WO2010005175A3 - 신규한 결정형 실라스타틴 암모늄염 및 그 제조방법 - Google Patents

신규한 결정형 실라스타틴 암모늄염 및 그 제조방법 Download PDF

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Publication number
WO2010005175A3
WO2010005175A3 PCT/KR2009/003046 KR2009003046W WO2010005175A3 WO 2010005175 A3 WO2010005175 A3 WO 2010005175A3 KR 2009003046 W KR2009003046 W KR 2009003046W WO 2010005175 A3 WO2010005175 A3 WO 2010005175A3
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WO
WIPO (PCT)
Prior art keywords
cilastatin
water
ammonium salts
organic solvent
preparation
Prior art date
Application number
PCT/KR2009/003046
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English (en)
French (fr)
Other versions
WO2010005175A2 (ko
Inventor
김영훈
김정수
구영삼
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(주)하이텍팜
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Application filed by (주)하이텍팜 filed Critical (주)하이텍팜
Publication of WO2010005175A2 publication Critical patent/WO2010005175A2/ko
Publication of WO2010005175A3 publication Critical patent/WO2010005175A3/ko

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
    • C07C323/59—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton with acylated amino groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/22—Separation; Purification; Stabilisation; Use of additives
    • C07C231/24—Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

본 발명은 고순도 실라스타틴 나트륨염의 제조에 매우 유용하게 사용되는 화학식(1)의 새로운 결정형 실라스타틴 암모늄염의 제조방법 및 이 방법에 의하여 제조된 결정형 실라스티틴 암모늄염에 관한 것이다. 구체적으로, 본 발명은 하기 화학식(1)의 결정형 실라스타틴 암모늄염의 제조방법으로서, (i) 질소 기체 중에서, 용매로서 물을 사용하거나, 물과 혼합하여 사용할 수 있는 C1-C4의 알콜, 아세토니트릴 및 아세톤으로 이루어진 그룹으로부터 선택되는 하나 이상의 유기용매를 사용하거나, 물과 상기 유기용매를 혼합하여 사용하고, 촉매로서 브롬화 나트륨, 브롬화 칼륨 또는 요오드 나트륨을 사용하여, (a) 수산화 나트륨 또는 수산화 칼륨의 용액 중에서, (b) 화학식(2)의 (Z)-7-클로로-[[[(S)-2,2-디메틸시클로프로필]카르보닐]아미노]-2-헵탄산 또는 그의 염과, (c) 화학식(3)의 시스테인 또는 그의 염을, (a):(b):(c)의 당량비를 1:1:1~1:3:5으로 하여 50~80℃에서 3-15시간 반응시켜 실라스타틴을 제조하는 단계, (ii) 강산을 이용하여, 단계 (i)에서 제조된 실라스타틴의 pH를 1.0 ~ 5.0으로 조절한 후, 중성 흡착 수지에 흡착시킨 다음, 물로 세척하고, 암모니아수로 용출하고 농축하여 실라스타틴 암모늄염을 제조하는 단계, (iii) 단계 (ii)에서 제조된 실라스타틴 암모늄염을, 물, 암모니아수, 또는 물과 암모니아수의 혼합용액에 용해시키고, C1-C4의 알콜, 아세토니트릴 및 아세톤으로 이루어진 그룹으로부터 선택되는 하나 이상의 유기 용매 중에서, 실라스타틴 암모늄염: 물, 암모니아수, 또는 이들의 혼합용액: 유기용매의 당량비를 1:20:40(W/V/V) ~ 1:0.5:40(W/V/V)로 하여, 5~50℃에서 2-5시간 교반하여 결정을 생성하는 단계를 포함한다.
PCT/KR2009/003046 2008-07-09 2009-06-08 신규한 결정형 실라스타틴 암모늄염 및 그 제조방법 WO2010005175A2 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020080066378A KR100913694B1 (ko) 2008-07-09 2008-07-09 신규한 결정형 실라스타틴 암모늄염 및 그 제조방법
KR10-2008-0066378 2008-07-09

Publications (2)

Publication Number Publication Date
WO2010005175A2 WO2010005175A2 (ko) 2010-01-14
WO2010005175A3 true WO2010005175A3 (ko) 2010-03-11

Family

ID=41210167

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2009/003046 WO2010005175A2 (ko) 2008-07-09 2009-06-08 신규한 결정형 실라스타틴 암모늄염 및 그 제조방법

Country Status (2)

Country Link
KR (1) KR100913694B1 (ko)
WO (1) WO2010005175A2 (ko)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104649948B (zh) * 2013-11-19 2017-05-24 江苏迪赛诺制药有限公司 一种西司他丁钙结晶体及其制备方法和应用

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5147868A (en) * 1978-07-24 1992-09-15 Merck & Co., Inc. Thienamycin renal peptidase inhibitors
WO2003018544A1 (en) * 2001-08-24 2003-03-06 Ranbaxy Laboratories Limited Process for the preparation of cilastatin
WO2006022511A1 (en) * 2004-08-25 2006-03-02 Dong Kook Pharm. Co., Ltd. Novel process for the preparation of cilastatin sodium salt

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5147868A (en) * 1978-07-24 1992-09-15 Merck & Co., Inc. Thienamycin renal peptidase inhibitors
WO2003018544A1 (en) * 2001-08-24 2003-03-06 Ranbaxy Laboratories Limited Process for the preparation of cilastatin
JP2005525996A (ja) * 2001-08-24 2005-09-02 ランバクシー ラボラトリーズ リミテッド シラスタチン製造方法
WO2006022511A1 (en) * 2004-08-25 2006-03-02 Dong Kook Pharm. Co., Ltd. Novel process for the preparation of cilastatin sodium salt

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WO2010005175A2 (ko) 2010-01-14
KR100913694B1 (ko) 2009-08-24

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