JP2009539862A5 - - Google Patents
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- JP2009539862A5 JP2009539862A5 JP2009514424A JP2009514424A JP2009539862A5 JP 2009539862 A5 JP2009539862 A5 JP 2009539862A5 JP 2009514424 A JP2009514424 A JP 2009514424A JP 2009514424 A JP2009514424 A JP 2009514424A JP 2009539862 A5 JP2009539862 A5 JP 2009539862A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- enhancer
- dac
- fatty acid
- hydroxy
- 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.)
- Pending
Links
- -1 cyclic hydroxamic acids Chemical class 0.000 claims 23
- 239000000203 mixture Substances 0.000 claims 14
- 239000003623 enhancer Substances 0.000 claims 12
- 239000008194 pharmaceutical composition Substances 0.000 claims 10
- 239000003276 histone deacetylase inhibitor Substances 0.000 claims 9
- 239000002253 acid Substances 0.000 claims 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000005456 glyceride group Chemical group 0.000 claims 6
- 150000004820 halides Chemical group 0.000 claims 6
- 229940121372 histone deacetylase inhibitor Drugs 0.000 claims 6
- 150000004667 medium chain fatty acids Chemical class 0.000 claims 6
- JTDYUFSDZATMKU-UHFFFAOYSA-N 6-(1,3-dioxo-2-benzo[de]isoquinolinyl)-N-hydroxyhexanamide Chemical compound C1=CC(C(N(CCCCCC(=O)NO)C2=O)=O)=C3C2=CC=CC3=C1 JTDYUFSDZATMKU-UHFFFAOYSA-N 0.000 claims 5
- NIJJYAXOARWZEE-UHFFFAOYSA-N Valproic acid Chemical compound CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 claims 5
- OHRURASPPZQGQM-GCCNXGTGSA-N romidepsin Chemical compound O1C(=O)[C@H](C(C)C)NC(=O)C(=C/C)/NC(=O)[C@H]2CSSCC\C=C\[C@@H]1CC(=O)N[C@H](C(C)C)C(=O)N2 OHRURASPPZQGQM-GCCNXGTGSA-N 0.000 claims 5
- 229960003452 romidepsin Drugs 0.000 claims 5
- 108010091666 romidepsin Proteins 0.000 claims 5
- OHRURASPPZQGQM-UHFFFAOYSA-N romidepsin Natural products O1C(=O)C(C(C)C)NC(=O)C(=CC)NC(=O)C2CSSCCC=CC1CC(=O)NC(C(C)C)C(=O)N2 OHRURASPPZQGQM-UHFFFAOYSA-N 0.000 claims 5
- 150000008065 acid anhydrides Chemical group 0.000 claims 4
- HGDNKULJQQBFCT-UHFFFAOYSA-N antanapeptin d Chemical compound CN1C(=O)C(C(C)C)NC(=O)C(C)C(CCCC#C)OC(=O)C(C(C)C)N(C)C(=O)C2CCCN2C(=O)C(C(C)C)OC(=O)C1CC1=CC=CC=C1 HGDNKULJQQBFCT-UHFFFAOYSA-N 0.000 claims 4
- VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 claims 4
- HHNFORCFJOVQNF-UHFFFAOYSA-N cyl-1 Chemical compound N1C(=O)C(CCCCCC(=O)C2OC2)NC(=O)C2CCCN2C(=O)C(C(C)CC)NC(=O)C1CC1=CC=C(OC)C=C1 HHNFORCFJOVQNF-UHFFFAOYSA-N 0.000 claims 4
- PFRGXCVKLLPLIP-UHFFFAOYSA-N diallyl disulfide Chemical compound C=CCSSCC=C PFRGXCVKLLPLIP-UHFFFAOYSA-N 0.000 claims 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims 4
- 229930195729 fatty acid Natural products 0.000 claims 4
- 239000000194 fatty acid Substances 0.000 claims 4
- 239000007787 solid Substances 0.000 claims 4
- SUVMJBTUFCVSAD-UHFFFAOYSA-N sulforaphane Chemical compound CS(=O)CCCCN=C=S SUVMJBTUFCVSAD-UHFFFAOYSA-N 0.000 claims 4
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 239000002552 dosage form Substances 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 210000000936 intestine Anatomy 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 229960005480 sodium caprylate Drugs 0.000 claims 3
- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 claims 3
- 229940082004 sodium laurate Drugs 0.000 claims 3
- BYKRNSHANADUFY-UHFFFAOYSA-M sodium octanoate Chemical group [Na+].CCCCCCCC([O-])=O BYKRNSHANADUFY-UHFFFAOYSA-M 0.000 claims 3
- FIWQZURFGYXCEO-UHFFFAOYSA-M sodium;decanoate Chemical compound [Na+].CCCCCCCCCC([O-])=O FIWQZURFGYXCEO-UHFFFAOYSA-M 0.000 claims 3
- 108010060597 trapoxin A Proteins 0.000 claims 3
- RTKIYFITIVXBLE-QEQCGCAPSA-N trichostatin A Chemical compound ONC(=O)/C=C/C(/C)=C/[C@@H](C)C(=O)C1=CC=C(N(C)C)C=C1 RTKIYFITIVXBLE-QEQCGCAPSA-N 0.000 claims 3
- JWOGUUIOCYMBPV-GMFLJSBRSA-N (3S,6S,9S,12R)-3-[(2S)-Butan-2-yl]-6-[(1-methoxyindol-3-yl)methyl]-9-(6-oxooctyl)-1,4,7,10-tetrazabicyclo[10.4.0]hexadecane-2,5,8,11-tetrone Chemical compound N1C(=O)[C@H](CCCCCC(=O)CC)NC(=O)[C@H]2CCCCN2C(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H]1CC1=CN(OC)C2=CC=CC=C12 JWOGUUIOCYMBPV-GMFLJSBRSA-N 0.000 claims 2
- GNYCTMYOHGBSBI-SVZOTFJBSA-N (3s,6r,9s,12r)-6,9-dimethyl-3-[6-[(2s)-oxiran-2-yl]-6-oxohexyl]-1,4,7,10-tetrazabicyclo[10.3.0]pentadecane-2,5,8,11-tetrone Chemical compound C([C@H]1C(=O)N2CCC[C@@H]2C(=O)N[C@H](C(N[C@H](C)C(=O)N1)=O)C)CCCCC(=O)[C@@H]1CO1 GNYCTMYOHGBSBI-SVZOTFJBSA-N 0.000 claims 2
- LLOKIGWPNVSDGJ-AFBVCZJXSA-N (3s,6s,9s,12r)-3,6-dibenzyl-9-[6-[(2s)-oxiran-2-yl]-6-oxohexyl]-1,4,7,10-tetrazabicyclo[10.3.0]pentadecane-2,5,8,11-tetrone Chemical compound C([C@H]1C(=O)N2CCC[C@@H]2C(=O)N[C@H](C(N[C@@H](CC=2C=CC=CC=2)C(=O)N1)=O)CCCCCC(=O)[C@H]1OC1)C1=CC=CC=C1 LLOKIGWPNVSDGJ-AFBVCZJXSA-N 0.000 claims 2
- WANLLPADDCXPGO-WMKJBNATSA-N (6r,9s,12s)-3-[(2s)-butan-2-yl]-6-[(4-methoxyphenyl)methyl]-9-[6-(oxiran-2-yl)-6-oxohexyl]-1,4,7,10-tetrazabicyclo[10.4.0]hexadecane-2,5,8,11-tetrone Chemical compound C([C@@H]1C(=O)NC(C(N2CCCC[C@H]2C(=O)N[C@@H](CCCCCC(=O)C2OC2)C(=O)N1)=O)[C@@H](C)CC)C1=CC=C(OC)C=C1 WANLLPADDCXPGO-WMKJBNATSA-N 0.000 claims 2
- FFXUDLUXUIJFSS-NTCAYCPXSA-N (e)-3-[1-[2-(diethylamino)ethyl]-2-(2-phenylethyl)benzimidazol-5-yl]-n-hydroxyprop-2-enamide Chemical compound N=1C2=CC(\C=C\C(=O)NO)=CC=C2N(CCN(CC)CC)C=1CCC1=CC=CC=C1 FFXUDLUXUIJFSS-NTCAYCPXSA-N 0.000 claims 2
- QRPSQQUYPMFERG-LFYBBSHMSA-N (e)-5-[3-(benzenesulfonamido)phenyl]-n-hydroxypent-2-en-4-ynamide Chemical compound ONC(=O)\C=C\C#CC1=CC=CC(NS(=O)(=O)C=2C=CC=CC=2)=C1 QRPSQQUYPMFERG-LFYBBSHMSA-N 0.000 claims 2
- XZWCFUZJOAZGAI-SDNWHVSQSA-N (e)-n-hydroxy-3-[2-(2-phenylethyl)-1-(2-piperidin-1-ylethyl)benzimidazol-5-yl]prop-2-enamide Chemical compound C=1C=CC=CC=1CCC1=NC2=CC(/C=C/C(=O)NO)=CC=C2N1CCN1CCCCC1 XZWCFUZJOAZGAI-SDNWHVSQSA-N 0.000 claims 2
- RCDIZKAYZBEALO-JLHYYAGUSA-N (e)-n-hydroxy-3-[2-(2-phenylethyl)-1-(2-pyrrolidin-1-ylethyl)benzimidazol-5-yl]prop-2-enamide Chemical compound C=1C=CC=CC=1CCC1=NC2=CC(/C=C/C(=O)NO)=CC=C2N1CCN1CCCC1 RCDIZKAYZBEALO-JLHYYAGUSA-N 0.000 claims 2
- BWDQBBCUWLSASG-MDZDMXLPSA-N (e)-n-hydroxy-3-[4-[[2-hydroxyethyl-[2-(1h-indol-3-yl)ethyl]amino]methyl]phenyl]prop-2-enamide Chemical compound C=1NC2=CC=CC=C2C=1CCN(CCO)CC1=CC=C(\C=C\C(=O)NO)C=C1 BWDQBBCUWLSASG-MDZDMXLPSA-N 0.000 claims 2
- MAUCONCHVWBMHK-UHFFFAOYSA-N 3-[(dimethylamino)methyl]-N-[2-[4-[(hydroxyamino)-oxomethyl]phenoxy]ethyl]-2-benzofurancarboxamide Chemical compound O1C2=CC=CC=C2C(CN(C)C)=C1C(=O)NCCOC1=CC=C(C(=O)NO)C=C1 MAUCONCHVWBMHK-UHFFFAOYSA-N 0.000 claims 2
- KLWPBEWWHJTYDC-SNAWJCMRSA-N 3-[(e)-2-carboxyethenyl]benzoic acid Chemical compound OC(=O)\C=C\C1=CC=CC(C(O)=O)=C1 KLWPBEWWHJTYDC-SNAWJCMRSA-N 0.000 claims 2
- CLKAYMVZNUKCDR-UHFFFAOYSA-N 3-[4-(dimethylamino)phenyl]-n-hydroxyprop-2-enamide Chemical compound CN(C)C1=CC=C(C=CC(=O)NO)C=C1 CLKAYMVZNUKCDR-UHFFFAOYSA-N 0.000 claims 2
- RGWSSTALGUXZMU-UHFFFAOYSA-N 4-(dimethylamino)-n-[6-(hydroxyamino)-6-oxohexyl]benzamide Chemical compound CN(C)C1=CC=C(C(=O)NCCCCCC(=O)NO)C=C1 RGWSSTALGUXZMU-UHFFFAOYSA-N 0.000 claims 2
- WWMASNYTEATYTC-KPKJPENVSA-N 4-(dimethylamino)-n-[[4-[(e)-3-(hydroxyamino)-3-oxoprop-1-enyl]phenyl]methyl]benzamide Chemical compound C1=CC(N(C)C)=CC=C1C(=O)NCC1=CC=C(\C=C\C(=O)NO)C=C1 WWMASNYTEATYTC-KPKJPENVSA-N 0.000 claims 2
- SUVMJBTUFCVSAD-JTQLQIEISA-N 4-Methylsulfinylbutyl isothiocyanate Natural products C[S@](=O)CCCCN=C=S SUVMJBTUFCVSAD-JTQLQIEISA-N 0.000 claims 2
- KWPCQQHCIBCAQM-UHFFFAOYSA-N 4-[(2,2-dimethyl-4-phenylbutanoyl)amino]-n-hydroxybenzamide Chemical compound C=1C=C(C(=O)NO)C=CC=1NC(=O)C(C)(C)CCC1=CC=CC=C1 KWPCQQHCIBCAQM-UHFFFAOYSA-N 0.000 claims 2
- OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 claims 2
- OHUCIUMMEAYVKS-UHFFFAOYSA-N 5-[2-(dimethylamino)ethoxy]-n-[3-[4-(hydroxycarbamoyl)phenyl]prop-2-ynyl]-1h-indole-2-carboxamide Chemical compound C=1C2=CC(OCCN(C)C)=CC=C2NC=1C(=O)NCC#CC1=CC=C(C(=O)NO)C=C1 OHUCIUMMEAYVKS-UHFFFAOYSA-N 0.000 claims 2
- DWIYBCKFYUQVLU-UHFFFAOYSA-N 7-[4-(4-cyanophenyl)phenoxy]-n-hydroxyheptanamide Chemical compound C1=CC(OCCCCCCC(=O)NO)=CC=C1C1=CC=C(C#N)C=C1 DWIYBCKFYUQVLU-UHFFFAOYSA-N 0.000 claims 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical class NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 2
- 241001550224 Apha Species 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- DBBYYRWVNDQECM-CDWOPPGASA-N CG-1521 Chemical compound ONC(=O)\C=C\C=C\C=C\C1=CC=CC=C1 DBBYYRWVNDQECM-CDWOPPGASA-N 0.000 claims 2
- OYBMVMAXKOGYDC-UHFFFAOYSA-N CTPB Chemical compound CCCCCCCCCCCCCCCC1=CC=CC(OCC)=C1C(=O)NC1=CC=C(Cl)C(C(F)(F)F)=C1 OYBMVMAXKOGYDC-UHFFFAOYSA-N 0.000 claims 2
- 101100441844 Caenorhabditis elegans cyl-1 gene Proteins 0.000 claims 2
- 108010063406 Cyl-2 Proteins 0.000 claims 2
- WANLLPADDCXPGO-UHFFFAOYSA-N Cyl-2 Natural products N1C(=O)C(CCCCCC(=O)C2OC2)NC(=O)C2CCCCN2C(=O)C(C(C)CC)NC(=O)C1CC1=CC=C(OC)C=C1 WANLLPADDCXPGO-UHFFFAOYSA-N 0.000 claims 2
- DLVJMFOLJOOWFS-UHFFFAOYSA-N Depudecin Natural products CC(O)C1OC1C=CC1C(C(O)C=C)O1 DLVJMFOLJOOWFS-UHFFFAOYSA-N 0.000 claims 2
- 108010051041 HC toxin Proteins 0.000 claims 2
- 101100382953 Mus musculus Ccnd1 gene Proteins 0.000 claims 2
- PTJGLFIIZFVFJV-UHFFFAOYSA-N N'-hydroxy-N-(3-pyridinyl)octanediamide Chemical compound ONC(=O)CCCCCCC(=O)NC1=CC=CN=C1 PTJGLFIIZFVFJV-UHFFFAOYSA-N 0.000 claims 2
- IDQPVOFTURLJPT-UHFFFAOYSA-N N,N'-dihydroxyoctanediamide Chemical compound ONC(=O)CCCCCCC(=O)NO IDQPVOFTURLJPT-UHFFFAOYSA-N 0.000 claims 2
- HRNLUBSXIHFDHP-UHFFFAOYSA-N N-(2-aminophenyl)-4-[[[4-(3-pyridinyl)-2-pyrimidinyl]amino]methyl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1CNC1=NC=CC(C=2C=NC=CC=2)=N1 HRNLUBSXIHFDHP-UHFFFAOYSA-N 0.000 claims 2
- BHUZLJOUHMBZQY-YXQOSMAKSA-N N-[4-[(2R,4R,6S)-4-[[(4,5-diphenyl-2-oxazolyl)thio]methyl]-6-[4-(hydroxymethyl)phenyl]-1,3-dioxan-2-yl]phenyl]-N'-hydroxyoctanediamide Chemical compound C1=CC(CO)=CC=C1[C@H]1O[C@@H](C=2C=CC(NC(=O)CCCCCCC(=O)NO)=CC=2)O[C@@H](CSC=2OC(=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)C1 BHUZLJOUHMBZQY-YXQOSMAKSA-N 0.000 claims 2
- JWOGUUIOCYMBPV-UHFFFAOYSA-N OT-Key 11219 Natural products N1C(=O)C(CCCCCC(=O)CC)NC(=O)C2CCCCN2C(=O)C(C(C)CC)NC(=O)C1CC1=CN(OC)C2=CC=CC=C12 JWOGUUIOCYMBPV-UHFFFAOYSA-N 0.000 claims 2
- 229930189037 Trapoxin Natural products 0.000 claims 2
- GXVXXETYXSPSOA-UHFFFAOYSA-N Trapoxin A Natural products C1OC1C(=O)CCCCCC(C(NC(CC=1C=CC=CC=1)C(=O)N1)=O)NC(=O)C2CCCCN2C(=O)C1CC1=CC=CC=C1 GXVXXETYXSPSOA-UHFFFAOYSA-N 0.000 claims 2
- LLOKIGWPNVSDGJ-UHFFFAOYSA-N Trapoxin B Natural products C1OC1C(=O)CCCCCC(C(NC(CC=1C=CC=CC=1)C(=O)N1)=O)NC(=O)C2CCCN2C(=O)C1CC1=CC=CC=C1 LLOKIGWPNVSDGJ-UHFFFAOYSA-N 0.000 claims 2
- RTKIYFITIVXBLE-UHFFFAOYSA-N Trichostatin A Natural products ONC(=O)C=CC(C)=CC(C)C(=O)C1=CC=C(N(C)C)C=C1 RTKIYFITIVXBLE-UHFFFAOYSA-N 0.000 claims 2
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 claims 2
- 150000001242 acetic acid derivatives Chemical class 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 2
- 229930189439 antanapeptin Natural products 0.000 claims 2
- HEWGADDUUGVTPF-UHFFFAOYSA-N antanapeptin A Natural products CN1C(=O)C(C(C)C)NC(=O)C(C)C(CCCC#C)OC(=O)C(C(C)CC)N(C)C(=O)C2CCCN2C(=O)C(C(C)C)OC(=O)C1CC1=CC=CC=C1 HEWGADDUUGVTPF-UHFFFAOYSA-N 0.000 claims 2
- LZACOZXZESEOFK-UHFFFAOYSA-N antanapeptin B Natural products CN1C(=O)C(C(C)C)NC(=O)C(C)C(CCCC=C)OC(=O)C(C(C)CC)N(C)C(=O)C2CCCN2C(=O)C(C(C)C)OC(=O)C1CC1=CC=CC=C1 LZACOZXZESEOFK-UHFFFAOYSA-N 0.000 claims 2
- NIFSOTSGUFBSPF-UHFFFAOYSA-N antanapeptin C Natural products CN1C(=O)C(C(C)C)NC(=O)C(C)C(CCCCC)OC(=O)C(C(C)CC)N(C)C(=O)C2CCCN2C(=O)C(C(C)C)OC(=O)C1CC1=CC=CC=C1 NIFSOTSGUFBSPF-UHFFFAOYSA-N 0.000 claims 2
- 108010082820 apicidin Proteins 0.000 claims 2
- 229930186608 apicidin Natural products 0.000 claims 2
- NCNRHFGMJRPRSK-MDZDMXLPSA-N belinostat Chemical compound ONC(=O)\C=C\C1=CC=CC(S(=O)(=O)NC=2C=CC=CC=2)=C1 NCNRHFGMJRPRSK-MDZDMXLPSA-N 0.000 claims 2
- 229960003094 belinostat Drugs 0.000 claims 2
- GYKLFBYWXZYSOW-UHFFFAOYSA-N butanoyloxymethyl 2,2-dimethylpropanoate Chemical compound CCCC(=O)OCOC(=O)C(C)(C)C GYKLFBYWXZYSOW-UHFFFAOYSA-N 0.000 claims 2
- 239000002775 capsule Substances 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 229940109262 curcumin Drugs 0.000 claims 2
- 235000012754 curcumin Nutrition 0.000 claims 2
- 239000004148 curcumin Substances 0.000 claims 2
- DLVJMFOLJOOWFS-INMLLLKOSA-N depudecin Chemical compound C[C@@H](O)[C@@H]1O[C@H]1\C=C\[C@H]1[C@H]([C@H](O)C=C)O1 DLVJMFOLJOOWFS-INMLLLKOSA-N 0.000 claims 2
- QKSGNWJOQMSBEP-UHFFFAOYSA-N diethyl-[[6-[[4-(hydroxycarbamoyl)phenyl]carbamoyloxymethyl]naphthalen-2-yl]methyl]azanium;chloride Chemical compound [Cl-].C1=CC2=CC(C[NH+](CC)CC)=CC=C2C=C1COC(=O)NC1=CC=C(C(=O)NO)C=C1 QKSGNWJOQMSBEP-UHFFFAOYSA-N 0.000 claims 2
- VFLDPWHFBUODDF-UHFFFAOYSA-N diferuloylmethane Natural products C1=C(O)C(OC)=CC(C=CC(=O)CC(=O)C=CC=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-UHFFFAOYSA-N 0.000 claims 2
- NAOMMKDKLCMCHA-YDXQKAQTSA-N diheteropeptin Chemical compound C([C@H]1C(=O)N2CCC[C@@H]2C(=O)N[C@H](C(NC(C)(C)C(=O)N1)=O)CCCCC[C@@H](O)[C@H](O)C)C1=CC=CC=C1 NAOMMKDKLCMCHA-YDXQKAQTSA-N 0.000 claims 2
- NAOMMKDKLCMCHA-UHFFFAOYSA-N diheteropeptin Natural products N1C(=O)C(C)(C)NC(=O)C(CCCCCC(O)C(O)C)NC(=O)C2CCCN2C(=O)C1CC1=CC=CC=C1 NAOMMKDKLCMCHA-UHFFFAOYSA-N 0.000 claims 2
- GNYCTMYOHGBSBI-UHFFFAOYSA-N helminthsporium carbonum toxin Natural products N1C(=O)C(C)NC(=O)C(C)NC(=O)C2CCCN2C(=O)C1CCCCCC(=O)C1CO1 GNYCTMYOHGBSBI-UHFFFAOYSA-N 0.000 claims 2
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 150000002576 ketones Chemical class 0.000 claims 2
- 150000003951 lactams Chemical class 0.000 claims 2
- AAVPZQDZCOWSTD-IVTHGCCQSA-N n'-(2-aminophenyl)-n-[3-[(2s,4s,6r)-4-[(4-benzylpiperazin-1-yl)methyl]-6-[4-(hydroxymethyl)phenyl]-1,3-dioxan-2-yl]phenyl]heptanediamide Chemical compound NC1=CC=CC=C1NC(=O)CCCCCC(=O)NC1=CC=CC([C@H]2O[C@H](C[C@@H](CN3CCN(CC=4C=CC=CC=4)CC3)O2)C=2C=CC(CO)=CC=2)=C1 AAVPZQDZCOWSTD-IVTHGCCQSA-N 0.000 claims 2
- OYKBQNOPCSXWBL-SNAWJCMRSA-N n-hydroxy-3-[(e)-3-(hydroxyamino)-3-oxoprop-1-enyl]benzamide Chemical compound ONC(=O)\C=C\C1=CC=CC(C(=O)NO)=C1 OYKBQNOPCSXWBL-SNAWJCMRSA-N 0.000 claims 2
- LAMIXXKAWNLXOC-UHFFFAOYSA-N n-hydroxy-4-[(3-methyl-2-phenylbutanoyl)amino]benzamide Chemical compound C=1C=CC=CC=1C(C(C)C)C(=O)NC1=CC=C(C(=O)NO)C=C1 LAMIXXKAWNLXOC-UHFFFAOYSA-N 0.000 claims 2
- 239000006186 oral dosage form Substances 0.000 claims 2
- 150000002898 organic sulfur compounds Chemical class 0.000 claims 2
- 229950009215 phenylbutanoic acid Drugs 0.000 claims 2
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| CN101198316A (zh) * | 2005-03-17 | 2008-06-11 | 伊兰制药国际有限公司 | 纳米微粒双膦酸盐组合物 |
| IL174387A0 (en) * | 2005-03-31 | 2008-01-20 | Dexcel Pharma Technologies Ltd | A solid composition for intra-oral delivery of insulin |
| TW200716140A (en) * | 2005-06-17 | 2007-05-01 | Dynamis Therapeutics Inc | Treatment of inflammatory conditions |
| KR101191322B1 (ko) * | 2006-04-07 | 2012-10-16 | 메리온 리서치 Ⅲ 리미티드 | 증진제를 함유하는 고형 경구용 투여 제형 |
| US20090004281A1 (en) * | 2007-06-26 | 2009-01-01 | Biovail Laboratories International S.R.L. | Multiparticulate osmotic delivery system |
-
2007
- 2007-06-11 EP EP07795977A patent/EP2040731A4/en not_active Withdrawn
- 2007-06-11 US US11/761,233 patent/US20070292512A1/en not_active Abandoned
- 2007-06-11 CA CA002654566A patent/CA2654566A1/en not_active Abandoned
- 2007-06-11 JP JP2009514424A patent/JP2009539862A/ja active Pending
- 2007-06-11 WO PCT/US2007/013693 patent/WO2007146234A2/en not_active Ceased
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