BRPI0616308A2 - novas formas de cristal de cloridrato de irinotecano - Google Patents
novas formas de cristal de cloridrato de irinotecano Download PDFInfo
- Publication number
- BRPI0616308A2 BRPI0616308A2 BRPI0616308-4A BRPI0616308A BRPI0616308A2 BR PI0616308 A2 BRPI0616308 A2 BR PI0616308A2 BR PI0616308 A BRPI0616308 A BR PI0616308A BR PI0616308 A2 BRPI0616308 A2 BR PI0616308A2
- Authority
- BR
- Brazil
- Prior art keywords
- crystalline form
- irinotecan hydrochloride
- hydrochloride
- irinotecan
- hydrochloric acid
- 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 abstract description 93
- 229960000779 irinotecan hydrochloride Drugs 0.000 title claims abstract description 63
- 239000013078 crystal Substances 0.000 title abstract description 3
- 238000000034 method Methods 0.000 claims abstract description 13
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 68
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 40
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 32
- 238000009792 diffusion process Methods 0.000 claims description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 229960004768 irinotecan Drugs 0.000 claims description 10
- 238000002441 X-ray diffraction Methods 0.000 claims description 8
- 238000002425 crystallisation Methods 0.000 claims description 7
- 230000008025 crystallization Effects 0.000 claims description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 238000004090 dissolution Methods 0.000 claims 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 claims 1
- 206010061289 metastatic neoplasm Diseases 0.000 abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 7
- 210000001072 colon Anatomy 0.000 abstract description 6
- 208000011645 metastatic carcinoma Diseases 0.000 abstract description 2
- 210000000664 rectum Anatomy 0.000 abstract description 2
- 201000001275 rectum cancer Diseases 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 6
- 238000005464 sample preparation method Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000001394 metastastic effect Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 208000020615 rectal carcinoma Diseases 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 229940127557 pharmaceutical product Drugs 0.000 description 3
- 206010038038 rectal cancer Diseases 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000008355 dextrose injection Substances 0.000 description 2
- 229960002949 fluorouracil Drugs 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 229950010538 irinotecan hydrochloride trihydrate Drugs 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 230000037317 transdermal delivery Effects 0.000 description 2
- CUGZEDSDRBMZMY-UHFFFAOYSA-N trihydrate;hydrochloride Chemical compound O.O.O.Cl CUGZEDSDRBMZMY-UHFFFAOYSA-N 0.000 description 2
- QDVBKXJMLILLLB-UHFFFAOYSA-N 1,4'-bipiperidine Chemical compound C1CCCCN1C1CCNCC1 QDVBKXJMLILLLB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VVIAGPKUTFNRDU-UHFFFAOYSA-N 6S-folinic acid Natural products C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 241000759905 Camptotheca acuminata Species 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 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 1
- 241000124008 Mammalia Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 229940034982 antineoplastic agent Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940088954 camptosar Drugs 0.000 description 1
- 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 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- VVIAGPKUTFNRDU-ABLWVSNPSA-N folinic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-ABLWVSNPSA-N 0.000 description 1
- 235000008191 folinic acid Nutrition 0.000 description 1
- 239000011672 folinic acid Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000001990 intravenous administration Methods 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
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229960001691 leucovorin Drugs 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000008354 sodium chloride injection Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71882705P | 2005-09-20 | 2005-09-20 | |
| US60/718.827 | 2005-09-20 | ||
| PCT/US2006/036437 WO2007035709A2 (en) | 2005-09-20 | 2006-09-19 | Novel crystal forms of irinotecan hydrochloride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0616308A2 true BRPI0616308A2 (pt) | 2011-06-14 |
Family
ID=37889452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0616308-4A BRPI0616308A2 (pt) | 2005-09-20 | 2006-09-19 | novas formas de cristal de cloridrato de irinotecano |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7435818B2 (enExample) |
| EP (2) | EP2082741A1 (enExample) |
| JP (1) | JP5119153B2 (enExample) |
| KR (1) | KR101150504B1 (enExample) |
| CN (1) | CN101277694B (enExample) |
| AR (1) | AR056082A1 (enExample) |
| AT (1) | ATE460162T1 (enExample) |
| AU (1) | AU2006292328B2 (enExample) |
| BR (1) | BRPI0616308A2 (enExample) |
| CA (1) | CA2623117C (enExample) |
| DE (1) | DE602006012871D1 (enExample) |
| ES (1) | ES2343204T3 (enExample) |
| NZ (1) | NZ566807A (enExample) |
| WO (1) | WO2007035709A2 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US7572803B2 (en) * | 2007-10-25 | 2009-08-11 | The Christus Stehlin Foundation For Cancer Research | Hydrated crystalline esters of camptothecin |
| IT1391757B1 (it) * | 2008-11-11 | 2012-01-27 | Antibioticos Spa | Irinotecan cloridrato cristallino e metodi per la sua preparazione |
| 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 |
| WO2012007952A1 (en) * | 2010-07-12 | 2012-01-19 | Hetero Research Foundation | Novel polymorph of irinotecan hydrochloride |
| 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 |
| CN102617584B (zh) * | 2012-03-14 | 2013-10-16 | 海南锦瑞制药股份有限公司 | 一种盐酸伊立替康化合物及其药物组合物 |
| CN102850363B (zh) * | 2012-09-18 | 2013-07-10 | 山东罗欣药业股份有限公司 | 盐酸伊立替康化合物及其药物组合物 |
| EP2986739B1 (en) | 2013-04-15 | 2018-04-04 | Regeneron Pharmaceuticals, Inc. | Markers of tumor cell response to anti-cancer therapy |
| CN105713004A (zh) * | 2016-03-23 | 2016-06-29 | 杭州华东医药集团新药研究院有限公司 | 一种高品质盐酸伊立替康三水合物晶型的制备方法 |
| US10919905B2 (en) * | 2019-05-16 | 2021-02-16 | Scinopharm Taiwan, Ltd. | Polymorphism for irinotecan free base |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6019790A (ja) | 1983-07-14 | 1985-01-31 | Yakult Honsha Co Ltd | 新規なカンプトテシン誘導体 |
| MA24682A1 (fr) * | 1997-10-23 | 1999-07-01 | Smithkline Beecham Corp | Formes polymorphes nouvelles de cipamfylline, procede pour leur preparation et compositions les contenant |
| SK9742002A3 (en) * | 2000-01-07 | 2003-02-04 | Transform Pharmaceuticals Inc | High-throughput formation, identification, and analysis of diverse solid-forms |
| PL372318A1 (en) | 2002-03-01 | 2005-07-11 | Pharmacia Italia S.P.A. | Crystalline polymorphic form of irinotecan hydrochloride |
| CZ20022250A3 (cs) * | 2002-06-27 | 2004-02-18 | Pliva-Lachema A. S. | Způsob výroby irinotekanu |
| AU2004215560B2 (en) | 2003-02-25 | 2009-09-24 | Kabushiki Kaisha Yakult Honsha | Method for preparing polymorphism of irinotecan hydrochloride |
| WO2006016203A1 (en) * | 2004-08-09 | 2006-02-16 | Shilpa Medicare Limited | An improved process for the preparation of irinotecan hydrochloride trihydrate |
| US20060046993A1 (en) * | 2004-09-01 | 2006-03-02 | Pharmacia Italia S.P.A. | Crystalline polymorphic form of irinotecan hydrochloride |
| ATE446299T1 (de) * | 2005-02-07 | 2009-11-15 | Fermion Oy | Verfahren zur herstellung von 7-ethyl-10- hydroxycamptothecin |
| EP1928883B1 (en) * | 2005-02-08 | 2013-10-30 | Fermion Oy | Process for the preparation of irinotecan hydrochloride |
-
2006
- 2006-09-19 AU AU2006292328A patent/AU2006292328B2/en not_active Ceased
- 2006-09-19 CA CA2623117A patent/CA2623117C/en not_active Expired - Fee Related
- 2006-09-19 WO PCT/US2006/036437 patent/WO2007035709A2/en not_active Ceased
- 2006-09-19 EP EP09155420A patent/EP2082741A1/en not_active Withdrawn
- 2006-09-19 US US11/523,367 patent/US7435818B2/en not_active Expired - Fee Related
- 2006-09-19 NZ NZ566807A patent/NZ566807A/en unknown
- 2006-09-19 AT AT06803842T patent/ATE460162T1/de not_active IP Right Cessation
- 2006-09-19 BR BRPI0616308-4A patent/BRPI0616308A2/pt not_active IP Right Cessation
- 2006-09-19 CN CN2006800345941A patent/CN101277694B/zh not_active Expired - Fee Related
- 2006-09-19 EP EP06803842A patent/EP1951235B1/en not_active Not-in-force
- 2006-09-19 KR KR1020087009534A patent/KR101150504B1/ko not_active Expired - Fee Related
- 2006-09-19 DE DE602006012871T patent/DE602006012871D1/de active Active
- 2006-09-19 JP JP2008531427A patent/JP5119153B2/ja not_active Expired - Fee Related
- 2006-09-19 ES ES06803842T patent/ES2343204T3/es active Active
- 2006-09-21 AR ARP060104123A patent/AR056082A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2006292328A1 (en) | 2007-03-29 |
| CA2623117A1 (en) | 2007-03-29 |
| US20070072890A1 (en) | 2007-03-29 |
| ES2343204T3 (es) | 2010-07-26 |
| KR20080059244A (ko) | 2008-06-26 |
| DE602006012871D1 (de) | 2010-04-22 |
| WO2007035709A3 (en) | 2007-10-25 |
| CA2623117C (en) | 2013-12-10 |
| EP1951235A4 (en) | 2008-10-29 |
| CN101277694B (zh) | 2011-04-20 |
| NZ566807A (en) | 2011-05-27 |
| WO2007035709A2 (en) | 2007-03-29 |
| JP2009508874A (ja) | 2009-03-05 |
| AR056082A1 (es) | 2007-09-19 |
| CN101277694A (zh) | 2008-10-01 |
| EP1951235A2 (en) | 2008-08-06 |
| EP2082741A1 (en) | 2009-07-29 |
| US7435818B2 (en) | 2008-10-14 |
| JP5119153B2 (ja) | 2013-01-16 |
| EP1951235B1 (en) | 2010-03-10 |
| KR101150504B1 (ko) | 2012-07-09 |
| ATE460162T1 (de) | 2010-03-15 |
| AU2006292328B2 (en) | 2012-12-20 |
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