CA1090702A - Sterolins and their use - Google Patents
Sterolins and their useInfo
- Publication number
- CA1090702A CA1090702A CA294,045A CA294045A CA1090702A CA 1090702 A CA1090702 A CA 1090702A CA 294045 A CA294045 A CA 294045A CA 1090702 A CA1090702 A CA 1090702A
- Authority
- CA
- Canada
- Prior art keywords
- glucoside
- sterol
- sitosteryl
- sterolins
- sterolin
- 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
Links
- 229930182558 Sterol Natural products 0.000 claims abstract description 32
- 235000003702 sterols Nutrition 0.000 claims abstract description 32
- 201000005569 Gout Diseases 0.000 claims abstract description 17
- -1 Sterol glycosides Chemical class 0.000 claims abstract description 14
- 229930182470 glycoside Natural products 0.000 claims abstract description 11
- 150000002148 esters Chemical class 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims description 26
- 150000003432 sterols Chemical class 0.000 claims description 23
- 229930182478 glucoside Natural products 0.000 claims description 15
- 150000008131 glucosides Chemical class 0.000 claims description 12
- 235000010469 Glycine max Nutrition 0.000 claims description 10
- 244000068988 Glycine max Species 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- NPJICTMALKLTFW-NEOYQNEMSA-N Sitosteryl glucoside Chemical compound O([C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CC[C@@H](CC)C(C)C)[C@@H]1OC(CO)[C@@H](O)C(O)C1O NPJICTMALKLTFW-NEOYQNEMSA-N 0.000 claims description 6
- 210000002307 prostate Anatomy 0.000 claims description 5
- 239000003784 tall oil Substances 0.000 claims description 5
- 206010020880 Hypertrophy Diseases 0.000 claims description 4
- VWDLOXMZIGUBKM-UHFFFAOYSA-N stigmasterol-3beta-O-D-glucoside Natural products C1CC2(C)C3CCC4(C)C(C(C)C=CC(CC)C(C)C)CCC4C3CC=C2CC1OC1OC(CO)C(O)C(O)C1O VWDLOXMZIGUBKM-UHFFFAOYSA-N 0.000 claims description 4
- VWDLOXMZIGUBKM-PLWLBJPKSA-N Stigmasteryl glucoside Chemical compound O([C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@H]1OC(CO)[C@@H](O)C(O)C1O VWDLOXMZIGUBKM-PLWLBJPKSA-N 0.000 claims description 3
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 2
- QXMNTPFFZFYQAI-IMDKZJJXSA-N beta-sitosterol 3-O-beta-D-glucopyranoside Natural products CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O[C@@H]5C[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C(C)C QXMNTPFFZFYQAI-IMDKZJJXSA-N 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 208000024891 symptom Diseases 0.000 abstract description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
- 239000000243 solution Substances 0.000 description 32
- 150000001875 compounds Chemical class 0.000 description 27
- 238000011282 treatment Methods 0.000 description 26
- NPJICTMALKLTFW-OFUAXYCQSA-N daucosterol Chemical class O([C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CC[C@@H](CC)C(C)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O NPJICTMALKLTFW-OFUAXYCQSA-N 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 description 16
- 230000000694 effects Effects 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000002245 particle Substances 0.000 description 14
- 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 13
- 239000008101 lactose Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- KZJWDPNRJALLNS-VPUBHVLGSA-N (-)-beta-Sitosterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@@H](C(C)C)CC)C)CC4)CC3)CC=2)CC1 KZJWDPNRJALLNS-VPUBHVLGSA-N 0.000 description 12
- CSVWWLUMXNHWSU-UHFFFAOYSA-N (22E)-(24xi)-24-ethyl-5alpha-cholest-22-en-3beta-ol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(CC)C(C)C)C1(C)CC2 CSVWWLUMXNHWSU-UHFFFAOYSA-N 0.000 description 12
- KLEXDBGYSOIREE-UHFFFAOYSA-N 24xi-n-propylcholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CCC)C(C)C)C1(C)CC2 KLEXDBGYSOIREE-UHFFFAOYSA-N 0.000 description 12
- LPZCCMIISIBREI-MTFRKTCUSA-N Citrostadienol Natural products CC=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C LPZCCMIISIBREI-MTFRKTCUSA-N 0.000 description 12
- ARVGMISWLZPBCH-UHFFFAOYSA-N Dehydro-beta-sitosterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCC(CC)C(C)C)CCC33)C)C3=CC=C21 ARVGMISWLZPBCH-UHFFFAOYSA-N 0.000 description 12
- MJVXAPPOFPTTCA-UHFFFAOYSA-N beta-Sistosterol Natural products CCC(CCC(C)C1CCC2C3CC=C4C(C)C(O)CCC4(C)C3CCC12C)C(C)C MJVXAPPOFPTTCA-UHFFFAOYSA-N 0.000 description 12
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 description 12
- 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 12
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol 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)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 12
- 229950005143 sitosterol Drugs 0.000 description 12
- 235000015500 sitosterol Nutrition 0.000 description 12
- NLQLSVXGSXCXFE-UHFFFAOYSA-N sitosterol Natural products CC=C(/CCC(C)C1CC2C3=CCC4C(C)C(O)CCC4(C)C3CCC2(C)C1)C(C)C NLQLSVXGSXCXFE-UHFFFAOYSA-N 0.000 description 12
- 241000196324 Embryophyta Species 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000009467 reduction Effects 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- 150000002338 glycosides Chemical class 0.000 description 7
- 230000037396 body weight Effects 0.000 description 6
- 230000000875 corresponding effect Effects 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 229960002895 phenylbutazone Drugs 0.000 description 6
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 210000002700 urine Anatomy 0.000 description 6
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 5
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 5
- 206010003246 arthritis Diseases 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000006866 deterioration Effects 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 description 4
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 description 4
- SGNBVLSWZMBQTH-FGAXOLDCSA-N Campesterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@H](C(C)C)C)C)CC4)CC3)CC=2)CC1 SGNBVLSWZMBQTH-FGAXOLDCSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- BTEISVKTSQLKST-UHFFFAOYSA-N Haliclonasterol Natural products CC(C=CC(C)C(C)(C)C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C BTEISVKTSQLKST-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- HZYXFRGVBOPPNZ-UHFFFAOYSA-N UNPD88870 Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)=CCC(CC)C(C)C)C1(C)CC2 HZYXFRGVBOPPNZ-UHFFFAOYSA-N 0.000 description 4
- 239000002260 anti-inflammatory agent Substances 0.000 description 4
- SGNBVLSWZMBQTH-PODYLUTMSA-N campesterol 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)CC[C@@H](C)C(C)C)[C@@]1(C)CC2 SGNBVLSWZMBQTH-PODYLUTMSA-N 0.000 description 4
- 235000000431 campesterol Nutrition 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 235000012000 cholesterol Nutrition 0.000 description 4
- 229940107161 cholesterol Drugs 0.000 description 4
- 230000010339 dilation Effects 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
- 229940068065 phytosterols Drugs 0.000 description 4
- HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol 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)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 description 4
- 229940032091 stigmasterol Drugs 0.000 description 4
- 235000016831 stigmasterol Nutrition 0.000 description 4
- BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
- 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 3
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 3
- 206010061218 Inflammation Diseases 0.000 description 3
- 206010061876 Obstruction Diseases 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- 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 3
- 208000025865 Ulcer Diseases 0.000 description 3
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000008298 dragée Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 210000000548 hind-foot Anatomy 0.000 description 3
- 229960001680 ibuprofen Drugs 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 230000002757 inflammatory effect Effects 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 235000012054 meals Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229940127557 pharmaceutical product Drugs 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000006104 solid solution Substances 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- 231100000397 ulcer Toxicity 0.000 description 3
- OSELKOCHBMDKEJ-UHFFFAOYSA-N (10R)-3c-Hydroxy-10r.13c-dimethyl-17c-((R)-1-methyl-4-isopropyl-hexen-(4c)-yl)-(8cH.9tH.14tH)-Delta5-tetradecahydro-1H-cyclopenta[a]phenanthren Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(=CC)C(C)C)C1(C)CC2 OSELKOCHBMDKEJ-UHFFFAOYSA-N 0.000 description 2
- BQPPJGMMIYJVBR-UHFFFAOYSA-N (10S)-3c-Acetoxy-4.4.10r.13c.14t-pentamethyl-17c-((R)-1.5-dimethyl-hexen-(4)-yl)-(5tH)-Delta8-tetradecahydro-1H-cyclopenta[a]phenanthren Natural products CC12CCC(OC(C)=O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C BQPPJGMMIYJVBR-UHFFFAOYSA-N 0.000 description 2
- CHGIKSSZNBCNDW-UHFFFAOYSA-N (3beta,5alpha)-4,4-Dimethylcholesta-8,24-dien-3-ol Natural products CC12CCC(O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21 CHGIKSSZNBCNDW-UHFFFAOYSA-N 0.000 description 2
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 2
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 2
- XYTLYKGXLMKYMV-UHFFFAOYSA-N 14alpha-methylzymosterol Natural products CC12CCC(O)CC1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C XYTLYKGXLMKYMV-UHFFFAOYSA-N 0.000 description 2
- XZEUYTKSAYNYPK-UHFFFAOYSA-N 3beta-29-Norcycloart-24-en-3-ol Natural products C1CC2(C)C(C(CCC=C(C)C)C)CCC2(C)C2CCC3C(C)C(O)CCC33C21C3 XZEUYTKSAYNYPK-UHFFFAOYSA-N 0.000 description 2
- FPTJELQXIUUCEY-UHFFFAOYSA-N 3beta-Hydroxy-lanostan Natural products C1CC2C(C)(C)C(O)CCC2(C)C2C1C1(C)CCC(C(C)CCCC(C)C)C1(C)CC2 FPTJELQXIUUCEY-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- RRTBTJPVUGMUNR-UHFFFAOYSA-N Cycloartanol Natural products C12CCC(C(C(O)CC3)(C)C)C3C2(CC)CCC2(C)C1(C)CCC2C(C)CCCC(C)C RRTBTJPVUGMUNR-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- BKLIAINBCQPSOV-UHFFFAOYSA-N Gluanol Natural products CC(C)CC=CC(C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(O)C(C)(C)C4CC3 BKLIAINBCQPSOV-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- HVXLSFNCWWWDPA-UHFFFAOYSA-N Isocycloartenol Natural products C1CC(O)C(C)(C)C2C31CC13CCC3(C)C(C(CCCC(C)=C)C)CCC3(C)C1CC2 HVXLSFNCWWWDPA-UHFFFAOYSA-N 0.000 description 2
- LOPKHWOTGJIQLC-UHFFFAOYSA-N Lanosterol Natural products CC(CCC=C(C)C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(C)(O)C(C)(C)C4CC3 LOPKHWOTGJIQLC-UHFFFAOYSA-N 0.000 description 2
- CAHGCLMLTWQZNJ-UHFFFAOYSA-N Nerifoliol Natural products CC12CCC(O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C CAHGCLMLTWQZNJ-UHFFFAOYSA-N 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- HXQRIQXPGMPSRW-UHZRDUGNSA-N Pollinastanol Natural products O[C@@H]1C[C@H]2[C@@]3([C@]4([C@H]([C@@]5(C)[C@@](C)([C@H]([C@H](CCCC(C)C)C)CC5)CC4)CC2)C3)CC1 HXQRIQXPGMPSRW-UHZRDUGNSA-N 0.000 description 2
- 206010051482 Prostatomegaly Diseases 0.000 description 2
- 208000025747 Rheumatic disease Diseases 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 2
- CYAYKKUWALRRPA-RGDJUOJXSA-N [(2r,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-bromooxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O CYAYKKUWALRRPA-RGDJUOJXSA-N 0.000 description 2
- MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-N 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 230000000721 bacterilogical effect Effects 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
- 229960003677 chloroquine Drugs 0.000 description 2
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 2
- ONQRKEUAIJMULO-YBXTVTTCSA-N cycloartenol Chemical compound CC(C)([C@@H](O)CC1)[C@H]2[C@@]31C[C@@]13CC[C@]3(C)[C@@H]([C@@H](CCC=C(C)C)C)CC[C@@]3(C)[C@@H]1CC2 ONQRKEUAIJMULO-YBXTVTTCSA-N 0.000 description 2
- YNBJLDSWFGUFRT-UHFFFAOYSA-N cycloartenol Natural products CC(CCC=C(C)C)C1CCC2(C)C1(C)CCC34CC35CCC(O)C(C)(C)C5CCC24C YNBJLDSWFGUFRT-UHFFFAOYSA-N 0.000 description 2
- FODTZLFLDFKIQH-UHFFFAOYSA-N cycloartenol trans-ferulate Natural products C1=C(O)C(OC)=CC(C=CC(=O)OC2C(C3CCC4C5(C)CCC(C5(C)CCC54CC53CC2)C(C)CCC=C(C)C)(C)C)=C1 FODTZLFLDFKIQH-UHFFFAOYSA-N 0.000 description 2
- QBSJHOGDIUQWTH-UHFFFAOYSA-N dihydrolanosterol Natural products CC(C)CCCC(C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(C)(O)C(C)(C)C4CC3 QBSJHOGDIUQWTH-UHFFFAOYSA-N 0.000 description 2
- 150000002016 disaccharides Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 2
- LPEPZBJOKDYZAD-UHFFFAOYSA-N flufenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 LPEPZBJOKDYZAD-UHFFFAOYSA-N 0.000 description 2
- 229960004369 flufenamic acid Drugs 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 208000007475 hemolytic anemia Diseases 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 229960000905 indomethacin Drugs 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 description 2
- 229960000991 ketoprofen Drugs 0.000 description 2
- CAHGCLMLTWQZNJ-RGEKOYMOSA-N lanosterol Chemical compound C([C@]12C)C[C@@H](O)C(C)(C)[C@H]1CCC1=C2CC[C@]2(C)[C@H]([C@H](CCC=C(C)C)C)CC[C@@]21C CAHGCLMLTWQZNJ-RGEKOYMOSA-N 0.000 description 2
- 229940058690 lanosterol Drugs 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 229960000649 oxyphenbutazone Drugs 0.000 description 2
- HFHZKZSRXITVMK-UHFFFAOYSA-N oxyphenbutazone Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=C(O)C=C1 HFHZKZSRXITVMK-UHFFFAOYSA-N 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 239000000419 plant extract Substances 0.000 description 2
- 239000003790 pyrimidine antagonist Substances 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 210000000813 small intestine Anatomy 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 210000005070 sphincter Anatomy 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 210000003708 urethra Anatomy 0.000 description 2
- 229940116269 uric acid Drugs 0.000 description 2
- 210000001635 urinary tract Anatomy 0.000 description 2
- MCWVPSBQQXUCTB-UHFFFAOYSA-N (24Z)-5alpha-Stigmasta-7,24(28)-dien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCC(=CC)C(C)C)CCC33)C)C3=CCC21 MCWVPSBQQXUCTB-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
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-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
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 1
- CQSRUKJFZKVYCY-UHFFFAOYSA-N 5alpha-isofucostan-3beta-ol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(=CC)C(C)C)C1(C)CC2 CQSRUKJFZKVYCY-UHFFFAOYSA-N 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- 201000010000 Agranulocytosis Diseases 0.000 description 1
- 208000031295 Animal disease Diseases 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 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
- 125000002353 D-glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- GBBBJSKVBYJMBG-QTWVXCTBSA-N Fucosterol Natural products CC=C(CC[C@@H](C)[C@@H]1CC[C@@H]2[C@H]3C=C[C@@H]4C[C@H](O)CC[C@@]4(C)[C@@H]3CC[C@@]12C)C(C)C GBBBJSKVBYJMBG-QTWVXCTBSA-N 0.000 description 1
- 208000035150 Hypercholesterolemia Diseases 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
- OSELKOCHBMDKEJ-VRUYXKNBSA-N Isofucosterol Natural products CC=C(CC[C@@H](C)[C@H]1CC[C@@H]2[C@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C)C(C)C OSELKOCHBMDKEJ-VRUYXKNBSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- UZHDGDDPOPDJGM-UHFFFAOYSA-N Stigmatellin A Natural products COC1=CC(OC)=C2C(=O)C(C)=C(CCC(C)C(OC)C(C)C(C=CC=CC(C)=CC)OC)OC2=C1O UZHDGDDPOPDJGM-UHFFFAOYSA-N 0.000 description 1
- 206010046555 Urinary retention Diseases 0.000 description 1
- 208000025609 Urogenital disease Diseases 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 208000038016 acute inflammation Diseases 0.000 description 1
- 230000006022 acute inflammation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000001919 adrenal effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 229960003459 allopurinol Drugs 0.000 description 1
- OFCNXPDARWKPPY-UHFFFAOYSA-N allopurinol Chemical compound OC1=NC=NC2=C1C=NN2 OFCNXPDARWKPPY-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000002255 antigout agent Substances 0.000 description 1
- 229960002708 antigout preparations Drugs 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 230000002917 arthritic effect Effects 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- MCWVPSBQQXUCTB-OQTIOYDCSA-N avenasterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@H](C)CC/C(=C/C)C(C)C)CC[C@H]33)C)C3=CC[C@H]21 MCWVPSBQQXUCTB-OQTIOYDCSA-N 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000004820 blood count Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229960001338 colchicine Drugs 0.000 description 1
- 229960004544 cortisone Drugs 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 230000002497 edematous effect Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 210000002683 foot Anatomy 0.000 description 1
- 235000021022 fresh fruits Nutrition 0.000 description 1
- OSELKOCHBMDKEJ-JUGJNGJRSA-N fucosterol 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)CC\C(=C/C)C(C)C)[C@@]1(C)CC2 OSELKOCHBMDKEJ-JUGJNGJRSA-N 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 229960001031 glucose Drugs 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- 210000000244 kidney pelvis Anatomy 0.000 description 1
- 230000006651 lactation Effects 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 229960002160 maltose Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 1
- 229960003081 probenecid Drugs 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229910001958 silver carbonate Inorganic materials 0.000 description 1
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- VWDLOXMZIGUBKM-AUGXRQBFSA-N stigmasterol 3-O-beta-D-glucoside Chemical compound O([C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VWDLOXMZIGUBKM-AUGXRQBFSA-N 0.000 description 1
- 229960003329 sulfinpyrazone Drugs 0.000 description 1
- MBGGBVCUIVRRBF-UHFFFAOYSA-N sulfinpyrazone Chemical compound O=C1N(C=2C=CC=CC=2)N(C=2C=CC=CC=2)C(=O)C1CCS(=O)C1=CC=CC=C1 MBGGBVCUIVRRBF-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003648 triterpenes Chemical class 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2659466 | 1976-12-30 | ||
| DE19762659466 DE2659466A1 (de) | 1976-12-30 | 1976-12-30 | Steroline und deren verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1090702A true CA1090702A (en) | 1980-12-02 |
Family
ID=5996974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA294,045A Expired CA1090702A (en) | 1976-12-30 | 1977-12-29 | Sterolins and their use |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4188379A (2) |
| AU (1) | AU516060B2 (2) |
| BE (1) | BE862433A (2) |
| CA (1) | CA1090702A (2) |
| DE (1) | DE2659466A1 (2) |
| DK (1) | DK584777A (2) |
| ES (1) | ES463990A1 (2) |
| FI (1) | FI773954A7 (2) |
| FR (1) | FR2375865A1 (2) |
| GB (1) | GB1595247A (2) |
| GR (1) | GR66083B (2) |
| IE (1) | IE48246B1 (2) |
| IT (1) | IT1089246B (2) |
| LU (1) | LU78793A1 (2) |
| NL (1) | NL7714524A (2) |
| NZ (1) | NZ186147A (2) |
| PT (1) | PT67475B (2) |
| SE (1) | SE7714950L (2) |
| YU (1) | YU40306B (2) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56113799A (en) * | 1980-02-08 | 1981-09-07 | Nippon Shinyaku Co Ltd | Glucoside derivative |
| US4612370A (en) * | 1982-04-02 | 1986-09-16 | The Regents Of The University Of California | Lipid-saccharide reaction products |
| US4602003A (en) * | 1982-05-17 | 1986-07-22 | Medical Research Foundation Of Oregon | Synthetic compounds to inhibit intestinal absorption of cholesterol in the treatment of hypercholesterolemia |
| US4614796A (en) * | 1983-03-25 | 1986-09-30 | Nippon Shinyaku Co., Ltd. | Liposome and method of manufacture therefor |
| DE3401178A1 (de) * | 1984-01-14 | 1985-07-18 | Roecar Holdings (Netherlands Antilles) N.V., Willemstad, Curacao, Niederländische Antillen | Verwendung von phytosterolglykosiden zur behandlung erhoehter 5(6)(alpha)-epoxicholesterolspiegel |
| US4814324A (en) * | 1987-03-06 | 1989-03-21 | Merck & Co., Inc. | Sterol inhibitors of testosterone 5α-reductase |
| DE3829641A1 (de) * | 1988-09-01 | 1990-03-15 | Roecar Holdings Nv | Transdermal anwendbare pharmazeutische zubereitungen mit sterolinen und/oder spiroketalinen |
| DE69213804T2 (de) * | 1991-03-28 | 1997-03-27 | Rooperol Na Nv | Zusammensetzungen von Phytosterolen mit Phytosterolinen als Immunmodulatoren |
| CA2389670A1 (en) * | 1999-11-01 | 2001-05-10 | Forbes Medi-Tech Inc. | Novel glycosides comprising pentose mono-, di-, tri-, or oligosaccharides and phytosterols and/or phytostanols |
| US20040048810A1 (en) * | 2000-11-03 | 2004-03-11 | Shaw Christopher Ariel | Sterol glucoside toxins |
| CZ300722B6 (cs) * | 2006-09-27 | 2009-07-22 | Univerzita Karlova v Praze, Prírodovedecká fakulta | Zpusob prípravy inkluzního komplexu pentacyklických a tetracyklických terpenoidu a farmaceutického prostredku obsahujícího tento inkluzní komplex, inkluzní komplex pentacyklického nebo tetracyklického terpenoidu a farmaceutický prostredek obsahující |
| CN107349209A (zh) * | 2008-10-31 | 2017-11-17 | 神经机能生命科学公司 | 神经毒性甾醇糖苷 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE35018B1 (en) * | 1970-03-18 | 1975-10-15 | Liebenberg R W | Therapeutic agent |
| ZA72698B (en) * | 1972-02-03 | 1973-09-26 | Liebenberg R W | Method of preparing medicinal compositions |
| ZA721855B (en) * | 1972-03-17 | 1973-05-30 | Liebenberg R W | Extraction of sterolins from plant material |
| US3966918A (en) * | 1973-12-12 | 1976-06-29 | Nippon Shinyaku Co., Ltd. | Method of preparing aqueous solutions of sterol glycosides and their ester derivatives |
| GB1468473A (en) * | 1974-08-14 | 1977-03-30 | Nippon Shinyaku Co Ltd | Method for the preparation of steryl beta-d-glucoside palmitates |
| JPS51118817A (en) * | 1975-04-08 | 1976-10-19 | Nippon Shinyaku Co Ltd | A process for preparing absorbable steroid glycoside pharmaceutical |
-
1976
- 1976-12-30 DE DE19762659466 patent/DE2659466A1/de not_active Ceased
-
1977
- 1977-08-22 YU YU2013/77A patent/YU40306B/xx unknown
- 1977-10-19 US US05/843,496 patent/US4188379A/en not_active Expired - Lifetime
- 1977-11-10 ES ES463990A patent/ES463990A1/es not_active Expired
- 1977-12-22 GR GR55038A patent/GR66083B/el unknown
- 1977-12-27 FR FR7739313A patent/FR2375865A1/fr active Granted
- 1977-12-28 BE BE183937A patent/BE862433A/xx not_active IP Right Cessation
- 1977-12-28 FI FI773954A patent/FI773954A7/fi not_active Application Discontinuation
- 1977-12-29 PT PT67475A patent/PT67475B/pt unknown
- 1977-12-29 CA CA294,045A patent/CA1090702A/en not_active Expired
- 1977-12-29 DK DK584777A patent/DK584777A/da not_active Application Discontinuation
- 1977-12-29 GB GB54215/77A patent/GB1595247A/en not_active Expired
- 1977-12-29 LU LU78793A patent/LU78793A1/xx unknown
- 1977-12-29 NL NL7714524A patent/NL7714524A/xx not_active Application Discontinuation
- 1977-12-30 IT IT31424/77A patent/IT1089246B/it active
- 1977-12-30 AU AU32090/77A patent/AU516060B2/en not_active Expired
- 1977-12-30 IE IE2666/77A patent/IE48246B1/en not_active IP Right Cessation
- 1977-12-30 SE SE7714950A patent/SE7714950L/ unknown
-
1978
- 1978-01-05 NZ NZ186147A patent/NZ186147A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK584777A (da) | 1978-07-01 |
| FI773954A7 (fi) | 1978-07-01 |
| DE2659466A1 (de) | 1979-02-15 |
| GR66083B (2) | 1981-01-15 |
| IE772666L (en) | 1978-06-30 |
| LU78793A1 (2) | 1978-04-17 |
| IT1089246B (it) | 1985-06-18 |
| BE862433A (fr) | 1978-04-14 |
| PT67475B (en) | 1979-05-28 |
| GB1595247A (en) | 1981-08-12 |
| AU516060B2 (en) | 1981-05-14 |
| FR2375865A1 (fr) | 1978-07-28 |
| NZ186147A (en) | 1979-10-25 |
| PT67475A (en) | 1978-01-01 |
| YU40306B (en) | 1985-12-31 |
| NL7714524A (nl) | 1978-07-04 |
| ES463990A1 (es) | 1979-10-01 |
| AU3209077A (en) | 1979-07-05 |
| US4188379A (en) | 1980-02-12 |
| SE7714950L (sv) | 1978-07-01 |
| YU201377A (en) | 1983-01-21 |
| FR2375865B1 (2) | 1981-10-30 |
| IE48246B1 (en) | 1984-11-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4260603A (en) | Sterol glycoside with activity as prostaglandin synthetase inhibitor | |
| US4524067A (en) | Soybean saponins, and a method of isolating the same | |
| CA1090702A (en) | Sterolins and their use | |
| JP5106392B2 (ja) | レイン複合物、その調整方法及び糖尿病ネフローゼ薬物、腸癒着薬物、骨関節炎薬物への利用 | |
| US4339442A (en) | Gynosaponins, their use and a process for preparing the same | |
| KR20010030746A (ko) | 스테로이드성 사포닌을 이용한 치매의 예방 치료와스테로이드성 사포닌 화합물 | |
| US6225342B1 (en) | Use of calendula glycosides for the treatment of psoriasis | |
| JPS5942680B2 (ja) | ステリルグリコシドのヘミエステル化合物 | |
| Chawla et al. | A review of chemistry and biological activities of the genus Aerva--a desert plant | |
| CA1113006A (en) | Medicine with activity as prostaglandin-synthetase inhibitor | |
| JPH01157995A (ja) | 鎮痛−抗炎症活性を有するガングリオシドの内部エステル | |
| JP2003508444A (ja) | 植物抽出物混合物及びそれらの使用 | |
| EP1848449A2 (en) | Bioactive complex of triterpene acids, its production process and medicinal products with therapeutical uses | |
| US5942231A (en) | Method of treatment of atopic dermatitis with dried guava leaves | |
| CA1140857A (en) | Spiroketalins and their applications | |
| WO2006081771A1 (en) | Artemisine (qinghaosu) derivatives, their preparation methods and their use, and pharmaceutical compositions containing the same | |
| US4198401A (en) | Active plant extracts of hypoxidaceae and their use | |
| JPS6016925B2 (ja) | 代謝作用薬剤 | |
| GB2024624A (en) | Anti inflammatory spiroketalins | |
| US4160860A (en) | Active plant extracts of hypoxidaceae and their use | |
| JP4516958B2 (ja) | 抗糖尿病用組成物 | |
| US3271250A (en) | Therapy and control of atherosclerotic diseases | |
| JP3717189B2 (ja) | 鎮痛抗炎症剤 | |
| JPS5843385B2 (ja) | シジミの薬効成分及びその製造法 | |
| KR830000630B1 (ko) | 스피로케탈-스테로이드 글리코 사이드의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |