NZ552187A - Thiophene-2-carboxamide derivatives - Google Patents

Info

Publication number

NZ552187A

NZ552187A NZ552187A NZ55218705A NZ552187A NZ 552187 A NZ552187 A NZ 552187A NZ 552187 A NZ552187 A NZ 552187A NZ 55218705 A NZ55218705 A NZ 55218705A NZ 552187 A NZ552187 A NZ 552187A

Authority

NZ

New Zealand

Prior art keywords

chloro

methyl

thiophene

phenyl

isoxazol

Prior art date

2004-06-18

Links

• Espacenet
• Global Dossier
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• DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical class NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 title claims abstract description 139
• 150000001875 compounds Chemical class 0.000 claims abstract description 605
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 151
• 239000000203 mixture Substances 0.000 claims abstract description 136
• 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 120
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 72
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 64
• 125000001424 substituent group Chemical group 0.000 claims abstract description 64
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 61
• 150000003839 salts Chemical class 0.000 claims abstract description 40
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 36
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 33
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 30
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 28
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 22
• 239000001257 hydrogen Substances 0.000 claims abstract description 22
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 22
• 125000005843 halogen group Chemical group 0.000 claims abstract description 21
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 20
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 19
• 208000007536 Thrombosis Diseases 0.000 claims abstract description 14
• 239000003814 drug Substances 0.000 claims abstract description 12
• 241000124008 Mammalia Species 0.000 claims abstract description 9
• 239000003146 anticoagulant agent Substances 0.000 claims abstract description 9
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
• 239000001301 oxygen Substances 0.000 claims abstract description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 7
• 230000001732 thrombotic effect Effects 0.000 claims abstract description 6
• 206010047249 Venous thrombosis Diseases 0.000 claims abstract description 5
• 208000004476 Acute Coronary Syndrome Diseases 0.000 claims abstract description 3
• 206010002383 Angina Pectoris Diseases 0.000 claims abstract description 3
• 206010002388 Angina unstable Diseases 0.000 claims abstract description 3
• 208000033386 Buerger disease Diseases 0.000 claims abstract description 3
• 206010053567 Coagulopathies Diseases 0.000 claims abstract description 3
• 206010014498 Embolic stroke Diseases 0.000 claims abstract description 3
• 208000010378 Pulmonary Embolism Diseases 0.000 claims abstract description 3
• 206010043540 Thromboangiitis obliterans Diseases 0.000 claims abstract description 3
• 206010043647 Thrombotic Stroke Diseases 0.000 claims abstract description 3
• 201000007023 Thrombotic Thrombocytopenic Purpura Diseases 0.000 claims abstract description 3
• 208000032109 Transient ischaemic attack Diseases 0.000 claims abstract description 3
• 208000007814 Unstable Angina Diseases 0.000 claims abstract description 3
• 208000015294 blood coagulation disease Diseases 0.000 claims abstract description 3
• 230000000747 cardiac effect Effects 0.000 claims abstract description 3
• 208000009190 disseminated intravascular coagulation Diseases 0.000 claims abstract description 3
• 210000003709 heart valve Anatomy 0.000 claims abstract description 3
• 201000004332 intermediate coronary syndrome Diseases 0.000 claims abstract description 3
• 238000004519 manufacturing process Methods 0.000 claims abstract description 3
• 230000001404 mediated effect Effects 0.000 claims abstract description 3
• 208000010125 myocardial infarction Diseases 0.000 claims abstract description 3
• 238000010577 post-coronary angioplasty Methods 0.000 claims abstract description 3
• 208000011580 syndromic disease Diseases 0.000 claims abstract description 3
• 238000002560 therapeutic procedure Methods 0.000 claims abstract description 3
• 201000010875 transient cerebral ischemia Diseases 0.000 claims abstract description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 9
• 206010051055 Deep vein thrombosis Diseases 0.000 claims abstract 2
• 238000000034 method Methods 0.000 claims description 406
• QZLSBOVWPHXCLT-UHFFFAOYSA-N 5-chlorothiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Cl)S1 QZLSBOVWPHXCLT-UHFFFAOYSA-N 0.000 claims description 319
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 174
• -1 pyridimidine Chemical compound 0.000 claims description 113
• 125000003118 aryl group Chemical group 0.000 claims description 73
• 150000002367 halogens Chemical class 0.000 claims description 51
• 150000003857 carboxamides Chemical class 0.000 claims description 46
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 38
• 125000004429 atom Chemical group 0.000 claims description 36
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 34
• 125000005842 heteroatom Chemical group 0.000 claims description 33
• 229920006395 saturated elastomer Polymers 0.000 claims description 31
• 125000001188 haloalkyl group Chemical group 0.000 claims description 30
• 239000002253 acid Substances 0.000 claims description 28
• 229910052799 carbon Inorganic materials 0.000 claims description 28
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 26
• 125000002947 alkylene group Chemical group 0.000 claims description 24
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 19
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 19
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
• 125000004450 alkenylene group Chemical group 0.000 claims description 17
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 15
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 15
• 125000004419 alkynylene group Chemical group 0.000 claims description 14
• 150000001408 amides Chemical class 0.000 claims description 14
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 13
• 125000003971 isoxazolinyl group Chemical group 0.000 claims description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 10
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
• 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims description 10
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
• 125000002619 bicyclic group Chemical group 0.000 claims description 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
• 125000002950 monocyclic group Chemical group 0.000 claims description 9
• 125000004434 sulfur atom Chemical group 0.000 claims description 9
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
• 230000002401 inhibitory effect Effects 0.000 claims description 8
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
• 230000015271 coagulation Effects 0.000 claims description 6
• 238000005345 coagulation Methods 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 6
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
• 238000000338 in vitro Methods 0.000 claims description 5
• SRJOCJYGOFTFLH-UHFFFAOYSA-M piperidine-4-carboxylate Chemical compound [O-]C(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-M 0.000 claims description 5
• 229930192474 thiophene Natural products 0.000 claims description 5
• 229910052727 yttrium Inorganic materials 0.000 claims description 5
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
• 210000004369 blood Anatomy 0.000 claims description 4
• 239000008280 blood Substances 0.000 claims description 4
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims description 3
• BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 3
• YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 claims description 3
• FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 3
• QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 3
• WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims description 3
• DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 claims description 3
• WMSNMRKQRRALOR-UHFFFAOYSA-N 4-[5-[[(5-chlorothiophene-2-carbonyl)amino]methyl]-4,5-dihydro-1,2-oxazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1)=NOC1CNC(=O)C1=CC=C(Cl)S1 WMSNMRKQRRALOR-UHFFFAOYSA-N 0.000 claims description 3
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 3
• ZIZBWBUESVSKIA-UHFFFAOYSA-N 5-chloro-n-[(3-phenyl-1,2-oxazol-5-yl)methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CC(C=2C=CC=CC=2)=NO1 ZIZBWBUESVSKIA-UHFFFAOYSA-N 0.000 claims description 3
• WCXXGOULPJCIGY-UHFFFAOYSA-N 5-chloro-n-[(3-phenyl-4,5-dihydro-1,2-oxazol-5-yl)methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1ON=C(C=2C=CC=CC=2)C1 WCXXGOULPJCIGY-UHFFFAOYSA-N 0.000 claims description 3
• BPZBWVROIASGRE-UHFFFAOYSA-N 5-chloro-n-[(3-piperidin-4-yl-1,2-oxazol-5-yl)methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CC(C2CCNCC2)=NO1 BPZBWVROIASGRE-UHFFFAOYSA-N 0.000 claims description 3
• VWSFDANIIDCCRZ-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(5-methyl-2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1=C(C)C=CC(=O)N1C1=CC=C(N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=C1 VWSFDANIIDCCRZ-UHFFFAOYSA-N 0.000 claims description 3
• FCZZAWFYUPMFRJ-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(n,n-dimethylcarbamimidoyl)phenyl]imidazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)C)=CC=C1N1C=C(CNC(=O)C=2SC(Cl)=CC=2)N=C1 FCZZAWFYUPMFRJ-UHFFFAOYSA-N 0.000 claims description 3
• YTQMATLMIUBDCS-UHFFFAOYSA-N 5-chloro-n-[[3-(3-pyridin-3-ylphenyl)-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CC(C=2C=C(C=CC=2)C=2C=NC=CC=2)=NO1 YTQMATLMIUBDCS-UHFFFAOYSA-N 0.000 claims description 3
• XTGMYFCSBMFJES-UHFFFAOYSA-N 5-chloro-n-[[3-(4-cyanophenyl)-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CC(C=2C=CC(=CC=2)C#N)=NO1 XTGMYFCSBMFJES-UHFFFAOYSA-N 0.000 claims description 3
• FQFJGBNPVKERDX-UHFFFAOYSA-N 5-chloro-n-[[3-(4-methoxyphenyl)-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=NOC(CNC(=O)C=2SC(Cl)=CC=2)=C1 FQFJGBNPVKERDX-UHFFFAOYSA-N 0.000 claims description 3
• ZYICNRUPDOYIPV-UHFFFAOYSA-N 5-chloro-n-[[3-(4-methylphenyl)-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C)=CC=C1C1=NOC(CNC(=O)C=2SC(Cl)=CC=2)=C1 ZYICNRUPDOYIPV-UHFFFAOYSA-N 0.000 claims description 3
• ZIHUWXDRJQVQPT-UHFFFAOYSA-N 5-chloro-n-[[3-(4-pyridin-3-ylphenyl)-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CC(C=2C=CC(=CC=2)C=2C=NC=CC=2)=NO1 ZIHUWXDRJQVQPT-UHFFFAOYSA-N 0.000 claims description 3
• ADTJJZXARPXFNF-UHFFFAOYSA-N 5-chloro-n-[[3-(4-pyridin-4-ylphenyl)-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CC(C=2C=CC(=CC=2)C=2C=CN=CC=2)=NO1 ADTJJZXARPXFNF-UHFFFAOYSA-N 0.000 claims description 3
• UPEIREKSUWZFLA-UHFFFAOYSA-N 5-chloro-n-[[3-[2-(4-methoxyphenoxy)-4-(1-methyl-4,5-dihydroimidazol-2-yl)phenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(OC)=CC=C1OC1=CC(C=2N(CCN=2)C)=CC=C1C1=NOC(CNC(=O)C=2SC(Cl)=CC=2)=C1 UPEIREKSUWZFLA-UHFFFAOYSA-N 0.000 claims description 3
• CURRBYUDQZROFX-UHFFFAOYSA-N 5-chloro-n-[[3-[2-ethoxy-4-(1-methyl-4,5-dihydroimidazol-2-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound CCOC1=CC(C=2N(CCN=2)C)=CC=C1C(C1)=NOC1CNC(=O)C1=CC=C(Cl)S1 CURRBYUDQZROFX-UHFFFAOYSA-N 0.000 claims description 3
• VWTYUJLVLFMEOM-UHFFFAOYSA-N 5-chloro-n-[[3-[2-methylsulfanyl-4-(pyrrolidine-1-carboximidoyl)phenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound CSC1=CC(C(=N)N2CCCC2)=CC=C1C(=NO1)C=C1CNC(=O)C1=CC=C(Cl)S1 VWTYUJLVLFMEOM-UHFFFAOYSA-N 0.000 claims description 3
• YFOIFNZMFMSUNB-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(1-methyl-4,5-dihydroimidazol-2-yl)-2-morpholin-4-ylphenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound CN1CCN=C1C(C=C1N2CCOCC2)=CC=C1C1=NOC(CNC(=O)C=2SC(Cl)=CC=2)=C1 YFOIFNZMFMSUNB-UHFFFAOYSA-N 0.000 claims description 3
• LWIDVUORNBJLOB-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(1-methyl-4,5-dihydroimidazol-2-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound CN1CCN=C1C1=CC=C(C=2CC(CNC(=O)C=3SC(Cl)=CC=3)ON=2)C=C1 LWIDVUORNBJLOB-UHFFFAOYSA-N 0.000 claims description 3
• MUKQOUFQVFMRME-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(n,n-dimethylcarbamimidoyl)-2-[2-methoxyethyl(methyl)amino]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound COCCN(C)C1=CC(C(=N)N(C)C)=CC=C1C(C1)=NOC1CNC(=O)C1=CC=C(Cl)S1 MUKQOUFQVFMRME-UHFFFAOYSA-N 0.000 claims description 3
• TUUMMUYISIIIEG-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(n,n-dimethylcarbamimidoyl)-2-fluorophenyl]-2,3-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound FC1=CC(C(=N)N(C)C)=CC=C1C1C=C(CNC(=O)C=2SC(Cl)=CC=2)ON1 TUUMMUYISIIIEG-UHFFFAOYSA-N 0.000 claims description 3
• HDQXJOJPVCJDLN-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(n,n-dimethylcarbamimidoyl)-2-methoxyphenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound COC1=CC(C(=N)N(C)C)=CC=C1C(C1)=NOC1CNC(=O)C1=CC=C(Cl)S1 HDQXJOJPVCJDLN-UHFFFAOYSA-N 0.000 claims description 3
• YGQWWNWLGSWPJU-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(n-ethyl-n-methylcarbamimidoyl)phenyl]-5-methyl-4h-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)CC)=CC=C1C(C1)=NOC1(C)CNC(=O)C1=CC=C(Cl)S1 YGQWWNWLGSWPJU-UHFFFAOYSA-N 0.000 claims description 3
• OOFGMSFNOJHYRS-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(piperidine-1-carboximidoyl)-2-pyrrolidin-1-ylphenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1ON=C(C=2C(=CC(=CC=2)C(=N)N2CCCCC2)N2CCCC2)C1 OOFGMSFNOJHYRS-UHFFFAOYSA-N 0.000 claims description 3
• YSMQDPHMNDRLKQ-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[(3-methylpyridin-4-yl)amino]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound CC1=CN=CC=C1NC1=CC=C(C=2CC(CNC(=O)C=3SC(Cl)=CC=3)ON=2)C=C1 YSMQDPHMNDRLKQ-UHFFFAOYSA-N 0.000 claims description 3
• DRJRZOGOFCVNIS-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[2-[[2-methoxyethyl(methyl)amino]methyl]phenyl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound COCCN(C)CC1=CC=CC=C1C1=CC=C(C=2CC(CNC(=O)C=3SC(Cl)=CC=3)ON=2)C=C1 DRJRZOGOFCVNIS-UHFFFAOYSA-N 0.000 claims description 3
• QFLJBKVWAJNBME-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[n-(2-methoxyethyl)-n-methylcarbamimidoyl]phenyl]-1,2-oxazol-5-yl]methyl]-n-methylthiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)CCOC)=CC=C1C1=NOC(CN(C)C(=O)C=2SC(Cl)=CC=2)=C1 QFLJBKVWAJNBME-UHFFFAOYSA-N 0.000 claims description 3
• LCNACLACZBBXML-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[n-(2-methoxyethyl)-n-methylcarbamimidoyl]phenyl]-5-methyl-4h-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)CCOC)=CC=C1C(C1)=NOC1(C)CNC(=O)C1=CC=C(Cl)S1 LCNACLACZBBXML-UHFFFAOYSA-N 0.000 claims description 3
• GJQUEZXVJLLEFW-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[n-[2-(dimethylamino)ethyl]-n-methylcarbamimidoyl]phenyl]-1,2-oxazol-5-yl]methyl]-n-methylthiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)CCN(C)C)=CC=C1C1=NOC(CN(C)C(=O)C=2SC(Cl)=CC=2)=C1 GJQUEZXVJLLEFW-UHFFFAOYSA-N 0.000 claims description 3
• XZHNMYNVPRYOOC-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[n-[2-(dimethylamino)ethyl]-n-methylcarbamimidoyl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)CCN(C)C)=CC=C1C(C1)=NOC1CNC(=O)C1=CC=C(Cl)S1 XZHNMYNVPRYOOC-UHFFFAOYSA-N 0.000 claims description 3
• YSFBKMBUNSFYCF-UHFFFAOYSA-N 5-chloro-n-[[4-[4-(1-methyl-4,5-dihydroimidazol-2-yl)phenyl]-1,3-thiazol-2-yl]methyl]thiophene-2-carboxamide Chemical compound CN1CCN=C1C1=CC=C(C=2N=C(CNC(=O)C=3SC(Cl)=CC=3)SC=2)C=C1 YSFBKMBUNSFYCF-UHFFFAOYSA-N 0.000 claims description 3
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• IAOZMHAUCOEXDM-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(1-methyl-4,5-dihydroimidazol-2-yl)phenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound CN1CCN=C1C1=CC=C(C2=NOC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=C1 IAOZMHAUCOEXDM-UHFFFAOYSA-N 0.000 claims description 2
• YIMQZXOAFHXTDG-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(1-methyl-4,5-dihydroimidazol-2-yl)phenyl]phenyl]methyl]thiophene-2-carboxamide Chemical compound CN1CCN=C1C1=CC=C(C=2C=C(CNC(=O)C=3SC(Cl)=CC=3)C=CC=2)C=C1 YIMQZXOAFHXTDG-UHFFFAOYSA-N 0.000 claims description 2
• ZDWFKXNWDXPFCR-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(2-chlorophenyl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1ON=C(C=2C=CC(=CC=2)C=2C(=CC=CC=2)Cl)C1 ZDWFKXNWDXPFCR-UHFFFAOYSA-N 0.000 claims description 2
• RWWCKNDSGVGSPK-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(2-formylphenyl)phenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CC(C=2C=CC(=CC=2)C=2C(=CC=CC=2)C=O)=NO1 RWWCKNDSGVGSPK-UHFFFAOYSA-N 0.000 claims description 2
• SEPWBBFISRJQRG-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(2-formylphenyl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1ON=C(C=2C=CC(=CC=2)C=2C(=CC=CC=2)C=O)C1 SEPWBBFISRJQRG-UHFFFAOYSA-N 0.000 claims description 2
• WCDQLLDAMBAYCT-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(2-methylpyrrolidine-1-carbonyl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound CC1CCCN1C(=O)C1=CC=C(C=2CC(CNC(=O)C=3SC(Cl)=CC=3)ON=2)C=C1 WCDQLLDAMBAYCT-UHFFFAOYSA-N 0.000 claims description 2
• OEYWGDSPHMYUKL-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(2-methylsulfanylphenyl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound CSC1=CC=CC=C1C1=CC=C(C=2CC(CNC(=O)C=3SC(Cl)=CC=3)ON=2)C=C1 OEYWGDSPHMYUKL-UHFFFAOYSA-N 0.000 claims description 2
• LUSPCGRDHXMKJY-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(2-oxopiperidin-1-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1ON=C(C=2C=CC(=CC=2)N2C(CCCC2)=O)C1 LUSPCGRDHXMKJY-UHFFFAOYSA-N 0.000 claims description 2
• SYMWPWSMXCSKGV-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(2-oxopyridin-1-yl)phenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CC(C=2C=CC(=CC=2)N2C(C=CC=C2)=O)=NO1 SYMWPWSMXCSKGV-UHFFFAOYSA-N 0.000 claims description 2
• GSOPKPYARNNIAH-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(3-methyl-2-oxoimidazolidin-1-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound O=C1N(C)CCN1C1=CC=C(C=2CC(CNC(=O)C=3SC(Cl)=CC=3)ON=2)C=C1 GSOPKPYARNNIAH-UHFFFAOYSA-N 0.000 claims description 2
• MZAVNNXGGLWTQJ-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(3-oxomorpholin-4-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1ON=C(C=2C=CC(=CC=2)N2C(COCC2)=O)C1 MZAVNNXGGLWTQJ-UHFFFAOYSA-N 0.000 claims description 2
• SQWAXWWILGFCAD-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(3-oxothiomorpholin-4-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1ON=C(C=2C=CC(=CC=2)N2C(CSCC2)=O)C1 SQWAXWWILGFCAD-UHFFFAOYSA-N 0.000 claims description 2
• WLBNKKXWYGQSBV-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(4-fluoroanilino)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(F)=CC=C1NC1=CC=C(C=2CC(CNC(=O)C=3SC(Cl)=CC=3)ON=2)C=C1 WLBNKKXWYGQSBV-UHFFFAOYSA-N 0.000 claims description 2
• KWCAXMRQECRACF-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(4-methyl-2-oxopyridin-1-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound O=C1C=C(C)C=CN1C1=CC=C(C=2CC(CNC(=O)C=3SC(Cl)=CC=3)ON=2)C=C1 KWCAXMRQECRACF-UHFFFAOYSA-N 0.000 claims description 2
• DKJSKOOIRDRMOE-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(n'-methylcarbamimidoyl)phenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)NC)=CC=C1C1=NOC(CNC(=O)C=2SC(Cl)=CC=2)=C1 DKJSKOOIRDRMOE-UHFFFAOYSA-N 0.000 claims description 2
• FLBFEQHPRFGFBA-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(n,n-dimethylcarbamimidoyl)-2-methoxyphenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound COC1=CC(C(=N)N(C)C)=CC=C1C1=NOC(CNC(=O)C=2SC(Cl)=CC=2)=C1 FLBFEQHPRFGFBA-UHFFFAOYSA-N 0.000 claims description 2
• ZNQFAMBWAQNSFQ-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(n,n-dimethylcarbamimidoyl)-2-methylsulfanylphenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound CSC1=CC(C(=N)N(C)C)=CC=C1C(C1)=NOC1CNC(=O)C1=CC=C(Cl)S1 ZNQFAMBWAQNSFQ-UHFFFAOYSA-N 0.000 claims description 2
• IWHOQWRXSPXNKM-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(n,n-dimethylcarbamimidoyl)-2-morpholin-4-ylphenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1COCCN1C1=CC(C(=N)N(C)C)=CC=C1C(=NO1)C=C1CNC(=O)C1=CC=C(Cl)S1 IWHOQWRXSPXNKM-UHFFFAOYSA-N 0.000 claims description 2
• BKYUOBYEVIZXQZ-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(n,n-dimethylcarbamimidoyl)phenyl]-1,2-oxazol-5-yl]methyl]-n-methylthiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)C)=CC=C1C1=NOC(CN(C)C(=O)C=2SC(Cl)=CC=2)=C1 BKYUOBYEVIZXQZ-UHFFFAOYSA-N 0.000 claims description 2
• ZJVPMGUGQGRFSK-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(n,n-dimethylcarbamimidoyl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)C)=CC=C1C(C1)=NOC1CNC(=O)C1=CC=C(Cl)S1 ZJVPMGUGQGRFSK-UHFFFAOYSA-N 0.000 claims description 2
• OHTDNFSUMRLHBB-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(n-methyl-n-prop-2-ynylcarbamimidoyl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(CC#C)C)=CC=C1C(C1)=NOC1CNC(=O)C1=CC=C(Cl)S1 OHTDNFSUMRLHBB-UHFFFAOYSA-N 0.000 claims description 2
• LVVDVBHNRZMULC-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(n-methyl-n-propylcarbamimidoyl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)CCC)=CC=C1C(C1)=NOC1CNC(=O)C1=CC=C(Cl)S1 LVVDVBHNRZMULC-UHFFFAOYSA-N 0.000 claims description 2
• CHZFEHMVVXBLOV-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(piperidine-1-carboximidoyl)-2-propan-2-yloxyphenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound CC(C)OC1=CC(C(=N)N2CCCCC2)=CC=C1C(=NO1)C=C1CNC(=O)C1=CC=C(Cl)S1 CHZFEHMVVXBLOV-UHFFFAOYSA-N 0.000 claims description 2
• CCMYUQJGGTXDFJ-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(piperidine-1-carboximidoyl)phenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CC(C=2C=CC(=CC=2)C(=N)N2CCCCC2)=NO1 CCMYUQJGGTXDFJ-UHFFFAOYSA-N 0.000 claims description 2
• PDMQOLMXXRYRFL-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(pyridin-2-ylamino)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1ON=C(C=2C=CC(NC=3N=CC=CC=3)=CC=2)C1 PDMQOLMXXRYRFL-UHFFFAOYSA-N 0.000 claims description 2
• KFGNPJGHISPLKS-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(pyridin-4-ylamino)phenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CC(C=2C=CC(NC=3C=CN=CC=3)=CC=2)=NO1 KFGNPJGHISPLKS-UHFFFAOYSA-N 0.000 claims description 2
• SCODFBIAJZEVOR-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(pyrrolidine-1-carbonyl)phenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CC(C=2C=CC(=CC=2)C(=O)N2CCCC2)=NO1 SCODFBIAJZEVOR-UHFFFAOYSA-N 0.000 claims description 2
• MUBQYLKJPQAGMZ-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(pyrrolidine-1-carbonyl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1ON=C(C=2C=CC(=CC=2)C(=O)N2CCCC2)C1 MUBQYLKJPQAGMZ-UHFFFAOYSA-N 0.000 claims description 2
• AZBPVQNJIGBXEN-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[(1-methylpiperidin-4-yl)amino]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1CN(C)CCC1NC1=CC=C(C=2CC(CNC(=O)C=3SC(Cl)=CC=3)ON=2)C=C1 AZBPVQNJIGBXEN-UHFFFAOYSA-N 0.000 claims description 2
• JIRLQUVHZUABQD-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[2-(diethylamino)ethyl-methylcarbamoyl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=O)N(C)CCN(CC)CC)=CC=C1C(C1)=NOC1CNC(=O)C1=CC=C(Cl)S1 JIRLQUVHZUABQD-UHFFFAOYSA-N 0.000 claims description 2
• ZTHWFKOYHUAHLN-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[2-(hydroxymethyl)-4-methoxyphenyl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound OCC1=CC(OC)=CC=C1C1=CC=C(C=2CC(CNC(=O)C=3SC(Cl)=CC=3)ON=2)C=C1 ZTHWFKOYHUAHLN-UHFFFAOYSA-N 0.000 claims description 2
• XMYGVNFOBRELHM-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[2-[(4-methylpiperazin-1-yl)methyl]phenyl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1CN(C)CCN1CC1=CC=CC=C1C1=CC=C(C=2CC(CNC(=O)C=3SC(Cl)=CC=3)ON=2)C=C1 XMYGVNFOBRELHM-UHFFFAOYSA-N 0.000 claims description 2
• ZFVWQMQGCRIMER-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[3-[(dimethylamino)methyl]phenyl]phenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound CN(C)CC1=CC=CC(C=2C=CC(=CC=2)C2=NOC(CNC(=O)C=3SC(Cl)=CC=3)=C2)=C1 ZFVWQMQGCRIMER-UHFFFAOYSA-N 0.000 claims description 2
• HGLFOBVJOSVZKF-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[4-methoxy-2-(pyrrolidin-1-ylmethyl)phenyl]phenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C=1C(OC)=CC=C(C=2C=CC(=CC=2)C2=NOC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=1CN1CCCC1 HGLFOBVJOSVZKF-UHFFFAOYSA-N 0.000 claims description 2
• ZVMSJANFBJSXAK-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[5-chloro-2-(pyrrolidin-1-ylmethyl)phenyl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1ON=C(C=2C=CC(=CC=2)C=2C(=CC=C(Cl)C=2)CN2CCCC2)C1 ZVMSJANFBJSXAK-UHFFFAOYSA-N 0.000 claims description 2
• UTUAKQIEXNQUAT-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[[6-(trifluoromethyl)quinolin-4-yl]amino]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C12=CC(C(F)(F)F)=CC=C2N=CC=C1NC(C=C1)=CC=C1C(C1)=NOC1CNC(=O)C1=CC=C(Cl)S1 UTUAKQIEXNQUAT-UHFFFAOYSA-N 0.000 claims description 2
• NPKLBZXEOHDSKT-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[[7-(trifluoromethyl)quinolin-4-yl]amino]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C=1C=NC2=CC(C(F)(F)F)=CC=C2C=1NC(C=C1)=CC=C1C(C1)=NOC1CNC(=O)C1=CC=C(Cl)S1 NPKLBZXEOHDSKT-UHFFFAOYSA-N 0.000 claims description 2
• XGXRAFFUVCTWAT-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[methyl(pyridin-4-yl)amino]phenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C=1C=C(C2=NOC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=CC=1N(C)C1=CC=NC=C1 XGXRAFFUVCTWAT-UHFFFAOYSA-N 0.000 claims description 2
• RLXIWJWTLIDRDF-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[n-(furan-2-ylmethyl)-n-methylcarbamimidoyl]phenyl]-5-methyl-4h-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C=1C=C(C=2CC(C)(CNC(=O)C=3SC(Cl)=CC=3)ON=2)C=CC=1C(=N)N(C)CC1=CC=CO1 RLXIWJWTLIDRDF-UHFFFAOYSA-N 0.000 claims description 2
• YWPNIOXQDWKJBT-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[n-[2-(dimethylamino)ethyl]-n-methylcarbamimidoyl]phenyl]-5-methyl-4h-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)CCN(C)C)=CC=C1C(C1)=NOC1(C)CNC(=O)C1=CC=C(Cl)S1 YWPNIOXQDWKJBT-UHFFFAOYSA-N 0.000 claims description 2
• KFAHQGHQWIARCF-UHFFFAOYSA-N 5-chloro-n-[[4-[4-(n,n-dimethylcarbamimidoyl)phenyl]-1,3-thiazol-2-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)C)=CC=C1C1=CSC(CNC(=O)C=2SC(Cl)=CC=2)=N1 KFAHQGHQWIARCF-UHFFFAOYSA-N 0.000 claims description 2
• JVJFPAIWUYRASS-UHFFFAOYSA-N 5-chloro-n-[[4-fluoro-3-[4-(1-methyl-4,5-dihydroimidazol-2-yl)phenyl]phenyl]methyl]thiophene-2-carboxamide Chemical compound CN1CCN=C1C1=CC=C(C=2C(=CC=C(CNC(=O)C=3SC(Cl)=CC=3)C=2)F)C=C1 JVJFPAIWUYRASS-UHFFFAOYSA-N 0.000 claims description 2
• NNCGJDBKCQKYSV-UHFFFAOYSA-N 5-chloro-n-[[5-[4-(n,n-dimethylcarbamimidoyl)phenyl]-2-fluorophenyl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)C)=CC=C1C1=CC=C(F)C(CNC(=O)C=2SC(Cl)=CC=2)=C1 NNCGJDBKCQKYSV-UHFFFAOYSA-N 0.000 claims description 2
• FHAMQVFPOHLFPT-UHFFFAOYSA-N 5-chloro-n-[[5-methyl-3-(4-methylphenyl)-4h-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C)=CC=C1C(C1)=NOC1(C)CNC(=O)C1=CC=C(Cl)S1 FHAMQVFPOHLFPT-UHFFFAOYSA-N 0.000 claims description 2
• YOZCKVNTKCOLLU-UHFFFAOYSA-N 5-chloro-n-methyl-n-[[3-[4-(n'-methylcarbamimidoyl)phenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)NC)=CC=C1C1=NOC(CN(C)C(=O)C=2SC(Cl)=CC=2)=C1 YOZCKVNTKCOLLU-UHFFFAOYSA-N 0.000 claims description 2
• QOEMOSFXWCVVSB-UHFFFAOYSA-N 5-chloro-n-methyl-n-[[3-[4-(piperidine-1-carboximidoyl)phenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C=1C=C(Cl)SC=1C(=O)N(C)CC(ON=1)=CC=1C(C=C1)=CC=C1C(=N)N1CCCCC1 QOEMOSFXWCVVSB-UHFFFAOYSA-N 0.000 claims description 2
• RREUQSITENYGES-UHFFFAOYSA-N ethyl 1-[4-[5-[[(5-chlorothiophene-2-carbonyl)amino]methyl]-5-methyl-4h-1,2-oxazol-3-yl]benzenecarboximidoyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C(=N)C1=CC=C(C=2CC(C)(CNC(=O)C=3SC(Cl)=CC=3)ON=2)C=C1 RREUQSITENYGES-UHFFFAOYSA-N 0.000 claims description 2
• 125000002883 imidazolyl group Chemical group 0.000 claims description 2
• 229910052740 iodine Inorganic materials 0.000 claims description 2
• LQLHTIXRMSEXTG-UHFFFAOYSA-N methyl 3-[4-[5-[[(5-chlorothiophene-2-carbonyl)amino]methyl]-4,5-dihydro-1,2-oxazol-3-yl]anilino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C=CC(=CC=2)C=2CC(CNC(=O)C=3SC(Cl)=CC=3)ON=2)=C1 LQLHTIXRMSEXTG-UHFFFAOYSA-N 0.000 claims description 2
• FZLNDSSXLXXLCU-UHFFFAOYSA-N methyl 4-[5-[[(5-chlorothiophene-2-carbonyl)amino]methyl]-1,2-oxazol-3-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NOC(CNC(=O)C=2SC(Cl)=CC=2)=C1 FZLNDSSXLXXLCU-UHFFFAOYSA-N 0.000 claims description 2
• YETNZFWQQMPWCH-UHFFFAOYSA-N n-[[1-[4-(azetidine-1-carboximidoyl)phenyl]imidazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C=CC(=CC=2)C(=N)N2CCC2)C=N1 YETNZFWQQMPWCH-UHFFFAOYSA-N 0.000 claims description 2
• TYOMYOZJHUAERX-UHFFFAOYSA-N n-[[1-[4-(azetidine-1-carboximidoyl)phenyl]pyrazol-4-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C=CC(=CC=2)C(=N)N2CCC2)N=C1 TYOMYOZJHUAERX-UHFFFAOYSA-N 0.000 claims description 2
• VRYJELNOIUQQPQ-UHFFFAOYSA-N n-[[3-(1-benzylpiperidin-4-yl)-4,5-dihydro-1,2-oxazol-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1ON=C(C2CCN(CC=3C=CC=CC=3)CC2)C1 VRYJELNOIUQQPQ-UHFFFAOYSA-N 0.000 claims description 2
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