ES2238843T3 - Disoluciones acuosas transparentes de acidos biliares. - Google Patents
Disoluciones acuosas transparentes de acidos biliares.Info
- Publication number
- ES2238843T3 ES2238843T3 ES99935313T ES99935313T ES2238843T3 ES 2238843 T3 ES2238843 T3 ES 2238843T3 ES 99935313 T ES99935313 T ES 99935313T ES 99935313 T ES99935313 T ES 99935313T ES 2238843 T3 ES2238843 T3 ES 2238843T3
- Authority
- ES
- Spain
- Prior art keywords
- acid
- aqueous solution
- solution according
- aqueous
- bile
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000003613 bile acid Substances 0.000 title claims abstract description 115
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 239000000243 solution Substances 0.000 claims abstract description 64
- 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 63
- 239000007864 aqueous solution Substances 0.000 claims abstract description 63
- 229920002472 Starch Polymers 0.000 claims abstract description 41
- 239000008107 starch Substances 0.000 claims abstract description 41
- 235000019698 starch Nutrition 0.000 claims abstract description 41
- 239000012084 conversion product Substances 0.000 claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 150000001412 amines Chemical class 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 8
- 239000002244 precipitate Substances 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims description 104
- 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 72
- 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 64
- 229960001661 ursodiol Drugs 0.000 claims description 63
- 150000003839 salts Chemical class 0.000 claims description 36
- 229920002774 Maltodextrin Polymers 0.000 claims description 27
- 239000005913 Maltodextrin Substances 0.000 claims description 27
- 229940035034 maltodextrin Drugs 0.000 claims description 27
- 238000004090 dissolution Methods 0.000 claims description 23
- 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 22
- 238000002360 preparation method Methods 0.000 claims description 21
- 210000000941 bile Anatomy 0.000 claims description 20
- 238000010521 absorption reaction Methods 0.000 claims description 17
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 16
- 150000007513 acids Chemical class 0.000 claims description 16
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 16
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 14
- 229940024606 amino acid Drugs 0.000 claims description 13
- 150000001413 amino acids Chemical class 0.000 claims description 13
- 210000000936 intestine Anatomy 0.000 claims description 13
- 208000004998 Abdominal Pain Diseases 0.000 claims description 12
- 208000002881 Colic Diseases 0.000 claims description 12
- 229920002307 Dextran Polymers 0.000 claims description 11
- -1 cetrizine 2HCl Chemical compound 0.000 claims description 11
- 239000002671 adjuvant Substances 0.000 claims description 10
- 229960001091 chenodeoxycholic acid Drugs 0.000 claims description 9
- 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 9
- 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 claims description 8
- 102000004877 Insulin Human genes 0.000 claims description 8
- 108090001061 Insulin Proteins 0.000 claims description 8
- 229960003964 deoxycholic acid Drugs 0.000 claims description 8
- 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 8
- 229960002897 heparin Drugs 0.000 claims description 8
- 229920000669 heparin Polymers 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 229940125396 insulin Drugs 0.000 claims description 8
- BNRNXUUZRGQAQC-UHFFFAOYSA-N sildenafil Chemical compound CCCC1=NN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C)CC1 BNRNXUUZRGQAQC-UHFFFAOYSA-N 0.000 claims description 8
- BHTRKEVKTKCXOH-UHFFFAOYSA-N Taurochenodesoxycholsaeure Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(=O)NCCS(O)(=O)=O)C)C1(C)CC2 BHTRKEVKTKCXOH-UHFFFAOYSA-N 0.000 claims description 7
- 229960003080 taurine Drugs 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 210000002784 stomach Anatomy 0.000 claims description 6
- 229920001353 Dextrin Polymers 0.000 claims description 5
- 239000004375 Dextrin Substances 0.000 claims description 5
- DGABKXLVXPYZII-UHFFFAOYSA-N Hyodeoxycholic acid Natural products C1C(O)C2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 DGABKXLVXPYZII-UHFFFAOYSA-N 0.000 claims description 5
- 235000019425 dextrin Nutrition 0.000 claims description 5
- DGABKXLVXPYZII-SIBKNCMHSA-N hyodeoxycholic acid Chemical compound C([C@H]1[C@@H](O)C2)[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 DGABKXLVXPYZII-SIBKNCMHSA-N 0.000 claims description 5
- 238000002347 injection Methods 0.000 claims description 5
- 239000007924 injection Substances 0.000 claims description 5
- BHTRKEVKTKCXOH-LBSADWJPSA-N tauroursodeoxycholic 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)NCCS(O)(=O)=O)C)[C@@]2(C)CC1 BHTRKEVKTKCXOH-LBSADWJPSA-N 0.000 claims description 5
- UBCHPRBFMUDMNC-UHFFFAOYSA-N 1-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(C(N)C)C3 UBCHPRBFMUDMNC-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 4
- BLGXFZZNTVWLAY-CCZXDCJGSA-N Yohimbine Natural products C1=CC=C2C(CCN3C[C@@H]4CC[C@@H](O)[C@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-CCZXDCJGSA-N 0.000 claims description 4
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 4
- 229960003805 amantadine Drugs 0.000 claims description 4
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims description 4
- 229960004046 apomorphine Drugs 0.000 claims description 4
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 claims description 4
- BLGXFZZNTVWLAY-UHFFFAOYSA-N beta-Yohimbin Natural products C1=CC=C2C(CCN3CC4CCC(O)C(C4CC33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-UHFFFAOYSA-N 0.000 claims description 4
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 4
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims description 4
- 239000000693 micelle Substances 0.000 claims description 4
- 239000002324 mouth wash Substances 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 229960000329 ribavirin Drugs 0.000 claims description 4
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 4
- 229960000888 rimantadine Drugs 0.000 claims description 4
- 229960003310 sildenafil Drugs 0.000 claims description 4
- 229960003991 trazodone Drugs 0.000 claims description 4
- PHLBKPHSAVXXEF-UHFFFAOYSA-N trazodone Chemical compound ClC1=CC=CC(N2CCN(CCCN3C(N4C=CC=CC4=N3)=O)CC2)=C1 PHLBKPHSAVXXEF-UHFFFAOYSA-N 0.000 claims description 4
- 229960000317 yohimbine Drugs 0.000 claims description 4
- BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 claims description 4
- AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 claims description 4
- 241000792859 Enema Species 0.000 claims description 3
- 241000282414 Homo sapiens Species 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000007920 enema Substances 0.000 claims description 3
- AWDRATDZQPNJFN-VAYUFCLWSA-N taurodeoxycholic 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)NCCS(O)(=O)=O)C)[C@@]2(C)[C@@H](O)C1 AWDRATDZQPNJFN-VAYUFCLWSA-N 0.000 claims description 3
- 239000011782 vitamin Substances 0.000 claims description 3
- 229940088594 vitamin Drugs 0.000 claims description 3
- 235000013343 vitamin Nutrition 0.000 claims description 3
- 229930003231 vitamin Natural products 0.000 claims description 3
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 claims description 2
- SDOFMBGMRVAJNF-SLPGGIOYSA-N (2r,3r,4r,5s)-6-aminohexane-1,2,3,4,5-pentol Chemical compound NC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO SDOFMBGMRVAJNF-SLPGGIOYSA-N 0.000 claims description 2
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 claims description 2
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 claims description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 2
- 239000004475 Arginine Substances 0.000 claims description 2
- 102000055006 Calcitonin Human genes 0.000 claims description 2
- 108060001064 Calcitonin Proteins 0.000 claims description 2
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 claims description 2
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 claims description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 2
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 2
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 2
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims description 2
- 229930012538 Paclitaxel Natural products 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- ITBPIKUGMIZTJR-UHFFFAOYSA-N [bis(hydroxymethyl)amino]methanol Chemical compound OCN(CO)CO ITBPIKUGMIZTJR-UHFFFAOYSA-N 0.000 claims description 2
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 claims description 2
- 229960000723 ampicillin Drugs 0.000 claims description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 2
- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 claims description 2
- 229960004015 calcitonin Drugs 0.000 claims description 2
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 claims description 2
- 235000005487 catechin Nutrition 0.000 claims description 2
- 229960001231 choline Drugs 0.000 claims description 2
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 2
- 229950001002 cianidanol Drugs 0.000 claims description 2
- 229960001380 cimetidine Drugs 0.000 claims description 2
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 claims description 2
- 229960004544 cortisone Drugs 0.000 claims description 2
- 239000002537 cosmetic Substances 0.000 claims description 2
- 229960003957 dexamethasone Drugs 0.000 claims description 2
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims description 2
- 229940095399 enema Drugs 0.000 claims description 2
- PGBHMTALBVVCIT-VCIWKGPPSA-N framycetin Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CN)O2)N)O[C@@H]1CO PGBHMTALBVVCIT-VCIWKGPPSA-N 0.000 claims description 2
- 150000002337 glycosamines Chemical class 0.000 claims description 2
- 229960000890 hydrocortisone Drugs 0.000 claims description 2
- JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 claims description 2
- 229960001627 lamivudine Drugs 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 229960003105 metformin Drugs 0.000 claims description 2
- 229940053050 neomycin sulfate Drugs 0.000 claims description 2
- 229960003512 nicotinic acid Drugs 0.000 claims description 2
- 235000001968 nicotinic acid Nutrition 0.000 claims description 2
- 239000011664 nicotinic acid Substances 0.000 claims description 2
- 229960003104 ornithine Drugs 0.000 claims description 2
- 229960001592 paclitaxel Drugs 0.000 claims description 2
- 229960005205 prednisolone Drugs 0.000 claims description 2
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- GGWBHVILAJZWKJ-KJEVSKRMSA-N ranitidine hydrochloride Chemical compound [H+].[Cl-].[O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 GGWBHVILAJZWKJ-KJEVSKRMSA-N 0.000 claims description 2
- 229960003471 retinol Drugs 0.000 claims description 2
- 235000020944 retinol Nutrition 0.000 claims description 2
- 239000011607 retinol Substances 0.000 claims description 2
- 150000003431 steroids Chemical class 0.000 claims description 2
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 2
- 230000000699 topical effect Effects 0.000 claims description 2
- 229960001727 tretinoin Drugs 0.000 claims description 2
- 229960005294 triamcinolone Drugs 0.000 claims description 2
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 claims description 2
- 229960001124 trientine Drugs 0.000 claims description 2
- 229940051866 mouthwash Drugs 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 229960000510 ammonia Drugs 0.000 claims 1
- 239000011260 aqueous acid Substances 0.000 claims 1
- 229960003121 arginine Drugs 0.000 claims 1
- 229960003646 lysine Drugs 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 42
- 150000001408 amides Chemical class 0.000 abstract description 2
- 239000003814 drug Substances 0.000 description 31
- 238000009472 formulation Methods 0.000 description 28
- 229940079593 drug Drugs 0.000 description 22
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 20
- 239000003833 bile salt Substances 0.000 description 18
- 230000009102 absorption Effects 0.000 description 16
- 238000001556 precipitation Methods 0.000 description 16
- 210000004185 liver Anatomy 0.000 description 15
- 229940093761 bile salts Drugs 0.000 description 14
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 11
- 235000012000 cholesterol Nutrition 0.000 description 10
- 230000002378 acidificating effect Effects 0.000 description 9
- 230000002209 hydrophobic effect Effects 0.000 description 8
- 238000013112 stability test Methods 0.000 description 8
- 239000003981 vehicle Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000004471 Glycine Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 235000003599 food sweetener Nutrition 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000003765 sweetening agent Substances 0.000 description 6
- 241000282412 Homo Species 0.000 description 5
- SMEROWZSTRWXGI-HVATVPOCSA-N lithocholic 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)CC1 SMEROWZSTRWXGI-HVATVPOCSA-N 0.000 description 5
- 239000008194 pharmaceutical composition Substances 0.000 description 5
- 210000002966 serum Anatomy 0.000 description 5
- 230000007928 solubilization Effects 0.000 description 5
- 238000005063 solubilization Methods 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 150000005693 branched-chain amino acids Chemical class 0.000 description 4
- 230000002496 gastric effect Effects 0.000 description 4
- 210000001035 gastrointestinal tract Anatomy 0.000 description 4
- GHCZAUBVMUEKKP-XROMFQGDSA-N glycoursodeoxycholic 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)NCC(O)=O)C)[C@@]2(C)CC1 GHCZAUBVMUEKKP-XROMFQGDSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000013268 sustained release Methods 0.000 description 4
- 239000012730 sustained-release form Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- GHCZAUBVMUEKKP-UHFFFAOYSA-N ursodeoxycholic acid glycine-conjugate Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(=O)NCC(O)=O)C)C1(C)CC2 GHCZAUBVMUEKKP-UHFFFAOYSA-N 0.000 description 4
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 3
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 3
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 3
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 3
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000003858 bile acid conjugate Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 201000001883 cholelithiasis Diseases 0.000 description 3
- 230000021615 conjugation Effects 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003623 enhancer Substances 0.000 description 3
- 210000004051 gastric juice Anatomy 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 229960000310 isoleucine Drugs 0.000 description 3
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 3
- 229940067606 lecithin Drugs 0.000 description 3
- 239000000787 lecithin Substances 0.000 description 3
- 235000010445 lecithin Nutrition 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 210000004877 mucosa Anatomy 0.000 description 3
- 239000007922 nasal spray Substances 0.000 description 3
- 229940097496 nasal spray Drugs 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 230000032258 transport Effects 0.000 description 3
- 239000004474 valine Substances 0.000 description 3
- CABVTRNMFUVUDM-VRHQGPGLSA-N (3S)-3-hydroxy-3-methylglutaryl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C[C@@](O)(CC(O)=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 CABVTRNMFUVUDM-VRHQGPGLSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- BPYKTIZUTYGOLE-IFADSCNNSA-N Bilirubin Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(\C=C/3C(=C(C=C)C(=O)N\3)C)N2)CCC(O)=O)N1 BPYKTIZUTYGOLE-IFADSCNNSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 210000003445 biliary tract Anatomy 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000008827 biological function Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000006735 deficit Effects 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- 238000012377 drug delivery Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 230000010235 enterohepatic circulation Effects 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 208000019423 liver disease Diseases 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 2
- 230000036470 plasma concentration Effects 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000008137 solubility enhancer Substances 0.000 description 2
- 230000003637 steroidlike Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- OCUSNPIJIZCRSZ-ZTZWCFDHSA-N (2s)-2-amino-3-methylbutanoic acid;(2s)-2-amino-4-methylpentanoic acid;(2s,3s)-2-amino-3-methylpentanoic acid Chemical compound CC(C)[C@H](N)C(O)=O.CC[C@H](C)[C@H](N)C(O)=O.CC(C)C[C@H](N)C(O)=O OCUSNPIJIZCRSZ-ZTZWCFDHSA-N 0.000 description 1
- GOLXRNDWAUTYKT-UHFFFAOYSA-N 3-(1H-indol-3-yl)propanoic acid Chemical compound C1=CC=C2C(CCC(=O)O)=CNC2=C1 GOLXRNDWAUTYKT-UHFFFAOYSA-N 0.000 description 1
- 102000018616 Apolipoproteins B Human genes 0.000 description 1
- 108010027006 Apolipoproteins B Proteins 0.000 description 1
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 description 1
- 208000033222 Biliary cirrhosis primary Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 206010008609 Cholangitis sclerosing Diseases 0.000 description 1
- 102000004410 Cholesterol 7-alpha-monooxygenases Human genes 0.000 description 1
- 108090000943 Cholesterol 7-alpha-monooxygenases Proteins 0.000 description 1
- 206010008909 Chronic Hepatitis Diseases 0.000 description 1
- 208000006154 Chronic hepatitis C Diseases 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 1
- 206010013911 Dysgeusia Diseases 0.000 description 1
- 208000005189 Embolism Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 208000005176 Hepatitis C Diseases 0.000 description 1
- 206010019755 Hepatitis chronic active Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 102000011965 Lipoprotein Receptors Human genes 0.000 description 1
- 108010061306 Lipoprotein Receptors Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 208000012654 Primary biliary cholangitis Diseases 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- WBWWGRHZICKQGZ-UHFFFAOYSA-N Taurocholic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(=O)NCCS(O)(=O)=O)C)C1(C)C(O)C2 WBWWGRHZICKQGZ-UHFFFAOYSA-N 0.000 description 1
- 208000001435 Thromboembolism Diseases 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000009056 active transport Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229940078967 bile acid preparations for bile therapy Drugs 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000006696 biosynthetic metabolic pathway Effects 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 238000004820 blood count Methods 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000001906 cholesterol absorption Effects 0.000 description 1
- 150000001841 cholesterols Chemical class 0.000 description 1
- 208000019425 cirrhosis of liver Diseases 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 230000000112 colonic effect Effects 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000005906 dihydroxylation reaction Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 239000003596 drug target Substances 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- 229940079360 enema for constipation Drugs 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- 238000009505 enteric coating Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 210000000232 gallbladder Anatomy 0.000 description 1
- 208000001130 gallstones Diseases 0.000 description 1
- 229940097042 glucuronate Drugs 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 208000010710 hepatitis C virus infection Diseases 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 208000008384 ileus Diseases 0.000 description 1
- 239000012729 immediate-release (IR) formulation Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 108010022197 lipoprotein cholesterol Proteins 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000005229 liver cell Anatomy 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 210000004379 membrane Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 210000002850 nasal mucosa Anatomy 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000003186 pharmaceutical solution Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 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
- 150000003904 phospholipids Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 201000000742 primary sclerosing cholangitis Diseases 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000012762 regulation of cholesterol biosynthetic process Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 208000010157 sclerosing cholangitis Diseases 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- NRHMKIHPTBHXPF-TUJRSCDTSA-M sodium cholate 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-])=O)C)[C@@]2(C)[C@@H](O)C1 NRHMKIHPTBHXPF-TUJRSCDTSA-M 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 125000002328 sterol group Chemical group 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- BHTRKEVKTKCXOH-AYSJQVDDSA-N taurochenodeoxycholic acid Chemical compound C([C@H]1C[C@@H]2O)[C@H](O)CC[C@]1(C)C1C2C2CC[C@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)CC1 BHTRKEVKTKCXOH-AYSJQVDDSA-N 0.000 description 1
- BHTRKEVKTKCXOH-BJLOMENOSA-N taurochenodeoxycholic 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)NCCS(O)(=O)=O)C)[C@@]2(C)CC1 BHTRKEVKTKCXOH-BJLOMENOSA-N 0.000 description 1
- WBWWGRHZICKQGZ-GIHLXUJPSA-N taurocholic 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)NCCS(O)(=O)=O)C)[C@@]2(C)[C@H](O)C1 WBWWGRHZICKQGZ-GIHLXUJPSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000002676 xenobiotic agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/08—Solutions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/28—Steroids, e.g. cholesterol, bile acids or glycyrrhetinic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- 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
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- 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
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Dermatology (AREA)
- Inorganic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Diabetes (AREA)
- Gastroenterology & Hepatology (AREA)
- Otolaryngology (AREA)
- Pulmonology (AREA)
- Nutrition Science (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9406998P | 1998-07-24 | 1998-07-24 | |
| US94069P | 1998-07-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2238843T3 true ES2238843T3 (es) | 2005-09-01 |
Family
ID=22242686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES99935313T Expired - Lifetime ES2238843T3 (es) | 1998-07-24 | 1999-07-20 | Disoluciones acuosas transparentes de acidos biliares. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6251428B1 (enExample) |
| EP (1) | EP1113785B1 (enExample) |
| JP (2) | JP4790123B2 (enExample) |
| KR (1) | KR100524358B1 (enExample) |
| CN (1) | CN1205922C (enExample) |
| AT (1) | ATE292956T1 (enExample) |
| AU (1) | AU758679B2 (enExample) |
| BR (1) | BR9912395A (enExample) |
| CA (1) | CA2338457C (enExample) |
| DE (1) | DE69924740T2 (enExample) |
| ES (1) | ES2238843T3 (enExample) |
| ID (1) | ID29632A (enExample) |
| IL (2) | IL140986A0 (enExample) |
| PT (1) | PT1113785E (enExample) |
| RU (1) | RU2224523C2 (enExample) |
| WO (1) | WO2000004875A2 (enExample) |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100314496B1 (ko) | 1998-05-28 | 2001-11-22 | 윤동진 | 항혈전성이 있는 헤파린 유도체, 그의 제조방법 및 용도 |
| US20050158408A1 (en) * | 1998-07-24 | 2005-07-21 | Yoo Seo H. | Dried forms of aqueous solubilized bile acid dosage formulation: preparation and uses thereof |
| US7772220B2 (en) * | 2004-10-15 | 2010-08-10 | Seo Hong Yoo | Methods and compositions for reducing toxicity of a pharmaceutical compound |
| US7303768B2 (en) | 1998-07-24 | 2007-12-04 | Seo Hong Yoo | Preparation of aqueous clear solution dosage forms with bile acids |
| US20070072828A1 (en) * | 1998-07-24 | 2007-03-29 | Yoo Seo H | Bile preparations for colorectal disorders |
| DE19834814A1 (de) * | 1998-08-01 | 2000-02-03 | Beiersdorf Ag | Kosmetische und dermatologische Zubereitungen mit einem wirksamen Gehalt an Gallensäuren, ihren Salzen und/oder ihren Derivaten |
| US6417179B1 (en) * | 1998-10-13 | 2002-07-09 | Craig G. Burkhart | Ear wax solution |
| GB2355009A (en) * | 1999-07-30 | 2001-04-11 | Univ Glasgow | Peptides conjugated to bile acids/salts |
| AU2006203315B2 (en) * | 2000-02-04 | 2008-08-28 | Seo Hong Yoo | Preparation of aqueous clear solution dosage forms with bile acids |
| WO2001056547A2 (en) * | 2000-02-04 | 2001-08-09 | Seo Hong Yoo | Preparation of aqueous clear solution dosage forms with bile acids |
| DE60028339T2 (de) * | 2000-04-20 | 2007-05-10 | Bioprogress S.P.A. | Verfahren zur Herstellung ursodeoxycholsäure enthaltender pharmazeutischer Zusammensetzungen in flüssiger Form |
| FR2809310B1 (fr) * | 2000-05-26 | 2004-02-13 | Centre Nat Rech Scient | Utilisation de derives de biguanide pour fabriquer un medicament ayant un effet cicatrisant |
| KR100368936B1 (ko) * | 2000-10-04 | 2003-01-24 | 주식회사 대웅 | 우루소데옥시콜린산을 함유한 환경호르몬 독성의 예방 및치료제 |
| GB0103046D0 (en) * | 2001-02-07 | 2001-03-21 | Novartis Ag | Organic Compounds |
| EP2591806A1 (en) * | 2001-06-14 | 2013-05-15 | Otsuka Pharmaceutical Co., Ltd. | Medicinal composition |
| US6702850B1 (en) | 2002-09-30 | 2004-03-09 | Mediplex Corporation Korea | Multi-coated drug-eluting stent for antithrombosis and antirestenosis |
| US20080026077A1 (en) * | 2002-11-12 | 2008-01-31 | John Hilfinger | Methods and compositions of gene delivery agents for systemic and local therapy |
| US7145125B2 (en) | 2003-06-23 | 2006-12-05 | Advanced Optical Technologies, Llc | Integrating chamber cone light using LED sources |
| US7754230B2 (en) * | 2004-05-19 | 2010-07-13 | The Regents Of The University Of California | Methods and related compositions for reduction of fat |
| EP3424508B1 (en) * | 2004-05-19 | 2021-05-05 | Lundquist Institute for Biomedical Innovation at Harbor-UCLA Medical Center | Use of sodium deoxycholate for the removal of localized fat accumulation |
| US20060127468A1 (en) * | 2004-05-19 | 2006-06-15 | Kolodney Michael S | Methods and related compositions for reduction of fat and skin tightening |
| US7906137B2 (en) * | 2004-05-21 | 2011-03-15 | Mediplex Corporation, Korea | Delivery agents for enhancing mucosal absorption of therapeutic agents |
| CA2577268A1 (en) * | 2004-08-30 | 2006-03-09 | Seo Hong Yoo | Neuroprotective effect of solubilized udca in focal ischemic model |
| DE602005027727D1 (de) * | 2004-10-15 | 2011-06-09 | Seo Hong Yoo | Zusammensetzungen zur verringerung der toxizität von cisplatin, carboplatin und oxaliplatin |
| CA2585471A1 (en) * | 2004-11-01 | 2006-05-11 | Seo Hong Yoo | Methods and compositions for reducing neurodegeneration in amyotrophic lateral sclerosis |
| ES2358089T3 (es) * | 2004-11-01 | 2011-05-05 | Seo Hong Yoo | Métodos y composiciones para reducir la neurodegeneración en esclerosis lateral amiotrófica. |
| SI2727583T1 (sl) | 2004-12-22 | 2022-01-31 | Nitto Denko Corporation | Nosilec učinkovine in komplet nosilca učinkovine za zaviranje fibroze |
| US20120269886A1 (en) | 2004-12-22 | 2012-10-25 | Nitto Denko Corporation | Therapeutic agent for pulmonary fibrosis |
| US9572886B2 (en) | 2005-12-22 | 2017-02-21 | Nitto Denko Corporation | Agent for treating myelofibrosis |
| CN101023940A (zh) * | 2006-02-20 | 2007-08-29 | 郝守祝 | 一种紫杉烷类化合物的药用组合物、制备方法及用途 |
| CN101547699A (zh) * | 2006-09-15 | 2009-09-30 | 柳署弘 | 用于结肠直肠病症的胆汁制剂 |
| TWI407971B (zh) | 2007-03-30 | 2013-09-11 | Nitto Denko Corp | Cancer cells and tumor-related fibroblasts |
| ITMI20071573A1 (it) * | 2007-07-31 | 2009-02-01 | Acraf | Composizione farmaceutica liquida stabile a base di trazodone |
| WO2009036368A2 (en) | 2007-09-14 | 2009-03-19 | Nitto Denko Corporation | Drug carriers |
| US9295677B2 (en) | 2008-02-26 | 2016-03-29 | Qing Bile Therapeutics Inc. | Polyhydroxylated bile acids for treatment of biliary disorders |
| US20100021538A1 (en) * | 2008-02-29 | 2010-01-28 | Youngro Byun | Pharmaceutical compositions containing heparin derivatives |
| US8101593B2 (en) | 2009-03-03 | 2012-01-24 | Kythera Biopharmaceuticals, Inc. | Formulations of deoxycholic acid and salts thereof |
| JP5420946B2 (ja) * | 2009-03-23 | 2014-02-19 | 富士フイルム株式会社 | 胆汁酸を含むミノキシジル水性組成物 |
| JP5909774B2 (ja) * | 2009-08-25 | 2016-04-27 | クィン ビル セラピューティクス インコーポレイテッド | 胆道疾患を治療するためのポリヒドロキシル化胆汁酸 |
| MX363465B (es) | 2011-02-18 | 2019-03-25 | Kythera Biopharmaceuticals Inc | Tratamiento de la grasa submental. |
| US8653058B2 (en) | 2011-04-05 | 2014-02-18 | Kythera Biopharmaceuticals, Inc. | Compositions comprising deoxycholic acid and salts thereof suitable for use in treating fat deposits |
| EA029305B1 (ru) * | 2011-08-23 | 2018-03-30 | Китера Биофармасьютикалз, Инк. | Составы дезоксихолевой кислоты и ее солей |
| CN104039327B (zh) | 2012-01-06 | 2017-02-15 | 大熊制药株式会社 | 含有牛磺熊去氧胆酸的组合物 |
| MX371392B (es) * | 2013-03-15 | 2020-01-28 | Janssen Pharmaceutica Nv | Composicion farmaceutica de clorhidrato de s-ketamina. |
| WO2014195950A1 (en) | 2013-06-06 | 2014-12-11 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Bile acid-basic amino acid conjugates and uses thereof |
| EP3082428A4 (en) | 2013-12-09 | 2017-08-02 | Respira Therapeutics, Inc. | Pde5 inhibitor powder formulations and methods relating thereto |
| EP3179993B1 (en) | 2014-08-13 | 2021-01-20 | Janssen Pharmaceutica NV | Esketamine for use in a method for the treatment of depression |
| CA2961208A1 (en) | 2014-09-15 | 2016-03-24 | Janssen Pharmaceutica Nv | Val66met (snp rs6265) genotype specific dosing regimens and methods for the treatment of depression |
| US20160332962A1 (en) | 2015-05-13 | 2016-11-17 | Janssen Pharmaceutica Nv | (s)-csa salt of s-ketamine, (r)-csa salt of s-ketamine and processes for the preparation of s-ketamine |
| WO2017168174A1 (en) | 2016-04-02 | 2017-10-05 | N4 Pharma Uk Limited | New pharmaceutical forms of sildenafil |
| KR20180036580A (ko) * | 2016-09-30 | 2018-04-09 | 주식회사 유스바이오팜 | 수가용화(水加溶化)된 우르소데옥시콜산을 함유하는 염증성 피부질환 또는 중증 소양증 예방 또는 치료용 조성물 |
| WO2018062922A1 (ko) * | 2016-09-30 | 2018-04-05 | 주식회사 유스바이오팜 | 수가용화된 우르소데옥시콜산을 함유하는 염증성 피부질환 또는 중증 소양증 예방 또는 치료용 조성물 |
| KR102252450B1 (ko) * | 2017-02-09 | 2021-05-14 | 주식회사 아미코젠파마 | 우르소데옥시콜산을 함유하는 시각장애 예방 또는 치료용 조성물 |
| WO2018147685A1 (ko) * | 2017-02-09 | 2018-08-16 | 주식회사 유스바이오팜 | 우르소데옥시콜산을 함유하는 시각장애 예방 또는 치료용 조성물 |
| US20200009081A1 (en) | 2017-09-13 | 2020-01-09 | Janssen Pharmaceutica N.V. | Delivery Of Esketamine For The Treatment Of Depression |
| BR112020012473A2 (pt) | 2017-12-22 | 2020-11-24 | Janssen Pharmaceuticals, Inc. | escetamina para o tratamento da depressão |
| JP2019127471A (ja) * | 2018-01-26 | 2019-08-01 | 株式会社ヤマザキ | 美肌用組成物 |
| AU2020231172A1 (en) | 2019-03-05 | 2021-09-23 | Janssen Pharmaceuticals, Inc. | Esketamine for the treatment of depression |
| EP4499107A1 (en) * | 2022-03-31 | 2025-02-05 | NZP UK Limited | 7-ketolithocholic acid for use in the treatment of gut dysbiosis and as a prebiotic |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3845770A (en) | 1972-06-05 | 1974-11-05 | Alza Corp | Osmatic dispensing device for releasing beneficial agent |
| US3916899A (en) | 1973-04-25 | 1975-11-04 | Alza Corp | Osmotic dispensing device with maximum and minimum sizes for the passageway |
| JPS5522616A (en) * | 1978-08-04 | 1980-02-18 | Tokyo Tanabe Co Ltd | Bile acid inclusion compound and injection containing the same |
| US4327725A (en) | 1980-11-25 | 1982-05-04 | Alza Corporation | Osmotic device with hydrogel driving member |
| GB8417895D0 (en) | 1984-07-13 | 1984-08-15 | Marples B A | Pharmaceutical anti-fungal composition |
| JPS62153220A (ja) * | 1985-12-27 | 1987-07-08 | Tokyo Tanabe Co Ltd | 胆汁酸内用水剤 |
| HU203204B (en) | 1987-09-15 | 1991-06-28 | Sandoz Ag | Process for producing suppository containing calcitonin and taurocholic acid |
| ZA887658B (en) * | 1987-10-15 | 1990-06-27 | Syntex Inc | Intranasal administration of polypeptides in powdered form |
| HU206367B (en) * | 1988-04-30 | 1992-10-28 | Sandoz Ag | Process for producing acid addition salts of steroid carboxylic acid-amidated taurine and glycine, as well as pharmaceutical compositions comprising such salts |
| AU658565B2 (en) * | 1990-04-04 | 1995-04-27 | Berwind Pharmaceutical Services, Inc. | Aqueous maltodextrin and cellulosic polymer film coatings |
| US5057321A (en) | 1990-06-13 | 1991-10-15 | Alza Corporation | Dosage form comprising drug and maltodextrin |
| JPH0749438B2 (ja) * | 1990-10-31 | 1995-05-31 | 東京田辺製薬株式会社 | タウリン抱合型胆汁酸の精製方法 |
| IT1245889B (it) | 1991-04-12 | 1994-10-25 | Alfa Wassermann Spa | Formulazioni farmaceutiche per uso orale gastroresistenti contenenti sali di acidi biliari. |
| IT1245890B (it) | 1991-04-12 | 1994-10-25 | Alfa Wassermann Spa | Formulazioni farmaceutiche per uso orale gastroresistenti contenenti acidi biliari. |
| IT1245891B (it) | 1991-04-12 | 1994-10-25 | Alfa Wassermann Spa | Formulazioni farmaceutiche a rilascio controllato per uso orale gastroresistenti contenenti acidi biliari e loro sali. |
| CH680704A5 (enExample) | 1991-05-15 | 1992-10-30 | Medichemie Ag | |
| HU209251B (en) | 1992-03-13 | 1994-04-28 | Synepos Ag | Process for producing stable, peroral solution drug forms with controlled release of active ingredient and comprising beta-blocking pharmacons |
| US5260074A (en) | 1992-06-22 | 1993-11-09 | Digestive Care Inc. | Compositions of digestive enzymes and salts of bile acids and process for preparation thereof |
| US5578304A (en) | 1992-06-22 | 1996-11-26 | Digestive Care Inc. | Compositions of digestive enzymes and salts of bile acids and process for preparation thereof |
| US5302400A (en) | 1992-06-22 | 1994-04-12 | Digestive Care Inc. | Preparation of gastric acid-resistant microspheres containing digestive enzymes and buffered-bile acids |
| US5863550A (en) | 1993-03-31 | 1999-01-26 | Tokyo Tanabe Company Limited | Cholestasis ameliorant |
| JPH06321783A (ja) * | 1993-05-12 | 1994-11-22 | Sekisui Chem Co Ltd | 胆汁酸腸管吸収抑制剤 |
| ES2121599T3 (es) * | 1993-08-30 | 1998-12-01 | Medichemie Ag | Medicamento que contiene acido ursodeoxicolico en forma de administracion liquida. |
| DE4432708A1 (de) | 1994-09-14 | 1996-03-21 | Hoechst Ag | Modifizierte Gallensäuren, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US5653987A (en) * | 1995-05-16 | 1997-08-05 | Modi; Pankaj | Liquid formulations for proteinic pharmaceuticals |
| US5686588A (en) | 1995-08-16 | 1997-11-11 | Yoo; Seo Hong | Amine acid salt compounds and process for the production thereof |
| US5763435A (en) * | 1995-11-21 | 1998-06-09 | Children's Hospital Medical Center | Sulfate conjugates of ursodeoxycholic acid, and their beneficial use in inflammatory disorders |
| US5843929A (en) | 1996-03-22 | 1998-12-01 | Mayo Foundation For Medical Education And Research | Chemoprevention of metachronous adenomatous colorectal polyps |
| ATE394107T1 (de) * | 1996-05-23 | 2008-05-15 | Novartis Pharma Gmbh | Vorbeugung und behandlung von kolonadenom oder kolonmikroadenom mit 6-fluorursodeoxycholsäure |
| DE29717252U1 (de) | 1997-09-26 | 1998-02-19 | Dr. Falk Pharma GmbH, 79108 Freiburg | Arzneimittelkit aus einem Budesonid-haltigen und einem Ursodesoxycholsäure-haltigen Arzneimittel zur Behandlung von cholestatischen Lebererkrankungen |
-
1999
- 1999-07-20 JP JP2000560868A patent/JP4790123B2/ja not_active Expired - Fee Related
- 1999-07-20 RU RU2001105906/15A patent/RU2224523C2/ru not_active IP Right Cessation
- 1999-07-20 CA CA002338457A patent/CA2338457C/en not_active Expired - Fee Related
- 1999-07-20 KR KR10-2001-7001037A patent/KR100524358B1/ko not_active Expired - Lifetime
- 1999-07-20 ES ES99935313T patent/ES2238843T3/es not_active Expired - Lifetime
- 1999-07-20 WO PCT/US1999/012840 patent/WO2000004875A2/en not_active Ceased
- 1999-07-20 AU AU50819/99A patent/AU758679B2/en not_active Ceased
- 1999-07-20 IL IL14098699A patent/IL140986A0/xx active IP Right Grant
- 1999-07-20 BR BR9912395-9A patent/BR9912395A/pt not_active Application Discontinuation
- 1999-07-20 US US09/357,549 patent/US6251428B1/en not_active Expired - Fee Related
- 1999-07-20 AT AT99935313T patent/ATE292956T1/de active
- 1999-07-20 EP EP99935313A patent/EP1113785B1/en not_active Expired - Lifetime
- 1999-07-20 PT PT99935313T patent/PT1113785E/pt unknown
- 1999-07-20 CN CNB998101478A patent/CN1205922C/zh not_active Expired - Fee Related
- 1999-07-20 ID IDW20010199D patent/ID29632A/id unknown
- 1999-07-20 DE DE69924740T patent/DE69924740T2/de not_active Expired - Lifetime
-
2001
- 2001-01-18 IL IL140986A patent/IL140986A/en not_active IP Right Cessation
-
2010
- 2010-10-18 JP JP2010233252A patent/JP2011021031A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CA2338457C (en) | 2009-11-17 |
| JP2011021031A (ja) | 2011-02-03 |
| DE69924740T2 (de) | 2005-09-01 |
| WO2000004875A2 (en) | 2000-02-03 |
| PT1113785E (pt) | 2005-08-31 |
| CA2338457A1 (en) | 2000-02-03 |
| JP2002522357A (ja) | 2002-07-23 |
| IL140986A0 (en) | 2002-02-10 |
| WO2000004875A3 (en) | 2001-05-03 |
| CN1205922C (zh) | 2005-06-15 |
| DE69924740D1 (de) | 2005-05-19 |
| KR100524358B1 (ko) | 2005-10-26 |
| AU758679B2 (en) | 2003-03-27 |
| BR9912395A (pt) | 2001-10-16 |
| CN1348360A (zh) | 2002-05-08 |
| JP4790123B2 (ja) | 2011-10-12 |
| RU2224523C2 (ru) | 2004-02-27 |
| US6251428B1 (en) | 2001-06-26 |
| IL140986A (en) | 2006-08-01 |
| AU5081999A (en) | 2000-02-14 |
| EP1113785A2 (en) | 2001-07-11 |
| ATE292956T1 (de) | 2005-04-15 |
| EP1113785B1 (en) | 2005-04-13 |
| KR20010074748A (ko) | 2001-08-09 |
| ID29632A (id) | 2001-09-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2238843T3 (es) | Disoluciones acuosas transparentes de acidos biliares. | |
| US7303768B2 (en) | Preparation of aqueous clear solution dosage forms with bile acids | |
| US7166299B2 (en) | Preparation of aqueous clear solution dosage forms with bile acids | |
| JP2002522357A5 (enExample) | ||
| IL151132A (en) | Patridine compounds for the treatment of psoriasis | |
| US5089482A (en) | Pharmaceutical compositions for nasal administration containing steroid hormones and dimethyl-β-cyclodextrin | |
| ES2615484T3 (es) | Composiciones medicinales que contienen grelina | |
| US20050158408A1 (en) | Dried forms of aqueous solubilized bile acid dosage formulation: preparation and uses thereof | |
| AU2004325203A1 (en) | Dried forms of aqueous solubilized bile acid dosage formulation: preparation and uses thereof | |
| CN101048164B (zh) | 降低肌萎缩性侧索硬化中神经变性的组合物 | |
| CN114276535A (zh) | 聚乙二醇脂质及其应用 | |
| JP2009511577A (ja) | 胃腸疾患用胆汁製剤 | |
| ES2360809T3 (es) | Micelas inversas basadas en fitoesteroles y acilgliceroles y uso terapéutico de las mismas. | |
| ES2828692T3 (es) | Derivado de ácido condroitinsulfúrico y fármaco para tratar enfermedades de vejiga | |
| CN101480404B (zh) | 谷维素的药用产品及其制备方法 | |
| Axelrod et al. | Intestinal transport of gentamicin with a novel, glycosteroid drug transport agent | |
| AU2006203315B2 (en) | Preparation of aqueous clear solution dosage forms with bile acids | |
| JP5201546B2 (ja) | Ｎ‐アセチルシステイン抱合型胆汁酸、それを含有する医薬組成物及びその製造方法 | |
| CN1905888A (zh) | 用作经口或肠胃外医药产品的元素硫 |