O)N(C)C(OC)=O Chemical compound C[C@@H](C(O)=O)N(C)C(OC)=O LMUVIOBZBRHXMY-BYPYZUCNSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 150000008575 L-amino acids Chemical class 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- DDKMFOUTRRODRE-UHFFFAOYSA-N chloromethanone Chemical compound Cl[C]=O DDKMFOUTRRODRE-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 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 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000000105 evaporative light scattering detection Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D263/44—Two oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyridine Compounds (AREA)
- Peptides Or Proteins (AREA)
Description
アルキル基:直鎖のまたは分岐した飽和脂肪族炭化水素系の基。例として、メチル、エチル、プロピル、イソプロピル、ブチル、イソブチルおよびtert−ブチル基が挙げられ得る。これは、好ましくは(C1−C4)基である。
R1およびR2は、互いに独立して、アルキル(例えば、メチル、エチル、イソプロピル)、アルケニル(例えば、アリル)、シクロアルキル、シクロアルキルアルキル(例えば、−CH2−シクロヘキシル)、アリールアルキル(例えば、ベンジル)またはアリール基を示し、
R3は、アルキル(例えば、メチル、エチル、tert−ブチル)またはアリールアルキル(例えば、ベンジル)基を示す。)、
(i)式(IIa)(または別々に(IIb))の化合物を、溶媒中でSOCl2と接触させるステップ、
(ii)非溶媒を用いて、ステップ(i)において形成されるN−カルボン酸無水物を沈殿させるステップおよび
(iii)N−カルボン酸無水物を回収するステップ
を含む、方法
に関する。
ステップ(i)の溶媒は、ジクロロメタン等の塩素化溶媒、例えばテトラヒドロフラン、2−メチルテトラヒドロフランまたは1,4−ジオキサン等のアルキルまたはアリールのエーテル、例えばトルエン、キシレンまたはトリフルオロメチルベンゼン等の芳香族溶媒、例えばアセトン、メチルイソブチルケトンまたはメチルエチルケトン等のケトンであることができる。これらの溶媒の2種以上の混合物を用いることも可能である。
ステップ(i)において形成されたN−カルボン酸無水物の沈殿は、非溶媒を用い行われる。液体アルカン(例えば、n−ヘプタンもしくはオクタン)または石油留分(例えば、石油エーテル)が有利に使用される。N−カルボン酸無水物は、まず、ステップ(i)の反応からのいくらかの溶媒を除去することにより濃縮され得る。
N−カルボン酸無水物は、濾過/乾燥により簡単に回収され得る。これは、本発明の方法の長所の一つであり、すなわち、十分な純度および良好な収率を得るための再結晶または昇華のステップを必要としない。ステップ(ii)において液体アルカンを用いる利点は、N−カルボン酸無水物を容易に乾燥できることにある。
式(IIa)(または(IIb))の化合物は、以下の反応
当業者は、以下の2つの実施例に開示されている条件から、有利に着想することができる。
前に得られた生成物1g(6.2mmol)を、CH2Cl23ml中に溶解し、約20℃で5分間攪拌し、次いで、SOCl2(500μl、1.1当量)により処理した。反応媒体を、次いで、約30℃で加熱し、加熱を約30分間維持した。反応媒体を、次いで、約1.5体積に濃縮し、なお攪拌しつつ、n−ヘプタン10mlを加えた。このようにして得られた白色の塊を、次いで、約−20℃に冷却し、この温度で1時間攪拌した。懸濁液を、次いで、焼結ガラスを通して濾過し、固体をn−ヘプタン3mlで3回洗浄した。空気中で2時間乾燥した後、生成物(700mg、87.4%)が、白色針状晶の形で得られた。
Claims (16)
- 式(IIIa)または(IIIb)
式(IIa)(または、(IIb))
(式中、
R1およびR2は、互いに独立して、アルキル、アルケニル、シクロアルキル、シクロアルキルアルキル、アリールアルキルまたはアリール基を示し、
R3は、アルキルまたはアリールアルキル基を示す)、
(i)式(IIa)(または(IIb))の化合物を、溶媒中でSOCl2と接触させるステップ、
(ii)非溶媒を用いて、ステップ(i)において形成されるN−カルボン酸無水物を沈殿させるステップおよび
(iii)N−カルボン酸無水物を回収するステップ
を含み、
N−カルボン酸無水物の再結晶ステップも昇華ステップも含まない、方法。 - R3が、メチルまたはエチル基を示す請求項1に記載の方法。
- R1およびR2が、互いに独立して、メチルまたはエチル基を示す請求項1および2のいずれかに記載の方法。
- R1、R2およびR3が、メチル基を示す請求項1に記載の方法。
- 反応が、ステップ(i)に先んずるステップを構成する、請求項5に記載の方法。
- ステップ(i)の反応が、−10から50℃の間の温度で行われる、請求項1から7の一項に記載の方法。
- ステップ(i)の反応が、0から30℃の間の温度で行われる、請求項8に記載の方法。
- ステップ(i)の反応が、20から30℃の間の温度で行われる、請求項9に記載の方法。
- ステップ(i)の反応が、化合物(IIa)(もしくは(IIb))または(C)(もしくは(D))に対して、1から3当量のSOCl2により行われる、請求項1から10の一項に記載の方法。
- ステップ(ii)の非溶媒が、液体アルカンまたは石油留分である、請求項1から11の一項に記載の方法。
- 溶媒/非溶媒の組として、塩素化溶媒と、液体アルカンまたは石油留分を使用する、請求項1から12の一項に記載の方法。
- 溶媒/非溶媒の組として、ジクロロメタン/n−ヘプタンの組を使用する、請求項13に記載の方法。
- ステップ(iii)からのN−カルボン酸無水物の回収が、濾過/乾燥の操作である、請求項1から14のいずれか一項に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0703702A FR2916444B1 (fr) | 2007-05-25 | 2007-05-25 | Procede de preparation de n-carboxyanhydride enantiomeriquement enrichi. |
FR0703702 | 2007-05-25 | ||
PCT/FR2008/000703 WO2009004141A2 (fr) | 2007-05-25 | 2008-05-22 | Procede de preparation de n-carboxyanhydride enantiomeriquement enrichi |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2010527975A JP2010527975A (ja) | 2010-08-19 |
JP2010527975A5 JP2010527975A5 (ja) | 2013-10-17 |
JP5485142B2 true JP5485142B2 (ja) | 2014-05-07 |
Family
ID=38863061
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2010508878A Active JP5485142B2 (ja) | 2007-05-25 | 2008-05-22 | 鏡像異性体に富化したn−カルボン酸無水物の調製方法 |
Country Status (12)
Country | Link |
---|---|
US (2) | US8119813B2 (ja) |
EP (1) | EP2152680B1 (ja) |
JP (1) | JP5485142B2 (ja) |
AR (1) | AR066704A1 (ja) |
CL (1) | CL2008001512A1 (ja) |
ES (1) | ES2547651T3 (ja) |
FR (1) | FR2916444B1 (ja) |
PA (1) | PA8781401A1 (ja) |
PE (1) | PE20090719A1 (ja) |
TW (1) | TWI430996B (ja) |
UY (1) | UY31104A1 (ja) |
WO (1) | WO2009004141A2 (ja) |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
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IT1299341B1 (it) * | 1998-02-09 | 2000-03-16 | Pfc Italiana Srl | Processo per la produzione di alcossicarbonildipeptidi intermedi nella sintesi del lisinopril. |
FR2825705B1 (fr) * | 2001-06-08 | 2005-05-20 | Aventis Pharma Sa | Nouveaux composes heterocycliques, leur preparation et leur utilisation comme medicaments, notamment comme anti-bacteriens |
-
2007
- 2007-05-25 FR FR0703702A patent/FR2916444B1/fr active Active
-
2008
- 2008-05-21 TW TW097118694A patent/TWI430996B/zh not_active IP Right Cessation
- 2008-05-22 JP JP2010508878A patent/JP5485142B2/ja active Active
- 2008-05-22 EP EP08805594.2A patent/EP2152680B1/fr active Active
- 2008-05-22 WO PCT/FR2008/000703 patent/WO2009004141A2/fr active Application Filing
- 2008-05-22 ES ES08805594.2T patent/ES2547651T3/es active Active
- 2008-05-23 PA PA20088781401A patent/PA8781401A1/es unknown
- 2008-05-23 PE PE2008000886A patent/PE20090719A1/es not_active Application Discontinuation
- 2008-05-23 AR ARP080102183A patent/AR066704A1/es unknown
- 2008-05-23 CL CL2008001512A patent/CL2008001512A1/es unknown
- 2008-05-23 UY UY31104A patent/UY31104A1/es not_active Application Discontinuation
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2009
- 2009-11-12 US US12/617,398 patent/US8119813B2/en active Active
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Also Published As
Publication number | Publication date |
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WO2009004141A2 (fr) | 2009-01-08 |
US20120215007A1 (en) | 2012-08-23 |
CL2008001512A1 (es) | 2009-09-25 |
JP2010527975A (ja) | 2010-08-19 |
TWI430996B (zh) | 2014-03-21 |
ES2547651T3 (es) | 2015-10-07 |
US20100113797A1 (en) | 2010-05-06 |
UY31104A1 (es) | 2009-01-05 |
TW200914432A (en) | 2009-04-01 |
US8119813B2 (en) | 2012-02-21 |
PA8781401A1 (es) | 2008-12-18 |
EP2152680B1 (fr) | 2015-06-24 |
PE20090719A1 (es) | 2009-07-13 |
AR066704A1 (es) | 2009-09-09 |
FR2916444B1 (fr) | 2011-02-11 |
FR2916444A1 (fr) | 2008-11-28 |
EP2152680A2 (fr) | 2010-02-17 |
WO2009004141A3 (fr) | 2009-04-09 |
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