KR910000780A - 신규 안트라사이클린 및 그 제조방법과 이것을 포함한 의약품 - Google Patents

신규 안트라사이클린 및 그 제조방법과 이것을 포함한 의약품 Download PDF

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KR910000780A
KR910000780A KR1019900008324A KR900008324A KR910000780A KR 910000780 A KR910000780 A KR 910000780A KR 1019900008324 A KR1019900008324 A KR 1019900008324A KR 900008324 A KR900008324 A KR 900008324A KR 910000780 A KR910000780 A KR 910000780A
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tridioxy
tetrahydroxy
hexahydro
cis
rxy
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끌로드 몬네레
쟝-끌로드 플로랑
길베르 고델
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원본미기재
라보러터리즈 획스트
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    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/24—Condensed ring systems having three or more rings
    • C07H15/244—Anthraquinone radicals, e.g. sennosides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D309/30—Oxygen atoms, e.g. delta-lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/24—Condensed ring systems having three or more rings
    • C07H15/252—Naphthacene radicals, e.g. daunomycins, adriamycins

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Abstract

내용 없음

Description

신규 안트라사이클린 및 그 제조방법과 이것을 포함한 의약품
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (22)

  1. 다음식Ⅰ로 나타낸 안트라사이클린
    여기서 R1은 수소원자 또는 R4가 C1-C8알킬그룹을 나타내는 COR4그룹은 나타낸다.
    R2는 수소원자나 요오드 원자를 나타낸다.
    R3는 아지드그룹, 모르폴리노그룹, 일차아민, R6가 COCF3그룹이나COCH3그룹 또는 프탈이미도그룹을 나타내는 이차아민 NHR6또는 R7이 벤질이나 메틸 또는 아미노니트릴인 삼차아민 NR7을 나타낸다.
    R5는 수소원자, 선택적으로 치환된 C2-C4아실그룹 또는 선택적으로 치환된 벤질그룹을 나타낸다.
  2. 제1항에 있어서, 다음식 6의 (S)-시스-1-O-(4-아지도-2, 4, 6-트리디옥시-α-L-릭소-헥소피라노실)-1, 2, 3, 4, 6, 11-헥사히드로-1, 3, 5, 12-테트라히드록시-3-히드록시메틸-6, 11-나프타센디온으로된 아트라사이클린
    (6)
  3. 제1항에 있어서, 다음식 12의 (S)-시스-1-0-(4-아지도-2, 4, 6-트리디옥시-α-L-릭소-헥소피라노실)-1, 2, 3, 4, 6, 11-헥사히드로-1, 3, 5, 12-테트라히드록시-3-히드록시메틸-6, 11-나프타센디온으로된 안트라사이클린
  4. 제1항에 있어서, 다음식 13의 (S)-시스-1-0-(4-아미노-2, 4, 6-트리디옥시-α-L-릭소-헥소피라노실)-1, 2, 3, 4, 6, 11-헥사히드로-1, 3, 5, 12-테트라히드록시-3-히드록시메틸-6, 11-나프타센디온으로된 안트라사이클린
  5. 제1항에 있어서, 다음식 14의 (S)-시스-1-0-(4-모르폴리노-2, 4, 6-트리디옥시-α-L-릭소-헥소피라노실)-1, 2, 3, 4, 6, 11-헥사히드로-1, 3, 5, 12-테트라히드록시-3-히드록시메틸-6, 11-나프타센디온으로된 안트라사이클린
  6. 제1항에 있어서, 다음식 19의 (S)-시스-1-0-(4-아미노-2, 4, 6-트리디옥시-2-아이오노-α-L-탈로-헥소피라노실)-1, 2, 3, 4, 6, 11-헥사히드-1, 3, 5, 12-테트라히드록시-3-히드록시메틸-6, 11-나프타센디온으로 된 안트라사이클린
  7. 다음의 (1), (2), (3), (4)단계로된 방법으로 제1항에서 제6항중 어느 한 항에 따른 안트라사이클린의 제조방법.
    (1) 다음의 1의 아글리콘을 다음의 1'의 당과 함께 글리코시드화
    여기서 X는 브롬원자 또는 C1'-C2'이중결합을 나타내고, R3및 R5는 상술한 바와 같은 의미를 가진다.
  8. 제7항에 있어서, R3가 이차아민 작용기라면 이 제조방법은 상기 이차아민 작용기로부터 보호기를 제거하는 단계를 포함하는 안트라사이클린의 제조방법.
  9. 제7항에 있어서, X가 브롬원자일때 글리코시드화는 다음 반응기구 Ⅰ에 따라 KOENINGS-KNORR반응에 따라 이루어지는 안트라사이클린의 제조방법.
  10. 제7항에서 제9항중 어느 한 항에 있어서, 아글리콘 1은 다음 반응기구 Ⅱ에 따라 당의 동움으로글리코시드화에 의해 안트라사이클린으로 전환되는 안트라사이클린의 제조방법.
  11. 제7항에서 제9항중 어느 한 항에 있어서, 아글리콘 1은 다음 반응기구 Ⅲ에 따라 식 8의 당의 도움으로 글리코시드화에 의해 안트라사이클린으로 전화되는 안트라사이클린의 제조방법.
  12. 제7항에 있어서, X가 이중결합일 때 글리코시드화는 다음 반응기구 Ⅳ에 따라 N-아이오도숙신이미드의 존재하에 이루어지는 안트라사이클린의 제조방법.
  13. 제10항의 제조방법에서 중간체인 다음식 2의 1-O-아세틸-4-아지도-3-아세틸-2, 4, 6-트리디옥시-L-릭소-헥소피라노즈.
  14. 제10항의 제조방법에서 중간체인 다음식 3의 4-아지도-3-아세틸-2, 4, 6-트리디옥시-L-릭소-헥소피라노즈 브로마이드.
  15. 제11항의 제조방법에서 중간체인 다음식 8의 3-O-벤조일-4-트리플루오로아세트아미도-α-L-릭소-헥소피라노즈브로마이드.
  16. 제12항의 제조방법에서 중간체인 다음식 15의 1, 5-안하이드로-3-O-벤조일-4-트리플루오로아세트아미도-2, 6-디디옥소-D-릭소-1-헥세니톨
  17. 제10항의 제조방법에서 중간체인 다음식 4의(S)-시스-1-O-(3-O-아세틸-4-아지도-2, 4, 6-트리디옥시-α-L-릭소-헥소피라노실)-1, 2, 3, 4, 6, 11-헥사히드로-1, 3, 5, 12-테트라히드록시-3-히드록시메틸-3, 13-이소프로필리덴-6, 11-나프타센디온.
  18. 제10항의 제조방법에서 중간체인 다음식 5의 (S)-시스-1-O-(3-O-아세틸-4-아지도-2, 4, 6-트리디옥시-α-L-릭소-헥소피라노실)-1, 2, 3,4, 6, 11-헥사히드로-1, 3, 5, 12-테트라히드록시-3-히드록시메틸-6, 11-나프타센디온.
  19. 제11항의 제조방법에서 중간체인 다음식 9의 (S)-시스-1-O-(3-O-벤조일-2, 4, 6-트리디옥시-4-(트리플루오로아세트아미도)-α-L-릭소-헥소피라노실)-1, 2, 3, 4, 6, 11-헥사히드로-1, 3, 5, 12-테트라히드록시-3-히드록시메틸-3, 13-이소프로필리덴-6, 11-나프타센디온.
  20. 제11항의 제조방법에서 중간체인 다음식 10의 (S)-시스-1-O-(3-O-벤조일-2, 4, 6-트리디옥시-4-(트리플루오로아세트아미도)-α-L-릭소-헥소피라노실)-1, 2, 3, 4, 6, 11-헥사히드로-1, 3, 5, 12-테트라히드록시-3-히드록시메틸-6, 11-나프타센디온.
  21. 제11항의 제조방법에서 중간체인 다음식 11의 (S)-시스-1-O-2, 4, 6-트리디옥시-4-(트리플루오로아세트아미도)-α-L-릭소-헥소피라실)-1, 2, 3, 4, 6, 11-헥사히드로-1, 3, 5, 12-테트라히드록시-6, 11-나프타센디온.
  22. 활성성분으로 제1항에서 제6항 중 어느 한 항에 따른 안트라사이클린으로 포함하는 제약학적 조성물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019900008324A 1989-06-07 1990-06-07 신규 안트라사이클린 및 그 제조방법과 이것을 포함한 의약품 KR910000780A (ko)

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Application Number Priority Date Filing Date Title
FR8907544A FR2648137A1 (fr) 1989-06-07 1989-06-07 Nouvelles anthracyclines, leur procede de preparation ainsi que medicaments les contenant
FR8907544 1989-06-07

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EP (1) EP0402259A1 (ko)
JP (1) JPH03193798A (ko)
KR (1) KR910000780A (ko)
AU (1) AU5688890A (ko)
CA (1) CA2018480A1 (ko)
FR (1) FR2648137A1 (ko)
PT (1) PT94309A (ko)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100462288B1 (ko) * 2002-04-02 2004-12-17 한국과학기술연구원 혈장 중의 썰트랄린의 검출방법

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU778910B2 (en) * 1999-03-19 2004-12-23 Houston Pharmaceuticals, Inc. Methods and compositions for the manufacture of C-3' and C-4' anthracycline antibiotics

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8508079D0 (en) * 1985-03-28 1985-05-01 Erba Farmitalia Antitumor anthracyclines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100462288B1 (ko) * 2002-04-02 2004-12-17 한국과학기술연구원 혈장 중의 썰트랄린의 검출방법

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CA2018480A1 (fr) 1990-12-07
JPH03193798A (ja) 1991-08-23
AU5688890A (en) 1990-12-13
PT94309A (pt) 1991-02-08
EP0402259A1 (fr) 1990-12-12

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