IL33860A - 25-hydroxycholecalciferol derivatives - Google Patents
25-hydroxycholecalciferol derivativesInfo
- Publication number
- IL33860A IL33860A IL33860A IL3386070A IL33860A IL 33860 A IL33860 A IL 33860A IL 33860 A IL33860 A IL 33860A IL 3386070 A IL3386070 A IL 3386070A IL 33860 A IL33860 A IL 33860A
- Authority
- IL
- Israel
- Prior art keywords
- group
- compound
- hydrogen
- diol
- less
- Prior art date
Links
- JWUBBDSIWDLEOM-DTOXIADCSA-N calcidiol Chemical class C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=C\C=C1\C[C@@H](O)CCC1=C JWUBBDSIWDLEOM-DTOXIADCSA-N 0.000 title claims description 85
- 150000001875 compounds Chemical class 0.000 claims description 101
- -1 acyl radical Chemical class 0.000 claims description 59
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 55
- 238000000034 method Methods 0.000 claims description 45
- JWUBBDSIWDLEOM-UHFFFAOYSA-N 25-Hydroxycholecalciferol Natural products C1CCC2(C)C(C(CCCC(C)(C)O)C)CCC2C1=CC=C1CC(O)CCC1=C JWUBBDSIWDLEOM-UHFFFAOYSA-N 0.000 claims description 44
- 239000003872 25-hydroxy-cholecalciferol Substances 0.000 claims description 44
- 235000021318 Calcifediol Nutrition 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000002252 acyl group Chemical group 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 229910052744 lithium Inorganic materials 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- 239000007818 Grignard reagent Substances 0.000 claims 1
- 150000004795 grignard reagents Chemical class 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 52
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 30
- 239000002253 acid Substances 0.000 description 29
- 150000004677 hydrates Chemical class 0.000 description 24
- 239000000047 product Substances 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 20
- 229910052791 calcium Inorganic materials 0.000 description 20
- 239000011575 calcium Substances 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 238000004809 thin layer chromatography Methods 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 11
- 230000000875 corresponding effect Effects 0.000 description 11
- 239000013078 crystal Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000003246 corticosteroid Substances 0.000 description 10
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- 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 description 8
- 238000010521 absorption reaction Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 230000009102 absorption Effects 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 229940093499 ethyl acetate Drugs 0.000 description 7
- 235000019439 ethyl acetate Nutrition 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- 241000271566 Aves Species 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 229960001334 corticosteroids Drugs 0.000 description 6
- ALEXXDVDDISNDU-JZYPGELDSA-N cortisol 21-acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O ALEXXDVDDISNDU-JZYPGELDSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 210000002966 serum Anatomy 0.000 description 6
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- 229940088594 vitamin Drugs 0.000 description 6
- 229930003231 vitamin Natural products 0.000 description 6
- 235000013343 vitamin Nutrition 0.000 description 6
- 239000011782 vitamin Substances 0.000 description 6
- 241000124008 Mammalia Species 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 208000001132 Osteoporosis Diseases 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 229930003316 Vitamin D Natural products 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 235000019166 vitamin D Nutrition 0.000 description 5
- 239000011710 vitamin D Substances 0.000 description 5
- 150000003710 vitamin D derivatives Chemical class 0.000 description 5
- 229940046008 vitamin d Drugs 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- HIAJCGFYHIANNA-LXFNFDHFSA-N (4r)-4-[(8s,9s,10r,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoic acid Chemical compound C1C=C2CC(O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CCC(O)=O)C)[C@@]1(C)CC2 HIAJCGFYHIANNA-LXFNFDHFSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000031709 bromination Effects 0.000 description 4
- 238000005893 bromination reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 229960002061 ergocalciferol Drugs 0.000 description 4
- PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 4
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000002808 molecular sieve Substances 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 229960005205 prednisolone Drugs 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 150000003431 steroids Chemical class 0.000 description 4
- 230000009466 transformation Effects 0.000 description 4
- 239000011653 vitamin D2 Substances 0.000 description 4
- 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 description 4
- 150000003722 vitamin derivatives Chemical class 0.000 description 4
- DCROKXXPZPPINM-YHJXBONMSA-N (1r,3z)-3-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-6-methylhept-5-en-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCC=C(C)C)C)=C\C=C1\C[C@H](O)CCC1=C DCROKXXPZPPINM-YHJXBONMSA-N 0.000 description 3
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- 101150041968 CDC13 gene Proteins 0.000 description 3
- YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-UHFFFAOYSA-N 0.000 description 3
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 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 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000004792 aryl magnesium halides Chemical class 0.000 description 3
- 210000000988 bone and bone Anatomy 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical compound OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 125000001033 ether group Chemical group 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
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- 230000000968 intestinal effect Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229960004584 methylprednisolone Drugs 0.000 description 3
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical group Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 3
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 3
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 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 3
- 235000001892 vitamin D2 Nutrition 0.000 description 3
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- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical class O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 2
- HLBOAQSKBNNHMW-UHFFFAOYSA-N 3-(3-methoxyphenyl)pyridine Chemical group COC1=CC=CC(C=2C=NC=CC=2)=C1 HLBOAQSKBNNHMW-UHFFFAOYSA-N 0.000 description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
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- 102000003982 Parathyroid hormone Human genes 0.000 description 2
- 108090000445 Parathyroid hormone Proteins 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- DIPPFEXMRDPFBK-UHFFFAOYSA-N Vitamin D4 Natural products C1CCC2(C)C(C(C)CCC(C)C(C)C)CCC2C1=CC=C1CC(O)CCC1=C DIPPFEXMRDPFBK-UHFFFAOYSA-N 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 150000004791 alkyl magnesium halides Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- VQNPSCRXHSIJTH-UHFFFAOYSA-N cadmium(2+);carbanide Chemical compound [CH3-].[CH3-].[Cd+2] VQNPSCRXHSIJTH-UHFFFAOYSA-N 0.000 description 2
- PAOZEKFIIFTEAW-UHFFFAOYSA-N cadmium(2+);propane Chemical compound [Cd+2].C[CH-]C.C[CH-]C PAOZEKFIIFTEAW-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 208000020832 chronic kidney disease Diseases 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
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- 229960004618 prednisone Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009103 reabsorption Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000024622 response to vitamin Effects 0.000 description 1
- 208000007442 rickets Diseases 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 229940001593 sodium carbonate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007905 soft elastic gelatin capsule Substances 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 208000032349 type 2B vitamin D-dependent rickets Diseases 0.000 description 1
- 229940070710 valerate Drugs 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/24—All rings being cycloaliphatic the ring system containing nine carbon atoms, e.g. perhydroindane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00807929A US3833622A (en) | 1969-03-17 | 1969-03-17 | Crystalline 25-hydroxycholecalciferol hydrate and structurally related compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL33860A0 IL33860A0 (en) | 1970-04-20 |
| IL33860A true IL33860A (en) | 1973-10-25 |
Family
ID=25197461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL33860A IL33860A (en) | 1969-03-17 | 1970-02-09 | 25-hydroxycholecalciferol derivatives |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3833622A (de) |
| JP (1) | JPS4934980B1 (de) |
| BE (1) | BE747492A (de) |
| CA (1) | CA968789A (de) |
| CH (1) | CH528500A (de) |
| DE (1) | DE2012167C2 (de) |
| FR (1) | FR2035000B1 (de) |
| GB (1) | GB1286761A (de) |
| IL (1) | IL33860A (de) |
| NL (1) | NL7003686A (de) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4012509A (en) * | 1974-06-10 | 1977-03-15 | The Upjohn Company | Composition of matter and process |
| US3907843A (en) * | 1974-06-14 | 1975-09-23 | Wisconsin Alumni Res Found | 1{60 -Hydroxyergocalciferol and processes for preparing same |
| US3906014A (en) * | 1974-06-17 | 1975-09-16 | Wisconsin Alumni Res Found | 3-Deoxy-1{60 -hydroxycholecalciferol |
| US4001096A (en) * | 1975-02-21 | 1977-01-04 | The Upjohn Company | Process for preparing 25-hydroxycholecalciferol intermediates |
| US3993675A (en) * | 1975-02-24 | 1976-11-23 | Hoffmann-La Roche Inc. | Process for the preparation of 1α,25-dihydroxycholecalciferol |
| US4069321A (en) * | 1975-10-14 | 1978-01-17 | Merck & Co., Inc. | Blocked cholecalciferol and dihydrotachysterol 3 derivatives |
| JPS603045B2 (ja) * | 1976-04-19 | 1985-01-25 | 中外製薬株式会社 | １α―ヒドロキシビタミンＤ類軟カプセルの製造方法 |
| USRE30538E (en) * | 1977-03-07 | 1981-03-03 | Wisconsin Alumni Research Foundation | 3-Deoxy-1α-hydroxycholecalciferol |
| US4217288A (en) * | 1977-03-24 | 1980-08-12 | Wisconsin Alumni Research Foundation | Anti-vitamin D compounds |
| US4119647A (en) * | 1977-04-11 | 1978-10-10 | Hoffmann-La Roche Inc. | 25-Hydroxycholecalciferol-23,24-3 H and process for the preparation thereof |
| JPS6039278B2 (ja) * | 1977-05-23 | 1985-09-05 | 中外製薬株式会社 | ステロイド誘導体 |
| US4183852A (en) * | 1977-07-18 | 1980-01-15 | Kaiser Emil T | Process for preparing 25-hydroxycholesterol |
| JPS5822479B2 (ja) * | 1977-09-07 | 1983-05-09 | 帝人株式会社 | １α−ヒドロキシ−２４−オキソ−ビタミンＤ↓３およびその製造法 |
| US4188345A (en) * | 1978-07-26 | 1980-02-12 | Wisconsin Alumni Research Foundation | Fluorovitamin D compounds and processes for their preparation |
| US4225596A (en) * | 1978-10-13 | 1980-09-30 | Wisconsin Alumni Research Foundation | Method for treating calcium imbalance and improving calcium absorption in mammals |
| US4269777A (en) * | 1979-05-21 | 1981-05-26 | Wisconsin Alumni Research Foundation | Isotopically labeled vitamin D derivatives and processes for preparing same |
| FR2457282A1 (fr) * | 1979-05-23 | 1980-12-19 | Roussel Uclaf | Nouveau derive du 1a,25 dihydroxy cholecalciferol, son procede de preparation et son application comme medicament |
| IL60270A0 (en) * | 1979-06-14 | 1980-09-16 | Diamond Shamrock Corp | Preparation of 25-ydroxycholesterol |
| US4252797A (en) * | 1979-07-19 | 1981-02-24 | Walter Rosenthal | Corticosteroid calcium compositions and treatment of rheumatic diseases therewith |
| US4260804A (en) * | 1980-02-20 | 1981-04-07 | Wisconsin Alumni Research Foundation | Processes for preparing calcitroic acid and esters thereof |
| JPS62500301A (ja) * | 1984-10-04 | 1987-02-05 | ウイスコンシン アラムナイ リサ−チ フオンデ−シヨン | ２４―ホモビタミンｄ誘導体 |
| US5043170A (en) * | 1989-02-14 | 1991-08-27 | Hoffmann-La Roche Inc. | Animal feed composition containing a vitamin D metabolite |
| AU666529B2 (en) * | 1992-04-24 | 1996-02-15 | Wisconsin Alumni Research Foundation | Method of treating osteoporosis with 1 alpha, 24 (R)-dihydroxy-22 (E)-dehydro-vitamin D3 |
| KR960013798B1 (ko) * | 1992-04-24 | 1996-10-10 | 재단법인 한국전자통신연구소 | 평면 도파로형 공간 스위치 |
| US5194431A (en) * | 1992-07-08 | 1993-03-16 | Wisconsin Alumni Research Foundation | 24-cyclopropane vitamin D derivatives |
| MX9604831A (es) | 1994-04-15 | 1998-05-31 | Upjohn Co | Formas nuevas de cristal de 1-[5-metanosulfonamidoindolil-2-carbonil]-4-[3-(1-metiletila mino)-2-piridinil]-piperazina. |
| US6432936B1 (en) | 1999-01-20 | 2002-08-13 | Wisconsin Alumni Research Foundation | Crystalline 1α-hydroxyvitamin D2 and method of purification thereof |
| US7235655B2 (en) * | 2002-03-22 | 2007-06-26 | Pharmacia & Upjohn Company | Processes to prepare eplerenone |
| US8426391B2 (en) | 2006-02-03 | 2013-04-23 | Proventiv Therapeutics, Llc | Treating vitamin D insufficiency and deficiency with 25-hydroxyvitamin D2 and 25-hydroxyvitamin D3 |
| SI2679228T1 (en) | 2006-06-21 | 2018-06-29 | Opko Ireland Global Holdings, Ltd. | THERAPY WITH THE USE OF VITAMIN D ADDITIONAL FIBER AND HORMON RESISTANCE OF VITAMIN D |
| KR20190028822A (ko) | 2007-04-25 | 2019-03-19 | 사이토크로마 인코포레이티드 | 비타민 ｄ 화합물과 밀랍성 담체를 포함하는 경구 조절성 방출 조성물 |
| ES3047207T3 (en) | 2007-04-25 | 2025-12-03 | Opko Renal Llc | Method of safely and effectively treating and preventing secondary hyperparathyroidism in chronic kidney disease |
| PT2148684E (pt) | 2007-04-25 | 2013-04-19 | Cytochroma Inc | Método de tratamento para a insuficiência e deficiência de vitamina d |
| CA2714996C (en) | 2008-04-02 | 2020-04-07 | Cytochroma Inc. | Methods, compositions, uses, and kits useful for vitamin d deficiency and related disorders |
| RS60087B1 (sr) | 2010-03-29 | 2020-05-29 | Opko Ireland Global Holdings Ltd | Postupci i kompozicije za snižavanje nivoa paratireoidnog hormona |
| KR101847947B1 (ko) | 2013-03-15 | 2018-05-28 | 옵코 아이피 홀딩스 Ⅱ 인코포레이티드 | 안정화되고 변형된 비타민 ｄ 방출 제형 |
| US10220047B2 (en) | 2014-08-07 | 2019-03-05 | Opko Ireland Global Holdings, Ltd. | Adjunctive therapy with 25-hydroxyvitamin D and articles therefor |
| SG11201808227YA (en) | 2016-03-28 | 2018-10-30 | Opko Ireland Global Holdings Limited | Methods of vitamin d treatment |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL150682B (nl) * | 1968-07-01 | 1976-09-15 | Wisconsin Alumni Res Found | Werkwijze ter bereiding van een farmacologisch werkzaam preparaat, dat een vitamine d-derivaat bevat, alsmede gevormde voedingsmiddelen. |
-
1969
- 1969-03-17 US US00807929A patent/US3833622A/en not_active Expired - Lifetime
-
1970
- 1970-02-04 CA CA073,970A patent/CA968789A/en not_active Expired
- 1970-02-09 IL IL33860A patent/IL33860A/en unknown
- 1970-02-11 GB GB6597/70A patent/GB1286761A/en not_active Expired
- 1970-03-14 DE DE2012167A patent/DE2012167C2/de not_active Expired
- 1970-03-16 FR FR7009330A patent/FR2035000B1/fr not_active Expired
- 1970-03-16 NL NL7003686A patent/NL7003686A/xx unknown
- 1970-03-17 CH CH398070A patent/CH528500A/de not_active IP Right Cessation
- 1970-03-17 BE BE747492D patent/BE747492A/xx not_active IP Right Cessation
- 1970-03-17 JP JP45022231A patent/JPS4934980B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1286761A (en) | 1972-08-23 |
| NL7003686A (de) | 1970-09-21 |
| FR2035000B1 (de) | 1974-01-11 |
| DE2012167A1 (de) | 1970-10-01 |
| JPS4934980B1 (de) | 1974-09-19 |
| FR2035000A1 (de) | 1970-12-18 |
| CA968789A (en) | 1975-06-03 |
| CH528500A (de) | 1972-09-30 |
| US3833622A (en) | 1974-09-03 |
| BE747492A (fr) | 1970-09-17 |
| DE2012167C2 (de) | 1982-09-23 |
| IL33860A0 (en) | 1970-04-20 |
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