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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (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)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (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 (fr) |
| EP (1) | EP0737686B1 (fr) |
| KR (1) | KR100400941B1 (fr) |
| CN (1) | CN1050131C (fr) |
| AT (1) | ATE181919T1 (fr) |
| CA (1) | CA2173671A1 (fr) |
| DE (1) | DE69603117T2 (fr) |
| DK (1) | DK0737686T3 (fr) |
| EA (1) | EA000036B1 (fr) |
| ES (1) | ES2136338T3 (fr) |
| GR (1) | GR3031400T3 (fr) |
| NO (1) | NO314085B1 (fr) |
| TW (1) | TW382630B (fr) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0108728A (pt) | 2000-02-28 | 2003-12-30 | Aventis Pharma Sa | Combinação farmacêutica terapêutica, e, método para tratar um c ncer. |
| 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 |
| WO2002034244A2 (fr) | 2000-10-27 | 2002-05-02 | Aventis Pharma S.A. | Combinaison de camptothecine et d'un derive de stilbene pour le traitement du cancer |
| WO2012050591A1 (fr) | 2010-10-15 | 2012-04-19 | Rutgers, The State University Of New Jersey | Formulation d'hydrogel pour une administration dermique et oculaire |
| US20090104254A1 (en) | 2004-12-22 | 2009-04-23 | Rutgers, The State University Of New Jersey | Controlled Release Hydrogels |
| AU2007232206B2 (en) | 2006-03-30 | 2013-04-04 | Drais Pharmaceuticals, Inc. | Camptothecin-cell penetrating peptide conjugates and pharmaceutical compositions containing the same |
| US8173621B2 (en) | 2008-06-11 | 2012-05-08 | Gilead Pharmasset Llc | Nucleoside cyclicphosphates |
| US8716263B2 (en) | 2008-12-23 | 2014-05-06 | Gilead Pharmasset Llc | Synthesis of purine nucleosides |
| EP3222628A1 (fr) | 2008-12-23 | 2017-09-27 | Gilead Pharmasset LLC | Phosphoramidates nucléosidiques |
| US8551973B2 (en) | 2008-12-23 | 2013-10-08 | Gilead Pharmasset Llc | Nucleoside analogs |
| PT3290428T (pt) | 2010-03-31 | 2021-12-27 | Gilead Pharmasset Llc | Comprimido compreendendo 2-(((s)-(((2r,3r,4r,5r)-5-(2,4-dioxo-3,4-dihidropirimidin-1-(2h)-il)¿4¿fluoro¿3¿hidroxi¿4¿metiltetrahidrofuran¿2¿il)metoxi) (fenoxi)fosforil)amino)propanoato de (s)- isopropil cristalino |
| HUE039000T2 (hu) * | 2012-10-11 | 2018-12-28 | Daiichi Sankyo Co Ltd | Antitest-gyógyszer konjugát |
| EP2910573B1 (fr) | 2012-10-19 | 2020-02-19 | Daiichi Sankyo Company, Limited | Conjugué anticorps-médicament produit par liaison par l'intermédiaire d'un lieur ayant une structure hydrophile |
| CA2933666C (fr) | 2013-12-25 | 2021-08-03 | Sapporo Medical University | Conjugue anticorps anti-trop2-medicament |
| DK3466976T3 (da) | 2014-01-31 | 2021-12-13 | Daiichi Sankyo Co Ltd | Anti-her2-antistof-lægemiddelkonjugat |
| US11185594B2 (en) | 2014-04-10 | 2021-11-30 | Daiichi Sankyo Company, Limited | (Anti-HER2 antibody)-drug conjugate |
| KR102624244B1 (ko) | 2014-04-10 | 2024-01-11 | 다이이찌 산쿄 가부시키가이샤 | 항her3 항체-약물 콘주게이트 |
| IL290959B2 (en) | 2015-06-29 | 2023-04-01 | Daiichi Sankyo Co Ltd | Preparations containing antibody-drug conjugates and methods for their production |
| US11273155B2 (en) | 2016-12-12 | 2022-03-15 | Daiichi Sankyo Company, Limited | Combination of antibody-drug conjugate and immune checkpoint inhibitor |
| WO2018135501A1 (fr) | 2017-01-17 | 2018-07-26 | 第一三共株式会社 | Anticorps anti-gpr20 et conjugué anticorps-médicament anti-gpr20 |
| TW202330036A (zh) | 2017-05-15 | 2023-08-01 | 日商第一三共股份有限公司 | 抗體-藥物結合物之製造方法 |
| CA3073924C (fr) | 2017-08-31 | 2023-10-17 | Daiichi Sankyo Company, Limited | Procede ameliore de production d'un conjugue anticorps-medicament |
| KR102630307B1 (ko) * | 2017-08-31 | 2024-01-29 | 다이이찌 산쿄 가부시키가이샤 | 항체-약물 콘주게이트의 신규 제조 방법 |
| CA3100608A1 (fr) | 2018-05-18 | 2019-11-21 | Daiichi Sankyo Co., Ltd. | Conjugue anticorps-medicament anti-muc1 |
| KR20210066833A (ko) | 2018-09-26 | 2021-06-07 | 지앙수 헨그루이 메디슨 컴퍼니 리미티드 | 엑사테칸 유사체의 리간드-약물 접합체, 이를 위한 제조 방법, 및 이의 적용 |
| AU2019351427A1 (en) | 2018-09-30 | 2021-04-15 | Changzhou Hansoh Pharmaceutical Co., Ltd. | Anti-B7H3 antibody-exatecan analog conjugate and medicinal use thereof |
| US20220211863A1 (en) | 2019-03-29 | 2022-07-07 | Medimmune Limited | Compounds and conjugates thereof |
| MX2022000449A (es) | 2019-07-10 | 2022-04-25 | Cybrexa 2 Inc | Conjugados peptídicos de citotoxinas como terapéuticos. |
| EP3996749A1 (fr) | 2019-07-10 | 2022-05-18 | Cybrexa 3, Inc. | Conjugués peptidiques d'agents de ciblage de microtubules en tant qu'agents thérapeutiques |
| EP4074345A4 (fr) | 2019-12-12 | 2023-10-25 | Jiangsu Hengrui Pharmaceuticals Co., Ltd. | Conjugué anticorps anti-claudine-médicament et son utilisation pharmaceutique |
| JP2023510905A (ja) | 2020-01-22 | 2023-03-15 | 江蘇恒瑞医薬股▲ふん▼有限公司 | 抗ｔｒｏｐ－２抗体－エキサテカン類似体複合体及びその医薬用途 |
| CN115103691A (zh) | 2020-03-25 | 2022-09-23 | 江苏恒瑞医药股份有限公司 | 一种含抗体药物偶联物的药物组合物及其用途 |
| JP2023521956A (ja) | 2020-03-25 | 2023-05-26 | 江蘇恒瑞医薬股▲ふん▼有限公司 | 抗体薬物複合体の調製方法 |
| AU2021240756A1 (en) | 2020-03-25 | 2022-11-17 | Jiangsu Hengrui Pharmaceuticals Co., Ltd. | Anti-PSMA antibody-exatecan analogue conjugate and medical use thereof |
| WO2023030364A1 (fr) * | 2021-09-01 | 2023-03-09 | 上海弼领生物技术有限公司 | Composé camptothécine, son procédé de préparation et son utilisation |
| WO2024149193A1 (fr) * | 2023-01-09 | 2024-07-18 | 四川科伦博泰生物医药股份有限公司 | Procédé de préparation d'un composé cyclique fusionné contenant de l'azote |
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 |
| US5658920A (en) * | 1991-01-16 | 1997-08-19 | Daiichi Pharmaceutical Co., Ltd. | Substituted 1H,12H-benz-[DE]pyrano[3',4':6,7] indolizino[1,2-B]quinoline-10,13(9H,15H)-dione compound |
| JP3008226B2 (ja) * | 1991-01-16 | 2000-02-14 | 第一製薬株式会社 | 六環性化合物 |
| 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 NO NO19961405A patent/NO314085B1/no unknown
- 1996-04-09 CA CA002173671A patent/CA2173671A1/fr not_active Abandoned
- 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
- 1996-04-10 EP EP96105661A patent/EP0737686B1/fr not_active Expired - Lifetime
- 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
- 1996-04-10 DE DE69603117T patent/DE69603117T2/de not_active Expired - Fee Related
-
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 |
|---|---|
| DK0737686T3 (da) | 1999-11-22 |
| KR960037682A (ko) | 1996-11-19 |
| EP0737686A1 (fr) | 1996-10-16 |
| US6552197B2 (en) | 2003-04-22 |
| CN1050131C (zh) | 2000-03-08 |
| EA199600018A3 (ru) | 1997-03-31 |
| EA000036B1 (ru) | 1998-02-26 |
| AU5056696A (en) | 1996-10-24 |
| ES2136338T3 (es) | 1999-11-16 |
| DE69603117T2 (de) | 1999-10-28 |
| EP0737686B1 (fr) | 1999-07-07 |
| GR3031400T3 (en) | 2000-01-31 |
| US20010034446A1 (en) | 2001-10-25 |
| AU692078B2 (en) | 1998-05-28 |
| KR100400941B1 (ko) | 2003-12-24 |
| CN1133290A (zh) | 1996-10-16 |
| TW382630B (en) | 2000-02-21 |
| ATE181919T1 (de) | 1999-07-15 |
| NO961405D0 (no) | 1996-04-09 |
| NO961405L (no) | 1996-10-11 |
| CA2173671A1 (fr) | 1996-10-11 |
| DE69603117D1 (de) | 1999-08-12 |
| EA199600018A2 (ru) | 1996-10-01 |
| US6504029B1 (en) | 2003-01-07 |
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