UA72439C2 - Pharmaceutical compositions containing appetite suppressant agent - Google Patents
Pharmaceutical compositions containing appetite suppressant agent Download PDFInfo
- Publication number
- UA72439C2 UA72439C2 UA99116170A UA99116170A UA72439C2 UA 72439 C2 UA72439 C2 UA 72439C2 UA 99116170 A UA99116170 A UA 99116170A UA 99116170 A UA99116170 A UA 99116170A UA 72439 C2 UA72439 C2 UA 72439C2
- Authority
- UA
- Ukraine
- Prior art keywords
- compound
- extract
- formula
- noodia
- treatment
- Prior art date
Links
- 239000002830 appetite depressant Substances 0.000 title claims abstract description 75
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 264
- 238000000034 method Methods 0.000 claims abstract description 105
- 239000000284 extract Substances 0.000 claims abstract description 95
- 230000000694 effects Effects 0.000 claims abstract description 85
- 241000196324 Embryophyta Species 0.000 claims abstract description 71
- 239000003814 drug Substances 0.000 claims abstract description 22
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 claims abstract description 15
- 241001465754 Metazoa Species 0.000 claims description 139
- 239000000203 mixture Substances 0.000 claims description 125
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 97
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 94
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 90
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 84
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 68
- -1 monosaccharide compound Chemical class 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 235000011389 fruit/vegetable juice Nutrition 0.000 claims description 48
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 48
- 239000002904 solvent Substances 0.000 claims description 43
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 40
- 150000003431 steroids Chemical class 0.000 claims description 40
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 38
- 239000000463 material Substances 0.000 claims description 36
- 208000008589 Obesity Diseases 0.000 claims description 35
- 235000020824 obesity Nutrition 0.000 claims description 35
- 230000036528 appetite Effects 0.000 claims description 27
- 235000019789 appetite Nutrition 0.000 claims description 26
- 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 claims description 23
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 23
- 150000002895 organic esters Chemical group 0.000 claims description 23
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 claims description 22
- 239000000843 powder Substances 0.000 claims description 22
- 239000008103 glucose Substances 0.000 claims description 21
- 235000014633 carbohydrates Nutrition 0.000 claims description 20
- 238000000605 extraction Methods 0.000 claims description 19
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 19
- 150000001720 carbohydrates Chemical class 0.000 claims description 18
- 150000002772 monosaccharides Chemical class 0.000 claims description 18
- 230000002265 prevention Effects 0.000 claims description 15
- 229920006395 saturated elastomer Polymers 0.000 claims description 15
- 241000894007 species Species 0.000 claims description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 14
- 229930002534 steroid glycoside Natural products 0.000 claims description 14
- 150000004043 trisaccharides Chemical class 0.000 claims description 14
- 150000002016 disaccharides Chemical class 0.000 claims description 13
- 239000003480 eluent Substances 0.000 claims description 11
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 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 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003638 chemical reducing agent Substances 0.000 claims description 8
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims description 7
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 7
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 7
- 238000012545 processing Methods 0.000 claims description 7
- 239000011780 sodium chloride Substances 0.000 claims description 7
- 239000001119 stannous chloride Substances 0.000 claims description 7
- 235000011150 stannous chloride Nutrition 0.000 claims description 7
- 241000282414 Homo sapiens Species 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 230000003993 interaction Effects 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000008024 pharmaceutical diluent Substances 0.000 claims description 6
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 6
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- VJMQFIRIMMSSRW-UHFFFAOYSA-N trimethyl(phenylsulfanyl)silane Chemical compound C[Si](C)(C)SC1=CC=CC=C1 VJMQFIRIMMSSRW-UHFFFAOYSA-N 0.000 claims description 5
- 241000282412 Homo Species 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 235000013361 beverage Nutrition 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 238000003825 pressing Methods 0.000 claims description 4
- 125000005607 tigloyl group Chemical group 0.000 claims description 4
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 claims description 3
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 claims description 3
- 239000002552 dosage form Substances 0.000 claims description 3
- 235000011056 potassium acetate Nutrition 0.000 claims description 3
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 claims description 3
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 claims description 3
- 239000007868 Raney catalyst Substances 0.000 claims description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 29
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims 16
- 238000013375 chromatographic separation Methods 0.000 claims 6
- 239000003085 diluting agent Substances 0.000 claims 6
- 239000013543 active substance Substances 0.000 claims 4
- 150000008143 steroidal glycosides Chemical class 0.000 claims 3
- 238000006165 Knowles reaction Methods 0.000 claims 2
- WIOBOUWMWWLZKG-QBZJCNLTSA-N Sarcostin Chemical compound C1C[C@H](O)CC2=CC[C@@]3(O)[C@@]4(O)CC[C@]([C@@H](O)C)(O)[C@@]4(C)[C@H](O)C[C@@H]3[C@]21C WIOBOUWMWWLZKG-QBZJCNLTSA-N 0.000 claims 2
- OLHRMWGUPWKSSC-UHFFFAOYSA-N Sarcostin Natural products CC(O)C1(O)CCC2(O)C3CC=C4CC(O)CCC4(C)C3C(O)C2(O)C1 OLHRMWGUPWKSSC-UHFFFAOYSA-N 0.000 claims 2
- 125000005601 angeloyl group Chemical group 0.000 claims 2
- 150000002430 hydrocarbons Chemical class 0.000 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- NPKKRSHVJIQBKU-UHFFFAOYSA-N ornogenin Natural products CC(OC(=O)C=Cc1ccccc1)C2(O)CCC3(O)C4(O)CC=C5CC(O)CCC5(C)C4CC(OC(=O)C=Cc6ccccc6)C23C NPKKRSHVJIQBKU-UHFFFAOYSA-N 0.000 claims 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 1
- OUYHTSFXOODGQT-UHFFFAOYSA-N OS(C(F)(F)F)(=O)=O.OS(C(F)(F)F)(=O)=O.OS(C(F)(F)F)(=O)=O.N Chemical compound OS(C(F)(F)F)(=O)=O.OS(C(F)(F)F)(=O)=O.OS(C(F)(F)F)(=O)=O.N OUYHTSFXOODGQT-UHFFFAOYSA-N 0.000 claims 1
- 241000220317 Rosa Species 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- HMBPRCCUFZTWRS-UHFFFAOYSA-N trimethylsilyl fluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)CF HMBPRCCUFZTWRS-UHFFFAOYSA-N 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 21
- 238000003786 synthesis reaction Methods 0.000 abstract description 12
- 241001504226 Hoodia Species 0.000 abstract 2
- 235000017277 hoodia Nutrition 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 239000000523 sample Substances 0.000 description 84
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 72
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 62
- 239000000243 solution Substances 0.000 description 57
- 230000037396 body weight Effects 0.000 description 42
- 239000011541 reaction mixture Substances 0.000 description 39
- 239000010410 layer Substances 0.000 description 37
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 34
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 31
- 235000019341 magnesium sulphate Nutrition 0.000 description 31
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 238000012360 testing method Methods 0.000 description 27
- 241000700159 Rattus Species 0.000 description 26
- 210000004185 liver Anatomy 0.000 description 26
- 235000012631 food intake Nutrition 0.000 description 25
- 235000013305 food Nutrition 0.000 description 23
- 230000037406 food intake Effects 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 239000000741 silica gel Substances 0.000 description 20
- 229910002027 silica gel Inorganic materials 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 230000001965 increasing effect Effects 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- 230000007423 decrease Effects 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 230000002354 daily effect Effects 0.000 description 15
- 238000002474 experimental method Methods 0.000 description 14
- 235000017557 sodium bicarbonate Nutrition 0.000 description 14
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
- 239000003981 vehicle Substances 0.000 description 14
- 238000001228 spectrum Methods 0.000 description 13
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 12
- 230000002829 reductive effect Effects 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 230000007170 pathology Effects 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 231100000161 signs of toxicity Toxicity 0.000 description 10
- DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 9
- 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 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 229960001582 fenfluramine Drugs 0.000 description 9
- 239000012280 lithium aluminium hydride Substances 0.000 description 9
- 229960003387 progesterone Drugs 0.000 description 9
- 239000000186 progesterone Substances 0.000 description 9
- 230000009467 reduction Effects 0.000 description 9
- 239000012047 saturated solution Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 230000008859 change Effects 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 230000007850 degeneration Effects 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 210000003494 hepatocyte Anatomy 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 238000011886 postmortem examination Methods 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- 230000008961 swelling Effects 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 238000007385 chemical modification Methods 0.000 description 5
- 230000034994 death Effects 0.000 description 5
- 206010061428 decreased appetite Diseases 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- 230000003902 lesion Effects 0.000 description 5
- 239000000401 methanolic extract Substances 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 5
- 230000003880 negative regulation of appetite Effects 0.000 description 5
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 5
- 229920001592 potato starch Polymers 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- PNLYLUYLYDYNFK-LKBIUASMSA-N 5-[(8r,9s,10s,13s,14s,17s)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2,3-dihydro-1,4-dioxine Chemical compound C1([C@H]2CC[C@H]3[C@H]4[C@@H]([C@]5(CCCCC5CC4)C)CC[C@@]32C)=COCCO1 PNLYLUYLYDYNFK-LKBIUASMSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- GOYBREOSJSERKM-DSYKOEDSSA-N D-cymarose Chemical compound O=CC[C@H](OC)[C@H](O)[C@@H](C)O GOYBREOSJSERKM-DSYKOEDSSA-N 0.000 description 4
- 229940117029 Melanocortin receptor agonist Drugs 0.000 description 4
- 208000004756 Respiratory Insufficiency Diseases 0.000 description 4
- 206010038678 Respiratory depression Diseases 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000008188 altrosides Chemical class 0.000 description 4
- 239000000287 crude extract Substances 0.000 description 4
- 235000005911 diet Nutrition 0.000 description 4
- 230000037213 diet Effects 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 230000006742 locomotor activity Effects 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000000336 melanocortin receptor agonist Substances 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 4
- 239000000419 plant extract Substances 0.000 description 4
- 150000003146 progesterones Chemical class 0.000 description 4
- 230000001624 sedative effect Effects 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 235000019786 weight gain Nutrition 0.000 description 4
- 239000011592 zinc chloride Substances 0.000 description 4
- 235000005074 zinc chloride Nutrition 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 101100123850 Caenorhabditis elegans her-1 gene Proteins 0.000 description 3
- 206010010904 Convulsion Diseases 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 230000036760 body temperature Effects 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 230000036461 convulsion Effects 0.000 description 3
- 235000021316 daily nutritional intake Nutrition 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 238000006073 displacement reaction Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 231100000673 dose–response relationship Toxicity 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 150000008131 glucosides Chemical class 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 230000002503 metabolic effect Effects 0.000 description 3
- 235000018770 reduced food intake Nutrition 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 230000029058 respiratory gaseous exchange Effects 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000001694 spray drying Methods 0.000 description 3
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 3
- UIERETOOQGIECD-ARJAWSKDSA-M 2-Methyl-2-butenoic acid Natural products C\C=C(\C)C([O-])=O UIERETOOQGIECD-ARJAWSKDSA-M 0.000 description 2
- 244000099147 Ananas comosus Species 0.000 description 2
- 235000007119 Ananas comosus Nutrition 0.000 description 2
- UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 description 2
- 206010002942 Apathy Diseases 0.000 description 2
- 241000283707 Capra Species 0.000 description 2
- 101800001982 Cholecystokinin Proteins 0.000 description 2
- 102100025841 Cholecystokinin Human genes 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- WZUVPPKBWHMQCE-UHFFFAOYSA-N Haematoxylin Chemical compound C12=CC(O)=C(O)C=C2CC2(O)C1C1=CC=C(O)C(O)=C1OC2 WZUVPPKBWHMQCE-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 102000004378 Melanocortin Receptors Human genes 0.000 description 2
- 108090000950 Melanocortin Receptors Proteins 0.000 description 2
- 108090000189 Neuropeptides Proteins 0.000 description 2
- 241000283984 Rodentia Species 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 230000004596 appetite loss Effects 0.000 description 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
- 238000004166 bioassay Methods 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 229940107137 cholecystokinin Drugs 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000001086 cytosolic effect Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 244000144993 groups of animals Species 0.000 description 2
- 230000037219 healthy weight Effects 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 210000004969 inflammatory cell Anatomy 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000007928 intraperitoneal injection Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 210000005229 liver cell Anatomy 0.000 description 2
- 208000019017 loss of appetite Diseases 0.000 description 2
- 235000021266 loss of appetite Nutrition 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 230000036186 satiety Effects 0.000 description 2
- 235000019627 satiety Nutrition 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 2
- 208000016261 weight loss Diseases 0.000 description 2
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 2
- FOLRUCXBTYDAQK-SFZUHQLGSA-N (4ar,7r,8r,8as)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-6,7,8-triol Chemical compound C([C@H]1OC([C@@H]([C@@H](O)[C@@H]1O1)O)O)OC1C1=CC=CC=C1 FOLRUCXBTYDAQK-SFZUHQLGSA-N 0.000 description 1
- XOJIHVCRNAFVAJ-JIFZMYKYSA-N (8S,9S,10R,13S,14S,17R)-17-acetyl-16,16-dihydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,17-decahydro-1H-cyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC(O)(O)[C@H](C(=O)C)[C@@]1(C)CC2 XOJIHVCRNAFVAJ-JIFZMYKYSA-N 0.000 description 1
- ZSOGJMQVUVGFEW-NTHVCZEQSA-N 2-[(8R,9S,10S,13S,14S,17S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethene-1,1,2-triol Chemical compound OC(=C(O)O)[C@H]1CC[C@H]2[C@@H]3CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C ZSOGJMQVUVGFEW-NTHVCZEQSA-N 0.000 description 1
- AYIBFUOYFKMFIV-XMJUESPCSA-N 2-[(8r,9s,10r,13r,17s)-10,13-dimethyl-2,7,8,9,11,12,16,17-octahydro-1h-cyclopenta[a]phenanthren-17-yl]-1,4-dioxane Chemical compound C1([C@H]2CC=C3[C@H]4[C@@H]([C@]5(CCC=CC5=CC4)C)CC[C@@]32C)COCCO1 AYIBFUOYFKMFIV-XMJUESPCSA-N 0.000 description 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- CUCUKLJLRRAKFN-UHFFFAOYSA-N 7-Hydroxy-(S)-usnate Chemical compound CC12C(=O)C(C(=O)C)C(=O)C=C1OC1=C2C(O)=C(C)C(O)=C1C(C)=O CUCUKLJLRRAKFN-UHFFFAOYSA-N 0.000 description 1
- 206010000060 Abdominal distension Diseases 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 1
- 206010003497 Asphyxia Diseases 0.000 description 1
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- 208000031648 Body Weight Changes Diseases 0.000 description 1
- 108010051479 Bombesin Proteins 0.000 description 1
- 102000013585 Bombesin Human genes 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000566113 Branta sandvicensis Species 0.000 description 1
- 101100314454 Caenorhabditis elegans tra-1 gene Proteins 0.000 description 1
- 241000282832 Camelidae Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000600039 Chromis punctipinnis Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- GOYBREOSJSERKM-UHFFFAOYSA-N D-oleandrose Natural products O=CCC(OC)C(O)C(C)O GOYBREOSJSERKM-UHFFFAOYSA-N 0.000 description 1
- 206010052804 Drug tolerance Diseases 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241001201696 Eulia Species 0.000 description 1
- 206010015548 Euthanasia Diseases 0.000 description 1
- 206010015995 Eyelid ptosis Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- 208000005422 Foreign-Body reaction Diseases 0.000 description 1
- 102400000322 Glucagon-like peptide 1 Human genes 0.000 description 1
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 description 1
- 101800000224 Glucagon-like peptide 1 Proteins 0.000 description 1
- 101000939500 Homo sapiens UBX domain-containing protein 11 Proteins 0.000 description 1
- 206010020880 Hypertrophy Diseases 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- 206010051602 Laziness Diseases 0.000 description 1
- 102000016267 Leptin Human genes 0.000 description 1
- 108010092277 Leptin Proteins 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- 229940122865 Melanocortin MC-4 receptor agonist Drugs 0.000 description 1
- 108010008364 Melanocortins Proteins 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000282339 Mustela Species 0.000 description 1
- 241001318330 Nenia Species 0.000 description 1
- 102100038842 Neuropeptide B Human genes 0.000 description 1
- 102000003797 Neuropeptides Human genes 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 240000000220 Panda oleosa Species 0.000 description 1
- 235000016496 Panda oleosa Nutrition 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 235000004789 Rosa xanthina Nutrition 0.000 description 1
- 241000109329 Rosa xanthina Species 0.000 description 1
- 101000941926 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) Carboxypeptidase Y inhibitor Proteins 0.000 description 1
- 241000716515 Sapovirus GIV Species 0.000 description 1
- 244000300264 Spinacia oleracea Species 0.000 description 1
- 235000009337 Spinacia oleracea Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000000692 Student's t-test Methods 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
- 241000282887 Suidae Species 0.000 description 1
- 102000008316 Type 4 Melanocortin Receptor Human genes 0.000 description 1
- 108010021436 Type 4 Melanocortin Receptor Proteins 0.000 description 1
- 102100029645 UBX domain-containing protein 11 Human genes 0.000 description 1
- 241001178076 Zaga Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- KQCRAJUZKQWICM-FQHFXROUSA-N [(8r,9s,10r,13r,17s)-17-acetyl-3-acetyloxy-10,13-dimethyl-2,7,8,9,11,12,16,17-octahydro-1h-cyclopenta[a]phenanthren-12-yl] acetate Chemical compound C1=C(OC(C)=O)CC[C@]2(C)[C@H]3CC(OC(=O)C)[C@]4(C)[C@@H](C(C)=O)CC=C4[C@@H]3CC=C21 KQCRAJUZKQWICM-FQHFXROUSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- QXAITBQSYVNQDR-UHFFFAOYSA-N amitraz Chemical compound C=1C=C(C)C=C(C)C=1N=CN(C)C=NC1=CC=C(C)C=C1C QXAITBQSYVNQDR-UHFFFAOYSA-N 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000012455 bioassay technique Methods 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 230000004579 body weight change Effects 0.000 description 1
- DNDCVAGJPBKION-DOPDSADYSA-N bombesin Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC=1NC2=CC=CC=C2C=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1NC(=O)CC1)C(C)C)C1=CN=CN1 DNDCVAGJPBKION-DOPDSADYSA-N 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 235000019577 caloric intake Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000012292 cell migration Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000001268 conjugating effect Effects 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- NFDFQCUYFHCNBW-SCGPFSFSSA-N dienestrol Chemical compound C=1C=C(O)C=CC=1\C(=C/C)\C(=C\C)\C1=CC=C(O)C=C1 NFDFQCUYFHCNBW-SCGPFSFSSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 230000020595 eating behavior Effects 0.000 description 1
- 230000002497 edematous effect Effects 0.000 description 1
- 230000000816 effect on animals Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000019439 energy homeostasis Effects 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- 230000002327 eosinophilic effect Effects 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 210000000744 eyelid Anatomy 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000004761 fibrosis Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 230000030136 gastric emptying Effects 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 230000000762 glandular Effects 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- 230000026781 habituation Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000011132 hemopoiesis Effects 0.000 description 1
- 231100000234 hepatic damage Toxicity 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 239000002035 hexane extract Substances 0.000 description 1
- 239000002044 hexane fraction Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000010562 histological examination Methods 0.000 description 1
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000001146 hypoxic effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 description 1
- 229940039781 leptin Drugs 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 230000008818 liver damage Effects 0.000 description 1
- 208000020442 loss of weight Diseases 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 230000000527 lymphocytic effect Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000002865 melanocortin Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- ZYCFMHCDZSVIGF-UHFFFAOYSA-N methyl 4-amino-1-(2-aminoethyl)-2-butylimidazo[4,5-c]quinoline-7-carboxylate Chemical compound NC1=NC=2C=C(C=CC=2C2=C1N=C(N2CCN)CCCC)C(=O)OC ZYCFMHCDZSVIGF-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000004660 morphological change Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 108010085094 neuropeptide B Proteins 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 231100000915 pathological change Toxicity 0.000 description 1
- 230000036285 pathological change Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 201000003004 ptosis Diseases 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000003893 regulation of appetite Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000028527 righting reflex Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 230000001331 thermoregulatory effect Effects 0.000 description 1
- 230000035922 thirst Effects 0.000 description 1
- 230000003868 tissue accumulation Effects 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 210000003934 vacuole Anatomy 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/33—Cactaceae (Cactus family), e.g. pricklypear or Cereus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/765—Polymers containing oxygen
- A61K31/78—Polymers containing oxygen of acrylic acid or derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/27—Asclepiadaceae (Milkweed family), e.g. hoya
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/04—Disaccharides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/08—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to sulfur, selenium or tellurium
- C07H5/10—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to sulfur, selenium or tellurium to sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J15/00—Stereochemically pure steroids containing carbon, hydrogen, halogen or oxygen having a partially or totally inverted skeleton, e.g. retrosteroids, L-isomers
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa
- C07J7/002—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa not substituted in position 16
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa
- C07J7/0025—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa substituted in position 16
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa
- C07J7/0025—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa substituted in position 16
- C07J7/0035—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa substituted in position 16 by a hydroxy group free esterified or etherified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/0065—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by an OH group free esterified or etherified
- C07J7/007—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by an OH group free esterified or etherified not substituted in position 17 alfa
-
- 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
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Biotechnology (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Botany (AREA)
- Mycology (AREA)
- Microbiology (AREA)
- Medical Informatics (AREA)
- Alternative & Traditional Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Nutrition Science (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Food Science & Technology (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Medicinal Preparation (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ZA973201 | 1997-04-15 | ||
PCT/GB1998/001100 WO1998046243A2 (en) | 1997-04-15 | 1998-04-15 | Pharmaceutical compositions having appetite suppressant activity |
Publications (1)
Publication Number | Publication Date |
---|---|
UA72439C2 true UA72439C2 (en) | 2005-03-15 |
Family
ID=25586362
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
UA99116170A UA72439C2 (en) | 1997-04-15 | 1998-04-15 | Pharmaceutical compositions containing appetite suppressant agent |
Country Status (40)
Country | Link |
---|---|
US (6) | US6376657B1 (ja) |
EP (5) | EP1598054B1 (ja) |
JP (3) | JP3553086B2 (ja) |
KR (2) | KR100510614B1 (ja) |
CN (3) | CN101239089A (ja) |
AP (3) | AP2003002730A0 (ja) |
AT (3) | ATE344046T1 (ja) |
AU (1) | AU746414B2 (ja) |
BG (1) | BG103795A (ja) |
BR (1) | BR9808593A (ja) |
CA (2) | CA2584411A1 (ja) |
DE (3) | DE69836321T2 (ja) |
DK (1) | DK0973534T3 (ja) |
EA (2) | EA200200392A1 (ja) |
EE (1) | EE9900497A (ja) |
ES (3) | ES2276460T3 (ja) |
GB (3) | GB2360519B (ja) |
GE (2) | GEP20022709B (ja) |
GT (3) | GT199800076A (ja) |
HK (1) | HK1026373A1 (ja) |
HU (1) | HUP0000838A3 (ja) |
ID (1) | ID22888A (ja) |
IL (3) | IL158466A0 (ja) |
IS (1) | IS5196A (ja) |
MY (1) | MY141674A (ja) |
NO (1) | NO994992L (ja) |
NZ (5) | NZ525022A (ja) |
OA (1) | OA11166A (ja) |
PE (1) | PE85699A1 (ja) |
PL (3) | PL201487B1 (ja) |
PT (2) | PT1213020E (ja) |
SA (1) | SA98190501B1 (ja) |
SG (1) | SG120054A1 (ja) |
SK (1) | SK141899A3 (ja) |
TR (2) | TR199902540T2 (ja) |
TW (3) | TW539551B (ja) |
UA (1) | UA72439C2 (ja) |
WO (1) | WO1998046243A2 (ja) |
YU (1) | YU52199A (ja) |
ZA (1) | ZA983170B (ja) |
Families Citing this family (70)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998046243A2 (en) * | 1997-04-15 | 1998-10-22 | Csir | Pharmaceutical compositions having appetite suppressant activity |
BR0012984A (pt) * | 1999-08-04 | 2002-07-16 | Millennium Pharm Inc | Método para tratar um estado associado com o mc4-r em um mamìfero, composto de ligação ao mc4-r, e, composição farmacêutica |
GB2355657B (en) * | 1999-10-27 | 2004-07-28 | Phytopharm Plc | Inhibitors Of Gastric Acid Secretion |
GB2363985B (en) * | 2000-06-30 | 2004-09-29 | Phytopharm Plc | Extracts,compounds & pharmaceutical compositions having anti-diabetic activity and their use |
KR20040015670A (ko) * | 2001-01-24 | 2004-02-19 | 트리콘 호울딩즈 리미티드 | 탄탈륨 필름 침착방법 |
US7008648B2 (en) | 2001-11-16 | 2006-03-07 | Novartis Nutrition Ag | Plant derived or derivable material with appetite suppressing activity |
US20040265398A1 (en) * | 2002-04-25 | 2004-12-30 | Fleischner Albert M. | Herbal composition for weight control |
TW200505461A (en) * | 2003-02-14 | 2005-02-16 | Phytopharm Plc | Moldulation of ATP production or content in the hypothalamus |
US7060308B2 (en) * | 2003-06-04 | 2006-06-13 | Ramaswamy Rajendran | Caralluma extract products and processes for making the same |
US7976880B2 (en) * | 2003-06-04 | 2011-07-12 | Ramaswamy Rajendran | Pregnane glycoside compositions and Caralluma extract products and uses thereof |
US7265101B2 (en) * | 2004-04-07 | 2007-09-04 | Rutgers, The State University Of New Jersey | Appetite-suppressing compositions and methods |
GB0411703D0 (en) * | 2004-05-25 | 2004-06-30 | Phytopharm Plc | Selective separation or extraction of steroidal glycosides |
US20050276839A1 (en) * | 2004-06-10 | 2005-12-15 | Rifkin Calman H | Appetite satiation and hydration beverage |
US20050276869A1 (en) * | 2004-06-14 | 2005-12-15 | Century Systems | Appetite-suppressing, lipase-inhibiting herbal composition |
US7500679B2 (en) * | 2004-10-08 | 2009-03-10 | Wade James T | Board for supporting front of snow vehicle |
US20060083795A1 (en) * | 2004-10-19 | 2006-04-20 | Lima Shatkina | Meal replacement products having appetite suppressing qualities |
GB0425172D0 (en) * | 2004-11-15 | 2004-12-15 | Phyto Res Ltd | Plant cells and uses thereof |
CA2596311A1 (en) * | 2005-01-20 | 2006-07-27 | Stephen Holt | Herbal compositions containing hoodia |
AU2006279602B2 (en) * | 2005-08-17 | 2009-06-04 | Elc Management Llc | Delivery system for appetite suppressant |
US20070082085A1 (en) * | 2005-10-07 | 2007-04-12 | Catani Steven J | Compositions and methods for reducing food intake and controlling weight |
US20070082029A1 (en) * | 2005-10-07 | 2007-04-12 | Aimutis William R | Fiber satiety compositions |
US20070082108A1 (en) * | 2005-10-07 | 2007-04-12 | Aimutis William R Jr | Methods for reducing calorie intake |
US20070082115A1 (en) * | 2005-10-07 | 2007-04-12 | Aimutis William Ronald Jr | Methods for inducing satiety, reducing food intake and reducing weight |
US20070082025A1 (en) * | 2005-10-07 | 2007-04-12 | Catani Steven J | Methods for achieving and maintaining weight loss |
US20070082028A1 (en) * | 2005-10-07 | 2007-04-12 | Aimutis William R Jr | Compositions and methods for inducing satiety and reducing caloric intake |
US20070082114A1 (en) * | 2005-10-07 | 2007-04-12 | Catani Steven J | Methods for reducing weight |
US20070082026A1 (en) * | 2005-10-07 | 2007-04-12 | Aimutis William R Jr | Compositions and methods for reducing food intake and controlling weight |
US20070082084A1 (en) * | 2005-10-07 | 2007-04-12 | Catani Steven J | Methods for weight management |
US20070082030A1 (en) * | 2005-10-07 | 2007-04-12 | Aimutis William R | Fiber satiety compositions |
US20070104805A1 (en) * | 2005-11-01 | 2007-05-10 | Udell Ronald G | Compositions of Hoodia Gordonii and Pinolenic Acid Derivatives |
US8945652B2 (en) * | 2005-11-23 | 2015-02-03 | The Coca-Cola Company | High-potency sweetener for weight management and compositions sweetened therewith |
US20070207227A1 (en) * | 2006-02-23 | 2007-09-06 | Conopco, Inc., D/B/A Unilever, A Corporation Of New York | Appetite suppressant compositions |
US20070196436A1 (en) * | 2006-02-23 | 2007-08-23 | Conopco, Inc., D/B/A Unilever | Process for preparing an edible composition comprising steroidal glycosides |
RU2009100892A (ru) * | 2006-06-13 | 2010-07-20 | Юнилевер Н.В. (Nl) | Порционные композиции для подавления аппетита со стероидными гликозидами |
JP5281234B2 (ja) * | 2006-06-27 | 2013-09-04 | ポーラ化成工業株式会社 | 毛様体過緊張による疲れ目の改善・予防のための経口投与組成物 |
MX2009001571A (es) | 2006-08-17 | 2009-02-19 | Unilever Nv | Proceso para la produccion de la planta de hoodia que contiene glucosidos esteroides. |
CA2661593A1 (en) * | 2006-08-24 | 2008-02-28 | Unilever Plc | Process for preparing a composition comprising steroidal glycosides |
US20080085354A1 (en) * | 2006-10-06 | 2008-04-10 | Teresa Marie Paeschke | Controlled hydration of hydrocolloids |
US20080138447A1 (en) * | 2006-12-06 | 2008-06-12 | Erin John Riggins | Method for administering appetite suppressant and composition thereof |
WO2008074656A1 (en) * | 2006-12-21 | 2008-06-26 | Unilever N.V. | Process for harvesting plants of the apocynaceae family |
US20080188447A1 (en) * | 2007-02-02 | 2008-08-07 | Svyatoslav Komarnytsky | Glucocorticoid-lowering composition |
US8580236B2 (en) * | 2007-03-19 | 2013-11-12 | Richard P. De Maria | Hair sustaining formulation |
EP2052727A3 (en) * | 2007-10-02 | 2010-06-02 | Unilever N.V. | Hoodia extract oil compositions comprising unsaturated monoacylglycerides |
US20100316736A1 (en) * | 2007-10-24 | 2010-12-16 | Desert Labs Agriculture Cooperative Association Ltd. | Appetite suppressant |
US20090110774A1 (en) * | 2007-10-26 | 2009-04-30 | The Hershey Company | High antioxidant levels in cocoa-based beverages |
ATE502620T1 (de) | 2007-11-17 | 2011-04-15 | Cognis Ip Man Gmbh | Verfahren zur herstellung von wirkstoffkonzentraten |
EP2080517A1 (en) * | 2008-01-18 | 2009-07-22 | Unilever N.V. | Process for obtaining dried plant material |
US20090324757A1 (en) * | 2008-03-31 | 2009-12-31 | Rutgers, The State University Of New Jersey | Compositions and Methods for Modulating Visceral Sensation and/or Gastrointestinal Reflex Activity |
JP5276885B2 (ja) * | 2008-04-11 | 2013-08-28 | 株式会社耐熱性酵素研究所 | キチン又はキトサンを含む分解性複合材料 |
US20090263510A1 (en) | 2008-04-21 | 2009-10-22 | Conopco, Inc., D/B/A Unilever | Process of making Hoodia plant extract with improved flavor |
US7923435B2 (en) * | 2008-04-21 | 2011-04-12 | Phytopharm Plc | Hoodia plant extract with improved flavor |
AU2009325842A1 (en) | 2008-12-08 | 2011-07-14 | Bio-Mass Ltd. | Method of treatment of diseases using Hoodia extracts |
US20110003021A1 (en) | 2009-07-01 | 2011-01-06 | Jason Christian Grovenor Halford | Composition and method for reducing food intake |
EP2329836A1 (en) | 2009-12-03 | 2011-06-08 | I.R.B. Istituto Di Ricerche Biotecnologiche S.r.l. | Extracts obtained from hoodia gordonii cells lines, their preparation and use |
CA2827050A1 (en) * | 2010-02-18 | 2011-08-25 | The Hershey Company | Cocoa-based exercise recovery beverages |
WO2012022880A2 (fr) | 2010-07-29 | 2012-02-23 | Universite De Strasbourg | Procede de synthese de steroïdes |
CN102462690B (zh) * | 2010-11-11 | 2013-04-17 | 中国科学院上海药物研究所 | 3,8,12,14,17,20位氧取***甾烯糖苷类化合物在制备抑制食欲的药物中的用途 |
CA2923351C (en) | 2010-12-20 | 2019-01-22 | Hill's Pet Nutrition, Inc. | Pet food compositions for inducing a satiety response |
HUE051738T2 (hu) | 2011-01-07 | 2021-03-29 | Anji Pharma Us Llc | Kemoszenzoros receptorligandum-alapú terápiák |
WO2013103384A1 (en) | 2012-01-06 | 2013-07-11 | Elcelyx Therapeutics, Inc. | Biguanide compositions and methods of treating metabolic disorders |
US9795792B2 (en) | 2011-02-25 | 2017-10-24 | Medtronic, Inc. | Emergency mode switching for non-pacing modes |
BR112014016810A8 (pt) | 2012-01-06 | 2017-07-04 | Elcelyx Therapeutics Inc | composições e métodos para tratamento de distúrbios metabólicos |
US9456916B2 (en) | 2013-03-12 | 2016-10-04 | Medibotics Llc | Device for selectively reducing absorption of unhealthy food |
AR091739A1 (es) | 2012-07-11 | 2015-02-25 | Elcelyx Therapeutics Inc | Composiciones y metodos para reducir el riesgo cardiometabolico |
US20140193498A1 (en) | 2013-01-05 | 2014-07-10 | Elcelyx Therapeutics, Inc. | Compositions and Methods for Treating Metabolic Disorders |
US9067070B2 (en) | 2013-03-12 | 2015-06-30 | Medibotics Llc | Dysgeusia-inducing neurostimulation for modifying consumption of a selected nutrient type |
US9011365B2 (en) | 2013-03-12 | 2015-04-21 | Medibotics Llc | Adjustable gastrointestinal bifurcation (AGB) for reduced absorption of unhealthy food |
US20160176914A1 (en) * | 2013-05-29 | 2016-06-23 | Northeastern University | Glycosylated cardiotonic steroids |
CN103755762B (zh) * | 2014-01-30 | 2016-06-01 | 中国科学院上海有机化学研究所 | 果同尼皂苷f及其衍生物的中间体、制备方法和用途及果同尼皂苷f衍生物 |
GB2544416B (en) * | 2015-11-13 | 2017-11-01 | Lykke Res Ltd | A method for producing a medium containing steroidal glycosides from plant cells of the genus Hoodia |
Family Cites Families (78)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4062950A (en) * | 1973-09-22 | 1977-12-13 | Bayer Aktiengesellschaft | Amino sugar derivatives |
FR2348655A1 (fr) | 1976-04-20 | 1977-11-18 | Sopharga Lab | Nouvelle substance alimentaire ou dietetique ayant une structure alveolaire et son procede de preparation |
US4185116A (en) | 1976-09-28 | 1980-01-22 | Pfizer Inc. | L- and DL- Phenylglycines to treat diseases or conditions attributable to reduced carbohydrate metabolism |
USPP4199P (en) | 1977-01-18 | 1978-01-24 | B. L. Cobia, Inc. | Milkweed plant family |
DE2719912C3 (de) * | 1977-05-04 | 1979-12-06 | Bayer Ag, 5090 Leverkusen | Verfahren zur Isolierung von 0- |4,6-Dideoxy-4- [JJl S-O,4,6/5)-4,5,6-trihydroxy-3-hydroxymethyl-2cyclohexen-1-yl] -amino] - a -D-glucopyranosyl} -(I Pfeil nach rechts 4)-0- a D-glucopyranosyl-(l Pfeil nach rechts 4)-D-glucopyranose aus Kulturbrühen |
US4130714A (en) * | 1977-05-23 | 1978-12-19 | Pfizer Inc. | Hydantoin therapeutic agents |
NO154918C (no) * | 1977-08-27 | 1987-01-14 | Bayer Ag | Analogifremgangsmaate til fremstilling av terapeutisk aktive derivater av 3,4,5-trihydroksypiperidin. |
JPS5953920B2 (ja) * | 1977-12-28 | 1984-12-27 | 東洋醸造株式会社 | 新規なアミノ糖化合物およびその製法 |
IE47592B1 (en) * | 1977-12-29 | 1984-05-02 | Ici Ltd | Enzyme inhibitory phthalazin-4-ylacetic acid derivatives, pharmaceutical compositions thereof,and process for their manufacture |
US4273763A (en) | 1978-01-23 | 1981-06-16 | Efamol Limited | Pharmaceutical and dietary compositions |
JPS5745185A (en) * | 1980-07-21 | 1982-03-13 | Eisai Co Ltd | Hydantoin derivative and its preparation |
JPS5740478A (en) * | 1980-08-22 | 1982-03-06 | Ono Pharmaceut Co Ltd | Rhodanine derivative, its preparation and aldose reductase inhibitor containing rhodanine derivative |
US4791126A (en) * | 1980-08-22 | 1988-12-13 | Ono Pharmaceutical Co., Ltd. | Rhodanine derivatives, process for their preparation, and aldose reductase inhibitor containing the rhodanine derivatives as active ingredients |
EP0056194B1 (en) * | 1981-01-05 | 1984-09-12 | Takeda Chemical Industries, Ltd. | N-substituted pseudo-aminosugars, their production and use |
CA1176269A (en) * | 1981-03-02 | 1984-10-16 | Kazimir Sestanj | N-naphthoylglycine derivatives |
US4377500A (en) | 1981-07-08 | 1983-03-22 | The Standard Oil Co. | Catalysts |
US4436745A (en) * | 1982-04-15 | 1984-03-13 | Alcon Laboratories, Inc. | Method of inhibiting aldose reductase activity |
US4438272A (en) * | 1982-04-15 | 1984-03-20 | Alcon Laboratories, Inc. | Spiro-(fluoren-9,4'-imidazolidine)-2',5'-diones |
JPS58194818A (ja) | 1982-05-10 | 1983-11-12 | Iwasaki Shuzo | サボテン中の水溶性多糖及び繊維の取得方法 |
ES524614A0 (es) | 1982-08-12 | 1984-05-01 | Nativelle Sa Ets | Procedimiento de preparacion de nuevos amino-14 esteroides. |
AU570439B2 (en) | 1983-03-28 | 1988-03-17 | Compression Labs, Inc. | A combined intraframe and interframe transform coding system |
HU201675B (en) | 1983-08-26 | 1990-12-28 | Ivan Balkanyi | Process for producing oral pharmaceutical compositions with unappetizing effect |
US5066659A (en) * | 1984-10-30 | 1991-11-19 | Pfizer Inc. | Spiro-heteroazalones for treatment of diabetic complications |
US4634765A (en) * | 1984-12-18 | 1987-01-06 | Merrell Dow Pharmaceuticals Inc. | Homodisaccharide hypoglycemic agents |
US5246960A (en) | 1984-12-21 | 1993-09-21 | Hoffmann-La Roche Inc. | Oxetanones |
CA1270837A (en) | 1984-12-21 | 1990-06-26 | Hoffmann-La Roche Limited | Oxetanones |
IT1207504B (it) | 1985-09-26 | 1989-05-25 | Crinos Industria Farmaco | Composizione moderatrice dell'appetito ed antigastrica. |
IT1190400B (it) | 1985-10-04 | 1988-02-16 | Istituto Biochimico Italiano | Derivati dell'acido 19,20-bis,nor-prostanoico ad attivita' antiulcera e anoressivca,procedimento per la loro preparazione e composizioni farmaceutiche |
GB8524663D0 (en) * | 1985-10-07 | 1985-11-13 | Fujisawa Pharmaceutical Co | Quinazoline derivatives |
US4939140A (en) * | 1985-11-07 | 1990-07-03 | Pfizer Inc. | Heterocyclic oxophthalazinyl acetic acids |
US4757151A (en) | 1985-11-14 | 1988-07-12 | Warner-Lambert Company | 2-substituted-[2-substituted-amino]-N-arylalkyl-3-[indol-3-yl] |
US4652553A (en) * | 1985-11-25 | 1987-03-24 | Merck & Co., Inc. | Steroidal glycolipids as host resistance stimulators |
GB8600489D0 (en) | 1986-01-09 | 1986-02-12 | Erba Farmitalia | Aminoglycoside steroids |
AU602641B2 (en) * | 1986-04-17 | 1990-10-18 | Senju Pharmaceutical Co., Ltd. | Thiolactam-N-acetic acid derivatives, their production and use |
EP0264586B1 (en) | 1986-08-28 | 1991-04-03 | Sanwa Kagaku Kenkyusho Co., Ltd. | Hydantoin derivatives for treating complications of diabetes |
ZA883929B (en) | 1987-06-22 | 1990-02-28 | Hoffmann La Roche | Cholecystokinin analogs for controlling appetite |
US5175154A (en) * | 1987-11-25 | 1992-12-29 | Research Corporation Technologies, Inc. | 5 α-pregnan-20-ones and 5-pregnen-20-ones and related compounds |
US5192772A (en) * | 1987-12-09 | 1993-03-09 | Nippon Shinyaku Co. Ltd. | Therapeutic agents |
GB8801037D0 (en) * | 1988-01-18 | 1988-02-17 | Plessey Co Ltd | Improvements relating to fuel supply systems |
US5252572A (en) * | 1988-02-03 | 1993-10-12 | Chinoin Gyogyszer- Es Vegyeszeti Termekek Gyara Rt. | Pyridopyrimidine derivatives, pharmaceutical compositions containing them and process for preparing same |
EP0344383A1 (en) * | 1988-06-02 | 1989-12-06 | Merrell Dow Pharmaceuticals Inc. | Novel alpha-Glucosidase inhibitors |
DE3836675A1 (de) * | 1988-10-28 | 1990-05-03 | Hoechst Ag | Glykosidase-inhibitor salbostatin, verfahren zu seiner herstellung und seine verwendung |
US4978669A (en) | 1989-06-08 | 1990-12-18 | Neurex Corporation | Method of suppressing appetite by administration of tetrahydro-beta-carboline derivatives |
JPH03120227A (ja) | 1989-10-02 | 1991-05-22 | Shigeo Ochi | 飲食物消化分解産物吸収抑制剤 |
US4980357A (en) * | 1990-03-01 | 1990-12-25 | Pfizer Inc. | Azolidinedione derivatives |
US5037831A (en) * | 1990-05-21 | 1991-08-06 | American Home Products Corporation | Spiro-isoquinoline-pyrrolidines and analogs thereof useful as aldose reductase inhibitors |
US5504078A (en) * | 1990-06-08 | 1996-04-02 | Merrell Dow Pharmaceuticals Inc. | α-glucosidase inhibitors |
GB9016978D0 (en) * | 1990-08-02 | 1990-09-19 | Ici Plc | Acetamide derivatives |
US5217877A (en) * | 1990-09-28 | 1993-06-08 | Bristol-Myers Squibb Company | Process for the preparation of α-glucosidase inhibitor, pradimicin Q |
US5091418A (en) * | 1990-09-28 | 1992-02-25 | Bristol-Myers Squibb Company | Novel alpha-glucosidase inhibitor, pradimicin Q |
US6100048A (en) | 1992-04-10 | 2000-08-08 | Oregon Health Sciences University | Methods and reagents for discovering and using mammalian melanocortin receptor agonists and antagonists to modulate feeding behavior in animals |
AU683620B2 (en) * | 1992-09-28 | 1997-11-20 | Pfizer Inc. | Substituted pyrimidines for control of diabetic complications |
RU2115255C1 (ru) | 1992-09-30 | 1998-07-10 | Моторола, Инк. | Способ доставки сообщений, система связи и портативный приемник селективного вызова для осуществления способа |
GB9307833D0 (en) | 1993-04-15 | 1993-06-02 | Glaxo Inc | Modulators of cholecystokinin and gastrin |
FR2706255B1 (fr) | 1993-06-17 | 1995-10-27 | Univ Rennes | Composition à usage alimentaire et/ou pharmaceutique pauvre en polyamines et applications thérapeutiques. |
CA2165200A1 (en) | 1993-06-18 | 1995-01-05 | Ambikaipakan Balasubramaniam | Neuropeptide y antagonists and agonists |
US5516516A (en) | 1993-10-19 | 1996-05-14 | Cherksey; Bruce D. | Method of preparing muira puama extract and its use for decreasing body fat percentage and increasing lean muscle mass |
JPH07184548A (ja) | 1993-12-28 | 1995-07-25 | Meiji Seito Kk | 口腔用組成物 |
US6309853B1 (en) * | 1994-08-17 | 2001-10-30 | The Rockfeller University | Modulators of body weight, corresponding nucleic acids and proteins, and diagnostic and therapeutic uses thereof |
US5698199A (en) | 1995-03-10 | 1997-12-16 | Kao Corporation | Lipolysis acceleration method |
ATE205477T1 (de) | 1995-06-06 | 2001-09-15 | Pfizer | Substituierte n-(indol-2-carbonyl)-amide und derivate als glycogen phosphorylase inhibitoren |
MX9709875A (es) | 1995-06-06 | 1998-03-31 | Pfizer | N-(indol-2-carbonil)-glicinamidas substituidas y derivados como inhibidores de glicogeno fosforilasa, composiciones que las contienen y uso de las mismas. |
JPH08332028A (ja) | 1995-06-12 | 1996-12-17 | Takashi Mizuno | サボテン成分入り冷菓とその製法 |
US5693327A (en) | 1995-07-12 | 1997-12-02 | Shah; Eladevi | Herbal compositions |
EP0862631A1 (en) | 1995-10-26 | 1998-09-09 | The Board Of Regents, The University Of Texas System | Luminal cholecystokinin-releasing factor |
US5824668A (en) | 1996-11-07 | 1998-10-20 | Supergen, Inc. | Formulation for administration of steroid compounds |
TW432073B (en) | 1995-12-28 | 2001-05-01 | Pfizer | Pyrazolopyridine compounds |
US5932779A (en) * | 1996-06-10 | 1999-08-03 | Millennium Pharmaceuticals, Inc. | Screening methods for compounds useful in the regulation of body weight |
US5908609A (en) | 1996-06-10 | 1999-06-01 | Millennium Pharmaceuticals, Inc. | Screening methods for compounds useful in the regulation of body weight |
AU5243798A (en) | 1996-11-06 | 1998-05-29 | Children's Medical Center Corporation | Transgenic animal expressing a syndecan in the regions of hypothalamus |
WO1998027113A2 (en) * | 1996-12-17 | 1998-06-25 | Quadrant Holdings Cambridge Limited | Melanocortin derivatives for specific binding of melanocortin receptor 3, 4 or 5 |
CA2217698A1 (en) | 1996-12-20 | 1998-06-20 | Eli Lilly And Company | Anti-obesity proteins |
US5798101A (en) | 1997-01-22 | 1998-08-25 | Hpf, L.L.C. | Herbal appetite suppressant and weight loss composition |
EP0971957A1 (en) | 1997-03-26 | 2000-01-19 | Novo Nordisk A/S | Polypeptide with appetite regulating activity |
WO1998046243A2 (en) * | 1997-04-15 | 1998-10-22 | Csir | Pharmaceutical compositions having appetite suppressant activity |
FR2771105A1 (fr) | 1997-11-20 | 1999-05-21 | Vitasterol | Utilisation du fusarium monoliforme pour la preparation des derives 7alpha-hydroxyles de la dehydroepiandrosterone et de la pregnenolone |
GB2355657B (en) | 1999-10-27 | 2004-07-28 | Phytopharm Plc | Inhibitors Of Gastric Acid Secretion |
GB2363985B (en) * | 2000-06-30 | 2004-09-29 | Phytopharm Plc | Extracts,compounds & pharmaceutical compositions having anti-diabetic activity and their use |
-
1998
- 1998-04-15 WO PCT/GB1998/001100 patent/WO1998046243A2/en active Application Filing
- 1998-04-15 GB GB0117039A patent/GB2360519B/en not_active Expired - Fee Related
- 1998-04-15 YU YU52199A patent/YU52199A/sh unknown
- 1998-04-15 IL IL15846698A patent/IL158466A0/xx unknown
- 1998-04-15 ID IDW991200A patent/ID22888A/id unknown
- 1998-04-15 ES ES98917372T patent/ES2276460T3/es not_active Expired - Lifetime
- 1998-04-15 JP JP54363398A patent/JP3553086B2/ja not_active Expired - Fee Related
- 1998-04-15 GB GB9919797A patent/GB2338235B/en not_active Expired - Fee Related
- 1998-04-15 EP EP05017768A patent/EP1598054B1/en not_active Expired - Lifetime
- 1998-04-15 DE DE69836321T patent/DE69836321T2/de not_active Expired - Lifetime
- 1998-04-15 AP APAP/P/2003/002730A patent/AP2003002730A0/en unknown
- 1998-04-15 SK SK1418-99A patent/SK141899A3/sk unknown
- 1998-04-15 EA EA200200392A patent/EA200200392A1/ru unknown
- 1998-04-15 CN CNA2008100057254A patent/CN101239089A/zh active Pending
- 1998-04-15 NZ NZ525022A patent/NZ525022A/en unknown
- 1998-04-15 AT AT98917372T patent/ATE344046T1/de active
- 1998-04-15 US US09/402,962 patent/US6376657B1/en not_active Expired - Lifetime
- 1998-04-15 EP EP04002070A patent/EP1438965A1/en not_active Withdrawn
- 1998-04-15 DE DE69840552T patent/DE69840552D1/de not_active Expired - Lifetime
- 1998-04-15 PT PT02004101T patent/PT1213020E/pt unknown
- 1998-04-15 IL IL13165998A patent/IL131659A/xx not_active IP Right Cessation
- 1998-04-15 CN CNB988041650A patent/CN100378118C/zh not_active Expired - Fee Related
- 1998-04-15 PL PL380957A patent/PL201487B1/pl not_active IP Right Cessation
- 1998-04-15 DK DK98917372T patent/DK0973534T3/da active
- 1998-04-15 EE EEP199900497A patent/EE9900497A/xx unknown
- 1998-04-15 TR TR1999/02540T patent/TR199902540T2/xx unknown
- 1998-04-15 KR KR10-2003-7005297A patent/KR100510614B1/ko not_active IP Right Cessation
- 1998-04-15 NZ NZ516696A patent/NZ516696A/en unknown
- 1998-04-15 MY MYPI98001667A patent/MY141674A/en unknown
- 1998-04-15 CN CNA2008100057269A patent/CN101239090A/zh active Pending
- 1998-04-15 NZ NZ337422A patent/NZ337422A/en unknown
- 1998-04-15 SG SG200106269A patent/SG120054A1/en unknown
- 1998-04-15 ES ES02004101T patent/ES2321162T3/es not_active Expired - Lifetime
- 1998-04-15 GE GEAP19985030A patent/GEP20022709B/en unknown
- 1998-04-15 AP APAP/P/1999/001673A patent/AP1291A/en active
- 1998-04-15 ZA ZA9803170A patent/ZA983170B/xx unknown
- 1998-04-15 IL IL15846598A patent/IL158465A0/xx unknown
- 1998-04-15 EA EA199900932A patent/EA002885B1/ru not_active IP Right Cessation
- 1998-04-15 EP EP98917372A patent/EP0973534B1/en not_active Expired - Lifetime
- 1998-04-15 EP EP02004100.0A patent/EP1222927B1/en not_active Expired - Lifetime
- 1998-04-15 TR TR2000/01846T patent/TR200001846T2/xx unknown
- 1998-04-15 GE GEAP19985544A patent/GEP20022788B/en unknown
- 1998-04-15 NZ NZ516695A patent/NZ516695A/en unknown
- 1998-04-15 DE DE69842189T patent/DE69842189D1/de not_active Expired - Lifetime
- 1998-04-15 BR BR9808593-0A patent/BR9808593A/pt not_active Application Discontinuation
- 1998-04-15 AT AT02004101T patent/ATE422359T1/de active
- 1998-04-15 PL PL374521A patent/PL197783B1/pl not_active IP Right Cessation
- 1998-04-15 UA UA99116170A patent/UA72439C2/uk unknown
- 1998-04-15 CA CA002584411A patent/CA2584411A1/en not_active Abandoned
- 1998-04-15 EP EP02004101A patent/EP1213020B1/en not_active Expired - Lifetime
- 1998-04-15 AT AT05017768T patent/ATE502041T1/de not_active IP Right Cessation
- 1998-04-15 AU AU70613/98A patent/AU746414B2/en not_active Ceased
- 1998-04-15 PL PL98336498A patent/PL196015B1/pl not_active IP Right Cessation
- 1998-04-15 HU HU0000838A patent/HUP0000838A3/hu unknown
- 1998-04-15 ES ES05017768T patent/ES2363230T3/es not_active Expired - Lifetime
- 1998-04-15 KR KR1019997009513A patent/KR100891756B1/ko not_active IP Right Cessation
- 1998-04-15 PT PT98917372T patent/PT973534E/pt unknown
- 1998-04-15 NZ NZ525021A patent/NZ525021A/en unknown
- 1998-04-15 CA CA002283564A patent/CA2283564C/en not_active Expired - Fee Related
- 1998-04-15 AP APAP/P/2003/002729A patent/AP2003002729A0/en unknown
- 1998-04-15 GB GB0117041A patent/GB2360520B/en not_active Expired - Fee Related
- 1998-06-02 TW TW087108667A patent/TW539551B/zh active
- 1998-06-02 TW TW091137164A patent/TWI253932B/zh not_active IP Right Cessation
- 1998-06-02 TW TW091137165A patent/TW589187B/zh not_active IP Right Cessation
- 1998-06-09 GT GT199800076A patent/GT199800076A/es unknown
- 1998-06-09 PE PE1998000485A patent/PE85699A1/es not_active Application Discontinuation
- 1998-06-09 GT GT199800076AK patent/GT199800076AA/es unknown
- 1998-06-09 GT GT199800076BL patent/GT199800076BA/es unknown
- 1998-09-06 SA SA98190501A patent/SA98190501B1/ar unknown
-
1999
- 1999-09-24 IS IS5196A patent/IS5196A/is unknown
- 1999-10-08 OA OA9900225A patent/OA11166A/en unknown
- 1999-10-11 BG BG103795A patent/BG103795A/xx unknown
- 1999-10-14 NO NO994992A patent/NO994992L/no not_active Application Discontinuation
-
2000
- 2000-09-14 HK HK00105778A patent/HK1026373A1/xx not_active IP Right Cessation
-
2002
- 2002-01-10 JP JP2002003897A patent/JP2002205997A/ja active Pending
- 2002-02-13 US US10/073,357 patent/US20020168427A1/en not_active Abandoned
- 2002-06-14 US US10/170,750 patent/US20030086984A1/en not_active Abandoned
- 2002-06-25 JP JP2002184593A patent/JP2003026591A/ja active Pending
-
2004
- 2004-06-22 US US10/872,567 patent/US7166611B2/en not_active Expired - Fee Related
- 2004-06-22 US US10/872,463 patent/US20040234634A1/en not_active Abandoned
-
2006
- 2006-02-28 US US11/363,057 patent/US20060205931A1/en not_active Abandoned
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
UA72439C2 (en) | Pharmaceutical compositions containing appetite suppressant agent | |
AU780886B2 (en) | Appetite suppresant steroidal glycosides | |
CZ359999A3 (cs) | Farmaceutická kompozice snižující chuť k jídlu | |
MXPA99009443A (en) | Pharmaceutical compositions having appetite suppressant activity |