CA3213549A1 - Pharmaceutical compositions comprising meloxicam - Google Patents
Pharmaceutical compositions comprising meloxicamInfo
- Publication number
- CA3213549A1 CA3213549A1 CA3213549A CA3213549A CA3213549A1 CA 3213549 A1 CA3213549 A1 CA 3213549A1 CA 3213549 A CA3213549 A CA 3213549A CA 3213549 A CA3213549 A CA 3213549A CA 3213549 A1 CA3213549 A1 CA 3213549A1
- Authority
- CA
- Canada
- Prior art keywords
- meloxicam
- dosage form
- rizatriptan
- migraine
- hours
- 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.)
- Pending
Links
- ZRVUJXDFFKFLMG-UHFFFAOYSA-N Meloxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=C(C)S1 ZRVUJXDFFKFLMG-UHFFFAOYSA-N 0.000 title claims abstract description 420
- 229960001929 meloxicam Drugs 0.000 title claims abstract description 414
- 239000008194 pharmaceutical composition Substances 0.000 title description 12
- 229960000425 rizatriptan Drugs 0.000 claims abstract description 327
- 206010027599 migraine Diseases 0.000 claims abstract description 255
- 208000019695 Migraine disease Diseases 0.000 claims abstract description 245
- 208000002193 Pain Diseases 0.000 claims abstract description 154
- 230000036407 pain Effects 0.000 claims abstract description 146
- 241000282414 Homo sapiens Species 0.000 claims abstract description 140
- 238000000034 method Methods 0.000 claims abstract description 112
- 238000011282 treatment Methods 0.000 claims abstract description 78
- TXHZXHICDBAVJW-UHFFFAOYSA-N rizatriptan Chemical compound C=1[C]2C(CCN(C)C)=CN=C2C=CC=1CN1C=NC=N1 TXHZXHICDBAVJW-UHFFFAOYSA-N 0.000 claims abstract 13
- 239000002552 dosage form Substances 0.000 claims description 230
- 229920000858 Cyclodextrin Polymers 0.000 claims description 157
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 79
- 239000006186 oral dosage form Substances 0.000 claims description 60
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 58
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 40
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 40
- 206010028813 Nausea Diseases 0.000 claims description 29
- 230000008693 nausea Effects 0.000 claims description 29
- 230000004044 response Effects 0.000 claims description 29
- 206010054956 Phonophobia Diseases 0.000 claims description 26
- 206010034960 Photophobia Diseases 0.000 claims description 26
- NZAQRZWBQUIBSF-UHFFFAOYSA-N 4-(4-sulfobutoxy)butane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCCOCCCCS(O)(=O)=O NZAQRZWBQUIBSF-UHFFFAOYSA-N 0.000 claims description 21
- 230000036470 plasma concentration Effects 0.000 claims description 21
- 230000009467 reduction Effects 0.000 claims description 21
- 150000003839 salts Chemical group 0.000 claims description 16
- JPRXYLQNJJVCMZ-UHFFFAOYSA-N Rizatriptan benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1.C1=C2C(CC[NH+](C)C)=CNC2=CC=C1CN1C=NC=N1 JPRXYLQNJJVCMZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000012458 free base Substances 0.000 claims description 10
- 230000001225 therapeutic effect Effects 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 4
- 229960004789 rizatriptan benzoate Drugs 0.000 claims description 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 abstract description 25
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 abstract description 25
- 230000001154 acute effect Effects 0.000 abstract description 24
- 206010003246 arthritis Diseases 0.000 abstract description 9
- 239000000203 mixture Substances 0.000 abstract description 9
- 208000000060 Migraine with aura Diseases 0.000 abstract description 2
- ULFRLSNUDGIQQP-UHFFFAOYSA-N rizatriptan Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1CN1C=NC=N1 ULFRLSNUDGIQQP-UHFFFAOYSA-N 0.000 description 314
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 54
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 49
- 239000003826 tablet Substances 0.000 description 48
- 239000000902 placebo Substances 0.000 description 31
- 229940068196 placebo Drugs 0.000 description 31
- 230000002459 sustained effect Effects 0.000 description 26
- 229910000027 potassium carbonate Inorganic materials 0.000 description 24
- -1 cyclic polysaccharides Chemical class 0.000 description 23
- 206010019233 Headaches Diseases 0.000 description 22
- 239000002253 acid Substances 0.000 description 20
- 230000006872 improvement Effects 0.000 description 20
- 235000015320 potassium carbonate Nutrition 0.000 description 20
- 208000024891 symptom Diseases 0.000 description 20
- ZISSAWUMDACLOM-UHFFFAOYSA-N triptane Chemical compound CC(C)C(C)(C)C ZISSAWUMDACLOM-UHFFFAOYSA-N 0.000 description 20
- 208000004454 Hyperalgesia Diseases 0.000 description 19
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- 229940079593 drug Drugs 0.000 description 14
- 239000003814 drug Substances 0.000 description 14
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
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- 239000000243 solution Substances 0.000 description 9
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 8
- 206010047700 Vomiting Diseases 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 229940103177 maxalt Drugs 0.000 description 8
- 230000008673 vomiting Effects 0.000 description 8
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- 229940112801 mobic Drugs 0.000 description 6
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- 229940126409 proton pump inhibitor Drugs 0.000 description 6
- 239000000612 proton pump inhibitor Substances 0.000 description 6
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- 239000003795 chemical substances by application Substances 0.000 description 5
- 229960004770 esomeprazole Drugs 0.000 description 5
- SUBDBMMJDZJVOS-DEOSSOPVSA-N esomeprazole Chemical compound C([S@](=O)C1=NC2=CC=C(C=C2N1)OC)C1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-DEOSSOPVSA-N 0.000 description 5
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- 208000004296 neuralgia Diseases 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 238000007920 subcutaneous administration Methods 0.000 description 5
- KRQUFUKTQHISJB-YYADALCUSA-N 2-[(E)-N-[2-(4-chlorophenoxy)propoxy]-C-propylcarbonimidoyl]-3-hydroxy-5-(thian-3-yl)cyclohex-2-en-1-one Chemical compound CCC\C(=N/OCC(C)OC1=CC=C(Cl)C=C1)C1=C(O)CC(CC1=O)C1CCCSC1 KRQUFUKTQHISJB-YYADALCUSA-N 0.000 description 4
- 206010065390 Inflammatory pain Diseases 0.000 description 4
- 206010028391 Musculoskeletal Pain Diseases 0.000 description 4
- 208000012902 Nervous system disease Diseases 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 238000009505 enteric coating Methods 0.000 description 4
- 239000002702 enteric coating Substances 0.000 description 4
- 238000002483 medication Methods 0.000 description 4
- 208000021722 neuropathic pain Diseases 0.000 description 4
- 238000005457 optimization Methods 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- 239000002356 single layer Substances 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 208000025705 Axial Spondyloarthritis Diseases 0.000 description 3
- 208000008035 Back Pain Diseases 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 206010061218 Inflammation Diseases 0.000 description 3
- 208000012659 Joint disease Diseases 0.000 description 3
- 208000003456 Juvenile Arthritis Diseases 0.000 description 3
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- 208000025966 Neurological disease Diseases 0.000 description 3
- 208000008589 Obesity Diseases 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 201000002661 Spondylitis Diseases 0.000 description 3
- 208000027418 Wounds and injury Diseases 0.000 description 3
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- 230000000202 analgesic effect Effects 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000013626 chemical specie Substances 0.000 description 3
- 208000019069 chronic childhood arthritis Diseases 0.000 description 3
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- 201000002215 juvenile rheumatoid arthritis Diseases 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 235000020824 obesity Nutrition 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- 239000011736 potassium bicarbonate Substances 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- MAVJDLHBPIXVJL-UHFFFAOYSA-N 1-[8-methoxy-4-(2-methylanilino)quinolin-3-yl]butan-1-one Chemical compound CCCC(=O)C1=CN=C2C(OC)=CC=CC2=C1NC1=CC=CC=C1C MAVJDLHBPIXVJL-UHFFFAOYSA-N 0.000 description 2
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-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
- 208000007815 Acquired Hyperostosis Syndrome Diseases 0.000 description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 description 2
- 241000167854 Bourreria succulenta Species 0.000 description 2
- 108090000932 Calcitonin Gene-Related Peptide Proteins 0.000 description 2
- 102100025588 Calcitonin gene-related peptide 1 Human genes 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 206010058019 Cancer Pain Diseases 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- 208000006561 Cluster Headache Diseases 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
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- 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 2
- 241001465754 Metazoa Species 0.000 description 2
- 208000005268 Neurogenic Arthropathy Diseases 0.000 description 2
- 206010029326 Neuropathic arthropathy Diseases 0.000 description 2
- MITFXPHMIHQXPI-UHFFFAOYSA-N Oraflex Chemical compound N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 2
- 208000001132 Osteoporosis Diseases 0.000 description 2
- IQPSEEYGBUAQFF-UHFFFAOYSA-N Pantoprazole Chemical compound COC1=CC=NC(CS(=O)C=2NC3=CC=C(OC(F)F)C=C3N=2)=C1OC IQPSEEYGBUAQFF-UHFFFAOYSA-N 0.000 description 2
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 2
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
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- VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
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- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
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- PPQREHKVAOVYBT-UHFFFAOYSA-H dialuminum;tricarbonate Chemical compound [Al+3].[Al+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O PPQREHKVAOVYBT-UHFFFAOYSA-H 0.000 description 2
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- MJIHNNLFOKEZEW-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-UHFFFAOYSA-N 0.000 description 2
- 238000001294 liquid chromatography-tandem mass spectrometry Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- 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
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- YREYEVIYCVEVJK-UHFFFAOYSA-N rabeprazole Chemical compound COCCCOC1=CC=NC(CS(=O)C=2NC3=CC=CC=C3N=2)=C1C YREYEVIYCVEVJK-UHFFFAOYSA-N 0.000 description 2
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- 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 description 2
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- NXPLYKRKIFPEOA-BLLLJJGKSA-N 7-[(4-fluorophenyl)methoxy]-2,3-dimethyl-1-[[(1s,2s)-2-methylcyclopropyl]methyl]pyrrolo[2,3-d]pyridazine Chemical compound C[C@H]1C[C@@H]1CN1C2=C(OCC=3C=CC(F)=CC=3)N=NC=C2C(C)=C1C NXPLYKRKIFPEOA-BLLLJJGKSA-N 0.000 description 1
- GHVIMBCFLRTFHI-UHFFFAOYSA-N 8-[(2,6-dimethylphenyl)methylamino]-n-(2-hydroxyethyl)-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound C=1C(C(=O)NCCO)=CN2C(C)=C(C)N=C2C=1NCC1=C(C)C=CC=C1C GHVIMBCFLRTFHI-UHFFFAOYSA-N 0.000 description 1
- IDSZXCFCCNVXER-UHFFFAOYSA-N 8-[(2-ethyl-6-methylphenyl)methylamino]-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound CCC1=CC=CC(C)=C1CNC1=CC(C(N)=O)=CN2C1=NC(C)=C2C IDSZXCFCCNVXER-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
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- A61K31/5415—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with carbocyclic ring systems, e.g. phenothiazine, chlorpromazine, piroxicam
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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Landscapes
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Applications Claiming Priority (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962802198P | 2019-02-06 | 2019-02-06 | |
| US62/802,198 | 2019-02-06 | ||
| US201962803756P | 2019-02-11 | 2019-02-11 | |
| US62/803,756 | 2019-02-11 | ||
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| US20040214861A1 (en) * | 2003-03-28 | 2004-10-28 | Pharmacia Corporation | Compositions of a cyclooxygenase-2 selective inhibitors and 5-HT1B1D antagonists for the treatment and prevention of migraine |
| US8268791B2 (en) * | 2004-08-25 | 2012-09-18 | Aegis Therapeutics, Llc. | Alkylglycoside compositions for drug administration |
| US20090068262A1 (en) * | 2007-04-04 | 2009-03-12 | Ilan Zalit | Rapid dissolution of combination products |
| KR101743591B1 (ko) * | 2009-05-13 | 2017-06-20 | 사이덱스 파마슈티칼스, 인크. | 프라수그렐 및 사이클로덱스트린 유도체를 포함하는 약학 조성물 및 그의 제조 및 사용 방법 |
| US9821075B2 (en) * | 2015-02-10 | 2017-11-21 | Axsome Therapeutics, Inc. | Pharmaceutical compositions comprising meloxicam |
| KR102465027B1 (ko) * | 2015-02-10 | 2022-11-09 | 액섬 테라퓨틱스, 인크. | 멜록시캄을 포함하는 약학 조성물 |
| WO2018055574A1 (en) * | 2016-09-23 | 2018-03-29 | Teva Pharmaceuticals International Gmbh | Treating refractory migraine |
| PT3565550T (pt) * | 2017-01-04 | 2021-01-20 | Axsome Therapeutics Inc | Composições farmacêuticas compreendendo meloxicam e rizatriptano |
| US10471014B2 (en) * | 2017-01-04 | 2019-11-12 | Axsome Therapeutics, Inc. | Pharmaceutical compositions comprising meloxicam |
| NZ758664A (en) * | 2017-05-10 | 2022-08-26 | Axsome Therapeutics Inc | Pharmaceutical compositions comprising meloxicam |
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| EP3920909A4 (en) | 2022-11-30 |
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| PE20212157A1 (es) | 2021-11-09 |
| WO2020163620A1 (en) | 2020-08-13 |
| CA3128940C (en) | 2023-11-07 |
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| CA3128940A1 (en) | 2020-08-13 |
| CL2021002070A1 (es) | 2022-04-01 |
| MX2021009435A (es) | 2021-09-10 |
| JP2022519670A (ja) | 2022-03-24 |
| KR20210118880A (ko) | 2021-10-01 |
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