KR100685336B1 - C-21 변형 에포틸론 - Google Patents
C-21 변형 에포틸론 Download PDFInfo
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- KR100685336B1 KR100685336B1 KR1020017010421A KR20017010421A KR100685336B1 KR 100685336 B1 KR100685336 B1 KR 100685336B1 KR 1020017010421 A KR1020017010421 A KR 1020017010421A KR 20017010421 A KR20017010421 A KR 20017010421A KR 100685336 B1 KR100685336 B1 KR 100685336B1
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- South Korea
- Prior art keywords
- methyl
- dihydroxy
- thiazolyl
- dioxabicyclo
- heptadecane
- Prior art date
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- 0 C[C@@](CCCC(*)=CC[C@](C(C)=Cc1c[s]c(C)n1)OC(C[C@@](C(C)(C)C([C@@]1C)=O)O)=O)[C@@]1O Chemical compound C[C@@](CCCC(*)=CC[C@](C(C)=Cc1c[s]c(C)n1)OC(C[C@@](C(C)(C)C([C@@]1C)=O)O)=O)[C@@]1O 0.000 description 4
- DYLJBXNDAZULIH-QOBAVYGRSA-N C[C@H]([C@@](C[C@@]1(C)[C@H](C2)O)([C@@H](C)CCC[C@@]3(C)O[C@H]3C[C@@H](/C(/C)=C/c3c[s]c(CN(C)C)n3)OC2=O)O)C1=O Chemical compound C[C@H]([C@@](C[C@@]1(C)[C@H](C2)O)([C@@H](C)CCC[C@@]3(C)O[C@H]3C[C@@H](/C(/C)=C/c3c[s]c(CN(C)C)n3)OC2=O)O)C1=O DYLJBXNDAZULIH-QOBAVYGRSA-N 0.000 description 1
- URQUXVJCMZEOKZ-HBSQXNATSA-N C[C@H]([C@@](C[C@@]1(C)[C@H](C2)O)([C@@H](C)CCC[C@@]3(C)O[C@H]3C[C@@H](/C(/C)=C/c3c[s]c(CN4CCN(C)CC4)n3)OC2=O)O)C1=O Chemical compound C[C@H]([C@@](C[C@@]1(C)[C@H](C2)O)([C@@H](C)CCC[C@@]3(C)O[C@H]3C[C@@H](/C(/C)=C/c3c[s]c(CN4CCN(C)CC4)n3)OC2=O)O)C1=O URQUXVJCMZEOKZ-HBSQXNATSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
Description
화합물 | L929 마우스 | KB-3.1 경부 | KB-V1* 경부 | PC-3-전립선 | SK-OV-3-난소 | A-549 폐 | K-562/U-937 백혈병 |
IC50[ng/㎖] | |||||||
21-클로로-에포 A[3] | 170 | 60 | 8 | 10 | 12 (K-562) | ||
에포 A-20-카르발독심 [22a] | 7 | ||||||
에포 A-20-카르발데히드 히드라존 | 12 | ||||||
21-아지도-에포 A [22b] | 6 | ||||||
21-아미노-에포 A [9] | 8 | 4 | 30 | 3 | 4 | 3 (U-937) | |
20-비닐-에포 A [15] | 3 | 3 | 3 | 0.4 | 1 | 1.5 (U-937) | |
21-아지도-에포 B [7] | 0.6 | 0.5 | 0.5 | 0.4 | |||
21-아미노-에포 B [9] | 0.5 | 0.4 | 1.5 | 1.5 | |||
* 다중내성 세포주 |
Claims (33)
- 하기 화학식 Ia 또는 Ib의 화합물.<화학식 Ia><화학식 Ib>식 중,P-Q는 탄소-탄소 이중 결합이거나 또는 에폭시드이고,R은 H 또는 C1-6 알킬이고,G1은 H, C1-6 알킬 또는 할로겐이고,G2는 H 또는 C1-6 알킬이고,G3은 NZ1이고,G4는 H, C1-6 알킬, OZ2, NZ2Z3, Z2C=O 및 Z4SO2로 이루어진 군으로부터 선택되고,G5는 N3, NCS, SH, CN, NC, N(Z1)3 +, 톨루오일, 이미다졸 및 피페르지닐로 이루어진 군으로부터 선택되고,Z1은 H 또는 C1-6 알킬이고,Z2는 H, C1-6 알킬 또는 나프틸이고,Z3은 H 또는 C1-6 알킬이고,Z4는 C1-6 알킬 또는 톨루오일이다.
- 제1항에 있어서, R이 H 원자 또는 메틸기인 화학식 Ia의 화합물.
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- 제1항에 있어서, R은 H 원자 또는 메틸기인 화학식 Ib의 화합물.
- 제6항에 있어서, G5가 N3기인 화합물.
- 제6항에 있어서, G5가 NCS기인 화합물.
- 제6항에 있어서, G5가 SH기인 화합물.
- 제6항에 있어서, G5가 CN기인 화합물.
- 제6항에 있어서, G5가 NC기인 화합물.
- 제6항에 있어서, G5가 톨루오일, 이미다졸 또는 피페르지닐기인 화합물.
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- [1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-3-[2-[2-(아지도메틸)-4-티아졸릴]-1-메틸에테닐]-7,11-디히드록시-8,8,10,12,16-펜타메틸-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-3-[2-[2-(아미노메틸)-4-티아졸릴]-1-메틸에테닐]-7,11-디히드록시-8,8,10,12,16-펜타메틸-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-3-[2-[2-[[[(1,1-디메틸에톡시)카르보닐]아미노]메틸]-4-티아졸릴]-1-메틸에테닐]-7,11-디히드록시-8,8,10,12,16-펜타메틸-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[4S-[4R*,7S*,8R*,9R*,15R*(E)]]-16-[2-[2-[[[(1,1-디메틸에톡시)카르보닐]아미노]메틸]-4-티아졸릴]-1-메틸에테닐]-4,8-디히드록시-5,5,7,9,13-펜타메틸-1-옥사-13(Z)-시클로헥사데센-2,6-디온,[4S-[4R*,7S*,8R*,9R*,15R*(E)]]-16-[2-[2-(아미노메틸)-4-티아졸릴]-1-메틸에테닐]-4,8-디히드록시-5,5,7,9,13-펜타메틸-1-옥사-13(Z)-시클로헥사데센-2,6-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-7,11-디히드록시-8,8,10,12-테트라메틸-3-[1-메틸-2-[2-[(펜타노일옥시)메틸]-4-티아졸릴]에테닐]-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-7,11-디히드록시-8,8,10,12-테트라메틸-3-[1-메틸-2-[2-[(나프토일옥시)메틸]-4-티아졸릴]에테닐]-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-7,11-디히드록시-3-[2-[2-[[(2-메톡시에톡시)아세틸옥시]메틸]-1-메틸-4-티아졸릴]에테닐]-8,8,10,12-테트라메틸-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-7,11-디히드록시-8,8,10,12-테트라메틸-3-[1-메틸-2-[2-[(N-프로피오닐아미노)메틸]-4-티아졸릴]에테닐]-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-3-[2-(3-아세틸-2,3-디히드로-2-메틸렌-4-티아졸릴)-1-메틸에테닐]-7,11-디히드록시-8,8,10,12-테트라메틸-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온, N-옥시드,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-7,11-디히드록시-3-[2-[2-(메톡시메틸)-4-티아졸릴]-1-메틸에테닐]-8,8,10,12-테트라메틸-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-7,11-디히드록시-8,8,10,12,16-펜타메틸-3-[1-메틸-2-[2-(페녹시메틸)-4-티아졸릴]에테닐]-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-3-[2-[2-[(에틸티오)메틸]-4-티아졸릴]-1-메틸에테닐]-7,11-디히드록시-8,8,10,12,16-펜타메틸-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-3-[2-[2-(에톡시메틸)-4-티아졸릴]-1-메틸에테닐]-7,11-디히드록시-8,8,10,12-테트라메틸-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-7,11-디히드록시-8,8,10,12-테트라메틸-3-[1-메틸-2-[2-[(2,3,4,6-테트라아세틸-알파-글루코실옥시)메틸]-4-티아졸릴]에테닐]-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-7,11-디히드록시-8,8,10,12-테트라메틸-3-[1-메틸-2-[2-[(2',3',4',6'-테트라아세틸-베타-글루코실옥시)메틸]-4-티아졸릴]에테닐]-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-7,11-디히드록시-8,8,10,12-테트라메틸-3-[1-메틸-2-[2-[(6'-아세틸-알파-글루코실옥시)메틸]-4-티아졸릴]에테닐]-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-7,11-디히드록시-8,8,10,12-테트라메틸-3-[1-메틸-2-[2-[[(페닐메틸)이미노]메틸]-4-티아졸릴]에테닐]-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-3-[2-(2-아세틸-4-티아졸릴)-1-메틸에테닐]-7,11-디히드록시-8,8,10,12-테트라메틸-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-7,11-디히드록시-8,8,10,12-테트라메틸-3-[1-메틸-2-(2-옥시라닐-4-티아졸릴)에테닐]-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-7,11-디히드록시-3-[2-[2-(2-요오도에테닐)-4-티아졸릴]-1-메틸에테닐]-8,8,10,12-테트라메틸-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-3-[2-(2-에티닐-4-티아졸릴)-1-메틸에테닐]-7,11-디히드록시-8,8,10,12-테트라메틸-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-7,11-디히드록시-8,8,10,12,16-펜타메틸-3-[1-메틸-2-[2-[(메틸아미노)메틸]-4-티아졸릴]에테닐]-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-3-[2-[2-[[[2-(디메틸아미노)에틸]아미노]메틸]-4-티아졸릴]-1-메틸에테닐]-7,11-디히드록시-8,8,10,12,16-펜타메틸-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-3-[2-[2-[(디메틸아미노)메틸]-4-티아졸릴]-1-메틸에테닐]-7,11-디히드록시-8,8,10,12,16-펜타메틸-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-3-[2-[2-[[비스(2-메톡시에틸)아미노]메틸]-4-티아졸릴]-1-메틸에테닐-7,11-디히드록시-8,8,10,12,16-펜타메틸-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-7,11-디히드록시-8,8,10,12,16-펜타메틸-3-[1-메틸-2-[2-[(4-메틸-1-피페라지닐)메틸]-4-티아졸릴]-에테닐]-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-7,11-디히드록시-8,8,10,12,16-펜타메틸-3-[1-메틸-2-[2-[(p-톨루엔술포닐옥시)메틸]-4-티아졸릴]에테닐]-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-3-[2-[2-(브로모메틸)-4-티아졸릴]-1-메틸에테닐]-7,11-디히드록시-8,8,10,12-테트라메틸-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-3-[2-(5-(브로모-2-메틸-4-티아졸릴)-1-메틸에테닐]-7,11-디히드록시-8,8,10,12-테트라메틸-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-3-[2-[2-(시아노메틸)-4-티아졸릴]-1-메틸에테닐]-7,11-디히드록시-8,8,10,12,16-펜타메틸-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[4S-[4R*,7S*,8R*,9R*,15R*(E)]]-16-[2-[2-(시아노메틸)-4-티아졸릴]-1-메틸에테닐]-4,8-디히드록시-5,5,7,9,13-펜타메틸-1-옥사-13(Z)-시클로헥사데센-2,6-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-7,11-디히드록시-3-[2-[2-(1H-이미다졸-1-일메틸)-4-티아졸릴]-1-메틸에테닐]-8,8,10,12,16-펜타메틸-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-3-[2-(2-포르밀-4-티아졸릴)-1-메틸에테닐]-7,11-디히드록시-8,8,10,12-테트라메틸-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-3-[2-(2-포르밀-4-티아졸릴)-1-메틸에테닐]-7,11-디히드록시-8,8,10,12,16-펜타메틸-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-3-[2-(2-에테닐-4-티아졸릴)-1-메틸에테닐]-7,11-디히드록시-8,8,10,12-테트라메틸-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-7,11-디히드록시-3-[2-[2-(메톡시이미노)-4-티아졸릴)-1-메틸에테닐]-8,8,10,12-테트라메틸-4,17-디옥사비시클로[14.1.0]헵타데칸-5,9-디온,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-4-[2-(7,11-디히드록시-8,8,10,12-테트라메틸-5,9-디옥소-4,17-디옥사비시클로[14.1.0]헵타데칸-3-일)-1-프로페닐]-2-티아졸카르복실산,[1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-4-[2-(7,11-디히드록시-8,8,10,12-테트라메틸-5,9-디옥소-4,17-디옥사비시클로[14.1.0]헵타데칸-3-일)-1-프로페닐]-2-티아졸카르복실산 메틸 에스테르로 이루어진 군으로부터 선택된 화합물 또는 그의 제약학적으로 허용가능한 염, 용매 또는 수화물.
- 삭제
- 제21항에 있어서, 환원을 (i) 린들라 (Lindlar) 촉매를 사용한 수소화로 수행하거나 또는 (ii) 포스핀을 사용하여 수행하는 방법.
- 삭제
- 삭제
- 삭제
- 삭제
- 삭제
- 삭제
- 삭제
- 활성 성분으로서, 제1항, 제2항, 제6항 내지 제12항 및 제20항 중 어느 한 항에 따른 화합물 군으로부터 선택되는 화합물 또는 그의 제약학적으로 허용되는 염, 및 1종 이상의 제약학적으로 허용되는 담체, 부형제 또는 희석제를 포함하는, 암을 치료하기 위한 제약 조성물.
- 활성 성분으로서, 제31항에 따른 화합물 및 1종 이상의 제약학적으로 허용되는 담체, 부형제 또는 희석제를 포함하는, 암을 치료하기 위한 제약 조성물.
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DE1999107588 DE19907588A1 (de) | 1999-02-22 | 1999-02-22 | C-21 Modifizierte Epothilone |
DE19907588.3 | 1999-02-22 | ||
DE1999130111 DE19930111A1 (de) | 1999-07-01 | 1999-07-01 | C-21 Modifizierte Epothilone |
DE19930111.5 | 1999-07-01 |
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