IL123998A - Conjugates of bile salts and pharmaceutical preparations containing them - Google Patents

Conjugates of bile salts and pharmaceutical preparations containing them

Info

Publication number: IL123998A
Authority: IL; Israel
Prior art keywords: acid; bile; fatty acid; dihydroxy; oic
Prior art date: 1998-04-08

Application number

IL12399898A

Other languages

English (en)

Hebrew (he)

Original Assignee

Galmed Int Ltd

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.)

1998-04-08

Filing date

1998-04-08

Publication date

2004-09-27

1998-04-08 Application filed by Galmed Int Ltd filed Critical Galmed Int Ltd

1998-04-08 Priority to IL12399898A priority Critical patent/IL123998A/en

1999-03-25 Priority to KR1020007010903A priority patent/KR100615560B1/ko

1999-03-25 Priority to PCT/IL1999/000173 priority patent/WO1999052932A1/en

1999-03-25 Priority to DE69902647T priority patent/DE69902647T2/de

1999-03-25 Priority to DK99912026T priority patent/DK1071702T3/da

1999-03-25 Priority to EA200000888A priority patent/EA003392B1/ru

1999-03-25 Priority to AT99912026T priority patent/ATE222923T1/de

1999-03-25 Priority to SI9930142T priority patent/SI1071702T1/xx

1999-03-25 Priority to NZ507309A priority patent/NZ507309A/xx

1999-03-25 Priority to ES99912026T priority patent/ES2183526T3/es

1999-03-25 Priority to IDW20001998A priority patent/ID26042A/id

1999-03-25 Priority to PL343360A priority patent/PL199271B1/pl

1999-03-25 Priority to EP99912026A priority patent/EP1071702B1/en

1999-03-25 Priority to AU30515/99A priority patent/AU742944B2/en

1999-03-25 Priority to UA2000095546A priority patent/UA70318C2/uk

1999-03-25 Priority to TR2000/02876T priority patent/TR200002876T2/xx

1999-03-25 Priority to JP2000543488A priority patent/JP5031942B2/ja

1999-03-25 Priority to PT99912026T priority patent/PT1071702E/pt

1999-03-25 Priority to CZ20003625A priority patent/CZ300824B6/cs

1999-03-25 Priority to BRPI9909908A priority patent/BRPI9909908B8/pt

1999-03-25 Priority to CNB998049034A priority patent/CN100386339C/zh

1999-03-25 Priority to HU0101653A priority patent/HU229513B1/hu

1999-03-25 Priority to CA002325933A priority patent/CA2325933C/en

2000-09-29 Priority to US09/675,656 priority patent/US6395722B1/en

2000-10-04 Priority to NO20004998A priority patent/NO316875B1/no

2000-10-23 Priority to US09/693,928 priority patent/US6384024B1/en

2001-04-17 Priority to IL142650A priority patent/IL142650A/en

2002-02-21 Priority to US10/078,671 priority patent/US6589946B2/en

2004-09-27 Publication of IL123998A publication Critical patent/IL123998A/en

Links

239000003833 bile salt Substances 0.000 title claims abstract description 26
239000008194 pharmaceutical composition Substances 0.000 title claims description 10
239000003613 bile acid Substances 0.000 claims abstract description 34
235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 34
229930195729 fatty acid Natural products 0.000 claims abstract description 34
239000000194 fatty acid Substances 0.000 claims abstract description 34
HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-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-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims abstract description 24
150000004665 fatty acids Chemical class 0.000 claims abstract description 21
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
150000001413 amino acids Chemical class 0.000 claims abstract description 4
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 64
210000000941 bile Anatomy 0.000 claims description 56
235000012000 cholesterol Nutrition 0.000 claims description 32
239000000203 mixture Substances 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 19
201000001883 cholelithiasis Diseases 0.000 claims description 19
BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 claims description 15
230000015572 biosynthetic process Effects 0.000 claims description 14
150000001875 compounds Chemical class 0.000 claims description 12
230000002265 prevention Effects 0.000 claims description 11
KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 claims description 9
238000004090 dissolution Methods 0.000 claims description 8
BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 claims description 7
RUDATBOHQWOJDD-UHFFFAOYSA-N (3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 RUDATBOHQWOJDD-UHFFFAOYSA-N 0.000 claims description 7
206010003210 Arteriosclerosis Diseases 0.000 claims description 7
239000004380 Cholic acid Substances 0.000 claims description 7
235000021355 Stearic acid Nutrition 0.000 claims description 7
208000011775 arteriosclerosis disease Diseases 0.000 claims description 7
229960002471 cholic acid Drugs 0.000 claims description 7
235000019416 cholic acid Nutrition 0.000 claims description 7
230000021615 conjugation Effects 0.000 claims description 7
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 7
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
239000008117 stearic acid Substances 0.000 claims description 7
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 6
230000009467 reduction Effects 0.000 claims description 6
239000004480 active ingredient Substances 0.000 claims description 4
VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 claims description 4
230000028327 secretion Effects 0.000 claims description 4
XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims description 4
RUDATBOHQWOJDD-UZVSRGJWSA-N ursodeoxycholic acid Chemical compound C([C@H]1C[C@@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-UZVSRGJWSA-N 0.000 claims description 4
229960001661 ursodiol Drugs 0.000 claims description 4
239000004471 Glycine Substances 0.000 claims description 3
229960001091 chenodeoxycholic acid Drugs 0.000 claims description 3
RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 claims description 3
150000004671 saturated fatty acids Chemical class 0.000 claims description 3
238000003786 synthesis reaction Methods 0.000 claims description 3
238000010521 absorption reaction Methods 0.000 claims description 2
239000002775 capsule Substances 0.000 claims description 2
229960003964 deoxycholic acid Drugs 0.000 claims description 2
KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 claims description 2
239000003995 emulsifying agent Substances 0.000 claims description 2
239000000839 emulsion Substances 0.000 claims description 2
239000003623 enhancer Substances 0.000 claims description 2
239000003112 inhibitor Substances 0.000 claims description 2
229960003080 taurine Drugs 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 67
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 47
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
229940093499 ethyl acetate Drugs 0.000 description 30
235000019439 ethyl acetate Nutrition 0.000 description 30
150000004702 methyl esters Chemical class 0.000 description 27
239000011541 reaction mixture Substances 0.000 description 20
150000003904 phospholipids Chemical class 0.000 description 18
238000003756 stirring Methods 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
239000013078 crystal Substances 0.000 description 13
238000000034 method Methods 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
239000002244 precipitate Substances 0.000 description 12
229940099352 cholate Drugs 0.000 description 11
238000002425 crystallisation Methods 0.000 description 11
230000008025 crystallization Effects 0.000 description 11
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 11
150000002632 lipids Chemical class 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
229940086542 triethylamine Drugs 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
230000000694 effects Effects 0.000 description 9
210000004185 liver Anatomy 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000012223 aqueous fraction Substances 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
238000005160 1H NMR spectroscopy Methods 0.000 description 6
101150041968 CDC13 gene Proteins 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
-1 bile acid fatty acid Chemical class 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
229910000041 hydrogen chloride Inorganic materials 0.000 description 6
JAJWGJBVLPIOOH-IZYKLYLVSA-M sodium taurocholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS([O-])(=O)=O)C)[C@@]2(C)[C@@H](O)C1 JAJWGJBVLPIOOH-IZYKLYLVSA-M 0.000 description 6
230000002792 vascular Effects 0.000 description 6
JQWAHKMIYCERGA-UHFFFAOYSA-N (2-nonanoyloxy-3-octadeca-9,12-dienoyloxypropoxy)-[2-(trimethylazaniumyl)ethyl]phosphinate Chemical compound CCCCCCCCC(=O)OC(COP([O-])(=O)CC[N+](C)(C)C)COC(=O)CCCCCCCC=CCC=CCCCCC JQWAHKMIYCERGA-UHFFFAOYSA-N 0.000 description 5
235000021314 Palmitic acid Nutrition 0.000 description 5
230000010235 enterohepatic circulation Effects 0.000 description 5
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 5
230000006911 nucleation Effects 0.000 description 5
238000010899 nucleation Methods 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
229940093761 bile salts Drugs 0.000 description 4
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
210000000232 gallbladder Anatomy 0.000 description 4
208000001130 gallstones Diseases 0.000 description 4
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
230000002401 inhibitory effect Effects 0.000 description 4
210000000936 intestine Anatomy 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
230000007928 solubilization Effects 0.000 description 4
238000005063 solubilization Methods 0.000 description 4
241000894007 species Species 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
241000699800 Cricetinae Species 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
239000008280 blood Substances 0.000 description 3
210000002751 lymph Anatomy 0.000 description 3
125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
230000001839 systemic circulation Effects 0.000 description 3
238000002560 therapeutic procedure Methods 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
238000003556 assay Methods 0.000 description 2
239000003858 bile acid conjugate Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
229960002449 glycine Drugs 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000011534 incubation Methods 0.000 description 2
230000031891 intestinal absorption Effects 0.000 description 2
239000000463 material Substances 0.000 description 2
HOGDNTQCSIKEEV-UHFFFAOYSA-N n'-hydroxybutanediamide Chemical compound NC(=O)CCC(=O)NO HOGDNTQCSIKEEV-UHFFFAOYSA-N 0.000 description 2
WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
210000003240 portal vein Anatomy 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000011160 research Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
235000003441 saturated fatty acids Nutrition 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
230000032258 transport Effects 0.000 description 2
GTRMJEVFVTWDIU-KPNWGBFJSA-N (3s,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-ol;hydrate Chemical compound O.C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 GTRMJEVFVTWDIU-KPNWGBFJSA-N 0.000 description 1
IFABLCIRROMTAN-MDZDMXLPSA-N (e)-1-chlorooctadec-9-ene Chemical compound CCCCCCCC\C=C\CCCCCCCCCl IFABLCIRROMTAN-MDZDMXLPSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 1
GIUTUZDGHNZVIA-UHFFFAOYSA-N 2-(ethylamino)acetic acid;hydrochloride Chemical compound Cl.CCNCC(O)=O GIUTUZDGHNZVIA-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
QHOINBKBMJLHPY-UHFFFAOYSA-N 2-chloroethyl formate Chemical compound ClCCOC=O QHOINBKBMJLHPY-UHFFFAOYSA-N 0.000 description 1
TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
UNSAJINGUOTTRA-UHFFFAOYSA-N 3-(3-bromophenyl)prop-2-yn-1-ol Chemical compound OCC#CC1=CC=CC(Br)=C1 UNSAJINGUOTTRA-UHFFFAOYSA-N 0.000 description 1
239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 1
ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
241000282412 Homo Species 0.000 description 1
239000005639 Lauric acid Substances 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
235000021360 Myristic acid Nutrition 0.000 description 1
TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
ATBOMIWRCZXYSZ-XZBBILGWSA-N [1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-hexadecanoyloxypropan-2-yl] (9e,12e)-octadeca-9,12-dienoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCC\C=C\C\C=C\CCCCC ATBOMIWRCZXYSZ-XZBBILGWSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000002192 cholecystectomy Methods 0.000 description 1
229960001231 choline Drugs 0.000 description 1
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
238000001514 detection method Methods 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000000378 dietary effect Effects 0.000 description 1
235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 1
QTHQYNCAWSGBCE-UHFFFAOYSA-N docosanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCCCCCC(Cl)=O QTHQYNCAWSGBCE-UHFFFAOYSA-N 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000037406 food intake Effects 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
230000005802 health problem Effects 0.000 description 1
ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 1
YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
BXZBGYJQEFZICM-UHFFFAOYSA-N icosanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCCCC(Cl)=O BXZBGYJQEFZICM-UHFFFAOYSA-N 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
WVJVHUWVQNLPCR-UHFFFAOYSA-N octadecanoyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCC WVJVHUWVQNLPCR-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000001907 polarising light microscopy Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000011343 solid material Substances 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000004575 stone Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
230000007723 transport mechanism Effects 0.000 description 1
229940014499 ursodeoxycholate Drugs 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- 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
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Vascular Medicine (AREA)
Cardiology (AREA)
Urology & Nephrology (AREA)
Gastroenterology & Hepatology (AREA)
Steroid Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Fats And Perfumes (AREA)

IL12399898A 1998-04-08 1998-04-08 Conjugates of bile salts and pharmaceutical preparations containing them IL123998A (en)

Priority Applications (28)

Application Number	Priority Date	Filing Date	Title
IL12399898A IL123998A (en)	1998-04-08	1998-04-08	Conjugates of bile salts and pharmaceutical preparations containing them
KR1020007010903A KR100615560B1 (ko)	1998-04-08	1999-03-25	담즙산 및 담즙산 유도체의 지방산 유도체
PCT/IL1999/000173 WO1999052932A1 (en)	1998-04-08	1999-03-25	Fatty acid derivatives of bile acids and bile acid derivatives
DE69902647T DE69902647T2 (de)	1998-04-08	1999-03-25	Fettsäurederivate von gallensäure und gallensäurederivaten
DK99912026T DK1071702T3 (da)	1998-04-08	1999-03-25	Fedtsyrederivater af galdesyre og galdesyrederivater
EA200000888A EA003392B1 (ru)	1998-04-08	1999-03-25	Производные желчных кислот
AT99912026T ATE222923T1 (de)	1998-04-08	1999-03-25	Fettsäurederivate von gallensäure und gallensäurederivaten
SI9930142T SI1071702T1 (en)	1998-04-08	1999-03-25	Fatty acid derivatives of bile acids and bile acid derivatives
NZ507309A NZ507309A (en)	1998-04-08	1999-03-25	Fatty acid derivatives of bile acids and bile acid derivatives
ES99912026T ES2183526T3 (es)	1998-04-08	1999-03-25	Derivados de acidos grasos de acidos biliares y derivados del acido biliar.
IDW20001998A ID26042A (id)	1998-04-08	1999-03-25	Turunan-turunan asam lemak dari asam-asam empedu dan asam empedu
PL343360A PL199271B1 (pl)	1998-04-08	1999-03-25	Koniugaty kwasu żółciowego lub soli żółciowej z kwasem tłuszczowym, zawierająca je kompozycja farmaceutyczna oraz ich zastosowanie
EP99912026A EP1071702B1 (en)	1998-04-08	1999-03-25	Fatty acid derivatives of bile acids and bile acid derivatives
AU30515/99A AU742944B2 (en)	1998-04-08	1999-03-25	Fatty acid derivatives of bile acids and bile acid derivatives
UA2000095546A UA70318C2 (uk)	1998-04-08	1999-03-25	Жирнокислотні похідні жовчних кислот та похідних жовчної кислоти, фармацевтичний препарат для розчинення холестеринових жовчних каменів і запобігання атеросклерозу, спосіб лікування (варіанти)
TR2000/02876T TR200002876T2 (tr)	1998-04-08	1999-03-25	Safra asit türevlerinin ve safra asitlerinin yağ asit türevleri
JP2000543488A JP5031942B2 (ja)	1998-04-08	1999-03-25	胆汁酸および胆汁酸誘導体の脂肪酸誘導体
PT99912026T PT1071702E (pt)	1998-04-08	1999-03-25	Derivados de acidos gordos de acidos biliares e derivados de acidos biliares
CZ20003625A CZ300824B6 (cs)	1998-04-08	1999-03-25	Konjugáty žlucové kyseliny nebo žlucové soli s mastnou kyselinou a farmaceutický prostredek je obsahující
BRPI9909908A BRPI9909908B8 (pt)	1998-04-08	1999-03-25	conjugados de ácido graxo de sal ou ácido biliar, composição farmacêutica compreendendo os mesmos e seus usos
CNB998049034A CN100386339C (zh)	1998-04-08	1999-03-25	胆汁酸和胆汁酸衍生物的脂肪酸衍生物
HU0101653A HU229513B1 (en)	1998-04-08	1999-03-25	Fatty acid derivatives of bile acids and bile acid derivatives
CA002325933A CA2325933C (en)	1998-04-08	1999-03-25	Fatty acid derivatives of bile acids and bile acid derivatives
US09/675,656 US6395722B1 (en)	1998-04-08	2000-09-29	Fatty acid derivatives of bile acids and bile acid derivatives
NO20004998A NO316875B1 (no)	1998-04-08	2000-10-04	Fettsyrederivater av gallesyrer og gallesyrederivater
US09/693,928 US6384024B1 (en)	1998-04-08	2000-10-23	Bile salt conjugates
IL142650A IL142650A (en)	1998-04-08	2001-04-17	Use of bile acid or bile salt fatty acids conjugates for the preparation of pharmaceutical compositions for reducing cholesterol, treating fatty liver and treating hyperglycemia and diabetes
US10/078,671 US6589946B2 (en)	1998-04-08	2002-02-21	Bile salt conjugates

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IL12399898A IL123998A (en)	1998-04-08	1998-04-08	Conjugates of bile salts and pharmaceutical preparations containing them

Publications (1)

Publication Number	Publication Date
IL123998A true IL123998A (en)	2004-09-27

Family

ID=11071405

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL12399898A IL123998A (en)	1998-04-08	1998-04-08	Conjugates of bile salts and pharmaceutical preparations containing them

Country Status (25)

Country	Link
US (3)	US6395722B1 (cs)
EP (1)	EP1071702B1 (cs)
JP (1)	JP5031942B2 (cs)
KR (1)	KR100615560B1 (cs)
CN (1)	CN100386339C (cs)
AT (1)	ATE222923T1 (cs)
AU (1)	AU742944B2 (cs)
BR (1)	BRPI9909908B8 (cs)
CA (1)	CA2325933C (cs)
CZ (1)	CZ300824B6 (cs)
DE (1)	DE69902647T2 (cs)
DK (1)	DK1071702T3 (cs)
EA (1)	EA003392B1 (cs)
ES (1)	ES2183526T3 (cs)
HU (1)	HU229513B1 (cs)
ID (1)	ID26042A (cs)
IL (1)	IL123998A (cs)
NO (1)	NO316875B1 (cs)
NZ (1)	NZ507309A (cs)
PL (1)	PL199271B1 (cs)
PT (1)	PT1071702E (cs)
SI (1)	SI1071702T1 (cs)
TR (1)	TR200002876T2 (cs)
UA (1)	UA70318C2 (cs)
WO (1)	WO1999052932A1 (cs)

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WO2008131419A2 (en)	2007-04-23	2008-10-30	Alnylam Pharmaceuticals, Inc.	Glycoconjugates of rna interference agents
US20080287429A1 (en) *	2007-05-15	2008-11-20	Z & Z Medical Holdings, Inc.	Dissolution of Arterial Cholesterol Plaques by Pharmacologically Induced Elevation of Endogenous Bile Salts
SI2182954T1 (sl) *	2007-07-25	2019-04-30	Medizinische Universitat Graz	Uporaba nor-žolčnih kislin pri zdravljenju arterioskleroze
CN101367859B (zh) *	2007-08-17	2011-05-11	中国人民解放军军事医学科学院毒物药物研究所	脂肪酸胆汁酸偶合物及其医药用途
CZ301037B6 (cs) *	2007-09-06	2009-10-21	Vysoká škola chemicko-technologická v Praze	Amidové konjugáty steroidních a žlucových kyselin s D-glukosaminem a zpusob jejich prípravy
US8507455B2 (en)	2007-12-04	2013-08-13	Alnylam Pharmaceuticals, Inc.	Folate conjugates
EP2229186A2 (en)	2007-12-04	2010-09-22	Alnylam Pharmaceuticals Inc.	Carbohydrate conjugates as delivery agents for oligonucleotides
US20100021538A1 (en) *	2008-02-29	2010-01-28	Youngro Byun	Pharmaceutical compositions containing heparin derivatives
US8575123B2 (en)	2008-04-11	2013-11-05	Tekmira Pharmaceuticals Corporation	Site-specific delivery of nucleic acids by combining targeting ligands with endosomolytic components
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US20120157419A1 (en) *	2009-02-02	2012-06-21	Tuvia Gilat	Methods and compositions for treating alzheimer's disease
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CN102115486B (zh) *	2009-12-30	2015-06-03	上海特化医药科技有限公司	一种3-β-花生酰胺基-7α,12α,5β-胆烷-24-羧酸的制备方法
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CN105611919A (zh) *	2013-08-08	2016-05-25	盖尔德姆疗法有限公司	包含胆汁酸-脂肪酸缀合物的抗痤疮组合物
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1998
- 1998-04-08 IL IL12399898A patent/IL123998A/en not_active IP Right Cessation
1999
- 1999-03-25 BR BRPI9909908A patent/BRPI9909908B8/pt not_active IP Right Cessation
- 1999-03-25 NZ NZ507309A patent/NZ507309A/xx not_active IP Right Cessation
- 1999-03-25 DE DE69902647T patent/DE69902647T2/de not_active Expired - Lifetime
- 1999-03-25 CZ CZ20003625A patent/CZ300824B6/cs not_active IP Right Cessation
- 1999-03-25 AU AU30515/99A patent/AU742944B2/en not_active Expired
- 1999-03-25 PT PT99912026T patent/PT1071702E/pt unknown
- 1999-03-25 ES ES99912026T patent/ES2183526T3/es not_active Expired - Lifetime
- 1999-03-25 WO PCT/IL1999/000173 patent/WO1999052932A1/en not_active Ceased
- 1999-03-25 AT AT99912026T patent/ATE222923T1/de active
- 1999-03-25 HU HU0101653A patent/HU229513B1/hu unknown
- 1999-03-25 KR KR1020007010903A patent/KR100615560B1/ko not_active Expired - Lifetime
- 1999-03-25 JP JP2000543488A patent/JP5031942B2/ja not_active Expired - Lifetime
- 1999-03-25 SI SI9930142T patent/SI1071702T1/xx unknown
- 1999-03-25 DK DK99912026T patent/DK1071702T3/da active
- 1999-03-25 CN CNB998049034A patent/CN100386339C/zh not_active Expired - Lifetime
- 1999-03-25 PL PL343360A patent/PL199271B1/pl unknown
- 1999-03-25 EA EA200000888A patent/EA003392B1/ru not_active IP Right Cessation
- 1999-03-25 EP EP99912026A patent/EP1071702B1/en not_active Expired - Lifetime
- 1999-03-25 ID IDW20001998A patent/ID26042A/id unknown
- 1999-03-25 UA UA2000095546A patent/UA70318C2/uk unknown
- 1999-03-25 TR TR2000/02876T patent/TR200002876T2/xx unknown
- 1999-03-25 CA CA002325933A patent/CA2325933C/en not_active Expired - Lifetime
2000
- 2000-09-29 US US09/675,656 patent/US6395722B1/en not_active Expired - Lifetime
- 2000-10-04 NO NO20004998A patent/NO316875B1/no not_active IP Right Cessation
- 2000-10-23 US US09/693,928 patent/US6384024B1/en not_active Expired - Lifetime
2002
- 2002-02-21 US US10/078,671 patent/US6589946B2/en not_active Expired - Lifetime

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2015186126A1 (en) *	2014-06-01	2015-12-10	Galmed Research And Development Ltd.	Fatty acid bile acid conjugates for treatment of lipodystrophy

Also Published As

Publication number	Publication date
CA2325933A1 (en)	1999-10-21
US6395722B1 (en)	2002-05-28
BR9909908A (pt)	2000-12-26
CZ20003625A3 (cs)	2001-01-17
BR9909908B1 (pt)	2014-03-18
CN1296492A (zh)	2001-05-23
EP1071702B1 (en)	2002-08-28
PL199271B1 (pl)	2008-09-30
SI1071702T1 (en)	2003-04-30
WO1999052932A1 (en)	1999-10-21
NO20004998D0 (no)	2000-10-04
EA200000888A1 (ru)	2001-04-23
ATE222923T1 (de)	2002-09-15
US20020091111A1 (en)	2002-07-11
US6384024B1 (en)	2002-05-07
PT1071702E (pt)	2003-01-31
ID26042A (id)	2000-11-16
EP1071702A1 (en)	2001-01-31
CN100386339C (zh)	2008-05-07
HUP0101653A2 (hu)	2001-12-28
UA70318C2 (uk)	2004-10-15
DE69902647T2 (de)	2003-04-24
US6589946B2 (en)	2003-07-08
AU742944B2 (en)	2002-01-17
CZ300824B6 (cs)	2009-08-19
JP5031942B2 (ja)	2012-09-26
TR200002876T2 (tr)	2000-12-21
DK1071702T3 (da)	2002-12-30
ES2183526T3 (es)	2003-03-16
NO316875B1 (no)	2004-06-07
PL343360A1 (en)	2001-08-13
BRPI9909908B8 (pt)	2021-05-25
DE69902647D1 (de)	2002-10-02
NZ507309A (en)	2003-06-30
KR100615560B1 (ko)	2006-08-25
AU3051599A (en)	1999-11-01
EA003392B1 (ru)	2003-04-24
KR20010042342A (ko)	2001-05-25
HUP0101653A3 (en)	2002-02-28
JP2002511482A (ja)	2002-04-16
HU229513B1 (en)	2014-01-28
NO20004998L (no)	2000-12-06
CA2325933C (en)	2008-06-10

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Date	Code	Title	Description
2005-01-24	ERR	Corrigendum	Free format text: JOURNAL 7/04 P. 2594 PATENT APPLICATION NO. 123998 IN THE ABSTRACT, REPLACE... 18-22... BY... 6-22...
2005-02-20	FF	Patent granted
2005-06-19	KB	Patent renewed
2008-06-05	KB	Patent renewed
2012-04-30	KB	Patent renewed
2018-10-31	EXP	Patent expired

Publication	Publication Date	Title
US6384024B1 (en)	2002-05-07	Bile salt conjugates
US5571795A (en)	1996-11-05	Derivative-compound-conjugates and pharmaceutical compositions comprising same
US5264424A (en)	1993-11-23	Modified gangliosides and the functional derivatives thereof
US5693769A (en)	1997-12-02	Glycosylated steroid derivatives for transport across biological membranes and process for making and using same
US5627270A (en)	1997-05-06	Glycosylated steroid derivatives for transport across biological membranes and process for making and using same
US5583239A (en)	1996-12-10	Antimicrobial sterol conjugates
EP0676410B1 (en)	1997-12-03	Bile acids derivatives useful in the therapy of the biliary calculosis from cholesterol and of the pathologies caused by cholestasis
Parmentier et al.	1977	Synthesis and characteristics of the specific monosulfates of chenodeoxycholate, deoxycholate and their taurine or glycine conjugates
US5455268A (en)	1995-10-03	Esculetin derivatives and pharmaceutical composition
AU696090B2 (en)	1998-09-03	New glucocorticoids
US3867413A (en)	1975-02-18	Fusidic acid conjugates
US5266566A (en)	1993-11-30	Method of treating fungal infections using sterodial ester compounds
Roda et al.	1994	New 6-substituted bile acids: physico-chemical and biological properties of 6 alpha-methyl ursodeoxycholic acid and 6 alpha-methyl-7-epicholic acid.
US5677285A (en)	1997-10-14	Derivatives of neuraminic acid
MXPA00009863A (en)	2002-05-09	Fatty acid derivatives of bile acids and bile acid derivatives
EP0092073A1 (en)	1983-10-26	Magnesium salt of chenodeoxycholic acid and ursodeoxycholic acid, the process for its preparation, and therapeutic compositions which contain it as active principle
Roda et al.	1994	New 6-substituted bile acids: physico-chemical and biological properties of 6~ methyl ursodeoxycholic acid and 6a-methylg% epicholic acid
JPH06192266A (ja)	1994-07-12	抗生物質ｎｋ８６−０２７９−ｉの新規誘導体、その製造法及び用途

IL123998A - Conjugates of bile salts and pharmaceutical preparations containing them - Google Patents

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