ZA200406927B - Crystalline polymorphic form of irinotecan hydrochloride - Google Patents
Crystalline polymorphic form of irinotecan hydrochloride Download PDFInfo
- Publication number
- ZA200406927B ZA200406927B ZA200406927A ZA200406927A ZA200406927B ZA 200406927 B ZA200406927 B ZA 200406927B ZA 200406927 A ZA200406927 A ZA 200406927A ZA 200406927 A ZA200406927 A ZA 200406927A ZA 200406927 B ZA200406927 B ZA 200406927B
- Authority
- ZA
- South Africa
- Prior art keywords
- cancer
- polymorph
- irinotecan hydrochloride
- composition
- irinotecan
- Prior art date
Links
- GURKHSYORGJETM-WAQYZQTGSA-N irinotecan hydrochloride (anhydrous) Chemical compound Cl.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 GURKHSYORGJETM-WAQYZQTGSA-N 0.000 title claims description 70
- 229960000779 irinotecan hydrochloride Drugs 0.000 title claims description 40
- 238000000034 method Methods 0.000 claims description 28
- 206010028980 Neoplasm Diseases 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 201000011510 cancer Diseases 0.000 claims description 12
- 206010009944 Colon cancer Diseases 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 9
- 206010017993 Gastrointestinal neoplasms Diseases 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 239000002552 dosage form Substances 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 4
- 239000002002 slurry Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 238000002329 infrared spectrum Methods 0.000 claims description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229960004768 irinotecan Drugs 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- 239000000843 powder Substances 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000008186 active pharmaceutical agent Substances 0.000 description 5
- 229940088954 camptosar Drugs 0.000 description 5
- 229940088679 drug related substance Drugs 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 229940102223 injectable solution Drugs 0.000 description 5
- 239000004310 lactic acid Substances 0.000 description 5
- 235000014655 lactic acid Nutrition 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000000862 absorption spectrum Methods 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 239000008355 dextrose injection Substances 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001802 infusion Methods 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
- 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 description 3
- 208000029742 colonic neoplasm Diseases 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229950010538 irinotecan hydrochloride trihydrate Drugs 0.000 description 3
- 208000020816 lung neoplasm Diseases 0.000 description 3
- 239000006201 parenteral dosage form Substances 0.000 description 3
- 229960002920 sorbitol Drugs 0.000 description 3
- 238000011269 treatment regimen Methods 0.000 description 3
- -1 trihydrate salt Chemical class 0.000 description 3
- FJHBVJOVLFPMQE-QFIPXVFZSA-N 7-Ethyl-10-Hydroxy-Camptothecin Chemical compound C1=C(O)C=C2C(CC)=C(CN3C(C4=C([C@@](C(=O)OC4)(O)CC)C=C33)=O)C3=NC2=C1 FJHBVJOVLFPMQE-QFIPXVFZSA-N 0.000 description 2
- 206010008342 Cervix carcinoma Diseases 0.000 description 2
- 229940123780 DNA topoisomerase I inhibitor Drugs 0.000 description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000365 Topoisomerase I Inhibitor Substances 0.000 description 2
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 201000010881 cervical cancer Diseases 0.000 description 2
- 210000001072 colon Anatomy 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000012738 dissolution medium Substances 0.000 description 2
- 210000002919 epithelial cell Anatomy 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 208000011645 metastatic carcinoma Diseases 0.000 description 2
- 206010061289 metastatic neoplasm Diseases 0.000 description 2
- 230000009826 neoplastic cell growth Effects 0.000 description 2
- 210000000664 rectum Anatomy 0.000 description 2
- 201000001275 rectum cancer Diseases 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000008354 sodium chloride injection Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- IPVYMXZYXFFDGW-UHFFFAOYSA-N 1-methylpiperidin-4-ol;hydrochloride Chemical compound Cl.CN1CCC(O)CC1 IPVYMXZYXFFDGW-UHFFFAOYSA-N 0.000 description 1
- 206010004146 Basal cell carcinoma Diseases 0.000 description 1
- 206010005003 Bladder cancer Diseases 0.000 description 1
- 206010005949 Bone cancer Diseases 0.000 description 1
- 208000018084 Bone neoplasm Diseases 0.000 description 1
- 208000003174 Brain Neoplasms Diseases 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 241000759905 Camptotheca acuminata Species 0.000 description 1
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 description 1
- 102000004308 Carboxylic Ester Hydrolases Human genes 0.000 description 1
- 108090000863 Carboxylic Ester Hydrolases Proteins 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 208000000461 Esophageal Neoplasms Diseases 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 201000003741 Gastrointestinal carcinoma Diseases 0.000 description 1
- 238000010268 HPLC based assay Methods 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 206010030155 Oesophageal carcinoma Diseases 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 208000006265 Renal cell carcinoma Diseases 0.000 description 1
- 208000000453 Skin Neoplasms Diseases 0.000 description 1
- 206010041067 Small cell lung cancer Diseases 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 208000009956 adenocarcinoma Diseases 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 229960000074 biopharmaceutical Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 238000007707 calorimetry Methods 0.000 description 1
- 229940127093 camptothecin Drugs 0.000 description 1
- WUQLBTLTPNTZDA-UHFFFAOYSA-N carbamic acid;1h-pyridin-2-one Chemical compound NC(O)=O.OC1=CC=CC=N1 WUQLBTLTPNTZDA-UHFFFAOYSA-N 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009096 combination chemotherapy Methods 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 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 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 201000004101 esophageal cancer Diseases 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 201000002313 intestinal cancer Diseases 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 208000037922 refractory disease Diseases 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 201000000849 skin cancer Diseases 0.000 description 1
- 208000000587 small cell lung carcinoma Diseases 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 235000020138 yakult Nutrition 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
- C07D491/22—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
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36068402P | 2002-03-01 | 2002-03-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200406927B true ZA200406927B (en) | 2006-06-28 |
Family
ID=27789001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200406927A ZA200406927B (en) | 2002-03-01 | 2004-08-31 | Crystalline polymorphic form of irinotecan hydrochloride |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP1487840B1 (xx) |
| JP (1) | JP2005525367A (xx) |
| KR (1) | KR20040091083A (xx) |
| CN (1) | CN1276923C (xx) |
| AR (1) | AR038618A1 (xx) |
| AT (1) | ATE364610T1 (xx) |
| AU (1) | AU2003215594A1 (xx) |
| BR (1) | BR0308133A (xx) |
| CA (1) | CA2477926A1 (xx) |
| DE (1) | DE60314378T2 (xx) |
| DK (1) | DK1487840T3 (xx) |
| ES (1) | ES2287495T3 (xx) |
| HK (1) | HK1075044A1 (xx) |
| IL (1) | IL163820A0 (xx) |
| MX (1) | MXPA04008484A (xx) |
| NO (1) | NO20044138L (xx) |
| NZ (1) | NZ534999A (xx) |
| PE (1) | PE20030923A1 (xx) |
| PL (1) | PL372318A1 (xx) |
| PT (1) | PT1487840E (xx) |
| RU (1) | RU2300535C2 (xx) |
| TW (1) | TWI270374B (xx) |
| WO (1) | WO2003074527A1 (xx) |
| ZA (1) | ZA200406927B (xx) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004076460A1 (ja) * | 2003-02-25 | 2004-09-10 | Kabushiki Kaisha Yakult Honsha | イリノテカン塩酸塩の結晶多形の製造方法 |
| ES2245891B1 (es) * | 2004-07-09 | 2006-11-16 | Clinmet S.L. | "metodo para la obtencion de un excipiente universal para la administracion oral de principios activos farmaceuticos y composiciones de excipientes resultantes del metodo". |
| EP1828196B1 (en) | 2004-12-21 | 2012-10-17 | SIGMA-TAU Industrie Farmaceutiche Riunite S.p.A. | Stereoselective process and crystalline forms of a camptothecin |
| PL1846412T3 (pl) | 2005-02-07 | 2010-03-31 | Fermion Oy | Sposób wytwarzania 7-etylo-10-hydroksykamptotecyny |
| PL1928883T3 (pl) * | 2005-02-08 | 2014-03-31 | Fermion Oy | Sposób otrzymywania chlorowodorku irynotekanu |
| JP5133703B2 (ja) | 2005-02-08 | 2013-01-30 | フェルミオン オサケ ユキチュア | ［１，４’］ビピペリジニル−１’−カルボニルクロリドまたはその塩酸塩の製造方法 |
| BRPI0616308A2 (pt) * | 2005-09-20 | 2011-06-14 | Scinopharm Singapore Pte Ltd | novas formas de cristal de cloridrato de irinotecano |
| CN101318964B (zh) * | 2007-06-07 | 2010-12-15 | 上海迪赛诺医药发展有限公司 | 盐酸伊立替康新晶型及其制备方法 |
| FR2918279B1 (fr) * | 2007-07-05 | 2010-10-22 | Aventis Pharma Sa | Combinaisons antitumorales contenant un agent inhibiteur de vegf et de l'irinotecan |
| IT1391757B1 (it) * | 2008-11-11 | 2012-01-27 | Antibioticos Spa | Irinotecan cloridrato cristallino e metodi per la sua preparazione |
| CN101659667B (zh) * | 2009-09-07 | 2011-11-02 | 重庆泰濠制药有限公司 | 一种盐酸伊立替康的纯化方法 |
| US8546573B2 (en) | 2009-11-18 | 2013-10-01 | Cadila Healthcare Limited | Process for the preparation of 7-ethyl-10-[4-(1-piperidino)-1-piperdino] carbonyloxy-camptothecin hydrochloride trihydrate |
| JO3283B1 (ar) | 2011-04-26 | 2018-09-16 | Sanofi Sa | تركيب يتضمن أفليبيرسيبت, حمض فولينيك, 5- فلورويوراسيل (5- Fu) وإرينوسيتان (FOLFIRI) |
| CN102866126B (zh) * | 2011-07-05 | 2016-03-23 | 重庆华邦制药有限公司 | 一种定量测定化合物中晶型比例的方法 |
| CN102311443B (zh) * | 2011-08-24 | 2014-07-16 | 上海北卡医药技术有限公司 | 盐酸伊立替康的新晶型及其制备方法 |
| RU2529831C2 (ru) * | 2012-11-30 | 2014-09-27 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Российский университет дружбы народов" (РУДН) | Способ лечения рака толстой кишки |
| MX2017000840A (es) | 2014-07-18 | 2017-05-04 | Sanofi Sa | Metodo para predecir el resultado de un tratamiento con aflibercept de un paciente que se sospecha que padece un cancer. |
| KR102293907B1 (ko) * | 2015-06-30 | 2021-08-26 | 한미약품 주식회사 | 이리노테칸 함유 경구용 고형제제 및 그 제조방법 |
| KR102066402B1 (ko) * | 2017-12-22 | 2020-01-15 | 대화제약 주식회사 | 이리노테칸 또는 그의 약제학적으로 허용가능한 염을 포함하는 경구투여용 약제학적 조성물 |
| US10919905B2 (en) * | 2019-05-16 | 2021-02-16 | Scinopharm Taiwan, Ltd. | Polymorphism for irinotecan free base |
-
2003
- 2003-02-26 ES ES03743335T patent/ES2287495T3/es not_active Expired - Lifetime
- 2003-02-26 DE DE60314378T patent/DE60314378T2/de not_active Expired - Fee Related
- 2003-02-26 IL IL16382003A patent/IL163820A0/xx unknown
- 2003-02-26 MX MXPA04008484A patent/MXPA04008484A/es not_active Application Discontinuation
- 2003-02-26 NZ NZ534999A patent/NZ534999A/en unknown
- 2003-02-26 CA CA002477926A patent/CA2477926A1/en not_active Abandoned
- 2003-02-26 KR KR10-2004-7013621A patent/KR20040091083A/ko not_active Application Discontinuation
- 2003-02-26 AU AU2003215594A patent/AU2003215594A1/en not_active Abandoned
- 2003-02-26 EP EP03743335A patent/EP1487840B1/en not_active Expired - Lifetime
- 2003-02-26 PT PT03743335T patent/PT1487840E/pt unknown
- 2003-02-26 JP JP2003572995A patent/JP2005525367A/ja not_active Withdrawn
- 2003-02-26 WO PCT/EP2003/001948 patent/WO2003074527A1/en active IP Right Grant
- 2003-02-26 CN CNB038072726A patent/CN1276923C/zh not_active Expired - Fee Related
- 2003-02-26 RU RU2004129307/04A patent/RU2300535C2/ru not_active IP Right Cessation
- 2003-02-26 PL PL03372318A patent/PL372318A1/xx not_active Application Discontinuation
- 2003-02-26 BR BR0308133-8A patent/BR0308133A/pt not_active IP Right Cessation
- 2003-02-26 DK DK03743335T patent/DK1487840T3/da active
- 2003-02-26 AT AT03743335T patent/ATE364610T1/de not_active IP Right Cessation
- 2003-02-27 TW TW092104194A patent/TWI270374B/zh not_active IP Right Cessation
- 2003-02-28 PE PE2003000196A patent/PE20030923A1/es not_active Application Discontinuation
- 2003-02-28 AR ARP030100656A patent/AR038618A1/es unknown
-
2004
- 2004-08-31 ZA ZA200406927A patent/ZA200406927B/en unknown
- 2004-09-29 NO NO20044138A patent/NO20044138L/no not_active Application Discontinuation
-
2005
- 2005-08-22 HK HK05107303A patent/HK1075044A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE60314378T2 (de) | 2008-02-28 |
| WO2003074527A1 (en) | 2003-09-12 |
| KR20040091083A (ko) | 2004-10-27 |
| ES2287495T3 (es) | 2007-12-16 |
| EP1487840A1 (en) | 2004-12-22 |
| RU2004129307A (ru) | 2005-04-10 |
| RU2300535C2 (ru) | 2007-06-10 |
| DE60314378D1 (en) | 2007-07-26 |
| CA2477926A1 (en) | 2003-09-12 |
| NZ534999A (en) | 2007-03-30 |
| AU2003215594A1 (en) | 2003-09-16 |
| PE20030923A1 (es) | 2003-10-29 |
| TW200303753A (en) | 2003-09-16 |
| NO20044138L (no) | 2004-11-29 |
| PL372318A1 (en) | 2005-07-11 |
| CN1642958A (zh) | 2005-07-20 |
| BR0308133A (pt) | 2005-01-04 |
| TWI270374B (en) | 2007-01-11 |
| DK1487840T3 (da) | 2007-07-16 |
| PT1487840E (pt) | 2007-09-11 |
| CN1276923C (zh) | 2006-09-27 |
| MXPA04008484A (es) | 2004-12-06 |
| HK1075044A1 (en) | 2005-12-02 |
| IL163820A0 (en) | 2005-12-18 |
| EP1487840B1 (en) | 2007-06-13 |
| JP2005525367A (ja) | 2005-08-25 |
| ATE364610T1 (de) | 2007-07-15 |
| AR038618A1 (es) | 2005-01-19 |
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