JP2016534071A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2016534071A5 JP2016534071A5 JP2016525902A JP2016525902A JP2016534071A5 JP 2016534071 A5 JP2016534071 A5 JP 2016534071A5 JP 2016525902 A JP2016525902 A JP 2016525902A JP 2016525902 A JP2016525902 A JP 2016525902A JP 2016534071 A5 JP2016534071 A5 JP 2016534071A5
- Authority
- JP
- Japan
- Prior art keywords
- tyrosine
- methyl
- amino
- propanoate
- chloro
- 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
- 150000003667 tyrosine derivatives Chemical class 0.000 claims description 76
- 238000000034 method Methods 0.000 claims description 61
- 239000007787 solid Substances 0.000 claims description 59
- 239000011236 particulate material Substances 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 49
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 29
- -1 2-chloro-3,4-dimethoxyphenyl Chemical group 0.000 claims description 24
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 claims description 20
- VXYFARNRGZWHTJ-SBSPUUFOSA-N hydron;methyl (2r)-2-amino-3-(4-hydroxyphenyl)propanoate;chloride Chemical compound Cl.COC(=O)[C@H](N)CC1=CC=C(O)C=C1 VXYFARNRGZWHTJ-SBSPUUFOSA-N 0.000 claims description 20
- OUYCCCASQSFEME-MRVPVSSYSA-N D-tyrosine Chemical compound OC(=O)[C@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-MRVPVSSYSA-N 0.000 claims description 16
- 206010028980 Neoplasm Diseases 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 15
- 201000011510 cancer Diseases 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 13
- 229940079593 drug Drugs 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 10
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims description 10
- MDKCFLQDBWCQCV-UHFFFAOYSA-N benzyl isothiocyanate Chemical compound S=C=NCC1=CC=CC=C1 MDKCFLQDBWCQCV-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 230000006907 apoptotic process Effects 0.000 claims description 9
- 239000013618 particulate matter Substances 0.000 claims description 8
- 239000002245 particle Substances 0.000 claims description 7
- NHTGHBARYWONDQ-JTQLQIEISA-N L-α-methyl-Tyrosine Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C=C1 NHTGHBARYWONDQ-JTQLQIEISA-N 0.000 claims description 6
- OOTFAHIVGAQXOL-LBPRGKRZSA-N (2,5-dioxopyrrolidin-1-yl) (2s)-3-(4-hydroxy-3,5-diiodophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound C([C@H](NC(=O)OC(C)(C)C)C(=O)ON1C(CCC1=O)=O)C1=CC(I)=C(O)C(I)=C1 OOTFAHIVGAQXOL-LBPRGKRZSA-N 0.000 claims description 5
- NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 claims description 5
- JZKXXXDKRQWDET-UHFFFAOYSA-N 2-azaniumyl-3-(3-hydroxyphenyl)propanoate Chemical compound OC(=O)C(N)CC1=CC=CC(O)=C1 JZKXXXDKRQWDET-UHFFFAOYSA-N 0.000 claims description 5
- WRFPVMFCRNYQNR-UHFFFAOYSA-N 2-hydroxyphenylalanine Chemical compound OC(=O)C(N)CC1=CC=CC=C1O WRFPVMFCRNYQNR-UHFFFAOYSA-N 0.000 claims description 5
- WWYDYZMNFQIYPT-UHFFFAOYSA-L 2-phenylpropanedioate Chemical compound [O-]C(=O)C(C([O-])=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-L 0.000 claims description 5
- ACWBBAGYTKWBCD-ZETCQYMHSA-N 3-chloro-L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(Cl)=C1 ACWBBAGYTKWBCD-ZETCQYMHSA-N 0.000 claims description 5
- FBTSQILOGYXGMD-LURJTMIESA-N 3-nitro-L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C([N+]([O-])=O)=C1 FBTSQILOGYXGMD-LURJTMIESA-N 0.000 claims description 5
- SHGAZHPCJJPHSC-ZVCIMWCZSA-N 9-cis-retinoic acid Chemical compound OC(=O)/C=C(\C)/C=C/C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-ZVCIMWCZSA-N 0.000 claims description 5
- BFYIZQONLCFLEV-DAELLWKTSA-N Aromasine Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(=C)C2=C1 BFYIZQONLCFLEV-DAELLWKTSA-N 0.000 claims description 5
- MLDQJTXFUGDVEO-UHFFFAOYSA-N BAY-43-9006 Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 MLDQJTXFUGDVEO-UHFFFAOYSA-N 0.000 claims description 5
- 190000008236 Carboplatin Chemical compound 0.000 claims description 5
- ZBNZXTGUTAYRHI-UHFFFAOYSA-N Dasatinib Chemical compound C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1Cl ZBNZXTGUTAYRHI-UHFFFAOYSA-N 0.000 claims description 5
- VWUXBMIQPBEWFH-WCCTWKNTSA-N Fulvestrant Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3[C@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)CC2=C1 VWUXBMIQPBEWFH-WCCTWKNTSA-N 0.000 claims description 5
- 239000005411 L01XE02 - Gefitinib Substances 0.000 claims description 5
- 239000005551 L01XE03 - Erlotinib Substances 0.000 claims description 5
- 239000002147 L01XE04 - Sunitinib Substances 0.000 claims description 5
- 239000005511 L01XE05 - Sorafenib Substances 0.000 claims description 5
- 239000002067 L01XE06 - Dasatinib Substances 0.000 claims description 5
- 239000002136 L01XE07 - Lapatinib Substances 0.000 claims description 5
- 239000005536 L01XE08 - Nilotinib Substances 0.000 claims description 5
- 239000003798 L01XE11 - Pazopanib Substances 0.000 claims description 5
- 239000002118 L01XE12 - Vandetanib Substances 0.000 claims description 5
- 239000002145 L01XE14 - Bosutinib Substances 0.000 claims description 5
- 239000002176 L01XE26 - Cabozantinib Substances 0.000 claims description 5
- QAADZYUXQLUXFX-UHFFFAOYSA-N N-phenylmethylthioformamide Natural products S=CNCC1=CC=CC=C1 QAADZYUXQLUXFX-UHFFFAOYSA-N 0.000 claims description 5
- CBPNZQVSJQDFBE-FUXHJELOSA-N Temsirolimus Chemical compound C1C[C@@H](OC(=O)C(C)(CO)CO)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 CBPNZQVSJQDFBE-FUXHJELOSA-N 0.000 claims description 5
- VXYFARNRGZWHTJ-UHFFFAOYSA-N [3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]azanium;chloride Chemical compound Cl.COC(=O)C(N)CC1=CC=C(O)C=C1 VXYFARNRGZWHTJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 5
- 229960001445 alitretinoin Drugs 0.000 claims description 5
- 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 5
- 229960002932 anastrozole Drugs 0.000 claims description 5
- YBBLVLTVTVSKRW-UHFFFAOYSA-N anastrozole Chemical compound N#CC(C)(C)C1=CC(C(C)(C#N)C)=CC(CN2N=CN=C2)=C1 YBBLVLTVTVSKRW-UHFFFAOYSA-N 0.000 claims description 5
- 230000033115 angiogenesis Effects 0.000 claims description 5
- 239000003886 aromatase inhibitor Substances 0.000 claims description 5
- GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 claims description 5
- 229960001467 bortezomib Drugs 0.000 claims description 5
- UBPYILGKFZZVDX-UHFFFAOYSA-N bosutinib Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCCN4CCN(C)CC4)C=C3N=CC=2C#N)=C1Cl UBPYILGKFZZVDX-UHFFFAOYSA-N 0.000 claims description 5
- 229960003736 bosutinib Drugs 0.000 claims description 5
- 229960001292 cabozantinib Drugs 0.000 claims description 5
- ONIQOQHATWINJY-UHFFFAOYSA-N cabozantinib Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1)=CC=C1NC(=O)C1(C(=O)NC=2C=CC(F)=CC=2)CC1 ONIQOQHATWINJY-UHFFFAOYSA-N 0.000 claims description 5
- 229960004562 carboplatin Drugs 0.000 claims description 5
- BLMPQMFVWMYDKT-NZTKNTHTSA-N carfilzomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)[C@]1(C)OC1)NC(=O)CN1CCOCC1)CC1=CC=CC=C1 BLMPQMFVWMYDKT-NZTKNTHTSA-N 0.000 claims description 5
- 229960002438 carfilzomib Drugs 0.000 claims description 5
- 108010021331 carfilzomib Proteins 0.000 claims description 5
- 229960002448 dasatinib Drugs 0.000 claims description 5
- 229960002923 denileukin diftitox Drugs 0.000 claims description 5
- 108010017271 denileukin diftitox Proteins 0.000 claims description 5
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229960001433 erlotinib Drugs 0.000 claims description 5
- AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- BQULAXAVRFIAHN-UHFFFAOYSA-N ethyl 2-amino-3-(4-hydroxyphenyl)propanoate;hydron;chloride Chemical compound Cl.CCOC(=O)C(N)CC1=CC=C(O)C=C1 BQULAXAVRFIAHN-UHFFFAOYSA-N 0.000 claims description 5
- 229960000255 exemestane Drugs 0.000 claims description 5
- JZUZJVFERQWLNC-FQEVSTJZSA-N fmoc-3-nitro-l-tyrosine Chemical compound C([C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=C(O)C([N+]([O-])=O)=C1 JZUZJVFERQWLNC-FQEVSTJZSA-N 0.000 claims description 5
- 229960002258 fulvestrant Drugs 0.000 claims description 5
- 229960002584 gefitinib Drugs 0.000 claims description 5
- XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 claims description 5
- 230000014509 gene expression Effects 0.000 claims description 5
- 229960003685 imatinib mesylate Drugs 0.000 claims description 5
- YLMAHDNUQAMNNX-UHFFFAOYSA-N imatinib methanesulfonate Chemical compound CS(O)(=O)=O.C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 YLMAHDNUQAMNNX-UHFFFAOYSA-N 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 5
- 229960004891 lapatinib Drugs 0.000 claims description 5
- BCFGMOOMADDAQU-UHFFFAOYSA-N lapatinib Chemical compound O1C(CNCCS(=O)(=O)C)=CC=C1C1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4C=C(F)C=CC=4)=CC=3)C2=C1 BCFGMOOMADDAQU-UHFFFAOYSA-N 0.000 claims description 5
- 229960003881 letrozole Drugs 0.000 claims description 5
- HPJKCIUCZWXJDR-UHFFFAOYSA-N letrozole Chemical compound C1=CC(C#N)=CC=C1C(N1N=CN=C1)C1=CC=C(C#N)C=C1 HPJKCIUCZWXJDR-UHFFFAOYSA-N 0.000 claims description 5
- BICWDWHXTTXTDU-MRVPVSSYSA-N methyl (2r)-2-amino-3-(2,6-dichloro-3,4-dimethoxyphenyl)propanoate Chemical compound COC(=O)[C@H](N)CC1=C(Cl)C=C(OC)C(OC)=C1Cl BICWDWHXTTXTDU-MRVPVSSYSA-N 0.000 claims description 5
- BPKBTKQFMPZVNO-SSDOTTSWSA-N methyl (2r)-2-amino-3-(2,6-dichloro-3-hydroxy-4-methoxyphenyl)propanoate Chemical compound COC(=O)[C@H](N)CC1=C(Cl)C=C(OC)C(O)=C1Cl BPKBTKQFMPZVNO-SSDOTTSWSA-N 0.000 claims description 5
- WOOVWLVXVNIALE-SSDOTTSWSA-N methyl (2r)-2-amino-3-(2-chloro-3-hydroxy-4-methoxyphenyl)propanoate Chemical compound COC(=O)[C@H](N)CC1=CC=C(OC)C(O)=C1Cl WOOVWLVXVNIALE-SSDOTTSWSA-N 0.000 claims description 5
- URTGFUAPYILQFF-SECBINFHSA-N methyl (2r)-2-amino-3-(2-chloro-4-hydroxyphenyl)propanoate Chemical group COC(=O)[C@H](N)CC1=CC=C(O)C=C1Cl URTGFUAPYILQFF-SECBINFHSA-N 0.000 claims description 5
- JRBGZVHYLIYGFT-SECBINFHSA-N methyl (2r)-2-amino-3-(3-chloro-4,5-dimethoxyphenyl)propanoate Chemical compound COC(=O)[C@H](N)CC1=CC(Cl)=C(OC)C(OC)=C1 JRBGZVHYLIYGFT-SECBINFHSA-N 0.000 claims description 5
- YBYSJBGPVNPDJO-MRVPVSSYSA-N methyl (2r)-2-amino-3-(3-chloro-4-hydroxy-5-methoxyphenyl)propanoate Chemical compound COC(=O)[C@H](N)CC1=CC(Cl)=C(O)C(OC)=C1 YBYSJBGPVNPDJO-MRVPVSSYSA-N 0.000 claims description 5
- KWTIOVPQMRSIJF-MRVPVSSYSA-N methyl (2r)-2-amino-3-(3-chloro-4-hydroxyphenyl)propanoate Chemical compound COC(=O)[C@H](N)CC1=CC=C(O)C(Cl)=C1 KWTIOVPQMRSIJF-MRVPVSSYSA-N 0.000 claims description 5
- QUBSTZJVDZUTFR-SECBINFHSA-N methyl (2r)-2-amino-3-(3-chloro-4-methoxyphenyl)propanoate Chemical compound COC(=O)[C@H](N)CC1=CC=C(OC)C(Cl)=C1 QUBSTZJVDZUTFR-SECBINFHSA-N 0.000 claims description 5
- ZSDSFDQBWLLWEN-MRVPVSSYSA-N methyl (2r)-2-amino-3-(3-chloro-5-fluoro-4-hydroxyphenyl)propanoate Chemical compound COC(=O)[C@H](N)CC1=CC(F)=C(O)C(Cl)=C1 ZSDSFDQBWLLWEN-MRVPVSSYSA-N 0.000 claims description 5
- MWZPENIJLUWBSY-SECBINFHSA-N methyl (2r)-2-amino-3-(4-hydroxyphenyl)propanoate Chemical compound COC(=O)[C@H](N)CC1=CC=C(O)C=C1 MWZPENIJLUWBSY-SECBINFHSA-N 0.000 claims description 5
- ZXXAWWHROSUPMV-MRXNPFEDSA-N methyl (2r)-2-amino-3-[4-[(2-chloro-6-fluorophenyl)methoxy]phenyl]propanoate Chemical compound C1=CC(C[C@@H](N)C(=O)OC)=CC=C1OCC1=C(F)C=CC=C1Cl ZXXAWWHROSUPMV-MRXNPFEDSA-N 0.000 claims description 5
- HHZIURLSWUIHRB-UHFFFAOYSA-N nilotinib Chemical compound C1=NC(C)=CN1C1=CC(NC(=O)C=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 HHZIURLSWUIHRB-UHFFFAOYSA-N 0.000 claims description 5
- 229960001346 nilotinib Drugs 0.000 claims description 5
- DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 claims description 5
- 229960001756 oxaliplatin Drugs 0.000 claims description 5
- 229960000639 pazopanib Drugs 0.000 claims description 5
- CUIHSIWYWATEQL-UHFFFAOYSA-N pazopanib Chemical compound C1=CC2=C(C)N(C)N=C2C=C1N(C)C(N=1)=CC=NC=1NC1=CC=C(C)C(S(N)(=O)=O)=C1 CUIHSIWYWATEQL-UHFFFAOYSA-N 0.000 claims description 5
- OGSBUKJUDHAQEA-WMCAAGNKSA-N pralatrexate Chemical compound C1=NC2=NC(N)=NC(N)=C2N=C1CC(CC#C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OGSBUKJUDHAQEA-WMCAAGNKSA-N 0.000 claims description 5
- 229960000214 pralatrexate Drugs 0.000 claims description 5
- 108090000623 proteins and genes Proteins 0.000 claims description 5
- 102000004169 proteins and genes Human genes 0.000 claims description 5
- 229960003787 sorafenib Drugs 0.000 claims description 5
- 229960001796 sunitinib Drugs 0.000 claims description 5
- WINHZLLDWRZWRT-ATVHPVEESA-N sunitinib Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C WINHZLLDWRZWRT-ATVHPVEESA-N 0.000 claims description 5
- 229960001603 tamoxifen Drugs 0.000 claims description 5
- 229960000235 temsirolimus Drugs 0.000 claims description 5
- QFJCIRLUMZQUOT-UHFFFAOYSA-N temsirolimus Natural products C1CC(O)C(OC)CC1CC(C)C1OC(=O)C2CCCCN2C(=O)C(=O)C(O)(O2)C(C)CCC2CC(OC)C(C)=CC=CC=CC(C)CC(C)C(=O)C(OC)C(O)C(C)=CC(C)C(=O)C1 QFJCIRLUMZQUOT-UHFFFAOYSA-N 0.000 claims description 5
- 230000001225 therapeutic effect Effects 0.000 claims description 5
- XFCLJVABOIYOMF-QPLCGJKRSA-N toremifene Chemical compound C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 XFCLJVABOIYOMF-QPLCGJKRSA-N 0.000 claims description 5
- 229960005026 toremifene Drugs 0.000 claims description 5
- 229960001727 tretinoin Drugs 0.000 claims description 5
- 229960000241 vandetanib Drugs 0.000 claims description 5
- UHTHHESEBZOYNR-UHFFFAOYSA-N vandetanib Chemical compound COC1=CC(C(/N=CN2)=N/C=3C(=CC(Br)=CC=3)F)=C2C=C1OCC1CCN(C)CC1 UHTHHESEBZOYNR-UHFFFAOYSA-N 0.000 claims description 5
- 230000019491 signal transduction Effects 0.000 claims description 4
- NHTGHBARYWONDQ-UHFFFAOYSA-N (+-)-α-methyl-tyrosine Chemical compound OC(=O)C(N)(C)CC1=CC=C(O)C=C1 NHTGHBARYWONDQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000919 ceramic Substances 0.000 claims description 3
- 230000001133 acceleration Effects 0.000 claims description 2
- 229940122815 Aromatase inhibitor Drugs 0.000 claims 1
- HKVAMNSJSFKALM-GKUWKFKPSA-N Everolimus Chemical compound C1C[C@@H](OCCO)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 HKVAMNSJSFKALM-GKUWKFKPSA-N 0.000 claims 1
- 239000002146 L01XE16 - Crizotinib Substances 0.000 claims 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 claims 1
- 229960004373 acetylcholine Drugs 0.000 claims 1
- 108010081667 aflibercept Proteins 0.000 claims 1
- 229960004316 cisplatin Drugs 0.000 claims 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims 1
- 229960005061 crizotinib Drugs 0.000 claims 1
- KTEIFNKAUNYNJU-GFCCVEGCSA-N crizotinib Chemical compound O([C@H](C)C=1C(=C(F)C=CC=1Cl)Cl)C(C(=NC=1)N)=CC=1C(=C1)C=NN1C1CCNCC1 KTEIFNKAUNYNJU-GFCCVEGCSA-N 0.000 claims 1
- GITKQXFBNJTMRP-QRPNPIFTSA-N ethyl (2s)-2-amino-3-(4-hydroxy-3-nitrophenyl)propanoate;hydrochloride Chemical compound Cl.CCOC(=O)[C@@H](N)CC1=CC=C(O)C([N+]([O-])=O)=C1 GITKQXFBNJTMRP-QRPNPIFTSA-N 0.000 claims 1
- 229960005167 everolimus Drugs 0.000 claims 1
- RAXWZGMSMQUDTR-UHFFFAOYSA-N methyl 2-amino-3-(4-hydroxy-3,5-diiodophenyl)propanoate;hydrochloride Chemical compound Cl.COC(=O)C(N)CC1=CC(I)=C(O)C(I)=C1 RAXWZGMSMQUDTR-UHFFFAOYSA-N 0.000 claims 1
- 229940095743 selective estrogen receptor modulator Drugs 0.000 claims 1
- 239000000333 selective estrogen receptor modulator Substances 0.000 claims 1
- GPXBXXGIAQBQNI-UHFFFAOYSA-N vemurafenib Chemical compound CCCS(=O)(=O)NC1=CC=C(F)C(C(=O)C=2C3=CC(=CN=C3NC=2)C=2C=CC(Cl)=CC=2)=C1F GPXBXXGIAQBQNI-UHFFFAOYSA-N 0.000 claims 1
- 229960003862 vemurafenib Drugs 0.000 claims 1
- 229960002760 ziv-aflibercept Drugs 0.000 claims 1
- AXDLCFOOGCNDST-SECBINFHSA-N (2r)-3-(4-hydroxyphenyl)-2-(methylazaniumyl)propanoate Chemical compound CN[C@@H](C(O)=O)CC1=CC=C(O)C=C1 AXDLCFOOGCNDST-SECBINFHSA-N 0.000 description 4
- VDFGKWYGLJURQQ-QMMMGPOBSA-N 4-[(2s)-2-azaniumyl-3-ethoxy-3-oxopropyl]-2-nitrophenolate Chemical compound CCOC(=O)[C@@H](N)CC1=CC=C(O)C([N+]([O-])=O)=C1 VDFGKWYGLJURQQ-QMMMGPOBSA-N 0.000 description 4
- NAVMQTYZDKMPEU-UHFFFAOYSA-N Targretin Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C(=C)C1=CC=C(C(O)=O)C=C1 NAVMQTYZDKMPEU-UHFFFAOYSA-N 0.000 description 4
- 229940046844 aromatase inhibitors Drugs 0.000 description 4
- 229960002938 bexarotene Drugs 0.000 description 4
- 230000003915 cell function Effects 0.000 description 4
- 239000002834 estrogen receptor modulator Substances 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- UPIXZLGONUBZLK-UHFFFAOYSA-N platinum Chemical compound [Pt].[Pt] UPIXZLGONUBZLK-UHFFFAOYSA-N 0.000 description 4
- 229960003452 romidepsin Drugs 0.000 description 4
- 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 description 4
- 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 description 4
- 108010091666 romidepsin Proteins 0.000 description 4
- 229910052714 tellurium Inorganic materials 0.000 description 4
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 4
- 230000005672 electromagnetic field Effects 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- NHTGHBARYWONDQ-SNVBAGLBSA-N (2r)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid Chemical group OC(=O)[C@@](N)(C)CC1=CC=C(O)C=C1 NHTGHBARYWONDQ-SNVBAGLBSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005007 materials handling Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361894279P | 2013-10-22 | 2013-10-22 | |
| US61/894,279 | 2013-10-22 | ||
| US14/062,194 | 2013-10-24 | ||
| US14/062,194 US9585841B2 (en) | 2013-10-22 | 2013-10-24 | Tyrosine derivatives and compositions comprising them |
| PCT/US2014/061527 WO2015061288A1 (en) | 2013-10-22 | 2014-10-21 | Tyrosine derivatives and compositions comprising them |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016534071A JP2016534071A (ja) | 2016-11-04 |
| JP2016534071A5 true JP2016534071A5 (enExample) | 2019-10-10 |
| JP6684210B2 JP6684210B2 (ja) | 2020-04-22 |
Family
ID=52826750
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016525902A Expired - Fee Related JP6684210B2 (ja) | 2013-10-22 | 2014-10-21 | チロシン誘導体及びそれを含む組成物 |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US9585841B2 (enExample) |
| EP (1) | EP3060200B1 (enExample) |
| JP (1) | JP6684210B2 (enExample) |
| KR (1) | KR102292206B1 (enExample) |
| CN (1) | CN106232105A (enExample) |
| AU (1) | AU2014340263B2 (enExample) |
| CA (1) | CA2927980C (enExample) |
| CY (1) | CY1124386T1 (enExample) |
| DK (1) | DK3060200T3 (enExample) |
| ES (1) | ES2879947T3 (enExample) |
| HR (1) | HRP20210999T1 (enExample) |
| HU (1) | HUE055110T2 (enExample) |
| IL (1) | IL245173B (enExample) |
| LT (1) | LT3060200T (enExample) |
| MX (1) | MX384083B (enExample) |
| PH (1) | PH12016500729A1 (enExample) |
| PL (1) | PL3060200T3 (enExample) |
| PT (1) | PT3060200T (enExample) |
| RS (1) | RS62216B1 (enExample) |
| SI (1) | SI3060200T1 (enExample) |
| SM (1) | SMT202100437T1 (enExample) |
| WO (1) | WO2015061288A1 (enExample) |
| ZA (1) | ZA201602770B (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9585841B2 (en) * | 2013-10-22 | 2017-03-07 | Tyme, Inc. | Tyrosine derivatives and compositions comprising them |
| CA3024501A1 (en) * | 2016-05-18 | 2017-11-23 | Tyme, Inc. | Dihydrotestosterone and dihydrotestosterone derivatives and promoters in the treatment of cancer |
| CA3040922A1 (en) * | 2016-11-15 | 2018-05-24 | Tyme, Inc. | Pharmaceutical compositions and methods for the treatment of cancer |
| MX2019006326A (es) * | 2016-11-30 | 2019-07-12 | Tyme Inc | Derivados de tirosina y composiciones que los comprenden. |
| US11040027B2 (en) | 2017-01-17 | 2021-06-22 | Heparegenix Gmbh | Protein kinase inhibitors for promoting liver regeneration or reducing or preventing hepatocyte death |
| KR20190138683A (ko) * | 2017-04-21 | 2019-12-13 | 스티븐 호프만 | 망막병증을 치료하기 위한 조성물 및 방법 |
| KR20200038481A (ko) * | 2017-07-19 | 2020-04-13 | 호프만 테크놀로지스, 인크. | 스트레스-관련 장애를 치료하기 위한 조성물 |
| WO2019059634A1 (ko) * | 2017-09-19 | 2019-03-28 | 주식회사 스킨큐씨 | D-타이로신 또는 이를 포함하는 펩타이드를 포함하는 피부 미백용 조성물 |
| RU2719575C1 (ru) * | 2019-02-01 | 2020-04-21 | Общество с ограниченной ответственностью "Центр ранней диагностики нейродегенеративных заболеваний (НДЗ)" | Фармацевтическая композиция на основе альфа-метил-п-тирозина и способ ранней диагностики болезни Паркинсона |
| EP3968785A4 (en) | 2019-05-14 | 2023-01-11 | Tyme, Inc. | COMPOSITIONS AND METHODS FOR TREATMENT OF CANCER |
| US20210106549A1 (en) * | 2019-10-15 | 2021-04-15 | Tyme, Inc. | Pharmaceutical compositions and methods |
| CN115515575A (zh) * | 2020-01-17 | 2022-12-23 | 迪美公司 | 用于调节癌症的酪氨酸衍生物 |
| US10905698B1 (en) | 2020-05-14 | 2021-02-02 | Tyme, Inc. | Methods of treating SARS-COV-2 infections |
| WO2023128791A1 (ru) * | 2021-12-30 | 2023-07-06 | Общество С Ограниченной Ответственностью "Центр Ранней Диагностики Нейродегенеративных Заболеваний" | Комбинированное лекарственное средство для ранней диагностики болезни паркинсона |
Family Cites Families (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4189604A (en) | 1975-07-22 | 1980-02-19 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Bestatin |
| CA1108180A (en) | 1976-07-21 | 1981-09-01 | Hamao Umezawa | Analogs of bestatin |
| US4165382A (en) | 1977-10-17 | 1979-08-21 | Jose Pozuelo | Method of pharmacologically treating schizophrenia with alpha-methyl-para-tyrosine |
| US4117161A (en) | 1977-05-16 | 1978-09-26 | Jose Pozuelo | Method of pharmacologically treating drug addiction with alpha-methyl-para-tyrosine |
| US4389415A (en) | 1978-01-24 | 1983-06-21 | Merck & Co., Inc. | Method of treating hypertension |
| US5206018A (en) | 1978-11-03 | 1993-04-27 | Ayerst, Mckenna & Harrison, Inc. | Use of rapamycin in treatment of tumors |
| US5674839A (en) | 1987-05-22 | 1997-10-07 | Competitive Technologies, Inc. | Cyclic analogs of alpha-MSH fragments |
| US5683981A (en) | 1987-05-22 | 1997-11-04 | Competitive Technologies, Inc. | Cyclic bridged analogs of α-MSH and methods thereof |
| JP2668880B2 (ja) * | 1987-06-23 | 1997-10-27 | 日本油脂株式会社 | 被覆アミノ酸類の製造方法 |
| US4806360A (en) * | 1987-10-23 | 1989-02-21 | Advanced Polymer Systems | Synthetic melanin aggregates |
| US5073541A (en) | 1987-11-18 | 1991-12-17 | Administrators Of The Tulane Educational Fund | Treatment of small cell lung cancer with somatostatin analogs |
| JPH02286602A (ja) * | 1989-04-28 | 1990-11-26 | Nippon Tokushu Noyaku Seizo Kk | 徐放性農薬粒剤 |
| US5225435A (en) | 1990-05-18 | 1993-07-06 | Yale University | Soluble melanin |
| US5310539A (en) * | 1991-04-15 | 1994-05-10 | Board Of Regents, The University Of Texas System | Melanin-based agents for image enhancement |
| WO1994010968A1 (en) * | 1992-11-19 | 1994-05-26 | Bristol-Myers Squibb Company | Compositions and methods for temporarily coloring hair using solubilized melanin |
| AU6146994A (en) * | 1993-03-04 | 1994-09-26 | Minister Of Agriculture Fisheries And Food In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland, The | Selective binding materials and assays |
| WO1994022460A1 (en) | 1993-04-05 | 1994-10-13 | University Patents, Inc. | Diagnosis and treatment of erectile dysfunction |
| US8828432B2 (en) * | 1996-10-28 | 2014-09-09 | General Mills, Inc. | Embedding and encapsulation of sensitive components into a matrix to obtain discrete controlled release particles |
| IT1291633B1 (it) | 1997-04-22 | 1999-01-11 | Pharmaconsult S A S | Uso dell'alfa-metil-p-tirosina per inibire la produzione di melanina nei melanociti dell'iride |
| US20030059471A1 (en) | 1997-12-15 | 2003-03-27 | Compton Bruce Jon | Oral delivery formulation |
| AU757658B2 (en) | 1998-03-09 | 2003-02-27 | Zealand Pharma A/S | Pharmacologically active peptide conjugates having a reduced tendency towards enzymatic hydrolysis |
| WO2000010507A2 (en) | 1998-08-21 | 2000-03-02 | The Children's Medical Center Corporation | Use of melanin for inhibition of angiogenesis and macular degeneration |
| CA2405549A1 (en) * | 2000-04-03 | 2001-10-11 | Hybridon, Inc. | Sensitization of cells to cytotoxic agents using oligonucleotides directed to nucleotide excision repair or transcription coupled repair genes |
| US20030114362A1 (en) | 2001-06-08 | 2003-06-19 | Novaspin Biotech Gmbh | Penta-or tetrapeptide binding to somatostatin receptors and the use of the same |
| US7482018B2 (en) * | 2001-12-21 | 2009-01-27 | Soane Family Trust | Use of oligomers and polymers for drug solubilization, stabilization, and delivery |
| US8620406B2 (en) * | 2004-01-23 | 2013-12-31 | Boston Scientific Scimed, Inc. | Medical devices visible by magnetic resonance imaging |
| EP3075247B1 (en) * | 2004-02-02 | 2022-10-12 | BioSight Ltd. | Conjugates for cancer therapy and diagnosis |
| WO2006080951A2 (en) * | 2004-07-01 | 2006-08-03 | Yale University | Targeted and high density drug loaded polymeric materials |
| WO2006099288A2 (en) | 2005-03-11 | 2006-09-21 | Indevus Pharmaceuticals, Inc. | Controlled release formulations of octreotide |
| ES2327421T3 (es) | 2005-03-11 | 2009-10-29 | Gpc Biotech Ag | Terapia antiproliferativa combinada que comprende satraplatino o jm118 y docetaxel. |
| KR101288729B1 (ko) * | 2005-04-01 | 2013-07-23 | 인터자인 테크놀로지스, 인코포레이티드 | 약물 전달용 중합체성 마이셀 |
| US8758723B2 (en) * | 2006-04-19 | 2014-06-24 | The Board Of Regents Of The University Of Texas System | Compositions and methods for cellular imaging and therapy |
| DK2013221T3 (en) | 2006-04-19 | 2015-09-28 | Univ Texas | Compositions and methods for cellular imaging and therapy |
| US20090142337A1 (en) * | 2006-05-08 | 2009-06-04 | Astex Therapeutics Limited | Pharmaceutical Combinations of Diazole Derivatives for Cancer Treatment |
| CN101138634A (zh) * | 2006-09-07 | 2008-03-12 | 于保法 | 用于治疗肿瘤的组合物 |
| FR2918990B1 (fr) * | 2007-07-20 | 2012-12-21 | Innov Ia | Procede de preparation de compositions pulverulentes stables |
| WO2009054001A1 (en) | 2007-10-22 | 2009-04-30 | Biocon Limited | A pharmaceutical composition and a process thereof |
| AU2009221120A1 (en) | 2008-03-07 | 2009-09-11 | Pharma Mar, S.A. | Improved antitumoral treatments |
| EP2106806A1 (en) * | 2008-03-31 | 2009-10-07 | Fraunhofer-Gesellschaft zur Förderung der Angewandten Forschung e.V. | Nanoparticles for targeted delivery of active agents to the lung |
| WO2009131631A1 (en) | 2008-04-14 | 2009-10-29 | Poniard Pharmaceuticals, Inc. | Rapamycin analogs as anti-cancer agents |
| KR101078302B1 (ko) * | 2008-05-29 | 2011-10-31 | (주)프로넥스 | 약물전달체 |
| WO2010022243A1 (en) | 2008-08-20 | 2010-02-25 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Chemoprevention of head and neck squamous cell carcinomas |
| US8110578B2 (en) | 2008-10-27 | 2012-02-07 | Signal Pharmaceuticals, Llc | Pyrazino[2,3-b]pyrazine mTOR kinase inhibitors for oncology indications and diseases associated with the mTOR/PI3K/Akt pathway |
| WO2010118419A2 (en) | 2009-04-10 | 2010-10-14 | Haiyan Qi | Novel anti-aging agents and methods to identify them |
| WO2011112576A1 (en) | 2010-03-10 | 2011-09-15 | Ambrilia Biopharma Inc. | Microspheres for sustained release of octreotide acetate |
| WO2012012305A2 (en) * | 2010-07-18 | 2012-01-26 | Niiki Pharma Inc. | Combination therapy using a ruthenium complex |
| WO2013109610A1 (en) | 2012-01-17 | 2013-07-25 | Steven Hoffman | Pharmaceutical compositions and methods |
| US9724657B2 (en) * | 2013-10-22 | 2017-08-08 | Tyme, Inc. | High-speed centrifugal mixing devices and methods of use |
| US9585841B2 (en) * | 2013-10-22 | 2017-03-07 | Tyme, Inc. | Tyrosine derivatives and compositions comprising them |
-
2013
- 2013-10-24 US US14/062,194 patent/US9585841B2/en not_active Expired - Fee Related
-
2014
- 2014-10-21 SI SI201431874T patent/SI3060200T1/sl unknown
- 2014-10-21 HU HUE14802529A patent/HUE055110T2/hu unknown
- 2014-10-21 DK DK14802529.9T patent/DK3060200T3/da active
- 2014-10-21 SM SM20210437T patent/SMT202100437T1/it unknown
- 2014-10-21 LT LTEP14802529.9T patent/LT3060200T/lt unknown
- 2014-10-21 HR HRP20210999TT patent/HRP20210999T1/hr unknown
- 2014-10-21 KR KR1020167013133A patent/KR102292206B1/ko not_active Expired - Fee Related
- 2014-10-21 MX MX2016005166A patent/MX384083B/es unknown
- 2014-10-21 CN CN201480058302.2A patent/CN106232105A/zh active Pending
- 2014-10-21 AU AU2014340263A patent/AU2014340263B2/en not_active Ceased
- 2014-10-21 PL PL14802529T patent/PL3060200T3/pl unknown
- 2014-10-21 EP EP14802529.9A patent/EP3060200B1/en active Active
- 2014-10-21 RS RS20210705A patent/RS62216B1/sr unknown
- 2014-10-21 ES ES14802529T patent/ES2879947T3/es active Active
- 2014-10-21 WO PCT/US2014/061527 patent/WO2015061288A1/en not_active Ceased
- 2014-10-21 CA CA2927980A patent/CA2927980C/en active Active
- 2014-10-21 PT PT148025299T patent/PT3060200T/pt unknown
- 2014-10-21 JP JP2016525902A patent/JP6684210B2/ja not_active Expired - Fee Related
-
2016
- 2016-04-18 IL IL245173A patent/IL245173B/en active IP Right Grant
- 2016-04-19 PH PH12016500729A patent/PH12016500729A1/en unknown
- 2016-04-21 ZA ZA2016/02770A patent/ZA201602770B/en unknown
-
2017
- 2017-03-06 US US15/451,029 patent/US11058638B2/en not_active Expired - Fee Related
-
2021
- 2021-07-30 CY CY20211100682T patent/CY1124386T1/el unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP7745708B2 (ja) | 癌を治療するための方法 | |
| JP6684210B2 (ja) | チロシン誘導体及びそれを含む組成物 | |
| ES2909910T3 (es) | Tratamiento contra el cáncer usando combinaciones de inhibidores de ERK y RAF | |
| JP2017518334A5 (enExample) | ||
| JP2014511383A5 (enExample) | ||
| JP2017513809A5 (enExample) | ||
| JP2012525387A5 (enExample) | ||
| WO2007064945A2 (en) | Cancer therapies and pharmaceutical compositions used therein | |
| JP2019518048A (ja) | がんの予防および／または治療のための化合物、組成物および方法 | |
| JP2019516726A5 (enExample) | ||
| RU2013126798A (ru) | Комбинированная терапия дексаметазоном | |
| JP2017504567A5 (enExample) | ||
| RU2017132445A (ru) | Дозы панобиностата для множественной миеломы | |
| HK40064613A (en) | Methods for treating cancer | |
| EA201992690A1 (ru) | Применение вибегрона для лечения гиперактивного мочевого пузыря | |
| NZ719457B2 (en) | Tyrosine derivatives and compositions comprising them |