JP2011507916A5 - - Google Patents
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- Publication number
- JP2011507916A5 JP2011507916A5 JP2010540047A JP2010540047A JP2011507916A5 JP 2011507916 A5 JP2011507916 A5 JP 2011507916A5 JP 2010540047 A JP2010540047 A JP 2010540047A JP 2010540047 A JP2010540047 A JP 2010540047A JP 2011507916 A5 JP2011507916 A5 JP 2011507916A5
- Authority
- JP
- Japan
- Prior art keywords
- carbonyl
- pyrazole
- phenyl
- amino
- piperazine
- 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
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- -1 8-aza-bicyclo [3.2.1] octanyl Chemical group 0.000 claims 87
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 28
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 10
- 125000002947 alkylene group Chemical group 0.000 claims 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 5
- 125000004494 ethyl ester group Chemical group 0.000 claims 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- HTFFABIIOAKIBH-UHFFFAOYSA-N diazinane Chemical compound C1CCNNC1 HTFFABIIOAKIBH-UHFFFAOYSA-N 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000002053 thietanyl group Chemical group 0.000 claims 2
- FATCDYQHHGXCFN-FQEVSTJZSA-N (3s)-3-[[5-(3,3-dimethyl-2-oxobutoxy)-1-phenylpyrazole-3-carbonyl]amino]-4-(4-ethoxycarbonylpiperazin-1-yl)-4-oxobutanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OCC(=O)C(C)(C)C)=C1 FATCDYQHHGXCFN-FQEVSTJZSA-N 0.000 claims 1
- LWQJXIGNFUHBSI-INIZCTEOSA-N (4s)-4-[(5-carbamoyl-1-phenylpyrazole-3-carbonyl)amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(C(N)=O)=C1 LWQJXIGNFUHBSI-INIZCTEOSA-N 0.000 claims 1
- YJQLQIFMAXFPHI-SFHVURJKSA-N (4s)-4-[(5-ethoxycarbonyl-1-phenylpyrazole-3-carbonyl)amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(C(=O)OCC)=C1 YJQLQIFMAXFPHI-SFHVURJKSA-N 0.000 claims 1
- JLVASMKWKWVKDY-QFIPXVFZSA-N (4s)-4-[[1-(2,3-dimethylphenyl)-5-(1-ethoxycarbonylcyclobutyl)oxypyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C(=C(C)C=CC=2)C)C(OC2(CCC2)C(=O)OCC)=C1 JLVASMKWKWVKDY-QFIPXVFZSA-N 0.000 claims 1
- ZJGMXLREBZTUQG-FQEVSTJZSA-N (4s)-4-[[1-(2,5-difluorophenyl)-5-(1-ethoxycarbonylcyclobutyl)oxypyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C(=CC=C(F)C=2)F)C(OC2(CCC2)C(=O)OCC)=C1 ZJGMXLREBZTUQG-FQEVSTJZSA-N 0.000 claims 1
- AEYDCOLAHOBQRG-QFIPXVFZSA-N (4s)-4-[[1-(2,5-dimethylphenyl)-5-(1-ethoxycarbonylcyclobutyl)oxypyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C(=CC=C(C)C=2)C)C(OC2(CCC2)C(=O)OCC)=C1 AEYDCOLAHOBQRG-QFIPXVFZSA-N 0.000 claims 1
- JRGRROQEFDHVRI-FQEVSTJZSA-N (4s)-4-[[1-(2,6-dichlorophenyl)-5-(1-ethoxycarbonylcyclobutyl)oxypyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C(=CC=CC=2Cl)Cl)C(OC2(CCC2)C(=O)OCC)=C1 JRGRROQEFDHVRI-FQEVSTJZSA-N 0.000 claims 1
- JNOLSGDAZRKFFF-QHCPKHFHSA-N (4s)-4-[[1-(3,5-dimethylphenyl)-5-(1-ethoxycarbonylcyclobutyl)oxypyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=C(C)C=C(C)C=2)C(OC2(CCC2)C(=O)OCC)=C1 JNOLSGDAZRKFFF-QHCPKHFHSA-N 0.000 claims 1
- KJPBHMBUAYPVKB-NRFANRHFSA-N (4s)-4-[[1-(3,5-dimethylphenyl)-5-(2-ethoxy-2-oxoethoxy)pyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound CCOC(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OCC)=NN1C1=CC(C)=CC(C)=C1 KJPBHMBUAYPVKB-NRFANRHFSA-N 0.000 claims 1
- RNLQGOZWWBLKIT-IBGZPJMESA-N (4s)-4-[[1-(3-chloro-2-fluorophenyl)-5-(1-ethoxycarbonylcyclobutyl)oxypyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C(=C(Cl)C=CC=2)F)C(OC2(CCC2)C(=O)OCC)=C1 RNLQGOZWWBLKIT-IBGZPJMESA-N 0.000 claims 1
- JWLVYWADVBWIKS-NRFANRHFSA-N (4s)-4-[[1-(3-chloro-4-fluorophenyl)-5-(1-ethoxycarbonylcyclobutyl)oxypyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=C(Cl)C(F)=CC=2)C(OC2(CCC2)C(=O)OCC)=C1 JWLVYWADVBWIKS-NRFANRHFSA-N 0.000 claims 1
- UQRGCHRRXVKPFH-QFIPXVFZSA-N (4s)-4-[[1-(3-chloro-4-methylphenyl)-5-(1-ethoxycarbonylcyclobutyl)oxypyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=C(Cl)C(C)=CC=2)C(OC2(CCC2)C(=O)OCC)=C1 UQRGCHRRXVKPFH-QFIPXVFZSA-N 0.000 claims 1
- CRCFLMLKTSYYHA-FQEVSTJZSA-N (4s)-4-[[1-(3-chloro-4-methylphenyl)-5-(2-ethoxy-2-oxoethoxy)pyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound CCOC(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OCC)=NN1C1=CC=C(C)C(Cl)=C1 CRCFLMLKTSYYHA-FQEVSTJZSA-N 0.000 claims 1
- ICVLUAPOGHECHI-FQEVSTJZSA-N (4s)-4-[[1-(3-cyanophenyl)-5-(2-ethoxy-2-oxoethoxy)pyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound CCOC(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OCC)=NN1C1=CC=CC(C#N)=C1 ICVLUAPOGHECHI-FQEVSTJZSA-N 0.000 claims 1
- ODNCZPGHZMOQGT-NRFANRHFSA-N (4s)-4-[[1-cyclohexyl-5-(1-ethoxycarbonylcyclobutyl)oxypyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C2CCCCC2)C(OC2(CCC2)C(=O)OCC)=C1 ODNCZPGHZMOQGT-NRFANRHFSA-N 0.000 claims 1
- HLHYOWOMLPWRLN-FQEVSTJZSA-N (4s)-4-[[5-(1,3-diethoxy-1,3-dioxopropan-2-yl)oxy-1-phenylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound CCOC(=O)C(C(=O)OCC)OC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OCC)=NN1C1=CC=CC=C1 HLHYOWOMLPWRLN-FQEVSTJZSA-N 0.000 claims 1
- RGOGNOBEGMXDDJ-IBGZPJMESA-N (4s)-4-[[5-(1-carbamoylcyclobutyl)oxy-1-phenylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OC2(CCC2)C(N)=O)=C1 RGOGNOBEGMXDDJ-IBGZPJMESA-N 0.000 claims 1
- ACRSDASPFAYHQV-DAFXYXGESA-N (4s)-4-[[5-(1-carboxyethoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OC(C)C(O)=O)=C1 ACRSDASPFAYHQV-DAFXYXGESA-N 0.000 claims 1
- IRSZXCCNDKDQAX-KRWDZBQOSA-N (4s)-4-[[5-(1-ethoxycarbonylcyclobutyl)oxy-1-(1,3-thiazol-2-yl)pyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2SC=CN=2)C(OC2(CCC2)C(=O)OCC)=C1 IRSZXCCNDKDQAX-KRWDZBQOSA-N 0.000 claims 1
- OQZHQURTYQEOAZ-QFIPXVFZSA-N (4s)-4-[[5-(1-ethoxycarbonylcyclobutyl)oxy-1-(2-ethylphenyl)pyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C(=CC=CC=2)CC)C(OC2(CCC2)C(=O)OCC)=C1 OQZHQURTYQEOAZ-QFIPXVFZSA-N 0.000 claims 1
- RQFYDNWESOTXBH-FQEVSTJZSA-N (4s)-4-[[5-(1-ethoxycarbonylcyclobutyl)oxy-1-(2-fluorophenyl)pyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C(=CC=CC=2)F)C(OC2(CCC2)C(=O)OCC)=C1 RQFYDNWESOTXBH-FQEVSTJZSA-N 0.000 claims 1
- QLMRASWCJBPVSC-NRFANRHFSA-N (4s)-4-[[5-(1-ethoxycarbonylcyclobutyl)oxy-1-(3-nitrophenyl)pyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=C(C=CC=2)[N+]([O-])=O)C(OC2(CCC2)C(=O)OCC)=C1 QLMRASWCJBPVSC-NRFANRHFSA-N 0.000 claims 1
- KRMTZTDCMUJQOX-QHCPKHFHSA-N (4s)-4-[[5-(1-ethoxycarbonylcyclobutyl)oxy-1-(4-ethylphenyl)pyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC(CC)=CC=2)C(OC2(CCC2)C(=O)OCC)=C1 KRMTZTDCMUJQOX-QHCPKHFHSA-N 0.000 claims 1
- WANZHPFOGIWQSL-QFIPXVFZSA-N (4s)-4-[[5-(1-ethoxycarbonylcyclobutyl)oxy-1-(4-methylphenyl)pyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC(C)=CC=2)C(OC2(CCC2)C(=O)OCC)=C1 WANZHPFOGIWQSL-QFIPXVFZSA-N 0.000 claims 1
- CHOWJPBJNURBNU-QFIPXVFZSA-N (4s)-4-[[5-(1-ethoxycarbonylcyclobutyl)oxy-1-(4-methylsulfanylphenyl)pyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC(SC)=CC=2)C(OC2(CCC2)C(=O)OCC)=C1 CHOWJPBJNURBNU-QFIPXVFZSA-N 0.000 claims 1
- VKIIPZULZIVGEC-NRFANRHFSA-N (4s)-4-[[5-(1-ethoxycarbonylcyclobutyl)oxy-1-(4-sulfamoylphenyl)pyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC(=CC=2)S(N)(=O)=O)C(OC2(CCC2)C(=O)OCC)=C1 VKIIPZULZIVGEC-NRFANRHFSA-N 0.000 claims 1
- MDWNAPKZJUTFNL-NRFANRHFSA-N (4s)-4-[[5-(1-ethoxycarbonylcyclobutyl)oxy-1-[4-(trifluoromethoxy)phenyl]pyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC(OC(F)(F)F)=CC=2)C(OC2(CCC2)C(=O)OCC)=C1 MDWNAPKZJUTFNL-NRFANRHFSA-N 0.000 claims 1
- HPOGWKAXMNHFEI-DEOSSOPVSA-N (4s)-4-[[5-(1-ethoxycarbonylcyclobutyl)oxy-1-naphthalen-1-ylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C3=CC=CC=C3C=CC=2)C(OC2(CCC2)C(=O)OCC)=C1 HPOGWKAXMNHFEI-DEOSSOPVSA-N 0.000 claims 1
- HPSHQEAEJMOGDO-NRFANRHFSA-N (4s)-4-[[5-(1-ethoxycarbonylcyclobutyl)oxy-1-phenylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OC2(CCC2)C(=O)OCC)=C1 HPSHQEAEJMOGDO-NRFANRHFSA-N 0.000 claims 1
- QAYHDWCQFQMRGI-VWLOTQADSA-N (4s)-4-[[5-(1-ethoxycarbonylcyclobutyl)oxy-1-phenylpyrazole-3-carbonyl]amino]-5-oxo-5-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]pentanoic acid Chemical compound C=1C(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C=2C=C(C=CC=2)C(F)(F)F)=NN(C=2C=CC=CC=2)C=1OC1(C(=O)OCC)CCC1 QAYHDWCQFQMRGI-VWLOTQADSA-N 0.000 claims 1
- WJOMCTWYXVOQSD-SFHVURJKSA-N (4s)-4-[[5-(1-ethoxycarbonylcyclobutyl)oxy-1-propan-2-ylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C(C)C)C(OC2(CCC2)C(=O)OCC)=C1 WJOMCTWYXVOQSD-SFHVURJKSA-N 0.000 claims 1
- OMLOSBPIDYMRJK-NRFANRHFSA-N (4s)-4-[[5-(2-amino-2-oxoethoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-oxo-5-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]pentanoic acid Chemical compound NC(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C=2C=C(C=CC=2)C(F)(F)F)=NN1C1=CC=CC=C1 OMLOSBPIDYMRJK-NRFANRHFSA-N 0.000 claims 1
- UZXYCDYCNCJWCH-NRFANRHFSA-N (4s)-4-[[5-(2-cyclobutyl-2-oxoethoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OCC(=O)C2CCC2)=C1 UZXYCDYCNCJWCH-NRFANRHFSA-N 0.000 claims 1
- ORMSOLPCVAXNFM-FQEVSTJZSA-N (4s)-4-[[5-(2-cyclopropyl-2-oxoethoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OCC(=O)C2CC2)=C1 ORMSOLPCVAXNFM-FQEVSTJZSA-N 0.000 claims 1
- QCZLBDRHYLMYFR-NRFANRHFSA-N (4s)-4-[[5-(3,3-dimethyl-2-oxobutoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonyl-1,4-diazepan-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OCC(=O)C(C)(C)C)=C1 QCZLBDRHYLMYFR-NRFANRHFSA-N 0.000 claims 1
- CSFVXWFYYYPFHZ-NRFANRHFSA-N (4s)-4-[[5-(3,3-dimethyl-2-oxobutoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperidin-1-yl)-5-oxopentanoic acid Chemical compound C1CC(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OCC(=O)C(C)(C)C)=C1 CSFVXWFYYYPFHZ-NRFANRHFSA-N 0.000 claims 1
- NXFDSQXFDJPTRO-IBGZPJMESA-N (4s)-4-[[5-(3,3-dimethyl-2-oxobutoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-(4-methoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OCC(=O)C(C)(C)C)=C1 NXFDSQXFDJPTRO-IBGZPJMESA-N 0.000 claims 1
- SRVNGGMHTCKWNP-DEOSSOPVSA-N (4s)-4-[[5-(3,3-dimethyl-2-oxobutoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-[4-(4-fluorophenoxy)carbonylpiperazin-1-yl]-5-oxopentanoic acid Chemical compound CC(C)(C)C(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OC=2C=CC(F)=CC=2)=NN1C1=CC=CC=C1 SRVNGGMHTCKWNP-DEOSSOPVSA-N 0.000 claims 1
- YPGMCQNHHWBWJT-DEOSSOPVSA-N (4s)-4-[[5-(3,3-dimethyl-2-oxobutoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]-5-oxopentanoic acid Chemical compound CC(C)(C)C(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCC(CC2)C=2C3=CC=C(F)C=C3ON=2)=NN1C1=CC=CC=C1 YPGMCQNHHWBWJT-DEOSSOPVSA-N 0.000 claims 1
- XDHOKXGJFNSUBM-DEOSSOPVSA-N (4s)-4-[[5-(3,3-dimethyl-2-oxobutoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-oxo-5-(4-phenoxycarbonylpiperazin-1-yl)pentanoic acid Chemical compound CC(C)(C)C(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OC=2C=CC=CC=2)=NN1C1=CC=CC=C1 XDHOKXGJFNSUBM-DEOSSOPVSA-N 0.000 claims 1
- QFINLHNVMUOFTM-VWLOTQADSA-N (4s)-4-[[5-(3,3-dimethyl-2-oxobutoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-oxo-5-(4-phenylsulfanylpiperidin-1-yl)pentanoic acid Chemical compound CC(C)(C)C(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCC(CC2)SC=2C=CC=CC=2)=NN1C1=CC=CC=C1 QFINLHNVMUOFTM-VWLOTQADSA-N 0.000 claims 1
- GQYRWVLNEIEMJN-NRFANRHFSA-N (4s)-4-[[5-(3,3-dimethyl-2-oxobutoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-oxo-5-(4-propan-2-yloxycarbonylpiperazin-1-yl)pentanoic acid Chemical compound C1CN(C(=O)OC(C)C)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OCC(=O)C(C)(C)C)=C1 GQYRWVLNEIEMJN-NRFANRHFSA-N 0.000 claims 1
- PFGSRRYNEWYLTE-NRFANRHFSA-N (4s)-4-[[5-(3,3-dimethyl-2-oxobutoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-oxo-5-(4-propoxycarbonylpiperazin-1-yl)pentanoic acid Chemical compound C1CN(C(=O)OCCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OCC(=O)C(C)(C)C)=C1 PFGSRRYNEWYLTE-NRFANRHFSA-N 0.000 claims 1
- CNQIPANQVBCNHU-QHCPKHFHSA-N (4s)-4-[[5-(3,3-dimethyl-2-oxobutoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-oxo-5-[4-(2-oxo-2-pyrrolidin-1-ylethyl)piperazin-1-yl]pentanoic acid Chemical compound CC(C)(C)C(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC(=O)N3CCCC3)CC2)=NN1C1=CC=CC=C1 CNQIPANQVBCNHU-QHCPKHFHSA-N 0.000 claims 1
- MCNLXEOHUYXBAF-FQEVSTJZSA-N (4s)-4-[[5-(3,3-dimethyl-2-oxobutoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-oxo-5-[4-(3,3,3-trifluoropropoxycarbonyl)piperazin-1-yl]pentanoic acid Chemical compound CC(C)(C)C(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OCCC(F)(F)F)=NN1C1=CC=CC=C1 MCNLXEOHUYXBAF-FQEVSTJZSA-N 0.000 claims 1
- HUTBQTSNOBUELP-QFIPXVFZSA-N (4s)-4-[[5-(3,3-dimethyl-2-oxobutoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-oxo-5-[4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]pentanoic acid Chemical compound CC(C)(C)C(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C=2N=CC=C(C=2)C(F)(F)F)=NN1C1=CC=CC=C1 HUTBQTSNOBUELP-QFIPXVFZSA-N 0.000 claims 1
- HVHMMCXMULZEQA-FQEVSTJZSA-N (4s)-4-[[5-(cyclopropylmethoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OCC2CC2)=C1 HVHMMCXMULZEQA-FQEVSTJZSA-N 0.000 claims 1
- YWRZUKVMWUZOPA-DEOSSOPVSA-N (4s)-4-[[5-(cyclopropylmethoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-oxo-5-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]pentanoic acid Chemical compound N([C@@H](CCC(=O)O)C(=O)N1CCN(CC1)C=1C=C(C=CC=1)C(F)(F)F)C(=O)C(=NN1C=2C=CC=CC=2)C=C1OCC1CC1 YWRZUKVMWUZOPA-DEOSSOPVSA-N 0.000 claims 1
- JSRPOZYDYCGWBJ-SFHVURJKSA-N (4s)-4-[[5-(dimethylcarbamoyl)-1-phenylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(C(=O)N(C)C)=C1 JSRPOZYDYCGWBJ-SFHVURJKSA-N 0.000 claims 1
- BDODQRIDUGHPBH-SANMLTNESA-N (4s)-4-[[5-[(3,5-dimethyl-1,2-oxazol-4-yl)methoxy]-1-phenylpyrazole-3-carbonyl]amino]-5-oxo-5-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]pentanoic acid Chemical compound CC1=NOC(C)=C1COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C=2C=C(C=CC=2)C(F)(F)F)=NN1C1=CC=CC=C1 BDODQRIDUGHPBH-SANMLTNESA-N 0.000 claims 1
- LGNMKOGWIGKBPV-ZYZRXSCRSA-N (4s)-4-[[5-[1-(cyclopropylamino)-1-oxopropan-2-yl]oxy-1-phenylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OC(C)C(=O)NC2CC2)=C1 LGNMKOGWIGKBPV-ZYZRXSCRSA-N 0.000 claims 1
- WCGLHVLMDKPEAA-NRFANRHFSA-N (4s)-4-[[5-[1-(cyclopropylamino)-2-methyl-1-oxopropan-2-yl]oxy-1-phenylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OC(C)(C)C(=O)NC2CC2)=C1 WCGLHVLMDKPEAA-NRFANRHFSA-N 0.000 claims 1
- OMNFXYMOWQNXMO-QHCPKHFHSA-N (4s)-4-[[5-[1-(cyclopropylmethylcarbamoyl)cyclobutyl]oxy-1-phenylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OC2(CCC2)C(=O)NCC2CC2)=C1 OMNFXYMOWQNXMO-QHCPKHFHSA-N 0.000 claims 1
- BZQFGYCEKYXDRP-QHCPKHFHSA-N (4s)-4-[[5-[1-(diethylcarbamoyl)cyclobutyl]oxy-1-phenylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OC2(CCC2)C(=O)N(CC)CC)=C1 BZQFGYCEKYXDRP-QHCPKHFHSA-N 0.000 claims 1
- YGGHUIBVSMMDDQ-NRFANRHFSA-N (4s)-4-[[5-[1-(dimethylcarbamoyl)cyclobutyl]oxy-1-phenylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OC2(CCC2)C(=O)N(C)C)=C1 YGGHUIBVSMMDDQ-NRFANRHFSA-N 0.000 claims 1
- CZBWLEFSGLAWMC-FQEVSTJZSA-N (4s)-4-[[5-[1-[(2-amino-2-oxoethyl)carbamoyl]cyclobutyl]oxy-1-phenylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OC2(CCC2)C(=O)NCC(N)=O)=C1 CZBWLEFSGLAWMC-FQEVSTJZSA-N 0.000 claims 1
- ROYNBDJQNSPLJA-BPARTEKVSA-N (4s)-4-[[5-[1-[[2-(cyclopropylamino)-2-oxoethyl]amino]-1-oxopropan-2-yl]oxy-1-phenylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OC(C)C(=O)NCC(=O)NC2CC2)=C1 ROYNBDJQNSPLJA-BPARTEKVSA-N 0.000 claims 1
- SQWNWYDDBVKMIG-IBGZPJMESA-N (4s)-4-[[5-[2-(dimethylamino)-2-oxoethoxy]-1-phenylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OCC(=O)N(C)C)=C1 SQWNWYDDBVKMIG-IBGZPJMESA-N 0.000 claims 1
- OJEOEMNSOGTKMP-HKUYNNGSSA-N (4s)-4-[[5-[2-[[(1s)-1-carboxyethyl]amino]-2-oxoethoxy]-1-phenylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OCC(=O)N[C@@H](C)C(O)=O)=C1 OJEOEMNSOGTKMP-HKUYNNGSSA-N 0.000 claims 1
- BWXMZZFVLOKSPU-DEOSSOPVSA-N (4s)-4-[[5-[2-[[1-(cyclobutylcarbamoyl)cyclobutyl]amino]-2-oxoethoxy]-1-phenylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OCC(=O)NC2(CCC2)C(=O)NC2CCC2)=C1 BWXMZZFVLOKSPU-DEOSSOPVSA-N 0.000 claims 1
- QUNWVNCXZFYCSP-QHCPKHFHSA-N (4s)-4-[[5-[2-[[1-(cyclopropylcarbamoyl)cyclobutyl]amino]-2-oxoethoxy]-1-phenylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OCC(=O)NC2(CCC2)C(=O)NC2CC2)=C1 QUNWVNCXZFYCSP-QHCPKHFHSA-N 0.000 claims 1
- ADOGCKFVJZOWSY-DEOSSOPVSA-N (4s)-4-[[5-[2-[[1-(cyclopropylmethylcarbamoyl)cyclobutyl]amino]-2-oxoethoxy]-1-phenylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OCC(=O)NC2(CCC2)C(=O)NCC2CC2)=C1 ADOGCKFVJZOWSY-DEOSSOPVSA-N 0.000 claims 1
- DAGGFVVDRRVKOX-VWLOTQADSA-N (4s)-4-[[5-[2-[[1-[cyclobutyl(methyl)carbamoyl]cyclobutyl]amino]-2-oxoethoxy]-1-phenylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OCC(=O)NC2(CCC2)C(=O)N(C)C2CCC2)=C1 DAGGFVVDRRVKOX-VWLOTQADSA-N 0.000 claims 1
- URTYHVKVSFMUKU-VWLOTQADSA-N (4s)-4-[[5-[2-[carbamoyl-(1-cyclopentylcyclobutyl)amino]-2-oxoethoxy]-1-phenylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OCC(=O)N(C(N)=O)C2(CCC2)C2CCCC2)=C1 URTYHVKVSFMUKU-VWLOTQADSA-N 0.000 claims 1
- QHIYANGVRIPGPQ-IBGZPJMESA-N (4s)-4-[[5-[2-[carboxymethyl(methyl)amino]-2-oxoethoxy]-1-phenylpyrazole-3-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OCC(=O)N(C)CC(O)=O)=C1 QHIYANGVRIPGPQ-IBGZPJMESA-N 0.000 claims 1
- GOKWUQMJZPWXBY-SANMLTNESA-N (4s)-5-(4-acetyl-4-phenylpiperidin-1-yl)-4-[[5-(3,3-dimethyl-2-oxobutoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound N([C@@H](CCC(O)=O)C(=O)N1CCC(CC1)(C(=O)C)C=1C=CC=CC=1)C(=O)C(=N1)C=C(OCC(=O)C(C)(C)C)N1C1=CC=CC=C1 GOKWUQMJZPWXBY-SANMLTNESA-N 0.000 claims 1
- VDEJAHUOJHLYEP-DEOSSOPVSA-N (4s)-5-(4-benzoylpiperazin-1-yl)-4-[[5-(3,3-dimethyl-2-oxobutoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound CC(C)(C)C(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)C=2C=CC=CC=2)=NN1C1=CC=CC=C1 VDEJAHUOJHLYEP-DEOSSOPVSA-N 0.000 claims 1
- QVAMQIJYFRHAAA-QFIPXVFZSA-N (4s)-5-(4-butoxycarbonylpiperazin-1-yl)-4-[[5-(3,3-dimethyl-2-oxobutoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCCCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OCC(=O)C(C)(C)C)=C1 QVAMQIJYFRHAAA-QFIPXVFZSA-N 0.000 claims 1
- IZKBBINEAXSFSO-BBQAJUCSSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[5-(1-ethoxy-1-oxopentan-2-yl)oxy-1-phenylpyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound CCOC(=O)C(CCC)OC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OCC)=NN1C1=CC=CC=C1 IZKBBINEAXSFSO-BBQAJUCSSA-N 0.000 claims 1
- HRIUYNFTWLMBPL-IJHRGXPZSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[5-(1-ethoxy-1-oxopropan-2-yl)oxy-1-phenylpyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound CCOC(=O)C(C)OC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OCC)=NN1C1=CC=CC=C1 HRIUYNFTWLMBPL-IJHRGXPZSA-N 0.000 claims 1
- MOIITRDQFKUEJO-FQEVSTJZSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[5-(1-ethoxy-2-methyl-1-oxopropan-2-yl)oxy-1-phenylpyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OC(C)(C)C(=O)OCC)=C1 MOIITRDQFKUEJO-FQEVSTJZSA-N 0.000 claims 1
- VCRDWPZZBQKIPS-ZZDYIDRTSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[5-(2-ethoxy-2-oxo-1-phenylethoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)OCC)OC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OCC)=NN1C1=CC=CC=C1 VCRDWPZZBQKIPS-ZZDYIDRTSA-N 0.000 claims 1
- LSKVQHJCCPOXLA-IBGZPJMESA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[5-(2-ethoxy-2-oxoethoxy)-1-(3-fluorophenyl)pyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound CCOC(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OCC)=NN1C1=CC=CC(F)=C1 LSKVQHJCCPOXLA-IBGZPJMESA-N 0.000 claims 1
- CZPHRFHAHQDVOB-FQEVSTJZSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[5-(2-ethoxy-2-oxoethoxy)-1-(3-methoxyphenyl)pyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound CCOC(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OCC)=NN1C1=CC=CC(OC)=C1 CZPHRFHAHQDVOB-FQEVSTJZSA-N 0.000 claims 1
- QYNJGMHGHFNSCX-FQEVSTJZSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[5-(2-ethoxy-2-oxoethoxy)-1-(3-methylphenyl)pyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound CCOC(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OCC)=NN1C1=CC=CC(C)=C1 QYNJGMHGHFNSCX-FQEVSTJZSA-N 0.000 claims 1
- AMKNFZWJYVUBKH-IBGZPJMESA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[5-(2-ethoxy-2-oxoethoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound CCOC(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OCC)=NN1C1=CC=CC=C1 AMKNFZWJYVUBKH-IBGZPJMESA-N 0.000 claims 1
- WJVXSIRHFZEGCE-INIZCTEOSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[5-(2-ethoxy-2-oxoethoxy)-1-propan-2-ylpyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound CC(C)N1C(OCC(=O)OCC)=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OCC)=N1 WJVXSIRHFZEGCE-INIZCTEOSA-N 0.000 claims 1
- AJZRDOHUIDDVIY-FQEVSTJZSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[5-(2-ethoxyethoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound CCOCCOC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OCC)=NN1C1=CC=CC=C1 AJZRDOHUIDDVIY-FQEVSTJZSA-N 0.000 claims 1
- PBVOEVKOXSOSNV-FQEVSTJZSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[5-(3-ethoxy-3-oxopropoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound CCOC(=O)CCOC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OCC)=NN1C1=CC=CC=C1 PBVOEVKOXSOSNV-FQEVSTJZSA-N 0.000 claims 1
- BXXQGOCVZKIPRE-FQEVSTJZSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[5-(3-methoxypropoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OCCCOC)=C1 BXXQGOCVZKIPRE-FQEVSTJZSA-N 0.000 claims 1
- OMLLRSLJQNMFRV-NRFANRHFSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[5-(4-ethoxy-2,4-dioxobutoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound CCOC(=O)CC(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OCC)=NN1C1=CC=CC=C1 OMLLRSLJQNMFRV-NRFANRHFSA-N 0.000 claims 1
- RIUCUGWYZWUTTP-FQEVSTJZSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[5-(4-hydroxybutoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OCCCCO)=C1 RIUCUGWYZWUTTP-FQEVSTJZSA-N 0.000 claims 1
- IUWDSZTVYCWBLA-QUCCMNQESA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[5-[(2r)-3-hydroxy-2-methylpropoxy]-1-phenylpyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OC[C@H](C)CO)=C1 IUWDSZTVYCWBLA-QUCCMNQESA-N 0.000 claims 1
- TWENZKYOWAPPCJ-QHCPKHFHSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[5-[1-(2-methylpropylcarbamoyl)cyclobutyl]oxy-1-phenylpyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OC2(CCC2)C(=O)NCC(C)C)=C1 TWENZKYOWAPPCJ-QHCPKHFHSA-N 0.000 claims 1
- AYUKNHUMPMSRMY-QHCPKHFHSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[5-[1-[methyl(propan-2-yl)carbamoyl]cyclobutyl]oxy-1-phenylpyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OC2(CCC2)C(=O)N(C)C(C)C)=C1 AYUKNHUMPMSRMY-QHCPKHFHSA-N 0.000 claims 1
- NYRSZTJJKVFOLG-QHCPKHFHSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[5-[1-[methyl(propyl)carbamoyl]cyclobutyl]oxy-1-phenylpyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound C=1C(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OCC)=NN(C=2C=CC=CC=2)C=1OC1(C(=O)N(C)CCC)CCC1 NYRSZTJJKVFOLG-QHCPKHFHSA-N 0.000 claims 1
- IVXPNPQJAXFMFH-FQEVSTJZSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[5-[2-(1-methylcyclopropyl)-2-oxoethoxy]-1-phenylpyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OCC(=O)C2(C)CC2)=C1 IVXPNPQJAXFMFH-FQEVSTJZSA-N 0.000 claims 1
- REILQUBGWYTIJB-QHCPKHFHSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxo-4-[(1-phenyl-5-phenylmethoxypyrazole-3-carbonyl)amino]pentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OCC=2C=CC=CC=2)=C1 REILQUBGWYTIJB-QHCPKHFHSA-N 0.000 claims 1
- ZHENDZSOMFWIEA-QFIPXVFZSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxo-4-[[1-phenyl-5-[1-(propan-2-ylcarbamoyl)cyclobutyl]oxypyrazole-3-carbonyl]amino]pentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OC2(CCC2)C(=O)NC(C)C)=C1 ZHENDZSOMFWIEA-QFIPXVFZSA-N 0.000 claims 1
- OAKNFOCLTQWNTJ-FQEVSTJZSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxo-4-[[5-(2-oxo-2-propan-2-yloxyethoxy)-1-phenylpyrazole-3-carbonyl]amino]pentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OCC(=O)OC(C)C)=C1 OAKNFOCLTQWNTJ-FQEVSTJZSA-N 0.000 claims 1
- DBOHWRWAVVXQBB-FQEVSTJZSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxo-4-[[5-(2-oxobutoxy)-1-phenylpyrazole-3-carbonyl]amino]pentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OCC(=O)CC)=C1 DBOHWRWAVVXQBB-FQEVSTJZSA-N 0.000 claims 1
- SUKHUEGKYPBVOO-LROBGIAVSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxo-4-[[5-(2-oxooxolan-3-yl)oxy-1-phenylpyrazole-3-carbonyl]amino]pentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OC2C(OCC2)=O)=C1 SUKHUEGKYPBVOO-LROBGIAVSA-N 0.000 claims 1
- NKNZRGCNJFMTFD-VWLOTQADSA-N (4s)-5-[4-(3,4-difluorobenzoyl)piperidin-1-yl]-4-[[5-(3,3-dimethyl-2-oxobutoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound CC(C)(C)C(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCC(CC2)C(=O)C=2C=C(F)C(F)=CC=2)=NN1C1=CC=CC=C1 NKNZRGCNJFMTFD-VWLOTQADSA-N 0.000 claims 1
- LSSZQBTYFCRUCO-SANMLTNESA-N (4s)-5-[4-(3,5-dimethoxyphenyl)piperazin-1-yl]-4-[[5-(3,3-dimethyl-2-oxobutoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound COC1=CC(OC)=CC(N2CCN(CC2)C(=O)[C@H](CCC(O)=O)NC(=O)C2=NN(C(OCC(=O)C(C)(C)C)=C2)C=2C=CC=CC=2)=C1 LSSZQBTYFCRUCO-SANMLTNESA-N 0.000 claims 1
- RHMUFKQUGLFFBK-QFIPXVFZSA-N (4s)-5-[4-(4,6-dimethoxypyrimidin-2-yl)piperidin-1-yl]-4-[[5-(3,3-dimethyl-2-oxobutoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound COC1=CC(OC)=NC(C2CCN(CC2)C(=O)[C@H](CCC(O)=O)NC(=O)C2=NN(C(OCC(=O)C(C)(C)C)=C2)C=2C=CC=CC=2)=N1 RHMUFKQUGLFFBK-QFIPXVFZSA-N 0.000 claims 1
- IBTSIAXBOPPVBR-QFIPXVFZSA-N (4s)-5-[4-(cyclopropylmethoxycarbonyl)piperazin-1-yl]-4-[[5-(3,3-dimethyl-2-oxobutoxy)-1-phenylpyrazole-3-carbonyl]amino]-5-oxopentanoic acid Chemical compound CC(C)(C)C(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OCC2CC2)=NN1C1=CC=CC=C1 IBTSIAXBOPPVBR-QFIPXVFZSA-N 0.000 claims 1
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- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical compound C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 claims 1
- PTIQUOGPXDNREG-INIZCTEOSA-N 5-[[(2s)-4-carboxy-1-(4-ethoxycarbonylpiperazin-1-yl)-1-oxobutan-2-yl]carbamoyl]-2-phenylpyrazole-3-carboxylic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(C(O)=O)=C1 PTIQUOGPXDNREG-INIZCTEOSA-N 0.000 claims 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims 1
- JZFICWYCTCCINF-UHFFFAOYSA-N Thiadiazin Chemical compound S=C1SC(C)NC(C)N1CCN1C(=S)SC(C)NC1C JZFICWYCTCCINF-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims 1
- 125000005602 azabenzimidazolyl group Chemical group 0.000 claims 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims 1
- 125000002785 azepinyl group Chemical group 0.000 claims 1
- 125000004069 aziridinyl group Chemical group 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
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- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 1
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- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
- 125000004623 carbolinyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
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- YUEPZSOKBARKRK-QFIPXVFZSA-N ethyl 4-[(2s)-2-[[5-(1-ethoxycarbonylcyclobutyl)oxy-1-phenylpyrazole-3-carbonyl]amino]-4-methylsulfonylbutanoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCS(C)(=O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OC2(CCC2)C(=O)OCC)=C1 YUEPZSOKBARKRK-QFIPXVFZSA-N 0.000 claims 1
- GNMHSTPIFZZQRP-QFIPXVFZSA-N ethyl 4-[(2s)-2-[[5-(1-ethoxycarbonylcyclobutyl)oxy-1-phenylpyrazole-3-carbonyl]amino]-5-methoxy-5-oxopentanoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(=O)OC)NC(=O)C1=NN(C=2C=CC=CC=2)C(OC2(CCC2)C(=O)OCC)=C1 GNMHSTPIFZZQRP-QFIPXVFZSA-N 0.000 claims 1
- UIDKWLIOQMENFK-QFIPXVFZSA-N ethyl 4-[(2s)-2-[[5-(3,3-dimethyl-2-oxobutoxy)-1-phenylpyrazole-3-carbonyl]amino]-3-[(2-ethoxy-3,4-dioxocyclobuten-1-yl)amino]propanoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@@H](NC(=O)C1=NN(C(OCC(=O)C(C)(C)C)=C1)C=1C=CC=CC=1)CNC1=C(OCC)C(=O)C1=O UIDKWLIOQMENFK-QFIPXVFZSA-N 0.000 claims 1
- RXVWOORYOIEIMH-FQEVSTJZSA-N ethyl 4-[(2s)-2-[[5-(3,3-dimethyl-2-oxobutoxy)-1-phenylpyrazole-3-carbonyl]amino]-3-[(2-hydroxy-3,4-dioxocyclobuten-1-yl)amino]propanoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@@H](NC(=O)C1=NN(C(OCC(=O)C(C)(C)C)=C1)C=1C=CC=CC=1)CNC1=C(O)C(=O)C1=O RXVWOORYOIEIMH-FQEVSTJZSA-N 0.000 claims 1
- ALKNMJTUTFKFFU-NRFANRHFSA-N ethyl 4-[(2s)-2-[[5-(3,3-dimethyl-2-oxobutoxy)-1-phenylpyrazole-3-carbonyl]amino]-4-(methanesulfonamido)-4-oxobutanoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CC(=O)NS(C)(=O)=O)NC(=O)C1=NN(C=2C=CC=CC=2)C(OCC(=O)C(C)(C)C)=C1 ALKNMJTUTFKFFU-NRFANRHFSA-N 0.000 claims 1
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 1
- 125000003838 furazanyl group Chemical group 0.000 claims 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims 1
- 125000002636 imidazolinyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims 1
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims 1
- 125000005438 isoindazolyl group Chemical group 0.000 claims 1
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 125000003965 isoxazolidinyl group Chemical group 0.000 claims 1
- 125000003971 isoxazolinyl group Chemical group 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000003431 oxalo group Chemical group 0.000 claims 1
- OXUZCBDDXOMZAM-UHFFFAOYSA-N oxathiepane Chemical compound C1CCOSCC1 OXUZCBDDXOMZAM-UHFFFAOYSA-N 0.000 claims 1
- SFJGCXYXEFWEBK-UHFFFAOYSA-N oxazepine Chemical compound O1C=CC=CC=N1 SFJGCXYXEFWEBK-UHFFFAOYSA-N 0.000 claims 1
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 1
- 125000005968 oxazolinyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000003566 oxetanyl group Chemical group 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 1
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims 1
- 125000002755 pyrazolinyl group Chemical group 0.000 claims 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 claims 1
- 150000003536 tetrazoles Chemical class 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000001984 thiazolidinyl group Chemical group 0.000 claims 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims 1
- 125000002769 thiazolinyl group Chemical group 0.000 claims 1
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 claims 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
- UOBKULMUFKXXEA-UHFFFAOYSA-N triazepane Chemical compound C1CCNNNC1 UOBKULMUFKXXEA-UHFFFAOYSA-N 0.000 claims 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims 1
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| EP07291628.1 | 2007-12-26 | ||
| PCT/EP2008/010573 WO2009080227A2 (en) | 2007-12-26 | 2008-12-12 | Pyrazole-carboxamide derivatives as p2y12 antagonists |
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| JP2011507916A JP2011507916A (ja) | 2011-03-10 |
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| BRPI0819696B1 (pt) | 2007-11-29 | 2018-10-23 | Actelion Pharmaceuticals Ltd | compostos de derivados de 2-fenil-pirimidina, composição farmacêutica e uso de um composto |
| AR071652A1 (es) | 2008-04-11 | 2010-07-07 | Actelion Pharmaceuticals Ltd | Derivados 2- fenil-piridina substituidos |
| AR071653A1 (es) | 2008-04-11 | 2010-07-07 | Actelion Pharmaceuticals Ltd | Derivados 2-fenil-4-ciclopropil-pirimidina |
| WO2010116328A2 (en) | 2009-04-08 | 2010-10-14 | Actelion Pharmaceuticals Ltd | 6-(3-aza-bicyclo[3.1.0]hex-3-yl)-2-phenyl-pyrimidines |
| KR101728180B1 (ko) * | 2009-04-22 | 2017-04-18 | 액테리온 파마슈티칼 리미티드 | 티아졸 유도체들 및 ｐ2ｙ12 수용체 길항제로서 이들의 용도 |
| TWI532725B (zh) | 2010-01-26 | 2016-05-11 | 賽諾菲阿凡提斯公司 | 經氧取代之３－雜芳醯基胺基－丙酸衍生物及其作為藥物之用途 |
| TWI523844B (zh) | 2011-01-26 | 2016-03-01 | 賽諾菲公司 | 經胺基取代之３－雜芳醯基胺基－丙酸衍生物及其作為藥物之用途 |
| AR085013A1 (es) | 2011-01-26 | 2013-08-07 | Sanofi Aventis | Derivados de acido 3-heteroaroilamino-propionico sustituidos y su uso como sustancias farmaceuticas |
| ES2560381T3 (es) | 2011-07-26 | 2016-02-18 | Sanofi | Derivados de ácido 3-heteroaroilamino-propiónico y su uso como productos farmacéuticos |
| KR20140049020A (ko) | 2011-07-26 | 2014-04-24 | 사노피 | 치환된 ３-（티아졸-４-카보닐）- 또는 ３-（티아졸-２-카보닐）아미노프로피온산 유도체 및 이의 약제로서의 용도 |
| US9539246B2 (en) | 2011-08-30 | 2017-01-10 | University Of Utah Research Foundation | Methods and compositions for treating nephrogenic diabetes insipidus |
| US20130123276A1 (en) | 2011-11-14 | 2013-05-16 | Sven Ruf | Use of telaprevir and related compounds in atherosclerosis, heart failure, renal diseases, liver diseases or inflammatory diseases |
| US20130123325A1 (en) | 2011-11-14 | 2013-05-16 | Sven Ruf | Use of boceprevir and related compounds in atherosclerosis, heart failure, renal diseases, liver diseases or inflammatory diseases |
| JP6257596B2 (ja) | 2012-05-18 | 2018-01-10 | サノフイ | ピラゾール誘導体およびｌｐａｒ５アンタゴニストとしてのその使用 |
| US9346757B2 (en) | 2012-05-18 | 2016-05-24 | Sanofi | Pyridine derivatives and their use in the treatment of conditions associated with pathological thrombus formation |
| JO3215B1 (ar) | 2012-08-09 | 2018-03-08 | Phenex Pharmaceuticals Ag | حلقات غير متجانسة بها 5 ذرات تحتوي على النيتروجين بها استبدال بكربوكساميد أو سلفوناميد كمعدلات لمستقبل نووي غير محمي RORy |
| EP2725025A1 (fr) * | 2012-10-26 | 2014-04-30 | Sanofi | Dérives de 1H-indole-3-carboxamide et leurs utilisation comme antagonistes du P2Y12 |
| EP2978754B1 (en) | 2013-03-28 | 2017-05-10 | Sanofi | Biaryl-propionic acid derivatives and their use as pharmaceuticals |
| TW201522318A (zh) | 2013-03-28 | 2015-06-16 | Sanofi Sa | 聯芳基丙酸及其作為醫藥品之用途 |
| EP3184095A1 (en) | 2013-05-23 | 2017-06-28 | IP Gesellschaft für Management mbH | Administration units comprising polymorph 1 of 2-(2-methylamino-pyrimidin-4-yl]-1h-indole-5-carboxylic acid [(s)-1-carbamoyl-2-(phenyl-pyrimidin-2-yl-amino)-ethyl]-amide |
| CN107759662B (zh) * | 2013-08-28 | 2020-10-30 | 北京赛而生物药业有限公司 | 一种抗凝血化合物、其制备方法和用途、及包含其的药物组合物 |
| CN103626630B (zh) * | 2013-11-15 | 2015-08-19 | 深圳致君制药有限公司 | 利伐沙班中间体及其制备方法 |
| US9231217B2 (en) * | 2013-11-28 | 2016-01-05 | Semiconductor Energy Laboratory Co., Ltd. | Synthesis method of organometallic complex, synthesis method of pyrazine derivative, 5,6-diaryl-2-pyrazyl triflate, light-emitting element, light-emitting device, electronic device, and lighting device |
| HUE057772T2 (hu) | 2016-09-22 | 2022-06-28 | Idorsia Pharmaceuticals Ltd | Kristályos formák |
| US11179390B2 (en) | 2017-03-15 | 2021-11-23 | Idorsia Pharmaceuticals Ltd | Subcutaneous administration of a P2Y12 receptor antagonist |
| CN110204541B (zh) * | 2018-02-28 | 2020-06-23 | 新发药业有限公司 | 一种阿哌沙班的制备方法 |
| US11696902B2 (en) | 2018-08-14 | 2023-07-11 | AltaThera Pharmaceuticals, LLC | Method of initiating and escalating sotalol hydrochloride dosing |
| US10512620B1 (en) | 2018-08-14 | 2019-12-24 | AltaThera Pharmaceuticals, LLC | Method of initiating and escalating sotalol hydrochloride dosing |
| US12396970B2 (en) | 2021-08-20 | 2025-08-26 | AltaThera Pharmaceuticals LLC | Anti-arrhythmic compositions and methods |
| US11610660B1 (en) | 2021-08-20 | 2023-03-21 | AltaThera Pharmaceuticals LLC | Antiarrhythmic drug dosing methods, medical devices, and systems |
| US11344518B2 (en) | 2018-08-14 | 2022-05-31 | AltaThera Pharmaceuticals LLC | Method of converting atrial fibrillation to normal sinus rhythm and loading oral sotalol in a shortened time frame |
| CN112778184B (zh) * | 2021-01-29 | 2022-05-17 | 绍兴文理学院 | 一种叔胺α位的芳基化方法 |
| CN119930579A (zh) * | 2025-01-15 | 2025-05-06 | 四川轻化工大学 | 哌啶环类化合物及其合成方法、药学上可接受的盐与应用 |
Family Cites Families (9)
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| GB9824310D0 (en) * | 1998-11-05 | 1998-12-30 | Univ London | Activators of soluble guanylate cyclase |
| KR20040081182A (ko) | 2002-02-05 | 2004-09-20 | 다이닛본 세이야꾸 가부시끼가이샤 | 엘라스타제-저해 활성을 가진 이종고리 화합물 및 그 중간체 |
| BR0317659A (pt) * | 2002-12-23 | 2005-12-06 | Aventis Pharma Gmbh | Derivados de pirazol como inibidores de fator xa |
| AU2003249865A1 (en) | 2003-06-24 | 2005-01-21 | Actelion Pharmaceuticals Ltd | Pyrazolidinedione derivatives and their use as platelet aggregation inhibitors |
| TW200526641A (en) | 2003-12-26 | 2005-08-16 | Daiichi Seiyaku Co | Amidopyrazole derivatives |
| US7029587B2 (en) | 2004-04-02 | 2006-04-18 | Lynntech, Inc. | Water purification |
| FR2884666B1 (fr) | 2005-04-19 | 2007-06-22 | Thales Sa | Procede et dispositif de determination d'une adresse au sein d'un reseau aeronautique de telecommunication |
| TW200640877A (en) * | 2005-04-28 | 2006-12-01 | Actelion Pharmaceuticals Ltd | Pyrimidine derivatives |
| US7601844B2 (en) * | 2006-01-27 | 2009-10-13 | Bristol-Myers Squibb Company | Piperidinyl derivatives as modulators of chemokine receptor activity |
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2008
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- 2008-12-12 EP EP08865091A patent/EP2238127B1/en not_active Not-in-force
- 2008-12-12 WO PCT/EP2008/010573 patent/WO2009080227A2/en not_active Ceased
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2010
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