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 PDF

Info

Publication number: HU206083B
Authority: HU; Hungary
Prior art keywords: formula; compound; vitamin; group; hexane
Prior art date: 1988-04-29

Application number

HU892989A

Other languages

English (en)

Hungarian (hu)

Other versions

HU892989D0 (en

HUT52475A (en

Inventor

Hector Floyd Deluca

Heinrich Konstantine Schnoes

Kato Leonard Perlman

Andrzej Kutner

Original Assignee

Wisconsin Alumni Res Found

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1988-04-29

Filing date

1989-04-18

Publication date

1992-08-28

1989-04-18 Application filed by Wisconsin Alumni Res Found filed Critical Wisconsin Alumni Res Found

1990-06-28 Publication of HU892989D0 publication Critical patent/HU892989D0/hu

1990-07-28 Publication of HUT52475A publication Critical patent/HUT52475A/hu

1992-08-28 Publication of HU206083B publication Critical patent/HU206083B/hu

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
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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
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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
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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
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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)

HU892989A 1988-04-29 1989-04-18 Process for producing vitamn d3 compounds causing cell differentiation and pharmaceutical compositions comprising same HU206083B (en)

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 (2)
EP (1)	EP0375757A1 (2)
JP (2)	JPH0725730B2 (2)
KR (1)	KR930011151B1 (2)
AU (1)	AU630096B2 (2)
CA (1)	CA1340615C (2)
DK (2)	DK666589A (2)
FR (1)	FR2630740A1 (2)
GB (1)	GB2217715A (2)
HU (1)	HU206083B (2)
IE (1)	IE67868B1 (2)
IL (1)	IL90066A (2)
IN (1)	IN170659B (2)
NL (1)	NL8920414A (2)
WO (1)	WO1989010353A1 (2)

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* Cited by examiner, † Cited by third party
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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
CZ282294B6 (cs) *	1993-12-01	1997-06-11	Sankyo Company Limited	Inhibitor tvorby zánětlivého cytokinu obsahující polyprenylové deriváty, činidlo pro profylaxi a terapii zánětlivých střevních onemocnění a použití polyprenylových derivátů
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
IL118156A (en) *	1995-05-09	2001-08-26	Duphar Int Res	Vitamin d compounds, their preparation and pharmaceutical compositions containing them
AUPO727097A0 (en) *	1997-06-10	1997-07-03	Unisearch Limited	Method of treatment of hepatoma and pharmaceutical compositions for use therein
JP2002509888A (ja) *	1998-03-27	2002-04-02	オレゴンヘルスサイエンシーズユニバーシティー	腫瘍および他の過増殖性疾患の治療におけるビタミンｄおよびその類似体
ES2274785T3 (es) *	1999-04-01	2007-06-01	Johns Hopkins University	Analogos de 1-alfa,25-dihidroxi vitamina d3 no calcemicos, antiproliferativos, transcripcionalmente activos que contienen azufre.
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
US20080039434A1 (en) *	2004-03-01	2008-02-14	Bioxell S. P.A.	Treatment of Interstitial Cystitis with Vitamin D Compounds
CA2586679A1 (en)	2004-11-12	2006-05-18	Bioxell Spa	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
SG173119A1 (en) *	2009-01-27	2011-08-29	Berg Biosystems Llc	Vitamin d3 and analogs thereof for alleviating side effects associated with chemotherapy
MX366076B (es)	2009-08-14	2019-06-27	Berg Llc	Vitamina d3 y analogos de la misma para tratar alopecia.
US8754067B2 (en)	2010-11-12	2014-06-17	Wisconsin Alumni Research Foundation	22-haloacetoxy-homopregnacalciferol analogs and their uses
SG10201709894RA (en)	2013-05-29	2018-01-30	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

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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
EP0211863B1 (en) *	1985-01-17	1992-12-30	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
KR940003360B1 (ko) *	1988-04-29	1994-04-21	위스콘신 알럼나이 리써취 파운데이션	불포화 측쇄를 갖는 1α-히드록시비타민 D동족체

1988
- 1988-04-29 US US07/187,680 patent/US4927815A/en not_active Expired - Fee Related
1989
- 1989-04-18 AU AU35730/89A patent/AU630096B2/en not_active Ceased
- 1989-04-18 KR KR1019890702481A patent/KR930011151B1/ko not_active Expired - Lifetime
- 1989-04-18 NL NL8920414A patent/NL8920414A/nl not_active Application Discontinuation
- 1989-04-18 EP EP89905880A patent/EP0375757A1/en not_active Ceased
- 1989-04-18 WO PCT/US1989/001633 patent/WO1989010353A1/en not_active Ceased
- 1989-04-18 JP JP1505852A patent/JPH0725730B2/ja not_active Expired - Lifetime
- 1989-04-18 HU HU892989A patent/HU206083B/hu not_active IP Right Cessation
- 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
GB8909570D0 (en)	1989-06-14
IL90066A (en)	1995-12-08
IE891406L (en)	1989-10-29
GB2217715A (en)	1989-11-01
US4927815A (en)	1990-05-22
KR900700449A (ko)	1990-08-13
HU892989D0 (en)	1990-06-28
JPH0725730B2 (ja)	1995-03-22
AU630096B2 (en)	1992-10-22
IE67868B1 (en)	1996-05-01
KR930011151B1 (ko)	1993-11-24
JP2505713B2 (ja)	1996-06-12
DK666589A (da)	1990-02-28
EP0375757A1 (en)	1990-07-04
WO1989010353A1 (en)	1989-11-02
FR2630740A1 (fr)	1989-11-03
DK666589D0 (da)	1989-12-22
DK89091A (da)	1991-05-13
DK89091D0 (da)	1991-05-13
IL90066A0 (en)	1989-12-15
AU3573089A (en)	1989-11-24
JPH0748343A (ja)	1995-02-21
US5061699A (en)	1991-10-29
JPH02504154A (ja)	1990-11-29
HUT52475A (en)	1990-07-28
NL8920414A (nl)	1990-04-02
IN170659B (2)	1992-05-02
CA1340615C (en)	1999-06-29

Legal Events

Date	Code	Title
1992-02-28	HRH9	Withdrawal of annulment decision
1994-10-28	HMM4	Cancellation of final prot. due to non-payment of fee
2002-01-28	HMM4	Cancellation of final prot. due to non-payment of fee

Publication	Publication Date	Title
US4927815A (en)	1990-05-22	Compounds effective in inducing cell differentiation and process for preparing same
EP0407461B1 (en)	1993-03-31	Novel cyclopentano-vitamin d analogs
US4717721A (en)	1988-01-05	Sidechain homo-vitamin D compounds with preferential anti-cancer activity
HUT68263A (en)	1995-06-28	20-methyl-substituted vitamin d derivatives, process for their production, pharmaceutical compositions and intermediates
US5936105A (en)	1999-08-10	14-EPI-19-nor-vitamin D compounds and methods
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