KR930007882A - 세포독성 비시클로[7.3.1]트리데 - 4 - 센 - 2,6디인 화합물 및 그의 제조방법 - Google Patents
세포독성 비시클로[7.3.1]트리데 - 4 - 센 - 2,6디인 화합물 및 그의 제조방법 Download PDFInfo
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- KR930007882A KR930007882A KR1019920019668A KR920019668A KR930007882A KR 930007882 A KR930007882 A KR 930007882A KR 1019920019668 A KR1019920019668 A KR 1019920019668A KR 920019668 A KR920019668 A KR 920019668A KR 930007882 A KR930007882 A KR 930007882A
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- 150000001875 compounds Chemical class 0.000 title claims abstract 36
- 231100000433 cytotoxic Toxicity 0.000 title 1
- 230000001472 cytotoxic effect Effects 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- 201000011510 cancer Diseases 0.000 claims abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 24
- 239000001257 hydrogen Substances 0.000 claims 24
- 125000000217 alkyl group Chemical group 0.000 claims 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 239000004593 Epoxy Substances 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 3
- 230000000259 anti-tumor effect Effects 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- -1 n-heptanoyl Chemical group 0.000 claims 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 abstract 2
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 abstract 1
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 abstract 1
- 229930189413 Esperamicin Natural products 0.000 abstract 1
- 241000124008 Mammalia Species 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 125000002619 bicyclic group Chemical group 0.000 abstract 1
- 229940127089 cytotoxic agent Drugs 0.000 abstract 1
- 239000002254 cytotoxic agent Substances 0.000 abstract 1
- 231100000599 cytotoxic agent Toxicity 0.000 abstract 1
- LJQQFQHBKUKHIS-WJHRIEJJSA-N esperamicin Chemical compound O1CC(NC(C)C)C(OC)CC1OC1C(O)C(NOC2OC(C)C(SC)C(O)C2)C(C)OC1OC1C(\C2=C/CSSSC)=C(NC(=O)OC)C(=O)C(OC3OC(C)C(O)C(OC(=O)C=4C(=CC(OC)=C(OC)C=4)NC(=O)C(=C)OC)C3)C2(O)C#C\C=C/C#C1 LJQQFQHBKUKHIS-WJHRIEJJSA-N 0.000 abstract 1
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 abstract 1
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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Abstract
본 발명은 에스페라미신의 아글리콘의 일부인 8-히드록시-비시클로[7,3,1]-트리데-4-센-2,6-디인 고리계의 새롭고도 효과적인 제조방법과 상기 비시클릭 고리계를 갖는 신규한 세포독성제제에 관한 것이다.
본 발명은 또한 악성종양에 걸린 포유동물에게 본 발명의 화합물의 항종양 유효량을 투여하는 것으로 되는, 종양치료 방법도 제공한다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (32)
- 다음 일반식을 갖는 화합물 또는 약리적으로 허용되는 그의 염.상기식중,----는 이중결합, 단일결합 또는 에폭시; Rx또는 Ry중 하나는 수소이고 다른 하나는 수소 또는 히드록시; 또는 Rx와 Ry는 함께 옥소기를 형성하고; RW는 수고, -C(O)Rs, -C(O)NRtRu또는 -C(O)ORv, Rz및 Rz1은 각각 수고, 또는 Rz나 Rz1중 하나는 수소이고 다른 하나는 히드록시, -OC(O)Rs, -OC(O)NRtRu또는 -OC(O)ORv이며, Rs는 수소, C1-8알킬, C3-6시클로알킬, C6-10아릴, C7-14아르알킬 또는 퀴놀살릴; Rt및 Ru는 독립적으로 소수, C1-8알킬, 아미노-치환된 C1-8알킬, C3-6시클로알킬, C6-10아릴, C7-14아르알킬, 피리딜 또는 퀴녹살릴이며; Rv는 C1-8알킬, 할로-치환된 C1-8알킬, C3-6시클로알킬, C6-10아릴 또는 C7-14아르알킬이고; Rw, Rx, 및 Rz1이 각각 수소이고,----가 이중 결합이면 Rz는 히드록시 아님.
- 제1항에 있어서, 다음 일반식을 갖는 화합물 또는 그의 약리적으로 허용되는 염.상기식중,----는 이중결합, 단일결합 또는 에폭시; Rx또는 Ry중 하나는 수소이고 다른 하나는 수소 또는 히드록시; 또는 Rx와 Ry는 함께 옥소기를 형성하고; RW는 수고, -C(O)Rs, -C(O)NRtRu또는 -C(O)ORv, Rz는 수소, 히드록시, -OC(O)Rs, -OC(O)NRtRu또는 -OC(O)ORv이며, Rs는 수소, C1-8알킬, C3-6시클로알킬, C6-10아릴, C7-14아르알킬 또는 퀴놀살릴; Rt및 Ru는 독립적으로 소수, C1-8알킬, 아미노-치환된 C1-8알킬, C3-6시클로알킬, C1-10아릴, C7-14아르알킬, 피리딜 또는 퀴녹살릴이며; Rv는 C1-8알킬, 할로-치환된 C1-8알킬, C3-6시클로알킬, C1-10아릴 또는 C7-14아르알킬이고; Rw, Rx, 및 Ry이 각각 수소이고,----가 이중 결합이면 Rz는 히드록시 아님.
- 제2항에 있어서, Rw가 수소인 것이 특징인 화합물.
- 제3항에 있어서, Rz가 히드록시, -C(O)Rs, -C(O)NRtRu또는 -C(O)ORv이고, Rs,Rt,Ru및 Rv는 제1항에서 정의된 바와 같으며; Rz및 Ry가 수소이고----가 이중결합이며, RZ는 히드록시가 아닌 것이 특징인 화합물.
- 제4항에 있어서, Rz와 Ry는 각각 수소이고----이 이중결합이면, RZ는 히드록시가 아닌 것이 특징인 화합물.
- 제5항에 있어서,----이 이중결합 또는 에폭시인 것이 특징인 화합물.
- 제6항에 있어서,----이 이중결합인 것이 특징인 화합물.
- 제7항에 있어서, Rz이 -OC(O)Rs이고, Rs는 수소, C1-8알킬 또는 퀴녹살린인 것이 특징인 화합물.
- 제7항에 있어서, Rz이 -OC(O)NRtRu이고, Rt는 수소, Ru는 C1-8알킬, 아미노-치환된 C1-8알킬, 피리딜 또는 퀴녹살릴이며; 또는 Rt및 Ru는 각각 C1-8알킬인 것이 특징인 화합물.
- 제7항에 있어서, Rz이 -OC(O)ORv;Rv는 할로-치환된 C1-8알킬인 것이 특징인 화합물.
- 제8항에 있어서, Rs가 메틸인 것이 특징인 화합물.
- 제8항에 있어서, Rs가 퀴녹살릴인 것이 특징인 화합물.
- 제8항에 있어서, Rs가 수소인 것이 특징인 화합물.
- 제8항에 있어서, Rs가 n-헵타노일인 것이 특징인 화합물.
- 제9항에 있어서, Rt가 수소이고 Ru는 메틸인 것이 특징인 화합물.
- 제9항에 있어서, Rt가 수소이고 Ru는 퀴녹살릴인 것이 특징인 화합물.
- 제9항에 있어서, Rt와 Ru가 각각 에틸인 것이 특징인 화합물.
- 제9항에 있어서, Rt가수소이고 Ru는 5-아미노펜틸인 것이 특징인 화합물.
- 제9항에 있어서, Rt가 수소이고 Ru는 2-피리딜인 것이 특징인 화합물.
- 제10항에 있어서, Rv가 2,2,2-트리클로로에틸인 것이 특징인 화합물.
- 제6항에 있어서,----가 각각 에틸인 것이 특징인 화합물.
- 제21항에 있어서, Rz이 히드록시인 것이 특징인 화합물.
- 제3항에 있어서, Rz이 수소인 것이 특징인 화합물.
- 제23항에 있어서,----가 단일 결합인 것이 특징인 화합물.
- 제24항에 있어서, Rx와 Ry가 각각 수소인 것이 특징인 화합물.
- 제23항에 있어서,----가 이중 결합인 것이 특징인 화합물.
- 제26항에 있어서, Rx와 Ry가 각각 수소인 것이 특징인 화합물.
- 제26항에 있어서, Rx와 Ry중 하나가 히드록시인 것이 특징인 화합물.
- 제26항에 있어서, Rx와 Ry가 함께 옥소기를 나타내는 것이 특징인 화합물.
- 제3항에 있어서, Rz이 히드록시이고, Rx또는 Ry중 하나는 히드록시이며 다른 하나는 수소이고,----는 이중결합인 것이 특징인 화합물.
- 제1항의 화합물에 민감한 악성 종양에 걸린 동물에게 제1항의 화합물의 항종양 유효량을 투여하는 것으로 이루어지는 제1항의 화합물에 민감한 악성 종양에 걸린 동물의 치료방법.
- 제1항의 화합물의 항종양 유효량과 약리적으로 허용되는 담체로 이루어지는 항종양 제약 조성물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/782,942 US5198560A (en) | 1990-04-27 | 1991-10-25 | Cytotoxic bicyclo[7.3.1]tridec-4-ene-2,6-diyne compounds and process for the preparation thereof |
US782,942 | 1991-10-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
KR930007882A true KR930007882A (ko) | 1993-05-20 |
Family
ID=25127668
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019920019668A KR930007882A (ko) | 1991-10-25 | 1992-10-24 | 세포독성 비시클로[7.3.1]트리데 - 4 - 센 - 2,6디인 화합물 및 그의 제조방법 |
Country Status (14)
Country | Link |
---|---|
US (1) | US5198560A (ko) |
EP (1) | EP0538898A3 (ko) |
JP (1) | JPH07242585A (ko) |
KR (1) | KR930007882A (ko) |
CN (1) | CN1071912A (ko) |
AU (1) | AU658230B2 (ko) |
CA (1) | CA2081007A1 (ko) |
FI (1) | FI924777A (ko) |
HU (1) | HUT62251A (ko) |
IL (1) | IL103516A0 (ko) |
MX (1) | MX9206064A (ko) |
NZ (1) | NZ244871A (ko) |
TW (1) | TW218867B (ko) |
ZA (1) | ZA928158B (ko) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100476467B1 (ko) * | 2001-07-24 | 2005-03-18 | 주식회사 코오롱 | 알칼리 이용성 폴리에스테르의 제조방법 |
KR20230055507A (ko) | 2021-10-19 | 2023-04-26 | 농업회사법인 파인 주식회사 | 난황유 용매 추출시 잔유용매 제거방법 |
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US6214345B1 (en) | 1993-05-14 | 2001-04-10 | Bristol-Myers Squibb Co. | Lysosomal enzyme-cleavable antitumor drug conjugates |
DK0871490T3 (da) * | 1995-12-22 | 2003-07-07 | Bristol Myers Squibb Co | Forgrenede hydrazonlinkere |
US6908978B2 (en) * | 2001-11-02 | 2005-06-21 | Bausch & Lomb Incorporated | High refractive index polymeric siloxysilane compositions |
TWI349422B (en) | 2007-03-21 | 2011-09-21 | Delta Electronics Inc | Control system and method for tuning the system thereof |
CA2836338C (en) | 2011-05-16 | 2022-05-03 | Koninklijke Philips N.V. | Tetrazine derivatives used in bio-orthogonal drug activation |
FI2922574T3 (fi) | 2012-11-22 | 2023-08-11 | Tagworks Pharmaceuticals B V | Kemiallisesti pilkkoutuva ryhmä |
RU2019105549A (ru) | 2012-12-21 | 2019-03-28 | Биоэллаенс К. В. | Гидрофильные саморазрушающиеся линкеры и их конъюгаты |
AU2015276821A1 (en) | 2014-06-20 | 2017-01-12 | Abgenomics International Inc. | Anti-folate receptor aplha (FRA) antibody-drug conjugates and methods of using thereof |
CN105218362B (zh) * | 2015-08-28 | 2017-03-22 | 吉林大学 | 一种共轭炔酮的还原酰化反应方法 |
RU2766000C2 (ru) | 2016-01-08 | 2022-02-07 | АльтруБио Инк. | Четырехвалентные антитела к psgl-1 и их применения |
EP3474901A1 (en) | 2016-06-27 | 2019-05-01 | Tagworks Pharmaceuticals B.V. | Cleavable tetrazine used in bio-orthogonal drug activation |
US20210308207A1 (en) | 2018-05-04 | 2021-10-07 | Tagworks Pharmaceuticals B.V. | Compounds comprising a linker for increasing transcyclooctene stability |
WO2019212356A1 (en) | 2018-05-04 | 2019-11-07 | Tagworks Pharmaceuticals B .V. | Tetrazines for high click conjugation yield in vivo and high click release yield |
IL289094A (en) | 2019-06-17 | 2022-02-01 | Tagworks Pharmaceuticals B V | Tetrazines for increasing the speed and yield of the "click release" reaction |
US20230121556A1 (en) | 2019-06-17 | 2023-04-20 | Tagworks Pharmaceuticals B.V. | Compounds for fast and efficient click release |
ES2963003T3 (es) | 2020-10-27 | 2024-03-22 | Elucida Oncology Inc | Conjugados de nanopartículas y fármacos dirigidos a receptor de folato y usos de los mismos |
CN113214283B (zh) * | 2021-04-12 | 2022-09-30 | 华南理工大学 | 一种呋喃大环化合物制备方法及制备的呋喃大环化合物和应用 |
WO2023158305A1 (en) | 2022-02-15 | 2023-08-24 | Tagworks Pharmaceuticals B.V. | Masked il12 protein |
WO2024080872A1 (en) | 2022-10-12 | 2024-04-18 | Tagworks Pharmaceuticals B.V. | Strained bicyclononenes |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2040855A1 (en) * | 1990-04-27 | 1991-10-28 | John F. Kadow | Cytotoxic bicyclo¬7.3.1| tridec-4-ene-2,6-diyne compounds and process for the preparation thereof |
-
1991
- 1991-10-25 US US07/782,942 patent/US5198560A/en not_active Expired - Fee Related
-
1992
- 1992-10-16 TW TW081108254A patent/TW218867B/zh active
- 1992-10-19 AU AU27108/92A patent/AU658230B2/en not_active Expired - Fee Related
- 1992-10-20 CA CA002081007A patent/CA2081007A1/en not_active Abandoned
- 1992-10-21 FI FI924777A patent/FI924777A/fi unknown
- 1992-10-22 ZA ZA928158A patent/ZA928158B/xx unknown
- 1992-10-22 MX MX9206064A patent/MX9206064A/es unknown
- 1992-10-22 IL IL103516A patent/IL103516A0/xx unknown
- 1992-10-22 HU HU9203322A patent/HUT62251A/hu unknown
- 1992-10-23 EP EP19920118220 patent/EP0538898A3/en not_active Withdrawn
- 1992-10-23 NZ NZ244871A patent/NZ244871A/en unknown
- 1992-10-24 CN CN92112589A patent/CN1071912A/zh active Pending
- 1992-10-24 KR KR1019920019668A patent/KR930007882A/ko not_active Application Discontinuation
- 1992-10-26 JP JP4327146A patent/JPH07242585A/ja active Pending
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100476467B1 (ko) * | 2001-07-24 | 2005-03-18 | 주식회사 코오롱 | 알칼리 이용성 폴리에스테르의 제조방법 |
KR20230055507A (ko) | 2021-10-19 | 2023-04-26 | 농업회사법인 파인 주식회사 | 난황유 용매 추출시 잔유용매 제거방법 |
Also Published As
Publication number | Publication date |
---|---|
HU9203322D0 (en) | 1992-12-28 |
AU2710892A (en) | 1993-04-29 |
IL103516A0 (en) | 1993-03-15 |
HUT62251A (en) | 1993-04-28 |
EP0538898A2 (en) | 1993-04-28 |
FI924777A (fi) | 1993-04-26 |
AU658230B2 (en) | 1995-04-06 |
FI924777A0 (fi) | 1992-10-21 |
CA2081007A1 (en) | 1993-04-26 |
NZ244871A (en) | 1995-05-26 |
ZA928158B (en) | 1993-04-28 |
MX9206064A (es) | 1993-04-01 |
TW218867B (ko) | 1994-01-11 |
US5198560A (en) | 1993-03-30 |
JPH07242585A (ja) | 1995-09-19 |
EP0538898A3 (en) | 1993-06-23 |
CN1071912A (zh) | 1993-05-12 |
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