NZ555278A - 17,20(e)-dehydro vitamin D analogs and their uses - Google Patents
17,20(e)-dehydro vitamin D analogs and their usesInfo
- Publication number
- NZ555278A NZ555278A NZ555278A NZ55527805A NZ555278A NZ 555278 A NZ555278 A NZ 555278A NZ 555278 A NZ555278 A NZ 555278A NZ 55527805 A NZ55527805 A NZ 55527805A NZ 555278 A NZ555278 A NZ 555278A
- Authority
- NZ
- New Zealand
- Prior art keywords
- group
- hydroxy
- medicament
- hydrogen
- formulated
- Prior art date
Links
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 title claims description 45
- 239000011710 vitamin D Substances 0.000 title claims description 44
- 229940046008 vitamin d Drugs 0.000 title claims description 44
- 229930003316 Vitamin D Natural products 0.000 title claims description 40
- 235000019166 vitamin D Nutrition 0.000 title claims description 40
- 150000003710 vitamin D derivatives Chemical class 0.000 title claims description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 91
- 229940021056 vitamin d3 Drugs 0.000 claims abstract description 26
- 239000011647 vitamin D3 Substances 0.000 claims abstract description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
- 201000004681 Psoriasis Diseases 0.000 claims abstract description 11
- 201000010099 disease Diseases 0.000 claims abstract description 11
- 208000032839 leukemia Diseases 0.000 claims abstract description 8
- 201000006417 multiple sclerosis Diseases 0.000 claims abstract description 6
- 239000003814 drug Substances 0.000 claims description 96
- 229910052739 hydrogen Inorganic materials 0.000 claims description 94
- 239000001257 hydrogen Substances 0.000 claims description 94
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 94
- 150000002431 hydrogen Chemical class 0.000 claims description 67
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 48
- 241001465754 Metazoa Species 0.000 claims description 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 24
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000001153 fluoro group Chemical group F* 0.000 claims description 22
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 21
- 229910052805 deuterium Inorganic materials 0.000 claims description 21
- 125000004043 oxo group Chemical group O=* 0.000 claims description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 108090000623 proteins and genes Proteins 0.000 claims description 17
- 238000007911 parenteral administration Methods 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 230000004069 differentiation Effects 0.000 claims description 15
- 230000002401 inhibitory effect Effects 0.000 claims description 14
- 125000001118 alkylidene group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000005345 deuteroalkyl group Chemical group 0.000 claims description 11
- 230000035897 transcription Effects 0.000 claims description 10
- 238000013518 transcription Methods 0.000 claims description 10
- 208000023275 Autoimmune disease Diseases 0.000 claims description 9
- 210000000577 adipose tissue Anatomy 0.000 claims description 9
- 206010006187 Breast cancer Diseases 0.000 claims description 7
- 208000026310 Breast neoplasm Diseases 0.000 claims description 7
- 208000013725 Chronic Kidney Disease-Mineral and Bone disease Diseases 0.000 claims description 7
- 206010009944 Colon cancer Diseases 0.000 claims description 7
- 208000008589 Obesity Diseases 0.000 claims description 7
- 206010060862 Prostate cancer Diseases 0.000 claims description 7
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 7
- 208000000453 Skin Neoplasms Diseases 0.000 claims description 7
- AEDMQUAPBVOJNN-UHFFFAOYSA-N [3-[2-[4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl]-1,3-thiazol-5-yl]-1,2,4-oxadiazol-5-yl]methanol Chemical compound O1C(CO)=NC(C=2SC(=NC=2)N2CCC(CC2)OC=2C(=CC=CC=2)C(F)(F)F)=N1 AEDMQUAPBVOJNN-UHFFFAOYSA-N 0.000 claims description 7
- 208000029742 colonic neoplasm Diseases 0.000 claims description 7
- 208000027866 inflammatory disease Diseases 0.000 claims description 7
- 235000020824 obesity Nutrition 0.000 claims description 7
- 201000006409 renal osteodystrophy Diseases 0.000 claims description 7
- 201000000849 skin cancer Diseases 0.000 claims description 7
- 230000002500 effect on skin Effects 0.000 claims description 6
- 230000036571 hydration Effects 0.000 claims description 6
- 238000006703 hydration reaction Methods 0.000 claims description 6
- 210000002374 sebum Anatomy 0.000 claims description 6
- 230000028327 secretion Effects 0.000 claims description 6
- 230000037393 skin firmness Effects 0.000 claims description 6
- 238000011200 topical administration Methods 0.000 claims description 6
- 230000037303 wrinkles Effects 0.000 claims description 6
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
- 206010052779 Transplant rejections Diseases 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 5
- 206010025135 lupus erythematosus Diseases 0.000 claims description 5
- 210000000056 organ Anatomy 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims description 5
- 235000005282 vitamin D3 Nutrition 0.000 claims 5
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 abstract description 5
- 201000011510 cancer Diseases 0.000 abstract description 3
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 abstract 1
- 229940126657 Compound 17 Drugs 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 69
- 239000000243 solution Substances 0.000 description 43
- -1 vitamin D compounds Chemical class 0.000 description 39
- 230000000694 effects Effects 0.000 description 35
- 239000011575 calcium Substances 0.000 description 25
- 229910052791 calcium Inorganic materials 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 21
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 21
- 101150041968 CDC13 gene Proteins 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
- 229940088594 vitamin Drugs 0.000 description 16
- 229930003231 vitamin Natural products 0.000 description 16
- 235000013343 vitamin Nutrition 0.000 description 16
- 239000011782 vitamin Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000005481 NMR spectroscopy Methods 0.000 description 15
- 238000011282 treatment Methods 0.000 description 15
- 150000003722 vitamin derivatives Chemical class 0.000 description 15
- 229960005084 calcitriol Drugs 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 14
- 230000024245 cell differentiation Effects 0.000 description 14
- 150000002576 ketones Chemical class 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- 230000027455 binding Effects 0.000 description 12
- 210000000988 bone and bone Anatomy 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 125000002252 acyl group Chemical group 0.000 description 10
- 230000004071 biological effect Effects 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 102000009310 vitamin D receptors Human genes 0.000 description 10
- 108050000156 vitamin D receptors Proteins 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 230000000968 intestinal effect Effects 0.000 description 9
- 230000032258 transport Effects 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000012300 argon atmosphere Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000001727 in vivo Methods 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 210000001789 adipocyte Anatomy 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000012230 colorless oil Substances 0.000 description 6
- 235000005911 diet Nutrition 0.000 description 6
- 230000037213 diet Effects 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- 102000004169 proteins and genes Human genes 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 101000573199 Homo sapiens Protein PML Proteins 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- 239000005556 hormone Substances 0.000 description 5
- 229940088597 hormone Drugs 0.000 description 5
- 102000054896 human PML Human genes 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 230000027425 release of sequestered calcium ion into cytosol Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 208000005770 Secondary Hyperparathyroidism Diseases 0.000 description 4
- WLLIXJBWWFGEHT-UHFFFAOYSA-N [tert-butyl(dimethyl)silyl] trifluoromethanesulfonate Chemical compound CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F WLLIXJBWWFGEHT-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000002246 antineoplastic agent Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 230000000125 calcaemic effect Effects 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- 229940124597 therapeutic agent Drugs 0.000 description 4
- 230000005758 transcription activity Effects 0.000 description 4
- STMPXDBGVJZCEX-UHFFFAOYSA-N triethylsilyl trifluoromethanesulfonate Chemical compound CC[Si](CC)(CC)OS(=O)(=O)C(F)(F)F STMPXDBGVJZCEX-UHFFFAOYSA-N 0.000 description 4
- 206010013786 Dry skin Diseases 0.000 description 3
- 108060001084 Luciferase Proteins 0.000 description 3
- 239000005089 Luciferase Substances 0.000 description 3
- 208000001132 Osteoporosis Diseases 0.000 description 3
- 241000286209 Phasianidae Species 0.000 description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 230000001413 cellular effect Effects 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 230000037336 dry skin Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- DBYQHFPBWKKZAT-UHFFFAOYSA-N lithium;benzene Chemical compound [Li+].C1=CC=[C-]C=C1 DBYQHFPBWKKZAT-UHFFFAOYSA-N 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- PKFBWEUIKKCWEW-WEZTXPJVSA-N (1r,3r)-5-[(2e)-2-[(1r,3as,7ar)-1-[(2r)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]cyclohexane-1,3-diol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=C\C=C1C[C@@H](O)C[C@H](O)C1 PKFBWEUIKKCWEW-WEZTXPJVSA-N 0.000 description 2
- MGTWXWKLYUMAON-UHFFFAOYSA-N 4-methylbenzenesulfonoperoxoic acid Chemical compound CC1=CC=C(S(=O)(=O)OO)C=C1 MGTWXWKLYUMAON-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- 208000002874 Acne Vulgaris Diseases 0.000 description 2
- 201000004384 Alopecia Diseases 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 208000015943 Coeliac disease Diseases 0.000 description 2
- 206010009900 Colitis ulcerative Diseases 0.000 description 2
- 208000011231 Crohn disease Diseases 0.000 description 2
- 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 2
- 206010020772 Hypertension Diseases 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 description 2
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 2
- 206010000496 acne Diseases 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000000746 allylic group Chemical group 0.000 description 2
- 231100000360 alopecia Toxicity 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000002449 bone cell Anatomy 0.000 description 2
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000010261 cell growth Effects 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000012903 everted gut sac method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 210000000987 immune system Anatomy 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 210000000936 intestine Anatomy 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 2
- 230000036210 malignancy Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 230000001483 mobilizing effect Effects 0.000 description 2
- 230000003020 moisturizing effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 210000002990 parathyroid gland Anatomy 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000001962 taste-modifying agent Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 230000002103 transcriptional effect Effects 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 2
- SQTAVUCHOVVOFD-OBRBSRNPSA-N (25S)-Delta(7)-dafachronic acid Chemical compound C1C(=O)CC[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@@H](CCC[C@H](C)C(O)=O)C)CC[C@H]33)C)C3=CC[C@H]21 SQTAVUCHOVVOFD-OBRBSRNPSA-N 0.000 description 1
- AEVBPXDFDKBGLT-YOUFYPILSA-N (2s,3s,4r,5r)-n-[2-[4-(diethoxyphosphorylmethyl)anilino]-2-oxoethyl]-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolane-2-carboxamide Chemical compound C1=CC(CP(=O)(OCC)OCC)=CC=C1NC(=O)CNC(=O)[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C(NC(=O)C=C2)=O)O1 AEVBPXDFDKBGLT-YOUFYPILSA-N 0.000 description 1
- GMRQFYUYWCNGIN-UHFFFAOYSA-N 1,25-Dihydroxy-vitamin D3' Natural products C1CCC2(C)C(C(CCCC(C)(C)O)C)CCC2C1=CC=C1CC(O)CC(O)C1=C GMRQFYUYWCNGIN-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 1
- BGQUPQDZDIVJHO-UHFFFAOYSA-N 5-bromo-2-methylpentan-2-ol Chemical compound CC(C)(O)CCCBr BGQUPQDZDIVJHO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 1
- 108020004705 Codon Proteins 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 241000792859 Enema Species 0.000 description 1
- 241000305071 Enterobacterales Species 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 241001198387 Escherichia coli BL21(DE3) Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 108700008625 Reporter Genes Proteins 0.000 description 1
- 241001125048 Sardina Species 0.000 description 1
- 229920002684 Sepharose Polymers 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000007984 Tris EDTA buffer Substances 0.000 description 1
- MECHNRXZTMCUDQ-UHFFFAOYSA-N Vitamin D2 Natural products C1CCC2(C)C(C(C)C=CC(C)C(C)C)CCC2C1=CC=C1CC(O)CCC1=C MECHNRXZTMCUDQ-UHFFFAOYSA-N 0.000 description 1
- 201000006035 X-linked dominant hypophosphatemic rickets Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000001479 atomic absorption spectroscopy Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000008512 biological response Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 210000004899 c-terminal region Anatomy 0.000 description 1
- GMRQFYUYWCNGIN-NKMMMXOESA-N calcitriol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C GMRQFYUYWCNGIN-NKMMMXOESA-N 0.000 description 1
- 230000004094 calcium homeostasis Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000001721 carboxyacetyl group Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- UMCMPZBLKLEWAF-UHFFFAOYSA-N chaps detergent Chemical compound OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(=O)NCCC[N+](C)(C)CCCS([O-])(=O)=O)C)C1(C)C(O)C2 UMCMPZBLKLEWAF-UHFFFAOYSA-N 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 208000037765 diseases and disorders Diseases 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000007920 enema Substances 0.000 description 1
- 229940095399 enema Drugs 0.000 description 1
- 229960002061 ergocalciferol Drugs 0.000 description 1
- 150000002137 ergosterols Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- XBPOBCXHALHJFP-UHFFFAOYSA-N ethyl 4-bromobutanoate Chemical compound CCOC(=O)CCCBr XBPOBCXHALHJFP-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 244000144993 groups of animals Species 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 125000000487 histidyl group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C([H])=N1 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 229910052588 hydroxylapatite Inorganic materials 0.000 description 1
- 230000000121 hypercalcemic effect Effects 0.000 description 1
- 208000011111 hypophosphatemic rickets Diseases 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- JPXMTWWFLBLUCD-UHFFFAOYSA-N nitro blue tetrazolium(2+) Chemical compound COC1=CC(C=2C=C(OC)C(=CC=2)[N+]=2N(N=C(N=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)[N+]([O-])=O)=CC=C1[N+]1=NC(C=2C=CC=CC=2)=NN1C1=CC=C([N+]([O-])=O)C=C1 JPXMTWWFLBLUCD-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 230000000242 pagocytic effect Effects 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 108010091624 preproparathormone Proteins 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 210000004765 promyelocyte Anatomy 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 208000032349 type 2B vitamin D-dependent rickets Diseases 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 239000011653 vitamin D2 Substances 0.000 description 1
- 235000001892 vitamin D2 Nutrition 0.000 description 1
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C401/00—Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
-
- 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
- A61P17/06—Antipsoriatics
-
- 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
-
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- 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
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- 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
- 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
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- 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
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Physical Education & Sports Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Obesity (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Biomedical Technology (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Nutrition Science (AREA)
- Oncology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Child & Adolescent Psychology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
- Medicinal Preparation (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63000704P | 2004-11-22 | 2004-11-22 | |
| PCT/US2005/041670 WO2006057885A2 (en) | 2004-11-22 | 2005-11-18 | 17,20(e)-dehydro vitamin d analogs and their uses |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ555278A true NZ555278A (en) | 2010-12-24 |
Family
ID=36216285
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ555278A NZ555278A (en) | 2004-11-22 | 2005-11-18 | 17,20(e)-dehydro vitamin D analogs and their uses |
| NZ555277A NZ555277A (en) | 2004-11-22 | 2005-11-18 | 2-methylene-19-nor-1alpha-hydroxy-17-ene-homopregnacalciferol and its uses |
| NZ555282A NZ555282A (en) | 2004-11-22 | 2005-11-18 | 17,20(z)-dehydro vitamin D analogs and their uses |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ555277A NZ555277A (en) | 2004-11-22 | 2005-11-18 | 2-methylene-19-nor-1alpha-hydroxy-17-ene-homopregnacalciferol and its uses |
| NZ555282A NZ555282A (en) | 2004-11-22 | 2005-11-18 | 17,20(z)-dehydro vitamin D analogs and their uses |
Country Status (11)
| Country | Link |
|---|---|
| US (6) | US7241752B2 (cg-RX-API-DMAC7.html) |
| EP (3) | EP1846370B1 (cg-RX-API-DMAC7.html) |
| JP (3) | JP5161582B2 (cg-RX-API-DMAC7.html) |
| AT (3) | ATE469883T1 (cg-RX-API-DMAC7.html) |
| AU (3) | AU2005309806B2 (cg-RX-API-DMAC7.html) |
| CA (3) | CA2588410C (cg-RX-API-DMAC7.html) |
| DE (3) | DE602005021538D1 (cg-RX-API-DMAC7.html) |
| ES (3) | ES2346774T3 (cg-RX-API-DMAC7.html) |
| MX (3) | MX2007006262A (cg-RX-API-DMAC7.html) |
| NZ (3) | NZ555278A (cg-RX-API-DMAC7.html) |
| WO (3) | WO2006057885A2 (cg-RX-API-DMAC7.html) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030188756A1 (en) * | 2002-08-19 | 2003-10-09 | Cantorna Margherita T | Treatment of inflammatory bowel disease with vitamin d compounds |
| US8404667B2 (en) * | 2006-12-29 | 2013-03-26 | Wisconsin Alumni Research Foundation | Compounds, compositions, kits and methods of use to orally and topically treat acne and other skin conditions by 19-Nor vitamin D analog |
| US7244719B2 (en) * | 2004-11-22 | 2007-07-17 | Wisconsin Alumni Research Foundation | 2-methylene-19,26,27-trinor-(20S)-1α-hydroxyvitamin D3 and its uses |
| NZ555278A (en) * | 2004-11-22 | 2010-12-24 | Wisconsin Alumni Res Found | 17,20(e)-dehydro vitamin D analogs and their uses |
| WO2008091686A2 (en) * | 2007-01-25 | 2008-07-31 | Bioxell S.P.A. | SYNTHESIS OF 1α-FLUORO-25-HYDROXY-16-23E-DIENE-26,27-BISHOMO-20-EPI-CHOLECALCIFEROL |
| US7888339B2 (en) * | 2008-07-10 | 2011-02-15 | Wisconsin Alumni Research Foundation | 2-methylene-20(21)-dehydro-19-nor-vitamin D analogs |
| US7893043B2 (en) * | 2008-07-10 | 2011-02-22 | Wisconsin Alumni Research Foundation | 2-methylene-(17Z)-17(20)-dehydro-19,21-dinor-vitamin D analogs |
| US20110274743A1 (en) * | 2009-01-16 | 2011-11-10 | Pharmaceutical Compounding Nz Limited | Medicament for the Treatment of Pain and Inflammation |
| US20120237472A1 (en) * | 2009-07-24 | 2012-09-20 | The Johns Hopkins University | Methods and compositions for treating or preventing autoimmune diseases using immunomodulatory agents |
| MX2012003883A (es) * | 2009-10-02 | 2012-06-27 | Wisconsin Alumni Res Found | Analogos de (20s,22e)-2-metileno-19-nor-22-ene-1a,25-dihidroxovita mina d3. |
| ES2545403T3 (es) * | 2010-03-23 | 2015-09-10 | Wisconsin Alumni Research Foundation | (20S)-2-metilen-19-nor-22-dimetil-1alfa,25-dihidroxivitamina D3 y (20R)-2-metilen-19-nor-22-dimetil-1alfa,25-hidroxivitamina D3 |
| WO2011119622A1 (en) * | 2010-03-23 | 2011-09-29 | Wisconsin Alumni Research Foundation | DIASTEREOMERS OF 2-METHYLENE-19-NOR-22-METHYL-1α,25- DIHYDROXYVITAMIN D3 |
| US8664206B2 (en) | 2010-03-23 | 2014-03-04 | Wisconsin Alumni Research Foundation | Diastereomers of 2-methylene-19-nor-22-methyl-1α,25-dihydroxyvitamin D3 |
| US8410080B1 (en) * | 2011-10-21 | 2013-04-02 | Wisconsin Alumni Research Foundation | 2-methylene-vitamin D analogs and their uses |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4666634A (en) * | 1984-12-05 | 1987-05-19 | Chugai Seiyaku Kabushiki Kaisha | vitamin D3 derivatives having a substituent at 2-position |
| US5145846A (en) * | 1988-01-20 | 1992-09-08 | Hoffmann-La Roche Inc. | Vitamin D3 analogs |
| US5362719A (en) * | 1990-03-01 | 1994-11-08 | Leo Pharmaceutical Products, Ltd. A/S Lovens Kemiske Fabrik Produktionsaktieselskab) | Use of vitamin-D analogues in the treatment of acne |
| GB9004544D0 (en) * | 1990-03-01 | 1990-04-25 | Leo Pharm Prod Ltd | Novel treatment ii |
| ES2070307T3 (es) * | 1990-07-04 | 1995-06-01 | Marcin Krotkiewski | Una preparacion para el tratamiento de la hipertension. |
| US5086191A (en) * | 1991-05-28 | 1992-02-04 | Wisconsin Alumni Research Foundation | Intermediates for the synthesis of 19-nor vitamin D compounds |
| GB9214202D0 (en) * | 1992-07-03 | 1992-08-12 | Leo Pharm Prod Ltd | Chemical compounds |
| DE69400495T2 (de) * | 1993-04-05 | 1997-04-30 | Wisconsin Alumni Res Found | 19-Nor-vitamin-D3-Verbindung mit einem Substituent an die 2. Stelle |
| US5552392A (en) * | 1993-11-03 | 1996-09-03 | Wisconsin Alumni Research Foundation | Method of treating hypoparathyroidism with (20S) vitamin D compounds |
| EP0717034B1 (en) * | 1994-12-14 | 1999-04-07 | Duphar International Research B.V | Vitamin D compounds and method of preparing these compounds |
| GB9625271D0 (en) * | 1996-12-04 | 1997-01-22 | Leo Pharm Prod Ltd | Chemical compounds |
| KR20000071039A (ko) * | 1997-02-13 | 2000-11-25 | 비숍 찰스 더블유. | 비타민 ｄ 화합물의 표적화된 치료학적 전달 |
| US5843928A (en) * | 1997-03-17 | 1998-12-01 | Wisconsin Alumni Research Foundation | 2-alkylidene-19-nor-vitamin D compounds |
| US6316642B1 (en) * | 1997-03-17 | 2001-11-13 | Wisconsin Alumni Research Foundation | 26,27-Homologated-20-EPI-2alkyl-19-nor-vitamin D compounds |
| US6392071B1 (en) * | 1997-03-17 | 2002-05-21 | Wisconsin Alumni: Research Foundation | 26,27-homologated-20-EPI-2-alkylidene-19-nor-vitamin D compounds |
| US6306844B1 (en) * | 1997-03-17 | 2001-10-23 | Wisconsin Alumni Research Foundation | Use of 2α-methyl-19-nor-20(S)-1α, 25-dihydroxyvitamin D3 to increase bone strength |
| US5945410A (en) * | 1997-03-17 | 1999-08-31 | Wisconsin Alumni Research Foundation | 2-alkyl-19-nor-vitamin D compounds |
| US5936105A (en) * | 1997-06-13 | 1999-08-10 | Tetrionics, Inc. | 14-EPI-19-nor-vitamin D compounds and methods |
| DE69829279T2 (de) * | 1997-06-25 | 2006-03-30 | Teijin Ltd. | Vitamin-d3-derivate und aus diesen hergestellte heilmittel gegen entzündliche erkrankungen der atemwege |
| GB9721156D0 (en) * | 1997-10-06 | 1997-12-03 | Leo Pharm Prod Ltd | Novel vitamin d analogues |
| ES2368824T3 (es) * | 1998-03-27 | 2011-11-22 | Oregon Health & Science University | Vitamina d y sus análogos en el tratamiento de tumores y otros desórdenes hiperproliferativos. |
| AU2001265272B2 (en) * | 2000-05-31 | 2006-08-17 | Wisconsin Alumni Research Foundation | 2-ethyl and 2-ethylidene-19-nor-vitamin d compounds |
| CA2414407A1 (en) * | 2000-07-18 | 2002-01-24 | Bone Care International, Inc. | Stabilized 1.alpha.-hydroxy vitamin d |
| BR0113703A (pt) * | 2000-09-08 | 2003-07-22 | Wisconsin Alumni Researcg Foun | Compostos e métodos de tratamento de psorìase, leucemia, câncer do cólon, do seio ou da próstata, osteodistrofia renal, de doenças auto-imune, inflamatória e de condição de pele |
| WO2002094247A2 (en) | 2001-05-22 | 2002-11-28 | Bioxell S.P.A. | Use of a vitamin d3 analogue for the treatment of autoimmune diabetes |
| US6627622B2 (en) | 2002-02-18 | 2003-09-30 | Wisconsin Alumni Research Foundation | (20S)-1α-hydroxy-2-methylene-19-nor-bishomopregnacalciferol and its uses |
| US6566352B1 (en) * | 2002-02-18 | 2003-05-20 | Wisconsin Alumni Research Foudation | 1 α-hydroxy-2-methylene-19-nor-pregnacalciferol and its uses |
| DE60310050T2 (de) * | 2002-03-29 | 2007-07-05 | Wisconsin Alumni Research Foundation, Madison | Ein verfahren zur herstellung von 1-alpha-hydroxy-2-methylen-19-nor-homopregnacalciferol |
| US6846811B2 (en) * | 2002-04-22 | 2005-01-25 | Wisconsin Alumni Research Foundation | (20S) 1α-hydroxy-2α-methyl and 2β-methyl-19-nor-vitamin D3 and their uses |
| GB0305332D0 (en) | 2003-03-10 | 2003-04-09 | Leuven K U Res & Dev | Biological evaluation of novel vitamin D analogues |
| US20050009792A1 (en) | 2003-07-08 | 2005-01-13 | Deluca Hector F. | (20S)-1alpha-hydroxy-2-methylene-19-nor-vitamin D3 and its uses |
| US7053075B2 (en) * | 2003-11-25 | 2006-05-30 | Deluca Hector F | Methods for reducing body fat using vitamin D compounds |
| CA2544502A1 (en) * | 2003-11-25 | 2005-06-09 | Wisconsin Alumni Research Foundation | Vitamin d analogs for obesity prevention and treatment |
| NZ555278A (en) * | 2004-11-22 | 2010-12-24 | Wisconsin Alumni Res Found | 17,20(e)-dehydro vitamin D analogs and their uses |
| CA2588406A1 (en) | 2004-11-22 | 2006-06-01 | Wisconsin Alumni Research Foundation | 2-.alpha.-methyl and 2-.beta.-methyl analogs of 19,26,27-trinor-(20s-1.alpha.-hydroxyvitamin d3 and their uses |
| WO2008035207A2 (en) | 2006-04-06 | 2008-03-27 | Wisconsin Alumni Research Foundation | 2-methylene-1alpha-hydroxy-19,21-dinorvitamin d3 analogs and uses thereof |
| KR101495578B1 (ko) * | 2007-04-25 | 2015-02-25 | 사이토크로마 인코포레이티드 | 비타민 ｄ 부족 및 결핍의 치료 방법 |
-
2005
- 2005-11-18 NZ NZ555278A patent/NZ555278A/en not_active IP Right Cessation
- 2005-11-18 ES ES05849730T patent/ES2346774T3/es not_active Expired - Lifetime
- 2005-11-18 AT AT05851805T patent/ATE469883T1/de not_active IP Right Cessation
- 2005-11-18 US US11/283,291 patent/US7241752B2/en not_active Expired - Lifetime
- 2005-11-18 WO PCT/US2005/041670 patent/WO2006057885A2/en not_active Ceased
- 2005-11-18 WO PCT/US2005/041819 patent/WO2006057900A2/en not_active Ceased
- 2005-11-18 JP JP2007543268A patent/JP5161582B2/ja not_active Expired - Fee Related
- 2005-11-18 ES ES05851757T patent/ES2344989T3/es not_active Expired - Lifetime
- 2005-11-18 CA CA2588410A patent/CA2588410C/en not_active Expired - Fee Related
- 2005-11-18 MX MX2007006262A patent/MX2007006262A/es active IP Right Grant
- 2005-11-18 MX MX2007006546A patent/MX2007006546A/es active IP Right Grant
- 2005-11-18 CA CA2588401A patent/CA2588401C/en not_active Expired - Fee Related
- 2005-11-18 AU AU2005309806A patent/AU2005309806B2/en not_active Expired - Fee Related
- 2005-11-18 NZ NZ555277A patent/NZ555277A/en not_active IP Right Cessation
- 2005-11-18 EP EP05851805A patent/EP1846370B1/en not_active Expired - Lifetime
- 2005-11-18 US US11/283,125 patent/US7241750B2/en not_active Expired - Lifetime
- 2005-11-18 MX MX2007006261A patent/MX2007006261A/es active IP Right Grant
- 2005-11-18 CA CA2588396A patent/CA2588396C/en not_active Expired - Fee Related
- 2005-11-18 ES ES05851805T patent/ES2347058T3/es not_active Expired - Lifetime
- 2005-11-18 DE DE602005021538T patent/DE602005021538D1/de not_active Expired - Lifetime
- 2005-11-18 DE DE602005020842T patent/DE602005020842D1/de not_active Expired - Lifetime
- 2005-11-18 NZ NZ555282A patent/NZ555282A/en not_active IP Right Cessation
- 2005-11-18 EP EP05851757A patent/EP1828114B1/en not_active Expired - Lifetime
- 2005-11-18 AT AT05851757T patent/ATE465144T1/de not_active IP Right Cessation
- 2005-11-18 WO PCT/US2005/041820 patent/WO2006057901A2/en not_active Ceased
- 2005-11-18 EP EP05849730A patent/EP1817279B1/en not_active Expired - Lifetime
- 2005-11-18 US US11/283,090 patent/US7241748B2/en not_active Expired - Lifetime
- 2005-11-18 AU AU2005309790A patent/AU2005309790B2/en not_active Ceased
- 2005-11-18 DE DE602005021702T patent/DE602005021702D1/de not_active Expired - Lifetime
- 2005-11-18 AU AU2005309805A patent/AU2005309805B2/en not_active Ceased
- 2005-11-18 JP JP2007543269A patent/JP2008520705A/ja active Pending
- 2005-11-18 AT AT05849730T patent/ATE469127T1/de not_active IP Right Cessation
- 2005-11-18 JP JP2007543228A patent/JP5043673B2/ja not_active Expired - Fee Related
-
2007
- 2007-07-09 US US11/775,117 patent/US7704982B2/en not_active Expired - Fee Related
- 2007-07-09 US US11/775,108 patent/US7741313B2/en not_active Expired - Fee Related
- 2007-07-09 US US11/775,061 patent/US8232263B2/en not_active Expired - Fee Related
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US8232263B2 (en) | 17,20(Z)-dehydro vitamin D analogs and their uses | |
| AU2009268567B2 (en) | 2-methylene-(17Z)-17(20)-dehydro-19,21-dinor-vitamin D analogs | |
| US8222236B2 (en) | 2-methylene-(20E)-20(22)-dehydro-19-nor-vitamin D analogs | |
| US7888339B2 (en) | 2-methylene-20(21)-dehydro-19-nor-vitamin D analogs |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RENW | Renewal (renewal fees accepted) | ||
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 18 NOV 2016 BY CPA GLOBAL Effective date: 20151002 |
|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 18 NOV 2017 BY CPA GLOBAL Effective date: 20161007 |
|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 18 NOV 2018 BY CPA GLOBAL Effective date: 20171005 |
|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 18 NOV 2019 BY CPA GLOBAL Effective date: 20181004 |
|
| LAPS | Patent lapsed |