KR890016029A - 박카틴 ⅲ 및 10-데아세틸박카틴 ⅲ의 유도체를 제조하는 방법 - Google Patents
박카틴 ⅲ 및 10-데아세틸박카틴 ⅲ의 유도체를 제조하는 방법 Download PDFInfo
- Publication number
- KR890016029A KR890016029A KR1019890004540A KR890004540A KR890016029A KR 890016029 A KR890016029 A KR 890016029A KR 1019890004540 A KR1019890004540 A KR 1019890004540A KR 890004540 A KR890004540 A KR 890004540A KR 890016029 A KR890016029 A KR 890016029A
- Authority
- KR
- South Korea
- Prior art keywords
- hydroxy
- iii
- protecting group
- trichloroethoxycarbonyl
- activator
- Prior art date
Links
- YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 title 2
- 150000004200 baccatin III derivatives Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims 11
- -1 β-trimethylsilylethoxy Chemical group 0.000 claims 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 239000012190 activator Substances 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 238000006482 condensation reaction Methods 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical group CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- YWLXLRUDGLRYDR-LUPIKGFISA-N 7-epi-10-deacetylbaccatin iii Chemical group O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-LUPIKGFISA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical group C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000003849 aromatic solvent Substances 0.000 claims 1
- 150000001718 carbodiimides Chemical group 0.000 claims 1
- GCSAXWHQFYOIFE-UHFFFAOYSA-N dipyridin-2-yl carbonate Chemical compound C=1C=CC=NC=1OC(=O)OC1=CC=CC=N1 GCSAXWHQFYOIFE-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Description
Claims (11)
- 하기 일반식(Ⅲ)의 산을 하기 일반식(Ⅳ)의 탁산 유도체와 축합시킨 다음, 이들 식중의 보호기 R1, R3및 적당한 경우 R2를 수소로 치환시키는, 하기 일반식(Ⅰ)의 박카딘 Ⅲ 또는 10-데아세틸 박카딘 Ⅲ의 유도체를 제조하는 방법 :상기식들에서, R은 수소 또는 아세틸을 나타내고, R1은 히드록시-보호기이며, R2는 아세틸기 또는 히드록시-보호기이고, R3는 히드록시-보호기이다.
- 제 1 항에 있어서, R1이 1-에톡시에틸인, 벤질옥시메팅, (β-트리메틸시릴에톡시)메틸, 테트라 히드로피라닐 및 2,2,2-트리클로로에톡시카르보닐을 포함하는 군에서 선택되는 방법.
- 제 2 항에 있어서, R1이 1-에톡시에틸인 방법.
- 제 1 항에 있어서, 같거나 다를 수 있는 히드록시-보호기 R2및 R3가 2,2,2-트리클로로에톡시카르보닐 또는 알킬 부분이 C1-C3를 포함하는 트리알킬실릴기로부터 선택되는 방법.
- 제 4 항에 있어서, 히드록시-보호기가 2,2,2-트리클로로에톡시카르보닐인 방법.
- 제 1 항에 있어서, 축합 반응이 축합제와 활성화제 존재하에서 수행되는 방법.
- 제 6 항에 있어서, 축합제가 카르보디이미드와 반응성카르보네이트로에서 선택되고 활성화제가 디알킬아미노피리딘으로 선택된 방법.
- 제 7 항에 있어서, 축합제가 디시클로헥실카르보디이미드와 디-2-피리딜 카르보네이트로에서 선택되고, 활성화제가 4-디메틸아미노 피리딘으로 선택된 방법.
- 제 1 항에 있어서, 축합 반응이 벤젠, 톨루엔, 크실렌, 에틸벤젠, 이소프로필벤젠 및 클로로벤젠에서 선택된 방향성 용매 내에서 수행되는 방법.
- 제 1 항에 있어서, 축합 반응이 60~90℃의 온도에서 수행되는 방법.
- 제 1 항에 있어서, 하기 중간체를 아세트산 존재내에서 아연으로, 또는 C1-C3지방족 알콜내에 용해된 무기 또는 유기산으로 처리하는 것을 포함하는, 하기 일반식 중간체 생성물상의 보호기 R1-C3및 적당한 경우, R2를 수소로 치환시키는 방법:※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR8804513 | 1988-04-06 | ||
FR8804513A FR2629819B1 (fr) | 1988-04-06 | 1988-04-06 | Procede de preparation de derives de la baccatine iii et de la desacetyl-10 baccatine iii |
Publications (2)
Publication Number | Publication Date |
---|---|
KR890016029A true KR890016029A (ko) | 1989-11-28 |
KR970009729B1 KR970009729B1 (ko) | 1997-06-17 |
Family
ID=9364992
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019890004540A KR970009729B1 (ko) | 1988-04-06 | 1989-04-06 | 박카틴 ⅲ 및 10-데아세틸박카틴 ⅲ의 유도체를 제조하는 방법. |
Country Status (13)
Country | Link |
---|---|
US (1) | US4924012A (ko) |
EP (1) | EP0336841B1 (ko) |
JP (1) | JPH0686441B2 (ko) |
KR (1) | KR970009729B1 (ko) |
AT (1) | ATE89823T1 (ko) |
AU (1) | AU618333B2 (ko) |
CA (1) | CA1308417C (ko) |
DE (1) | DE68906705T2 (ko) |
ES (1) | ES2055119T3 (ko) |
FR (1) | FR2629819B1 (ko) |
GR (1) | GR3007982T3 (ko) |
IL (1) | IL89831A (ko) |
ZA (1) | ZA892474B (ko) |
Families Citing this family (136)
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---|---|---|---|---|
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US4960790A (en) * | 1989-03-09 | 1990-10-02 | University Of Kansas | Derivatives of taxol, pharmaceutical compositions thereof and methods for the preparation thereof |
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US5304670A (en) * | 1989-08-23 | 1994-04-19 | Centre National De La Recherche Scientifique | Process for the enantioselective preparation of phenylisoserine derivatives |
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FR2658513B1 (fr) * | 1990-02-21 | 1994-02-04 | Rhone Poulenc Sante | Procede de preparation de l'acide cis-beta-phenylglycidique-(2r,3r). |
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FR2678930B1 (fr) * | 1991-07-10 | 1995-01-13 | Rhone Poulenc Rorer Sa | Procede de preparation de derives de la baccatine iii et de la desacetyl-10 baccatine iii. |
US5481010A (en) * | 1991-07-16 | 1996-01-02 | Centre National De La Recherche Scientifique | 7-deacetoxy beccatine IV derivative and preparation and use thereof |
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FR2680506B1 (fr) * | 1991-08-19 | 1994-09-02 | Rhone Poulenc Rorer Sa | Procede de preparation de derives de la beta-phenylisoserine et leur utilisation. |
US6335362B1 (en) | 1991-09-23 | 2002-01-01 | Florida State University | Taxanes having an alkyl substituted side-chain and pharmaceutical compositions containing them |
US5350866A (en) * | 1991-09-23 | 1994-09-27 | Bristol-Myers Squibb Company | 10-desacetoxytaxol derivatives |
US5399726A (en) * | 1993-01-29 | 1995-03-21 | Florida State University | Process for the preparation of baccatin III analogs bearing new C2 and C4 functional groups |
US7074945B2 (en) * | 1991-09-23 | 2006-07-11 | Florida State University | Metal alkoxide taxane derivatives |
US5728850A (en) * | 1991-09-23 | 1998-03-17 | Florida State University | Taxanes having a butenyl substituted side-chain and pharmaceutical compositions containing them |
US5243045A (en) * | 1991-09-23 | 1993-09-07 | Florida State University | Certain alkoxy substituted taxanes and pharmaceutical compositions containing them |
US5229526A (en) * | 1991-09-23 | 1993-07-20 | Florida State University | Metal alkoxides |
US5739362A (en) * | 1991-09-23 | 1998-04-14 | Florida State University | Taxanes having an alkoxy, alkenoxy or aryloxy substituted side-chain and pharmaceutical compositions containing them |
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US5721268A (en) * | 1991-09-23 | 1998-02-24 | Florida State University | C7 taxane derivatives and pharmaceutical compositions containing them |
US6028205A (en) * | 1991-09-23 | 2000-02-22 | Florida State University | C2 tricyclic taxanes |
US5283253A (en) * | 1991-09-23 | 1994-02-01 | Florida State University | Furyl or thienyl carbonyl substituted taxanes and pharmaceutical compositions containing them |
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Publication number | Priority date | Publication date | Assignee | Title |
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FR2601675B1 (fr) * | 1986-07-17 | 1988-09-23 | Rhone Poulenc Sante | Derives du taxol, leur preparation et les compositions pharmaceutiques qui les contiennent |
FR2601676B1 (fr) * | 1986-07-17 | 1988-09-23 | Rhone Poulenc Sante | Procede de preparation du taxol et du desacetyl-10 taxol |
FR2629818B1 (fr) * | 1988-04-06 | 1990-11-16 | Centre Nat Rech Scient | Procede de preparation du taxol |
-
1988
- 1988-04-06 FR FR8804513A patent/FR2629819B1/fr not_active Expired - Lifetime
-
1989
- 1989-04-03 US US07/331,758 patent/US4924012A/en not_active Expired - Lifetime
- 1989-04-03 IL IL89831A patent/IL89831A/xx unknown
- 1989-04-04 AU AU32426/89A patent/AU618333B2/en not_active Expired
- 1989-04-04 ZA ZA892474A patent/ZA892474B/xx unknown
- 1989-04-05 CA CA000595731A patent/CA1308417C/fr not_active Expired - Lifetime
- 1989-04-05 ES ES89400935T patent/ES2055119T3/es not_active Expired - Lifetime
- 1989-04-05 DE DE8989400935T patent/DE68906705T2/de not_active Expired - Lifetime
- 1989-04-05 JP JP1084916A patent/JPH0686441B2/ja not_active Expired - Lifetime
- 1989-04-05 AT AT89400935T patent/ATE89823T1/de not_active IP Right Cessation
- 1989-04-05 EP EP89400935A patent/EP0336841B1/fr not_active Expired - Lifetime
- 1989-04-06 KR KR1019890004540A patent/KR970009729B1/ko not_active IP Right Cessation
-
1993
- 1993-05-27 GR GR930400035T patent/GR3007982T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
US4924012A (en) | 1990-05-08 |
EP0336841B1 (fr) | 1993-05-26 |
ES2055119T3 (es) | 1994-08-16 |
DE68906705T2 (de) | 1993-09-16 |
JPH01305077A (ja) | 1989-12-08 |
FR2629819B1 (fr) | 1990-11-16 |
JPH0686441B2 (ja) | 1994-11-02 |
IL89831A (en) | 1992-12-01 |
EP0336841A1 (fr) | 1989-10-11 |
KR970009729B1 (ko) | 1997-06-17 |
ATE89823T1 (de) | 1993-06-15 |
IL89831A0 (en) | 1989-12-15 |
AU618333B2 (en) | 1991-12-19 |
ZA892474B (en) | 1989-12-27 |
DE68906705D1 (de) | 1993-07-01 |
GR3007982T3 (ko) | 1993-08-31 |
CA1308417C (fr) | 1992-10-06 |
FR2629819A1 (fr) | 1989-10-13 |
AU3242689A (en) | 1989-10-12 |
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