CH667087A5 - In der seitenkette ungesaettigte 1-hydroxyvitamin d-verbindungen. - Google Patents
In der seitenkette ungesaettigte 1-hydroxyvitamin d-verbindungen. Download PDFInfo
- Publication number
- CH667087A5 CH667087A5 CH4259/85A CH425985A CH667087A5 CH 667087 A5 CH667087 A5 CH 667087A5 CH 4259/85 A CH4259/85 A CH 4259/85A CH 425985 A CH425985 A CH 425985A CH 667087 A5 CH667087 A5 CH 667087A5
- Authority
- CH
- Switzerland
- Prior art keywords
- compounds
- compound
- hydroxy
- vitamin
- side chain
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 69
- 239000000203 mixture Substances 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 239000000047 product Substances 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 150000003722 vitamin derivatives Chemical class 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 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
- 230000027455 binding Effects 0.000 description 8
- 238000001819 mass spectrum Methods 0.000 description 8
- 102000005962 receptors Human genes 0.000 description 8
- 108020003175 receptors Proteins 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 238000010828 elution Methods 0.000 description 7
- -1 nitrobenzoyl Chemical group 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 229940088594 vitamin Drugs 0.000 description 7
- 229930003231 vitamin Natural products 0.000 description 7
- 235000013343 vitamin Nutrition 0.000 description 7
- 239000011782 vitamin Substances 0.000 description 7
- 239000011710 vitamin D Substances 0.000 description 7
- 229940046008 vitamin d Drugs 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RQOCXCFLRBRBCS-PUEWYXROSA-N (3s,9s,10r,13r,14r,17r)-10,13-dimethyl-17-[(z,2r)-6-methylhept-3-en-2-yl]-2,3,4,9,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthren-3-ol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@H](C)\C=C/CC(C)C)CC[C@H]33)C)C3=CC=C21 RQOCXCFLRBRBCS-PUEWYXROSA-N 0.000 description 5
- 229930003316 Vitamin D Natural products 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000003797 solvolysis reaction Methods 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- 235000019166 vitamin D Nutrition 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000002207 metabolite Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- 150000003710 vitamin D derivatives Chemical class 0.000 description 4
- 239000011647 vitamin D3 Substances 0.000 description 4
- 229940021056 vitamin d3 Drugs 0.000 description 4
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 238000005805 hydroxylation reaction Methods 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 235000005282 vitamin D3 Nutrition 0.000 description 3
- 125000003903 2-propenyl group Chemical class [H]C([*])([H])C([H])=C([H])[H] 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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 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 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
- 229960005084 calcitriol Drugs 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229960002061 ergocalciferol Drugs 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 230000003211 malignant effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 235000001892 vitamin D2 Nutrition 0.000 description 2
- 239000011653 vitamin D2 Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 description 1
- RQOCXCFLRBRBCS-UHFFFAOYSA-N (22E)-cholesta-5,7,22-trien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CCC(C)C)CCC33)C)C3=CC=C21 RQOCXCFLRBRBCS-UHFFFAOYSA-N 0.000 description 1
- BPEQZNMKGFTMQE-LXHCYJFYSA-N (e,3r,6r)-6-[(1r,3as,4e,7ar)-4-[(2z)-2-[(5s)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1h-inden-1-yl]-2,3-dimethylhept-4-ene-2,3-diol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](\C=C\[C@@](C)(O)C(C)(C)O)C)=C\C=C1\C[C@@H](O)CCC1=C BPEQZNMKGFTMQE-LXHCYJFYSA-N 0.000 description 1
- GMRQFYUYWCNGIN-ZVUFCXRFSA-N 1,25-dihydroxy vitamin D3 Chemical compound C1([C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=CC=C1C[C@@H](O)C[C@H](O)C1=C GMRQFYUYWCNGIN-ZVUFCXRFSA-N 0.000 description 1
- HVAVRRBYXYEBNC-RKULPTJNSA-N 24-hydroxyvitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/C(C)(O)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C HVAVRRBYXYEBNC-RKULPTJNSA-N 0.000 description 1
- KJKIIUAXZGLUND-ICCVIKJNSA-N 25-hydroxyvitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](\C=C\[C@H](C)C(C)(C)O)C)=C\C=C1\C[C@@H](O)CCC1=C KJKIIUAXZGLUND-ICCVIKJNSA-N 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
- MIDSOQFBMMUFDM-UHFFFAOYSA-N 3-methylbutylphosphanium;bromide Chemical compound [Br-].CC(C)CC[PH3+] MIDSOQFBMMUFDM-UHFFFAOYSA-N 0.000 description 1
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 description 1
- 206010006956 Calcium deficiency Diseases 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- DNVPQKQSNYMLRS-NXVQYWJNSA-N Ergosterol Natural products CC(C)[C@@H](C)C=C[C@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C DNVPQKQSNYMLRS-NXVQYWJNSA-N 0.000 description 1
- 208000000038 Hypoparathyroidism Diseases 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000004094 calcium homeostasis Effects 0.000 description 1
- 125000001721 carboxyacetyl group Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000009137 competitive binding Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical class [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- PTVDYARBVCBHSL-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu] PTVDYARBVCBHSL-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229960003839 dienestrol Drugs 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- DNVPQKQSNYMLRS-SOWFXMKYSA-N ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H](CC[C@]3([C@H]([C@H](C)/C=C/[C@@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-SOWFXMKYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000013632 homeostatic process Effects 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 102000027411 intracellular receptors Human genes 0.000 description 1
- 108091008582 intracellular receptors Proteins 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting 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
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 208000007442 rickets Diseases 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003704 vitamin D3 derivatives Chemical class 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- 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
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0036—Nitrogen-containing hetero ring
- C07J71/0042—Nitrogen only
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Nutrition Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57511684A | 1984-01-30 | 1984-01-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH667087A5 true CH667087A5 (de) | 1988-09-15 |
Family
ID=24299022
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH4259/85A CH667087A5 (de) | 1984-01-30 | 1985-01-07 | In der seitenkette ungesaettigte 1-hydroxyvitamin d-verbindungen. |
Country Status (11)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0972762B1 (en) * | 1993-07-09 | 2003-10-01 | Laboratoire Theramex | Novel structural analogues of vitamin D |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3697559A (en) * | 1971-02-25 | 1972-10-10 | Wisconsin Alumni Res Found | 1,25-dihydroxycholecalciferol |
| US3741996A (en) * | 1971-12-02 | 1973-06-26 | Wisconsin Alumni Res Found | 1{60 -hydroxycholecalciferol |
| US3907843A (en) * | 1974-06-14 | 1975-09-23 | Wisconsin Alumni Res Found | 1{60 -Hydroxyergocalciferol and processes for preparing same |
| US4225596A (en) * | 1978-10-13 | 1980-09-30 | Wisconsin Alumni Research Foundation | Method for treating calcium imbalance and improving calcium absorption in mammals |
| US4264513A (en) * | 1979-05-21 | 1981-04-28 | Wisconsin Alumni Research Foundation | 1α-hydroxy-25-keto-27-nor-cholecalciferol and processes for preparing same |
| NL8320218A (nl) * | 1982-07-26 | 1984-06-01 | Wisconsin Alumni Res Found | Nieuwe vitamine d analogen. |
| US4508651A (en) * | 1983-03-21 | 1985-04-02 | Hoffmann-La Roche Inc. | Synthesis of 1α,25-dihydroxyergocalciferol |
| AU587174B2 (en) * | 1984-01-30 | 1989-08-10 | Wisconsin Alumni Research Foundation | 1a, 25-dihydroxy-22z-dehydrovitamin d compound |
-
1985
- 1985-01-07 DE DE19853590020 patent/DE3590020T1/de active Pending
- 1985-01-07 DE DE3590020A patent/DE3590020C2/de not_active Expired - Fee Related
- 1985-01-07 JP JP60500388A patent/JPS61501146A/ja active Granted
- 1985-01-07 NL NL8520003A patent/NL8520003A/nl unknown
- 1985-01-07 CH CH4259/85A patent/CH667087A5/de not_active IP Right Cessation
- 1985-01-07 AU AU38317/85A patent/AU589113B2/en not_active Ceased
- 1985-01-07 WO PCT/US1985/000016 patent/WO1985003299A1/en active Application Filing
- 1985-01-29 FR FR8501232A patent/FR2558830B1/fr not_active Expired
- 1985-01-29 GB GB08502163A patent/GB2153359B/en not_active Expired
- 1985-01-29 BE BE0/214413A patent/BE901602A/fr not_active IP Right Cessation
- 1985-01-29 IE IE212/85A patent/IE57947B1/en not_active IP Right Cessation
- 1985-09-27 DK DK437585A patent/DK437585D0/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE3590020C2 (de) | 1995-03-09 |
| IE57947B1 (en) | 1993-05-19 |
| JPS61501146A (ja) | 1986-06-12 |
| FR2558830B1 (fr) | 1987-11-20 |
| GB8502163D0 (en) | 1985-02-27 |
| WO1985003299A1 (en) | 1985-08-01 |
| DK437585A (da) | 1985-09-27 |
| FR2558830A1 (fr) | 1985-08-02 |
| BE901602A (fr) | 1985-05-17 |
| AU589113B2 (en) | 1989-10-05 |
| GB2153359B (en) | 1987-08-12 |
| GB2153359A (en) | 1985-08-21 |
| DE3590020T1 (de) | 1986-01-23 |
| AU3831785A (en) | 1985-08-09 |
| NL8520003A (nl) | 1985-12-02 |
| IE850212L (en) | 1985-07-30 |
| DK437585D0 (da) | 1985-09-27 |
| JPH0455424B2 (enrdf_load_stackoverflow) | 1992-09-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69006052T2 (de) | 19-Nor-Vitamin-D-Derivate. | |
| US5532391A (en) | Homologated vitamin D2 compounds and the corresponding 1α-hydroxylated derivatives | |
| DE69415690T2 (de) | (e)-20(22)-dehydrovitamin-d-verbindungen | |
| US4719205A (en) | Side-chain unsaturated 1-hydroxyvitamin D compounds | |
| DE69233074T2 (de) | Verfahren zur Herstellung von 1-alpha-24-dihydroxy-Vitamin D2 | |
| DE69412476T2 (de) | Vitamin-d-amid-derivate | |
| CH671222A5 (enrdf_load_stackoverflow) | ||
| DE2526981C3 (de) | lalpha^4-Dihyaroxycholecalciferol-Derivate, Verfahren zu ihrer Herstellung und pharmazeutische Mittel | |
| DE69208478T2 (de) | Amid derivate von vitamin d | |
| DE69300196T2 (de) | 24-Cyclopropan-Vitamin-D-Derivate. | |
| DE69316910T2 (de) | Neue vitamin d derivate | |
| US4769181A (en) | 1,25-dihydroxyvitamin D2 compounds | |
| DE3590232C2 (de) | 1,24-Dihydroxy- 22-Vitamin D3-Derivate, diese enthaltende Arzneimittel sowie Cholesterinderivate alsZwischenprodukte | |
| DE69109006T2 (de) | HOMOLOGIERTE VITAMIN-D2-VERBINDUNGEN UND KORRESPONDIERENDE 1alpha-HYDROXYLIERTE VERBINDUNGEN. | |
| CH665834A5 (de) | Verfahren zur herstellung von 1alpha,25-dihydroxyliertem vitamin d(2) und verwandten verbindungen. | |
| US4505906A (en) | Hydroxyvitamin D2 isomers | |
| DE69325253T2 (de) | 1alpha,24(s)-dihydroxy vitamin d2, seine synthese und verwendung | |
| DE69214617T2 (de) | 26,27-Dimethylen-1-Alpha, 25-Dihydroxyvitamin-D2 und 26,27-Dihydroxyvitamin-D2 und Verfahren zu ihrer Herstellung | |
| DE69608701T2 (de) | Vitamin d analoge | |
| DE69510189T2 (de) | Vitamin-d-amid derivate | |
| DE69820481T2 (de) | Verfahren zur herstellung von cholecalciferol-derivaten und zwischenverbindungen | |
| DE3590021C2 (de) | 1alpha-Hydroxyvitamin D-Derivat und dieses enthaltendes Arzneimittel | |
| DE3590020C2 (de) | In der Seitenkette ungesättigte 1-Hydroxyvitamin D-Verbindungen | |
| DE3590080C2 (enrdf_load_stackoverflow) | ||
| US5036061A (en) | Process for the preparation of 1 alpha,25-dihydroxylated vitamin D2 and related compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |