KR880006246A - 레베카마이신 동족체 - Google Patents
레베카마이신 동족체 Download PDFInfo
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- KR880006246A KR880006246A KR870013102A KR870013102A KR880006246A KR 880006246 A KR880006246 A KR 880006246A KR 870013102 A KR870013102 A KR 870013102A KR 870013102 A KR870013102 A KR 870013102A KR 880006246 A KR880006246 A KR 880006246A
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- South Korea
- Prior art keywords
- alkyl
- amino
- alkoxycarbonyl
- mono
- aryl
- Prior art date
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- INSACQSBHKIWNS-QZQSLCQPSA-N rebeccamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](OC)[C@@H](CO)O[C@H]1N1C2=C3N=C4[C](Cl)C=CC=C4C3=C3C(=O)NC(=O)C3=C2C2=CC=CC(Cl)=C21 INSACQSBHKIWNS-QZQSLCQPSA-N 0.000 title abstract 4
- ZGCSNRKSJLVANE-UHFFFAOYSA-N Aglycone-Rebeccamycin Natural products N1C2=C3NC4=C(Cl)C=CC=C4C3=C(C(=O)NC3=O)C3=C2C2=C1C(Cl)=CC=C2 ZGCSNRKSJLVANE-UHFFFAOYSA-N 0.000 title abstract 3
- QEHOIJJIZXRMAN-UHFFFAOYSA-N Rebeccamycin Natural products OC1C(O)C(OC)C(CO)OC1N1C2=C3NC4=C(Cl)C=CC=C4C3=C3C(=O)NC(=O)C3=C2C2=CC=CC(Cl)=C21 QEHOIJJIZXRMAN-UHFFFAOYSA-N 0.000 title abstract 3
- 229960005567 rebeccamycin Drugs 0.000 title abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 20
- 125000003118 aryl group Chemical group 0.000 claims abstract 16
- 150000001875 compounds Chemical class 0.000 claims abstract 16
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 14
- -1 nitro, carboxyl Chemical group 0.000 claims abstract 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 11
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 9
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract 8
- 239000002253 acid Substances 0.000 claims abstract 5
- 229910052794 bromium Inorganic materials 0.000 claims abstract 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 5
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 5
- 239000001257 hydrogen Substances 0.000 claims abstract 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 4
- 206010028980 Neoplasm Diseases 0.000 claims abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 3
- 239000012048 reactive intermediate Substances 0.000 claims abstract 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 2
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 238000007792 addition Methods 0.000 claims 4
- 150000001447 alkali salts Chemical class 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 238000000034 method Methods 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 102000001742 Tumor Suppressor Proteins Human genes 0.000 claims 2
- 108010040002 Tumor Suppressor Proteins Proteins 0.000 claims 2
- 150000001450 anions Chemical class 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 230000036210 malignancy Effects 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 2
- 230000004614 tumor growth Effects 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000012010 growth Effects 0.000 claims 1
- 150000004679 hydroxides Chemical class 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 238000010171 animal model Methods 0.000 abstract 1
- 230000000118 anti-neoplastic effect Effects 0.000 abstract 1
- 239000002246 antineoplastic agent Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/044—Pyrrole radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/23—Heterocyclic radicals containing two or more heterocyclic rings condensed among themselves or condensed with a common carbocyclic ring system, not provided for in groups C07H19/14 - C07H19/22
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Compounds Of Unknown Constitution (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines Containing Plant Substances (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Description
Claims (15)
- 다음 일반식을 가진 화합물 그의 제약상 허용되는 산부가 및 염기성염.상기식에서, n은 1-6의 정수이고, A6및 A13은 H와 -(CH2)n NR1R2중에서 선택되며 A6와 A13중의 최소한 하나는 -(CH2)n-NR1R2이고, R1과 R2는 각각 수소, 비치환 및 치환 C1-C6알킬, 알킬 성분중에 1-3개의 탄소원자를 갖고 아릴성분내에 비치환 페닐 또는 1-3개의 알킬, 알콕시, 히드록시, 할로 카르복실, 알콕시카르보닐 및 아미노 모노-및 디-저급-알킬아미노기로써 치환된 페닐를 가진 알랄킬, 및 비치환페닐 및 1-3개의 알킬, 알콕시, 히드록시, 할로, 아미노, 모노-및 디알킬아미노, 니트로, 카르복실, 알콕시카르보닐 및 시아노기로써 치환된 페닐중에서 선택된 아릴기중에서 선택되며, 단, R1과 R2는 다같이 아릴이 될수 없고, 다함께 취할때 R1과 R2는 N-원자와 함께 5- 또는 6-원환을 형성하기 위하여 -(CH2)4-와 (CH2)2-R3-(CH2)2-(여기서, R3은 CH2, NH, O 및 S에서 선택됨)에서 선택될 수 있으며, X는 H, F, Br, C1-C3알킬, OH, 카르복실, 알콕시카르보닐 및 알콕시(알킬성분이 C1-C3알킬임), 벤질 옥시, 아미노 및 모노-및 디알킬아미노중에서 선택되며, R4는 H 및 CH3에서 선택됨.
- 제1항에 있어서, 다음 일반식을 가진 화합물 및 그의 제약상 허용되는 산부가 및 염기성염.상기식에서, n은 1-6의 정수이고, R1및 R2는 비치환 및 치환 C1-C6알킬, 알킬 성분중에 1-3개의 탄소원자를 갖고 아릴성분내에 비치환 페닐, 또는 1-3개의 알킬, 알콕시, 히드록시, 할로, 카르복실, 알콕시카르보닐 및 아미노 모노-및 디-저급-알킬아미노기로써 치환된 페닐기를 가진 알랄킬, 및 비치환 페닐 및 1-3개의 알킬, 알콕시, 히드록시, 할로, 아미노, 모노-및 디알킬아미노, 니트로, 카르복실, 알콕시카르보닐 및 시아노기로써 치환된 페닐에서 선택된 아릴기중에서 선택되며, 단, R1과 R2는 다같이 아릴이 될수 없고, 다함께 취할때 R1과 R2는 N-원자와 함께 5- 또는 6-원환을 형성하기 위하여 -(CH2)4-와 (CH2)2-R3-(CH2)2-(여기서, R3은 CH2, NH O 및 S에서 선택됨)에서 선택될 수 있으며, X는 H, F, Br, C1-C3알킬, OH, 카르복실, 알콕시카르보닐 및 알콕시(알킬성분이 C1-C3알킬임), 벤질옥시, 아미노 및 모노-및 디알킬아미노중에서 선택되며, R4는 H 및 CH3에서 선택됨.
- 제2항에 있어서, X가 H, CI, Br, OH, OCH3및 OCH2C6H5중에서 선택된 것이 특징인 화합물.
- 제3항에 있어서, n은 정수 1,2 및 3에서 선택되며, R1및 R2는 각각 H, C1-C3알킬 및 -(CH2)4-에서 선택된 것이 특징인 화합물.
- 제4항에 있어서, X는 1- 및 11- 위치에 각각 결합한 CI인 것이 특징인 화합물.
- 제5항에 있어서, n은 정수 2 및 3에서 선택되며, R1및 R2는 각각 C2H5인 것이 특징인 화합물.
- 다음 일반식을 가진 화합물 및 그의 제약상 허용되는 산부가 및 염기성염.상기식중, n은 1-6의 정수이고, R1과 R2는 각각 수소, 비치환 및 치환 C1-C6알킬, 알킬 성분중에 1-3개의 탄소원자를 갖고 아릴성분내에 비치환 페닐, 또는 1-3개의 알킬, 알콕시, 히드록시, 할로, 카르복실, 알콕시카르보닐 및 아미노 및 아릴 성분내에 모노-및 디-저급-알킬아미노기로써 치환된 페닐기를 가진 아랄킬, 및 비치환 페닐 및 1-3개의 알킬, 알콕시, 히드록시, 할로, 아미노, 모노-및 디알킬아미노, 니트로, 카르복실, 알콕시 카르보닐 및 시아노기로써 치환된 페닐중에서 선택된 아릴기중에서 선택되며, 단, R1과 R2는 다같이 아릴이 될수 없고, 다함께 취할때 R1과 R2는 N-원자와 함께 5- 또는 6-원환을 형성하기 위하여 -(CH2)4-와 (CH2)2-R3-(CH2)2-(여기서, R3은 CH2, NH O 및 S에서 선택됨)에서 선택될 수 있으며, X는 H, F, Br, C1-C3알킬, OH, 카르복실, 알콕시카르보닐 및 알콕시(알킬성분이 C1-C3알킬임), 벤질옥시, 아미노 및 모노-및 디알킬아미노중에서 선택되며, R4는 H 및 CH3에서 선택됨.
- 제7항에 있어서, R4는 CH3이고, X는 고리계의 1-및 11-위치에 각각 결합한 CI, Br, OH, OCH3및 OCH2C4H5에서 선택된 것이 특징인 화합물.
- 제8항에 있어서, n은 정수 1,2 및 3에서 선택되며, R1과 R2는 각각 H, C1-C3알킬 및 -(CH2)4-에서 선택된 것이 특징인 화합물.
- 제9항에 있어서, X는 1- 및 11- 위치에 각각 결합한 CI인 것이 특징인 화합물.
- 제10항에 있어서, n가 2 및 3에서 선택되며, R1및 R2는 각각 C2H5인 것이 특징인 화합물.
- 다음 일반식(Ⅱ) 및 (Ⅲ)을 가진 화합물과 제약상 허용되는 그의 산부가 및 염기성염에서 선택된 최소한 1개 이상의 화합물의 종양성장 억제량과 제약상 허용되는 담체로된 종양억제 조성물.상기식중, n은 1-6의 정수이고, R1과 R2는 각각 수소, 비치환 및 치환 C1-C6알킬, 알킬 성분중에 1-3개의 탄소원자를 갖고 아릴성분내에 비치환 페닐, 또는 1-3개의 알킬, 알콕시, 히드록시, 할로, 카르복실, 알콕시카르보닐 및 라미노및 아릴성분내에 모노-및 디-저급-알킬아미노기로써 치환된 페닐기를 가진 아랄킬, 및 비치환 페닐 및 1-3개의 알킬, 알콕시, 히드록시, 할로, 아미노, 모노-및 디알킬아미노, 니트로, 카르복실, 알콕시 카르보닐 및 시아노기로써 치환된 페닐중에서 선택된 아릴기중에서 선택되며, 단, R1과 R2는 다같이 아릴이 될수 없고, 다함께 취할때 R1과 R2는 N-원자와 함께 5- 또는 6-원환을 형성하기 위하여 -(CH2)4-와 (CH2)2-R3-(CH2)2-(여기서, R3은 CH2, NH O 및 S에서 선택됨)에서 선택될 수 있으며, X는 H, F, Br, C1-C3알킬, OH, 카르복실, 알콕시카르보닐 및 알콕시(알킬성분이 C1-C3알킬임), 벤질옥시, 아미노 및 모노-및 디알킬아미노중에서 선택되며, R4는 H 및 CH3에서 선택됨.
- 악성종양에 걸린 포유동물 숙주에 제1항의 화합물의 조양성장 억제량을 투여함을 특징으로 하는 레버카마이신과 그의 유도체 및 동족체에 민감한 악성종양에 걸린 포유동물 숙주를 치료하는 방법.
- 악성종양에 걸린 포유동물 숙주에 제12항의 종양억제 조성물을 종양성장 억제에 충분한 양으로 투여함을 특징으로 하는 페베카마이신과 그의 유도체 및 동족체에 민감한 악성종양에 걸린 포유동물 숙주를 치료하는 방법.
- (a) 레베카마이신 또는 그의 유도체중의 하나를 출발물질로 제공하고, (b) 적당한 비반응성 용매에 용해시킨 상기 (a)의 출발물질을 적당량의 강염기와 반응시켜 (i) 6-위치에 음전하를 가진 레베카마이신 음이온, (ⅱ) 13-위치에 음전하를 가진 레베카마이신 (ⅲ) 음이온과 6-및 13-위치에 음전하를 가진 레베 카마이신 2음이온에서 선택된 반응성 중간체를 얻고, (c) 상기 (b)에 얻은 방응성 중간체를 일반식 L-(CH2)n-NR1R2(여기서, L은 화학적 잔기이고 n, R1및 R2는 위에서 정의한 것과 같음)으로 표시되는 아미노알킬 화합물과 반응시켜, (d) 상기 (c)에서 얻은 혼합물로 부터 레베카마이신의 아미노알킬 유도체를 회수함을 특징으로 하는 다음 일반식을 가진 제1항의 화합물을 제조하는 방법.상기식중 N, A6,A13및 R4는 제1항에서 정의한 것과 같음.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US933428 | 1986-11-21 | ||
US06/933,428 US4785085A (en) | 1986-11-21 | 1986-11-21 | Rebeccamycin analogs |
US933,428 | 1992-08-21 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR880006246A true KR880006246A (ko) | 1988-07-22 |
KR910000897B1 KR910000897B1 (ko) | 1991-02-12 |
Family
ID=25463937
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019870013102A KR910000897B1 (ko) | 1986-11-21 | 1987-11-20 | 레베카마이신 동족체 |
Country Status (28)
Country | Link |
---|---|
US (1) | US4785085A (ko) |
EP (1) | EP0269025B1 (ko) |
JP (1) | JPS63198695A (ko) |
KR (1) | KR910000897B1 (ko) |
CN (1) | CN1019806B (ko) |
AT (1) | ATE84539T1 (ko) |
AU (1) | AU614068B2 (ko) |
CA (1) | CA1287349C (ko) |
CS (1) | CS265248B2 (ko) |
CY (1) | CY1701A (ko) |
DE (1) | DE3783577T2 (ko) |
DK (1) | DK165986C (ko) |
EG (1) | EG18409A (ko) |
ES (1) | ES2053510T3 (ko) |
FI (1) | FI86189C (ko) |
GR (1) | GR3006776T3 (ko) |
HK (1) | HK49093A (ko) |
HU (1) | HU201773B (ko) |
IE (1) | IE60595B1 (ko) |
IL (1) | IL84515A (ko) |
MX (1) | MX9202849A (ko) |
MY (1) | MY102722A (ko) |
NO (1) | NO167741C (ko) |
NZ (1) | NZ222544A (ko) |
PT (1) | PT86188B (ko) |
SG (1) | SG25193G (ko) |
YU (1) | YU46087B (ko) |
ZA (1) | ZA878714B (ko) |
Families Citing this family (51)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07113027B2 (ja) * | 1987-12-24 | 1995-12-06 | 協和醗酵工業株式会社 | K−252誘導体 |
US5438050A (en) * | 1988-02-06 | 1995-08-01 | Godecke Aktiengesellschaft | Indolocarbazole derivatives, processes for their preparation and compositions containing them |
DE3835842A1 (de) * | 1988-10-21 | 1990-04-26 | Goedecke Ag | Indolocarbazol-derivate, verfahren zu deren herstellung und deren verwendung als arzneimittel |
US5015578A (en) * | 1989-03-23 | 1991-05-14 | Bristol-Myers Squibb Company | BMY-41950 antitumor antibiotic |
IL94274A0 (en) * | 1989-05-05 | 1991-03-10 | Goedecke Ag | Maleinimide derivatives,process for the preparation thereof and pharmaceutical compositions containing the same |
US5496809A (en) * | 1989-05-10 | 1996-03-05 | Bristol-Myers Squibb Co | Stable solutions of rebeccamycin analog |
IL97233A (en) * | 1990-03-06 | 1995-03-30 | Bristol Myers Squibb Co | Analogs of rabamycin, their manufacture and pharmaceutical preparations containing them |
EP0445736A1 (en) * | 1990-03-06 | 1991-09-11 | Bristol-Myers Squibb Company | Rebeccamycin analog and pharmaceutical composition containing it |
US5344823A (en) * | 1990-03-06 | 1994-09-06 | Bristol-Myers Squibb Company | Antitumor antibiotic BMY-41219 |
US5158938A (en) * | 1990-03-06 | 1992-10-27 | Bristol-Myers Squibb Company | Rebeccamycin |
ATE158298T1 (de) * | 1990-05-11 | 1997-10-15 | Banyu Pharma Co Ltd | Be-13793c-derivat mit antitumorwirkung |
US5478813A (en) * | 1990-05-11 | 1995-12-26 | Banyu Pharmaceutical Co., Ltd. | Antitumor substance BE-13793C derivatives |
US5591842A (en) * | 1991-11-29 | 1997-01-07 | Banyu Pharmaceutical Co., Ltd. | Indolopyrrolocarbazole derivatives |
US5589365A (en) * | 1991-11-29 | 1996-12-31 | Banyu Pharmaceutical Co., Ltd. | Process for producing glycosylated indolopyrrolocarbazole derivatives by culturing certain microorganisms |
US5437996A (en) * | 1992-11-24 | 1995-08-01 | Banyu Pharmaceutical Co., Ltd. | Microtetraspora strain for preparation of indolopyrrolocarbazole derivatives |
NZ245203A (en) * | 1991-11-29 | 1997-07-27 | Banyu Pharma Co Ltd | 5h-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6h)-dione derivatives substituted in position-13 by a pentose or hexose group; corresponding indolo-furano(anhydride)intermediates |
DE69323183T2 (de) * | 1992-03-20 | 1999-05-27 | The Wellcome Foundation Ltd., Greenford | Weitere indolderivate mit antiviraler wirkung |
JP3603322B2 (ja) * | 1992-12-14 | 2004-12-22 | 萬有製薬株式会社 | インドロピロロカルバゾール誘導体の製造法 |
EP0657411B1 (en) * | 1993-12-07 | 1999-06-09 | Eli Lilly And Company | Synthesis of bisindolylmaleimides |
US5541347A (en) * | 1993-12-07 | 1996-07-30 | Eli Lilly And Company | Synthesis of bisindolylmaleimides |
US5843935A (en) * | 1993-12-07 | 1998-12-01 | Eli Lilly And Company | Protein kinase C inhibitors |
US5723456A (en) * | 1993-12-07 | 1998-03-03 | Eli Lilly & Company | Therapeutic treatment for cardiovascular diseases |
US5624949A (en) * | 1993-12-07 | 1997-04-29 | Eli Lilly And Company | Protein kinase C inhibitors |
PL182124B1 (pl) * | 1993-12-07 | 2001-11-30 | Lilly Co Eli | Nowe zwiazki oraz srodek farmaceutyczny przeznaczony do leczenia powiklan cukrzycowych lub do leczenia nowotworów PL PL PL PL PL PL PL PL |
JP3998261B2 (ja) * | 1993-12-23 | 2007-10-24 | イーライ・リリー・アンド・カンパニー | プロテインキナーゼc阻害剤 |
US5545636A (en) * | 1993-12-23 | 1996-08-13 | Eli Lilly And Company | Protein kinase C inhibitors |
US5922860A (en) * | 1994-05-09 | 1999-07-13 | Banyu Pharmaceutical Co., Ltd. | Antitumor indolopyrrolocarbazole derivatives |
WO1995030682A1 (fr) * | 1994-05-09 | 1995-11-16 | Banyu Pharmaceutical Co., Ltd. | Derive d'indolopyrolocarbazole antitumoral |
US5804564A (en) * | 1994-05-09 | 1998-09-08 | Banyu Pharmaceutical Co., Ltd. | Antitumor indolopyrrolocarbazole derivatives |
US5861293A (en) * | 1994-06-13 | 1999-01-19 | Banyu Pharmaceutical Co., Ltd. | Gene encoding glycosyltransferase and its uses |
US5491242A (en) * | 1994-06-22 | 1996-02-13 | Eli Lilly And Company | Protein kinase C inhibitors |
US5481003A (en) * | 1994-06-22 | 1996-01-02 | Eli Lilly And Company | Protein kinase C inhibitors |
EP0695755B1 (en) * | 1994-08-04 | 1998-10-21 | F. Hoffmann-La Roche AG | Pyrrolocarbazole |
AU6836696A (en) * | 1995-09-05 | 1997-03-27 | Banyu Pharmaceutical Co., Ltd. | Antitumor indolopyrrolocarbazole derivatives |
IL126272A0 (en) * | 1996-03-20 | 1999-05-09 | Lilly Co Eli | Synthesis of indolylmaleimides |
US5859261A (en) * | 1997-03-20 | 1999-01-12 | Eli Lilly And Company | Synthesis of indolylmaleimides |
US6677450B2 (en) | 2000-10-06 | 2004-01-13 | Bristol-Myers Squibb Company | Topoisomerase inhibitors |
US6610727B2 (en) | 2000-10-06 | 2003-08-26 | Bristol-Myers Squibb Company | Anhydro sugar derivatives of indolocarbazoles |
US6653290B2 (en) * | 2000-10-06 | 2003-11-25 | Bristol-Myers Squibb Company | Tumor proliferation inhibitors |
MXPA03008589A (es) | 2001-03-22 | 2003-12-08 | Bristol Myers Squibb Co | Derivados de azucar citotoxicos selectivos de topoisomerasa i de indolopirrolocarbazoles. |
EP1554572B1 (en) | 2001-07-25 | 2009-10-14 | Raptor Pharmaceutical Inc. | Compositions and methods for modulating blood-brain barrier transport |
CA2393720C (en) * | 2002-07-12 | 2010-09-14 | Eli Lilly And Company | Crystalline 2,5-dione-3-(1-methyl-1h-indol-3-yl)-4-[1-(pyridin-2-ylmethyl)piperidin-4-yl]-1h-indol-3-yl]-1h-pyrrole mono-hydrochloride |
EP1666485A1 (en) * | 2003-09-16 | 2006-06-07 | Banyu Pharmaceutical Co., Ltd. | Novel indolopyrrolocarbazole derivative with antitumor activity |
DK1889198T3 (da) | 2005-04-28 | 2015-02-09 | Proteus Digital Health Inc | Farma-informatiksystem |
US8795627B2 (en) | 2007-03-21 | 2014-08-05 | Raptor Pharmaceuticals Inc. | Treatment of liver disorders by administration of RAP conjugates |
ES2326459B1 (es) | 2008-04-08 | 2010-05-28 | Universidad De Oviedo | Indolocarbazoles glicosilados, su procedimiento de obtencion y sus usos. |
DK3395372T3 (da) | 2009-02-20 | 2022-04-19 | Enhanx Biopharm Inc | System til afgivelse af glutathion-baseret medikament |
US8445002B2 (en) | 2009-05-06 | 2013-05-21 | Laboratory Skin Care, Inc. | Dermal delivery compositions comprising active agent-calcium phosphate particle complexes and methods of using the same |
US20120077778A1 (en) | 2010-09-29 | 2012-03-29 | Andrea Bourdelais | Ladder-Frame Polyether Conjugates |
CN102125578B (zh) * | 2010-11-24 | 2013-03-27 | 河南师范大学 | 具有抗癌活性的蝴蝶霉素类似物及合成方法 |
CN102898489B (zh) * | 2010-11-24 | 2014-04-02 | 河南师范大学 | 具有抗癌活性的蝴蝶霉素类似物及合成方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4487925A (en) * | 1983-01-28 | 1984-12-11 | Bristol-Myers Company | Rebeccamycin and process for its preparation |
US4552842A (en) * | 1983-01-28 | 1985-11-12 | Bristol-Myers Company | Process for producing rebeccamycin |
US4524145A (en) * | 1984-09-04 | 1985-06-18 | Bristol-Myers Company | 4'-Deschlororebeccamycin pharmaceutical composition and method of use |
JPS62220196A (ja) * | 1986-03-20 | 1987-09-28 | Kyowa Hakko Kogyo Co Ltd | 新規物質ucn―01 |
-
1986
- 1986-11-21 US US06/933,428 patent/US4785085A/en not_active Expired - Lifetime
-
1987
- 1987-11-12 AU AU81148/87A patent/AU614068B2/en not_active Expired
- 1987-11-13 NZ NZ222544A patent/NZ222544A/en unknown
- 1987-11-17 CS CS878249A patent/CS265248B2/cs not_active IP Right Cessation
- 1987-11-17 EG EG656/87A patent/EG18409A/xx active
- 1987-11-18 YU YU208687A patent/YU46087B/sh unknown
- 1987-11-18 IL IL84515A patent/IL84515A/xx not_active IP Right Cessation
- 1987-11-18 FI FI875091A patent/FI86189C/fi not_active IP Right Cessation
- 1987-11-20 CN CN87107928A patent/CN1019806B/zh not_active Expired
- 1987-11-20 IE IE315287A patent/IE60595B1/en not_active IP Right Cessation
- 1987-11-20 NO NO874857A patent/NO167741C/no not_active IP Right Cessation
- 1987-11-20 KR KR1019870013102A patent/KR910000897B1/ko not_active IP Right Cessation
- 1987-11-20 HU HU875164A patent/HU201773B/hu unknown
- 1987-11-20 EP EP87117167A patent/EP0269025B1/en not_active Expired - Lifetime
- 1987-11-20 DE DE8787117167T patent/DE3783577T2/de not_active Expired - Lifetime
- 1987-11-20 ES ES87117167T patent/ES2053510T3/es not_active Expired - Lifetime
- 1987-11-20 DK DK612987A patent/DK165986C/da not_active IP Right Cessation
- 1987-11-20 CA CA000552337A patent/CA1287349C/en not_active Expired - Lifetime
- 1987-11-20 ZA ZA878714A patent/ZA878714B/xx unknown
- 1987-11-20 PT PT86188A patent/PT86188B/pt unknown
- 1987-11-20 AT AT87117167T patent/ATE84539T1/de not_active IP Right Cessation
- 1987-11-20 JP JP62293854A patent/JPS63198695A/ja active Granted
- 1987-11-20 MY MYPI87003080A patent/MY102722A/en unknown
-
1992
- 1992-06-12 MX MX9202849A patent/MX9202849A/es unknown
-
1993
- 1993-01-14 GR GR920402547T patent/GR3006776T3/el unknown
- 1993-03-06 SG SG251/93A patent/SG25193G/en unknown
- 1993-05-20 HK HK490/93A patent/HK49093A/xx not_active IP Right Cessation
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1994
- 1994-01-14 CY CY170194A patent/CY1701A/xx unknown
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