JP2010527940A5 - - Google Patents
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- Publication number
- JP2010527940A5 JP2010527940A5 JP2010508677A JP2010508677A JP2010527940A5 JP 2010527940 A5 JP2010527940 A5 JP 2010527940A5 JP 2010508677 A JP2010508677 A JP 2010508677A JP 2010508677 A JP2010508677 A JP 2010508677A JP 2010527940 A5 JP2010527940 A5 JP 2010527940A5
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- formulation
- polyethylene oxide
- amphotericin
- salt
- 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
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- 239000000203 mixture Substances 0.000 claims description 119
- 238000009472 formulation Methods 0.000 claims description 88
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 75
- 229930195729 fatty acid Natural products 0.000 claims description 75
- 239000000194 fatty acid Substances 0.000 claims description 75
- -1 fatty acid glycerol esters Chemical class 0.000 claims description 71
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 59
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 58
- 239000003814 drug Substances 0.000 claims description 47
- LVNGJLRDBYCPGB-UHFFFAOYSA-N 1,2-distearoylphosphatidylethanolamine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(COP([O-])(=O)OCC[NH3+])OC(=O)CCCCCCCCCCCCCCCCC LVNGJLRDBYCPGB-UHFFFAOYSA-N 0.000 claims description 34
- 239000002202 Polyethylene glycol Substances 0.000 claims description 29
- 229920001223 polyethylene glycol Polymers 0.000 claims description 29
- 229940124597 therapeutic agent Drugs 0.000 claims description 24
- APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 claims description 23
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 claims description 23
- 229960003942 amphotericin b Drugs 0.000 claims description 23
- 150000002334 glycols Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 150000003904 phospholipids Chemical class 0.000 claims description 13
- 229940079593 drug Drugs 0.000 claims description 12
- 150000004665 fatty acids Chemical class 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 9
- 208000015181 infectious disease Diseases 0.000 claims description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 4
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 4
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims description 4
- 239000005642 Oleic acid Substances 0.000 claims description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- 150000002027 dodecanoic acid esters Chemical class 0.000 claims description 4
- XPJRQAIZZQMSCM-UHFFFAOYSA-N heptaethylene glycol Polymers OCCOCCOCCOCCOCCOCCOCCO XPJRQAIZZQMSCM-UHFFFAOYSA-N 0.000 claims description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 4
- 150000002943 palmitic acids Chemical class 0.000 claims description 4
- 150000008104 phosphatidylethanolamines Chemical class 0.000 claims description 4
- 229940113116 polyethylene glycol 1000 Drugs 0.000 claims description 4
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 150000003626 triacylglycerols Chemical class 0.000 claims description 4
- 206010017533 Fungal infection Diseases 0.000 claims description 3
- 208000031888 Mycoses Diseases 0.000 claims description 3
- 238000012377 drug delivery Methods 0.000 claims description 3
- 229940126585 therapeutic drug Drugs 0.000 claims description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 3
- 206010001935 American trypanosomiasis Diseases 0.000 claims description 2
- 201000002909 Aspergillosis Diseases 0.000 claims description 2
- 208000036641 Aspergillus infections Diseases 0.000 claims description 2
- 241000222122 Candida albicans Species 0.000 claims description 2
- 206010007134 Candida infections Diseases 0.000 claims description 2
- 208000024699 Chagas disease Diseases 0.000 claims description 2
- 241000223205 Coccidioides immitis Species 0.000 claims description 2
- 201000007336 Cryptococcosis Diseases 0.000 claims description 2
- 241000221204 Cryptococcus neoformans Species 0.000 claims description 2
- 208000002633 Febrile Neutropenia Diseases 0.000 claims description 2
- 201000002563 Histoplasmosis Diseases 0.000 claims description 2
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- 206010033767 Paracoccidioides infections Diseases 0.000 claims description 2
- 201000000301 Paracoccidioidomycosis Diseases 0.000 claims description 2
- 206010041736 Sporotrichosis Diseases 0.000 claims description 2
- 241000223109 Trypanosoma cruzi Species 0.000 claims description 2
- 206010047505 Visceral leishmaniasis Diseases 0.000 claims description 2
- 206010061418 Zygomycosis Diseases 0.000 claims description 2
- 229940035676 analgesics Drugs 0.000 claims description 2
- 239000000730 antalgic agent Substances 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- 230000003474 anti-emetic effect Effects 0.000 claims description 2
- 230000000843 anti-fungal effect Effects 0.000 claims description 2
- 230000000389 anti-prion effect Effects 0.000 claims description 2
- 239000000043 antiallergic agent Substances 0.000 claims description 2
- 229940088710 antibiotic agent Drugs 0.000 claims description 2
- 229940125683 antiemetic agent Drugs 0.000 claims description 2
- 239000002111 antiemetic agent Substances 0.000 claims description 2
- 229940121375 antifungal agent Drugs 0.000 claims description 2
- 239000002246 antineoplastic agent Substances 0.000 claims description 2
- 229940041181 antineoplastic drug Drugs 0.000 claims description 2
- 239000003443 antiviral agent Substances 0.000 claims description 2
- 239000002249 anxiolytic agent Substances 0.000 claims description 2
- 230000000949 anxiolytic effect Effects 0.000 claims description 2
- 229940005530 anxiolytics Drugs 0.000 claims description 2
- 201000003984 candidiasis Diseases 0.000 claims description 2
- 201000003486 coccidioidomycosis Diseases 0.000 claims description 2
- 239000003018 immunosuppressive agent Substances 0.000 claims description 2
- 229940124589 immunosuppressive drug Drugs 0.000 claims description 2
- 239000003589 local anesthetic agent Substances 0.000 claims description 2
- 229960005015 local anesthetics Drugs 0.000 claims description 2
- 206010027599 migraine Diseases 0.000 claims description 2
- 201000003152 motion sickness Diseases 0.000 claims description 2
- 201000007524 mucormycosis Diseases 0.000 claims description 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 2
- 229940125723 sedative agent Drugs 0.000 claims description 2
- 239000000932 sedative agent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 6
- 230000000699 topical effect Effects 0.000 claims 6
- 208000035473 Communicable disease Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 235000003441 saturated fatty acids Nutrition 0.000 claims 2
- 241000222722 Leishmania <genus> Species 0.000 claims 1
- 239000004698 Polyethylene Substances 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- 229920000573 polyethylene Polymers 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 229960004365 benzoic acid Drugs 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 description 1
- FELGMEQIXOGIFQ-CYBMUJFWSA-N (3r)-9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1h-carbazol-4-one Chemical compound CC1=NC=CN1C[C@@H]1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 FELGMEQIXOGIFQ-CYBMUJFWSA-N 0.000 description 1
- DIWRORZWFLOCLC-HNNXBMFYSA-N (3s)-7-chloro-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound N([C@H](C(NC1=CC=C(Cl)C=C11)=O)O)=C1C1=CC=CC=C1Cl DIWRORZWFLOCLC-HNNXBMFYSA-N 0.000 description 1
- FJIKWRGCXUCUIG-HNNXBMFYSA-N (3s)-7-chloro-5-(2-chlorophenyl)-3-hydroxy-1-methyl-3h-1,4-benzodiazepin-2-one Chemical compound O=C([C@H](O)N=1)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1Cl FJIKWRGCXUCUIG-HNNXBMFYSA-N 0.000 description 1
- SGKRLCUYIXIAHR-AKNGSSGZSA-N (4s,4ar,5s,5ar,6r,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1=CC=C2[C@H](C)[C@@H]([C@H](O)[C@@H]3[C@](C(O)=C(C(N)=O)C(=O)[C@H]3N(C)C)(O)C3=O)C3=C(O)C2=C1O SGKRLCUYIXIAHR-AKNGSSGZSA-N 0.000 description 1
- LEZWWPYKPKIXLL-UHFFFAOYSA-N 1-{2-(4-chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl}imidazole Chemical compound C1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 LEZWWPYKPKIXLL-UHFFFAOYSA-N 0.000 description 1
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 1
- VHVPQPYKVGDNFY-DFMJLFEVSA-N 2-[(2r)-butan-2-yl]-4-[4-[4-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound O=C1N([C@H](C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(OC3)C=3C(=CC(Cl)=CC=3)Cl)=CC=2)C=C1 VHVPQPYKVGDNFY-DFMJLFEVSA-N 0.000 description 1
- FJHBVJOVLFPMQE-QFIPXVFZSA-N 7-Ethyl-10-Hydroxy-Camptothecin Chemical compound C1=C(O)C=C2C(CC)=C(CN3C(C4=C([C@@](C(=O)OC4)(O)CC)C=C33)=O)C3=NC2=C1 FJHBVJOVLFPMQE-QFIPXVFZSA-N 0.000 description 1
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- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
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- BYBLEWFAAKGYCD-UHFFFAOYSA-N Miconazole Chemical compound ClC1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 BYBLEWFAAKGYCD-UHFFFAOYSA-N 0.000 description 1
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- 239000000006 Nitroglycerin Substances 0.000 description 1
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- 229960003120 clonazepam Drugs 0.000 description 1
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- 229960003529 diazepam Drugs 0.000 description 1
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
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| NO2252275T3 (https=) * | 2008-02-13 | 2018-04-28 | ||
| CN102389401B (zh) * | 2011-11-22 | 2013-05-22 | 陆荣政 | 一种右旋布洛芬颗粒及其制备方法 |
| WO2014152207A1 (en) | 2013-03-15 | 2014-09-25 | Mylan Laboratories, Inc. | Hot melt granulation formulations of poorly water-soluble active agents |
| US20170217976A1 (en) * | 2014-03-21 | 2017-08-03 | Chironwells Gmbh | 6-(amino acid)-morphinan derivatives in combination with permeation enhancers for use as an orally, rectally, transdermally or nasally administered medicament |
| KR101542364B1 (ko) * | 2014-10-31 | 2015-08-07 | 대화제약 주식회사 | 탁산을 포함하는 경구 투여용 약학 조성물 |
| WO2016112339A1 (en) * | 2015-01-09 | 2016-07-14 | Ico Therapeutics Inc. | Stable formulations for the oral administration of amphotericin b and related methods |
| CN105018542B (zh) * | 2015-07-10 | 2018-01-02 | 北京师范大学 | 烟曲霉teqa在制备奥沙西泮中的应用 |
| CN106063779A (zh) * | 2016-06-12 | 2016-11-02 | 上海上药第生化药业有限公司 | 一种维生素k1药物的新剂型及制备方法 |
| EP3585397A4 (en) * | 2017-02-21 | 2020-11-25 | iCo Therapeutics Inc. | ORAL AMPHOTERICIN B SOLID FORMULATIONS |
| US20230310465A1 (en) * | 2020-08-18 | 2023-10-05 | Leiutis Pharmaceuticals Llp | Nano lipid carrier system for improving permeation of active ingredients |
| BR102020022824A8 (pt) * | 2020-11-09 | 2024-01-02 | Fundacao Oswaldo Cruz | Composição, composição farmacêutica, e, uso de uma composição tópica estável compreendendo uma nanoemulsão, e de pelo menos um composto antileishmanial |
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| AU598958B2 (en) * | 1987-11-12 | 1990-07-05 | Vestar, Inc. | Improved amphotericin b liposome preparation |
| WO1993011777A1 (en) * | 1991-12-11 | 1993-06-24 | Temple University - Of The Commonwealth System Of Higher Education | Amphotericin b composition with enhanced antifungal activity |
| FR2710535B1 (fr) * | 1993-09-30 | 1995-11-24 | Gattefosse Ets Sa | Composition à usage pharmaceutique ou cosmétique apte à former une microémulsion. |
| US6217886B1 (en) * | 1997-07-14 | 2001-04-17 | The Board Of Trustees Of The University Of Illinois | Materials and methods for making improved micelle compositions |
| US6248363B1 (en) * | 1999-11-23 | 2001-06-19 | Lipocine, Inc. | Solid carriers for improved delivery of active ingredients in pharmaceutical compositions |
| US6294192B1 (en) * | 1999-02-26 | 2001-09-25 | Lipocine, Inc. | Triglyceride-free compositions and methods for improved delivery of hydrophobic therapeutic agents |
| US6852334B1 (en) * | 1999-04-20 | 2005-02-08 | The University Of British Columbia | Cationic peg-lipids and methods of use |
| US20030236236A1 (en) | 1999-06-30 | 2003-12-25 | Feng-Jing Chen | Pharmaceutical compositions and dosage forms for administration of hydrophobic drugs |
| US6596306B1 (en) * | 2000-07-07 | 2003-07-22 | David Ho Sue San Ho | Drug delivery system:formulation for fat-soluble drugs |
| IN188843B (https=) * | 2000-06-22 | 2002-11-09 | Vinod Daftary Gautam Dr | |
| DE10036871A1 (de) * | 2000-07-28 | 2002-02-14 | Pharmasol Gmbh | Dispersionen zur Formulierung wenig oder schwer löslicher Wirkstoffe |
| AU2002214854A1 (en) * | 2000-10-25 | 2002-05-06 | Inex Pharmaceuticals Corporation | Lipid formulations for target delivery |
| US8067032B2 (en) * | 2000-12-22 | 2011-11-29 | Baxter International Inc. | Method for preparing submicron particles of antineoplastic agents |
| FR2827770B1 (fr) * | 2001-07-27 | 2005-08-19 | Gattefosse Ets Sa | Composition pharmaceutique a usage oral comprenant un principe actif susceptible de subir un important effet de premier passage intestinal |
| US6660761B2 (en) * | 2002-02-06 | 2003-12-09 | Council Of Scientific And Industrial Research | Method of treatment for fungal infections with a synergistic formulation of antifungal agents |
| JP2003252750A (ja) | 2002-02-26 | 2003-09-10 | ▲寛▼治 ▲高▼田 | 水溶性の難・低吸収性薬物のバイオアベイラビリティ改善技術 |
| CN1290893C (zh) * | 2002-05-03 | 2006-12-20 | 詹森药业有限公司 | 聚合物微乳状液 |
| US20040116360A1 (en) * | 2002-10-15 | 2004-06-17 | Kwon Glen S. | Encapsulation and deaggregation of polyene antibiotics using poly(ethylene glycol)-phospholipid micelles |
| AU2002350719A1 (en) * | 2002-11-29 | 2004-06-23 | Janssen Pharmaceutica N.V. | Pharmaceutical compositions comprising a basic respectively acidic drug compound, a surfactant and a physiologically tolerable water-soluble acid respectively base |
| US7731947B2 (en) * | 2003-11-17 | 2010-06-08 | Intarcia Therapeutics, Inc. | Composition and dosage form comprising an interferon particle formulation and suspending vehicle |
| CN1897918A (zh) * | 2003-11-17 | 2007-01-17 | 阿尔萨公司 | 包含两亲性分子作为混悬载体的组合物和剂型 |
| EP1706098A4 (en) * | 2003-11-26 | 2012-08-15 | Supernus Pharmaceuticals Inc | MICRO-LAYER SYSTEMS FOR THE TRANSPORT OF LIPOPHILES AND BZW. HYDROPHOBIC COMPOUNDS |
| MXPA06015220A (es) * | 2004-06-21 | 2007-12-13 | Nektar Therapeutics | Composiciones comprendiendo anfotericina b, metodos y sistemas. |
| CN100418536C (zh) * | 2005-04-06 | 2008-09-17 | 河南省眼科研究所 | 一种用于眼科的抗真菌药物组合物 |
| CA2604943C (en) | 2005-04-15 | 2013-09-17 | Clarus Therapeutics, Inc. | Pharmaceutical delivery systems for hydrophobic drugs and compositions comprising same |
| CN100418537C (zh) * | 2005-07-15 | 2008-09-17 | 同济大学 | 两性霉素b缓释微球及其制备方法 |
| WO2008058234A2 (en) | 2006-11-08 | 2008-05-15 | Memory Pharmaceuticals Corporation | Pharmaceutical formulations for 1,4-dihyrdropyridine compounds having improved solubility |
| KR20100017109A (ko) * | 2007-05-18 | 2010-02-16 | 싸이도우스 엘엘씨. | 지프라시돈 제제 |
-
2008
- 2008-05-23 CN CN200880023444.XA patent/CN101687044B/zh active Active
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- 2008-05-23 KR KR1020157013456A patent/KR20150064232A/ko not_active Ceased
- 2008-05-23 RU RU2009148315/15A patent/RU2485975C2/ru active
- 2008-05-23 NZ NZ582332A patent/NZ582332A/en not_active IP Right Cessation
- 2008-05-23 KR KR1020167005288A patent/KR20160029866A/ko not_active Ceased
- 2008-05-23 WO PCT/CA2008/000975 patent/WO2008144888A1/en not_active Ceased
- 2008-05-23 JP JP2010508677A patent/JP5501224B2/ja active Active
- 2008-05-23 KR KR1020097027108A patent/KR20100017928A/ko not_active Ceased
- 2008-05-23 MX MX2009012782A patent/MX2009012782A/es active IP Right Grant
- 2008-05-23 US US12/601,676 patent/US8592382B2/en active Active
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2009
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- 2009-12-15 ZA ZA2009/08928A patent/ZA200908928B/en unknown
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2013
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