CA2654566A1

CA2654566A1 - Solid oral dosage form containing an enhancer

Solid oral dosage form containing an enhancer Download PDF

Info

Publication number: CA2654566A1
Authority: CA; Canada
Prior art keywords: dosage form; enhancer; acid; composition; antanapeptin
Prior art date: 2006-06-09
Legal status : Abandoned

Application number

CA002654566A

Other languages

English (en)

French (fr)

Inventor

Thomas W. Leonard

Edel O'toole

Orlagh Feeney

Current Assignee

Merrion Research Ill Ltd

Original Assignee

Individual

Priority date

2006-06-09

Filing date

2007-06-11

Publication date

2007-12-21

2007-06-11 Application filed by Individual filed Critical Individual

2007-12-21 Publication of CA2654566A1 publication Critical patent/CA2654566A1/en

Status Abandoned legal-status Critical Current

Links

239000003623 enhancer Substances 0.000 title claims abstract description 181
239000007787 solid Substances 0.000 title claims abstract description 32
239000006186 oral dosage form Substances 0.000 title claims abstract description 27
239000002552 dosage form Substances 0.000 claims abstract description 98
239000003112 inhibitor Substances 0.000 claims abstract description 66
150000004667 medium chain fatty acids Chemical class 0.000 claims abstract description 42
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 33
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 29
230000003111 delayed effect Effects 0.000 claims abstract description 21
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
239000003826 tablet Substances 0.000 claims description 125
239000000203 mixture Substances 0.000 claims description 110
239000003814 drug Substances 0.000 claims description 96
229940079593 drug Drugs 0.000 claims description 95
-1 aroyl pyrrolyl hydroxyamides Chemical class 0.000 claims description 94
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 description 88
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 description 85
108010091666 romidepsin Proteins 0.000 claims description 84
229960003452 romidepsin Drugs 0.000 claims description 84
FIWQZURFGYXCEO-UHFFFAOYSA-M sodium;decanoate Chemical compound [Na+].CCCCCCCCCC([O-])=O FIWQZURFGYXCEO-UHFFFAOYSA-M 0.000 claims description 69
238000000034 method Methods 0.000 claims description 38
239000002775 capsule Substances 0.000 claims description 31
235000014113 dietary fatty acids Nutrition 0.000 claims description 30
229930195729 fatty acid Natural products 0.000 claims description 30
239000000194 fatty acid Substances 0.000 claims description 30
239000008187 granular material Substances 0.000 claims description 29
150000003839 salts Chemical class 0.000 claims description 29
239000002253 acid Substances 0.000 claims description 27
125000005456 glyceride group Chemical group 0.000 claims description 22
150000001875 compounds Chemical class 0.000 claims description 21
NIJJYAXOARWZEE-UHFFFAOYSA-N Valproic acid Chemical compound CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 claims description 20
238000004519 manufacturing process Methods 0.000 claims description 20
229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 19
239000001267 polyvinylpyrrolidone Substances 0.000 claims description 18
235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 18
238000000576 coating method Methods 0.000 claims description 16
150000002148 esters Chemical class 0.000 claims description 16
150000004820 halides Chemical group 0.000 claims description 16
239000002245 particle Substances 0.000 claims description 16
238000011282 treatment Methods 0.000 claims description 16
BYKRNSHANADUFY-UHFFFAOYSA-M sodium octanoate Chemical group [Na+].CCCCCCCC([O-])=O BYKRNSHANADUFY-UHFFFAOYSA-M 0.000 claims description 15
VAZAPHZUAVEOMC-UHFFFAOYSA-N tacedinaline Chemical compound C1=CC(NC(=O)C)=CC=C1C(=O)NC1=CC=CC=C1N VAZAPHZUAVEOMC-UHFFFAOYSA-N 0.000 claims description 15
239000011248 coating agent Substances 0.000 claims description 14
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 description 14
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 description 14
PFRGXCVKLLPLIP-UHFFFAOYSA-N diallyl disulfide Chemical compound C=CCSSCC=C PFRGXCVKLLPLIP-UHFFFAOYSA-N 0.000 claims description 14
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 description 14
229960005480 sodium caprylate Drugs 0.000 claims description 14
SUVMJBTUFCVSAD-UHFFFAOYSA-N sulforaphane Chemical compound CS(=O)CCCCN=C=S SUVMJBTUFCVSAD-UHFFFAOYSA-N 0.000 claims description 14
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 description 13
239000000463 material Substances 0.000 claims description 13
229920000642 polymer Polymers 0.000 claims description 13
108090000765 processed proteins & peptides Proteins 0.000 claims description 13
239000000546 pharmaceutical excipient Substances 0.000 claims description 12
230000008569 process Effects 0.000 claims description 12
239000008185 minitablet Substances 0.000 claims description 11
239000002861 polymer material Substances 0.000 claims description 11
159000000000 sodium salts Chemical group 0.000 claims description 11
229960000237 vorinostat Drugs 0.000 claims description 11
WAEXFXRVDQXREF-UHFFFAOYSA-N vorinostat Chemical compound ONC(=O)CCCCCCC(=O)NC1=CC=CC=C1 WAEXFXRVDQXREF-UHFFFAOYSA-N 0.000 claims description 11
206010028980 Neoplasm Diseases 0.000 claims description 10
102000004196 processed proteins & peptides Human genes 0.000 claims description 10
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 description 10
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 description 9
210000000936 intestine Anatomy 0.000 claims description 9
239000008188 pellet Substances 0.000 claims description 9
BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 claims description 9
229940082004 sodium laurate Drugs 0.000 claims description 9
238000012384 transportation and delivery Methods 0.000 claims description 9
IDQPVOFTURLJPT-UHFFFAOYSA-N N,N'-dihydroxyoctanediamide Chemical compound ONC(=O)CCCCCCC(=O)NO IDQPVOFTURLJPT-UHFFFAOYSA-N 0.000 claims description 8
108010060597 trapoxin A Proteins 0.000 claims description 8
LMAFSGDNHVBIHU-XUIWWLCJSA-N (2e)-3-(3-bromo-4-hydroxyphenyl)-n-[2-[2-[[(2e)-3-(3-bromo-4-hydroxyphenyl)-2-hydroxyiminopropanoyl]amino]ethyldisulfanyl]ethyl]-2-hydroxyiminopropanamide Chemical compound C=1C=C(O)C(Br)=CC=1C/C(=N\O)C(=O)NCCSSCCNC(=O)C(=N/O)/CC1=CC=C(O)C(Br)=C1 LMAFSGDNHVBIHU-XUIWWLCJSA-N 0.000 claims description 7
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 description 7
DYQZJCUKWTVTLH-HTUOISEFSA-N (3s,6r,9s,12s)-6-benzyl-3-(2-methylpropyl)-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)N[C@H](C(N2CCCC[C@H]2C(=O)N[C@@H](CCCCCC(=O)C2OC2)C(=O)N1)=O)CC(C)C)C1=CC=CC=C1 DYQZJCUKWTVTLH-HTUOISEFSA-N 0.000 claims description 7
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 description 7
SGYJGGKDGBXCNY-QXUYBEEESA-N (3s,9s,12r)-3-benzyl-6,6-dimethyl-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)NC(C(N[C@@H](CC=2C=CC=CC=2)C(=O)N2CCC[C@@H]2C(=O)N1)=O)(C)C)CCCCC(=O)[C@@H]1CO1 SGYJGGKDGBXCNY-QXUYBEEESA-N 0.000 claims description 7
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 description 7
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 description 7
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 description 7
JUNHQBJCWZVSAT-BQYQJAHWSA-N (e)-n-hydroxy-3-[1-methyl-4-(4-methylbenzoyl)pyrrol-2-yl]prop-2-enamide Chemical compound C1=CC(C)=CC=C1C(=O)C1=CN(C)C(\C=C\C(=O)NO)=C1 JUNHQBJCWZVSAT-BQYQJAHWSA-N 0.000 claims description 7
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 description 7
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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 description 7
RANXASMHOHQHDA-YBFXNURJSA-N 2-[2-[2-[[(2e)-3-(3-bromo-4-hydroxyphenyl)-2-hydroxyiminopropanoyl]amino]ethyldisulfanyl]ethylamino]-2-oxoacetic acid Chemical compound OC(=O)C(=O)NCCSSCCNC(=O)C(=N/O)/CC1=CC=C(O)C(Br)=C1 RANXASMHOHQHDA-YBFXNURJSA-N 0.000 claims description 7
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 description 7
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 description 7
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 description 7
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 description 7
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OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 claims description 7
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 description 7
FUZYTVDVLBBXDL-UHFFFAOYSA-N 6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide Chemical compound N1C2=CC=C(Cl)C=C2C2=C1C(C(=O)N)CCC2 FUZYTVDVLBBXDL-UHFFFAOYSA-N 0.000 claims description 7
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 description 7
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical class NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 7
ZHDYUIWBYAYXJQ-UHFFFAOYSA-N Amijiol Natural products C1CC2(C)C(O)CCC(=C)C2(O)CC2(C)CCC(C(C)C)=C21 ZHDYUIWBYAYXJQ-UHFFFAOYSA-N 0.000 claims description 7
241001550224 Apha Species 0.000 claims description 7
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical group CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 7
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 7
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 description 7
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 description 7
101100441844 Caenorhabditis elegans cyl-1 gene Proteins 0.000 claims description 7
SGYJGGKDGBXCNY-UHFFFAOYSA-N Chlamydocin Natural products N1C(=O)C2CCCN2C(=O)C(CC=2C=CC=CC=2)NC(=O)C(C)(C)NC(=O)C1CCCCCC(=O)C1CO1 SGYJGGKDGBXCNY-UHFFFAOYSA-N 0.000 claims description 7
108010063406 Cyl-2 Proteins 0.000 claims description 7
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DLVJMFOLJOOWFS-UHFFFAOYSA-N Depudecin Natural products CC(O)C1OC1C=CC1C(C(O)C=C)O1 DLVJMFOLJOOWFS-UHFFFAOYSA-N 0.000 claims description 7
108010051041 HC toxin Proteins 0.000 claims description 7
101100382953 Mus musculus Ccnd1 gene Proteins 0.000 claims description 7
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 description 7
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 description 7
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 description 7
DISXKJJDDVRQSD-KLMIADJASA-N Spiruchostatin C Chemical compound C1SSCC\C=C\[C@H]2OC(=O)C[C@H](O)[C@@H]([C@@H](C)CC)NC(=O)[C@@H]1NC(=O)[C@@H](CCS(C)=O)NC(=O)C2 DISXKJJDDVRQSD-KLMIADJASA-N 0.000 claims description 7
229930189037 Trapoxin Natural products 0.000 claims description 7
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150000001242 acetic acid derivatives Chemical class 0.000 claims description 7
229930189439 antanapeptin Natural products 0.000 claims description 7
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 description 7
229960003094 belinostat Drugs 0.000 claims description 7
229940054066 benzamide antipsychotics Drugs 0.000 claims description 7
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GYKLFBYWXZYSOW-UHFFFAOYSA-N butanoyloxymethyl 2,2-dimethylpropanoate Chemical compound CCCC(=O)OCOC(=O)C(C)(C)C GYKLFBYWXZYSOW-UHFFFAOYSA-N 0.000 claims description 7
UXJFDYIHRJGPFS-WPWMEQJKSA-N chembl380797 Chemical compound C=1C=CC=C(\N=C\C=2C3=CC=CC=C3C=CC=2O)C=1C(=O)NC(C)C1=CC=CC=C1 UXJFDYIHRJGPFS-WPWMEQJKSA-N 0.000 claims description 7
108700023145 chlamydocin Proteins 0.000 claims description 7
229940109262 curcumin Drugs 0.000 claims description 7
235000012754 curcumin Nutrition 0.000 claims description 7
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125000004122 cyclic group Chemical group 0.000 claims description 7
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 description 7
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 description 7
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