CA2143192A1 - N-arylheteroarylalkyl-1-cycloalkylimidazol-2-ones, utiles pour le traitement des troubles de la circulation - Google Patents

N-arylheteroarylalkyl-1-cycloalkylimidazol-2-ones, utiles pour le traitement des troubles de la circulation

Info

Publication number: CA2143192A1
Authority: CA; Canada
Prior art keywords: methyl; butyl; phenyl; imidazol; pyridinyl
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.): Abandoned

Application number

CA002143192A

Other languages

English (en)

Inventor

David B. Reitz

Robert E. Manning

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

GD Searle LLC

Original Assignee

Individual

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

1994-04-28

1993-06-16 Application filed by Individual filed Critical Individual

1994-04-28 Publication of CA2143192A1 publication Critical patent/CA2143192A1/fr

Status Abandoned legal-status Critical Current

Links

-1 hydroxy, carboxyl Chemical group 0.000 claims abstract description 434
150000001875 compounds Chemical class 0.000 claims abstract description 271
150000003839 salts Chemical class 0.000 claims abstract description 118
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 73
125000001145 hydrido group Chemical group *[H] 0.000 claims abstract description 51
239000005557 antagonist Substances 0.000 claims abstract description 19
125000000217 alkyl group Chemical group 0.000 claims abstract description 17
206010020772 Hypertension Diseases 0.000 claims abstract description 14
230000002378 acidificating effect Effects 0.000 claims abstract description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
206010007559 Cardiac failure congestive Diseases 0.000 claims abstract description 5
206010019280 Heart failures Diseases 0.000 claims abstract description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 593
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 552
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 122
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 105
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 104
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 95
125000004043 oxo group Chemical group O=* 0.000 claims description 63
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 53
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 53
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 53
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 53
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 52
125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 51
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 50
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 49
238000000034 method Methods 0.000 claims description 23
125000001153 fluoro group Chemical group F* 0.000 claims description 20
239000000203 mixture Substances 0.000 claims description 18
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 14
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 13
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 13
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 12
229940123413 Angiotensin II antagonist Drugs 0.000 claims description 12
239000002333 angiotensin II receptor antagonist Substances 0.000 claims description 12
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 12
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 12
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 12
125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 12
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 11
125000005843 halogen group Chemical group 0.000 claims description 11
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 10
208000024172 Cardiovascular disease Diseases 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
125000003282 alkyl amino group Chemical group 0.000 claims description 5
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 5
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 description 4
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 description 4
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 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 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
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 4
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 4
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 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
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 4
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 description 4
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 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
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 4
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 description 4
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 description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
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 3
239000003085 diluting agent Substances 0.000 claims description 3
AMUSQYPDJYPSCI-UHFFFAOYSA-N 1-(2-acetyl-5-ethylcyclopentyl)-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)CCC1C(C)=O AMUSQYPDJYPSCI-UHFFFAOYSA-N 0.000 claims description 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 description 2
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 claims description 2
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 description 2
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 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
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 claims description 2
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 2
FXFASFKCSCUKTL-UHFFFAOYSA-N 4-butyl-1-(2-ethylcyclopentyl)-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)=CN1C1CCCC1CC FXFASFKCSCUKTL-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
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 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 claims description 2
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 description 2
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 description 2
208000010412 Glaucoma Diseases 0.000 claims description 2
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000003884 phenylalkyl group Chemical group 0.000 claims description 2
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 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 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 6
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 3
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 3
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 3
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 3
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WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
239000002953 phosphate buffered saline Substances 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
229960005235 piperonyl butoxide Drugs 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
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000009117 preventive therapy Methods 0.000 description 1
150000003140 primary amides Chemical class 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
230000008569 process Effects 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
239000000047 product Substances 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-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 compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 1
RVQZKNOMKUSGCI-UHFFFAOYSA-N pyridine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC=NC=C1 RVQZKNOMKUSGCI-UHFFFAOYSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
PFGWGEPQIUAZME-NXSMLHPHSA-N saralasin Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)CNC)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C)C(O)=O)C1=CC=C(O)C=C1 PFGWGEPQIUAZME-NXSMLHPHSA-N 0.000 description 1
229960004785 saralasin Drugs 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
235000015424 sodium 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
UISHOHGMISMAQN-UHFFFAOYSA-M sodium;2-[2-butyl-5-chloro-3-[(2-chlorophenyl)methyl]imidazol-4-yl]acetate Chemical compound [Na+].CCCCC1=NC(Cl)=C(CC([O-])=O)N1CC1=CC=CC=C1Cl UISHOHGMISMAQN-UHFFFAOYSA-M 0.000 description 1
230000009870 specific binding Effects 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
208000037804 stenosis Diseases 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000005720 sucrose Substances 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
230000002889 sympathetic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
XOIZCOKQILOFFG-UHFFFAOYSA-N tert-butyl n-[(2-methylpropan-2-yl)oxycarbonylcarbamoyl]carbamate Chemical class CC(C)(C)OC(=O)NC(=O)NC(=O)OC(C)(C)C XOIZCOKQILOFFG-UHFFFAOYSA-N 0.000 description 1
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 1
150000003852 triazoles Chemical group 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
230000002792 vascular Effects 0.000 description 1
239000005526 vasoconstrictor agent Substances 0.000 description 1
229960003726 vasopressin Drugs 0.000 description 1
238000005303 weighing Methods 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)

CA002143192A 1992-10-13 1993-06-16 N-arylheteroarylalkyl-1-cycloalkylimidazol-2-ones, utiles pour le traitement des troubles de la circulation Abandoned CA2143192A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US95957592A	1992-10-13	1992-10-13
US07/959,575		1992-10-13

Publications (1)

Publication Number	Publication Date
CA2143192A1 true CA2143192A1 (fr)	1994-04-28

Family

ID=25502163

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002143192A Abandoned CA2143192A1 (fr)	1992-10-13	1993-06-16	N-arylheteroarylalkyl-1-cycloalkylimidazol-2-ones, utiles pour le traitement des troubles de la circulation

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
JPH08502285A (ja)	1996-03-12
AU4533693A (en)	1994-05-09
EP0664803A1 (fr)	1995-08-02
WO1994008989A1 (fr)	1994-04-28

Legal Events

Date	Code	Title	Description
2001-06-18	FZDE	Discontinued
2023-05-26	FZDE	Discontinued	Effective date: 20010618

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
US5451593A (en)	1995-09-19	Method of using 5-arylheteroarylalkyl-1,3,5-trisubstituted-1,2,4-triazole compounds for treatment of a glaucoma disorder
US5187271A (en)	1993-02-16	N-substituted (α-imidazolyl-toluyl) pyrrole compounds for treatment of circulatory disorders
EP0508445B1 (fr)	1996-06-12	Composés de 1H-1,2,4-triazole 1-Arylhétéroarylalkyl substitués dans le traitement de troubles circulatoires
EP0690854B1 (fr)	2000-07-12	Composes 1-phenyle-imidazole-2-one biphenylmethyle destines au traitement des desordres circulatoires
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
EP0664802B1 (fr)	2000-03-15	Composes n-arylheteroarylalkyle 1-phenyle-imidazole-2-ones pour le traitement des maladies circulatoires
US6492397B1 (en)	2002-12-10	N-arylheteroarylalkyl imidazol-2-one compounds for treatment of arteriosclerosis
CA2143192A1 (fr)	1994-04-28	N-arylheteroarylalkyl-1-cycloalkylimidazol-2-ones, utiles pour le traitement des troubles de la circulation
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