JP2014506253A5 - - Google Patents
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- JP2014506253A5 JP2014506253A5 JP2013547456A JP2013547456A JP2014506253A5 JP 2014506253 A5 JP2014506253 A5 JP 2014506253A5 JP 2013547456 A JP2013547456 A JP 2013547456A JP 2013547456 A JP2013547456 A JP 2013547456A JP 2014506253 A5 JP2014506253 A5 JP 2014506253A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- borono
- propyl
- hexanoic acid
- acid
- 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 description 79
- 125000001424 substituent group Chemical group 0.000 claims description 78
- 125000001072 heteroaryl group Chemical group 0.000 claims description 77
- 125000003118 aryl group Chemical group 0.000 claims description 76
- 239000000203 mixture Substances 0.000 claims description 75
- 150000001875 compounds Chemical class 0.000 claims description 66
- 238000000034 method Methods 0.000 claims description 49
- 229910052757 nitrogen Inorganic materials 0.000 claims description 48
- 229910052799 carbon Inorganic materials 0.000 claims description 46
- -1 alpha amino acid compound Chemical class 0.000 claims description 44
- 241000124008 Mammalia Species 0.000 claims description 39
- 210000002460 smooth muscle Anatomy 0.000 claims description 38
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
- 238000009472 formulation Methods 0.000 claims description 21
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- IFXZVZTUTKSTCF-UHFFFAOYSA-N 2-[3-(4-acetylpiperazin-1-yl)propyl]-2-amino-6-boronohexanoic acid Chemical compound CC(=O)N1CCN(CCCC(N)(CCCCB(O)O)C(O)=O)CC1 IFXZVZTUTKSTCF-UHFFFAOYSA-N 0.000 claims description 14
- PJZAICPWHIIMRF-UHFFFAOYSA-N 2-amino-6-borono-2-(3-piperazin-1-ylpropyl)hexanoic acid Chemical compound OB(O)CCCCC(N)(C(O)=O)CCCN1CCNCC1 PJZAICPWHIIMRF-UHFFFAOYSA-N 0.000 claims description 14
- KZLKEYDLEVVVGJ-UHFFFAOYSA-N 2-amino-6-borono-2-[3-[4-[(3-methoxyphenyl)carbamoyl]piperazin-1-yl]propyl]hexanoic acid Chemical group COC1=CC=CC(NC(=O)N2CCN(CCCC(N)(CCCCB(O)O)C(O)=O)CC2)=C1 KZLKEYDLEVVVGJ-UHFFFAOYSA-N 0.000 claims description 14
- 102000004452 Arginase Human genes 0.000 claims description 14
- 108700024123 Arginases Proteins 0.000 claims description 14
- AVPJLCOJTXEOAV-UHFFFAOYSA-N C1CN(CCCC(CCCC)C(O)=O)CCN1C(=O)C1=CC=C(C#N)C=C1 Chemical compound C1CN(CCCC(CCCC)C(O)=O)CCN1C(=O)C1=CC=C(C#N)C=C1 AVPJLCOJTXEOAV-UHFFFAOYSA-N 0.000 claims description 14
- WFBHRSAKANVBKH-UHFFFAOYSA-N N-hydroxyguanidine Chemical group NC(=N)NO WFBHRSAKANVBKH-UHFFFAOYSA-N 0.000 claims description 14
- 125000005620 boronic acid group Chemical group 0.000 claims description 14
- 230000002685 pulmonary effect Effects 0.000 claims description 14
- 235000008206 alpha-amino acids Nutrition 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 238000007918 intramuscular administration Methods 0.000 claims description 12
- 238000001990 intravenous administration Methods 0.000 claims description 12
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 12
- 238000007920 subcutaneous administration Methods 0.000 claims description 12
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 11
- 206010028980 Neoplasm Diseases 0.000 claims description 11
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims description 11
- 201000011510 cancer Diseases 0.000 claims description 11
- 239000003112 inhibitor Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 210000005070 sphincter Anatomy 0.000 claims description 7
- MSYGAHOHLUJIKV-UHFFFAOYSA-N 3,5-dimethyl-1-(3-nitrophenyl)-1h-pyrazole-4-carboxylic acid ethyl ester Chemical compound CC1=C(C(=O)OCC)C(C)=NN1C1=CC=CC([N+]([O-])=O)=C1 MSYGAHOHLUJIKV-UHFFFAOYSA-N 0.000 claims description 6
- 101001098814 Dictyostelium discoideum 3',5'-cyclic-nucleotide phosphodiesterase regA Proteins 0.000 claims description 6
- 101001117086 Dictyostelium discoideum cAMP/cGMP-dependent 3',5'-cAMP/cGMP phosphodiesterase A Proteins 0.000 claims description 6
- 101001098806 Dictyostelium discoideum cGMP-specific 3',5'-cGMP phosphodiesterase 3 Proteins 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 206010063837 Reperfusion injury Diseases 0.000 claims description 6
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims description 6
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- 238000003384 imaging method Methods 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- UHJHOMWGKLNKSW-UHFFFAOYSA-N 2-amino-2-[3-[benzyl(ethyl)amino]propyl]-6-boronohexanoic acid Chemical compound OB(O)CCCCC(N)(C(O)=O)CCCN(CC)CC1=CC=CC=C1 UHJHOMWGKLNKSW-UHFFFAOYSA-N 0.000 claims description 4
- 208000035143 Bacterial infection Diseases 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 4
- 239000002872 contrast media Substances 0.000 claims description 4
- 239000002961 echo contrast media Substances 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 239000007850 fluorescent dye Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 208000012947 ischemia reperfusion injury Diseases 0.000 claims description 4
- 239000002405 nuclear magnetic resonance imaging agent Substances 0.000 claims description 4
- 230000002018 overexpression Effects 0.000 claims description 4
- 201000004193 respiratory failure Diseases 0.000 claims description 4
- 238000002054 transplantation Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 210000005226 corpus cavernosum Anatomy 0.000 claims description 3
- 230000003176 fibrotic effect Effects 0.000 claims description 3
- 230000002496 gastric effect Effects 0.000 claims description 3
- 210000003734 kidney Anatomy 0.000 claims description 3
- 210000004072 lung Anatomy 0.000 claims description 3
- 210000003205 muscle Anatomy 0.000 claims description 3
- 230000003169 placental effect Effects 0.000 claims description 3
- DMZDUZBVSGSJKK-ACGXKRRESA-N (2S)-2-amino-6-borono-2-[3-(1-carboxyethylamino)propyl]hexanoic acid Chemical compound OC(=O)C(C)NCCC[C@](N)(C(O)=O)CCCCB(O)O DMZDUZBVSGSJKK-ACGXKRRESA-N 0.000 claims description 2
- DKYMUJJLXCTWSM-CVRLYYSRSA-N (2s)-2-amino-6-borono-2-[3-[(1-carboxy-3-methylbutyl)amino]propyl]hexanoic acid Chemical compound CC(C)CC(C(O)=O)NCCC[C@](N)(C(O)=O)CCCCB(O)O DKYMUJJLXCTWSM-CVRLYYSRSA-N 0.000 claims description 2
- YHSUWYJIWKJAFG-VYIIXAMBSA-N (2s)-2-amino-6-borono-2-[3-[(1-methoxy-4-methyl-1-oxopentan-2-yl)amino]propyl]hexanoic acid Chemical compound COC(=O)C(CC(C)C)NCCC[C@](N)(C(O)=O)CCCCB(O)O YHSUWYJIWKJAFG-VYIIXAMBSA-N 0.000 claims description 2
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims description 2
- CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 claims description 2
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 2
- OIOSDHQLKMVRQD-UHFFFAOYSA-N 2-[2-amino-2-[3-[4-(2-chlorophenyl)pyrazol-1-yl]piperidin-1-yl]propyl]-6-boronohexanoic acid Chemical compound C1N(C(N)(CC(CCCCB(O)O)C(O)=O)C)CCCC1N1N=CC(C=2C(=CC=CC=2)Cl)=C1 OIOSDHQLKMVRQD-UHFFFAOYSA-N 0.000 claims description 2
- CCFTXZXKNCVCRW-UHFFFAOYSA-N 2-[3-[4-(4-fluorophenyl)piperidin-1-yl]propyl]hexanoic acid Chemical compound C1CN(CCCC(CCCC)C(O)=O)CCC1C1=CC=C(F)C=C1 CCFTXZXKNCVCRW-UHFFFAOYSA-N 0.000 claims description 2
- XJLITJHUQRBWPN-UHFFFAOYSA-N 2-acetamidoacetic acid;4-[2-(4-carbamimidoylphenyl)iminohydrazinyl]benzenecarboximidamide Chemical compound CC(=O)NCC(O)=O.C1=CC(C(=N)N)=CC=C1NN=NC1=CC=C(C(N)=N)C=C1 XJLITJHUQRBWPN-UHFFFAOYSA-N 0.000 claims description 2
- JRPAMPYUINVTRE-UHFFFAOYSA-N 2-amino-2-(4-boronobutyl)-6-(3,4-dihydro-1h-isoquinolin-2-yl)hexanoic acid Chemical compound C1=CC=C2CN(CCCCC(CCCCB(O)O)(N)C(O)=O)CCC2=C1 JRPAMPYUINVTRE-UHFFFAOYSA-N 0.000 claims description 2
- KDWYCCPYIHPYCH-UHFFFAOYSA-N 2-amino-2-(4-boronobutyl)-6-[2-(4-fluorophenyl)piperidin-1-yl]hexanoic acid Chemical compound OB(O)CCCCC(N)(C(O)=O)CCCCN1CCCCC1C1=CC=C(F)C=C1 KDWYCCPYIHPYCH-UHFFFAOYSA-N 0.000 claims description 2
- JVXBSROYIBBRFJ-UHFFFAOYSA-N 2-amino-2-(4-boronobutyl)-6-[4-(3,4-dichlorophenyl)piperazin-1-yl]hexanoic acid Chemical compound C1CN(CCCCC(CCCCB(O)O)(N)C(O)=O)CCN1C1=CC=C(Cl)C(Cl)=C1 JVXBSROYIBBRFJ-UHFFFAOYSA-N 0.000 claims description 2
- XKKSNZAYJGFESW-UHFFFAOYSA-N 2-amino-2-(4-boronobutyl)-6-[4-[(3,4-difluorophenyl)methyl]piperidin-1-yl]hexanoic acid Chemical compound C1CN(CCCCC(CCCCB(O)O)(N)C(O)=O)CCC1CC1=CC=C(F)C(F)=C1 XKKSNZAYJGFESW-UHFFFAOYSA-N 0.000 claims description 2
- BPBSCILZHOHUHO-UHFFFAOYSA-N 2-amino-2-(4-boronobutyl)-6-piperazin-1-ylhexanoic acid Chemical compound OB(O)CCCCC(N)(C(O)=O)CCCCN1CCNCC1 BPBSCILZHOHUHO-UHFFFAOYSA-N 0.000 claims description 2
- ISQZWVMUKBCATQ-UHFFFAOYSA-N 2-amino-2-[3-(2-benzylpiperidin-1-yl)propyl]-6-boronohexanoic acid Chemical compound OB(O)CCCCC(N)(C(O)=O)CCCN1CCCCC1CC1=CC=CC=C1 ISQZWVMUKBCATQ-UHFFFAOYSA-N 0.000 claims description 2
- ABRLPVPSSCYJFO-UHFFFAOYSA-N 2-amino-2-[3-(4-benzamidopiperidin-1-yl)propyl]-6-boronohexanoic acid Chemical compound C1CN(CCCC(CCCCB(O)O)(N)C(O)=O)CCC1NC(=O)C1=CC=CC=C1 ABRLPVPSSCYJFO-UHFFFAOYSA-N 0.000 claims description 2
- BRWBTRDLVZIMIM-UHFFFAOYSA-N 2-amino-2-[3-(4-benzhydrylpiperazin-1-yl)propyl]-6-boronohexanoic acid Chemical compound C1CN(CCCC(CCCCB(O)O)(N)C(O)=O)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 BRWBTRDLVZIMIM-UHFFFAOYSA-N 0.000 claims description 2
- PRQHZEBQSNCYEO-UHFFFAOYSA-N 2-amino-2-[3-(4-benzylpiperazin-1-yl)propyl]-6-boronohexanoic acid Chemical compound C1CN(CCCC(CCCCB(O)O)(N)C(O)=O)CCN1CC1=CC=CC=C1 PRQHZEBQSNCYEO-UHFFFAOYSA-N 0.000 claims description 2
- SJSURLHRMWNOEB-UHFFFAOYSA-N 2-amino-2-[3-(azetidin-1-yl)propyl]-6-boronohexanoic acid Chemical compound OB(O)CCCCC(N)(C(O)=O)CCCN1CCC1 SJSURLHRMWNOEB-UHFFFAOYSA-N 0.000 claims description 2
- GCUCLBYXPNHVCP-UHFFFAOYSA-N 2-amino-2-[3-(benzimidazol-1-yl)propyl]-6-boronohexanoic acid Chemical compound C1=CC=C2N(CCCC(CCCCB(O)O)(N)C(O)=O)C=NC2=C1 GCUCLBYXPNHVCP-UHFFFAOYSA-N 0.000 claims description 2
- SDISAHFEZPRFNC-UHFFFAOYSA-N 2-amino-2-[3-[3-(1,3-benzoxazol-2-yl)piperidin-1-yl]propyl]-6-boronohexanoic acid Chemical compound C1N(CCCC(CCCCB(O)O)(N)C(O)=O)CCCC1C1=NC2=CC=CC=C2O1 SDISAHFEZPRFNC-UHFFFAOYSA-N 0.000 claims description 2
- ZYPABFVXOIZNME-UCFFOFKASA-N 2-amino-2-[3-[4-[(2s)-2-amino-3-methylbutanoyl]oxypiperidin-1-yl]propyl]-6-boronohexanoic acid Chemical compound CC(C)[C@H](N)C(=O)OC1CCN(CCCC(N)(CCCCB(O)O)C(O)=O)CC1 ZYPABFVXOIZNME-UCFFOFKASA-N 0.000 claims description 2
- WHORZLUFVHMYES-UHFFFAOYSA-N 2-amino-3-[3-(4-benzyl-4-decanoyloxypiperidin-1-yl)propyl]-6-boronohexanoic acid Chemical compound C=1C=CC=CC=1CC1(OC(=O)CCCCCCCCC)CCN(CCCC(CCCB(O)O)C(N)C(O)=O)CC1 WHORZLUFVHMYES-UHFFFAOYSA-N 0.000 claims description 2
- MHUBXSPFADMQDW-UHFFFAOYSA-N 2-amino-6-borono-2-(2-piperazin-1-ylethyl)hexanoic acid Chemical compound OB(O)CCCCC(N)(C(O)=O)CCN1CCNCC1 MHUBXSPFADMQDW-UHFFFAOYSA-N 0.000 claims description 2
- FPLQQVASXNNHMZ-UHFFFAOYSA-N 2-amino-6-borono-2-(2-piperidin-2-ylethyl)hexanoic acid Chemical compound OB(O)CCCCC(N)(C(O)=O)CCC1CCCCN1 FPLQQVASXNNHMZ-UHFFFAOYSA-N 0.000 claims description 2
- YZYDQVUTKBQKTJ-UHFFFAOYSA-N 2-amino-6-borono-2-(3-imidazol-1-ylpropyl)hexanoic acid Chemical compound OB(O)CCCCC(N)(C(O)=O)CCCN1C=CN=C1 YZYDQVUTKBQKTJ-UHFFFAOYSA-N 0.000 claims description 2
- ORZSJZSNPWNMAZ-UHFFFAOYSA-N 2-amino-6-borono-2-(3-morpholin-4-ylpropyl)hexanoic acid Chemical compound OB(O)CCCCC(N)(C(O)=O)CCCN1CCOCC1 ORZSJZSNPWNMAZ-UHFFFAOYSA-N 0.000 claims description 2
- ZXBYEQISFHBUQA-UHFFFAOYSA-N 2-amino-6-borono-2-(3-pyrrolidin-1-ylpropyl)hexanoic acid Chemical compound OB(O)CCCCC(N)(C(O)=O)CCCN1CCCC1 ZXBYEQISFHBUQA-UHFFFAOYSA-N 0.000 claims description 2
- RBVAUPSKVSBIOG-UHFFFAOYSA-N 2-amino-6-borono-2-(3-spiro[1h-2-benzofuran-3,4'-piperidine]-1'-ylpropyl)hexanoic acid Chemical compound C1CN(CCCC(CCCCB(O)O)(N)C(O)=O)CCC21C1=CC=CC=C1CO2 RBVAUPSKVSBIOG-UHFFFAOYSA-N 0.000 claims description 2
- UZBXQNBMFCPICE-UHFFFAOYSA-N 2-amino-6-borono-2-(3-thiomorpholin-4-ylpropyl)hexanoic acid Chemical compound OB(O)CCCCC(N)(C(O)=O)CCCN1CCSCC1 UZBXQNBMFCPICE-UHFFFAOYSA-N 0.000 claims description 2
- KZHIKBONRPBXNG-UHFFFAOYSA-N 2-amino-6-borono-2-[2-[1-[(3,4-dichlorophenyl)methyl]piperidin-2-yl]ethyl]hexanoic acid Chemical compound OB(O)CCCCC(N)(C(O)=O)CCC1CCCCN1CC1=CC=C(Cl)C(Cl)=C1 KZHIKBONRPBXNG-UHFFFAOYSA-N 0.000 claims description 2
- WCYRKXCGRYIJRH-UHFFFAOYSA-N 2-amino-6-borono-2-[2-[1-[(3,4-dichlorophenyl)methyl]piperidin-3-yl]ethyl]hexanoic acid Chemical compound C1C(CCC(CCCCB(O)O)(N)C(O)=O)CCCN1CC1=CC=C(Cl)C(Cl)=C1 WCYRKXCGRYIJRH-UHFFFAOYSA-N 0.000 claims description 2
- YYJVYSBXZGKIJR-UHFFFAOYSA-N 2-amino-6-borono-2-[2-[1-[(3,4-difluorophenyl)methyl]piperidin-2-yl]ethyl]hexanoic acid Chemical compound OB(O)CCCCC(N)(C(O)=O)CCC1CCCCN1CC1=CC=C(F)C(F)=C1 YYJVYSBXZGKIJR-UHFFFAOYSA-N 0.000 claims description 2
- FLGMBTLQHHKAQB-UHFFFAOYSA-N 2-amino-6-borono-2-[2-[1-[(3,5-difluorophenyl)methyl]piperidin-2-yl]ethyl]hexanoic acid Chemical compound OB(O)CCCCC(N)(C(O)=O)CCC1CCCCN1CC1=CC(F)=CC(F)=C1 FLGMBTLQHHKAQB-UHFFFAOYSA-N 0.000 claims description 2
- GPYLVJBNODICFF-UHFFFAOYSA-N 2-amino-6-borono-2-[2-[4-[(3,4-dichlorophenyl)methyl]piperazin-1-yl]ethyl]hexanoic acid Chemical compound C1CN(CCC(CCCCB(O)O)(N)C(O)=O)CCN1CC1=CC=C(Cl)C(Cl)=C1 GPYLVJBNODICFF-UHFFFAOYSA-N 0.000 claims description 2
- AULXBFOVMWZDJD-UHFFFAOYSA-N 2-amino-6-borono-2-[3-(1,3-thiazolidin-2-yl)propyl]hexanoic acid Chemical compound OB(O)CCCCC(N)(C(O)=O)CCCC1NCCS1 AULXBFOVMWZDJD-UHFFFAOYSA-N 0.000 claims description 2
- FEWFZHXFKDOVJY-UHFFFAOYSA-N 2-amino-6-borono-2-[3-(2-methoxyethylamino)propyl]hexanoic acid Chemical compound COCCNCCCC(N)(C(O)=O)CCCCB(O)O FEWFZHXFKDOVJY-UHFFFAOYSA-N 0.000 claims description 2
- HOLSSIRGZOSRNR-UHFFFAOYSA-N 2-amino-6-borono-2-[3-(2-phenylethylamino)propyl]hexanoic acid Chemical compound OB(O)CCCCC(N)(C(O)=O)CCCNCCC1=CC=CC=C1 HOLSSIRGZOSRNR-UHFFFAOYSA-N 0.000 claims description 2
- CAIUNHCJFOTQGB-UHFFFAOYSA-N 2-amino-6-borono-2-[3-(3,4-dihydro-1h-isoquinolin-2-yl)propyl]hexanoic acid Chemical compound C1=CC=C2CN(CCCC(CCCCB(O)O)(N)C(O)=O)CCC2=C1 CAIUNHCJFOTQGB-UHFFFAOYSA-N 0.000 claims description 2
- AUYUFTCGRPMQTR-UHFFFAOYSA-N 2-amino-6-borono-2-[3-(3-fluoro-4-phenylpiperidin-1-yl)propyl]hexanoic acid Chemical compound FC1CN(CCCC(CCCCB(O)O)(N)C(O)=O)CCC1C1=CC=CC=C1 AUYUFTCGRPMQTR-UHFFFAOYSA-N 0.000 claims description 2
- GMAMYAZILAOVSG-UHFFFAOYSA-N 2-amino-6-borono-2-[3-(3-phenylazetidin-1-yl)propyl]hexanoic acid Chemical compound C1N(CCCC(CCCCB(O)O)(N)C(O)=O)CC1C1=CC=CC=C1 GMAMYAZILAOVSG-UHFFFAOYSA-N 0.000 claims description 2
- DCDSJOGIRPSVDK-UHFFFAOYSA-N 2-amino-6-borono-2-[3-(3-phenylpiperidin-1-yl)propyl]hexanoic acid Chemical compound C1N(CCCC(CCCCB(O)O)(N)C(O)=O)CCCC1C1=CC=CC=C1 DCDSJOGIRPSVDK-UHFFFAOYSA-N 0.000 claims description 2
- FFJFBFSKGTUCRE-UHFFFAOYSA-N 2-amino-6-borono-2-[3-(4-ethylpiperazin-1-yl)propyl]hexanoic acid Chemical compound CCN1CCN(CCCC(N)(CCCCB(O)O)C(O)=O)CC1 FFJFBFSKGTUCRE-UHFFFAOYSA-N 0.000 claims description 2
- XNFZOEQJCMLVHJ-UHFFFAOYSA-N 2-amino-6-borono-2-[3-(4-hydroxypiperidin-1-yl)propyl]hexanoic acid Chemical compound OB(O)CCCCC(N)(C(O)=O)CCCN1CCC(O)CC1 XNFZOEQJCMLVHJ-UHFFFAOYSA-N 0.000 claims description 2
- SWDAOXKFESLGRZ-UHFFFAOYSA-N 2-amino-6-borono-2-[3-(4-methyl-2-phenylpiperazin-1-yl)propyl]hexanoic acid Chemical compound C1N(C)CCN(CCCC(N)(CCCCB(O)O)C(O)=O)C1C1=CC=CC=C1 SWDAOXKFESLGRZ-UHFFFAOYSA-N 0.000 claims description 2
- MJDKZPARBWCXBG-UHFFFAOYSA-N 2-amino-6-borono-2-[3-(4-methylpiperazin-1-yl)propyl]hexanoic acid Chemical compound CN1CCN(CCCC(N)(CCCCB(O)O)C(O)=O)CC1 MJDKZPARBWCXBG-UHFFFAOYSA-N 0.000 claims description 2
- QJHUGBUKOMUTGT-UHFFFAOYSA-N 2-amino-6-borono-2-[3-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-8-yl)propyl]hexanoic acid Chemical compound C1CN(CCCC(CCCCB(O)O)(N)C(O)=O)CCC21C(=O)NCN2C1=CC=CC=C1 QJHUGBUKOMUTGT-UHFFFAOYSA-N 0.000 claims description 2
- VVWYKAHJILQCLR-UHFFFAOYSA-N 2-amino-6-borono-2-[3-(5-phenyl-2,3-dihydropyrrol-1-yl)propyl]hexanoic acid Chemical compound OB(O)CCCCC(N)(C(O)=O)CCCN1CCC=C1C1=CC=CC=C1 VVWYKAHJILQCLR-UHFFFAOYSA-N 0.000 claims description 2
- MSKGXUQDAKTGRQ-UHFFFAOYSA-N 2-amino-6-borono-2-[3-(carboxymethylamino)propyl]hexanoic acid Chemical compound OB(O)CCCCC(N)(C(O)=O)CCCNCC(O)=O MSKGXUQDAKTGRQ-UHFFFAOYSA-N 0.000 claims description 2
- AZDJHLHWFPOSQP-UHFFFAOYSA-N 2-amino-6-borono-2-[3-(cyclohexylamino)propyl]hexanoic acid Chemical compound OB(O)CCCCC(N)(C(O)=O)CCCNC1CCCCC1 AZDJHLHWFPOSQP-UHFFFAOYSA-N 0.000 claims description 2
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- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 208000021331 vascular occlusion disease Diseases 0.000 claims 1
- 0 C*1CN(*)C(CCC(CC=CCB(O)O)(C(O)=O)N)CCC1 Chemical compound C*1CN(*)C(CCC(CC=CCB(O)O)(C(O)=O)N)CCC1 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
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| DK2632927T3 (en) | 2010-10-26 | 2016-04-11 | Mars Inc | Boronates AS ARGINSASEINHIBITORER |
| US9266908B2 (en) | 2011-10-19 | 2016-02-23 | Mars, Incorporated | Inhibitors of arginase and their therapeutic applications |
| CA2944903A1 (en) | 2014-04-24 | 2015-10-29 | Dana-Farber Cancer Institute, Inc. | Tumor suppressor and oncogene biomarkers predictive of anti-immune checkpoint inhibitor response |
| PL410665A1 (pl) | 2014-12-29 | 2016-07-04 | Oncoarendi Therapeutics Spółka Z Ograniczoną Odpowiedzialnością | Inhibitory arginazy oraz ich zastosowania terapeutyczne |
| KR20180021117A (ko) | 2015-06-23 | 2018-02-28 | 칼리테라 바이오사이언시즈, 인코포레이티드 | 아르기나제 활성 억제를 위한 조성물 및 방법 |
| CN108601767A (zh) * | 2015-10-05 | 2018-09-28 | 卡利泰拉生物科技公司 | 用谷氨酰胺酶抑制剂和免疫肿瘤学药剂的组合疗法 |
| JP6807322B2 (ja) * | 2015-10-16 | 2021-01-06 | 武田薬品工業株式会社 | 複素環化合物の製造方法 |
| WO2017075363A1 (en) * | 2015-10-30 | 2017-05-04 | Calithera Biosciences, Inc. | Compositions and methods for inhibiting arginase activity |
| PL417066A1 (pl) | 2016-05-04 | 2017-11-06 | Oncoarendi Therapeutics Spółka Z Ograniczoną Odpowiedzialnością | Inhibitory arginazy oraz ich zastosowania terapeutyczne |
| EP3538111B1 (en) | 2016-11-08 | 2022-01-19 | Calithera Biosciences, Inc. | Arginase inhibitor combination therapies |
| SMT202100573T1 (it) | 2016-12-22 | 2021-11-12 | Calithera Biosciences Inc | Composizioni e metodi per l'inibizione dell'attivita' dell'arginasi |
| WO2018209290A1 (en) | 2017-05-12 | 2018-11-15 | Calithera Biosciences, Inc. | Method of preparing (3r,4s)-3-acetamido-4-allyl-n-(tert-butyl)pyrrolidine-3-carboxamide |
| TWI803574B (zh) * | 2018-02-17 | 2023-06-01 | 瑞典商阿斯特捷利康公司 | 精胺酸酶抑制劑及其使用方法 |
| CN111818928A (zh) | 2018-03-05 | 2020-10-23 | 艾库斯生物科学有限公司 | 精氨酸酶抑制剂 |
| EP3765006A4 (en) | 2018-03-13 | 2022-02-23 | Merck Sharp & Dohme Corp. | ARGINASE INHIBITORS AND METHODS OF USE |
| EP3774843B1 (en) | 2018-03-29 | 2022-05-25 | Molecure SA | Dipeptide piperidine derivatives |
| WO2019205979A1 (zh) * | 2018-04-27 | 2019-10-31 | 四川科伦博泰生物医药股份有限公司 | 非天然氨基酸类衍生物、包含其的药物组合物及其制备方法和用途 |
| EP3810615B1 (en) | 2018-06-20 | 2026-01-28 | Merck Sharp & Dohme LLC | Arginase inhibitors and methods of use |
| ES3034676T3 (en) | 2018-11-16 | 2025-08-21 | Arcus Biosciences Inc | Inhibitors of arg1 and/or arg2 |
| US12240867B2 (en) | 2018-12-18 | 2025-03-04 | Merck Sharp & Dohme Llc | Arginase inhibitors and methods of use |
| CN119119095A (zh) * | 2019-07-23 | 2024-12-13 | 阿斯利康(瑞典)有限公司 | 精氨酸酶抑制剂及其使用方法 |
| CA3180529A1 (en) * | 2020-04-17 | 2021-10-21 | Bio-Cancer Treatment International Limited | Methods of treating viral infections using arginase |
| TW202228720A (zh) | 2020-12-22 | 2022-08-01 | 波蘭商昂科艾倫迪治療法股份公司 | 精胺酸酶抑制劑及其使用方法 |
| WO2022272268A1 (en) * | 2021-06-23 | 2022-12-29 | Yale University | Compounds for molecular imaging of collagen turnover and methods using same |
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| US4477391A (en) | 1981-08-14 | 1984-10-16 | Collins James F | Amino acid isomers, their production and their medicinal use |
| US5792769A (en) * | 1995-09-29 | 1998-08-11 | 3-Dimensional Pharmaceuticals, Inc. | Guanidino protease inhibitors |
| WO1997024135A1 (en) * | 1995-12-29 | 1997-07-10 | 3-Dimensional Pharmaceuticals, Inc. | Amidino protease inhibitors |
| US5891909A (en) * | 1996-03-29 | 1999-04-06 | 3-Dimensional Pharmaceuticals, Inc. | Amidinohydrazones as protease inhibitors |
| TW499412B (en) * | 1996-11-26 | 2002-08-21 | Dimensional Pharm Inc | Aminoguanidines and alkoxyguanidines as protease inhibitors |
| WO1999019295A1 (en) * | 1997-10-10 | 1999-04-22 | Trustees Of The University Of Pennsylvania | Compositions and methods for inhibiting arginase activity |
| TWI222441B (en) * | 1997-11-26 | 2004-10-21 | Dimensional Pharm Inc | Heteroaryl aminoguanidines and alkoxyguanidines and their use as protease inhibitors |
| US6344486B1 (en) * | 1998-04-03 | 2002-02-05 | 3-Dimensional Pharmaceuticals, Inc. | Benzamide and sulfonamide substituted aminoguanidines and alkoxyguanidines as protease inhibitors |
| WO1999055355A1 (en) * | 1998-04-24 | 1999-11-04 | 3-Dimensional Pharmaceuticals, Inc. | Amino acid amidinohydrazones, alkoxyguanidines and aminoguanidines as protease inhibitors |
| JP4554077B2 (ja) * | 1998-06-11 | 2010-09-29 | オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド | ピラジノンプロテアーゼインヒビター |
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| CA2415932A1 (en) * | 2000-07-17 | 2002-01-24 | 3-Dimensional Pharmaceuticals, Inc. | Cyclic oxyguanidine pyrazinones as protease inhibitors |
| CA2417914A1 (en) * | 2000-08-04 | 2002-02-14 | 3-Dimensional Pharmaceuticals, Inc. | Cyclic oxyguanidine protease inhibitors |
| UA75093C2 (en) * | 2000-10-06 | 2006-03-15 | Dimensional Pharm Inc | Aminopyridinyl-,aminoguanidinyl-, and alkoxyguanidinesubstituted phenylsubstituted phenylacetamides as protease inhibitors |
| AU2003218099A1 (en) * | 2002-03-12 | 2003-09-29 | Lsu Medical Center | Modulation of the immune response through the manipulation of arginine levels |
| US20050176651A1 (en) * | 2002-09-09 | 2005-08-11 | Trigen Limited | Peptide boronic acids useful in making salts thereof |
| GB0405267D0 (en) | 2004-03-09 | 2004-04-21 | Trigen Ltd | Compounds |
| EP1863431A1 (en) * | 2005-03-18 | 2007-12-12 | L'Oréal | Hair and/or eyelash care composition containing aminexil in combination with an agent for promoting the no production and uses thereof |
| CN101932599A (zh) * | 2005-11-10 | 2010-12-29 | 阿波罗生命科学有限公司 | 分子及其嵌合分子 |
| SI2389352T1 (sl) * | 2009-01-26 | 2019-08-30 | The Trustees Of The University Of Pennsylvania, Center For Technology Transfer | Inhibitorji arginaze in postopki uporabe |
| CN103068830B (zh) * | 2010-04-22 | 2016-06-29 | 马尔斯公司 | 精氨酸酶抑制剂及其治疗应用 |
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