JP2004517045A - 癌およびｈｉｖの治療用ベツリン酸誘導体のプロドラッグ - Google Patents
癌およびｈｉｖの治療用ベツリン酸誘導体のプロドラッグ Download PDFInfo
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- JP2004517045A JP2004517045A JP2002521491A JP2002521491A JP2004517045A JP 2004517045 A JP2004517045 A JP 2004517045A JP 2002521491 A JP2002521491 A JP 2002521491A JP 2002521491 A JP2002521491 A JP 2002521491A JP 2004517045 A JP2004517045 A JP 2004517045A
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- alkyl
- betulinic acid
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- CFCUWKMKBJTWLW-BKHRDMLASA-N mithramycin Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@H]1O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1C)O[C@@H]1O[C@H](C)[C@@H](O)[C@H](O[C@@H]2O[C@H](C)[C@H](O)[C@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@@](C)(O)C3)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@@H](O)[C@H](O)[C@@H](C)O1 CFCUWKMKBJTWLW-BKHRDMLASA-N 0.000 description 1
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- 210000004498 neuroglial cell Anatomy 0.000 description 1
- 231100000065 noncytotoxic Toxicity 0.000 description 1
- 230000002020 noncytotoxic effect Effects 0.000 description 1
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- 239000003921 oil Substances 0.000 description 1
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- HYFHYPWGAURHIV-JFIAXGOJSA-N omacetaxine mepesuccinate Chemical compound C1=C2CCN3CCC[C@]43C=C(OC)[C@@H](OC(=O)[C@@](O)(CCCC(C)(C)O)CC(=O)OC)[C@H]4C2=CC2=C1OCO2 HYFHYPWGAURHIV-JFIAXGOJSA-N 0.000 description 1
- 229960002230 omacetaxine mepesuccinate Drugs 0.000 description 1
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- 229910052763 palladium Inorganic materials 0.000 description 1
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- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
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- 238000009521 phase II clinical trial Methods 0.000 description 1
- 230000000865 phosphorylative effect Effects 0.000 description 1
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- 239000002504 physiological saline solution Substances 0.000 description 1
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- 230000036470 plasma concentration Effects 0.000 description 1
- 229960003171 plicamycin Drugs 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000009097 single-agent therapy Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 208000000587 small cell lung carcinoma Diseases 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012439 solid excipient Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 108060007951 sulfatase Proteins 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229960001603 tamoxifen Drugs 0.000 description 1
- 125000002456 taxol group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QCIWZIYBBNEPKB-UHFFFAOYSA-N tert-butyl(dimethyl)silane Chemical compound C[SiH](C)C(C)(C)C QCIWZIYBBNEPKB-UHFFFAOYSA-N 0.000 description 1
- 150000003527 tetrahydropyrans Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000003104 tissue culture media Substances 0.000 description 1
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 1
- 229960000303 topotecan Drugs 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 150000003648 triterpenes Chemical class 0.000 description 1
- 210000005239 tubule Anatomy 0.000 description 1
- 230000005748 tumor development Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Virology (AREA)
- Neurology (AREA)
- Epidemiology (AREA)
- AIDS & HIV (AREA)
- Urology & Nephrology (AREA)
- Molecular Biology (AREA)
- Neurosurgery (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Biomedical Technology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22653600P | 2000-08-18 | 2000-08-18 | |
| PCT/US2001/025581 WO2002016395A1 (en) | 2000-08-18 | 2001-08-15 | Prodrugs of betulinic acid derivatives for the treatment of cancer and hiv |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004517045A true JP2004517045A (ja) | 2004-06-10 |
| JP2004517045A5 JP2004517045A5 (enExample) | 2008-10-02 |
Family
ID=22849310
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002521491A Pending JP2004517045A (ja) | 2000-08-18 | 2001-08-15 | 癌およびｈｉｖの治療用ベツリン酸誘導体のプロドラッグ |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US6569842B2 (enExample) |
| EP (1) | EP1309605A1 (enExample) |
| JP (1) | JP2004517045A (enExample) |
| AU (2) | AU8494601A (enExample) |
| CA (1) | CA2418479C (enExample) |
| NO (1) | NO20030748L (enExample) |
| NZ (1) | NZ524087A (enExample) |
| WO (1) | WO2002016395A1 (enExample) |
| ZA (1) | ZA200301269B (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007525527A (ja) * | 2004-08-02 | 2007-09-06 | アンブリリア・バイオファーマ・インコーポレーテッド | リシンをベースにした化合物類 |
| JP2008518970A (ja) * | 2004-11-05 | 2008-06-05 | メルク エンド カムパニー インコーポレーテッド | ｛３−［２（ｒ）−［（１ｒ）−１−［３，５−ビス（トリフルオロメチル）フェニル］エトキシ］−３（ｓ）−（４−フルオロフェニル）モルホリン−４−イル］メチル］−５−オキソ−４，５−ジヒドロ−［１，２，４］−トリアゾール−１−イル｝ホスホン酸を調製する方法 |
| WO2015080396A1 (ko) * | 2013-11-27 | 2015-06-04 | 주식회사 휴메딕스 | 페길레이션된 베튤린 유도체를 포함하는 경구 투여용 항암제 조성물 |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6943260B2 (en) * | 2002-02-02 | 2005-09-13 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Process for obtaining betulinic acid |
| ATE350383T1 (de) * | 2002-08-23 | 2007-01-15 | Sloan Kettering Inst Cancer | Synthese von epothilonen, zwischenprodukte dafür, analoga und deren verwendungen |
| US7365221B2 (en) | 2002-09-26 | 2008-04-29 | Panacos Pharmaceuticals, Inc. | Monoacylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof |
| EP1594885B8 (de) * | 2003-02-11 | 2009-03-25 | Novelix Pharmaceuticals, Inc. | Medikament zur wachstumsinhibierung von tumoren |
| DE602004024966D1 (de) | 2003-03-24 | 2010-02-25 | Sterix Ltd | Oestrogenderivate als steroid sulphatase inhibitoren |
| JP2007510621A (ja) * | 2003-07-29 | 2007-04-26 | シグニチャー アールアンドディー ホールディングス，エルエルシー． | アミノ酸プロドラッグ |
| WO2005112929A2 (en) * | 2004-05-20 | 2005-12-01 | Cornell Research Foundation, Inc. | Anti-hiv-1 activity of betulinol derivatives |
| US8008280B2 (en) * | 2004-09-10 | 2011-08-30 | Biorings Llc | Betulinol derivatives as anti-HIV agents |
| JP4810642B2 (ja) * | 2004-11-30 | 2011-11-09 | 秋田県 | 癌転移抑制用トリテルペン誘導体及び該トリテルペン誘導体を用いた癌転移抑制用組成物 |
| WO2006105356A2 (en) * | 2005-03-29 | 2006-10-05 | Regents Of The University Of Minnesota | Methods of manufacturing bioactive 3-esters of betulinic aldehyde and betulinic acid |
| US20070111936A1 (en) | 2005-11-15 | 2007-05-17 | Vladimir Pak | Complex of alpha-fetoprotein and inducers of apoptosis for the treatment of cancer |
| ZA200805703B (en) * | 2005-12-16 | 2009-10-28 | Panacos Pharmaceuticals Inc | Preparation of pharmaceutical salts of 3-0-(3',3'-dimethyl-succinyl) betulinic acid |
| GB0604535D0 (en) | 2006-03-07 | 2006-04-12 | Sndv Sprl | Betulonic acid derivatives |
| US20110152229A1 (en) * | 2006-11-22 | 2011-06-23 | Duke University | Betulinic acid derivatives as anti-hiv agents |
| WO2009020732A1 (en) * | 2007-08-03 | 2009-02-12 | Advanced Life Sciences, Inc. | Lupane-type triterpenoids modified at 30-position and analogues thereof |
| EP2303280A2 (en) * | 2008-05-30 | 2011-04-06 | Novelix Pharmaceuticals, Inc. | Compositions and methods for treatment of inflammation and hyperkeratotic lesions |
| US8372808B2 (en) * | 2008-10-31 | 2013-02-12 | Wisconsin Alumni Research Foundation | Suppression of glial fibrillary acidic protein |
| WO2010068668A1 (en) * | 2008-12-10 | 2010-06-17 | Advanced Life Sciences, Inc. | 23-substituted derivatives of lupane-type pentacyclic triterpenoids |
| RU2551647C2 (ru) * | 2012-11-12 | 2015-05-27 | Федеральное государственное бюджетное учреждение науки Институт нефтехимии и катализа Российской академии наук | Трифенилфосфониевые соли лупановых тритерпеноидов, способ получения и применение в качестве противоопухолевых веществ |
| CN107011406A (zh) * | 2016-01-28 | 2017-08-04 | 思路迪（北京）医药科技有限公司 | 一种具有抗肿瘤作用的化合物及其制备方法和应用 |
| CA3075729A1 (en) | 2017-09-14 | 2019-03-21 | Phoenix Biotechnology, Inc. | Use of oleandrin to treatn viral infection |
| CN111417384A (zh) | 2017-09-14 | 2020-07-14 | 菲尼克斯生物技术公司 | 用于治疗神经系统病况的方法和改进的神经保护性组合物 |
| WO2020006510A1 (en) | 2018-06-29 | 2020-01-02 | Dfh Therapeutics | Triterpene amine derivatives |
| WO2020124043A1 (en) * | 2018-12-13 | 2020-06-18 | Gordon Erlinda M | Methods of exploiting oncogenic drivers along the human cyclin g1 pathway for cancer gene therapy |
| EP4295854A3 (en) | 2020-03-31 | 2024-04-03 | Phoenix Biotechnology, Inc. | Method and compositions for treating coronavirus infection |
| KR20220151038A (ko) | 2020-03-31 | 2022-11-11 | 피닉스 바이오테크놀러지 인코포레이티드. | 코로나바이러스 감염 예방를 위한 조성물 |
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| JPH0987156A (ja) * | 1995-09-19 | 1997-03-31 | Pola Chem Ind Inc | 光老化防止剤及び皮膚化粧料 |
| EP0943620B1 (en) * | 1998-03-18 | 2005-11-16 | Dabur Pharma Ltd. | Betulinic acid derivatives for inhibiting cancer growth |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2683531B1 (fr) * | 1991-11-13 | 1993-12-31 | Rhone Poulenc Rorer Sa | Nouveaux derives du lupane, leur preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2705097B1 (fr) * | 1993-05-11 | 1995-08-04 | Rhone Poulenc Rorer Sa | Nouveaux dérivés du lupane, leur préparation et les compositions pharmaceutiques qui les contiennent. |
| US5869535A (en) | 1995-03-21 | 1999-02-09 | The Board Of Trustees Of The University Of Illinois | Method and composition for selectively inhibiting melanoma |
| US5658947A (en) | 1995-03-21 | 1997-08-19 | Board Of Trustees Of The University Of Illinois | Method and composition for selectively inhibiting melanoma using betalinic acid |
| US5962527A (en) | 1995-03-21 | 1999-10-05 | The Board Of Trustees Of The University Of Illinois | Method and composition for treating cancers |
| US5804575A (en) | 1997-03-27 | 1998-09-08 | The Board Of Trustees Of The University Of Illinois | Methods of manufacturing betulinic acid |
| US6048847A (en) * | 1997-09-30 | 2000-04-11 | Dabur Research Foundation | Use of betulinic acid and its derivatives for inhibiting cancer growth and a method of monitoring this |
| US6670345B1 (en) * | 1997-09-30 | 2003-12-30 | Dabur Research Foundation | Betulinic acid derivatives for inhabiting cancer growth and process for the manufacture of betulinic acid |
| EP1131337B1 (en) | 1998-11-18 | 2009-01-14 | Dabur Pharma Ltd. | Novel betulinic acid derivatives, processes for preparing such derivatives and its use as cancer growth inhibitors |
| EP1189607A2 (en) | 1999-04-07 | 2002-03-27 | Washington State University Research Foundation | Anti-tumor activity of vitamin e, cholesterol, taxol and betulinic acid derivatives |
| EP1321145A4 (en) * | 2000-07-31 | 2006-03-22 | Nisshin Oillio Ltd | ANTITUMOR SUBSTANCES |
-
2001
- 2001-08-15 CA CA002418479A patent/CA2418479C/en not_active Expired - Fee Related
- 2001-08-15 WO PCT/US2001/025581 patent/WO2002016395A1/en not_active Ceased
- 2001-08-15 US US09/930,656 patent/US6569842B2/en not_active Expired - Fee Related
- 2001-08-15 JP JP2002521491A patent/JP2004517045A/ja active Pending
- 2001-08-15 AU AU8494601A patent/AU8494601A/xx active Pending
- 2001-08-15 AU AU2001284946A patent/AU2001284946B2/en not_active Ceased
- 2001-08-15 NZ NZ524087A patent/NZ524087A/en unknown
- 2001-08-15 EP EP01964047A patent/EP1309605A1/en not_active Ceased
-
2003
- 2003-01-13 US US10/340,934 patent/US7091195B2/en not_active Expired - Fee Related
- 2003-02-17 ZA ZA200301269A patent/ZA200301269B/xx unknown
- 2003-02-17 NO NO20030748A patent/NO20030748L/no not_active Application Discontinuation
-
2006
- 2006-06-28 US US11/477,177 patent/US20070072835A1/en not_active Abandoned
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0987156A (ja) * | 1995-09-19 | 1997-03-31 | Pola Chem Ind Inc | 光老化防止剤及び皮膚化粧料 |
| EP0943620B1 (en) * | 1998-03-18 | 2005-11-16 | Dabur Pharma Ltd. | Betulinic acid derivatives for inhibiting cancer growth |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007525527A (ja) * | 2004-08-02 | 2007-09-06 | アンブリリア・バイオファーマ・インコーポレーテッド | リシンをベースにした化合物類 |
| JP2008518970A (ja) * | 2004-11-05 | 2008-06-05 | メルク エンド カムパニー インコーポレーテッド | ｛３−［２（ｒ）−［（１ｒ）−１−［３，５−ビス（トリフルオロメチル）フェニル］エトキシ］−３（ｓ）−（４−フルオロフェニル）モルホリン−４−イル］メチル］−５−オキソ−４，５−ジヒドロ−［１，２，４］−トリアゾール−１−イル｝ホスホン酸を調製する方法 |
| WO2015080396A1 (ko) * | 2013-11-27 | 2015-06-04 | 주식회사 휴메딕스 | 페길레이션된 베튤린 유도체를 포함하는 경구 투여용 항암제 조성물 |
| KR101531821B1 (ko) * | 2013-11-27 | 2015-06-24 | 주식회사 휴메딕스 | 페길레이션된 베튤린 유도체를 포함하는 경구 투여용 항암제 조성물 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20070072835A1 (en) | 2007-03-29 |
| US20020052352A1 (en) | 2002-05-02 |
| AU2001284946B2 (en) | 2007-02-01 |
| CA2418479A1 (en) | 2002-02-28 |
| CA2418479C (en) | 2007-12-18 |
| NZ524087A (en) | 2004-08-27 |
| NO20030748D0 (no) | 2003-02-17 |
| US7091195B2 (en) | 2006-08-15 |
| ZA200301269B (en) | 2003-11-03 |
| AU8494601A (en) | 2002-03-04 |
| NO20030748L (no) | 2003-04-15 |
| EP1309605A1 (en) | 2003-05-14 |
| US6569842B2 (en) | 2003-05-27 |
| US20030186945A1 (en) | 2003-10-02 |
| WO2002016395A1 (en) | 2002-02-28 |
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