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 US6204257B1 (en) | 1998-08-07 | 1998-08-07 | Water soluble prodrugs of hindered alcohols |
| US09/131,385 | 1998-08-07 | ||
| 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 (https=) | 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 (https=) |
| EP (2) | EP1683803A1 (https=) |
| JP (1) | JP4554081B2 (https=) |
| KR (1) | KR100662799B1 (https=) |
| CN (2) | CN1680402A (https=) |
| AT (1) | ATE319723T1 (https=) |
| AU (1) | AU769755B2 (https=) |
| BR (1) | BR9912853A (https=) |
| CA (1) | CA2339834C (https=) |
| CY (1) | CY1105043T1 (https=) |
| CZ (1) | CZ304020B6 (https=) |
| DE (1) | DE69930269T2 (https=) |
| DK (1) | DK1102776T3 (https=) |
| ES (1) | ES2268876T3 (https=) |
| HK (1) | HK1047939B (https=) |
| HU (1) | HU229401B1 (https=) |
| IL (1) | IL141316A (https=) |
| MX (1) | MXPA01001431A (https=) |
| NO (1) | NO330357B1 (https=) |
| NZ (1) | NZ509795A (https=) |
| PL (1) | PL198141B1 (https=) |
| PT (1) | PT1102776E (https=) |
| RU (1) | RU2235727C2 (https=) |
| TR (1) | TR200100772T2 (https=) |
| UA (1) | UA73479C2 (https=) |
| WO (1) | WO2000008033A1 (https=) |
| ZA (1) | ZA200101039B (https=) |
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 |
| DE69912441T2 (de) | 1998-08-19 | 2004-08-19 | Skyepharma Canada Inc., Verdun | Injizierbare wässerige propofoldispersionen |
| 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 |
| US6995139B2 (en) * | 2001-04-20 | 2006-02-07 | Debiopharm S.A. | Cyclic undecapeptide pro-drugs and uses thereof |
| CA2459125A1 (en) * | 2001-09-26 | 2003-04-03 | Theravance, Inc. | Substituted phenol compounds useful for anesthesia and sedation |
| JP4369237B2 (ja) * | 2001-12-21 | 2009-11-18 | エーザイ コーポレーション オブ ノース アメリカ | アルコールおよびフェノールの水溶性ホスホノオキシメチル誘導体の調製法 |
| NZ533536A (en) * | 2001-12-28 | 2006-11-30 | Mgi Gp Inc | Aqueous based pharmaceutical formulations of water-soluble prodrugs of propofol such as O-phosphonooxymethyl propofol |
| HUP0600241A2 (en) * | 2002-04-08 | 2006-07-28 | Mgi Gp | Pharmaceutical compositions containing water-soluble prodrugs of propofol and methods of administering same |
| 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 |
| US7538084B2 (en) | 2003-03-17 | 2009-05-26 | Amr Technology, Inc. | Cyclosporins |
| AU2003901815A0 (en) * | 2003-04-15 | 2003-05-01 | Vital Health Sciences Pty Ltd | Phosphate derivatives |
| US7230003B2 (en) * | 2003-09-09 | 2007-06-12 | Xenoport, Inc. | Aromatic prodrugs of propofol, compositions and uses thereof |
| US7250412B2 (en) * | 2003-10-24 | 2007-07-31 | Auspex Pharmaceuticals, Inc. | PH sensitive prodrugs of 2,6-Diisopropylphenol |
| US7834043B2 (en) * | 2003-12-11 | 2010-11-16 | Abbott Laboratories | HIV protease inhibiting compounds |
| BRPI0417472A (pt) * | 2003-12-17 | 2007-05-08 | Mgi Gp Inc | métodos para administração de prodrogas de propofol solúveis em água para sedação prolongada |
| US8198270B2 (en) * | 2004-04-15 | 2012-06-12 | Onyx Therapeutics, Inc. | Compounds for proteasome enzyme inhibition |
| 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 |
| EP2030981B1 (en) * | 2004-05-10 | 2014-07-09 | Onyx Therapeutics, Inc. | Compounds for proteasome enzyme inhibition |
| AU2005243140A1 (en) * | 2004-05-10 | 2005-11-24 | Proteolix, Inc. | Synthesis of amino acid keto-epoxides |
| CA2571726C (en) * | 2004-07-06 | 2013-05-21 | Abbott Laboratories | Prodrugs of hiv protease inhibitors |
| US7241807B2 (en) * | 2004-07-12 | 2007-07-10 | Xenoport, Inc. | Prodrugs of propofol, compositions and uses thereof |
| DE602005010270D1 (de) * | 2004-07-12 | 2008-11-20 | Xenoport Inc | Von aminosäuren abgeleitete prodrugs von propofolzusammensetzungen und anwendungen davon |
| US20060014677A1 (en) * | 2004-07-19 | 2006-01-19 | Isotechnika International Inc. | Method for maximizing efficacy and predicting and minimizing toxicity of calcineurin inhibitor compounds |
| KR20070053214A (ko) * | 2004-08-26 | 2007-05-23 | 니콜라스 피라말 인디아 리미티드 | 신규 생분해성 링커를 함유하는 프로드럭 |
| 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 |
| JP2008514702A (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 | 新規シクロスポリン類似体およびそれらの薬学的使用 |
| JP2008515886A (ja) | 2004-10-06 | 2008-05-15 | 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およびそれらの医用薬剤としての有用性 |
| EP1844000B1 (en) * | 2004-12-23 | 2010-01-27 | Xenoport, Inc. | Serine amino acid derived prodrugs of propofol, compositions, uses and crystalline forms thereof |
| US9168216B2 (en) | 2005-06-17 | 2015-10-27 | Vital Health Sciences Pty. Ltd. | 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 |
| WO2007022437A2 (en) * | 2005-08-18 | 2007-02-22 | Auspex Pharmaceuticals, Inc. | Therapeutic agents for the treatment of cancer and metabolic disorders |
| EP2277560B1 (en) | 2005-08-18 | 2013-10-09 | Zimmer GmbH | Ultra high molecular weight polyethylene articles and methods od forming ultra high molecular weight polyethylene articles |
| US7589239B2 (en) * | 2005-09-02 | 2009-09-15 | Auspex Pharmaceuticals | Therapeutic agents for the treatment of cancer, metabolic diseases and skin disorders |
| JP4981673B2 (ja) * | 2005-09-13 | 2012-07-25 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 安定性が改善されたクロロメチルフォスフェイト誘導体を含む組成物およびその製造方法 |
| MY171061A (en) * | 2005-11-09 | 2019-09-24 | Onyx Therapeutics Inc | Compounds for enzyme inhibition |
| CA2657213C (en) | 2006-06-19 | 2017-01-03 | Proteolix, Inc. | Peptide epoxyketones for proteasome inhibition |
| KR20090059136A (ko) * | 2006-10-05 | 2009-06-10 | 에이자이 코포레이션 오브 노쓰아메리카 | 프로포폴의 수용성 프로드럭의 수성 약제학적 제제 |
| WO2008052044A2 (en) * | 2006-10-26 | 2008-05-02 | Xenoport, Inc. | Use of derivatives of propofol for treating diseases associated with oxidative stress |
| EP2150285B1 (en) | 2007-04-10 | 2012-02-08 | Zimmer, Inc. | An antioxidant stabilized crosslinked ultra-high molecular weight polyethylene for medical device applications |
| US8664290B2 (en) | 2007-04-10 | 2014-03-04 | Zimmer, Inc. | Antioxidant stabilized crosslinked ultra-high molecular weight polyethylene for medical device applications |
| MY147215A (en) | 2007-05-09 | 2012-11-14 | Pharmacofore Inc | Therapeutic compunds |
| CN101715437B (zh) | 2007-05-09 | 2013-06-12 | 特色疗法股份有限公司 | 立体异构异丙酚治疗性化合物 |
| WO2008157627A1 (en) * | 2007-06-21 | 2008-12-24 | 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 |
| WO2009036305A1 (en) * | 2007-09-13 | 2009-03-19 | Aerosat Corporation | Communication system with broadband antenna |
| US20090076141A1 (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 |
| KR20170125413A (ko) | 2007-10-04 | 2017-11-14 | 오닉스 세라퓨틱스, 인크. | 결정형 펩티드 에폭시 케톤 프로테아제 저해제 및 아미노산 케토-에폭시드의 합성 |
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- 1999-08-06 WO PCT/US1999/017779 patent/WO2000008033A1/en not_active Ceased
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- 1999-08-06 KR KR1020017001674A patent/KR100662799B1/ko not_active Expired - Fee Related
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- 1999-08-06 DE DE69930269T patent/DE69930269T2/de not_active Expired - Lifetime
- 1999-08-06 HK HK03100006.9A patent/HK1047939B/zh not_active IP Right Cessation
- 1999-08-06 EP EP99939030A patent/EP1102776B1/en not_active Expired - Lifetime
- 1999-08-06 PT PT99939030T patent/PT1102776E/pt unknown
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