SK287404B6 - Pseudopolymorfná forma (-)-cis-2-(2-chlórfenyl)-5,7-dihydroxy- 8[4R-(3S-hydroxy-1-metyl)piperidinyl]-4H-1-benzopyran-4- ónhydrochloridu, spôsob jej prípravy a farmaceutická kompozícia, ktorá ju obsahuje - Google Patents
Pseudopolymorfná forma (-)-cis-2-(2-chlórfenyl)-5,7-dihydroxy- 8[4R-(3S-hydroxy-1-metyl)piperidinyl]-4H-1-benzopyran-4- ónhydrochloridu, spôsob jej prípravy a farmaceutická kompozícia, ktorá ju obsahuje Download PDFInfo
- Publication number
- SK287404B6 SK287404B6 SK1036-2002A SK10362002A SK287404B6 SK 287404 B6 SK287404 B6 SK 287404B6 SK 10362002 A SK10362002 A SK 10362002A SK 287404 B6 SK287404 B6 SK 287404B6
- Authority
- SK
- Slovakia
- Prior art keywords
- flavopiridol
- pseudopolymorph
- thick
- forms
- pharmaceutical composition
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 125000003386 piperidinyl group Chemical group 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 claims abstract description 36
- 239000002904 solvent Substances 0.000 claims abstract description 23
- 238000010533 azeotropic distillation Methods 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- BIIVYFLTOXDAOV-YVEFUNNKSA-N alvocidib Chemical group O[C@@H]1CN(C)CC[C@@H]1C1=C(O)C=C(O)C2=C1OC(C=1C(=CC=CC=1)Cl)=CC2=O BIIVYFLTOXDAOV-YVEFUNNKSA-N 0.000 claims description 24
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 20
- 229950010817 alvocidib Drugs 0.000 claims description 19
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 15
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- 125000005936 piperidyl group Chemical group 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
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- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 125000005808 2,4,6-trimethoxyphenyl group Chemical group [H][#6]-1=[#6](-[#8]C([H])([H])[H])-[#6](-*)=[#6](-[#8]C([H])([H])[H])-[#6]([H])=[#6]-1-[#8]C([H])([H])[H] 0.000 description 1
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- 208000002495 Uterine Neoplasms Diseases 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- SNZXMAHBUQXQSE-UHFFFAOYSA-N acetonitrile;benzene Chemical compound CC#N.C1=CC=CC=C1 SNZXMAHBUQXQSE-UHFFFAOYSA-N 0.000 description 1
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- 239000004480 active ingredient Substances 0.000 description 1
- -1 aliphatic nitriles Chemical class 0.000 description 1
- LGMSNQNWOCSPIK-LWHGMNCYSA-N alvocidib hydrochloride Chemical compound Cl.O[C@@H]1CN(C)CC[C@@H]1C1=C(O)C=C(O)C2=C1OC(C=1C(=CC=CC=1)Cl)=CC2=O LGMSNQNWOCSPIK-LWHGMNCYSA-N 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
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- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
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- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
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- JAVRNIFMYIJXIE-UHFFFAOYSA-N methyl 2-chlorobenzoate Chemical compound COC(=O)C1=CC=CC=C1Cl JAVRNIFMYIJXIE-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Stereophonic System (AREA)
- Inorganic Insulating Materials (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48471700A | 2000-01-18 | 2000-01-18 | |
| PCT/US2001/000519 WO2001053293A1 (en) | 2000-01-18 | 2001-01-08 | Pseudopolymorph of (-)-cis-2-(2-chlorophenyl)-5,7-dihydroxy-8[4r-(3s-hydroxy-1-methyl)piperidinyl]-4h-1-benzopyran-4-one |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK10362002A3 SK10362002A3 (sk) | 2003-01-09 |
| SK287404B6 true SK287404B6 (sk) | 2010-09-07 |
Family
ID=23925305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1036-2002A SK287404B6 (sk) | 2000-01-18 | 2001-01-08 | Pseudopolymorfná forma (-)-cis-2-(2-chlórfenyl)-5,7-dihydroxy- 8[4R-(3S-hydroxy-1-metyl)piperidinyl]-4H-1-benzopyran-4- ónhydrochloridu, spôsob jej prípravy a farmaceutická kompozícia, ktorá ju obsahuje |
Country Status (26)
| Country | Link |
|---|---|
| EP (1) | EP1259507B1 (cs) |
| JP (1) | JP2003520797A (cs) |
| KR (1) | KR100806464B1 (cs) |
| CN (1) | CN1174977C (cs) |
| AT (1) | ATE273303T1 (cs) |
| AU (1) | AU2001226346A1 (cs) |
| BR (1) | BR0107726A (cs) |
| CA (1) | CA2397593C (cs) |
| CZ (1) | CZ301195B6 (cs) |
| DE (1) | DE60104822T2 (cs) |
| DK (1) | DK1259507T3 (cs) |
| EA (1) | EA005247B1 (cs) |
| ES (1) | ES2222332T3 (cs) |
| HU (1) | HUP0204126A3 (cs) |
| IL (2) | IL150638A0 (cs) |
| MX (1) | MXPA02007005A (cs) |
| NO (1) | NO322572B1 (cs) |
| NZ (1) | NZ520280A (cs) |
| PL (1) | PL200696B1 (cs) |
| PT (1) | PT1259507E (cs) |
| SI (1) | SI1259507T1 (cs) |
| SK (1) | SK287404B6 (cs) |
| TR (1) | TR200402036T4 (cs) |
| TW (1) | TWI284129B (cs) |
| WO (1) | WO2001053293A1 (cs) |
| ZA (1) | ZA200205639B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG11201901472TA (en) | 2016-08-23 | 2019-03-28 | Eisai R&D Man Co Ltd | Combination therapies for the treatment of hepatocellular carcinoma |
| AU2018234903B2 (en) | 2017-03-16 | 2024-02-08 | Eisai R&D Management Co., Ltd. | Combination therapies for the treatment of breast cancer |
| CA3124330A1 (en) | 2018-12-21 | 2020-06-25 | Daiichi Sankyo Company, Limited | Combination of antibody-drug conjugate and kinase inhibitor |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN164232B (cs) * | 1986-04-11 | 1989-02-04 | Hoechst India | |
| US5284856A (en) * | 1988-10-28 | 1994-02-08 | Hoechst Aktiengesellschaft | Oncogene-encoded kinases inhibition using 4-H-1-benzopyran-4-one derivatives |
| US5908934A (en) * | 1996-09-26 | 1999-06-01 | Bristol-Myers Squibb Company | Process for the preparation of chiral ketone intermediates useful for the preparation of flavopiridol and analogs |
-
2001
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- 2001-01-08 WO PCT/US2001/000519 patent/WO2001053293A1/en active IP Right Grant
- 2001-01-08 PT PT01900939T patent/PT1259507E/pt unknown
- 2001-01-08 AT AT01900939T patent/ATE273303T1/de active
- 2001-01-08 ES ES01900939T patent/ES2222332T3/es not_active Expired - Lifetime
- 2001-01-08 CA CA002397593A patent/CA2397593C/en not_active Expired - Lifetime
- 2001-01-08 IL IL15063801A patent/IL150638A0/xx unknown
- 2001-01-08 DK DK01900939T patent/DK1259507T3/da active
- 2001-01-08 KR KR1020027009215A patent/KR100806464B1/ko not_active Expired - Lifetime
- 2001-01-08 EA EA200200775A patent/EA005247B1/ru not_active IP Right Cessation
- 2001-01-08 AU AU2001226346A patent/AU2001226346A1/en not_active Abandoned
- 2001-01-08 DE DE60104822T patent/DE60104822T2/de not_active Expired - Lifetime
- 2001-01-08 PL PL356165A patent/PL200696B1/pl unknown
- 2001-01-08 CZ CZ20022466A patent/CZ301195B6/cs not_active IP Right Cessation
- 2001-01-08 BR BR0107726-0A patent/BR0107726A/pt not_active Application Discontinuation
- 2001-01-08 CN CNB018038476A patent/CN1174977C/zh not_active Expired - Lifetime
- 2001-01-08 EP EP01900939A patent/EP1259507B1/en not_active Expired - Lifetime
- 2001-01-08 TR TR2004/02036T patent/TR200402036T4/xx unknown
- 2001-01-08 JP JP2001553767A patent/JP2003520797A/ja active Pending
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