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 PDF

Info

Publication number: NO314085B1
Authority: NO; Norway
Prior art keywords: compound; methanesulfonate; methanesulfonic acid; preparation; represented
Prior art date: 1995-04-10

Application number

NO19961405A

Other languages

English (en)

Norwegian (no)

Other versions

NO961405L (no

NO961405D0 (no

Inventor

Shinji Kamihara

Kazuaki Kanai

Shigeru Noguchi

Hirofumi Terasawa

Hiroaki Kitaoka

Original Assignee

Daiichi Seiyaku Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1995-04-10

Filing date

1996-04-09

Publication date

2003-01-27

1996-04-09 Application filed by Daiichi Seiyaku Co filed Critical Daiichi Seiyaku Co

1996-04-09 Publication of NO961405D0 publication Critical patent/NO961405D0/no

1996-10-11 Publication of NO961405L publication Critical patent/NO961405L/no

2003-01-27 Publication of NO314085B1 publication Critical patent/NO314085B1/no

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)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Saccharide Compounds (AREA)

NO19961405A 1995-04-10 1996-04-09 Kondenserte heksacykliske forbindelser og fremgangsmåter for fremstilling derav, samt farmasöytiske preparater inneholdende dem NO314085B1 (no)

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 (de)
EP (1)	EP0737686B1 (de)
KR (1)	KR100400941B1 (de)
CN (1)	CN1050131C (de)
AT (1)	ATE181919T1 (de)
CA (1)	CA2173671A1 (de)
DE (1)	DE69603117T2 (de)
DK (1)	DK0737686T3 (de)
EA (1)	EA000036B1 (de)
ES (1)	ES2136338T3 (de)
GR (1)	GR3031400T3 (de)
NO (1)	NO314085B1 (de)
TW (1)	TW382630B (de)

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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
AU1602902A (en)	2000-10-27	2002-05-06	Aventis Pharma Sa	A combination comprising camptothecin and a stilbene derivative for the treatment of cancer
WO2012050591A1 (en)	2010-10-15	2012-04-19	Rutgers, The State University Of New Jersey	Hydrogel formulation for dermal and ocular delivery
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
AU2009329872B2 (en)	2008-12-23	2016-07-07	Gilead Pharmasset Llc	Synthesis of purine nucleosides
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AU2014371934B2 (en)	2013-12-25	2020-01-23	Daiichi Sankyo Company, Limited	Anti-TROP2 antibody-drug conjugate
IL310627B2 (en)	2014-01-31	2026-04-01	Daiichi Sankyo Co Ltd	Anti-HER2 antibody-drug conjugates, compositions containing them and uses thereof
KR102445502B1 (ko)	2014-04-10	2022-09-21	다이이찌 산쿄 가부시키가이샤	항her3 항체-약물 콘주게이트
EP3130608B1 (de)	2014-04-10	2019-09-04	Daiichi Sankyo Co., Ltd.	(anti-her2-antikörper)-arzneimittelkonjugat
CN116059395A (zh)	2015-06-29	2023-05-05	第一三共株式会社	用于选择性制造抗体-药物缀合物的方法
US11273155B2 (en)	2016-12-12	2022-03-15	Daiichi Sankyo Company, Limited	Combination of antibody-drug conjugate and immune checkpoint inhibitor
JP6679762B2 (ja)	2017-01-17	2020-04-15	第一三共株式会社	抗ｇｐｒ２０抗体及び抗ｇｐｒ２０抗体−薬物コンジュゲート
TW202532104A (zh)	2017-05-15	2025-08-16	日商第一三共股份有限公司	抗體－藥物結合物及其用途
CA3074208C (en) *	2017-08-31	2023-10-03	Daiichi Sankyo Company, Limited	Novel method for producing antibody-drug conjugate
IL324591A (en)	2017-08-31	2026-01-01	Daiichi Sankyo Co Ltd	Improved antibody-drug conjugate production methods
SG11202010496WA (en)	2018-05-18	2020-12-30	Daiichi Sankyo Co Ltd	Anti-muc1 antibody-drug conjugate
WO2020022475A1 (ja)	2018-07-27	2020-01-30	第一三共株式会社	抗体－薬物コンジュゲートの薬物部位を認識する蛋白質
CA3108044A1 (en)	2018-07-31	2020-02-06	Daiichi Sankyo Company, Limited	Treatment of metastatic brain tumor by administration of antibody-drug conjugate
WO2020063676A1 (zh)	2018-09-26	2020-04-02	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
CA3114474A1 (en)	2018-09-30	2020-04-02	Jiangsu Hengrui Medicine Co., Ltd.	Anti-b7h3 antibody-exatecan analog conjugate and medicinal use thereof
MX2021011812A (es)	2019-03-29	2021-10-22	Medimmune Ltd	Compuestos y conjugados de estos.
US11555019B2 (en)	2019-07-10	2023-01-17	Cybrexa 3, Inc.	Peptide conjugates of microtubule-targeting agents as therapeutics
MX2022000449A (es)	2019-07-10	2022-04-25	Cybrexa 2 Inc	Conjugados peptídicos de citotoxinas como terapéuticos.
US20230054458A1 (en)	2019-12-12	2023-02-23	Jiangsu Hengrui Medicine Co., Ltd.	Anti-claudin antibody-drug conjugate and pharmaceutical use thereof
JP7781064B2 (ja)	2020-01-22	2025-12-05	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
CN115103858B (zh)	2020-03-25	2025-07-15	江苏恒瑞医药股份有限公司	一种抗体药物偶联物的制备方法
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.
BR112022019073A2 (pt)	2020-03-25	2022-11-08	Jiangsu Hengrui Pharmaceuticals Co Ltd	Composição farmacêutica que compreende conjugado anticorpo-fármaco e uso da mesma
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CN117986268A (zh) *	2022-10-28	2024-05-07	安徽皓元药业有限公司	一种依喜替康甲磺酸盐的晶型及其制备方法
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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
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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
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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 Expired - Fee Related
- 1996-04-09 NO NO19961405A patent/NO314085B1/no unknown
- 1996-04-09 CA CA002173671A patent/CA2173671A1/en not_active Abandoned
- 1996-04-09 TW TW085104156A patent/TW382630B/zh not_active IP Right Cessation
- 1996-04-09 EA EA199600018A patent/EA000036B1/ru not_active IP Right Cessation
- 1996-04-10 ES ES96105661T patent/ES2136338T3/es 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 EP EP96105661A patent/EP0737686B1/de 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
DK0737686T3 (da)	1999-11-22
EA000036B1 (ru)	1998-02-26
CN1050131C (zh)	2000-03-08
CN1133290A (zh)	1996-10-16
EA199600018A3 (ru)	1997-03-31
US6552197B2 (en)	2003-04-22
GR3031400T3 (en)	2000-01-31
KR100400941B1 (ko)	2003-12-24
ATE181919T1 (de)	1999-07-15
NO961405L (no)	1996-10-11
AU5056696A (en)	1996-10-24
CA2173671A1 (en)	1996-10-11
ES2136338T3 (es)	1999-11-16
NO961405D0 (no)	1996-04-09
EA199600018A2 (ru)	1996-10-01
DE69603117T2 (de)	1999-10-28
US20010034446A1 (en)	2001-10-25
AU692078B2 (en)	1998-05-28
EP0737686A1 (de)	1996-10-16
KR960037682A (ko)	1996-11-19
TW382630B (en)	2000-02-21
DE69603117D1 (de)	1999-08-12
EP0737686B1 (de)	1999-07-07
US6504029B1 (en)	2003-01-07

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