ZA200503989B - Mandelic acid derivatives - Google Patents
Mandelic acid derivatives Download PDFInfo
- Publication number
- ZA200503989B ZA200503989B ZA200503989A ZA200503989A ZA200503989B ZA 200503989 B ZA200503989 B ZA 200503989B ZA 200503989 A ZA200503989 A ZA 200503989A ZA 200503989 A ZA200503989 A ZA 200503989A ZA 200503989 B ZA200503989 B ZA 200503989B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- alkoxy
- methoxy
- carbamimidoyl
- phenyl
- Prior art date
Links
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical class O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 89
- 229910052739 hydrogen Inorganic materials 0.000 claims description 77
- 239000001257 hydrogen Substances 0.000 claims description 77
- -1 lower-alkyl-carbonyl Chemical group 0.000 claims description 77
- 150000002431 hydrogen Chemical group 0.000 claims description 51
- 229910052736 halogen Inorganic materials 0.000 claims description 35
- 150000002367 halogens Chemical group 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- 125000004104 aryloxy group Chemical group 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 206010047249 Venous thrombosis Diseases 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 108010039209 Blood Coagulation Factors Proteins 0.000 claims description 9
- 102000015081 Blood Coagulation Factors Human genes 0.000 claims description 9
- 108090000190 Thrombin Proteins 0.000 claims description 9
- 108010000499 Thromboplastin Proteins 0.000 claims description 9
- 102000002262 Thromboplastin Human genes 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 239000003114 blood coagulation factor Substances 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000011737 fluorine Chemical group 0.000 claims description 9
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 9
- 229960004072 thrombin Drugs 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 108010054265 Factor VIIa Proteins 0.000 claims description 7
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 7
- 229940012414 factor viia Drugs 0.000 claims description 7
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 6
- 206010003658 Atrial Fibrillation Diseases 0.000 claims description 6
- 206010051055 Deep vein thrombosis Diseases 0.000 claims description 6
- 206010061216 Infarction Diseases 0.000 claims description 6
- 206010061218 Inflammation Diseases 0.000 claims description 6
- 208000010378 Pulmonary Embolism Diseases 0.000 claims description 6
- 208000007814 Unstable Angina Diseases 0.000 claims description 6
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 6
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 6
- 230000000747 cardiac effect Effects 0.000 claims description 6
- 230000007574 infarction Effects 0.000 claims description 6
- 230000004054 inflammatory process Effects 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000005116 aryl carbamoyl group Chemical group 0.000 claims description 5
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- DQHCYASUSUULKJ-UHFFFAOYSA-N ethyl (nz)-n-[amino-[4-[[[2-(2-fluoro-4-methoxyphenyl)-2-methoxyacetyl]amino]methyl]phenyl]methylidene]carbamate Chemical compound C1=CC(C(N)=NC(=O)OCC)=CC=C1CNC(=O)C(OC)C1=CC=C(OC)C=C1F DQHCYASUSUULKJ-UHFFFAOYSA-N 0.000 claims description 2
- RPJBGGCMUIXRFK-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-(2-fluoro-4-pyridin-3-ylphenyl)-2-methoxyacetamide;hydrochloride Chemical compound Cl.C=1C=C(C=2C=NC=CC=2)C=C(F)C=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 RPJBGGCMUIXRFK-UHFFFAOYSA-N 0.000 claims description 2
- CITXZGVAYSIRCC-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-[2-fluoro-4-(3-methoxyphenyl)phenyl]-2-methoxyacetamide;hydrochloride Chemical compound Cl.C=1C=C(C=2C=C(OC)C=CC=2)C=C(F)C=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 CITXZGVAYSIRCC-UHFFFAOYSA-N 0.000 claims description 2
- PSRXUBUCTFMDRJ-UHFFFAOYSA-N n-[[2-(2-amino-2-oxoethoxy)-4-carbamimidoylphenyl]methyl]-2-(2,6-difluoro-4-methoxyphenyl)-2-ethoxyacetamide;hydrochloride Chemical compound Cl.FC=1C=C(OC)C=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1OCC(N)=O PSRXUBUCTFMDRJ-UHFFFAOYSA-N 0.000 claims description 2
- VCEXMSOCCXAXMW-UHFFFAOYSA-N n-[[4-carbamimidoyl-2-(pyridin-2-ylmethoxy)phenyl]methyl]-2-(2,6-difluoro-4-methoxyphenyl)-2-methoxyacetamide;hydrochloride Chemical compound Cl.FC=1C=C(OC)C=C(F)C=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1OCC1=CC=CC=N1 VCEXMSOCCXAXMW-UHFFFAOYSA-N 0.000 claims description 2
- LQTPYKZQWLYWKY-UHFFFAOYSA-N n-[[4-carbamimidoyl-2-[2-(2-methoxyethylamino)-2-oxoethoxy]phenyl]methyl]-2-(2,6-difluoro-4-methoxyphenyl)-2-ethoxyacetamide;hydrochloride Chemical compound Cl.FC=1C=C(OC)C=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1OCC(=O)NCCOC LQTPYKZQWLYWKY-UHFFFAOYSA-N 0.000 claims description 2
- 238000011321 prophylaxis Methods 0.000 claims 13
- 230000001225 therapeutic effect Effects 0.000 claims 13
- 239000000126 substance Substances 0.000 claims 8
- 206010028980 Neoplasm Diseases 0.000 claims 5
- 206010003178 Arterial thrombosis Diseases 0.000 claims 4
- 239000013543 active substance Substances 0.000 claims 4
- 241001465754 Metazoa Species 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- DXQOFSIGKHAKKC-UHFFFAOYSA-N 2-(4-bromo-2,6-difluorophenyl)-n-[(4-carbamimidoylphenyl)methyl]-2-ethoxyacetamide;hydrochloride Chemical compound Cl.FC=1C=C(Br)C=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1 DXQOFSIGKHAKKC-UHFFFAOYSA-N 0.000 claims 1
- HLVQFPOEIQANME-UHFFFAOYSA-N 2-[4-(2-aminopyrimidin-5-yl)-2,6-difluorophenyl]-n-[(4-carbamimidoylphenyl)methyl]-2-ethoxyacetamide;hydrochloride Chemical compound Cl.FC=1C=C(C=2C=NC(N)=NC=2)C=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1 HLVQFPOEIQANME-UHFFFAOYSA-N 0.000 claims 1
- CJLZDXANBNSBGQ-UHFFFAOYSA-N 2-[4-(5-aminopyridin-2-yl)-2,6-difluorophenyl]-n-[(4-carbamimidoylphenyl)methyl]-2-ethoxyacetamide;hydrochloride Chemical compound Cl.FC=1C=C(C=2N=CC(N)=CC=2)C=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1 CJLZDXANBNSBGQ-UHFFFAOYSA-N 0.000 claims 1
- WDSSEQIKVBFNIH-UHFFFAOYSA-N 3-[2-(2-amino-2-oxoethoxy)-4-carbamimidoylphenyl]-2-[2,6-difluoro-4-(pyridin-2-ylmethoxy)phenyl]-2-ethoxypropanamide;hydrochloride Chemical compound Cl.FC=1C=C(OCC=2N=CC=CC=2)C=C(F)C=1C(OCC)(C(N)=O)CC1=CC=C(C(N)=N)C=C1OCC(N)=O WDSSEQIKVBFNIH-UHFFFAOYSA-N 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- GFKUWRNVWKEKGV-UHFFFAOYSA-N acetic acid;2-[4-(6-aminopyridin-3-yl)-2,6-difluorophenyl]-n-[(4-carbamimidoyl-2,6-difluorophenyl)methyl]-2-ethoxyacetamide Chemical compound CC(O)=O.FC=1C=C(C=2C=NC(N)=CC=2)C=C(F)C=1C(OCC)C(=O)NCC1=C(F)C=C(C(N)=N)C=C1F GFKUWRNVWKEKGV-UHFFFAOYSA-N 0.000 claims 1
- YPYKRPZHMHVRHO-UHFFFAOYSA-N acetic acid;n-[[2-(benzylamino)-4-carbamimidoylphenyl]methyl]-2-ethoxy-2-(2-fluoro-4-methoxyphenyl)acetamide Chemical compound CC(O)=O.C=1C=C(OC)C=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1NCC1=CC=CC=C1 YPYKRPZHMHVRHO-UHFFFAOYSA-N 0.000 claims 1
- UGQAWWNEYRHZTR-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-(2,6-difluoro-4-methoxyphenyl)-2-methoxyacetamide;hydrochloride Chemical compound Cl.FC=1C=C(OC)C=C(F)C=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 UGQAWWNEYRHZTR-UHFFFAOYSA-N 0.000 claims 1
- AVWAZRCESKECFA-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-(2,6-difluoro-4-pyridin-3-ylphenyl)-2-ethoxyacetamide;hydrochloride Chemical compound Cl.FC=1C=C(C=2C=NC=CC=2)C=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1 AVWAZRCESKECFA-UHFFFAOYSA-N 0.000 claims 1
- YMNBWWQZRPLZDS-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-[2,6-difluoro-4-(pyridin-2-ylmethoxy)phenyl]-2-ethoxyacetamide;hydrochloride Chemical compound Cl.FC=1C=C(OCC=2N=CC=CC=2)C=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1 YMNBWWQZRPLZDS-UHFFFAOYSA-N 0.000 claims 1
- BXADRBFJERDPKB-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-ethoxy-2-(2-fluoro-4-methoxyphenyl)acetamide;hydrochloride Chemical compound Cl.C=1C=C(OC)C=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1 BXADRBFJERDPKB-UHFFFAOYSA-N 0.000 claims 1
- 125000002560 nitrile group Chemical group 0.000 claims 1
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 6
- AXJDEHNQPMZKOS-UHFFFAOYSA-N acetylazanium;chloride Chemical compound [Cl-].CC([NH3+])=O AXJDEHNQPMZKOS-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- GSNFOKGMUXXBNX-UHFFFAOYSA-N 2-ethoxyacetamide;hydrochloride Chemical compound Cl.CCOCC(N)=O GSNFOKGMUXXBNX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- BQVFLKANBKXMRQ-UHFFFAOYSA-N 2-ethoxyacetamide dihydrochloride Chemical compound Cl.Cl.CCOCC(N)=O BQVFLKANBKXMRQ-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229940082863 Factor VIIa inhibitor Drugs 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 125000002757 morpholinyl group Chemical group 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- DRNOMNIKQVWPMA-XFULWGLBSA-N (2r)-n-[(4-carbamimidoylphenyl)methyl]-2-methoxy-2-phenylacetamide;hydrochloride Chemical compound Cl.O=C([C@H](OC)C=1C=CC=CC=1)NCC1=CC=C(C(N)=N)C=C1 DRNOMNIKQVWPMA-XFULWGLBSA-N 0.000 description 1
- DRNOMNIKQVWPMA-RSAXXLAASA-N (2s)-n-[(4-carbamimidoylphenyl)methyl]-2-methoxy-2-phenylacetamide;hydrochloride Chemical compound Cl.O=C([C@@H](OC)C=1C=CC=CC=1)NCC1=CC=C(C(N)=N)C=C1 DRNOMNIKQVWPMA-RSAXXLAASA-N 0.000 description 1
- DONDQHCJKIFRIN-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-n-[(4-carbamimidoylphenyl)methyl]-2-ethoxyacetamide;hydrochloride Chemical compound Cl.C=1C=C2OCOC2=CC=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1 DONDQHCJKIFRIN-UHFFFAOYSA-N 0.000 description 1
- HHPMBWVNZVAVCY-UHFFFAOYSA-N 2-(2-fluoro-4-methoxyphenyl)-n-[[4-(n'-hydroxycarbamimidoyl)phenyl]methyl]-2-methoxyacetamide Chemical compound C=1C=C(OC)C=C(F)C=1C(OC)C(=O)NCC1=CC=C(C(=N)NO)C=C1 HHPMBWVNZVAVCY-UHFFFAOYSA-N 0.000 description 1
- QDEWLEIXBORAIY-UHFFFAOYSA-N 2-(4-acetamidophenyl)-n-[(4-carbamimidoylphenyl)methyl]-2-methoxyacetamide;hydrochloride Chemical compound Cl.C=1C=C(NC(C)=O)C=CC=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 QDEWLEIXBORAIY-UHFFFAOYSA-N 0.000 description 1
- YCTZTHQNGVDWBW-UHFFFAOYSA-N 2-(4-bromo-2,6-difluorophenyl)-n-[(4-carbamimidoylphenyl)methyl]-2-methoxyacetamide;hydrochloride Chemical compound Cl.FC=1C=C(Br)C=C(F)C=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 YCTZTHQNGVDWBW-UHFFFAOYSA-N 0.000 description 1
- IQQQPYOYCYNENO-UHFFFAOYSA-N 2-(4-bromo-2-fluorophenyl)-n-[(4-carbamimidoylphenyl)methyl]-2-methoxyacetamide;hydrochloride Chemical compound Cl.C=1C=C(Br)C=C(F)C=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 IQQQPYOYCYNENO-UHFFFAOYSA-N 0.000 description 1
- DBWLLLGHEBAJSB-UHFFFAOYSA-N 2-(4-bromo-2-fluorophenyl)-n-[(4-carbamimidoylphenyl)methyl]-2-propoxyacetamide;hydrochloride Chemical compound Cl.C=1C=C(Br)C=C(F)C=1C(OCCC)C(=O)NCC1=CC=C(C(N)=N)C=C1 DBWLLLGHEBAJSB-UHFFFAOYSA-N 0.000 description 1
- PDCKDBNTELHWRL-UHFFFAOYSA-N 2-(5-bromo-2-fluorophenyl)-n-[(4-carbamimidoylphenyl)methyl]-2-methoxyacetamide;hydrochloride Chemical compound Cl.C=1C(Br)=CC=C(F)C=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 PDCKDBNTELHWRL-UHFFFAOYSA-N 0.000 description 1
- LYVNGSKDFCNFQA-UHFFFAOYSA-N 2-[2-(2-amino-2-oxoethoxy)-6-fluorophenyl]-n-[(4-carbamimidoylphenyl)methyl]-2-methoxyacetamide;hydrochloride Chemical compound Cl.FC=1C=CC=C(OCC(N)=O)C=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 LYVNGSKDFCNFQA-UHFFFAOYSA-N 0.000 description 1
- MZPVIBZWINCWGZ-UHFFFAOYSA-N 2-[3-(1-acetylpiperidin-4-yl)oxy-5-ethoxy-2-fluorophenyl]-n-[(4-carbamimidoylphenyl)methyl]-2-methoxyacetamide;hydrochloride Chemical compound Cl.FC=1C(C(OC)C(=O)NCC=2C=CC(=CC=2)C(N)=N)=CC(OCC)=CC=1OC1CCN(C(C)=O)CC1 MZPVIBZWINCWGZ-UHFFFAOYSA-N 0.000 description 1
- LUYNFUVZLRRHIG-UHFFFAOYSA-N 2-[3-(2-amino-2-oxoethoxy)-4-methoxyphenyl]-n-[(4-carbamimidoylphenyl)methyl]-2-ethoxyacetamide;hydrochloride Chemical compound Cl.C=1C=C(OC)C(OCC(N)=O)=CC=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1 LUYNFUVZLRRHIG-UHFFFAOYSA-N 0.000 description 1
- ICZDYSOSHXELOF-UHFFFAOYSA-N 2-[3-(2-amino-2-oxoethoxy)-4-methoxyphenyl]-n-[(4-carbamimidoylphenyl)methyl]-2-methoxyacetamide;hydrochloride Chemical compound Cl.C=1C=C(OC)C(OCC(N)=O)=CC=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 ICZDYSOSHXELOF-UHFFFAOYSA-N 0.000 description 1
- JGUSWDZJAMHHHJ-UHFFFAOYSA-N 2-[3-[1-(benzenesulfonyl)piperidin-4-yl]oxy-5-ethoxy-2-fluorophenyl]-n-[(4-carbamimidoylphenyl)methyl]-2-methoxyacetamide;hydrochloride Chemical compound Cl.FC=1C(C(OC)C(=O)NCC=2C=CC(=CC=2)C(N)=N)=CC(OCC)=CC=1OC(CC1)CCN1S(=O)(=O)C1=CC=CC=C1 JGUSWDZJAMHHHJ-UHFFFAOYSA-N 0.000 description 1
- DXOSQOFUIWPWRS-UHFFFAOYSA-N 2-[4-[2-[(4-carbamimidoylphenyl)methylamino]-1-methoxy-2-oxoethyl]phenoxy]acetic acid Chemical compound C=1C=C(OCC(O)=O)C=CC=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 DXOSQOFUIWPWRS-UHFFFAOYSA-N 0.000 description 1
- SSWJUVFZLLFIKH-XDYBDFTFSA-N 2-[5-carbamimidoyl-2-[[[(2r)-2-ethoxy-2-(2-fluoro-4-methoxyphenyl)acetyl]amino]methyl]phenoxy]propanamide;hydrochloride Chemical compound Cl.O=C([C@H](OCC)C=1C(=CC(OC)=CC=1)F)NCC1=CC=C(C(N)=N)C=C1OC(C)C(N)=O SSWJUVFZLLFIKH-XDYBDFTFSA-N 0.000 description 1
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- XOFGSHZCZXPIQA-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-[2,6-difluoro-3-(3-pyridin-4-ylpropoxy)phenyl]-2-ethoxyacetamide;dihydrochloride Chemical compound Cl.Cl.FC=1C=CC(OCCCC=2C=CN=CC=2)=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1 XOFGSHZCZXPIQA-UHFFFAOYSA-N 0.000 description 1
- IJBPSFKRJFAIOD-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-[2,6-difluoro-3-[(1-methylcyclopropyl)methoxy]phenyl]-2-ethoxyacetamide;hydrochloride Chemical compound Cl.FC=1C=CC(OCC2(C)CC2)=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1 IJBPSFKRJFAIOD-UHFFFAOYSA-N 0.000 description 1
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- JNTOLBMVPOFFRV-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-[2,6-difluoro-3-[(1-methylpiperidin-3-yl)methoxy]phenyl]-2-ethoxyacetamide;dihydrochloride Chemical compound Cl.Cl.FC=1C=CC(OCC2CN(C)CCC2)=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1 JNTOLBMVPOFFRV-UHFFFAOYSA-N 0.000 description 1
- ZKUSALDDDDWKEJ-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-[2,6-difluoro-3-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]phenyl]-2-ethoxyacetamide;hydrochloride Chemical compound Cl.FC=1C=CC(OCCOCCOCCOC)=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1 ZKUSALDDDDWKEJ-UHFFFAOYSA-N 0.000 description 1
- JOALMXUWWYKCOX-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-[2,6-difluoro-4-(2-morpholin-4-ylethoxy)phenyl]-2-ethoxyacetamide;dihydrochloride Chemical compound Cl.Cl.FC=1C=C(OCCN2CCOCC2)C=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1 JOALMXUWWYKCOX-UHFFFAOYSA-N 0.000 description 1
- HANLNXGQJORZJP-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-[2-fluoro-4-(2-methoxyphenyl)phenyl]-2-methoxyacetamide;hydrochloride Chemical compound Cl.C=1C=C(C=2C(=CC=CC=2)OC)C=C(F)C=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 HANLNXGQJORZJP-UHFFFAOYSA-N 0.000 description 1
- UGDYSFBNSJEZBP-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-[2-fluoro-4-(2-methylpropoxy)phenyl]-2-methoxyacetamide;hydrochloride Chemical compound Cl.C=1C=C(OCC(C)C)C=C(F)C=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 UGDYSFBNSJEZBP-UHFFFAOYSA-N 0.000 description 1
- ZVZSZSFSOXFRDW-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-[2-fluoro-4-(4-methoxyphenyl)phenyl]-2-methoxyacetamide;hydrochloride Chemical compound Cl.C=1C=C(C=2C=CC(OC)=CC=2)C=C(F)C=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 ZVZSZSFSOXFRDW-UHFFFAOYSA-N 0.000 description 1
- NIVCXWODPQIBCS-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-[2-fluoro-4-(trifluoromethyl)phenyl]-2-methoxyacetamide;hydrochloride Chemical compound Cl.C=1C=C(C(F)(F)F)C=C(F)C=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 NIVCXWODPQIBCS-UHFFFAOYSA-N 0.000 description 1
- IGHVETFRRLVWLU-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-[2-fluoro-4-[2-(4-fluorophenyl)ethoxy]phenyl]-2-methoxyacetamide;hydrochloride Chemical compound Cl.C=1C=C(OCCC=2C=CC(F)=CC=2)C=C(F)C=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 IGHVETFRRLVWLU-UHFFFAOYSA-N 0.000 description 1
- SHERSGSXIXPJNJ-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-[2-fluoro-5-(trifluoromethyl)phenyl]-2-methoxyacetamide;hydrochloride Chemical compound Cl.C=1C(C(F)(F)F)=CC=C(F)C=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 SHERSGSXIXPJNJ-UHFFFAOYSA-N 0.000 description 1
- HYIQNMCGQYLYIR-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-[2-fluoro-6-(2-hydroxyethoxy)phenyl]-2-methoxyacetamide;hydrochloride Chemical compound Cl.FC=1C=CC=C(OCCO)C=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 HYIQNMCGQYLYIR-UHFFFAOYSA-N 0.000 description 1
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- BYYOTDWOKSTIME-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-[3-[2-(diethylamino)-2-oxoethoxy]-2,6-difluorophenyl]-2-ethoxyacetamide;hydrochloride Chemical compound Cl.FC=1C=CC(OCC(=O)N(CC)CC)=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1 BYYOTDWOKSTIME-UHFFFAOYSA-N 0.000 description 1
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- DNFJIGXERSASEC-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-[4-(4-cyanophenoxy)-2,6-difluorophenyl]-2-ethoxyacetamide;hydrochloride Chemical compound Cl.FC=1C=C(OC=2C=CC(=CC=2)C#N)C=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1 DNFJIGXERSASEC-UHFFFAOYSA-N 0.000 description 1
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- JRDDPMOGPDEIBL-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-ethoxy-2-(3-ethoxy-2,6-difluorophenyl)acetamide;hydrochloride Chemical compound Cl.FC=1C=CC(OCC)=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1 JRDDPMOGPDEIBL-UHFFFAOYSA-N 0.000 description 1
- GOFOGFCBPYEMBC-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-ethoxy-2-(4-phenylphenyl)propanamide;hydrochloride Chemical compound Cl.C=1C=C(C=2C=CC=CC=2)C=CC=1C(C)(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1 GOFOGFCBPYEMBC-UHFFFAOYSA-N 0.000 description 1
- SQBSOSXLSFXAIA-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-ethoxy-2-phenylacetamide;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1 SQBSOSXLSFXAIA-UHFFFAOYSA-N 0.000 description 1
- GEAKVHFMJOYEMC-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-methoxy-2-(2-morpholin-4-ylphenyl)acetamide;hydrochloride Chemical compound Cl.C=1C=CC=C(N2CCOCC2)C=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 GEAKVHFMJOYEMC-UHFFFAOYSA-N 0.000 description 1
- HLUNMNSZPCXXGJ-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-methoxy-2-(3-phenoxyphenyl)acetamide;hydrochloride Chemical compound Cl.C=1C=CC(OC=2C=CC=CC=2)=CC=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 HLUNMNSZPCXXGJ-UHFFFAOYSA-N 0.000 description 1
- WCNVOMIUERTKNL-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-methoxy-2-(4-morpholin-4-ylphenyl)acetamide;hydrochloride Chemical compound Cl.C=1C=C(N2CCOCC2)C=CC=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 WCNVOMIUERTKNL-UHFFFAOYSA-N 0.000 description 1
- GFBPHEKCHUWBGZ-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-methoxy-2-(4-phenoxyphenyl)acetamide;hydrochloride Chemical compound Cl.C=1C=C(OC=2C=CC=CC=2)C=CC=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 GFBPHEKCHUWBGZ-UHFFFAOYSA-N 0.000 description 1
- HPQWQMAWXUKXAY-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-methoxy-2-(4-phenylmethoxyphenyl)acetamide;hydrochloride Chemical compound Cl.C=1C=C(OCC=2C=CC=CC=2)C=CC=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 HPQWQMAWXUKXAY-UHFFFAOYSA-N 0.000 description 1
- OACNXGINDGJGRR-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-methoxy-2-(4-phenylphenyl)acetamide;hydrochloride Chemical compound Cl.C=1C=C(C=2C=CC=CC=2)C=CC=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 OACNXGINDGJGRR-UHFFFAOYSA-N 0.000 description 1
- CUIWDOFGQKYNON-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-methoxy-2-(4-propan-2-yloxyphenyl)acetamide;hydrochloride Chemical compound Cl.C=1C=C(OC(C)C)C=CC=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 CUIWDOFGQKYNON-UHFFFAOYSA-N 0.000 description 1
- GHMRBKZUGDFEAH-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-methoxy-2-(4-pyrrolidin-1-ylphenyl)acetamide;hydrochloride Chemical compound Cl.C=1C=C(N2CCCC2)C=CC=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 GHMRBKZUGDFEAH-UHFFFAOYSA-N 0.000 description 1
- ZTANWVJOHSPRSE-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-methoxy-2-(6-methoxynaphthalen-2-yl)acetamide;hydrochloride Chemical compound Cl.C=1C=C2C=C(OC)C=CC2=CC=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 ZTANWVJOHSPRSE-UHFFFAOYSA-N 0.000 description 1
- LVKMQSNRFNKSCD-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-methoxy-2-[4-(1-methylpiperidin-4-yl)oxyphenyl]acetamide;hydrochloride Chemical compound Cl.C=1C=C(OC2CCN(C)CC2)C=CC=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 LVKMQSNRFNKSCD-UHFFFAOYSA-N 0.000 description 1
- KYIWEXBMEFTLPB-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-methoxy-2-phenylpropanamide;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C)(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 KYIWEXBMEFTLPB-UHFFFAOYSA-N 0.000 description 1
- JHHGVEAWAIKYJD-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-methoxy-2-pyridin-2-ylacetamide;hydrochloride Chemical compound Cl.C=1C=CC=NC=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1 JHHGVEAWAIKYJD-UHFFFAOYSA-N 0.000 description 1
- XBRQUJLMAOOPMS-UHFFFAOYSA-N n-[(4-carbamimidoylphenyl)methyl]-2-methylsulfonyl-2-phenylacetamide;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(S(=O)(=O)C)C(=O)NCC1=CC=C(C(N)=N)C=C1 XBRQUJLMAOOPMS-UHFFFAOYSA-N 0.000 description 1
- RYKRGNJAZUUTHM-UHFFFAOYSA-N n-[[2-(5-aminopyridin-2-yl)oxy-4-carbamimidoylphenyl]methyl]-2-ethoxy-2-(2-fluoro-4-methoxyphenyl)acetamide;hydrochloride Chemical compound Cl.C=1C=C(OC)C=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1OC1=CC=C(N)C=N1 RYKRGNJAZUUTHM-UHFFFAOYSA-N 0.000 description 1
- XUZSLWRUIOUCEC-UHFFFAOYSA-N n-[[4-(n'-hydroxycarbamimidoyl)phenyl]methyl]-2-(2-hydroxy-4-methoxyphenyl)-2-methoxyacetamide Chemical compound C=1C=C(OC)C=C(O)C=1C(OC)C(=O)NCC1=CC=C(C(=N)NO)C=C1 XUZSLWRUIOUCEC-UHFFFAOYSA-N 0.000 description 1
- QKBDLBMHKUELMH-UHFFFAOYSA-N n-[[4-carbamimidoyl-2-(1,2,4-oxadiazol-3-ylmethoxy)phenyl]methyl]-2-(2,6-difluoro-4-methoxyphenyl)-2-ethoxyacetamide;hydrochloride Chemical compound Cl.FC=1C=C(OC)C=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1OCC=1N=CON=1 QKBDLBMHKUELMH-UHFFFAOYSA-N 0.000 description 1
- OCDMMEFTKHJMCP-UHFFFAOYSA-N n-[[4-carbamimidoyl-2-(2-hydroxycyclopentyl)oxyphenyl]methyl]-2-(2,6-difluoro-4-methoxyphenyl)-2-ethoxyacetamide;hydrochloride Chemical compound Cl.FC=1C=C(OC)C=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1OC1CCCC1O OCDMMEFTKHJMCP-UHFFFAOYSA-N 0.000 description 1
- SDQXTVRHZPSKHM-UHFFFAOYSA-N n-[[4-carbamimidoyl-2-(2-methylphenoxy)phenyl]methyl]-2-ethoxy-2-(2-fluoro-4-methoxyphenyl)acetamide;hydrochloride Chemical compound Cl.C=1C=C(OC)C=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1OC1=CC=CC=C1C SDQXTVRHZPSKHM-UHFFFAOYSA-N 0.000 description 1
- FUZJHUABIPUWEK-UHFFFAOYSA-N n-[[4-carbamimidoyl-2-(4-fluorophenoxy)phenyl]methyl]-2-ethoxy-2-(2-fluoro-4-methoxyphenyl)acetamide;hydrochloride Chemical compound Cl.C=1C=C(OC)C=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1OC1=CC=C(F)C=C1 FUZJHUABIPUWEK-UHFFFAOYSA-N 0.000 description 1
- MTOILEFMASLUFW-UHFFFAOYSA-N n-[[4-carbamimidoyl-2-(5-nitropyridin-2-yl)oxyphenyl]methyl]-2-ethoxy-2-(2-fluoro-4-methoxyphenyl)acetamide;hydrochloride Chemical compound Cl.C=1C=C(OC)C=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1OC1=CC=C([N+]([O-])=O)C=N1 MTOILEFMASLUFW-UHFFFAOYSA-N 0.000 description 1
- WYQIQKQINKYJOV-UHFFFAOYSA-N n-[[4-carbamimidoyl-2-(pyridin-3-ylmethoxy)phenyl]methyl]-2-(2,6-difluoro-4-methoxyphenyl)-2-methoxyacetamide;hydrochloride Chemical compound Cl.FC=1C=C(OC)C=C(F)C=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1OCC1=CC=CN=C1 WYQIQKQINKYJOV-UHFFFAOYSA-N 0.000 description 1
- YHBJSECOSQHDIB-UHFFFAOYSA-N n-[[4-carbamimidoyl-2-[(2-fluorophenyl)methoxy]phenyl]methyl]-2-(2,6-difluoro-4-methoxyphenyl)-2-ethoxyacetamide;hydrochloride Chemical compound Cl.FC=1C=C(OC)C=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1OCC1=CC=CC=C1F YHBJSECOSQHDIB-UHFFFAOYSA-N 0.000 description 1
- DSXYGGRGKNOBPB-UHFFFAOYSA-N n-[[4-carbamimidoyl-2-[(5-chloro-2-fluorophenyl)methoxy]phenyl]methyl]-2-(2,6-difluoro-4-methoxyphenyl)-2-ethoxyacetamide;hydrochloride Chemical compound Cl.FC=1C=C(OC)C=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1OCC1=CC(Cl)=CC=C1F DSXYGGRGKNOBPB-UHFFFAOYSA-N 0.000 description 1
- RRNSVXBTWWPEJP-UHFFFAOYSA-N n-[[4-carbamimidoyl-2-[2-(2-morpholin-4-ylethylamino)-2-oxoethoxy]phenyl]methyl]-2-(2,6-difluoro-4-methoxyphenyl)-2-ethoxyacetamide;hydrochloride Chemical compound Cl.FC=1C=C(OC)C=C(F)C=1C(OCC)C(=O)NCC1=CC=C(C(N)=N)C=C1OCC(=O)NCCN1CCOCC1 RRNSVXBTWWPEJP-UHFFFAOYSA-N 0.000 description 1
- SQNNORGCNZZRGP-UHFFFAOYSA-N n-[[4-carbamimidoyl-2-[2-(4-fluoroanilino)-2-oxoethoxy]phenyl]methyl]-2-(2,6-difluoro-4-methoxyphenyl)-2-methoxyacetamide;hydrochloride Chemical compound Cl.FC=1C=C(OC)C=C(F)C=1C(OC)C(=O)NCC1=CC=C(C(N)=N)C=C1OCC(=O)NC1=CC=C(F)C=C1 SQNNORGCNZZRGP-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000005309 thioalkoxy group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
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US7247654B2 (en) * | 2003-06-04 | 2007-07-24 | Bristol-Myers Squibb Company | 3,4-disubstituted benzamidines and benzylamines, and analogues thereof, useful as serine protease inhibitors |
US7056932B2 (en) | 2003-12-19 | 2006-06-06 | Hoffman-La Roche Inc. | Heterocyclyl substituted 1-alkoxy acetic acid amides |
UA87854C2 (en) * | 2004-06-07 | 2009-08-25 | Мерк Энд Ко., Инк. | N-(2-benzyl)-2-phenylbutanamides as androgen receptor modulators |
CA2577608A1 (en) * | 2004-09-06 | 2006-03-16 | F. Hoffmann-La Roche Ag | 4-aminomethyl benzamidine derivatives and their use as factor viia inhibitors |
EP1912945A4 (en) * | 2005-08-02 | 2010-06-16 | Merck Sharp & Dohme | N- (PYRIDIN-4-YL) -2-PHENYLBUTANAMIDES AS MODULATORS OF THE ANDROGEN RECEPTOR |
WO2008136093A1 (ja) * | 2007-04-24 | 2008-11-13 | Nippon Soda Co., Ltd. | 置換メチルアミン化合物の製造方法及びトリアジン誘導体 |
CN103641776A (zh) * | 2007-04-24 | 2014-03-19 | 日本曹达株式会社 | N-亚甲基取代甲胺多聚物的制造方法和三嗪衍生物 |
CN104370804A (zh) * | 2007-04-24 | 2015-02-25 | 日本曹达株式会社 | 取代甲胺化合物的制造方法 |
RU2527177C2 (ru) * | 2007-12-20 | 2014-08-27 | Энвиво Фармасьютикалз, Инк. | Четырехзамещенные бензолы |
WO2010022148A1 (en) * | 2008-08-19 | 2010-02-25 | The Trustees Of The University Of Pennsylvania | Methods for the preparation of irciniastatin and analogs thereof |
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2003
- 2003-11-19 TW TW092132416A patent/TW200410921A/zh unknown
- 2003-11-20 PA PA20038589201A patent/PA8589201A1/es unknown
- 2003-11-21 JP JP2004554412A patent/JP4271657B2/ja not_active Expired - Fee Related
- 2003-11-21 CN CNA2003801035506A patent/CN1714079A/zh active Pending
- 2003-11-21 BR BR0316508-6A patent/BR0316508A/pt not_active IP Right Cessation
- 2003-11-21 AU AU2003292072A patent/AU2003292072B2/en not_active Ceased
- 2003-11-21 CA CA002505542A patent/CA2505542A1/en not_active Abandoned
- 2003-11-21 EP EP03767602A patent/EP1567498B1/en not_active Expired - Lifetime
- 2003-11-21 MX MXPA05005446A patent/MXPA05005446A/es active IP Right Grant
- 2003-11-21 US US10/720,790 patent/US7129238B2/en not_active Expired - Fee Related
- 2003-11-21 RU RU2005120146/04A patent/RU2005120146A/ru not_active Application Discontinuation
- 2003-11-21 DE DE60318890T patent/DE60318890T2/de not_active Expired - Fee Related
- 2003-11-21 WO PCT/EP2003/013087 patent/WO2004048335A2/en active IP Right Grant
- 2003-11-21 KR KR1020057009363A patent/KR100705156B1/ko not_active IP Right Cessation
- 2003-11-21 AT AT03767602T patent/ATE384696T1/de not_active IP Right Cessation
- 2003-11-21 ES ES03767602T patent/ES2298583T3/es not_active Expired - Lifetime
- 2003-11-21 GT GT200300252A patent/GT200300252A/es unknown
- 2003-11-21 PE PE2003001183A patent/PE20040696A1/es not_active Application Discontinuation
- 2003-11-21 AR ARP030104302A patent/AR042109A1/es not_active Application Discontinuation
- 2003-11-21 PL PL377511A patent/PL377511A1/pl not_active Application Discontinuation
- 2003-11-24 UY UY28090A patent/UY28090A1/es not_active Application Discontinuation
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2005
- 2005-05-11 NO NO20052311A patent/NO20052311L/no unknown
- 2005-05-17 ZA ZA200503989A patent/ZA200503989B/en unknown
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GT200300252A (es) | 2004-06-28 |
PA8589201A1 (es) | 2004-07-26 |
BR0316508A (pt) | 2005-10-04 |
RU2005120146A (ru) | 2006-05-10 |
WO2004048335A3 (en) | 2004-08-19 |
JP2006515284A (ja) | 2006-05-25 |
ES2298583T3 (es) | 2008-05-16 |
CA2505542A1 (en) | 2004-06-10 |
MXPA05005446A (es) | 2005-08-26 |
DE60318890T2 (de) | 2009-01-15 |
AR042109A1 (es) | 2005-06-08 |
CO5570663A2 (es) | 2005-10-31 |
UY28090A1 (es) | 2004-05-31 |
AU2003292072A1 (en) | 2004-06-18 |
JP4271657B2 (ja) | 2009-06-03 |
CN1714079A (zh) | 2005-12-28 |
PL377511A1 (pl) | 2006-02-06 |
ATE384696T1 (de) | 2008-02-15 |
EP1567498B1 (en) | 2008-01-23 |
AU2003292072B2 (en) | 2006-12-07 |
TW200410921A (en) | 2004-07-01 |
PE20040696A1 (es) | 2004-10-08 |
US20040122057A1 (en) | 2004-06-24 |
US7129238B2 (en) | 2006-10-31 |
NO20052311L (no) | 2005-06-16 |
WO2004048335A2 (en) | 2004-06-10 |
DE60318890D1 (de) | 2008-03-13 |
EP1567498A2 (en) | 2005-08-31 |
KR100705156B1 (ko) | 2007-04-09 |
KR20050086774A (ko) | 2005-08-30 |
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