JP2018514562A5 - - Google Patents
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- Publication number
- JP2018514562A5 JP2018514562A5 JP2017556837A JP2017556837A JP2018514562A5 JP 2018514562 A5 JP2018514562 A5 JP 2018514562A5 JP 2017556837 A JP2017556837 A JP 2017556837A JP 2017556837 A JP2017556837 A JP 2017556837A JP 2018514562 A5 JP2018514562 A5 JP 2018514562A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aralkyl
- aryl
- group
- thienylmethyl
- 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
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- 125000000217 alkyl group Chemical group 0.000 claims 120
- 125000003710 aryl alkyl group Chemical group 0.000 claims 104
- 125000003118 aryl group Chemical group 0.000 claims 88
- 229910052739 hydrogen Inorganic materials 0.000 claims 72
- 239000001257 hydrogen Substances 0.000 claims 72
- -1 1- (1,3-benzodioxol-5-yl) -3-ethoxy-3-oxopropyl Chemical group 0.000 claims 69
- 150000002431 hydrogen Chemical class 0.000 claims 55
- 150000001875 compounds Chemical class 0.000 claims 42
- 125000000623 heterocyclic group Chemical group 0.000 claims 40
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 36
- 125000000753 cycloalkyl group Chemical group 0.000 claims 36
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 36
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 32
- 239000000203 mixture Substances 0.000 claims 25
- 125000003282 alkyl amino group Chemical group 0.000 claims 24
- 125000001188 haloalkyl group Chemical group 0.000 claims 24
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 24
- 125000004663 dialkyl amino group Chemical group 0.000 claims 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 17
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 16
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 13
- 230000003213 activating effect Effects 0.000 claims 12
- 125000004171 alkoxy aryl group Chemical group 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 12
- 125000001769 aryl amino group Chemical group 0.000 claims 12
- 125000004104 aryloxy group Chemical group 0.000 claims 12
- 150000001540 azides Chemical class 0.000 claims 12
- 125000004986 diarylamino group Chemical group 0.000 claims 12
- 125000004438 haloalkoxy group Chemical group 0.000 claims 12
- 125000003106 haloaryl group Chemical group 0.000 claims 12
- 125000001475 halogen functional group Chemical group 0.000 claims 12
- 125000005027 hydroxyaryl group Chemical group 0.000 claims 12
- YGGXZTQSGNFKPJ-UHFFFAOYSA-N methyl 2-naphthalen-1-ylacetate Chemical compound C1=CC=C2C(CC(=O)OC)=CC=CC2=C1 YGGXZTQSGNFKPJ-UHFFFAOYSA-N 0.000 claims 12
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims 11
- 229960005486 vaccine Drugs 0.000 claims 10
- 102000006495 integrins Human genes 0.000 claims 9
- 108010044426 integrins Proteins 0.000 claims 9
- GVZBSJKQWTYUDD-UHFFFAOYSA-N thiophen-2-ylmethyl carbamate Chemical compound NC(=O)OCC1=CC=CS1 GVZBSJKQWTYUDD-UHFFFAOYSA-N 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 239000002671 adjuvant Substances 0.000 claims 7
- HTHOAMZINQDBNL-UHFFFAOYSA-N N'-(thiophen-2-ylmethyl)pentanediamide Chemical compound C(CCCC(=O)N)(=O)NCC=1SC=CC=1 HTHOAMZINQDBNL-UHFFFAOYSA-N 0.000 claims 6
- 238000009472 formulation Methods 0.000 claims 6
- 239000003446 ligand Substances 0.000 claims 5
- NUSUVAXSYQWLDK-FIBWVYCGSA-N methyl (3s)-3-(1,3-benzodioxol-5-yl)-3-[[(2s)-1-[bis[(4-methoxyphenyl)methyl]carbamoyloxy]hexan-2-yl]carbamoylamino]propanoate Chemical compound C([C@H](CCCC)NC(=O)N[C@@H](CC(=O)OC)C=1C=C2OCOC2=CC=1)OC(=O)N(CC=1C=CC(OC)=CC=1)CC1=CC=C(OC)C=C1 NUSUVAXSYQWLDK-FIBWVYCGSA-N 0.000 claims 5
- 239000000126 substance Substances 0.000 claims 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 4
- 241001024304 Mino Species 0.000 claims 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 4
- 210000004027 cell Anatomy 0.000 claims 4
- 125000005265 dialkylamine group Chemical group 0.000 claims 4
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 4
- 230000001404 mediated effect Effects 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 239000007983 Tris buffer Substances 0.000 claims 3
- 230000002708 enhancing effect Effects 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 230000003993 interaction Effects 0.000 claims 3
- 210000000581 natural killer T-cell Anatomy 0.000 claims 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 2
- 229940076838 Immune checkpoint inhibitor Drugs 0.000 claims 2
- 102000037984 Inhibitory immune checkpoint proteins Human genes 0.000 claims 2
- 108091008026 Inhibitory immune checkpoint proteins Proteins 0.000 claims 2
- 239000000427 antigen Substances 0.000 claims 2
- 102000036639 antigens Human genes 0.000 claims 2
- 108091007433 antigens Proteins 0.000 claims 2
- 239000012274 immune-checkpoint protein inhibitor Substances 0.000 claims 2
- QWDGYRDMZTZEHQ-URXFXBBRSA-N methyl (3s)-3-(1,3-benzodioxol-5-yl)-3-[[(2s)-1-[bis(thiophen-2-ylmethyl)carbamoyloxy]hexan-2-yl]carbamoylamino]propanoate Chemical compound C([C@H](CCCC)NC(=O)N[C@@H](CC(=O)OC)C=1C=C2OCOC2=CC=1)OC(=O)N(CC=1SC=CC=1)CC1=CC=CS1 QWDGYRDMZTZEHQ-URXFXBBRSA-N 0.000 claims 2
- 210000000822 natural killer cell Anatomy 0.000 claims 2
- 102000004169 proteins and genes Human genes 0.000 claims 2
- 108090000623 proteins and genes Proteins 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- AKNNEGZIBPJZJG-MSOLQXFVSA-N (-)-noscapine Chemical compound CN1CCC2=CC=3OCOC=3C(OC)=C2[C@@H]1[C@@H]1C2=CC=C(OC)C(OC)=C2C(=O)O1 AKNNEGZIBPJZJG-MSOLQXFVSA-N 0.000 claims 1
- SDEOSHAQCMPJIJ-UHFFFAOYSA-N (4-methoxyphenyl)methyl carbamate Chemical compound COC1=CC=C(COC(N)=O)C=C1 SDEOSHAQCMPJIJ-UHFFFAOYSA-N 0.000 claims 1
- BUMALLJGDIKZCQ-OWOJBTEDSA-N (E)-N,N,N',N'-tetrakis(thiophen-2-ylmethyl)hex-3-enediamide Chemical compound C=1C=CSC=1CN(CC=1SC=CC=1)C(=O)C\C=C\CC(=O)N(CC=1SC=CC=1)CC1=CC=CS1 BUMALLJGDIKZCQ-OWOJBTEDSA-N 0.000 claims 1
- QZVHYFUVMQIGGM-UHFFFAOYSA-N 2-Hexylthiophene Chemical compound CCCCCCC1=CC=CS1 QZVHYFUVMQIGGM-UHFFFAOYSA-N 0.000 claims 1
- ILXPKVPEKRTBJP-UHFFFAOYSA-N 2-[2-[bis(thiophen-2-ylmethyl)amino]-2-oxoethoxy]-n,n-bis(thiophen-2-ylmethyl)acetamide Chemical compound C=1C=CSC=1CN(CC=1SC=CC=1)C(=O)COCC(=O)N(CC=1SC=CC=1)CC1=CC=CS1 ILXPKVPEKRTBJP-UHFFFAOYSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- IVBBJDFNLLFWLO-UHFFFAOYSA-N 2-n,2-n,6-n,6-n-tetrakis(thiophen-2-ylmethyl)pyridine-2,6-dicarboxamide Chemical compound C=1C=CC(C(=O)N(CC=2SC=CC=2)CC=2SC=CC=2)=NC=1C(=O)N(CC=1SC=CC=1)CC1=CC=CS1 IVBBJDFNLLFWLO-UHFFFAOYSA-N 0.000 claims 1
- PFIFIFFFWQWIDK-UHFFFAOYSA-N 3-(3-hydroxypropyl)-1,1-bis(thiophen-2-ylmethyl)urea Chemical compound C=1C=CSC=1CN(C(=O)NCCCO)CC1=CC=CS1 PFIFIFFFWQWIDK-UHFFFAOYSA-N 0.000 claims 1
- ULBLPVWNQUWLII-AWEZNQCLSA-N 3-[(2s)-1-hydroxyhexan-2-yl]-1,1-bis(thiophen-2-ylmethyl)urea Chemical compound C=1C=CSC=1CN(C(=O)N[C@H](CO)CCCC)CC1=CC=CS1 ULBLPVWNQUWLII-AWEZNQCLSA-N 0.000 claims 1
- HLKRVPQDXDMMTK-UHFFFAOYSA-N 3-[[2-(methylaminomethoxy)ethylamino]methylamino]propanoic acid Chemical compound CNCOCCNCNCCC(=O)O HLKRVPQDXDMMTK-UHFFFAOYSA-N 0.000 claims 1
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 claims 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 241000193830 Bacillus <bacterium> Species 0.000 claims 1
- FWJUZXRUWKZLMC-UHFFFAOYSA-N CCCCCCOC(=O)N(CC1=CC=CC=C1)CC2=CC=CC=C2 Chemical compound CCCCCCOC(=O)N(CC1=CC=CC=C1)CC2=CC=CC=C2 FWJUZXRUWKZLMC-UHFFFAOYSA-N 0.000 claims 1
- 101100463133 Caenorhabditis elegans pdl-1 gene Proteins 0.000 claims 1
- 101000633756 Echis pyramidum leakeyi Snaclec 4 Proteins 0.000 claims 1
- 101150021185 FGF gene Proteins 0.000 claims 1
- 102000016359 Fibronectins Human genes 0.000 claims 1
- 108010067306 Fibronectins Proteins 0.000 claims 1
- 108010017080 Granulocyte Colony-Stimulating Factor Proteins 0.000 claims 1
- 102000004269 Granulocyte Colony-Stimulating Factor Human genes 0.000 claims 1
- 102000018071 Immunoglobulin Fc Fragments Human genes 0.000 claims 1
- 108010091135 Immunoglobulin Fc Fragments Proteins 0.000 claims 1
- 102100040061 Indoleamine 2,3-dioxygenase 1 Human genes 0.000 claims 1
- 101710120843 Indoleamine 2,3-dioxygenase 1 Proteins 0.000 claims 1
- 108010064593 Intercellular Adhesion Molecule-1 Proteins 0.000 claims 1
- 102100037877 Intercellular adhesion molecule 1 Human genes 0.000 claims 1
- 102100037872 Intercellular adhesion molecule 2 Human genes 0.000 claims 1
- 101710148794 Intercellular adhesion molecule 2 Proteins 0.000 claims 1
- 102100028793 Mucosal addressin cell adhesion molecule 1 Human genes 0.000 claims 1
- 101710139349 Mucosal addressin cell adhesion molecule 1 Proteins 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 101710089372 Programmed cell death protein 1 Proteins 0.000 claims 1
- 229940123384 Toll-like receptor (TLR) agonist Drugs 0.000 claims 1
- 108010000134 Vascular Cell Adhesion Molecule-1 Proteins 0.000 claims 1
- 102100023543 Vascular cell adhesion protein 1 Human genes 0.000 claims 1
- XAJBEVYPOBLZFK-HNNXBMFYSA-N [(2s)-2-(methylcarbamoylamino)hexyl] n,n-bis(thiophen-2-ylmethyl)carbamate Chemical compound C=1C=CSC=1CN(C(=O)OC[C@H](CCCC)NC(=O)NC)CC1=CC=CS1 XAJBEVYPOBLZFK-HNNXBMFYSA-N 0.000 claims 1
- OAAVIIVKPWATKE-SFHVURJKSA-N [(2s)-2-(morpholine-4-carbonylamino)hexyl] n,n-bis(thiophen-2-ylmethyl)carbamate Chemical compound C([C@H](CCCC)NC(=O)N1CCOCC1)OC(=O)N(CC=1SC=CC=1)CC1=CC=CS1 OAAVIIVKPWATKE-SFHVURJKSA-N 0.000 claims 1
- IMHJHTBYDGFTJW-URXFXBBRSA-N [(2s)-2-[[(1s)-1-(1,3-benzodioxol-5-yl)-3-hydroxypropyl]carbamoylamino]hexyl] n,n-bis(thiophen-2-ylmethyl)carbamate Chemical compound C([C@H](CCCC)NC(=O)N[C@@H](CCO)C=1C=C2OCOC2=CC=1)OC(=O)N(CC=1SC=CC=1)CC1=CC=CS1 IMHJHTBYDGFTJW-URXFXBBRSA-N 0.000 claims 1
- 229960000548 alemtuzumab Drugs 0.000 claims 1
- AKNNEGZIBPJZJG-UHFFFAOYSA-N alpha-noscapine Natural products CN1CCC2=CC=3OCOC=3C(OC)=C2C1C1C2=CC=C(OC)C(OC)=C2C(=O)O1 AKNNEGZIBPJZJG-UHFFFAOYSA-N 0.000 claims 1
- 229940037003 alum Drugs 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 229940022399 cancer vaccine Drugs 0.000 claims 1
- 239000013592 cell lysate Substances 0.000 claims 1
- 230000001413 cellular effect Effects 0.000 claims 1
- 229960005395 cetuximab Drugs 0.000 claims 1
- 125000004803 chlorobenzyl group Chemical group 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000028993 immune response Effects 0.000 claims 1
- 229960005386 ipilimumab Drugs 0.000 claims 1
- QWDGYRDMZTZEHQ-ZJSXRUAMSA-N methyl (3r)-3-(1,3-benzodioxol-5-yl)-3-[[(2r)-1-[bis(thiophen-2-ylmethyl)carbamoyloxy]hexan-2-yl]carbamoylamino]propanoate Chemical compound C([C@@H](CCCC)NC(=O)N[C@H](CC(=O)OC)C=1C=C2OCOC2=CC=1)OC(=O)N(CC=1SC=CC=1)CC1=CC=CS1 QWDGYRDMZTZEHQ-ZJSXRUAMSA-N 0.000 claims 1
- GWZUZFYMBASETI-FQEVSTJZSA-N methyl (3s)-3-(1,3-benzodioxol-5-yl)-3-[2-[bis(thiophen-2-ylmethyl)carbamoyloxy]ethylcarbamoylamino]propanoate Chemical compound N([C@@H](CC(=O)OC)C=1C=C2OCOC2=CC=1)C(=O)NCCOC(=O)N(CC=1SC=CC=1)CC1=CC=CS1 GWZUZFYMBASETI-FQEVSTJZSA-N 0.000 claims 1
- QWDGYRDMZTZEHQ-QPPBQGQZSA-N methyl (3s)-3-(1,3-benzodioxol-5-yl)-3-[[(2r)-1-[bis(thiophen-2-ylmethyl)carbamoyloxy]hexan-2-yl]carbamoylamino]propanoate Chemical compound C([C@@H](CCCC)NC(=O)N[C@@H](CC(=O)OC)C=1C=C2OCOC2=CC=1)OC(=O)N(CC=1SC=CC=1)CC1=CC=CS1 QWDGYRDMZTZEHQ-QPPBQGQZSA-N 0.000 claims 1
- GPHNIKRMYSGNLJ-NSOVKSMOSA-N methyl (3s)-3-(1,3-benzodioxol-5-yl)-3-[[(2s)-1-(dibenzylcarbamoyloxy)hexan-2-yl]carbamoylamino]propanoate Chemical compound C([C@H](CCCC)NC(=O)N[C@@H](CC(=O)OC)C=1C=C2OCOC2=CC=1)OC(=O)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 GPHNIKRMYSGNLJ-NSOVKSMOSA-N 0.000 claims 1
- UEEKBYJOLPRABO-AHWVRZQESA-N methyl (3s)-3-(1,3-benzodioxol-5-yl)-3-[[(2s)-1-[(4-bromophenyl)methyl-(thiophen-2-ylmethyl)carbamoyl]oxyhexan-2-yl]carbamoylamino]propanoate Chemical compound C([C@H](CCCC)NC(=O)N[C@@H](CC(=O)OC)C=1C=C2OCOC2=CC=1)OC(=O)N(CC=1C=CC(Br)=CC=1)CC1=CC=CS1 UEEKBYJOLPRABO-AHWVRZQESA-N 0.000 claims 1
- XCISHNWIYJLVPY-UNMCSNQZSA-N methyl (3s)-3-(1,3-benzodioxol-5-yl)-3-[[(2s)-1-[2-methoxyethyl(thiophen-2-ylmethyl)carbamoyl]oxyhexan-2-yl]carbamoylamino]propanoate Chemical compound C([C@H](CCCC)NC(=O)N[C@@H](CC(=O)OC)C=1C=C2OCOC2=CC=1)OC(=O)N(CCOC)CC1=CC=CS1 XCISHNWIYJLVPY-UNMCSNQZSA-N 0.000 claims 1
- LAVSLODIGOPBPX-IZEXYCQBSA-N methyl (3s)-3-(1,3-benzodioxol-5-yl)-3-[[(2s)-1-[bis(thiophen-2-ylmethyl)carbamoyloxy]-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoylamino]propanoate Chemical compound C([C@H](NC(=O)N[C@@H](CC(=O)OC)C=1C=C2OCOC2=CC=1)COC(=O)N(CC=1SC=CC=1)CC=1SC=CC=1)CCCNC(=O)OCC1=CC=CC=C1 LAVSLODIGOPBPX-IZEXYCQBSA-N 0.000 claims 1
- DVQYGQOZIPSOHG-URXFXBBRSA-N methyl (3s)-3-(1,3-benzodioxol-5-yl)-3-[[(2s)-1-[bis(thiophen-2-ylmethyl)carbamoylsulfanyl]hexan-2-yl]carbamoylamino]propanoate Chemical compound C([C@H](CCCC)NC(=O)N[C@@H](CC(=O)OC)C=1C=C2OCOC2=CC=1)SC(=O)N(CC=1SC=CC=1)CC1=CC=CS1 DVQYGQOZIPSOHG-URXFXBBRSA-N 0.000 claims 1
- JAMLSOOENJLVDO-ZEQRLZLVSA-N methyl (3s)-3-(1,3-benzodioxol-5-yl)-3-[[(2s)-1-[bis(thiophen-3-ylmethyl)carbamoyloxy]hexan-2-yl]carbamoylamino]propanoate Chemical compound C([C@H](CCCC)NC(=O)N[C@@H](CC(=O)OC)C=1C=C2OCOC2=CC=1)OC(=O)N(CC1=CSC=C1)CC=1C=CSC=1 JAMLSOOENJLVDO-ZEQRLZLVSA-N 0.000 claims 1
- IVYLRHCZYKXOIL-ICSRJNTNSA-N methyl (3s)-3-(1,3-benzodioxol-5-yl)-3-[[(2s)-1-[methyl(thiophen-2-ylmethyl)carbamoyl]oxyhexan-2-yl]carbamoylamino]propanoate Chemical compound C([C@H](CCCC)NC(=O)N[C@@H](CC(=O)OC)C=1C=C2OCOC2=CC=1)OC(=O)N(C)CC1=CC=CS1 IVYLRHCZYKXOIL-ICSRJNTNSA-N 0.000 claims 1
- FSCDFSOZNSUESM-DHLKQENFSA-N methyl (3s)-3-(1,3-benzodioxol-5-yl)-3-[[[(2s)-1-[bis(thiophen-2-ylmethyl)carbamoyloxy]hexan-2-yl]-methylcarbamoyl]amino]propanoate Chemical compound C([C@H](CCCC)N(C)C(=O)N[C@@H](CC(=O)OC)C=1C=C2OCOC2=CC=1)OC(=O)N(CC=1SC=CC=1)CC1=CC=CS1 FSCDFSOZNSUESM-DHLKQENFSA-N 0.000 claims 1
- DZINKXYJLFCVIN-UHFFFAOYSA-N methyl 2-[bis(thiophen-2-ylmethyl)carbamoyl-methylamino]acetate Chemical compound COC(=O)CN(C)C(=O)N(Cc1cccs1)Cc1cccs1 DZINKXYJLFCVIN-UHFFFAOYSA-N 0.000 claims 1
- SEUCLEHZDQIOPA-UHFFFAOYSA-N methyl 3-[2-[bis(thiophen-2-ylmethyl)carbamoyloxy]ethylcarbamoylamino]propanoate Chemical compound C=1C=CSC=1CN(C(=O)OCCNC(=O)NCCC(=O)OC)CC1=CC=CS1 SEUCLEHZDQIOPA-UHFFFAOYSA-N 0.000 claims 1
- OAZLNWRXFZPOHB-KRWDZBQOSA-N methyl 3-[[(2s)-1-[bis(thiophen-2-ylmethyl)carbamoyloxy]hexan-2-yl]carbamoylamino]propanoate Chemical compound C=1C=CSC=1CN(C(=O)OC[C@H](CCCC)NC(=O)NCCC(=O)OC)CC1=CC=CS1 OAZLNWRXFZPOHB-KRWDZBQOSA-N 0.000 claims 1
- XIVPIGHKZUIGDD-UHFFFAOYSA-N n,n,n',n'-tetrakis(thiophen-2-ylmethyl)heptanediamide Chemical compound C=1C=CSC=1CN(CC=1SC=CC=1)C(=O)CCCCCC(=O)N(CC=1SC=CC=1)CC1=CC=CS1 XIVPIGHKZUIGDD-UHFFFAOYSA-N 0.000 claims 1
- QRYMYTJPNXZDCW-UHFFFAOYSA-N n,n,n',n'-tetrakis(thiophen-2-ylmethyl)hexanediamide Chemical compound C=1C=CSC=1CN(CC=1SC=CC=1)C(=O)CCCCC(=O)N(CC=1SC=CC=1)CC1=CC=CS1 QRYMYTJPNXZDCW-UHFFFAOYSA-N 0.000 claims 1
- FJQNPWOSBDBGAM-UHFFFAOYSA-N n,n,n',n'-tetrakis(thiophen-2-ylmethyl)octanediamide Chemical compound C=1C=CSC=1CN(CC=1SC=CC=1)C(=O)CCCCCCC(=O)N(CC=1SC=CC=1)CC1=CC=CS1 FJQNPWOSBDBGAM-UHFFFAOYSA-N 0.000 claims 1
- NFFPPPJLKPVROB-UHFFFAOYSA-N n,n,n',n'-tetrakis(thiophen-2-ylmethyl)pentanediamide Chemical compound C=1C=CSC=1CN(CC=1SC=CC=1)C(=O)CCCC(=O)N(CC=1SC=CC=1)CC1=CC=CS1 NFFPPPJLKPVROB-UHFFFAOYSA-N 0.000 claims 1
- VSQKGBMBBRJXHT-UHFFFAOYSA-N n,n,n',n'-tetrakis[(3-methoxyphenyl)methyl]hexanediamide Chemical compound COC1=CC=CC(CN(CC=2C=C(OC)C=CC=2)C(=O)CCCCC(=O)N(CC=2C=C(OC)C=CC=2)CC=2C=C(OC)C=CC=2)=C1 VSQKGBMBBRJXHT-UHFFFAOYSA-N 0.000 claims 1
- GQVKTSKVXYHBHY-UHFFFAOYSA-N n,n,n',n'-tetrakis[(4-methoxyphenyl)methyl]heptanediamide Chemical compound C1=CC(OC)=CC=C1CN(C(=O)CCCCCC(=O)N(CC=1C=CC(OC)=CC=1)CC=1C=CC(OC)=CC=1)CC1=CC=C(OC)C=C1 GQVKTSKVXYHBHY-UHFFFAOYSA-N 0.000 claims 1
- IAMDTPCAUBMMRA-UHFFFAOYSA-N n,n,n',n'-tetrakis[(4-methoxyphenyl)methyl]hexanediamide Chemical compound C1=CC(OC)=CC=C1CN(C(=O)CCCCC(=O)N(CC=1C=CC(OC)=CC=1)CC=1C=CC(OC)=CC=1)CC1=CC=C(OC)C=C1 IAMDTPCAUBMMRA-UHFFFAOYSA-N 0.000 claims 1
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| US11311619B2 (en) * | 2016-04-28 | 2022-04-26 | 7 Hills Pharma Inc. and Texas Heart Institute | Integrin activator vaccine compositions |
| JP7069032B2 (ja) * | 2016-03-24 | 2022-05-17 | ミレニアム ファーマシューティカルズ， インコーポレイテッド | がん免疫治療における胃腸の免疫関連有害事象の治療方法 |
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| WO2021034697A1 (en) * | 2019-08-16 | 2021-02-25 | The Regents Of The University Of California | Combined cancer therapy involving chemical activation of integrins and targeted cell immunotherapy |
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