LV13338B - New substituted azetidinones as anti-inflammatory and antidegenerative agents - Google Patents

Info

Publication number

LV13338B

LV13338B LVP-05-69A LV050069A LV13338B LV 13338 B LV13338 B LV 13338B LV 050069 A LV050069 A LV 050069A LV 13338 B LV13338 B LV 13338B

Authority

LV

Latvia

Prior art keywords

alkyl

hydrogen

substituted

ch2ch2n

mono

Prior art date

1992-10-27

Links

• Espacenet
• Global Dossier
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• MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 title abstract description 13
• 230000003110 anti-inflammatory effect Effects 0.000 title abstract description 9
• 230000001796 anti-degenerative effect Effects 0.000 title abstract description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 131
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
• -1 morpholinecarbonylphenyl Chemical group 0.000 claims description 205
• 239000001257 hydrogen Substances 0.000 claims description 89
• 229910052739 hydrogen Inorganic materials 0.000 claims description 89
• 125000000217 alkyl group Chemical group 0.000 claims description 71
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 67
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 49
• 125000004429 atom Chemical group 0.000 claims description 45
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 40
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
• 125000005842 heteroatom Chemical group 0.000 claims description 27
• 125000001424 substituent group Chemical group 0.000 claims description 27
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 26
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
• 125000002950 monocyclic group Chemical group 0.000 claims description 25
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
• 150000002431 hydrogen Chemical group 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 21
• 229920006395 saturated elastomer Polymers 0.000 claims description 20
• 125000005843 halogen group Chemical group 0.000 claims description 19
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 16
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 14
• 125000002883 imidazolyl group Chemical group 0.000 claims description 12
• 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 12
• 125000003545 alkoxy group Chemical group 0.000 claims description 11
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
• 125000001425 triazolyl group Chemical group 0.000 claims description 11
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
• 125000005518 carboxamido group Chemical group 0.000 claims description 10
• 150000003839 salts Chemical class 0.000 claims description 10
• 125000004432 carbon atom Chemical group C* 0.000 claims description 9
• 125000001072 heteroaryl group Chemical group 0.000 claims description 9
• 125000004193 piperazinyl group Chemical group 0.000 claims description 9
• 125000003386 piperidinyl group Chemical group 0.000 claims description 9
• 125000004076 pyridyl group Chemical group 0.000 claims description 9
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
• 230000002401 inhibitory effect Effects 0.000 claims description 6
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
• 125000002393 azetidinyl group Chemical group 0.000 claims description 5
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 5
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 4
• 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 4
• 101000851058 Homo sapiens Neutrophil elastase Proteins 0.000 claims description 4
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• 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 claims description 4
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 4
• 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 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• 125000006202 diisopropylaminoethyl group Chemical group [H]C([H])([H])C([H])(N(C([H])([H])C([H])([H])*)C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
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• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
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• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
• 125000006183 2,4-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])*)C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 3
• 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 3
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• 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
• 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims description 2
• 150000001602 bicycloalkyls Chemical group 0.000 claims description 2
• 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims description 2
• 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 claims description 2
• 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 claims description 2
• 125000000286 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 2
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
• 125000003277 amino group Chemical group 0.000 claims 18
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 15
• 229910052736 halogen Inorganic materials 0.000 claims 8
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• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 7
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
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