ES2562069T3 - Formas en estado sólido de un fármaco - Google Patents
Formas en estado sólido de un fármaco Download PDFInfo
- Publication number
- ES2562069T3 ES2562069T3 ES09726748.8T ES09726748T ES2562069T3 ES 2562069 T3 ES2562069 T3 ES 2562069T3 ES 09726748 T ES09726748 T ES 09726748T ES 2562069 T3 ES2562069 T3 ES 2562069T3
- Authority
- ES
- Spain
- Prior art keywords
- androst
- triol
- eno
- crystalline
- ethynyl
- 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.)
- Active
Links
- 239000007787 solid Substances 0.000 title description 111
- 239000003814 drug Substances 0.000 title description 5
- 229940079593 drug Drugs 0.000 title description 2
- 239000000203 mixture Substances 0.000 description 78
- 229940125904 compound 1 Drugs 0.000 description 76
- 238000000634 powder X-ray diffraction Methods 0.000 description 63
- 238000009472 formulation Methods 0.000 description 56
- 238000000034 method Methods 0.000 description 51
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 47
- 238000001757 thermogravimetry curve Methods 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- 239000012453 solvate Substances 0.000 description 33
- 238000002411 thermogravimetry Methods 0.000 description 33
- 238000000113 differential scanning calorimetry Methods 0.000 description 32
- 238000004458 analytical method Methods 0.000 description 26
- 238000001069 Raman spectroscopy Methods 0.000 description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 24
- 239000000546 pharmaceutical excipient Substances 0.000 description 24
- 230000009102 absorption Effects 0.000 description 22
- 238000010521 absorption reaction Methods 0.000 description 22
- 239000013078 crystal Substances 0.000 description 21
- 201000010099 disease Diseases 0.000 description 21
- 239000000725 suspension Substances 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 20
- 238000002441 X-ray diffraction Methods 0.000 description 18
- 238000004455 differential thermal analysis Methods 0.000 description 18
- 239000000843 powder Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 208000016261 weight loss Diseases 0.000 description 16
- 230000004580 weight loss Effects 0.000 description 16
- 238000001237 Raman spectrum Methods 0.000 description 15
- 239000002245 particle Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- 230000001154 acute effect Effects 0.000 description 12
- 239000004094 surface-active agent Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 208000023275 Autoimmune disease Diseases 0.000 description 10
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 10
- 229960001031 glucose Drugs 0.000 description 10
- 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 9
- 239000002178 crystalline material Substances 0.000 description 9
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 9
- 239000008103 glucose Substances 0.000 description 9
- 230000003345 hyperglycaemic effect Effects 0.000 description 9
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 9
- 206010012601 diabetes mellitus Diseases 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- 206010022489 Insulin Resistance Diseases 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 206010009900 Colitis ulcerative Diseases 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 6
- 201000006704 Ulcerative Colitis Diseases 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 150000004677 hydrates Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 201000006417 multiple sclerosis Diseases 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 102000004877 Insulin Human genes 0.000 description 5
- 108090001061 Insulin Proteins 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 230000036571 hydration Effects 0.000 description 5
- 238000006703 hydration reaction Methods 0.000 description 5
- 201000001421 hyperglycemia Diseases 0.000 description 5
- 229940125396 insulin Drugs 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 206010039073 rheumatoid arthritis Diseases 0.000 description 5
- 238000010583 slow cooling Methods 0.000 description 5
- 208000011231 Crohn disease Diseases 0.000 description 4
- 208000002705 Glucose Intolerance Diseases 0.000 description 4
- 208000030836 Hashimoto thyroiditis Diseases 0.000 description 4
- 208000035150 Hypercholesterolemia Diseases 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 230000004054 inflammatory process Effects 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- 201000009104 prediabetes syndrome Diseases 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000011002 quantification Methods 0.000 description 4
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 4
- 238000010996 solid-state NMR spectroscopy Methods 0.000 description 4
- 238000002460 vibrational spectroscopy Methods 0.000 description 4
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- 208000001145 Metabolic Syndrome Diseases 0.000 description 3
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 208000003435 Optic Neuritis Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000007707 calorimetry Methods 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 208000027866 inflammatory disease Diseases 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 3
- 239000008108 microcrystalline cellulose Substances 0.000 description 3
- 229940016286 microcrystalline cellulose Drugs 0.000 description 3
- 230000000291 postprandial effect Effects 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- 238000000371 solid-state nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000004611 spectroscopical analysis Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 2
- 208000026310 Breast neoplasm Diseases 0.000 description 2
- QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- 206010021024 Hypolipidaemia Diseases 0.000 description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- 238000004497 NIR spectroscopy Methods 0.000 description 2
- 208000008589 Obesity Diseases 0.000 description 2
- 208000018737 Parkinson disease Diseases 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 238000005102 attenuated total reflection Methods 0.000 description 2
- 206010006451 bronchitis Diseases 0.000 description 2
- 239000006172 buffering agent Substances 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 230000001066 destructive effect Effects 0.000 description 2
- 238000012631 diagnostic technique Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000008394 flocculating agent Substances 0.000 description 2
- 230000003463 hyperproliferative effect Effects 0.000 description 2
- 208000006575 hypertriglyceridemia Diseases 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 210000004153 islets of langerhan Anatomy 0.000 description 2
- 239000012669 liquid formulation Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 229940057948 magnesium stearate Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 208000030159 metabolic disease Diseases 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 230000004770 neurodegeneration Effects 0.000 description 2
- 208000015122 neurodegenerative disease Diseases 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 description 2
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 description 2
- 235000020824 obesity Nutrition 0.000 description 2
- 239000006186 oral dosage form Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 238000000513 principal component analysis Methods 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 238000004445 quantitative analysis Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 238000002424 x-ray crystallography Methods 0.000 description 2
- 208000004611 Abdominal Obesity Diseases 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 206010052613 Allergic bronchitis Diseases 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 1
- 206010006458 Bronchitis chronic Diseases 0.000 description 1
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 206010065941 Central obesity Diseases 0.000 description 1
- 208000017667 Chronic Disease Diseases 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 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 1
- 206010014561 Emphysema Diseases 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 102000003676 Glucocorticoid Receptors Human genes 0.000 description 1
- 108090000079 Glucocorticoid Receptors Proteins 0.000 description 1
- 206010018429 Glucose tolerance impaired Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 206010020961 Hypocholesterolaemia Diseases 0.000 description 1
- 206010056997 Impaired fasting glucose Diseases 0.000 description 1
- 102000003746 Insulin Receptor Human genes 0.000 description 1
- 108010001127 Insulin Receptor Proteins 0.000 description 1
- 238000008214 LDL Cholesterol Methods 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 208000019693 Lung disease Diseases 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 208000036110 Neuroinflammatory disease Diseases 0.000 description 1
- 208000011623 Obstructive Lung disease Diseases 0.000 description 1
- 241000009328 Perro Species 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 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 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 208000024716 acute asthma Diseases 0.000 description 1
- 206010064930 age-related macular degeneration Diseases 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229960001040 ammonium chloride Drugs 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229940043379 ammonium hydroxide Drugs 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 230000002917 arthritic effect Effects 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 230000005784 autoimmunity Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- 229940067596 butylparaben Drugs 0.000 description 1
- RPPBZEBXAAZZJH-UHFFFAOYSA-N cadmium telluride Chemical compound [Te]=[Cd] RPPBZEBXAAZZJH-UHFFFAOYSA-N 0.000 description 1
- QHMBSVQNZZTUGM-ZWKOTPCHSA-N cannabidiol Chemical compound OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-ZWKOTPCHSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 208000023819 chronic asthma Diseases 0.000 description 1
- 208000007451 chronic bronchitis Diseases 0.000 description 1
- 208000019425 cirrhosis of liver Diseases 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- RKTYLMNFRDHKIL-UHFFFAOYSA-N copper;5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical compound [Cu+2].C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 RKTYLMNFRDHKIL-UHFFFAOYSA-N 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940099112 cornstarch Drugs 0.000 description 1
- 229960000913 crospovidone Drugs 0.000 description 1
- 239000008380 degradant Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000004807 desolvation Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940111685 dibasic potassium phosphate Drugs 0.000 description 1
- 229940061607 dibasic sodium phosphate Drugs 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 208000016097 disease of metabolism Diseases 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005315 distribution function Methods 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 208000010706 fatty liver disease Diseases 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- -1 fluidizers Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000009615 fourier-transform spectroscopy Methods 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000003914 insulin secretion Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 201000010901 lateral sclerosis Diseases 0.000 description 1
- 208000020442 loss of weight Diseases 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 208000002780 macular degeneration Diseases 0.000 description 1
- JNZGLUUWTFPBKG-UHFFFAOYSA-K magnesium;potassium;trichloride Chemical compound [Mg+2].[Cl-].[Cl-].[Cl-].[K+] JNZGLUUWTFPBKG-UHFFFAOYSA-K 0.000 description 1
- UNXVFOUTYUQFJD-UHFFFAOYSA-K magnesium;sodium;trichloride Chemical compound [Na+].[Cl-].Cl[Mg]Cl UNXVFOUTYUQFJD-UHFFFAOYSA-K 0.000 description 1
- STFVDQZWTZJIHE-UHFFFAOYSA-H magnesium;titanium(4+);hexachloride Chemical compound [Mg+2].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Ti+4] STFVDQZWTZJIHE-UHFFFAOYSA-H 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 208000037819 metastatic cancer Diseases 0.000 description 1
- 208000011575 metastatic malignant neoplasm Diseases 0.000 description 1
- 208000010658 metastatic prostate carcinoma Diseases 0.000 description 1
- GRWIABMEEKERFV-UHFFFAOYSA-N methanol;oxolane Chemical compound OC.C1CCOC1 GRWIABMEEKERFV-UHFFFAOYSA-N 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 238000007431 microscopic evaluation Methods 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940111688 monobasic potassium phosphate Drugs 0.000 description 1
- 229940045641 monobasic sodium phosphate Drugs 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 238000003333 near-infrared imaging Methods 0.000 description 1
- 230000003959 neuroinflammation Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000000399 optical microscopy Methods 0.000 description 1
- 239000008184 oral solid dosage form Substances 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 238000010238 partial least squares regression Methods 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 1
- 229960002702 piroxicam Drugs 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229940094025 potassium bicarbonate Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229940093956 potassium carbonate Drugs 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940093932 potassium hydroxide Drugs 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 208000005069 pulmonary fibrosis Diseases 0.000 description 1
- 229960001520 ranitidine hydrochloride Drugs 0.000 description 1
- GGWBHVILAJZWKJ-KJEVSKRMSA-N ranitidine hydrochloride Chemical compound [H+].[Cl-].[O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 GGWBHVILAJZWKJ-KJEVSKRMSA-N 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 238000000646 scanning calorimetry Methods 0.000 description 1
- 238000004626 scanning electron microscopy Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229940083608 sodium hydroxide Drugs 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000012439 solid excipient Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000004627 transmission electron microscopy Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 229940062627 tribasic potassium phosphate Drugs 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Obesity (AREA)
- Epidemiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Child & Adolescent Psychology (AREA)
- Pain & Pain Management (AREA)
- Ophthalmology & Optometry (AREA)
- Transplantation (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Endocrinology (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42240 | 1998-03-13 | ||
| US4224008P | 2008-04-03 | 2008-04-03 | |
| PCT/US2009/039567 WO2009124300A2 (en) | 2008-04-03 | 2009-04-03 | Solid state forms of a pharmaceutical |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2562069T3 true ES2562069T3 (es) | 2016-03-02 |
Family
ID=41136126
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09726748.8T Active ES2562069T3 (es) | 2008-04-03 | 2009-04-03 | Formas en estado sólido de un fármaco |
Country Status (13)
| Country | Link |
|---|---|
| US (9) | US8252947B2 (enExample) |
| EP (1) | EP2273994B1 (enExample) |
| JP (2) | JP2011527986A (enExample) |
| KR (1) | KR101545300B1 (enExample) |
| CN (1) | CN102215845A (enExample) |
| AU (1) | AU2009231589B2 (enExample) |
| CA (1) | CA2728889C (enExample) |
| DK (1) | DK2273994T3 (enExample) |
| ES (1) | ES2562069T3 (enExample) |
| HU (1) | HUE028337T2 (enExample) |
| PL (1) | PL2273994T3 (enExample) |
| PT (1) | PT2273994E (enExample) |
| WO (1) | WO2009124300A2 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009124300A2 (en) | 2008-04-03 | 2009-10-08 | Hollis-Eden Pharmaceuticals, Inc. | Solid state forms of a pharmaceutical |
| CA2724130C (en) | 2008-06-06 | 2016-04-26 | Harbor Biosciences, Inc. | Methods for preparing 17-alkynyl-7-hydroxy steroids and related compounds |
| US20120220560A1 (en) * | 2010-12-17 | 2012-08-30 | White Steven K | Steroid tetrol solid state forms |
| CN103768071B (zh) * | 2012-10-23 | 2016-08-17 | 中国医药工业研究总院 | 一种治疗糖尿病的口服制剂 |
| WO2019041078A1 (en) * | 2017-08-28 | 2019-03-07 | Zhejiang Jiachi Pharmaceutical Development Ltd. | ASYMMETRIC SYNTHESIS AND USES OF COMPOUNDS IN TREATMENT OF DISEASES |
| CA3218191A1 (en) * | 2021-05-18 | 2022-11-24 | Clarence Nathaniel Ahlem | Compositions for treatment of neurodegenerative conditions |
| WO2024054452A1 (en) * | 2022-09-06 | 2024-03-14 | Biovie Inc. | Methods for the treatment of mild cognitive impairment |
| CN120484042A (zh) * | 2025-05-16 | 2025-08-15 | 中国人民解放军军事科学院军事医学研究院 | 一种he3286的合成方法 |
Family Cites Families (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4329366A (en) * | 1979-11-08 | 1982-05-11 | Johnson & Johnson Products, Inc. | Topical acylaminophenols |
| US4898694A (en) * | 1987-11-25 | 1990-02-06 | Schwartz Arthur G | 17-Hydroxy-steroids |
| DE3801229A1 (de) | 1988-01-18 | 1989-07-27 | Krupp Polysius Ag | Mahlverfahren sowie mahlanlage |
| JP2642486B2 (ja) | 1989-08-04 | 1997-08-20 | 田辺製薬株式会社 | 難溶性薬物の超微粒子化法 |
| US5292730A (en) * | 1990-08-29 | 1994-03-08 | Humanetics Corporation | Modulation of immune system with Δ5-androstenes |
| AU647528B2 (en) * | 1990-08-29 | 1994-03-24 | Humanetics Corporation | Treatment process for promoting weight loss employing a substituted delta5-androstene |
| US5641766A (en) * | 1990-08-29 | 1997-06-24 | Humanetics Corporation | UP-regulation of immune system with Δ 5-Androstenes |
| US5271944A (en) | 1991-04-05 | 1993-12-21 | Biofor, Ltd. | Pharmacologically enhanced formulations |
| US5922701A (en) * | 1992-05-01 | 1999-07-13 | University Of Utah Research Foundation | Method for enhancing or accelerating re-epithelialization or re-endothelialization of a tissue |
| US5424077A (en) | 1993-07-13 | 1995-06-13 | Church & Dwight Co., Inc. | Co-micronized bicarbonate salt compositions |
| TW369521B (en) | 1993-09-17 | 1999-09-11 | Smithkline Beecham Corp | Androstenone derivative |
| US5455049A (en) | 1995-01-04 | 1995-10-03 | Ascent Pharmaceuticals, Inc. | Terfenadine oral powder |
| US5859000A (en) * | 1995-06-07 | 1999-01-12 | University Of Utah Research Foundation | Method for reducing mast cell mediated allergic reactions |
| US6686486B1 (en) * | 1997-05-07 | 2004-02-03 | Padma Marwah | Process for effecting allylic oxidation |
| US5869709A (en) * | 1997-05-07 | 1999-02-09 | Humanetics Corporation | Process for effecting allylic oxidation |
| ZA986614B (en) * | 1997-07-25 | 1999-01-27 | Gilead Sciences | Nucleotide analog composition |
| AU3088799A (en) * | 1998-03-18 | 1999-10-11 | Humanetics Corporation | Process for effecting allylic oxidation using dicarboxylic acid imides and chromium reagents |
| US20060079492A1 (en) * | 1999-10-25 | 2006-04-13 | Ahlem Clarence N | Compositions and treatment methods |
| US20080015174A1 (en) * | 1998-11-24 | 2008-01-17 | Reading Christopher L | Metabolic Disease Treatments |
| US20030060425A1 (en) * | 1998-11-24 | 2003-03-27 | Ahlem Clarence N. | Immune modulation method using steroid compounds |
| US6667299B1 (en) * | 2000-03-16 | 2003-12-23 | Hollis-Eden Pharmaceuticals, Inc. | Pharmaceutical compositions and treatment methods |
| US20030083231A1 (en) * | 1998-11-24 | 2003-05-01 | Ahlem Clarence N. | Blood cell deficiency treatment method |
| US20070129282A1 (en) * | 1998-11-24 | 2007-06-07 | Ahlem Clarence N | Pharmaceutical treatments and compositions |
| US7045513B1 (en) * | 1999-03-18 | 2006-05-16 | Genelabs Technologies, Inc. | DHEA composition and method |
| EP1228083A2 (en) * | 1999-09-30 | 2002-08-07 | Hollis-Eden Pharmaceuticals Inc. | Therapeutic treatment of androgen receptor driven conditions |
| CA2388939C (en) | 1999-10-25 | 2009-06-09 | Hollis-Eden Pharmaceuticals, Inc. | Therapeutic treatments for blood cell deficiencies |
| US6274746B1 (en) * | 2000-08-30 | 2001-08-14 | Padma Marwah | Process for allylic oxidation using metal hypochlorite and alkyl hydroperoxide |
| ATE307591T1 (de) * | 2000-12-14 | 2005-11-15 | Ortho Mcneil Pharm Inc | Zubereitungen enthaltend ein steroidhormon und ein stabilisierungsmittel in nicht-kristalliner form |
| FR2820745A1 (fr) * | 2001-02-14 | 2002-08-16 | Oreal | Procedes de preparation de la 7alpha-hydroxy- dehydroepiandrosterone |
| WO2003043570A2 (en) * | 2001-11-15 | 2003-05-30 | Galileo Laboratories, Inc. | Formulations and methods for treatment or amelioration of inflammatory conditions |
| JP2005534927A (ja) | 2002-08-06 | 2005-11-17 | エスエスシーアイ，インコーポレイティド | ファンダメンタルパラメータ法を用いたｘ線回折パターンの比較法 |
| WO2005045726A2 (en) | 2003-10-27 | 2005-05-19 | Ssci, Inc. | Method for monte carlo indexing of powder diffraction data |
| US20070243620A1 (en) | 2004-02-24 | 2007-10-18 | Simon Bates | Analysis and Screening of Solid Forms Using the Atomic Pair Distribution Function |
| CA2582231A1 (en) * | 2004-09-29 | 2006-10-19 | Hollis-Eden Pharmaceuticals, Inc. | Steroid analogs and uses |
| US20060073099A1 (en) * | 2004-10-01 | 2006-04-06 | Frincke James M | Treatment screening methods |
| US20060211604A1 (en) * | 2004-11-26 | 2006-09-21 | The Brigham And Women's Hospital, Inc. | Methods for treating inflammatory disorders using regulators of microvessel dilations |
| US7964604B2 (en) * | 2005-02-18 | 2011-06-21 | Solvay Pharmaceuticals B.V. | Bifeprunox mesylate maintenance dose compositions and methods for using the same |
| CN103211821A (zh) | 2006-04-22 | 2013-07-24 | 霍利斯—伊登医药公司 | 药物和用途 |
| US20080153792A1 (en) * | 2006-11-17 | 2008-06-26 | Frincke James M | Drug Identification and Treatment Method |
| US8354396B2 (en) * | 2006-11-17 | 2013-01-15 | Harbor Therapeutics, Inc. | Drug identification and treatment method |
| US20080221074A1 (en) * | 2006-11-17 | 2008-09-11 | Jaime Flores-Riveros | Drug Screen and Treatment Method |
| US8217025B2 (en) * | 2006-11-17 | 2012-07-10 | Harbor Therapeutics, Inc. | Drug screening and treatment methods |
| DE102007054497B3 (de) * | 2007-11-13 | 2009-07-23 | Sanofi-Aventis Deutschland Gmbh | Neue kristalline Diphenylazetidinonhydrate und Verfahren zu deren Herstellung |
| WO2009100258A1 (en) * | 2008-02-05 | 2009-08-13 | Hollis-Eden Pharmaceuticals, Inc. | Pharmaceutical solid state forms |
| WO2009124300A2 (en) | 2008-04-03 | 2009-10-08 | Hollis-Eden Pharmaceuticals, Inc. | Solid state forms of a pharmaceutical |
| CA2724130C (en) * | 2008-06-06 | 2016-04-26 | Harbor Biosciences, Inc. | Methods for preparing 17-alkynyl-7-hydroxy steroids and related compounds |
| US20100075937A1 (en) * | 2008-09-24 | 2010-03-25 | Hollis-Eden Pharmaceuticals, Inc. | Patient populations and treatment methods |
| US9310310B2 (en) | 2011-08-26 | 2016-04-12 | 3M Innovative Properties Company | Flowable dry powder composition |
-
2009
- 2009-04-03 WO PCT/US2009/039567 patent/WO2009124300A2/en not_active Ceased
- 2009-04-03 AU AU2009231589A patent/AU2009231589B2/en active Active
- 2009-04-03 PT PT97267488T patent/PT2273994E/pt unknown
- 2009-04-03 KR KR1020107024458A patent/KR101545300B1/ko active Active
- 2009-04-03 CA CA2728889A patent/CA2728889C/en active Active
- 2009-04-03 ES ES09726748.8T patent/ES2562069T3/es active Active
- 2009-04-03 US US12/418,559 patent/US8252947B2/en active Active
- 2009-04-03 CN CN2009801121621A patent/CN102215845A/zh active Pending
- 2009-04-03 EP EP09726748.8A patent/EP2273994B1/en active Active
- 2009-04-03 HU HUE09726748A patent/HUE028337T2/en unknown
- 2009-04-03 PL PL09726748T patent/PL2273994T3/pl unknown
- 2009-04-03 DK DK09726748.8T patent/DK2273994T3/en active
- 2009-04-03 JP JP2011503236A patent/JP2011527986A/ja not_active Withdrawn
-
2012
- 2012-08-01 US US13/563,982 patent/US20120296105A1/en not_active Abandoned
- 2012-08-01 US US13/563,996 patent/US20120302537A1/en not_active Abandoned
-
2014
- 2014-08-14 US US14/459,528 patent/US9555046B2/en active Active
- 2014-08-14 US US14/459,493 patent/US9877972B2/en active Active
- 2014-12-01 JP JP2014242946A patent/JP2015042686A/ja active Pending
-
2016
- 2016-11-10 US US15/348,107 patent/US9850271B2/en active Active
-
2017
- 2017-12-21 US US15/851,523 patent/US20180208623A1/en not_active Abandoned
-
2019
- 2019-10-10 US US16/598,694 patent/US10995112B2/en active Active
-
2021
- 2021-04-26 US US17/240,728 patent/US20220002338A1/en active Pending
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2562069T3 (es) | Formas en estado sólido de un fármaco | |
| ES2622181T3 (es) | Modificaciones cristalinas de elobixibat | |
| CN102791719B (zh) | 二胺衍生物的晶体及其制备方法 | |
| ES2550771T3 (es) | Sal de bismesilato etexilato de dabigatrán, formas en estado sólido y proceso para la preparación de las mismas | |
| BR112020017807A2 (pt) | Composto, e, processos para a preparação da forma i em estado sólido de solvato de abc em metanol variável, para a preparação da forma iii de hidrato e abemaciclib em estado sólido e para a preparação da forma ii de abemaciclib anidro em estado sólido | |
| Wu et al. | Preparation, characterization and pharmacokinetics of Cucurbitacin B solid dispersion | |
| RU2684278C1 (ru) | Фумарат пиридиламина и его кристаллы | |
| UA123218C2 (uk) | Солі палбоциклібу | |
| ES2349798T3 (es) | Hidrato variable cristalino de la sal hemisuccinato de (s)-6-(4-(2-((3-(9h-carbazol-4-iloxi)-2-hidroxipropil)amino)-2-metilpropil)fenoxi)-3-piridinocarboxamida. | |
| CN112142730A (zh) | 杂芳基并四氢吡啶类化合物的固体形式及其制备方法 | |
| EA042455B1 (ru) | Кристаллическая форма ингибитора, нацеленного на киназу cdk4/6 | |
| CN112047978A (zh) | 5-氯-n4-[2-(二甲基磷酰基)苯基]-n2-{2-甲氧基-4-[4-(4-甲基哌嗪-1-基)哌啶-1-基]苯基}嘧啶-2,4-二胺新晶型 | |
| HK1221224B (en) | Crystal modifications of elobixibat | |
| TW201636346A (zh) | 二－匹多莫德苄乙二胺及其固體型 | |
| HK1157679A (zh) | 藥學試劑的固體形式 |