NO314085B1 - Kondenserte heksacykliske forbindelser og fremgangsmåter for fremstilling derav, samt farmasöytiske preparater inneholdende dem - Google Patents
Kondenserte heksacykliske forbindelser og fremgangsmåter for fremstilling derav, samt farmasöytiske preparater inneholdende dem Download PDFInfo
- Publication number
- NO314085B1 NO314085B1 NO19961405A NO961405A NO314085B1 NO 314085 B1 NO314085 B1 NO 314085B1 NO 19961405 A NO19961405 A NO 19961405A NO 961405 A NO961405 A NO 961405A NO 314085 B1 NO314085 B1 NO 314085B1
- Authority
- NO
- Norway
- Prior art keywords
- compound
- methanesulfonate
- methanesulfonic acid
- preparation
- represented
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 71
- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims abstract description 74
- 229940098779 methanesulfonic acid Drugs 0.000 claims abstract description 23
- 238000001953 recrystallisation Methods 0.000 claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical class C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims description 10
- 125000006239 protecting group Chemical group 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 230000000259 anti-tumor effect Effects 0.000 claims description 3
- 238000000926 separation method Methods 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000013078 crystal Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- 238000010511 deprotection reaction Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- IGKWOGMVAOYVSJ-ZDUSSCGKSA-N (4s)-4-ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10-trione Chemical compound C1=C2C(=O)CCN2C(=O)C2=C1[C@](CC)(O)C(=O)OC2 IGKWOGMVAOYVSJ-ZDUSSCGKSA-N 0.000 description 2
- SRCUCWPOTBGIQM-IHZSNKTASA-N (9s)-1-acetylamino-9-ethyl-5-fluoro-2,3-dihydro-9-hydroxy-4-methyl-1h,12h-benzo[de]pyrano[3',4':6,7]-indolizino[1,2-b]quinoline-10,13(9h,15h)-dione Chemical compound C1CC(NC(C)=O)C2=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC3=CC(F)=C(C)C1=C32 SRCUCWPOTBGIQM-IHZSNKTASA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 150000004683 dihydrates Chemical class 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- SEFPQWAVZCZXTK-UHFFFAOYSA-N n-(8-amino-6-fluoro-5-methyl-1-oxo-3,4-dihydro-2h-naphthalen-2-yl)acetamide Chemical compound FC1=CC(N)=C2C(=O)C(NC(=O)C)CCC2=C1C SEFPQWAVZCZXTK-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- SYTBZMRGLBWNTM-SNVBAGLBSA-N (R)-flurbiprofen Chemical compound FC1=CC([C@H](C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-SNVBAGLBSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005042 acyloxymethyl group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- UAAKJEVCDBPTQS-UHFFFAOYSA-N methanesulfonic acid;dihydrate Chemical compound O.O.CS(O)(=O)=O UAAKJEVCDBPTQS-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 210000003371 toe Anatomy 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8371795 | 1995-04-10 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO961405D0 NO961405D0 (no) | 1996-04-09 |
| NO961405L NO961405L (no) | 1996-10-11 |
| NO314085B1 true NO314085B1 (no) | 2003-01-27 |
Family
ID=13810270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19961405A NO314085B1 (no) | 1995-04-10 | 1996-04-09 | Kondenserte heksacykliske forbindelser og fremgangsmåter for fremstilling derav, samt farmasöytiske preparater inneholdende dem |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US6504029B1 (ko) |
| EP (1) | EP0737686B1 (ko) |
| KR (1) | KR100400941B1 (ko) |
| CN (1) | CN1050131C (ko) |
| AT (1) | ATE181919T1 (ko) |
| CA (1) | CA2173671A1 (ko) |
| DE (1) | DE69603117T2 (ko) |
| DK (1) | DK0737686T3 (ko) |
| EA (1) | EA000036B1 (ko) |
| ES (1) | ES2136338T3 (ko) |
| GR (1) | GR3031400T3 (ko) |
| NO (1) | NO314085B1 (ko) |
| TW (1) | TW382630B (ko) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001062235A2 (en) | 2000-02-28 | 2001-08-30 | Aventis Pharma S.A. | A composition comprising camptothecin and a pyrimidine derivative for the treatment of cancer |
| US6545010B2 (en) | 2000-03-17 | 2003-04-08 | Aventis Pharma S.A. | Composition comprising camptothecin or a camptothecin derivative and a platin derivative for the treatment of cancer |
| US6548488B2 (en) | 2000-03-17 | 2003-04-15 | Aventis Pharma S.A. | Composition comprising camptothecin or a camptothecin derivative and an alkylating agent for the treatment of cancer |
| AR030207A1 (es) * | 2000-04-07 | 2003-08-13 | Daiichi Seiyaku Co | Composicion farmaceutica que contiene un derivado de camptotecina y procedimiento de preparacion de la misma |
| US6486320B2 (en) | 2000-09-15 | 2002-11-26 | Aventis Pharma S.A. | Preparation of camptothecin and of its derivatives |
| MXPA03002882A (es) | 2000-10-27 | 2004-12-03 | Aventis Pharma Sa | Una combinacion que contiene camptotecina y un derivado de estilbeno para el tratamiento del cancer. |
| WO2006069344A2 (en) | 2004-12-22 | 2006-06-29 | Rutgers, The State University Of New Jersey | Controlled release hydrogels |
| WO2012050591A1 (en) | 2010-10-15 | 2012-04-19 | Rutgers, The State University Of New Jersey | Hydrogel formulation for dermal and ocular delivery |
| US8410045B2 (en) | 2006-03-30 | 2013-04-02 | Drais Pharmaceuticals, Inc. | Camptothecin-peptide conjugates and pharmaceutical compositions containing the same |
| US8173621B2 (en) | 2008-06-11 | 2012-05-08 | Gilead Pharmasset Llc | Nucleoside cyclicphosphates |
| TW201031675A (en) | 2008-12-23 | 2010-09-01 | Pharmasset Inc | Synthesis of purine nucleosides |
| EP2376514A2 (en) | 2008-12-23 | 2011-10-19 | Pharmasset, Inc. | Nucleoside analogs |
| EP2376088B1 (en) | 2008-12-23 | 2017-02-22 | Gilead Pharmasset LLC | 6-O-Substituted-2-amino-purine nucleoside phosphoramidates |
| UY33311A (es) | 2010-03-31 | 2011-10-31 | Pharmasset Inc | Fosforamidatos de nucleosidos |
| SI3342785T1 (sl) | 2012-10-11 | 2020-02-28 | Daiichi Sankyo Company, Limited | Povezovalci za konjugate protitelesa in zdravila |
| WO2014061277A1 (ja) | 2012-10-19 | 2014-04-24 | 第一三共株式会社 | 親水性構造を含むリンカーで結合させた抗体－薬物コンジュゲート |
| WO2015098099A1 (ja) | 2013-12-25 | 2015-07-02 | 第一三共株式会社 | 抗ｔｒｏｐ２抗体－薬物コンジュゲート |
| RS62618B1 (sr) | 2014-01-31 | 2021-12-31 | Daiichi Sankyo Co Ltd | Anti-her2 antitelo-lek konjugat |
| WO2015155976A1 (ja) | 2014-04-10 | 2015-10-15 | 第一三共株式会社 | 抗ｈｅｒ２抗体－薬物コンジュゲート |
| EP3129063B1 (en) | 2014-04-10 | 2021-01-27 | Daiichi Sankyo Company, Limited | Anti-her3 antibody-drug conjugate |
| BR112017027690A2 (pt) | 2015-06-29 | 2018-10-09 | Daiichi Sankyo Co Ltd | método para produção de uma composição de conjugado anticorpo-fármaco, e, composição de conjugado anticorpo-fármaco |
| US11273155B2 (en) | 2016-12-12 | 2022-03-15 | Daiichi Sankyo Company, Limited | Combination of antibody-drug conjugate and immune checkpoint inhibitor |
| IL268102B1 (en) | 2017-01-17 | 2024-08-01 | Daiichi Sankyo Co Ltd | Anti-GPR 20 antibody and anti-GPR 20 antibody-drug conjugate |
| TWI794230B (zh) | 2017-05-15 | 2023-03-01 | 日商第一三共股份有限公司 | 抗ｃｄｈ６抗體及抗ｃｄｈ６抗體-藥物結合物、以及其製造方法 |
| BR112020003646A2 (pt) | 2017-08-31 | 2020-09-01 | Daiichi Sankyo Company, Limited | cristais, métodos para produção de cristais e de um conjugado anticorpo-fármaco, e, sal. |
| SG11202001514XA (en) * | 2017-08-31 | 2020-03-30 | Daiichi Sankyo Co Ltd | Novel method for producing antibody-drug conjugate |
| SI3794042T1 (sl) | 2018-05-18 | 2024-07-31 | Daiichi Sankyo Co., Ltd. | Konjugat protitelesa anti-MUC1-exatecan in citotoksično sredstvo |
| CN112512591B (zh) | 2018-09-26 | 2024-08-16 | 江苏恒瑞医药股份有限公司 | 依喜替康类似物的配体-药物偶联物及其制备方法和应用 |
| EP3854816A4 (en) | 2018-09-30 | 2022-09-07 | Jiangsu Hengrui Medicine Co., Ltd. | EXATECAN ANTI-B7H3-ANALOG ANTIBODY CONJUGATE AND ASSOCIATED MEDICAL USE |
| US20200306243A1 (en) | 2019-03-29 | 2020-10-01 | Medimmune Limited | Compounds and conjugates thereof |
| EP3996749A1 (en) | 2019-07-10 | 2022-05-18 | Cybrexa 3, Inc. | Peptide conjugates of microtubule-targeting agents as therapeutics |
| US11634508B2 (en) | 2019-07-10 | 2023-04-25 | Cybrexa 2, Inc. | Peptide conjugates of cytotoxins as therapeutics |
| TW202128227A (zh) | 2019-12-12 | 2021-08-01 | 大陸商江蘇恆瑞醫藥股份有限公司 | 抗密蛋白抗體藥物偶聯物及其醫藥用途 |
| AU2021210074A1 (en) | 2020-01-22 | 2022-07-28 | Jiangsu Hengrui Medicine Co., Ltd. | Anti-TROP-2 antibody-exatecan analog conjugate and medical use thereof |
| EP4129345A4 (en) | 2020-03-25 | 2023-11-29 | Jiangsu Hengrui Pharmaceuticals Co., Ltd. | PHARMACEUTICAL COMPOSITION COMPRISING AN ANTIBODY-DRUG CONJUGATE AND USE THEREOF |
| AU2021243080A1 (en) | 2020-03-25 | 2022-09-22 | Jiangsu Hengrui Pharmaceuticals Co., Ltd. | Preparation method for antibody medicament conjugate |
| MX2022011808A (es) | 2020-03-25 | 2022-12-06 | Jiangsu Hengrui Pharmaceuticals Co Ltd | Conjugado de anticuerpo anti-psma-analogo de exatecan y uso medico del mismo. |
| CN117940432A (zh) * | 2021-09-01 | 2024-04-26 | 上海弼领生物技术有限公司 | 一种喜树碱类化合物、其制备方法和用途 |
| WO2024149193A1 (zh) * | 2023-01-09 | 2024-07-18 | 四川科伦博泰生物医药股份有限公司 | 含氮稠环化合物的制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6087746A (ja) * | 1983-10-17 | 1985-05-17 | Hakubakumai Kk | 即席麺ないしは焼そば用蒸し麺の製造方法 |
| US4939255A (en) * | 1987-06-24 | 1990-07-03 | Daiichi Pharmaceutical Co., Ltd. | Hexa-cyclic camptothecin derivatives |
| US4943579A (en) * | 1987-10-06 | 1990-07-24 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Water soluble prodrugs of camptothecin |
| US5004758A (en) * | 1987-12-01 | 1991-04-02 | Smithkline Beecham Corporation | Water soluble camptothecin analogs useful for inhibiting the growth of animal tumor cells |
| JP3008226B2 (ja) * | 1991-01-16 | 2000-02-14 | 第一製薬株式会社 | 六環性化合物 |
| US5637770A (en) * | 1991-01-16 | 1997-06-10 | Daiichi Pharmaceutical Co., Ltd. | Hexa-cyclic compound |
| JP3359955B2 (ja) * | 1992-07-16 | 2002-12-24 | 第一製薬株式会社 | 抗腫瘍剤 |
| IS4152A (is) * | 1993-04-29 | 1994-10-30 | Glaxo Inc. | Vatnsuppleysanlegar Camptothecin afleiður og aðferð til framleiðslu þeirra |
| GB9319944D0 (en) * | 1993-09-28 | 1993-11-17 | Erba Carlo Spa | Process for the preparation of 9-amino camptothecin |
-
1995
- 1995-07-13 US US08/501,933 patent/US6504029B1/en not_active Expired - Fee Related
- 1995-09-18 CN CN95116111A patent/CN1050131C/zh not_active Expired - Fee Related
-
1996
- 1996-04-04 KR KR1019960010291A patent/KR100400941B1/ko not_active IP Right Cessation
- 1996-04-09 EA EA199600018A patent/EA000036B1/ru not_active IP Right Cessation
- 1996-04-09 TW TW085104156A patent/TW382630B/zh not_active IP Right Cessation
- 1996-04-09 NO NO19961405A patent/NO314085B1/no unknown
- 1996-04-09 CA CA002173671A patent/CA2173671A1/en not_active Abandoned
- 1996-04-10 EP EP96105661A patent/EP0737686B1/en not_active Expired - Lifetime
- 1996-04-10 DE DE69603117T patent/DE69603117T2/de not_active Expired - Fee Related
- 1996-04-10 AT AT96105661T patent/ATE181919T1/de not_active IP Right Cessation
- 1996-04-10 ES ES96105661T patent/ES2136338T3/es not_active Expired - Lifetime
- 1996-04-10 DK DK96105661T patent/DK0737686T3/da active
-
1999
- 1999-09-30 GR GR990402491T patent/GR3031400T3/el unknown
-
2001
- 2001-06-11 US US09/876,945 patent/US6552197B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES2136338T3 (es) | 1999-11-16 |
| NO961405D0 (no) | 1996-04-09 |
| DE69603117T2 (de) | 1999-10-28 |
| US6504029B1 (en) | 2003-01-07 |
| US6552197B2 (en) | 2003-04-22 |
| CN1050131C (zh) | 2000-03-08 |
| EP0737686B1 (en) | 1999-07-07 |
| NO961405L (no) | 1996-10-11 |
| DE69603117D1 (de) | 1999-08-12 |
| KR960037682A (ko) | 1996-11-19 |
| EP0737686A1 (en) | 1996-10-16 |
| DK0737686T3 (da) | 1999-11-22 |
| AU5056696A (en) | 1996-10-24 |
| KR100400941B1 (ko) | 2003-12-24 |
| EA199600018A2 (ru) | 1996-10-01 |
| EA199600018A3 (ru) | 1997-03-31 |
| ATE181919T1 (de) | 1999-07-15 |
| CN1133290A (zh) | 1996-10-16 |
| CA2173671A1 (en) | 1996-10-11 |
| TW382630B (en) | 2000-02-21 |
| GR3031400T3 (en) | 2000-01-31 |
| EA000036B1 (ru) | 1998-02-26 |
| AU692078B2 (en) | 1998-05-28 |
| US20010034446A1 (en) | 2001-10-25 |
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