CA1340615C - Compouds effective in inducing cell differentiation and process for preparing same - Google Patents
Compouds effective in inducing cell differentiation and process for preparing sameInfo
- Publication number
- CA1340615C CA1340615C CA000597715A CA597715A CA1340615C CA 1340615 C CA1340615 C CA 1340615C CA 000597715 A CA000597715 A CA 000597715A CA 597715 A CA597715 A CA 597715A CA 1340615 C CA1340615 C CA 1340615C
- Authority
- CA
- Canada
- Prior art keywords
- hydroxy
- compounds
- compound
- dihydroxyvitamin
- group
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Fee Related
Links
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- GMRQFYUYWCNGIN-CLVAPQHMSA-N (5e)-5-[(2e)-2-[1-(6-hydroxy-6-methylheptan-2-yl)-7a-methyl-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C1CCC2(C)C(C(CCCC(C)(C)O)C)CCC2\C1=C\C=C1/CC(O)CC(O)C1=C GMRQFYUYWCNGIN-CLVAPQHMSA-N 0.000 abstract 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 33
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
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- 101150041968 CDC13 gene Proteins 0.000 description 13
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 210000000988 bone and bone Anatomy 0.000 description 12
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 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 9
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- 230000002829 reductive effect Effects 0.000 description 9
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 241000700159 Rattus Species 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 230000000968 intestinal effect Effects 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
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- 238000006243 chemical reaction Methods 0.000 description 6
- DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 6
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
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- 229910018540 Si C Inorganic materials 0.000 description 4
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- 239000012230 colorless oil Substances 0.000 description 4
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 4
- 230000001747 exhibiting effect Effects 0.000 description 4
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 4
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 230000003389 potentiating effect Effects 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- 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
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- 229910000497 Amalgam Inorganic materials 0.000 description 1
- 241001530105 Anax Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 101100002344 Caenorhabditis elegans arid-1 gene Proteins 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000013725 Chronic Kidney Disease-Mineral and Bone disease Diseases 0.000 description 1
- 108010034984 D3 compound Proteins 0.000 description 1
- 108090000371 Esterases Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 208000000038 Hypoparathyroidism Diseases 0.000 description 1
- 206010024328 Leukaemoid reaction Diseases 0.000 description 1
- 229910010084 LiAlH4 Inorganic materials 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 208000007542 Paresis Diseases 0.000 description 1
- 206010057249 Phagocytosis Diseases 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 201000006035 X-linked dominant hypophosphatemic rickets Diseases 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 229960000583 acetic acid Drugs 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
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000719 anti-leukaemic effect Effects 0.000 description 1
- 239000000063 antileukemic agent Substances 0.000 description 1
- 229940034982 antineoplastic agent Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 238000004380 ashing Methods 0.000 description 1
- WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000008827 biological function Effects 0.000 description 1
- 230000018678 bone mineralization Effects 0.000 description 1
- 229940045348 brown mixture Drugs 0.000 description 1
- GMRQFYUYWCNGIN-NKMMMXOESA-N calcitriol Chemical group 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 1
- 208000022458 calcium metabolism disease Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001721 carboxyacetyl group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 1
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- VRLDVERQJMEPIF-UHFFFAOYSA-N dbdmh Chemical compound CC1(C)N(Br)C(=O)N(Br)C1=O VRLDVERQJMEPIF-UHFFFAOYSA-N 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000006326 desulfonation Effects 0.000 description 1
- 238000005869 desulfonation reaction Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- AASUFOVSZUIILF-UHFFFAOYSA-N diphenylmethanone;sodium Chemical compound [Na].C=1C=CC=CC=1C(=O)C1=CC=CC=C1 AASUFOVSZUIILF-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- HKXBNHCUPKIYDM-CGMHZMFXSA-N doxercalciferol 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)C[C@H](O)C1=C HKXBNHCUPKIYDM-CGMHZMFXSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002183 duodenal effect Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000003028 elevating effect Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 230000000121 hypercalcemic effect Effects 0.000 description 1
- 208000011111 hypophosphatemic rickets Diseases 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000001976 improved effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 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 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 208000012318 pareses Diseases 0.000 description 1
- 230000008782 phagocytosis Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 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
- 238000011045 prefiltration Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000001328 rachitogenic effect Effects 0.000 description 1
- 201000006409 renal osteodystrophy Diseases 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- SRJQTHAZUNRMPR-UYQKXTDMSA-N spinosyn A Chemical compound O([C@H]1CCC[C@@H](OC(=O)C[C@H]2[C@@H]3C=C[C@@H]4C[C@H](C[C@H]4[C@@H]3C=C2C(=O)[C@@H]1C)O[C@H]1[C@@H]([C@H](OC)[C@@H](OC)[C@H](C)O1)OC)CC)[C@H]1CC[C@H](N(C)C)[C@@H](C)O1 SRJQTHAZUNRMPR-UYQKXTDMSA-N 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
- 230000000638 stimulation Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000001962 taste-modifying agent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000007070 tosylation reaction Methods 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 208000032349 type 2B vitamin D-dependent rickets Diseases 0.000 description 1
- 150000003704 vitamin D3 derivatives Chemical class 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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 (2)
| 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 |
| US07/187,680 | 1988-04-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1340615C true CA1340615C (en) | 1999-06-29 |
Family
ID=22690003
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000597715A Expired - Fee Related CA1340615C (en) | 1988-04-29 | 1989-06-25 | Compouds effective in inducing cell differentiation and process for preparing same |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US4927815A (instruction) |
| EP (1) | EP0375757A1 (instruction) |
| JP (2) | JPH0725730B2 (instruction) |
| KR (1) | KR930011151B1 (instruction) |
| AU (1) | AU630096B2 (instruction) |
| CA (1) | CA1340615C (instruction) |
| DK (2) | DK666589A (instruction) |
| FR (1) | FR2630740A1 (instruction) |
| GB (1) | GB2217715A (instruction) |
| HU (1) | HU206083B (instruction) |
| IE (1) | IE67868B1 (instruction) |
| IL (1) | IL90066A (instruction) |
| IN (1) | IN170659B (instruction) |
| NL (1) | NL8920414A (instruction) |
| WO (1) | WO1989010353A1 (instruction) |
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 |
| US5276061A (en) * | 1990-08-24 | 1994-01-04 | Wisconsin Alumni Research Foundation | Cosmetic compositions containing 1α-hydroxyvitamin D homologs |
| US5459136A (en) * | 1990-08-24 | 1995-10-17 | Wisconsin Alumni Research Foundation | Methods using vitamin D compounds for improvement of skin conditions |
| 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 |
| AU683112B2 (en) * | 1993-12-01 | 1997-10-30 | Sankyo Company Limited | Inflammatory cytokine production inhibitor containing polyprenyl derivative as active ingredient |
| 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 |
| EP2340840B1 (en) * | 1998-03-27 | 2012-08-29 | Oregon Health Sciences University | Pulse dose Vitamin D drug for the treatment of hyperproliferative skin diseases |
| ES2614632T3 (es) * | 1999-04-01 | 2017-06-01 | Johns Hopkins University | Análogos no calcémicos, antiproliferativos, transcripcionalmente activos de 1-alfa 25-dihidroxi vitamina D3 que contienen azufre |
| AU2058701A (en) | 1999-12-02 | 2001-06-12 | F. Hoffmann-La Roche Ag | 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 |
| EP1497264A2 (en) * | 2002-04-11 | 2005-01-19 | Instytut Farmaceutyczny | Preparation of 24-alkyl analogs of cholecalciferol and non-racemic compounds |
| EP1737468A2 (en) | 2004-03-01 | 2007-01-03 | Bioxell S.p.a. | Treatment of interstitial cystitis with vitamin d compounds |
| JP2008519808A (ja) | 2004-11-12 | 2008-06-12 | ビオエクセル エスピーエー | 膀胱癌治療のためのビタミンｄ誘導体及び抗増殖薬の併用 |
| EP2144872A2 (en) * | 2007-04-18 | 2010-01-20 | Johns Hopkins University | Low calcemic, highly antiproliferative, analogs of calcitriol |
| WO2010088304A1 (en) | 2009-01-27 | 2010-08-05 | Cytotech Labs, Llc | Vitamin d3 and analogs thereof for alleviating side effects associated with chemotherapy |
| CA2770683C (en) | 2009-08-14 | 2018-09-04 | Berg Biosystems, Llc | Vitamin d3 and analogs thereof for treating alopecia |
| WO2012065050A1 (en) | 2010-11-12 | 2012-05-18 | Wisconsin Alumni Research Foundation | 22-haloacetoxy-homopregnacalciferol analogs and their uses |
| KR20160013201A (ko) | 2013-05-29 | 2016-02-03 | 버그 엘엘씨 | 비타민 d를 이용한 화학요법 유발 탈모증의 예방 또는 완화 |
| 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 |
| US4717721A (en) * | 1985-05-30 | 1988-01-05 | Howard W. Bremer | Sidechain homo-vitamin D compounds with preferential anti-cancer activity |
| DE3687377T2 (de) * | 1985-01-17 | 1993-04-29 | Wisconsin Alumni Res Found | Vitamin-d-abkoemmlinge und deren herstellungsverfahren. |
| 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 |
| WO1989010351A1 (en) * | 1988-04-21 | 1989-11-02 | Leo Pharmaceutical Products Ltd. A/S (Løvens Kemis | Novel vitamin d analogues |
| RU2057117C1 (ru) * | 1988-04-29 | 1996-03-27 | Висконсин Алюмни Рисерч Фаундейшн | 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 |
-
1988
- 1988-04-29 US US07/187,680 patent/US4927815A/en not_active Expired - Fee Related
-
1989
- 1989-04-18 WO PCT/US1989/001633 patent/WO1989010353A1/en not_active Application Discontinuation
- 1989-04-18 HU HU892989A patent/HU206083B/hu not_active IP Right Cessation
- 1989-04-18 EP EP89905880A patent/EP0375757A1/en not_active Ceased
- 1989-04-18 NL NL8920414A patent/NL8920414A/nl not_active Application Discontinuation
- 1989-04-18 KR KR1019890702481A patent/KR930011151B1/ko not_active Expired - Lifetime
- 1989-04-18 AU AU35730/89A patent/AU630096B2/en not_active Ceased
- 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 |
|---|---|
| IN170659B (instruction) | 1992-05-02 |
| KR930011151B1 (ko) | 1993-11-24 |
| IE67868B1 (en) | 1996-05-01 |
| JPH0748343A (ja) | 1995-02-21 |
| US5061699A (en) | 1991-10-29 |
| IE891406L (en) | 1989-10-29 |
| WO1989010353A1 (en) | 1989-11-02 |
| JP2505713B2 (ja) | 1996-06-12 |
| KR900700449A (ko) | 1990-08-13 |
| AU3573089A (en) | 1989-11-24 |
| EP0375757A1 (en) | 1990-07-04 |
| DK89091A (da) | 1991-05-13 |
| HU892989D0 (en) | 1990-06-28 |
| HU206083B (en) | 1992-08-28 |
| IL90066A0 (en) | 1989-12-15 |
| DK666589A (da) | 1990-02-28 |
| DK89091D0 (da) | 1991-05-13 |
| DK666589D0 (da) | 1989-12-22 |
| AU630096B2 (en) | 1992-10-22 |
| FR2630740A1 (fr) | 1989-11-03 |
| NL8920414A (nl) | 1990-04-02 |
| JPH02504154A (ja) | 1990-11-29 |
| IL90066A (en) | 1995-12-08 |
| GB8909570D0 (en) | 1989-06-14 |
| GB2217715A (en) | 1989-11-01 |
| JPH0725730B2 (ja) | 1995-03-22 |
| US4927815A (en) | 1990-05-22 |
| HUT52475A (en) | 1990-07-28 |
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