FI104373B - Förfarande för att framställa farmaceutiskt användbara 7-aminosubstituerade 10,11-metylendioxi- eller 10,11-etylendioxi-kamptotekinderivat - Google Patents
Förfarande för att framställa farmaceutiskt användbara 7-aminosubstituerade 10,11-metylendioxi- eller 10,11-etylendioxi-kamptotekinderivat Download PDFInfo
- Publication number
- FI104373B FI104373B FI924878A FI924878A FI104373B FI 104373 B FI104373 B FI 104373B FI 924878 A FI924878 A FI 924878A FI 924878 A FI924878 A FI 924878A FI 104373 B FI104373 B FI 104373B
- Authority
- FI
- Finland
- Prior art keywords
- compound
- formula
- camptothecin
- ethylenedioxy
- methylenedioxy
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/66—Nitrogen atoms not forming part of a nitro radical
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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Claims (7)
1. Förfarande för att framställa farmaceutiskt användbara 7-aminosubstitu-erade 10,11 -metylendioxi- eller 10,11 -etyiendioxi-kamptotekinderivat med 5 formeln (I) ..nrV /0YVva (CH,)n N-Y° 10. o w Tri där n är heltalet 1 eller 2; och 15 i) R1 och R2 är oberoende av varandra väte, C^-alkyl eller hydroxi-C^-alkyl; ii) R1 är väte och R2 är -COR3 4, där R3 är trifluor-C^-alkyl; eller 20 :. 5. · iii) R1 och R2 tillsammans med det förenande kvävet bildar azetidin, pyrrolidin, t : ’ · · piperidin, morfolin, tiomorfolin eller piperazin, vilken piperazln eventuellt är N- substituerad med lägre alkyl, fenyl, vilken fenyl kan vara substituerad med en trifluor-C^-alkyl- eller C^-alkoxigrupper; eller -COR5, där R5 är C^-alkoxi, « · • « · ·. *: 25 • I» ’ och deras farmaceutiskt acceptable salter eller solvater, kännetecknat därav, att • t* • · · • » · • M I I I \ ’ a) en förening med formeln (IV) 30 « · « « I «Il « · I I 2 « f 3 « f 4 «tl „ 104373 51 r^X (CH2)n N^/° - (ivi A-/ HO o där X är halogen, omsätts med en förening med formeln (V)
10 HNR1R2 (V) där R1 och R2 avser det samma som i föreningen med formeln (I); eller b) en förening med formeln (lla) 15 ^nrV / τι ^o (CHzn J (Ha) 20 I f '.:. ' där R1 och R2 avser det samma som i föreningen med formeln (I), omsätts med 1 · : * en förening med formeln (III) I· Qk === (ΙΙΙ,ΛΥ HO © t » » w • » » ] 30 och om sä erfordras och/eller vid behov underkastas den sa erhallna föreningen en eller flera tilläggsreaktioner, som är «f« I I · f · I I I I < I f 2 I t % 52 104373 i) omvandling av en erhallen förening med formeln (I) eller dess salt eller skyddade derivat till en annan förening med formeln (I), företrädesvis genom alkylering eller reducering, och/eller ii) eliminering av vilken som heist skyddgrupp och/eller 5 iii) omvandling av en förening med formeln (I) eller dess salt till dess fysiologiskt godtagbara salt eller soivat.
2. Förfarande enligt patentkravet 1 för framställning av 7-(4-metylpiperazino-metylen)-10,11-etylendioxi-20(R,S)-kamptotesin, kännetecknat därav, att 10 motsvarande utgangsämnen används.
3. Förfarande enligt patentkravet 1 för framställning av 7-(4-metylpiperazino-metylen)-10,11“etylendioxi-20(S)-kamptotesin, kännetecknat därav, att motsvarande utgängsämnen används. 15
4. Förfarande enligt patentkravet 1 för framställning av 7-(4-metylpiperazino-metylen)-10,11 -metylendioxi-20(S)-kamptotesin, kännetecknat därav, att motsvarande utgängsämnen används. 20 5. Förfarande enligt patentkraven 1 eller 2, kännetecknat därav, att i steget « i : : ! (a) utförs reaktionen i ett lösningsmedelssystem i närvaro av ett överskott av * < '·' ” en förening med formeln (V). < i « f I k • · ·«·
6. Förfarande enligt patentkravet 1, kännetecknat därav, att en erhällen • · · 25 förening det därtill omfattar steget där med formeln (I) eller dess farmaceutiskt mmm godtagbar sait eller soivat blandas med en farmaceutiskt godtagbar bärare. ·«· • · 1 • · «
7. Förfarande enligt nägot av föregäende patentkrav, kännetecknat därav, att • · · en förening med formeln (I), som uppvisar R-konfiguration, framställs. 1(1(1 : 30 • · « « i · < · ( (Il « » · f I I | I ( I
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78427591A | 1991-10-29 | 1991-10-29 | |
| US78427591 | 1991-10-29 | ||
| US82672992A | 1992-01-28 | 1992-01-28 | |
| US82672992 | 1992-01-28 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI924878A0 FI924878A0 (fi) | 1992-10-28 |
| FI924878A FI924878A (fi) | 1993-04-30 |
| FI104373B true FI104373B (sv) | 2000-01-14 |
Family
ID=27120258
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI924878A FI104373B (sv) | 1991-10-29 | 1992-10-28 | Förfarande för att framställa farmaceutiskt användbara 7-aminosubstituerade 10,11-metylendioxi- eller 10,11-etylendioxi-kamptotekinderivat |
| FI982185A FI982185A (sv) | 1991-10-29 | 1998-10-08 | Vattenlösliga kamptotesinderivat |
| FI20021090A FI20021090A (sv) | 1991-10-29 | 2002-06-07 | Vattenlösliga kamptotesinderiva |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI982185A FI982185A (sv) | 1991-10-29 | 1998-10-08 | Vattenlösliga kamptotesinderivat |
| FI20021090A FI20021090A (sv) | 1991-10-29 | 2002-06-07 | Vattenlösliga kamptotesinderiva |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP0540099B1 (sv) |
| JP (2) | JP3020760B2 (sv) |
| KR (1) | KR100246154B1 (sv) |
| CN (1) | CN1072683A (sv) |
| AP (1) | AP306A (sv) |
| AT (1) | ATE136898T1 (sv) |
| AU (1) | AU657007B2 (sv) |
| CA (1) | CA2081580A1 (sv) |
| CZ (1) | CZ284023B6 (sv) |
| DE (1) | DE69209969T2 (sv) |
| DK (1) | DK0540099T3 (sv) |
| ES (1) | ES2086643T3 (sv) |
| FI (3) | FI104373B (sv) |
| GR (1) | GR3020120T3 (sv) |
| HU (2) | HU217970B (sv) |
| IL (1) | IL103571A (sv) |
| IS (1) | IS1708B (sv) |
| MX (1) | MX9206211A (sv) |
| MY (1) | MY108261A (sv) |
| NO (1) | NO302073B1 (sv) |
| NZ (1) | NZ244914A (sv) |
| OA (1) | OA09767A (sv) |
| RU (1) | RU2119921C1 (sv) |
| SK (1) | SK323792A3 (sv) |
| TW (1) | TW221994B (sv) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5364858A (en) * | 1987-03-31 | 1994-11-15 | Research Triangle Institute | Camptothecin analogs as potent inhibitors of topoisomerase I |
| US5552154A (en) | 1989-11-06 | 1996-09-03 | The Stehlin Foundation For Cancer Research | Method for treating cancer with water-insoluble s-camptothecin of the closed lactone ring form and derivatives thereof |
| US6080751A (en) * | 1992-01-14 | 2000-06-27 | The Stehlin Foundation For Cancer Research | Method for treating pancreatic cancer in humans with water-insoluble S-camptothecin of the closed lactone ring form and derivatives thereof |
| AP9300587A0 (en) * | 1992-11-12 | 1995-05-05 | Glaxo Inc | Water soluble camptothecin derivatives. |
| DK1250926T3 (da) * | 1993-01-15 | 2008-07-07 | Stehlin Foundation For Cancer | Anvendelse af vanduoplöseligt S-camptothecin med en lukket lactonring i fremstilling af et medikament til behandling af coloncancer |
| US5369127A (en) * | 1993-04-21 | 1994-11-29 | Allergan, Inc. | 1,3-benzodioxole and 1,2-dialkoxybenzene derivatives as ocular hypotensive agents |
| IS4152A (is) * | 1993-04-29 | 1994-10-30 | Glaxo Inc. | Vatnsuppleysanlegar Camptothecin afleiður og aðferð til framleiðslu þeirra |
| EP0699201A1 (en) * | 1993-05-03 | 1996-03-06 | Smithkline Beecham Corporation | SUBSTITUTED METHYLENEDIOXY 3',4':6,7]INDOLIZINO- 1,2-$i(b)]QUINOLINONES |
| US5447936A (en) * | 1993-12-22 | 1995-09-05 | Bionumerik Pharmaceuticals, Inc. | Lactone stable formulation of 10-hydroxy 7-ethyl camptothecin and methods for uses thereof |
| US5491237A (en) * | 1994-05-03 | 1996-02-13 | Glaxo Wellcome Inc. | Intermediates in pharmaceutical camptothecin preparation |
| IT1269862B (it) * | 1994-05-30 | 1997-04-15 | Indena Spa | Alcaloidi da mappia foetida, loro uso e formulazioni che li contengono |
| US5646159A (en) * | 1994-07-20 | 1997-07-08 | Research Triangle Institute | Water-soluble esters of camptothecin compounds |
| KR960029336A (ko) * | 1995-01-09 | 1996-08-17 | 김충환 | 캄토테신 유도체, 그의 제조 방법 및 이를 함유하는 항암제 |
| US5496952A (en) * | 1995-02-07 | 1996-03-05 | North Carolina State University | Method of making asymmetric DE ring intermediates for the synthesis of camptothecin and camptothecin analogs |
| US5670500A (en) * | 1995-05-31 | 1997-09-23 | Smithkline Beecham Corporation | Water soluble camptothecin analogs |
| EP0837850B1 (en) * | 1995-06-27 | 2004-09-01 | Takeda Chemical Industries, Ltd. | 4-acylamino(halogeno) alkyl-quinoline derivatives, their preparation and their use as melatonin agonists |
| SG50747A1 (en) * | 1995-08-02 | 1998-07-20 | Tanabe Seiyaku Co | Comptothecin derivatives |
| WO1997019085A1 (en) * | 1995-11-22 | 1997-05-29 | Research Triangle Institute | Camptothecin compounds with combined topoisomerase i inhibition and dna alkylation properties |
| CA2192725C (en) | 1995-12-28 | 2004-04-20 | Kenji Tsujihara | Camptothecin derivatives |
| SG104284A1 (en) * | 1996-10-30 | 2004-06-21 | Tanabe Seiyaku Co | S type 2-substituted hydroxy-2-indolidinylbutyric ester compounds and process for preparation thereof |
| US6559309B2 (en) * | 1996-11-01 | 2003-05-06 | Osi Pharmaceuticals, Inc. | Preparation of a camptothecin derivative by intramolecular cyclisation |
| US6207673B1 (en) | 1997-03-12 | 2001-03-27 | The University Of North Carolina At Chapel Hill | Covalent conjugates of topoisomerase I and topoisomerase II inhibitors |
| US6046209A (en) * | 1997-05-27 | 2000-04-04 | Smithkline Beecham Corporation | Water soluble camptothecin analogs |
| US6288072B1 (en) * | 1999-12-29 | 2001-09-11 | Monroe E. Wall | Camptothecin β-alanine esters with topoisomerase I inhibition |
| CA2401191C (en) | 2000-02-28 | 2006-05-02 | Aventis Pharma S.A. | A composition comprising camptothecin and a pyrimidine 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 |
| 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 |
| US6486320B2 (en) | 2000-09-15 | 2002-11-26 | Aventis Pharma S.A. | Preparation of camptothecin and of its derivatives |
| CN1200712C (zh) | 2000-10-27 | 2005-05-11 | 阿文蒂斯药物股份有限公司 | 用于治疗癌症的含喜树碱和1,2－二苯乙烯衍生物的组合物 |
| ITRM20040240A1 (it) * | 2004-05-13 | 2004-08-13 | Ist Naz Stud Cura Dei Tumori | Camptotecine coniugate in posizione 7 con antagonisti delle integrine. |
| 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 |
| CN101407524B (zh) * | 2007-10-09 | 2012-07-18 | 江苏先声药物研究有限公司 | 噁嗪骈喜树碱衍生物及其制备方法和用途 |
| CN100592871C (zh) * | 2008-03-14 | 2010-03-03 | 浙江林学院 | 一种杀虫剂组合物及其加工方法 |
| ES2373172B1 (es) * | 2010-07-16 | 2012-12-10 | Consejo Superior De Investigaciones Científicas (Csic) | Proceso de obtención de derivados solubles en agua de 20 (s) camptotecina como agentes antitumorales. |
| US20140086975A1 (en) | 2010-10-15 | 2014-03-27 | Rutgers, The State University Of New Jersey | Hydrogel formulation for dermal and ocular delivery |
| CN103313992B (zh) * | 2011-01-12 | 2016-04-27 | 天堃医药科技（杭州）有限公司 | 具有hdac抑制作用的喜树碱衍生物 |
| US20190343828A1 (en) * | 2018-04-06 | 2019-11-14 | Seattle Genetics, Inc. | Camptothecin peptide conjugates |
| TWI851577B (zh) | 2018-06-07 | 2024-08-11 | 美商思進公司 | 喜樹鹼結合物 |
| CN110590796B (zh) * | 2018-06-12 | 2022-07-15 | 青岛海洋生物医药研究院股份有限公司 | 喜树碱衍生物及其制备方法和应用 |
| AU2022330892A1 (en) * | 2021-08-19 | 2024-03-21 | Hainan Simcere Zaiming Pharmaceutical Co., Ltd. | Camptothecin derivative, and pharmaceutical composition and use thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5004758A (en) * | 1987-12-01 | 1991-04-02 | Smithkline Beecham Corporation | Water soluble camptothecin analogs useful for inhibiting the growth of animal tumor cells |
-
1992
- 1992-10-23 EP EP92203263A patent/EP0540099B1/en not_active Expired - Lifetime
- 1992-10-23 AT AT92203263T patent/ATE136898T1/de not_active IP Right Cessation
- 1992-10-23 ES ES92203263T patent/ES2086643T3/es not_active Expired - Lifetime
- 1992-10-23 DK DK92203263.6T patent/DK0540099T3/da active
- 1992-10-23 DE DE69209969T patent/DE69209969T2/de not_active Expired - Fee Related
- 1992-10-27 SK SK3237-92A patent/SK323792A3/sk unknown
- 1992-10-27 CZ CS923237A patent/CZ284023B6/cs not_active IP Right Cessation
- 1992-10-27 TW TW081108539A patent/TW221994B/zh active
- 1992-10-28 NO NO924158A patent/NO302073B1/no unknown
- 1992-10-28 MY MYPI92001954A patent/MY108261A/en unknown
- 1992-10-28 FI FI924878A patent/FI104373B/sv active
- 1992-10-28 AU AU27385/92A patent/AU657007B2/en not_active Ceased
- 1992-10-28 KR KR1019920019884A patent/KR100246154B1/ko not_active IP Right Cessation
- 1992-10-28 AP APAP/P/1992/000439A patent/AP306A/en active
- 1992-10-28 IL IL103571A patent/IL103571A/en not_active IP Right Cessation
- 1992-10-28 HU HU9203384A patent/HU217970B/hu not_active IP Right Cessation
- 1992-10-28 CA CA002081580A patent/CA2081580A1/en not_active Abandoned
- 1992-10-28 MX MX9206211A patent/MX9206211A/es unknown
- 1992-10-28 NZ NZ244914A patent/NZ244914A/xx not_active IP Right Cessation
- 1992-10-28 OA OA60295A patent/OA09767A/en unknown
- 1992-10-28 IS IS3936A patent/IS1708B/is unknown
- 1992-10-28 CN CN92113782A patent/CN1072683A/zh not_active Withdrawn
- 1992-10-28 RU RU92004336A patent/RU2119921C1/ru not_active IP Right Cessation
- 1992-10-28 JP JP4312862A patent/JP3020760B2/ja not_active Expired - Fee Related
-
1995
- 1995-06-14 HU HU95P/P00203P patent/HU211349A9/hu unknown
-
1996
- 1996-05-31 GR GR960401497T patent/GR3020120T3/el unknown
-
1998
- 1998-10-08 FI FI982185A patent/FI982185A/sv unknown
-
1999
- 1999-11-02 JP JP31294099A patent/JP3229298B2/ja not_active Expired - Fee Related
-
2002
- 2002-06-07 FI FI20021090A patent/FI20021090A/sv not_active Application Discontinuation
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