NZ571869A - Heterocyclic GPCR agonists - Google Patents

Info

Publication number

NZ571869A

NZ571869A NZ571869A NZ57186907A NZ571869A NZ 571869 A NZ571869 A NZ 571869A NZ 571869 A NZ571869 A NZ 571869A NZ 57186907 A NZ57186907 A NZ 57186907A NZ 571869 A NZ571869 A NZ 571869A

Authority

NZ

New Zealand

Prior art keywords

oxadiazol

piperidine

ethoxy

carboxylic acid

fluoro

Prior art date

2006-04-06

Links

• Espacenet
• Global Dossier
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• 125000000623 heterocyclic group Chemical group 0.000 title claims description 23
• 229940125633 GPCR agonist Drugs 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 205
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims abstract description 66
• NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 44
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 35
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 22
• -1 piperidine oxadiazole compound Chemical class 0.000 claims abstract description 21
• 125000001424 substituent group Chemical group 0.000 claims abstract description 13
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
• 150000003839 salts Chemical class 0.000 claims description 58
• 125000000217 alkyl group Chemical group 0.000 claims description 51
• 238000011282 treatment Methods 0.000 claims description 44
• 229910052717 sulfur Inorganic materials 0.000 claims description 27
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
• 125000005843 halogen group Chemical group 0.000 claims description 23
• 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 23
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• 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
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• 125000003118 aryl group Chemical group 0.000 claims description 10
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• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 9
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 7
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• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 7
• DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 claims description 6
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• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 5
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• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
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• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 claims description 3
• 125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 3
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• 239000003937 drug carrier Substances 0.000 claims description 3
• 150000002431 hydrogen Chemical group 0.000 claims description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
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• 239000002609 medium Substances 0.000 claims description 3
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
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• 206010022489 Insulin Resistance Diseases 0.000 claims description 2
• 208000017442 Retinal disease Diseases 0.000 claims description 2
• 206010038923 Retinopathy Diseases 0.000 claims description 2
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
• 230000002159 abnormal effect Effects 0.000 claims description 2
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• 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 claims 13
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• IPNNHZFPBGQLRG-CYBMUJFWSA-N 3-(3-fluoro-4-methylsulfanylphenyl)-5-[(1r)-1-[1-(3-propan-2-yl-1,2,4-oxadiazol-5-yl)piperidin-4-yl]oxyethyl]-1,2,4-oxadiazole Chemical compound C1=C(F)C(SC)=CC=C1C1=NOC([C@@H](C)OC2CCN(CC2)C=2ON=C(N=2)C(C)C)=N1 IPNNHZFPBGQLRG-CYBMUJFWSA-N 0.000 abstract 1
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