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
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07291628 | 2007-12-26 | ||
| EP07291628.1 | 2007-12-26 | ||
| PCT/EP2008/010573 WO2009080227A2 (en) | 2007-12-26 | 2008-12-12 | Pyrazole-carboxamide derivatives as p2y12 antagonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011507916A JP2011507916A (ja) | 2011-03-10 |
| JP2011507916A5 true JP2011507916A5 (https=) | 2012-02-02 |
| JP5560202B2 JP5560202B2 (ja) | 2014-07-23 |
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| EP (1) | EP2238127B1 (https=) |
| JP (1) | JP5560202B2 (https=) |
| WO (1) | WO2009080227A2 (https=) |
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| EP2225253B1 (en) | 2007-11-29 | 2012-06-27 | Actelion Pharmaceuticals Ltd. | Phosphonic acid derivates and their use as p2y12 receptor antagonists |
| AR071653A1 (es) | 2008-04-11 | 2010-07-07 | Actelion Pharmaceuticals Ltd | Derivados 2-fenil-4-ciclopropil-pirimidina |
| AR071652A1 (es) | 2008-04-11 | 2010-07-07 | Actelion Pharmaceuticals Ltd | Derivados 2- fenil-piridina substituidos |
| MA33260B1 (fr) | 2009-04-08 | 2012-05-02 | Actelion Pharmaceuticals Ltd | 6-(3-azabicyclo[3.1.0.]hex-3-yl)-2-phenylpyrimidines |
| CA2756654C (en) * | 2009-04-22 | 2017-08-22 | Actelion Pharmaceuticals Ltd | Thiazole derivatives and their use as p2y12 receptor antagonists |
| 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 |
| 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 |
| MY169319A (en) | 2011-07-26 | 2019-03-21 | Sanofi Sa | 3-heteroaroylamino-propionic acid derivatives and their use as pharmaceuticals |
| US9539246B2 (en) | 2011-08-30 | 2017-01-10 | University Of Utah Research Foundation | Methods and compositions for treating nephrogenic diabetes insipidus |
| WO2013072328A1 (en) | 2011-11-14 | 2013-05-23 | Sanofi | 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 |
| JP2015521183A (ja) * | 2012-05-18 | 2015-07-27 | サノフイ | ピリジン誘導体および病理学的血栓形成に関連する状態の治療へのその使用 |
| PL2882715T3 (pl) | 2012-05-18 | 2017-04-28 | Sanofi | Pochodne pirazolowe i ich zastosowanie jako antagonistów LPAR5 |
| 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 |
| 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 |
| SG11201506190QA (en) | 2013-03-28 | 2015-09-29 | Sanofi Sa | Biaryl-propionic acid derivatives and their use as pharmaceuticals |
| 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 |
| EP3515924B1 (en) | 2016-09-22 | 2021-12-15 | Idorsia Pharmaceuticals Ltd | Crystalline forms |
| MA49887A (fr) | 2017-03-15 | 2020-06-24 | Idorsia Pharmaceuticals Ltd | Administration sous-cutanée d'un antagoniste du récepteur p2y12 |
| 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 |
| US10512620B1 (en) | 2018-08-14 | 2019-12-24 | AltaThera Pharmaceuticals, LLC | Method of initiating and escalating sotalol hydrochloride dosing |
| US11610660B1 (en) | 2021-08-20 | 2023-03-21 | AltaThera Pharmaceuticals LLC | Antiarrhythmic drug dosing methods, medical devices, and systems |
| US11696902B2 (en) | 2018-08-14 | 2023-07-11 | AltaThera Pharmaceuticals, LLC | Method of initiating and escalating sotalol hydrochloride dosing |
| 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 |
| US12396970B2 (en) | 2021-08-20 | 2025-08-26 | AltaThera Pharmaceuticals LLC | Anti-arrhythmic compositions and methods |
| 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 |
| WO2003066671A1 (en) | 2002-02-05 | 2003-08-14 | Dainippon Pharmaceutical Co., Ltd. | Heterocyclic compounds having elastase-inhibiting activity and intermediates thereof |
| CA2511321A1 (en) * | 2002-12-23 | 2004-07-08 | Aventis Pharma Deutschland Gmbh | Pyrazole-derivatives as factor xa inhibitors |
| 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
- 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
- 2008-12-12 JP JP2010540047A patent/JP5560202B2/ja not_active Expired - Fee Related
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2010
- 2010-06-17 US US12/817,868 patent/US8598179B2/en not_active Expired - Fee Related
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