MXPA05002701A - Agentes antibacterianos de tetrahidroquinolina triciclicos. - Google Patents

Info

Publication number

MXPA05002701A

MXPA05002701A MXPA05002701A MXPA05002701A MXPA05002701A MX PA05002701 A MXPA05002701 A MX PA05002701A MX PA05002701 A MXPA05002701 A MX PA05002701A MX PA05002701 A MXPA05002701 A MX PA05002701A MX PA05002701 A MXPA05002701 A MX PA05002701A

Authority

MX

Mexico

Prior art keywords

tetrahydro

oxazino

quinolin

dimethyl

optionally substituted

Prior art date

2002-10-07

Links

• Espacenet
• Global Dossier
• Discuss

• LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 title abstract description 6
• 239000003242 anti bacterial agent Substances 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 141
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
• 239000000203 mixture Substances 0.000 claims description 92
• 125000000217 alkyl group Chemical group 0.000 claims description 56
• 238000002360 preparation method Methods 0.000 claims description 55
• -1 piperazino Chemical group 0.000 claims description 53
• 125000005843 halogen group Chemical group 0.000 claims description 37
• 125000003003 spiro group Chemical group 0.000 claims description 34
• 125000001072 heteroaryl group Chemical group 0.000 claims description 30
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
• 125000003118 aryl group Chemical group 0.000 claims description 27
• 238000000034 method Methods 0.000 claims description 27
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
• 150000003839 salts Chemical class 0.000 claims description 22
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 21
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 21
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 19
• 125000001424 substituent group Chemical group 0.000 claims description 18
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 15
• 229920006395 saturated elastomer Polymers 0.000 claims description 15
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 11
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
• 101100212791 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) YBL068W-A gene Proteins 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 150000001412 amines Chemical class 0.000 claims description 9
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 9
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
• 229910052739 hydrogen Inorganic materials 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• 239000011593 sulfur Substances 0.000 claims description 7
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• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• 125000002950 monocyclic group Chemical group 0.000 claims description 6
• 125000006413 ring segment Chemical group 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
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• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
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• 125000002619 bicyclic group Chemical group 0.000 claims description 4
• 229910052736 halogen Inorganic materials 0.000 claims description 4
• BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 3
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• 150000002367 halogens Chemical class 0.000 claims description 3
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• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
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• 235000001258 Cinchona calisaya Nutrition 0.000 claims description 2
• CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical compound [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 claims description 2
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• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
• LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims description 2
• HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical group O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 claims description 2
• LOGSONSNCYTHPS-UHFFFAOYSA-N cyclopentane-1,3-dione Chemical group O=C1CCC(=O)C1 LOGSONSNCYTHPS-UHFFFAOYSA-N 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 208000015181 infectious disease Diseases 0.000 claims description 2
• JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
• 229960000948 quinine Drugs 0.000 claims description 2
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
• 230000002194 synthesizing effect Effects 0.000 claims description 2
• WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical compound C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 claims 1
• 229960001653 citalopram Drugs 0.000 claims 1
• 230000000813 microbial effect Effects 0.000 claims 1
• 150000004682 monohydrates Chemical class 0.000 claims 1
• 239000012454 non-polar solvent Substances 0.000 claims 1
• 125000004043 oxo group Chemical group O=* 0.000 claims 1
• 239000003586 protic polar solvent Substances 0.000 claims 1
• LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims 1
• 230000008707 rearrangement Effects 0.000 claims 1
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• 244000052769 pathogen Species 0.000 abstract description 4
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 121
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• 238000005481 NMR spectroscopy Methods 0.000 description 74
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