FI93643B - Förfarande för framställning av nya terapeutiskt användbara 24-homo-D-vitaminderivat - Google Patents

Förfarande för framställning av nya terapeutiskt användbara 24-homo-D-vitaminderivat Download PDF

Info

Publication number: FI93643B
Authority: FI; Finland
Prior art keywords: formula; compound; group; homo; vitamin
Prior art date: 1989-10-02

Application number

FI904850A

Other languages

English (en)

Finnish (fi)

Other versions

FI93643C (sv

FI904850A0 (sv

Inventor

Katica Schwarz

Petra Rach

Gerald Dr Kirsch

Guenter Dr Neef

Matthias Dr Braeutigam

Ruth Dr Thieroff-Eckerdt

Original Assignee

Schering Ag

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.)

1989-10-02

Filing date

1990-10-02

Publication date

1995-01-31

1990-10-02 Application filed by Schering Ag filed Critical Schering Ag

1990-10-02 Publication of FI904850A0 publication Critical patent/FI904850A0/sv

1995-01-31 Publication of FI93643B publication Critical patent/FI93643B/sv

1995-05-10 Application granted granted Critical

1995-05-10 Publication of FI93643C publication Critical patent/FI93643C/sv

Links

238000002360 preparation method Methods 0.000 title claims abstract description 13
238000000034 method Methods 0.000 title claims abstract description 5
230000008569 process Effects 0.000 title claims abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 63
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
229910052799 carbon Inorganic materials 0.000 claims abstract description 4
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
125000004432 carbon atom Chemical group C* 0.000 claims abstract 6
239000000203 mixture Substances 0.000 claims description 15
125000006239 protecting group Chemical group 0.000 claims description 6
230000009467 reduction Effects 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
238000009472 formulation Methods 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 description 2
241000766026 Coregonus nasus Species 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 abstract description 3
230000009471 action Effects 0.000 abstract description 2
239000003814 drug Substances 0.000 abstract description 2
238000004519 manufacturing process Methods 0.000 abstract description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
125000002252 acyl group Chemical group 0.000 abstract 1
125000004423 acyloxy group Chemical group 0.000 abstract 1
125000000217 alkyl group Chemical group 0.000 abstract 1
125000002837 carbocyclic group Chemical group 0.000 abstract 1
229940079593 drug Drugs 0.000 abstract 1
239000001257 hydrogen Substances 0.000 abstract 1
239000008194 pharmaceutical composition Substances 0.000 abstract 1
230000035755 proliferation Effects 0.000 abstract 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 17
-1 dimethyl-tert-butylsilyl group Chemical group 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 14
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000003921 oil Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000012074 organic phase Substances 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 10
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
238000012360 testing method Methods 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
210000004027 cell Anatomy 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
239000002904 solvent Substances 0.000 description 8
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
230000008018 melting Effects 0.000 description 7
238000002844 melting Methods 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
239000007787 solid Substances 0.000 description 7
239000000126 substance Substances 0.000 description 7
HITWOXBWRQTWNE-UHFFFAOYSA-N 6,8-bis(bromomethyl)-3,11-dimethyltridecan-7-one Chemical compound CCC(C)CCC(CBr)C(=O)C(CBr)CCC(C)CC HITWOXBWRQTWNE-UHFFFAOYSA-N 0.000 description 6
239000011575 calcium Substances 0.000 description 6
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
150000003710 vitamin D derivatives Chemical class 0.000 description 6
RQMUKAMOPYYFPO-UHFFFAOYSA-N 5-methyl-1-(triphenyl-$l^{5}-phosphanylidene)heptan-2-one Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)CCC(C)CC)C1=CC=CC=C1 RQMUKAMOPYYFPO-UHFFFAOYSA-N 0.000 description 5
NMPPJSFYRRZRIB-UHFFFAOYSA-N 5-methyl-1-(triphenyl-$l^{5}-phosphanylidene)hexan-2-one Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)CCC(C)C)C1=CC=CC=C1 NMPPJSFYRRZRIB-UHFFFAOYSA-N 0.000 description 5
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
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 5
239000011612 calcitriol Substances 0.000 description 5
229910052791 calcium Inorganic materials 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
210000003491 skin Anatomy 0.000 description 5
239000011734 sodium Substances 0.000 description 5
FGOUEHWCUDUZTK-UHFFFAOYSA-N 1-cyclopentyl-3-(triphenyl-$l^{5}-phosphanylidene)propan-2-one Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)=CC(=O)CC1CCCC1 FGOUEHWCUDUZTK-UHFFFAOYSA-N 0.000 description 4
QKMFSGUNPGTQPT-UHFFFAOYSA-N 4-ethylhexan-2-one Chemical compound CCC(CC)CC(C)=O QKMFSGUNPGTQPT-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
229930003316 Vitamin D Natural products 0.000 description 4
235000020964 calcitriol Nutrition 0.000 description 4
GMRQFYUYWCNGIN-NKMMMXOESA-N calcitriol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C GMRQFYUYWCNGIN-NKMMMXOESA-N 0.000 description 4
229960005084 calcitriol Drugs 0.000 description 4
230000024245 cell differentiation Effects 0.000 description 4
239000012230 colorless oil Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 4
102000005962 receptors Human genes 0.000 description 4
108020003175 receptors Proteins 0.000 description 4
239000013558 reference substance Substances 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
229940088594 vitamin Drugs 0.000 description 4
229930003231 vitamin Natural products 0.000 description 4
235000013343 vitamin Nutrition 0.000 description 4
239000011782 vitamin Substances 0.000 description 4
239000011710 vitamin D Substances 0.000 description 4
235000019166 vitamin D Nutrition 0.000 description 4
229940046008 vitamin d Drugs 0.000 description 4
HCJUXWODMAMVGQ-UHFFFAOYSA-N 1-bromo-4-methylpentan-2-one Chemical compound CC(C)CC(=O)CBr HCJUXWODMAMVGQ-UHFFFAOYSA-N 0.000 description 3
WEZFYBVBPAUJAL-UHFFFAOYSA-N 2-ethylpentanenitrile Chemical compound CCCC(CC)C#N WEZFYBVBPAUJAL-UHFFFAOYSA-N 0.000 description 3
LUFPSOYGOSKNGD-UHFFFAOYSA-N 4-methyl-1-(triphenyl-$l^{5}-phosphanylidene)pentan-2-one Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)CC(C)C)C1=CC=CC=C1 LUFPSOYGOSKNGD-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
229910019142 PO4 Inorganic materials 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
239000012267 brine Substances 0.000 description 3
230000004663 cell proliferation Effects 0.000 description 3
229940125898 compound 5 Drugs 0.000 description 3
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
201000010099 disease Diseases 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000011521 glass Substances 0.000 description 3
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
229910052753 mercury Inorganic materials 0.000 description 3
230000004060 metabolic process Effects 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
239000002674 ointment Substances 0.000 description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
239000010452 phosphate Substances 0.000 description 3
239000002953 phosphate buffered saline Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 3
239000011647 vitamin D3 Substances 0.000 description 3
229940021056 vitamin d3 Drugs 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
WUAOFWYIMBQLIU-UHFFFAOYSA-M (4-methyl-2-oxopentyl)-triphenylphosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC(=O)CC(C)C)C1=CC=CC=C1 WUAOFWYIMBQLIU-UHFFFAOYSA-M 0.000 description 2
FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
229910004664 Cerium(III) chloride Inorganic materials 0.000 description 2
229940126062 Compound A Drugs 0.000 description 2
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
208000037147 Hypercalcaemia Diseases 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 description 2
229940125904 compound 1 Drugs 0.000 description 2
229940125773 compound 10 Drugs 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
230000004821 effect on bone Effects 0.000 description 2
230000033444 hydroxylation Effects 0.000 description 2
238000005805 hydroxylation reaction Methods 0.000 description 2
230000000148 hypercalcaemia Effects 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000011534 incubation Methods 0.000 description 2
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
239000002609 medium Substances 0.000 description 2
QGNJRVVDBSJHIZ-QHLGVNSISA-N retinyl acetate Chemical compound CC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C QGNJRVVDBSJHIZ-QHLGVNSISA-N 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
239000003104 tissue culture media Substances 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
YYJCNNFQNIAISZ-UHFFFAOYSA-N 1-cyclopentylpropan-2-one Chemical compound CC(=O)CC1CCCC1 YYJCNNFQNIAISZ-UHFFFAOYSA-N 0.000 description 1
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
GSNKRSKIWFBWEG-UHFFFAOYSA-N 3-ethylpentan-2-one Chemical compound CCC(CC)C(C)=O GSNKRSKIWFBWEG-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
206010006187 Breast cancer Diseases 0.000 description 1
208000026310 Breast neoplasm Diseases 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
QEURQYUTTXYFFU-UHFFFAOYSA-N C(C(C)C)C(=O)C=C1C(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C(C(C)C)C(=O)C=C1C(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 QEURQYUTTXYFFU-UHFFFAOYSA-N 0.000 description 1
UFEJVUMJSWGDAO-UHFFFAOYSA-N C(C)C(CCC(=O)C=[PH2]C1=CC=CC=C1)C Chemical compound C(C)C(CCC(=O)C=[PH2]C1=CC=CC=C1)C UFEJVUMJSWGDAO-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
206010009944 Colon cancer Diseases 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
229920002307 Dextran Polymers 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
108010067770 Endopeptidase K Proteins 0.000 description 1
241000287828 Gallus gallus Species 0.000 description 1
239000007995 HEPES buffer 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
241001465754 Metazoa Species 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
238000011785 NMRI mouse Methods 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
101710140091 Trypanin Proteins 0.000 description 1
MECHNRXZTMCUDQ-UHFFFAOYSA-N Vitamin D2 Natural products C1CCC2(C)C(C(C)C=CC(C)C(C)C)CCC2C1=CC=C1CC(O)CCC1=C MECHNRXZTMCUDQ-UHFFFAOYSA-N 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
230000004913 activation Effects 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
230000001028 anti-proliverative effect Effects 0.000 description 1
229940121375 antifungal agent Drugs 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
238000003556 assay Methods 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
102000023732 binding proteins Human genes 0.000 description 1
108091008324 binding proteins Proteins 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000006285 cell suspension Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
235000013330 chicken meat Nutrition 0.000 description 1
208000029742 colonic neoplasm Diseases 0.000 description 1
239000003086 colorant Substances 0.000 description 1
229940125797 compound 12 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000012258 culturing Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
230000004069 differentiation Effects 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
108010007093 dispase Proteins 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000000668 effect on calcium Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
210000001339 epidermal cell Anatomy 0.000 description 1
229960002061 ergocalciferol Drugs 0.000 description 1
239000012091 fetal bovine serum Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
230000003463 hyperproliferative effect Effects 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
230000031891 intestinal absorption Effects 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
239000006210 lotion Substances 0.000 description 1
VFZXMEQGIIWBFJ-UHFFFAOYSA-M magnesium;cyclopropane;bromide Chemical compound [Mg+2].[Br-].C1C[CH-]1 VFZXMEQGIIWBFJ-UHFFFAOYSA-M 0.000 description 1
230000036210 malignancy Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
WMCQOWCJBGPBCB-UHFFFAOYSA-M methyl-[2-(4-methylhexanoyl)phenyl]-diphenylphosphanium;bromide Chemical compound [Br-].CCC(C)CCC(=O)C1=CC=CC=C1[P+](C)(C=1C=CC=CC=1)C1=CC=CC=C1 WMCQOWCJBGPBCB-UHFFFAOYSA-M 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
229920002113 octoxynol Polymers 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000008063 pharmaceutical solvent Substances 0.000 description 1
VBQCHPIMZGQLAZ-UHFFFAOYSA-N phosphorane Chemical class [PH5] VBQCHPIMZGQLAZ-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
230000036470 plasma concentration Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
239000005297 pyrex Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000027425 release of sequestered calcium ion into cytosol Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
229960000342 retinol acetate Drugs 0.000 description 1
235000019173 retinyl acetate Nutrition 0.000 description 1
239000011770 retinyl acetate Substances 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
231100000489 sensitizer Toxicity 0.000 description 1
210000004927 skin cell Anatomy 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010186 staining Methods 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000003270 steroid hormone Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229940104230 thymidine Drugs 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
102000009310 vitamin D receptors Human genes 0.000 description 1
108050000156 vitamin D receptors Proteins 0.000 description 1
235000001892 vitamin D2 Nutrition 0.000 description 1
239000011653 vitamin D2 Substances 0.000 description 1
MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 1
QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
235000005282 vitamin D3 Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C401/00—Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Nutrition Science (AREA)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Steroid Compounds (AREA)
Medicinal Preparation (AREA)

FI904850A 1989-10-02 1990-10-02 Förfarande för framställning av nya terapeutiskt användbara 24-homo-D-vitaminderivat FI93643C (sv)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3933034A DE3933034A1 (de)	1989-10-02	1989-10-02	24-homo-vitamin-d-derivate, verfahren zu ihrer herstellung
DE3933034		1989-10-02

Publications (3)

Publication Number	Publication Date
FI904850A0 FI904850A0 (sv)	1990-10-02
FI93643B true FI93643B (sv)	1995-01-31
FI93643C FI93643C (sv)	1995-05-10

Family

ID=6390762

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI904850A FI93643C (sv)	1989-10-02	1990-10-02	Förfarande för framställning av nya terapeutiskt användbara 24-homo-D-vitaminderivat

Country Status (18)

Country	Link
US (1)	US5665716A (sv)
EP (1)	EP0421561B1 (sv)
JP (1)	JPH03246273A (sv)
CN (2)	CN1031705C (sv)
AT (1)	ATE103893T1 (sv)
AU (1)	AU639717B2 (sv)
CA (1)	CA2026671C (sv)
DD (1)	DD299178A5 (sv)
DE (2)	DE3933034A1 (sv)
DK (1)	DK0421561T3 (sv)
ES (1)	ES2052166T3 (sv)
FI (1)	FI93643C (sv)
HU (1)	HU210032B (sv)
IE (1)	IE71227B1 (sv)
IL (1)	IL95872A (sv)
NO (1)	NO178923C (sv)
PT (1)	PT95473B (sv)
ZA (1)	ZA907876B (sv)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5030772A (en) *	1990-02-14	1991-07-09	Deluca Hector F	Process for preparing vitamin D2 compounds and the corresponding 1 α-hydroxylated derivatives
US5260290A (en) *	1990-02-14	1993-11-09	Wisconsin Alumni Research Foundation	Homologated vitamin D2 compounds and the corresponding 1α-hydroxylated derivatives
US20040009958A1 (en) *	1991-01-08	2004-01-15	Bone Care International, Inc.	Methods for preparation and use of 1alpha,24(S)-dihydroxyvitamin D2
DE4200783C2 (de) *	1992-01-10	1997-02-06	Schering Ag	(5Z,7E,22E)-(1S,3R,24S)-24-Benzyl-9,10-secochola-5,7,10(19),22-tetraen-1,3,24-triol, Verfahren zur Herstellung und Pharmazeutische Präparate
IL107185A (en) *	1992-10-06	1998-02-22	Schering Ag	Vitamin d, 25-carboxylic acid derivatives and pharmaceutical compositions containing the same
DE4328217C2 (de) *	1993-08-21	1996-01-11	Lohmann Therapie Syst Lts	Therapeutisches System zur Behandlung der Psoriasis
US6242434B1 (en) *	1997-08-08	2001-06-05	Bone Care International, Inc.	24-hydroxyvitamin D, analogs and uses thereof
DE19619036A1 (de)	1996-04-30	1997-11-13	Schering Ag	Neue Vitamin D-Derivate mit carbo- oder heterocyclischen Substituenten an C-25, Verfahren zu ihrer Herstellung und die Verwendung zur Herstellung von Arzneimitteln
US5939408A (en)	1996-05-23	1999-08-17	Hoffman-La Roche Inc.	Vitamin D3 analogs
US20020128240A1 (en) *	1996-12-30	2002-09-12	Bone Care International, Inc.	Treatment of hyperproliferative diseases using active vitamin D analogues
US20030129194A1 (en) *	1997-02-13	2003-07-10	Bone Care International, Inc.	Targeted therapeutic delivery of vitamin D compounds
DE19935771A1 (de)	1999-07-23	2001-02-01	Schering Ag	Neue Vitamin D-Derivate mit cyclischen Substrukturen in den Seitenketten, Verfahren und Zwischenprodukte zu ihrer Herstellung und die Verwendung zur Herstellung von Arzneimitteln
IL153378A0 (en) *	2000-07-18	2003-07-06	Bone Care Internat Inc	STABILIZED 1alpha-HYDROXY VITAMIN D
DE10156596A1 (de) *	2001-11-13	2003-05-28	Schering Ag	Vitamin D-Derivate mit Acyloxygruppen in der Seitenkette, Verfahren zu ihrer Herstellung und die Verwendung zur Herstellung von Arzneimitteln
PL373677A1 (en) *	2002-01-10	2005-09-05	Teva Pharmaceutical Industries Ltd.	Selective enzymatic esterification and solvolysis of epimeric vitamin d analog and separation of the epimers
AU2003275987A1 (en) *	2002-06-13	2003-12-31	Teva Pharmaceutical Industries Ltd.	Epimerization of analogs of vitamin d
US7094775B2 (en)	2004-06-30	2006-08-22	Bone Care International, Llc	Method of treating breast cancer using a combination of vitamin D analogues and other agents
CN101505725A (zh) *	2006-08-29	2009-08-12	特瓦制药工业有限公司	包含含维生素D的化合物和皮质类固醇化合物的具有低pH相容性的稳定的药理学活性组合物
EP2299809B1 (en) *	2008-06-17	2018-10-17	Ben Gurion University Of The Negev R&D Authority	Substituted cyclohexylidene-ethylidene-octahydro-indene compounds
CN107019795A (zh)	2009-01-27	2017-08-08	博格有限责任公司	用于减轻与化疗有关的副作用的维生素d3化合物
CN102655869B (zh)	2009-08-14	2016-08-10	博格有限责任公司	用于治疗脱发的维生素d3及其类似物
KR20160013201A (ko)	2013-05-29	2016-02-03	버그 엘엘씨	비타민 d를 이용한 화학요법 유발 탈모증의 예방 또는 완화
US10548908B2 (en) *	2016-09-15	2020-02-04	Nostopharma, LLC	Compositions and methods for preventing and treating heterotopic ossification and pathologic calcification

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH672920A5 (sv) *	1984-10-04	1990-01-15	Wisconsin Alumni Res Found
WO1987003282A1 (fr) *	1985-11-21	1987-06-04	Taisho Pharmaceutical Co., Ltd.	Derive de la vitamine d3
US4847012A (en) *	1988-04-29	1989-07-11	Wisconsin Alumni Research Foundation	Vitamin D related compounds and processes for their preparation
US4927815A (en) *	1988-04-29	1990-05-22	Wisconsin Alumni Research Foundation	Compounds effective in inducing cell differentiation and process for preparing same
US5030772A (en) *	1990-02-14	1991-07-09	Deluca Hector F	Process for preparing vitamin D2 compounds and the corresponding 1 α-hydroxylated derivatives
US5260290A (en) *	1990-02-14	1993-11-09	Wisconsin Alumni Research Foundation	Homologated vitamin D2 compounds and the corresponding 1α-hydroxylated derivatives

1989
- 1989-10-02 DE DE3933034A patent/DE3933034A1/de not_active Withdrawn
1990
- 1990-10-01 DE DE90250249T patent/DE59005254D1/de not_active Expired - Lifetime
- 1990-10-01 ES ES90250249T patent/ES2052166T3/es not_active Expired - Lifetime
- 1990-10-01 AT AT90250249T patent/ATE103893T1/de not_active IP Right Cessation
- 1990-10-01 PT PT95473A patent/PT95473B/pt not_active IP Right Cessation
- 1990-10-01 EP EP90250249A patent/EP0421561B1/de not_active Expired - Lifetime
- 1990-10-01 DD DD90344338A patent/DD299178A5/de not_active IP Right Cessation
- 1990-10-01 HU HU906284A patent/HU210032B/hu not_active IP Right Cessation
- 1990-10-01 DK DK90250249.1T patent/DK0421561T3/da active
- 1990-10-01 NO NO904269A patent/NO178923C/no not_active IP Right Cessation
- 1990-10-01 CN CN90108993A patent/CN1031705C/zh not_active Expired - Fee Related
- 1990-10-02 IL IL9587290A patent/IL95872A/en not_active IP Right Cessation
- 1990-10-02 US US07/592,017 patent/US5665716A/en not_active Expired - Fee Related
- 1990-10-02 IE IE352090A patent/IE71227B1/en not_active IP Right Cessation
- 1990-10-02 CA CA002026671A patent/CA2026671C/en not_active Expired - Fee Related
- 1990-10-02 AU AU63715/90A patent/AU639717B2/en not_active Ceased
- 1990-10-02 ZA ZA907876A patent/ZA907876B/xx unknown
- 1990-10-02 JP JP2263263A patent/JPH03246273A/ja active Pending
- 1990-10-02 FI FI904850A patent/FI93643C/sv not_active IP Right Cessation
1994
- 1994-08-18 CN CN94115050A patent/CN1053103C/zh not_active Expired - Fee Related

Also Published As

Publication number	Publication date
IE903520A1 (en)	1991-04-10
IL95872A (en)	1995-03-15
CN1051907A (zh)	1991-06-05
EP0421561B1 (de)	1994-04-06
EP0421561A2 (de)	1991-04-10
CA2026671A1 (en)	1991-04-03
DD299178A5 (de)	1992-04-02
NO904269D0 (no)	1990-10-01
HU210032B (en)	1995-01-30
NO178923C (no)	1996-07-03
IL95872A0 (en)	1991-07-18
PT95473A (pt)	1991-06-25
CN1106666A (zh)	1995-08-16
HUT55751A (en)	1991-06-28
AU6371590A (en)	1991-04-11
AU639717B2 (en)	1993-08-05
ATE103893T1 (de)	1994-04-15
DK0421561T3 (da)	1994-07-25
DE59005254D1 (de)	1994-05-11
FI93643C (sv)	1995-05-10
ES2052166T3 (es)	1994-07-01
PT95473B (pt)	1997-07-31
CN1031705C (zh)	1996-05-01
IE71227B1 (en)	1997-02-12
HU906284D0 (en)	1991-03-28
EP0421561A3 (en)	1991-06-12
ZA907876B (en)	1992-04-29
JPH03246273A (ja)	1991-11-01
CA2026671C (en)	1998-12-08
CN1053103C (zh)	2000-06-07
FI904850A0 (sv)	1990-10-02
NO904269L (no)	1991-04-03
US5665716A (en)	1997-09-09
NO178923B (no)	1996-03-25
DE3933034A1 (de)	1991-04-11

Publication	Publication Date	Title
FI93643B (sv)	1995-01-31	Förfarande för framställning av nya terapeutiskt användbara 24-homo-D-vitaminderivat
CA1340614C (en)	1999-06-29	Cyclopentano-vitamin d analogs
FI92929B (sv)	1994-10-14	Förfarande för framställning av nya farmaceutiskt verksamma vitamin D analoger
US5532228A (en)	1996-07-02	Side-chain homologous vitamin D derivatives, process for their production, pharmaceutical preparations containing these derivatives and their use as pharmaceutical agents
AU707942B2 (en)	1999-07-22	New vitamin D derivatives with substituents at C-25, process for their production, intermediate products and use for the production of pharmaceutical agents
IE74251B1 (en)	1997-07-16	23-oxa derivatives in the vitamin D series process for the preparation thereof pharmaceutical products containing these derivatives and the use thereof as medicaments
PL171403B1 (pl)	1997-04-30	Sposób wytwarzania nowych 20-metylo-podstawionych pochodnych witaminy D PL PL
EP0296800B1 (en)	1991-10-16	Vitamin d3 derivatives
CZ284926B6 (cs)	1999-04-14	Deriváty kyseliny 25-karboxylové v řadě vitaminu D, způsob jejich výroby, meziprodukty pro tento způsob, farmaceutické preparáty tyto sloučeniny obsahující, jakož i jejich použití pro výrobu léčiv
JPH04505468A (ja)	1992-09-24	同族化されたビタミンＤ↓２化合物および対応する１α―ヒドロキシル化誘導体
KR100202434B1 (ko)	1999-06-15	26,27-디메틸렌-1알파,25-디히드록시비타민d₂및 26,27-디메틸렌-24-에피1알파,25-디히드록시비타민d₂, 및 이들의 제조방법
FI100598B (sv)	1998-01-15	Förfarande för framställning av nya terapeutiskt användbara sidokedjeh omologa vitamin-D-derivat
EP0374219A1 (en)	1990-06-27	SIDE CHAIN UNSATURATED 1$g(a)-HYDROXYVITAMIN D HOMOLOGS
RU2175318C2 (ru)	2001-10-27	Производные витамина d3, способы его получения, фармацевтическая композиция
US5354744A (en)	1994-10-11	Side chain unsaturated 1 alpha-hydroxyvitamin D analogs
US5036061A (en)	1991-07-30	Process for the preparation of 1 alpha,25-dihydroxylated vitamin D2 and related compounds
JPWO1999043645A1 (ja)	2002-10-08	２４−ヒドロキシビタミンｄ誘導体
HUT77669A (hu)	1998-07-28	18-Nor-D-vitamin vegyületek, ezeket tartalmazó gyógyszerkészítmények és alkalmazásuk
EP0278732A1 (en)	1988-08-17	Fluorine-containing vitamin D2 derivatives
EP0874813A1 (en)	1998-11-04	24-homo-26,27-hexafluoro-cholecalciferols

Legal Events

Date	Code	Title	Description
1995-01-02	BB	Publication of examined application
2004-08-31	MM	Patent lapsed	Owner name: SCHERING AKTIENGESELLSCHAFT