HU206083B - Process for producing vitamn d3 compounds causing cell differentiation and pharmaceutical compositions comprising same - Google Patents
Process for producing vitamn d3 compounds causing cell differentiation and pharmaceutical compositions comprising same Download PDFInfo
- Publication number
- HU206083B HU206083B HU892989A HU298989A HU206083B HU 206083 B HU206083 B HU 206083B HU 892989 A HU892989 A HU 892989A HU 298989 A HU298989 A HU 298989A HU 206083 B HU206083 B HU 206083B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- compound
- vitamin
- group
- hexane
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 53
- 238000000034 method Methods 0.000 title claims description 30
- 230000008569 process Effects 0.000 title claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 230000024245 cell differentiation Effects 0.000 title description 21
- 239000011710 vitamin D Substances 0.000 claims description 27
- 150000003710 vitamin D derivatives Chemical class 0.000 claims description 27
- 229940046008 vitamin d Drugs 0.000 claims description 25
- 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 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 23
- 235000019166 vitamin D Nutrition 0.000 claims description 23
- 229930003316 Vitamin D Natural products 0.000 claims description 21
- -1 4-hydroxy-4-methylpentyl Chemical group 0.000 claims description 17
- 239000007858 starting material Substances 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 239000002893 slag Substances 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 239000011612 calcitriol Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000003704 vitamin D3 derivatives Chemical class 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 123
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- 239000000243 solution Substances 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- 239000011575 calcium Substances 0.000 description 32
- 229910052791 calcium Inorganic materials 0.000 description 32
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 31
- 150000002148 esters Chemical class 0.000 description 30
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 230000000694 effects Effects 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- 150000003457 sulfones Chemical class 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 230000001939 inductive effect Effects 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 17
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical class C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 17
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 239000000741 silica gel Substances 0.000 description 16
- 229910002027 silica gel Inorganic materials 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 15
- 238000001819 mass spectrum Methods 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 230000032258 transport Effects 0.000 description 13
- GMRQFYUYWCNGIN-ZVUFCXRFSA-N 1,25-dihydroxy vitamin D3 Chemical group 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 12
- 241001465754 Metazoa Species 0.000 description 12
- 206010028980 Neoplasm Diseases 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 230000000121 hypercalcemic effect Effects 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 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 11
- 201000011510 cancer Diseases 0.000 description 11
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 11
- 230000004071 biological effect Effects 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 210000000988 bone and bone Anatomy 0.000 description 9
- 230000004069 differentiation Effects 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 238000002211 ultraviolet spectrum Methods 0.000 description 8
- 241000282414 Homo sapiens Species 0.000 description 7
- 241000700159 Rattus Species 0.000 description 7
- 208000032839 leukemia Diseases 0.000 description 7
- 239000011877 solvent mixture Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- 230000000968 intestinal effect Effects 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 210000002966 serum Anatomy 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 5
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 229910001023 sodium amalgam Inorganic materials 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 229940088594 vitamin Drugs 0.000 description 5
- 229930003231 vitamin Natural products 0.000 description 5
- 235000013343 vitamin Nutrition 0.000 description 5
- 239000011782 vitamin Substances 0.000 description 5
- 150000003722 vitamin derivatives Chemical class 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 229910018540 Si C Inorganic materials 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 230000003913 calcium metabolism Effects 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 230000002349 favourable effect Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000011647 vitamin D3 Substances 0.000 description 4
- 229940021056 vitamin d3 Drugs 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- BQXUPNKLZNSUMC-YUQWMIPFSA-N CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 Chemical compound CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 BQXUPNKLZNSUMC-YUQWMIPFSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000002308 calcification Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000004113 cell culture Methods 0.000 description 3
- DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 230000000668 effect on calcium Effects 0.000 description 3
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 238000002953 preparative HPLC Methods 0.000 description 3
- 229910010271 silicon carbide Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- HBPVGJGBRWIVSX-UHFFFAOYSA-N 6-bromohexanoyl chloride Chemical compound ClC(=O)CCCCCBr HBPVGJGBRWIVSX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 206010002383 Angina Pectoris Diseases 0.000 description 2
- 108090000371 Esterases Proteins 0.000 description 2
- 208000037147 Hypercalcaemia Diseases 0.000 description 2
- 206010057249 Phagocytosis Diseases 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000005103 alkyl silyl group Chemical group 0.000 description 2
- 239000000538 analytical sample Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical group CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000000148 hypercalcaemia Effects 0.000 description 2
- 208000030915 hypercalcemia disease Diseases 0.000 description 2
- 239000000411 inducer Substances 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000008782 phagocytosis Effects 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000012453 sprague-dawley rat model Methods 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
- 210000000689 upper leg Anatomy 0.000 description 2
- 235000005282 vitamin D3 Nutrition 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- DIFSFFZHWQSHBX-CLECVEASSA-N (1ar,3s,4as,7s,8as)-3-[(1s,2r,3r)-3-[(2r,5s)-5,6-dimethylheptan-2-yl]-2-(2-hydroxyethyl)-2-methylcyclopentyl]-7-hydroxy-4a-methyl-2,3,5,6,7,8-hexahydro-1ah-naphtho[4,4a-b]oxiren-4-one Chemical class OCC[C@]1(C)[C@@H]([C@H](C)CC[C@H](C)C(C)C)CC[C@H]1[C@H]1C(=O)[C@@]2(C)CC[C@H](O)C[C@@]32O[C@@H]3C1 DIFSFFZHWQSHBX-CLECVEASSA-N 0.000 description 1
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 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 1
- WGTYYNCSWCKXAI-UHFFFAOYSA-N 3-(benzenesulfonyl)propanoic acid Chemical compound OC(=O)CCS(=O)(=O)C1=CC=CC=C1 WGTYYNCSWCKXAI-UHFFFAOYSA-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
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- HCBIDLRKPXILPU-UHFFFAOYSA-N 4-chloropentanoyl chloride Chemical compound CC(Cl)CCC(Cl)=O HCBIDLRKPXILPU-UHFFFAOYSA-N 0.000 description 1
- 229910000761 Aluminium amalgam Inorganic materials 0.000 description 1
- 229910000497 Amalgam Inorganic materials 0.000 description 1
- 108010051152 Carboxylesterase Proteins 0.000 description 1
- 102000013392 Carboxylesterase Human genes 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 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 1
- 241000218922 Magnoliophyta Species 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 230000000719 anti-leukaemic effect Effects 0.000 description 1
- 239000000063 antileukemic agent Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 230000018678 bone mineralization Effects 0.000 description 1
- 229940045348 brown mixture Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000001721 carboxyacetyl group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003915 cell function Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- YGHUUVGIRWMJGE-UHFFFAOYSA-N chlorodimethylsilane Chemical compound C[SiH](C)Cl YGHUUVGIRWMJGE-UHFFFAOYSA-N 0.000 description 1
- UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940127204 compound 29 Drugs 0.000 description 1
- 229940125807 compound 37 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 230000006104 desulfonylation Effects 0.000 description 1
- 238000005688 desulfonylation reaction Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229960002061 ergocalciferol Drugs 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000031891 intestinal absorption Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000011164 ossification Effects 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- 210000002990 parathyroid gland Anatomy 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 230000009711 regulatory function Effects 0.000 description 1
- 230000027425 release of sequestered calcium ion into cytosol Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 210000004767 rumen Anatomy 0.000 description 1
- JBYXPOFIGCOSSB-UQGDGPGGSA-N rumenic acid Chemical class CCCCCC\C=C/C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-UQGDGPGGSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- CHLCPTJLUJHDBO-UHFFFAOYSA-M sodium;benzenesulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CC=C1 CHLCPTJLUJHDBO-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 150000003453 sulfinic acid esters Chemical class 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
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000007070 tosylation reaction Methods 0.000 description 1
- WILBTFWIBAOWLN-UHFFFAOYSA-N triethyl(triethylsilyloxy)silane Chemical compound CC[Si](CC)(CC)O[Si](CC)(CC)CC WILBTFWIBAOWLN-UHFFFAOYSA-N 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
- 239000011653 vitamin D2 Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
-
- 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
- A61P35/00—Antineoplastic agents
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/187,680 US4927815A (en) | 1988-04-29 | 1988-04-29 | Compounds effective in inducing cell differentiation and process for preparing same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HU892989D0 HU892989D0 (en) | 1990-06-28 |
| HUT52475A HUT52475A (en) | 1990-07-28 |
| HU206083B true HU206083B (en) | 1992-08-28 |
Family
ID=22690003
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU892989A HU206083B (en) | 1988-04-29 | 1989-04-18 | Process for producing vitamn d3 compounds causing cell differentiation and pharmaceutical compositions comprising same |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US4927815A (forum.php) |
| EP (1) | EP0375757A1 (forum.php) |
| JP (2) | JPH0725730B2 (forum.php) |
| KR (1) | KR930011151B1 (forum.php) |
| AU (1) | AU630096B2 (forum.php) |
| CA (1) | CA1340615C (forum.php) |
| DK (2) | DK666589A (forum.php) |
| FR (1) | FR2630740A1 (forum.php) |
| GB (1) | GB2217715A (forum.php) |
| HU (1) | HU206083B (forum.php) |
| IE (1) | IE67868B1 (forum.php) |
| IL (1) | IL90066A (forum.php) |
| IN (1) | IN170659B (forum.php) |
| NL (1) | NL8920414A (forum.php) |
| WO (1) | WO1989010353A1 (forum.php) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5250523A (en) * | 1988-04-29 | 1993-10-05 | Wisconsin Alumni Research Foundation | Side chain unsaturated 1α-hydroxyvitanim D homologs |
| CA1339383C (en) * | 1989-03-09 | 1997-08-26 | Hector Floyd Deluca | Method for preparing intermediates for the synthesis of steroid side chains in optically active form |
| DE3933034A1 (de) * | 1989-10-02 | 1991-04-11 | Schering Ag | 24-homo-vitamin-d-derivate, verfahren zu ihrer herstellung |
| GB9007236D0 (en) * | 1990-03-30 | 1990-05-30 | Leo Pharm Prod Ltd | Chemical compounds |
| RU2123338C1 (ru) * | 1990-06-15 | 1998-12-20 | Сайтел Корпорейшн | Фармацевтическая композиция на основе медиатора межклеточной адгезии (варианты), способ ингибирования межклеточной адгезии, способ лечения воспалительного заболевания, способ анализа тестируемого соединения на способность ингибировать клеточную адгезию, способ получения соединения |
| US5459136A (en) * | 1990-08-24 | 1995-10-17 | Wisconsin Alumni Research Foundation | Methods using vitamin D compounds for improvement of skin conditions |
| US5276061A (en) * | 1990-08-24 | 1994-01-04 | Wisconsin Alumni Research Foundation | Cosmetic compositions containing 1α-hydroxyvitamin D homologs |
| US5756783A (en) * | 1990-09-21 | 1998-05-26 | Bone Care International, Inc. | 1α-Hydroxy-24-EPI-vitamin D4 |
| DE4221961A1 (de) * | 1992-06-30 | 1994-01-05 | Schering Ag | 22-En-25-oxa-Derivate in der Vitamin D-Reihe, Verfahren zu ihrer Herstellung, diese Derivate enthaltenen pharmazeutische Präparate sowie deren Verwendung als Arzneimittel |
| US5380720A (en) * | 1993-05-11 | 1995-01-10 | Wisconsin Alumni Research Foundation | Iodo vitamin D3 compounds and method for preparing same |
| RU2141318C1 (ru) * | 1993-12-01 | 1999-11-20 | Санкио Компани Лимитед | Ингибитор образования воспалительного цитокина, средство для профилактики и лечения воспалительных заболеваний пищеварительного тракта и синдрома бехчета, способ профилактики и лечения воспалительных заболеваний и язвенного колита |
| PE28297A1 (es) * | 1995-01-26 | 1997-08-20 | Hoffmann La Roche | Empleo dermatologico de derivados de vitamina d |
| US5744128A (en) * | 1995-05-03 | 1998-04-28 | Holick; Michael F. | Use of emu oil for stimulating skin and hair growth |
| CA2175881A1 (en) * | 1995-05-09 | 1996-11-10 | Andrzej Kutner | Vitamin d compounds and methods of preparing these compounds |
| AUPO727097A0 (en) * | 1997-06-10 | 1997-07-03 | Unisearch Limited | Method of treatment of hepatoma and pharmaceutical compositions for use therein |
| 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. |
| CA2366586C (en) * | 1999-04-01 | 2004-06-22 | Johns Hopkins University | Non-calcemic, antiproliferative, transcriptionally active sulfur-containing analogs of 1.alpha., 25-dihydroxy vitamin d3 |
| WO2001040177A2 (en) | 1999-12-02 | 2001-06-07 | Women And Infants Hospital | Esters of vitamin d3 and uses thereof |
| US7166585B2 (en) * | 2001-08-22 | 2007-01-23 | Cytochroma Inc. | 24-Sulfur-substituted analogs of 1α,25-dihydroxy vitamin D3 |
| WO2003087048A2 (en) * | 2002-04-11 | 2003-10-23 | Instytut Farmaceutyczny | Preparation of 24 alkyl analogs of cholecalciferol and non-racemic compounds |
| BRPI0508333A (pt) * | 2004-03-01 | 2007-07-17 | Bioxell Spa | uso de um composto de vitamina d, método de prevenir e/ou tratar cistite intersticial, formulação farmacêutica, composto de vitamina d, e, kit |
| EP1812011A1 (en) | 2004-11-12 | 2007-08-01 | Bioxell S.p.a. | Combined use of vitamin d derivatives and anti-proliferative agents for treating bladder cancer |
| WO2008131267A2 (en) * | 2007-04-18 | 2008-10-30 | Johns Hopkins University | Low calcemic, highly antiproliferative, analogs of calcitriol |
| CA2981549A1 (en) | 2009-01-27 | 2010-08-05 | Berg Llc | Vitamin d3 and analogs thereof for alleviating side effects associated with chemotherapy |
| EA201270226A1 (ru) | 2009-08-14 | 2012-09-28 | БЕРГ БАЙОСИСТЕМЗ, ЭлЭлСи | Витамин d3 и его аналогии для лечения алопеции |
| US8754067B2 (en) | 2010-11-12 | 2014-06-17 | Wisconsin Alumni Research Foundation | 22-haloacetoxy-homopregnacalciferol analogs and their uses |
| NZ714801A (en) | 2013-05-29 | 2021-07-30 | Berg Llc | Preventing or mitigating chemotherapy induced alopecia using vitamin d |
| CN110981765A (zh) * | 2019-11-07 | 2020-04-10 | 肇庆巨元生化有限公司 | 一种25-羟基维生素d3中间体的制备方法 |
| CN112920096A (zh) * | 2019-12-05 | 2021-06-08 | 四川大学 | 一种制备2-甲基-4-(苯磺酰基)-2-丁醇的方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO1986004333A1 (en) * | 1985-01-17 | 1986-07-31 | Wisconsin Alumni Research Foundation | Vitamin d derivatives and methods for preparing same |
| US4717721A (en) * | 1985-05-30 | 1988-01-05 | Howard W. Bremer | Sidechain homo-vitamin D compounds with preferential anti-cancer activity |
| IL77668A (en) * | 1986-01-21 | 1989-03-31 | Teva Pharma | Production of cholecalciferol derivatives and novel intermediates used therefor |
| US4804502A (en) * | 1988-01-20 | 1989-02-14 | Hoffmann-La Roche Inc. | Vitamin D compounds |
| US5206229A (en) * | 1988-04-21 | 1993-04-27 | Leo Pharmaceutical Products Ltd | Vitamin d analogues |
| AU629831B2 (en) * | 1988-04-29 | 1992-10-15 | Wisconsin Alumni Research Foundation | Side chain unsaturated 1 alpha-hydroxyvitamin d homologs for the treatment of leukemia |
-
1988
- 1988-04-29 US US07/187,680 patent/US4927815A/en not_active Expired - Fee Related
-
1989
- 1989-04-18 KR KR1019890702481A patent/KR930011151B1/ko not_active Expired - Lifetime
- 1989-04-18 EP EP89905880A patent/EP0375757A1/en not_active Ceased
- 1989-04-18 HU HU892989A patent/HU206083B/hu not_active IP Right Cessation
- 1989-04-18 AU AU35730/89A patent/AU630096B2/en not_active Ceased
- 1989-04-18 NL NL8920414A patent/NL8920414A/nl not_active Application Discontinuation
- 1989-04-18 WO PCT/US1989/001633 patent/WO1989010353A1/en not_active Application Discontinuation
- 1989-04-18 JP JP1505852A patent/JPH0725730B2/ja not_active Expired - Lifetime
- 1989-04-24 IL IL9006689A patent/IL90066A/en not_active IP Right Cessation
- 1989-04-26 GB GB8909570A patent/GB2217715A/en not_active Withdrawn
- 1989-04-28 FR FR8905753A patent/FR2630740A1/fr active Pending
- 1989-04-28 IE IE140689A patent/IE67868B1/en not_active IP Right Cessation
- 1989-05-01 IN IN383/DEL/89A patent/IN170659B/en unknown
- 1989-06-25 CA CA000597715A patent/CA1340615C/en not_active Expired - Fee Related
- 1989-10-10 US US07/419,347 patent/US5061699A/en not_active Expired - Fee Related
- 1989-12-22 DK DK666589A patent/DK666589A/da unknown
-
1991
- 1991-05-13 DK DK91890A patent/DK89091D0/da unknown
-
1994
- 1994-06-14 JP JP6131616A patent/JP2505713B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| IL90066A (en) | 1995-12-08 |
| IN170659B (forum.php) | 1992-05-02 |
| CA1340615C (en) | 1999-06-29 |
| IE891406L (en) | 1989-10-29 |
| DK89091A (da) | 1991-05-13 |
| IE67868B1 (en) | 1996-05-01 |
| EP0375757A1 (en) | 1990-07-04 |
| JPH0748343A (ja) | 1995-02-21 |
| IL90066A0 (en) | 1989-12-15 |
| HUT52475A (en) | 1990-07-28 |
| US5061699A (en) | 1991-10-29 |
| KR930011151B1 (ko) | 1993-11-24 |
| FR2630740A1 (fr) | 1989-11-03 |
| DK89091D0 (da) | 1991-05-13 |
| JPH02504154A (ja) | 1990-11-29 |
| GB8909570D0 (en) | 1989-06-14 |
| KR900700449A (ko) | 1990-08-13 |
| JP2505713B2 (ja) | 1996-06-12 |
| DK666589A (da) | 1990-02-28 |
| GB2217715A (en) | 1989-11-01 |
| NL8920414A (nl) | 1990-04-02 |
| JPH0725730B2 (ja) | 1995-03-22 |
| US4927815A (en) | 1990-05-22 |
| AU3573089A (en) | 1989-11-24 |
| AU630096B2 (en) | 1992-10-22 |
| WO1989010353A1 (en) | 1989-11-02 |
| DK666589D0 (da) | 1989-12-22 |
| HU892989D0 (en) | 1990-06-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HU206083B (en) | Process for producing vitamn d3 compounds causing cell differentiation and pharmaceutical compositions comprising same | |
| EP0407461B1 (en) | Novel cyclopentano-vitamin d analogs | |
| CA2125476C (en) | 20-methyl-substituted vitamin d derivatives | |
| US4717721A (en) | Sidechain homo-vitamin D compounds with preferential anti-cancer activity | |
| US5936105A (en) | 14-EPI-19-nor-vitamin D compounds and methods | |
| US5250523A (en) | Side chain unsaturated 1α-hydroxyvitanim D homologs | |
| HUP9904333A2 (hu) | D-vitamin-analógok, eljárás előállításukra és ezeket tartalmazó gyógyszerkészítmények | |
| RU2057117C1 (ru) | ГОМОЛОГИ 1α - ГИДРОКСИВИТАМИНА D3 С НЕНАСЫЩЕННОЙ БОКОВОЙ ЦЕПЬЮ, КОМПОЗИЦИЯ, СПОСОБСТВУЮЩАЯ СТИМУЛЯЦИИ И УСИЛЕНИЮ ДИФФЕРЕНЦИАЦИИ ЗЛОКАЧЕСТВЕННЫХ КЛЕТОК ЛЕЙКЕМИИ ЧЕЛОВЕКА, СПОСОБ СТИМУЛЯЦИИ И УСИЛЕНИЯ ДИФФЕРЕНЦИАЦИИ ЗЛОКАЧЕСТВЕННЫХ КЛЕТОК ЛЕЙКЕМИИ ЧЕЛОВЕКА | |
| JP4988551B2 (ja) | ２−アルキリデン１８，１９−ジノル−ビタミンｄ化合物 | |
| US5354744A (en) | Side chain unsaturated 1 alpha-hydroxyvitamin D analogs | |
| JP5043674B2 (ja) | ２−メチレン−１８，１９−ジノル−１α−ヒドロキシ−ホモプレグナカルシフェロール及びその使用 | |
| IE70239B1 (en) | Side-chain homologous vitamin D derivatives process for their production pharmaceutical preparations containing these derivatives and their use as pharmaceutical agents | |
| AU587174B2 (en) | 1a, 25-dihydroxy-22z-dehydrovitamin d compound | |
| HUT77669A (hu) | 18-Nor-D-vitamin vegyületek, ezeket tartalmazó gyógyszerkészítmények és alkalmazásuk | |
| Sicinski et al. | New highly calcemic 1α, 25-dihydroxy-19-norvitamin D3 compounds with modified side chain: 26, 27-dihomo-and 26, 27-dimethylene analogs in 20S-series | |
| FR2550789A1 (fr) | 23,23-difluoro-25-hydroxy- et 1a,25-dihydroxy-vitamine d3 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HRH9 | Withdrawal of annulment decision | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |