JP2010536752A5

JP2010536752A5 -

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Publication number: JP2010536752A5
Authority: JP; Japan
Prior art keywords: methyl; amino; carbamoyloxy; fluorophenyl; chloro
Prior art date: 2008-08-11
Legal status : Granted

Application number

JP2010521009A

Other languages

English (en)

Japanese (ja)

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JP2010536752A (ja

JP5670731B2 (ja

Filing date

2008-08-11

Publication date

2014-01-09

2008-08-11 Application filed filed Critical

2008-08-11 Priority claimed from PCT/US2008/009636 external-priority patent/WO2009023193A1/en

2010-12-02 Publication of JP2010536752A publication Critical patent/JP2010536752A/ja

2014-01-09 Publication of JP2010536752A5 publication Critical patent/JP2010536752A5/ja

2015-02-18 Application granted granted Critical

2015-02-18 Publication of JP5670731B2 publication Critical patent/JP5670731B2/ja

Status Expired - Fee Related legal-status Critical Current

2028-08-11 Anticipated expiration legal-status Critical

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-1 pyridino [4,3-d] pyridinyl Chemical group 0.000 claims description 347
239000000203 mixture Substances 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 161
150000001875 compounds Chemical class 0.000 claims 78
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 74
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 34
150000003857 carboxamides Chemical class 0.000 claims 27
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 25
229910019142 PO4 Inorganic materials 0.000 claims 25
239000010452 phosphate Substances 0.000 claims 25
229910052739 hydrogen Inorganic materials 0.000 claims 24
239000001257 hydrogen Substances 0.000 claims 24
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 22
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 20
150000003839 salts Chemical class 0.000 claims 19
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 15
HNGXTXJLCUFYQL-UHFFFAOYSA-N 1-[(2-chloro-3-fluorophenyl)methyl]-3-methylurea Chemical compound CNC(=O)NCC1=CC=CC(F)=C1Cl HNGXTXJLCUFYQL-UHFFFAOYSA-N 0.000 claims 14
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 13
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 13
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 13
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 13
125000000592 heterocycloalkyl group Chemical group 0.000 claims 12
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 12
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 12
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 11
150000002431 hydrogen Chemical class 0.000 claims 11
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 11
125000000217 alkyl group Chemical group 0.000 claims 10
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 10
RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 claims 9
125000003107 substituted aryl group Chemical group 0.000 claims 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 8
HNBDRPTVWVGKBR-UHFFFAOYSA-N n-pentanoic acid methyl ester Natural products CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 claims 8
125000005017 substituted alkenyl group Chemical group 0.000 claims 8
125000000547 substituted alkyl group Chemical group 0.000 claims 8
125000005843 halogen group Chemical group 0.000 claims 6
125000001072 heteroaryl group Chemical group 0.000 claims 6
AKOOLKBOVMJJML-UHFFFAOYSA-N 1-[(2,3-difluorophenyl)methyl]-3-methylurea Chemical compound CNC(=O)NCC1=CC=CC(F)=C1F AKOOLKBOVMJJML-UHFFFAOYSA-N 0.000 claims 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 5
125000004429 atom Chemical group 0.000 claims 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims 5
125000005415 substituted alkoxy group Chemical group 0.000 claims 5
125000004426 substituted alkynyl group Chemical group 0.000 claims 5
125000005346 substituted cycloalkyl group Chemical group 0.000 claims 5
125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
125000004104 aryloxy group Chemical group 0.000 claims 4
229910052799 carbon Inorganic materials 0.000 claims 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 claims 4
125000004551 isoquinolin-3-yl group Chemical group C1=NC(=CC2=CC=CC=C12)* 0.000 claims 4
NUKZAGXMHTUAFE-UHFFFAOYSA-N methyl hexanoate Chemical group CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 claims 4
239000008194 pharmaceutical composition Substances 0.000 claims 4
125000004193 piperazinyl group Chemical group 0.000 claims 4
125000004076 pyridyl group Chemical group 0.000 claims 4
125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 3
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 3
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 3
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 3
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 3
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 3
201000010099 disease Diseases 0.000 claims 3
JQVXMIPNQMYRPE-UHFFFAOYSA-N ethyl dimethyl phosphate Chemical compound CCOP(=O)(OC)OC JQVXMIPNQMYRPE-UHFFFAOYSA-N 0.000 claims 3
125000005553 heteroaryloxy group Chemical group 0.000 claims 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 3
125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims 3
IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 claims 3
HNVBNDIMWOYRFU-DHLKQENFSA-N tert-butyl n-[(2s)-1-[[(4s)-4-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-(1,7-naphthyridin-6-ylcarbamoyloxy)pentyl]amino]-3-hydroxy-1-oxopropan-2-yl]carbamate Chemical compound CC(=O)N([C@@H](CCCNC(=O)[C@H](CO)NC(=O)OC(C)(C)C)COC(=O)NC=1N=CC2=NC=CC=C2C=1)NCC1=CC=CC(F)=C1Cl HNVBNDIMWOYRFU-DHLKQENFSA-N 0.000 claims 3
125000001544 thienyl group Chemical group 0.000 claims 3
125000003396 thiol group Chemical group [H]S* 0.000 claims 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
KRZJRNZICWNMOA-GXSJLCMTSA-N (3s,4r)-4,8-dihydroxy-3-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2[C@@H](O)[C@@H](OC)CC(=O)C2=C1O KRZJRNZICWNMOA-GXSJLCMTSA-N 0.000 claims 2
125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
229930195711 D-Serine Natural products 0.000 claims 2
241000124008 Mammalia Species 0.000 claims 2
QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 2
102000003505 Myosin Human genes 0.000 claims 2
108060008487 Myosin Proteins 0.000 claims 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 2
XFWKFGDFHGECLY-IJBYHRAESA-N [(2s)-2-[acetyl-[(2-chlorophenyl)methylamino]amino]-4-hydroxy-3,4-dimethylpentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C(C)C(C)(C)O)NCC1=CC=CC=C1Cl XFWKFGDFHGECLY-IJBYHRAESA-N 0.000 claims 2
239000002253 acid Substances 0.000 claims 2
125000002252 acyl group Chemical group 0.000 claims 2
125000004423 acyloxy group Chemical group 0.000 claims 2
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 2
125000003943 azolyl group Chemical group 0.000 claims 2
125000005873 benzo[d]thiazolyl group Chemical group 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
229940095102 methyl benzoate Drugs 0.000 claims 2
DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 2
125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 2
NVTPMUHPCAUGCB-UHFFFAOYSA-N pentyl dihydrogen phosphate Chemical compound CCCCCOP(O)(O)=O NVTPMUHPCAUGCB-UHFFFAOYSA-N 0.000 claims 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
229910052698 phosphorus Inorganic materials 0.000 claims 2
239000011574 phosphorus Substances 0.000 claims 2
DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 2
125000003386 piperidinyl group Chemical group 0.000 claims 2
125000000714 pyrimidinyl group Chemical group 0.000 claims 2
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 2
OUXZKHNRJZPAFC-UHFFFAOYSA-N (2-chloro-3-fluorophenyl)methylurea Chemical compound ClC1=C(C=CC=C1F)CNC(=O)N OUXZKHNRJZPAFC-UHFFFAOYSA-N 0.000 claims 1
SJHHSPYALALONO-SFHVURJKSA-N (2s)-n-[(2-chloro-3-fluorophenyl)methyl]-2-[[(6-fluoroisoquinolin-3-yl)carbamoylamino]methyl]pyrrolidine-1-carboxamide Chemical compound C([C@H]1CNC(=O)NC=2N=CC3=CC=C(C=C3C=2)F)CCN1C(=O)NCC1=CC=CC(F)=C1Cl SJHHSPYALALONO-SFHVURJKSA-N 0.000 claims 1
LPQNEJNHQWFWAX-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl)urea Chemical compound OCC(C)(C)CNC(N)=O LPQNEJNHQWFWAX-UHFFFAOYSA-N 0.000 claims 1
PSPXARYONNFEBB-SFHVURJKSA-N (3s)-3-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4-[(6-fluoroisoquinolin-3-yl)carbamoyloxy]butanoic acid Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CC(O)=O)NCC1=CC=CC(F)=C1Cl PSPXARYONNFEBB-SFHVURJKSA-N 0.000 claims 1
KWUBYCCZXAYOSX-IBGZPJMESA-N (4s)-4-[acetyl-[(2,3-difluorophenyl)methylamino]amino]-5-(isoquinolin-3-ylcarbamoyloxy)pentanoic acid Chemical compound CC(=O)N([C@@H](CCC(O)=O)COC(=O)NC=1N=CC2=CC=CC=C2C=1)NCC1=CC=CC(F)=C1F KWUBYCCZXAYOSX-IBGZPJMESA-N 0.000 claims 1
JVMKVJSQJXTCKN-IBGZPJMESA-N (4s)-4-[acetyl-[(2,3-difluorophenyl)methylamino]amino]-5-[(6-fluoroisoquinolin-3-yl)carbamoyloxy]pentanoic acid Chemical compound CC(=O)N([C@@H](CCC(O)=O)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)NCC1=CC=CC(F)=C1F JVMKVJSQJXTCKN-IBGZPJMESA-N 0.000 claims 1
GFYZBSDGENFVCY-HNNXBMFYSA-N (4s)-4-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-(1,3-benzothiazol-2-ylcarbamoyloxy)pentanoic acid Chemical compound CC(=O)N([C@@H](CCC(O)=O)COC(=O)NC=1SC2=CC=CC=C2N=1)NCC1=CC=CC(F)=C1Cl GFYZBSDGENFVCY-HNNXBMFYSA-N 0.000 claims 1
CNUOKKKCWGIDQS-IBGZPJMESA-N (4s)-4-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-(isoquinolin-3-ylcarbamoyloxy)pentanoic acid Chemical compound CC(=O)N([C@@H](CCC(O)=O)COC(=O)NC=1N=CC2=CC=CC=C2C=1)NCC1=CC=CC(F)=C1Cl CNUOKKKCWGIDQS-IBGZPJMESA-N 0.000 claims 1
FFNVIWGRJFGSKY-IBGZPJMESA-N (4s)-4-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-[(6-fluoroisoquinolin-3-yl)carbamoyloxy]pentanoic acid Chemical compound CC(=O)N([C@@H](CCC(O)=O)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)NCC1=CC=CC(F)=C1Cl FFNVIWGRJFGSKY-IBGZPJMESA-N 0.000 claims 1
MFVREXSIOFPYNE-IBGZPJMESA-N (5s)-5-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-6-(2,6-naphthyridin-3-ylcarbamoyloxy)hexanoic acid Chemical compound CC(=O)N([C@@H](CCCC(O)=O)COC(=O)NC=1N=CC2=CC=NC=C2C=1)NCC1=CC=CC(F)=C1Cl MFVREXSIOFPYNE-IBGZPJMESA-N 0.000 claims 1
GPUINJLFSODRFL-NRFANRHFSA-N (5s)-5-[acetyl-[(2-chlorophenyl)methylamino]amino]-6-(isoquinolin-3-ylcarbamoyloxy)hexanoic acid Chemical compound CC(=O)N([C@@H](CCCC(O)=O)COC(=O)NC=1N=CC2=CC=CC=C2C=1)NCC1=CC=CC=C1Cl GPUINJLFSODRFL-NRFANRHFSA-N 0.000 claims 1
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 1
VCDGOBCNQULOOV-UHFFFAOYSA-N 1-[(2-bromophenyl)methyl]-3-methylurea Chemical compound CNC(=O)NCC1=CC=CC=C1Br VCDGOBCNQULOOV-UHFFFAOYSA-N 0.000 claims 1
NJYSFYSJTHLLKP-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-3-methylurea Chemical compound CNC(=O)NCC1=CC=CC=C1Cl NJYSFYSJTHLLKP-UHFFFAOYSA-N 0.000 claims 1
IROXYQACBUQVKM-UHFFFAOYSA-N 1-[(3-chloro-2-fluorophenyl)methyl]-3-methylurea Chemical compound ClC=1C(=C(C=CC=1)CNC(=O)NC)F IROXYQACBUQVKM-UHFFFAOYSA-N 0.000 claims 1
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
RYIKQVNVGSOMEY-UHFFFAOYSA-N 2-[(2,5-dichlorophenyl)methylcarbamoyl-methylamino]ethyl n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCN(C)C(=O)NCC1=CC(Cl)=CC=C1Cl RYIKQVNVGSOMEY-UHFFFAOYSA-N 0.000 claims 1
OFVIQOGKUSMRFT-UHFFFAOYSA-N 2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-(2,2,2-trifluoroethyl)amino]ethyl n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCN(CC(F)(F)F)C(=O)NCC1=CC=CC(F)=C1Cl OFVIQOGKUSMRFT-UHFFFAOYSA-N 0.000 claims 1
MNLOJRCFBDMBJW-UHFFFAOYSA-N 2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-(2,2-difluoroethyl)amino]ethyl n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCN(CC(F)F)C(=O)NCC1=CC=CC(F)=C1Cl MNLOJRCFBDMBJW-UHFFFAOYSA-N 0.000 claims 1
OBXPJVBBYATXKQ-UHFFFAOYSA-N 2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-(2-hydroxy-2-methylpropyl)amino]ethyl n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCN(CC(C)(O)C)C(=O)NCC1=CC=CC(F)=C1Cl OBXPJVBBYATXKQ-UHFFFAOYSA-N 0.000 claims 1
AOYRKCWAGAPRQS-UHFFFAOYSA-N 2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-(3,3,3-trifluoropropyl)amino]ethyl n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCN(CCC(F)(F)F)C(=O)NCC1=CC=CC(F)=C1Cl AOYRKCWAGAPRQS-UHFFFAOYSA-N 0.000 claims 1
VTQDQNWRGZTFJE-UHFFFAOYSA-N 2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-ethylamino]ethyl n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCN(CC)C(=O)NCC1=CC=CC(F)=C1Cl VTQDQNWRGZTFJE-UHFFFAOYSA-N 0.000 claims 1
JKNIOOOCZGNJAD-UHFFFAOYSA-N 2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]ethyl n-(1,6-naphthyridin-7-yl)carbamate Chemical compound C=1C2=NC=CC=C2C=NC=1NC(=O)OCCN(C)C(=O)NCC1=CC=CC(F)=C1Cl JKNIOOOCZGNJAD-UHFFFAOYSA-N 0.000 claims 1
DJMTWSGPMXHLQY-UHFFFAOYSA-N 2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]ethyl n-(1,7-naphthyridin-6-yl)carbamate Chemical compound C=1C2=CC=CN=C2C=NC=1NC(=O)OCCN(C)C(=O)NCC1=CC=CC(F)=C1Cl DJMTWSGPMXHLQY-UHFFFAOYSA-N 0.000 claims 1
VISAHVFMOFGYKW-UHFFFAOYSA-N 2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]ethyl n-(2,6-naphthyridin-3-yl)carbamate Chemical compound C=1C2=CN=CC=C2C=NC=1NC(=O)OCCN(C)C(=O)NCC1=CC=CC(F)=C1Cl VISAHVFMOFGYKW-UHFFFAOYSA-N 0.000 claims 1
OSGZRNLKGKOLEQ-UHFFFAOYSA-N 2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]ethyl n-(4,5-dimethylpyridin-2-yl)carbamate Chemical compound C=1C=CC(F)=C(Cl)C=1CNC(=O)N(C)CCOC(=O)NC1=CC(C)=C(C)C=N1 OSGZRNLKGKOLEQ-UHFFFAOYSA-N 0.000 claims 1
ZVSUIHDNCDNWDS-UHFFFAOYSA-N 2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]ethyl n-(5-acetylisoquinolin-3-yl)carbamate Chemical compound C=1C2=C(C(C)=O)C=CC=C2C=NC=1NC(=O)OCCN(C)C(=O)NCC1=CC=CC(F)=C1Cl ZVSUIHDNCDNWDS-UHFFFAOYSA-N 0.000 claims 1
LPXBGBBHLSJKJO-UHFFFAOYSA-N 2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]ethyl n-(5-bromo-4-methylpyridin-2-yl)carbamate Chemical compound C=1C=CC(F)=C(Cl)C=1CNC(=O)N(C)CCOC(=O)NC1=CC(C)=C(Br)C=N1 LPXBGBBHLSJKJO-UHFFFAOYSA-N 0.000 claims 1
DABCKRNRDYPSPG-UHFFFAOYSA-N 2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]ethyl n-(5-bromoisoquinolin-3-yl)carbamate Chemical compound C=1C2=C(Br)C=CC=C2C=NC=1NC(=O)OCCN(C)C(=O)NCC1=CC=CC(F)=C1Cl DABCKRNRDYPSPG-UHFFFAOYSA-N 0.000 claims 1
NLVWKHNOTNRVEB-UHFFFAOYSA-N 2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]ethyl n-(5-cyano-4-methylpyridin-2-yl)carbamate Chemical compound C=1C=CC(F)=C(Cl)C=1CNC(=O)N(C)CCOC(=O)NC1=CC(C)=C(C#N)C=N1 NLVWKHNOTNRVEB-UHFFFAOYSA-N 0.000 claims 1
BPFOQZPBLGYXKV-UHFFFAOYSA-N 2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]ethyl n-[5-(hydroxymethyl)isoquinolin-3-yl]carbamate Chemical compound C=1C2=C(CO)C=CC=C2C=NC=1NC(=O)OCCN(C)C(=O)NCC1=CC=CC(F)=C1Cl BPFOQZPBLGYXKV-UHFFFAOYSA-N 0.000 claims 1
YYCPIWWEZBROGY-UHFFFAOYSA-N 2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]ethyl n-[6-(hydroxymethyl)isoquinolin-3-yl]carbamate Chemical compound C=1C2=CC(CO)=CC=C2C=NC=1NC(=O)OCCN(C)C(=O)NCC1=CC=CC(F)=C1Cl YYCPIWWEZBROGY-UHFFFAOYSA-N 0.000 claims 1
ALYAAUZNCGQVQQ-UHFFFAOYSA-N 2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]ethyl n-[7-(hydroxymethyl)isoquinolin-3-yl]carbamate Chemical compound C=1C2=CC=C(CO)C=C2C=NC=1NC(=O)OCCN(C)C(=O)NCC1=CC=CC(F)=C1Cl ALYAAUZNCGQVQQ-UHFFFAOYSA-N 0.000 claims 1
CZNHDHIYKHYNRZ-UHFFFAOYSA-N 2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]ethyl n-isoquinolin-3-ylcarbamate Chemical compound C=1C2=CC=CC=C2C=NC=1NC(=O)OCCN(C)C(=O)NCC1=CC=CC(F)=C1Cl CZNHDHIYKHYNRZ-UHFFFAOYSA-N 0.000 claims 1
XXYZWZXXNXETPY-UHFFFAOYSA-N 2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-propan-2-ylamino]ethyl n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCN(C(C)C)C(=O)NCC1=CC=CC(F)=C1Cl XXYZWZXXNXETPY-UHFFFAOYSA-N 0.000 claims 1
IXEOPCWHCZNSOL-UHFFFAOYSA-N 2-[(2-chloro-3-hydroxyphenyl)methylcarbamoyl-methylamino]ethyl n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCN(C)C(=O)NCC1=CC=CC(O)=C1Cl IXEOPCWHCZNSOL-UHFFFAOYSA-N 0.000 claims 1
SYSGMEGVUJPITH-UHFFFAOYSA-N 2-[(2-chloro-3-methoxyphenyl)methylcarbamoyl-methylamino]ethyl n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound COC1=CC=CC(CNC(=O)N(C)CCOC(=O)NC=2N=CC3=CC=C(F)C=C3C=2)=C1Cl SYSGMEGVUJPITH-UHFFFAOYSA-N 0.000 claims 1
YHNPLIBMDGUXDN-UHFFFAOYSA-N 2-[(2-chloro-4-fluorophenyl)methylcarbamoyl-ethylamino]ethyl n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCN(CC)C(=O)NCC1=CC=C(F)C=C1Cl YHNPLIBMDGUXDN-UHFFFAOYSA-N 0.000 claims 1
ZWVMYTLYDHJQQJ-UHFFFAOYSA-N 2-[(2-chloro-4-fluorophenyl)methylcarbamoyl-propan-2-ylamino]ethyl n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCN(C(C)C)C(=O)NCC1=CC=C(F)C=C1Cl ZWVMYTLYDHJQQJ-UHFFFAOYSA-N 0.000 claims 1
IBADXMBYPPWTLU-UHFFFAOYSA-N 2-[(2-chloro-5-fluorophenyl)methylcarbamoyl-methylamino]ethyl n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCN(C)C(=O)NCC1=CC(F)=CC=C1Cl IBADXMBYPPWTLU-UHFFFAOYSA-N 0.000 claims 1
BRLLGDBWSYDQQY-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylcarbamoyl-[2-(2-hydroxyethoxy)ethyl]amino]ethyl n-isoquinolin-3-ylcarbamate Chemical compound C=1C2=CC=CC=C2C=NC=1NC(=O)OCCN(CCOCCO)C(=O)NCC1=CC=CC=C1Cl BRLLGDBWSYDQQY-UHFFFAOYSA-N 0.000 claims 1
YFFXFYYWFZFNFS-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylcarbamoyl-[2-[2-(dimethylamino)ethoxy]ethyl]amino]ethyl n-isoquinolin-3-ylcarbamate Chemical compound C=1C2=CC=CC=C2C=NC=1NC(=O)OCCN(CCOCCN(C)C)C(=O)NCC1=CC=CC=C1Cl YFFXFYYWFZFNFS-UHFFFAOYSA-N 0.000 claims 1
BSDSQHNXOUNOFO-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylcarbamoyl-methylamino]ethyl n-(1,3-benzothiazol-2-yl)carbamate Chemical compound N=1C2=CC=CC=C2SC=1NC(=O)OCCN(C)C(=O)NCC1=CC=CC=C1Cl BSDSQHNXOUNOFO-UHFFFAOYSA-N 0.000 claims 1
AOTAZZXZPBIYRK-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylcarbamoyl-methylamino]ethyl n-(1,3-benzothiazol-6-yl)carbamate Chemical compound C=1C=C2N=CSC2=CC=1NC(=O)OCCN(C)C(=O)NCC1=CC=CC=C1Cl AOTAZZXZPBIYRK-UHFFFAOYSA-N 0.000 claims 1
CCAHKADHVLDACM-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylcarbamoyl-methylamino]ethyl n-(1-phenylpyrazol-3-yl)carbamate Chemical compound C=1C=CC=C(Cl)C=1CNC(=O)N(C)CCOC(=O)NC(=N1)C=CN1C1=CC=CC=C1 CCAHKADHVLDACM-UHFFFAOYSA-N 0.000 claims 1
UFCSYLDSXDMCIX-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylcarbamoyl-methylamino]ethyl n-(4,5-dimethylpyridin-2-yl)carbamate Chemical compound C=1C=CC=C(Cl)C=1CNC(=O)N(C)CCOC(=O)NC1=CC(C)=C(C)C=N1 UFCSYLDSXDMCIX-UHFFFAOYSA-N 0.000 claims 1
JACDDCSEGQPKIZ-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylcarbamoyl-methylamino]ethyl n-(4-methyl-1,3-benzothiazol-2-yl)carbamate Chemical compound N=1C2=C(C)C=CC=C2SC=1NC(=O)OCCN(C)C(=O)NCC1=CC=CC=C1Cl JACDDCSEGQPKIZ-UHFFFAOYSA-N 0.000 claims 1
XTKDXRVHYHUSJV-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylcarbamoyl-methylamino]ethyl n-(5-acetylpyridin-2-yl)carbamate Chemical compound C=1C=CC=C(Cl)C=1CNC(=O)N(C)CCOC(=O)NC1=CC=C(C(C)=O)C=N1 XTKDXRVHYHUSJV-UHFFFAOYSA-N 0.000 claims 1
RUYSFGZOPLHFFD-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylcarbamoyl-methylamino]ethyl n-(5-bromopyrazin-2-yl)carbamate Chemical compound C=1C=CC=C(Cl)C=1CNC(=O)N(C)CCOC(=O)NC1=CN=C(Br)C=N1 RUYSFGZOPLHFFD-UHFFFAOYSA-N 0.000 claims 1
NMZNJOPWYFQSPO-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylcarbamoyl-methylamino]ethyl n-(5-bromopyrimidin-2-yl)carbamate Chemical compound C=1C=CC=C(Cl)C=1CNC(=O)N(C)CCOC(=O)NC1=NC=C(Br)C=N1 NMZNJOPWYFQSPO-UHFFFAOYSA-N 0.000 claims 1
IWYPQWOMLOSOLQ-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylcarbamoyl-methylamino]ethyl n-(5-chloropyridin-2-yl)carbamate Chemical compound C=1C=CC=C(Cl)C=1CNC(=O)N(C)CCOC(=O)NC1=CC=C(Cl)C=N1 IWYPQWOMLOSOLQ-UHFFFAOYSA-N 0.000 claims 1
BGFDNLNCVWGOQD-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylcarbamoyl-methylamino]ethyl n-(5-fluoro-4-methylpyridin-2-yl)carbamate Chemical compound C=1C=CC=C(Cl)C=1CNC(=O)N(C)CCOC(=O)NC1=CC(C)=C(F)C=N1 BGFDNLNCVWGOQD-UHFFFAOYSA-N 0.000 claims 1
ZUBOHQLVYOIWTE-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylcarbamoyl-methylamino]ethyl n-(5-methylpyrazin-2-yl)carbamate Chemical compound C=1C=CC=C(Cl)C=1CNC(=O)N(C)CCOC(=O)NC1=CN=C(C)C=N1 ZUBOHQLVYOIWTE-UHFFFAOYSA-N 0.000 claims 1
CQCSBLBTEKVHFH-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylcarbamoyl-methylamino]ethyl n-(6-methyl-1,3-benzothiazol-2-yl)carbamate Chemical compound N=1C2=CC=C(C)C=C2SC=1NC(=O)OCCN(C)C(=O)NCC1=CC=CC=C1Cl CQCSBLBTEKVHFH-UHFFFAOYSA-N 0.000 claims 1
TYZXRTQAFDLBGX-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylcarbamoyl-methylamino]ethyl n-(6-methylpyridin-3-yl)carbamate Chemical compound C=1C=CC=C(Cl)C=1CNC(=O)N(C)CCOC(=O)NC1=CC=C(C)N=C1 TYZXRTQAFDLBGX-UHFFFAOYSA-N 0.000 claims 1
FVVYHQQKJRFURB-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylcarbamoyl-methylamino]ethyl n-[5-(2-hydroxyethyl)pyridin-2-yl]carbamate Chemical compound C=1C=CC=C(Cl)C=1CNC(=O)N(C)CCOC(=O)NC1=CC=C(CCO)C=N1 FVVYHQQKJRFURB-UHFFFAOYSA-N 0.000 claims 1
SAOWFHFHEFXMAY-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylcarbamoyl-methylamino]ethyl n-[5-(2-hydroxypropan-2-yl)pyridin-2-yl]carbamate Chemical compound C=1C=CC=C(Cl)C=1CNC(=O)N(C)CCOC(=O)NC1=CC=C(C(C)(C)O)C=N1 SAOWFHFHEFXMAY-UHFFFAOYSA-N 0.000 claims 1
QQDLKSUPWDSHSA-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylcarbamoyl-methylamino]ethyl n-[5-(hydroxymethyl)pyridin-2-yl]carbamate Chemical compound C=1C=CC=C(Cl)C=1CNC(=O)N(C)CCOC(=O)NC1=CC=C(CO)C=N1 QQDLKSUPWDSHSA-UHFFFAOYSA-N 0.000 claims 1
UBEILMZSWSACTD-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylcarbamoyl-methylamino]ethyl n-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]carbamate Chemical compound C=1C=CC=C(Cl)C=1CNC(=O)N(C)CCOC(=O)NC1=NN=C(C(F)(F)F)S1 UBEILMZSWSACTD-UHFFFAOYSA-N 0.000 claims 1
OWNNXHSYYMNOIQ-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylcarbamoyl-methylamino]ethyl n-[6-(trifluoromethyl)pyridin-3-yl]carbamate Chemical compound C=1C=CC=C(Cl)C=1CNC(=O)N(C)CCOC(=O)NC1=CC=C(C(F)(F)F)N=C1 OWNNXHSYYMNOIQ-UHFFFAOYSA-N 0.000 claims 1
GOLMZVDRXLPEGZ-UHFFFAOYSA-N 2-[(5-bromo-2-chlorophenyl)methylcarbamoyl-methylamino]ethyl n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCN(C)C(=O)NCC1=CC(Br)=CC=C1Cl GOLMZVDRXLPEGZ-UHFFFAOYSA-N 0.000 claims 1
CGBPJTZAJVOEON-UHFFFAOYSA-N 2-[(5-chloro-2-fluorophenyl)methylcarbamoyl-methylamino]ethyl n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCN(C)C(=O)NCC1=CC(Cl)=CC=C1F CGBPJTZAJVOEON-UHFFFAOYSA-N 0.000 claims 1
VZGKIDHXZDOPIY-UHFFFAOYSA-N 2-[1-[(2-chloro-4-fluorophenyl)methyl]-3-methyl-2-oxopyrrolidin-3-yl]ethyl n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound O=C1C(C)(CCOC(=O)NC=2N=CC3=CC=C(F)C=C3C=2)CCN1CC1=CC=C(F)C=C1Cl VZGKIDHXZDOPIY-UHFFFAOYSA-N 0.000 claims 1
JQMYCUOWRQPMPH-UHFFFAOYSA-N 2-[2-(2-aminoethoxy)ethyl-[(2-chlorophenyl)methylcarbamoyl]amino]ethyl n-isoquinolin-3-ylcarbamate Chemical compound C=1C2=CC=CC=C2C=NC=1NC(=O)OCCN(CCOCCN)C(=O)NCC1=CC=CC=C1Cl JQMYCUOWRQPMPH-UHFFFAOYSA-N 0.000 claims 1
CXEWHLZCJXBRHL-LJQANCHMSA-N 2-[[(2R)-2-amino-3-hydroxypropyl]-[(2-chlorophenyl)methylcarbamoyl]amino]ethyl N-isoquinolin-3-ylcarbamate Chemical compound C=1C2=CC=CC=C2C=NC=1NC(=O)OCCN(C[C@H](CO)N)C(=O)NCC1=CC=CC=C1Cl CXEWHLZCJXBRHL-LJQANCHMSA-N 0.000 claims 1
JNDVNIPVVSXACP-UHFFFAOYSA-N 2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]ethyl N-[1-(trifluoromethyl)isoquinolin-3-yl]carbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)CCOC(=O)NC=1N=C(C2=CC=CC=C2C1)C(F)(F)F JNDVNIPVVSXACP-UHFFFAOYSA-N 0.000 claims 1
QPQVTEGRYLVQGM-UHFFFAOYSA-N 2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]ethyl n-(6-bromoisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(Br)=CC=C2C=NC=1NC(=O)OCCN(C(=O)C)NCC1=CC=CC(F)=C1Cl QPQVTEGRYLVQGM-UHFFFAOYSA-N 0.000 claims 1
MROZTJKFNSEYDT-UHFFFAOYSA-N 2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]ethyl n-(7-bromoisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC=C(Br)C=C2C=NC=1NC(=O)OCCN(C(=O)C)NCC1=CC=CC(F)=C1Cl MROZTJKFNSEYDT-UHFFFAOYSA-N 0.000 claims 1
JCMNWIHKBZFPLB-UHFFFAOYSA-N 2-[acetyl-[(2-chlorophenyl)methylamino]amino]ethyl N-(2,7-naphthyridin-3-yl)carbamate Chemical compound C=1C2=CC=NC=C2C=NC=1NC(=O)OCCN(C(=O)C)NCC1=CC=CC=C1Cl JCMNWIHKBZFPLB-UHFFFAOYSA-N 0.000 claims 1
IPOHMPUJMOUBAG-UHFFFAOYSA-N 2-[acetyl-[(2-chlorophenyl)methylamino]amino]ethyl N-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)carbamate Chemical compound ClC1=C(C=CC=C1)CNN(C(=O)C)CCOC(=O)NC=1SC2=C(N1)CCCC2 IPOHMPUJMOUBAG-UHFFFAOYSA-N 0.000 claims 1
BGSAVRBJQHOUCU-UHFFFAOYSA-N 2-[acetyl-[(2-chlorophenyl)methylamino]amino]ethyl N-(4-methylpyridin-2-yl)carbamate Chemical compound ClC1=C(C=CC=C1)CNN(C(=O)C)CCOC(=O)NC1=NC=CC(=C1)C BGSAVRBJQHOUCU-UHFFFAOYSA-N 0.000 claims 1
IBHSBZOFXCGNNV-UHFFFAOYSA-N 2-[acetyl-[(2-chlorophenyl)methylamino]amino]ethyl N-(5-cyanopyridin-2-yl)carbamate Chemical compound ClC1=C(C=CC=C1)CNN(C(=O)C)CCOC(=O)NC1=NC=C(C=C1)C#N IBHSBZOFXCGNNV-UHFFFAOYSA-N 0.000 claims 1
ILAIHYMDTSBMQL-UHFFFAOYSA-N 2-[acetyl-[(2-chlorophenyl)methylamino]amino]ethyl N-(5-ethenylpyridin-2-yl)carbamate Chemical compound ClC1=C(C=CC=C1)CNN(C(=O)C)CCOC(=O)NC1=NC=C(C=C1)C=C ILAIHYMDTSBMQL-UHFFFAOYSA-N 0.000 claims 1
UIZUJUNHBCQFRE-UHFFFAOYSA-N 2-[acetyl-[(2-chlorophenyl)methylamino]amino]ethyl N-(5-methyl-1,3-thiazol-2-yl)carbamate Chemical compound ClC1=C(C=CC=C1)CNN(C(=O)C)CCOC(=O)NC=1SC(=CN1)C UIZUJUNHBCQFRE-UHFFFAOYSA-N 0.000 claims 1
ZABHUZHVZNDIHH-UHFFFAOYSA-N 2-[acetyl-[(2-chlorophenyl)methylamino]amino]ethyl N-(5-methylpyridin-2-yl)carbamate Chemical compound ClC1=C(C=CC=C1)CNN(C(=O)C)CCOC(=O)NC1=NC=C(C=C1)C ZABHUZHVZNDIHH-UHFFFAOYSA-N 0.000 claims 1
AAXWNZIXHJYIGG-UHFFFAOYSA-N 2-[acetyl-[(2-chlorophenyl)methylamino]amino]ethyl N-(6-methylsulfonyl-1,3-benzothiazol-2-yl)carbamate Chemical compound ClC1=C(C=CC=C1)CNN(C(=O)C)CCOC(=O)NC=1SC2=C(N1)C=CC(=C2)S(=O)(=O)C AAXWNZIXHJYIGG-UHFFFAOYSA-N 0.000 claims 1
RAQSOCQBDWZSBT-UHFFFAOYSA-N 2-[acetyl-[(2-chlorophenyl)methylamino]amino]ethyl N-([1,3]thiazolo[5,4-b]pyridin-2-yl)carbamate Chemical compound ClC1=C(C=CC=C1)CNN(C(=O)C)CCOC(=O)NC=1SC2=NC=CC=C2N1 RAQSOCQBDWZSBT-UHFFFAOYSA-N 0.000 claims 1
PQRJTKYUAMGXBI-UHFFFAOYSA-N 2-[acetyl-[(2-chlorophenyl)methylamino]amino]ethyl N-isoquinolin-3-ylcarbamate Chemical compound ClC1=C(C=CC=C1)CNN(C(=O)C)CCOC(=O)NC=1N=CC2=CC=CC=C2C1 PQRJTKYUAMGXBI-UHFFFAOYSA-N 0.000 claims 1
SYEFEJQWRLNBOO-UHFFFAOYSA-N 2-[acetyl-[(2-chlorophenyl)methylamino]amino]ethyl N-pyridin-2-ylcarbamate Chemical compound ClC1=C(C=CC=C1)CNN(C(=O)C)CCOC(=O)NC1=NC=CC=C1 SYEFEJQWRLNBOO-UHFFFAOYSA-N 0.000 claims 1
XDAZMGXHTMRZAZ-UHFFFAOYSA-N 2-[acetyl-[(2-chlorophenyl)methylamino]amino]ethyl N-quinoxalin-2-ylcarbamate Chemical compound ClC1=C(C=CC=C1)CNN(C(=O)C)CCOC(=O)NC1=NC2=CC=CC=C2N=C1 XDAZMGXHTMRZAZ-UHFFFAOYSA-N 0.000 claims 1
DWSVXZFPAQNSNO-UHFFFAOYSA-N 2-[acetyl-[(2-chlorophenyl)methylamino]amino]ethyl n-(4,5-dimethyl-1,3-thiazol-2-yl)carbamate Chemical compound C=1C=CC=C(Cl)C=1CNN(C(=O)C)CCOC(=O)NC1=NC(C)=C(C)S1 DWSVXZFPAQNSNO-UHFFFAOYSA-N 0.000 claims 1
NHUMMAKMMUBQGK-UHFFFAOYSA-N 2-[acetyl-[(2-chlorophenyl)methylamino]amino]ethyl n-(4-methoxy-1,3-benzothiazol-2-yl)carbamate Chemical compound N=1C=2C(OC)=CC=CC=2SC=1NC(=O)OCCN(C(C)=O)NCC1=CC=CC=C1Cl NHUMMAKMMUBQGK-UHFFFAOYSA-N 0.000 claims 1
LRXFNFCEPWHJGJ-UHFFFAOYSA-N 2-[acetyl-[(2-chlorophenyl)methylamino]amino]ethyl n-(5,6-dichloro-1,3-benzothiazol-2-yl)carbamate Chemical compound N=1C2=CC(Cl)=C(Cl)C=C2SC=1NC(=O)OCCN(C(=O)C)NCC1=CC=CC=C1Cl LRXFNFCEPWHJGJ-UHFFFAOYSA-N 0.000 claims 1
CSYJJKHUAIXNNG-UHFFFAOYSA-N 2-[acetyl-[(2-chlorophenyl)methylamino]amino]ethyl n-(5,6-difluoro-1,3-benzothiazol-2-yl)carbamate Chemical compound N=1C2=CC(F)=C(F)C=C2SC=1NC(=O)OCCN(C(=O)C)NCC1=CC=CC=C1Cl CSYJJKHUAIXNNG-UHFFFAOYSA-N 0.000 claims 1
BVODPUOLBPZVHI-UHFFFAOYSA-N 2-[acetyl-[(2-chlorophenyl)methylamino]amino]ethyl n-(5,6-dimethyl-1,3-benzothiazol-2-yl)carbamate Chemical compound N=1C2=CC(C)=C(C)C=C2SC=1NC(=O)OCCN(C(=O)C)NCC1=CC=CC=C1Cl BVODPUOLBPZVHI-UHFFFAOYSA-N 0.000 claims 1
RGTOZODPNZJOBM-UHFFFAOYSA-N 2-[acetyl-[(2-chlorophenyl)methylamino]amino]ethyl n-(5-bromopyridin-2-yl)carbamate Chemical compound C=1C=CC=C(Cl)C=1CNN(C(=O)C)CCOC(=O)NC1=CC=C(Br)C=N1 RGTOZODPNZJOBM-UHFFFAOYSA-N 0.000 claims 1
DNNMTDMQPAUFRX-UHFFFAOYSA-N 2-[acetyl-[(2-chlorophenyl)methylamino]amino]ethyl n-(5-ethylpyridin-2-yl)carbamate Chemical compound N1=CC(CC)=CC=C1NC(=O)OCCN(C(C)=O)NCC1=CC=CC=C1Cl DNNMTDMQPAUFRX-UHFFFAOYSA-N 0.000 claims 1
UJFWHOZEPGZTMK-UHFFFAOYSA-N 2-[acetyl-[(2-chlorophenyl)methylamino]amino]ethyl n-(5-phenyl-1,3,4-oxadiazol-2-yl)carbamate Chemical compound C=1C=CC=C(Cl)C=1CNN(C(=O)C)CCOC(=O)NC(O1)=NN=C1C1=CC=CC=C1 UJFWHOZEPGZTMK-UHFFFAOYSA-N 0.000 claims 1
NVTFOYISZNYQGQ-UHFFFAOYSA-N 2-[acetyl-[(2-chlorophenyl)methylamino]amino]ethyl n-(6-methoxy-1,3-benzothiazol-2-yl)carbamate Chemical compound S1C2=CC(OC)=CC=C2N=C1NC(=O)OCCN(C(C)=O)NCC1=CC=CC=C1Cl NVTFOYISZNYQGQ-UHFFFAOYSA-N 0.000 claims 1
RRGXRSPQKJGJCE-UHFFFAOYSA-N 2-[acetyl-[(2-chlorophenyl)methylamino]amino]ethyl n-[5-(trifluoromethyl)pyridin-2-yl]carbamate Chemical compound C=1C=CC=C(Cl)C=1CNN(C(=O)C)CCOC(=O)NC1=CC=C(C(F)(F)F)C=N1 RRGXRSPQKJGJCE-UHFFFAOYSA-N 0.000 claims 1
KCOKGNZYUPVSOQ-UHFFFAOYSA-N 2-[acetyl-[(2-chlorophenyl)methylamino]amino]ethyl n-[6-(trifluoromethyl)-1,3-benzothiazol-2-yl]carbamate Chemical compound N=1C2=CC=C(C(F)(F)F)C=C2SC=1NC(=O)OCCN(C(=O)C)NCC1=CC=CC=C1Cl KCOKGNZYUPVSOQ-UHFFFAOYSA-N 0.000 claims 1
GWQNUDJPKHTJQD-UHFFFAOYSA-N 2-[benzylcarbamoyl(methyl)amino]ethyl n-(5-ethylpyridin-2-yl)carbamate Chemical compound N1=CC(CC)=CC=C1NC(=O)OCCN(C)C(=O)NCC1=CC=CC=C1 GWQNUDJPKHTJQD-UHFFFAOYSA-N 0.000 claims 1
ULPUWBNARFWSSQ-UHFFFAOYSA-N 2-methylpentyl dihydrogen phosphate Chemical compound CCCC(C)COP(O)(O)=O ULPUWBNARFWSSQ-UHFFFAOYSA-N 0.000 claims 1
125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 1
CQTKCUDXZKGASB-UHFFFAOYSA-N 3-(3-fluorophenyl)-1,2-oxazole Chemical compound FC1=CC=CC(C2=NOC=C2)=C1 CQTKCUDXZKGASB-UHFFFAOYSA-N 0.000 claims 1
DTBDAFLSBDGPEA-UHFFFAOYSA-N 3-Methylquinoline Natural products C1=CC=CC2=CC(C)=CN=C21 DTBDAFLSBDGPEA-UHFFFAOYSA-N 0.000 claims 1
NPNCDCLUYRJANH-UHFFFAOYSA-N 3-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]butan-2-yl n-isoquinolin-3-ylcarbamate Chemical compound C=1C2=CC=CC=C2C=NC=1NC(=O)OC(C)C(C)N(C)C(=O)NCC1=CC=CC(F)=C1Cl NPNCDCLUYRJANH-UHFFFAOYSA-N 0.000 claims 1
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
JLAKCHGEEBPDQI-UHFFFAOYSA-N 4-(4-fluorobenzyl)piperidine Chemical compound C1=CC(F)=CC=C1CC1CCNCC1 JLAKCHGEEBPDQI-UHFFFAOYSA-N 0.000 claims 1
JQRDUBYISJYKBW-QHCPKHFHSA-N 4-[(5s)-5-[acetyl-[(2,3-difluorophenyl)methylamino]amino]-6-(isoquinolin-3-ylcarbamoyloxy)hexoxy]-4-oxobutanoic acid Chemical compound CC(=O)N([C@@H](CCCCOC(=O)CCC(O)=O)COC(=O)NC=1N=CC2=CC=CC=C2C=1)NCC1=CC=CC(F)=C1F JQRDUBYISJYKBW-QHCPKHFHSA-N 0.000 claims 1
VSPMAHXVUGOFMD-UHFFFAOYSA-N 4-benzoylbenzamide Chemical compound C1=CC(C(=O)N)=CC=C1C(=O)C1=CC=CC=C1 VSPMAHXVUGOFMD-UHFFFAOYSA-N 0.000 claims 1
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
PWFLAHNAMVDOQT-UHFFFAOYSA-N 6,8-dihydro-5h-imidazo[1,5-a]pyrazine-7-carboxylic acid Chemical compound C1N(C(=O)O)CCN2C=NC=C21 PWFLAHNAMVDOQT-UHFFFAOYSA-N 0.000 claims 1
206010006482 Bronchospasm Diseases 0.000 claims 1
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 1
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
208000010228 Erectile Dysfunction Diseases 0.000 claims 1
208000030644 Esophageal Motility disease Diseases 0.000 claims 1
208000010412 Glaucoma Diseases 0.000 claims 1
206010020772 Hypertension Diseases 0.000 claims 1
206010021639 Incontinence Diseases 0.000 claims 1
239000004727 Noryl Substances 0.000 claims 1
229920001207 Noryl Polymers 0.000 claims 1
208000014934 Oesophageal motility disease Diseases 0.000 claims 1
208000033045 Premenstrual cramps Diseases 0.000 claims 1
208000006011 Stroke Diseases 0.000 claims 1
208000032851 Subarachnoid Hemorrhage Diseases 0.000 claims 1
YPYNHPMDBPZDTB-FGZHOGPDSA-N [(1r,2r)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-ethylamino]cyclohexyl] n-isoquinolin-3-ylcarbamate Chemical compound CCN([C@H]1[C@@H](CCCC1)OC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl YPYNHPMDBPZDTB-FGZHOGPDSA-N 0.000 claims 1
ZTPBYLNADYFKAZ-UXHICEINSA-N [(1s,2r)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]cyclopentyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@H]1[C@H](CCC1)OC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl ZTPBYLNADYFKAZ-UXHICEINSA-N 0.000 claims 1
SEFLCZWBGLVSKY-SFTDATJTSA-N [(1s,2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]cyclohexyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H]1[C@H](CCCC1)OC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl SEFLCZWBGLVSKY-SFTDATJTSA-N 0.000 claims 1
LIEXWVDNCVCNAK-WOJBJXKFSA-N [(2R)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-3-[(4R)-2-oxo-1,3-dioxolan-4-yl]propyl] N-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound O=C1OC[C@H](O1)C[C@H](COC(=O)NC=1N=CC2=CC=C(C=C2C1)F)N(C(=O)C)NCC1=C(C(=CC=C1)F)Cl LIEXWVDNCVCNAK-WOJBJXKFSA-N 0.000 claims 1
QNHVVKICMVUVOS-HSZRJFAPSA-N [(2R)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-oxo-5-piperazin-1-ylpentyl] N-isoquinolin-3-ylcarbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@@H](COC(=O)NC=1N=CC2=CC=CC=C2C1)CCC(N1CCNCC1)=O QNHVVKICMVUVOS-HSZRJFAPSA-N 0.000 claims 1
WUJONBMBDGEVKC-WOJBJXKFSA-N [(2R,4R)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4,5-dihydroxypentyl] N-isoquinolin-3-ylcarbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@@H](COC(=O)NC=1N=CC2=CC=CC=C2C1)C[C@H](CO)O WUJONBMBDGEVKC-WOJBJXKFSA-N 0.000 claims 1
LGAPYFJAIAQASB-FQEVSTJZSA-N [(2S)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-isocyanatopentyl] N-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound ClC1=C(C=CC=C1F)CNC(=O)N(C)[C@@H](CCCN=C=O)COC(NC=1N=CC2=CC=C(C=C2C1)F)=O LGAPYFJAIAQASB-FQEVSTJZSA-N 0.000 claims 1
DVHIZTWVDZBSSB-QFIPXVFZSA-N [(2S)-2-[acetyl-[(2,3-difluorophenyl)methylamino]amino]-4-oxo-4-piperazin-1-ylbutyl] N-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound FC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=C(C=C2C1)F)CC(N1CCNCC1)=O DVHIZTWVDZBSSB-QFIPXVFZSA-N 0.000 claims 1
ACKBWIKQKXBRMZ-QFIPXVFZSA-N [(2S)-2-[acetyl-[(2,3-difluorophenyl)methylamino]amino]-4-oxo-4-piperazin-1-ylbutyl] N-isoquinolin-3-ylcarbamate Chemical compound FC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)CC(N1CCNCC1)=O ACKBWIKQKXBRMZ-QFIPXVFZSA-N 0.000 claims 1
GRCPZCPJLWJTIB-QFIPXVFZSA-N [(2S)-2-[acetyl-[(2,3-difluorophenyl)methylamino]amino]-5-oxo-5-piperazin-1-ylpentyl] N-(3-phenyl-1,2-oxazol-5-yl)carbamate Chemical compound FC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC1=CC(=NO1)C1=CC=CC=C1)CCC(N1CCNCC1)=O GRCPZCPJLWJTIB-QFIPXVFZSA-N 0.000 claims 1
RBTYAHJPVMRMDJ-NRFANRHFSA-N [(2S)-2-[acetyl-[(2,3-difluorophenyl)methylamino]amino]-6-hydroxyhexyl] N-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound FC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=C(C=C2C1)F)CCCCO RBTYAHJPVMRMDJ-NRFANRHFSA-N 0.000 claims 1
MFHNHXGTAAARLF-QFIPXVFZSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-3-(1-methylimidazol-4-yl)propyl] N-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=C(C=C2C1)F)CC=1N=CN(C1)C MFHNHXGTAAARLF-QFIPXVFZSA-N 0.000 claims 1
NLHYBUWVSPNJIB-IBGZPJMESA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-3-(2,2,2-trifluoroethylamino)propyl] N-isoquinolin-3-ylcarbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=CC=C2C1)CNCC(F)(F)F NLHYBUWVSPNJIB-IBGZPJMESA-N 0.000 claims 1
XXSGOQATBGMCSA-FQEVSTJZSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-3-(2-fluoroethylamino)propyl] N-isoquinolin-3-ylcarbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=CC=C2C1)CNCCF XXSGOQATBGMCSA-FQEVSTJZSA-N 0.000 claims 1
UESZZPMVDWUWSO-FQEVSTJZSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-3-(2-hydroxyethylamino)propyl] N-isoquinolin-3-ylcarbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=CC=C2C1)CNCCO UESZZPMVDWUWSO-FQEVSTJZSA-N 0.000 claims 1
JMGOXNADEVCJDS-NRFANRHFSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-3-[(2-hydroxy-2-methylpropyl)amino]propyl] N-isoquinolin-3-ylcarbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=CC=C2C1)CNCC(C)(C)O JMGOXNADEVCJDS-NRFANRHFSA-N 0.000 claims 1
PHMYILWCAYIFRF-KRWDZBQOSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-3-aminopropyl] N-(5-phenyl-1,2-oxazol-3-yl)carbamate Chemical compound NC[C@@H](COC(=O)NC1=NOC(=C1)C1=CC=CC=C1)N(C(=O)C)NCC1=C(C(=CC=C1)F)Cl PHMYILWCAYIFRF-KRWDZBQOSA-N 0.000 claims 1
BCXRMGAQNNSRPU-QHCPKHFHSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-3-pyridin-2-ylpropyl] N-isoquinolin-3-ylcarbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=CC=C2C1)CC1=NC=CC=C1 BCXRMGAQNNSRPU-QHCPKHFHSA-N 0.000 claims 1
DDHMQNOGYUZPSA-IBGZPJMESA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4-aminobutyl] N-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound NCC[C@@H](COC(=O)NC=1N=CC2=CC=C(C=C2C1)F)N(C(=O)C)NCC1=C(C(=CC=C1)F)Cl DDHMQNOGYUZPSA-IBGZPJMESA-N 0.000 claims 1
GCOJLUYIYYULQR-SFHVURJKSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4-hydroxy-4-methylpentyl] N-(5-fluoroisoquinolin-3-yl)carbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=CC(=C2C1)F)CC(C)(C)O GCOJLUYIYYULQR-SFHVURJKSA-N 0.000 claims 1
FOHCSOSWYQKOOM-FQEVSTJZSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4-hydroxy-4-methylpentyl] N-(7-fluoroisoquinolin-3-yl)carbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC(=CC=C2C1)F)CC(C)(C)O FOHCSOSWYQKOOM-FQEVSTJZSA-N 0.000 claims 1
AWRUHELYGYHBLP-QFIPXVFZSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4-oxo-4-piperazin-1-ylbutyl] N-isoquinolin-3-ylcarbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=CC=C2C1)CC(N1CCNCC1)=O AWRUHELYGYHBLP-QFIPXVFZSA-N 0.000 claims 1
QFGOCCNJVZVATI-SANMLTNESA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-(4-cyclopropylpiperazin-1-yl)-5-oxopentyl] N-isoquinolin-3-ylcarbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=CC=C2C1)CCC(=O)N1CCN(CC1)C1CC1 QFGOCCNJVZVATI-SANMLTNESA-N 0.000 claims 1
IMGBIAHHLODVRU-QHCPKHFHSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-(4-methylpiperazin-1-yl)-5-oxopentyl] N-(3-phenyl-1,2-oxazol-5-yl)carbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC1=CC(=NO1)C1=CC=CC=C1)CCC(=O)N1CCN(CC1)C IMGBIAHHLODVRU-QHCPKHFHSA-N 0.000 claims 1
OXLZINBYPSTAHG-QHCPKHFHSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-(4-methylpiperazin-1-yl)-5-oxopentyl] N-[3-(3-fluorophenyl)-1,2-oxazol-5-yl]carbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC1=CC(=NO1)C1=CC(=CC=C1)F)CCC(=O)N1CCN(CC1)C OXLZINBYPSTAHG-QHCPKHFHSA-N 0.000 claims 1
NVGRIEPXZLHPSP-QHCPKHFHSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-(6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl)-5-oxopentyl] N-isoquinolin-3-ylcarbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=CC=C2C1)CCC(N1CC=2N(CC1)C=NN2)=O NVGRIEPXZLHPSP-QHCPKHFHSA-N 0.000 claims 1
MNHPXJYVDJLBPL-DEOSSOPVSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-(6,8-dihydro-5H-imidazo[1,2-a]pyrazin-7-yl)-5-oxopentyl] N-isoquinolin-3-ylcarbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=CC=C2C1)CCC(=O)N1CC=2N(CC1)C=CN2 MNHPXJYVDJLBPL-DEOSSOPVSA-N 0.000 claims 1
QNNMTZMKOJIWBU-DVECYGJZSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-[(2R)-2-methylpiperazin-1-yl]-5-oxopentyl] N-isoquinolin-3-ylcarbamate Chemical compound C[C@@H]1CNCCN1C(=O)CC[C@H](N(NCC=1C(=C(F)C=CC=1)Cl)C(C)=O)COC(=O)NC1=CC2=CC=CC=C2C=N1 QNNMTZMKOJIWBU-DVECYGJZSA-N 0.000 claims 1
QNNMTZMKOJIWBU-CYFREDJKSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-[(2S)-2-methylpiperazin-1-yl]-5-oxopentyl] N-isoquinolin-3-ylcarbamate Chemical compound C[C@@H]1N(CCNC1)C(CC[C@@H](COC(=O)NC=1N=CC2=CC=CC=C2C1)N(C(=O)C)NCC1=C(C(=CC=C1)F)Cl)=O QNNMTZMKOJIWBU-CYFREDJKSA-N 0.000 claims 1
ULUQHAMEOHXUCG-DVECYGJZSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-[(3R)-3-methylpiperazin-1-yl]-5-oxopentyl] N-isoquinolin-3-ylcarbamate Chemical compound C[C@@H]1CN(CCN1)C(CC[C@@H](COC(=O)NC=1N=CC2=CC=CC=C2C1)N(C(=O)C)NCC1=C(C(=CC=C1)F)Cl)=O ULUQHAMEOHXUCG-DVECYGJZSA-N 0.000 claims 1
BKAQVTLKTHGTQD-DFIYOIEZSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-[(3S,5R)-3,5-dimethylpiperazin-1-yl]-5-oxopentyl] N-isoquinolin-3-ylcarbamate Chemical compound C[C@H]1CN(C[C@H](N1)C)C(CC[C@@H](COC(=O)NC=1N=CC2=CC=CC=C2C1)N(C(=O)C)NCC1=C(C(=CC=C1)F)Cl)=O BKAQVTLKTHGTQD-DFIYOIEZSA-N 0.000 claims 1
ADDHBBGNZUQSJN-VWLOTQADSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-[4-(2-hydroxyethyl)piperazin-1-yl]-5-oxopentyl] N-isoquinolin-3-ylcarbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=CC=C2C1)CCC(=O)N1CCN(CC1)CCO ADDHBBGNZUQSJN-VWLOTQADSA-N 0.000 claims 1
BNPAOHJNWPHWRJ-FQEVSTJZSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-hydrazinylpentyl] N-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@@H](CCCNN)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)NCC1=CC=CC(F)=C1Cl BNPAOHJNWPHWRJ-FQEVSTJZSA-N 0.000 claims 1
HRISXMXRUMHXPF-NRFANRHFSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-hydroxy-4,4-dimethylpentyl] N-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=C(C=C2C1)F)CC(CO)(C)C HRISXMXRUMHXPF-NRFANRHFSA-N 0.000 claims 1
KKACBKDSHAWVPA-NRFANRHFSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-hydroxy-4,4-dimethylpentyl] N-isoquinolin-3-ylcarbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=CC=C2C1)CC(CO)(C)C KKACBKDSHAWVPA-NRFANRHFSA-N 0.000 claims 1
VYGLLGCOLIUZQD-VWLOTQADSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-oxo-5-(4-propan-2-ylpiperazin-1-yl)pentyl] N-(3-phenyl-1,2-oxazol-5-yl)carbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC1=CC(=NO1)C1=CC=CC=C1)CCC(=O)N1CCN(CC1)C(C)C VYGLLGCOLIUZQD-VWLOTQADSA-N 0.000 claims 1
QQLVFYQLTWMAJU-VWLOTQADSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-oxo-5-(4-propan-2-ylpiperazin-1-yl)pentyl] N-(5-phenyl-1,2-oxazol-3-yl)carbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC1=NOC(=C1)C1=CC=CC=C1)CCC(=O)N1CCN(CC1)C(C)C QQLVFYQLTWMAJU-VWLOTQADSA-N 0.000 claims 1
SINNIMHCRVOPLY-VWLOTQADSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-oxo-5-(4-propan-2-ylpiperazin-1-yl)pentyl] N-[3-(3-fluorophenyl)-1,2-oxazol-5-yl]carbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC1=CC(=NO1)C1=CC(=CC=C1)F)CCC(=O)N1CCN(CC1)C(C)C SINNIMHCRVOPLY-VWLOTQADSA-N 0.000 claims 1
IEZYJDGESNKQNB-VWLOTQADSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-oxo-5-(4-propan-2-ylpiperazin-1-yl)pentyl] N-[5-(3-fluorophenyl)-1,2-oxazol-3-yl]carbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC1=NOC(=C1)C1=CC(=CC=C1)F)CCC(=O)N1CCN(CC1)C(C)C IEZYJDGESNKQNB-VWLOTQADSA-N 0.000 claims 1
AWWUMJKMFVMAMC-SANMLTNESA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-oxo-5-(4-propan-2-ylpiperazin-1-yl)pentyl] N-isoquinolin-3-ylcarbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=CC=C2C1)CCC(=O)N1CCN(CC1)C(C)C AWWUMJKMFVMAMC-SANMLTNESA-N 0.000 claims 1
SKQVRKWBGPCXIS-QFIPXVFZSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-oxo-5-piperazin-1-ylpentyl] N-[3-(3-fluorophenyl)-1,2-oxazol-5-yl]carbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC1=CC(=NO1)C1=CC(=CC=C1)F)CCC(N1CCNCC1)=O SKQVRKWBGPCXIS-QFIPXVFZSA-N 0.000 claims 1
PSEANGVMDQTEPX-QFIPXVFZSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-oxo-5-piperazin-1-ylpentyl] N-[5-(3-fluorophenyl)-1,2-oxazol-3-yl]carbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC1=NOC(=C1)C1=CC(=CC=C1)F)CCC(N1CCNCC1)=O PSEANGVMDQTEPX-QFIPXVFZSA-N 0.000 claims 1
QNHVVKICMVUVOS-QHCPKHFHSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-oxo-5-piperazin-1-ylpentyl] N-isoquinolin-3-ylcarbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=CC=C2C1)CCC(N1CCNCC1)=O QNHVVKICMVUVOS-QHCPKHFHSA-N 0.000 claims 1
ICDWVTCJYMLLJC-INIZCTEOSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]pent-4-enyl] N-(5-chloropyridin-2-yl)carbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC1=NC=C(C=C1)Cl)CC=C ICDWVTCJYMLLJC-INIZCTEOSA-N 0.000 claims 1
QYZLTONMERJURR-FQEVSTJZSA-N [(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]pent-4-enyl] N-isoquinolin-3-ylcarbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=CC=C2C1)CC=C QYZLTONMERJURR-FQEVSTJZSA-N 0.000 claims 1
URKPWFMYRUPPDS-IBGZPJMESA-N [(2S)-2-[acetyl-[(2-chloro-4-fluorophenyl)methylamino]amino]-4-hydroxy-4-methylpentyl] N-(5-fluoroisoquinolin-3-yl)carbamate Chemical compound ClC1=C(C=CC(=C1)F)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=CC(=C2C1)F)CC(C)(C)O URKPWFMYRUPPDS-IBGZPJMESA-N 0.000 claims 1
NTSAOCFTVFLANP-JOCHJYFZSA-N [(2S)-2-[acetyl-[(2-chlorophenyl)methylamino]amino]-3-methylbutyl] N-isoquinolin-3-ylcarbamate Chemical compound ClC1=C(C=CC=C1)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=CC=C2C1)C(C)C NTSAOCFTVFLANP-JOCHJYFZSA-N 0.000 claims 1
YWGLYMABEOVCCH-IBGZPJMESA-N [(2S)-2-[acetyl-[(2-chlorophenyl)methylamino]amino]-4-hydroxy-4-methylpentyl] N-(5-fluoroisoquinolin-3-yl)carbamate Chemical compound ClC1=C(C=CC=C1)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=CC(=C2C1)F)CC(C)(C)O YWGLYMABEOVCCH-IBGZPJMESA-N 0.000 claims 1
KNNHWWREMUPKAF-IBGZPJMESA-N [(2S)-2-[acetyl-[(2-chlorophenyl)methylamino]amino]-4-methylpentyl] N-(6-methyl-1,3-benzothiazol-2-yl)carbamate Chemical compound ClC1=C(C=CC=C1)CNN(C(=O)C)[C@H](COC(=O)NC=1SC2=C(N1)C=CC(=C2)C)CC(C)C KNNHWWREMUPKAF-IBGZPJMESA-N 0.000 claims 1
ZJNJARNMTRCKJF-NRFANRHFSA-N [(2S)-2-[acetyl-[(2-chlorophenyl)methylamino]amino]-5-aminopentyl] N-isoquinolin-3-ylcarbamate Chemical compound NCCC[C@@H](COC(=O)NC=1N=CC2=CC=CC=C2C1)N(C(=O)C)NCC1=C(C=CC=C1)Cl ZJNJARNMTRCKJF-NRFANRHFSA-N 0.000 claims 1
FVAZQWFNOJTCPG-QFIPXVFZSA-N [(2S)-2-[acetyl-[(2-chlorophenyl)methylamino]amino]-6-[(2-diazo-3,3,3-trifluoropropanoyl)amino]hexyl] N-isoquinolin-3-ylcarbamate Chemical compound CC(=O)N(NCc1ccccc1Cl)[C@@H](CCCCNC(=O)C(=[N+]=[N-])C(F)(F)F)COC(=O)Nc1cc2ccccc2cn1 FVAZQWFNOJTCPG-QFIPXVFZSA-N 0.000 claims 1
AULLRWXPLFNIFH-FQEVSTJZSA-N [(2S)-2-[acetyl-[(3-fluorophenyl)methylamino]amino]-3-aminopropyl] N-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@@H](CN)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)NCC1=CC=CC(F)=C1 AULLRWXPLFNIFH-FQEVSTJZSA-N 0.000 claims 1
NYQPTBDDQQHCOR-HMTLIYDFSA-N [(2S)-2-[acetyl-[(3-fluorophenyl)methylamino]amino]-4,5-dihydroxypentyl] N-isoquinolin-3-ylcarbamate Chemical compound FC=1C=C(C=CC1)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=CC=C2C1)CC(CO)O NYQPTBDDQQHCOR-HMTLIYDFSA-N 0.000 claims 1
LWXZREGKVGWIJG-JKSUJKDBSA-N [(2S,4R)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4,5-dihydroxypentyl] N-(1,3-benzothiazol-2-yl)carbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1SC2=C(N1)C=CC=C2)C[C@H](CO)O LWXZREGKVGWIJG-JKSUJKDBSA-N 0.000 claims 1
ZVROFHCWQAMMLR-UONOGXRCSA-N [(2S,4R)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4,5-dihydroxypentyl] N-(5,6-difluoro-1,3-benzothiazol-2-yl)carbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1SC2=C(N1)C=C(C(=C2)F)F)C[C@H](CO)O ZVROFHCWQAMMLR-UONOGXRCSA-N 0.000 claims 1
NLFKCIXQJKSWAW-ZWKOTPCHSA-N [(2S,4R)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4,5-dihydroxypentyl] N-(5,6-dimethyl-1,3-benzothiazol-2-yl)carbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1SC2=C(N1)C=C(C(=C2)C)C)C[C@H](CO)O NLFKCIXQJKSWAW-ZWKOTPCHSA-N 0.000 claims 1
DNGGBLXHIFARSQ-JKSUJKDBSA-N [(2S,4R)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4,5-dihydroxypentyl] N-(6-fluoro-1,3-benzothiazol-2-yl)carbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1SC2=C(N1)C=CC(=C2)F)C[C@H](CO)O DNGGBLXHIFARSQ-JKSUJKDBSA-N 0.000 claims 1
OWWSZDYBDFFHEK-DLBZAZTESA-N [(2S,4R)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4,5-dihydroxypentyl] N-(6-methyl-1,3-benzothiazol-2-yl)carbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1SC2=C(N1)C=CC(=C2)C)C[C@H](CO)O OWWSZDYBDFFHEK-DLBZAZTESA-N 0.000 claims 1
WUJONBMBDGEVKC-VQTJNVASSA-N [(2S,4R)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4,5-dihydroxypentyl] N-isoquinolin-3-ylcarbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=CC=C2C1)C[C@H](CO)O WUJONBMBDGEVKC-VQTJNVASSA-N 0.000 claims 1
WUJONBMBDGEVKC-PMACEKPBSA-N [(2S,4S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4,5-dihydroxypentyl] N-isoquinolin-3-ylcarbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=CC=C2C1)C[C@@H](CO)O WUJONBMBDGEVKC-PMACEKPBSA-N 0.000 claims 1
LMGWOYLAYVVJGR-OAHLLOKOSA-N [(2r)-2-[acetyl-[(2-chlorophenyl)methylamino]amino]propyl] n-isoquinolin-3-ylcarbamate Chemical compound CC(=O)N([C@@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)C)NCC1=CC=CC=C1Cl LMGWOYLAYVVJGR-OAHLLOKOSA-N 0.000 claims 1
VQGVPNKQIIOIOO-WOJBJXKFSA-N [(2r,4r)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4-hydroxy-5-phosphonooxypentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C[C@@H](O)COP(O)(O)=O)NCC1=CC=CC(F)=C1Cl VQGVPNKQIIOIOO-WOJBJXKFSA-N 0.000 claims 1
OLYRUYIFLZDDBM-DNQXCXABSA-N [(2r,4r)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-diethoxyphosphoryloxy-4-hydroxypentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C[C@@H](O)COP(=O)(OCC)OCC)NCC1=CC=CC(F)=C1Cl OLYRUYIFLZDDBM-DNQXCXABSA-N 0.000 claims 1
VQGVPNKQIIOIOO-UXHICEINSA-N [(2r,4s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4-hydroxy-5-phosphonooxypentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C[C@H](O)COP(O)(O)=O)NCC1=CC=CC(F)=C1Cl VQGVPNKQIIOIOO-UXHICEINSA-N 0.000 claims 1
OLYRUYIFLZDDBM-RPWUZVMVSA-N [(2r,4s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-diethoxyphosphoryloxy-4-hydroxypentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C[C@H](O)COP(=O)(OCC)OCC)NCC1=CC=CC(F)=C1Cl OLYRUYIFLZDDBM-RPWUZVMVSA-N 0.000 claims 1
YCYCIIZNBZOQLM-NRFANRHFSA-N [(2s)-2-[(2,3-dichlorophenyl)methylcarbamoyl-methylamino]-6-hydroxy-6-methylheptyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](CCCC(C)(C)O)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=CC(Cl)=C1Cl YCYCIIZNBZOQLM-NRFANRHFSA-N 0.000 claims 1
YUXNFSUBCOIOGR-FQEVSTJZSA-N [(2s)-2-[(2,3-dichlorophenyl)methylcarbamoyl-methylamino]-6-hydroxyhexyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](CCCCO)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=CC(Cl)=C1Cl YUXNFSUBCOIOGR-FQEVSTJZSA-N 0.000 claims 1
ITMFPKQIICKDME-PMACEKPBSA-N [(2s)-2-[(2,3-difluorophenyl)methylcarbamoyl-methylamino]-3-[(2s)-2,3-dihydroxypropoxy]propyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](COC[C@@H](O)CO)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=CC(F)=C1F ITMFPKQIICKDME-PMACEKPBSA-N 0.000 claims 1
YYXFPQKDUGLWEV-VQTJNVASSA-N [(2s)-2-[(2,3-difluorophenyl)methylcarbamoyl-methylamino]-3-[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]propyl] n-(5-phenyl-1,2-oxazol-3-yl)carbamate Chemical compound C([C@@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)F)C[C@H]1OC(C)(C)OC1)OC(=O)NC(=NO1)C=C1C1=CC=CC=C1 YYXFPQKDUGLWEV-VQTJNVASSA-N 0.000 claims 1
ROTUDUXNMAFJHG-LEWJYISDSA-N [(2s)-2-[(2,3-difluorophenyl)methylcarbamoyl-methylamino]-3-[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]propyl] n-isoquinolin-3-ylcarbamate Chemical compound C([C@@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)N(C)C(=O)NCC=1C(=C(F)C=CC=1)F)[C@@H]1COC(C)(C)O1 ROTUDUXNMAFJHG-LEWJYISDSA-N 0.000 claims 1
POQOKRRETJRPHT-OYKVQYDMSA-N [(2s)-2-[(2,3-difluorophenyl)methylcarbamoyl-methylamino]-4,5-dihydroxypentyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)CC(O)CO)C(=O)NCC1=CC=CC(F)=C1F POQOKRRETJRPHT-OYKVQYDMSA-N 0.000 claims 1
LCJNNTQWQOIDPX-IBGZPJMESA-N [(2s)-2-[(2,3-difluorophenyl)methylcarbamoyl-methylamino]-5-hydroxypentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@@H](CCCO)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C(=O)NCC1=CC=CC(F)=C1F LCJNNTQWQOIDPX-IBGZPJMESA-N 0.000 claims 1
KTCPZIDFBSASSE-IBGZPJMESA-N [(2s)-2-[(2,3-difluorophenyl)methylcarbamoyl-methylamino]-5-hydroxypentyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](CCCO)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=CC(F)=C1F KTCPZIDFBSASSE-IBGZPJMESA-N 0.000 claims 1
ULPSRCNZMUWRSA-QFIPXVFZSA-N [(2s)-2-[(2,3-difluorophenyl)methylcarbamoyl-methylamino]-5-oxo-5-piperazin-1-ylpentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C([C@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)F)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CC(=O)N1CCNCC1 ULPSRCNZMUWRSA-QFIPXVFZSA-N 0.000 claims 1
HQDPVLBJCJOOPF-QFIPXVFZSA-N [(2s)-2-[(2,3-difluorophenyl)methylcarbamoyl-methylamino]-5-oxo-5-piperazin-1-ylpentyl] n-isoquinolin-3-ylcarbamate Chemical compound C([C@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)F)COC(=O)NC=1N=CC2=CC=CC=C2C=1)CC(=O)N1CCNCC1 HQDPVLBJCJOOPF-QFIPXVFZSA-N 0.000 claims 1
GPXLZGYBJVSMSO-NRFANRHFSA-N [(2s)-2-[(2,3-difluorophenyl)methylcarbamoyl-methylamino]-6-hydroxy-6-methylheptyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](CCCC(C)(C)O)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=CC(F)=C1F GPXLZGYBJVSMSO-NRFANRHFSA-N 0.000 claims 1
XBRMGMITPOXTQD-IBGZPJMESA-N [(2s)-2-[(2,3-difluorophenyl)methylcarbamoyl-methylamino]-6-hydroxyhexyl] n-(5-phenyl-1,2-oxazol-3-yl)carbamate Chemical compound C([C@H](CCCCO)N(C)C(=O)NCC=1C(=C(F)C=CC=1)F)OC(=O)NC(=NO1)C=C1C1=CC=CC=C1 XBRMGMITPOXTQD-IBGZPJMESA-N 0.000 claims 1
DVDJXFLTWGTZON-IBGZPJMESA-N [(2s)-2-[(2,3-difluorophenyl)methylcarbamoyl-methylamino]-6-hydroxyhexyl] n-[3-(4-bromophenyl)-1,2-oxazol-5-yl]carbamate Chemical compound C([C@H](CCCCO)N(C)C(=O)NCC=1C(=C(F)C=CC=1)F)OC(=O)NC(ON=1)=CC=1C1=CC=C(Br)C=C1 DVDJXFLTWGTZON-IBGZPJMESA-N 0.000 claims 1
RRLIVPZHHZKSDI-FQEVSTJZSA-N [(2s)-2-[(2,3-difluorophenyl)methylcarbamoyl-methylamino]-6-hydroxyhexyl] n-[3-(4-cyanophenyl)-1,2-oxazol-5-yl]carbamate Chemical compound C([C@H](CCCCO)N(C)C(=O)NCC=1C(=C(F)C=CC=1)F)OC(=O)NC(ON=1)=CC=1C1=CC=C(C#N)C=C1 RRLIVPZHHZKSDI-FQEVSTJZSA-N 0.000 claims 1
OYYQWXXFQQNIMO-IBGZPJMESA-N [(2s)-2-[(2,3-difluorophenyl)methylcarbamoyl-methylamino]-6-hydroxyhexyl] n-[5-(3-chlorophenyl)-1,2-oxazol-3-yl]carbamate Chemical compound C([C@H](CCCCO)N(C)C(=O)NCC=1C(=C(F)C=CC=1)F)OC(=O)NC(=NO1)C=C1C1=CC=CC(Cl)=C1 OYYQWXXFQQNIMO-IBGZPJMESA-N 0.000 claims 1
ZPYQHRVQJCOZIH-IBGZPJMESA-N [(2s)-2-[(2,3-difluorophenyl)methylcarbamoyl-methylamino]-6-hydroxyhexyl] n-[5-(3-fluorophenyl)-1,2-oxazol-3-yl]carbamate Chemical compound C([C@H](CCCCO)N(C)C(=O)NCC=1C(=C(F)C=CC=1)F)OC(=O)NC(=NO1)C=C1C1=CC=CC(F)=C1 ZPYQHRVQJCOZIH-IBGZPJMESA-N 0.000 claims 1
CJMBYNKZUOOONJ-IBGZPJMESA-N [(2s)-2-[(2,3-difluorophenyl)methylcarbamoyl-methylamino]-6-hydroxyhexyl] n-[5-(4-chlorophenyl)-1,2-oxazol-3-yl]carbamate Chemical compound C([C@H](CCCCO)N(C)C(=O)NCC=1C(=C(F)C=CC=1)F)OC(=O)NC(=NO1)C=C1C1=CC=C(Cl)C=C1 CJMBYNKZUOOONJ-IBGZPJMESA-N 0.000 claims 1
YIHURIMTSNNPER-FQEVSTJZSA-N [(2s)-2-[(2,3-difluorophenyl)methylcarbamoyl-methylamino]-6-hydroxyhexyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](CCCCO)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=CC(F)=C1F YIHURIMTSNNPER-FQEVSTJZSA-N 0.000 claims 1
RZLPMYQABUWAMG-IBGZPJMESA-N [(2s)-2-[(2,3-difluorophenyl)methylcarbamoyl-methylamino]pent-4-enyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)CC=C)C(=O)NCC1=CC=CC(F)=C1F RZLPMYQABUWAMG-IBGZPJMESA-N 0.000 claims 1
PGDPLACMERQPQJ-QFIPXVFZSA-N [(2s)-2-[(2,4-dichlorophenyl)methylcarbamoyl-methylamino]-6-hydroxy-6-methylheptyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](CCCC(C)(C)O)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=C(Cl)C=C1Cl PGDPLACMERQPQJ-QFIPXVFZSA-N 0.000 claims 1
GFAOIMMEHCZTKE-QFIPXVFZSA-N [(2s)-2-[(2,4-difluorophenyl)methylcarbamoyl-methylamino]-6-hydroxy-6-methylheptyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](CCCC(C)(C)O)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=C(F)C=C1F GFAOIMMEHCZTKE-QFIPXVFZSA-N 0.000 claims 1
NKTNDADUYGKAKC-IBGZPJMESA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-3-(2-hydroxyethoxy)propyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@@H](COCCO)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl NKTNDADUYGKAKC-IBGZPJMESA-N 0.000 claims 1
VCVHGVHSGAUBOA-NRFANRHFSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-3-(3-hydroxy-2,2-dimethylpropoxy)propyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@@H](COCC(C)(C)CO)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl VCVHGVHSGAUBOA-NRFANRHFSA-N 0.000 claims 1
DZRZWOFSMMKYRO-IBGZPJMESA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-3-(dimethylamino)propyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CN(C)C)C(=O)NCC1=CC=CC(F)=C1Cl DZRZWOFSMMKYRO-IBGZPJMESA-N 0.000 claims 1
CGQVJQDUUJPIEZ-VQTJNVASSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-3-[(2r)-2,3-dihydroxypropoxy]propyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](COC[C@H](O)CO)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl CGQVJQDUUJPIEZ-VQTJNVASSA-N 0.000 claims 1
MVHHEGWRUILCBP-PMACEKPBSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-3-[(2s)-2,3-dihydroxypropoxy]propyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@@H](COC[C@@H](O)CO)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl MVHHEGWRUILCBP-PMACEKPBSA-N 0.000 claims 1
GNRHMRNHRBPFGW-RBUKOAKNSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-3-[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]propyl] n-(5-phenyl-1,2,4-oxadiazol-3-yl)carbamate Chemical compound C([C@@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)C[C@H]1OC(C)(C)OC1)OC(=O)NC(N=1)=NOC=1C1=CC=CC=C1 GNRHMRNHRBPFGW-RBUKOAKNSA-N 0.000 claims 1
UQXMXVDOEAAZLT-VQTJNVASSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-3-[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]propyl] n-(5-phenyl-1,2-oxazol-3-yl)carbamate Chemical compound C([C@@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)C[C@H]1OC(C)(C)OC1)OC(=O)NC(=NO1)C=C1C1=CC=CC=C1 UQXMXVDOEAAZLT-VQTJNVASSA-N 0.000 claims 1
XUHDGKBQWCCCQO-VQTJNVASSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-3-[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]propyl] n-[5-(3-chlorophenyl)-1,2-oxazol-3-yl]carbamate Chemical compound C([C@@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)C[C@H]1OC(C)(C)OC1)OC(=O)NC(=NO1)C=C1C1=CC=CC(Cl)=C1 XUHDGKBQWCCCQO-VQTJNVASSA-N 0.000 claims 1
BOHKVJPARDAZPJ-VQTJNVASSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-3-[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]propyl] n-[5-(3-fluorophenyl)-1,2-oxazol-3-yl]carbamate Chemical compound C([C@@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)C[C@H]1OC(C)(C)OC1)OC(=O)NC(=NO1)C=C1C1=CC=CC(F)=C1 BOHKVJPARDAZPJ-VQTJNVASSA-N 0.000 claims 1
FUKHYSYRJPMDPD-KRWDZBQOSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-4,4-difluoro-5-hydroxypentyl] n-(3-phenyl-1,2-oxazol-5-yl)carbamate Chemical compound C([C@@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)CC(F)(F)CO)OC(=O)NC(ON=1)=CC=1C1=CC=CC=C1 FUKHYSYRJPMDPD-KRWDZBQOSA-N 0.000 claims 1
CCFSPBBCRNQIMU-SFHVURJKSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-4,4-difluoro-5-hydroxypentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CC(F)(F)CO)C(=O)NCC1=CC=CC(F)=C1Cl CCFSPBBCRNQIMU-SFHVURJKSA-N 0.000 claims 1
FZPCPVGNAOGFPU-KRWDZBQOSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-4,4-difluoro-5-hydroxypentyl] n-[3-(3-fluorophenyl)-1,2-oxazol-5-yl]carbamate Chemical compound C([C@@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)CC(F)(F)CO)OC(=O)NC(ON=1)=CC=1C1=CC=CC(F)=C1 FZPCPVGNAOGFPU-KRWDZBQOSA-N 0.000 claims 1
IMQKIJZHEAIZSK-KRWDZBQOSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-4,4-difluoro-5-hydroxypentyl] n-[5-(3-fluorophenyl)-1,2-oxazol-3-yl]carbamate Chemical compound C([C@@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)CC(F)(F)CO)OC(=O)NC(=NO1)C=C1C1=CC=CC(F)=C1 IMQKIJZHEAIZSK-KRWDZBQOSA-N 0.000 claims 1
AHLDMPKZAPHBRU-SFHVURJKSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-4,4-difluoro-5-hydroxypentyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)CC(F)(F)CO)C(=O)NCC1=CC=CC(F)=C1Cl AHLDMPKZAPHBRU-SFHVURJKSA-N 0.000 claims 1
KOMVGXUBOGVICD-ZENAZSQFSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-4,5-dihydroxypentyl] n-(2,6-naphthyridin-3-yl)carbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=NC=C2C=1)CC(O)CO)C(=O)NCC1=CC=CC(F)=C1Cl KOMVGXUBOGVICD-ZENAZSQFSA-N 0.000 claims 1
XHRUTYOGFDLXAI-OYKVQYDMSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-4,5-dihydroxypentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CC(O)CO)C(=O)NCC1=CC=CC(F)=C1Cl XHRUTYOGFDLXAI-OYKVQYDMSA-N 0.000 claims 1
UBSNYCLTNCGHFC-QFIPXVFZSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyrazin-3-yl)butyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](CCC=1N2CCNCC2=CN=1)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl UBSNYCLTNCGHFC-QFIPXVFZSA-N 0.000 claims 1
YWMBTKHGZYRAAD-NRFANRHFSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-4-[3-[(dimethylamino)methyl]-1,2,4-oxadiazol-5-yl]butyl] n-isoquinolin-3-ylcarbamate Chemical compound CN(C)CC1=NOC(CC[C@@H](COC(=O)NC=2N=CC3=CC=CC=C3C=2)N(C)C(=O)NCC=2C(=C(F)C=CC=2)Cl)=N1 YWMBTKHGZYRAAD-NRFANRHFSA-N 0.000 claims 1
JPYFWTXKCQSTGK-ZDUSSCGKSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-4-hydroxy-4-methylpentyl] n-(5,6-difluoro-1,3-benzothiazol-2-yl)carbamate Chemical compound CN([C@H](COC(=O)NC=1SC2=CC(F)=C(F)C=C2N=1)CC(C)(C)O)C(=O)NCC1=CC=CC(F)=C1Cl JPYFWTXKCQSTGK-ZDUSSCGKSA-N 0.000 claims 1
MLYFDCNFWJSNHO-IBGZPJMESA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-4-hydroxy-4-methylpentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CC(C)(C)O)C(=O)NCC1=CC=CC(F)=C1Cl MLYFDCNFWJSNHO-IBGZPJMESA-N 0.000 claims 1
JZFWQSNJUHWHRI-SFHVURJKSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-4-hydroxy-4-methylpentyl] n-[5-(3-fluorophenyl)-1,2-oxazol-3-yl]carbamate Chemical compound C([C@@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)CC(C)(C)O)OC(=O)NC(=NO1)C=C1C1=CC=CC(F)=C1 JZFWQSNJUHWHRI-SFHVURJKSA-N 0.000 claims 1
FKTWDPKMRWNNOJ-IBGZPJMESA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-4-hydroxy-4-methylpentyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)CC(C)(C)O)C(=O)NCC1=CC=CC(F)=C1Cl FKTWDPKMRWNNOJ-IBGZPJMESA-N 0.000 claims 1
AQRAUVGSILPNCZ-QHCPKHFHSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-(1,3-dioxoisoindol-2-yl)pentyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](CCCN1C(C2=CC=CC=C2C1=O)=O)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl AQRAUVGSILPNCZ-QHCPKHFHSA-N 0.000 claims 1
XHRKJXVXSVLHNJ-FQEVSTJZSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-(2,2,2-trifluoroethylamino)pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@@H](CCCNCC(F)(F)F)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl XHRKJXVXSVLHNJ-FQEVSTJZSA-N 0.000 claims 1
MMPPBVVHSMDLSZ-FQEVSTJZSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-(2,2-difluoroethylamino)pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@@H](CCCNCC(F)F)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl MMPPBVVHSMDLSZ-FQEVSTJZSA-N 0.000 claims 1
LCBCYNNSCKPZOX-NRFANRHFSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-(2-fluoroethylamino)pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@@H](CCCNCCF)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl LCBCYNNSCKPZOX-NRFANRHFSA-N 0.000 claims 1
TYCQFLDGDRUVIS-QHCPKHFHSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-(2-methyl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl)-5-oxopentyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](CCC(=O)N1CC=2N=C(C)NC=2CC1)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl TYCQFLDGDRUVIS-QHCPKHFHSA-N 0.000 claims 1
UILNXSFBKLMMHZ-QFIPXVFZSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-(2-oxopiperazin-1-yl)pentyl] n-isoquinolin-3-ylcarbamate Chemical compound C([C@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)COC(=O)NC=1N=CC2=CC=CC=C2C=1)CCN1CCNCC1=O UILNXSFBKLMMHZ-QFIPXVFZSA-N 0.000 claims 1
IMMXOUCDBPOSTM-NRFANRHFSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-(3,3-difluoroazetidin-1-yl)pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C([C@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CCN1CC(F)(F)C1 IMMXOUCDBPOSTM-NRFANRHFSA-N 0.000 claims 1
HQBNHMNYQYUNEH-QFIPXVFZSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-(3,3-difluoropyrrolidin-1-yl)pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C([C@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CCN1CCC(F)(F)C1 HQBNHMNYQYUNEH-QFIPXVFZSA-N 0.000 claims 1
YDVZMJLGPWFTTL-CGAIIQECSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-(3-fluoropiperidin-1-yl)pentyl] n-isoquinolin-3-ylcarbamate Chemical compound C([C@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)COC(=O)NC=1N=CC2=CC=CC=C2C=1)CCN1CCCC(F)C1 YDVZMJLGPWFTTL-CGAIIQECSA-N 0.000 claims 1
ZZCJZOCGXXTIIM-DEOSSOPVSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-(4-ethylpiperazin-1-yl)-5-oxopentyl] n-isoquinolin-3-ylcarbamate Chemical compound C1CN(CC)CCN1C(=O)CC[C@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)COC(=O)NC1=CC2=CC=CC=C2C=N1 ZZCJZOCGXXTIIM-DEOSSOPVSA-N 0.000 claims 1
MWQAFBYGNSHPMQ-DEOSSOPVSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-(4-methylpiperazin-1-yl)pentyl] n-isoquinolin-3-ylcarbamate Chemical compound C([C@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)COC(=O)NC=1N=CC2=CC=CC=C2C=1)CCN1CCN(C)CC1 MWQAFBYGNSHPMQ-DEOSSOPVSA-N 0.000 claims 1
UWQVPDZZYMEWQA-DEOSSOPVSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-(6,8-dihydro-5h-imidazo[1,5-a]pyrazin-7-yl)pentyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](CCCN1CC2=CN=CN2CC1)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl UWQVPDZZYMEWQA-DEOSSOPVSA-N 0.000 claims 1
ZKQVEEVNWDHTIK-IBGZPJMESA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-(diaminomethylideneamino)pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@@H](CCCNC(N)=N)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl ZKQVEEVNWDHTIK-IBGZPJMESA-N 0.000 claims 1
WHWALWOYRJAQAB-NRFANRHFSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-(dimethylsulfamoylamino)pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CCCNS(=O)(=O)N(C)C)C(=O)NCC1=CC=CC(F)=C1Cl WHWALWOYRJAQAB-NRFANRHFSA-N 0.000 claims 1
WEAPGHMBEDVLFV-QHCPKHFHSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-(piperazine-1-carbonylamino)pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C([C@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CCNC(=O)N1CCNCC1 WEAPGHMBEDVLFV-QHCPKHFHSA-N 0.000 claims 1
FRNXNHCJNQAPQU-QFIPXVFZSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-(propylsulfonylamino)pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CCCNS(=O)(=O)CCC)C(=O)NCC1=CC=CC(F)=C1Cl FRNXNHCJNQAPQU-QFIPXVFZSA-N 0.000 claims 1
VSWNYWCCTKMEEP-IBGZPJMESA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-(sulfamoylamino)pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@@H](CCCNS(N)(=O)=O)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl VSWNYWCCTKMEEP-IBGZPJMESA-N 0.000 claims 1
JVACUXXCYZLVAN-QFIPXVFZSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-[(2-hydroxy-2-methylpropyl)amino]pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@@H](CCCNCC(C)(C)O)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl JVACUXXCYZLVAN-QFIPXVFZSA-N 0.000 claims 1
LMPDNXCGJHWHIJ-PKTZIBPZSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-[(3r)-3-(hydroxymethyl)piperazin-1-yl]-5-oxopentyl] n-isoquinolin-3-ylcarbamate Chemical compound C([C@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)COC(=O)NC=1N=CC2=CC=CC=C2C=1)CC(=O)N1CCN[C@@H](CO)C1 LMPDNXCGJHWHIJ-PKTZIBPZSA-N 0.000 claims 1
LMPDNXCGJHWHIJ-GOTSBHOMSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-[(3s)-3-(hydroxymethyl)piperazin-1-yl]-5-oxopentyl] n-isoquinolin-3-ylcarbamate Chemical compound C([C@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)COC(=O)NC=1N=CC2=CC=CC=C2C=1)CC(=O)N1CCN[C@H](CO)C1 LMPDNXCGJHWHIJ-GOTSBHOMSA-N 0.000 claims 1
QIUZZHNTDVFWAN-NRFANRHFSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-[(n-cyano-n'-methylcarbamimidoyl)amino]pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CCCNC(/NC)=N/C#N)C(=O)NCC1=CC=CC(F)=C1Cl QIUZZHNTDVFWAN-NRFANRHFSA-N 0.000 claims 1
LMPDNXCGJHWHIJ-WCSIJFPASA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-[3-(hydroxymethyl)piperazin-1-yl]-5-oxopentyl] n-isoquinolin-3-ylcarbamate Chemical compound C([C@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)COC(=O)NC=1N=CC2=CC=CC=C2C=1)CC(=O)N1CCNC(CO)C1 LMPDNXCGJHWHIJ-WCSIJFPASA-N 0.000 claims 1
NALHHAPEAFWOIO-DEOSSOPVSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-[4-(2,2,2-trifluoroethyl)piperazin-1-yl]pentyl] n-isoquinolin-3-ylcarbamate Chemical compound C([C@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)COC(=O)NC=1N=CC2=CC=CC=C2C=1)CCN1CCN(CC(F)(F)F)CC1 NALHHAPEAFWOIO-DEOSSOPVSA-N 0.000 claims 1
OTSKNHYFYJPTDD-SFHVURJKSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-[[(cyanoamino)-(2-hydroxyethylamino)methylidene]amino]pentyl] n-(1,3-benzothiazol-2-yl)carbamate Chemical compound CN([C@@H](CCCN\C(NCCO)=N/C#N)COC(=O)NC=1SC2=CC=CC=C2N=1)C(=O)NCC1=CC=CC(F)=C1Cl OTSKNHYFYJPTDD-SFHVURJKSA-N 0.000 claims 1
LQWBFIQFJBYAMS-QFIPXVFZSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-[[(cyanoamino)-(2-hydroxyethylamino)methylidene]amino]pentyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](CCCN\C(NCCO)=N/C#N)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl LQWBFIQFJBYAMS-QFIPXVFZSA-N 0.000 claims 1
OHAUIICTWKRYGV-QFIPXVFZSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-[[(cyanoamino)-(dimethylamino)methylidene]amino]pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CCCN/C(N(C)C)=N/C#N)C(=O)NCC1=CC=CC(F)=C1Cl OHAUIICTWKRYGV-QFIPXVFZSA-N 0.000 claims 1
BYMISGXDBYIDQI-IBGZPJMESA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-hydroxy-4,4-dimethylpentyl] n-(3-phenyl-1,2-oxazol-5-yl)carbamate Chemical compound C([C@@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)CC(C)(C)CO)OC(=O)NC(ON=1)=CC=1C1=CC=CC=C1 BYMISGXDBYIDQI-IBGZPJMESA-N 0.000 claims 1
BGVWTWFFNOGQGY-IBGZPJMESA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-hydroxy-5-methylhexyl] n-(3-phenyl-1,2-oxazol-5-yl)carbamate Chemical compound C([C@H](CCC(C)(C)O)N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)OC(=O)NC(ON=1)=CC=1C1=CC=CC=C1 BGVWTWFFNOGQGY-IBGZPJMESA-N 0.000 claims 1
WGZIYXHDUUJMPQ-IBGZPJMESA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-hydroxypentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@@H](CCCO)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl WGZIYXHDUUJMPQ-IBGZPJMESA-N 0.000 claims 1
VRNNDCBOZACTPK-VWLOTQADSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-oxo-5-(4-propylpiperazin-1-yl)pentyl] n-isoquinolin-3-ylcarbamate Chemical compound C1CN(CCC)CCN1C(=O)CC[C@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)COC(=O)NC1=CC2=CC=CC=C2C=N1 VRNNDCBOZACTPK-VWLOTQADSA-N 0.000 claims 1
PSAOTDWEWWYFDA-QFIPXVFZSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-oxo-5-piperazin-1-ylpentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C([C@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CC(=O)N1CCNCC1 PSAOTDWEWWYFDA-QFIPXVFZSA-N 0.000 claims 1
NGJGGGWRXHINCU-QHCPKHFHSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-piperazin-1-ylpentyl] n-isoquinolin-3-ylcarbamate Chemical compound C([C@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)COC(=O)NC=1N=CC2=CC=CC=C2C=1)CCN1CCNCC1 NGJGGGWRXHINCU-QHCPKHFHSA-N 0.000 claims 1
FCEDSFPCEZDAKD-IBGZPJMESA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-6-hydroxyhexyl] n-(2,7-naphthyridin-3-yl)carbamate Chemical compound CN([C@@H](CCCCO)COC(=O)NC=1N=CC2=CN=CC=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl FCEDSFPCEZDAKD-IBGZPJMESA-N 0.000 claims 1
CHRYDBCEXPPJTI-FQEVSTJZSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-6-hydroxyhexyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@@H](CCCCO)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl CHRYDBCEXPPJTI-FQEVSTJZSA-N 0.000 claims 1
MZJJMMYDKKXLOD-FQEVSTJZSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-6-hydroxyhexyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](CCCCO)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl MZJJMMYDKKXLOD-FQEVSTJZSA-N 0.000 claims 1
OKDUBSWTAWMLOY-SFHVURJKSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]pent-4-enyl] n-(2,6-naphthyridin-3-yl)carbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=NC=C2C=1)CC=C)C(=O)NCC1=CC=CC(F)=C1Cl OKDUBSWTAWMLOY-SFHVURJKSA-N 0.000 claims 1
FWMBTEOTHACGLA-SFHVURJKSA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]pent-4-enyl] n-(2,7-naphthyridin-3-yl)carbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CN=CC=C2C=1)CC=C)C(=O)NCC1=CC=CC(F)=C1Cl FWMBTEOTHACGLA-SFHVURJKSA-N 0.000 claims 1
XVOKFVSAAOSLLK-IBGZPJMESA-N [(2s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]pent-4-enyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CC=C)C(=O)NCC1=CC=CC(F)=C1Cl XVOKFVSAAOSLLK-IBGZPJMESA-N 0.000 claims 1
RHCQXAUPVIICHG-NRFANRHFSA-N [(2s)-2-[(2-chloro-4-fluorophenyl)methylcarbamoyl-ethylamino]-4-hydroxy-4-methylpentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CCN([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CC(C)(C)O)C(=O)NCC1=CC=C(F)C=C1Cl RHCQXAUPVIICHG-NRFANRHFSA-N 0.000 claims 1
GEZOGDLXULPGTP-AWEZNQCLSA-N [(2s)-2-[(2-chloro-4-fluorophenyl)methylcarbamoyl-methylamino]-4-hydroxy-4-methylpentyl] n-(5,6-difluoro-1,3-benzothiazol-2-yl)carbamate Chemical compound CN([C@H](COC(=O)NC=1SC2=CC(F)=C(F)C=C2N=1)CC(C)(C)O)C(=O)NCC1=CC=C(F)C=C1Cl GEZOGDLXULPGTP-AWEZNQCLSA-N 0.000 claims 1
YTTZQTBATVLYOE-FQEVSTJZSA-N [(2s)-2-[(2-chloro-4-fluorophenyl)methylcarbamoyl-methylamino]-4-hydroxy-4-methylpentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CC(C)(C)O)C(=O)NCC1=CC=C(F)C=C1Cl YTTZQTBATVLYOE-FQEVSTJZSA-N 0.000 claims 1
UBXVCCXDGQRXDM-FQEVSTJZSA-N [(2s)-2-[(2-chloro-4-fluorophenyl)methylcarbamoyl-methylamino]-4-hydroxy-4-methylpentyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)CC(C)(C)O)C(=O)NCC1=CC=C(F)C=C1Cl UBXVCCXDGQRXDM-FQEVSTJZSA-N 0.000 claims 1
YDADDAQOLSBHQQ-QFIPXVFZSA-N [(2s)-2-[(2-chloro-4-fluorophenyl)methylcarbamoyl-methylamino]-6-hydroxy-6-methylheptyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](CCCC(C)(C)O)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=C(F)C=C1Cl YDADDAQOLSBHQQ-QFIPXVFZSA-N 0.000 claims 1
ZDXQWEZWCIQXNR-NRFANRHFSA-N [(2s)-2-[(2-chloro-4-fluorophenyl)methylcarbamoyl-methylamino]-6-hydroxyhexyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](CCCCO)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=C(F)C=C1Cl ZDXQWEZWCIQXNR-NRFANRHFSA-N 0.000 claims 1
UQDRUAKNJQDEIU-NRFANRHFSA-N [(2s)-2-[(2-chlorophenyl)methylcarbamoyl-ethylamino]-4-hydroxy-4-methylpentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CCN([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CC(C)(C)O)C(=O)NCC1=CC=CC=C1Cl UQDRUAKNJQDEIU-NRFANRHFSA-N 0.000 claims 1
PPXRFXMLXSMDJJ-NRFANRHFSA-N [(2s)-2-[(2-chlorophenyl)methylcarbamoyl-methylamino]-3-(3-oxopiperazin-1-yl)propyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C([C@@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)N(C)C(=O)NCC=1C(=CC=CC=1)Cl)N1CCNC(=O)C1 PPXRFXMLXSMDJJ-NRFANRHFSA-N 0.000 claims 1
CEXAXFPXMXTAOL-SFHVURJKSA-N [(2s)-2-[(2-chlorophenyl)methylcarbamoyl-methylamino]-3-hydroxypropyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](CO)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=CC=C1Cl CEXAXFPXMXTAOL-SFHVURJKSA-N 0.000 claims 1
UBXXSGBVJMWLHL-QFIPXVFZSA-N [(2s)-2-[(2-chlorophenyl)methylcarbamoyl-methylamino]-3-morpholin-4-ylpropyl] n-isoquinolin-3-ylcarbamate Chemical compound C([C@@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)N(C)C(=O)NCC=1C(=CC=CC=1)Cl)N1CCOCC1 UBXXSGBVJMWLHL-QFIPXVFZSA-N 0.000 claims 1
BCXIHPKVJJVFAY-VWLOTQADSA-N [(2s)-2-[(2-chlorophenyl)methylcarbamoyl-methylamino]-3-phenylmethoxypropyl] n-isoquinolin-3-ylcarbamate Chemical compound C([C@H](N(C)C(=O)NCC=1C(=CC=CC=1)Cl)COC(=O)NC=1N=CC2=CC=CC=C2C=1)OCC1=CC=CC=C1 BCXIHPKVJJVFAY-VWLOTQADSA-N 0.000 claims 1
COPAYETUSHDQFC-QFIPXVFZSA-N [(2s)-2-[(2-chlorophenyl)methylcarbamoyl-methylamino]-4-(3-oxopiperazin-1-yl)butyl] n-isoquinolin-3-ylcarbamate Chemical compound C([C@H](N(C)C(=O)NCC=1C(=CC=CC=1)Cl)COC(=O)NC=1N=CC2=CC=CC=C2C=1)CN1CCNC(=O)C1 COPAYETUSHDQFC-QFIPXVFZSA-N 0.000 claims 1
DDMNLQIIEVSUNN-QHCPKHFHSA-N [(2s)-2-[(2-chlorophenyl)methylcarbamoyl-methylamino]-4-(4-methyl-3-oxopiperazin-1-yl)butyl] n-isoquinolin-3-ylcarbamate Chemical compound C([C@H](N(C)C(=O)NCC=1C(=CC=CC=1)Cl)COC(=O)NC=1N=CC2=CC=CC=C2C=1)CN1CCN(C)C(=O)C1 DDMNLQIIEVSUNN-QHCPKHFHSA-N 0.000 claims 1
NUQGPRNSHNSYAC-DEOSSOPVSA-N [(2s)-2-[(2-chlorophenyl)methylcarbamoyl-methylamino]-4-(4-methylsulfonylpiperazin-1-yl)butyl] n-isoquinolin-3-ylcarbamate Chemical compound C([C@H](N(C)C(=O)NCC=1C(=CC=CC=1)Cl)COC(=O)NC=1N=CC2=CC=CC=C2C=1)CN1CCN(S(C)(=O)=O)CC1 NUQGPRNSHNSYAC-DEOSSOPVSA-N 0.000 claims 1
NLKFBCMZXPHLBR-FQEVSTJZSA-N [(2s)-2-[(2-chlorophenyl)methylcarbamoyl-methylamino]-4-hydroxy-4-methylpentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CC(C)(C)O)C(=O)NCC1=CC=CC=C1Cl NLKFBCMZXPHLBR-FQEVSTJZSA-N 0.000 claims 1
FRKRDQRYBRBUPR-FQEVSTJZSA-N [(2s)-2-[(2-chlorophenyl)methylcarbamoyl-methylamino]-4-hydroxy-4-methylpentyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)CC(C)(C)O)C(=O)NCC1=CC=CC=C1Cl FRKRDQRYBRBUPR-FQEVSTJZSA-N 0.000 claims 1
NEPHNHQRUPMSAH-NRFANRHFSA-N [(2s)-2-[(2-chlorophenyl)methylcarbamoyl-methylamino]-5-hydroxy-5-methylhexyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](CCC(C)(C)O)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=CC=C1Cl NEPHNHQRUPMSAH-NRFANRHFSA-N 0.000 claims 1
FYFXFSXIISCHGD-QFIPXVFZSA-N [(2s)-2-[(2-chlorophenyl)methylcarbamoyl-methylamino]-6-hydroxy-6-methylheptyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](CCCC(C)(C)O)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=CC=C1Cl FYFXFSXIISCHGD-QFIPXVFZSA-N 0.000 claims 1
YNEZRWOVWRCIAU-YSYXNDDBSA-N [(2s)-2-[(2-chlorophenyl)methylcarbamoyl-methylamino]-6-hydroxyheptyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)CCCC(O)C)C(=O)NCC1=CC=CC=C1Cl YNEZRWOVWRCIAU-YSYXNDDBSA-N 0.000 claims 1
RJRSBHXVTNMPSK-NRFANRHFSA-N [(2s)-2-[(2-chlorophenyl)methylcarbamoyl-methylamino]-6-hydroxyhexyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@@H](CCCCO)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C(=O)NCC1=CC=CC=C1Cl RJRSBHXVTNMPSK-NRFANRHFSA-N 0.000 claims 1
LJKOJTODDNVCLT-NRFANRHFSA-N [(2s)-2-[(2-chlorophenyl)methylcarbamoyl-methylamino]-6-hydroxyhexyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](CCCCO)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=CC=C1Cl LJKOJTODDNVCLT-NRFANRHFSA-N 0.000 claims 1
FUHWYPDOJNTRPN-QFIPXVFZSA-N [(2s)-2-[(2-chlorophenyl)methylcarbamoyl-methylamino]-6-oxoheptyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](CCCC(C)=O)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=CC=C1Cl FUHWYPDOJNTRPN-QFIPXVFZSA-N 0.000 claims 1
NRSGFRUYUYIOOI-QFIPXVFZSA-N [(2s)-2-[(2-chlorophenyl)methylcarbamoyl-propan-2-ylamino]-4-hydroxy-4-methylpentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(C)N([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CC(C)(C)O)C(=O)NCC1=CC=CC=C1Cl NRSGFRUYUYIOOI-QFIPXVFZSA-N 0.000 claims 1
PGUIGYSGCQGJOO-NRFANRHFSA-N [(2s)-2-[(3-chloro-2-fluorophenyl)methylcarbamoyl-methylamino]-6-hydroxy-6-methylheptyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](CCCC(C)(C)O)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=CC(Cl)=C1F PGUIGYSGCQGJOO-NRFANRHFSA-N 0.000 claims 1
ZIBJPRVJFJJFIW-BGERDNNASA-N [(2s)-2-[(3-fluorophenyl)methylcarbamoyl-methylamino]-4,5-dihydroxypentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CC(O)CO)C(=O)NCC1=CC=CC(F)=C1 ZIBJPRVJFJJFIW-BGERDNNASA-N 0.000 claims 1
OSBUKVPHMMEFSI-IBGZPJMESA-N [(2s)-2-[acetyl-[(2,3-difluorophenyl)methylamino]amino]-3-[(2-aminoacetyl)amino]propyl] n-isoquinolin-3-ylcarbamate Chemical compound CC(=O)N([C@@H](CNC(=O)CN)COC(=O)NC=1N=CC2=CC=CC=C2C=1)NCC1=CC=CC(F)=C1F OSBUKVPHMMEFSI-IBGZPJMESA-N 0.000 claims 1
QPPJEGJPTYAURH-SFTDATJTSA-N [(2s)-2-[acetyl-[(2,3-difluorophenyl)methylamino]amino]-3-[(2s)-2-hydroxy-3-phosphonooxypropoxy]propyl] n-isoquinolin-3-ylcarbamate Chemical compound CC(=O)N([C@@H](COC[C@H](O)COP(O)(O)=O)COC(=O)NC=1N=CC2=CC=CC=C2C=1)NCC1=CC=CC(F)=C1F QPPJEGJPTYAURH-SFTDATJTSA-N 0.000 claims 1
VUALHMOUTMGKDK-NRFANRHFSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-3-(1h-imidazol-5-yl)propyl] n-isoquinolin-3-ylcarbamate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)CC=1NC=NC=1)NCC1=CC=CC(F)=C1Cl VUALHMOUTMGKDK-NRFANRHFSA-N 0.000 claims 1
YUAJBSPRRDFWIK-SFHVURJKSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-3-(2,2-difluoroethylamino)propyl] n-(5-phenyl-1,2-oxazol-3-yl)carbamate Chemical compound CC(=O)N([C@@H](CNCC(F)F)COC(=O)NC1=NOC(=C1)C=1C=CC=CC=1)NCC1=CC=CC(F)=C1Cl YUAJBSPRRDFWIK-SFHVURJKSA-N 0.000 claims 1
DHSPIHMAHAFAEY-SFHVURJKSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-3-(2,2-difluoroethylamino)propyl] n-[3-(3-fluorophenyl)-1,2-oxazol-5-yl]carbamate Chemical compound CC(=O)N([C@@H](CNCC(F)F)COC(=O)NC=1ON=C(C=1)C=1C=C(F)C=CC=1)NCC1=CC=CC(F)=C1Cl DHSPIHMAHAFAEY-SFHVURJKSA-N 0.000 claims 1
OGWVVEDQURXJRK-IBGZPJMESA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-3-(2,2-difluoroethylamino)propyl] n-isoquinolin-3-ylcarbamate Chemical compound CC(=O)N([C@@H](CNCC(F)F)COC(=O)NC=1N=CC2=CC=CC=C2C=1)NCC1=CC=CC(F)=C1Cl OGWVVEDQURXJRK-IBGZPJMESA-N 0.000 claims 1
XFOUBJICCFVVHR-QFIPXVFZSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-3-(2,2-dimethyl-3-phosphonooxypropoxy)propyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@@H](COCC(C)(C)COP(O)(O)=O)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)NCC1=CC=CC(F)=C1Cl XFOUBJICCFVVHR-QFIPXVFZSA-N 0.000 claims 1
LIENKLXCWPGNGE-IBGZPJMESA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-3-[(2-aminoacetyl)amino]propyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@@H](CNC(=O)CN)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)NCC1=CC=CC(F)=C1Cl LIENKLXCWPGNGE-IBGZPJMESA-N 0.000 claims 1
OFTUJWKIMOARTN-IBGZPJMESA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-3-[(2-aminoacetyl)amino]propyl] n-isoquinolin-3-ylcarbamate Chemical compound CC(=O)N([C@@H](CNC(=O)CN)COC(=O)NC=1N=CC2=CC=CC=C2C=1)NCC1=CC=CC(F)=C1Cl OFTUJWKIMOARTN-IBGZPJMESA-N 0.000 claims 1
MISBRHFXBXUMAU-LEWJYISDSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-3-[(2r)-2-hydroxy-3-phosphonooxypropoxy]propyl] n-isoquinolin-3-ylcarbamate Chemical compound CC(=O)N([C@@H](COC[C@@H](O)COP(O)(O)=O)COC(=O)NC=1N=CC2=CC=CC=C2C=1)NCC1=CC=CC(F)=C1Cl MISBRHFXBXUMAU-LEWJYISDSA-N 0.000 claims 1
YTDPGLUVPDGFSJ-PMERELPUSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-3-[(3-benzoylbenzoyl)amino]propyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@@H](CNC(=O)C=1C=C(C=CC=1)C(=O)C=1C=CC=CC=1)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)NCC1=CC=CC(F)=C1Cl YTDPGLUVPDGFSJ-PMERELPUSA-N 0.000 claims 1
OHKLEKHBJJKBOV-PZJWPPBQSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-3-[[(2r)-2-amino-3-hydroxypropanoyl]amino]propyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@@H](CNC(=O)[C@H](N)CO)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)NCC1=CC=CC(F)=C1Cl OHKLEKHBJJKBOV-PZJWPPBQSA-N 0.000 claims 1
ILFOPYOYXQJDMB-QFIPXVFZSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-3-[bis(2-hydroxyethyl)amino]propyl] n-isoquinolin-3-ylcarbamate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)CN(CCO)CCO)NCC1=CC=CC(F)=C1Cl ILFOPYOYXQJDMB-QFIPXVFZSA-N 0.000 claims 1
YGZXJNIDEAQUFE-INIZCTEOSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-3-aminopropyl] n-(4-iodo-5-phenyl-1,2-oxazol-3-yl)carbamate Chemical compound CC(=O)N([C@@H](CN)COC(=O)NC=1C(=C(ON=1)C=1C=CC=CC=1)I)NCC1=CC=CC(F)=C1Cl YGZXJNIDEAQUFE-INIZCTEOSA-N 0.000 claims 1
FWOPWIXUNRVUAP-NRFANRHFSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4,4-dimethyl-5-phosphonooxypentyl] n-isoquinolin-3-ylcarbamate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)CC(C)(C)COP(O)(O)=O)NCC1=CC=CC(F)=C1Cl FWOPWIXUNRVUAP-NRFANRHFSA-N 0.000 claims 1
BZYIPCAOYPGRBJ-FQEVSTJZSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4-[(2-aminoacetyl)amino]butyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@@H](CCNC(=O)CN)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)NCC1=CC=CC(F)=C1Cl BZYIPCAOYPGRBJ-FQEVSTJZSA-N 0.000 claims 1
CTZKVKRXGSGNNT-RBBKRZOGSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4-[[(2r)-2-amino-3-hydroxypropanoyl]amino]butyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@@H](CCNC(=O)[C@H](N)CO)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)NCC1=CC=CC(F)=C1Cl CTZKVKRXGSGNNT-RBBKRZOGSA-N 0.000 claims 1
BVHSHZKDZLZNGZ-BGERDNNASA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4-hydroxy-5-[hydroxy(methoxy)phosphoryl]oxypentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CC(O)COP(O)(=O)OC)NCC1=CC=CC(F)=C1Cl BVHSHZKDZLZNGZ-BGERDNNASA-N 0.000 claims 1
VQGVPNKQIIOIOO-XJDOXCRVSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4-hydroxy-5-phosphonooxypentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CC(O)COP(O)(O)=O)NCC1=CC=CC(F)=C1Cl VQGVPNKQIIOIOO-XJDOXCRVSA-N 0.000 claims 1
LYAPCGMJWHAOLT-XJDOXCRVSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4-hydroxy-5-sulfooxypentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CC(O)COS(O)(=O)=O)NCC1=CC=CC(F)=C1Cl LYAPCGMJWHAOLT-XJDOXCRVSA-N 0.000 claims 1
UYTJPQNAAFTZEF-QFIPXVFZSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4-morpholin-4-yl-4-oxobutyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CC(=O)N1CCOCC1)NCC1=CC=CC(F)=C1Cl UYTJPQNAAFTZEF-QFIPXVFZSA-N 0.000 claims 1
OVNHDWYGZASBKR-BBQAJUCSSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-(2,3-dihydroxypropanoylamino)pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@@H](CCCNC(=O)C(O)CO)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)NCC1=CC=CC(F)=C1Cl OVNHDWYGZASBKR-BBQAJUCSSA-N 0.000 claims 1
QPPDTLYPCNJQJN-NRFANRHFSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-(2-hydroxyethylcarbamoylamino)pentyl] n-(3-phenyl-1,2-oxazol-5-yl)carbamate Chemical compound CC(=O)N([C@@H](CCCNC(=O)NCCO)COC(=O)NC=1ON=C(C=1)C=1C=CC=CC=1)NCC1=CC=CC(F)=C1Cl QPPDTLYPCNJQJN-NRFANRHFSA-N 0.000 claims 1
YTSWRESUVYCCGD-QFIPXVFZSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-(2-hydroxyethylcarbamoylamino)pentyl] n-isoquinolin-3-ylcarbamate Chemical compound CC(=O)N([C@@H](CCCNC(=O)NCCO)COC(=O)NC=1N=CC2=CC=CC=C2C=1)NCC1=CC=CC(F)=C1Cl YTSWRESUVYCCGD-QFIPXVFZSA-N 0.000 claims 1
VLJFUKLLFJXSDL-QHCPKHFHSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-(3-hydroxypropylcarbamoylamino)pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@@H](CCCNC(=O)NCCCO)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)NCC1=CC=CC(F)=C1Cl VLJFUKLLFJXSDL-QHCPKHFHSA-N 0.000 claims 1
JNAICMSXPIBZAA-MHZLTWQESA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-(4-cyclobutylpiperazin-1-yl)-5-oxopentyl] n-isoquinolin-3-ylcarbamate Chemical compound CC(=O)N([C@@H](CCC(=O)N1CCN(CC1)C1CCC1)COC(=O)NC=1N=CC2=CC=CC=C2C=1)NCC1=CC=CC(F)=C1Cl JNAICMSXPIBZAA-MHZLTWQESA-N 0.000 claims 1
GQHSYOWSJLXBDA-QHCPKHFHSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-(4-methylpiperazin-1-yl)-5-oxopentyl] n-(5-phenyl-1,2-oxazol-3-yl)carbamate Chemical compound C1CN(C)CCN1C(=O)CC[C@H](N(NCC=1C(=C(F)C=CC=1)Cl)C(C)=O)COC(=O)NC1=NOC(C=2C=CC=CC=2)=C1 GQHSYOWSJLXBDA-QHCPKHFHSA-N 0.000 claims 1
CLNOTPMHJVGZKC-DEOSSOPVSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-(4-methylpiperazin-1-yl)-5-oxopentyl] n-isoquinolin-3-ylcarbamate Chemical compound C1CN(C)CCN1C(=O)CC[C@H](N(NCC=1C(=C(F)C=CC=1)Cl)C(C)=O)COC(=O)NC1=CC2=CC=CC=C2C=N1 CLNOTPMHJVGZKC-DEOSSOPVSA-N 0.000 claims 1
GHVIWEYDWAPOLQ-QHCPKHFHSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-[(2,2-dimethyl-3-phosphonooxypropyl)amino]-5-oxopentyl] n-isoquinolin-3-ylcarbamate Chemical compound CC(=O)N([C@@H](CCC(=O)NCC(C)(C)COP(O)(O)=O)COC(=O)NC=1N=CC2=CC=CC=C2C=1)NCC1=CC=CC(F)=C1Cl GHVIWEYDWAPOLQ-QHCPKHFHSA-N 0.000 claims 1
YIFOTHVMVVNXAJ-DEOSSOPVSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-[(2,2-dimethyl-3-phosphonooxypropyl)carbamoylamino]pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@@H](CCCNC(=O)NCC(C)(C)COP(O)(O)=O)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)NCC1=CC=CC(F)=C1Cl YIFOTHVMVVNXAJ-DEOSSOPVSA-N 0.000 claims 1
MSVHAZSESGCPOQ-NRFANRHFSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-[(2-aminoacetyl)amino]pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@@H](CCCNC(=O)CN)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)NCC1=CC=CC(F)=C1Cl MSVHAZSESGCPOQ-NRFANRHFSA-N 0.000 claims 1
DEMYIAALEDYHTA-NRFANRHFSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-[(2-hydroxyacetyl)amino]pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@@H](CCCNC(=O)CO)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)NCC1=CC=CC(F)=C1Cl DEMYIAALEDYHTA-NRFANRHFSA-N 0.000 claims 1
KBHCZLPTCJKZNS-YTTGMZPUSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-[(3-benzoylbenzoyl)amino]pentyl] n-isoquinolin-3-ylcarbamate Chemical compound CC(=O)N([C@@H](CCCNC(=O)C=1C=C(C=CC=1)C(=O)C=1C=CC=CC=1)COC(=O)NC=1N=CC2=CC=CC=C2C=1)NCC1=CC=CC(F)=C1Cl KBHCZLPTCJKZNS-YTTGMZPUSA-N 0.000 claims 1
URXZSZLCMXMZBU-JTHBVZDNSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-[[(2r)-2-amino-3-hydroxypropanoyl]amino]pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@@H](CCCNC(=O)[C@H](N)CO)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)NCC1=CC=CC(F)=C1Cl URXZSZLCMXMZBU-JTHBVZDNSA-N 0.000 claims 1
RWYRWAURVXXVBY-JTHBVZDNSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-[[(2r)-2-amino-3-hydroxypropanoyl]amino]pentyl] n-isoquinolin-3-ylcarbamate Chemical compound CC(=O)N([C@@H](CCCNC(=O)[C@H](N)CO)COC(=O)NC=1N=CC2=CC=CC=C2C=1)NCC1=CC=CC(F)=C1Cl RWYRWAURVXXVBY-JTHBVZDNSA-N 0.000 claims 1
ZDLFELLIWDAXAR-UNMCSNQZSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-[[(2s)-2-amino-3-hydroxypropanoyl]amino]pentyl] n-(2,7-naphthyridin-3-yl)carbamate Chemical compound CC(=O)N([C@@H](CCCNC(=O)[C@@H](N)CO)COC(=O)NC=1N=CC2=CN=CC=C2C=1)NCC1=CC=CC(F)=C1Cl ZDLFELLIWDAXAR-UNMCSNQZSA-N 0.000 claims 1
URXZSZLCMXMZBU-GMAHTHKFSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-[[(2s)-2-amino-3-hydroxypropanoyl]amino]pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@@H](CCCNC(=O)[C@@H](N)CO)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)NCC1=CC=CC(F)=C1Cl URXZSZLCMXMZBU-GMAHTHKFSA-N 0.000 claims 1
RUAHTSNCLARDAE-NRFANRHFSA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-[methoxy(methyl)amino]-5-oxopentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CCC(=O)N(C)OC)NCC1=CC=CC(F)=C1Cl RUAHTSNCLARDAE-NRFANRHFSA-N 0.000 claims 1
LXIROZUWAYGAKO-WCSIJFPASA-N [(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-oxo-5-(pyrrolidin-3-ylamino)pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@@H](CCC(=O)NC1CNCC1)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)NCC1=CC=CC(F)=C1Cl LXIROZUWAYGAKO-WCSIJFPASA-N 0.000 claims 1
DGIDABLAOUWKQK-NRFANRHFSA-N [(2s)-2-[acetyl-[(2-chloro-4-fluorophenyl)methylamino]amino]-4-hydroxy-4-methylpentyl] n-(7-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC(F)=CC=C2C=1)CC(C)(C)O)NCC1=CC=C(F)C=C1Cl DGIDABLAOUWKQK-NRFANRHFSA-N 0.000 claims 1
SNQGQUMKVURZQZ-HXUWFJFHSA-N [(2s)-2-[acetyl-[(2-chlorophenyl)methylamino]amino]-3-methylbutyl] n-(6-methyl-1,3-benzothiazol-2-yl)carbamate Chemical compound CC(=O)N([C@H](COC(=O)NC=1SC2=CC(C)=CC=C2N=1)C(C)C)NCC1=CC=CC=C1Cl SNQGQUMKVURZQZ-HXUWFJFHSA-N 0.000 claims 1
FJEKXRLLDPLTFU-NRFANRHFSA-N [(2s)-2-[acetyl-[(2-chlorophenyl)methylamino]amino]-4-[methoxy(methyl)amino]-4-oxobutyl] n-isoquinolin-3-ylcarbamate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)CC(=O)N(C)OC)NCC1=CC=CC=C1Cl FJEKXRLLDPLTFU-NRFANRHFSA-N 0.000 claims 1
SQPPREGDZHEQMI-NRFANRHFSA-N [(2s)-2-[acetyl-[(2-chlorophenyl)methylamino]amino]-4-hydroxy-4-methylpentyl] n-(7-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC(F)=CC=C2C=1)CC(C)(C)O)NCC1=CC=CC=C1Cl SQPPREGDZHEQMI-NRFANRHFSA-N 0.000 claims 1
JLYQDMIHKWPLAK-FQEVSTJZSA-N [(2s)-2-[acetyl-[(2-chlorophenyl)methylamino]amino]-4-hydroxybutyl] n-isoquinolin-3-ylcarbamate Chemical compound CC(=O)N([C@@H](CCO)COC(=O)NC=1N=CC2=CC=CC=C2C=1)NCC1=CC=CC=C1Cl JLYQDMIHKWPLAK-FQEVSTJZSA-N 0.000 claims 1
QEEMZVIZAGCYNY-NRFANRHFSA-N [(2s)-2-[acetyl-[(2-chlorophenyl)methylamino]amino]-5-hydroxypentyl] n-isoquinolin-3-ylcarbamate Chemical compound CC(=O)N([C@@H](CCCO)COC(=O)NC=1N=CC2=CC=CC=C2C=1)NCC1=CC=CC=C1Cl QEEMZVIZAGCYNY-NRFANRHFSA-N 0.000 claims 1
CBWKOHITAFJKPS-KRWDZBQOSA-N [(2s)-2-[acetyl-[(2-chlorophenyl)methylamino]amino]butyl] n-(6-methyl-1,3-benzothiazol-2-yl)carbamate Chemical compound CC(=O)N([C@H](COC(=O)NC=1SC2=CC(C)=CC=C2N=1)CC)NCC1=CC=CC=C1Cl CBWKOHITAFJKPS-KRWDZBQOSA-N 0.000 claims 1
OGFJHBUKELWHSV-FQEVSTJZSA-N [(2s)-2-[acetyl-[(2-chlorophenyl)methylamino]amino]butyl] n-isoquinolin-3-ylcarbamate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)CC)NCC1=CC=CC=C1Cl OGFJHBUKELWHSV-FQEVSTJZSA-N 0.000 claims 1
LMGWOYLAYVVJGR-HNNXBMFYSA-N [(2s)-2-[acetyl-[(2-chlorophenyl)methylamino]amino]propyl] n-isoquinolin-3-ylcarbamate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)C)NCC1=CC=CC=C1Cl LMGWOYLAYVVJGR-HNNXBMFYSA-N 0.000 claims 1
SGZLMSSAFUTARY-ZDUSSCGKSA-N [(2s)-3-amino-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]propyl] n-(5-chloropyridin-2-yl)carbamate Chemical compound C([C@H](CN)N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)OC(=O)NC1=CC=C(Cl)C=N1 SGZLMSSAFUTARY-ZDUSSCGKSA-N 0.000 claims 1
LWCSGLDZVGJCQR-INIZCTEOSA-N [(2s)-3-amino-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]propyl] n-[3-(3-chlorophenyl)-1,2-oxazol-5-yl]carbamate Chemical compound C([C@H](CN)N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)OC(=O)NC(ON=1)=CC=1C1=CC=CC(Cl)=C1 LWCSGLDZVGJCQR-INIZCTEOSA-N 0.000 claims 1
FNSZQIKAINWLEP-INIZCTEOSA-N [(2s)-3-amino-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]propyl] n-[5-(3-fluorophenyl)-1,2-oxazol-3-yl]carbamate Chemical compound C([C@H](CN)N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)OC(=O)NC(=NO1)C=C1C1=CC=CC(F)=C1 FNSZQIKAINWLEP-INIZCTEOSA-N 0.000 claims 1
UREUPJWPNLLFKM-KRWDZBQOSA-N [(2s)-3-amino-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]propyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](CN)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl UREUPJWPNLLFKM-KRWDZBQOSA-N 0.000 claims 1
IRIYODHXEPUMQK-GGYWPGCISA-N [(2s)-4,5-diamino-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CC(N)CN)C(=O)NCC1=CC=CC(F)=C1Cl IRIYODHXEPUMQK-GGYWPGCISA-N 0.000 claims 1
FGKXUGHKJLGVFL-IBGZPJMESA-N [(2s)-5-[[amino-(carbamoylamino)methylidene]amino]-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@@H](CCCN\C(N)=N\C(N)=O)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl FGKXUGHKJLGVFL-IBGZPJMESA-N 0.000 claims 1
QVXFTOOIEZEXBU-FQEVSTJZSA-N [(2s)-5-[[amino-(cyanoamino)methylidene]amino]-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@@H](CCCN\C(N)=N\C#N)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl QVXFTOOIEZEXBU-FQEVSTJZSA-N 0.000 claims 1
KWYFDXWKYURCQP-VWLOTQADSA-N [(2s)-5-[bis(2-hydroxy-2-methylpropyl)amino]-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@@H](CCCN(CC(C)(C)O)CC(C)(C)O)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl KWYFDXWKYURCQP-VWLOTQADSA-N 0.000 claims 1
RVXKGQSVUKHEPB-SFHVURJKSA-N [(2s)-5-amino-2-[(2,3-difluorophenyl)methylcarbamoyl-methylamino]-4,4-difluoropentyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)CC(F)(F)CN)C(=O)NCC1=CC=CC(F)=C1F RVXKGQSVUKHEPB-SFHVURJKSA-N 0.000 claims 1
QXUSEWRHWGONFZ-HNNXBMFYSA-N [(2s)-5-amino-2-[(2,3-difluorophenyl)methylcarbamoyl-methylamino]pentyl] n-(1,3-benzothiazol-2-yl)carbamate Chemical compound CN([C@@H](CCCN)COC(=O)NC=1SC2=CC=CC=C2N=1)C(=O)NCC1=CC=CC(F)=C1F QXUSEWRHWGONFZ-HNNXBMFYSA-N 0.000 claims 1
BGAUYBRSCZLHNB-SFHVURJKSA-N [(2s)-5-amino-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-4,4-difluoropentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CC(F)(F)CN)C(=O)NCC1=CC=CC(F)=C1Cl BGAUYBRSCZLHNB-SFHVURJKSA-N 0.000 claims 1
LNRNJPXEXQOOKV-KRWDZBQOSA-N [(2s)-5-amino-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-4,4-difluoropentyl] n-[3-(3-fluorophenyl)-1,2-oxazol-5-yl]carbamate Chemical compound C([C@@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)CC(F)(F)CN)OC(=O)NC(ON=1)=CC=1C1=CC=CC(F)=C1 LNRNJPXEXQOOKV-KRWDZBQOSA-N 0.000 claims 1
YOJFJYMLKGMUCP-SFHVURJKSA-N [(2s)-5-amino-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-4,4-difluoropentyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)CC(F)(F)CN)C(=O)NCC1=CC=CC(F)=C1Cl YOJFJYMLKGMUCP-SFHVURJKSA-N 0.000 claims 1
BWPKIDZZVLYIEP-GGYWPGCISA-N [(2s)-5-amino-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-4-fluoropentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CC(F)CN)C(=O)NCC1=CC=CC(F)=C1Cl BWPKIDZZVLYIEP-GGYWPGCISA-N 0.000 claims 1
QITMFPIVFHCACM-SFHVURJKSA-N [(2s)-5-amino-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-iminopentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@@H](CCC(N)=N)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl QITMFPIVFHCACM-SFHVURJKSA-N 0.000 claims 1
VJQHEOCTJPCKQV-MBABXSBOSA-N [(2s)-5-amino-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]hexyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CCC(N)C)C(=O)NCC1=CC=CC(F)=C1Cl VJQHEOCTJPCKQV-MBABXSBOSA-N 0.000 claims 1
SMSIGAYLMVFWOQ-KRWDZBQOSA-N [(2s)-5-amino-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]pentyl] n-(1,7-naphthyridin-6-yl)carbamate Chemical compound CN([C@@H](CCCN)COC(=O)NC=1N=CC2=NC=CC=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl SMSIGAYLMVFWOQ-KRWDZBQOSA-N 0.000 claims 1
ISNRZHTUBGCMOV-SFHVURJKSA-N [(2s)-5-amino-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]pentyl] n-(2,7-naphthyridin-3-yl)carbamate Chemical compound CN([C@@H](CCCN)COC(=O)NC=1N=CC2=CN=CC=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl ISNRZHTUBGCMOV-SFHVURJKSA-N 0.000 claims 1
BZNRBOWDZOHITP-SFHVURJKSA-N [(2s)-5-amino-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]pentyl] n-(3-phenyl-1,2-oxazol-5-yl)carbamate Chemical compound C([C@H](CCCN)N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)OC(=O)NC(ON=1)=CC=1C1=CC=CC=C1 BZNRBOWDZOHITP-SFHVURJKSA-N 0.000 claims 1
TZTONEYVSXOKEE-IBGZPJMESA-N [(2s)-5-amino-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@@H](CCCN)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl TZTONEYVSXOKEE-IBGZPJMESA-N 0.000 claims 1
RRABPIMPBONLHI-HNNXBMFYSA-N [(2s)-5-amino-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]pentyl] n-[5-(trifluoromethyl)pyridin-2-yl]carbamate Chemical compound C([C@H](CCCN)N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)OC(=O)NC1=CC=C(C(F)(F)F)C=N1 RRABPIMPBONLHI-HNNXBMFYSA-N 0.000 claims 1
LCDVQGLSSYFJLA-IBGZPJMESA-N [(2s)-5-amino-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]pentyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](CCCN)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl LCDVQGLSSYFJLA-IBGZPJMESA-N 0.000 claims 1
DIXQEOLUWPSKGH-FQEVSTJZSA-N [(2s)-5-amino-2-[(2-chloro-4-fluorophenyl)methylcarbamoyl-methylamino]pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@@H](CCCN)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C(=O)NCC1=CC=C(F)C=C1Cl DIXQEOLUWPSKGH-FQEVSTJZSA-N 0.000 claims 1
GXZFEIMCPGUGSK-FQEVSTJZSA-N [(2s)-5-amino-2-[(2-chloro-4-fluorophenyl)methylcarbamoyl-methylamino]pentyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@@H](CCCN)COC(=O)NC=1N=CC2=CC=CC=C2C=1)C(=O)NCC1=CC=C(F)C=C1Cl GXZFEIMCPGUGSK-FQEVSTJZSA-N 0.000 claims 1
XIAVUGALURLVBR-ZQRQZVKFSA-N [(2s)-5-amino-2-[(2-chlorophenyl)methylcarbamoyl-methylamino]-6,6-difluorohexyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@@H](CCC(N)C(F)F)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C(=O)NCC1=CC=CC=C1Cl XIAVUGALURLVBR-ZQRQZVKFSA-N 0.000 claims 1
IUWYEJQOQBFIFU-FQEVSTJZSA-N [(2s)-5-amino-2-[(2-chlorophenyl)methylcarbamoyl-methylamino]pentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@@H](CCCN)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C(=O)NCC1=CC=CC=C1Cl IUWYEJQOQBFIFU-FQEVSTJZSA-N 0.000 claims 1
CWITUDSXBRSWMJ-DEOSSOPVSA-N [(2s)-6-acetamido-2-[acetyl-[(2-chlorophenyl)methylamino]amino]hexyl] n-isoquinolin-3-ylcarbamate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)CCCCNC(=O)C)NCC1=CC=CC=C1Cl CWITUDSXBRSWMJ-DEOSSOPVSA-N 0.000 claims 1
MDBBNPUCOSAGHZ-ZWKOTPCHSA-N [(2s,4r)-2-[(2,3-difluorophenyl)methylcarbamoyl-methylamino]-4,5-dihydroxypentyl] n-(5-phenyl-1,2-oxazol-3-yl)carbamate Chemical compound C([C@@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)F)C[C@@H](O)CO)OC(=O)NC(=NO1)C=C1C1=CC=CC=C1 MDBBNPUCOSAGHZ-ZWKOTPCHSA-N 0.000 claims 1
WMTXVQUFOCIMHC-ZWKOTPCHSA-N [(2s,4r)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-4,5-dihydroxypentyl] n-(3-phenyl-1,2-oxazol-5-yl)carbamate Chemical compound C([C@@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)C[C@@H](O)CO)OC(=O)NC(ON=1)=CC=1C1=CC=CC=C1 WMTXVQUFOCIMHC-ZWKOTPCHSA-N 0.000 claims 1
WHIVJEXKFOXDPN-ZWKOTPCHSA-N [(2s,4r)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-4,5-dihydroxypentyl] n-(5-phenyl-1,2-oxazol-3-yl)carbamate Chemical compound C([C@@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)C[C@@H](O)CO)OC(=O)NC(=NO1)C=C1C1=CC=CC=C1 WHIVJEXKFOXDPN-ZWKOTPCHSA-N 0.000 claims 1
PHIFDXQWSHKXLO-RBUKOAKNSA-N [(2s,4r)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-4,5-dihydroxypentyl] n-(6-fluoro-2-hydroxy-1h-isoquinolin-3-yl)carbamate Chemical compound CN([C@H](COC(=O)NC=1N(CC2=CC=C(F)C=C2C=1)O)C[C@@H](O)CO)C(=O)NCC1=CC=CC(F)=C1Cl PHIFDXQWSHKXLO-RBUKOAKNSA-N 0.000 claims 1
XHRUTYOGFDLXAI-RBUKOAKNSA-N [(2s,4r)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-4,5-dihydroxypentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C[C@@H](O)CO)C(=O)NCC1=CC=CC(F)=C1Cl XHRUTYOGFDLXAI-RBUKOAKNSA-N 0.000 claims 1
IQXCHFJQHHQRPI-ZWKOTPCHSA-N [(2s,4r)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-4,5-dihydroxypentyl] n-[5-(3-fluorophenyl)-1,2-oxazol-3-yl]carbamate Chemical compound C([C@@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)C[C@@H](O)CO)OC(=O)NC(=NO1)C=C1C1=CC=CC(F)=C1 IQXCHFJQHHQRPI-ZWKOTPCHSA-N 0.000 claims 1
BICGFHYCRGUTIN-UZLBHIALSA-N [(2s,4r)-2-[(2-chlorophenyl)methylcarbamoyl-methylamino]-4-hydroxypentyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)C[C@H](O)C)C(=O)NCC1=CC=CC=C1Cl BICGFHYCRGUTIN-UZLBHIALSA-N 0.000 claims 1
HXQNENQXFZDDJK-RBUKOAKNSA-N [(2s,4r)-2-[acetyl-[(2,3-difluorophenyl)methylamino]amino]-4-hydroxy-5-phosphonooxypentyl] n-(5-phenyl-1,2-oxazol-3-yl)carbamate Chemical compound CC(=O)N([C@H](COC(=O)NC1=NOC(=C1)C=1C=CC=CC=1)C[C@@H](O)COP(O)(O)=O)NCC1=CC=CC(F)=C1F HXQNENQXFZDDJK-RBUKOAKNSA-N 0.000 claims 1
SXKBFVQUEZUZKK-JKSUJKDBSA-N [(2s,4r)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4-hydroxy-5-phosphonooxypentyl] n-(1,3-benzothiazol-2-yl)carbamate Chemical compound CC(=O)N([C@H](COC(=O)NC=1SC2=CC=CC=C2N=1)C[C@@H](O)COP(O)(O)=O)NCC1=CC=CC(F)=C1Cl SXKBFVQUEZUZKK-JKSUJKDBSA-N 0.000 claims 1
WCKBDBAAIBWDGK-JKSUJKDBSA-N [(2s,4r)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4-hydroxy-5-phosphonooxypentyl] n-(6-chloro-1,3-benzothiazol-2-yl)carbamate Chemical compound CC(=O)N([C@H](COC(=O)NC=1SC2=CC(Cl)=CC=C2N=1)C[C@@H](O)COP(O)(O)=O)NCC1=CC=CC(F)=C1Cl WCKBDBAAIBWDGK-JKSUJKDBSA-N 0.000 claims 1
INTOAFVFTVGIJQ-JKSUJKDBSA-N [(2s,4r)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4-hydroxy-5-phosphonooxypentyl] n-(6-fluoro-1,3-benzothiazol-2-yl)carbamate Chemical compound CC(=O)N([C@H](COC(=O)NC=1SC2=CC(F)=CC=C2N=1)C[C@@H](O)COP(O)(O)=O)NCC1=CC=CC(F)=C1Cl INTOAFVFTVGIJQ-JKSUJKDBSA-N 0.000 claims 1
VQGVPNKQIIOIOO-VQTJNVASSA-N [(2s,4r)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4-hydroxy-5-phosphonooxypentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C[C@@H](O)COP(O)(O)=O)NCC1=CC=CC(F)=C1Cl VQGVPNKQIIOIOO-VQTJNVASSA-N 0.000 claims 1
ZPFWKXFDWAWVQS-RBUKOAKNSA-N [(2s,4r)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4-hydroxy-5-phosphonooxypentyl] n-[5-(3-chlorophenyl)-1,2-oxazol-3-yl]carbamate Chemical compound CC(=O)N([C@H](COC(=O)NC1=NOC(=C1)C=1C=C(Cl)C=CC=1)C[C@@H](O)COP(O)(O)=O)NCC1=CC=CC(F)=C1Cl ZPFWKXFDWAWVQS-RBUKOAKNSA-N 0.000 claims 1
ZDMDGGILTLWAAP-RBUKOAKNSA-N [(2s,4r)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4-hydroxy-5-phosphonooxypentyl] n-[5-(3-fluorophenyl)-1,2-oxazol-3-yl]carbamate Chemical compound CC(=O)N([C@H](COC(=O)NC1=NOC(=C1)C=1C=C(F)C=CC=1)C[C@@H](O)COP(O)(O)=O)NCC1=CC=CC(F)=C1Cl ZDMDGGILTLWAAP-RBUKOAKNSA-N 0.000 claims 1
CQYCLWKQHDDDEQ-MOPGFXCFSA-N [(2s,4r)-4-[(2-aminoacetyl)amino]-1-[(2-chloro-3-fluorophenyl)methylcarbamoyl]pyrrolidin-2-yl]methyl n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound N1([C@H](COC(=O)NC=2N=CC3=CC=C(F)C=C3C=2)C[C@H](C1)NC(=O)CN)C(=O)NCC1=CC=CC(F)=C1Cl CQYCLWKQHDDDEQ-MOPGFXCFSA-N 0.000 claims 1
POQOKRRETJRPHT-OALUTQOASA-N [(2s,4s)-2-[(2,3-difluorophenyl)methylcarbamoyl-methylamino]-4,5-dihydroxypentyl] n-isoquinolin-3-ylcarbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)C[C@H](O)CO)C(=O)NCC1=CC=CC(F)=C1F POQOKRRETJRPHT-OALUTQOASA-N 0.000 claims 1
XHRUTYOGFDLXAI-OALUTQOASA-N [(2s,4s)-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-4,5-dihydroxypentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C[C@H](O)CO)C(=O)NCC1=CC=CC(F)=C1Cl XHRUTYOGFDLXAI-OALUTQOASA-N 0.000 claims 1
VQGVPNKQIIOIOO-PMACEKPBSA-N [(2s,4s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-4-hydroxy-5-phosphonooxypentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C[C@H](O)COP(O)(O)=O)NCC1=CC=CC(F)=C1Cl VQGVPNKQIIOIOO-PMACEKPBSA-N 0.000 claims 1
ZAGNPSXGEFYFHJ-OALUTQOASA-N [(2s,4s)-5-amino-2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-4-hydroxypentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C[C@H](O)CN)C(=O)NCC1=CC=CC(F)=C1Cl ZAGNPSXGEFYFHJ-OALUTQOASA-N 0.000 claims 1
LKQOGHQKUGXELT-AXUWQRLWSA-N [(4s)-4-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-[(6-fluoroisoquinolin-3-yl)carbamoyloxy]-2-hydroxypentyl] (2r)-2-amino-3-hydroxypropanoate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CC(O)COC(=O)[C@H](N)CO)NCC1=CC=CC(F)=C1Cl LKQOGHQKUGXELT-AXUWQRLWSA-N 0.000 claims 1
LKQOGHQKUGXELT-PDATXNNJSA-N [(4s)-4-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-[(6-fluoroisoquinolin-3-yl)carbamoyloxy]-2-hydroxypentyl] (2s)-2-amino-3-hydroxypropanoate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CC(O)COC(=O)[C@@H](N)CO)NCC1=CC=CC(F)=C1Cl LKQOGHQKUGXELT-PDATXNNJSA-N 0.000 claims 1
OPBMAWLZRHHXSK-IQAFUUOHSA-N [(4s)-4-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-[(6-fluoroisoquinolin-3-yl)carbamoyloxy]-2-hydroxypentyl] (2s)-2-amino-3-methylbutanoate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CC(O)COC(=O)[C@@H](N)C(C)C)NCC1=CC=CC(F)=C1Cl OPBMAWLZRHHXSK-IQAFUUOHSA-N 0.000 claims 1
CDEGHZGCJNBPCC-UHFFFAOYSA-N [1-(2-aminoacetyl)-4-[(2,3-dichlorophenyl)methylcarbamoyl]piperidin-4-yl]methyl n-(5-bromopyridin-2-yl)carbamate Chemical compound C1CN(C(=O)CN)CCC1(C(=O)NCC=1C(=C(Cl)C=CC=1)Cl)COC(=O)NC1=CC=C(Br)C=N1 CDEGHZGCJNBPCC-UHFFFAOYSA-N 0.000 claims 1
VARQFRMJFDUYRW-UHFFFAOYSA-N [1-(2-aminoacetyl)-4-[(2-chlorophenyl)methylcarbamoyl]piperidin-4-yl]methyl n-(4-methyl-1,3-benzothiazol-2-yl)carbamate Chemical compound N=1C=2C(C)=CC=CC=2SC=1NC(=O)OCC1(C(=O)NCC=2C(=CC=CC=2)Cl)CCN(C(=O)CN)CC1 VARQFRMJFDUYRW-UHFFFAOYSA-N 0.000 claims 1
LXKFTDIOKXHRDX-UHFFFAOYSA-N [1-(2-aminoacetyl)-4-[(2-chlorophenyl)methylcarbamoyl]piperidin-4-yl]methyl n-(5-phenyl-1,3,4-thiadiazol-2-yl)carbamate Chemical compound C1CN(C(=O)CN)CCC1(C(=O)NCC=1C(=CC=CC=1)Cl)COC(=O)NC1=NN=C(C=2C=CC=CC=2)S1 LXKFTDIOKXHRDX-UHFFFAOYSA-N 0.000 claims 1
AGPSPKAEBKPPQL-UHFFFAOYSA-N [1-(2-aminoacetyl)-4-[(2-chlorophenyl)methylcarbamoyl]piperidin-4-yl]methyl n-(6-methyl-1,3-benzothiazol-2-yl)carbamate Chemical compound S1C2=CC(C)=CC=C2N=C1NC(=O)OCC1(C(=O)NCC=2C(=CC=CC=2)Cl)CCN(C(=O)CN)CC1 AGPSPKAEBKPPQL-UHFFFAOYSA-N 0.000 claims 1
DSPBNHZJYYXVCV-UHFFFAOYSA-N [1-(2-aminoacetyl)-4-[(2-chlorophenyl)methylcarbamoyl]piperidin-4-yl]methyl n-[6-(trifluoromethyl)-1,3-benzothiazol-2-yl]carbamate Chemical compound C1CN(C(=O)CN)CCC1(C(=O)NCC=1C(=CC=CC=1)Cl)COC(=O)NC1=NC2=CC=C(C(F)(F)F)C=C2S1 DSPBNHZJYYXVCV-UHFFFAOYSA-N 0.000 claims 1
ITIMLIOIYCMBMX-UHFFFAOYSA-N [1-(2-aminoacetyl)-4-[(2-chlorophenyl)methylcarbamoyl]piperidin-4-yl]methyl n-isoquinolin-3-ylcarbamate Chemical compound C1CN(C(=O)CN)CCC1(C(=O)NCC=1C(=CC=CC=1)Cl)COC(=O)NC1=CC2=CC=CC=C2C=N1 ITIMLIOIYCMBMX-UHFFFAOYSA-N 0.000 claims 1
QTSYZQUODMYDOL-UHFFFAOYSA-N [1-(2-aminoacetyl)-4-[(2-chlorophenyl)methylcarbamoyl]piperidin-4-yl]methyl n-thiophen-2-ylcarbamate Chemical compound C1CN(C(=O)CN)CCC1(C(=O)NCC=1C(=CC=CC=1)Cl)COC(=O)NC1=CC=CS1 QTSYZQUODMYDOL-UHFFFAOYSA-N 0.000 claims 1
IDNZIAYMCKXWBD-UHFFFAOYSA-N [2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-3-(1-methylimidazol-2-yl)propyl] n-isoquinolin-3-ylcarbamate Chemical compound C=1C=CC(F)=C(Cl)C=1CNC(=O)N(C)C(COC(=O)NC=1N=CC2=CC=CC=C2C=1)CC1=NC=CN1C IDNZIAYMCKXWBD-UHFFFAOYSA-N 0.000 claims 1
TZICYEUBQZSBGY-UHFFFAOYSA-N [2-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-3-(1h-imidazol-2-yl)propyl] n-isoquinolin-3-ylcarbamate Chemical compound C=1C=CC(F)=C(Cl)C=1CNC(=O)N(C)C(COC(=O)NC=1N=CC2=CC=CC=C2C=1)CC1=NC=CN1 TZICYEUBQZSBGY-UHFFFAOYSA-N 0.000 claims 1
ZIMGSJCTWAYYTR-UHFFFAOYSA-N [3-[(2-chloro-3-fluorophenyl)methylcarbamoyl]-3-methylhex-5-enyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCC(C)(CC=C)C(=O)NCC1=CC=CC(F)=C1Cl ZIMGSJCTWAYYTR-UHFFFAOYSA-N 0.000 claims 1
NOYDWDYVPDDGLF-UHFFFAOYSA-N [3-[(2-chloro-3-fluorophenyl)methylcarbamoyl]-3-methylhexyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCC(C)(CCC)C(=O)NCC1=CC=CC(F)=C1Cl NOYDWDYVPDDGLF-UHFFFAOYSA-N 0.000 claims 1
DAVDXSDADTWEIP-UHFFFAOYSA-N [3-[(2-chloro-3-fluorophenyl)methylcarbamoyl]-5-(2,3-dihydroxypropanoylamino)-3-methylpentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCC(CCNC(=O)C(O)CO)(C)C(=O)NCC1=CC=CC(F)=C1Cl DAVDXSDADTWEIP-UHFFFAOYSA-N 0.000 claims 1
BILRWSPWSFWIMH-UHFFFAOYSA-N [3-[(2-chloro-3-fluorophenyl)methylcarbamoyl]-5-hydroxy-3-methylpentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCC(CCO)(C)C(=O)NCC1=CC=CC(F)=C1Cl BILRWSPWSFWIMH-UHFFFAOYSA-N 0.000 claims 1
ZBRJCZMILXMOKH-UHFFFAOYSA-N [3-[(2-chloro-3-fluorophenyl)methylcarbamoyl]-6,7-dihydroxy-3-methylheptyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCC(C)(CCC(O)CO)C(=O)NCC1=CC=CC(F)=C1Cl ZBRJCZMILXMOKH-UHFFFAOYSA-N 0.000 claims 1
RABCQFVRVRZQMG-UHFFFAOYSA-N [3-[(2-chloro-3-fluorophenyl)methylcarbamoyl]-6-hydroxy-3-methylhexyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCC(CCCO)(C)C(=O)NCC1=CC=CC(F)=C1Cl RABCQFVRVRZQMG-UHFFFAOYSA-N 0.000 claims 1
IWIAAIWVHFUZDY-UHFFFAOYSA-N [4-[(2-chloro-3-fluorophenyl)methylamino]-3,3-dimethyl-4-oxobutyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCC(C)(C)C(=O)NCC1=CC=CC(F)=C1Cl IWIAAIWVHFUZDY-UHFFFAOYSA-N 0.000 claims 1
MODJKUSLHRLDJP-UHFFFAOYSA-N [4-[(2-chloro-3-fluorophenyl)methylamino]-3-methyl-4-oxobutyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCC(C)C(=O)NCC1=CC=CC(F)=C1Cl MODJKUSLHRLDJP-UHFFFAOYSA-N 0.000 claims 1
QCNJDEHZHGAQSH-UHFFFAOYSA-N [5-[(2-aminoacetyl)amino]-3-[(2-chloro-3-fluorophenyl)methylcarbamoyl]-3-methylpentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCC(CCNC(=O)CN)(C)C(=O)NCC1=CC=CC(F)=C1Cl QCNJDEHZHGAQSH-UHFFFAOYSA-N 0.000 claims 1
FRJUFFIXWJGUOP-LWAJAQLZSA-N [5-[[(2s)-2-amino-3-hydroxypropanoyl]amino]-3-[(2-chloro-3-fluorophenyl)methylcarbamoyl]-3-methylpentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCC(CCNC(=O)[C@@H](N)CO)(C)C(=O)NCC1=CC=CC(F)=C1Cl FRJUFFIXWJGUOP-LWAJAQLZSA-N 0.000 claims 1
JZHJKLBRUSATPN-UHFFFAOYSA-N [5-amino-3-[(2-chloro-3-fluorophenyl)methylcarbamoyl]-3-methylpentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCC(CCN)(C)C(=O)NCC1=CC=CC(F)=C1Cl JZHJKLBRUSATPN-UHFFFAOYSA-N 0.000 claims 1
YJMVWSKZHVEXIZ-UHFFFAOYSA-N [5-amino-3-[(2-chloro-4-fluorophenyl)methylcarbamoyl]-3-methylpentyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCC(CCN)(C)C(=O)NCC1=CC=C(F)C=C1Cl YJMVWSKZHVEXIZ-UHFFFAOYSA-N 0.000 claims 1
QSDKHCBMAZULFU-UHFFFAOYSA-N [6-[(2-aminoacetyl)amino]-3-[(2-chloro-3-fluorophenyl)methylcarbamoyl]-3-methylhexyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCC(CCCNC(=O)CN)(C)C(=O)NCC1=CC=CC(F)=C1Cl QSDKHCBMAZULFU-UHFFFAOYSA-N 0.000 claims 1
OUTXNGWCUMLRNK-UHFFFAOYSA-N [6-amino-3-[(2-chloro-3-fluorophenyl)methylcarbamoyl]-3-methylhexyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCC(CCCN)(C)C(=O)NCC1=CC=CC(F)=C1Cl OUTXNGWCUMLRNK-UHFFFAOYSA-N 0.000 claims 1
VONYQZAORIPTTB-UHFFFAOYSA-N [7-[(2-aminoacetyl)amino]-3-[(2-chloro-3-fluorophenyl)methylcarbamoyl]-3-methylheptyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCC(CCCCNC(=O)CN)(C)C(=O)NCC1=CC=CC(F)=C1Cl VONYQZAORIPTTB-UHFFFAOYSA-N 0.000 claims 1
AHMFUGVRUYGQPX-UHFFFAOYSA-N [7-amino-3-[(2-chloro-3-fluorophenyl)methylcarbamoyl]-3-methylheptyl] n-(6-fluoroisoquinolin-3-yl)carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCC(CCCCN)(C)C(=O)NCC1=CC=CC(F)=C1Cl AHMFUGVRUYGQPX-UHFFFAOYSA-N 0.000 claims 1
239000000443 aerosol Substances 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 claims 1
125000004103 aminoalkyl group Chemical group 0.000 claims 1
PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims 1
208000006673 asthma Diseases 0.000 claims 1
UGUUDTWORXNLAK-UHFFFAOYSA-N azidoalcohol Chemical compound ON=[N+]=[N-] UGUUDTWORXNLAK-UHFFFAOYSA-N 0.000 claims 1
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
CMBUTBAXZXBQGV-VWLOTQADSA-N benzyl N-[(2S)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-3-[(6-fluoroisoquinolin-3-yl)carbamoyloxy]propyl]carbamate Chemical compound ClC1=C(C=CC=C1F)CNN(C(=O)C)[C@H](COC(=O)NC=1N=CC2=CC=C(C=C2C1)F)CNC(=O)OCC1=CC=CC=C1 CMBUTBAXZXBQGV-VWLOTQADSA-N 0.000 claims 1
UMWZZAJHUNJVEI-PVCWFJFTSA-N benzyl n-[(5s)-5-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-1,1-difluoro-6-[(6-fluoroisoquinolin-3-yl)carbamoyloxy]hexan-2-yl]carbamate Chemical compound C([C@H](N(C)C(=O)NCC=1C(=C(F)C=CC=1)Cl)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CC(C(F)F)NC(=O)OCC1=CC=CC=C1 UMWZZAJHUNJVEI-PVCWFJFTSA-N 0.000 claims 1
GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims 1
230000007885 bronchoconstriction Effects 0.000 claims 1
DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
DWSYMNWJOYKKCK-UHFFFAOYSA-N butyl diethyl phosphate Chemical compound CCCCOP(=O)(OCC)OCC DWSYMNWJOYKKCK-UHFFFAOYSA-N 0.000 claims 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
239000002775 capsule Substances 0.000 claims 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
150000007942 carboxylates Chemical class 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
125000004093 cyano group Chemical group *C#N 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
ITJPTURSPJESQC-UHFFFAOYSA-N diethyl pentyl phosphate Chemical compound CCCCCOP(=O)(OCC)OCC ITJPTURSPJESQC-UHFFFAOYSA-N 0.000 claims 1
NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
201000011191 dyskinesia of esophagus Diseases 0.000 claims 1
LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 claims 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 claims 1
VDRBDINALVEVEB-UHFFFAOYSA-N hexyl dimethyl phosphate Chemical compound CCCCCCOP(=O)(OC)OC VDRBDINALVEVEB-UHFFFAOYSA-N 0.000 claims 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
201000001881 impotence Diseases 0.000 claims 1
208000002551 irritable bowel syndrome Diseases 0.000 claims 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
HVLHXIVRXGSVJC-UHFFFAOYSA-N isocyanato propanoate Chemical compound CCC(=O)ON=C=O HVLHXIVRXGSVJC-UHFFFAOYSA-N 0.000 claims 1
125000000842 isoxazolyl group Chemical group 0.000 claims 1
208000037805 labour Diseases 0.000 claims 1
239000007788 liquid Substances 0.000 claims 1
125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims 1
238000000034 method Methods 0.000 claims 1
BHXIROMQXDGQLY-FQEVSTJZSA-N methyl (4s)-4-[acetyl-[(2,3-difluorophenyl)methylamino]amino]-5-[(6-fluoroisoquinolin-3-yl)carbamoyloxy]pentanoate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CCC(=O)OC)NCC1=CC=CC(F)=C1F BHXIROMQXDGQLY-FQEVSTJZSA-N 0.000 claims 1
GPPZSESNHDVRLA-OAQYLSRUSA-N methyl (5r)-5-[acetyl-[(2,3-difluorophenyl)methylamino]amino]-6-(isoquinolin-3-ylcarbamoyloxy)hexanoate Chemical compound CC(=O)N([C@@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)CCCC(=O)OC)NCC1=CC=CC(F)=C1F GPPZSESNHDVRLA-OAQYLSRUSA-N 0.000 claims 1
XRIMHRZWOANPLW-FQEVSTJZSA-N methyl (5s)-5-[[2-[(2,3-difluorophenyl)methylamino]-2-oxoethyl]amino]-6-[[5-(4-methylphenyl)-1,2-oxazol-3-yl]carbamoyloxy]hexanoate Chemical compound C([C@H](CCCC(=O)OC)NCC(=O)NCC=1C(=C(F)C=CC=1)F)OC(=O)NC(=NO1)C=C1C1=CC=C(C)C=C1 XRIMHRZWOANPLW-FQEVSTJZSA-N 0.000 claims 1
UVMPXVLAGSCZHW-NRFANRHFSA-N methyl (5s)-5-[acetyl-[(2,3-dichlorophenyl)methylamino]amino]-6-(isoquinolin-3-ylcarbamoyloxy)hexanoate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)CCCC(=O)OC)NCC1=CC=CC(Cl)=C1Cl UVMPXVLAGSCZHW-NRFANRHFSA-N 0.000 claims 1
XWTWKVOSDJRIQS-NRFANRHFSA-N methyl (5s)-5-[acetyl-[(2,3-difluorophenyl)methylamino]amino]-6-[(2-methyl-5-phenylpyrazol-3-yl)carbamoyloxy]hexanoate Chemical compound C([C@H](CCCC(=O)OC)N(NCC=1C(=C(F)C=CC=1)F)C(C)=O)OC(=O)NC(N(N=1)C)=CC=1C1=CC=CC=C1 XWTWKVOSDJRIQS-NRFANRHFSA-N 0.000 claims 1
CKHFCBWPWCWXJN-KRWDZBQOSA-N methyl (5s)-5-[acetyl-[(2,3-difluorophenyl)methylamino]amino]-6-[(5-tert-butyl-1,2-oxazol-3-yl)carbamoyloxy]hexanoate Chemical compound C([C@H](CCCC(=O)OC)N(NCC=1C(=C(F)C=CC=1)F)C(C)=O)OC(=O)NC=1C=C(C(C)(C)C)ON=1 CKHFCBWPWCWXJN-KRWDZBQOSA-N 0.000 claims 1
LWTVKENLUMHYOD-KRWDZBQOSA-N methyl (5s)-5-[acetyl-[(2,3-difluorophenyl)methylamino]amino]-6-[[5-(2-fluorophenyl)-1,3,4-thiadiazol-2-yl]carbamoyloxy]hexanoate Chemical compound C([C@H](CCCC(=O)OC)N(NCC=1C(=C(F)C=CC=1)F)C(C)=O)OC(=O)NC(S1)=NN=C1C1=CC=CC=C1F LWTVKENLUMHYOD-KRWDZBQOSA-N 0.000 claims 1
RUHMKWCISDRRTF-IBGZPJMESA-N methyl (5s)-5-[acetyl-[(2,3-difluorophenyl)methylamino]amino]-6-[[5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl]carbamoyloxy]hexanoate Chemical compound C([C@H](CCCC(=O)OC)N(NCC=1C(=C(F)C=CC=1)F)C(C)=O)OC(=O)NC(S1)=NN=C1C1=CC=C(Br)C=C1 RUHMKWCISDRRTF-IBGZPJMESA-N 0.000 claims 1
ICQCKQRFKGZXDR-FQEVSTJZSA-N methyl (5s)-5-[acetyl-[(2,3-difluorophenyl)methylamino]amino]-6-[[5-(4-cyanophenyl)-1,3,4-thiadiazol-2-yl]carbamoyloxy]hexanoate Chemical compound C([C@H](CCCC(=O)OC)N(NCC=1C(=C(F)C=CC=1)F)C(C)=O)OC(=O)NC(S1)=NN=C1C1=CC=C(C#N)C=C1 ICQCKQRFKGZXDR-FQEVSTJZSA-N 0.000 claims 1
MOIUGWXMLJKUIK-IBGZPJMESA-N methyl (5s)-5-[acetyl-[(2,3-difluorophenyl)methylamino]amino]-6-[[5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl]carbamoyloxy]hexanoate Chemical compound C([C@H](CCCC(=O)OC)N(NCC=1C(=C(F)C=CC=1)F)C(C)=O)OC(=O)NC(S1)=NN=C1C1=CC=C(OC)C=C1 MOIUGWXMLJKUIK-IBGZPJMESA-N 0.000 claims 1
WICWVCCLEIXRQP-FQEVSTJZSA-N methyl (5s)-5-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-6-(2,7-naphthyridin-3-ylcarbamoyloxy)hexanoate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CN=CC=C2C=1)CCCC(=O)OC)NCC1=CC=CC(F)=C1Cl WICWVCCLEIXRQP-FQEVSTJZSA-N 0.000 claims 1
KUENXMOJKRSHHG-QFIPXVFZSA-N methyl (5s)-5-[acetyl-[(2-chloro-4-fluorophenyl)methylamino]amino]-6-(isoquinolin-3-ylcarbamoyloxy)hexanoate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)CCCC(=O)OC)NCC1=CC=C(F)C=C1Cl KUENXMOJKRSHHG-QFIPXVFZSA-N 0.000 claims 1
CSSIICKTWVZLQW-QFIPXVFZSA-N methyl (5s)-5-[acetyl-[(2-chlorophenyl)methylamino]amino]-6-(isoquinolin-3-ylcarbamoyloxy)hexanoate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)CCCC(=O)OC)NCC1=CC=CC=C1Cl CSSIICKTWVZLQW-QFIPXVFZSA-N 0.000 claims 1
XPXSUVOWUXDJEB-NRFANRHFSA-N methyl (5s)-5-[acetyl-[(3-chloro-2-fluorophenyl)methylamino]amino]-6-(isoquinolin-3-ylcarbamoyloxy)hexanoate Chemical compound CC(=O)N([C@H](COC(=O)NC=1N=CC2=CC=CC=C2C=1)CCCC(=O)OC)NCC1=CC=CC(Cl)=C1F XPXSUVOWUXDJEB-NRFANRHFSA-N 0.000 claims 1
ODQZNBWVRPKMKN-UHFFFAOYSA-N methyl piperazine-2-carboxylate Chemical compound COC(=O)C1CNCCN1 ODQZNBWVRPKMKN-UHFFFAOYSA-N 0.000 claims 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
ATHHXGZTWNVVOU-UHFFFAOYSA-N monomethyl-formamide Natural products CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims 1
210000003205 muscle Anatomy 0.000 claims 1
UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 claims 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
235000005152 nicotinamide Nutrition 0.000 claims 1
239000011570 nicotinamide Substances 0.000 claims 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
125000001715 oxadiazolyl group Chemical group 0.000 claims 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
239000000843 powder Substances 0.000 claims 1
LZMATGARSSLFMQ-UHFFFAOYSA-N propan-2-ylurea Chemical compound CC(C)NC(N)=O LZMATGARSSLFMQ-UHFFFAOYSA-N 0.000 claims 1
125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 1
125000003373 pyrazinyl group Chemical group 0.000 claims 1
125000003226 pyrazolyl group Chemical group 0.000 claims 1
NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 1
125000005493 quinolyl group Chemical group 0.000 claims 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
238000007634 remodeling Methods 0.000 claims 1
210000002460 smooth muscle Anatomy 0.000 claims 1
239000000829 suppository Substances 0.000 claims 1
239000000725 suspension Substances 0.000 claims 1
239000003826 tablet Substances 0.000 claims 1
DCIAHNZYMKFMKZ-QHCPKHFHSA-N tert-butyl N-[[(4S)-4-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-5-[(6-fluoroisoquinolin-3-yl)carbamoyloxy]pentyl]sulfamoyl]carbamate Chemical compound CC(=O)N([C@@H](CCCNS(=O)(=O)NC(=O)OC(C)(C)C)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)NCC1=CC=CC(F)=C1Cl DCIAHNZYMKFMKZ-QHCPKHFHSA-N 0.000 claims 1
WXGIKZYRVVBFOQ-RUBXLXHKSA-N tert-butyl n-[(2s)-1-[[3-[(2-chloro-3-fluorophenyl)methylcarbamoyl]-5-[(6-fluoroisoquinolin-3-yl)carbamoyloxy]-3-methylpentyl]amino]-3-hydroxy-1-oxopropan-2-yl]carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCC(C)(CCNC(=O)[C@H](CO)NC(=O)OC(C)(C)C)C(=O)NCC1=CC=CC(F)=C1Cl WXGIKZYRVVBFOQ-RUBXLXHKSA-N 0.000 claims 1
JLTZMJZRXZAKIL-NRFANRHFSA-N tert-butyl n-[(2s)-2-[acetyl-[(2-chloro-3-fluorophenyl)methylamino]amino]-3-[(6-fluoroisoquinolin-3-yl)carbamoyloxy]propyl]carbamate Chemical compound CC(=O)N([C@@H](CNC(=O)OC(C)(C)C)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)NCC1=CC=CC(F)=C1Cl JLTZMJZRXZAKIL-NRFANRHFSA-N 0.000 claims 1
QPYGVIOKHHGQMA-NRFANRHFSA-N tert-butyl n-[(4s)-4-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-2,2-difluoro-5-[(6-fluoroisoquinolin-3-yl)carbamoyloxy]pentyl]carbamate Chemical compound CN([C@H](COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)CC(F)(F)CNC(=O)OC(C)(C)C)C(=O)NCC1=CC=CC(F)=C1Cl QPYGVIOKHHGQMA-NRFANRHFSA-N 0.000 claims 1
GNDMUDSNIZKJTA-QFIPXVFZSA-N tert-butyl n-[(4s)-4-[(2-chloro-3-fluorophenyl)methylcarbamoyl-methylamino]-5-[(6-fluoroisoquinolin-3-yl)carbamoyloxy]pentyl]carbamate Chemical compound CN([C@@H](CCCNC(=O)OC(C)(C)C)COC(=O)NC=1N=CC2=CC=C(F)C=C2C=1)C(=O)NCC1=CC=CC(F)=C1Cl GNDMUDSNIZKJTA-QFIPXVFZSA-N 0.000 claims 1
GLLYZBNBSSUSAD-UHFFFAOYSA-N tert-butyl n-[2-[[2-[(2-chloro-3-fluorophenyl)methylcarbamoyl]-4-[(6-fluoroisoquinolin-3-yl)carbamoyloxy]-2-methylbutyl]amino]-2-oxoethyl]carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCC(C)(CNC(=O)CNC(=O)OC(C)(C)C)C(=O)NCC1=CC=CC(F)=C1Cl GLLYZBNBSSUSAD-UHFFFAOYSA-N 0.000 claims 1
OTMSETWSXLUIMK-UHFFFAOYSA-N tert-butyl n-[2-[[3-[(2-chloro-3-fluorophenyl)methylcarbamoyl]-5-[(6-fluoroisoquinolin-3-yl)carbamoyloxy]-3-methylpentyl]amino]-2-oxoethyl]carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCC(C)(CCNC(=O)CNC(=O)OC(C)(C)C)C(=O)NCC1=CC=CC(F)=C1Cl OTMSETWSXLUIMK-UHFFFAOYSA-N 0.000 claims 1
UYWASBMTPHWEGY-UHFFFAOYSA-N tert-butyl n-[3-[(2-chloro-3-fluorophenyl)methylcarbamoyl]-5-[(6-fluoroisoquinolin-3-yl)carbamoyloxy]-3-methylpentyl]carbamate Chemical compound C=1C2=CC(F)=CC=C2C=NC=1NC(=O)OCCC(C)(CCNC(=O)OC(C)(C)C)C(=O)NCC1=CC=CC(F)=C1Cl UYWASBMTPHWEGY-UHFFFAOYSA-N 0.000 claims 1
125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
125000001113 thiadiazolyl group Chemical group 0.000 claims 1
125000000335 thiazolyl group Chemical group 0.000 claims 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
238000004007 reversed phase HPLC Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 1
239000000706 filtrate Substances 0.000 description 1

JP2010521009A 2007-08-15 2008-08-11 ある種の化学物質、組成物、および方法 Expired - Fee Related JP5670731B2 (ja)