OA11848A - Inhibitors of IMPDH enzyme. - Google Patents

Info

Publication number

OA11848A

OA11848A OA1200100235A OA1200100235A OA11848A OA 11848 A OA11848 A OA 11848A OA 1200100235 A OA1200100235 A OA 1200100235A OA 1200100235 A OA1200100235 A OA 1200100235A OA 11848 A OA11848 A OA 11848A

Authority

OA

OAPI

Prior art keywords

straight

alkynyl

branched alkyl

alkenyl

compound

Prior art date

1999-03-19

Links

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• 101710200424 Inosine-5'-monophosphate dehydrogenase Proteins 0.000 title claims abstract description 39
• 108090000790 Enzymes Proteins 0.000 title abstract description 13
• 102000004190 Enzymes Human genes 0.000 title abstract description 13
• 239000003112 inhibitor Substances 0.000 title description 17
• 150000001875 compounds Chemical class 0.000 claims abstract description 93
• 238000000034 method Methods 0.000 claims abstract description 36
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 20
• 230000001404 mediated effect Effects 0.000 claims abstract description 7
• 239000000203 mixture Substances 0.000 claims description 69
• 125000000217 alkyl group Chemical group 0.000 claims description 42
• 125000000304 alkynyl group Chemical group 0.000 claims description 41
• 125000003342 alkenyl group Chemical group 0.000 claims description 37
• 241000124008 Mammalia Species 0.000 claims description 33
• 239000003795 chemical substances by application Substances 0.000 claims description 25
• -1 3-tetrahydrofuranyl Chemical group 0.000 claims description 24
• 229910052739 hydrogen Inorganic materials 0.000 claims description 23
• 239000001257 hydrogen Substances 0.000 claims description 22
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
• 201000010099 disease Diseases 0.000 claims description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
• 206010028980 Neoplasm Diseases 0.000 claims description 11
• 239000003443 antiviral agent Substances 0.000 claims description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
• 239000002552 dosage form Substances 0.000 claims description 10
• RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims description 10
• 241000700605 Viruses Species 0.000 claims description 9
• 239000003018 immunosuppressive agent Substances 0.000 claims description 9
• 230000003612 virological effect Effects 0.000 claims description 9
• 239000002260 anti-inflammatory agent Substances 0.000 claims description 8
• 229940121363 anti-inflammatory agent Drugs 0.000 claims description 8
• 229960003444 immunosuppressant agent Drugs 0.000 claims description 8
• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
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• 239000002246 antineoplastic agent Substances 0.000 claims description 7
• 125000004122 cyclic group Chemical group 0.000 claims description 7
• 125000005843 halogen group Chemical group 0.000 claims description 7
• 125000006413 ring segment Chemical group 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
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• 229940002612 prodrug Drugs 0.000 claims description 6
• 239000000651 prodrug Substances 0.000 claims description 6
• 229940121375 antifungal agent Drugs 0.000 claims description 5
• 239000003429 antifungal agent Substances 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 125000000623 heterocyclic group Chemical group 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
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• 150000002431 hydrogen Chemical group 0.000 claims description 4
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• 125000002950 monocyclic group Chemical group 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
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• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
• 230000036262 stenosis Effects 0.000 claims description 3
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• XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 2
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
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• 241000702263 Reovirus sp. Species 0.000 claims description 2
• 241000711975 Vesicular stomatitis virus Species 0.000 claims description 2
• 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 2
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• 230000003494 hepatotrophic effect Effects 0.000 claims description 2
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• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 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 2
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• 201000005404 rubella Diseases 0.000 claims description 2
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
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• 241001529453 unidentified herpesvirus Species 0.000 claims description 2
• 241001430294 unidentified retrovirus Species 0.000 claims description 2
• SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 5
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• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
• 206010014599 encephalitis Diseases 0.000 claims 1
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
• 229960004717 insulin aspart Drugs 0.000 claims 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
• VOMXSOIBEJBQNF-UTTRGDHVSA-N novorapid Chemical compound C([C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CS)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CS)NC(=O)[C@H](CS)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(O)=O)C1=CC=C(O)C=C1.C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CS)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CS)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CN=CN1 VOMXSOIBEJBQNF-UTTRGDHVSA-N 0.000 claims 1
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