CN1344270A - 作为趋化因子受体调节剂的官能化杂环 - Google Patents

Info

Publication number

CN1344270A

CN1344270A CN99816475A CN99816475A CN1344270A CN 1344270 A CN1344270 A CN 1344270A CN 99816475 A CN99816475 A CN 99816475A CN 99816475 A CN99816475 A CN 99816475A CN 1344270 A CN1344270 A CN 1344270A

Authority

CN

China

Prior art keywords

methyl

quinolizine

chromene

decahydro

pyrrolo

Prior art date

1999-01-13

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Pending

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• 102000009410 Chemokine receptor Human genes 0.000 title abstract description 10
• 108050000299 Chemokine receptor Proteins 0.000 title abstract description 10
• 125000000623 heterocyclic group Chemical group 0.000 title abstract description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 125
• 230000000694 effects Effects 0.000 claims abstract description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
• 230000002265 prevention Effects 0.000 claims abstract description 6
• QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 claims description 720
• KQFZOWUXULRDDS-UHFFFAOYSA-N 4h-quinolizine-1-carboxylic acid Chemical compound C1=CC=CN2CC=CC(C(=O)O)=C21 KQFZOWUXULRDDS-UHFFFAOYSA-N 0.000 claims description 668
• -1 N-oxide compound Chemical class 0.000 claims description 413
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 273
• 238000000034 method Methods 0.000 claims description 174
• 125000004494 ethyl ester group Chemical group 0.000 claims description 149
• 208000030507 AIDS Diseases 0.000 claims description 75
• 125000000217 alkyl group Chemical group 0.000 claims description 60
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 57
• 150000002148 esters Chemical class 0.000 claims description 43
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
• 150000004702 methyl esters Chemical class 0.000 claims description 37
• 229910052757 nitrogen Inorganic materials 0.000 claims description 37
• 150000003839 salts Chemical class 0.000 claims description 34
• 239000002253 acid Substances 0.000 claims description 30
• 238000002360 preparation method Methods 0.000 claims description 27
• 125000003118 aryl group Chemical group 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
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 24
• 150000008065 acid anhydrides Chemical class 0.000 claims description 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 19
• 102100035875 C-C chemokine receptor type 5 Human genes 0.000 claims description 18
• 101710149870 C-C chemokine receptor type 5 Proteins 0.000 claims description 18
• BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 18
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
• 125000004429 atom Chemical group 0.000 claims description 15
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 14
• QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims description 13
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• GDRVFDDBLLKWRI-UHFFFAOYSA-N 4H-quinolizine Chemical compound C1=CC=CN2CC=CC=C21 GDRVFDDBLLKWRI-UHFFFAOYSA-N 0.000 claims description 11
• DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 229910052736 halogen Inorganic materials 0.000 claims description 8
• 150000002367 halogens Chemical class 0.000 claims description 8
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• 239000001301 oxygen Substances 0.000 claims description 7
• 239000004593 Epoxy Substances 0.000 claims description 6
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
• DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 6
• 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 5
• IAKNLKLKKBPMHN-UHFFFAOYSA-N 4h-quinolizine-2-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CCN21 IAKNLKLKKBPMHN-UHFFFAOYSA-N 0.000 claims description 5
• QSSJZLPUHJDYKF-UHFFFAOYSA-N methyl 4-methylbenzoate Chemical class COC(=O)C1=CC=C(C)C=C1 QSSJZLPUHJDYKF-UHFFFAOYSA-N 0.000 claims description 5
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 5
• UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 4
• SZTRCMOSUUQMBM-UHFFFAOYSA-N 2h-azepine Chemical class C1C=CC=CC=N1 SZTRCMOSUUQMBM-UHFFFAOYSA-N 0.000 claims description 4
• WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 claims description 4
• 150000001538 azepines Chemical class 0.000 claims description 4
• 102000005962 receptors Human genes 0.000 claims description 4
• 108020003175 receptors Proteins 0.000 claims description 4
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• CNSFNWDNZRTKQN-UHFFFAOYSA-N 4h-quinolizine-1-carbaldehyde Chemical compound C1=CC=CN2CC=CC(C=O)=C21 CNSFNWDNZRTKQN-UHFFFAOYSA-N 0.000 claims description 3
• DXCSVLKTQJOVQZ-UHFFFAOYSA-N C1(=CC=CC=C1)C#CCOC(C1(CC(C(=O)O)=CC=C1)C)=O Chemical compound C1(=CC=CC=C1)C#CCOC(C1(CC(C(=O)O)=CC=C1)C)=O DXCSVLKTQJOVQZ-UHFFFAOYSA-N 0.000 claims description 3
• AYDQIZKZTQHYIY-UHFFFAOYSA-N OC(=O)C1(C)CC(C(O)=O)=CC=C1 Chemical compound OC(=O)C1(C)CC(C(O)=O)=CC=C1 AYDQIZKZTQHYIY-UHFFFAOYSA-N 0.000 claims description 3
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
• 125000002252 acyl group Chemical group 0.000 claims description 3
• 235000010290 biphenyl Nutrition 0.000 claims description 3
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 3
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• PZQSQRCNMZGWFT-QXMHVHEDSA-N propan-2-yl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC(C)C PZQSQRCNMZGWFT-QXMHVHEDSA-N 0.000 claims description 3
• 150000003250 quinolizines Chemical class 0.000 claims description 3
• HUBFMENNWDPKMA-UHFFFAOYSA-N 2-(4H-quinolizin-1-yl)acetic acid Chemical compound C=1(C=CCN2C=CC=CC=12)CC(=O)O HUBFMENNWDPKMA-UHFFFAOYSA-N 0.000 claims description 2
• MRPJPNSLXVZHTL-UHFFFAOYSA-N C(OC1=CC=CC=C1)(=O)Cl.CC1(C(=O)O)CC(C(=O)O)=CC=C1 Chemical compound C(OC1=CC=CC=C1)(=O)Cl.CC1(C(=O)O)CC(C(=O)O)=CC=C1 MRPJPNSLXVZHTL-UHFFFAOYSA-N 0.000 claims description 2
• 102000019034 Chemokines Human genes 0.000 claims description 2
• 108010012236 Chemokines Proteins 0.000 claims description 2
• HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 claims description 2
• 208000027866 inflammatory disease Diseases 0.000 claims description 2
• 150000004880 oxines Chemical class 0.000 claims 4
• 241000124008 Mammalia Species 0.000 claims 1
• 239000003085 diluting agent Substances 0.000 claims 1
• 239000000546 pharmaceutical excipient Substances 0.000 claims 1
• 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
• 241000725303 Human immunodeficiency virus Species 0.000 abstract description 42
• 239000000543 intermediate Substances 0.000 abstract description 13
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 350
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 274
• 239000000243 solution Substances 0.000 description 185
• 239000007787 solid Substances 0.000 description 183
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 153
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 149
• 238000005160 1H NMR spectroscopy Methods 0.000 description 143
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 129
• 235000019439 ethyl acetate Nutrition 0.000 description 126
• 239000000203 mixture Substances 0.000 description 118
• 238000010205 computational analysis Methods 0.000 description 114
• 239000000047 product Substances 0.000 description 111
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• 239000011541 reaction mixture Substances 0.000 description 88
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 87
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 69
• 239000012043 crude product Substances 0.000 description 67
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 66
• 239000000741 silica gel Substances 0.000 description 66
• 229910002027 silica gel Inorganic materials 0.000 description 66
• 229960001866 silicon dioxide Drugs 0.000 description 66
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 64
• 235000019441 ethanol Nutrition 0.000 description 57
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
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• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 49
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• APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 37
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• 235000011152 sodium sulphate Nutrition 0.000 description 35
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