JP2016508487A5

JP2016508487A5 -

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Publication number: JP2016508487A5
Authority: JP; Japan
Prior art keywords: phenyl; naphthyridin; hydrazinecarbonyl; ethynyl; biphenyl
Prior art date: 2014-01-27
Legal status : Pending

Application number

JP2015555384A

Other languages

English (en)

Japanese (ja)

Other versions

JP2016508487A (ja

Filing date

2014-01-27

Publication date

2017-03-02

2014-01-27 Application filed filed Critical

2014-01-27 Priority claimed from PCT/US2014/013204 external-priority patent/WO2014117090A1/en

2016-03-22 Publication of JP2016508487A publication Critical patent/JP2016508487A/ja

2017-03-02 Publication of JP2016508487A5 publication Critical patent/JP2016508487A5/ja

Status Pending legal-status Critical Current

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150000001875 compounds Chemical class 0.000 claims 62
-1 hydroxy, amino Chemical group 0.000 claims 45
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 27
238000000034 method Methods 0.000 claims 26
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 24
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 24
125000000217 alkyl group Chemical group 0.000 claims 24
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 22
229910052736 halogen Inorganic materials 0.000 claims 21
150000002367 halogens Chemical class 0.000 claims 21
125000001072 heteroaryl group Chemical group 0.000 claims 18
125000004356 hydroxy functional group Chemical group O* 0.000 claims 18
DXVASWYJLYDQNC-UHFFFAOYSA-N 2-[4-[4-(2-hydroxyethylamino)phenyl]phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C1=CC=C(NCCO)C=C1 DXVASWYJLYDQNC-UHFFFAOYSA-N 0.000 claims 17
229910052739 hydrogen Inorganic materials 0.000 claims 17
239000001257 hydrogen Substances 0.000 claims 17
201000010099 disease Diseases 0.000 claims 15
125000000592 heterocycloalkyl group Chemical group 0.000 claims 14
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QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 11
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108010078554 Aromatase Proteins 0.000 claims 10
125000003709 fluoroalkyl group Chemical group 0.000 claims 10
150000002431 hydrogen Chemical class 0.000 claims 9
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239000011159 matrix material Substances 0.000 claims 7
125000000547 substituted alkyl group Chemical group 0.000 claims 7
AGYUINAIDZBPHL-UHFFFAOYSA-N 1-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]piperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1C(=O)N1CCCCC1C(O)=O AGYUINAIDZBPHL-UHFFFAOYSA-N 0.000 claims 6
UEGNBWPAKROMQW-UHFFFAOYSA-N 1-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]piperidine-3-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1C(=O)N1CCCC(C(O)=O)C1 UEGNBWPAKROMQW-UHFFFAOYSA-N 0.000 claims 6
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150000001732 carboxylic acid derivatives Chemical class 0.000 claims 6
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CAHGCLMLTWQZNJ-UHFFFAOYSA-N Nerifoliol Natural products CC12CCC(O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C CAHGCLMLTWQZNJ-UHFFFAOYSA-N 0.000 claims 5
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125000000623 heterocyclic group Chemical group 0.000 claims 5
CAHGCLMLTWQZNJ-RGEKOYMOSA-N lanosterol Chemical compound C([C@]12C)C[C@@H](O)C(C)(C)[C@H]1CCC1=C2CC[C@]2(C)[C@H]([C@H](CCC=C(C)C)C)CC[C@@]21C CAHGCLMLTWQZNJ-RGEKOYMOSA-N 0.000 claims 5
229940058690 lanosterol Drugs 0.000 claims 5
230000001404 mediated effect Effects 0.000 claims 5
241000894007 species Species 0.000 claims 5
RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 claims 5
WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical compound C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 claims 4
102100027518 1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial Human genes 0.000 claims 4
UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 claims 4
QZDDFQLIQRYMBV-UHFFFAOYSA-N 2-[3-nitro-2-(2-nitrophenyl)-4-oxochromen-8-yl]acetic acid Chemical compound OC(=O)CC1=CC=CC(C(C=2[N+]([O-])=O)=O)=C1OC=2C1=CC=CC=C1[N+]([O-])=O QZDDFQLIQRYMBV-UHFFFAOYSA-N 0.000 claims 4
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ITFJLETYAUTYKZ-RUZDIDTESA-N (2r)-1-[2-[4-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]phenoxy]acetyl]pyrrolidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C(C=C1)=CC=C1OCC(=O)N1CCC[C@@H]1C(O)=O ITFJLETYAUTYKZ-RUZDIDTESA-N 0.000 claims 2
CZXPEVNPLACHTK-AREMUKBSSA-N (2r)-1-[3-[4-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]phenyl]-1,2-oxazole-5-carbonyl]pyrrolidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C(C=C1)=CC=C1C(=NO1)C=C1C(=O)N1CCC[C@@H]1C(O)=O CZXPEVNPLACHTK-AREMUKBSSA-N 0.000 claims 2
SHTXBSGYVONNQG-HHHXNRCGSA-N (2r)-1-[3-[4-[4-[4-[hydroxy(methyl)carbamoyl]-1,6-naphthyridin-2-yl]phenyl]phenyl]-1,2-oxazole-5-carbonyl]pyrrolidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)N(O)C)=CC=1C(C=C1)=CC=C1C(C=C1)=CC=C1C(=NO1)C=C1C(=O)N1CCC[C@@H]1C(O)=O SHTXBSGYVONNQG-HHHXNRCGSA-N 0.000 claims 2
SBUVEHNNSQBSBZ-AREMUKBSSA-N (2r)-1-[3-chloro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]sulfonylpyrrolidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C(=C1)Cl)=CC=C1S(=O)(=O)N1CCC[C@@H]1C(O)=O SBUVEHNNSQBSBZ-AREMUKBSSA-N 0.000 claims 2
KWTPUHGTULVDDP-HHHXNRCGSA-N (2r)-1-[3-fluoro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]sulfonylpiperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C(=C1)F)=CC=C1S(=O)(=O)N1CCCC[C@@H]1C(O)=O KWTPUHGTULVDDP-HHHXNRCGSA-N 0.000 claims 2
MTLRVDAPINIDFM-AREMUKBSSA-N (2r)-1-[4-[2-[4-[4-(2,5-dioxoimidazolidin-1-yl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]sulfonylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@H]1CCCN1S(=O)(=O)C1=CC=C(C#CC=2C=CC(=CC=2)C=2N=C3C=CN=CC3=C(N3C(NCC3=O)=O)C=2)C=C1 MTLRVDAPINIDFM-AREMUKBSSA-N 0.000 claims 2
DPXXSHFFMNONBG-AREMUKBSSA-N (2r)-1-[4-[2-[4-[4-(5-oxo-2-sulfanylideneimidazolidin-1-yl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]sulfonylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@H]1CCCN1S(=O)(=O)C1=CC=C(C#CC=2C=CC(=CC=2)C=2N=C3C=CN=CC3=C(N3C(NCC3=O)=S)C=2)C=C1 DPXXSHFFMNONBG-AREMUKBSSA-N 0.000 claims 2
ROGXZXPWQGGAPU-AREMUKBSSA-N (2r)-1-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]pyrrolidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1C(=O)N1CCC[C@@H]1C(O)=O ROGXZXPWQGGAPU-AREMUKBSSA-N 0.000 claims 2
UPTPYXPRCBLVIT-AREMUKBSSA-N (2r)-1-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]sulfonylpyrrolidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1S(=O)(=O)N1CCC[C@@H]1C(O)=O UPTPYXPRCBLVIT-AREMUKBSSA-N 0.000 claims 2
ZDKOSBDWEUVSOZ-RUZDIDTESA-N (2r)-1-[[4-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]phenyl]methylsulfonyl]pyrrolidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C(C=C1)=CC=C1CS(=O)(=O)N1CCC[C@@H]1C(O)=O ZDKOSBDWEUVSOZ-RUZDIDTESA-N 0.000 claims 2
VGXDOHIJVISLSE-AREMUKBSSA-N (2r)-1-[[5-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]pyridin-2-yl]methyl]pyrrolidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=N1)=CC=C1CN1CCC[C@@H]1C(O)=O VGXDOHIJVISLSE-AREMUKBSSA-N 0.000 claims 2
NUDPVHAOXUYCFW-MHZLTWQESA-N (2s)-1-[3-chloro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]-n-hydroxypiperidine-2-carboxamide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C(=C1)Cl)=CC=C1C(=O)N1CCCC[C@H]1C(=O)NO NUDPVHAOXUYCFW-MHZLTWQESA-N 0.000 claims 2
UQSLKCRQZXGZCS-MHZLTWQESA-N (2s)-1-[3-chloro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]piperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C(=C1)Cl)=CC=C1C(=O)N1CCCC[C@H]1C(O)=O UQSLKCRQZXGZCS-MHZLTWQESA-N 0.000 claims 2
PKWGMSSVLULEKD-MHZLTWQESA-N (2s)-1-[3-chloro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]sulfonylpiperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C(=C1)Cl)=CC=C1S(=O)(=O)N1CCCC[C@H]1C(O)=O PKWGMSSVLULEKD-MHZLTWQESA-N 0.000 claims 2
WEWZDWHDBQYRBK-KHTLXAHUSA-N (2s)-1-[3-chloro-4-[2-[4-[4-(hydrazinecarbonyl)-7-(3-methoxypyrrolidin-1-yl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]piperidine-2-carboxylic acid Chemical compound C1C(OC)CCN1C1=CC2=NC(C=3C=CC(=CC=3)C#CC=3C(=CC(=CC=3)C(=O)N3[C@@H](CCCC3)C(O)=O)Cl)=CC(C(=O)NN)=C2C=N1 WEWZDWHDBQYRBK-KHTLXAHUSA-N 0.000 claims 2
QFCFOSMDNCVOGR-MHZLTWQESA-N (2s)-1-[3-chloro-4-[2-[4-[4-(hydrazinecarbonyl)-7-(methanesulfonamido)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]piperidine-2-carboxylic acid Chemical compound C=1C(C(=O)NN)=C2C=NC(NS(=O)(=O)C)=CC2=NC=1C(C=C1)=CC=C1C#CC(C(=C1)Cl)=CC=C1C(=O)N1CCCC[C@H]1C(O)=O QFCFOSMDNCVOGR-MHZLTWQESA-N 0.000 claims 2
ULDDRTOZLHRJRY-MHZLTWQESA-N (2s)-1-[3-chloro-4-[2-[4-[4-(hydrazinecarbonyl)-7-methoxy-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]piperidine-2-carboxylic acid Chemical compound C=1C(C(=O)NN)=C2C=NC(OC)=CC2=NC=1C(C=C1)=CC=C1C#CC(C(=C1)Cl)=CC=C1C(=O)N1CCCC[C@H]1C(O)=O ULDDRTOZLHRJRY-MHZLTWQESA-N 0.000 claims 2
WAKMIBSUDHGAQB-PMERELPUSA-N (2s)-1-[3-chloro-4-[2-[4-[4-(hydrazinecarbonyl)-7-morpholin-4-yl-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]piperidine-2-carboxylic acid Chemical compound N=1C=C2C(C(=O)NN)=CC(C=3C=CC(=CC=3)C#CC=3C(=CC(=CC=3)C(=O)N3[C@@H](CCCC3)C(O)=O)Cl)=NC2=CC=1N1CCOCC1 WAKMIBSUDHGAQB-PMERELPUSA-N 0.000 claims 2
KWTPUHGTULVDDP-MHZLTWQESA-N (2s)-1-[3-fluoro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]sulfonylpiperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C(=C1)F)=CC=C1S(=O)(=O)N1CCCC[C@H]1C(O)=O KWTPUHGTULVDDP-MHZLTWQESA-N 0.000 claims 2
ROGXZXPWQGGAPU-SANMLTNESA-N (2s)-1-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]pyrrolidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1C(=O)N1CCC[C@H]1C(O)=O ROGXZXPWQGGAPU-SANMLTNESA-N 0.000 claims 2
UPTPYXPRCBLVIT-SANMLTNESA-N (2s)-1-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]sulfonylpyrrolidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1S(=O)(=O)N1CCC[C@H]1C(O)=O UPTPYXPRCBLVIT-SANMLTNESA-N 0.000 claims 2
ZNXUUMXRRXGGBK-MHZLTWQESA-N (2s)-1-[4-[2-[4-[7-(carboxymethylsulfonylamino)-4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]-3-chlorobenzoyl]piperidine-2-carboxylic acid Chemical compound N=1C2=CC(NS(=O)(=O)CC(O)=O)=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C(=C1)Cl)=CC=C1C(=O)N1CCCC[C@H]1C(O)=O ZNXUUMXRRXGGBK-MHZLTWQESA-N 0.000 claims 2
FDRFBCZLFQZQEA-MHZLTWQESA-N (2s)-1-[4-[2-[4-[7-[(2-aminoacetyl)amino]-4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]-3-chlorobenzoyl]piperidine-2-carboxylic acid Chemical compound C=1C(C(=O)NN)=C2C=NC(NC(=O)CN)=CC2=NC=1C(C=C1)=CC=C1C#CC(C(=C1)Cl)=CC=C1C(=O)N1CCCC[C@H]1C(O)=O FDRFBCZLFQZQEA-MHZLTWQESA-N 0.000 claims 2
FWDOPQSEJOFZGR-MHZLTWQESA-N (2s)-1-[4-[2-[4-[7-[(2-carboxyacetyl)amino]-4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]-3-chlorobenzoyl]piperidine-2-carboxylic acid Chemical compound N=1C2=CC(NC(=O)CC(O)=O)=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C(=C1)Cl)=CC=C1C(=O)N1CCCC[C@H]1C(O)=O FWDOPQSEJOFZGR-MHZLTWQESA-N 0.000 claims 2
GXKXZKKMAZNWRR-UHFFFAOYSA-N 1-[2,3-difluoro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]piperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C(=C1F)F)=CC=C1C(=O)N1CCCCC1C(O)=O GXKXZKKMAZNWRR-UHFFFAOYSA-N 0.000 claims 2
QDVDTZOLPKLYQD-UHFFFAOYSA-N 1-[2,5-difluoro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]piperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C(=C1)F)=CC(F)=C1C(=O)N1CCCCC1C(O)=O QDVDTZOLPKLYQD-UHFFFAOYSA-N 0.000 claims 2
CKZWTJQKFCHFLS-UHFFFAOYSA-N 1-[2-[4-(4-fluorophenyl)phenyl]-1,6-naphthyridin-4-yl]imidazolidin-2-one Chemical compound C1=CC(F)=CC=C1C1=CC=C(C=2N=C3C=CN=CC3=C(N3C(NCC3)=O)C=2)C=C1 CKZWTJQKFCHFLS-UHFFFAOYSA-N 0.000 claims 2
ZDBMZFWEZSCGEK-UHFFFAOYSA-N 1-[2-[4-(4-fluorophenyl)phenyl]-1,6-naphthyridin-4-yl]imidazolidine-2,4-dione Chemical compound C1=CC(F)=CC=C1C1=CC=C(C=2N=C3C=CN=CC3=C(N3C(NC(=O)C3)=O)C=2)C=C1 ZDBMZFWEZSCGEK-UHFFFAOYSA-N 0.000 claims 2
DJLBMPPFKLBPST-UHFFFAOYSA-N 1-[2-chloro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]piperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1Cl)=CC=C1C(=O)N1CCCCC1C(O)=O DJLBMPPFKLBPST-UHFFFAOYSA-N 0.000 claims 2
HQZCBRFYXXGNLJ-UHFFFAOYSA-N 1-[2-fluoro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]piperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1F)=CC=C1C(=O)N1CCCCC1C(O)=O HQZCBRFYXXGNLJ-UHFFFAOYSA-N 0.000 claims 2
ZJFRCWZYNFKFHF-UHFFFAOYSA-N 1-[3,5-difluoro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]piperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C(=C1)F)=C(F)C=C1C(=O)N1CCCCC1C(O)=O ZJFRCWZYNFKFHF-UHFFFAOYSA-N 0.000 claims 2
KDKZQLKDUFBSHZ-UHFFFAOYSA-N 1-[3-[4-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]phenyl]-1,2-oxazole-5-carbonyl]piperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C(C=C1)=CC=C1C(=NO1)C=C1C(=O)N1CCCCC1C(O)=O KDKZQLKDUFBSHZ-UHFFFAOYSA-N 0.000 claims 2
UQSLKCRQZXGZCS-UHFFFAOYSA-N 1-[3-chloro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]piperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C(=C1)Cl)=CC=C1C(=O)N1CCCCC1C(O)=O UQSLKCRQZXGZCS-UHFFFAOYSA-N 0.000 claims 2
SJECBEVAFANIEO-UHFFFAOYSA-N 1-[3-chloro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]piperidine-3-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C(=C1)Cl)=CC=C1C(=O)N1CCCC(C(O)=O)C1 SJECBEVAFANIEO-UHFFFAOYSA-N 0.000 claims 2
KCVYFWLKIMVMDB-UHFFFAOYSA-N 1-[3-chloro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]sulfonylpiperidine-3-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C(=C1)Cl)=CC=C1S(=O)(=O)N1CCCC(C(O)=O)C1 KCVYFWLKIMVMDB-UHFFFAOYSA-N 0.000 claims 2
ACHOFQHPOZJCFY-UHFFFAOYSA-N 1-[3-fluoro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]piperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C(=C1)F)=CC=C1C(=O)N1CCCCC1C(O)=O ACHOFQHPOZJCFY-UHFFFAOYSA-N 0.000 claims 2
QOQCBYVSLIVZFS-UHFFFAOYSA-N 1-[3-fluoro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]piperidine-3-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C(=C1)F)=CC=C1C(=O)N1CCCC(C(O)=O)C1 QOQCBYVSLIVZFS-UHFFFAOYSA-N 0.000 claims 2
CMABZNGIUMJVLU-UHFFFAOYSA-N 1-[3-fluoro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]sulfonylpiperidine-3-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C(=C1)F)=CC=C1S(=O)(=O)N1CCCC(C(O)=O)C1 CMABZNGIUMJVLU-UHFFFAOYSA-N 0.000 claims 2
QILVYKJILCQWIJ-UHFFFAOYSA-N 1-[4-[2-[2-chloro-4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]piperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1Cl)=CC=C1C#CC(C=C1)=CC=C1C(=O)N1CCCCC1C(O)=O QILVYKJILCQWIJ-UHFFFAOYSA-N 0.000 claims 2
AEONYPFDJVZSNL-UHFFFAOYSA-N 1-[4-[2-[2-fluoro-4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]piperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1F)=CC=C1C#CC(C=C1)=CC=C1C(=O)N1CCCCC1C(O)=O AEONYPFDJVZSNL-UHFFFAOYSA-N 0.000 claims 2
XHRXVLQJSDTJEI-UHFFFAOYSA-N 1-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]-2-hydroxyphenyl]ethynyl]benzoyl]piperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1O)=CC=C1C#CC(C=C1)=CC=C1C(=O)N1CCCCC1C(O)=O XHRXVLQJSDTJEI-UHFFFAOYSA-N 0.000 claims 2
SRTPMSQAYHWJPE-UHFFFAOYSA-N 1-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]-2-methoxyphenyl]ethynyl]benzoyl]piperidine-2-carboxylic acid Chemical compound COC1=CC(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)=CC=C1C#CC(C=C1)=CC=C1C(=O)N1CCCCC1C(O)=O SRTPMSQAYHWJPE-UHFFFAOYSA-N 0.000 claims 2
KXCIOKGUTNAXFY-UHFFFAOYSA-N 1-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]-2-hydroxybenzoyl]piperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1O)=CC=C1C(=O)N1CCCCC1C(O)=O KXCIOKGUTNAXFY-UHFFFAOYSA-N 0.000 claims 2
ZOABVZKLOQFYQN-UHFFFAOYSA-N 1-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]-2-methoxybenzoyl]piperidine-2-carboxylic acid Chemical compound COC1=CC(C#CC=2C=CC(=CC=2)C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)=CC=C1C(=O)N1CCCCC1C(O)=O ZOABVZKLOQFYQN-UHFFFAOYSA-N 0.000 claims 2
ZGYWDPQMIRTHES-UHFFFAOYSA-N 1-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]-3-hydroxybenzoyl]piperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C(=C1)O)=CC=C1C(=O)N1CCCCC1C(O)=O ZGYWDPQMIRTHES-UHFFFAOYSA-N 0.000 claims 2
GVKMRIPUOXRXDQ-UHFFFAOYSA-N 1-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]-3-methoxybenzoyl]piperidine-2-carboxylic acid Chemical compound C=1C=C(C#CC=2C=CC(=CC=2)C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C(OC)=CC=1C(=O)N1CCCCC1C(O)=O GVKMRIPUOXRXDQ-UHFFFAOYSA-N 0.000 claims 2
OILUCMJIQOZCQY-UHFFFAOYSA-N 1-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]-4-hydroxypiperidine-3-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1C(=O)N1CCC(O)C(C(O)=O)C1 OILUCMJIQOZCQY-UHFFFAOYSA-N 0.000 claims 2
WLQHRWIBTPWOOP-UHFFFAOYSA-N 1-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]azetidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1C(=O)N1CCC1C(O)=O WLQHRWIBTPWOOP-UHFFFAOYSA-N 0.000 claims 2
FPPQABWOMNKWMC-UHFFFAOYSA-N 1-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]piperidine-4-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1C(=O)N1CCC(C(O)=O)CC1 FPPQABWOMNKWMC-UHFFFAOYSA-N 0.000 claims 2
DZWYQFYASOGJFD-UHFFFAOYSA-N 1-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]pyrrolidine-3-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1C(=O)N1CCC(C(O)=O)C1 DZWYQFYASOGJFD-UHFFFAOYSA-N 0.000 claims 2
FNUIBSFAHFPSIY-UHFFFAOYSA-N 1-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]sulfonylazetidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1S(=O)(=O)N1CCC1C(O)=O FNUIBSFAHFPSIY-UHFFFAOYSA-N 0.000 claims 2
FZUMXCCIVGJJJB-UHFFFAOYSA-N 1-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]sulfonylpiperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1S(=O)(=O)N1CCCCC1C(O)=O FZUMXCCIVGJJJB-UHFFFAOYSA-N 0.000 claims 2
MZQRESYDHTYCPN-UHFFFAOYSA-N 1-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]sulfonylpiperidine-3-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1S(=O)(=O)N1CCCC(C(O)=O)C1 MZQRESYDHTYCPN-UHFFFAOYSA-N 0.000 claims 2
YBGSNSKSTCVLKZ-UHFFFAOYSA-N 1-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]sulfonylpiperidine-4-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1S(=O)(=O)N1CCC(C(O)=O)CC1 YBGSNSKSTCVLKZ-UHFFFAOYSA-N 0.000 claims 2
XKICMRLBMPIPNN-UHFFFAOYSA-N 1-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]sulfonylpyrrolidine-3-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1S(=O)(=O)N1CCC(C(O)=O)C1 XKICMRLBMPIPNN-UHFFFAOYSA-N 0.000 claims 2
BCVDINKATMUENM-UHFFFAOYSA-N 1-[4-[2-[5-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]pyridin-2-yl]ethynyl]benzoyl]piperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=N1)=CC=C1C#CC(C=C1)=CC=C1C(=O)N1CCCCC1C(O)=O BCVDINKATMUENM-UHFFFAOYSA-N 0.000 claims 2
LKHDTZAMQJZFHG-UHFFFAOYSA-N 1-[4-[2-[5-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]thiophen-2-yl]ethynyl]benzoyl]piperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(S1)=CC=C1C#CC(C=C1)=CC=C1C(=O)N1CCCCC1C(O)=O LKHDTZAMQJZFHG-UHFFFAOYSA-N 0.000 claims 2
VPXQQJPIGHUQFP-UHFFFAOYSA-N 1-[4-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]benzoyl]piperidine-3-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)N1CCCC(C(O)=O)C1 VPXQQJPIGHUQFP-UHFFFAOYSA-N 0.000 claims 2
WZKGFTNGBQBQRA-UHFFFAOYSA-N 1-[4-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]phenyl]piperidine-3-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C(C=C1)=CC=C1N1CCCC(C(O)=O)C1 WZKGFTNGBQBQRA-UHFFFAOYSA-N 0.000 claims 2
CRUNSQFTLHKBPO-UHFFFAOYSA-N 1-[4-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]phenyl]piperidine-4-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C(C=C1)=CC=C1N1CCC(C(O)=O)CC1 CRUNSQFTLHKBPO-UHFFFAOYSA-N 0.000 claims 2
HJLHWGCGHYWGHL-UHFFFAOYSA-N 1-[4-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]phenyl]pyrrolidine-3-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C(C=C1)=CC=C1N1CCC(C(O)=O)C1 HJLHWGCGHYWGHL-UHFFFAOYSA-N 0.000 claims 2
CCIVUDFZCVQVFF-UHFFFAOYSA-N 1-[4-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]phenyl]sulfonylpiperidine-3-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C(C=C1)=CC=C1S(=O)(=O)N1CCCC(C(O)=O)C1 CCIVUDFZCVQVFF-UHFFFAOYSA-N 0.000 claims 2
UYZRCGRVQFVRPC-UHFFFAOYSA-N 1-[5-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]furan-2-carbonyl]piperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(O1)=CC=C1C(=O)N1CCCCC1C(O)=O UYZRCGRVQFVRPC-UHFFFAOYSA-N 0.000 claims 2
AFNWIRHODLPKRY-UHFFFAOYSA-N 1-[5-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]furan-2-carbonyl]piperidine-3-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(O1)=CC=C1C(=O)N1CCCC(C(O)=O)C1 AFNWIRHODLPKRY-UHFFFAOYSA-N 0.000 claims 2
CNEHLNQDZUHLJS-UHFFFAOYSA-N 1-[5-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]pyridine-2-carbonyl]piperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=N1)=CC=C1C(=O)N1CCCCC1C(O)=O CNEHLNQDZUHLJS-UHFFFAOYSA-N 0.000 claims 2
LYHDJSTUFSGGIF-UHFFFAOYSA-N 1-[5-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]thiophene-2-carbonyl]piperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(S1)=CC=C1C(=O)N1CCCCC1C(O)=O LYHDJSTUFSGGIF-UHFFFAOYSA-N 0.000 claims 2
ZILMEMNNWBQUCH-UHFFFAOYSA-N 1-[5-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]thiophene-2-carbonyl]piperidine-3-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(S1)=CC=C1C(=O)N1CCCC(C(O)=O)C1 ZILMEMNNWBQUCH-UHFFFAOYSA-N 0.000 claims 2
NFGWBOMBZSWJNE-UHFFFAOYSA-N 1-[6-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]pyridine-3-carbonyl]piperidine-2-carboxylic acid Chemical compound NNC(=O)c1cc(nc2ccncc12)-c1ccc(cc1)C#Cc1ccc(cn1)C(=O)N1CCCCC1C(O)=O NFGWBOMBZSWJNE-UHFFFAOYSA-N 0.000 claims 2
KEMHFVVJQHJMEI-UHFFFAOYSA-N 1-[[3-[4-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]phenyl]-1,2-oxazol-5-yl]methyl]-3-methylurea Chemical compound O1C(CNC(=O)NC)=CC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)=N1 KEMHFVVJQHJMEI-UHFFFAOYSA-N 0.000 claims 2
CFRUTPWWEMADDB-UHFFFAOYSA-N 1-[[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]carbamoyl]piperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1NC(=O)N1CCCCC1C(O)=O CFRUTPWWEMADDB-UHFFFAOYSA-N 0.000 claims 2
GRWNFJASVZOGBT-UHFFFAOYSA-N 1-amino-3-[2-[4-[4-(2-hydroxyethylamino)phenyl]phenyl]-1,6-naphthyridin-4-yl]urea Chemical compound N=1C2=CC=NC=C2C(NC(=O)NN)=CC=1C(C=C1)=CC=C1C1=CC=C(NCCO)C=C1 GRWNFJASVZOGBT-UHFFFAOYSA-N 0.000 claims 2
WEBUPOPCPCKGSB-UHFFFAOYSA-N 2-(4-phenylphenyl)-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C1=CC=CC=C1 WEBUPOPCPCKGSB-UHFFFAOYSA-N 0.000 claims 2
JEWIRUCRCSCNIS-UHFFFAOYSA-N 2-(4-pyridin-2-ylphenyl)-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C1=CC=CC=N1 JEWIRUCRCSCNIS-UHFFFAOYSA-N 0.000 claims 2
QMCDTXCSCIQSCS-UHFFFAOYSA-N 2-(4-pyridin-3-ylphenyl)-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C1=CC=CN=C1 QMCDTXCSCIQSCS-UHFFFAOYSA-N 0.000 claims 2
QXKAOVXZVJIOTJ-UHFFFAOYSA-N 2-(4-pyridin-4-ylphenyl)-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C1=CC=NC=C1 QXKAOVXZVJIOTJ-UHFFFAOYSA-N 0.000 claims 2
CHZHWUGQQVQXFB-UHFFFAOYSA-N 2-[1-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]piperidin-2-yl]acetic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1C(=O)N1CCCCC1CC(O)=O CHZHWUGQQVQXFB-UHFFFAOYSA-N 0.000 claims 2
VDBBUSBJMYIVPP-UHFFFAOYSA-N 2-[1-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]pyrrolidin-2-yl]acetic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1C(=O)N1CCCC1CC(O)=O VDBBUSBJMYIVPP-UHFFFAOYSA-N 0.000 claims 2
WEMBXCIEAUYPAC-UHFFFAOYSA-N 2-[2-[4-[4-(2-hydroxyethylamino)phenyl]phenyl]quinolin-4-yl]acetohydrazide Chemical compound N=1C2=CC=CC=C2C(CC(=O)NN)=CC=1C(C=C1)=CC=C1C1=CC=C(NCCO)C=C1 WEMBXCIEAUYPAC-UHFFFAOYSA-N 0.000 claims 2
RJEXAUAPEAQHJK-UHFFFAOYSA-N 2-[4-(1,3-oxazol-2-yl)phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C1=NC=CO1 RJEXAUAPEAQHJK-UHFFFAOYSA-N 0.000 claims 2
LGEDDJDCYXJGEJ-UHFFFAOYSA-N 2-[4-(1,3-oxazol-5-yl)phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C1=CN=CO1 LGEDDJDCYXJGEJ-UHFFFAOYSA-N 0.000 claims 2
WVZQGJZPEXIJKT-UHFFFAOYSA-N 2-[4-(1,3-thiazol-2-yl)phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C1=NC=CS1 WVZQGJZPEXIJKT-UHFFFAOYSA-N 0.000 claims 2
ORLQCWJOCZOSMH-UHFFFAOYSA-N 2-[4-(1h-pyrazol-4-yl)phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C=1C=NNC=1 ORLQCWJOCZOSMH-UHFFFAOYSA-N 0.000 claims 2
IFIBSONFSZDDSO-UHFFFAOYSA-N 2-[4-(1h-pyrazol-5-yl)phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C1=CC=NN1 IFIBSONFSZDDSO-UHFFFAOYSA-N 0.000 claims 2
AMLXGCMHWPGLNX-UHFFFAOYSA-N 2-[4-(2-hydroxyphenyl)phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound NNC(=O)c1cc(nc2ccncc12)-c1ccc(cc1)-c1ccccc1O AMLXGCMHWPGLNX-UHFFFAOYSA-N 0.000 claims 2
VICQTNLMHJGYJZ-UHFFFAOYSA-N 2-[4-(3,4-dihydroxyphenyl)phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound NNC(=O)c1cc(nc2ccncc12)-c1ccc(cc1)-c1ccc(O)c(O)c1 VICQTNLMHJGYJZ-UHFFFAOYSA-N 0.000 claims 2
JRKZCTISSJZQBE-UHFFFAOYSA-N 2-[4-(4-cyanophenyl)phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C1=CC=C(C#N)C=C1 JRKZCTISSJZQBE-UHFFFAOYSA-N 0.000 claims 2
MEBUFQBZXQOHOL-UHFFFAOYSA-N 2-[4-(4-cyanophenyl)phenyl]quinoline-4-carbohydrazide Chemical compound N=1C2=CC=CC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C1=CC=C(C#N)C=C1 MEBUFQBZXQOHOL-UHFFFAOYSA-N 0.000 claims 2
KLOSIAYFFVLDLA-UHFFFAOYSA-N 2-[4-(4-cyanophenyl)phenyl]quinoline-4-carboxylic acid Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C(C=C1)=CC=C1C1=CC=C(C#N)C=C1 KLOSIAYFFVLDLA-UHFFFAOYSA-N 0.000 claims 2
XACLZMBUAMUMCJ-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C1=CC=C(F)C=C1 XACLZMBUAMUMCJ-UHFFFAOYSA-N 0.000 claims 2
FBJFZAWCWVYEGS-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)phenyl]-6-oxido-1,6-naphthyridin-6-ium-4-carbohydrazide Chemical compound NNC(=O)c1cc(nc2cc[n+]([O-])cc12)-c1ccc(cc1)-c1ccc(F)cc1 FBJFZAWCWVYEGS-UHFFFAOYSA-N 0.000 claims 2
BWFFCCJTSPLQTE-UHFFFAOYSA-N 2-[4-(4-methylsulfonylphenyl)phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 BWFFCCJTSPLQTE-UHFFFAOYSA-N 0.000 claims 2
YIZQQFOPUVIHSN-UHFFFAOYSA-N 2-[4-(4-morpholin-4-ylsulfonylphenyl)phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound O1CCN(CC1)S(=O)(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=NC2=CC=NC=C2C(=C1)C(=O)NN YIZQQFOPUVIHSN-UHFFFAOYSA-N 0.000 claims 2
JLJIDUGIBCRABE-UHFFFAOYSA-N 2-[4-[2-(4-morpholin-4-ylsulfonylphenyl)ethynyl]phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1S(=O)(=O)N1CCOCC1 JLJIDUGIBCRABE-UHFFFAOYSA-N 0.000 claims 2
LXQNIGBHFAGRFC-UHFFFAOYSA-N 2-[4-[2-[1-(2-hydroxyethyl)-2-oxopyridin-4-yl]ethynyl]phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC=1C=CN(CCO)C(=O)C=1 LXQNIGBHFAGRFC-UHFFFAOYSA-N 0.000 claims 2
ZEHHDQLFCUQFNO-UHFFFAOYSA-N 2-[4-[2-[4-(2-hydroxyethylamino)phenyl]ethynyl]phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC1=CC=C(NCCO)C=C1 ZEHHDQLFCUQFNO-UHFFFAOYSA-N 0.000 claims 2
IVFCNCWWEXVJPA-UHFFFAOYSA-N 2-[4-[2-[4-(2-oxo-1,3-oxazolidin-5-yl)phenyl]ethynyl]phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1C1CNC(=O)O1 IVFCNCWWEXVJPA-UHFFFAOYSA-N 0.000 claims 2
WXPYGAZXOIFBBW-UHFFFAOYSA-N 2-[4-[2-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]ethynyl]phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=C(C#CC=2C=CC(=CC=2)C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 WXPYGAZXOIFBBW-UHFFFAOYSA-N 0.000 claims 2
GOXCPXIEWSGKNK-UHFFFAOYSA-N 2-[4-[2-[4-(4-methylpiperazine-1-carbonyl)phenyl]ethynyl]phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C#CC=2C=CC(=CC=2)C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 GOXCPXIEWSGKNK-UHFFFAOYSA-N 0.000 claims 2
FMBMQUQOMLZJIZ-UHFFFAOYSA-N 2-[4-[2-[4-(morpholin-4-ylmethyl)phenyl]ethynyl]phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1CN1CCOCC1 FMBMQUQOMLZJIZ-UHFFFAOYSA-N 0.000 claims 2
AQUVHUVXTSVHQP-UHFFFAOYSA-N 2-[4-[2-[4-(morpholine-4-carbonyl)phenyl]ethynyl]phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1C(=O)N1CCOCC1 AQUVHUVXTSVHQP-UHFFFAOYSA-N 0.000 claims 2
XAHHPAKNJYOJHR-MHZLTWQESA-N 2-[4-[2-[4-[(2s)-2-carboxypiperidine-1-carbonyl]-2-chlorophenyl]ethynyl]phenyl]-1,6-naphthyridine-4-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCCN1C(=O)C(C=C1Cl)=CC=C1C#CC1=CC=C(C=2N=C3C=CN=CC3=C(C(O)=O)C=2)C=C1 XAHHPAKNJYOJHR-MHZLTWQESA-N 0.000 claims 2
VYEHBIIZUUSKGH-UHFFFAOYSA-N 2-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]-2-oxopyridin-1-yl]acetic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC=1C=CN(CC(O)=O)C(=O)C=1 VYEHBIIZUUSKGH-UHFFFAOYSA-N 0.000 claims 2
KKKQFYNZGYYWKP-UHFFFAOYSA-N 2-[4-[4-(2-aminoethoxy)phenyl]phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound C1=CC(OCCN)=CC=C1C1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 KKKQFYNZGYYWKP-UHFFFAOYSA-N 0.000 claims 2
LXTYPVAJYSZFJJ-UHFFFAOYSA-N 2-[4-[4-(2-hydroxyethylamino)phenyl]phenyl]-1,6-naphthyridine-4-carboxylic acid Chemical compound C1=CC(NCCO)=CC=C1C1=CC=C(C=2N=C3C=CN=CC3=C(C(O)=O)C=2)C=C1 LXTYPVAJYSZFJJ-UHFFFAOYSA-N 0.000 claims 2
IOVQWGRBFDCAQA-UHFFFAOYSA-N 2-[4-[4-(2-hydroxyethylamino)phenyl]phenyl]-3-methoxy-1,6-naphthyridine-4-carbohydrazide Chemical compound N1=C2C=CN=CC2=C(C(=O)NN)C(OC)=C1C(C=C1)=CC=C1C1=CC=C(NCCO)C=C1 IOVQWGRBFDCAQA-UHFFFAOYSA-N 0.000 claims 2
JNXCDMRCTDCVKV-UHFFFAOYSA-N 2-[4-[4-(2-hydroxyethylamino)phenyl]phenyl]-3-methoxy-1,6-naphthyridine-4-carboxylic acid Chemical compound N1=C2C=CN=CC2=C(C(O)=O)C(OC)=C1C(C=C1)=CC=C1C1=CC=C(NCCO)C=C1 JNXCDMRCTDCVKV-UHFFFAOYSA-N 0.000 claims 2
OUGNBFPJDDCBOQ-UHFFFAOYSA-N 2-[4-[4-(2-hydroxyethylamino)phenyl]phenyl]-3-methyl-1,6-naphthyridine-4-carbohydrazide Chemical compound N1=C2C=CN=CC2=C(C(=O)NN)C(C)=C1C(C=C1)=CC=C1C1=CC=C(NCCO)C=C1 OUGNBFPJDDCBOQ-UHFFFAOYSA-N 0.000 claims 2
UMYOPEXLDSGSIR-UHFFFAOYSA-N 2-[4-[4-(2-hydroxyethylamino)phenyl]phenyl]-3-methyl-1,6-naphthyridine-4-carboxylic acid Chemical compound N1=C2C=CN=CC2=C(C(O)=O)C(C)=C1C(C=C1)=CC=C1C1=CC=C(NCCO)C=C1 UMYOPEXLDSGSIR-UHFFFAOYSA-N 0.000 claims 2
VDCYWHZGILQHBR-UHFFFAOYSA-N 2-[4-[4-(2-hydroxyethylamino)phenyl]phenyl]quinoline-4-carbohydrazide Chemical compound N=1C2=CC=CC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C1=CC=C(NCCO)C=C1 VDCYWHZGILQHBR-UHFFFAOYSA-N 0.000 claims 2
CURMNQUFPKDJLE-UHFFFAOYSA-N 2-[4-[4-(2-hydroxyethylamino)phenyl]phenyl]quinoline-4-carboxylic acid Chemical compound C1=CC(NCCO)=CC=C1C1=CC=C(C=2N=C3C=CC=CC3=C(C(O)=O)C=2)C=C1 CURMNQUFPKDJLE-UHFFFAOYSA-N 0.000 claims 2
ASBIQYGKCJEBTH-UHFFFAOYSA-N 2-[4-[4-(2-morpholin-4-yl-2-oxoethoxy)phenyl]phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C(C=C1)=CC=C1OCC(=O)N1CCOCC1 ASBIQYGKCJEBTH-UHFFFAOYSA-N 0.000 claims 2
NHMJBRHAZLRFBZ-UHFFFAOYSA-N 2-[4-[4-(2-morpholin-4-yl-2-oxoethyl)phenyl]phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C(C=C1)=CC=C1CC(=O)N1CCOCC1 NHMJBRHAZLRFBZ-UHFFFAOYSA-N 0.000 claims 2
GZJSNRVMLJZEPT-UHFFFAOYSA-N 2-[4-[4-(3-aminopropoxy)phenyl]phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound C1=CC(OCCCN)=CC=C1C1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 GZJSNRVMLJZEPT-UHFFFAOYSA-N 0.000 claims 2
JJDNVGBXSDKYEA-UHFFFAOYSA-N 2-[4-[4-(4-hydrazinyl-4-oxobutoxy)phenyl]phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound C1=CC(OCCCC(=O)NN)=CC=C1C1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 JJDNVGBXSDKYEA-UHFFFAOYSA-N 0.000 claims 2
LBUXKKMMIUHJLW-UHFFFAOYSA-N 2-[4-[4-(4-hydroxybutoxy)phenyl]phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C1=CC=C(OCCCCO)C=C1 LBUXKKMMIUHJLW-UHFFFAOYSA-N 0.000 claims 2
RWIQJWHLCBLWKN-UHFFFAOYSA-N 2-[4-[4-(morpholin-4-ylmethyl)phenyl]phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C(C=C1)=CC=C1CN1CCOCC1 RWIQJWHLCBLWKN-UHFFFAOYSA-N 0.000 claims 2
ZQCOYCKSDOAAQY-UHFFFAOYSA-N 2-[4-[4-(morpholin-4-ylsulfonylmethyl)phenyl]phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C(C=C1)=CC=C1CS(=O)(=O)N1CCOCC1 ZQCOYCKSDOAAQY-UHFFFAOYSA-N 0.000 claims 2
HQCAOJYHMCULHF-UHFFFAOYSA-N 2-[4-[4-(morpholine-4-carbonyl)phenyl]phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)N1CCOCC1 HQCAOJYHMCULHF-UHFFFAOYSA-N 0.000 claims 2
LQQOWVIXTAJUCG-UHFFFAOYSA-N 2-[4-[5-(4-hydroxybutoxy)pyridin-2-yl]phenyl]-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C1=CC=C(OCCCCO)C=N1 LQQOWVIXTAJUCG-UHFFFAOYSA-N 0.000 claims 2
UEQIPDLQPMGJLS-UHFFFAOYSA-N 2-[5-[4-(2-hydroxyethylamino)phenyl]pyridin-2-yl]-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(N=C1)=CC=C1C1=CC=C(NCCO)C=C1 UEQIPDLQPMGJLS-UHFFFAOYSA-N 0.000 claims 2
OZWYLLOKXBBAHF-UHFFFAOYSA-N 2-[6-[4-(2-hydroxyethylamino)phenyl]pyridin-3-yl]-1,6-naphthyridine-4-carbohydrazide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=N1)=CC=C1C1=CC=C(NCCO)C=C1 OZWYLLOKXBBAHF-UHFFFAOYSA-N 0.000 claims 2
OLNWVHVHCIJSMO-UHFFFAOYSA-N 2-[[2-[4-[2-[2-chloro-4-(morpholine-4-carbonyl)phenyl]ethynyl]phenyl]-4-(hydrazinecarbonyl)-1,6-naphthyridin-7-yl]-methylsulfamoyl]acetic acid Chemical compound C=1C(C(=O)NN)=C2C=NC(N(C)S(=O)(=O)CC(O)=O)=CC2=NC=1C(C=C1)=CC=C1C#CC(C(=C1)Cl)=CC=C1C(=O)N1CCOCC1 OLNWVHVHCIJSMO-UHFFFAOYSA-N 0.000 claims 2
OTFGAWBKWLBCAL-UHFFFAOYSA-N 2-[[3-fluoro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]sulfonyl-(2-methylpropyl)amino]acetic acid Chemical compound FC1=CC(S(=O)(=O)N(CC(O)=O)CC(C)C)=CC=C1C#CC1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 OTFGAWBKWLBCAL-UHFFFAOYSA-N 0.000 claims 2
WRLBHCSUOPSFEC-UHFFFAOYSA-N 2-[[3-fluoro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]sulfonyl-methylamino]-3-methylpentanoic acid Chemical compound FC1=CC(S(=O)(=O)N(C)C(C(C)CC)C(O)=O)=CC=C1C#CC1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 WRLBHCSUOPSFEC-UHFFFAOYSA-N 0.000 claims 2
FKSWVIJCNZVQBS-UHFFFAOYSA-N 2-[[3-fluoro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound CN(S(=O)(=O)C1=CC(=C(C=C1)C#CC1=CC=C(C=C1)C1=NC2=CC=NC=C2C(=C1)C(=O)NN)F)C(C(=O)O)CC1=CC=CC=C1 FKSWVIJCNZVQBS-UHFFFAOYSA-N 0.000 claims 2
IKMQWPAYONXAPU-UHFFFAOYSA-N 2-[[3-fluoro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]sulfonylamino]-3-methylpentanoic acid Chemical compound FC1=CC(S(=O)(=O)NC(C(C)CC)C(O)=O)=CC=C1C#CC1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 IKMQWPAYONXAPU-UHFFFAOYSA-N 0.000 claims 2
WFCXYUZMXPCHMK-UHFFFAOYSA-N 2-[[3-fluoro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C(=C1)F)=CC=C1S(=O)(=O)NC(C(O)=O)CC1=CC=CC=C1 WFCXYUZMXPCHMK-UHFFFAOYSA-N 0.000 claims 2
UZBJQZVQRXXEBM-UHFFFAOYSA-N 2-[[4-(hydrazinecarbonyl)-2-[4-[4-(4-hydroxybutoxy)phenyl]phenyl]-1,6-naphthyridin-7-yl]sulfamoyl]acetic acid Chemical compound N=1C2=CC(NS(=O)(=O)CC(O)=O)=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C1=CC=C(OCCCCO)C=C1 UZBJQZVQRXXEBM-UHFFFAOYSA-N 0.000 claims 2
JRZHHJAWDNZGJE-UHFFFAOYSA-N 2-[[4-(hydrazinecarbonyl)-2-[4-[4-[5-(hydroxymethyl)-1,2-oxazol-3-yl]phenyl]phenyl]-1,6-naphthyridin-7-yl]sulfamoyl]acetic acid Chemical compound N=1C2=CC(NS(=O)(=O)CC(O)=O)=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C(C=C1)=CC=C1C=1C=C(CO)ON=1 JRZHHJAWDNZGJE-UHFFFAOYSA-N 0.000 claims 2
DGYQDZBGURKRDW-UHFFFAOYSA-N 2-[[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]-methylamino]acetic acid Chemical compound C1=CC(C(=O)N(CC(O)=O)C)=CC=C1C#CC1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 DGYQDZBGURKRDW-UHFFFAOYSA-N 0.000 claims 2
DKCVJEAAXZRVKF-UHFFFAOYSA-N 2-[[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]-methylamino]propanoic acid Chemical compound C1=CC(C(=O)N(C)C(C)C(O)=O)=CC=C1C#CC1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 DKCVJEAAXZRVKF-UHFFFAOYSA-N 0.000 claims 2
GZERHQGNLAJIBI-UHFFFAOYSA-N 2-[[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]amino]-2-methylpropanoic acid Chemical compound C1=CC(C(=O)NC(C)(C)C(O)=O)=CC=C1C#CC1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 GZERHQGNLAJIBI-UHFFFAOYSA-N 0.000 claims 2
YPZDANGLKPOVIC-UHFFFAOYSA-N 2-[[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]amino]butanedioic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC1=CC=C(C(=O)NC(CC(O)=O)C(O)=O)C=C1 YPZDANGLKPOVIC-UHFFFAOYSA-N 0.000 claims 2
JLIULPGSVKLRSG-UHFFFAOYSA-N 2-[[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]amino]pentanedioic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 JLIULPGSVKLRSG-UHFFFAOYSA-N 0.000 claims 2
ZHTIQSLZCMXNQC-UHFFFAOYSA-N 2-[[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]amino]propanedioic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC1=CC=C(C(=O)NC(C(O)=O)C(O)=O)C=C1 ZHTIQSLZCMXNQC-UHFFFAOYSA-N 0.000 claims 2
QPJPQJMTMKNUEO-UHFFFAOYSA-N 2-[[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]sulfonyl-methylamino]-3-methylpentanoic acid Chemical compound C1=CC(S(=O)(=O)N(C)C(C(C)CC)C(O)=O)=CC=C1C#CC1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 QPJPQJMTMKNUEO-UHFFFAOYSA-N 0.000 claims 2
UAPSLKYRZNMQPM-UHFFFAOYSA-N 2-[[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]sulfonyl-methylamino]-3-phenylpropanoic acid Chemical compound C=1C=C(C#CC=2C=CC(=CC=2)C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=CC=1S(=O)(=O)N(C)C(C(O)=O)CC1=CC=CC=C1 UAPSLKYRZNMQPM-UHFFFAOYSA-N 0.000 claims 2
ZKPGEMXVKXWCMA-UHFFFAOYSA-N 2-[[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]sulfonylamino]-3-methylpentanoic acid Chemical compound C1=CC(S(=O)(=O)NC(C(C)CC)C(O)=O)=CC=C1C#CC1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 ZKPGEMXVKXWCMA-UHFFFAOYSA-N 0.000 claims 2
NAGLUKMXXJXSAT-UHFFFAOYSA-N 2-[[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]sulfonylamino]acetic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC1=CC=C(S(=O)(=O)NCC(O)=O)C=C1 NAGLUKMXXJXSAT-UHFFFAOYSA-N 0.000 claims 2
XGCSUCMYAYUOTC-UHFFFAOYSA-N 2-amino-3-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenoxy]propanoic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC1=CC=C(OCC(N)C(O)=O)C=C1 XGCSUCMYAYUOTC-UHFFFAOYSA-N 0.000 claims 2
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 2
FWNKGJRWKKTSKS-UHFFFAOYSA-N 3-[2-[4-(4-fluorophenyl)phenyl]-1,6-naphthyridin-4-yl]-2-sulfanylideneimidazolidin-4-one Chemical compound C1=CC(F)=CC=C1C1=CC=C(C=2N=C3C=CN=CC3=C(N3C(NCC3=O)=S)C=2)C=C1 FWNKGJRWKKTSKS-UHFFFAOYSA-N 0.000 claims 2
KAPCNQDTTRESKZ-UHFFFAOYSA-N 3-[2-[4-(4-fluorophenyl)phenyl]-1,6-naphthyridin-4-yl]imidazolidine-2,4-dione Chemical compound C1=CC(F)=CC=C1C1=CC=C(C=2N=C3C=CN=CC3=C(N3C(NCC3=O)=O)C=2)C=C1 KAPCNQDTTRESKZ-UHFFFAOYSA-N 0.000 claims 2
DZFJADYCPDCBSP-UHFFFAOYSA-N 3-[2-[4-[2-[4-(morpholin-4-ylmethyl)phenyl]ethynyl]phenyl]-1,6-naphthyridin-4-yl]-2-sulfanylideneimidazolidin-4-one Chemical compound O=C1CNC(=S)N1C1=CC(C=2C=CC(=CC=2)C#CC=2C=CC(CN3CCOCC3)=CC=2)=NC2=CC=NC=C12 DZFJADYCPDCBSP-UHFFFAOYSA-N 0.000 claims 2
KHCWGXZMJKYQGI-UHFFFAOYSA-N 3-[2-[4-[4-(2-hydroxyethylamino)phenyl]phenyl]quinolin-4-yl]imidazolidine-2,4-dione Chemical compound C1=CC(NCCO)=CC=C1C1=CC=C(C=2N=C3C=CC=CC3=C(N3C(NCC3=O)=O)C=2)C=C1 KHCWGXZMJKYQGI-UHFFFAOYSA-N 0.000 claims 2
BCCGTQUOGSDXQT-UHFFFAOYSA-N 3-[2-[4-[4-(4-hydroxybutoxy)phenyl]phenyl]-1,6-naphthyridin-4-yl]-2-sulfanylideneimidazolidin-4-one Chemical compound C1=CC(OCCCCO)=CC=C1C1=CC=C(C=2N=C3C=CN=CC3=C(N3C(NCC3=O)=S)C=2)C=C1 BCCGTQUOGSDXQT-UHFFFAOYSA-N 0.000 claims 2
XSGXURTUTUIFQF-UHFFFAOYSA-N 3-[2-[4-[4-(4-hydroxybutoxy)phenyl]phenyl]quinolin-4-yl]imidazolidine-2,4-dione Chemical compound C1=CC(OCCCCO)=CC=C1C1=CC=C(C=2N=C3C=CC=CC3=C(N3C(NCC3=O)=O)C=2)C=C1 XSGXURTUTUIFQF-UHFFFAOYSA-N 0.000 claims 2
IDMMWSOKPDQQJJ-UHFFFAOYSA-N 3-[2-[4-[4-[4-(oxan-2-yloxy)butoxy]phenyl]phenyl]-1,6-naphthyridin-4-yl]-2-sulfanylideneimidazolidin-4-one Chemical compound O=C1CNC(=S)N1C1=CC(C=2C=CC(=CC=2)C=2C=CC(OCCCCOC3OCCCC3)=CC=2)=NC2=CC=NC=C12 IDMMWSOKPDQQJJ-UHFFFAOYSA-N 0.000 claims 2
OTJUWHUUGKLPLI-UHFFFAOYSA-N 3-[2-[4-[4-[4-(oxan-2-yloxy)butoxy]phenyl]phenyl]-1,6-naphthyridin-4-yl]imidazolidine-2,4-dione Chemical compound O=C1CNC(=O)N1C1=CC(C=2C=CC(=CC=2)C=2C=CC(OCCCCOC3OCCCC3)=CC=2)=NC2=CC=NC=C12 OTJUWHUUGKLPLI-UHFFFAOYSA-N 0.000 claims 2
CNFRVHAQZWHCBY-UHFFFAOYSA-N 3-[2-[4-[5-(4-hydroxybutoxy)pyridin-2-yl]phenyl]-1,6-naphthyridin-4-yl]-2-sulfanylideneimidazolidin-4-one Chemical compound N1=CC(OCCCCO)=CC=C1C1=CC=C(C=2N=C3C=CN=CC3=C(N3C(NCC3=O)=S)C=2)C=C1 CNFRVHAQZWHCBY-UHFFFAOYSA-N 0.000 claims 2
HIWSJUILEHKLBU-UHFFFAOYSA-N 3-[4-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]phenyl]-1,2-oxazole-5-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C(C=C1)=CC=C1C=1C=C(C(O)=O)ON=1 HIWSJUILEHKLBU-UHFFFAOYSA-N 0.000 claims 2
XOZJWOPNOJXGFD-UHFFFAOYSA-N 3-[[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]-methylamino]-2-methylpropanoic acid Chemical compound C1=CC(C(=O)N(C)CC(C)C(O)=O)=CC=C1C#CC1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 XOZJWOPNOJXGFD-UHFFFAOYSA-N 0.000 claims 2
UITJBEMXOQMEPR-UHFFFAOYSA-N 3-[[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]-methylamino]butanoic acid Chemical compound C1=CC(C(=O)N(C)C(CC(O)=O)C)=CC=C1C#CC1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 UITJBEMXOQMEPR-UHFFFAOYSA-N 0.000 claims 2
YTVGCMBKRUXIEC-UHFFFAOYSA-N 3-[[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]-methylamino]propanoic acid Chemical compound C1=CC(C(=O)N(CCC(O)=O)C)=CC=C1C#CC1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 YTVGCMBKRUXIEC-UHFFFAOYSA-N 0.000 claims 2
RPOVPBDYXCXAIJ-UHFFFAOYSA-N 3-[[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]amino]-2-methylpropanoic acid Chemical compound C1=CC(C(=O)NCC(C)C(O)=O)=CC=C1C#CC1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 RPOVPBDYXCXAIJ-UHFFFAOYSA-N 0.000 claims 2
AWVBZKZELVCWKS-UHFFFAOYSA-N 3-[[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]amino]-2-phenylpropanoic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1C(=O)NCC(C(O)=O)C1=CC=CC=C1 AWVBZKZELVCWKS-UHFFFAOYSA-N 0.000 claims 2
GYQMTXPVNPDDKC-UHFFFAOYSA-N 3-[[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]amino]propanoic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC1=CC=C(C(=O)NCCC(O)=O)C=C1 GYQMTXPVNPDDKC-UHFFFAOYSA-N 0.000 claims 2
CIXQAXMWANWOHG-UHFFFAOYSA-N 4-(hydrazinecarbonyl)-2-[4-[4-(4-hydroxybutoxy)phenyl]phenyl]-1,6-naphthyridine-7-carboxylic acid Chemical compound N=1C2=CC(C(O)=O)=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C1=CC=C(OCCCCO)C=C1 CIXQAXMWANWOHG-UHFFFAOYSA-N 0.000 claims 2
IJZBBVDZSREWHW-UHFFFAOYSA-N 4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C#CC1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 IJZBBVDZSREWHW-UHFFFAOYSA-N 0.000 claims 2
UXZNBBVMFLGTKS-UHFFFAOYSA-N 4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]-n-methylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1C#CC1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 UXZNBBVMFLGTKS-UHFFFAOYSA-N 0.000 claims 2
FNCOGVYABGIUQO-UHFFFAOYSA-N 4-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]morpholine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1C(=O)N1CCOC(C(O)=O)C1 FNCOGVYABGIUQO-UHFFFAOYSA-N 0.000 claims 2
YPNZCTOGCOVGMX-UHFFFAOYSA-N 4-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]morpholine-3-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1C(=O)N1CCOCC1C(O)=O YPNZCTOGCOVGMX-UHFFFAOYSA-N 0.000 claims 2
MYGWOOUDQLTRSZ-UHFFFAOYSA-N 4-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]thiomorpholine-3-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1C(=O)N1CCSCC1C(O)=O MYGWOOUDQLTRSZ-UHFFFAOYSA-N 0.000 claims 2
OVIOZNABAWHSQS-UHFFFAOYSA-N 4-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 OVIOZNABAWHSQS-UHFFFAOYSA-N 0.000 claims 2
DJAXFSGXHPWJJU-UHFFFAOYSA-N 4-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]-n-methylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1C1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 DJAXFSGXHPWJJU-UHFFFAOYSA-N 0.000 claims 2
LCSOVGDDRFCIJR-UHFFFAOYSA-N 4-[4-[4-[4-(2,5-dioxoimidazolidin-1-yl)-1,6-naphthyridin-2-yl]phenyl]phenoxy]-n-hydroxybutanamide Chemical compound C1=CC(OCCCC(=O)NO)=CC=C1C1=CC=C(C=2N=C3C=CN=CC3=C(N3C(NCC3=O)=O)C=2)C=C1 LCSOVGDDRFCIJR-UHFFFAOYSA-N 0.000 claims 2
ZYHCJBFIMUIXOE-UHFFFAOYSA-N 4-[4-[4-[4-(2,5-dioxoimidazolidin-1-yl)-1,6-naphthyridin-2-yl]phenyl]phenoxy]butanoic acid Chemical compound C1=CC(OCCCC(=O)O)=CC=C1C1=CC=C(C=2N=C3C=CN=CC3=C(N3C(NCC3=O)=O)C=2)C=C1 ZYHCJBFIMUIXOE-UHFFFAOYSA-N 0.000 claims 2
QYXALDUMPBZDJW-UHFFFAOYSA-N 4-[4-[4-[4-(5-oxo-2-sulfanylideneimidazolidin-1-yl)-1,6-naphthyridin-2-yl]phenyl]phenoxy]butanoic acid Chemical compound C1=CC(OCCCC(=O)O)=CC=C1C1=CC=C(C=2N=C3C=CN=CC3=C(N3C(NCC3=O)=S)C=2)C=C1 QYXALDUMPBZDJW-UHFFFAOYSA-N 0.000 claims 2
HCVYUZZWZABULE-UHFFFAOYSA-N 4-[4-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]phenoxy]-n-hydroxybutanamide Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C1=CC=C(OCCCC(=O)NO)C=C1 HCVYUZZWZABULE-UHFFFAOYSA-N 0.000 claims 2
VMTFQURLMUYSED-UHFFFAOYSA-N 4-[4-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]phenoxy]butanoic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C1=CC=C(OCCCC(O)=O)C=C1 VMTFQURLMUYSED-UHFFFAOYSA-N 0.000 claims 2
SDWNJOBBSRPRIS-UHFFFAOYSA-N 4-[[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]amino]-2-hydroxybenzoic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1C(=O)NC1=CC=C(C(O)=O)C(O)=C1 SDWNJOBBSRPRIS-UHFFFAOYSA-N 0.000 claims 2
DGAASMNVMMOJNQ-UHFFFAOYSA-N 5-[2-[4-[4-(2-hydroxyethylamino)phenyl]phenyl]-1,6-naphthyridin-4-yl]-5-methylimidazolidine-2,4-dione Chemical compound C=1C(C=2C=CC(=CC=2)C=2C=CC(NCCO)=CC=2)=NC2=CC=NC=C2C=1C1(C)NC(=O)NC1=O DGAASMNVMMOJNQ-UHFFFAOYSA-N 0.000 claims 2
RPSULLUOUGXDHT-UHFFFAOYSA-N 5-[[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]amino]-2-hydroxybenzoic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C=C1)=CC=C1C(=O)NC1=CC=C(O)C(C(O)=O)=C1 RPSULLUOUGXDHT-UHFFFAOYSA-N 0.000 claims 2
208000035143 Bacterial infection Diseases 0.000 claims 2
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 2
208000024172 Cardiovascular disease Diseases 0.000 claims 2
102000029793 Isoleucine-tRNA ligase Human genes 0.000 claims 2
108700040464 Isoleucine-tRNA ligases Proteins 0.000 claims 2
UXRLIEKZANGCIC-UHFFFAOYSA-N NNC(=O)c1cc(nc2cc[n+]([O-])cc12)-c1ccc(cc1)-c1ccc(NCCO)cc1 Chemical compound NNC(=O)c1cc(nc2cc[n+]([O-])cc12)-c1ccc(cc1)-c1ccc(NCCO)cc1 UXRLIEKZANGCIC-UHFFFAOYSA-N 0.000 claims 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
108090001087 RNA ligase (ATP) Proteins 0.000 claims 2
239000002253 acid Substances 0.000 claims 2
239000002246 antineoplastic agent Substances 0.000 claims 2
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125000004429 atom Chemical group 0.000 claims 2
208000022362 bacterial infectious disease Diseases 0.000 claims 2
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DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims 2
125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 2
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims 2
229940127089 cytotoxic agent Drugs 0.000 claims 2
230000001419 dependent effect Effects 0.000 claims 2
208000016097 disease of metabolism Diseases 0.000 claims 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
125000004428 fluoroalkoxy group Chemical group 0.000 claims 2
230000002538 fungal effect Effects 0.000 claims 2
230000000855 fungicidal effect Effects 0.000 claims 2
239000000417 fungicide Substances 0.000 claims 2
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims 2
230000003993 interaction Effects 0.000 claims 2
208000030159 metabolic disease Diseases 0.000 claims 2
HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 2
244000005700 microbiome Species 0.000 claims 2
LQHKCVXBQXACBG-UHFFFAOYSA-N n-[2-[4-[2-[2-chloro-4-(morpholine-4-carbonyl)phenyl]ethynyl]phenyl]-4-(hydrazinecarbonyl)-1,6-naphthyridin-7-yl]-n-methylmethanesulfonamide Chemical compound C=1C(C(=O)NN)=C2C=NC(N(C)S(C)(=O)=O)=CC2=NC=1C(C=C1)=CC=C1C#CC(C(=C1)Cl)=CC=C1C(=O)N1CCOCC1 LQHKCVXBQXACBG-UHFFFAOYSA-N 0.000 claims 2
VQTYLKPHYOUQRB-UHFFFAOYSA-N n-[2-[4-[2-[2-chloro-4-(morpholine-4-carbonyl)phenyl]ethynyl]phenyl]-4-(hydrazinecarbonyl)-1,6-naphthyridin-7-yl]methanesulfonamide Chemical compound C=1C(C(=O)NN)=C2C=NC(NS(=O)(=O)C)=CC2=NC=1C(C=C1)=CC=C1C#CC(C(=C1)Cl)=CC=C1C(=O)N1CCOCC1 VQTYLKPHYOUQRB-UHFFFAOYSA-N 0.000 claims 2
KNOAERBJLMZTAF-UHFFFAOYSA-N n-[2-[4-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]phenoxy]ethyl]-2-methylpropanamide Chemical compound C1=CC(OCCNC(=O)C(C)C)=CC=C1C1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 KNOAERBJLMZTAF-UHFFFAOYSA-N 0.000 claims 2
IWLIDTAUOUZDEM-UHFFFAOYSA-N n-[2-[4-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]phenoxy]ethyl]propanamide Chemical compound C1=CC(OCCNC(=O)CC)=CC=C1C1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 IWLIDTAUOUZDEM-UHFFFAOYSA-N 0.000 claims 2
IETPUIMDPNMXRW-UHFFFAOYSA-N n-[3-[4-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]phenoxy]propyl]-2-methylpropanamide Chemical compound C1=CC(OCCCNC(=O)C(C)C)=CC=C1C1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 IETPUIMDPNMXRW-UHFFFAOYSA-N 0.000 claims 2
QOXWXKZYNMSFIK-UHFFFAOYSA-N n-[3-[4-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]phenoxy]propyl]acetamide Chemical compound C1=CC(OCCCNC(=O)C)=CC=C1C1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 QOXWXKZYNMSFIK-UHFFFAOYSA-N 0.000 claims 2
DZAOZGHEWYKUED-UHFFFAOYSA-N n-[3-[4-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]phenoxy]propyl]propanamide Chemical compound C1=CC(OCCCNC(=O)CC)=CC=C1C1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 DZAOZGHEWYKUED-UHFFFAOYSA-N 0.000 claims 2
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LNZZCOJLTIYHQQ-UHFFFAOYSA-N n-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C#CC1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 LNZZCOJLTIYHQQ-UHFFFAOYSA-N 0.000 claims 2
VSTBFVUQZKXQHC-UHFFFAOYSA-N n-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]ethanesulfonamide Chemical compound C1=CC(NS(=O)(=O)CC)=CC=C1C#CC1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 VSTBFVUQZKXQHC-UHFFFAOYSA-N 0.000 claims 2
RTOGWTQUCCCIOK-UHFFFAOYSA-N n-[4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]phenyl]propane-2-sulfonamide Chemical compound C1=CC(NS(=O)(=O)C(C)C)=CC=C1C#CC1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 RTOGWTQUCCCIOK-UHFFFAOYSA-N 0.000 claims 2
VHVFGTDUAYSRIK-UHFFFAOYSA-N n-[4-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 VHVFGTDUAYSRIK-UHFFFAOYSA-N 0.000 claims 2
HVQNXYBXIPMAJO-UHFFFAOYSA-N n-[4-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=CC=C(C=2N=C3C=CN=CC3=C(C(=O)NN)C=2)C=C1 HVQNXYBXIPMAJO-UHFFFAOYSA-N 0.000 claims 2
NEKPMRGLQVQZPG-UHFFFAOYSA-N n-hydroxy-2-[4-[4-(2-hydroxyethylamino)phenyl]phenyl]-n-methyl-1,6-naphthyridine-4-carboxamide Chemical compound N=1C2=CC=NC=C2C(C(=O)N(O)C)=CC=1C(C=C1)=CC=C1C1=CC=C(NCCO)C=C1 NEKPMRGLQVQZPG-UHFFFAOYSA-N 0.000 claims 2
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YJDZFCJZFYPEFL-UHFFFAOYSA-N n-hydroxy-n-methyl-2-[4-[2-[4-(trifluoromethylsulfonylamino)phenyl]ethynyl]phenyl]-1,6-naphthyridine-4-carboxamide Chemical compound N=1C2=CC=NC=C2C(C(=O)N(O)C)=CC=1C(C=C1)=CC=C1C#CC1=CC=C(NS(=O)(=O)C(F)(F)F)C=C1 YJDZFCJZFYPEFL-UHFFFAOYSA-N 0.000 claims 2
AEULOUHXGHFSID-UHFFFAOYSA-N n-hydroxy-n-methyl-2-[4-[2-[6-(trifluoromethylsulfonylamino)pyridin-3-yl]ethynyl]phenyl]-1,6-naphthyridine-4-carboxamide Chemical compound N=1C2=CC=NC=C2C(C(=O)N(O)C)=CC=1C(C=C1)=CC=C1C#CC1=CC=C(NS(=O)(=O)C(F)(F)F)N=C1 AEULOUHXGHFSID-UHFFFAOYSA-N 0.000 claims 2
SJHNDIBSYCAALB-UHFFFAOYSA-N n-hydroxy-n-methyl-2-[4-[4-[5-(morpholine-4-carbonyl)-1,2-oxazol-3-yl]phenyl]phenyl]-1,6-naphthyridine-4-carboxamide Chemical compound N=1C2=CC=NC=C2C(C(=O)N(O)C)=CC=1C(C=C1)=CC=C1C(C=C1)=CC=C1C(=NO1)C=C1C(=O)N1CCOCC1 SJHNDIBSYCAALB-UHFFFAOYSA-N 0.000 claims 2
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ILXLTSGJHCUAGS-XMMPIXPASA-N (2R)-1-[4-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]phenyl]sulfonylpyrrolidine-2-carboxylic acid Chemical compound N(N)C(=O)C1=CC(=NC2=CC=NC=C12)C1=CC=C(C=C1)C1=CC=C(C=C1)S(=O)(=O)N1[C@H](CCC1)C(=O)O ILXLTSGJHCUAGS-XMMPIXPASA-N 0.000 claims 1
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ACHOFQHPOZJCFY-MHZLTWQESA-N (2S)-1-[3-fluoro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]piperidine-2-carboxylic acid Chemical compound NNC(=O)c1cc(nc2ccncc12)-c1ccc(cc1)C#Cc1ccc(cc1F)C(=O)N1CCCC[C@H]1C(O)=O ACHOFQHPOZJCFY-MHZLTWQESA-N 0.000 claims 1
NDMNJCUCJIUXHN-AREMUKBSSA-N (2r)-1-[3-chloro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]pyrrolidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C(=C1)Cl)=CC=C1C(=O)N1CCC[C@@H]1C(O)=O NDMNJCUCJIUXHN-AREMUKBSSA-N 0.000 claims 1
ACHOFQHPOZJCFY-HHHXNRCGSA-N (2r)-1-[3-fluoro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]piperidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C(=C1)F)=CC=C1C(=O)N1CCCC[C@@H]1C(O)=O ACHOFQHPOZJCFY-HHHXNRCGSA-N 0.000 claims 1
GDRGORZDGHUZOC-AREMUKBSSA-N (2r)-1-[3-fluoro-4-[2-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]ethynyl]benzoyl]pyrrolidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C#CC(C(=C1)F)=CC=C1C(=O)N1CCC[C@@H]1C(O)=O GDRGORZDGHUZOC-AREMUKBSSA-N 0.000 claims 1
OIBUKLGDQLSUKJ-MUUNZHRXSA-N (2r)-1-[4-(hydrazinecarbonyl)-2-[4-[4-(4-hydroxybutoxy)phenyl]phenyl]-1,6-naphthyridine-7-carbonyl]pyrrolidine-2-carboxylic acid Chemical compound N=1C=C2C(C(=O)NN)=CC(C=3C=CC(=CC=3)C=3C=CC(OCCCCO)=CC=3)=NC2=CC=1C(=O)N1CCC[C@@H]1C(O)=O OIBUKLGDQLSUKJ-MUUNZHRXSA-N 0.000 claims 1
QEZFAYWVOQRNMJ-XMMPIXPASA-N (2r)-1-[4-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]benzoyl]pyrrolidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)N1CCC[C@@H]1C(O)=O QEZFAYWVOQRNMJ-XMMPIXPASA-N 0.000 claims 1
GOCMSMTUYHTZRN-XMMPIXPASA-N (2r)-1-[4-[4-[4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl]phenyl]phenyl]pyrrolidine-2-carboxylic acid Chemical compound N=1C2=CC=NC=C2C(C(=O)NN)=CC=1C(C=C1)=CC=C1C(C=C1)=CC=C1N1CCC[C@@H]1C(O)=O GOCMSMTUYHTZRN-XMMPIXPASA-N 0.000 claims 1
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JP2015555384A 2013-01-28 2014-01-27 金属酵素阻害剤化合物 Pending JP2016508487A (ja)