JP2014512366A5 - - Google Patents
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- Publication number
- JP2014512366A5 JP2014512366A5 JP2014504327A JP2014504327A JP2014512366A5 JP 2014512366 A5 JP2014512366 A5 JP 2014512366A5 JP 2014504327 A JP2014504327 A JP 2014504327A JP 2014504327 A JP2014504327 A JP 2014504327A JP 2014512366 A5 JP2014512366 A5 JP 2014512366A5
- Authority
- JP
- Japan
- Prior art keywords
- sodium
- decanoyl
- dodecanoyl
- capric
- lauroyl
- 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.)
- Granted
Links
- 239000011734 sodium Substances 0.000 claims 61
- 229910052708 sodium Inorganic materials 0.000 claims 61
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 55
- 125000000400 lauroyl 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])[H] 0.000 claims 14
- 239000008203 oral pharmaceutical composition Substances 0.000 claims 12
- 229940024606 amino acid Drugs 0.000 claims 10
- 235000001014 amino acid Nutrition 0.000 claims 10
- 150000001413 amino acids Chemical class 0.000 claims 9
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 7
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 6
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 6
- -1 cationic amino acid Chemical group 0.000 claims 6
- 229940045944 sodium lauroyl glutamate Drugs 0.000 claims 6
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 claims 6
- IWIUXJGIDSGWDN-UQKRIMTDSA-M sodium;(2s)-2-(dodecanoylamino)pentanedioate;hydron Chemical compound [Na+].CCCCCCCCCCCC(=O)N[C@H](C([O-])=O)CCC(O)=O IWIUXJGIDSGWDN-UQKRIMTDSA-M 0.000 claims 6
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 5
- 108700004121 sarkosyl Proteins 0.000 claims 5
- 229940045885 sodium lauroyl sarcosinate Drugs 0.000 claims 5
- QNAYBMKLOCPYGJ-UHFFFAOYSA-M alaninate Chemical compound CC(N)C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-M 0.000 claims 4
- XUJNEKJLAYXESH-UHFFFAOYSA-L cysteinate(2-) Chemical compound [S-]CC(N)C([O-])=O XUJNEKJLAYXESH-UHFFFAOYSA-L 0.000 claims 4
- 229940049906 glutamate Drugs 0.000 claims 4
- 229930195712 glutamate Natural products 0.000 claims 4
- 229960000310 isoleucine Drugs 0.000 claims 4
- LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 claims 4
- 229960002429 proline Drugs 0.000 claims 4
- 229940079781 sodium cocoyl glutamate Drugs 0.000 claims 4
- 229940078455 sodium lauroyl aspartate Drugs 0.000 claims 4
- IEXXLSKKBWIDAC-ZOWNYOTGSA-M sodium;(3s)-3-(dodecanoylamino)-4-hydroxy-4-oxobutanoate Chemical compound [Na+].CCCCCCCCCCCC(=O)N[C@H](C([O-])=O)CC(O)=O IEXXLSKKBWIDAC-ZOWNYOTGSA-M 0.000 claims 4
- IKGKWKGYFJBGQJ-UHFFFAOYSA-M sodium;2-(dodecanoylamino)acetate Chemical compound [Na+].CCCCCCCCCCCC(=O)NCC([O-])=O IKGKWKGYFJBGQJ-UHFFFAOYSA-M 0.000 claims 4
- QIVBCDIJIAJPQS-UHFFFAOYSA-M tryptophanate Chemical compound C1=CC=C2C(CC(N)C([O-])=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-M 0.000 claims 4
- OUYCCCASQSFEME-UHFFFAOYSA-L tyrosinate(2-) Chemical compound [O-]C(=O)C(N)CC1=CC=C([O-])C=C1 OUYCCCASQSFEME-UHFFFAOYSA-L 0.000 claims 4
- KZSNJWFQEVHDMF-UHFFFAOYSA-M valinate Chemical compound CC(C)C(N)C([O-])=O KZSNJWFQEVHDMF-UHFFFAOYSA-M 0.000 claims 4
- 239000004471 Glycine Substances 0.000 claims 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 3
- 239000004473 Threonine Substances 0.000 claims 3
- 229960001230 asparagine Drugs 0.000 claims 3
- 229940009098 aspartate Drugs 0.000 claims 3
- 150000004665 fatty acids Chemical group 0.000 claims 3
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 3
- 229960004452 methionine Drugs 0.000 claims 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims 3
- ONIBWKKTOPOVIA-UHFFFAOYSA-M prolinate Chemical compound [O-]C(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-M 0.000 claims 3
- 235000018102 proteins Nutrition 0.000 claims 3
- 108090000623 proteins and genes Proteins 0.000 claims 3
- 102000004169 proteins and genes Human genes 0.000 claims 3
- 229940071089 sarcosinate Drugs 0.000 claims 3
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 claims 3
- 229960002898 threonine Drugs 0.000 claims 3
- 229960004295 valine Drugs 0.000 claims 3
- CZJJQSUIALCKCZ-NSHDSACASA-N (2r)-2-(decanoylamino)-3-sulfanylpropanoic acid Chemical compound CCCCCCCCCC(=O)N[C@@H](CS)C(O)=O CZJJQSUIALCKCZ-NSHDSACASA-N 0.000 claims 2
- SZJKBLZPBALIGH-ZDUSSCGKSA-N (2r)-2-(dodecanoylamino)-3-sulfanylpropanoic acid Chemical compound CCCCCCCCCCCC(=O)N[C@@H](CS)C(O)=O SZJKBLZPBALIGH-ZDUSSCGKSA-N 0.000 claims 2
- AJWFQCNUNFFTHX-HNNXBMFYSA-N (2s)-1-dodecanoylpyrrolidine-2-carboxylic acid Chemical compound CCCCCCCCCCCC(=O)N1CCC[C@H]1C(O)=O AJWFQCNUNFFTHX-HNNXBMFYSA-N 0.000 claims 2
- BKVABDKAKQZLJF-AWEZNQCLSA-N (2s)-2-(decanoylamino)-3-(1h-imidazol-5-yl)propanoic acid Chemical compound CCCCCCCCCC(=O)N[C@H](C(O)=O)CC1=CN=CN1 BKVABDKAKQZLJF-AWEZNQCLSA-N 0.000 claims 2
- AYFVGKNJGXCSDI-IBGZPJMESA-N (2s)-2-(decanoylamino)-3-(1h-indol-3-yl)propanoic acid Chemical compound C1=CC=C2C(C[C@H](NC(=O)CCCCCCCCC)C(O)=O)=CNC2=C1 AYFVGKNJGXCSDI-IBGZPJMESA-N 0.000 claims 2
- DJPVXOYGQKTRPA-KRWDZBQOSA-N (2s)-2-(decanoylamino)-3-(4-hydroxyphenyl)propanoic acid Chemical compound CCCCCCCCCC(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 DJPVXOYGQKTRPA-KRWDZBQOSA-N 0.000 claims 2
- AFYMQZVURIZOSA-NSHDSACASA-N (2s)-2-(decanoylamino)-3-hydroxypropanoic acid Chemical compound CCCCCCCCCC(=O)N[C@@H](CO)C(O)=O AFYMQZVURIZOSA-NSHDSACASA-N 0.000 claims 2
- BPZWMTJHFOPXCT-KRWDZBQOSA-N (2s)-2-(decanoylamino)-3-phenylpropanoic acid Chemical compound CCCCCCCCCC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 BPZWMTJHFOPXCT-KRWDZBQOSA-N 0.000 claims 2
- KDQCSJBLQLMYLH-AWEZNQCLSA-N (2s)-2-(decanoylamino)-4-methylpentanoic acid Chemical compound CCCCCCCCCC(=O)N[C@H](C(O)=O)CC(C)C KDQCSJBLQLMYLH-AWEZNQCLSA-N 0.000 claims 2
- WSJCTRAECJWNOS-NSHDSACASA-N (2s)-2-(decanoylamino)butanedioic acid Chemical compound CCCCCCCCCC(=O)N[C@H](C(O)=O)CC(O)=O WSJCTRAECJWNOS-NSHDSACASA-N 0.000 claims 2
- OBACDZMAJJOBJC-LBPRGKRZSA-N (2s)-2-(decanoylamino)pentanedioic acid Chemical compound CCCCCCCCCC(=O)N[C@H](C(O)=O)CCC(O)=O OBACDZMAJJOBJC-LBPRGKRZSA-N 0.000 claims 2
- KMJDEJIZLJQIQI-NSHDSACASA-N (2s)-2-(decanoylamino)propanoic acid Chemical compound CCCCCCCCCC(=O)N[C@@H](C)C(O)=O KMJDEJIZLJQIQI-NSHDSACASA-N 0.000 claims 2
- IGMAHSCLECVIDN-INIZCTEOSA-N (2s)-2-(dodecanoylamino)-3-(1h-imidazol-5-yl)propanoic acid Chemical compound CCCCCCCCCCCC(=O)N[C@H](C(O)=O)CC1=CNC=N1 IGMAHSCLECVIDN-INIZCTEOSA-N 0.000 claims 2
- MTYLJFSVEPZMIY-NRFANRHFSA-N (2s)-2-(dodecanoylamino)-3-(1h-indol-3-yl)propanoic acid Chemical compound C1=CC=C2C(C[C@H](NC(=O)CCCCCCCCCCC)C(O)=O)=CNC2=C1 MTYLJFSVEPZMIY-NRFANRHFSA-N 0.000 claims 2
- XGFQVJQXCLZRFH-ZDUSSCGKSA-N (2s)-2-(dodecanoylamino)-3-hydroxypropanoic acid Chemical compound CCCCCCCCCCCC(=O)N[C@@H](CO)C(O)=O XGFQVJQXCLZRFH-ZDUSSCGKSA-N 0.000 claims 2
- WQHXCNGQDLRDMP-INIZCTEOSA-N (2s)-2-(dodecanoylamino)-3-methylbutanoic acid Chemical compound CCCCCCCCCCCC(=O)N[C@@H](C(C)C)C(O)=O WQHXCNGQDLRDMP-INIZCTEOSA-N 0.000 claims 2
- RKQUHHNIJVGMIG-IBGZPJMESA-N (2s)-2-(dodecanoylamino)-3-phenylpropanoic acid Chemical compound CCCCCCCCCCCC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 RKQUHHNIJVGMIG-IBGZPJMESA-N 0.000 claims 2
- CDOCNWRWMUMCLP-INIZCTEOSA-N (2s)-2-(dodecanoylamino)-4-methylpentanoic acid Chemical compound CCCCCCCCCCCC(=O)N[C@H](C(O)=O)CC(C)C CDOCNWRWMUMCLP-INIZCTEOSA-N 0.000 claims 2
- PFSGUIFKRGNSHV-HNNXBMFYSA-N (2s)-2-(dodecanoylamino)-4-methylsulfanylbutanoic acid Chemical compound CCCCCCCCCCCC(=O)N[C@H](C(O)=O)CCSC PFSGUIFKRGNSHV-HNNXBMFYSA-N 0.000 claims 2
- AVBJHQDHVYGQLS-AWEZNQCLSA-N (2s)-2-(dodecanoylamino)pentanedioic acid Chemical compound CCCCCCCCCCCC(=O)N[C@H](C(O)=O)CCC(O)=O AVBJHQDHVYGQLS-AWEZNQCLSA-N 0.000 claims 2
- UYTOHYBIBPDOKX-ZDUSSCGKSA-N (2s)-2-(dodecanoylamino)propanoic acid Chemical compound CCCCCCCCCCCC(=O)N[C@@H](C)C(O)=O UYTOHYBIBPDOKX-ZDUSSCGKSA-N 0.000 claims 2
- GDJYINIIGLKESK-ZDUSSCGKSA-N (2s)-4-amino-2-(dodecanoylamino)-4-oxobutanoic acid Chemical compound CCCCCCCCCCCC(=O)N[C@H](C(O)=O)CC(N)=O GDJYINIIGLKESK-ZDUSSCGKSA-N 0.000 claims 2
- MZUBOXLGCNTCGH-LBPRGKRZSA-N (2s)-5-amino-2-(decanoylamino)-5-oxopentanoic acid Chemical compound CCCCCCCCCC(=O)N[C@H](C(O)=O)CCC(N)=O MZUBOXLGCNTCGH-LBPRGKRZSA-N 0.000 claims 2
- USMCNVFGYLZLGM-AWEZNQCLSA-N (2s)-5-amino-2-(dodecanoylamino)-5-oxopentanoic acid Chemical compound CCCCCCCCCCCC(=O)N[C@H](C(O)=O)CCC(N)=O USMCNVFGYLZLGM-AWEZNQCLSA-N 0.000 claims 2
- BHPUZXHJBNPVQQ-HIFRSBDPSA-N (2s,3r)-2-(dodecanoylamino)-3-hydroxybutanoic acid Chemical compound CCCCCCCCCCCC(=O)N[C@@H]([C@@H](C)O)C(O)=O BHPUZXHJBNPVQQ-HIFRSBDPSA-N 0.000 claims 2
- IVNYHFWUYNDIDY-RDJZCZTQSA-N (2s,3s)-2-(dodecanoylamino)-3-methylpentanoic acid Chemical compound CCCCCCCCCCCC(=O)N[C@H](C(O)=O)[C@@H](C)CC IVNYHFWUYNDIDY-RDJZCZTQSA-N 0.000 claims 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 claims 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 2
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 2
- DJPVXOYGQKTRPA-UHFFFAOYSA-N N-decanoyl-L-tyrosine Natural products CCCCCCCCCC(=O)NC(C(O)=O)CC1=CC=C(O)C=C1 DJPVXOYGQKTRPA-UHFFFAOYSA-N 0.000 claims 2
- SVQAZCRYIXURJT-UHFFFAOYSA-N N-dodecanoyl-L-tyrosine Natural products CCCCCCCCCCCC(=O)NC(C(O)=O)CC1=CC=C(O)C=C1 SVQAZCRYIXURJT-UHFFFAOYSA-N 0.000 claims 2
- BVQYSBCMUYMJKE-ZOWNYOTGSA-N N[C@@H](CO)C(=O)OC(CCCCCCCCCCC)=O.[Na] Chemical compound N[C@@H](CO)C(=O)OC(CCCCCCCCCCC)=O.[Na] BVQYSBCMUYMJKE-ZOWNYOTGSA-N 0.000 claims 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 2
- 108010077895 Sarcosine Proteins 0.000 claims 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 2
- 125000000539 amino acid group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229960002885 histidine Drugs 0.000 claims 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 2
- 229960003136 leucine Drugs 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- SVQAZCRYIXURJT-IBGZPJMESA-N n-dodecanoyl-l-tyrosine Chemical compound CCCCCCCCCCCC(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 SVQAZCRYIXURJT-IBGZPJMESA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- COLNVLDHVKWLRT-UHFFFAOYSA-M phenylalaninate Chemical compound [O-]C(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-M 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-M serinate Chemical compound OCC(N)C([O-])=O MTCFGRXMJLQNBG-UHFFFAOYSA-M 0.000 claims 2
- 229940065859 sodium cocoyl glycinate Drugs 0.000 claims 2
- 229940077092 sodium myristoyl glutamate Drugs 0.000 claims 2
- 229940045898 sodium stearoyl glutamate Drugs 0.000 claims 2
- FCBUGCHAVCFTHW-NTISSMGPSA-N sodium;(2s)-2-(tetradecanoylamino)pentanedioic acid Chemical compound [Na].CCCCCCCCCCCCCC(=O)N[C@H](C(O)=O)CCC(O)=O FCBUGCHAVCFTHW-NTISSMGPSA-N 0.000 claims 2
- KDHFCTLPQJQDQI-BDQAORGHSA-M sodium;(4s)-4-amino-5-octadecanoyloxy-5-oxopentanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC(=O)OC(=O)[C@@H](N)CCC([O-])=O KDHFCTLPQJQDQI-BDQAORGHSA-M 0.000 claims 2
- VLKIFCBXANYYCK-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enoyl]amino]acetate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CC([O-])=O VLKIFCBXANYYCK-GMFCBQQYSA-M 0.000 claims 2
- QKHBMQWPOUUMQZ-BDQAORGHSA-M sodium;hydron;(2s)-2-(octadecanoylamino)pentanedioate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC(=O)N[C@H](C(O)=O)CCC([O-])=O QKHBMQWPOUUMQZ-BDQAORGHSA-M 0.000 claims 2
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 1
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- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
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- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 1
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- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 1
- 229940043230 sarcosine Drugs 0.000 claims 1
- 229960001153 serine Drugs 0.000 claims 1
- KQYAHAGYCNNBCD-FYZYNONXSA-M sodium;(2s)-2-(dodecanoylamino)-3-phenylpropanoate Chemical compound [Na+].CCCCCCCCCCCC(=O)N[C@H](C([O-])=O)CC1=CC=CC=C1 KQYAHAGYCNNBCD-FYZYNONXSA-M 0.000 claims 1
- WTWSHHITWMVLBX-DKWTVANSSA-M sodium;(2s)-2-aminobutanedioate;hydron Chemical compound [Na+].[O-]C(=O)[C@@H](N)CC(O)=O WTWSHHITWMVLBX-DKWTVANSSA-M 0.000 claims 1
- ZNYIJXQYUNSKDX-NTISSMGPSA-M sodium;hydron;(2s)-2-(tetradecanoylamino)pentanedioate Chemical compound [Na+].CCCCCCCCCCCCCC(=O)N[C@H](C([O-])=O)CCC(O)=O ZNYIJXQYUNSKDX-NTISSMGPSA-M 0.000 claims 1
- 229960004799 tryptophan Drugs 0.000 claims 1
- 229960004441 tyrosine Drugs 0.000 claims 1
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- 239000004474 valine Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
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| US61/477,719 | 2011-04-21 | ||
| PCT/EP2012/056708 WO2012140155A1 (en) | 2011-04-14 | 2012-04-12 | Fatty acid acylated amino acids for oral peptide delivery |
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| WO2014060512A1 (en) * | 2012-10-17 | 2014-04-24 | Novo Nordisk Health Care Ag | Fatty acid acylated amino acids for growth hormone delivery |
| WO2014060472A1 (en) * | 2012-10-17 | 2014-04-24 | Novo Nordisk A/S | Fatty acid acylated amino acids for oral peptide delivery |
| JP6285447B2 (ja) * | 2012-10-17 | 2018-02-28 | ノヴォ ノルディスク アー／エス | 経口ペプチド送達用の脂肪酸アシル化ｄ−アミノ酸 |
| WO2015162195A1 (en) * | 2014-04-23 | 2015-10-29 | Novo Nordisk A/S | Fatty acid acylated amino acids for oral peptide delivery |
| DK3006045T3 (en) | 2014-10-07 | 2017-07-17 | Cyprumed Gmbh | Pharmaceutical formulations for oral administration of peptide or protein drugs |
| CN104961687B (zh) * | 2015-06-03 | 2017-07-25 | 苏州维泰生物技术有限公司 | 1,2‑二嗪衍生物及其制剂、用途 |
| CN111759823B (zh) * | 2015-09-17 | 2022-12-30 | 阿赖耶识（上海）生物技术有限公司 | 一种高稳定的非囊泡型纳米颗粒及其在治疗微生物感染中的应用 |
| EP3359181A1 (en) | 2015-10-07 | 2018-08-15 | Cyprumed GmbH | Pharmaceutical formulations for the oral delivery of peptide drugs |
| WO2018065634A1 (en) | 2016-10-07 | 2018-04-12 | Cyprumed Gmbh | Pharmaceutical compositions for the nasal delivery of peptide or protein drugs |
| BR112020002804A2 (pt) | 2017-08-24 | 2020-07-28 | Novo Nordisk A/S | composição farmacêutica líquida, e, kit |
| TWI751379B (zh) | 2017-09-21 | 2022-01-01 | 奧孟亞股份有限公司 | 用於遞送胜肽之藥物組合物 |
| WO2019108739A1 (en) * | 2017-11-30 | 2019-06-06 | Dana-Farber Cancer Institute, Inc. | Chemical uncouplers of respiration and methods of use thereof |
| FR3075197B1 (fr) * | 2017-12-20 | 2019-11-15 | Societe D'exploitation De Produits Pour Les Industries Chimiques Seppic | Nouvelle composition de lipoaminoacides et de diols, le procede pour leur preparation et composition cosmetique ou pharmaceutique en resultant |
| US20210087250A1 (en) | 2018-04-06 | 2021-03-25 | Cyprumed Gmbh | Pharmaceutical compositions for the transmucosal delivery of therapeutic peptides and proteins |
| KR102853071B1 (ko) | 2019-02-07 | 2025-09-02 | 베이진 엘티디 | Tlr7 작용제로서의 이미다조[2,1-f][1,2,4]트리아진-4-아민 유도체 |
| WO2022049310A1 (en) | 2020-09-07 | 2022-03-10 | Cyprumed Gmbh | Improved pharmaceutical formulations of glp-1 receptor agonists |
| EP4180060A1 (en) | 2021-11-15 | 2023-05-17 | Adocia | Solid compositions comprising a peptide or a protein and an acylated amino acid |
| EP4299057A1 (en) | 2022-06-30 | 2024-01-03 | Adocia | Solid compositions comprising a peptide or a protein and an acylated amino acid |
| EP4433093A1 (en) | 2021-11-15 | 2024-09-25 | Adocia | Solid compositions comprising a peptide or a protein and an acylated amino acid |
| WO2023166179A1 (en) | 2022-03-03 | 2023-09-07 | Cyprumed Gmbh | Improved oral pharmaceutical formulations of therapeutic peptides and proteins |
| EP4299071A1 (en) | 2022-07-01 | 2024-01-03 | Adocia | Compositions comprising a peptide or a protein and an acylated amino acid |
| CN121001710A (zh) | 2022-12-30 | 2025-11-21 | 阿尔吉法玛公司 | 提高口服多肽治疗剂的全身生物利用度的组合物和方法 |
| US12544349B1 (en) | 2024-12-30 | 2026-02-10 | Adocia | Compositions comprising pemvidutide and an acylated amino acid |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2772168A (en) * | 1951-11-28 | 1956-11-27 | Colgate Palmolive Co | Fermentable carbohydrate food products |
| US4258029A (en) * | 1979-04-23 | 1981-03-24 | Connaught Laboratories Limited | Synthetic adjuvants for stimulation of antigenic responses |
| US4749694A (en) * | 1984-04-26 | 1988-06-07 | Merck & Co., Inc. | Novel lysine esters used as absorption |
| US5270032A (en) * | 1990-10-04 | 1993-12-14 | The Research Foundation Of State University Of New York | Composition and method for the prevention and treatment of candidiasis |
| US5498420A (en) * | 1991-04-12 | 1996-03-12 | Merz & Co. Gmbh & Co. | Stable small particle liposome preparations, their production and use in topical cosmetic, and pharmaceutical compositions |
| US6624754B1 (en) * | 1998-01-20 | 2003-09-23 | Hoffman Resources Llc | Personal security and tracking system |
| FR2767064B1 (fr) * | 1997-08-07 | 1999-11-12 | Centre Nat Rech Scient | Procede de liberation d'un principe actif contenu dans une emulsion multiple |
| WO2001035998A1 (en) | 1999-11-12 | 2001-05-25 | Pharmaderm Laboratories, Ltd. | Compositions for transdermal and transmucosal administration of therapeutic agents |
| FR2828102B1 (fr) * | 2001-03-28 | 2004-07-09 | Ifc Sa | Utilisation des lipoaminoacides dans une composition pharmaceutique comme promoteur et systeme disperse a usage pharmaceutique contenant de tels composes |
| US6951655B2 (en) | 2001-10-11 | 2005-10-04 | Imi Biomed, Inc. | Pro-micelle pharmaceutical compositions |
| US8088734B2 (en) | 2003-01-21 | 2012-01-03 | Unigene Laboratories Inc. | Oral delivery of peptides |
| AU2004261353B2 (en) | 2003-08-05 | 2009-12-10 | Novo Nordisk A/S | Novel insulin derivatives |
| US20050282756A1 (en) | 2004-06-18 | 2005-12-22 | Mehta Nozer M | Oral delivery of peptide pharmaceutical compositions |
| JP4147235B2 (ja) * | 2004-09-27 | 2008-09-10 | キヤノン株式会社 | 吐出用液体、吐出方法、液滴化方法、液体吐出カートリッジ及び吐出装置 |
| CN101541830A (zh) | 2006-09-22 | 2009-09-23 | 诺沃-诺迪斯克有限公司 | 蛋白酶抗性的胰岛素类似物 |
| GB0623838D0 (en) * | 2006-11-29 | 2007-01-10 | Malvern Cosmeceutics Ltd | Novel compositions |
| EP2514406A1 (en) | 2007-06-01 | 2012-10-24 | Novo Nordisk A/S | Spontaneously dispersible preconcentrates including a peptide drug in a solid or semisolid carrier |
| HUE032284T2 (en) | 2008-03-18 | 2017-09-28 | Novo Nordisk As | Protease-stabilized, acylated insulin analogues |
| CN102227213A (zh) * | 2008-11-28 | 2011-10-26 | 诺沃—诺迪斯克有限公司 | 适合于衍生化的胰岛素肽的口服施用的药物组合物 |
| JP5123922B2 (ja) | 2009-12-02 | 2013-01-23 | 独立行政法人科学技術振興機構 | 融合糖タンパク質から成るエンベロープを有する逆行性輸送ウィルスベクター系 |
-
2012
- 2012-04-12 CN CN201280017853.5A patent/CN103458873B/zh not_active Expired - Fee Related
- 2012-04-12 EP EP12713173.8A patent/EP2696847A1/en not_active Withdrawn
- 2012-04-12 US US14/111,274 patent/US20140056953A1/en not_active Abandoned
- 2012-04-12 WO PCT/EP2012/056708 patent/WO2012140155A1/en not_active Ceased
- 2012-04-12 JP JP2014504327A patent/JP6030630B2/ja not_active Expired - Fee Related
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