PT1828196E - Processo estereo-selectivo e formas cristalinas de uma camptotecina - Google Patents
Processo estereo-selectivo e formas cristalinas de uma camptotecina Download PDFInfo
- Publication number
- PT1828196E PT1828196E PT05849781T PT05849781T PT1828196E PT 1828196 E PT1828196 E PT 1828196E PT 05849781 T PT05849781 T PT 05849781T PT 05849781 T PT05849781 T PT 05849781T PT 1828196 E PT1828196 E PT 1828196E
- Authority
- PT
- Portugal
- Prior art keywords
- compound
- camptothecin
- ray diffraction
- cosolvent
- butyloxyiminomethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 31
- 229940127093 camptothecin Drugs 0.000 title claims description 29
- 230000008569 process Effects 0.000 title claims description 25
- 230000000707 stereoselective effect Effects 0.000 title claims description 9
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 title description 10
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 title description 8
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 title description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
- 239000006184 cosolvent Substances 0.000 claims description 15
- XKIDBQHJMYSFPX-NRFANRHFSA-N 80758-83-4 Chemical compound C1=CC=C2C(C=O)=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 XKIDBQHJMYSFPX-NRFANRHFSA-N 0.000 claims description 14
- 238000002441 X-ray diffraction Methods 0.000 claims description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 12
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical group COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 9
- 239000002244 precipitate Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 238000001228 spectrum Methods 0.000 claims description 7
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 claims description 6
- 150000001241 acetals Chemical class 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000003158 alcohol group Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims 2
- 239000002775 capsule Substances 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- HUYRNQWVAPCTQZ-UHFFFAOYSA-N o-butylhydroxylamine;hydrochloride Chemical compound Cl.CCCCON HUYRNQWVAPCTQZ-UHFFFAOYSA-N 0.000 claims 1
- 230000001173 tumoral effect Effects 0.000 claims 1
- 239000000843 powder Substances 0.000 description 12
- UIVFUQKYVFCEKJ-OPTOVBNMSA-N gimatecan Chemical compound C1=CC=C2C(\C=N\OC(C)(C)C)=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UIVFUQKYVFCEKJ-OPTOVBNMSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229940079593 drug Drugs 0.000 description 7
- 229950009073 gimatecan Drugs 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 230000000259 anti-tumor effect Effects 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- 150000002923 oximes Chemical class 0.000 description 5
- -1 4,5-di hydroxyazolyl Chemical group 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000011097 chromatography purification Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- ZBDXGNXNXXPKJI-UHFFFAOYSA-N o-tert-butylhydroxylamine;hydrochloride Chemical compound Cl.CC(C)(C)ON ZBDXGNXNXXPKJI-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 230000001472 cytotoxic effect Effects 0.000 description 3
- 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 3
- 239000007787 solid Substances 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 229960000303 topotecan Drugs 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- HPDRGGNSEBLDKL-NRFANRHFSA-N ac1l3zgz Chemical compound C1=CC=C2C(CO)=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 HPDRGGNSEBLDKL-NRFANRHFSA-N 0.000 description 2
- 230000001028 anti-proliverative effect Effects 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000003013 cytotoxicity Effects 0.000 description 2
- 231100000135 cytotoxicity Toxicity 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 208000032839 leukemia Diseases 0.000 description 2
- 208000037841 lung tumor Diseases 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 231100001274 therapeutic index Toxicity 0.000 description 2
- FBDOJYYTMIHHDH-OZBJMMHXSA-N (19S)-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-2,4,6,8,10,14,20-heptaen-18-one Chemical compound CC[C@@]1(O)C(=O)OCC2=CN3Cc4cc5ccccc5nc4C3C=C12 FBDOJYYTMIHHDH-OZBJMMHXSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 206010065553 Bone marrow failure Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 description 1
- 206010011793 Cystitis haemorrhagic Diseases 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 206010059024 Gastrointestinal toxicity Diseases 0.000 description 1
- 206010018338 Glioma Diseases 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 241000209018 Nyssaceae Species 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229940088954 camptosar Drugs 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000005111 carboxyalkoxy group Chemical group 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 231100000050 cytotoxic potential Toxicity 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003534 dna topoisomerase inhibitor Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 231100000414 gastrointestinal toxicity Toxicity 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 201000002802 hemorrhagic cystitis Diseases 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 229940088013 hycamtin Drugs 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229960004768 irinotecan Drugs 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 201000002364 leukopenia Diseases 0.000 description 1
- 231100001022 leukopenia Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- WCVVIGQKJZLJDB-UHFFFAOYSA-N o-butylhydroxylamine Chemical compound CCCCON WCVVIGQKJZLJDB-UHFFFAOYSA-N 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 206010043554 thrombocytopenia Diseases 0.000 description 1
- 229940044693 topoisomerase inhibitor Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
Classifications
-
- 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
- C07D491/12—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 three hetero rings
- C07D491/14—Ortho-condensed systems
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
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)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04030246 | 2004-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PT1828196E true PT1828196E (pt) | 2012-11-19 |
Family
ID=34927884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT05849781T PT1828196E (pt) | 2004-12-21 | 2005-12-16 | Processo estereo-selectivo e formas cristalinas de uma camptotecina |
Country Status (18)
| Country | Link |
|---|---|
| US (3) | US7799921B2 (enExample) |
| EP (1) | EP1828196B1 (enExample) |
| JP (2) | JP5491699B2 (enExample) |
| KR (1) | KR101355121B1 (enExample) |
| CN (1) | CN101084221B (enExample) |
| AU (1) | AU2005318227B2 (enExample) |
| BR (1) | BRPI0515832A (enExample) |
| CA (1) | CA2590756C (enExample) |
| CY (1) | CY1117243T1 (enExample) |
| DK (1) | DK1828196T3 (enExample) |
| ES (1) | ES2395930T3 (enExample) |
| HR (1) | HRP20120926T1 (enExample) |
| ME (1) | ME01495B (enExample) |
| PL (1) | PL1828196T3 (enExample) |
| PT (1) | PT1828196E (enExample) |
| RS (1) | RS52585B (enExample) |
| SI (1) | SI1828196T1 (enExample) |
| WO (1) | WO2006067092A2 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1828196B1 (en) * | 2004-12-21 | 2012-10-17 | SIGMA-TAU Industrie Farmaceutiche Riunite S.p.A. | Stereoselective process and crystalline forms of a camptothecin |
| ITRM20050418A1 (it) * | 2005-08-04 | 2007-02-05 | Sigma Tau Ind Farmaceuti | Sistemi terapeutici a rilascio immediato per il migliorato assorbimento orale di 7-[(e)-t-butilossimminometil] camptotecina. |
| FR2938534B1 (fr) | 2008-11-14 | 2012-10-26 | Sanofi Aventis | Procede de preparation de l'hemifumarate d'eplivanserine |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03271278A (ja) * | 1990-03-16 | 1991-12-03 | Nissan Chem Ind Ltd | ２―アニリノピリミジン誘導体および農園芸用殺菌剤 |
| JP3046401B2 (ja) * | 1991-06-18 | 2000-05-29 | イハラケミカル工業株式会社 | ６−〔１−（ｎ−アルコキシイミノ）エチル〕サリチル酸誘導体及びその製造法 |
| IL106786A (en) * | 1992-09-10 | 1997-02-18 | Basf Ag | Substituted pyridine derivatives and fungicidal compositions containing them |
| EP1044977B1 (en) * | 1999-03-09 | 2002-05-02 | Sigma-Tau Industrie Farmaceutiche Riunite S.p.A. | Camptothecin derivatives having antitumor activity |
| AU2003215594A1 (en) * | 2002-03-01 | 2003-09-16 | Pharmacia Italia S.P.A. | Crystalline polymorphic form of irinotecan hydrochloride |
| EP1828196B1 (en) * | 2004-12-21 | 2012-10-17 | SIGMA-TAU Industrie Farmaceutiche Riunite S.p.A. | Stereoselective process and crystalline forms of a camptothecin |
-
2005
- 2005-12-16 EP EP05849781A patent/EP1828196B1/en not_active Expired - Lifetime
- 2005-12-16 HR HRP20120926TT patent/HRP20120926T1/hr unknown
- 2005-12-16 ME MEP-2012-128A patent/ME01495B/me unknown
- 2005-12-16 PT PT05849781T patent/PT1828196E/pt unknown
- 2005-12-16 DK DK05849781.9T patent/DK1828196T3/da active
- 2005-12-16 CA CA2590756A patent/CA2590756C/en not_active Expired - Fee Related
- 2005-12-16 ES ES05849781T patent/ES2395930T3/es not_active Expired - Lifetime
- 2005-12-16 KR KR1020077016814A patent/KR101355121B1/ko not_active Expired - Fee Related
- 2005-12-16 PL PL05849781T patent/PL1828196T3/pl unknown
- 2005-12-16 SI SI200531610T patent/SI1828196T1/sl unknown
- 2005-12-16 AU AU2005318227A patent/AU2005318227B2/en not_active Ceased
- 2005-12-16 CN CN2005800440829A patent/CN101084221B/zh not_active Expired - Lifetime
- 2005-12-16 WO PCT/EP2005/056849 patent/WO2006067092A2/en not_active Ceased
- 2005-12-16 RS RS20120505A patent/RS52585B/sr unknown
- 2005-12-16 US US11/721,282 patent/US7799921B2/en not_active Expired - Fee Related
- 2005-12-16 JP JP2007547467A patent/JP5491699B2/ja not_active Expired - Fee Related
- 2005-12-16 BR BRPI0515832-0A patent/BRPI0515832A/pt not_active Application Discontinuation
-
2010
- 2010-08-17 US US12/857,743 patent/US8124769B2/en not_active Expired - Fee Related
- 2010-08-17 US US12/857,776 patent/US8101758B2/en not_active Expired - Fee Related
-
2012
- 2012-10-30 CY CY20121101034T patent/CY1117243T1/el unknown
- 2012-11-09 JP JP2012247587A patent/JP5982261B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20100311783A1 (en) | 2010-12-09 |
| HK1113487A1 (en) | 2008-10-03 |
| WO2006067092A3 (en) | 2006-11-02 |
| EP1828196A2 (en) | 2007-09-05 |
| RS52585B (sr) | 2013-04-30 |
| US7799921B2 (en) | 2010-09-21 |
| CN101084221B (zh) | 2011-05-11 |
| PL1828196T3 (pl) | 2013-02-28 |
| AU2005318227A1 (en) | 2006-06-29 |
| EP1828196B1 (en) | 2012-10-17 |
| ES2395930T3 (es) | 2013-02-18 |
| KR101355121B1 (ko) | 2014-01-24 |
| JP5982261B2 (ja) | 2016-08-31 |
| CN101084221A (zh) | 2007-12-05 |
| US8124769B2 (en) | 2012-02-28 |
| KR20070097535A (ko) | 2007-10-04 |
| CY1117243T1 (el) | 2017-04-05 |
| US20090239893A1 (en) | 2009-09-24 |
| JP2013067629A (ja) | 2013-04-18 |
| ME01495B (me) | 2014-04-20 |
| DK1828196T3 (da) | 2012-11-26 |
| BRPI0515832A (pt) | 2008-08-05 |
| CA2590756C (en) | 2014-09-02 |
| US20100311784A1 (en) | 2010-12-09 |
| JP5491699B2 (ja) | 2014-05-14 |
| JP2008524306A (ja) | 2008-07-10 |
| CA2590756A1 (en) | 2006-06-29 |
| WO2006067092A2 (en) | 2006-06-29 |
| HRP20120926T1 (hr) | 2012-12-31 |
| SI1828196T1 (sl) | 2012-12-31 |
| AU2005318227B2 (en) | 2011-08-18 |
| US8101758B2 (en) | 2012-01-24 |
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