LT4893B - RAS-FARNEZILTRANSFERAZĖS INHIBITORIAUS IR SULFOBUTILETER-7-ß-CIKLODEKSTRINO ARBA 2-HIDROKSIPROPIL-ß-CIKLODEKSTRINO KOMPLEKSAS IR JO GAVIMO BŪDAS - Google Patents
RAS-FARNEZILTRANSFERAZĖS INHIBITORIAUS IR SULFOBUTILETER-7-ß-CIKLODEKSTRINO ARBA 2-HIDROKSIPROPIL-ß-CIKLODEKSTRINO KOMPLEKSAS IR JO GAVIMO BŪDAS Download PDFInfo
- Publication number
- LT4893B LT4893B LT2001064A LT2001064A LT4893B LT 4893 B LT4893 B LT 4893B LT 2001064 A LT2001064 A LT 2001064A LT 2001064 A LT2001064 A LT 2001064A LT 4893 B LT4893 B LT 4893B
- Authority
- LT
- Lithuania
- Prior art keywords
- cyclodextrin
- inhibitor
- benzodiazepine
- phenylmethyl
- imidazol
- Prior art date
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- 229920000858 Cyclodextrin Polymers 0.000 title claims abstract description 41
- 239000003528 protein farnesyltransferase inhibitor Substances 0.000 title claims abstract description 21
- 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 claims abstract description 18
- 229940124226 Farnesyltransferase inhibitor Drugs 0.000 title claims abstract description 17
- 229960004853 betadex Drugs 0.000 title abstract description 14
- 239000001116 FEMA 4028 Substances 0.000 title abstract description 13
- 238000000034 method Methods 0.000 title abstract description 6
- -1 sulfobutyl Chemical group 0.000 claims abstract description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000003112 inhibitor Substances 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 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 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000003287 1H-imidazol-4-ylmethyl group Chemical group [H]N1C([H])=NC(C([H])([H])[*])=C1[H] 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 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 6
- 239000000872 buffer Substances 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 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 4
- 238000007911 parenteral administration Methods 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- WDIWKDRZXKMPAH-HSZRJFAPSA-N (3r)-3-benzyl-1-(1h-imidazol-5-ylmethyl)-4-propylsulfonyl-3,5-dihydro-2h-1,4-benzodiazepine-7-carbonitrile Chemical compound CCCS(=O)(=O)N([C@@H](C1)CC=2C=CC=CC=2)CC2=CC(C#N)=CC=C2N1CC1=CNC=N1 WDIWKDRZXKMPAH-HSZRJFAPSA-N 0.000 claims description 3
- KJFQITPHGCFLGP-RUZDIDTESA-N (3r)-3-benzyl-4-(4-fluorophenyl)sulfonyl-1-(1h-imidazol-5-ylmethyl)-3,5-dihydro-2h-1,4-benzodiazepine-7-carbonitrile Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1[C@H](CC=2C=CC=CC=2)CN(CC=2N=CNC=2)C2=CC=C(C#N)C=C2C1 KJFQITPHGCFLGP-RUZDIDTESA-N 0.000 claims description 3
- 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 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 239000003937 drug carrier Substances 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
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 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
- ZCOJTDGEOXTSLT-UHFFFAOYSA-N 1-thiophen-2-ylsulfonyl-1,4-benzodiazepine Chemical compound C1=CN=CC2=CC=CC=C2N1S(=O)(=O)C1=CC=CS1 ZCOJTDGEOXTSLT-UHFFFAOYSA-N 0.000 claims 2
- RHXLRBJBYOPEAL-RUZDIDTESA-N (3r)-4-(benzenesulfonyl)-3-benzyl-1-(1h-imidazol-5-ylmethyl)-3,5-dihydro-2h-1,4-benzodiazepine-7-carbonitrile Chemical compound C=1C=CC=CC=1S(=O)(=O)N([C@@H](C1)CC=2C=CC=CC=2)CC2=CC(C#N)=CC=C2N1CC1=CNC=N1 RHXLRBJBYOPEAL-RUZDIDTESA-N 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 abstract description 7
- 239000002246 antineoplastic agent Substances 0.000 abstract description 4
- 206010028980 Neoplasm Diseases 0.000 abstract description 3
- 201000011510 cancer Diseases 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 27
- 229940125904 compound 1 Drugs 0.000 description 17
- 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 description 10
- 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 9
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- 125000001424 substituent group Chemical group 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000008367 deionised water Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 6
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 6
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- 239000012458 free base Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- NZAQRZWBQUIBSF-UHFFFAOYSA-N 4-(4-sulfobutoxy)butane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCCOCCCCS(O)(=O)=O NZAQRZWBQUIBSF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- RTUHZLGYTXOVIJ-UHFFFAOYSA-N 1h-1,4-benzodiazepine-7-carbonitrile Chemical compound N1C=CN=CC2=CC(C#N)=CC=C21 RTUHZLGYTXOVIJ-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11664799P | 1999-01-21 | 1999-01-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LT2001064A LT2001064A (en) | 2001-10-25 |
| LT4893B true LT4893B (lt) | 2002-02-25 |
Family
ID=22368422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LT2001064A LT4893B (lt) | 1999-01-21 | 2001-06-21 | RAS-FARNEZILTRANSFERAZĖS INHIBITORIAUS IR SULFOBUTILETER-7-ß-CIKLODEKSTRINO ARBA 2-HIDROKSIPROPIL-ß-CIKLODEKSTRINO KOMPLEKSAS IR JO GAVIMO BŪDAS |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US6218375B1 (pl) |
| EP (1) | EP1143796A4 (pl) |
| JP (1) | JP2002535253A (pl) |
| KR (1) | KR100708360B1 (pl) |
| CN (1) | CN1219517C (pl) |
| AR (1) | AR022323A1 (pl) |
| AU (1) | AU772204B2 (pl) |
| BG (1) | BG105666A (pl) |
| BR (1) | BR9916566A (pl) |
| CA (1) | CA2359646C (pl) |
| CO (1) | CO5160253A1 (pl) |
| CZ (1) | CZ20012601A3 (pl) |
| EE (1) | EE200100382A (pl) |
| GE (1) | GEP20043214B (pl) |
| HK (1) | HK1038865A1 (pl) |
| HU (1) | HUP0105160A3 (pl) |
| ID (1) | ID30139A (pl) |
| IL (1) | IL144025A (pl) |
| LT (1) | LT4893B (pl) |
| LV (1) | LV12712B (pl) |
| MY (1) | MY119700A (pl) |
| NO (1) | NO20013585L (pl) |
| NZ (1) | NZ511995A (pl) |
| PE (1) | PE20001419A1 (pl) |
| PL (1) | PL195280B1 (pl) |
| RU (1) | RU2230062C2 (pl) |
| SK (1) | SK9602001A3 (pl) |
| TR (1) | TR200102109T2 (pl) |
| TW (1) | TWI232752B (pl) |
| UA (1) | UA67825C2 (pl) |
| UY (2) | UY25987A1 (pl) |
| WO (1) | WO2000042849A1 (pl) |
| ZA (1) | ZA200104416B (pl) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US6818662B2 (en) * | 2002-05-28 | 2004-11-16 | Taisho Pharmaceutical Co., Ltd. | Pharmaceutical composition |
| US20040009972A1 (en) * | 2002-06-17 | 2004-01-15 | Ding Charles Z. | Benzodiazepine inhibitors of mitochondial F1F0 ATP hydrolase and methods of inhibiting F1F0 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 |
| EP1928464B1 (en) | 2005-09-30 | 2014-05-14 | Lundbeck Inc. | Novel parenteral carbamazepine formulation |
| US20100204178A1 (en) | 2006-10-02 | 2010-08-12 | James Cloyd | Novel parenteral carbamazepine formulation |
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