ES2254443T3 - Suspensiones acuosas estabilizadas para uso parenteral. - Google Patents
Suspensiones acuosas estabilizadas para uso parenteral.Info
- Publication number
- ES2254443T3 ES2254443T3 ES01945040T ES01945040T ES2254443T3 ES 2254443 T3 ES2254443 T3 ES 2254443T3 ES 01945040 T ES01945040 T ES 01945040T ES 01945040 T ES01945040 T ES 01945040T ES 2254443 T3 ES2254443 T3 ES 2254443T3
- Authority
- ES
- Spain
- Prior art keywords
- weight
- volume
- formulation according
- formulation
- methionine
- 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.)
- Expired - Lifetime
Links
- 239000000725 suspension Substances 0.000 title description 66
- 239000000203 mixture Substances 0.000 claims abstract description 97
- 238000009472 formulation Methods 0.000 claims abstract description 87
- FFEARJCKVFRZRR-UHFFFAOYSA-N L-Methionine Natural products CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 claims abstract description 51
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims abstract description 51
- 229930195722 L-methionine Natural products 0.000 claims abstract description 51
- 229960004452 methionine Drugs 0.000 claims abstract description 51
- 239000006172 buffering agent Substances 0.000 claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 239000007900 aqueous suspension Substances 0.000 claims abstract description 25
- 230000003637 steroidlike Effects 0.000 claims abstract description 18
- 239000000654 additive Substances 0.000 claims abstract description 15
- 230000001276 controlling effect Effects 0.000 claims abstract description 12
- 238000007911 parenteral administration Methods 0.000 claims abstract description 10
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 claims description 32
- 229960002985 medroxyprogesterone acetate Drugs 0.000 claims description 22
- 239000000872 buffer Substances 0.000 claims description 21
- 229910019142 PO4 Inorganic materials 0.000 claims description 20
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 20
- 230000000694 effects Effects 0.000 claims description 18
- BFYIZQONLCFLEV-DAELLWKTSA-N Aromasine Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(=C)C2=C1 BFYIZQONLCFLEV-DAELLWKTSA-N 0.000 claims description 17
- 239000008363 phosphate buffer Substances 0.000 claims description 17
- 229960000255 exemestane Drugs 0.000 claims description 16
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 15
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 15
- UOACKFBJUYNSLK-XRKIENNPSA-N Estradiol Cypionate Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H](C4=CC=C(O)C=C4CC3)CC[C@@]21C)C(=O)CCC1CCCC1 UOACKFBJUYNSLK-XRKIENNPSA-N 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 229960005416 estradiol cypionate Drugs 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 11
- 230000003139 buffering effect Effects 0.000 claims description 10
- 229960004616 medroxyprogesterone Drugs 0.000 claims description 10
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000000375 suspending agent Substances 0.000 claims description 8
- 229920001223 polyethylene glycol Polymers 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- HPFVBGJFAYZEBE-XNBTXCQYSA-N [(8r,9s,10r,13s,14s)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] 3-cyclopentylpropanoate Chemical compound C([C@H]1[C@H]2[C@@H]([C@]3(CCC(=O)C=C3CC2)C)CC[C@@]11C)CC1OC(=O)CCC1CCCC1 HPFVBGJFAYZEBE-XNBTXCQYSA-N 0.000 claims description 6
- 239000003963 antioxidant agent Substances 0.000 claims description 6
- 238000007920 subcutaneous administration Methods 0.000 claims description 6
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims description 5
- 229960005309 estradiol Drugs 0.000 claims description 5
- 229930182833 estradiol Natural products 0.000 claims description 5
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical group [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 4
- 230000003078 antioxidant effect Effects 0.000 claims description 4
- 238000007918 intramuscular administration Methods 0.000 claims description 4
- 239000003755 preservative agent Substances 0.000 claims description 4
- 150000003573 thiols Chemical class 0.000 claims description 4
- 239000002738 chelating agent Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 150000003016 phosphoric acids Chemical class 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 239000002562 thickening agent Substances 0.000 claims description 3
- XYGMEFJSKQEBTO-KUJXMBTLSA-N Clostebol acetate Chemical compound C1CC2=C(Cl)C(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)C)[C@@]1(C)CC2 XYGMEFJSKQEBTO-KUJXMBTLSA-N 0.000 claims description 2
- KHKDIUPVDIEHAH-KXLSUQFWSA-N Oxabolone cipionate Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@H]4CCC(=O)C(O)=C4CC3)CC[C@@]21C)C(=O)CCC1CCCC1 KHKDIUPVDIEHAH-KXLSUQFWSA-N 0.000 claims description 2
- 239000007979 citrate buffer Substances 0.000 claims description 2
- 229960002039 clostebol acetate Drugs 0.000 claims description 2
- 229960001293 methylprednisolone acetate Drugs 0.000 claims description 2
- PLBHSZGDDKCEHR-LFYFAGGJSA-N methylprednisolone acetate Chemical compound C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(C)=O)CC[C@H]21 PLBHSZGDDKCEHR-LFYFAGGJSA-N 0.000 claims description 2
- 239000001488 sodium phosphate Substances 0.000 claims description 2
- 229910000162 sodium phosphate Inorganic materials 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 239000002202 Polyethylene glycol Substances 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 1
- 230000002335 preservative effect Effects 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- HPFVBGJFAYZEBE-ZLQWOROUSA-N testosterone cypionate Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(CCC(=O)C=C4CC3)C)CC[C@@]21C)C(=O)CCC1CCCC1 HPFVBGJFAYZEBE-ZLQWOROUSA-N 0.000 claims 1
- 229960000921 testosterone cypionate Drugs 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
- 239000010452 phosphate Substances 0.000 description 18
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 14
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 229940022663 acetate Drugs 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 238000003860 storage Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 230000007423 decrease Effects 0.000 description 8
- 230000008901 benefit Effects 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 7
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 7
- 229960002216 methylparaben Drugs 0.000 description 7
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 7
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 7
- 229920000053 polysorbate 80 Polymers 0.000 description 7
- 229940068968 polysorbate 80 Drugs 0.000 description 7
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 7
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 7
- 229960003415 propylparaben Drugs 0.000 description 7
- 230000006641 stabilisation Effects 0.000 description 7
- 238000011105 stabilization Methods 0.000 description 7
- 239000008215 water for injection Substances 0.000 description 6
- 210000000707 wrist Anatomy 0.000 description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 5
- 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 5
- 239000008186 active pharmaceutical agent Substances 0.000 description 5
- 238000005189 flocculation Methods 0.000 description 5
- 230000016615 flocculation Effects 0.000 description 5
- 150000007522 mineralic acids Chemical class 0.000 description 5
- 239000007971 pharmaceutical suspension Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 5
- 230000002195 synergetic effect Effects 0.000 description 5
- ZCTSINFCZHUVLI-UHFFFAOYSA-M 4-methyl-1-tetradecylpyridin-1-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+]1=CC=C(C)C=C1 ZCTSINFCZHUVLI-UHFFFAOYSA-M 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- 230000001627 detrimental effect Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920000609 methyl cellulose Polymers 0.000 description 4
- 239000001923 methylcellulose Substances 0.000 description 4
- 235000010981 methylcellulose Nutrition 0.000 description 4
- 230000020477 pH reduction Effects 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 229940050929 polyethylene glycol 3350 Drugs 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229940078693 1-myristylpicolinium Drugs 0.000 description 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229920002562 Polyethylene Glycol 3350 Polymers 0.000 description 3
- NEDJKVIUOSOCNB-AWPSVMBFSA-N [(6s,8r,9s,10r,13s,14s,17r)-17-acetyl-6,10,13-trimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-yl] acetate;[(8r,9s,13s,14s,17s)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] 3-cyclo Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21.O([C@H]1CC[C@H]2[C@H]3[C@@H](C4=CC=C(O)C=C4CC3)CC[C@@]21C)C(=O)CCC1CCCC1 NEDJKVIUOSOCNB-AWPSVMBFSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- -1 aliphatic amino acid Chemical class 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000003906 humectant Substances 0.000 description 3
- 239000000787 lecithin Substances 0.000 description 3
- 235000010445 lecithin Nutrition 0.000 description 3
- 229940067606 lecithin Drugs 0.000 description 3
- 229940045641 monobasic sodium phosphate Drugs 0.000 description 3
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 3
- 235000019799 monosodium phosphate Nutrition 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 3
- 229940001584 sodium metabisulfite Drugs 0.000 description 3
- 235000010262 sodium metabisulphite Nutrition 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 230000001954 sterilising effect Effects 0.000 description 3
- CKDULIWBRNAIIU-MOBQZEGBSA-N (2s)-2-azanyl-4-methylsulfanyl-butanoic acid Chemical compound CSCC[C@H](N)C(O)=O.CSCC[C@H](N)C(O)=O.CSCC[C@H](N)C(O)=O CKDULIWBRNAIIU-MOBQZEGBSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- GPIHAUAAQOAXNW-UHFFFAOYSA-N O.O.O.O.O.O.O.O.O.O.O.O.[Na] Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.[Na] GPIHAUAAQOAXNW-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920001030 Polyethylene Glycol 4000 Polymers 0.000 description 2
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
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- 230000015556 catabolic process Effects 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 229940061607 dibasic sodium phosphate Drugs 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 229940124274 edetate disodium Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/34—Gestagens
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
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| KR101288265B1 (ko) * | 2003-09-03 | 2013-07-26 | 미스콘 트레이딩 에스.에이. | 자궁 내막증의 치료 방법 |
| US20050171167A1 (en) * | 2003-11-04 | 2005-08-04 | Haby Thomas A. | Process and formulation containing epothilones and analogs thereof |
| US20050106214A1 (en) * | 2003-11-14 | 2005-05-19 | Guohua Chen | Excipients in drug delivery vehicles |
| CA2581076A1 (en) * | 2004-09-14 | 2006-03-23 | Molecular Therapeutics, Inc. | D-methionine formulation with improved biopharmaceutical properties |
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| US20070154546A1 (en) * | 2005-12-30 | 2007-07-05 | Zhang Jack Y | Sustained release pharmaceutical compositions |
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| GB0625962D0 (en) * | 2006-12-23 | 2007-02-07 | Renovo Ltd | Medicaments and methods for wound healing |
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| JPS5831210B2 (ja) * | 1973-04-09 | 1983-07-05 | 武田薬品工業株式会社 | アンテイナスイセイケンダクエキノセイゾウホウ |
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| US5208261A (en) * | 1989-12-06 | 1993-05-04 | Akzo N.V. | Stabilized solutions of psychotropic agents |
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| JP3862295B2 (ja) * | 1993-09-30 | 2006-12-27 | 独立行政法人理化学研究所 | 抗肥満剤 |
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| DE59805732D1 (de) | 1997-09-23 | 2002-10-31 | Rentschler Biotech Gmbh | Flüssige interferon-beta-formulierungen |
| US5968918A (en) * | 1997-10-17 | 1999-10-19 | Kanda; Iwao | Method for the prevention of coronary artery spasm |
| US5972921A (en) * | 1997-12-12 | 1999-10-26 | Hormos Medical Oy Ltd. | Use of an aromatase inhibitor in the treatment of decreased androgen to estrogen ratio and detrusor urethral sphincter dyssynergia in men |
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| ATE464062T1 (de) | 1999-10-04 | 2010-04-15 | Novartis Vaccines & Diagnostic | Stabilisierte flüssige pharmazeutische zusammensetzung enthaltend tfpi |
| US6495534B2 (en) * | 2000-05-15 | 2002-12-17 | Pharmacia & Upjohn Spa | Stabilized aqueous suspensions for parenteral use |
-
2000
- 2000-05-15 US US09/571,395 patent/US6495534B2/en not_active Expired - Lifetime
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2001
- 2001-04-25 NZ NZ522324A patent/NZ522324A/en not_active IP Right Cessation
- 2001-04-25 JP JP2001583735A patent/JP4205341B2/ja not_active Expired - Lifetime
- 2001-04-25 WO PCT/EP2001/004643 patent/WO2001087266A1/en not_active Ceased
- 2001-04-25 DK DK01945040T patent/DK1282402T3/da active
- 2001-04-25 BR BR0110841-7A patent/BR0110841A/pt not_active Application Discontinuation
- 2001-04-25 CA CA002409059A patent/CA2409059C/en not_active Expired - Lifetime
- 2001-04-25 ES ES01945040T patent/ES2254443T3/es not_active Expired - Lifetime
- 2001-04-25 IL IL152537A patent/IL152537A/en active IP Right Grant
- 2001-04-25 HU HU0302021A patent/HU229800B1/hu unknown
- 2001-04-25 PL PL365793A patent/PL203075B1/pl unknown
- 2001-04-25 AU AU2001267371A patent/AU2001267371B2/en not_active Expired
- 2001-04-25 EE EEP200200631A patent/EE05376B1/xx unknown
- 2001-04-25 HK HK03106493.6A patent/HK1054194B/zh not_active IP Right Cessation
- 2001-04-25 EA EA200201208A patent/EA007682B1/ru not_active IP Right Cessation
- 2001-04-25 SI SI200130485T patent/SI1282402T1/sl unknown
- 2001-04-25 IN IN1996CH2002 patent/IN224279B/en unknown
- 2001-04-25 EP EP01945040A patent/EP1282402B1/en not_active Expired - Lifetime
- 2001-04-25 AT AT01945040T patent/ATE313316T1/de active
- 2001-04-25 CZ CZ20023750A patent/CZ303872B6/cs not_active IP Right Cessation
- 2001-04-25 MX MXPA02011195A patent/MXPA02011195A/es active IP Right Grant
- 2001-04-25 CN CNB018095895A patent/CN100473376C/zh not_active Expired - Lifetime
- 2001-04-25 DE DE60116084T patent/DE60116084T2/de not_active Expired - Lifetime
- 2001-04-25 SK SK1598-2002A patent/SK287641B6/sk not_active IP Right Cessation
- 2001-04-25 AU AU6737101A patent/AU6737101A/xx active Pending
- 2001-04-25 KR KR1020027015431A patent/KR100828957B1/ko not_active Expired - Lifetime
- 2001-05-09 TW TW090111029A patent/TWI256310B/zh not_active IP Right Cessation
- 2001-05-14 AR ARP010102268A patent/AR029924A1/es not_active Application Discontinuation
- 2001-05-14 PE PE2001000431A patent/PE20011322A1/es active IP Right Grant
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2002
- 2002-08-21 US US10/225,320 patent/US20030114430A1/en not_active Abandoned
- 2002-10-10 US US10/267,690 patent/US20030130245A1/en not_active Abandoned
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- 2002-11-13 NO NO20025431A patent/NO332215B1/no not_active IP Right Cessation
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