BR112020009972A2 - inibidores de c5ar para uso no tratamento de dor iatrogênica induzida por quimioterapia - Google Patents
inibidores de c5ar para uso no tratamento de dor iatrogênica induzida por quimioterapia Download PDFInfo
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- BR112020009972A2 BR112020009972A2 BR112020009972-4A BR112020009972A BR112020009972A2 BR 112020009972 A2 BR112020009972 A2 BR 112020009972A2 BR 112020009972 A BR112020009972 A BR 112020009972A BR 112020009972 A2 BR112020009972 A2 BR 112020009972A2
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- BR
- Brazil
- Prior art keywords
- phenyl
- group
- ethyl
- alkyl
- branched
- Prior art date
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- 238000011282 treatment Methods 0.000 title claims abstract description 64
- 208000002193 Pain Diseases 0.000 title claims abstract description 47
- 239000003112 inhibitor Substances 0.000 title claims abstract description 38
- 238000002512 chemotherapy Methods 0.000 title claims abstract description 34
- 230000000642 iatrogenic effect Effects 0.000 title claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 230000002265 prevention Effects 0.000 claims abstract description 25
- 102100032957 C5a anaphylatoxin chemotactic receptor 1 Human genes 0.000 claims abstract description 17
- 101710098483 C5a anaphylatoxin chemotactic receptor 1 Proteins 0.000 claims abstract 15
- 229930012538 Paclitaxel Natural products 0.000 claims description 73
- 229960001592 paclitaxel Drugs 0.000 claims description 73
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 72
- -1 2-oxazolyl Chemical group 0.000 claims description 60
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 208000004454 Hyperalgesia Diseases 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 20
- 229940079593 drug Drugs 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 206010053552 allodynia Diseases 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- 239000002246 antineoplastic agent Substances 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 12
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
- 229940127089 cytotoxic agent Drugs 0.000 claims description 10
- 229910052717 sulfur Chemical group 0.000 claims description 10
- 229910052757 nitrogen Chemical group 0.000 claims description 9
- 241000689227 Cora <basidiomycete fungus> Species 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- 241000036848 Porzana carolina Species 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 6
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 229930192474 thiophene Natural products 0.000 claims description 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 5
- UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 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
- 108010021331 carfilzomib Proteins 0.000 claims description 5
- 229960002438 carfilzomib Drugs 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- GOTYRUGSSMKFNF-UHFFFAOYSA-N lenalidomide Chemical compound C1C=2C(N)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O GOTYRUGSSMKFNF-UHFFFAOYSA-N 0.000 claims description 5
- 229960004942 lenalidomide Drugs 0.000 claims description 5
- UVSMNLNDYGZFPF-UHFFFAOYSA-N pomalidomide Chemical compound O=C1C=2C(N)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O UVSMNLNDYGZFPF-UHFFFAOYSA-N 0.000 claims description 5
- 229960000688 pomalidomide Drugs 0.000 claims description 5
- 229960003433 thalidomide Drugs 0.000 claims description 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004419 alkynylene group Chemical group 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 229960001467 bortezomib Drugs 0.000 claims description 4
- 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 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229960003649 eribulin Drugs 0.000 claims description 4
- UFNVPOGXISZXJD-XJPMSQCNSA-N eribulin Chemical compound C([C@H]1CC[C@@H]2O[C@@H]3[C@H]4O[C@H]5C[C@](O[C@H]4[C@H]2O1)(O[C@@H]53)CC[C@@H]1O[C@H](C(C1)=C)CC1)C(=O)C[C@@H]2[C@@H](OC)[C@@H](C[C@H](O)CN)O[C@H]2C[C@@H]2C(=C)[C@H](C)C[C@H]1O2 UFNVPOGXISZXJD-XJPMSQCNSA-N 0.000 claims description 4
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 4
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 229960001756 oxaliplatin Drugs 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 150000003536 tetrazoles Chemical class 0.000 claims description 4
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 4
- 150000003852 triazoles Chemical class 0.000 claims description 4
- 229960004528 vincristine Drugs 0.000 claims description 4
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 claims description 4
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 claims description 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 3
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims description 3
- 229930013930 alkaloid Natural products 0.000 claims description 3
- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 claims description 3
- 229960001573 cabazitaxel Drugs 0.000 claims description 3
- BMQGVNUXMIRLCK-OAGWZNDDSA-N cabazitaxel Chemical compound O([C@H]1[C@@H]2[C@]3(OC(C)=O)CO[C@@H]3C[C@@H]([C@]2(C(=O)[C@H](OC)C2=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=3C=CC=CC=3)C[C@]1(O)C2(C)C)C)OC)C(=O)C1=CC=CC=C1 BMQGVNUXMIRLCK-OAGWZNDDSA-N 0.000 claims description 3
- 229960004562 carboplatin Drugs 0.000 claims description 3
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 3
- 229960004316 cisplatin Drugs 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229960003668 docetaxel Drugs 0.000 claims description 3
- 229960005420 etoposide Drugs 0.000 claims description 3
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims description 3
- 229960002014 ixabepilone Drugs 0.000 claims description 3
- FABUFPQFXZVHFB-CFWQTKTJSA-N ixabepilone Chemical compound C/C([C@@H]1C[C@@H]2O[C@]2(C)CCC[C@@H]([C@@H]([C@H](C)C(=O)C(C)(C)[C@H](O)CC(=O)N1)O)C)=C\C1=CSC(C)=N1 FABUFPQFXZVHFB-CFWQTKTJSA-N 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 229960003048 vinblastine Drugs 0.000 claims description 3
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 claims description 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 2
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 2
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- PWNMDNDIVOXBSU-SSDOTTSWSA-N 4-[(1r)-1-[4-[[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino]phenyl]ethyl]-1,2,5-thiadiazol-3-one Chemical compound C1([C@H](C)C=2C=CC(NC=3SC=C(N=3)C(F)(F)F)=CC=2)=NSN=C1O PWNMDNDIVOXBSU-SSDOTTSWSA-N 0.000 claims description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 2
- RCKAGEAESHXMIH-MRVPVSSYSA-N 4-methyl-5-[(1r)-1-[4-[[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino]phenyl]ethyl]-1,2-oxazol-3-one Chemical compound C=1([C@H](C)C=2C=CC(NC=3SC=C(N=3)C(F)(F)F)=CC=2)ON=C(O)C=1C RCKAGEAESHXMIH-MRVPVSSYSA-N 0.000 claims description 2
- PBGXUWBEWSDLKD-SECBINFHSA-N 4-methyl-n-[4-[(1r)-1-(2h-tetrazol-5-yl)ethyl]phenyl]-1,3-oxazol-2-amine Chemical compound C1([C@H](C)C=2C=CC(NC=3OC=C(C)N=3)=CC=2)=NN=NN1 PBGXUWBEWSDLKD-SECBINFHSA-N 0.000 claims description 2
- PXZXTAVGDFWJEH-SECBINFHSA-N 4-methyl-n-[4-[(1r)-1-(2h-tetrazol-5-yl)ethyl]phenyl]-1,3-thiazol-2-amine Chemical compound C1([C@H](C)C=2C=CC(NC=3SC=C(C)N=3)=CC=2)=NN=NN1 PXZXTAVGDFWJEH-SECBINFHSA-N 0.000 claims description 2
- KEBGAGJQQZSMHV-SNVBAGLBSA-N 4-tert-butyl-n-[4-[(1r)-1-(2h-tetrazol-5-yl)ethyl]phenyl]-1,3-thiazol-2-amine Chemical compound C1([C@H](C)C=2C=CC(NC=3SC=C(N=3)C(C)(C)C)=CC=2)=NN=NN1 KEBGAGJQQZSMHV-SNVBAGLBSA-N 0.000 claims description 2
- JZCYGJPMWDIUIJ-MRVPVSSYSA-N 5-[(1r)-1-[4-[[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino]phenyl]ethyl]-1,2-oxazol-3-one Chemical compound C1([C@H](C)C=2C=CC(NC=3SC=C(N=3)C(F)(F)F)=CC=2)=CC(O)=NO1 JZCYGJPMWDIUIJ-MRVPVSSYSA-N 0.000 claims description 2
- XLIYNKPPYHDVHC-MRVPVSSYSA-N 5-[(1r)-1-[4-[[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino]phenyl]ethyl]-1,2-thiazol-3-one Chemical compound C1([C@H](C)C=2C=CC(NC=3SC=C(N=3)C(F)(F)F)=CC=2)=CC(O)=NS1 XLIYNKPPYHDVHC-MRVPVSSYSA-N 0.000 claims description 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 229930013356 epothilone Natural products 0.000 claims description 2
- HESCAJZNRMSMJG-KKQRBIROSA-N epothilone A Chemical class C/C([C@@H]1C[C@@H]2O[C@@H]2CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(C)=N1 HESCAJZNRMSMJG-KKQRBIROSA-N 0.000 claims description 2
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- ZEVFLVXOLQXIAV-CQSZACIVSA-N n-[(1r)-1-(3-benzoylphenyl)ethyl]cyclobutanecarboxamide Chemical compound N([C@H](C)C=1C=C(C=CC=1)C(=O)C=1C=CC=CC=1)C(=O)C1CCC1 ZEVFLVXOLQXIAV-CQSZACIVSA-N 0.000 claims description 2
- NZXOOPPMMVMGAQ-MRVPVSSYSA-N n-[4-[(1r)-1-(2-hydroxy-1,2,4-triazol-3-yl)ethyl]phenyl]-4-(trifluoromethyl)-1,3-thiazol-2-amine Chemical compound C1([C@H](C)C=2C=CC(NC=3SC=C(N=3)C(F)(F)F)=CC=2)=NC=NN1O NZXOOPPMMVMGAQ-MRVPVSSYSA-N 0.000 claims description 2
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Landscapes
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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| Application Number | Priority Date | Filing Date | Title |
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| EP17206813.2 | 2017-12-12 | ||
| EP17206813.2A EP3498269A1 (en) | 2017-12-12 | 2017-12-12 | C5ar inhibitors for use in the treatment of chemotherapy-induced iatrogenic pain |
| PCT/EP2018/084277 WO2019115493A2 (en) | 2017-12-12 | 2018-12-11 | C5ar inhibitors for use in the treatment of chemotherapy-induced iatrogenic pain |
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| EP (2) | EP3498269A1 (enExample) |
| JP (2) | JP7430141B2 (enExample) |
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| EP4059497A1 (en) * | 2021-03-17 | 2022-09-21 | Dompé farmaceutici S.p.a. | C5ar1 inhibitors for treating hypersensitivity reactions to taxanes |
| EP4397306A1 (en) * | 2023-01-05 | 2024-07-10 | Dompe' Farmaceutici S.P.A. | C5ar1 inhibitors for use in the treatment of ocular mucous membrane pemphigoid and/or oral mucous membrane pemphigoid |
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| CN1934077B (zh) * | 2004-03-23 | 2010-09-29 | 冬姆佩制药股份公司 | 2-苯基丙酸衍生物及含有它们的药物组合物 |
| HRP20161260T1 (hr) | 2005-11-24 | 2016-11-18 | Dompé Farmaceutici S.P.A. | Derivati (r)-arilkilamina i farmaceutski pripravci koji ih sadrže |
| SG187396A1 (en) | 2007-07-19 | 2013-02-28 | Lundbeck & Co As H | 5-membered heterocyclic amides and related compounds |
| AU2008313669B2 (en) * | 2007-10-18 | 2014-01-16 | Dompe' Farmaceutici S.P.A. | (R)-4-(heteroaryl) phenylethyl derivatives and pharmaceutical compositions containing them |
| DK3402474T3 (da) * | 2016-01-15 | 2021-10-11 | Dompe Farm Spa | Il-8-inhibitorer til anvendelse i behandlingen af kemoterapi-induceret perifer neuropati |
| EP3192504A1 (en) * | 2016-01-15 | 2017-07-19 | Dompé farmaceutici S.p.A. | Il-8 inhibitors for use in the treatment of chemotherapy-induced peripheral neuropathy |
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| AU2018385364B2 (en) | 2024-04-04 |
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| US20200397725A1 (en) | 2020-12-24 |
| EP3723744A2 (en) | 2020-10-21 |
| EP3498269A1 (en) | 2019-06-19 |
| CA3082762A1 (en) | 2019-06-20 |
| US20240398731A1 (en) | 2024-12-05 |
| KR20250041193A (ko) | 2025-03-25 |
| AU2018385364A1 (en) | 2020-07-09 |
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