RU2007101073A - Пятичленные гетероциклы, применимые в качестве ингибиторов сериновой протеазы - Google Patents
Пятичленные гетероциклы, применимые в качестве ингибиторов сериновой протеазы Download PDFInfo
- Publication number
- RU2007101073A RU2007101073A RU2007101073/04A RU2007101073A RU2007101073A RU 2007101073 A RU2007101073 A RU 2007101073A RU 2007101073/04 A RU2007101073/04 A RU 2007101073/04A RU 2007101073 A RU2007101073 A RU 2007101073A RU 2007101073 A RU2007101073 A RU 2007101073A
- Authority
- RU
- Russia
- Prior art keywords
- substituted
- phenyl
- imidazol
- benzyl
- alkyl
- Prior art date
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- 239000003001 serine protease inhibitor Substances 0.000 title 1
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 155
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 94
- 125000005842 heteroatom Chemical group 0.000 claims abstract 81
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 80
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 79
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 63
- 150000001875 compounds Chemical class 0.000 claims abstract 42
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 14
- 150000003839 salts Chemical class 0.000 claims abstract 13
- 239000012453 solvate Substances 0.000 claims abstract 13
- 239000000651 prodrug Substances 0.000 claims abstract 12
- 229940002612 prodrug Drugs 0.000 claims abstract 12
- -1 carbocycle Chemical group 0.000 claims 205
- 125000000217 alkyl group Chemical group 0.000 claims 130
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 92
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 52
- 229910052799 carbon Inorganic materials 0.000 claims 49
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 45
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 34
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 33
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 32
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 31
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 27
- 125000003118 aryl group Chemical group 0.000 claims 22
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 18
- 125000004429 atom Chemical group 0.000 claims 16
- 125000001624 naphthyl group Chemical group 0.000 claims 14
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 12
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 10
- 125000004076 pyridyl group Chemical group 0.000 claims 10
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 9
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 9
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 8
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 7
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 6
- 125000004606 5,6,7,8-tetrahydroisoquinolinyl group Chemical group C1(=NC=CC=2CCCCC12)* 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 6
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 6
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 6
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 6
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 claims 5
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 4
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 3
- 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 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 125000004537 indazol-5-yl group Chemical group N1N=CC2=CC(=CC=C12)* 0.000 claims 3
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 2
- WENDBLUMXCYTNC-CVCZCXRASA-N 1-amino-2-[(1s)-1-[4-(4-carbamoylphenyl)-5-chloro-1h-imidazol-2-yl]-2-phenylethyl]-5,6,7,8-tetrahydro-1h-isoquinoline-6-carboxylic acid Chemical compound C([C@H](N1C(C2=C(CC(CC2)C(O)=O)C=C1)N)C=1NC(Cl)=C(N=1)C=1C=CC(=CC=1)C(N)=O)C1=CC=CC=C1 WENDBLUMXCYTNC-CVCZCXRASA-N 0.000 claims 2
- YAWQINPGEUGUKE-IAXKEJLGSA-N 1-amino-n-[(1s)-1-[4-(4-carbamoylphenyl)-5-chloro-1h-imidazol-2-yl]-2-phenylethyl]-5,6,7,8-tetrahydroisoquinoline-6-carboxamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=C(Cl)NC([C@H](CC=2C=CC=CC=2)NC(=O)C2CC3=CC=NC(N)=C3CC2)=N1 YAWQINPGEUGUKE-IAXKEJLGSA-N 0.000 claims 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 206010047249 Venous thrombosis Diseases 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 230000002526 effect on cardiovascular system Effects 0.000 claims 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- YDLAQBRNNOLMIH-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]formamide Chemical group ClC1=CC=C(CNC=O)C=C1 YDLAQBRNNOLMIH-UHFFFAOYSA-N 0.000 claims 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 125000006413 ring segment Chemical group 0.000 claims 2
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 230000009424 thromboembolic effect Effects 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- ICSJXVUUSDNFIJ-AVRDEDQJSA-N (6s)-1-amino-n-[(1s)-1-[4-(3-amino-1h-indazol-6-yl)-5-chloro-1h-imidazol-2-yl]-2-phenylethyl]-5,6,7,8-tetrahydroisoquinoline-6-carboxamide Chemical compound C([C@@H](C1=NC(=C(N1)Cl)C=1C=C2NN=C(C2=CC=1)N)NC(=O)[C@@H]1CC2=CC=NC(N)=C2CC1)C1=CC=CC=C1 ICSJXVUUSDNFIJ-AVRDEDQJSA-N 0.000 claims 1
- ICSJXVUUSDNFIJ-HXBUSHRASA-N (6s)-1-amino-n-[1-[4-(3-amino-1h-indazol-6-yl)-5-chloro-1h-imidazol-2-yl]-2-phenylethyl]-5,6,7,8-tetrahydroisoquinoline-6-carboxamide Chemical compound C=1C=C2C(N)=NNC2=CC=1C(=C(N1)Cl)N=C1C(NC(=O)[C@@H]1CC2=CC=NC(N)=C2CC1)CC1=CC=CC=C1 ICSJXVUUSDNFIJ-HXBUSHRASA-N 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical group C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims 1
- KCOPAESEGCGTKM-UHFFFAOYSA-N 1,3-oxazol-4-one Chemical class O=C1COC=N1 KCOPAESEGCGTKM-UHFFFAOYSA-N 0.000 claims 1
- KWHJKKRXFUNBAJ-QFIPXVFZSA-N 1-amino-n-[(1s)-1-[4-(3-amino-1h-indazol-6-yl)-5-chloro-1h-imidazol-2-yl]-2-phenylethyl]isoquinoline-6-carboxamide Chemical compound C([C@@H](C1=NC(=C(N1)Cl)C=1C=C2NN=C(C2=CC=1)N)NC(=O)C=1C=C2C=CN=C(N)C2=CC=1)C1=CC=CC=C1 KWHJKKRXFUNBAJ-QFIPXVFZSA-N 0.000 claims 1
- ZBNZAJFNDPPMDT-UHFFFAOYSA-N 1h-imidazole-5-carboxamide Chemical compound NC(=O)C1=CNC=N1 ZBNZAJFNDPPMDT-UHFFFAOYSA-N 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
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims 1
- RRHJIQKUXUNEBA-IRSIHTCSSA-N 2-[3-[2-[(1s)-1-[[4-(aminomethyl)cyclohexanecarbonyl]amino]-2-phenylethyl]-1h-imidazol-5-yl]phenyl]acetic acid Chemical compound C1CC(CN)CCC1C(=O)N[C@H](C=1NC=C(N=1)C=1C=C(CC(O)=O)C=CC=1)CC1=CC=CC=C1 RRHJIQKUXUNEBA-IRSIHTCSSA-N 0.000 claims 1
- WWUIZLHTDBGHFH-UHFFFAOYSA-N 2-[5-(4-carbamimidoylphenyl)-1h-imidazol-2-yl]-n,3-diphenylpropanamide Chemical compound C1=CC(C(=N)N)=CC=C1C1=CNC(C(CC=2C=CC=CC=2)C(=O)NC=2C=CC=CC=2)=N1 WWUIZLHTDBGHFH-UHFFFAOYSA-N 0.000 claims 1
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 1
- PKSAIJQAOZGOKV-IBGZPJMESA-N 3-amino-n-[(1s)-1-[4-(3-amino-1h-indazol-6-yl)-5-chloro-1h-imidazol-2-yl]-2-phenylethyl]-1,2-benzoxazole-6-carboxamide Chemical compound C([C@@H](C1=NC(=C(N1)Cl)C=1C=C2NN=C(C2=CC=1)N)NC(=O)C=1C=C2ON=C(N)C2=CC=1)C1=CC=CC=C1 PKSAIJQAOZGOKV-IBGZPJMESA-N 0.000 claims 1
- IAJDAQJCIKJYEG-FQEVSTJZSA-N 3-amino-n-[(1s)-1-[4-(3-amino-1h-indazol-6-yl)-5-chloro-1h-imidazol-2-yl]-2-phenylethyl]-1h-indazole-5-carboxamide Chemical compound C([C@@H](C1=NC(=C(N1)Cl)C=1C=C2NN=C(C2=CC=1)N)NC(=O)C=1C=C2C(N)=NNC2=CC=1)C1=CC=CC=C1 IAJDAQJCIKJYEG-FQEVSTJZSA-N 0.000 claims 1
- QEDSKDDUNJZZHC-FQEVSTJZSA-N 3-amino-n-[(1s)-1-[4-(3-amino-1h-indazol-6-yl)-5-chloro-1h-imidazol-2-yl]-2-phenylethyl]-1h-indazole-6-carboxamide Chemical compound C([C@H](NC(=O)C=1C=C2NN=C(C2=CC=1)N)C=1NC(Cl)=C(N=1)C=1C=C2NN=C(N)C2=CC=1)C1=CC=CC=C1 QEDSKDDUNJZZHC-FQEVSTJZSA-N 0.000 claims 1
- YVUNSWOVNWOOSB-NRFANRHFSA-N 3-amino-n-[(1s)-1-[5-(4-carbamimidoylphenyl)-1h-imidazol-2-yl]-2-phenylethyl]-1h-indazole-5-carboxamide Chemical compound C1=CC(C(=N)N)=CC=C1C1=CNC([C@H](CC=2C=CC=CC=2)NC(=O)C=2C=C3C(N)=NNC3=CC=2)=N1 YVUNSWOVNWOOSB-NRFANRHFSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- ZEJLTWLVGBBHBH-FYPSYCSSSA-N 4-[(1S)-1-[4-(4-aminoquinazolin-7-yl)-5-chloro-1H-imidazol-2-yl]-2-phenylethyl]-3-fluorocyclohexa-1,5-diene-1,4-dicarboxamide Chemical compound NC1=NC=NC2=CC(=CC=C12)C=1N=C(NC1Cl)[C@@H](CC1=CC=CC=C1)C1(C(=O)N)C(C=C(C(=O)N)C=C1)F ZEJLTWLVGBBHBH-FYPSYCSSSA-N 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims 1
- 206010003178 Arterial thrombosis Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010003658 Atrial Fibrillation Diseases 0.000 claims 1
- SFZTUAGLDAGVMT-SKPFHBQLSA-N C([C@@H](C=1NC(=C(N=1)C=1C=C2NN=CC2=CC=1)C)NC(=O)[C@@H]1CC[C@@H](CN)CC1)C1=CC=CC=C1 Chemical compound C([C@@H](C=1NC(=C(N=1)C=1C=C2NN=CC2=CC=1)C)NC(=O)[C@@H]1CC[C@@H](CN)CC1)C1=CC=CC=C1 SFZTUAGLDAGVMT-SKPFHBQLSA-N 0.000 claims 1
- DHIHJHBYWNQABC-VIQNHZKISA-N C1=CC(NC(=O)OC)=CC=C1C1=C(C)NC(C(CC=2C=CC=CC=2)NC(=O)[C@@H]2CC[C@@H](CN)CC2)=N1 Chemical compound C1=CC(NC(=O)OC)=CC=C1C1=C(C)NC(C(CC=2C=CC=CC=2)NC(=O)[C@@H]2CC[C@@H](CN)CC2)=N1 DHIHJHBYWNQABC-VIQNHZKISA-N 0.000 claims 1
- SZQZCQKMZHGHRO-MCPCIJHBSA-N C1=CC=C(C=C1)C[C@H](C2=NC(=C(N2)Cl)C3=CC4=C(C=C3)C(=NN4)N)C5(C=CC(=CC5F)C(=O)N)C(=O)N Chemical compound C1=CC=C(C=C1)C[C@H](C2=NC(=C(N2)Cl)C3=CC4=C(C=C3)C(=NN4)N)C5(C=CC(=CC5F)C(=O)N)C(=O)N SZQZCQKMZHGHRO-MCPCIJHBSA-N 0.000 claims 1
- PMPZBVXOHYLBLZ-CCCGKPSOSA-N C1C[C@@H](CN)CC[C@@H]1C(=O)NC(C=1NC(Cl)=C(N=1)C=1C=C2NN=C(N)C2=CC=1)CC1=CC=CC(OC(F)F)=C1 Chemical compound C1C[C@@H](CN)CC[C@@H]1C(=O)NC(C=1NC(Cl)=C(N=1)C=1C=C2NN=C(N)C2=CC=1)CC1=CC=CC(OC(F)F)=C1 PMPZBVXOHYLBLZ-CCCGKPSOSA-N 0.000 claims 1
- CGWMVOBUPNPZBP-BDWYFLKXSA-N C1C[C@@H](CN)CC[C@@H]1C(=O)NC(C=1NC(Cl)=C(N=1)C=1SC(=CC=1)C(O)=O)CC1=CC=CC=C1 Chemical compound C1C[C@@H](CN)CC[C@@H]1C(=O)NC(C=1NC(Cl)=C(N=1)C=1SC(=CC=1)C(O)=O)CC1=CC=CC=C1 CGWMVOBUPNPZBP-BDWYFLKXSA-N 0.000 claims 1
- KDTNBPJFLDIYKY-FAHCRBBMSA-N C1C[C@@H](CN)CC[C@@H]1C(=O)NC(C=1NC=C(N=1)C=1C=C2NN=C(N)C2=CC=1)CC1=CC=CC=C1OCC1=CC=CC=C1 Chemical compound C1C[C@@H](CN)CC[C@@H]1C(=O)NC(C=1NC=C(N=1)C=1C=C2NN=C(N)C2=CC=1)CC1=CC=CC=C1OCC1=CC=CC=C1 KDTNBPJFLDIYKY-FAHCRBBMSA-N 0.000 claims 1
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- SXHMJNGJPFLPLF-NRFANRHFSA-N n-[(1s)-1-[4-(3-amino-1h-indazol-6-yl)-5-chloro-1h-imidazol-2-yl]-2-phenylethyl]-4-(aminomethyl)-2-fluorobenzamide Chemical compound FC1=CC(CN)=CC=C1C(=O)N[C@H](C=1NC(Cl)=C(N=1)C=1C=C2NN=C(N)C2=CC=1)CC1=CC=CC=C1 SXHMJNGJPFLPLF-NRFANRHFSA-N 0.000 claims 1
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- RPVDITCKHCKYBN-LJAQVGFWSA-N n-[(1s)-1-[4-(4-carbamimidoylphenyl)-1-(2-phenylethyl)imidazol-2-yl]-2-phenylethyl]benzamide Chemical compound C1=CC(C(=N)N)=CC=C1C(N=C1[C@H](CC=2C=CC=CC=2)NC(=O)C=2C=CC=CC=2)=CN1CCC1=CC=CC=C1 RPVDITCKHCKYBN-LJAQVGFWSA-N 0.000 claims 1
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- HMOMOTNEBKIQEO-QFIPXVFZSA-N n-[(1s)-1-[4-(4-carbamimidoylphenyl)-1-methylimidazol-2-yl]-2-phenylethyl]benzamide Chemical compound C([C@@H](C1=NC(=CN1C)C=1C=CC(=CC=1)C(N)=N)NC(=O)C=1C=CC=CC=1)C1=CC=CC=C1 HMOMOTNEBKIQEO-QFIPXVFZSA-N 0.000 claims 1
- KRXIFLREGAPDHE-IRZJEQJZSA-N n-[(1s)-1-[5-(3-amino-1h-indazol-6-yl)-1h-imidazol-2-yl]-4-[(5-methylpyrazin-2-yl)methylamino]-4-oxobutyl]-4-(aminomethyl)cyclohexane-1-carboxamide Chemical compound C1=NC(C)=CN=C1CNC(=O)CC[C@@H](C=1NC(=CN=1)C=1C=C2NN=C(N)C2=CC=1)NC(=O)C1CCC(CN)CC1 KRXIFLREGAPDHE-IRZJEQJZSA-N 0.000 claims 1
- AZKBLOTXRUYVCR-QHCPKHFHSA-N n-[(1s)-1-[5-(4-carbamimidoylphenyl)-1h-imidazol-2-yl]-2-phenylethyl]-1h-indole-6-carboxamide Chemical compound C1=CC(C(=N)N)=CC=C1C1=CNC([C@H](CC=2C=CC=CC=2)NC(=O)C=2C=C3NC=CC3=CC=2)=N1 AZKBLOTXRUYVCR-QHCPKHFHSA-N 0.000 claims 1
- MMARSDSMJMHKLL-NRFANRHFSA-N n-[(1s)-1-[5-(4-carbamimidoylphenyl)-1h-imidazol-2-yl]-2-phenylethyl]benzamide Chemical compound C1=CC(C(=N)N)=CC=C1C1=CNC([C@H](CC=2C=CC=CC=2)NC(=O)C=2C=CC=CC=2)=N1 MMARSDSMJMHKLL-NRFANRHFSA-N 0.000 claims 1
- NVCGCCVEGKNTRF-UHFFFAOYSA-N n-[1-[4-(3-amino-1h-indazol-6-yl)-5-chloro-1h-imidazol-2-yl]-2-phenylethyl]-2-fluoro-4-methylbenzamide Chemical compound FC1=CC(C)=CC=C1C(=O)NC(C=1NC(Cl)=C(N=1)C=1C=C2NN=C(N)C2=CC=1)CC1=CC=CC=C1 NVCGCCVEGKNTRF-UHFFFAOYSA-N 0.000 claims 1
- 230000000414 obstructive effect Effects 0.000 claims 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 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
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims 1
- 239000010802 sludge Substances 0.000 claims 1
- 239000002689 soil Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 claims 1
- 201000005060 thrombophlebitis Diseases 0.000 claims 1
- 206010044008 tonsillitis Diseases 0.000 claims 1
- 230000001052 transient effect Effects 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 8
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 abstract 2
Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D235/08—Radicals containing only hydrogen and carbon atoms
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- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
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- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- 2005-06-13 US US11/151,667 patent/US7453002B2/en active Active
- 2005-06-14 ES ES05773261.2T patent/ES2628279T3/es not_active Expired - Lifetime
- 2005-06-14 BR BRPI0512084-5A patent/BRPI0512084A/pt not_active IP Right Cessation
- 2005-06-14 AU AU2005254102A patent/AU2005254102A1/en not_active Abandoned
- 2005-06-14 JP JP2007516703A patent/JP4791460B2/ja not_active Expired - Fee Related
- 2005-06-14 CA CA002570472A patent/CA2570472A1/en not_active Abandoned
- 2005-06-14 EP EP05773261.2A patent/EP1773786B1/en not_active Expired - Lifetime
- 2005-06-14 MX MXPA06014642A patent/MXPA06014642A/es active IP Right Grant
- 2005-06-14 WO PCT/US2005/021212 patent/WO2005123050A2/en not_active Ceased
- 2005-06-14 KR KR1020067026365A patent/KR20070024601A/ko not_active Ceased
- 2005-06-14 RU RU2007101073/04A patent/RU2007101073A/ru not_active Application Discontinuation
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2006
- 2006-12-05 IL IL179844A patent/IL179844A0/en unknown
- 2006-12-15 NO NO20065864A patent/NO20065864L/no not_active Application Discontinuation
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2008
- 2008-09-12 US US12/209,235 patent/US8101778B2/en active Active
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2011
- 2011-12-15 US US13/326,809 patent/US8716492B2/en not_active Expired - Lifetime
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2014
- 2014-03-19 US US14/219,311 patent/US9079860B2/en not_active Expired - Lifetime
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2015
- 2015-05-27 US US14/722,434 patent/US9617224B2/en not_active Expired - Lifetime
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2017
- 2017-02-23 US US15/440,346 patent/US10112936B2/en not_active Expired - Lifetime
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| AU2005254102A1 (en) | 2005-12-29 |
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| US8101778B2 (en) | 2012-01-24 |
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| US20090036438A1 (en) | 2009-02-05 |
| JP2008502700A (ja) | 2008-01-31 |
| US7453002B2 (en) | 2008-11-18 |
| WO2005123050A3 (en) | 2007-01-04 |
| KR20070024601A (ko) | 2007-03-02 |
| EP1773786B1 (en) | 2017-04-26 |
| BRPI0512084A (pt) | 2008-02-06 |
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| US20170166560A1 (en) | 2017-06-15 |
| US9079860B2 (en) | 2015-07-14 |
| NO20065864L (no) | 2007-03-02 |
| ES2628279T3 (es) | 2017-08-02 |
| US20140206706A1 (en) | 2014-07-24 |
| US20050282805A1 (en) | 2005-12-22 |
| JP4791460B2 (ja) | 2011-10-12 |
| US8716492B2 (en) | 2014-05-06 |
| US10112936B2 (en) | 2018-10-30 |
| CA2570472A1 (en) | 2005-12-29 |
| IL179844A0 (en) | 2007-07-04 |
| US20120088758A1 (en) | 2012-04-12 |
| US9617224B2 (en) | 2017-04-11 |
| US20150259297A1 (en) | 2015-09-17 |
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