CN1197452A - 用于治疗动脉粥样硬化的氮杂环丁烷酮衍生物 - Google Patents

Info

Publication number

CN1197452A

CN1197452A CN96196661A CN96196661A CN1197452A CN 1197452 A CN1197452 A CN 1197452A CN 96196661 A CN96196661 A CN 96196661A CN 96196661 A CN96196661 A CN 96196661A CN 1197452 A CN1197452 A CN 1197452A

Authority

CN

China

Prior art keywords

oxo

azetidin

benzyl

diastereomer

hexyl

Prior art date

1995-07-01

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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• MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 title claims abstract description 10
• 201000001320 Atherosclerosis Diseases 0.000 title abstract description 11
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 110
• 125000003118 aryl group Chemical group 0.000 claims abstract description 55
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 52
• 239000001257 hydrogen Substances 0.000 claims abstract description 44
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 38
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 37
• 239000001301 oxygen Substances 0.000 claims abstract description 33
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 33
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 31
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 17
• 150000002367 halogens Chemical class 0.000 claims abstract description 17
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 12
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract 2
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 247
• 150000001875 compounds Chemical class 0.000 claims description 219
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 198
• -1 benzyl sulfinyl Chemical group 0.000 claims description 191
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 138
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 108
• NXFFJDQHYLNEJK-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1h-cyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)C)=CC(F)=CC=2C=2CCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 NXFFJDQHYLNEJK-UHFFFAOYSA-N 0.000 claims description 81
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 80
• 239000002585 base Substances 0.000 claims description 72
• 238000000034 method Methods 0.000 claims description 69
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 69
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 65
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 64
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 64
• RKOTXQYWCBGZLP-UHFFFAOYSA-N N-[(2,4-difluorophenyl)methyl]-2-ethyl-9-hydroxy-3-methoxy-1,8-dioxospiro[3H-pyrido[1,2-a]pyrazine-4,3'-oxolane]-7-carboxamide Chemical compound CCN1C(OC)C2(CCOC2)N2C=C(C(=O)NCC3=C(F)C=C(F)C=C3)C(=O)C(O)=C2C1=O RKOTXQYWCBGZLP-UHFFFAOYSA-N 0.000 claims description 33
• 239000002253 acid Substances 0.000 claims description 29
• 150000001412 amines Chemical class 0.000 claims description 28
• 229910052799 carbon Inorganic materials 0.000 claims description 27
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
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• 150000003839 salts Chemical class 0.000 claims description 19
• ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical compound CCCCCC(N)=O ALBYIUDWACNRRB-UHFFFAOYSA-N 0.000 claims description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
• 125000001118 alkylidene group Chemical group 0.000 claims description 11
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• 125000000623 heterocyclic group Chemical group 0.000 claims description 8
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• 125000002769 thiazolinyl group Chemical group 0.000 claims description 5
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• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
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• 239000002502 liposome Substances 0.000 claims description 4
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
• 210000001616 monocyte Anatomy 0.000 claims description 4
• 208000010125 myocardial infarction Diseases 0.000 claims description 4
• 201000003068 rheumatic fever Diseases 0.000 claims description 4
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• 206010002383 Angina Pectoris Diseases 0.000 claims description 3
• 206010003497 Asphyxia Diseases 0.000 claims description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
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• 235000021588 free fatty acids Nutrition 0.000 claims description 3
• AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims description 3
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• 201000000980 schizophrenia Diseases 0.000 claims description 3
• ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 3
• QHOINBKBMJLHPY-UHFFFAOYSA-N 2-chloroethyl formate Chemical compound ClCCOC=O QHOINBKBMJLHPY-UHFFFAOYSA-N 0.000 claims description 2
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
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• 239000012190 activator Substances 0.000 claims description 2
• 125000000304 alkynyl group Chemical group 0.000 claims description 2
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• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 13
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 7
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 3
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• NDAWQPHKPGPJEV-UHFFFAOYSA-N 4-benzylsulfinyl-1-[2-[6-(4-chlorophenyl)hexoxy]ethyl]azetidin-2-one Chemical compound C1=CC(Cl)=CC=C1CCCCCCOCCN1C(=O)CC1S(=O)CC1=CC=CC=C1 NDAWQPHKPGPJEV-UHFFFAOYSA-N 0.000 claims 2
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