BRPI0707338A2 - derivados de imidazol, composições, e métodos substituìdos de uso como inibidores de ptpase - Google Patents

Info

Publication number

BRPI0707338A2

BRPI0707338A2 BRPI0707338-0A BRPI0707338A BRPI0707338A2 BR PI0707338 A2 BRPI0707338 A2 BR PI0707338A2 BR PI0707338 A BRPI0707338 A BR PI0707338A BR PI0707338 A2 BRPI0707338 A2 BR PI0707338A2

Authority

BR

Brazil

Prior art keywords

phenyl

alkyl

dichloro

imidazol

formula

Prior art date

2006-01-30

Links

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• 239000003112 inhibitor Substances 0.000 title claims abstract description 21
• 238000000034 method Methods 0.000 title abstract description 387
• 239000000203 mixture Substances 0.000 title abstract description 102
• 150000002460 imidazoles Chemical class 0.000 title abstract description 8
• 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title abstract description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 220
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 31
• 201000010099 disease Diseases 0.000 claims abstract description 23
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 23
• 238000002360 preparation method Methods 0.000 claims abstract description 18
• 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 claims abstract description 10
• 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 claims abstract description 10
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 9
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims abstract description 8
• 230000001404 mediated effect Effects 0.000 claims abstract description 8
• 102000004169 proteins and genes Human genes 0.000 claims abstract description 7
• 108090000623 proteins and genes Proteins 0.000 claims abstract description 7
• 102000002727 Protein Tyrosine Phosphatase Human genes 0.000 claims abstract description 4
• 108020000494 protein-tyrosine phosphatase Proteins 0.000 claims abstract description 4
• -1 4,5-diazaindanyl Chemical group 0.000 claims description 411
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 177
• 125000000217 alkyl group Chemical group 0.000 claims description 123
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 90
• 229910052739 hydrogen Inorganic materials 0.000 claims description 84
• 239000001257 hydrogen Substances 0.000 claims description 79
• 229910052799 carbon Inorganic materials 0.000 claims description 60
• 239000002253 acid Substances 0.000 claims description 57
• 150000003839 salts Chemical class 0.000 claims description 56
• 125000003118 aryl group Chemical group 0.000 claims description 54
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
• 229910052757 nitrogen Chemical group 0.000 claims description 46
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 42
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
• 125000002947 alkylene group Chemical group 0.000 claims description 28
• 125000000623 heterocyclic group Chemical group 0.000 claims description 28
• 125000000304 alkynyl group Chemical group 0.000 claims description 27
• 229910052721 tungsten Inorganic materials 0.000 claims description 27
• 125000001072 heteroaryl group Chemical group 0.000 claims description 25
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 24
• 239000003814 drug Substances 0.000 claims description 24
• 125000003342 alkenyl group Chemical group 0.000 claims description 23
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 23
• 229910052727 yttrium Inorganic materials 0.000 claims description 22
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• 125000001424 substituent group Chemical group 0.000 claims description 21
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 20
• 125000001188 haloalkyl group Chemical group 0.000 claims description 19
• 238000004519 manufacturing process Methods 0.000 claims description 18
• 125000004432 carbon atom Chemical group C* 0.000 claims description 17
• 239000000460 chlorine Substances 0.000 claims description 15
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 14
• 125000005843 halogen group Chemical group 0.000 claims description 14
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 14
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 13
• 230000015572 biosynthetic process Effects 0.000 claims description 13
• 125000005842 heteroatom Chemical group 0.000 claims description 13
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 13
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
• 230000002401 inhibitory effect Effects 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• 125000005275 alkylenearyl group Chemical group 0.000 claims description 11
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
• 239000001301 oxygen Substances 0.000 claims description 11
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 11
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
• 229910052801 chlorine Inorganic materials 0.000 claims description 10
• 208000026278 immune system disease Diseases 0.000 claims description 10
• 239000012453 solvate Substances 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• 238000003786 synthesis reaction Methods 0.000 claims description 10
• 229940124597 therapeutic agent Drugs 0.000 claims description 10
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
• 239000011593 sulfur Chemical group 0.000 claims description 9
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
• 102000018997 Growth Hormone Human genes 0.000 claims description 8
• 108010051696 Growth Hormone Proteins 0.000 claims description 8
• 125000004450 alkenylene group Chemical group 0.000 claims description 8
• 125000004429 atom Chemical group 0.000 claims description 8
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 8
• 239000000122 growth hormone Substances 0.000 claims description 8
• 229940002612 prodrug Drugs 0.000 claims description 8
• 239000000651 prodrug Substances 0.000 claims description 8
• 229910052702 rhenium Inorganic materials 0.000 claims description 8
• 102000004877 Insulin Human genes 0.000 claims description 7
• 108090001061 Insulin Proteins 0.000 claims description 7
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 7
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
• 150000002367 halogens Chemical class 0.000 claims description 7
• 229940088597 hormone Drugs 0.000 claims description 7
• 239000005556 hormone Substances 0.000 claims description 7
• 229940125396 insulin Drugs 0.000 claims description 7
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 6
• 208000024827 Alzheimer disease Diseases 0.000 claims description 6
• 206010028980 Neoplasm Diseases 0.000 claims description 6
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
• 150000002500 ions Chemical class 0.000 claims description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
• YQDGQEKUTLYWJU-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinoline Chemical compound C1=CC=C2CCCCC2=N1 YQDGQEKUTLYWJU-UHFFFAOYSA-N 0.000 claims description 5
• 208000030507 AIDS Diseases 0.000 claims description 5
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• 102000004127 Cytokines Human genes 0.000 claims description 5
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• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
• 208000002705 Glucose Intolerance Diseases 0.000 claims description 5
• 206010018429 Glucose tolerance impaired Diseases 0.000 claims description 5
• 125000005218 alkyleneheteroaryl group Chemical group 0.000 claims description 5
• 208000026935 allergic disease Diseases 0.000 claims description 5
• XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 claims description 5
• 201000011510 cancer Diseases 0.000 claims description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• 239000011737 fluorine Substances 0.000 claims description 5
• 229910052731 fluorine Inorganic materials 0.000 claims description 5
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 5
• 208000027866 inflammatory disease Diseases 0.000 claims description 5
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• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 5
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
• 101710198884 GATA-type zinc finger protein 1 Proteins 0.000 claims description 4
• DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 claims description 4
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• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 claims description 3
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