ZA200301593B - Amorphous form of cell cycle inhibitor. - Google Patents
Amorphous form of cell cycle inhibitor. Download PDFInfo
- Publication number
- ZA200301593B ZA200301593B ZA200301593A ZA200301593A ZA200301593B ZA 200301593 B ZA200301593 B ZA 200301593B ZA 200301593 A ZA200301593 A ZA 200301593A ZA 200301593 A ZA200301593 A ZA 200301593A ZA 200301593 B ZA200301593 B ZA 200301593B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- formula
- organic solvent
- crystalline
- amorphous
- Prior art date
Links
- 229940123587 Cell cycle inhibitor Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 172
- 238000000034 method Methods 0.000 claims description 63
- 239000003960 organic solvent Substances 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 239000012530 fluid Substances 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 229920000831 ionic polymer Polymers 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 7
- 239000003381 stabilizer Substances 0.000 claims description 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 5
- 239000001569 carbon dioxide Substances 0.000 claims description 5
- -1 glycofural Chemical compound 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims description 5
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 5
- 235000013772 propylene glycol Nutrition 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 4
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims description 4
- 238000004108 freeze drying Methods 0.000 claims description 4
- 238000001694 spray drying Methods 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
- 239000012943 hotmelt Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 26
- 238000009472 formulation Methods 0.000 description 19
- 238000004090 dissolution Methods 0.000 description 13
- 239000000843 powder Substances 0.000 description 11
- 239000002245 particle Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000005469 granulation Methods 0.000 description 8
- 230000003179 granulation Effects 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 238000000634 powder X-ray diffraction Methods 0.000 description 7
- 239000008213 purified water Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 241000282472 Canis lupus familiaris Species 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 239000000454 talc Substances 0.000 description 6
- 235000012222 talc Nutrition 0.000 description 6
- 229910052623 talc Inorganic materials 0.000 description 6
- 238000000113 differential scanning calorimetry Methods 0.000 description 5
- 238000002356 laser light scattering Methods 0.000 description 5
- 239000000825 pharmaceutical preparation Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000001757 thermogravimetry curve Methods 0.000 description 5
- GUBGYTABKSRVRQ-DCSYEGIMSA-N Beta-Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-DCSYEGIMSA-N 0.000 description 4
- 229920003091 Methocel™ Polymers 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229920003093 Methocel™ K100 LV Polymers 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 239000012738 dissolution medium Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 230000036470 plasma concentration Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- HQOWCDPFDSRYRO-CDKVKFQUSA-N CCCCCCc1ccc(cc1)C1(c2cc3-c4sc5cc(\C=C6/C(=O)c7ccccc7C6=C(C#N)C#N)sc5c4C(c3cc2-c2sc3cc(C=C4C(=O)c5ccccc5C4=C(C#N)C#N)sc3c12)(c1ccc(CCCCCC)cc1)c1ccc(CCCCCC)cc1)c1ccc(CCCCCC)cc1 Chemical compound CCCCCCc1ccc(cc1)C1(c2cc3-c4sc5cc(\C=C6/C(=O)c7ccccc7C6=C(C#N)C#N)sc5c4C(c3cc2-c2sc3cc(C=C4C(=O)c5ccccc5C4=C(C#N)C#N)sc3c12)(c1ccc(CCCCCC)cc1)c1ccc(CCCCCC)cc1)c1ccc(CCCCCC)cc1 HQOWCDPFDSRYRO-CDKVKFQUSA-N 0.000 description 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 101000959883 Solanum tuberosum Aspartic protease inhibitor 3 Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000011978 dissolution method Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000009474 hot melt extrusion Methods 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000001294 liquid chromatography-tandem mass spectrometry Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S977/00—Nanotechnology
- Y10S977/902—Specified use of nanostructure
- Y10S977/904—Specified use of nanostructure for medical, immunological, body treatment, or diagnosis
- Y10S977/915—Therapeutic or pharmaceutical composition
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Extraction Or Liquid Replacement (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23756300P | 2000-10-03 | 2000-10-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200301593B true ZA200301593B (en) | 2004-06-22 |
Family
ID=22894259
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200301593A ZA200301593B (en) | 2000-10-03 | 2003-02-26 | Amorphous form of cell cycle inhibitor. |
Country Status (15)
| Country | Link |
|---|---|
| US (4) | US6482847B2 (de) |
| EP (1) | EP1366040B1 (de) |
| JP (3) | JP2004510771A (de) |
| KR (1) | KR100554933B1 (de) |
| CN (1) | CN1250541C (de) |
| AR (1) | AR035064A1 (de) |
| AT (1) | ATE447566T1 (de) |
| AU (2) | AU1396502A (de) |
| BR (1) | BRPI0114156B8 (de) |
| CA (1) | CA2423286C (de) |
| DE (1) | DE60140382D1 (de) |
| ES (1) | ES2334012T3 (de) |
| MX (1) | MXPA03002858A (de) |
| WO (1) | WO2002028855A2 (de) |
| ZA (1) | ZA200301593B (de) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6482847B2 (en) * | 2000-10-03 | 2002-11-19 | Hoffmann-La Roche Inc. | Amorphous form of cell cycle inhibitor having improved solubility and bioavailability |
| US20030139373A1 (en) * | 2001-11-20 | 2003-07-24 | Breimer Lars Holger | Method for cancer therapy |
| EP1469827B1 (de) * | 2002-01-09 | 2017-12-27 | Emisphere Technologies, Inc. | Polymorphe von natrium-4-(4-chlor-2-hydroxybenzoyl)aminobutanoat |
| WO2003087335A2 (en) * | 2002-04-11 | 2003-10-23 | Medimmune Vaccines, Inc. | Preservation of bioactive materials by spray drying |
| CA2702935A1 (en) * | 2007-10-19 | 2009-04-23 | Purdue Research Foundation | Solid formulations of crystalline compounds |
| US8268354B2 (en) * | 2007-11-07 | 2012-09-18 | Aridis Pharmaceuticals | Sonic low pressure spray drying |
| ES2531040T3 (es) * | 2009-05-12 | 2015-03-10 | Corcept Therapeutics Inc | Formas sólidas y procedimiento de preparación |
| US8969588B2 (en) * | 2012-06-05 | 2015-03-03 | Gilead Pharmasset Llc | Solid forms of an antiviral compound |
| JP6339364B2 (ja) * | 2013-12-27 | 2018-06-06 | カズマパートナーズ株式会社 | 無定形ブリモニジン酒石酸塩及びその製造方法 |
| GB201502073D0 (en) * | 2015-02-09 | 2015-03-25 | Cubic Pharmaceuticals Ltd And Delta Pharmaceuticals Ltd | HDEG technology |
| PT108370B (pt) * | 2015-03-30 | 2018-10-25 | Hovione Farm S A | Processo de preparação de brometo de aclidínio |
| EP3896075A1 (de) * | 2015-12-18 | 2021-10-20 | Galecto Biotech AB | Polymorphe formen und verfahren |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ227850A (en) * | 1988-02-10 | 1991-11-26 | Hoffmann La Roche | Indole substituted pyrrole derivatives; preparatory process and medicaments for use against inflammatory immunological, bronchopulmonary or vascular disorders |
| USRE36736E (en) | 1989-02-06 | 2000-06-13 | Hoffman-La Roche Inc. | Substituted pyrroles |
| JPH08208478A (ja) * | 1994-10-14 | 1996-08-13 | Japan Energy Corp | 抗エイズ薬製剤およびその製造方法 |
| TW487582B (en) * | 1995-08-11 | 2002-05-21 | Nissan Chemical Ind Ltd | Method for converting sparingly water-soluble medical substance to amorphous state |
| PT1064279E (pt) | 1998-03-17 | 2003-10-31 | Hoffmann La Roche | Bisindolilmaleimidas substituidas para a inibicao da proliferacao celular |
| US6036736A (en) | 1998-04-03 | 2000-03-14 | Wells Manufacturing Company, Inc. | Ventilating method and apparatus |
| US6350786B1 (en) | 1998-09-22 | 2002-02-26 | Hoffmann-La Roche Inc. | Stable complexes of poorly soluble compounds in ionic polymers |
| SE9803261D0 (sv) | 1998-09-25 | 1998-09-25 | Siemens Elema Ab | Andningsapparat |
| KR20020003864A (ko) * | 1999-03-03 | 2002-01-15 | 피터 지. 스트링거 | 에키노칸딘/탄수화물 착물 |
| US6326501B1 (en) | 2000-04-19 | 2001-12-04 | Hoffmann-La Roche Inc. | Methylation of indole compounds using dimethyl carbonate |
| US6482847B2 (en) * | 2000-10-03 | 2002-11-19 | Hoffmann-La Roche Inc. | Amorphous form of cell cycle inhibitor having improved solubility and bioavailability |
-
2001
- 2001-08-13 US US09/928,635 patent/US6482847B2/en not_active Expired - Lifetime
- 2001-09-26 ES ES01982358T patent/ES2334012T3/es not_active Expired - Lifetime
- 2001-09-26 KR KR1020037004648A patent/KR100554933B1/ko not_active Expired - Lifetime
- 2001-09-26 AT AT01982358T patent/ATE447566T1/de active
- 2001-09-26 CA CA002423286A patent/CA2423286C/en not_active Expired - Lifetime
- 2001-09-26 BR BR0114156-2 patent/BRPI0114156B8/pt not_active IP Right Cessation
- 2001-09-26 MX MXPA03002858A patent/MXPA03002858A/es active IP Right Grant
- 2001-09-26 WO PCT/EP2001/011119 patent/WO2002028855A2/en not_active Ceased
- 2001-09-26 CN CNB018166318A patent/CN1250541C/zh not_active Expired - Lifetime
- 2001-09-26 EP EP01982358A patent/EP1366040B1/de not_active Expired - Lifetime
- 2001-09-26 JP JP2002532438A patent/JP2004510771A/ja not_active Withdrawn
- 2001-09-26 AU AU1396502A patent/AU1396502A/xx active Pending
- 2001-09-26 DE DE60140382T patent/DE60140382D1/de not_active Expired - Lifetime
- 2001-09-26 AU AU2002213965A patent/AU2002213965B2/en not_active Expired
- 2001-10-01 AR ARP010104627A patent/AR035064A1/es not_active Application Discontinuation
-
2002
- 2002-04-11 US US10/121,036 patent/US6486329B1/en not_active Expired - Lifetime
- 2002-04-11 US US10/120,463 patent/US6469180B1/en not_active Expired - Lifetime
- 2002-04-11 US US10/120,460 patent/US6492530B1/en not_active Expired - Lifetime
-
2003
- 2003-02-26 ZA ZA200301593A patent/ZA200301593B/en unknown
-
2007
- 2007-08-24 JP JP2007218828A patent/JP5341331B2/ja not_active Expired - Lifetime
-
2012
- 2012-02-17 JP JP2012032566A patent/JP2012136534A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP1366040B1 (de) | 2009-11-04 |
| CN1468231A (zh) | 2004-01-14 |
| JP5341331B2 (ja) | 2013-11-13 |
| US20020061922A1 (en) | 2002-05-23 |
| JP2012136534A (ja) | 2012-07-19 |
| ES2334012T3 (es) | 2010-03-04 |
| US6492530B1 (en) | 2002-12-10 |
| MXPA03002858A (es) | 2003-07-14 |
| CA2423286A1 (en) | 2002-04-11 |
| JP2008056670A (ja) | 2008-03-13 |
| US6469180B1 (en) | 2002-10-22 |
| US20020173532A1 (en) | 2002-11-21 |
| BRPI0114156B8 (pt) | 2021-05-25 |
| DE60140382D1 (de) | 2009-12-17 |
| US6486329B1 (en) | 2002-11-26 |
| AU2002213965B2 (en) | 2007-07-19 |
| JP2004510771A (ja) | 2004-04-08 |
| WO2002028855A3 (en) | 2003-09-12 |
| BRPI0114156B1 (pt) | 2018-09-11 |
| US20020173533A1 (en) | 2002-11-21 |
| AR035064A1 (es) | 2004-04-14 |
| CA2423286C (en) | 2008-10-28 |
| EP1366040A2 (de) | 2003-12-03 |
| KR100554933B1 (ko) | 2006-03-03 |
| US20020173534A1 (en) | 2002-11-21 |
| CN1250541C (zh) | 2006-04-12 |
| AU1396502A (en) | 2002-04-15 |
| WO2002028855A2 (en) | 2002-04-11 |
| US6482847B2 (en) | 2002-11-19 |
| BR0114156A (pt) | 2003-07-29 |
| KR20030036872A (ko) | 2003-05-09 |
| ATE447566T1 (de) | 2009-11-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5341331B2 (ja) | 細胞周期阻害物質の非晶質形態 | |
| KR102013440B1 (ko) | Parp 억제제 고체약물제형 및 그 용도 | |
| JP5479912B2 (ja) | 複素環式化合物の非晶質体、それを含む固体分散体、薬剤、およびその製造法 | |
| IL189587A (en) | Solid dispersion, a pharmaceutical composition comprising the solid dispersion and process of preparing the solid dispersion | |
| EP3279201B1 (de) | Cdk-inhibitor, eutektisches kristall von mek-inhibitor und herstellungsverfahren dafür | |
| TWI786579B (zh) | 包含藥物二聚體的奈米粒子及其用途 | |
| AU2002213965A1 (en) | Amorphous form of cell cycle inhibitor | |
| CN113288859B (zh) | 奥拉帕尼药物组合物及其制剂、制备方法和用途 | |
| EP3486233A1 (de) | Schlecht löslicher komplex oder solvat davon, pharmazeutische zusammensetzung und anwendung davon | |
| US6469179B1 (en) | Amorphous form of cell cycle inhibitor having improved solubility and bioavailability | |
| CN105753869B (zh) | 一种cdk抑制剂和mek抑制剂的共晶及其制备方法 | |
| EP1466914B1 (de) | Amorphe substanz eines tricyclischen triazolobenzazepinderivats | |
| CN105732642B (zh) | 一种cdk抑制剂和mek抑制剂的共晶及其制备方法 |