IE61308B1 - Novel anthracycline derivatives, a process for preparing same and their use as medicaments - Google Patents
Novel anthracycline derivatives, a process for preparing same and their use as medicamentsInfo
- Publication number
- IE61308B1 IE61308B1 IE330187A IE330187A IE61308B1 IE 61308 B1 IE61308 B1 IE 61308B1 IE 330187 A IE330187 A IE 330187A IE 330187 A IE330187 A IE 330187A IE 61308 B1 IE61308 B1 IE 61308B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- group
- formula
- hydroxyl
- denotes
- Prior art date
Links
- 229940045799 anthracyclines and related substance Drugs 0.000 title claims abstract description 6
- 239000003814 drug Substances 0.000 title claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 94
- 238000002360 preparation method Methods 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 24
- 230000000259 anti-tumor effect Effects 0.000 claims abstract description 10
- IBZGBXXTIGCACK-CWKPULSASA-N Adriamycinone Chemical compound C1[C@@](O)(C(=O)CO)C[C@H](O)C2=C1C(O)=C1C(=O)C(C=CC=C3OC)=C3C(=O)C1=C2O IBZGBXXTIGCACK-CWKPULSASA-N 0.000 claims description 11
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Chemical group 0.000 claims description 3
- 229910052740 iodine Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
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- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- NJSUFZNXBBXAAC-UHFFFAOYSA-N ethanol;toluene Chemical compound CCO.CC1=CC=CC=C1 NJSUFZNXBBXAAC-UHFFFAOYSA-N 0.000 description 1
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- RYZCLUQMCYZBJQ-UHFFFAOYSA-H lead(2+);dicarbonate;dihydroxide Chemical compound [OH-].[OH-].[Pb+2].[Pb+2].[Pb+2].[O-]C([O-])=O.[O-]C([O-])=O RYZCLUQMCYZBJQ-UHFFFAOYSA-H 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229940101209 mercuric oxide Drugs 0.000 description 1
- NGYIMTKLQULBOO-UHFFFAOYSA-L mercury dibromide Chemical compound Br[Hg]Br NGYIMTKLQULBOO-UHFFFAOYSA-L 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- NRTYMEPCRDJMPZ-UHFFFAOYSA-N pyridine;2,2,2-trifluoroacetic acid Chemical compound C1=CC=NC=C1.OC(=O)C(F)(F)F NRTYMEPCRDJMPZ-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- UJAXDXQEWRJGKO-UHFFFAOYSA-M sodium;7-hydroxy-7-oxoheptanoate Chemical compound [Na+].OC(=O)CCCCCC([O-])=O UJAXDXQEWRJGKO-UHFFFAOYSA-M 0.000 description 1
- SLVJLFOSPGAWHC-UHFFFAOYSA-M sodium;8-hydroxy-8-oxooctanoate Chemical compound [Na+].OC(=O)CCCCCCC([O-])=O SLVJLFOSPGAWHC-UHFFFAOYSA-M 0.000 description 1
- GOGGIOPQLKEIGC-UHFFFAOYSA-M sodium;hexanedioate;hydron Chemical compound [Na+].OC(=O)CCCCC([O-])=O GOGGIOPQLKEIGC-UHFFFAOYSA-M 0.000 description 1
- KRMPAXDXQYLVTA-UHFFFAOYSA-M sodium;hydron;pentanedioate Chemical compound [Na+].OC(=O)CCCC([O-])=O KRMPAXDXQYLVTA-UHFFFAOYSA-M 0.000 description 1
- LHYPLJGBYPAQAK-UHFFFAOYSA-M sodium;pentanoate Chemical compound [Na+].CCCCC([O-])=O LHYPLJGBYPAQAK-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61288993A JPH0742304B2 (ja) | 1986-12-05 | 1986-12-05 | 新規なアンスラサイクリン誘導体およびその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE873301L IE873301L (en) | 1988-06-05 |
| IE61308B1 true IE61308B1 (en) | 1994-10-19 |
Family
ID=17737453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE330187A IE61308B1 (en) | 1986-12-05 | 1987-12-04 | Novel anthracycline derivatives, a process for preparing same and their use as medicaments |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0275431B1 (en, 2012) |
| JP (1) | JPH0742304B2 (en, 2012) |
| KR (1) | KR880007556A (en, 2012) |
| AT (1) | ATE80890T1 (en, 2012) |
| CA (1) | CA1295326C (en, 2012) |
| DE (1) | DE3781879T2 (en, 2012) |
| DK (1) | DK165452C (en, 2012) |
| ES (1) | ES2044900T3 (en, 2012) |
| GR (1) | GR3006438T3 (en, 2012) |
| IE (1) | IE61308B1 (en, 2012) |
| PT (1) | PT86282B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0335369A3 (en) * | 1988-03-29 | 1990-03-28 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | New anthracycline derivatives and processes for the preparation of the same |
| JPH0742232B2 (ja) * | 1989-03-02 | 1995-05-10 | 明治製菓株式会社 | 制癌剤組成物 |
| US5220001A (en) * | 1989-10-25 | 1993-06-15 | Zaidan Hojim Biseibutsu Dong-A Pharm Co. | Anthracycline glycoside derivatives |
| KR100211417B1 (ko) * | 1990-11-30 | 1999-10-01 | 유충식 | L-탈로피라노시드 유도체 및 그의 제조방법 |
| ATE179426T1 (de) * | 1994-03-11 | 1999-05-15 | Zaidan Hojin Biseibutsu | Anthracyclin-derivate, die ein trifluormethylierte zuckereinheiten enthalten |
| DE69601908T2 (de) * | 1995-09-08 | 1999-07-29 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai, Tokio/Tokyo | Fluorenthaltende Anthracyclinderivate mit Mono- oder Di-0-aminoalkanoylaten Hydroxylgruppen in dem Zuckerrest |
| KR19990084528A (ko) * | 1998-05-07 | 1999-12-06 | 박상철 | 신규 안트라사이클린 유도체 및 제조방법 |
| SG11202101429YA (en) | 2018-08-23 | 2021-03-30 | Seagen Inc | Anti-tigit antibodies |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR79729B (en, 2012) * | 1982-12-20 | 1984-10-31 | Univ Ohio State Res Found |
-
1986
- 1986-12-05 JP JP61288993A patent/JPH0742304B2/ja not_active Expired - Lifetime
-
1987
- 1987-12-02 ES ES87117791T patent/ES2044900T3/es not_active Expired - Lifetime
- 1987-12-02 DE DE8787117791T patent/DE3781879T2/de not_active Expired - Fee Related
- 1987-12-02 CA CA000553359A patent/CA1295326C/en not_active Expired - Lifetime
- 1987-12-02 AT AT87117791T patent/ATE80890T1/de not_active IP Right Cessation
- 1987-12-02 EP EP87117791A patent/EP0275431B1/en not_active Expired - Lifetime
- 1987-12-03 PT PT86282A patent/PT86282B/pt not_active IP Right Cessation
- 1987-12-04 IE IE330187A patent/IE61308B1/en not_active IP Right Cessation
- 1987-12-04 DK DK638787A patent/DK165452C/da not_active IP Right Cessation
- 1987-12-05 KR KR870013871A patent/KR880007556A/ko not_active Ceased
-
1992
- 1992-12-02 GR GR920402802T patent/GR3006438T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE873301L (en) | 1988-06-05 |
| JPS63141992A (ja) | 1988-06-14 |
| ES2044900T3 (es) | 1994-01-16 |
| DE3781879D1 (de) | 1992-10-29 |
| PT86282A (en) | 1988-01-01 |
| ATE80890T1 (de) | 1992-10-15 |
| DK165452C (da) | 1993-04-13 |
| GR3006438T3 (en, 2012) | 1993-06-21 |
| CA1295326C (en) | 1992-02-04 |
| PT86282B (pt) | 1990-11-07 |
| JPH0742304B2 (ja) | 1995-05-10 |
| DE3781879T2 (de) | 1993-04-08 |
| KR880007556A (ko) | 1988-08-27 |
| DK638787A (da) | 1988-06-06 |
| EP0275431A1 (en) | 1988-07-27 |
| DK638787D0 (da) | 1987-12-04 |
| EP0275431B1 (en) | 1992-09-23 |
| DK165452B (da) | 1992-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |