BRPI0619536A2 - compostos imidazolil bis-heterocìclicos - Google Patents

Info

Publication number

BRPI0619536A2

BRPI0619536A2 BRPI0619536-9A BRPI0619536A BRPI0619536A2 BR PI0619536 A2 BRPI0619536 A2 BR PI0619536A2 BR PI0619536 A BRPI0619536 A BR PI0619536A BR PI0619536 A2 BRPI0619536 A2 BR PI0619536A2

Authority

BR

Brazil

Prior art keywords

substituted

unsubstituted

alkyl

alkoxy

hydrogen

Prior art date

2005-12-09

Links

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• 125000002883 imidazolyl group Chemical group 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 129
• 238000004519 manufacturing process Methods 0.000 claims abstract description 8
• 239000003814 drug Substances 0.000 claims abstract description 6
• -1 6,7-dihydro-5H-pyrrolo [1,2- c] imidazol-7-yl Chemical group 0.000 claims description 86
• 125000000623 heterocyclic group Chemical group 0.000 claims description 58
• 125000003545 alkoxy group Chemical group 0.000 claims description 50
• 229910052736 halogen Inorganic materials 0.000 claims description 48
• 150000002367 halogens Chemical class 0.000 claims description 47
• 229910052739 hydrogen Inorganic materials 0.000 claims description 45
• 239000001257 hydrogen Substances 0.000 claims description 45
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 44
• 150000003839 salts Chemical class 0.000 claims description 44
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 43
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 35
• 229910052805 deuterium Inorganic materials 0.000 claims description 35
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 33
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 31
• JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 30
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 29
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 27
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 23
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
• 125000004665 trialkylsilyl group Chemical group 0.000 claims description 23
• 125000003118 aryl group Chemical group 0.000 claims description 22
• 125000001424 substituent group Chemical group 0.000 claims description 22
• 125000003107 substituted aryl group Chemical group 0.000 claims description 22
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
• 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 17
• 125000004043 oxo group Chemical group O=* 0.000 claims description 16
• ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentaoxide Chemical compound [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 claims description 15
• 229960000890 hydrocortisone Drugs 0.000 claims description 15
• 150000002431 hydrogen Chemical class 0.000 claims description 14
• 238000000034 method Methods 0.000 claims description 12
• 230000000694 effects Effects 0.000 claims description 10
• 125000004414 alkyl thio group Chemical group 0.000 claims description 9
• 125000004432 carbon atom Chemical group C* 0.000 claims description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
• 125000004076 pyridyl group Chemical group 0.000 claims description 9
• 239000004480 active ingredient Substances 0.000 claims description 8
• 125000000217 alkyl group Chemical group 0.000 claims description 7
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• 201000009395 primary hyperaldosteronism Diseases 0.000 claims description 7
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 6
• 229910052757 nitrogen Inorganic materials 0.000 claims description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
• 125000001624 naphthyl group Chemical group 0.000 claims description 5
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• 230000036772 blood pressure Effects 0.000 claims description 4
• 125000001041 indolyl group Chemical group 0.000 claims description 4
• 230000000297 inotrophic effect Effects 0.000 claims description 4
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 3
• 125000004429 atom Chemical group 0.000 claims description 3
• 239000004305 biphenyl Substances 0.000 claims description 3
• 235000010290 biphenyl Nutrition 0.000 claims description 3
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 3
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
• 125000004532 benzofuran-3-yl group Chemical group O1C=C(C2=C1C=CC=C2)* 0.000 claims description 2
• 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 claims description 2
• 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 2
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
• 230000001575 pathological effect Effects 0.000 claims 2
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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
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