SK141899A3 - Pharmaceutical compositions having appetite suppressant activity - Google Patents

Pharmaceutical compositions having appetite suppressant activity Download PDF

Info

Publication number: SK141899A3
Authority: SK; Slovakia
Prior art keywords: compound; formula; extract; appetite; composition
Prior art date: 1997-04-15

Application number

SK1418-99A

Other languages

English (en)

Slovak (sk)

Inventor

Heerden Fanie Retief Van

Robert Vleggaar

Roelof Marthinus Horak

Robin Alec Learmonth

Vinesh Maharaj

Rory Desmond Whittal

Original Assignee

Csir Corporate Building

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-04-15

Filing date

1998-04-15

Publication date

2000-09-12

1998-04-15 Application filed by Csir Corporate Building filed Critical Csir Corporate Building

2000-09-12 Publication of SK141899A3 publication Critical patent/SK141899A3/sk

Links

230000000694 effects Effects 0.000 title claims abstract description 61
239000002830 appetite depressant Substances 0.000 title abstract description 4
239000008194 pharmaceutical composition Substances 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 143
238000000034 method Methods 0.000 claims abstract description 90
239000000284 extract Substances 0.000 claims abstract description 83
241001504226 Hoodia Species 0.000 claims abstract description 76
241000196324 Embryophyta Species 0.000 claims abstract description 45
235000017277 hoodia Nutrition 0.000 claims abstract description 40
230000008569 process Effects 0.000 claims abstract description 32
239000003814 drug Substances 0.000 claims abstract description 19
238000004519 manufacturing process Methods 0.000 claims abstract description 12
241001465754 Metazoa Species 0.000 claims description 129
239000000203 mixture Substances 0.000 claims description 101
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 92
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 87
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 78
230000036528 appetite Effects 0.000 claims description 72
235000019789 appetite Nutrition 0.000 claims description 72
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 66
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 63
125000000217 alkyl group Chemical group 0.000 claims description 51
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 42
230000001603 reducing effect Effects 0.000 claims description 42
235000011389 fruit/vegetable juice Nutrition 0.000 claims description 39
-1 Igloyl Chemical group 0.000 claims description 38
239000002904 solvent Substances 0.000 claims description 38
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 32
239000003638 chemical reducing agent Substances 0.000 claims description 31
239000000463 material Substances 0.000 claims description 31
235000013305 food Nutrition 0.000 claims description 28
150000003431 steroids Chemical class 0.000 claims description 25
150000002895 organic esters Chemical group 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 22
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 21
238000006243 chemical reaction Methods 0.000 claims description 21
230000008878 coupling Effects 0.000 claims description 21
238000010168 coupling process Methods 0.000 claims description 21
238000005859 coupling reaction Methods 0.000 claims description 21
239000008103 glucose Substances 0.000 claims description 18
229940125904 compound 1 Drugs 0.000 claims description 17
238000002360 preparation method Methods 0.000 claims description 17
125000005607 tigloyl group Chemical group 0.000 claims description 17
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 16
238000000605 extraction Methods 0.000 claims description 15
239000000843 powder Substances 0.000 claims description 15
150000001720 carbohydrates Chemical class 0.000 claims description 14
235000014633 carbohydrates Nutrition 0.000 claims description 13
208000008589 Obesity Diseases 0.000 claims description 12
235000020824 obesity Nutrition 0.000 claims description 12
150000004043 trisaccharides Chemical class 0.000 claims description 12
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 10
229940044601 receptor agonist Drugs 0.000 claims description 10
239000000018 receptor agonist Substances 0.000 claims description 10
239000007787 solid 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
GOYBREOSJSERKM-DSYKOEDSSA-N D-cymarose Chemical compound O=CC[C@H](OC)[C@H](O)[C@@H](C)O GOYBREOSJSERKM-DSYKOEDSSA-N 0.000 claims description 9
108010021436 Type 4 Melanocortin Receptor Proteins 0.000 claims description 9
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims description 9
150000002016 disaccharides Chemical class 0.000 claims description 8
239000002552 dosage form Substances 0.000 claims description 8
239000000546 pharmaceutical excipient Substances 0.000 claims description 8
FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 claims description 7
150000002772 monosaccharides Chemical class 0.000 claims description 7
VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 claims description 7
229940124531 pharmaceutical excipient Drugs 0.000 claims description 7
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 7
WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 claims description 6
241001504224 Hoodia gordonii Species 0.000 claims description 6
229940126208 compound 22 Drugs 0.000 claims description 6
239000003937 drug carrier Substances 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
GOYBREOSJSERKM-UHFFFAOYSA-N D-oleandrose Natural products O=CCC(OC)C(O)C(C)O GOYBREOSJSERKM-UHFFFAOYSA-N 0.000 claims description 5
229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
229940125758 compound 15 Drugs 0.000 claims description 5
235000011150 stannous chloride Nutrition 0.000 claims description 5
IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 4
239000000556 agonist Substances 0.000 claims description 4
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 4
235000013361 beverage Nutrition 0.000 claims description 4
238000013375 chromatographic separation Methods 0.000 claims description 4
229940125807 compound 37 Drugs 0.000 claims description 4
CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 claims description 4
YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 claims description 3
KAFZOLYKKCWUBI-HPMAGDRPSA-N (2s)-2-[[(2s)-2-[[(2s)-1-[(2s)-3-amino-2-[[(2s)-2-[[(2s)-2-(3-cyclohexylpropanoylamino)-4-methylpentanoyl]amino]-5-methylhexanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]butanediamide Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CCC(C)C)C(=O)N[C@@H](CN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CC(N)=O)C(N)=O)C(=O)CCC1CCCCC1 KAFZOLYKKCWUBI-HPMAGDRPSA-N 0.000 claims description 3
ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 claims description 3
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims description 3
UIERETOOQGIECD-ARJAWSKDSA-M 2-Methyl-2-butenoic acid Natural products C\C=C(\C)C([O-])=O UIERETOOQGIECD-ARJAWSKDSA-M 0.000 claims description 3
FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 claims description 3
UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 claims description 3
PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 claims description 3
239000013543 active substance Substances 0.000 claims description 3
229940127113 compound 57 Drugs 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
238000011156 evaluation Methods 0.000 claims description 3
238000000638 solvent extraction Methods 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
UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 claims description 3
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 3
VJMQFIRIMMSSRW-UHFFFAOYSA-N trimethyl(phenylsulfanyl)silane Chemical compound C[Si](C)(C)SC1=CC=CC=C1 VJMQFIRIMMSSRW-UHFFFAOYSA-N 0.000 claims 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 claims description 3
ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 claims description 2
UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 claims description 2
VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 claims description 2
WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 claims description 2
TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 claims description 2
QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 claims description 2
WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 claims description 2
229940127007 Compound 39 Drugs 0.000 claims description 2
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
LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 claims description 2
SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 claims description 2
XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 claims description 2
KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 claims description 2
229940125833 compound 23 Drugs 0.000 claims description 2
229940125961 compound 24 Drugs 0.000 claims description 2
229940125846 compound 25 Drugs 0.000 claims description 2
229940125851 compound 27 Drugs 0.000 claims description 2
229940127204 compound 29 Drugs 0.000 claims description 2
229940127271 compound 49 Drugs 0.000 claims description 2
229940126545 compound 53 Drugs 0.000 claims description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
FDBYIYFVSAHJLY-UHFFFAOYSA-N resmetirom Chemical compound N1C(=O)C(C(C)C)=CC(OC=2C(=CC(=CC=2Cl)N2C(NC(=O)C(C#N)=N2)=O)Cl)=N1 FDBYIYFVSAHJLY-UHFFFAOYSA-N 0.000 claims description 2
230000003637 steroidlike Effects 0.000 claims description 2
102000001796 Melanocortin 4 receptors Human genes 0.000 claims 5
GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims 3
241000446799 Curroria Species 0.000 claims 2
LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 claims 1
229910007926 ZrCl Inorganic materials 0.000 claims 1
GHPDOFCEIGAURF-UHFFFAOYSA-J [Ag](Cl)(Cl)(Cl)Cl Chemical compound [Ag](Cl)(Cl)(Cl)Cl GHPDOFCEIGAURF-UHFFFAOYSA-J 0.000 claims 1
239000003153 chemical reaction reagent Substances 0.000 claims 1
229940079593 drug Drugs 0.000 claims 1
239000012535 impurity Substances 0.000 claims 1
KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 claims 1
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
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- 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
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- C07J15/00—Stereochemically pure steroids containing carbon, hydrogen, halogen or oxygen having a partially or totally inverted skeleton, e.g. retrosteroids, L-isomers
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- 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
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- 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
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- 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
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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)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Natural Medicines & Medicinal Plants (AREA)
Biotechnology (AREA)
Epidemiology (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Genetics & Genomics (AREA)
Mycology (AREA)
Botany (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Microbiology (AREA)
Medical Informatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Alternative & Traditional Medicine (AREA)
Polymers & Plastics (AREA)
Hematology (AREA)
Obesity (AREA)
Food Science & Technology (AREA)
Nutrition Science (AREA)
Diabetes (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)
Saccharide Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Coloring Foods And Improving Nutritive Qualities (AREA)

SK1418-99A 1997-04-15 1998-04-15 Pharmaceutical compositions having appetite suppressant activity SK141899A3 (en)

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
SK141899A3 true SK141899A3 (en)	2000-09-12

Family

ID=25586362

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1418-99A SK141899A3 (en)	1997-04-15	1998-04-15	Pharmaceutical compositions having appetite suppressant activity

Country Status (39)

Country	Link
US (6)	US6376657B1 (de)
EP (5)	EP0973534B1 (de)
JP (3)	JP3553086B2 (de)
KR (2)	KR100891756B1 (de)
CN (3)	CN101239090A (de)
AP (3)	AP1291A (de)
AT (3)	ATE502041T1 (de)
AU (1)	AU746414B2 (de)
BG (1)	BG103795A (de)
BR (1)	BR9808593A (de)
CA (2)	CA2283564C (de)
DE (3)	DE69840552D1 (de)
DK (1)	DK0973534T3 (de)
EA (2)	EA200200392A1 (de)
EE (1)	EE9900497A (de)
ES (3)	ES2321162T3 (de)
GB (3)	GB2338235B (de)
GE (2)	GEP20022709B (de)
GT (3)	GT199800076AA (de)
HU (1)	HUP0000838A3 (de)
ID (1)	ID22888A (de)
IL (3)	IL158465A0 (de)
IS (1)	IS5196A (de)
MY (1)	MY141674A (de)
NO (1)	NO994992L (de)
NZ (5)	NZ525022A (de)
OA (1)	OA11166A (de)
PE (1)	PE85699A1 (de)
PL (3)	PL197783B1 (de)
PT (2)	PT973534E (de)
SA (1)	SA98190501B1 (de)
SG (1)	SG120054A1 (de)
SK (1)	SK141899A3 (de)
TR (2)	TR199902540T2 (de)
TW (3)	TW539551B (de)
UA (1)	UA72439C2 (de)
WO (1)	WO1998046243A2 (de)
YU (1)	YU52199A (de)
ZA (1)	ZA983170B (de)

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- 1998-04-15 YU YU52199A patent/YU52199A/sh unknown
- 1998-04-15 PT PT98917372T patent/PT973534E/pt unknown
- 1998-04-15 GE GEAP19985030A patent/GEP20022709B/en unknown
- 1998-04-15 DK DK98917372T patent/DK0973534T3/da active
- 1998-04-15 EP EP02004100.0A patent/EP1222927B1/de not_active Expired - Lifetime
- 1998-04-15 EP EP05017768A patent/EP1598054B1/de not_active Expired - Lifetime
- 1998-04-15 ZA ZA9803170A patent/ZA983170B/xx unknown
- 1998-04-15 PL PL374521A patent/PL197783B1/pl not_active IP Right Cessation
- 1998-04-15 AT AT05017768T patent/ATE502041T1/de not_active IP Right Cessation
- 1998-04-15 NZ NZ516695A patent/NZ516695A/en unknown
- 1998-04-15 PL PL380957A patent/PL201487B1/pl not_active IP Right Cessation
- 1998-04-15 CN CNB988041650A patent/CN100378118C/zh not_active Expired - Fee Related
- 1998-04-15 HU HU0000838A patent/HUP0000838A3/hu unknown
- 1998-04-15 CA CA002283564A patent/CA2283564C/en not_active Expired - Fee Related
- 1998-04-15 SK SK1418-99A patent/SK141899A3/sk unknown
- 1998-04-15 NZ NZ525021A patent/NZ525021A/en unknown
- 1998-04-15 US US09/402,962 patent/US6376657B1/en not_active Expired - Lifetime
- 1998-04-15 CA CA002584411A patent/CA2584411A1/en not_active Abandoned
- 1998-04-15 EP EP02004101A patent/EP1213020B1/de not_active Expired - Lifetime
- 1998-04-15 TR TR1999/02540T patent/TR199902540T2/xx unknown
- 1998-04-15 AT AT98917372T patent/ATE344046T1/de active
- 1998-04-15 ID IDW991200A patent/ID22888A/id unknown
- 1998-04-15 GB GB0117039A patent/GB2360519B/en not_active Expired - Fee Related
- 1998-04-15 AP APAP/P/2003/002729A patent/AP2003002729A0/en unknown
- 1998-04-15 IL IL15846698A patent/IL158466A0/xx unknown
- 1998-04-15 NZ NZ337422A patent/NZ337422A/en unknown
- 1998-04-15 EE EEP199900497A patent/EE9900497A/xx unknown
- 1998-04-15 ES ES98917372T patent/ES2276460T3/es not_active Expired - Lifetime
- 1998-04-15 ES ES05017768T patent/ES2363230T3/es not_active Expired - Lifetime
- 1998-04-15 AT AT02004101T patent/ATE422359T1/de active
- 1998-04-15 GE GEAP19985544A patent/GEP20022788B/en unknown
- 1998-04-15 EA EA199900932A patent/EA002885B1/ru not_active IP Right Cessation
- 1998-04-15 DE DE69836321T patent/DE69836321T2/de not_active Expired - Lifetime
- 1998-04-15 EP EP04002070A patent/EP1438965A1/de not_active Withdrawn
- 1998-04-15 TR TR2000/01846T patent/TR200001846T2/xx unknown
- 1998-04-15 PT PT02004101T patent/PT1213020E/pt unknown
- 1998-04-15 PL PL98336498A patent/PL196015B1/pl not_active IP Right Cessation
- 1998-04-15 CN CNA2008100057254A patent/CN101239089A/zh active Pending
- 1998-06-02 TW TW087108667A patent/TW539551B/zh active
- 1998-06-02 TW TW091137165A patent/TW589187B/zh not_active IP Right Cessation
- 1998-06-02 TW TW091137164A patent/TWI253932B/zh not_active IP Right Cessation
- 1998-06-09 GT GT199800076AK patent/GT199800076AA/es unknown
- 1998-06-09 PE PE1998000485A patent/PE85699A1/es not_active Application Discontinuation
- 1998-06-09 GT GT199800076A patent/GT199800076A/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
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

Publication number	Publication date
ES2321162T3 (es)	2009-06-03
US20040228935A1 (en)	2004-11-18
GB2338235A (en)	1999-12-15
GT199800076A (es)	1999-12-01
GT199800076AA (es)	1999-12-01
JP2003026591A (ja)	2003-01-29
DE69836321D1 (de)	2006-12-14
AP9901673A0 (en)	1999-12-31
GEP20022788B (en)	2002-09-25
EP1222927A3 (de)	2002-10-30
IL131659A (en)	2005-07-25
PL201487B1 (pl)	2009-04-30
US20030086984A1 (en)	2003-05-08
EP1222927B1 (de)	2013-11-20
HUP0000838A3 (en)	2001-04-28
CN1252000A (zh)	2000-05-03
EA200200392A1 (ru)	2002-08-29
GEP20022709B (en)	2002-06-25
TW200300093A (en)	2003-05-16
SA98190501B1 (ar)	2006-07-30
TW200300094A (en)	2003-05-16
PT1213020E (pt)	2009-04-24
EA199900932A1 (ru)	2000-04-24
NZ516695A (en)	2003-08-29
AU746414B2 (en)	2002-05-02
ES2276460T3 (es)	2007-06-16
NO994992L (no)	1999-12-14
DK0973534T3 (da)	2007-03-12
EP1598054A3 (de)	2009-06-10
AU7061398A (en)	1998-11-11
EP0973534A1 (de)	2000-01-26
KR20040004407A (ko)	2004-01-13
HUP0000838A2 (hu)	2000-10-28
NZ337422A (en)	2002-05-31
US7166611B2 (en)	2007-01-23
EP1213020B1 (de)	2009-02-11
JP2002205997A (ja)	2002-07-23
OA11166A (en)	2003-04-28
PL196015B1 (pl)	2007-11-30
CN101239090A (zh)	2008-08-13
TR200001846T2 (tr)	2000-11-21
KR20010006424A (ko)	2001-01-26
WO1998046243A2 (en)	1998-10-22
TWI253932B (en)	2006-05-01
AP2003002729A0 (en)	2003-06-30
NZ525021A (en)	2004-05-28
AP1291A (en)	2004-08-02
AP2003002730A0 (en)	2003-06-30
BG103795A (en)	2000-05-31
PL336498A1 (en)	2000-07-03
DE69836321T2 (de)	2007-06-28
GB2360519A (en)	2001-09-26
GB2360520A (en)	2001-09-26
NO994992D0 (no)	1999-10-14
GB9919797D0 (en)	1999-10-27
EP1213020A3 (de)	2005-03-09
PE85699A1 (es)	1999-09-15
EA002885B1 (ru)	2002-10-31
ATE344046T1 (de)	2006-11-15
EE9900497A (et)	2000-06-15
CN100378118C (zh)	2008-04-02
DE69842189D1 (de)	2011-04-28
IS5196A (is)	1999-09-24
EP1222927A2 (de)	2002-07-17
US20040234634A1 (en)	2004-11-25
SG120054A1 (en)	2006-03-28
EP1213020A8 (de)	2003-12-17
ATE422359T1 (de)	2009-02-15
EP1438965A1 (de)	2004-07-21
GB2360519B (en)	2001-11-28
GB0117039D0 (en)	2001-09-05
US6376657B1 (en)	2002-04-23
CN101239089A (zh)	2008-08-13
GB2360520B (en)	2001-11-07
CA2283564A1 (en)	1998-10-22
GT199800076BA (es)	1999-12-01
IL158466A0 (en)	2004-05-12
JP3553086B2 (ja)	2004-08-11
EP1598054A2 (de)	2005-11-23
GB0117041D0 (en)	2001-09-05
KR100891756B1 (ko)	2009-04-07
TW589187B (en)	2004-06-01
WO1998046243A3 (en)	1999-02-25
CA2584411A1 (en)	1998-10-22
NZ516696A (en)	2003-08-29
GB2338235B (en)	2001-11-14
UA72439C2 (en)	2005-03-15
TW539551B (en)	2003-07-01
BR9808593A (pt)	2000-05-23
PT973534E (pt)	2007-02-28
EP1598054B1 (de)	2011-03-16
US20020168427A1 (en)	2002-11-14
ES2363230T3 (es)	2011-07-27
YU52199A (sh)	2003-02-28
ATE502041T1 (de)	2011-04-15
PL197783B1 (pl)	2008-04-30
CA2283564C (en)	2007-07-10
US20060205931A1 (en)	2006-09-14
IL131659A0 (en)	2001-01-28
MY141674A (en)	2010-05-31
IL158465A0 (en)	2004-05-12
NZ525022A (en)	2004-05-28
DE69840552D1 (de)	2009-03-26
ID22888A (id)	1999-12-16
JP2000510482A (ja)	2000-08-15
KR100510614B1 (ko)	2005-08-30
HK1026373A1 (zh)	2000-12-15
EP1213020A2 (de)	2002-06-12
TR199902540T2 (xx)	2000-01-21
EP0973534B1 (de)	2006-11-02
ZA983170B (en)	1999-10-15

Publication	Publication Date	Title
SK141899A3 (en)	2000-09-12	Pharmaceutical compositions having appetite suppressant activity
AU780886B2 (en)	2005-04-21	Appetite suppresant steroidal glycosides
CZ359999A3 (cs)	2000-05-17	Farmaceutická kompozice snižující chuť k jídlu
MXPA99009443A (en)	2001-12-04	Pharmaceutical compositions having appetite suppressant activity
HK1124243A (en)	2009-07-10	Pharmaceutical compositions having appetite suppressant activity
HRP980456A2 (en)	2000-04-30	Pharmaceutical compositions having appetite suppressant activity
HK1026373B (en)	2009-01-30	Pharmaceutical compositions having appaetite suppressant activity
HK1124242A (en)	2009-07-10	Pharmaceutical compositions having appetite suppressant activity