JP2002522443A5 - - Google Patents
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- Publication number
- JP2002522443A5 JP2002522443A5 JP2000563666A JP2000563666A JP2002522443A5 JP 2002522443 A5 JP2002522443 A5 JP 2002522443A5 JP 2000563666 A JP2000563666 A JP 2000563666A JP 2000563666 A JP2000563666 A JP 2000563666A JP 2002522443 A5 JP2002522443 A5 JP 2002522443A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- group
- taxol
- pharmaceutically acceptable
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical group 0.000 description 29
- 239000003814 drug Substances 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 229940079593 drug Drugs 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 229930012538 Paclitaxel Natural products 0.000 description 6
- 229910001413 alkali metal ion Inorganic materials 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229960001592 paclitaxel Drugs 0.000 description 6
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- OLBCVFGFOZPWHH-UHFFFAOYSA-N propofol Chemical compound CC(C)C1=CC=CC(C(C)C)=C1O OLBCVFGFOZPWHH-UHFFFAOYSA-N 0.000 description 5
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229940127093 camptothecin Drugs 0.000 description 3
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229960004134 propofol Drugs 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 229930105110 Cyclosporin A Natural products 0.000 description 2
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 2
- 108010036949 Cyclosporine Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229930003427 Vitamin E Natural products 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 229960001265 ciclosporin Drugs 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 2
- 229960005420 etoposide Drugs 0.000 description 2
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 2
- CPZBTYRIGVOOMI-UHFFFAOYSA-N methylsulfanyl(methylsulfanylmethoxy)methane Chemical compound CSCOCSC CPZBTYRIGVOOMI-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229940046009 vitamin E Drugs 0.000 description 2
- 235000019165 vitamin E Nutrition 0.000 description 2
- 239000011709 vitamin E Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GCKMFJBGXUYNAG-UHFFFAOYSA-N 17alpha-methyltestosterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C)(O)C1(C)CC2 GCKMFJBGXUYNAG-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- GCKMFJBGXUYNAG-HLXURNFRSA-N Methyltestosterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 GCKMFJBGXUYNAG-HLXURNFRSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 1
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- KUCQYCKVKVOKAY-CTYIDZIISA-N atovaquone Chemical compound C1([C@H]2CC[C@@H](CC2)C2=C(C(C3=CC=CC=C3C2=O)=O)O)=CC=C(Cl)C=C1 KUCQYCKVKVOKAY-CTYIDZIISA-N 0.000 description 1
- 229960003159 atovaquone Drugs 0.000 description 1
- POZRVZJJTULAOH-LHZXLZLDSA-N danazol Chemical compound C1[C@]2(C)[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=CC2=C1C=NO2 POZRVZJJTULAOH-LHZXLZLDSA-N 0.000 description 1
- 229960000766 danazol Drugs 0.000 description 1
- 239000003118 drug derivative Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229960001566 methyltestosterone Drugs 0.000 description 1
- KADXVMRYQRCLAH-UHFFFAOYSA-N n'-iodobutanediamide Chemical compound NC(=O)CCC(=O)NI KADXVMRYQRCLAH-UHFFFAOYSA-N 0.000 description 1
- 125000006245 phosphate protecting group Chemical group 0.000 description 1
- -1 phosphonooxymethyl Chemical class 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/131,385 | 1998-08-07 | ||
| US09/131,385 US6204257B1 (en) | 1998-08-07 | 1998-08-07 | Water soluble prodrugs of hindered alcohols |
| PCT/US1999/017779 WO2000008033A1 (en) | 1998-08-07 | 1999-08-06 | Water soluble prodrugs of hindered alcohols or phenols |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002522443A JP2002522443A (ja) | 2002-07-23 |
| JP2002522443A5 true JP2002522443A5 (enExample) | 2006-09-28 |
| JP4554081B2 JP4554081B2 (ja) | 2010-09-29 |
Family
ID=22449234
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000563666A Expired - Fee Related JP4554081B2 (ja) | 1998-08-07 | 1999-08-06 | ヒンダードアルコールまたはフェノールの水溶性プロドラッグ |
Country Status (27)
| Country | Link |
|---|---|
| US (4) | US6204257B1 (enExample) |
| EP (2) | EP1683803A1 (enExample) |
| JP (1) | JP4554081B2 (enExample) |
| KR (1) | KR100662799B1 (enExample) |
| CN (2) | CN1680402A (enExample) |
| AT (1) | ATE319723T1 (enExample) |
| AU (1) | AU769755B2 (enExample) |
| BR (1) | BR9912853A (enExample) |
| CA (1) | CA2339834C (enExample) |
| CY (1) | CY1105043T1 (enExample) |
| CZ (1) | CZ304020B6 (enExample) |
| DE (1) | DE69930269T2 (enExample) |
| DK (1) | DK1102776T3 (enExample) |
| ES (1) | ES2268876T3 (enExample) |
| HK (1) | HK1047939B (enExample) |
| HU (1) | HU229401B1 (enExample) |
| IL (1) | IL141316A (enExample) |
| MX (1) | MXPA01001431A (enExample) |
| NO (1) | NO330357B1 (enExample) |
| NZ (1) | NZ509795A (enExample) |
| PL (1) | PL198141B1 (enExample) |
| PT (1) | PT1102776E (enExample) |
| RU (1) | RU2235727C2 (enExample) |
| TR (1) | TR200100772T2 (enExample) |
| UA (1) | UA73479C2 (enExample) |
| WO (1) | WO2000008033A1 (enExample) |
| ZA (1) | ZA200101039B (enExample) |
Families Citing this family (119)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6979456B1 (en) | 1998-04-01 | 2005-12-27 | Jagotec Ag | Anticancer compositions |
| US6204257B1 (en) * | 1998-08-07 | 2001-03-20 | Universtiy Of Kansas | Water soluble prodrugs of hindered alcohols |
| EP1105096B1 (en) | 1998-08-19 | 2003-10-29 | Skyepharma Canada Inc. | Injectable aqueous dispersions of propofol |
| US6362172B2 (en) * | 2000-01-20 | 2002-03-26 | Bristol-Myers Squibb Company | Water soluble prodrugs of azole compounds |
| US6362234B1 (en) * | 2000-08-15 | 2002-03-26 | Vyrex Corporation | Water-soluble prodrugs of propofol for treatment of migrane |
| US6448401B1 (en) * | 2000-11-20 | 2002-09-10 | Bristol-Myers Squibb Company | Process for water soluble azole compounds |
| ES2256450T3 (es) * | 2001-04-20 | 2006-07-16 | Debiopharm S.A. | Ciclosporina modificada utilizable como profarmaco y su uso. |
| US6815555B2 (en) | 2001-09-26 | 2004-11-09 | Theravance, Inc. | Substituted phenol compounds useful for anesthesia and sedation |
| KR101016969B1 (ko) * | 2001-12-21 | 2011-02-25 | 에이자이 아이엔씨. | 알콜 및 페놀의 수용성 포스포노옥시메틸 유도체를제조하는 방법 |
| BR0215303A (pt) * | 2001-12-28 | 2005-04-05 | Guilford Pharm Inc | Formulações farmacêuticas de base aquosa de pró-drogas solúveis em água de propofol |
| KR20070087004A (ko) * | 2002-04-08 | 2007-08-27 | 엠쥐아이 쥐피, 아이엔씨. | 프로포폴의 수용성 프로드럭을 함유하는 약제학적 조성물및 그것을 투여하는 방법 |
| ITRM20020306A1 (it) | 2002-05-31 | 2003-12-01 | Sigma Tau Ind Farmaceuti | Esteri in posizione 20 di camptotecine. |
| AU2002950713A0 (en) | 2002-08-09 | 2002-09-12 | Vital Health Sciences Pty Ltd | Carrier |
| ZA200504940B (en) * | 2003-01-28 | 2006-09-27 | Xenoport Inc | Amino acid derived prodrugs of propofol, compositions and uses thereof |
| CA2518265A1 (en) | 2003-03-17 | 2004-09-30 | Albany Molecular Research, Inc. | Novel cyclosporins |
| AU2003901815A0 (en) * | 2003-04-15 | 2003-05-01 | Vital Health Sciences Pty Ltd | Phosphate derivatives |
| WO2005023204A2 (en) * | 2003-09-09 | 2005-03-17 | Xenoport, Inc. | Aromatic prodrugs of propofol, compositions and uses thereof |
| CN1882548A (zh) * | 2003-10-24 | 2006-12-20 | 奥斯佩克斯制药公司 | 2,6－二异丙基苯酚的pH敏感性前药 |
| US7834043B2 (en) * | 2003-12-11 | 2010-11-16 | Abbott Laboratories | HIV protease inhibiting compounds |
| US20070202158A1 (en) * | 2003-12-17 | 2007-08-30 | Mgi Gp, Inc. | Methods Of Administering Water-Soluble Prodrugs Of Propofol For Extended Sedation |
| US8129346B2 (en) | 2004-04-15 | 2012-03-06 | Onyx Therapeutics, Inc. | Compounds for enzyme inhibition |
| US7232818B2 (en) * | 2004-04-15 | 2007-06-19 | Proteolix, Inc. | Compounds for enzyme inhibition |
| US8198270B2 (en) * | 2004-04-15 | 2012-06-12 | Onyx Therapeutics, Inc. | Compounds for proteasome enzyme inhibition |
| CA2565407A1 (en) * | 2004-05-10 | 2005-11-24 | Proteolix, Inc. | Compounds for enzyme inhibition |
| US20050256324A1 (en) * | 2004-05-10 | 2005-11-17 | Proteolix, Inc. | Synthesis of amino acid keto-epoxides |
| EP2336138A3 (en) * | 2004-07-06 | 2011-11-16 | Abbott Laboratories | Prodrugs of HIV protease inhibitors |
| US7241807B2 (en) * | 2004-07-12 | 2007-07-10 | Xenoport, Inc. | Prodrugs of propofol, compositions and uses thereof |
| PT1781596E (pt) * | 2004-07-12 | 2009-01-12 | Xenoport Inc | Pró-fármacos de propofol derivados de aminoácidos, composições e utilizações dos mesmos |
| US20060014677A1 (en) * | 2004-07-19 | 2006-01-19 | Isotechnika International Inc. | Method for maximizing efficacy and predicting and minimizing toxicity of calcineurin inhibitor compounds |
| EP2266622A3 (en) * | 2004-08-26 | 2012-06-20 | Piramal Life Sciences Limited | Prodrugs containing novel bio-cleavable linkers |
| WO2006033911A2 (en) * | 2004-09-17 | 2006-03-30 | Mgi Gp, Inc. | Methods of administering water-soluble prodrugs of propofol |
| JP2008514701A (ja) | 2004-09-29 | 2008-05-08 | エーエムアール テクノロジー インコーポレイテッド | シクロスポリンアルキン類似体およびそれらの薬学的使用 |
| US7511013B2 (en) | 2004-09-29 | 2009-03-31 | Amr Technology, Inc. | Cyclosporin analogues and their pharmaceutical uses |
| WO2006041631A2 (en) | 2004-10-06 | 2006-04-20 | Amr Technology, Inc. | Novel cyclosporin alkynes and their utility as pharmaceutical agents |
| ATE456552T1 (de) * | 2004-12-23 | 2010-02-15 | Xenoport Inc | Von serinaminosäure abgeleitete prodrugs von propofol, zusammensetzungen, anwendungen und kristalline formen davon |
| EP2548581A3 (en) | 2005-06-17 | 2013-02-20 | Vital Health Sciences Pty Ltd. | A carrier comprising one or more di and/or mono-(electron transfer agent) phosphate derivatives or complexes thereof |
| WO2007008869A1 (en) * | 2005-07-12 | 2007-01-18 | Mgi Gp, Inc. | Methods of dosing propofol prodrugs for inducing mild to moderate levels of sedation |
| US20080234229A1 (en) * | 2005-08-18 | 2008-09-25 | Auspex Pharmaceuticals, Inc. | Novel Therapeutic Agents for the Treatment of Cancer, Metabolic Diseases and Skin Disorders |
| ES2441608T3 (es) | 2005-08-18 | 2014-02-05 | Zimmer Gmbh | Artículos de polietileno de peso molecular ultra-alto y métodos para formar artículos de polietileno de peso molecular ulra-alto |
| WO2007028104A2 (en) * | 2005-09-02 | 2007-03-08 | Auspex Pharmaceuticals, Inc. | Novel therapeutic agents for the treatment of cancer, metabolic diseases and skin disorders |
| CN101282979B (zh) * | 2005-09-13 | 2011-09-21 | 卫材R&D管理有限公司 | 稳定性被改善的含有磷酸氯甲酯衍生物的组合物及其制备方法 |
| KR101434522B1 (ko) * | 2005-11-09 | 2014-08-26 | 오닉스 세라퓨틱스, 인크. | 효소 저해를 위한 화합물 |
| US7691852B2 (en) * | 2006-06-19 | 2010-04-06 | Onyx Therapeutics, Inc. | Compounds for enzyme inhibition |
| CN101583271B (zh) * | 2006-10-05 | 2013-07-17 | 卫材公司 | 丙泊酚水溶性前药的水基药物制剂 |
| US20080161400A1 (en) * | 2006-10-26 | 2008-07-03 | Xenoport, Inc. | Use of forms of propofol for treating diseases associated with oxidative stress |
| US8664290B2 (en) | 2007-04-10 | 2014-03-04 | Zimmer, Inc. | Antioxidant stabilized crosslinked ultra-high molecular weight polyethylene for medical device applications |
| ES2378721T3 (es) | 2007-04-10 | 2012-04-17 | Zimmer, Inc. | Polietileno reticulado de peso molecular ultra alto estabilizado por antioxidantes para aplicaciones en dispositivos médicos |
| PL2146946T3 (pl) | 2007-05-09 | 2011-04-29 | Pharmacofore Inc | (-)-Stereoizomer 2,6-di-sec-butylofenolu i jego analogi |
| CA2685813A1 (en) | 2007-05-09 | 2008-11-20 | Pharmacofore, Inc. | Therapeutic compounds |
| US20090005444A1 (en) * | 2007-06-21 | 2009-01-01 | Xenoport, Inc. | Use of propofol prodrugs for treating alcohol withdrawal, central pain, anxiety or pruritus |
| FI20070574A0 (fi) * | 2007-07-30 | 2007-07-30 | Kuopion Yliopisto | Vesiliukoinen propofolin etylideenifosfaatti-aihiolääke |
| US8427384B2 (en) | 2007-09-13 | 2013-04-23 | Aerosat Corporation | Communication system with broadband antenna |
| CN101842938B (zh) * | 2007-09-13 | 2014-11-05 | 天文电子学爱罗莎特股份有限公司 | 有宽带天线的通信系统 |
| WO2009036322A1 (en) * | 2007-09-14 | 2009-03-19 | Xenoport, Inc. | Use of propofol prodrugs for treating neuropathic pain |
| US20090075947A1 (en) * | 2007-09-17 | 2009-03-19 | Protia, Llc | Deuterium-enriched fospropofol |
| RS54847B2 (sr) | 2007-10-04 | 2019-09-30 | Onyx Therapeutics Inc | Inhibitori kristalne peptid epoksi keton proteaze i sinteza aminokiselinskih keto-epoksida |
| US20090098209A1 (en) * | 2007-10-15 | 2009-04-16 | University Of Kansas | Pharmaceutical compositions containing water-soluble derivatives of propofol and methods of administering same via pulmonary administration |
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- 1999-08-06 TR TR2001/00772T patent/TR200100772T2/xx unknown
- 1999-08-06 RU RU2001106614/04A patent/RU2235727C2/ru not_active IP Right Cessation
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- 1999-08-06 HK HK03100006.9A patent/HK1047939B/zh not_active IP Right Cessation
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- 1999-08-06 CN CNA2005100524949A patent/CN1680402A/zh active Pending
- 1999-08-06 KR KR1020017001674A patent/KR100662799B1/ko not_active Expired - Fee Related
- 1999-08-06 CZ CZ20010479A patent/CZ304020B6/cs not_active IP Right Cessation
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