JPH08502285A - 循環系障害処置用ｎ−アリールヘテロアリールアルキル１−シクロアルキル−イミダゾール−２−オン化合物 - Google Patents

循環系障害処置用ｎ−アリールヘテロアリールアルキル１−シクロアルキル−イミダゾール−２−オン化合物

Info

Publication number: JPH08502285A
Authority: JP; Japan
Prior art keywords: butyl; methyl; phenyl; pyridinyl; dihydro
Prior art date: 1992-10-13
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP6509961A

Other languages

English (en)

Japanese (ja)

Inventor

ビー．ライツ，デビッド

イー．マニング，ロバート

Original Assignee

ジー．ディー．サールアンドカンパニー

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1992-10-13

Filing date

1993-06-16

Publication date

1996-03-12

1993-06-16 Application filed by ジー．ディー．サールアンドカンパニー filed Critical ジー．ディー．サールアンドカンパニー

1996-03-12 Publication of JPH08502285A publication Critical patent/JPH08502285A/ja

Status Pending legal-status Critical Current

Links

208000024172 Cardiovascular disease Diseases 0.000 title claims abstract description 21
-1 hydroxy, carboxyl Chemical group 0.000 claims abstract description 1835
150000001875 compounds Chemical class 0.000 claims abstract description 380
150000003839 salts Chemical class 0.000 claims abstract description 191
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 106
150000004678 hydrides Chemical class 0.000 claims abstract description 97
230000002378 acidificating effect Effects 0.000 claims abstract description 40
125000000217 alkyl group Chemical group 0.000 claims abstract description 27
206010020772 Hypertension Diseases 0.000 claims abstract description 15
239000002333 angiotensin II receptor antagonist Substances 0.000 claims abstract description 12
229940123413 Angiotensin II antagonist Drugs 0.000 claims abstract description 11
125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 8
206010019280 Heart failures Diseases 0.000 claims abstract description 7
206010007559 Cardiac failure congestive Diseases 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 640
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 462
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 164
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 158
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 157
125000004043 oxo group Chemical group O=* 0.000 claims description 99
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 89
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 85
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 85
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 85
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 84
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 84
125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 79
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 67
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 48
238000000034 method Methods 0.000 claims description 34
WZELXJBMMZFDDU-UHFFFAOYSA-N Imidazol-2-one Chemical compound O=C1N=CC=N1 WZELXJBMMZFDDU-UHFFFAOYSA-N 0.000 claims description 24
125000001153 fluoro group Chemical group F* 0.000 claims description 22
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 description 20
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 20
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
239000000203 mixture Substances 0.000 claims description 19
239000005557 antagonist Substances 0.000 claims description 18
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
125000005843 halogen group Chemical group 0.000 claims description 17
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 description 15
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 15
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 description 15
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 15
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 15
125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 15
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 14
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 14
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 13
125000000753 cycloalkyl group Chemical group 0.000 claims description 13
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
125000003282 alkyl amino group Chemical group 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 7
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 7
WLNRVWDZZPYACO-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcyclohexyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1(C)C WLNRVWDZZPYACO-UHFFFAOYSA-N 0.000 claims description 6
PXJCLJXRQHYNRA-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-5-methylcyclopentyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCC1CC PXJCLJXRQHYNRA-UHFFFAOYSA-N 0.000 claims description 6
GYOMGXAIFSUPKX-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-6-methylcyclohexyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCC1CC GYOMGXAIFSUPKX-UHFFFAOYSA-N 0.000 claims description 6
FLHIJKKQZCLBJM-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-6-propan-2-ylcyclohexyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCC1C(C)C FLHIJKKQZCLBJM-UHFFFAOYSA-N 0.000 claims description 6
DRLWSYKKILFITI-UHFFFAOYSA-N 4-butyl-1-(2-methyl-6-propan-2-ylcyclohexyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCC1C(C)C DRLWSYKKILFITI-UHFFFAOYSA-N 0.000 claims description 6
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
WURCEMJIYOFZDQ-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-5-propan-2-ylcyclopentyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCC1C(C)C WURCEMJIYOFZDQ-UHFFFAOYSA-N 0.000 claims description 5
DIUOLGCUSJLVFR-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-1-yl]-3-methylcyclohexane-1-carboxylic acid Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCC1C(O)=O DIUOLGCUSJLVFR-UHFFFAOYSA-N 0.000 claims description 4
PNQYLNZBQCFEBU-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-1-yl]cyclohexane-1-carboxylic acid Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1C(O)=O PNQYLNZBQCFEBU-UHFFFAOYSA-N 0.000 claims description 4
GBXQWPCVQAHRBS-UHFFFAOYSA-N 4-butyl-1-(2,6-dimethylcyclohexyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCC1C GBXQWPCVQAHRBS-UHFFFAOYSA-N 0.000 claims description 4
HZAAPVSPYSIEPX-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-6-oxocyclohexyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCC1=O HZAAPVSPYSIEPX-UHFFFAOYSA-N 0.000 claims description 4
QCOGDPYPIHYKLW-UHFFFAOYSA-N 4-butyl-1-(2-methoxycyclohexyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1OC QCOGDPYPIHYKLW-UHFFFAOYSA-N 0.000 claims description 4
DUORFZHKSLBXFC-UHFFFAOYSA-N 4-butyl-1-(2-methyl-5-propan-2-ylcyclopentyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCC1C(C)C DUORFZHKSLBXFC-UHFFFAOYSA-N 0.000 claims description 4
VALIFUQXEXXZGU-UHFFFAOYSA-N 4-butyl-1-(2-propylcyclohexyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1CCC VALIFUQXEXXZGU-UHFFFAOYSA-N 0.000 claims description 4
XUENMLWFLLPPMI-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcyclohexyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1C(C)(C)C XUENMLWFLLPPMI-UHFFFAOYSA-N 0.000 claims description 4
208000010412 Glaucoma Diseases 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
125000003884 phenylalkyl group Chemical group 0.000 claims description 4
YZLYYKFPIXFQNI-UHFFFAOYSA-N 1-(2-acetylcyclohexyl)-4-butyl-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1C(C)=O YZLYYKFPIXFQNI-UHFFFAOYSA-N 0.000 claims description 3
YUVFWRDXXFSXHU-UHFFFAOYSA-N 4-butyl-1-(2,2-diethylcyclohexyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1(CC)CC YUVFWRDXXFSXHU-UHFFFAOYSA-N 0.000 claims description 3
BLWKASDKHCPZIV-UHFFFAOYSA-N 4-butyl-1-(2,4-dimethylcyclopentyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC(C)CC1C BLWKASDKHCPZIV-UHFFFAOYSA-N 0.000 claims description 3
MBJVGWLUSCIDQY-UHFFFAOYSA-N 4-butyl-1-(2,5-diethylcyclopentyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCC1CC MBJVGWLUSCIDQY-UHFFFAOYSA-N 0.000 claims description 3
OAGALTIDELJYTO-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-5-oxocyclopentyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCC1=O OAGALTIDELJYTO-UHFFFAOYSA-N 0.000 claims description 3
SSLPXSDURUYFRD-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycyclohexyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1O SSLPXSDURUYFRD-UHFFFAOYSA-N 0.000 claims description 3
WIHKGLGMPLNMJA-UHFFFAOYSA-N 4-butyl-1-(2-methyl-5-oxocyclopentyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCC1=O WIHKGLGMPLNMJA-UHFFFAOYSA-N 0.000 claims description 3
GDEWFWOFWINAQD-UHFFFAOYSA-N 4-butyl-1-(2-methyl-6-oxocyclohexyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCC1=O GDEWFWOFWINAQD-UHFFFAOYSA-N 0.000 claims description 3
IIBYUINBMNTZDE-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcyclohexyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1C(C)C IIBYUINBMNTZDE-UHFFFAOYSA-N 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
IRXOGFWNLRIKKD-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-1-yl]-3-ethylcyclohexane-1-carboxylic acid Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCC1C(O)=O IRXOGFWNLRIKKD-UHFFFAOYSA-N 0.000 claims description 2
PMLVDGQFWCLSGL-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-1-yl]-3-propan-2-ylcyclohexane-1-carboxylic acid Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CCCC1C(O)=O PMLVDGQFWCLSGL-UHFFFAOYSA-N 0.000 claims description 2
OOPUPOXOJCOABY-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-1-yl]cyclopentane-1-carboxylic acid Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1C(O)=O OOPUPOXOJCOABY-UHFFFAOYSA-N 0.000 claims description 2
SNGPUKKSHPUICX-UHFFFAOYSA-N 4-butyl-1-(2,2-diethylcyclopentyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1(CC)CC SNGPUKKSHPUICX-UHFFFAOYSA-N 0.000 claims description 2
NDFWJERMSBYDOX-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycyclopentyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1O NDFWJERMSBYDOX-UHFFFAOYSA-N 0.000 claims description 2
BEXAJHPLCICHHM-UHFFFAOYSA-N 4-butyl-1-(2-methoxycyclopentyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1OC BEXAJHPLCICHHM-UHFFFAOYSA-N 0.000 claims description 2
DQWBBBSQDHPDIX-UHFFFAOYSA-N 4-butyl-1-(2-oxo-6-propan-2-ylcyclohexyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CCCC1=O DQWBBBSQDHPDIX-UHFFFAOYSA-N 0.000 claims description 2
INENTDISMRZJGA-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcyclopentyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1C(C)C INENTDISMRZJGA-UHFFFAOYSA-N 0.000 claims description 2
UTDLKJICHMRSTJ-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcyclopentyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1C(C)(C)C UTDLKJICHMRSTJ-UHFFFAOYSA-N 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
FYJFKCHNFRORHU-UHFFFAOYSA-N 1-(2-acetyl-6-methylcyclohexyl)-4-butyl-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCC1C(C)=O FYJFKCHNFRORHU-UHFFFAOYSA-N 0.000 claims 3
ULSZFINYQHIOLI-UHFFFAOYSA-N 1-(2-acetyl-6-propan-2-ylcyclohexyl)-4-butyl-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CCCC1C(C)=O ULSZFINYQHIOLI-UHFFFAOYSA-N 0.000 claims 3
NONYNOUAMLTBIK-UHFFFAOYSA-N 4-butyl-1-(2-methylcyclohexyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1C NONYNOUAMLTBIK-UHFFFAOYSA-N 0.000 claims 3
XIBDZPULMDCKOG-UHFFFAOYSA-N 4-butyl-1-(2-oxocyclohexyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1=O XIBDZPULMDCKOG-UHFFFAOYSA-N 0.000 claims 3
GARCBUHTQIAHOA-UHFFFAOYSA-N 1-(2-acetyl-6-ethylcyclohexyl)-4-butyl-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCC1C(C)=O GARCBUHTQIAHOA-UHFFFAOYSA-N 0.000 claims 2
YHQWVXXNHGJYJQ-UHFFFAOYSA-N 4-butyl-1-[2,6-di(propan-2-yl)cyclohexyl]-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CCCC1C(C)C YHQWVXXNHGJYJQ-UHFFFAOYSA-N 0.000 claims 2
210000000748 cardiovascular system Anatomy 0.000 claims 2
IEJDOGSTGSDLEO-UHFFFAOYSA-N 1-(2-acetyl-5-methylcyclopentyl)-4-butyl-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCC1C(C)=O IEJDOGSTGSDLEO-UHFFFAOYSA-N 0.000 claims 1
VGUMXOPPGKIZHR-UHFFFAOYSA-N 1-(2-acetyl-5-propan-2-ylcyclopentyl)-4-butyl-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CCC1C(C)=O VGUMXOPPGKIZHR-UHFFFAOYSA-N 0.000 claims 1
LYGLXVUICCKJAX-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-1-yl]-3-ethylcyclopentane-1-carboxylic acid Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCC1C(O)=O LYGLXVUICCKJAX-UHFFFAOYSA-N 0.000 claims 1
IHJSCOOOHJVSBN-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-1-yl]-3-methylcyclopentane-1-carboxylic acid Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCC1C(O)=O IHJSCOOOHJVSBN-UHFFFAOYSA-N 0.000 claims 1
BOENCEXAGQWZHD-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-1-yl]-3-propan-2-ylcyclopentane-1-carboxylic acid Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CCC1C(O)=O BOENCEXAGQWZHD-UHFFFAOYSA-N 0.000 claims 1
JVPBMVGYOVWVEO-UHFFFAOYSA-N 4-butyl-1-(2-ethylcyclohexyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1CC JVPBMVGYOVWVEO-UHFFFAOYSA-N 0.000 claims 1
DOSMTZJNNCKZTK-UHFFFAOYSA-N 4-butyl-1-(2-methylcyclopentyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1C DOSMTZJNNCKZTK-UHFFFAOYSA-N 0.000 claims 1
LEAXLUYIQCSDGU-UHFFFAOYSA-N 4-butyl-1-(2-oxocyclopentyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1=O LEAXLUYIQCSDGU-UHFFFAOYSA-N 0.000 claims 1
RCBLQELGKPQKJJ-UHFFFAOYSA-N 4-butyl-1-(2-propylcyclopentyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1CCC RCBLQELGKPQKJJ-UHFFFAOYSA-N 0.000 claims 1
UUSRNVWPRFMWRO-UHFFFAOYSA-N 4-butyl-1-[2,5-di(propan-2-yl)cyclopentyl]-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CCC1C(C)C UUSRNVWPRFMWRO-UHFFFAOYSA-N 0.000 claims 1
JMVQFRFKXOIRBI-UHFFFAOYSA-N 4-methylimidazol-2-one Chemical compound CC1=NC(=O)N=C1 JMVQFRFKXOIRBI-UHFFFAOYSA-N 0.000 claims 1
206010059245 Angiopathy Diseases 0.000 claims 1
JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 claims 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
238000003419 tautomerization reaction Methods 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
208000019553 vascular disease Diseases 0.000 claims 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
125000001475 halogen functional group Chemical group 0.000 abstract 1
125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 130
238000010586 diagram Methods 0.000 description 91
239000003153 chemical reaction reagent Substances 0.000 description 34
238000004519 manufacturing process Methods 0.000 description 31
239000002253 acid Substances 0.000 description 29
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
102000015427 Angiotensins Human genes 0.000 description 17
108010064733 Angiotensins Proteins 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
229950006323 angiotensin ii Drugs 0.000 description 15
230000000694 effects Effects 0.000 description 15
102000005862 Angiotensin II Human genes 0.000 description 14
101800000733 Angiotensin-2 Proteins 0.000 description 14
CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 14
230000008878 coupling Effects 0.000 description 14
238000010168 coupling process Methods 0.000 description 14
238000005859 coupling reaction Methods 0.000 description 14
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 13
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 12
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 12
229910052794 bromium Inorganic materials 0.000 description 12
125000001309 chloro group Chemical group Cl* 0.000 description 12
239000012280 lithium aluminium hydride Substances 0.000 description 12
230000008569 process Effects 0.000 description 12
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 11
239000004202 carbamide Substances 0.000 description 11
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 11
238000010992 reflux Methods 0.000 description 11
238000012360 testing method Methods 0.000 description 11
241000700159 Rattus Species 0.000 description 10
239000004327 boric acid Substances 0.000 description 10
239000003814 drug Substances 0.000 description 10
230000002526 effect on cardiovascular system Effects 0.000 description 10
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 10
125000001145 hydrido group Chemical group *[H] 0.000 description 10
230000004044 response Effects 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 9
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 9
102000005962 receptors Human genes 0.000 description 9
108020003175 receptors Proteins 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
208000035475 disorder Diseases 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
239000000243 solution Substances 0.000 description 8
230000002152 alkylating effect Effects 0.000 description 7
WGQKYBSKWIADBV-UHFFFAOYSA-N aminomethyl benzene Natural products NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 7
230000037396 body weight Effects 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
241000894007 species Species 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 7
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 7
BIWQNIMLAISTBV-UHFFFAOYSA-N (4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1 BIWQNIMLAISTBV-UHFFFAOYSA-N 0.000 description 6
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 6
NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
230000027455 binding Effects 0.000 description 6
125000001246 bromo group Chemical group Br* 0.000 description 6
125000002883 imidazolyl group Chemical group 0.000 description 6
239000007924 injection Substances 0.000 description 6
238000002347 injection Methods 0.000 description 6
239000012948 isocyanate Substances 0.000 description 6
125000001979 organolithium group Chemical group 0.000 description 6
229910000077 silane Inorganic materials 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 5
FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 5
OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 5
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
150000001299 aldehydes Chemical class 0.000 description 5
238000003556 assay Methods 0.000 description 5
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 5
125000004122 cyclic group Chemical group 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
238000006467 substitution reaction Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
FYFARMAMPHSRIH-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-3-methylcyclopropyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)C1CC FYFARMAMPHSRIH-UHFFFAOYSA-N 0.000 description 4
QKCYTDDOYYRUPZ-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-3-methylcyclopropyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)C1CC QKCYTDDOYYRUPZ-UHFFFAOYSA-N 0.000 description 4
ZPLAASUZZFTZCQ-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-4-methylcyclobutyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CC1CC ZPLAASUZZFTZCQ-UHFFFAOYSA-N 0.000 description 4
GHPSIYSCYUMNIP-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-4-methylcyclobutyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CC1CC GHPSIYSCYUMNIP-UHFFFAOYSA-N 0.000 description 4
JARBFKPJVQSAJZ-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-5-methylcyclopentyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCC1CC JARBFKPJVQSAJZ-UHFFFAOYSA-N 0.000 description 4
LCNTVEWHXDFDDU-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-5-methylcyclopentyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCC1CC LCNTVEWHXDFDDU-UHFFFAOYSA-N 0.000 description 4
HXXOEGYPRVBATA-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-6-methylcyclohexyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCC1CC HXXOEGYPRVBATA-UHFFFAOYSA-N 0.000 description 4
XYUJDDVXCYGELP-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-6-methylcyclohexyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCC1CC XYUJDDVXCYGELP-UHFFFAOYSA-N 0.000 description 4
JKNRZQSLTPVADO-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-7-methylcycloheptyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCC1CC JKNRZQSLTPVADO-UHFFFAOYSA-N 0.000 description 4
BLRNPUHXIKNABS-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-8-methylcyclooctyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCCC1CC BLRNPUHXIKNABS-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
JJPDWWGVBSJWNW-UHFFFAOYSA-N C(C)C1C(C(CCCCC1)C)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound C(C)C1C(C(CCCCC1)C)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O JJPDWWGVBSJWNW-UHFFFAOYSA-N 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
235000011054 acetic acid Nutrition 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
230000000202 analgesic effect Effects 0.000 description 4
230000003276 anti-hypertensive effect Effects 0.000 description 4
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 4
125000004982 dihaloalkyl group Chemical group 0.000 description 4
201000010099 disease Diseases 0.000 description 4
229910052744 lithium Inorganic materials 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
ZQGJEUVBUVKZKS-UHFFFAOYSA-N n,2-dimethylpropan-2-amine Chemical compound CNC(C)(C)C ZQGJEUVBUVKZKS-UHFFFAOYSA-N 0.000 description 4
KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 4
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
230000028327 secretion Effects 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
210000001519 tissue Anatomy 0.000 description 4
WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 4
KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 3
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 3
OAKQBPGBNBJISS-UHFFFAOYSA-N 3-[(6-bromopyridin-3-yl)methyl]-1h-imidazol-2-one Chemical compound C1=NC(Br)=CC=C1CN1C(=O)NC=C1 OAKQBPGBNBJISS-UHFFFAOYSA-N 0.000 description 3
BSDGZUDFPKIYQG-UHFFFAOYSA-N 4-bromopyridine Chemical compound BrC1=CC=NC=C1 BSDGZUDFPKIYQG-UHFFFAOYSA-N 0.000 description 3
JBELKHJNQQPMCG-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-3-methylcyclopropyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)C1CC JBELKHJNQQPMCG-UHFFFAOYSA-N 0.000 description 3
REENNDVGJGGNPO-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-3-methylcyclopropyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)C1CC REENNDVGJGGNPO-UHFFFAOYSA-N 0.000 description 3
XLDVSXFLXYWFHK-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-3-methylcyclopropyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)C1CC XLDVSXFLXYWFHK-UHFFFAOYSA-N 0.000 description 3
XYFDGSCFYKCKEL-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-4-methylcyclobutyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CC1CC XYFDGSCFYKCKEL-UHFFFAOYSA-N 0.000 description 3
RTBADPHXMKYAKJ-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-4-methylcyclobutyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CC1CC RTBADPHXMKYAKJ-UHFFFAOYSA-N 0.000 description 3
IYUMKHZBSUTNTC-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-4-methylcyclobutyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CC1CC IYUMKHZBSUTNTC-UHFFFAOYSA-N 0.000 description 3
QJHFKLUREVUTJX-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-5-methylcyclopentyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCC1CC QJHFKLUREVUTJX-UHFFFAOYSA-N 0.000 description 3
LTWXVYMPAYTGKJ-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-5-methylcyclopentyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCC1CC LTWXVYMPAYTGKJ-UHFFFAOYSA-N 0.000 description 3
ZSZZAYSYGGNRQH-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-5-methylcyclopentyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCC1CC ZSZZAYSYGGNRQH-UHFFFAOYSA-N 0.000 description 3
GXKUAQQLGBBFIP-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-6-methylcyclohexyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCC1CC GXKUAQQLGBBFIP-UHFFFAOYSA-N 0.000 description 3
CLVJCAYTQYGAAQ-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-6-methylcyclohexyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCC1CC CLVJCAYTQYGAAQ-UHFFFAOYSA-N 0.000 description 3
BYUPRRZCVRLQPG-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-6-methylcyclohexyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCC1CC BYUPRRZCVRLQPG-UHFFFAOYSA-N 0.000 description 3
ZCPJCJRWJVWUBI-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-7-methylcycloheptyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCC1CC ZCPJCJRWJVWUBI-UHFFFAOYSA-N 0.000 description 3
BAULHBKLNDYVRL-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-8-methylcyclooctyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCCC1CC BAULHBKLNDYVRL-UHFFFAOYSA-N 0.000 description 3
XUYOJICHUHZMKX-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-8-methylcyclooctyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCCC1CC XUYOJICHUHZMKX-UHFFFAOYSA-N 0.000 description 3
VEYKHKWFWRMJJC-UHFFFAOYSA-N 4-butyl-1-(2-methyl-3-propan-2-ylcyclopropyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)C1C(C)C VEYKHKWFWRMJJC-UHFFFAOYSA-N 0.000 description 3
MGHDHKAUOJIPBH-UHFFFAOYSA-N 4-butyl-1-(2-methyl-3-propan-2-ylcyclopropyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)C1C(C)C MGHDHKAUOJIPBH-UHFFFAOYSA-N 0.000 description 3
GZJKTTRGLUDTSU-UHFFFAOYSA-N 4-butyl-1-(2-methyl-3-propan-2-ylcyclopropyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)C1C(C)C GZJKTTRGLUDTSU-UHFFFAOYSA-N 0.000 description 3
PIZCDPDZYXAUMB-UHFFFAOYSA-N 4-butyl-1-(2-methyl-3-propan-2-ylcyclopropyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)C1C(C)C PIZCDPDZYXAUMB-UHFFFAOYSA-N 0.000 description 3
YPYINWKLVFFZRE-UHFFFAOYSA-N 4-butyl-1-(2-methyl-5-propan-2-ylcyclopentyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCC1C(C)C YPYINWKLVFFZRE-UHFFFAOYSA-N 0.000 description 3
WIPBETLXUODXHB-UHFFFAOYSA-N 4-butyl-1-(2-methyl-5-propan-2-ylcyclopentyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCC1C(C)C WIPBETLXUODXHB-UHFFFAOYSA-N 0.000 description 3
MYRMBZJDTWPVMQ-UHFFFAOYSA-N 4-butyl-1-(2-methyl-5-propan-2-ylcyclopentyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCC1C(C)C MYRMBZJDTWPVMQ-UHFFFAOYSA-N 0.000 description 3
LUGULAFMPHRFPP-UHFFFAOYSA-N 4-butyl-1-(2-methyl-6-propan-2-ylcyclohexyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCC1C(C)C LUGULAFMPHRFPP-UHFFFAOYSA-N 0.000 description 3
CLZPYQZXXPPOGN-UHFFFAOYSA-N 4-butyl-1-(2-methyl-6-propan-2-ylcyclohexyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCC1C(C)C CLZPYQZXXPPOGN-UHFFFAOYSA-N 0.000 description 3
VPNVIAUQAMCEAG-UHFFFAOYSA-N 4-butyl-1-(2-methyl-6-propan-2-ylcyclohexyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCC1C(C)C VPNVIAUQAMCEAG-UHFFFAOYSA-N 0.000 description 3
CHGOBFKVBGMYOR-UHFFFAOYSA-N 4-butyl-1-(2-methyl-7-propan-2-ylcycloheptyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCC1C(C)C CHGOBFKVBGMYOR-UHFFFAOYSA-N 0.000 description 3
CGTZGPPAFAYIFM-UHFFFAOYSA-N 4-butyl-1-(2-methyl-7-propan-2-ylcycloheptyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCC1C(C)C CGTZGPPAFAYIFM-UHFFFAOYSA-N 0.000 description 3
NNHXVYAHVVSLGX-UHFFFAOYSA-N 4-butyl-1-(2-methyl-8-propan-2-ylcyclooctyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCCC1C(C)C NNHXVYAHVVSLGX-UHFFFAOYSA-N 0.000 description 3
WHEHRYACNQXFNK-UHFFFAOYSA-N 4-butyl-1-(2-methyl-8-propan-2-ylcyclooctyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCCC1C(C)C WHEHRYACNQXFNK-UHFFFAOYSA-N 0.000 description 3
FFQHNUKSUDQYBJ-UHFFFAOYSA-N 4-butyl-1-(2-methyl-8-propan-2-ylcyclooctyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCCC1C(C)C FFQHNUKSUDQYBJ-UHFFFAOYSA-N 0.000 description 3
VWUFCUWTPMDFGA-UHFFFAOYSA-N 4-butyl-1-(2-methyl-8-propan-2-ylcyclooctyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCCC1C(C)C VWUFCUWTPMDFGA-UHFFFAOYSA-N 0.000 description 3
ZQVLPMNLLKGGIU-UHFFFAOYSA-N 5-bromopyridine-2-carbaldehyde Chemical compound BrC1=CC=C(C=O)N=C1 ZQVLPMNLLKGGIU-UHFFFAOYSA-N 0.000 description 3
PVUKGNBRJFTFNJ-UHFFFAOYSA-N 6-bromopyridine-3-carbaldehyde Chemical compound BrC1=CC=C(C=O)C=N1 PVUKGNBRJFTFNJ-UHFFFAOYSA-N 0.000 description 3
FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo(3.3.1)nonane Chemical compound C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
239000005711 Benzoic acid Substances 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
ZHNAHMMDHFFNTP-UHFFFAOYSA-N C(C)(C)C1C(C(CCCC1)C)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound C(C)(C)C1C(C(CCCC1)C)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O ZHNAHMMDHFFNTP-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical class N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
241000124008 Mammalia Species 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
150000001450 anions Chemical class 0.000 description 3
239000011260 aqueous acid Substances 0.000 description 3
235000010233 benzoic acid Nutrition 0.000 description 3
FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 3
150000003939 benzylamines Chemical class 0.000 description 3
230000036772 blood pressure Effects 0.000 description 3
230000031709 bromination Effects 0.000 description 3
238000005893 bromination reaction Methods 0.000 description 3
239000000872 buffer Substances 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000002775 capsule Substances 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
229910052801 chlorine Inorganic materials 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
230000002860 competitive effect Effects 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
238000009472 formulation Methods 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
150000002466 imines Chemical class 0.000 description 3
150000002513 isocyanates Chemical class 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
235000005985 organic acids Nutrition 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
125000006684 polyhaloalkyl group Polymers 0.000 description 3
108090000765 processed proteins & peptides Proteins 0.000 description 3
210000002460 smooth muscle Anatomy 0.000 description 3
235000010288 sodium nitrite Nutrition 0.000 description 3
238000001356 surgical procedure Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
XUHRVZXFBWDCFB-QRTDKPMLSA-N (3R)-4-[[(3S,6S,9S,12R,15S,18R,21R,24R,27R,28R)-12-(3-amino-3-oxopropyl)-6-[(2S)-butan-2-yl]-3-(2-carboxyethyl)-18-(hydroxymethyl)-28-methyl-9,15,21,24-tetrakis(2-methylpropyl)-2,5,8,11,14,17,20,23,26-nonaoxo-1-oxa-4,7,10,13,16,19,22,25-octazacyclooctacos-27-yl]amino]-3-[[(2R)-2-[[(3S)-3-hydroxydecanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoic acid Chemical compound CCCCCCC[C@H](O)CC(=O)N[C@H](CC(C)C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H]1[C@@H](C)OC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CO)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC1=O)[C@@H](C)CC XUHRVZXFBWDCFB-QRTDKPMLSA-N 0.000 description 2
GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 2
MDTUWBLTRPRXBX-UHFFFAOYSA-N 1,2,4-triazol-3-one Chemical class O=C1N=CN=N1 MDTUWBLTRPRXBX-UHFFFAOYSA-N 0.000 description 2
WNWOTMKHOLCHRJ-UHFFFAOYSA-N 1,4-dihydrotriazol-5-one Chemical class O=C1CN=NN1 WNWOTMKHOLCHRJ-UHFFFAOYSA-N 0.000 description 2
HEFWAEQGHKJQBR-UHFFFAOYSA-N 1-(2-acetyl-4-methylcyclobutyl)-4-butyl-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CC1C(C)=O HEFWAEQGHKJQBR-UHFFFAOYSA-N 0.000 description 2
NCIKLYJBFBZVPQ-UHFFFAOYSA-N 1-(2-acetyl-4-methylcyclobutyl)-4-butyl-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CC1C(C)=O NCIKLYJBFBZVPQ-UHFFFAOYSA-N 0.000 description 2
LJWMLPLCUSSJFM-UHFFFAOYSA-N 1-(2-acetyl-4-methylcyclobutyl)-4-butyl-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CC1C(C)=O LJWMLPLCUSSJFM-UHFFFAOYSA-N 0.000 description 2
ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
PPVSSXLHMBNOIR-UHFFFAOYSA-N 2-[4-(bromomethyl)phenyl]pyridine-3-carbonitrile Chemical compound C1=CC(CBr)=CC=C1C1=NC=CC=C1C#N PPVSSXLHMBNOIR-UHFFFAOYSA-N 0.000 description 2
YPOAPQIVHZAASR-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-1-yl]-3-methylcyclopropane-1-carboxylic acid Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)C1C(O)=O YPOAPQIVHZAASR-UHFFFAOYSA-N 0.000 description 2
YWNJQQNBJQUKME-UHFFFAOYSA-N 2-bromo-5-methylpyridine Chemical compound CC1=CC=C(Br)N=C1 YWNJQQNBJQUKME-UHFFFAOYSA-N 0.000 description 2
XGQZPSFKHYKYCG-UHFFFAOYSA-N 3-(4-methylphenyl)pyridine-2-carbonitrile Chemical compound C1=CC(C)=CC=C1C1=CC=CN=C1C#N XGQZPSFKHYKYCG-UHFFFAOYSA-N 0.000 description 2
ZRISBZDLVDKESK-UHFFFAOYSA-N 3-(4-methylphenyl)pyridine-4-carbonitrile Chemical compound C1=CC(C)=CC=C1C1=CN=CC=C1C#N ZRISBZDLVDKESK-UHFFFAOYSA-N 0.000 description 2
OUNYOFFUHZUOLK-UHFFFAOYSA-N 3-[(4-bromophenyl)methyl]-1h-imidazol-2-one Chemical compound C1=CC(Br)=CC=C1CN1C(=O)NC=C1 OUNYOFFUHZUOLK-UHFFFAOYSA-N 0.000 description 2
LVGWTKJIPZCRNB-UHFFFAOYSA-N 3-[(5-bromopyridin-2-yl)methyl]-1h-imidazol-2-one Chemical compound N1=CC(Br)=CC=C1CN1C(=O)NC=C1 LVGWTKJIPZCRNB-UHFFFAOYSA-N 0.000 description 2
LZYFZTWAHPRNCI-UHFFFAOYSA-N 3-[4-(bromomethyl)phenyl]pyridine-2-carbonitrile Chemical compound C1=CC(CBr)=CC=C1C1=CC=CN=C1C#N LZYFZTWAHPRNCI-UHFFFAOYSA-N 0.000 description 2
XOMUKSZOSKOHML-UHFFFAOYSA-N 3-[4-(bromomethyl)phenyl]pyridine-4-carbonitrile Chemical compound C1=CC(CBr)=CC=C1C1=CN=CC=C1C#N XOMUKSZOSKOHML-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
GSQZOLXWFQQJHJ-UHFFFAOYSA-N 3-bromo-4-methylpyridine Chemical compound CC1=CC=NC=C1Br GSQZOLXWFQQJHJ-UHFFFAOYSA-N 0.000 description 2
WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 2
RGDQRXPEZUNWHX-UHFFFAOYSA-N 3-methylpyridin-2-amine Chemical compound CC1=CC=CN=C1N RGDQRXPEZUNWHX-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
RQKZEPOOEDPEPA-UHFFFAOYSA-N 4-[4-(bromomethyl)phenyl]pyridine-3-carbonitrile Chemical compound C1=CC(CBr)=CC=C1C1=CC=NC=C1C#N RQKZEPOOEDPEPA-UHFFFAOYSA-N 0.000 description 2
HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
DMQBJRMKGVMOHX-UHFFFAOYSA-N 4-bromopyridine-3-carbonitrile Chemical compound BrC1=CC=NC=C1C#N DMQBJRMKGVMOHX-UHFFFAOYSA-N 0.000 description 2
NVOCAXHEZWOKBZ-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcycloheptyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1(C)C NVOCAXHEZWOKBZ-UHFFFAOYSA-N 0.000 description 2
XNLYMFYQOCNCKF-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcyclopentyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1(C)C XNLYMFYQOCNCKF-UHFFFAOYSA-N 0.000 description 2
BMCMHFASBDFXJK-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcyclopropyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1(C)C BMCMHFASBDFXJK-UHFFFAOYSA-N 0.000 description 2
GFHROSZVLNQBMO-UHFFFAOYSA-N 4-butyl-1-(2,3-diethylcyclopropyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)C1CC GFHROSZVLNQBMO-UHFFFAOYSA-N 0.000 description 2
GEMJIINOEXIGBU-UHFFFAOYSA-N 4-butyl-1-(2,3-dimethylcyclopropyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)C1C GEMJIINOEXIGBU-UHFFFAOYSA-N 0.000 description 2
IFVYWDAGFWRCPE-UHFFFAOYSA-N 4-butyl-1-(2,3-dimethylcyclopropyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)C1C IFVYWDAGFWRCPE-UHFFFAOYSA-N 0.000 description 2
MIRWARKUNLWEID-UHFFFAOYSA-N 4-butyl-1-(2,3-dimethylcyclopropyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)C1C MIRWARKUNLWEID-UHFFFAOYSA-N 0.000 description 2
KISDYCJCUUPFBY-UHFFFAOYSA-N 4-butyl-1-(2,3-dimethylcyclopropyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)C1C KISDYCJCUUPFBY-UHFFFAOYSA-N 0.000 description 2
FAFWTCLRSZNQLH-UHFFFAOYSA-N 4-butyl-1-(2,4-diethylcyclobutyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CC1CC FAFWTCLRSZNQLH-UHFFFAOYSA-N 0.000 description 2
GUPYQFIDPRNTNX-UHFFFAOYSA-N 4-butyl-1-(2,4-dimethylcyclobutyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CC1C GUPYQFIDPRNTNX-UHFFFAOYSA-N 0.000 description 2
MJNKVWCTCPZLSK-UHFFFAOYSA-N 4-butyl-1-(2,4-dimethylcyclobutyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CC1C MJNKVWCTCPZLSK-UHFFFAOYSA-N 0.000 description 2
LUDBWRQBKNDGTL-UHFFFAOYSA-N 4-butyl-1-(2,4-dimethylcyclobutyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CC1C LUDBWRQBKNDGTL-UHFFFAOYSA-N 0.000 description 2
ATMLIBBSTJNPTF-UHFFFAOYSA-N 4-butyl-1-(2,4-dimethylcyclopentyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC(C)CC1C ATMLIBBSTJNPTF-UHFFFAOYSA-N 0.000 description 2
NIYZGHUPZDHDOX-UHFFFAOYSA-N 4-butyl-1-(2,4-dimethylcyclopentyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC(C)CC1C NIYZGHUPZDHDOX-UHFFFAOYSA-N 0.000 description 2
UTSCJKVPIHCHIA-UHFFFAOYSA-N 4-butyl-1-(2,5-diethylcyclopentyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCC1CC UTSCJKVPIHCHIA-UHFFFAOYSA-N 0.000 description 2
XZIOSIOOQORLIY-UHFFFAOYSA-N 4-butyl-1-(2,6-diethylcyclohexyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCC1CC XZIOSIOOQORLIY-UHFFFAOYSA-N 0.000 description 2
NWUOBZVOFKCGNF-UHFFFAOYSA-N 4-butyl-1-(2,6-dimethylcyclohexyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCC1C NWUOBZVOFKCGNF-UHFFFAOYSA-N 0.000 description 2
FSHCOGZEALOJSC-UHFFFAOYSA-N 4-butyl-1-(2,6-dimethylcyclohexyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCC1C FSHCOGZEALOJSC-UHFFFAOYSA-N 0.000 description 2
HFAOBCDCRPKHIY-UHFFFAOYSA-N 4-butyl-1-(2,7-dimethylcycloheptyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCC1C HFAOBCDCRPKHIY-UHFFFAOYSA-N 0.000 description 2
GVYYAIVQTFPSOP-UHFFFAOYSA-N 4-butyl-1-(2,7-dimethylcycloheptyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCC1C GVYYAIVQTFPSOP-UHFFFAOYSA-N 0.000 description 2
QHJBXOUCHPSQLZ-UHFFFAOYSA-N 4-butyl-1-(2,7-dimethylcycloheptyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCC1C QHJBXOUCHPSQLZ-UHFFFAOYSA-N 0.000 description 2
LXZSDNRRQUOYQY-UHFFFAOYSA-N 4-butyl-1-(2,8-dimethylcyclooctyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCCC1C LXZSDNRRQUOYQY-UHFFFAOYSA-N 0.000 description 2
HMIXMZGWSJUPMO-UHFFFAOYSA-N 4-butyl-1-(2,8-dimethylcyclooctyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCCC1C HMIXMZGWSJUPMO-UHFFFAOYSA-N 0.000 description 2
MQPHRPYZMPUURI-UHFFFAOYSA-N 4-butyl-1-(2,8-dimethylcyclooctyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCCC1C MQPHRPYZMPUURI-UHFFFAOYSA-N 0.000 description 2
KOEHIAUJHKNQTB-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-3-methylcyclopropyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)C1CC KOEHIAUJHKNQTB-UHFFFAOYSA-N 0.000 description 2
HMDXANXEHFDVKN-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-3-propan-2-ylcyclopropyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)C1C(C)C HMDXANXEHFDVKN-UHFFFAOYSA-N 0.000 description 2
QNCARSPFXJIMJK-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-3-propan-2-ylcyclopropyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)C1C(C)C QNCARSPFXJIMJK-UHFFFAOYSA-N 0.000 description 2
OFGZKAFUCDGZPY-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-4-methylcyclobutyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CC1CC OFGZKAFUCDGZPY-UHFFFAOYSA-N 0.000 description 2
BMIQWATWKJNYAM-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-5-propan-2-ylcyclopentyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCC1C(C)C BMIQWATWKJNYAM-UHFFFAOYSA-N 0.000 description 2
AXDOWDKXBJTFHB-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-5-propan-2-ylcyclopentyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCC1C(C)C AXDOWDKXBJTFHB-UHFFFAOYSA-N 0.000 description 2
CPADPFAORHUUHG-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-5-propan-2-ylcyclopentyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCC1C(C)C CPADPFAORHUUHG-UHFFFAOYSA-N 0.000 description 2
YZDJEJAZBZETAO-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-6-propan-2-ylcyclohexyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCC1C(C)C YZDJEJAZBZETAO-UHFFFAOYSA-N 0.000 description 2
LZFBVMNZBCLAFB-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-6-propan-2-ylcyclohexyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCC1C(C)C LZFBVMNZBCLAFB-UHFFFAOYSA-N 0.000 description 2
JRXNDXKCJLQMIZ-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-7-methylcycloheptyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCC1CC JRXNDXKCJLQMIZ-UHFFFAOYSA-N 0.000 description 2
XTQTWCRQVTXJNS-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-7-methylcycloheptyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCC1CC XTQTWCRQVTXJNS-UHFFFAOYSA-N 0.000 description 2
GFJYOWOFTWLAAQ-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-7-methylcycloheptyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCC1CC GFJYOWOFTWLAAQ-UHFFFAOYSA-N 0.000 description 2
YPJCTDGIPRODJI-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-7-propan-2-ylcycloheptyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCCC1C(C)C YPJCTDGIPRODJI-UHFFFAOYSA-N 0.000 description 2
BYEOMPZIKBYENZ-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-7-propan-2-ylcycloheptyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCCC1C(C)C BYEOMPZIKBYENZ-UHFFFAOYSA-N 0.000 description 2
BZUDAERSUFDYIH-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-7-propan-2-ylcycloheptyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCCC1C(C)C BZUDAERSUFDYIH-UHFFFAOYSA-N 0.000 description 2
NUYUPONLYJARPF-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-7-propan-2-ylcycloheptyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCCC1C(C)C NUYUPONLYJARPF-UHFFFAOYSA-N 0.000 description 2
FVOJULGOMQKTKT-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-8-methylcyclooctyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCCC1CC FVOJULGOMQKTKT-UHFFFAOYSA-N 0.000 description 2
NHOHJVURSWYVGV-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-8-methylcyclooctyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCCC1CC NHOHJVURSWYVGV-UHFFFAOYSA-N 0.000 description 2
VRUKREBSFQYPAU-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-8-propan-2-ylcyclooctyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCCCC1C(C)C VRUKREBSFQYPAU-UHFFFAOYSA-N 0.000 description 2
JXLSYTOUPBBHLU-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-8-propan-2-ylcyclooctyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCCCC1C(C)C JXLSYTOUPBBHLU-UHFFFAOYSA-N 0.000 description 2
PGHZUXAUVIGOSF-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-8-propan-2-ylcyclooctyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCCCC1C(C)C PGHZUXAUVIGOSF-UHFFFAOYSA-N 0.000 description 2
DEQRYZRBSHOIDO-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-8-propan-2-ylcyclooctyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCCCC1C(C)C DEQRYZRBSHOIDO-UHFFFAOYSA-N 0.000 description 2
QGSZDNNODUMYBJ-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-8-propan-2-ylcyclooctyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCCCC1C(C)C QGSZDNNODUMYBJ-UHFFFAOYSA-N 0.000 description 2
IYRHFDJLGZPQHP-UHFFFAOYSA-N 4-butyl-1-(2-methyl-3-oxocyclopropyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)C1=O IYRHFDJLGZPQHP-UHFFFAOYSA-N 0.000 description 2
CGQVMBAMKKANAA-UHFFFAOYSA-N 4-butyl-1-(2-methyl-3-oxocyclopropyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)C1=O CGQVMBAMKKANAA-UHFFFAOYSA-N 0.000 description 2
CFDXOVDEYQMJMI-UHFFFAOYSA-N 4-butyl-1-(2-methyl-3-oxocyclopropyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)C1=O CFDXOVDEYQMJMI-UHFFFAOYSA-N 0.000 description 2
OLHZJTXYOAAHRV-UHFFFAOYSA-N 4-butyl-1-(2-methyl-3-propan-2-ylcyclopropyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)C1C(C)C OLHZJTXYOAAHRV-UHFFFAOYSA-N 0.000 description 2
UTNPXFBOXPHIFG-UHFFFAOYSA-N 4-butyl-1-(2-methyl-4-oxocyclobutyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CC1=O UTNPXFBOXPHIFG-UHFFFAOYSA-N 0.000 description 2
AJPVLTFAOMKXNA-UHFFFAOYSA-N 4-butyl-1-(2-methyl-4-oxocyclobutyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CC1=O AJPVLTFAOMKXNA-UHFFFAOYSA-N 0.000 description 2
BQAYKEXTKZWWJO-UHFFFAOYSA-N 4-butyl-1-(2-methyl-4-oxocyclobutyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CC1=O BQAYKEXTKZWWJO-UHFFFAOYSA-N 0.000 description 2
NWXVVEFSPCPQRE-UHFFFAOYSA-N 4-butyl-1-(2-methyl-5-oxocyclopentyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCC1=O NWXVVEFSPCPQRE-UHFFFAOYSA-N 0.000 description 2
HPFOBNLEYWXFFG-UHFFFAOYSA-N 4-butyl-1-(2-methyl-5-oxocyclopentyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCC1=O HPFOBNLEYWXFFG-UHFFFAOYSA-N 0.000 description 2
BZRHWSXRWXZPRS-UHFFFAOYSA-N 4-butyl-1-(2-methyl-5-propan-2-ylcyclopentyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCC1C(C)C BZRHWSXRWXZPRS-UHFFFAOYSA-N 0.000 description 2
RRWJECTXMAEGLI-UHFFFAOYSA-N 4-butyl-1-(2-methyl-5-propan-2-ylcyclopentyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCC1C(C)C RRWJECTXMAEGLI-UHFFFAOYSA-N 0.000 description 2
IHMNHDKUCOOXJG-UHFFFAOYSA-N 4-butyl-1-(2-methyl-6-oxocyclohexyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCC1=O IHMNHDKUCOOXJG-UHFFFAOYSA-N 0.000 description 2
LWYBUIJCRKQWSF-UHFFFAOYSA-N 4-butyl-1-(2-methyl-7-oxocycloheptyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCC1=O LWYBUIJCRKQWSF-UHFFFAOYSA-N 0.000 description 2
JQNQTLBNWBYIQT-UHFFFAOYSA-N 4-butyl-1-(2-methyl-7-propan-2-ylcycloheptyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCC1C(C)C JQNQTLBNWBYIQT-UHFFFAOYSA-N 0.000 description 2
AOXRRICZGJFAIV-UHFFFAOYSA-N 4-butyl-1-(2-methyl-7-propan-2-ylcycloheptyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCC1C(C)C AOXRRICZGJFAIV-UHFFFAOYSA-N 0.000 description 2
NWZRLGKVOMQUML-UHFFFAOYSA-N 4-butyl-1-(2-methyl-8-oxocyclooctyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCCC1=O NWZRLGKVOMQUML-UHFFFAOYSA-N 0.000 description 2
RNSOTNZDPUOSAI-UHFFFAOYSA-N 4-butyl-1-(2-methyl-8-propan-2-ylcyclooctyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCCC1C(C)C RNSOTNZDPUOSAI-UHFFFAOYSA-N 0.000 description 2
PYTMRUSSECMPOB-UHFFFAOYSA-N 4-butyl-1-(2-methyl-8-propan-2-ylcyclooctyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCCC1C(C)C PYTMRUSSECMPOB-UHFFFAOYSA-N 0.000 description 2
TVGBPMLCBWANNF-UHFFFAOYSA-N 4-butyl-1-(2-oxo-5-propan-2-ylcyclopentyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CCC1=O TVGBPMLCBWANNF-UHFFFAOYSA-N 0.000 description 2
ZYKYQKAHQUZNRR-UHFFFAOYSA-N 4-butyl-1-cyclohexyl-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C=2NN=NN=2)C(CCCC)=CN1C1CCCCC1 ZYKYQKAHQUZNRR-UHFFFAOYSA-N 0.000 description 2
VDIKYULBOKWSQK-UHFFFAOYSA-N 4-butyl-1-cyclopentyl-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C=2NN=NN=2)C(CCCC)=CN1C1CCCC1 VDIKYULBOKWSQK-UHFFFAOYSA-N 0.000 description 2
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
OFKWIQJLYCKDNY-UHFFFAOYSA-N 5-bromo-2-methylpyridine Chemical compound CC1=CC=C(Br)C=N1 OFKWIQJLYCKDNY-UHFFFAOYSA-N 0.000 description 2
MGXIZNVJTQYIPT-UHFFFAOYSA-N 5-butyl-3-cyclohexyl-1h-imidazol-2-one Chemical compound O=C1NC(CCCC)=CN1C1CCCCC1 MGXIZNVJTQYIPT-UHFFFAOYSA-N 0.000 description 2
XJLYQNUUQQHADQ-UHFFFAOYSA-N 5-butyl-3-cyclopentyl-1h-imidazol-2-one Chemical compound O=C1NC(CCCC)=CN1C1CCCC1 XJLYQNUUQQHADQ-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 2
PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 description 2
102000008873 Angiotensin II receptor Human genes 0.000 description 2
108050000824 Angiotensin II receptor Proteins 0.000 description 2
206010002660 Anoxia Diseases 0.000 description 2
241000976983 Anoxia Species 0.000 description 2
206010003210 Arteriosclerosis Diseases 0.000 description 2
JSQBLBFXCSZRPT-UHFFFAOYSA-N C(C)C1C(C(CCCC1)C)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound C(C)C1C(C(CCCC1)C)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O JSQBLBFXCSZRPT-UHFFFAOYSA-N 0.000 description 2
NRMNOBRQXAPHFV-UHFFFAOYSA-N C(C)C1C(C(CCCCC1)CC)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound C(C)C1C(C(CCCCC1)CC)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O NRMNOBRQXAPHFV-UHFFFAOYSA-N 0.000 description 2
YHIINUFMBGNKHV-UHFFFAOYSA-N C(C)C1C(C1C(C)C)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound C(C)C1C(C1C(C)C)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O YHIINUFMBGNKHV-UHFFFAOYSA-N 0.000 description 2
LWTAGHAMCBJTSQ-UHFFFAOYSA-N CC1(C(CCCCCC1)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O)C Chemical compound CC1(C(CCCCCC1)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O)C LWTAGHAMCBJTSQ-UHFFFAOYSA-N 0.000 description 2
PWMWIUKZSFDXOC-UHFFFAOYSA-N CC1C(C(CCC1)C)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound CC1C(C(CCC1)C)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O PWMWIUKZSFDXOC-UHFFFAOYSA-N 0.000 description 2
XVUPTHXSRZNRSG-UHFFFAOYSA-N CC1C(C(CCCC1)C)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound CC1C(C(CCCC1)C)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O XVUPTHXSRZNRSG-UHFFFAOYSA-N 0.000 description 2
LYJYCEFXSRPAPJ-UHFFFAOYSA-N CC1C(C(CCCCC1)C)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound CC1C(C(CCCCC1)C)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O LYJYCEFXSRPAPJ-UHFFFAOYSA-N 0.000 description 2
QEQXSBSXCNJTJZ-UHFFFAOYSA-N CC1C(CC(C1)C)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound CC1C(CC(C1)C)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O QEQXSBSXCNJTJZ-UHFFFAOYSA-N 0.000 description 2
244000025254 Cannabis sativa Species 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
206010021143 Hypoxia Diseases 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 2
YMKBVJUAMATJML-UHFFFAOYSA-N O=C1C(C(CCC1)C)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound O=C1C(C(CCC1)C)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O YMKBVJUAMATJML-UHFFFAOYSA-N 0.000 description 2
SUNFDLZNAXNARJ-UHFFFAOYSA-N O=C1C(C(CCCC1)C)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound O=C1C(C(CCCC1)C)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O SUNFDLZNAXNARJ-UHFFFAOYSA-N 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
102100028255 Renin Human genes 0.000 description 2
108090000783 Renin Proteins 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
102000008068 Tensins Human genes 0.000 description 2
108010088950 Tensins Proteins 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
239000000556 agonist Substances 0.000 description 2
229960002478 aldosterone Drugs 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
230000003444 anaesthetic effect Effects 0.000 description 2
238000002399 angioplasty Methods 0.000 description 2
230000007953 anoxia Effects 0.000 description 2
230000003288 anthiarrhythmic effect Effects 0.000 description 2
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
230000000767 anti-ulcer Effects 0.000 description 2
239000003416 antiarrhythmic agent Substances 0.000 description 2
230000004872 arterial blood pressure Effects 0.000 description 2
208000011775 arteriosclerosis disease Diseases 0.000 description 2
RJNJWHFSKNJCTB-UHFFFAOYSA-N benzylurea Chemical class NC(=O)NCC1=CC=CC=C1 RJNJWHFSKNJCTB-UHFFFAOYSA-N 0.000 description 2
229910000085 borane Inorganic materials 0.000 description 2
210000000621 bronchi Anatomy 0.000 description 2
WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
208000026106 cerebrovascular disease Diseases 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000010339 dilation Effects 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000002934 diuretic Substances 0.000 description 2
229940030606 diuretics Drugs 0.000 description 2
231100000673 dose–response relationship Toxicity 0.000 description 2
229940079593 drug Drugs 0.000 description 2
WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
238000002825 functional assay Methods 0.000 description 2
230000002363 herbicidal effect Effects 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
230000003054 hormonal effect Effects 0.000 description 2
230000001631 hypertensive effect Effects 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
238000011534 incubation Methods 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
208000023589 ischemic disease Diseases 0.000 description 2
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
230000002147 killing effect Effects 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000003446 ligand Substances 0.000 description 2
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
125000006682 monohaloalkyl group Chemical group 0.000 description 2
235000001968 nicotinic acid Nutrition 0.000 description 2
229960003512 nicotinic acid Drugs 0.000 description 2
239000011664 nicotinic acid Substances 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
230000009871 nonspecific binding Effects 0.000 description 2
150000002923 oximes Chemical class 0.000 description 2
229940081066 picolinic acid Drugs 0.000 description 2
239000012286 potassium permanganate Substances 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000002243 precursor Substances 0.000 description 2
239000000651 prodrug Substances 0.000 description 2
229940002612 prodrug Drugs 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
230000036454 renin-angiotensin system Effects 0.000 description 2
208000037803 restenosis Diseases 0.000 description 2
125000006413 ring segment Chemical group 0.000 description 2
239000000932 sedative agent Substances 0.000 description 2
230000001624 sedative effect Effects 0.000 description 2
230000009870 specific binding Effects 0.000 description 2
208000010110 spontaneous platelet aggregation Diseases 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
150000003536 tetrazoles Chemical class 0.000 description 2
WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
229940125725 tranquilizer Drugs 0.000 description 2
239000003204 tranquilizing agent Substances 0.000 description 2
230000002936 tranquilizing effect Effects 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
150000003852 triazoles Chemical group 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
210000002700 urine Anatomy 0.000 description 2
239000005526 vasoconstrictor agent Substances 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
125000006002 1,1-difluoroethyl group Chemical group 0.000 description 1
XTCMQAVNRXZBRH-UHFFFAOYSA-N 1,3-dimethylcyclohexene Chemical compound CC1CCCC(C)=C1 XTCMQAVNRXZBRH-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
NBCXIJRCSBEGNK-UHFFFAOYSA-N 1-(2-acetyl-4-ethylcyclobutyl)-4-butyl-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CC1C(C)=O NBCXIJRCSBEGNK-UHFFFAOYSA-N 0.000 description 1
FEDPFPVODIDINM-UHFFFAOYSA-N 1-(2-acetyl-4-ethylcyclobutyl)-4-butyl-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CC1C(C)=O FEDPFPVODIDINM-UHFFFAOYSA-N 0.000 description 1
SFHSHWXXCAVHCR-UHFFFAOYSA-N 1-(2-acetyl-4-ethylcyclobutyl)-4-butyl-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CC1C(C)=O SFHSHWXXCAVHCR-UHFFFAOYSA-N 0.000 description 1
LREZHKLTCVWQAO-UHFFFAOYSA-N 1-(2-acetyl-4-ethylcyclobutyl)-4-butyl-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CC1C(C)=O LREZHKLTCVWQAO-UHFFFAOYSA-N 0.000 description 1
JRFBQMNGMZZXLY-UHFFFAOYSA-N 1-(2-acetyl-4-ethylcyclobutyl)-4-butyl-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CC1C(C)=O JRFBQMNGMZZXLY-UHFFFAOYSA-N 0.000 description 1
WTHPRWFOYXTCRL-UHFFFAOYSA-N 1-(2-acetyl-4-ethylcyclobutyl)-4-butyl-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CC1C(C)=O WTHPRWFOYXTCRL-UHFFFAOYSA-N 0.000 description 1
UDNKSUJLYQLDKI-UHFFFAOYSA-N 1-(2-acetyl-4-methylcyclobutyl)-4-butyl-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CC1C(C)=O UDNKSUJLYQLDKI-UHFFFAOYSA-N 0.000 description 1
JHKNXYQOQHBQRN-UHFFFAOYSA-N 1-(2-acetyl-4-propan-2-ylcyclobutyl)-4-butyl-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CC1C(C)=O JHKNXYQOQHBQRN-UHFFFAOYSA-N 0.000 description 1
RCUORZCDDJWUOY-UHFFFAOYSA-N 1-(2-acetylcycloheptyl)-4-butyl-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1C(C)=O RCUORZCDDJWUOY-UHFFFAOYSA-N 0.000 description 1
WGIZHNFWRGPBBY-UHFFFAOYSA-N 1-(2-acetylcycloheptyl)-4-butyl-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1C(C)=O WGIZHNFWRGPBBY-UHFFFAOYSA-N 0.000 description 1
GNZDYKWDZUNSLC-UHFFFAOYSA-N 1-(2-acetylcycloheptyl)-4-butyl-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1C(C)=O GNZDYKWDZUNSLC-UHFFFAOYSA-N 0.000 description 1
AMOLUYXTMFIKQJ-UHFFFAOYSA-N 1-(2-acetylcycloheptyl)-4-butyl-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1C(C)=O AMOLUYXTMFIKQJ-UHFFFAOYSA-N 0.000 description 1
GUNVGVXIHKKSHI-UHFFFAOYSA-N 1-(2-acetylcycloheptyl)-4-butyl-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1C(C)=O GUNVGVXIHKKSHI-UHFFFAOYSA-N 0.000 description 1
ZXBZOSGBXLBZAO-UHFFFAOYSA-N 1-(2-acetylcyclohexyl)-4-butyl-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1C(C)=O ZXBZOSGBXLBZAO-UHFFFAOYSA-N 0.000 description 1
YOTDUSPSZXNUST-UHFFFAOYSA-N 1-(2-acetylcyclohexyl)-4-butyl-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1C(C)=O YOTDUSPSZXNUST-UHFFFAOYSA-N 0.000 description 1
KGJMCQPOZHPOLW-UHFFFAOYSA-N 1-(2-acetylcyclohexyl)-4-butyl-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1C(C)=O KGJMCQPOZHPOLW-UHFFFAOYSA-N 0.000 description 1
RXLDVFGSSIKEJG-UHFFFAOYSA-N 1-(2-acetylcyclooctyl)-4-butyl-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1C(C)=O RXLDVFGSSIKEJG-UHFFFAOYSA-N 0.000 description 1
AFSLVAPXZXHDJE-UHFFFAOYSA-N 1-(2-acetylcyclooctyl)-4-butyl-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1C(C)=O AFSLVAPXZXHDJE-UHFFFAOYSA-N 0.000 description 1
FBCBGYPQJPIQIT-UHFFFAOYSA-N 1-(2-acetylcyclooctyl)-4-butyl-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1C(C)=O FBCBGYPQJPIQIT-UHFFFAOYSA-N 0.000 description 1
UBJVGENCYNQMBN-UHFFFAOYSA-N 1-(2-acetylcyclooctyl)-4-butyl-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1C(C)=O UBJVGENCYNQMBN-UHFFFAOYSA-N 0.000 description 1
GABLDPOFKWFQOD-UHFFFAOYSA-N 1-(2-acetylcyclopentyl)-4-butyl-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1C(C)=O GABLDPOFKWFQOD-UHFFFAOYSA-N 0.000 description 1
PHUCPLZWSCIRNC-UHFFFAOYSA-N 1-(2-acetylcyclopentyl)-4-butyl-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1C(C)=O PHUCPLZWSCIRNC-UHFFFAOYSA-N 0.000 description 1
FJBMRBOYYDEAGU-UHFFFAOYSA-N 1-(2-acetylcyclopentyl)-4-butyl-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1C(C)=O FJBMRBOYYDEAGU-UHFFFAOYSA-N 0.000 description 1
BIHOFCAJASWRER-UHFFFAOYSA-N 1-(2-acetylcyclopentyl)-4-butyl-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1C(C)=O BIHOFCAJASWRER-UHFFFAOYSA-N 0.000 description 1
YGIGLRGUBOJLGK-UHFFFAOYSA-N 1-(2-acetylcyclopropyl)-4-butyl-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1C(C)=O YGIGLRGUBOJLGK-UHFFFAOYSA-N 0.000 description 1
UDHPEQKIBCIFGN-UHFFFAOYSA-N 1-(2-acetylcyclopropyl)-4-butyl-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1C(C)=O UDHPEQKIBCIFGN-UHFFFAOYSA-N 0.000 description 1
INBLADKVNYMTTO-UHFFFAOYSA-N 1-(2-acetylcyclopropyl)-4-butyl-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1C(C)=O INBLADKVNYMTTO-UHFFFAOYSA-N 0.000 description 1
WBWNEKXUKRCZGQ-UHFFFAOYSA-N 1-(2-acetylcyclopropyl)-4-butyl-3-[[5-[2-(2H-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound C(C)(=O)C1C(C1)N1C(N(C(=C1)CCCC)CC1=NC=C(C=C1)C1=C(C=CC=C1)C1=NN=NN1)=O WBWNEKXUKRCZGQ-UHFFFAOYSA-N 0.000 description 1
YDPQGOZOSXDDNT-UHFFFAOYSA-N 1-(2-acetylcyclopropyl)-4-butyl-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1C(C)=O YDPQGOZOSXDDNT-UHFFFAOYSA-N 0.000 description 1
YLRBJYMANQKEAW-UHFFFAOYSA-N 1-bromo-4-(bromomethyl)benzene Chemical compound BrCC1=CC=C(Br)C=C1 YLRBJYMANQKEAW-UHFFFAOYSA-N 0.000 description 1
NFIFMJXUZUVLCC-UHFFFAOYSA-N 1-bromo-5-phenyltetrazole Chemical compound BrN1N=NN=C1C1=CC=CC=C1 NFIFMJXUZUVLCC-UHFFFAOYSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
XVXGXOJNGBLOKR-UHFFFAOYSA-N 2,2-dimethylcyclohexan-1-amine Chemical compound CC1(C)CCCCC1N XVXGXOJNGBLOKR-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
OFPWMRMIFDHXFE-UHFFFAOYSA-N 2-(bromomethyl)pyridine Chemical compound BrCC1=CC=CC=N1 OFPWMRMIFDHXFE-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
ASUUCGYEJLQCMW-UHFFFAOYSA-N 2-[4-[(3,5-dibutyl-1,2,4-triazol-4-yl)methyl]phenyl]benzoic acid Chemical compound CCCCC1=NN=C(CCCC)N1CC1=CC=C(C=2C(=CC=CC=2)C(O)=O)C=C1 ASUUCGYEJLQCMW-UHFFFAOYSA-N 0.000 description 1
VBWCFYLHARZXNE-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-1-yl]cyclobutane-1-carboxylic acid Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1C(O)=O VBWCFYLHARZXNE-UHFFFAOYSA-N 0.000 description 1
WXZOCIHJORWUEP-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-1-yl]cycloheptane-1-carboxylic acid Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1C(O)=O WXZOCIHJORWUEP-UHFFFAOYSA-N 0.000 description 1
QGXMMCFDNSZASM-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-1-yl]cyclohexane-1-carboxylic acid Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1C(O)=O QGXMMCFDNSZASM-UHFFFAOYSA-N 0.000 description 1
DNVXJJCTOICPQC-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-1-yl]cyclooctane-1-carboxylic acid Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1C(O)=O DNVXJJCTOICPQC-UHFFFAOYSA-N 0.000 description 1
YBMBMOIXOBSTDN-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-1-yl]cyclopentane-1-carboxylic acid Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1C(O)=O YBMBMOIXOBSTDN-UHFFFAOYSA-N 0.000 description 1
NZJNOCYYHJLKGJ-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-1-yl]cyclopropane-1-carboxylic acid Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1C(O)=O NZJNOCYYHJLKGJ-UHFFFAOYSA-N 0.000 description 1
NDHAXTOGOJPOTN-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-1-yl]cyclobutane-1-carboxylic acid Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1C(O)=O NDHAXTOGOJPOTN-UHFFFAOYSA-N 0.000 description 1
IOFCORPMLXDGAM-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-1-yl]cyclohexane-1-carboxylic acid Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1C(O)=O IOFCORPMLXDGAM-UHFFFAOYSA-N 0.000 description 1
MQVXIRPVAQNDTI-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-1-yl]cyclooctane-1-carboxylic acid Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1C(O)=O MQVXIRPVAQNDTI-UHFFFAOYSA-N 0.000 description 1
MCHXUNMEQMIANH-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-1-yl]cyclopentane-1-carboxylic acid Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1C(O)=O MCHXUNMEQMIANH-UHFFFAOYSA-N 0.000 description 1
ISRMDAAMWGAROG-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-1-yl]cyclopropane-1-carboxylic acid Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1C(O)=O ISRMDAAMWGAROG-UHFFFAOYSA-N 0.000 description 1
SPGPARDDNLFAHD-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-1-yl]cyclobutane-1-carboxylic acid Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1C(O)=O SPGPARDDNLFAHD-UHFFFAOYSA-N 0.000 description 1
WDDMALWZZPYFMB-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-1-yl]cyclohexane-1-carboxylic acid Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1C(O)=O WDDMALWZZPYFMB-UHFFFAOYSA-N 0.000 description 1
OTDXKOMUGDGUOD-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-1-yl]cyclooctane-1-carboxylic acid Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1C(O)=O OTDXKOMUGDGUOD-UHFFFAOYSA-N 0.000 description 1
UEORSVFKAOANPR-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-1-yl]cyclopentane-1-carboxylic acid Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1C(O)=O UEORSVFKAOANPR-UHFFFAOYSA-N 0.000 description 1
GRKKNRQKNLXELK-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-1-yl]cycloheptane-1-carboxylic acid Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1C(O)=O GRKKNRQKNLXELK-UHFFFAOYSA-N 0.000 description 1
WCNICMBOMFQRQV-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-1-yl]cyclohexane-1-carboxylic acid Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1C(O)=O WCNICMBOMFQRQV-UHFFFAOYSA-N 0.000 description 1
UEZODOAHAUPTMW-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-1-yl]cyclooctane-1-carboxylic acid Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1C(O)=O UEZODOAHAUPTMW-UHFFFAOYSA-N 0.000 description 1
OZXXKEWABDPLNX-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-1-yl]cyclopentane-1-carboxylic acid Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1C(O)=O OZXXKEWABDPLNX-UHFFFAOYSA-N 0.000 description 1
VYRSBFGKFOMLNH-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-1-yl]cyclopropane-1-carboxylic acid Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1C(O)=O VYRSBFGKFOMLNH-UHFFFAOYSA-N 0.000 description 1
UYUNAMVMHUIVII-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-1-yl]cycloheptane-1-carboxylic acid Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1C(O)=O UYUNAMVMHUIVII-UHFFFAOYSA-N 0.000 description 1
IASCQKIUASPSDS-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-1-yl]cyclohexane-1-carboxylic acid Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1C(O)=O IASCQKIUASPSDS-UHFFFAOYSA-N 0.000 description 1
NGOABFKBZUHJKL-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-1-yl]cyclooctane-1-carboxylic acid Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1C(O)=O NGOABFKBZUHJKL-UHFFFAOYSA-N 0.000 description 1
NOZPIZRHKICBLX-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-1-yl]cyclopentane-1-carboxylic acid Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1C(O)=O NOZPIZRHKICBLX-UHFFFAOYSA-N 0.000 description 1
NRGDVPGSYKCGGJ-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-1-yl]cyclopropane-1-carboxylic acid Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1C(O)=O NRGDVPGSYKCGGJ-UHFFFAOYSA-N 0.000 description 1
GTXPSNFIADDGMJ-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-1-yl]cyclobutane-1-carboxylic acid Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1C(O)=O GTXPSNFIADDGMJ-UHFFFAOYSA-N 0.000 description 1
XRQWZCXEBRFUNA-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-1-yl]cyclooctane-1-carboxylic acid Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1C(O)=O XRQWZCXEBRFUNA-UHFFFAOYSA-N 0.000 description 1
VVDXGVSAGFIAPN-UHFFFAOYSA-N 2-[4-butyl-2-oxo-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-1-yl]cyclopropane-1-carboxylic acid Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1C(O)=O VVDXGVSAGFIAPN-UHFFFAOYSA-N 0.000 description 1
NDOPHXWIAZIXPR-UHFFFAOYSA-N 2-bromobenzaldehyde Chemical compound BrC1=CC=CC=C1C=O NDOPHXWIAZIXPR-UHFFFAOYSA-N 0.000 description 1
IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
QIPXEPRGYVAQFI-UHFFFAOYSA-N 2-bromopyridine-3-carbonitrile Chemical compound BrC1=NC=CC=C1C#N QIPXEPRGYVAQFI-UHFFFAOYSA-N 0.000 description 1
LFSAPCRASZRSKS-UHFFFAOYSA-N 2-methylcyclohexan-1-one Chemical compound CC1CCCCC1=O LFSAPCRASZRSKS-UHFFFAOYSA-N 0.000 description 1
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
ZSFPJJJRNUZCEV-UHFFFAOYSA-N 2-methylpyridin-3-amine Chemical compound CC1=NC=CC=C1N ZSFPJJJRNUZCEV-UHFFFAOYSA-N 0.000 description 1
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
KHCXGFNZZRXOND-UHFFFAOYSA-N 3-(bromomethyl)pyridine Chemical compound BrCC1=CC=CN=C1 KHCXGFNZZRXOND-UHFFFAOYSA-N 0.000 description 1
WWVZGHDIWCIWNR-UHFFFAOYSA-N 3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]-1h-imidazol-2-one Chemical compound O=C1NC=CN1CC1=CC=C(C=2C(=CC=CC=2)C=2NN=NN=2)C=N1 WWVZGHDIWCIWNR-UHFFFAOYSA-N 0.000 description 1
AIPWPTPHMIYYOX-UHFFFAOYSA-N 3-bromo-2-methylpyridine Chemical compound CC1=NC=CC=C1Br AIPWPTPHMIYYOX-UHFFFAOYSA-N 0.000 description 1
HCOPIUVJCIZALB-UHFFFAOYSA-N 3-bromopyridine-2-carbonitrile Chemical compound BrC1=CC=CN=C1C#N HCOPIUVJCIZALB-UHFFFAOYSA-N 0.000 description 1
VPDIXJCBBUZNPO-UHFFFAOYSA-N 3-bromopyridine-4-carbonitrile Chemical compound BrC1=CN=CC=C1C#N VPDIXJCBBUZNPO-UHFFFAOYSA-N 0.000 description 1
CGZFEGUVDIMFPG-UHFFFAOYSA-N 4-[(4-bromophenyl)methyl]imidazol-2-one Chemical compound C1=CC(Br)=CC=C1CC1=NC(=O)N=C1 CGZFEGUVDIMFPG-UHFFFAOYSA-N 0.000 description 1
QDXKQDSDQCINRH-UHFFFAOYSA-N 4-[[4-[3-(2H-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound N1N=NN=C1C=1C=C(C=CC1)C1=CC(=NC=C1)CC1=NC(N=C1)=O QDXKQDSDQCINRH-UHFFFAOYSA-N 0.000 description 1
125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 1
LVOQUYJDSAYBNE-UHFFFAOYSA-N 4-bromoimidazol-2-one Chemical compound BrC1=NC(=O)N=C1 LVOQUYJDSAYBNE-UHFFFAOYSA-N 0.000 description 1
ZAGRQGIWYDZYDN-UHFFFAOYSA-N 4-butyl-1-(2,2-diethylcyclobutyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1(CC)CC ZAGRQGIWYDZYDN-UHFFFAOYSA-N 0.000 description 1
HKNRRUQNLOEHKQ-UHFFFAOYSA-N 4-butyl-1-(2,2-diethylcyclobutyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1(CC)CC HKNRRUQNLOEHKQ-UHFFFAOYSA-N 0.000 description 1
SPMZAJARPMGDKP-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcyclobutyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1(C)C SPMZAJARPMGDKP-UHFFFAOYSA-N 0.000 description 1
QZUDUEMXNLQRKU-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcyclobutyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1(C)C QZUDUEMXNLQRKU-UHFFFAOYSA-N 0.000 description 1
FMBVCTVLJMSOHC-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcyclobutyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1(C)C FMBVCTVLJMSOHC-UHFFFAOYSA-N 0.000 description 1
OGDBCVBQSFFIIZ-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcyclobutyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1(C)C OGDBCVBQSFFIIZ-UHFFFAOYSA-N 0.000 description 1
SHYOMIZDJBYQJS-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcyclobutyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1(C)C SHYOMIZDJBYQJS-UHFFFAOYSA-N 0.000 description 1
ASEDPVISYZJQFW-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcyclobutyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1(C)C ASEDPVISYZJQFW-UHFFFAOYSA-N 0.000 description 1
DTUNMUSXLSTOTH-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcycloheptyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1(C)C DTUNMUSXLSTOTH-UHFFFAOYSA-N 0.000 description 1
AULHADZGMKNZQE-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcycloheptyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1(C)C AULHADZGMKNZQE-UHFFFAOYSA-N 0.000 description 1
WJHJNFZDILTOOX-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcyclohexyl)-3-[[4-[3-(2H-tetrazol-5-yl)phenyl]-3H-pyridin-4-yl]methyl]imidazol-2-one Chemical compound CC1(C(CCCC1)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O)C WJHJNFZDILTOOX-UHFFFAOYSA-N 0.000 description 1
VSHQTUPQLHJTQX-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcyclohexyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1(C)C VSHQTUPQLHJTQX-UHFFFAOYSA-N 0.000 description 1
PXQQXZZMYXPTEY-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcyclooctyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1(C)C PXQQXZZMYXPTEY-UHFFFAOYSA-N 0.000 description 1
HCPCBLXIIQKPIV-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcyclooctyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1(C)C HCPCBLXIIQKPIV-UHFFFAOYSA-N 0.000 description 1
BKKQRQXWBZBZBP-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcyclooctyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1(C)C BKKQRQXWBZBZBP-UHFFFAOYSA-N 0.000 description 1
PANOPUAACXTVKJ-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcyclopentyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1(C)C PANOPUAACXTVKJ-UHFFFAOYSA-N 0.000 description 1
VLEHIVRTYFEEAN-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcyclopentyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1(C)C VLEHIVRTYFEEAN-UHFFFAOYSA-N 0.000 description 1
ZFXLZJJXJXKJLL-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcyclopentyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1(C)C ZFXLZJJXJXKJLL-UHFFFAOYSA-N 0.000 description 1
NJQWQVBKAPMHKI-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcyclopentyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1(C)C NJQWQVBKAPMHKI-UHFFFAOYSA-N 0.000 description 1
ZMIXCFYGOAUNLA-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcyclopentyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1(C)C ZMIXCFYGOAUNLA-UHFFFAOYSA-N 0.000 description 1
YGJZIFQIZODGBU-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcyclopropyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1(C)C YGJZIFQIZODGBU-UHFFFAOYSA-N 0.000 description 1
VPCBWQUGRIJNDF-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcyclopropyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1(C)C VPCBWQUGRIJNDF-UHFFFAOYSA-N 0.000 description 1
MBUQYVHIPLMSAW-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcyclopropyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1(C)C MBUQYVHIPLMSAW-UHFFFAOYSA-N 0.000 description 1
IPFLNDJMAFFUPW-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcyclopropyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1(C)C IPFLNDJMAFFUPW-UHFFFAOYSA-N 0.000 description 1
MDQSVIQNLIQWMV-UHFFFAOYSA-N 4-butyl-1-(2,2-dimethylcyclopropyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1(C)C MDQSVIQNLIQWMV-UHFFFAOYSA-N 0.000 description 1
OEBUNGIRBINIKR-UHFFFAOYSA-N 4-butyl-1-(2,3-diethylcyclopropyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)C1CC OEBUNGIRBINIKR-UHFFFAOYSA-N 0.000 description 1
SEJWJGDXEKOZES-UHFFFAOYSA-N 4-butyl-1-(2,3-diethylcyclopropyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)C1CC SEJWJGDXEKOZES-UHFFFAOYSA-N 0.000 description 1
XXSXRSGARCTTRI-UHFFFAOYSA-N 4-butyl-1-(2,3-diethylcyclopropyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)C1CC XXSXRSGARCTTRI-UHFFFAOYSA-N 0.000 description 1
QMMAYIODTVMLRY-UHFFFAOYSA-N 4-butyl-1-(2,3-diethylcyclopropyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)C1CC QMMAYIODTVMLRY-UHFFFAOYSA-N 0.000 description 1
AGJRCVVFIDSNEF-UHFFFAOYSA-N 4-butyl-1-(2,3-dimethylcyclopropyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)C1C AGJRCVVFIDSNEF-UHFFFAOYSA-N 0.000 description 1
SUFDKVOCUZGYGP-UHFFFAOYSA-N 4-butyl-1-(2,4-diethylcyclobutyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CC1CC SUFDKVOCUZGYGP-UHFFFAOYSA-N 0.000 description 1
IBCZUKLMQNPWQG-UHFFFAOYSA-N 4-butyl-1-(2,4-diethylcyclobutyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CC1CC IBCZUKLMQNPWQG-UHFFFAOYSA-N 0.000 description 1
NPYDTENHOMUWRD-UHFFFAOYSA-N 4-butyl-1-(2,4-diethylcyclobutyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CC1CC NPYDTENHOMUWRD-UHFFFAOYSA-N 0.000 description 1
CREUPGCWRHLHLK-UHFFFAOYSA-N 4-butyl-1-(2,4-diethylcyclobutyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CC1CC CREUPGCWRHLHLK-UHFFFAOYSA-N 0.000 description 1
JUGHSDBMQBFWMM-UHFFFAOYSA-N 4-butyl-1-(2,5-diethylcyclopentyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCC1CC JUGHSDBMQBFWMM-UHFFFAOYSA-N 0.000 description 1
CPYIKPILNYBLID-UHFFFAOYSA-N 4-butyl-1-(2,6-diethylcyclohexyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCC1CC CPYIKPILNYBLID-UHFFFAOYSA-N 0.000 description 1
WCTVROZYGCBSQN-UHFFFAOYSA-N 4-butyl-1-(2,6-diethylcyclohexyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCC1CC WCTVROZYGCBSQN-UHFFFAOYSA-N 0.000 description 1
XEGYXWQAPOYEDI-UHFFFAOYSA-N 4-butyl-1-(2,6-dimethylcyclohexyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCC1C XEGYXWQAPOYEDI-UHFFFAOYSA-N 0.000 description 1
ZXDHDIPZEPLLJG-UHFFFAOYSA-N 4-butyl-1-(2,7-diethylcycloheptyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCCC1CC ZXDHDIPZEPLLJG-UHFFFAOYSA-N 0.000 description 1
LBDDNUKHTHIWDE-UHFFFAOYSA-N 4-butyl-1-(2,7-diethylcycloheptyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCCC1CC LBDDNUKHTHIWDE-UHFFFAOYSA-N 0.000 description 1
TUTDSMLUAJVUIR-UHFFFAOYSA-N 4-butyl-1-(2,7-diethylcycloheptyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCCC1CC TUTDSMLUAJVUIR-UHFFFAOYSA-N 0.000 description 1
IVQXULZMPDPPTE-UHFFFAOYSA-N 4-butyl-1-(2,7-diethylcycloheptyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCCC1CC IVQXULZMPDPPTE-UHFFFAOYSA-N 0.000 description 1
SVVKRCZZNXCANQ-UHFFFAOYSA-N 4-butyl-1-(2,8-diethylcyclooctyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCCCC1CC SVVKRCZZNXCANQ-UHFFFAOYSA-N 0.000 description 1
LBWKWRDVGXLNBN-UHFFFAOYSA-N 4-butyl-1-(2,8-dimethylcyclooctyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCCC1C LBWKWRDVGXLNBN-UHFFFAOYSA-N 0.000 description 1
GTFQSGGPLQWBRL-UHFFFAOYSA-N 4-butyl-1-(2,8-dimethylcyclooctyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCCC1C GTFQSGGPLQWBRL-UHFFFAOYSA-N 0.000 description 1
WXOCVBTXYXURTQ-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-3-oxocyclopropyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)C1=O WXOCVBTXYXURTQ-UHFFFAOYSA-N 0.000 description 1
GIEKKDJQWXEILN-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-3-oxocyclopropyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)C1=O GIEKKDJQWXEILN-UHFFFAOYSA-N 0.000 description 1
FOVJPCXECLHRPS-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-3-oxocyclopropyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)C1=O FOVJPCXECLHRPS-UHFFFAOYSA-N 0.000 description 1
RCUNSKLKJHPYGH-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-3-oxocyclopropyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)C1=O RCUNSKLKJHPYGH-UHFFFAOYSA-N 0.000 description 1
OLPPFCUDLDKRAP-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-3-propan-2-ylcyclopropyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)C1C(C)C OLPPFCUDLDKRAP-UHFFFAOYSA-N 0.000 description 1
WGAISRAMMWOCBF-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-3-propan-2-ylcyclopropyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)C1C(C)C WGAISRAMMWOCBF-UHFFFAOYSA-N 0.000 description 1
ARTWDSJYGDHTGJ-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-4-oxocyclobutyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CC1=O ARTWDSJYGDHTGJ-UHFFFAOYSA-N 0.000 description 1
YRBFCDHURGXNPB-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-4-oxocyclobutyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CC1=O YRBFCDHURGXNPB-UHFFFAOYSA-N 0.000 description 1
ZAFVKJTYPHUZTM-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-4-oxocyclobutyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CC1=O ZAFVKJTYPHUZTM-UHFFFAOYSA-N 0.000 description 1
XTMOKIJWMUUZOI-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-4-oxocyclobutyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CC1=O XTMOKIJWMUUZOI-UHFFFAOYSA-N 0.000 description 1
AFHFRNZWHXHAAJ-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-5-oxocyclopentyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCC1=O AFHFRNZWHXHAAJ-UHFFFAOYSA-N 0.000 description 1
VBRUOCLUKXDLBD-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-5-oxocyclopentyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCC1=O VBRUOCLUKXDLBD-UHFFFAOYSA-N 0.000 description 1
FXEDPYHSTVAKBP-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-5-oxocyclopentyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCC1=O FXEDPYHSTVAKBP-UHFFFAOYSA-N 0.000 description 1
YCAWUMROEFUNMR-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-5-oxocyclopentyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCC1=O YCAWUMROEFUNMR-UHFFFAOYSA-N 0.000 description 1
LRLSXOPWMNSGBO-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-5-propan-2-ylcyclopentyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCC1C(C)C LRLSXOPWMNSGBO-UHFFFAOYSA-N 0.000 description 1
KHZIVZNYODHOHR-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-5-propan-2-ylcyclopentyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCC1C(C)C KHZIVZNYODHOHR-UHFFFAOYSA-N 0.000 description 1
YDQULLKMAVMKNQ-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-6-oxocyclohexyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCC1=O YDQULLKMAVMKNQ-UHFFFAOYSA-N 0.000 description 1
JSAVRNINXIBSBJ-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-6-oxocyclohexyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCC1=O JSAVRNINXIBSBJ-UHFFFAOYSA-N 0.000 description 1
OWQDXSORUSMXEQ-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-6-oxocyclohexyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCC1=O OWQDXSORUSMXEQ-UHFFFAOYSA-N 0.000 description 1
JESYHPVBQJGPBC-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-6-oxocyclohexyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCC1=O JESYHPVBQJGPBC-UHFFFAOYSA-N 0.000 description 1
DXPIXMJJJPWJDM-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-6-propan-2-ylcyclohexyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCC1C(C)C DXPIXMJJJPWJDM-UHFFFAOYSA-N 0.000 description 1
LVJWSFIFSMLIDJ-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-6-propan-2-ylcyclohexyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCC1C(C)C LVJWSFIFSMLIDJ-UHFFFAOYSA-N 0.000 description 1
FBVYMJDRCSVEDI-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-6-propan-2-ylcyclohexyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCC1C(C)C FBVYMJDRCSVEDI-UHFFFAOYSA-N 0.000 description 1
FIZDIWSGROOKTH-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-7-oxocycloheptyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCCC1=O FIZDIWSGROOKTH-UHFFFAOYSA-N 0.000 description 1
JTYFQMBDYJXEKF-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-7-oxocycloheptyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCCC1=O JTYFQMBDYJXEKF-UHFFFAOYSA-N 0.000 description 1
MHCVEVVWNRZOAN-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-7-oxocycloheptyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCCC1=O MHCVEVVWNRZOAN-UHFFFAOYSA-N 0.000 description 1
KWJOMMSMFKGUHN-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-7-oxocycloheptyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCCC1=O KWJOMMSMFKGUHN-UHFFFAOYSA-N 0.000 description 1
HQPAKTWWSYNPGQ-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-7-propan-2-ylcycloheptyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCCC1C(C)C HQPAKTWWSYNPGQ-UHFFFAOYSA-N 0.000 description 1
ZXOCDDPHINDZSC-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-7-propan-2-ylcycloheptyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCCC1C(C)C ZXOCDDPHINDZSC-UHFFFAOYSA-N 0.000 description 1
RUOGKXWLMIQLEQ-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-8-oxocyclooctyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCCCC1=O RUOGKXWLMIQLEQ-UHFFFAOYSA-N 0.000 description 1
JIZUUOGZNNMSMC-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-8-oxocyclooctyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCCCC1=O JIZUUOGZNNMSMC-UHFFFAOYSA-N 0.000 description 1
MYRSMMNBSCSFEK-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-8-oxocyclooctyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCCCC1=O MYRSMMNBSCSFEK-UHFFFAOYSA-N 0.000 description 1
NXUWCIHXHJSFHJ-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-8-oxocyclooctyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCCCC1=O NXUWCIHXHJSFHJ-UHFFFAOYSA-N 0.000 description 1
KDVKVJMWWYZYBD-UHFFFAOYSA-N 4-butyl-1-(2-ethyl-8-propan-2-ylcyclooctyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(CC)CCCCCC1C(C)C KDVKVJMWWYZYBD-UHFFFAOYSA-N 0.000 description 1
RMGGOKRWIXNIGG-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycyclobutyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1O RMGGOKRWIXNIGG-UHFFFAOYSA-N 0.000 description 1
WJSPDTSTNYTAJB-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycyclobutyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1O WJSPDTSTNYTAJB-UHFFFAOYSA-N 0.000 description 1
PTIUXRXPAUEVFP-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycyclobutyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1O PTIUXRXPAUEVFP-UHFFFAOYSA-N 0.000 description 1
MIXFHOWXNKIGGS-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycyclobutyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1O MIXFHOWXNKIGGS-UHFFFAOYSA-N 0.000 description 1
BRBOGSMEQITBIA-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycycloheptyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1O BRBOGSMEQITBIA-UHFFFAOYSA-N 0.000 description 1
JTSUQQWSMUAMSZ-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycycloheptyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1O JTSUQQWSMUAMSZ-UHFFFAOYSA-N 0.000 description 1
GNQWMYVEEJMULS-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycycloheptyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1O GNQWMYVEEJMULS-UHFFFAOYSA-N 0.000 description 1
YXQOVBJEFUUYQO-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycycloheptyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1O YXQOVBJEFUUYQO-UHFFFAOYSA-N 0.000 description 1
JSXZWKTYXXYFNW-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycyclohexyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1O JSXZWKTYXXYFNW-UHFFFAOYSA-N 0.000 description 1
HSEFCVLTJQDNMX-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycyclohexyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1O HSEFCVLTJQDNMX-UHFFFAOYSA-N 0.000 description 1
HHRNLKYVCFVPDL-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycyclohexyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1O HHRNLKYVCFVPDL-UHFFFAOYSA-N 0.000 description 1
LCAOILMAWWRNIE-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycyclohexyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1O LCAOILMAWWRNIE-UHFFFAOYSA-N 0.000 description 1
OUJRIOKVBYFLKW-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycyclohexyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1O OUJRIOKVBYFLKW-UHFFFAOYSA-N 0.000 description 1
QZUMMASNHOEILE-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycyclooctyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1O QZUMMASNHOEILE-UHFFFAOYSA-N 0.000 description 1
JECGRWXGFAXNFB-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycyclooctyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1O JECGRWXGFAXNFB-UHFFFAOYSA-N 0.000 description 1
QQFKGWMEDAHHRB-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycyclooctyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1O QQFKGWMEDAHHRB-UHFFFAOYSA-N 0.000 description 1
UAKJNQLVNNHDSD-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycyclooctyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1O UAKJNQLVNNHDSD-UHFFFAOYSA-N 0.000 description 1
QKDSLVAHWAMMET-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycyclopentyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1O QKDSLVAHWAMMET-UHFFFAOYSA-N 0.000 description 1
ZWHBLRDPCDIDES-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycyclopentyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1O ZWHBLRDPCDIDES-UHFFFAOYSA-N 0.000 description 1
DDYSRUCOPUCXQY-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycyclopentyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1O DDYSRUCOPUCXQY-UHFFFAOYSA-N 0.000 description 1
SWYAPYAHAJMOGM-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycyclopropyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1O SWYAPYAHAJMOGM-UHFFFAOYSA-N 0.000 description 1
YHNAQCFNRCIZST-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycyclopropyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1O YHNAQCFNRCIZST-UHFFFAOYSA-N 0.000 description 1
SBSQCERVHGXDQG-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycyclopropyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1O SBSQCERVHGXDQG-UHFFFAOYSA-N 0.000 description 1
UBWWQUYLHHSOAP-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycyclopropyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1O UBWWQUYLHHSOAP-UHFFFAOYSA-N 0.000 description 1
SFRWKEUUQDLRHU-UHFFFAOYSA-N 4-butyl-1-(2-hydroxycyclopropyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1O SFRWKEUUQDLRHU-UHFFFAOYSA-N 0.000 description 1
MREJESIXQOZJFS-UHFFFAOYSA-N 4-butyl-1-(2-methoxycycloheptyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1OC MREJESIXQOZJFS-UHFFFAOYSA-N 0.000 description 1
WOOMCFQZWJGLFB-UHFFFAOYSA-N 4-butyl-1-(2-methoxycycloheptyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1OC WOOMCFQZWJGLFB-UHFFFAOYSA-N 0.000 description 1
OCDJKTCZHURFSG-UHFFFAOYSA-N 4-butyl-1-(2-methoxycycloheptyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1OC OCDJKTCZHURFSG-UHFFFAOYSA-N 0.000 description 1
QUDNCCOKXZVYTA-UHFFFAOYSA-N 4-butyl-1-(2-methoxycyclohexyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1OC QUDNCCOKXZVYTA-UHFFFAOYSA-N 0.000 description 1
PCEFSZOSPJYINO-UHFFFAOYSA-N 4-butyl-1-(2-methoxycyclohexyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1OC PCEFSZOSPJYINO-UHFFFAOYSA-N 0.000 description 1
LFCSIMHPTOQLAI-UHFFFAOYSA-N 4-butyl-1-(2-methoxycyclohexyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1OC LFCSIMHPTOQLAI-UHFFFAOYSA-N 0.000 description 1
DNZGXCUJTWIMMD-UHFFFAOYSA-N 4-butyl-1-(2-methoxycyclohexyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1OC DNZGXCUJTWIMMD-UHFFFAOYSA-N 0.000 description 1
WZUBTFZIOJDWCN-UHFFFAOYSA-N 4-butyl-1-(2-methoxycyclooctyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1OC WZUBTFZIOJDWCN-UHFFFAOYSA-N 0.000 description 1
KZVXMXKDEPGITC-UHFFFAOYSA-N 4-butyl-1-(2-methoxycyclooctyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1OC KZVXMXKDEPGITC-UHFFFAOYSA-N 0.000 description 1
KSZMTMMIZCMAQU-UHFFFAOYSA-N 4-butyl-1-(2-methoxycyclooctyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1OC KSZMTMMIZCMAQU-UHFFFAOYSA-N 0.000 description 1
MCMRZQIUHTZFRU-UHFFFAOYSA-N 4-butyl-1-(2-methoxycyclooctyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1OC MCMRZQIUHTZFRU-UHFFFAOYSA-N 0.000 description 1
XNFISVHRIGULQF-UHFFFAOYSA-N 4-butyl-1-(2-methoxycyclopentyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1OC XNFISVHRIGULQF-UHFFFAOYSA-N 0.000 description 1
MWRHIJCJEPIWFG-UHFFFAOYSA-N 4-butyl-1-(2-methoxycyclopentyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1OC MWRHIJCJEPIWFG-UHFFFAOYSA-N 0.000 description 1
ZCJSXZHODCQVPT-UHFFFAOYSA-N 4-butyl-1-(2-methoxycyclopentyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1OC ZCJSXZHODCQVPT-UHFFFAOYSA-N 0.000 description 1
RDBDJEQAYUARMO-UHFFFAOYSA-N 4-butyl-1-(2-methoxycyclopentyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1OC RDBDJEQAYUARMO-UHFFFAOYSA-N 0.000 description 1
MXOZIWOTPPIQDK-UHFFFAOYSA-N 4-butyl-1-(2-methoxycyclopentyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1OC MXOZIWOTPPIQDK-UHFFFAOYSA-N 0.000 description 1
DRCIWOBBVHAZFI-UHFFFAOYSA-N 4-butyl-1-(2-methoxycyclopropyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1OC DRCIWOBBVHAZFI-UHFFFAOYSA-N 0.000 description 1
PLXFPUFIHMHYSC-UHFFFAOYSA-N 4-butyl-1-(2-methoxycyclopropyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1OC PLXFPUFIHMHYSC-UHFFFAOYSA-N 0.000 description 1
XLDMHUYWYLRSOV-UHFFFAOYSA-N 4-butyl-1-(2-methyl-3-oxocyclopropyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)C1=O XLDMHUYWYLRSOV-UHFFFAOYSA-N 0.000 description 1
GXDUMGNDZPBZDK-UHFFFAOYSA-N 4-butyl-1-(2-methyl-3-oxocyclopropyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)C1=O GXDUMGNDZPBZDK-UHFFFAOYSA-N 0.000 description 1
UASABZQTNCFKRL-UHFFFAOYSA-N 4-butyl-1-(2-methyl-3-propan-2-ylcyclopropyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)C1C(C)C UASABZQTNCFKRL-UHFFFAOYSA-N 0.000 description 1
DQLHRHJLMBCBSY-UHFFFAOYSA-N 4-butyl-1-(2-methyl-4-oxocyclobutyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CC1=O DQLHRHJLMBCBSY-UHFFFAOYSA-N 0.000 description 1
TZTJHCFIYRHEMI-UHFFFAOYSA-N 4-butyl-1-(2-methyl-4-oxocyclobutyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CC1=O TZTJHCFIYRHEMI-UHFFFAOYSA-N 0.000 description 1
GRSNEAGCCJESIQ-UHFFFAOYSA-N 4-butyl-1-(2-methyl-4-oxocyclobutyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CC1=O GRSNEAGCCJESIQ-UHFFFAOYSA-N 0.000 description 1
PSPHKYVAZBHABY-UHFFFAOYSA-N 4-butyl-1-(2-methyl-5-oxocyclopentyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCC1=O PSPHKYVAZBHABY-UHFFFAOYSA-N 0.000 description 1
AYPMOUGAXORQHX-UHFFFAOYSA-N 4-butyl-1-(2-methyl-5-oxocyclopentyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCC1=O AYPMOUGAXORQHX-UHFFFAOYSA-N 0.000 description 1
OAXJCGBRWIZNET-UHFFFAOYSA-N 4-butyl-1-(2-methyl-6-oxocyclohexyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCC1=O OAXJCGBRWIZNET-UHFFFAOYSA-N 0.000 description 1
SIFMLSLBVNJNPW-UHFFFAOYSA-N 4-butyl-1-(2-methyl-6-propan-2-ylcyclohexyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCC1C(C)C SIFMLSLBVNJNPW-UHFFFAOYSA-N 0.000 description 1
BAJNFUSEDBWGIF-UHFFFAOYSA-N 4-butyl-1-(2-methyl-7-oxocycloheptyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCC1=O BAJNFUSEDBWGIF-UHFFFAOYSA-N 0.000 description 1
OBEDMZFJTQYMDG-UHFFFAOYSA-N 4-butyl-1-(2-methyl-7-oxocycloheptyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCC1=O OBEDMZFJTQYMDG-UHFFFAOYSA-N 0.000 description 1
BQDKIEDBNSEXHE-UHFFFAOYSA-N 4-butyl-1-(2-methyl-7-propan-2-ylcycloheptyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCC1C(C)C BQDKIEDBNSEXHE-UHFFFAOYSA-N 0.000 description 1
XGBJWFOHKCEDKD-UHFFFAOYSA-N 4-butyl-1-(2-methyl-8-oxocyclooctyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCCC1=O XGBJWFOHKCEDKD-UHFFFAOYSA-N 0.000 description 1
MSCRRFQHQLTKHC-UHFFFAOYSA-N 4-butyl-1-(2-methyl-8-oxocyclooctyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCCC1=O MSCRRFQHQLTKHC-UHFFFAOYSA-N 0.000 description 1
OSDUCJQFGLMXDE-UHFFFAOYSA-N 4-butyl-1-(2-methyl-8-oxocyclooctyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCCC1=O OSDUCJQFGLMXDE-UHFFFAOYSA-N 0.000 description 1
BHZZUYCYYUUJIM-UHFFFAOYSA-N 4-butyl-1-(2-methyl-8-oxocyclooctyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C)CCCCCC1=O BHZZUYCYYUUJIM-UHFFFAOYSA-N 0.000 description 1
VFIXDOAZXULDFB-UHFFFAOYSA-N 4-butyl-1-(2-oxo-3-propan-2-ylcyclopropyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)C1=O VFIXDOAZXULDFB-UHFFFAOYSA-N 0.000 description 1
XZSZWUWYPIPCDA-UHFFFAOYSA-N 4-butyl-1-(2-oxo-3-propan-2-ylcyclopropyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)C1=O XZSZWUWYPIPCDA-UHFFFAOYSA-N 0.000 description 1
VRLWXUYFLUQRDE-UHFFFAOYSA-N 4-butyl-1-(2-oxo-3-propan-2-ylcyclopropyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)C1=O VRLWXUYFLUQRDE-UHFFFAOYSA-N 0.000 description 1
IOXLPKVZQBZMJX-UHFFFAOYSA-N 4-butyl-1-(2-oxo-3-propan-2-ylcyclopropyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)C1=O IOXLPKVZQBZMJX-UHFFFAOYSA-N 0.000 description 1
GFOJDOOJHLDRBG-UHFFFAOYSA-N 4-butyl-1-(2-oxo-5-propan-2-ylcyclopentyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CCC1=O GFOJDOOJHLDRBG-UHFFFAOYSA-N 0.000 description 1
OUDFHMYYASKEMR-UHFFFAOYSA-N 4-butyl-1-(2-oxo-5-propan-2-ylcyclopentyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CCC1=O OUDFHMYYASKEMR-UHFFFAOYSA-N 0.000 description 1
FYJFTLQKGQARKJ-UHFFFAOYSA-N 4-butyl-1-(2-oxo-5-propan-2-ylcyclopentyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CCC1=O FYJFTLQKGQARKJ-UHFFFAOYSA-N 0.000 description 1
ONFZJKAOALITSG-UHFFFAOYSA-N 4-butyl-1-(2-oxo-5-propan-2-ylcyclopentyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CCC1=O ONFZJKAOALITSG-UHFFFAOYSA-N 0.000 description 1
GZIDZTRMHUQDSY-UHFFFAOYSA-N 4-butyl-1-(2-oxo-6-propan-2-ylcyclohexyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CCCC1=O GZIDZTRMHUQDSY-UHFFFAOYSA-N 0.000 description 1
LSJFGVSGVCIPMD-UHFFFAOYSA-N 4-butyl-1-(2-oxo-6-propan-2-ylcyclohexyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CCCC1=O LSJFGVSGVCIPMD-UHFFFAOYSA-N 0.000 description 1
NGOVTWKBQNAHLF-UHFFFAOYSA-N 4-butyl-1-(2-oxo-6-propan-2-ylcyclohexyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CCCC1=O NGOVTWKBQNAHLF-UHFFFAOYSA-N 0.000 description 1
IGYNLQREGMDCIL-UHFFFAOYSA-N 4-butyl-1-(2-oxo-7-propan-2-ylcycloheptyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CCCCC1=O IGYNLQREGMDCIL-UHFFFAOYSA-N 0.000 description 1
QHZQPRJQASSCKP-UHFFFAOYSA-N 4-butyl-1-(2-oxo-7-propan-2-ylcycloheptyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CCCCC1=O QHZQPRJQASSCKP-UHFFFAOYSA-N 0.000 description 1
YIHUIFQJLTWEAT-UHFFFAOYSA-N 4-butyl-1-(2-oxo-7-propan-2-ylcycloheptyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CCCCC1=O YIHUIFQJLTWEAT-UHFFFAOYSA-N 0.000 description 1
YQJSBWGAGAZSQE-UHFFFAOYSA-N 4-butyl-1-(2-oxo-7-propan-2-ylcycloheptyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CCCCC1=O YQJSBWGAGAZSQE-UHFFFAOYSA-N 0.000 description 1
GGLHOTWWLLBWRB-UHFFFAOYSA-N 4-butyl-1-(2-oxo-8-propan-2-ylcyclooctyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CCCCCC1=O GGLHOTWWLLBWRB-UHFFFAOYSA-N 0.000 description 1
RWZMDHNVEIITBW-UHFFFAOYSA-N 4-butyl-1-(2-oxo-8-propan-2-ylcyclooctyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CCCCCC1=O RWZMDHNVEIITBW-UHFFFAOYSA-N 0.000 description 1
PAFFXGXACFEJBH-UHFFFAOYSA-N 4-butyl-1-(2-oxo-8-propan-2-ylcyclooctyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CCCCCC1=O PAFFXGXACFEJBH-UHFFFAOYSA-N 0.000 description 1
UMADHFJRQBWAQD-UHFFFAOYSA-N 4-butyl-1-(2-oxo-8-propan-2-ylcyclooctyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CCCCCC1=O UMADHFJRQBWAQD-UHFFFAOYSA-N 0.000 description 1
XXIBOBNPJJQQQM-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcyclobutyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1C(C)C XXIBOBNPJJQQQM-UHFFFAOYSA-N 0.000 description 1
VMZXTNQTHBUNNN-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcyclobutyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1C(C)C VMZXTNQTHBUNNN-UHFFFAOYSA-N 0.000 description 1
CPPNOBVLNMVPRI-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcyclobutyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1C(C)C CPPNOBVLNMVPRI-UHFFFAOYSA-N 0.000 description 1
AHGZPTMQTFLETQ-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcyclobutyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1C(C)C AHGZPTMQTFLETQ-UHFFFAOYSA-N 0.000 description 1
KYFSUKQZSWVLCS-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcyclobutyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1C(C)C KYFSUKQZSWVLCS-UHFFFAOYSA-N 0.000 description 1
RMEBFNKNNBIRHP-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcycloheptyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1C(C)C RMEBFNKNNBIRHP-UHFFFAOYSA-N 0.000 description 1
GTNMHJDHPCAAJS-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcycloheptyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1C(C)C GTNMHJDHPCAAJS-UHFFFAOYSA-N 0.000 description 1
ODDNCVKAELAEDK-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcycloheptyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1C(C)C ODDNCVKAELAEDK-UHFFFAOYSA-N 0.000 description 1
QFNMQFYOTMLTPR-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcycloheptyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1C(C)C QFNMQFYOTMLTPR-UHFFFAOYSA-N 0.000 description 1
VILDZPCAWCEDEO-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcyclohexyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1C(C)C VILDZPCAWCEDEO-UHFFFAOYSA-N 0.000 description 1
WNUYBLRIIBQKEL-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcyclohexyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1C(C)C WNUYBLRIIBQKEL-UHFFFAOYSA-N 0.000 description 1
WWFOVSLCMWTBLV-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcyclohexyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1C(C)C WWFOVSLCMWTBLV-UHFFFAOYSA-N 0.000 description 1
GFXWYWMVNHWPHJ-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcyclohexyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1C(C)C GFXWYWMVNHWPHJ-UHFFFAOYSA-N 0.000 description 1
VDKGJNMSVIWAJP-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcyclooctyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1C(C)C VDKGJNMSVIWAJP-UHFFFAOYSA-N 0.000 description 1
SHIHZNKCUQFDNB-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcyclooctyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1C(C)C SHIHZNKCUQFDNB-UHFFFAOYSA-N 0.000 description 1
ALPVXUISZYTOJX-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcyclooctyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1C(C)C ALPVXUISZYTOJX-UHFFFAOYSA-N 0.000 description 1
HUGNRNCONNYWIR-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcyclopentyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1C(C)C HUGNRNCONNYWIR-UHFFFAOYSA-N 0.000 description 1
TXZBENWMLMSZHM-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcyclopentyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1C(C)C TXZBENWMLMSZHM-UHFFFAOYSA-N 0.000 description 1
OFWUTNSYGUDXOF-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcyclopentyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1C(C)C OFWUTNSYGUDXOF-UHFFFAOYSA-N 0.000 description 1
KKZWIPZJOAPCBZ-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcyclopentyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1C(C)C KKZWIPZJOAPCBZ-UHFFFAOYSA-N 0.000 description 1
FFAQUNQHIIHVLT-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcyclopropyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1C(C)C FFAQUNQHIIHVLT-UHFFFAOYSA-N 0.000 description 1
KTWAFXGJLZNPAA-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcyclopropyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1C(C)C KTWAFXGJLZNPAA-UHFFFAOYSA-N 0.000 description 1
QATQTAJXTSEFJD-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcyclopropyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1C(C)C QATQTAJXTSEFJD-UHFFFAOYSA-N 0.000 description 1
NRZNUTSYWRPHDO-UHFFFAOYSA-N 4-butyl-1-(2-propan-2-ylcyclopropyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1C(C)C NRZNUTSYWRPHDO-UHFFFAOYSA-N 0.000 description 1
YUSGVRFFOHPZKX-UHFFFAOYSA-N 4-butyl-1-(2-propylcycloheptyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1CCC YUSGVRFFOHPZKX-UHFFFAOYSA-N 0.000 description 1
ITFUKAQWXKRXQC-UHFFFAOYSA-N 4-butyl-1-(2-propylcycloheptyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1CCC ITFUKAQWXKRXQC-UHFFFAOYSA-N 0.000 description 1
VYMBHNIRQBOEIF-UHFFFAOYSA-N 4-butyl-1-(2-propylcycloheptyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1CCC VYMBHNIRQBOEIF-UHFFFAOYSA-N 0.000 description 1
MHCJSJHFLAOQIA-UHFFFAOYSA-N 4-butyl-1-(2-propylcyclohexyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1CCC MHCJSJHFLAOQIA-UHFFFAOYSA-N 0.000 description 1
NJYXFEBMGSCYQX-UHFFFAOYSA-N 4-butyl-1-(2-propylcyclohexyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1CCC NJYXFEBMGSCYQX-UHFFFAOYSA-N 0.000 description 1
BXENQHNBOKKDRF-UHFFFAOYSA-N 4-butyl-1-(2-propylcyclohexyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1CCC BXENQHNBOKKDRF-UHFFFAOYSA-N 0.000 description 1
ZXYSDCYLZHPZGO-UHFFFAOYSA-N 4-butyl-1-(2-propylcyclooctyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1CCC ZXYSDCYLZHPZGO-UHFFFAOYSA-N 0.000 description 1
VKZUMSZRCOTIHW-UHFFFAOYSA-N 4-butyl-1-(2-propylcyclooctyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1CCC VKZUMSZRCOTIHW-UHFFFAOYSA-N 0.000 description 1
JLWOHRCLLRIERZ-UHFFFAOYSA-N 4-butyl-1-(2-propylcyclooctyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1CCC JLWOHRCLLRIERZ-UHFFFAOYSA-N 0.000 description 1
HNNNHMCDFOSMSE-UHFFFAOYSA-N 4-butyl-1-(2-propylcyclooctyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1CCC HNNNHMCDFOSMSE-UHFFFAOYSA-N 0.000 description 1
DHMZTYKNXJRKHM-UHFFFAOYSA-N 4-butyl-1-(2-propylcyclopentyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1CCC DHMZTYKNXJRKHM-UHFFFAOYSA-N 0.000 description 1
AUPCKCMKZJBBID-UHFFFAOYSA-N 4-butyl-1-(2-propylcyclopentyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1CCC AUPCKCMKZJBBID-UHFFFAOYSA-N 0.000 description 1
RFWNOPBTQBGFPT-UHFFFAOYSA-N 4-butyl-1-(2-propylcyclopentyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1CCC RFWNOPBTQBGFPT-UHFFFAOYSA-N 0.000 description 1
ZASXTRBFGPWQBB-UHFFFAOYSA-N 4-butyl-1-(2-propylcyclopentyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1CCC ZASXTRBFGPWQBB-UHFFFAOYSA-N 0.000 description 1
DUAKQVXFWOLLHB-UHFFFAOYSA-N 4-butyl-1-(2-propylcyclopropyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1CCC DUAKQVXFWOLLHB-UHFFFAOYSA-N 0.000 description 1
MKVSZDVPILNLAZ-UHFFFAOYSA-N 4-butyl-1-(2-propylcyclopropyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1CCC MKVSZDVPILNLAZ-UHFFFAOYSA-N 0.000 description 1
GITGQULTDCVUIX-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcyclobutyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1C(C)(C)C GITGQULTDCVUIX-UHFFFAOYSA-N 0.000 description 1
ITOGNFKRHRVUOJ-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcyclobutyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1C(C)(C)C ITOGNFKRHRVUOJ-UHFFFAOYSA-N 0.000 description 1
JVNDTKJYLLNDJV-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcyclobutyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1C(C)(C)C JVNDTKJYLLNDJV-UHFFFAOYSA-N 0.000 description 1
QHXWZJFARNLJMG-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcyclobutyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1C(C)(C)C QHXWZJFARNLJMG-UHFFFAOYSA-N 0.000 description 1
ZPHUKKKWOARDQO-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcyclobutyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCC1C(C)(C)C ZPHUKKKWOARDQO-UHFFFAOYSA-N 0.000 description 1
ZZYUSYUFFQCNFV-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcycloheptyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1C(C)(C)C ZZYUSYUFFQCNFV-UHFFFAOYSA-N 0.000 description 1
ZVSAFPHOOOBFTN-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcycloheptyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1C(C)(C)C ZVSAFPHOOOBFTN-UHFFFAOYSA-N 0.000 description 1
UGYDOBZJVFXMSX-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcycloheptyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCC1C(C)(C)C UGYDOBZJVFXMSX-UHFFFAOYSA-N 0.000 description 1
QFYJEZBONUGIFT-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcyclohexyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1C(C)(C)C QFYJEZBONUGIFT-UHFFFAOYSA-N 0.000 description 1
YVVINMZHVPLYHV-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcyclohexyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1C(C)(C)C YVVINMZHVPLYHV-UHFFFAOYSA-N 0.000 description 1
JBUJOPYOJGRUBM-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcyclohexyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1C(C)(C)C JBUJOPYOJGRUBM-UHFFFAOYSA-N 0.000 description 1
QSAMUUKGFJYILR-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcyclohexyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1C(C)(C)C QSAMUUKGFJYILR-UHFFFAOYSA-N 0.000 description 1
LAINOIMJSQYDIV-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcyclohexyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCC1C(C)(C)C LAINOIMJSQYDIV-UHFFFAOYSA-N 0.000 description 1
OZGDWMVWOQIKRE-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcyclooctyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1C(C)(C)C OZGDWMVWOQIKRE-UHFFFAOYSA-N 0.000 description 1
SLNBTFLVVZGYRL-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcyclooctyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1C(C)(C)C SLNBTFLVVZGYRL-UHFFFAOYSA-N 0.000 description 1
JEZBDKWFIQDQIO-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcyclooctyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCCCCC1C(C)(C)C JEZBDKWFIQDQIO-UHFFFAOYSA-N 0.000 description 1
CBFQHFHQNORVGM-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcyclopentyl)-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1C(C)(C)C CBFQHFHQNORVGM-UHFFFAOYSA-N 0.000 description 1
OJCRNTHMQRQSQG-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcyclopentyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1C(C)(C)C OJCRNTHMQRQSQG-UHFFFAOYSA-N 0.000 description 1
SWADEZYKRFYSRR-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcyclopentyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1C(C)(C)C SWADEZYKRFYSRR-UHFFFAOYSA-N 0.000 description 1
FGMHDGCNPSGTDA-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcyclopentyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1C(C)(C)C FGMHDGCNPSGTDA-UHFFFAOYSA-N 0.000 description 1
XZWVIVACMDNVFN-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcyclopentyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CCCC1C(C)(C)C XZWVIVACMDNVFN-UHFFFAOYSA-N 0.000 description 1
GZIJZHWLLCABEP-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcyclopropyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1C(C)(C)C GZIJZHWLLCABEP-UHFFFAOYSA-N 0.000 description 1
PHSPQFJEKSHUOI-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcyclopropyl)-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1C(C)(C)C PHSPQFJEKSHUOI-UHFFFAOYSA-N 0.000 description 1
FPYBZYOKJGLKQU-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcyclopropyl)-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1C(C)(C)C FPYBZYOKJGLKQU-UHFFFAOYSA-N 0.000 description 1
IJANIGLJTWCACI-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcyclopropyl)-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1C(C)(C)C IJANIGLJTWCACI-UHFFFAOYSA-N 0.000 description 1
TUEVHUCYCMNLDW-UHFFFAOYSA-N 4-butyl-1-(2-tert-butylcyclopropyl)-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1CC1C(C)(C)C TUEVHUCYCMNLDW-UHFFFAOYSA-N 0.000 description 1
VOOUJZCPIITLEI-UHFFFAOYSA-N 4-butyl-1-[2,4-di(propan-2-yl)cyclobutyl]-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CC1C(C)C VOOUJZCPIITLEI-UHFFFAOYSA-N 0.000 description 1
RKOYNEIEXZGWLJ-UHFFFAOYSA-N 4-butyl-1-[2,4-di(propan-2-yl)cyclobutyl]-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]-3h-pyridin-4-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC2(C=CN=CC2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CC1C(C)C RKOYNEIEXZGWLJ-UHFFFAOYSA-N 0.000 description 1
CALLAXRCHZBTKG-UHFFFAOYSA-N 4-butyl-1-[2,4-di(propan-2-yl)cyclobutyl]-3-[[4-[3-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC=C(C=2)C=2C=C(C=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CC1C(C)C CALLAXRCHZBTKG-UHFFFAOYSA-N 0.000 description 1
PYXFMQBYVTXIKO-UHFFFAOYSA-N 4-butyl-1-[2,4-di(propan-2-yl)cyclobutyl]-3-[[4-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C(=CC=NC=2)C=2C=CC(=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CC1C(C)C PYXFMQBYVTXIKO-UHFFFAOYSA-N 0.000 description 1
YKOPCNNQWXHYHO-UHFFFAOYSA-N 4-butyl-1-[2,4-di(propan-2-yl)cyclobutyl]-3-[[5-[2-(2h-tetrazol-5-yl)phenyl]pyridin-2-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2N=CC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CC1C(C)C YKOPCNNQWXHYHO-UHFFFAOYSA-N 0.000 description 1
SZSWFDDHHSLWCF-UHFFFAOYSA-N 4-butyl-1-[2,4-di(propan-2-yl)cyclobutyl]-3-[[6-[2-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]methyl]imidazol-2-one Chemical compound O=C1N(CC=2C=NC(=CC=2)C=2C(=CC=CC=2)C2=NNN=N2)C(CCCC)=CN1C1C(C(C)C)CC1C(C)C SZSWFDDHHSLWCF-UHFFFAOYSA-N 0.000 description 1
229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
IJIBRSFAXRFPPN-UHFFFAOYSA-N 5-bromo-2-methoxybenzaldehyde Chemical compound COC1=CC=C(Br)C=C1C=O IJIBRSFAXRFPPN-UHFFFAOYSA-N 0.000 description 1
OYVNZPTUCAKSPS-UHFFFAOYSA-N 5-butyl-3-(2,2-dimethylcyclohexyl)-1h-imidazol-2-one Chemical compound O=C1NC(CCCC)=CN1C1C(C)(C)CCCC1 OYVNZPTUCAKSPS-UHFFFAOYSA-N 0.000 description 1
CMBSSVKZOPZBKW-UHFFFAOYSA-N 5-methylpyridin-2-amine Chemical compound CC1=CC=C(N)N=C1 CMBSSVKZOPZBKW-UHFFFAOYSA-N 0.000 description 1
AMKGKYQBASDDJB-UHFFFAOYSA-N 9$l^{2}-borabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1[B]2 AMKGKYQBASDDJB-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
235000006491 Acacia senegal Nutrition 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
BHUVFMUOTFQAEP-UHFFFAOYSA-N C(=O)(O)C1C(CCCCC1)N1C(N(C(=C1)CCCC)CC1=NC=CC(=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound C(=O)(O)C1C(CCCCC1)N1C(N(C(=C1)CCCC)CC1=NC=CC(=C1)C1=CC(=CC=C1)C1=NN=NN1)=O BHUVFMUOTFQAEP-UHFFFAOYSA-N 0.000 description 1
UDIMZXVMYKCYAB-UHFFFAOYSA-N C(C)(=O)C1C(CCCC1)N1C(N(C(=C1)CCCC)CC=1C=NC=CC1C1=CC=C(C=C1)C1=NN=NN1)=O Chemical compound C(C)(=O)C1C(CCCC1)N1C(N(C(=C1)CCCC)CC=1C=NC=CC1C1=CC=C(C=C1)C1=NN=NN1)=O UDIMZXVMYKCYAB-UHFFFAOYSA-N 0.000 description 1
GGJZQNSRAWSMRT-UHFFFAOYSA-N C(C)(=O)C1C(CCCCC1)N1C(N(C(=C1)CCCC)CC1=NC=CC(=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound C(C)(=O)C1C(CCCCC1)N1C(N(C(=C1)CCCC)CC1=NC=CC(=C1)C1=CC(=CC=C1)C1=NN=NN1)=O GGJZQNSRAWSMRT-UHFFFAOYSA-N 0.000 description 1
UPDHNGHCJIHIMY-UHFFFAOYSA-N C(C)(C)(C)C1C(CCCCC1)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound C(C)(C)(C)C1C(CCCCC1)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O UPDHNGHCJIHIMY-UHFFFAOYSA-N 0.000 description 1
PGQPNSYEAPFPQC-UHFFFAOYSA-N C(C)(C)(C)C1C(CCCCCC1)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound C(C)(C)(C)C1C(CCCCCC1)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O PGQPNSYEAPFPQC-UHFFFAOYSA-N 0.000 description 1
KVLUSVMCPXMTGE-UHFFFAOYSA-N C(C)(C)C1C(C(CCC1)C(C)C)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound C(C)(C)C1C(C(CCC1)C(C)C)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O KVLUSVMCPXMTGE-UHFFFAOYSA-N 0.000 description 1
MBBMLCMKNYJUBT-UHFFFAOYSA-N C(C)(C)C1C(CCC1)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound C(C)(C)C1C(CCC1)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O MBBMLCMKNYJUBT-UHFFFAOYSA-N 0.000 description 1
SKOIDYYODDORAG-UHFFFAOYSA-N C(C)(C)C1C(CCCCC1)N1C(N(C(=C1)CCCC)CC1=NC=CC(=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound C(C)(C)C1C(CCCCC1)N1C(N(C(=C1)CCCC)CC1=NC=CC(=C1)C1=CC(=CC=C1)C1=NN=NN1)=O SKOIDYYODDORAG-UHFFFAOYSA-N 0.000 description 1
FYJCUTMJYOJJPB-UHFFFAOYSA-N C(C)C1C(C(CCC1)CC)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound C(C)C1C(C(CCC1)CC)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O FYJCUTMJYOJJPB-UHFFFAOYSA-N 0.000 description 1
JIANBPIJSZNVRC-UHFFFAOYSA-N C(C)C1C(C(CCC1)CC)N1C(N(C(=C1)CCCC)CC1=NC=CC(=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound C(C)C1C(C(CCC1)CC)N1C(N(C(=C1)CCCC)CC1=NC=CC(=C1)C1=CC(=CC=C1)C1=NN=NN1)=O JIANBPIJSZNVRC-UHFFFAOYSA-N 0.000 description 1
WMLTXSTVGGPCJH-UHFFFAOYSA-N C(C)C1C(C(CCC1)CC)N1C(N(C(=C1)CCCC)CC=1C=NC=CC1C1=CC=C(C=C1)C1=NN=NN1)=O Chemical compound C(C)C1C(C(CCC1)CC)N1C(N(C(=C1)CCCC)CC=1C=NC=CC1C1=CC=C(C=C1)C1=NN=NN1)=O WMLTXSTVGGPCJH-UHFFFAOYSA-N 0.000 description 1
RVZKAEKTRWGCQO-UHFFFAOYSA-N C(C)C1C(C(CCCC1)CC)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound C(C)C1C(C(CCCC1)CC)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O RVZKAEKTRWGCQO-UHFFFAOYSA-N 0.000 description 1
LVFFRKWXWLQFMM-UHFFFAOYSA-N C(C)C1C(C(CCCCC1)CC)N1C(N(C(=C1)CCCC)CC=1C=NC(=CC1)C1=C(C=CC=C1)C1=NN=NN1)=O Chemical compound C(C)C1C(C(CCCCC1)CC)N1C(N(C(=C1)CCCC)CC=1C=NC(=CC1)C1=C(C=CC=C1)C1=NN=NN1)=O LVFFRKWXWLQFMM-UHFFFAOYSA-N 0.000 description 1
YJVOXNARBUJLMC-UHFFFAOYSA-N C(CC)C1C(CCCCC1)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound C(CC)C1C(CCCCC1)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O YJVOXNARBUJLMC-UHFFFAOYSA-N 0.000 description 1
SVULEBCCNPVUNO-UHFFFAOYSA-N CC1C(CC(C1)C)N1C(N(C(=C1)CCCC)CC=1C=NC=CC1C1=CC=C(C=C1)C1=NN=NN1)=O Chemical compound CC1C(CC(C1)C)N1C(N(C(=C1)CCCC)CC=1C=NC=CC1C1=CC=C(C=C1)C1=NN=NN1)=O SVULEBCCNPVUNO-UHFFFAOYSA-N 0.000 description 1
HRATZNXJEWPJME-UHFFFAOYSA-N COC1C(CCCCC1)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound COC1C(CCCCC1)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O HRATZNXJEWPJME-UHFFFAOYSA-N 0.000 description 1
WFOKXEONESXODS-UHFFFAOYSA-N COC1C(CCCCC1)N1C(N(C(=C1)CCCC)CC1=NC=C(C=C1)C1=C(C=CC=C1)C1=NN=NN1)=O Chemical compound COC1C(CCCCC1)N1C(N(C(=C1)CCCC)CC1=NC=C(C=C1)C1=C(C=CC=C1)C1=NN=NN1)=O WFOKXEONESXODS-UHFFFAOYSA-N 0.000 description 1
IOLLRZYQFFZPKF-UHFFFAOYSA-M CV 2961 Chemical compound [Na+].CCCCC1=NC(Cl)=C(CC([O-])=O)N1CC1=CC=CC=C1[N+]([O-])=O IOLLRZYQFFZPKF-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 1
UNPLRYRWJLTVAE-UHFFFAOYSA-N Cloperastine hydrochloride Chemical class Cl.C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)OCCN1CCCCC1 UNPLRYRWJLTVAE-UHFFFAOYSA-N 0.000 description 1
206010010356 Congenital anomaly Diseases 0.000 description 1
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
229920005479 Lucite® Polymers 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
108010052285 Membrane Proteins Proteins 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
NZXKDOXHBHYTKP-UHFFFAOYSA-N Metohexital Chemical compound CCC#CC(C)C1(CC=C)C(=O)NC(=O)N(C)C1=O NZXKDOXHBHYTKP-UHFFFAOYSA-N 0.000 description 1
HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
MLQYBTMZZSMOHV-UHFFFAOYSA-N N(O)OS(=O)(=O)ONO Chemical compound N(O)OS(=O)(=O)ONO MLQYBTMZZSMOHV-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
CJNWRXQJJHBLGO-UHFFFAOYSA-N O=C1C(C(CC1)CC)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound O=C1C(C(CC1)CC)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O CJNWRXQJJHBLGO-UHFFFAOYSA-N 0.000 description 1
BZEILFUOTUZNAD-UHFFFAOYSA-N O=C1C(C(CCC1)C)N1C(N(C(=C1)CCCC)CC=1C=NC=CC1C1=CC=C(C=C1)C1=NN=NN1)=O Chemical compound O=C1C(C(CCC1)C)N1C(N(C(=C1)CCCC)CC=1C=NC=CC1C1=CC=C(C=C1)C1=NN=NN1)=O BZEILFUOTUZNAD-UHFFFAOYSA-N 0.000 description 1
ZFWCPVGZPZDQDX-UHFFFAOYSA-N O=C1C(C(CCCC1)C)N1C(N(C(=C1)CCCC)CC=1C=NC(=CC1)C1=C(C=CC=C1)C1=NN=NN1)=O Chemical compound O=C1C(C(CCCC1)C)N1C(N(C(=C1)CCCC)CC=1C=NC(=CC1)C1=C(C=CC=C1)C1=NN=NN1)=O ZFWCPVGZPZDQDX-UHFFFAOYSA-N 0.000 description 1
FANCTWJBNJHWGJ-UHFFFAOYSA-N O=C1C(C(CCCC1)CC)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound O=C1C(C(CCCC1)CC)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O FANCTWJBNJHWGJ-UHFFFAOYSA-N 0.000 description 1
YWTVVJISVBUUPY-UHFFFAOYSA-N O=C1C(C1C(C)C)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound O=C1C(C1C(C)C)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O YWTVVJISVBUUPY-UHFFFAOYSA-N 0.000 description 1
QJCCZNJHYWAOPL-UHFFFAOYSA-N O=C1C(C1CC)N1C(N(C(=C1)CCCC)CC=1C=NC=CC1C1=CC=C(C=C1)C1=NN=NN1)=O Chemical compound O=C1C(C1CC)N1C(N(C(=C1)CCCC)CC=1C=NC=CC1C1=CC=C(C=C1)C1=NN=NN1)=O QJCCZNJHYWAOPL-UHFFFAOYSA-N 0.000 description 1
RYFHDWHLVDUEGP-UHFFFAOYSA-N OC1C(CCCCC1)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound OC1C(CCCCC1)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O RYFHDWHLVDUEGP-UHFFFAOYSA-N 0.000 description 1
VRMSWDYYUISQSB-UHFFFAOYSA-N OC1C(CCCCCC1)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O Chemical compound OC1C(CCCCCC1)N1C(N(C(=C1)CCCC)CC1(CC=NC=C1)C1=CC(=CC=C1)C1=NN=NN1)=O VRMSWDYYUISQSB-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
241000577218 Phenes Species 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
229910052776 Thorium Inorganic materials 0.000 description 1
241000927721 Tritia Species 0.000 description 1
GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 description 1
108010004977 Vasopressins Proteins 0.000 description 1
102000002852 Vasopressins Human genes 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
RDEOBRVUTADVJO-UHFFFAOYSA-N acetic acid;1-oxidopyridin-1-ium Chemical compound CC(O)=O.[O-][N+]1=CC=CC=C1 RDEOBRVUTADVJO-UHFFFAOYSA-N 0.000 description 1
FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
230000009471 action Effects 0.000 description 1
230000004913 activation Effects 0.000 description 1
230000001919 adrenal effect Effects 0.000 description 1
IAJILQKETJEXLJ-RSJOWCBRSA-N aldehydo-D-galacturonic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-RSJOWCBRSA-N 0.000 description 1
IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
239000004855 amber Substances 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
229940030600 antihypertensive agent Drugs 0.000 description 1
210000002376 aorta thoracic Anatomy 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
238000013096 assay test Methods 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000012752 auxiliary agent Substances 0.000 description 1
OSJRGDBEYARHLX-UHFFFAOYSA-N azido(trimethyl)stannane Chemical compound [N-]=[N+]=[N-].C[Sn+](C)C OSJRGDBEYARHLX-UHFFFAOYSA-N 0.000 description 1
150000003851 azoles Chemical class 0.000 description 1
YTLQFZVCLXFFRK-UHFFFAOYSA-N bendazol Chemical class N=1C2=CC=CC=C2NC=1CC1=CC=CC=C1 YTLQFZVCLXFFRK-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
238000012925 biological evaluation Methods 0.000 description 1
ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
229940098773 bovine serum albumin Drugs 0.000 description 1
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
210000001715 carotid artery Anatomy 0.000 description 1
239000000969 carrier Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000004965 chloroalkyl group Chemical group 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 description 1
229960002023 chloroprocaine Drugs 0.000 description 1
KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
229960001231 choline Drugs 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
239000008139 complexing agent Substances 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
230000008602 contraction Effects 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
238000012937 correction Methods 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
239000013058 crude material Substances 0.000 description 1
XOVJAYNMQDTIJD-UHFFFAOYSA-N cyclopentobarbital Chemical compound C1CC=CC1C1(CC=C)C(=O)NC(=O)NC1=O XOVJAYNMQDTIJD-UHFFFAOYSA-N 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
125000004983 dialkoxyalkyl group Chemical group 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
229940043237 diethanolamine Drugs 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
230000002357 endometrial effect Effects 0.000 description 1
210000003038 endothelium Anatomy 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
210000001105 femoral artery Anatomy 0.000 description 1
210000003191 femoral vein Anatomy 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000000174 gluconic acid Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
229940097043 glucuronic acid Drugs 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
229960002897 heparin Drugs 0.000 description 1
229920000669 heparin Polymers 0.000 description 1
238000004896 high resolution mass spectrometry Methods 0.000 description 1
230000013632 homeostatic process Effects 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
230000000297 inotrophic effect Effects 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
210000002439 juxtaglomerular apparatus Anatomy 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
235000012245 magnesium oxide Nutrition 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Inorganic materials O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 1
230000008774 maternal effect Effects 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
229960003194 meglumine Drugs 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
229960002683 methohexital Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
LBBMOAOCCQOIAQ-UHFFFAOYSA-N methoxy(phenyl)borinic acid Chemical compound COB(O)C1=CC=CC=C1 LBBMOAOCCQOIAQ-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
210000002464 muscle smooth vascular Anatomy 0.000 description 1
230000002107 myocardial effect Effects 0.000 description 1
ACYBVNYNIZTUIL-UHFFFAOYSA-N n'-benzylethane-1,2-diamine Chemical compound NCCNCC1=CC=CC=C1 ACYBVNYNIZTUIL-UHFFFAOYSA-N 0.000 description 1
IWHZLXOVOHSRPU-UHFFFAOYSA-N n-tert-butyl-n-methylbenzamide Chemical compound CC(C)(C)N(C)C(=O)C1=CC=CC=C1 IWHZLXOVOHSRPU-UHFFFAOYSA-N 0.000 description 1
GZKMWSAXNHPVJH-UHFFFAOYSA-N n-tert-butyl-n-methylformamide Chemical compound O=CN(C)C(C)(C)C GZKMWSAXNHPVJH-UHFFFAOYSA-N 0.000 description 1
UPSWNZUMRHFAOC-UHFFFAOYSA-N n-tert-butyl-n-methylpyridine-2-carboxamide Chemical compound CC(C)(C)N(C)C(=O)C1=CC=CC=N1 UPSWNZUMRHFAOC-UHFFFAOYSA-N 0.000 description 1
RGEPBSUCDCONEO-UHFFFAOYSA-N n-tert-butyl-n-methylpyridine-3-carboxamide Chemical group CC(C)(C)N(C)C(=O)C1=CC=CN=C1 RGEPBSUCDCONEO-UHFFFAOYSA-N 0.000 description 1
XHQQXUFDSDWRHN-UHFFFAOYSA-N n-tert-butyl-n-methylpyridine-4-carboxamide Chemical compound CC(C)(C)N(C)C(=O)C1=CC=NC=C1 XHQQXUFDSDWRHN-UHFFFAOYSA-N 0.000 description 1
238000011587 new zealand white rabbit Methods 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
239000011713 pantothenic acid Substances 0.000 description 1
229940055726 pantothenic acid Drugs 0.000 description 1
235000019161 pantothenic acid Nutrition 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
230000010412 perfusion Effects 0.000 description 1
230000002688 persistence Effects 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical class O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
239000002953 phosphate buffered saline Substances 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000004926 polymethyl methacrylate Substances 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000343 potassium bisulfate Inorganic materials 0.000 description 1
230000002265 prevention Effects 0.000 description 1
238000009117 preventive therapy Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
239000000047 product Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
230000035485 pulse pressure Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
PSAYJRPASWETSH-UHFFFAOYSA-N pyridine-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CC=N1 PSAYJRPASWETSH-UHFFFAOYSA-N 0.000 description 1
ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical group ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
150000003254 radicals Chemical group 0.000 description 1
239000003087 receptor blocking agent Substances 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
PANBYUAFMMOFOV-UHFFFAOYSA-N sodium;sulfuric acid Chemical compound [Na].OS(O)(=O)=O PANBYUAFMMOFOV-UHFFFAOYSA-N 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229950000244 sulfanilic acid Drugs 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
210000002820 sympathetic nervous system Anatomy 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
229960003726 vasopressin Drugs 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/14—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 containing three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Heart & Thoracic Surgery (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

JP6509961A 1992-10-13 1993-06-16 循環系障害処置用ｎ−アリールヘテロアリールアルキル１−シクロアルキル−イミダゾール−２−オン化合物 Pending JPH08502285A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US95957592A	1992-10-13	1992-10-13
US07/959,575		1992-10-13
PCT/US1993/005601 WO1994008989A1 (fr)	1992-10-13	1993-06-16	Composes n-arylheteroarylalkyle 1-cycloalkyle-imidazole-2-one pour le traitement des maladies circulatoires

Publications (1)

Publication Number	Publication Date
JPH08502285A true JPH08502285A (ja)	1996-03-12

Family

ID=25502163

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP6509961A Pending JPH08502285A (ja)	1992-10-13	1993-06-16	循環系障害処置用ｎ−アリールヘテロアリールアルキル１−シクロアルキル−イミダゾール−２−オン化合物

Country Status (5)

Country	Link
EP (1)	EP0664803A1 (fr)
JP (1)	JPH08502285A (fr)
AU (1)	AU4533693A (fr)
CA (1)	CA2143192A1 (fr)
WO (1)	WO1994008989A1 (fr)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5087634A (en) *	1990-10-31	1992-02-11	G. D. Searle & Co.	N-substituted imidazol-2-one compounds for treatment of circulatory disorders
US5164403A (en) *	1991-04-05	1992-11-17	G. D. Searle & Co.	N-arylheteroarylalkyl imidazol-2-one compounds for treatment of circulatory disorders

1993
- 1993-06-16 EP EP93915307A patent/EP0664803A1/fr not_active Withdrawn
- 1993-06-16 AU AU45336/93A patent/AU4533693A/en not_active Abandoned
- 1993-06-16 WO PCT/US1993/005601 patent/WO1994008989A1/fr not_active Ceased
- 1993-06-16 JP JP6509961A patent/JPH08502285A/ja active Pending
- 1993-06-16 CA CA002143192A patent/CA2143192A1/fr not_active Abandoned

Also Published As

Publication number	Publication date
AU4533693A (en)	1994-05-09
CA2143192A1 (fr)	1994-04-28
EP0664803A1 (fr)	1995-08-02
WO1994008989A1 (fr)	1994-04-28

Publication	Publication Date	Title
US5451592A (en)	1995-09-19	Method of using N-arylheteroarylalkyl 1-heteroaryl-imidazol-2-one compounds for treatment of a glaucoma disorder
US5087634A (en)	1992-02-11	N-substituted imidazol-2-one compounds for treatment of circulatory disorders
US5451591A (en)	1995-09-19	Method of using 5-arylheteroarylalkyl-1,3 5-trisubstituted-1,24-triazole compounds for treatment of circulatory disorders
JPH07500579A (ja)	1995-01-19	イミダゾリル−アルケン酸
HU208537B (en)	1993-11-29	Process for producing imidazolyl-alkenic acids and pharmaceutical compositions containing them as active components
JPH03151379A (ja)	1991-06-27	置換５―［（テトラゾリル）アルケニル］イミダゾール
US5187271A (en)	1993-02-16	N-substituted (α-imidazolyl-toluyl) pyrrole compounds for treatment of circulatory disorders
JP3150149B2 (ja)	2001-03-26	循環器障害治療用の１−アリールヘテロアリールアルキル置換−１ｈ−１，２，４−トリアゾール化合物
JP3214856B2 (ja)	2001-10-02	イミダゾリル−アルケン酸
JPH08508249A (ja)	1996-09-03	循環系疾患の治療のための１−フェニル−イミダゾール−２−オンビフェニルメチル化合物
US5140036A (en)	1992-08-18	1,3,5-trisubstituted-1,2,4-triazole compounds for treatment of circulatory disorders
US5451597A (en)	1995-09-19	Treatment of circulatory disorders using n-substituted (α-imidazolyl-toluyl) pyrrole angiotensin II antagonists
US5594010A (en)	1997-01-14	Substituted monopyridylmethyl derivatives
US6492397B1 (en)	2002-12-10	N-arylheteroarylalkyl imidazol-2-one compounds for treatment of arteriosclerosis
EP0664802B1 (fr)	2000-03-15	Composes n-arylheteroarylalkyle 1-phenyle-imidazole-2-ones pour le traitement des maladies circulatoires
JPH08502285A (ja)	1996-03-12	循環系障害処置用ｎ−アリールヘテロアリールアルキル１−シクロアルキル−イミダゾール−２−オン化合物
US6008368A (en)	1999-12-28	Pharmaceutical compositions for treatment of circulatory disorders using N-substituted (α-imidazolyl-toluyl) pyrrole aniotensin II antagonists
US5238952A (en)	1993-08-24	N-substituted imidazol-2-one compounds for treatment of circulatory disorders
US5229406A (en)	1993-07-20	1,3,5-trisubstituted-1,2,4-triazole compounds for treatment of circulatory disorders