IL96982A - Hydroxy-steroidal glyceride production from hydroxy-steroids in the presence of a basic iodine in a new amount of glycoside-catalyzing glycolide and pharmaceutical preparations - Google Patents
Hydroxy-steroidal glyceride production from hydroxy-steroids in the presence of a basic iodine in a new amount of glycoside-catalyzing glycolide and pharmaceutical preparationsInfo
- Publication number
- IL96982A IL96982A IL9698291A IL9698291A IL96982A IL 96982 A IL96982 A IL 96982A IL 9698291 A IL9698291 A IL 9698291A IL 9698291 A IL9698291 A IL 9698291A IL 96982 A IL96982 A IL 96982A
- Authority
- IL
- Israel
- Prior art keywords
- cholesten
- dideoxy
- erythro
- hexyl
- delta5
- Prior art date
Links
- 229930182470 glycoside Natural products 0.000 title claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- -1 hydroxy-steroid glycosides Chemical class 0.000 title claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 10
- 230000003197 catalytic effect Effects 0.000 title claims description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 title description 8
- 229910052740 iodine Inorganic materials 0.000 title description 8
- 239000011630 iodine Substances 0.000 title description 7
- 238000000034 method Methods 0.000 claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 150000002338 glycosides Chemical class 0.000 claims abstract description 17
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims abstract description 8
- KVUXYQHEESDGIJ-UHFFFAOYSA-N 10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,16-diol Chemical compound C1CC2CC(O)CCC2(C)C2C1C1CC(O)CC1(C)CC2 KVUXYQHEESDGIJ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 206010028980 Neoplasm Diseases 0.000 claims description 13
- 201000011510 cancer Diseases 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000969 carrier Substances 0.000 claims description 6
- BCEIUDAMUFAQMG-UHFFFAOYSA-M CC(C)(C)O[Cr](O)(=O)=O Chemical compound CC(C)(C)O[Cr](O)(=O)=O BCEIUDAMUFAQMG-UHFFFAOYSA-M 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000004615 ingredient Substances 0.000 claims description 4
- 230000003204 osmotic effect Effects 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 239000000872 buffer Substances 0.000 claims description 3
- VTHIKKVKIVQWHV-UHFFFAOYSA-N chromium(6+) oxygen(2-) pyridine Chemical compound [O-2].[O-2].[O-2].[Cr+6].C1=CC=NC=C1 VTHIKKVKIVQWHV-UHFFFAOYSA-N 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 239000003995 emulsifying agent Substances 0.000 claims description 3
- 235000003599 food sweetener Nutrition 0.000 claims description 3
- 230000001279 glycosylating effect Effects 0.000 claims description 3
- 239000003906 humectant Substances 0.000 claims description 3
- 239000003755 preservative agent Substances 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- 239000003765 sweetening agent Substances 0.000 claims description 3
- 208000001431 Psychomotor Agitation Diseases 0.000 claims description 2
- 206010038743 Restlessness Diseases 0.000 claims description 2
- PRNFLFIICMGARJ-UHFFFAOYSA-N carbonochloridic acid;pyridine Chemical compound OC(Cl)=O.C1=CC=NC=C1 PRNFLFIICMGARJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 208000024891 symptom Diseases 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 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 abstract description 19
- 230000000694 effects Effects 0.000 abstract description 13
- 235000012000 cholesterol Nutrition 0.000 abstract description 9
- 238000006206 glycosylation reaction Methods 0.000 abstract description 9
- 230000013595 glycosylation Effects 0.000 abstract description 8
- 229930002534 steroid glycoside Natural products 0.000 abstract description 5
- 150000008143 steroidal glycosides Chemical class 0.000 abstract description 5
- 239000007809 chemical reaction catalyst Substances 0.000 abstract description 3
- 230000003211 malignant effect Effects 0.000 abstract description 3
- 230000003647 oxidation Effects 0.000 abstract description 3
- 238000007254 oxidation reaction Methods 0.000 abstract description 3
- 230000000144 pharmacologic effect Effects 0.000 abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 2
- RYVMUASDIZQXAA-UHFFFAOYSA-N pyranoside Natural products O1C2(OCC(C)C(OC3C(C(O)C(O)C(CO)O3)O)C2)C(C)C(C2(CCC3C4(C)CC5O)C)C1CC2C3CC=C4CC5OC(C(C1O)O)OC(CO)C1OC(C1OC2C(C(OC3C(C(O)C(O)C(CO)O3)O)C(O)C(CO)O2)O)OC(CO)C(O)C1OC1OCC(O)C(O)C1O RYVMUASDIZQXAA-UHFFFAOYSA-N 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 230000004957 immunoregulator effect Effects 0.000 abstract 1
- 230000001506 immunosuppresive effect Effects 0.000 abstract 1
- 238000001727 in vivo Methods 0.000 abstract 1
- 230000004936 stimulating effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 24
- 238000010586 diagram Methods 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000002905 orthoesters Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 150000003431 steroids Chemical class 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 238000004566 IR spectroscopy Methods 0.000 description 3
- 102000007330 LDL Lipoproteins Human genes 0.000 description 3
- 108010007622 LDL Lipoproteins Proteins 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- LLPWGHLVUPBSLP-UTUOFQBUSA-N [(2r,3s,4r)-3,4-diacetyloxy-3,4-dihydro-2h-pyran-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1OC=C[C@@H](OC(C)=O)[C@@H]1OC(C)=O LLPWGHLVUPBSLP-UTUOFQBUSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- YVECGMZCTULTIS-PBXRRBTRSA-N glucal Chemical compound OC[C@H]1OC=C[C@@H](O)[C@@H]1O YVECGMZCTULTIS-PBXRRBTRSA-N 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- YIKKMWSQVKJCOP-ABXCMAEBSA-N 7-ketocholesterol Chemical class C1C[C@H](O)CC2=CC(=O)[C@H]3[C@@H]4CC[C@H]([C@H](C)CCCC(C)C)[C@@]4(C)CC[C@@H]3[C@]21C YIKKMWSQVKJCOP-ABXCMAEBSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000255789 Bombyx mori Species 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 2
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 210000000170 cell membrane Anatomy 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001841 cholesterols Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 210000000822 natural killer cell Anatomy 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000003637 steroidlike Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 210000001541 thymus gland Anatomy 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 1
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 1
- ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
- ZESRJSPZRDMNHY-YFWFAHHUSA-N 11-deoxycorticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 ZESRJSPZRDMNHY-YFWFAHHUSA-N 0.000 description 1
- WHBHBVVOGNECLV-OBQKJFGGSA-N 11-deoxycortisol Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 WHBHBVVOGNECLV-OBQKJFGGSA-N 0.000 description 1
- JERGUCIJOXJXHF-TVWVXWENSA-N 17alpha-hydroxypregnenolone Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 JERGUCIJOXJXHF-TVWVXWENSA-N 0.000 description 1
- DBPWSSGDRRHUNT-CEGNMAFCSA-N 17α-hydroxyprogesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 DBPWSSGDRRHUNT-CEGNMAFCSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- INBGSXNNRGWLJU-ZHHJOTBYSA-N 25-hydroxycholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CCCC(C)(C)O)C)[C@@]1(C)CC2 INBGSXNNRGWLJU-ZHHJOTBYSA-N 0.000 description 1
- KJKIIUAXZGLUND-ICCVIKJNSA-N 25-hydroxyvitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](\C=C\[C@H](C)C(C)(C)O)C)=C\C=C1\C[C@@H](O)CCC1=C KJKIIUAXZGLUND-ICCVIKJNSA-N 0.000 description 1
- INBGSXNNRGWLJU-UHFFFAOYSA-N 25epsilon-Hydroxycholesterin Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(CCCC(C)(C)O)C)C1(C)CC2 INBGSXNNRGWLJU-UHFFFAOYSA-N 0.000 description 1
- XGGAWFDOIDZRPI-UHFFFAOYSA-N 4,6-Dihydroxy Natural products C1=C2OCOC2=CC(C2OC(C3C(OC(O)C32)C=2C=C3OCOC3=CC=2)O)=C1 XGGAWFDOIDZRPI-UHFFFAOYSA-N 0.000 description 1
- QGXBDMJGAMFCBF-HLUDHZFRSA-N 5α-Androsterone Chemical compound C1[C@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@H]21 QGXBDMJGAMFCBF-HLUDHZFRSA-N 0.000 description 1
- 241000751139 Beauveria bassiana Species 0.000 description 1
- 241000255791 Bombyx Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000003390 Chinese drug Substances 0.000 description 1
- 239000004380 Cholic acid Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 description 1
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 1
- QGXBDMJGAMFCBF-UHFFFAOYSA-N Etiocholanolone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC21 QGXBDMJGAMFCBF-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 108010024636 Glutathione Proteins 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
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229910010084 LiAlH4 Inorganic materials 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- JWIPGAFCGUDKEY-UHFFFAOYSA-L O[Cr](Cl)(=O)=O.C1=CC=NC=C1 Chemical compound O[Cr](Cl)(=O)=O.C1=CC=NC=C1 JWIPGAFCGUDKEY-UHFFFAOYSA-L 0.000 description 1
- ORNBQBCIOKFOEO-YQUGOWONSA-N Pregnenolone Natural products O=C(C)[C@@H]1[C@@]2(C)[C@H]([C@H]3[C@@H]([C@]4(C)C(=CC3)C[C@@H](O)CC4)CC2)CC1 ORNBQBCIOKFOEO-YQUGOWONSA-N 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- JXCOSKURGJMQSG-NGNMYJGKSA-N alpha-Allocortolone Chemical compound C[C@]12CC(=O)[C@H]3[C@@H](CC[C@H]4C[C@H](O)CC[C@]34C)[C@@H]1CC[C@]2(O)[C@@H](O)CO JXCOSKURGJMQSG-NGNMYJGKSA-N 0.000 description 1
- JXCOSKURGJMQSG-UHFFFAOYSA-N alpha-Cortolone Natural products C1C(O)CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(O)CO)C4C3CCC21 JXCOSKURGJMQSG-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940061641 androsterone Drugs 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 210000005056 cell body Anatomy 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000006037 cell lysis Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 1
- 235000019416 cholic acid Nutrition 0.000 description 1
- 229960002471 cholic acid Drugs 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 230000002016 colloidosmotic effect Effects 0.000 description 1
- 229940124301 concurrent medication Drugs 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 1
- 229960004544 cortisone Drugs 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229930007927 cymene Natural products 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 210000001151 cytotoxic T lymphocyte Anatomy 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- ZESRJSPZRDMNHY-UHFFFAOYSA-N de-oxy corticosterone Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 ZESRJSPZRDMNHY-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 1
- 229960003654 desoxycortone Drugs 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010218 electron microscopic analysis Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229960005309 estradiol Drugs 0.000 description 1
- 229960003399 estrone Drugs 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229960003180 glutathione Drugs 0.000 description 1
- XUPLQGYCPSEKNQ-UHFFFAOYSA-H hexasodium dioxido-oxo-sulfanylidene-lambda6-sulfane Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[O-]S([O-])(=O)=S.[O-]S([O-])(=O)=S.[O-]S([O-])(=O)=S XUPLQGYCPSEKNQ-UHFFFAOYSA-H 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229960002899 hydroxyprogesterone Drugs 0.000 description 1
- 208000013403 hyperactivity Diseases 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- FQGYCXFLEQVDJQ-UHFFFAOYSA-N mercury dicyanide Chemical compound N#C[Hg]C#N FQGYCXFLEQVDJQ-UHFFFAOYSA-N 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- ORNBQBCIOKFOEO-QGVNFLHTSA-N pregnenolone Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 ORNBQBCIOKFOEO-QGVNFLHTSA-N 0.000 description 1
- 229960000249 pregnenolone Drugs 0.000 description 1
- 229960003387 progesterone Drugs 0.000 description 1
- 239000000186 progesterone Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
- 229910001958 silver carbonate Inorganic materials 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- AODPIQQILQLWGS-GXBDJPPSSA-N tetrahydrocortisol Chemical compound C1[C@H](O)CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CC[C@@H]21 AODPIQQILQLWGS-GXBDJPPSSA-N 0.000 description 1
- 229940034252 thymus extracts Drugs 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 125000002640 tocopherol group Chemical group 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J17/005—Glycosides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4001895A DE4001895A1 (de) | 1990-01-23 | 1990-01-23 | Herstellung von insbesondere steroidglykosiden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL96982A0 IL96982A0 (en) | 1992-03-29 |
| IL96982A true IL96982A (en) | 1996-01-31 |
Family
ID=6398603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9698291A IL96982A (en) | 1990-01-23 | 1991-01-21 | Hydroxy-steroidal glyceride production from hydroxy-steroids in the presence of a basic iodine in a new amount of glycoside-catalyzing glycolide and pharmaceutical preparations |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5278296A (de) |
| EP (1) | EP0594581B1 (de) |
| JP (2) | JP2612123B2 (de) |
| KR (1) | KR100192005B1 (de) |
| CN (1) | CN1050365C (de) |
| AT (1) | ATE167868T1 (de) |
| AU (1) | AU7148991A (de) |
| CA (1) | CA2073692A1 (de) |
| DE (2) | DE4001895A1 (de) |
| HU (1) | HU214873B (de) |
| IL (1) | IL96982A (de) |
| WO (1) | WO1991011452A1 (de) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5496806A (en) * | 1990-01-23 | 1996-03-05 | R. Erich Klemke | Glycoside compounds and production and use thereof |
| US5693767A (en) * | 1991-01-22 | 1997-12-02 | Harrier Inc. | Glycoside derivatives of acetaminophen |
| IL102566A0 (en) * | 1991-07-22 | 1993-01-14 | Harrier Inc | Glycoside compounds and production and use thereof |
| US5677286A (en) * | 1995-04-27 | 1997-10-14 | The University Of Michigan | Glycosylated analogs of camptothecin |
| KR0169536B1 (ko) * | 1996-02-27 | 1999-01-15 | 손경식 | 신규한 인삼 사포닌, 그의 제조방법 및 이를 유효성분으로 하는 항종양제 |
| US6103884A (en) * | 1996-03-27 | 2000-08-15 | The University Of Michigan | Glycosylated analogs of fusidic acid |
| CN1064048C (zh) * | 1996-08-29 | 2001-04-04 | 中国科学院昆明植物研究所 | 青阳参甙丙至甙庚五个化合物及其制备方法和应用 |
| EP1742636B1 (de) * | 2004-05-05 | 2013-04-10 | Immunopharm Aktiengesellschaft | Präparat zur Behandlung von Krebs |
| FR2953154B1 (fr) * | 2009-11-30 | 2013-07-12 | Rhodia Operations | Procede de preparation d'un catalyseur de deperoxydation |
| US8921533B2 (en) | 2011-07-25 | 2014-12-30 | Chromatin Technologies | Glycosylated valproic acid analogs and uses thereof |
| WO2020097600A1 (en) * | 2018-11-09 | 2020-05-14 | Rmd Sciences Inc. | Compositions for the treatment of cancer and other conditions |
| KR102141656B1 (ko) | 2019-07-16 | 2020-08-05 | 선문대학교 산학협력단 | 글루코실트랜스퍼라제를 이용한 코르티코스테론의 생물 전환 방법 및 이로부터 얻어진 코르티코스테론 글루코시드 |
| CN119143829B (zh) * | 2024-11-06 | 2025-01-28 | 山东省食品药品检验研究院 | 一种c21甾体皂苷及其制备方法、应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI46067C (fi) * | 1968-04-06 | 1972-12-11 | Hoechst Ag | Menetelmä digitoksigeniiniglykosidien valmistamiseksi. |
| US3857832A (en) * | 1972-03-21 | 1974-12-31 | Warner Lambert Co | Process for the preparation of cardiotonic glycosides |
| US3859047A (en) * | 1973-05-29 | 1975-01-07 | Hoffmann La Roche | Standard for serum cholesterol determination |
| DE2523284B2 (de) * | 1975-05-26 | 1977-03-24 | Nippon Shiny aku Co., Ltd., Kyoto (Japan) | Haemostatische, gefaesstabilisierende und antischockmittel |
| GB1553540A (en) * | 1977-02-23 | 1979-09-26 | Green Cross Corp | Medicaments containing cholesterol derivatives |
| JPS56113799A (en) * | 1980-02-08 | 1981-09-07 | Nippon Shinyaku Co Ltd | Glucoside derivative |
| DE3127933A1 (de) * | 1980-07-18 | 1982-04-08 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von (delta)- oder (beta)-o-glycosyimidaten |
| US4415731A (en) * | 1981-03-30 | 1983-11-15 | Merck & Co., Inc. | Process for the preparation of methyl 2,6-dideoxy-α-D-arabino-hexopyranoside |
| US4629768A (en) * | 1986-05-02 | 1986-12-16 | Olin Corporation | Thermally stable polyurethane elastomers containing glycoside polyols and a method of producing them |
-
1990
- 1990-01-23 DE DE4001895A patent/DE4001895A1/de not_active Withdrawn
-
1991
- 1991-01-21 IL IL9698291A patent/IL96982A/en not_active IP Right Cessation
- 1991-01-22 CA CA002073692A patent/CA2073692A1/en not_active Abandoned
- 1991-01-22 WO PCT/EP1991/000115 patent/WO1991011452A1/en not_active Ceased
- 1991-01-22 HU HU9202121A patent/HU214873B/hu not_active IP Right Cessation
- 1991-01-22 EP EP91902953A patent/EP0594581B1/de not_active Expired - Lifetime
- 1991-01-22 DE DE69129700T patent/DE69129700T2/de not_active Expired - Fee Related
- 1991-01-22 US US07/644,002 patent/US5278296A/en not_active Expired - Lifetime
- 1991-01-22 CN CN91100394A patent/CN1050365C/zh not_active Expired - Fee Related
- 1991-01-22 JP JP3503078A patent/JP2612123B2/ja not_active Expired - Lifetime
- 1991-01-22 AT AT91902953T patent/ATE167868T1/de not_active IP Right Cessation
- 1991-01-22 AU AU71489/91A patent/AU7148991A/en not_active Abandoned
-
1992
- 1992-07-22 KR KR1019920701739A patent/KR100192005B1/ko not_active Expired - Fee Related
-
1995
- 1995-07-18 JP JP7181812A patent/JP2636208B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH08109192A (ja) | 1996-04-30 |
| WO1991011452A1 (en) | 1991-08-08 |
| DE4001895A1 (de) | 1991-07-25 |
| US5278296A (en) | 1994-01-11 |
| ATE167868T1 (de) | 1998-07-15 |
| HUT61778A (en) | 1993-03-01 |
| JP2612123B2 (ja) | 1997-05-21 |
| EP0594581A1 (de) | 1994-05-04 |
| DE69129700T2 (de) | 1999-02-18 |
| IL96982A0 (en) | 1992-03-29 |
| JP2636208B2 (ja) | 1997-07-30 |
| JPH05504565A (ja) | 1993-07-15 |
| AU7148991A (en) | 1991-08-21 |
| EP0594581B1 (de) | 1998-07-01 |
| CN1053239A (zh) | 1991-07-24 |
| HU9202121D0 (en) | 1992-12-28 |
| KR100192005B1 (en) | 1999-06-15 |
| CA2073692A1 (en) | 1991-07-24 |
| DE69129700D1 (de) | 1998-08-06 |
| CN1050365C (zh) | 2000-03-15 |
| HU214873B (hu) | 1998-07-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Wilds et al. | The facile synthesis of 19-nortestosterone and 19-norandrostenedione from estrone | |
| IL96982A (en) | Hydroxy-steroidal glyceride production from hydroxy-steroids in the presence of a basic iodine in a new amount of glycoside-catalyzing glycolide and pharmaceutical preparations | |
| GB1599863A (en) | Pharmaceutical compositions for use in the inhibition of the biosynthesis of mevalonic acid | |
| HK60297A (en) | Androstane 17-carboxylic-acid esters, their preparation and medicaments containing them | |
| Itoh et al. | Minor and trace sterols in marine invertebrates. 36.(24S)-24H-Isocalysterol: A new steroidal cyclopropene from the marine sponge Calyx niceaensis | |
| Sauer et al. | Ecdysterone biosynthesis in Podocarpus elata | |
| US5693767A (en) | Glycoside derivatives of acetaminophen | |
| US3380886A (en) | 7alpha-methyl-3beta-hydroxy-5-androstenes | |
| BHAVNANI et al. | Formation of Steroids by the Pregnant Mare. III. Metabolism of 14C-Squalene and 3H-Dehydroisoandrosterone Injected into the Fetal Circulation1 | |
| Tweit et al. | Microbiological transformations. XII. The substrate specificity of hydroxylations by a Penicillium sp., ATCC 12,556 | |
| EP0318490A1 (de) | 14,17-g(b)-ETHANO-14-g(b)-ESTRATRIENE, VERFAHREN ZU DEREN HERSTELLUNG UND DIESE ENTHALTENDE PHARMAZEUTISCHE PRÄPARATE. | |
| Iriarte et al. | Steroids. XCIX. Synthesis of Ring B Oxygenated Estrogens1 | |
| US5496806A (en) | Glycoside compounds and production and use thereof | |
| EP0597018B1 (de) | Glykosidierungsverfahren | |
| USRE37999E1 (en) | 20-(B)-20,25-dihydroperoxy-3β-hydroxycholest-5-ene and 20-(S)-20,25-dihydroperoxy-3β-hydroxycholest-5-ene | |
| JPS62155294A (ja) | １−メチル−１５α−アルキル−アンドロスタ−１，４−ジエン−３，１７−ジオン、その製法およびこれを含有するエストロゲン生合成を阻止する医薬調剤 | |
| MEYER et al. | Identification of three transformation products after an adrenal perfusion with epiandrosterone | |
| Pearlman | A Study of the Neutral, Non-Saponifiable Fraction of Ox Bile1 | |
| Wolff et al. | Synthesis and activity of some nitro steroids | |
| Anastasia et al. | Synthesis of 14. beta.-cholest-5-en-3. beta.-ol | |
| Poos et al. | Synthesis of a tricyclic analog of cortisone | |
| US3383282A (en) | 7alpha-methyl-3, 5-androstadiene-3, 17-diols and pharmaceutically active compositions thereof | |
| Camoutsis et al. | Formation of bishomoazasteroids by the beckmann rearrangement | |
| US3140302A (en) | 11-keto-12-dehydro-steroids and method for their preparation | |
| US3655652A (en) | Aromatically-unsaturated 9alpha-methyl steroids |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |