KR930703265A - Novel polymorphic cimetidine and preparation method thereof - Google Patents

Novel polymorphic cimetidine and preparation method thereof

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Publication number
KR930703265A
KR930703265A KR1019930702424A KR930702424A KR930703265A KR 930703265 A KR930703265 A KR 930703265A KR 1019930702424 A KR1019930702424 A KR 1019930702424A KR 930702424 A KR930702424 A KR 930702424A KR 930703265 A KR930703265 A KR 930703265A
Authority
KR
South Korea
Prior art keywords
methylthio
guanidine
cyano
ethyl
methyl
Prior art date
Application number
KR1019930702424A
Other languages
Korean (ko)
Inventor
제스젠스즈끼 안도르
베그 페렌크
벤크시크 페터
나기 라스즈로
헤게뒤스 벨라
괴뢰그 산도르
파프네 스지클라이 즈소피아
하즈노크지 마리안느
베레크케이 라스즈로
코즈마 게자네
카파스 마르기트
퇴뢰크 에바
Original Assignee
에바 프리드만
리크터 게데온 베게스제티 기야르 알티
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by 에바 프리드만, 리크터 게데온 베게스제티 기야르 알티 filed Critical 에바 프리드만
Publication of KR930703265A publication Critical patent/KR930703265A/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)

Abstract

본 발명은 적외선 분광학적 특성에 의하여 특정지워지는 N-시아노-N′-메틸-N″-{2-〔5-메틸이미다졸-4-일)-메틸티오〕-에틸}-구아니딘(시메티딘 “E”)의 신규한 다형태성 변형체 “E”에 관한 것이다.The present invention relates to N-cyano-N′-methyl-N ″-{2- [5-methylimidazol-4-yl) -methylthio] -ethyl} -guanidine (as specified by infrared spectroscopic characteristics). Novel polymorphic variant "E" of cimetidine "E").

본 발명의 방법에 따르면, 시메티딘 “E”는 30℃이하의 온도에서 N-시아노-N′-메틸-N″-{2-〔5-메틸이미다졸-4-일)-메틸티오〕-에틸}-구아니딘을 과포화시키고 40부피%이하의 양으로 수-혼화성 유기 용매를 함유하는 수성계를 제조하고, 결정핵제를 임의로 첨가하여 용액이나 현탁액을 결정화하며, 침전된 결정을 분리하고, 이들을 20℃이하의 온도에서 건조시키거나 결정의 수함량을 유기 용매로 제거한 다음 이들을 건조시켜 제조된다.According to the method of the present invention, cimetidine “E” is N-cyano-N′-methyl-N ″-{2- [5-methylimidazol-4-yl) -methylthio] at a temperature of 30 ° C. or less. Prepare an aqueous system which supersaturates -ethyl} -guanidine and contains a water-miscible organic solvent in an amount of up to 40% by volume, optionally adds a nucleating agent to crystallize the solution or suspension, to separate the precipitated crystals, They are prepared by drying at a temperature below 20 ° C. or by removing the water content of the crystals with an organic solvent and then drying them.

신규한 시메티딘의 변형체 “E”는 시메티딘 “A”의 것과 비교하여 더욱 양호한 유동학적 성질 및 유동성을 보여주며 약제 기술과 관련하여 몇가지 잇점을 제공한다.The new variant of cimetidine “E” shows better rheological properties and fluidity compared to that of cimetidine “A” and offers several advantages with regard to pharmaceutical technology.

Description

신규한 다형태성 시메티딘 및 이의 제조방법Novel polymorphic cimetidine and preparation method thereof

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

제1도는 본 발명의 변형체의 IR스펙트럼을 도시한 것이다. 제2도는 제1도에 나타낸 완전한 특성의 우측을 확대시킨 것이다. 제3도는 제1도에 나타낸 완전한 특성의 좌측을 확대시킨 것이다. 제4도는 스튜던트 t시험에서 얻어진 시간에 따른 시메티딘의 플라스마 수준을 나타낸 것이다.Figure 1 shows the IR spectrum of the variant of the present invention. FIG. 2 is an enlargement of the right side of the complete characteristic shown in FIG. 3 enlarges the left side of the complete characteristic shown in FIG. 4 shows the plasma levels of cimetidine over time obtained in the Student's t test.

Claims (5)

제1도에 나타낸 적외선 분광학적 특성에 의하여 특징지워지는 N-시아노-N′-메틸-N″-{2-〔5-메틸이미다졸-4-일)-메틸티오〕-에틸}-구아니딘(시메티딘)의 다형태성 변형체“E”.N-cyano-N′-methyl-N ″-{2- [5-methylimidazol-4-yl) -methylthio] -ethyl}-characterized by the infrared spectroscopic characteristics shown in FIG. Polymorphic variant of guanidine (cimetidine) "E". 약제학에서 통상적으로 사용되는 캐리어 및/또는 첨가제와 혼합하여, 활성 성분으로서 제1항에서 한정한 N-시아노-N′-메틸-N″-{2-〔5-메틸이미다졸-4-일)-메틸티오〕-에틸}-구아니딘의 신규한 다형태성 변형체 “E”를 함유하는 약제학적 조성물.N-cyano-N'-methyl-N "-{2- [5-methylimidazole-4- as defined in claim 1 as an active ingredient, in admixture with carriers and / or additives conventionally used in pharmaceuticals. A pharmaceutical composition containing the novel polymorphic variant “E” of I) -methylthio] -ethyl} -guanidine. N-시아노-N′-메틸-N″-{2-〔5-메틸이미다졸-4-일)-메틸티오〕-에틸}-구아니딘의 신규한 다형태성 변형체 “E”의 제조방법으로서, 30℃이하의 온도에서 N-시아노-N′-메틸-N″-{2-〔5-메틸이미다졸-4-일)-메틸티오〕-에틸}-구아니딘을 과포화시키고 40부피%이하의 양으로 수-혼화성 유기 용매를 함유하는 수성계를 제조하고, 결정핵제를 임의로 첨가하여 용액이나 현탁액을 결정화하며, 침전된 결정을 분리하고, 이들을 20℃이하의 온도에서 건조시키거나 결정의 수함량을 유기 용매로 제거한 다음 이들을 건조시키는 과정을 포함함을 특징으로 하는 제조방법.As a method for producing a novel polymorphic variant “E” of N-cyano-N′-methyl-N ″-{2- [5-methylimidazol-4-yl) -methylthio] -ethyl} -guanidine , Supersaturated N-cyano-N′-methyl-N ″-{2- [5-methylimidazol-4-yl) -methylthio] -ethyl} -guanidine at a temperature of 30 ° C. or below and 40% by volume. Prepare aqueous systems containing water-miscible organic solvents in the following amounts, crystallize solutions or suspensions by optionally adding nucleating agents, isolate precipitated crystals, and dry or crystallize them at temperatures below 20 ° C. Removing the water content with an organic solvent and then drying them. 제3항에 있어서, 수-혼화성 유기 용매로서 C1~3알칸을 또는 케톤을 사용하는 방법.The method of claim 3 wherein the water-miscible organic solvent as the use of the C 1 to 3 alkane or ketone. 활성 성분으로서 제1항에서 한정된 N-시아노-N′-메틸-N″-{2-〔5-메틸이미다졸-4-일)-메틸티오〕-에틸}-구아니딘의 신규한 다형태성 변형체 “E”를 약제학에서 통상적으로 사용되는 캐리어 및/또는 첨가제와 혼합하고 이들을 약제학적 조성물로 변형시킴을 특징으로 하는 약제학적 조성물의 제조방법.Novel polymorphism of N-cyano-N'-methyl-N "-{2- [5-methylimidazol-4-yl) -methylthio] -ethyl} -guanidine as active ingredient as defined in claim 1 A method of preparing a pharmaceutical composition characterized by mixing the variant “E” with carriers and / or additives commonly used in pharmaceuticals and transforming them into pharmaceutical compositions. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019930702424A 1991-02-15 1992-02-14 Novel polymorphic cimetidine and preparation method thereof KR930703265A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
HU91-502 1991-02-15
HU91502A HU208675B (en) 1991-02-15 1991-02-15 Process for producing a new cimetidine polymorph and pharmaceutical preparations comprising this compound
PCT/HU1992/000007 WO1992014713A1 (en) 1991-02-15 1992-02-14 Novel cimetidine polymorph and process for preparing same

Publications (1)

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KR930703265A true KR930703265A (en) 1993-11-29

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EP (1) EP0571463A1 (en)
JP (1) JPH06505247A (en)
KR (1) KR930703265A (en)
AU (1) AU653209B2 (en)
CA (1) CA2104027A1 (en)
HU (1) HU208675B (en)
WO (1) WO1992014713A1 (en)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH064601B2 (en) * 1987-11-04 1994-01-19 三井石油化学工業株式会社 Method for purifying N-cyano-N'-methyl-N "-[2-{(5-methyl-1H-imidazol-4-yl) methylthio} ethylguanidine

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Publication number Publication date
HUT60474A (en) 1992-09-28
AU653209B2 (en) 1994-09-22
CA2104027A1 (en) 1992-08-16
HU910502D0 (en) 1991-09-30
AU1264692A (en) 1992-09-15
WO1992014713A1 (en) 1992-09-03
EP0571463A1 (en) 1993-12-01
JPH06505247A (en) 1994-06-16
HU208675B (en) 1993-12-28

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