CA2609242A1 - Injectable compositions and process for preparation of such compositions - Google Patents
Injectable compositions and process for preparation of such compositions Download PDFInfo
- Publication number
- CA2609242A1 CA2609242A1 CA002609242A CA2609242A CA2609242A1 CA 2609242 A1 CA2609242 A1 CA 2609242A1 CA 002609242 A CA002609242 A CA 002609242A CA 2609242 A CA2609242 A CA 2609242A CA 2609242 A1 CA2609242 A1 CA 2609242A1
- Authority
- CA
- Canada
- Prior art keywords
- composition according
- cox
- solution
- mixture
- inhibitor
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 181
- 238000000034 method Methods 0.000 title claims abstract description 42
- 239000007972 injectable composition Substances 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims description 14
- 239000003112 inhibitor Substances 0.000 claims abstract description 57
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims abstract description 43
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims abstract description 42
- 239000004480 active ingredient Substances 0.000 claims abstract description 38
- 238000001990 intravenous administration Methods 0.000 claims abstract description 32
- 150000003839 salts Chemical class 0.000 claims abstract description 29
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 28
- 208000002193 Pain Diseases 0.000 claims abstract description 25
- 230000036407 pain Effects 0.000 claims abstract description 25
- 239000000651 prodrug Substances 0.000 claims abstract description 25
- 229940002612 prodrug Drugs 0.000 claims abstract description 25
- 239000012453 solvate Substances 0.000 claims abstract description 25
- 238000007911 parenteral administration Methods 0.000 claims abstract description 13
- 238000007918 intramuscular administration Methods 0.000 claims abstract description 10
- 230000001154 acute effect Effects 0.000 claims abstract description 9
- 208000025978 Athletic injury Diseases 0.000 claims abstract description 8
- 208000019695 Migraine disease Diseases 0.000 claims abstract description 8
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 8
- 208000008765 Sciatica Diseases 0.000 claims abstract description 8
- 201000002661 Spondylitis Diseases 0.000 claims abstract description 8
- 201000011510 cancer Diseases 0.000 claims abstract description 8
- 208000014674 injury Diseases 0.000 claims abstract description 8
- 206010027599 migraine Diseases 0.000 claims abstract description 8
- 230000000926 neurological effect Effects 0.000 claims abstract description 8
- 230000002980 postoperative effect Effects 0.000 claims abstract description 8
- 230000008733 trauma Effects 0.000 claims abstract description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
- 208000035475 disorder Diseases 0.000 claims abstract description 7
- 206010020751 Hypersensitivity Diseases 0.000 claims abstract description 6
- 206010061218 Inflammation Diseases 0.000 claims abstract description 6
- 206010037660 Pyrexia Diseases 0.000 claims abstract description 6
- 208000026935 allergic disease Diseases 0.000 claims abstract description 6
- 230000007815 allergy Effects 0.000 claims abstract description 6
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- 206010013935 Dysmenorrhoea Diseases 0.000 claims abstract description 5
- 208000004550 Postoperative Pain Diseases 0.000 claims abstract description 5
- 201000008482 osteoarthritis Diseases 0.000 claims abstract description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 123
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 117
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 83
- 229960000965 nimesulide Drugs 0.000 claims description 76
- HYWYRSMBCFDLJT-UHFFFAOYSA-N nimesulide Chemical compound CS(=O)(=O)NC1=CC=C([N+]([O-])=O)C=C1OC1=CC=CC=C1 HYWYRSMBCFDLJT-UHFFFAOYSA-N 0.000 claims description 76
- 229920001223 polyethylene glycol Polymers 0.000 claims description 61
- 239000002202 Polyethylene glycol Substances 0.000 claims description 58
- 239000000872 buffer Substances 0.000 claims description 51
- 239000004471 Glycine Substances 0.000 claims description 42
- 239000003795 chemical substances by application Substances 0.000 claims description 39
- 239000002904 solvent Substances 0.000 claims description 34
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 33
- 150000002334 glycols Chemical class 0.000 claims description 26
- LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 claims description 26
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 25
- 230000003113 alkalizing effect Effects 0.000 claims description 23
- 239000006172 buffering agent Substances 0.000 claims description 23
- 239000008240 homogeneous mixture Substances 0.000 claims description 17
- 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 claims description 16
- 238000002156 mixing Methods 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 229940079593 drug Drugs 0.000 claims description 11
- -1 itacoxib Chemical compound 0.000 claims description 9
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 8
- 229960000905 indomethacin Drugs 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 7
- 229960001259 diclofenac Drugs 0.000 claims description 7
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims description 7
- UAWXGRJVZSAUSZ-UHFFFAOYSA-N licofelone Chemical group OC(=O)CC=1N2CC(C)(C)CC2=C(C=2C=CC=CC=2)C=1C1=CC=C(Cl)C=C1 UAWXGRJVZSAUSZ-UHFFFAOYSA-N 0.000 claims description 7
- 229950003488 licofelone Drugs 0.000 claims description 7
- 229960000371 rofecoxib Drugs 0.000 claims description 7
- RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 claims description 7
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 6
- 239000004472 Lysine Substances 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 claims description 6
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims description 6
- 229960001680 ibuprofen Drugs 0.000 claims description 6
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 5
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 claims description 5
- 239000003963 antioxidant agent Substances 0.000 claims description 5
- 235000011187 glycerol Nutrition 0.000 claims description 5
- 150000007529 inorganic bases Chemical class 0.000 claims description 5
- 229960004662 parecoxib Drugs 0.000 claims description 5
- TZRHLKRLEZJVIJ-UHFFFAOYSA-N parecoxib Chemical compound C1=CC(S(=O)(=O)NC(=O)CC)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 TZRHLKRLEZJVIJ-UHFFFAOYSA-N 0.000 claims description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- 229920000858 Cyclodextrin Polymers 0.000 claims description 4
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 4
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims description 4
- 230000002708 enhancing effect Effects 0.000 claims description 4
- 229960002009 naproxen Drugs 0.000 claims description 4
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- 239000008363 phosphate buffer Substances 0.000 claims description 4
- 239000003755 preservative agent Substances 0.000 claims description 4
- 235000000346 sugar Nutrition 0.000 claims description 4
- 150000008163 sugars Chemical class 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 239000003981 vehicle Substances 0.000 claims description 4
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 claims description 3
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 230000003078 antioxidant effect Effects 0.000 claims description 3
- 229960002903 benzyl benzoate Drugs 0.000 claims description 3
- 229960000590 celecoxib Drugs 0.000 claims description 3
- RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 claims description 3
- 229940093471 ethyl oleate Drugs 0.000 claims description 3
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 claims description 3
- 229960002004 valdecoxib Drugs 0.000 claims description 3
- CTPDSKVQLSDPLC-UHFFFAOYSA-N 2-(oxolan-2-ylmethoxy)ethanol Chemical compound OCCOCC1CCCO1 CTPDSKVQLSDPLC-UHFFFAOYSA-N 0.000 claims description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 2
- 229920002556 Polyethylene Glycol 300 Polymers 0.000 claims description 2
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- 239000008351 acetate buffer Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 230000000845 anti-microbial effect Effects 0.000 claims description 2
- 239000004599 antimicrobial Substances 0.000 claims description 2
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical class OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims description 2
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims description 2
- 239000004067 bulking agent Substances 0.000 claims description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical class OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 2
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 claims description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 2
- 239000000920 calcium hydroxide Substances 0.000 claims description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 2
- 239000004359 castor oil Substances 0.000 claims description 2
- 239000002738 chelating agent Substances 0.000 claims description 2
- WAZQAZKAZLXFMK-UHFFFAOYSA-N deracoxib Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(C(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 WAZQAZKAZLXFMK-UHFFFAOYSA-N 0.000 claims description 2
- 229960003314 deracoxib Drugs 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 229960004945 etoricoxib Drugs 0.000 claims description 2
- MNJVRJDLRVPLFE-UHFFFAOYSA-N etoricoxib Chemical compound C1=NC(C)=CC=C1C1=NC=C(Cl)C=C1C1=CC=C(S(C)(=O)=O)C=C1 MNJVRJDLRVPLFE-UHFFFAOYSA-N 0.000 claims description 2
- 229950005722 flosulide Drugs 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical class OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- 229920001477 hydrophilic polymer Polymers 0.000 claims description 2
- 239000003589 local anesthetic agent Substances 0.000 claims description 2
- 229960005015 local anesthetics Drugs 0.000 claims description 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims description 2
- 239000001095 magnesium carbonate Substances 0.000 claims description 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 claims description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 2
- 239000000347 magnesium hydroxide Substances 0.000 claims description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 2
- 239000000395 magnesium oxide Substances 0.000 claims description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 2
- CXJONBHNIJFARE-UHFFFAOYSA-N n-[6-(2,4-difluorophenoxy)-1-oxo-2,3-dihydroinden-5-yl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=2CCC(=O)C=2C=C1OC1=CC=C(F)C=C1F CXJONBHNIJFARE-UHFFFAOYSA-N 0.000 claims description 2
- 239000002357 osmotic agent Substances 0.000 claims description 2
- 239000003002 pH adjusting agent Substances 0.000 claims description 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 2
- 230000002335 preservative effect Effects 0.000 claims description 2
- 229940075579 propyl gallate Drugs 0.000 claims description 2
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- 239000000080 wetting agent Substances 0.000 claims description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 2
- 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 claims 1
- 125000003289 ascorbyl group Chemical group [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 claims 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims 1
- 229960003194 meglumine Drugs 0.000 claims 1
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- 102000010907 Cyclooxygenase 2 Human genes 0.000 abstract description 5
- 108010037462 Cyclooxygenase 2 Proteins 0.000 abstract description 5
- 241000124008 Mammalia Species 0.000 abstract description 5
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 5
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- 239000004615 ingredient Substances 0.000 description 17
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- 241000283973 Oryctolagus cuniculus Species 0.000 description 8
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- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
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- JGMJQSFLQWGYMQ-UHFFFAOYSA-M sodium;2,6-dichloro-n-phenylaniline;acetate Chemical compound [Na+].CC([O-])=O.ClC1=CC=CC(Cl)=C1NC1=CC=CC=C1 JGMJQSFLQWGYMQ-UHFFFAOYSA-M 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
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- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
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- SHBUUTHKGIVMJT-UHFFFAOYSA-N Hydroxystearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OO SHBUUTHKGIVMJT-UHFFFAOYSA-N 0.000 description 2
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 description 2
- 229920002685 Polyoxyl 35CastorOil Polymers 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 206010070863 Toxicity to various agents Diseases 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 229960004217 benzyl alcohol Drugs 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 229940097362 cyclodextrins Drugs 0.000 description 2
- 210000003743 erythrocyte Anatomy 0.000 description 2
- 229940072106 hydroxystearate Drugs 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 229960002479 isosorbide Drugs 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- QUANRIQJNFHVEU-UHFFFAOYSA-N oxirane;propane-1,2,3-triol Chemical compound C1CO1.OCC(O)CO QUANRIQJNFHVEU-UHFFFAOYSA-N 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000008389 polyethoxylated castor oil Substances 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 230000007928 solubilization Effects 0.000 description 2
- 238000005063 solubilization Methods 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
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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
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| IN1357/DEL/2005 | 2005-05-27 | ||
| PCT/IN2006/000177 WO2006126214A2 (en) | 2005-05-27 | 2006-05-25 | Injectable compositions and process for preparation of such compositions |
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| NO (1) | NO20076468L (xx) |
| RS (1) | RS20070461A (xx) |
| TN (1) | TNSN07482A1 (xx) |
| WO (1) | WO2006126214A2 (xx) |
| ZA (1) | ZA200711068B (xx) |
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| ES2728785T3 (es) | 2007-09-07 | 2019-10-28 | United Therapeutics Corp | Soluciones tampón con actividad bactericida selectiva contra las bacterias gramnegativas y métodos para usarlas |
| KR20140014350A (ko) * | 2009-03-12 | 2014-02-06 | 큠버랜드 파마슈티컬즈 인코포레이티드 | 정맥 내 투여용 이부프로펜의 투여 |
| US8871810B2 (en) | 2009-07-15 | 2014-10-28 | Cumberland Pharmaceuticals Inc. | Treating critically ill patients with intravenous ibuprofen |
| CN102335114B (zh) * | 2010-07-23 | 2015-07-15 | 重庆医药工业研究院有限责任公司 | 一种稳定的布洛芬精氨酸注射剂及其制备方法 |
| CN102370615B (zh) * | 2010-08-19 | 2013-09-04 | 四川科伦药物研究有限公司 | 一种布洛芬注射制剂及其制备方法 |
| JP6051466B2 (ja) | 2011-10-18 | 2016-12-27 | ラクオリア創薬株式会社 | 医薬組成物 |
| CN102512383A (zh) * | 2011-12-25 | 2012-06-27 | 天津市嵩锐医药科技有限公司 | 供注射用的帕瑞昔布钠药物组合物 |
| US9072710B2 (en) | 2012-03-16 | 2015-07-07 | Cumberland Pharmaceuticals Inc. | Injectable ibuprofen formulation |
| CN103372216B (zh) * | 2012-04-26 | 2015-05-06 | 北京京卫燕康药物研究所有限公司 | 一种含有塞来昔布的固体药物组合物 |
| TWI646091B (zh) | 2012-12-28 | 2019-01-01 | 日商衛斯克慧特股份有限公司 | 鹽類及晶形 |
| US20140187635A1 (en) | 2012-12-28 | 2014-07-03 | Themis Medicare Limited | Diclofenac compositions |
| US20140275261A1 (en) | 2013-03-15 | 2014-09-18 | Dr. Reddy's Laboratories, Inc. | Diclofenac parenteral compositions |
| CN103263385B (zh) * | 2013-05-17 | 2016-04-27 | 江苏正大清江制药有限公司 | 一种塞来昔布长效纳米注射剂及其制备方法 |
| KR20170099911A (ko) * | 2014-12-20 | 2017-09-01 | 트로이카 파마슈티칼스 리미티드 | 파라세타몰 주사 제제 |
| WO2016170401A1 (en) * | 2015-04-20 | 2016-10-27 | Umedica Laboratories Pvt. Ltd | Novel injectable composition of diclofenac sodium |
| CN107303266B (zh) * | 2016-04-18 | 2020-09-08 | 重庆润泽医药有限公司 | 左旋奥拉西坦注射液及其制备方法 |
| CN107303264A (zh) * | 2016-04-18 | 2017-10-31 | 重庆润泽医药有限公司 | 无泡沫左旋奥拉西坦注射液及其制备方法 |
| FR3077984B1 (fr) * | 2018-02-16 | 2020-02-21 | Vetoquinol Sa | Composition multiusage de torasemide |
| CN109498852B (zh) * | 2018-12-29 | 2022-06-24 | 广州噢斯荣医药技术有限公司 | 治疗骨科疾病的生物降解材料及其应用 |
| CN111103381A (zh) * | 2019-12-25 | 2020-05-05 | 南京希麦迪医药科技有限公司 | 一种液质联用测定人血浆中尼美舒利浓度的方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5389681A (en) * | 1992-10-22 | 1995-02-14 | Ciba-Geigy Corporation | Parenteral solutions for diclofenac salts |
| IT1283252B1 (it) * | 1996-03-15 | 1998-04-16 | Pulitzer Italiana | Soluzioni di piroxicam iniettabili per via parenterale |
| IN187306B (xx) * | 1998-01-12 | 2002-03-23 | Panacea Biotec Ltd | |
| PE20021017A1 (es) * | 2001-04-03 | 2002-11-24 | Pharmacia Corp | Composicion parenteral reconstituible |
| AU2003249510A1 (en) * | 2002-08-12 | 2004-02-25 | Ranbaxy Laboratories Limited | A parenteral dosage form of selective cox-2 inhibitors |
-
2006
- 2006-05-25 EP EP06756263A patent/EP1895983A2/en not_active Withdrawn
- 2006-05-25 CA CA002609242A patent/CA2609242A1/en not_active Abandoned
- 2006-05-25 WO PCT/IN2006/000177 patent/WO2006126214A2/en active Application Filing
- 2006-05-25 MX MX2007014862A patent/MX2007014862A/es not_active Application Discontinuation
- 2006-05-25 AU AU2006250765A patent/AU2006250765A1/en not_active Abandoned
- 2006-05-25 KR KR1020077030585A patent/KR20080016689A/ko not_active Application Discontinuation
- 2006-05-25 RS RSP-2007/0461A patent/RS20070461A/sr unknown
- 2006-05-25 JP JP2008513009A patent/JP2008542260A/ja not_active Withdrawn
- 2006-05-25 CN CNA2006800250937A patent/CN101217939A/zh active Pending
- 2006-05-25 ZA ZA200711068A patent/ZA200711068B/xx unknown
- 2006-05-25 BR BRPI0611170-0A patent/BRPI0611170A2/pt not_active IP Right Cessation
- 2006-05-25 EA EA200702646A patent/EA200702646A1/ru unknown
-
2007
- 2007-12-14 NO NO20076468A patent/NO20076468L/no not_active Application Discontinuation
- 2007-12-19 CR CR9616A patent/CR9616A/es not_active Application Discontinuation
- 2007-12-21 TN TNP2007000482A patent/TNSN07482A1/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006126214A2 (en) | 2006-11-30 |
| CN101217939A (zh) | 2008-07-09 |
| WO2006126214A3 (en) | 2007-06-07 |
| NO20076468L (no) | 2008-02-27 |
| EA200702646A1 (ru) | 2008-06-30 |
| KR20080016689A (ko) | 2008-02-21 |
| JP2008542260A (ja) | 2008-11-27 |
| AU2006250765A1 (en) | 2006-11-30 |
| TNSN07482A1 (fr) | 2009-03-17 |
| CR9616A (es) | 2008-10-30 |
| BRPI0611170A2 (pt) | 2010-08-17 |
| MX2007014862A (es) | 2008-02-21 |
| RS20070461A (xx) | 2008-11-28 |
| ZA200711068B (en) | 2009-03-25 |
| EP1895983A2 (en) | 2008-03-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |