ZA200104416B - Complex of ras-farnesyltransferase inhibitor and sulfobutylether-7-β-cyclodextrin or 2-hydroxypropyl-β-cyclodextrin and method. - Google Patents
Complex of ras-farnesyltransferase inhibitor and sulfobutylether-7-β-cyclodextrin or 2-hydroxypropyl-β-cyclodextrin and method. Download PDFInfo
- Publication number
- ZA200104416B ZA200104416B ZA200104416A ZA200104416A ZA200104416B ZA 200104416 B ZA200104416 B ZA 200104416B ZA 200104416 A ZA200104416 A ZA 200104416A ZA 200104416 A ZA200104416 A ZA 200104416A ZA 200104416 B ZA200104416 B ZA 200104416B
- Authority
- ZA
- South Africa
- Prior art keywords
- cyclodextrin
- complex
- inhibitor
- phenylmethyl
- composition
- Prior art date
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- 229920000858 Cyclodextrin Polymers 0.000 title claims description 36
- 239000003528 protein farnesyltransferase inhibitor Substances 0.000 title claims description 28
- 229940124226 Farnesyltransferase inhibitor Drugs 0.000 title claims description 20
- 238000000034 method Methods 0.000 title description 8
- 229960004853 betadex Drugs 0.000 title description 5
- 239000001116 FEMA 4028 Substances 0.000 title description 3
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims description 29
- 239000003112 inhibitor Substances 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- DCQLZTSRKLWEAB-UHFFFAOYSA-N ac1ndudu Chemical compound O1C(C(C2OCC(C)O)OCC(C)O)C(COCC(C)O)OC2OC(C(C2OCC(C)O)OCC(C)O)C(COCC(C)O)OC2OC(C(C2OCC(C)O)OCC(C)O)C(COCC(C)O)OC2OC(C(C2OCC(C)O)OCC(C)O)C(COCC(C)O)OC2OC(C(OCC(C)O)C2OCC(C)O)C(COCC(O)C)OC2OC(C(C2OCC(C)O)OCC(C)O)C(COCC(C)O)OC2OC2C(OCC(C)O)C(OCC(C)O)C1OC2COCC(C)O DCQLZTSRKLWEAB-UHFFFAOYSA-N 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 11
- OLCWFLWEHWLBTO-HSZRJFAPSA-N BMS-214662 Chemical compound C=1C=CSC=1S(=O)(=O)N([C@@H](C1)CC=2C=CC=CC=2)CC2=CC(C#N)=CC=C2N1CC1=CN=CN1 OLCWFLWEHWLBTO-HSZRJFAPSA-N 0.000 claims description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 239000000872 buffer Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000003792 electrolyte Substances 0.000 claims description 3
- 238000007911 parenteral administration Methods 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- YDXZCFLYIHUBSR-HXUWFJFHSA-N (3r)-3-benzyl-7-bromo-1-(1h-imidazol-5-ylmethyl)-4-methylsulfonyl-3,5-dihydro-2h-1,4-benzodiazepine Chemical compound CS(=O)(=O)N([C@@H](C1)CC=2C=CC=CC=2)CC2=CC(Br)=CC=C2N1CC1=CNC=N1 YDXZCFLYIHUBSR-HXUWFJFHSA-N 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 239000000243 solution Substances 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
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- 229940079593 drug Drugs 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
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- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 7
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- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000001990 intravenous administration Methods 0.000 description 5
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 125000005842 heteroatom Chemical group 0.000 description 4
- 238000000527 sonication Methods 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- 229960001138 acetylsalicylic acid Drugs 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
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- 239000000706 filtrate Substances 0.000 description 3
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 3
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- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 2
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Classifications
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- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
- A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Nanotechnology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- General Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biophysics (AREA)
- Biotechnology (AREA)
- Medical Informatics (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Plural Heterocyclic Compounds (AREA)
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EP (1) | EP1143796A4 (pt) |
JP (1) | JP2002535253A (pt) |
KR (1) | KR100708360B1 (pt) |
CN (1) | CN1219517C (pt) |
AR (1) | AR022323A1 (pt) |
AU (1) | AU772204B2 (pt) |
BG (1) | BG105666A (pt) |
BR (1) | BR9916566A (pt) |
CA (1) | CA2359646C (pt) |
CO (1) | CO5160253A1 (pt) |
CZ (1) | CZ20012601A3 (pt) |
EE (1) | EE200100382A (pt) |
GE (1) | GEP20043214B (pt) |
HK (1) | HK1038865A1 (pt) |
HU (1) | HUP0105160A3 (pt) |
ID (1) | ID30139A (pt) |
IL (1) | IL144025A (pt) |
LT (1) | LT4893B (pt) |
LV (1) | LV12712B (pt) |
MY (1) | MY119700A (pt) |
NO (1) | NO20013585L (pt) |
NZ (1) | NZ511995A (pt) |
PE (1) | PE20001419A1 (pt) |
PL (1) | PL195280B1 (pt) |
RU (1) | RU2230062C2 (pt) |
SK (1) | SK9602001A3 (pt) |
TR (1) | TR200102109T2 (pt) |
TW (1) | TWI232752B (pt) |
UA (1) | UA67825C2 (pt) |
UY (2) | UY25986A1 (pt) |
WO (1) | WO2000042849A1 (pt) |
ZA (1) | ZA200104416B (pt) |
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TWI310684B (en) | 2000-03-27 | 2009-06-11 | Bristol Myers Squibb Co | Synergistic pharmaceutical kits for treating cancer |
JP2003063965A (ja) * | 2001-06-13 | 2003-03-05 | Otsuka Pharmaceut Factory Inc | 注射用シロスタゾール水性製剤 |
US6566347B1 (en) * | 2001-08-22 | 2003-05-20 | Duquesne University Of The Holy Ghost | Controlled release pharmaceutical |
WO2003041658A2 (en) * | 2001-11-13 | 2003-05-22 | Bristol-Myers Squibb Company | Process for the preparation of 3,7-disubstituted-2,3,4,5- tetrahydro-1h-1,4-benzodiazepine compounds |
KR100451485B1 (ko) | 2002-03-28 | 2004-10-06 | 주식회사종근당 | 푸마질롤 유도체 또는 그 염의 포접 화합물, 및 이를포함하는 약제학적 조성물 |
US6869939B2 (en) * | 2002-05-04 | 2005-03-22 | Cydex, Inc. | Formulations containing amiodarone and sulfoalkyl ether cyclodextrin |
AU2003276648A1 (en) * | 2002-06-17 | 2003-12-31 | Bristol-Myers Squibb Company | Benzodiazepine inhibitors of mitochondial f¿1?f¿0? atp hydrolase and methods of inhibiting f¿1?f¿0? atp hydrolase |
US7157446B2 (en) * | 2003-05-02 | 2007-01-02 | Bristol Myers Squibb Company | Complex of ras-farnesyltransferase inhibitor, a cyclodextrin, and ethanol |
US20070020299A1 (en) | 2003-12-31 | 2007-01-25 | Pipkin James D | Inhalant formulation containing sulfoalkyl ether cyclodextrin and corticosteroid |
US20100204178A1 (en) | 2006-10-02 | 2010-08-12 | James Cloyd | Novel parenteral carbamazepine formulation |
SI1928464T1 (sl) * | 2005-09-30 | 2014-09-30 | Lundbeck Inc. | Nova parenteralna karbamazepinska formulacija |
CN100503647C (zh) * | 2005-11-02 | 2009-06-24 | 南京师范大学 | 羟丙基-磺丁基-β-环糊精及其制备方法、分析方法以及在药学上的应用 |
TW200806284A (en) * | 2006-03-31 | 2008-02-01 | Alcon Mfg Ltd | Prenyltransferase inhibitors for ocular hypertension control and the treatment of glaucoma |
WO2008063634A1 (en) * | 2006-11-21 | 2008-05-29 | Novartis Ag | Stable parenteral formulation containing a rsv inhibitor of a benzodiazepine structure |
HUE057625T2 (hu) | 2008-10-22 | 2022-05-28 | Array Biopharma Inc | TRK kináz inhibitor szubsztituált pirazolo[1,5-a]pirimidin vegyületek |
ES2759605T3 (es) * | 2010-05-26 | 2020-05-11 | Neurophyxia B V | Formulaciones de 2-iminobiotina y usos de las mismas |
WO2012034038A2 (en) * | 2010-09-09 | 2012-03-15 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Dual inhibitors of farnesyltransferase and geranylgeranyltransferase i |
RU2632097C2 (ru) * | 2011-10-07 | 2017-10-02 | ПАЙСИЗ ТЕРАПЬЮТИКЗ ЭлЭлСи | Лечение злокачественных и незлокачественных заболеваний с помощью антагонистов ras |
CN105194685A (zh) * | 2015-10-15 | 2015-12-30 | 重庆大学 | 磺胺脒的磺丁基醚-β-环糊精包合物及其粉针制剂 |
PL3389653T3 (pl) | 2015-12-16 | 2024-02-26 | Neurophyxia B.V. | 2-iminobiotyna do zastosowania w leczeniu uszkodzeń komórek mózgowych |
US10045991B2 (en) | 2016-04-04 | 2018-08-14 | Loxo Oncology, Inc. | Methods of treating pediatric cancers |
WO2017176751A1 (en) | 2016-04-04 | 2017-10-12 | Loxo Oncology, Inc. | Liquid formulations of (s)-n-(5-((r)-2-(2,5-difluorophenyl)-pyrrolidin-1-yl)-pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxypyrrolidine-1-carboxamide |
JP7443057B2 (ja) | 2016-05-18 | 2024-03-05 | ロクソ オンコロジー, インコーポレイテッド | (S)-N-(5-((R)-2-(2,5-ジフルオロフェニル)ピロリジン-1-イル)-ピラゾロ[1,5-a]ピリミジン-3-イル)-3-ヒドロキシピロリジン-1-カルボキサミドの調製 |
JOP20190092A1 (ar) | 2016-10-26 | 2019-04-25 | Array Biopharma Inc | عملية لتحضير مركبات بيرازولو[1، 5-a]بيريميدين وأملاح منها |
US20210145816A1 (en) * | 2019-11-15 | 2021-05-20 | Cyclolab Cyclodextrin Research And Development Laboratory Ltd. | Pharmaceutical formulation of lonafarnib with a sulfobutylether beta-cyclodextrin |
WO2023113479A1 (en) * | 2021-12-15 | 2023-06-22 | Sillajen, Inc. | Pharmaceutical compositions comprising modified beta-cyclodextrins |
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JPS5630927A (en) * | 1979-08-24 | 1981-03-28 | Zeria Shinyaku Kogyo Kk | Stabilization of guaiazulene and its derivative |
US4371673A (en) * | 1980-07-21 | 1983-02-01 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Water soluble forms of retinoids |
US4727064A (en) * | 1984-04-25 | 1988-02-23 | The United States Of America As Represented By The Department Of Health And Human Services | Pharmaceutical preparations containing cyclodextrin derivatives |
US4596795A (en) * | 1984-04-25 | 1986-06-24 | The United States Of America As Represented By The Secretary, Dept. Of Health & Human Services | Administration of sex hormones in the form of hydrophilic cyclodextrin derivatives |
KR0166088B1 (ko) * | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
US5376645A (en) | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
JPH07165616A (ja) * | 1993-12-09 | 1995-06-27 | Hisamitsu Pharmaceut Co Inc | シクロデキストリンの複合組成物及び複合化法 |
US6011029A (en) * | 1996-02-26 | 2000-01-04 | Bristol-Myers Squibb Company | Inhibitors of farnesyl protein transferase |
JPH1067639A (ja) * | 1996-08-26 | 1998-03-10 | Shiseido Co Ltd | ビタミンe−ビタミンcリン酸ジエステル/シクロデキストリン包接物及び該包接物を配合した皮膚外用剤 |
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1999
- 1999-12-21 CA CA002359646A patent/CA2359646C/en not_active Expired - Fee Related
- 1999-12-21 CN CNB998157074A patent/CN1219517C/zh not_active Expired - Fee Related
- 1999-12-21 EE EEP200100382A patent/EE200100382A/xx unknown
- 1999-12-21 HU HU0105160A patent/HUP0105160A3/hu unknown
- 1999-12-21 ID IDW00200101596A patent/ID30139A/id unknown
- 1999-12-21 NZ NZ511995A patent/NZ511995A/en unknown
- 1999-12-21 AU AU23740/00A patent/AU772204B2/en not_active Ceased
- 1999-12-21 IL IL14402599A patent/IL144025A/en not_active IP Right Cessation
- 1999-12-21 RU RU2001118265/04A patent/RU2230062C2/ru not_active IP Right Cessation
- 1999-12-21 EP EP99967470A patent/EP1143796A4/en not_active Withdrawn
- 1999-12-21 KR KR1020017009131A patent/KR100708360B1/ko not_active IP Right Cessation
- 1999-12-21 TR TR2001/02109T patent/TR200102109T2/xx unknown
- 1999-12-21 CZ CZ20012601A patent/CZ20012601A3/cs unknown
- 1999-12-21 SK SK960-2001A patent/SK9602001A3/sk unknown
- 1999-12-21 BR BR9916566-0A patent/BR9916566A/pt not_active Application Discontinuation
- 1999-12-21 UA UA2001085843A patent/UA67825C2/uk unknown
- 1999-12-21 JP JP2000594323A patent/JP2002535253A/ja active Pending
- 1999-12-21 GE GEAP19995955A patent/GEP20043214B/en unknown
- 1999-12-21 PL PL99366338A patent/PL195280B1/pl not_active IP Right Cessation
- 1999-12-21 WO PCT/US1999/030424 patent/WO2000042849A1/en active IP Right Grant
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2000
- 2000-01-14 TW TW089100557A patent/TWI232752B/zh not_active IP Right Cessation
- 2000-01-17 US US09/483,840 patent/US6218375B1/en not_active Expired - Lifetime
- 2000-01-18 CO CO00002434A patent/CO5160253A1/es unknown
- 2000-01-20 AR ARP000100255A patent/AR022323A1/es unknown
- 2000-01-21 UY UY25986A patent/UY25986A1/es unknown
- 2000-01-21 UY UY25987A patent/UY25987A1/es not_active Application Discontinuation
- 2000-01-21 PE PE2000000046A patent/PE20001419A1/es not_active Application Discontinuation
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2001
- 2001-05-29 ZA ZA200104416A patent/ZA200104416B/en unknown
- 2001-06-21 LT LT2001064A patent/LT4893B/lt not_active IP Right Cessation
- 2001-07-03 BG BG105666A patent/BG105666A/xx unknown
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2002
- 2002-01-08 HK HK02100115.8A patent/HK1038865A1/zh unknown
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