HRP20020796A2 - Percyquinnin, a process for its production and its use as a pharmaceutical - Google Patents

Percyquinnin, a process for its production and its use as a pharmaceutical Download PDF

Info

Publication number: HRP20020796A2
Authority: HR; Croatia
Prior art keywords: pharmaceutically acceptable; persiquinine; persiquinin; compound; salts
Prior art date: 2000-04-07

Application number

Other languages

English (en)

Croatian (hr)

Inventor

Cordula Hopmann

Michael Kurz

Guenter Mueller

Luigi Toti

Original Assignee

Aventis Pharma Gmbh

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.)

2000-04-07

Filing date

2002-10-04

Publication date

2004-12-31

2002-10-04 Application filed by Aventis Pharma Gmbh filed Critical Aventis Pharma Gmbh

2004-12-31 Publication of HRP20020796A2 publication Critical patent/HRP20020796A2/hr

Links

238000000034 method Methods 0.000 title claims abstract description 19
238000004519 manufacturing process Methods 0.000 title claims abstract description 8
150000003839 salts Chemical class 0.000 claims abstract description 29
150000001875 compounds Chemical class 0.000 claims abstract description 27
241000233866 Fungi Species 0.000 claims abstract description 5
239000003814 drug Substances 0.000 claims abstract description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
239000000825 pharmaceutical preparation Substances 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
235000015097 nutrients Nutrition 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 5
238000000746 purification Methods 0.000 claims description 5
CHSAZBMOBSHGFV-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)phenyl]-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)C1=CC=C(CCO)C=C1 CHSAZBMOBSHGFV-UHFFFAOYSA-N 0.000 claims description 4
238000002955 isolation Methods 0.000 claims description 4
241000221198 Basidiomycota Species 0.000 claims description 3
229940086609 Lipase inhibitor Drugs 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims 1
241000894007 species Species 0.000 claims 1
239000003112 inhibitor Substances 0.000 abstract description 3
244000005700 microbiome Species 0.000 abstract description 3
239000008194 pharmaceutical composition Substances 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
235000002639 sodium chloride Nutrition 0.000 description 26
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 21
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
238000002360 preparation method Methods 0.000 description 11
239000000243 solution Substances 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 10
239000004480 active ingredient Substances 0.000 description 9
-1 dimethyloctylsilyl silica gel Chemical compound 0.000 description 9
239000007788 liquid Substances 0.000 description 9
239000004367 Lipase Substances 0.000 description 8
102000004882 Lipase Human genes 0.000 description 8
108090001060 Lipase Proteins 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
235000019421 lipase Nutrition 0.000 description 8
229920001817 Agar Polymers 0.000 description 7
230000005764 inhibitory process Effects 0.000 description 7
229940040461 lipase Drugs 0.000 description 7
239000000126 substance Substances 0.000 description 7
239000008272 agar Substances 0.000 description 6
239000003480 eluent Substances 0.000 description 6
239000002609 medium Substances 0.000 description 6
238000002156 mixing Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
239000003826 tablet Substances 0.000 description 6
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
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 5
229930006000 Sucrose Natural products 0.000 description 5
239000007983 Tris buffer Substances 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
238000000855 fermentation Methods 0.000 description 5
230000004151 fermentation Effects 0.000 description 5
239000008103 glucose Substances 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
238000011534 incubation Methods 0.000 description 5
239000004615 ingredient Substances 0.000 description 5
238000012423 maintenance Methods 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
239000005720 sucrose Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
235000010419 agar Nutrition 0.000 description 4
230000004071 biological effect Effects 0.000 description 4
239000008280 blood Substances 0.000 description 4
210000004369 blood Anatomy 0.000 description 4
229940041514 candida albicans extract Drugs 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
238000001514 detection method Methods 0.000 description 4
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000009472 formulation Methods 0.000 description 4
239000000499 gel Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000013587 production medium Substances 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000012138 yeast extract Substances 0.000 description 4
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 3
108010087765 Antipain Proteins 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
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 3
GDBQQVLCIARPGH-UHFFFAOYSA-N Leupeptin Natural products CC(C)CC(NC(C)=O)C(=O)NC(CC(C)C)C(=O)NC(C=O)CCCN=C(N)N GDBQQVLCIARPGH-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000002835 absorbance Methods 0.000 description 3
239000002253 acid Substances 0.000 description 3
210000001789 adipocyte Anatomy 0.000 description 3
SDNYTAYICBFYFH-TUFLPTIASA-N antipain Chemical compound NC(N)=NCCC[C@@H](C=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 SDNYTAYICBFYFH-TUFLPTIASA-N 0.000 description 3
238000003556 assay Methods 0.000 description 3
239000002585 base Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000000872 buffer Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000000969 carrier Substances 0.000 description 3
229940088598 enzyme Drugs 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
239000000284 extract Substances 0.000 description 3
235000019197 fats Nutrition 0.000 description 3
235000013312 flour Nutrition 0.000 description 3
239000008187 granular material Substances 0.000 description 3
GDBQQVLCIARPGH-ULQDDVLXSA-N leupeptin Chemical compound CC(C)C[C@H](NC(C)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C=O)CCCN=C(N)N GDBQQVLCIARPGH-ULQDDVLXSA-N 0.000 description 3
108010052968 leupeptin Proteins 0.000 description 3
229950000964 pepstatin Drugs 0.000 description 3
108010091212 pepstatin Proteins 0.000 description 3
FAXGPCHRFPCXOO-LXTPJMTPSA-N pepstatin A Chemical compound OC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)CC(C)C FAXGPCHRFPCXOO-LXTPJMTPSA-N 0.000 description 3
239000000651 prodrug Substances 0.000 description 3
229940002612 prodrug Drugs 0.000 description 3
239000000047 product Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000004611 spectroscopical analysis Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
235000013619 trace mineral Nutrition 0.000 description 3
239000011573 trace mineral Substances 0.000 description 3
244000215068 Acacia senegal Species 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
230000005526 G1 to G0 transition Effects 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
229920000084 Gum arabic Polymers 0.000 description 2
229940127470 Lipase Inhibitors Drugs 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
102000019280 Pancreatic lipases Human genes 0.000 description 2
108050006759 Pancreatic lipases Proteins 0.000 description 2
241000700159 Rattus Species 0.000 description 2
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
238000007239 Wittig reaction Methods 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
239000000205 acacia gum Substances 0.000 description 2
235000010489 acacia gum Nutrition 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
235000001014 amino acid Nutrition 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
235000011148 calcium chloride Nutrition 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
239000002775 capsule Substances 0.000 description 2
238000004140 cleaning Methods 0.000 description 2
235000005822 corn Nutrition 0.000 description 2
229910000388 diammonium phosphate Inorganic materials 0.000 description 2
235000019838 diammonium phosphate Nutrition 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
239000012530 fluid Substances 0.000 description 2
238000007710 freezing Methods 0.000 description 2
230000008014 freezing Effects 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
239000011539 homogenization buffer Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
201000001421 hyperglycemia Diseases 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
238000007918 intramuscular administration Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
230000037356 lipid metabolism Effects 0.000 description 2
230000004130 lipolysis Effects 0.000 description 2
239000007937 lozenge Substances 0.000 description 2
238000000465 moulding Methods 0.000 description 2
239000003921 oil Substances 0.000 description 2
229940116369 pancreatic lipase Drugs 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
159000000001 potassium salts Chemical class 0.000 description 2
238000002953 preparative HPLC Methods 0.000 description 2
238000004321 preservation Methods 0.000 description 2
239000002994 raw material Substances 0.000 description 2
238000004366 reverse phase liquid chromatography Methods 0.000 description 2
230000002441 reversible effect Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
230000003595 spectral effect Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000007920 subcutaneous administration Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
229910003208 (NH4)6Mo7O24·4H2O Inorganic materials 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
235000017060 Arachis glabrata Nutrition 0.000 description 1
244000105624 Arachis hypogaea Species 0.000 description 1
235000010777 Arachis hypogaea Nutrition 0.000 description 1
235000018262 Arachis monticola Nutrition 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
238000009631 Broth culture Methods 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
102000029816 Collagenase Human genes 0.000 description 1
108060005980 Collagenase Proteins 0.000 description 1
229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
229930091371 Fructose Natural products 0.000 description 1
239000005715 Fructose Substances 0.000 description 1
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
241000206672 Gelidium Species 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
229910004373 HOAc Inorganic materials 0.000 description 1
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
208000035150 Hypercholesterolemia Diseases 0.000 description 1
208000031226 Hyperlipidaemia Diseases 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
239000004166 Lanolin Substances 0.000 description 1
ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
229910010084 LiAlH4 Inorganic materials 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
102000005398 Monoacylglycerol Lipase Human genes 0.000 description 1
108020002334 Monoacylglycerol lipase Proteins 0.000 description 1
MSPCIZMDDUQPGJ-UHFFFAOYSA-N N-methyl-N-(trimethylsilyl)trifluoroacetamide Chemical compound C[Si](C)(C)N(C)C(=O)C(F)(F)F MSPCIZMDDUQPGJ-UHFFFAOYSA-N 0.000 description 1
208000008589 Obesity Diseases 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000001888 Peptone Substances 0.000 description 1
108010080698 Peptones Proteins 0.000 description 1
239000004264 Petrolatum Substances 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
101100421709 Schistosoma mansoni SM21.7 gene Proteins 0.000 description 1
229920002684 Sepharose Polymers 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
241000222646 Stereum Species 0.000 description 1
241000222647 Stereum complicatum Species 0.000 description 1
102000000019 Sterol Esterase Human genes 0.000 description 1
108010055297 Sterol Esterase Proteins 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
239000011149 active material Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
235000004279 alanine Nutrition 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229950003476 aminothiazole Drugs 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
229920006318 anionic polymer Polymers 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000012131 assay buffer Substances 0.000 description 1
235000015278 beef Nutrition 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
125000003180 beta-lactone group Chemical group 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000002051 biphasic effect Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
238000009924 canning Methods 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
238000004113 cell culture Methods 0.000 description 1
229940081734 cellulose acetate phthalate Drugs 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
229960002424 collagenase Drugs 0.000 description 1
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000013058 crude material Substances 0.000 description 1
238000007405 data analysis Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000000378 dietary effect Effects 0.000 description 1
235000013367 dietary fats Nutrition 0.000 description 1
239000003085 diluting agent Substances 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
235000019797 dipotassium phosphate Nutrition 0.000 description 1
229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
235000019800 disodium phosphate Nutrition 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000002451 electron ionisation mass spectrometry Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
210000002615 epidermis Anatomy 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
239000006167 equilibration buffer Substances 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000005188 flotation Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
229930182830 galactose Natural products 0.000 description 1
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000003292 glue Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229960002897 heparin Drugs 0.000 description 1
229920000669 heparin Polymers 0.000 description 1
238000004191 hydrophobic interaction chromatography Methods 0.000 description 1
229910052588 hydroxylapatite Inorganic materials 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000003978 infusion fluid Substances 0.000 description 1
230000010354 integration Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000004255 ion exchange chromatography Methods 0.000 description 1
125000000686 lactone group Chemical group 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019388 lanolin Nutrition 0.000 description 1
229940039717 lanolin Drugs 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
238000013332 literature search Methods 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
230000007774 longterm Effects 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
235000001055 magnesium Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
229910000357 manganese(II) sulfate Inorganic materials 0.000 description 1
229910052603 melanterite Inorganic materials 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
238000003808 methanol extraction Methods 0.000 description 1
XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
235000013379 molasses Nutrition 0.000 description 1
239000007932 molded tablet Substances 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
239000007764 o/w emulsion Substances 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
239000002674 ointment Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
238000006385 ozonation reaction Methods 0.000 description 1
238000005949 ozonolysis reaction Methods 0.000 description 1
239000005022 packaging material Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000006072 paste Substances 0.000 description 1
235000020232 peanut Nutrition 0.000 description 1
XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 1
235000019319 peptone Nutrition 0.000 description 1
230000035699 permeability Effects 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
150000003905 phosphatidylinositols Chemical class 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940068917 polyethylene glycols Drugs 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000002952 polymeric resin Substances 0.000 description 1
229940100467 polyvinyl acetate phthalate Drugs 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000004323 potassium nitrate Substances 0.000 description 1
235000010333 potassium nitrate Nutrition 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
239000008057 potassium phosphate buffer Substances 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000003825 pressing Methods 0.000 description 1
238000012545 processing Methods 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000011160 research Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
239000013049 sediment Substances 0.000 description 1
238000011218 seed culture Methods 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
238000002791 soaking Methods 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
239000012453 solvate Substances 0.000 description 1
235000013599 spices Nutrition 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
235000015113 tomato pastes and purées Nutrition 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
238000011282 treatment Methods 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
238000000108 ultra-filtration Methods 0.000 description 1
239000007762 w/o emulsion Substances 0.000 description 1
NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
229910000368 zinc sulfate Inorganic materials 0.000 description 1
239000011686 zinc sulphate Substances 0.000 description 1
235000009529 zinc sulphate Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/14—Fungi; Culture media therefor
- C12N1/145—Fungal isolates
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
- 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
- A61P3/06—Antihyperlipidemics
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/645—Fungi ; Processes using fungi

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Zoology (AREA)
Wood Science & Technology (AREA)
General Health & Medical Sciences (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Microbiology (AREA)
Biochemistry (AREA)
General Engineering & Computer Science (AREA)
Public Health (AREA)
Diabetes (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Botany (AREA)
Tropical Medicine & Parasitology (AREA)
Biomedical Technology (AREA)
Hematology (AREA)
Virology (AREA)
Obesity (AREA)
Mycology (AREA)
Epidemiology (AREA)
Endocrinology (AREA)
Emergency Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Micro-Organisms Or Cultivation Processes Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Epoxy Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

HRP20020796 2000-04-07 2002-10-04 Percyquinnin, a process for its production and its use as a pharmaceutical HRP20020796A2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP00107536A EP1142886A1 (en)	2000-04-07	2000-04-07	Percyquinnin, a process for its production and its use as a pharmaceutical
PCT/EP2001/003392 WO2001077094A1 (en)	2000-04-07	2001-03-24	Percyquinnin, a process for its production and its use as a pharmaceutical

Publications (1)

Publication Number	Publication Date
HRP20020796A2 true HRP20020796A2 (en)	2004-12-31

Family

ID=8168397

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HRP20020796 HRP20020796A2 (en)	2000-04-07	2002-10-04	Percyquinnin, a process for its production and its use as a pharmaceutical

Country Status (30)

Country	Link
US (1)	US6596518B2 (pt)
EP (2)	EP1142886A1 (pt)
JP (1)	JP2003530391A (pt)
KR (1)	KR100791798B1 (pt)
CN (1)	CN1199959C (pt)
AT (1)	ATE269855T1 (pt)
AU (2)	AU784902B2 (pt)
BR (1)	BR0109854A (pt)
CA (1)	CA2405066A1 (pt)
CZ (1)	CZ20023310A3 (pt)
DE (1)	DE60103995T2 (pt)
DK (1)	DK1274698T3 (pt)
EE (1)	EE200200572A (pt)
ES (1)	ES2222992T3 (pt)
HK (1)	HK1052005A1 (pt)
HR (1)	HRP20020796A2 (pt)
HU (1)	HUP0300327A3 (pt)
IL (2)	IL152073A0 (pt)
MX (1)	MXPA02007895A (pt)
NO (1)	NO20024772L (pt)
NZ (1)	NZ521782A (pt)
PL (1)	PL357909A1 (pt)
PT (1)	PT1274698E (pt)
RS (1)	RS50140B (pt)
RU (1)	RU2266290C2 (pt)
SI (1)	SI1274698T1 (pt)
SK (1)	SK14322002A3 (pt)
TR (1)	TR200401739T4 (pt)
WO (1)	WO2001077094A1 (pt)
ZA (1)	ZA200207910B (pt)

Families Citing this family (49)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1142886A1 (en) *	2000-04-07	2001-10-10	Aventis Pharma Deutschland GmbH	Percyquinnin, a process for its production and its use as a pharmaceutical
US7105526B2 (en)	2002-06-28	2006-09-12	Banyu Pharmaceuticals Co., Ltd.	Benzimidazole derivatives
US7772188B2 (en)	2003-01-28	2010-08-10	Ironwood Pharmaceuticals, Inc.	Methods and compositions for the treatment of gastrointestinal disorders
CN1902177A (zh)	2003-09-22	2007-01-24	万有制药株式会社	新哌啶衍生物
WO2005097127A2 (en)	2004-04-02	2005-10-20	Merck & Co., Inc.	Method of treating men with metabolic and anthropometric disorders
AU2005272627A1 (en)	2004-08-13	2006-02-23	Amgen Inc.	Substituted benzofused heterocycles
CA2618112A1 (en)	2005-08-10	2007-02-15	Banyu Pharmaceutical Co., Ltd.	Pyridone compound
WO2007024004A1 (ja)	2005-08-24	2007-03-01	Banyu Pharmaceutical Co., Ltd.	フェニルピリドン誘導体
US20090264426A1 (en)	2005-09-07	2009-10-22	Shunji Sakuraba	Bicyclic aromatic substituted pyridone derivative
CA2624030A1 (en)	2005-09-29	2007-04-12	Tianying Jian	Acylated spiropiperidine derivatives as melanocortin-4 receptor modulators
AU2006304836A1 (en)	2005-10-21	2007-04-26	Novartis Ag	Combination of a renin-inhibitor and an anti-dyslipidemic agent and/or an antiobesity agent
AU2006307046A1 (en)	2005-10-27	2007-05-03	Msd K.K.	Novel benzoxathiin derivative
ES2381205T3 (es)	2005-11-10	2012-05-24	Msd K.K.	Derivado espiro aza-sustituido
CN100417650C (zh) *	2006-08-17	2008-09-10	中国科学院昆明植物研究所	韧革菌素及其制备方法和在药物上的应用
EP2698157B1 (en)	2006-09-22	2015-05-20	Merck Sharp & Dohme Corp.	Method of treatment using fatty acid synthesis inhibitors
EP2072519A4 (en)	2006-09-28	2009-10-21	Banyu Pharma Co Ltd	DIARYLKETIMINDERIVAT
JP5319518B2 (ja)	2007-04-02	2013-10-16	Ｍｓｄ株式会社	インドールジオン誘導体
US20100120694A1 (en)	2008-06-04	2010-05-13	Synergy Pharmaceuticals, Inc.	Agonists of Guanylate Cyclase Useful for the Treatment of Gastrointestinal Disorders, Inflammation, Cancer and Other Disorders
EP2527360B1 (en)	2007-06-04	2015-10-28	Synergy Pharmaceuticals Inc.	Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders
US8969514B2 (en)	2007-06-04	2015-03-03	Synergy Pharmaceuticals, Inc.	Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases
AU2009220605A1 (en)	2008-03-06	2009-09-11	Msd K.K.	Alkylaminopyridine derivative
JPWO2009119726A1 (ja)	2008-03-28	2011-07-28	Ｍｓｄ株式会社	メラニン凝集ホルモン受容体拮抗作用を有するジアリールメチルアミド誘導体
AU2009261248A1 (en)	2008-06-19	2009-12-23	Banyu Pharmaceutical Co., Ltd.	Spirodiamine-diarylketoxime derivative
ES2624828T3 (es)	2008-07-16	2017-07-17	Synergy Pharmaceuticals Inc.	Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros
WO2010013595A1 (ja)	2008-07-30	2010-02-04	萬有製薬株式会社	５員－５員又は５員－６員縮環シクロアルキルアミン誘導体
AU2009307884B2 (en)	2008-10-22	2014-07-31	Merck Sharp & Dohme Corp.	Novel cyclic benzimidazole derivatives useful anti-diabetic agents
WO2010051236A1 (en)	2008-10-30	2010-05-06	Merck Sharp & Dohme Corp.	Isonicotinamide orexin receptor antagonists
CN102271509A (zh)	2008-10-31	2011-12-07	默沙东公司	用于抗糖尿病药的新型环苯并咪唑衍生物
WO2011106273A1 (en)	2010-02-25	2011-09-01	Merck Sharp & Dohme Corp.	Novel cyclic benzimidazole derivatives useful anti-diabetic agents
US9616097B2 (en)	2010-09-15	2017-04-11	Synergy Pharmaceuticals, Inc.	Formulations of guanylate cyclase C agonists and methods of use
BR112013021236B1 (pt)	2011-02-25	2021-05-25	Merck Sharp & Dohme Corp	composto derivado de benzimidazol, e, composição
AR088352A1 (es)	2011-10-19	2014-05-28	Merck Sharp & Dohme	Antagonistas del receptor de 2-piridiloxi-4-nitrilo orexina
WO2014022528A1 (en)	2012-08-02	2014-02-06	Merck Sharp & Dohme Corp.	Antidiabetic tricyclic compounds
AU2014219020A1 (en)	2013-02-22	2015-07-23	Merck Sharp & Dohme Corp.	Antidiabetic bicyclic compounds
US9650375B2 (en)	2013-03-14	2017-05-16	Merck Sharp & Dohme Corp.	Indole derivatives useful as anti-diabetic agents
WO2014151200A2 (en)	2013-03-15	2014-09-25	Synergy Pharmaceuticals Inc.	Compositions useful for the treatment of gastrointestinal disorders
WO2014151206A1 (en)	2013-03-15	2014-09-25	Synergy Pharmaceuticals Inc.	Agonists of guanylate cyclase and their uses
US10011637B2 (en)	2013-06-05	2018-07-03	Synergy Pharmaceuticals, Inc.	Ultra-pure agonists of guanylate cyclase C, method of making and using same
WO2015051496A1 (en)	2013-10-08	2015-04-16	Merck Sharp & Dohme Corp.	Antidiabetic tricyclic compounds
AU2015308350B2 (en)	2014-08-29	2020-03-05	Tes Pharma S.R.L.	Inhibitors of alpha-amino-beta-carboxymuconic acid semialdehyde decarboxylase
CN105906500B (zh) *	2016-04-22	2018-06-26	中国科学院昆明植物研究所	具有脂肪酶抑制作用的绵马次酸类化合物及其应用
CN109952292A (zh)	2016-10-14	2019-06-28	Tes制药有限责任公司	α-氨基-β-羧基己二烯二酸半醛去羧酶的抑制剂
US11072602B2 (en)	2016-12-06	2021-07-27	Merck Sharp & Dohme Corp.	Antidiabetic heterocyclic compounds
WO2018118670A1 (en)	2016-12-20	2018-06-28	Merck Sharp & Dohme Corp.	Antidiabetic spirochroman compounds
CN109055231B (zh) *	2018-07-26	2021-04-27	云南大学	一种真菌发酵液及其应用
AR117122A1 (es)	2018-11-20	2021-07-14	Tes Pharma S R L	INHIBIDORES DE LA ÁCIDO a-AMINO-b-CARBOXIMUCÓNICO SEMIALDEHÍDO DESCARBOXILASA
WO2020167706A1 (en)	2019-02-13	2020-08-20	Merck Sharp & Dohme Corp.	5-alkyl pyrrolidine orexin receptor agonists
WO2021026047A1 (en)	2019-08-08	2021-02-11	Merck Sharp & Dohme Corp.	Heteroaryl pyrrolidine and piperidine orexin receptor agonists
CN116249697A (zh)	2020-08-18	2023-06-09	默沙东有限责任公司	二环庚烷吡咯烷食欲素受体激动剂

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2344285A1 (fr) *	1976-03-19	1977-10-14	Roussel Uclaf	Nouvelles lactones derivees du cyclopentanol, leur procede de preparation et leur application comme medicaments
US5322779A (en) *	1992-04-16	1994-06-21	The Research And Development Institute, Inc. At Montana State University	Taxol production by taxomyces andreanae
EP1142886A1 (en) *	2000-04-07	2001-10-10	Aventis Pharma Deutschland GmbH	Percyquinnin, a process for its production and its use as a pharmaceutical

2000
- 2000-04-07 EP EP00107536A patent/EP1142886A1/en not_active Withdrawn
2001
- 2001-03-24 CZ CZ20023310A patent/CZ20023310A3/cs unknown
- 2001-03-24 ES ES01929453T patent/ES2222992T3/es not_active Expired - Lifetime
- 2001-03-24 AT AT01929453T patent/ATE269855T1/de not_active IP Right Cessation
- 2001-03-24 MX MXPA02007895A patent/MXPA02007895A/es active IP Right Grant
- 2001-03-24 RS YUP-740/02A patent/RS50140B/sr unknown
- 2001-03-24 BR BR0109854-3A patent/BR0109854A/pt not_active Application Discontinuation
- 2001-03-24 TR TR2004/01739T patent/TR200401739T4/xx unknown
- 2001-03-24 KR KR1020027013443A patent/KR100791798B1/ko not_active IP Right Cessation
- 2001-03-24 IL IL15207301A patent/IL152073A0/xx active IP Right Grant
- 2001-03-24 CN CNB018064981A patent/CN1199959C/zh not_active Expired - Fee Related
- 2001-03-24 PT PT01929453T patent/PT1274698E/pt unknown
- 2001-03-24 DK DK01929453T patent/DK1274698T3/da active
- 2001-03-24 HU HU0300327A patent/HUP0300327A3/hu unknown
- 2001-03-24 JP JP2001575568A patent/JP2003530391A/ja active Pending
- 2001-03-24 SI SI200130168T patent/SI1274698T1/xx unknown
- 2001-03-24 NZ NZ521782A patent/NZ521782A/en unknown
- 2001-03-24 DE DE60103995T patent/DE60103995T2/de not_active Expired - Lifetime
- 2001-03-24 CA CA002405066A patent/CA2405066A1/en not_active Abandoned
- 2001-03-24 AU AU56219/01A patent/AU784902B2/en not_active Ceased
- 2001-03-24 EE EEP200200572A patent/EE200200572A/xx unknown
- 2001-03-24 WO PCT/EP2001/003392 patent/WO2001077094A1/en active IP Right Grant
- 2001-03-24 EP EP01929453A patent/EP1274698B1/en not_active Expired - Lifetime
- 2001-03-24 PL PL01357909A patent/PL357909A1/xx not_active IP Right Cessation
- 2001-03-24 RU RU2002129890/04A patent/RU2266290C2/ru not_active IP Right Cessation
- 2001-03-24 SK SK1432-2002A patent/SK14322002A3/sk unknown
- 2001-04-06 US US09/826,866 patent/US6596518B2/en not_active Expired - Lifetime
2002
- 2002-10-02 IL IL152073A patent/IL152073A/en not_active IP Right Cessation
- 2002-10-02 ZA ZA200207910A patent/ZA200207910B/en unknown
- 2002-10-03 NO NO20024772A patent/NO20024772L/no not_active Application Discontinuation
- 2002-10-04 HR HRP20020796 patent/HRP20020796A2/hr not_active Application Discontinuation
2003
- 2003-06-12 HK HK03104187A patent/HK1052005A1/xx not_active IP Right Cessation
2006
- 2006-08-25 AU AU2006203704A patent/AU2006203704B8/en not_active Ceased

Also Published As

Publication number	Publication date
KR20020084299A (ko)	2002-11-04
AU2006203704A1 (en)	2006-09-21
DK1274698T3 (da)	2004-11-01
NO20024772D0 (no)	2002-10-03
NZ521782A (en)	2004-05-28
US20020039768A1 (en)	2002-04-04
PL357909A1 (en)	2004-08-09
EP1274698B1 (en)	2004-06-23
KR100791798B1 (ko)	2008-01-04
EE200200572A (et)	2004-04-15
ES2222992T3 (es)	2005-02-16
CZ20023310A3 (cs)	2003-01-15
IL152073A (en)	2007-12-03
RU2002129890A (ru)	2004-03-27
WO2001077094A1 (en)	2001-10-18
ZA200207910B (en)	2003-07-21
HUP0300327A3 (en)	2004-10-28
RS50140B (sr)	2009-03-25
IL152073A0 (en)	2003-05-29
TR200401739T4 (tr)	2004-08-23
CA2405066A1 (en)	2001-10-18
ATE269855T1 (de)	2004-07-15
MXPA02007895A (es)	2002-11-29
CN1418203A (zh)	2003-05-14
DE60103995D1 (de)	2004-07-29
JP2003530391A (ja)	2003-10-14
NO20024772L (no)	2002-10-03
BR0109854A (pt)	2003-06-03
YU74002A (sh)	2005-11-28
EP1142886A1 (en)	2001-10-10
DE60103995T2 (de)	2005-01-05
AU5621901A (en)	2001-10-23
AU2006203704B2 (en)	2008-06-26
RU2266290C2 (ru)	2005-12-20
CN1199959C (zh)	2005-05-04
PT1274698E (pt)	2004-10-29
HK1052005A1 (en)	2003-08-29
SK14322002A3 (sk)	2003-05-02
US6596518B2 (en)	2003-07-22
EP1274698A1 (en)	2003-01-15
SI1274698T1 (en)	2004-12-31
AU784902B2 (en)	2006-07-20
AU2006203704B8 (en)	2008-07-10
HUP0300327A2 (hu)	2003-06-28

Legal Events

Date	Code	Title	Description
2004-12-31	A1OB	Publication of a patent application
2005-06-29	ARAI	Request for the grant of a patent on the basis of the submitted results of a substantive examination of a patent application
2006-02-28	PNAN	Change of the applicant name, address/residence	Owner name: SANOFI-AVENTIS DEUTSCHLAND GMBH, DE
2008-03-21	ODRP	Renewal fee for the maintenance of a patent	Payment date: 20080321 Year of fee payment: 8
2011-03-02	ODBC	Application rejected

Publication	Publication Date	Title
HRP20020796A2 (en)	2004-12-31	Percyquinnin, a process for its production and its use as a pharmaceutical
KR830002438B1 (ko)	1983-10-26	저 콜레스테린 혈증성 발효 생성물의 제법
CA1161380A (en)	1984-01-31	Hypocholesteremic fermentation products and process of preparation
Sasse et al.	2003	Archazolids, new cytotoxic macrolactones from archangium gephyra (Myxobacteria) production, isolation, physico-chemical and biological properties
US5283256A (en)	1994-02-01	Cholesterol-lowering agents
IL108194A (en)	1998-02-22	Acid B, D, 6, 8-Tetrahydroxy- 2- Methyl-Hexahydronophthalin-1-Hepanoic History 8-Aster of D-Lectons Its pharmaceutical preparations containing the same
AU750509B2 (en)	2002-07-18	Mumbaistatin, a process for its production and its use as a pharmaceutical
IL152612A (en)	2009-11-18	Cyclipostins, a method for their preparation, and their use
JP4436134B2 (ja)	2010-03-24	ドレクスレラノール誘導体、その製法及び使用
ITMI950865A1 (it)	1996-10-28	Derivati della purporogallina
MXPA00011165A (es)	2001-07-31	Mumbaistatin, un proceso para su produccion y su empleo como un producto farmaceutico
MXPA04012309A (es)	2005-02-25	Derivados de acidos polienocarboxilicos, metodo para su produccion y el uso de los mismos.
JPH1017527A (ja)	1998-01-20	抗菌性物質ｂｅ−３９５８９類及びその製造法