JPH04502322A - 抗アテローム性動脈硬化症性および抗血栓性１―ベンゾピラン―４―オン類および２―アミノ―１，３―ベンゾオキサジン―４―オン類 - Google Patents

抗アテローム性動脈硬化症性および抗血栓性１―ベンゾピラン―４―オン類および２―アミノ―１，３―ベンゾオキサジン―４―オン類

Info

Publication number: JPH04502322A
Authority: JP; Japan
Prior art keywords: morpholinyl; benzopyran; methyl; alkyl; phenyl
Prior art date: 1988-12-21
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

Application number

JP2501394A

Other languages

English (en)

Japanese (ja)

Inventor

ガミル，ロナルド・ビー

ジャッジ，トーマス・エム

モリス，ジョエル

Original Assignee

ジ・アップジョン・カンパニー

Priority date (The priority date 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 date listed.)

1988-12-21

Filing date

1989-12-15

Publication date

1992-04-23

1989-12-15 Application filed by ジ・アップジョン・カンパニー filed Critical ジ・アップジョン・カンパニー

1992-04-23 Publication of JPH04502322A publication Critical patent/JPH04502322A/ja

Status Pending legal-status Critical Current

Links

230000000879 anti-atherosclerotic effect Effects 0.000 title description 12
150000004777 chromones Chemical class 0.000 title description 4
239000003146 anticoagulant agent Substances 0.000 title description 3
VRRIKQMIAFHSNY-UHFFFAOYSA-N 2-amino-1,3-benzoxazin-4-one Chemical class C1=CC=C2OC(N)=NC(=O)C2=C1 VRRIKQMIAFHSNY-UHFFFAOYSA-N 0.000 title description 2
230000002785 anti-thrombosis Effects 0.000 title description 2
125000005843 halogen group Chemical group 0.000 claims description 175
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 159
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 156
-1 -(CH2)qOH Chemical group 0.000 claims description 128
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 112
125000000217 alkyl group Chemical group 0.000 claims description 101
125000003545 alkoxy group Chemical group 0.000 claims description 70
150000001875 compounds Chemical class 0.000 claims description 68
229910052739 hydrogen Inorganic materials 0.000 claims description 59
239000001257 hydrogen Substances 0.000 claims description 50
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 46
OTAFHZMPRISVEM-UHFFFAOYSA-N benzo-gamma-pyrone Natural products C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 claims description 43
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 35
150000002431 hydrogen Chemical class 0.000 claims description 34
238000000034 method Methods 0.000 claims description 34
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 30
229910052757 nitrogen Inorganic materials 0.000 claims description 25
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 21
XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical group FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims description 19
150000001412 amines Chemical group 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 19
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims description 17
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 17
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 16
125000000623 heterocyclic group Chemical group 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 14
125000001624 naphthyl group Chemical group 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 12
229920006395 saturated elastomer Polymers 0.000 claims description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
239000000126 substance Substances 0.000 claims description 11
201000001320 Atherosclerosis Diseases 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 10
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
125000004076 pyridyl group Chemical group 0.000 claims description 10
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 9
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 9
125000001153 fluoro group Chemical group F* 0.000 claims description 8
125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 claims description 8
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 8
QNFWERYZJLBANZ-UHFFFAOYSA-N 2-morpholin-4-ylchromen-4-one Chemical compound O1C2=CC=CC=C2C(=O)C=C1N1CCOCC1 QNFWERYZJLBANZ-UHFFFAOYSA-N 0.000 claims description 7
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 7
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 7
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
KQOATKAFTRNONV-UHFFFAOYSA-N oxolan-2-amine Chemical compound NC1CCCO1 KQOATKAFTRNONV-UHFFFAOYSA-N 0.000 claims description 7
DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical compound OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 claims description 7
150000001204 N-oxides Chemical class 0.000 claims description 6
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
101100108853 Mus musculus Anp32e gene Proteins 0.000 claims description 5
ZVGFPYKCWIGTEM-UHFFFAOYSA-N O1C=CC(=O)C2=CC(N(C(O)=O)N(C)C)=CC=C21 Chemical compound O1C=CC(=O)C2=CC(N(C(O)=O)N(C)C)=CC=C21 ZVGFPYKCWIGTEM-UHFFFAOYSA-N 0.000 claims description 5
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
125000003373 pyrazinyl group Chemical group 0.000 claims description 5
FXHRAKUEZPSMLJ-UHFFFAOYSA-N 1-methyl-1,4-diazepane Chemical compound CN1CCCNCC1 FXHRAKUEZPSMLJ-UHFFFAOYSA-N 0.000 claims description 4
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 claims description 4
MDYDGUOQFUQOGE-UHFFFAOYSA-N 2-methylpropanethioic acid S-[7-oxo-7-[(4-phenyl-2-thiazolyl)amino]heptyl] ester Chemical compound S1C(NC(=O)CCCCCCSC(=O)C(C)C)=NC(C=2C=CC=CC=2)=C1 MDYDGUOQFUQOGE-UHFFFAOYSA-N 0.000 claims description 4
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
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 4
230000002265 prevention Effects 0.000 claims description 4
PAEBEUZTAPIOIO-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(1-methyl-3-oxo-2-phenyl-5-propan-2-ylpyrazol-4-yl)urea Chemical compound O=C1N(C=2C=CC=CC=2)N(C)C(C(C)C)=C1NC(=O)NC1=CC=C(Cl)C=C1 PAEBEUZTAPIOIO-UHFFFAOYSA-N 0.000 claims description 3
IKYWHIFAOVPXAQ-UHFFFAOYSA-N 2-(8-methyl-2-morpholin-4-yl-4-oxochromen-7-yl)oxy-n-pyridin-3-ylacetamide Chemical compound C1=CC(C(C=C(O2)N3CCOCC3)=O)=C2C(C)=C1OCC(=O)NC1=CC=CN=C1 IKYWHIFAOVPXAQ-UHFFFAOYSA-N 0.000 claims description 3
HGMBPBPNWJNTTL-UHFFFAOYSA-N 2-morpholin-4-yl-4-oxochromene-8-carbaldehyde Chemical compound O=CC1=CC=CC(C(C=2)=O)=C1OC=2N1CCOCC1 HGMBPBPNWJNTTL-UHFFFAOYSA-N 0.000 claims description 3
IFBVOPSOAQSXPU-UHFFFAOYSA-N 2-morpholin-4-yl-8-prop-1-enylchromen-4-one Chemical compound CC=CC1=CC=CC(C(C=2)=O)=C1OC=2N1CCOCC1 IFBVOPSOAQSXPU-UHFFFAOYSA-N 0.000 claims description 3
UMQLNVCIFMTIAZ-UHFFFAOYSA-N 4-[(2-morpholin-4-yl-4-oxochromen-8-yl)oxymethyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1COC1=CC=CC2=C1OC(N1CCOCC1)=CC2=O UMQLNVCIFMTIAZ-UHFFFAOYSA-N 0.000 claims description 3
XLLVCULLOGKYOO-UHFFFAOYSA-N 4-methoxy-n-[4-[(4-methoxyphenyl)sulfonylamino]naphthalen-1-yl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC(C1=CC=CC=C11)=CC=C1NS(=O)(=O)C1=CC=C(OC)C=C1 XLLVCULLOGKYOO-UHFFFAOYSA-N 0.000 claims description 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
MLXUHKKUWDAYQP-UHFFFAOYSA-N 8-methyl-7-[(1-methylpiperidin-3-yl)methoxy]-2-morpholin-4-ylchromen-4-one Chemical compound C1N(C)CCCC1COC1=CC=C2C(=O)C=C(N3CCOCC3)OC2=C1C MLXUHKKUWDAYQP-UHFFFAOYSA-N 0.000 claims description 3
101100221809 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cpd-7 gene Proteins 0.000 claims description 3
241000577218 Phenes Species 0.000 claims description 3
XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
229960003966 nicotinamide Drugs 0.000 claims description 3
235000005152 nicotinamide Nutrition 0.000 claims description 3
239000011570 nicotinamide Substances 0.000 claims description 3
DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 3
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 claims description 3
229910052727 yttrium Inorganic materials 0.000 claims description 3
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
RXSQQZJWJXKFMK-UHFFFAOYSA-N 8-methyl-2-morpholin-4-yl-1,3-benzoxazin-4-one Chemical compound CC1=CC=CC(C(N=2)=O)=C1OC=2N1CCOCC1 RXSQQZJWJXKFMK-UHFFFAOYSA-N 0.000 claims description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
150000003902 salicylic acid esters Chemical class 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 149
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 13
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 12
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 12
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 10
BCQZXOMGPXTTIC-UHFFFAOYSA-N halothane Chemical group FC(F)(F)C(Cl)Br BCQZXOMGPXTTIC-UHFFFAOYSA-N 0.000 claims 9
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 6
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 6
SHVXZNHKNBYMCJ-UHFFFAOYSA-N 8-methyl-2-morpholin-4-yl-7-(pyridin-2-ylmethoxy)chromen-4-one Chemical compound C1=CC(C(C=C(O2)N3CCOCC3)=O)=C2C(C)=C1OCC1=CC=CC=N1 SHVXZNHKNBYMCJ-UHFFFAOYSA-N 0.000 claims 5
AJQSBTLUPQKKBR-UHFFFAOYSA-N 2-(8-methyl-2-morpholin-4-yl-4-oxochromen-7-yl)oxy-n-(1-phenylethyl)acetamide Chemical compound C=1C=CC=CC=1C(C)NC(=O)COC(C=1C)=CC=C(C(C=2)=O)C=1OC=2N1CCOCC1 AJQSBTLUPQKKBR-UHFFFAOYSA-N 0.000 claims 4
NFQGALZPMSQQCY-UHFFFAOYSA-N 2-(8-methyl-2-morpholin-4-yl-4-oxochromen-7-yl)oxy-n-phenylacetamide Chemical compound C1=CC(C(C=C(O2)N3CCOCC3)=O)=C2C(C)=C1OCC(=O)NC1=CC=CC=C1 NFQGALZPMSQQCY-UHFFFAOYSA-N 0.000 claims 4
BHXUFMNUPPHMLG-UHFFFAOYSA-N 2-phenylmethoxychromen-4-one Chemical compound O1C2=CC=CC=C2C(=O)C=C1OCC1=CC=CC=C1 BHXUFMNUPPHMLG-UHFFFAOYSA-N 0.000 claims 4
WJTOXQVNPZRBLL-UHFFFAOYSA-N 6-[(1-cyclohexyltetrazol-5-yl)methoxy]-2-morpholin-4-ylchromen-4-one Chemical compound C1=C2C(=O)C=C(N3CCOCC3)OC2=CC=C1OCC1=NN=NN1C1CCCCC1 WJTOXQVNPZRBLL-UHFFFAOYSA-N 0.000 claims 4
XBTCRUAPKBPWAB-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methoxy]-2-morpholin-4-ylchromen-4-one Chemical compound C1=CC(OC)=CC=C1COC1=CC=CC2=C1OC(N1CCOCC1)=CC2=O XBTCRUAPKBPWAB-UHFFFAOYSA-N 0.000 claims 4
ZEWXXQYARSJHBL-UHFFFAOYSA-N [2-(dimethylamino)-8-methyl-4-oxochromen-7-yl]carbamic acid Chemical compound CN(C=1OC2=C(C(C=1)=O)C=CC(=C2C)NC(O)=O)C ZEWXXQYARSJHBL-UHFFFAOYSA-N 0.000 claims 4
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 4
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 4
YVNJNLWFEVGFIR-IBGZPJMESA-N (2s)-2-[[2-(8-methyl-2-morpholin-4-yl-4-oxochromen-7-yl)oxyacetyl]amino]-3-phenylpropanoic acid Chemical compound C([C@H](NC(=O)COC1=C(C2=C(C(C=C(O2)N2CCOCC2)=O)C=C1)C)C(O)=O)C1=CC=CC=C1 YVNJNLWFEVGFIR-IBGZPJMESA-N 0.000 claims 3
FGFGIKMFYALJEJ-UHFFFAOYSA-N 6,7-dimethoxy-2-morpholin-4-ylchromen-4-one Chemical compound C=1C(=O)C=2C=C(OC)C(OC)=CC=2OC=1N1CCOCC1 FGFGIKMFYALJEJ-UHFFFAOYSA-N 0.000 claims 3
XLHMEHJJNRTJMA-UHFFFAOYSA-N 7-[(1-cyclohexyltetrazol-5-yl)methoxy]-8-methyl-2-morpholin-4-ylchromen-4-one Chemical compound C1=CC(C(C=C(O2)N3CCOCC3)=O)=C2C(C)=C1OCC1=NN=NN1C1CCCCC1 XLHMEHJJNRTJMA-UHFFFAOYSA-N 0.000 claims 3
CVOITCRVIKSUNV-UHFFFAOYSA-N 8-methyl-2-morpholin-4-yl-7-(2-piperidin-1-ylethoxy)chromen-4-one Chemical compound C1=CC(C(C=C(O2)N3CCOCC3)=O)=C2C(C)=C1OCCN1CCCCC1 CVOITCRVIKSUNV-UHFFFAOYSA-N 0.000 claims 3
235000001674 Agaricus brunnescens Nutrition 0.000 claims 3
SBUKLPSBNFWJCU-UHFFFAOYSA-N ClIBr Chemical compound ClIBr SBUKLPSBNFWJCU-UHFFFAOYSA-N 0.000 claims 3
HXEACLLIILLPRG-YFKPBYRVSA-N L-pipecolic acid Chemical compound [O-]C(=O)[C@@H]1CCCC[NH2+]1 HXEACLLIILLPRG-YFKPBYRVSA-N 0.000 claims 3
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 3
229910000147 aluminium phosphate Inorganic materials 0.000 claims 3
KHDRVSWKJLLLOH-UHFFFAOYSA-N benzyl n-(2-morpholin-4-yl-4-oxochromen-6-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC(C=C1C(=O)C=2)=CC=C1OC=2N1CCOCC1 KHDRVSWKJLLLOH-UHFFFAOYSA-N 0.000 claims 3
HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 claims 3
GGWBHVILAJZWKJ-KJEVSKRMSA-N ranitidine hydrochloride Chemical compound [H+].[Cl-].[O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 GGWBHVILAJZWKJ-KJEVSKRMSA-N 0.000 claims 3
KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 claims 2
IZDWKMOOKVUWAI-UHFFFAOYSA-N 2-(2-morpholin-4-yl-4-oxochromen-8-yl)oxy-n-(1-phenylethyl)acetamide Chemical compound C=1C=CC=CC=1C(C)NC(=O)COC1=CC=CC(C(C=2)=O)=C1OC=2N1CCOCC1 IZDWKMOOKVUWAI-UHFFFAOYSA-N 0.000 claims 2
IAZJBMBBJGDCJI-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)chromen-4-one Chemical compound C1CN(C)CCN1C1=CC(=O)C2=CC=CC=C2O1 IAZJBMBBJGDCJI-UHFFFAOYSA-N 0.000 claims 2
DWMLBWWMACTPAW-UHFFFAOYSA-N 2-(dimethylamino)-8-methyl-7-phenylmethoxychromen-4-one Chemical compound CC1=C2OC(N(C)C)=CC(=O)C2=CC=C1OCC1=CC=CC=C1 DWMLBWWMACTPAW-UHFFFAOYSA-N 0.000 claims 2
GAAWVNYLMWBWQJ-UHFFFAOYSA-N 2-(dimethylamino)chromen-4-one Chemical compound C1=CC=C2OC(N(C)C)=CC(=O)C2=C1 GAAWVNYLMWBWQJ-UHFFFAOYSA-N 0.000 claims 2
KTVKQTNGWVJHFL-UHFFFAOYSA-N 2-ethylchromen-4-one Chemical compound C1=CC=C2OC(CC)=CC(=O)C2=C1 KTVKQTNGWVJHFL-UHFFFAOYSA-N 0.000 claims 2
WUHDRCLIPLEIRK-UHFFFAOYSA-N 2-ethynylchromen-4-one Chemical compound C(#C)C=1OC2=C(C(C=1)=O)C=CC=C2 WUHDRCLIPLEIRK-UHFFFAOYSA-N 0.000 claims 2
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 2
FEPWPCJBBOUBEB-UHFFFAOYSA-N 2-morpholin-4-yl-6-nitrochromen-4-one Chemical compound C=1C(=O)C2=CC([N+](=O)[O-])=CC=C2OC=1N1CCOCC1 FEPWPCJBBOUBEB-UHFFFAOYSA-N 0.000 claims 2
MFMUZQYOURNHOB-UHFFFAOYSA-N 2-morpholin-4-yl-8-(1-phenyltetrazol-5-yl)oxychromen-4-one Chemical compound C1=CC=C2C(=O)C=C(N3CCOCC3)OC2=C1OC1=NN=NN1C1=CC=CC=C1 MFMUZQYOURNHOB-UHFFFAOYSA-N 0.000 claims 2
FHWCKVKPRCRFJI-UHFFFAOYSA-N 2-morpholin-4-yl-8-(2-phenylethoxy)chromen-4-one Chemical compound C1=CC=C2C(=O)C=C(N3CCOCC3)OC2=C1OCCC1=CC=CC=C1 FHWCKVKPRCRFJI-UHFFFAOYSA-N 0.000 claims 2
FVCZHPDXMMYSDW-UHFFFAOYSA-N 2-morpholin-4-yl-8-(2-phenylethynyl)chromen-4-one Chemical compound C1=CC=C2C(=O)C=C(N3CCOCC3)OC2=C1C#CC1=CC=CC=C1 FVCZHPDXMMYSDW-UHFFFAOYSA-N 0.000 claims 2
QBDBJYQILZWJHD-UHFFFAOYSA-N 2-morpholin-4-yl-8-[(4-phenylmethoxyphenyl)methoxy]chromen-4-one Chemical compound C1=CC=C2C(=O)C=C(N3CCOCC3)OC2=C1OCC(C=C1)=CC=C1OCC1=CC=CC=C1 QBDBJYQILZWJHD-UHFFFAOYSA-N 0.000 claims 2
KAHUCGPFHJBNTD-UHFFFAOYSA-N 2-morpholin-4-yl-8-[[3-(trifluoromethyl)phenyl]methoxy]chromen-4-one Chemical compound FC(F)(F)C1=CC=CC(COC=2C3=C(C(C=C(O3)N3CCOCC3)=O)C=CC=2)=C1 KAHUCGPFHJBNTD-UHFFFAOYSA-N 0.000 claims 2
WTCUDNJDKCHSMB-UHFFFAOYSA-N 2-morpholin-4-yl-8-prop-2-enylchromen-4-one Chemical compound C=CCC1=CC=CC(C(C=2)=O)=C1OC=2N1CCOCC1 WTCUDNJDKCHSMB-UHFFFAOYSA-N 0.000 claims 2
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DREQEMXTAJXTHR-UHFFFAOYSA-N 3-bromo-2-morpholin-4-ylchromen-4-one Chemical compound O1C2=CC=CC=C2C(=O)C(Br)=C1N1CCOCC1 DREQEMXTAJXTHR-UHFFFAOYSA-N 0.000 claims 2
CDMRUXMNUKHHJJ-UHFFFAOYSA-N 3-chloro-2-morpholin-4-ylchromen-4-one Chemical compound O1C2=CC=CC=C2C(=O)C(Cl)=C1N1CCOCC1 CDMRUXMNUKHHJJ-UHFFFAOYSA-N 0.000 claims 2
CIERPRDYPKVDJO-UHFFFAOYSA-N 4-[[3-(carboxymethylsulfanyl)-4-hydroxynaphthalen-1-yl]sulfamoyl]benzoic acid Chemical compound C=12C=CC=CC2=C(O)C(SCC(=O)O)=CC=1NS(=O)(=O)C1=CC=C(C(O)=O)C=C1 CIERPRDYPKVDJO-UHFFFAOYSA-N 0.000 claims 2
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IBOFLWPLPLGPRY-UHFFFAOYSA-N 6-chloro-2-morpholin-4-ylchromen-4-one Chemical compound C=1C(=O)C2=CC(Cl)=CC=C2OC=1N1CCOCC1 IBOFLWPLPLGPRY-UHFFFAOYSA-N 0.000 claims 2
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CWSSLJBZRCFZPM-UHFFFAOYSA-N 8-(hydroxymethyl)-2-morpholin-4-ylchromen-4-one Chemical compound OCC1=CC=CC(C(C=2)=O)=C1OC=2N1CCOCC1 CWSSLJBZRCFZPM-UHFFFAOYSA-N 0.000 claims 2
FIYHQTAVXHZXRS-UHFFFAOYSA-N 8-[(1-cyclohexyltetrazol-5-yl)methoxy]-2-morpholin-4-ylchromen-4-one Chemical compound C1=CC=C2C(=O)C=C(N3CCOCC3)OC2=C1OCC1=NN=NN1C1CCCCC1 FIYHQTAVXHZXRS-UHFFFAOYSA-N 0.000 claims 2
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OSUBTTQNUXOTBB-UHFFFAOYSA-N 8-[(3-methoxyphenyl)methoxy]-2-morpholin-4-ylchromen-4-one Chemical compound COC1=CC=CC(COC=2C3=C(C(C=C(O3)N3CCOCC3)=O)C=CC=2)=C1 OSUBTTQNUXOTBB-UHFFFAOYSA-N 0.000 claims 2
PTDLHNORSCYAPL-UHFFFAOYSA-N 8-[(4-chlorophenyl)methoxy]-2-morpholin-4-ylchromen-4-one Chemical compound C1=CC(Cl)=CC=C1COC1=CC=CC2=C1OC(N1CCOCC1)=CC2=O PTDLHNORSCYAPL-UHFFFAOYSA-N 0.000 claims 2
YXLJPXODNXZXBI-UHFFFAOYSA-N 8-[(4-ethoxyphenyl)methoxy]-2-morpholin-4-ylchromen-4-one Chemical compound C1=CC(OCC)=CC=C1COC1=CC=CC2=C1OC(N1CCOCC1)=CC2=O YXLJPXODNXZXBI-UHFFFAOYSA-N 0.000 claims 2
ILDFUNWTQMICKC-UHFFFAOYSA-N 8-[(4-tert-butylphenyl)methoxy]-2-morpholin-4-ylchromen-4-one Chemical compound C1=CC(C(C)(C)C)=CC=C1COC1=CC=CC2=C1OC(N1CCOCC1)=CC2=O ILDFUNWTQMICKC-UHFFFAOYSA-N 0.000 claims 2
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DQSBDAZBOSVNSL-UHFFFAOYSA-N 8-ethyl-2-morpholin-4-yl-7-(2-piperidin-1-ylethoxy)chromen-4-one Chemical compound C1=CC(C(C=C(O2)N3CCOCC3)=O)=C2C(CC)=C1OCCN1CCCCC1 DQSBDAZBOSVNSL-UHFFFAOYSA-N 0.000 claims 2
IYZNYSMVRFPBRE-UHFFFAOYSA-N 8-methyl-2-(4-methylpiperazin-1-yl)-7-phenylmethoxychromen-4-one Chemical compound C1CN(C)CCN1C(OC1=C2C)=CC(=O)C1=CC=C2OCC1=CC=CC=C1 IYZNYSMVRFPBRE-UHFFFAOYSA-N 0.000 claims 2
XAXKIHNCQAQWLI-UHFFFAOYSA-N 8-methyl-2-(morpholin-4-ylmethyl)-7-phenylmethoxychromen-4-one Chemical compound C1=CC(C(C=C(CN2CCOCC2)O2)=O)=C2C(C)=C1OCC1=CC=CC=C1 XAXKIHNCQAQWLI-UHFFFAOYSA-N 0.000 claims 2
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WCIBMJUPHUDMNE-UHFFFAOYSA-N 8-methyl-2-morpholin-4-yl-7-(2-oxobutoxy)chromen-4-one Chemical compound CC=1C(OCC(=O)CC)=CC=C(C(C=2)=O)C=1OC=2N1CCOCC1 WCIBMJUPHUDMNE-UHFFFAOYSA-N 0.000 claims 2
BTKTXZNBJKXBCY-UHFFFAOYSA-N 8-methyl-2-morpholin-4-yl-7-(2-phenylethyl)chromen-4-one Chemical compound C1=CC(C(C=C(O2)N3CCOCC3)=O)=C2C(C)=C1CCC1=CC=CC=C1 BTKTXZNBJKXBCY-UHFFFAOYSA-N 0.000 claims 2
RNWDPCWPACKYHX-UHFFFAOYSA-N 8-methyl-2-morpholin-4-yl-7-(2-phenylethynyl)chromen-4-one Chemical compound CC1=C(C#CC=2C=CC=CC=2)C=CC(C(C=2)=O)=C1OC=2N1CCOCC1 RNWDPCWPACKYHX-UHFFFAOYSA-N 0.000 claims 2
VDEZRJUMCJLJDA-UHFFFAOYSA-N 8-methyl-2-morpholin-4-yl-7-(2-pyrrolidin-1-ylethoxy)chromen-4-one Chemical compound C1=CC(C(C=C(O2)N3CCOCC3)=O)=C2C(C)=C1OCCN1CCCC1 VDEZRJUMCJLJDA-UHFFFAOYSA-N 0.000 claims 2
WBJPDBZCJJMXDF-UHFFFAOYSA-N 8-methyl-2-morpholin-4-yl-7-(pyridin-3-ylmethoxy)chromen-4-one Chemical compound C1=CC(C(C=C(O2)N3CCOCC3)=O)=C2C(C)=C1OCC1=CC=CN=C1 WBJPDBZCJJMXDF-UHFFFAOYSA-N 0.000 claims 2
CLVOUOCNZHDCBY-UHFFFAOYSA-N 8-methyl-2-morpholin-4-yl-7-(quinolin-2-ylmethoxy)chromen-4-one Chemical compound CC1=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC(C(C=2)=O)=C1OC=2N1CCOCC1 CLVOUOCNZHDCBY-UHFFFAOYSA-N 0.000 claims 2
OZUPVBLJSIYWRH-UHFFFAOYSA-N 8-methyl-2-morpholin-4-yl-7-(quinoxalin-2-ylmethoxy)chromen-4-one Chemical compound CC1=C(OCC=2N=C3C=CC=CC3=NC=2)C=CC(C(C=2)=O)=C1OC=2N1CCOCC1 OZUPVBLJSIYWRH-UHFFFAOYSA-N 0.000 claims 2
RAVNJPFVXXAJPB-UHFFFAOYSA-N 8-methyl-2-morpholin-4-yl-7-[[3-(trifluoromethyl)phenyl]methoxy]chromen-4-one Chemical compound C1=CC(C(C=C(O2)N3CCOCC3)=O)=C2C(C)=C1OCC1=CC=CC(C(F)(F)F)=C1 RAVNJPFVXXAJPB-UHFFFAOYSA-N 0.000 claims 2
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NCGOSAASIOCCBF-UHFFFAOYSA-N 8-methyl-2-morpholin-4-yl-7-prop-2-enoxychromen-4-one Chemical compound CC1=C(OCC=C)C=CC(C(C=2)=O)=C1OC=2N1CCOCC1 NCGOSAASIOCCBF-UHFFFAOYSA-N 0.000 claims 2
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VHERNNOIQYJZCP-UHFFFAOYSA-N 7-chloro-2-morpholin-4-yl-1,3-benzoxazin-4-one Chemical compound C=1C(Cl)=CC=C(C(N=2)=O)C=1OC=2N1CCOCC1 VHERNNOIQYJZCP-UHFFFAOYSA-N 0.000 claims 1
VAIJDPFRNFUTMG-UHFFFAOYSA-N 7-chloro-2-morpholin-4-ylchromen-4-one Chemical compound C=1C(Cl)=CC=C(C(C=2)=O)C=1OC=2N1CCOCC1 VAIJDPFRNFUTMG-UHFFFAOYSA-N 0.000 claims 1
SPWDLNVJNBSWKE-UHFFFAOYSA-N 7-methoxy-2-morpholin-4-yl-1,3-benzoxazin-4-one Chemical compound C=1C(OC)=CC=C(C(N=2)=O)C=1OC=2N1CCOCC1 SPWDLNVJNBSWKE-UHFFFAOYSA-N 0.000 claims 1
CIURUWADRTYFFI-UHFFFAOYSA-N 8-[(2-methoxyphenyl)methoxy]-2-morpholin-4-ylchromen-4-one Chemical compound COC1=CC=CC=C1COC1=CC=CC2=C1OC(N1CCOCC1)=CC2=O CIURUWADRTYFFI-UHFFFAOYSA-N 0.000 claims 1
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GCVYSCYZXZLTES-UHFFFAOYSA-N 8-methyl-2-(morpholin-4-ylmethyl)-7-(pyridin-3-ylmethoxy)chromen-4-one Chemical compound C1=CC(C(C=C(CN2CCOCC2)O2)=O)=C2C(C)=C1OCC1=CC=CN=C1 GCVYSCYZXZLTES-UHFFFAOYSA-N 0.000 claims 1
OZPPFPUPYKDMGT-UHFFFAOYSA-N 8-methyl-2-morpholin-4-yl-7-(2-oxopropoxy)chromen-4-one Chemical compound CC=1C(OCC(=O)C)=CC=C(C(C=2)=O)C=1OC=2N1CCOCC1 OZPPFPUPYKDMGT-UHFFFAOYSA-N 0.000 claims 1
MDBHDLRVJRDYLU-UHFFFAOYSA-N 8-methyl-2-piperidin-1-yl-1,3-benzoxazin-4-one Chemical compound CC1=CC=CC(C(N=2)=O)=C1OC=2N1CCCCC1 MDBHDLRVJRDYLU-UHFFFAOYSA-N 0.000 claims 1
WDVOEEAOWKWIFU-UHFFFAOYSA-N 8-methyl-2-piperidin-1-yl-7-(pyridin-3-ylmethoxy)chromen-4-one Chemical compound C1=CC(C(C=C(O2)N3CCCCC3)=O)=C2C(C)=C1OCC1=CC=CN=C1 WDVOEEAOWKWIFU-UHFFFAOYSA-N 0.000 claims 1
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229910002091 carbon monoxide Inorganic materials 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
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125000001309 chloro group Chemical group Cl* 0.000 description 1
208000019425 cirrhosis of liver Diseases 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940125810 compound 20 Drugs 0.000 description 1
229940126208 compound 22 Drugs 0.000 description 1
229940125833 compound 23 Drugs 0.000 description 1
229940125851 compound 27 Drugs 0.000 description 1
239000004020 conductor Substances 0.000 description 1
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229910052802 copper Inorganic materials 0.000 description 1
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238000012937 correction Methods 0.000 description 1
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
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ZJULYDCRWUEPTK-UHFFFAOYSA-N dichloromethyl Chemical compound Cl[CH]Cl ZJULYDCRWUEPTK-UHFFFAOYSA-N 0.000 description 1
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238000007876 drug discovery Methods 0.000 description 1
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CJGXMNONHNZEQQ-UHFFFAOYSA-N ethyl 2-amino-3-phenylpropanoate Chemical compound CCOC(=O)C(N)CC1=CC=CC=C1 CJGXMNONHNZEQQ-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 description 1
RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 1
235000013305 food Nutrition 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000007429 general method Methods 0.000 description 1
239000010439 graphite Substances 0.000 description 1
229910002804 graphite Inorganic materials 0.000 description 1
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150000002391 heterocyclic compounds Chemical class 0.000 description 1
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229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
208000026621 hypolipoproteinemia Diseases 0.000 description 1
229940125721 immunosuppressive agent Drugs 0.000 description 1
239000003018 immunosuppressive agent Substances 0.000 description 1
239000000411 inducer Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
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208000014674 injury Diseases 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000011630 iodine Chemical group 0.000 description 1
208000028867 ischemia Diseases 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
150000004701 malic acid derivatives Chemical class 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
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125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 1
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208000010125 myocardial infarction Diseases 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
VQSRKMNBWMHJKY-YTEVENLXSA-N n-[3-[(4ar,7as)-2-amino-6-(5-fluoropyrimidin-2-yl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-7a-yl]-4-fluorophenyl]-5-methoxypyrazine-2-carboxamide Chemical compound C1=NC(OC)=CN=C1C(=O)NC1=CC=C(F)C([C@@]23[C@@H](CN(C2)C=2N=CC(F)=CN=2)CSC(N)=N3)=C1 VQSRKMNBWMHJKY-YTEVENLXSA-N 0.000 description 1
BVOCPVIXARZNQN-UHFFFAOYSA-N nipecotamide Chemical compound NC(=O)C1CCCNC1 BVOCPVIXARZNQN-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
239000004533 oil dispersion Substances 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
235000020323 palazzo Nutrition 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229960005190 phenylalanine Drugs 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
230000035479 physiological effects, processes and functions Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
PRAYXGYYVXRDDW-UHFFFAOYSA-N piperidin-2-ylmethanol Chemical compound OCC1CCCCN1 PRAYXGYYVXRDDW-UHFFFAOYSA-N 0.000 description 1
VUNPWIPIOOMCPT-UHFFFAOYSA-N piperidin-3-ylmethanol Chemical compound OCC1CCCNC1 VUNPWIPIOOMCPT-UHFFFAOYSA-N 0.000 description 1
230000008092 positive effect Effects 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229940068479 potassium sulfide Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
208000005069 pulmonary fibrosis Diseases 0.000 description 1
GZRKXKUVVPSREJ-UHFFFAOYSA-N pyridinylpiperazine Chemical compound C1CNCCN1C1=CC=CC=N1 GZRKXKUVVPSREJ-UHFFFAOYSA-N 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000004044 response Effects 0.000 description 1
230000008458 response to injury Effects 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000000523 sample Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229940082054 sodium bicarbonate / sodium chloride Drugs 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003900 succinic acid esters Chemical class 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
150000003899 tartaric acid esters Chemical class 0.000 description 1
IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
238000010998 test method Methods 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
201000010875 transient cerebral ischemia Diseases 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
238000013519 translation Methods 0.000 description 1
230000008733 trauma Effects 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
230000002792 vascular Effects 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/20—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 4
- C07D265/22—Oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Urology & Nephrology (AREA)
Pharmacology & Pharmacy (AREA)
Vascular Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pyrane Compounds (AREA)

JP2501394A 1988-12-21 1989-12-15 抗アテローム性動脈硬化症性および抗血栓性１―ベンゾピラン―４―オン類および２―アミノ―１，３―ベンゾオキサジン―４―オン類 Pending JPH04502322A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US28779688A	1988-12-21	1988-12-21
US287,796		1988-12-21

Publications (1)

Publication Number	Publication Date
JPH04502322A true JPH04502322A (ja)	1992-04-23

Family

ID=23104392

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2501394A Pending JPH04502322A (ja)	1988-12-21	1989-12-15	抗アテローム性動脈硬化症性および抗血栓性１―ベンゾピラン―４―オン類および２―アミノ―１，３―ベンゾオキサジン―４―オン類

Country Status (8)

Country	Link
EP (1)	EP0459983A1 (fr)
JP (1)	JPH04502322A (fr)
AU (1)	AU634994B2 (fr)
DK (1)	DK118791D0 (fr)
FI (1)	FI912995A7 (fr)
HU (2)	HUT58310A (fr)
RU (1)	RU2118321C1 (fr)
WO (1)	WO1990006921A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2002528544A (ja) *	1998-10-30	2002-09-03	メルクパテントゲゼルシャフトミットベシュレンクテルハフトング	インテグリン阻害剤としてのクロメノン及びクロマノンの誘導体
JP2005523312A (ja) *	2002-04-17	2005-08-04	サイトキネティクス・インコーポレーテッド	化合物、組成物および方法
JPWO2009038064A1 (ja) *	2007-09-19	2011-01-06	株式会社医薬分子設計研究所	Ｉ型１１βヒドロキシステロイド脱水素酵素阻害活性を有する複素環誘導体
JP2012504148A (ja) *	2008-09-29	2012-02-16	サートリスファーマシューティカルズ，インコーポレイテッド	サーチュインモジュレーターとしてのクロメノンアナログ
WO2014030688A1 (fr) *	2012-08-24	2014-02-27	第一三共株式会社	Chromone à chaîne latérale linéaire
JPWO2013111850A1 (ja) *	2012-01-26	2015-05-11	第一三共株式会社	骨形成促進作用を有するクロモン誘導体

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0525123B1 (fr) *	1990-06-20	1997-09-17	PHARMACIA & UPJOHN COMPANY	1-benzopyran-4-ones et 2-amino-1,3-benzoxazine-4-ones antiathero sclerotiques et antithrombotiques
US5302613A (en) *	1990-06-29	1994-04-12	The Upjohn Company	Antiatheroscleroic and antithrombotic 2-amino-6-phenyl-4H-pyran-4-ones
US5252735A (en) *	1990-06-29	1993-10-12	The Upjohn Company	Antiatherosclerotic and antithrombotic 2-amino-6-phenyl-4H-pyran-4-ones
ATE128128T1 (de) *	1990-06-29	1995-10-15	Upjohn Co	Antiatherosclerotische und antithrombotische 2- amino-6-phenyl-4h-pyran-4-one.
IL112764A0 (en) *	1994-03-18	1995-05-26	Ferrer Int	New chromene derivatives
CA2182932A1 (fr) *	1995-08-10	1997-02-11	Koju Watanabe	Derive de la chromone; methode de preparation et composition pharmaceutique a base de ce derive
AU3704400A (en) *	1999-03-04	2000-09-21	E.I. Du Pont De Nemours And Company	Fused bicyclic oxazinone and thiazinone fungicides
GB9920910D0 (en) *	1999-09-03	1999-11-10	Indena Spa	Novel chalcones
CN1891693A (zh)	2000-01-24	2007-01-10	基纳西亚股份有限公司	用于治疗的吗啉代基取代的化合物
DE10044091A1 (de) *	2000-09-07	2002-04-04	Merck Patent Gmbh	Chromanonderivate
GB0119863D0 (en)	2001-08-14	2001-10-10	Cancer Res Campaign Tech	DNA-PK inhibitors
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US7049313B2 (en)	2002-02-25	2006-05-23	Kudos Pharmaceuticals Ltd.	ATM inhibitors
DE60326248D1 (de)	2002-07-17	2009-04-02	Cytokinetics Inc	Verbindungen, zusammensetzungen und verfahren zur behandlung von zellulären proliferativen erkrankungen
CN100430389C (zh) *	2002-08-16	2008-11-05	阿斯利康(瑞典)有限公司	抑制磷酸肌醇3-激酶β
US7598377B2 (en) *	2002-08-16	2009-10-06	Astrazeneca Ab	Inhibition of phosphoinositide 3-kinase β
SI1631295T1 (sl) *	2003-06-06	2010-06-30	Arexis Ab	Uporaba kondenziranih heterocikličnih spojin kotSCCE inhibitorjev za zdravljenje kožnih bolezni
CN100518740C (zh) *	2003-06-06	2009-07-29	阿里克斯股份公司	杂环化合物作为scce抑制剂的制药用途
AU2004265149A1 (en)	2003-08-13	2005-02-24	Kudos Pharmaceuticals Limited	Aminopyrones and their use as ATM inhibitors
ATE447957T1 (de) *	2003-12-09	2009-11-15	Us Gov Health & Human Serv	Verfahren zur unterdrückung einer immunantwort oder zur behandlung von proliferativen erkrankungen
BRPI0515498A (pt)	2004-09-20	2008-07-29	Kudos Pharm Ltd	inibidores de dna-pk
EP1848712A1 (fr)	2005-02-09	2007-10-31	Kudos Pharmaceuticals Ltd	Inhibiteurs d'atm
AR053358A1 (es)	2005-04-15	2007-05-02	Cancer Rec Tech Ltd	Inhibidores de adn - pk
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RU2468018C1 (ru) *	2011-10-06	2012-11-27	Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Российский университет дружбы народов" (РУДН)	Способ получения производных 4-оксо-4h-хроменов, содержащих винильную и енаминную группировки
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CN108929329B (zh) *	2017-05-24	2020-12-11	中国医学科学院药物研究所	2-氮杂环-5-三氟甲基-8-硝基苯并(硫代)吡喃-4-酮类化合物
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KR20240004865A (ko)	2021-05-03	2024-01-11	페트라 파마 코포레이션	질환의 치료를 위한 포스포이노시티드 3-키나제 (pi3k)의 알로스테릭 크로메논 억제제
EP4347040A1 (fr)	2021-05-27	2024-04-10	Petra Pharma Corporation	Inhibiteurs chroménone allostériques de la phosphoinositide 3-kinase (pi3k) pour le traitement du cancer
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Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2205913A1 (de) *	1972-02-08	1973-08-16	Thiemann Chem Pharm Fab	2-amino-3-hydroxy-chromon-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE2555290A1 (de) *	1975-12-09	1977-06-16	Boehringer Mannheim Gmbh	Neue benzopyron-derivate und verfahren zu ihrer herstellung
US4412071A (en) *	1982-05-17	1983-10-25	The Upjohn Company	Antiatherosclerotic compositions
ZA873745B (en) *	1986-06-04	1988-10-26	Daiichi Seiyaku Co	Benzopyran derivatives
IL89840A (en) *	1988-04-06	1996-10-31	Lipha	Substituted flavonoid compounds and salts thereof their preparation and pharmaceutical composition containing them

1989
- 1989-12-15 AU AU48071/90A patent/AU634994B2/en not_active Ceased
- 1989-12-15 JP JP2501394A patent/JPH04502322A/ja active Pending
- 1989-12-15 FI FI912995A patent/FI912995A7/fi unknown
- 1989-12-15 RU SU4895676A patent/RU2118321C1/ru active
- 1989-12-15 EP EP90900649A patent/EP0459983A1/fr not_active Ceased
- 1989-12-15 WO PCT/US1989/005526 patent/WO1990006921A1/fr not_active Ceased
- 1989-12-15 HU HU90394A patent/HUT58310A/hu unknown
1991
- 1991-06-19 DK DK911187A patent/DK118791D0/da not_active Application Discontinuation
1995
- 1995-06-23 HU HU95P/P00411P patent/HU211339A9/hu unknown

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2002528544A (ja) *	1998-10-30	2002-09-03	メルクパテントゲゼルシャフトミットベシュレンクテルハフトング	インテグリン阻害剤としてのクロメノン及びクロマノンの誘導体
JP2005523312A (ja) *	2002-04-17	2005-08-04	サイトキネティクス・インコーポレーテッド	化合物、組成物および方法
US7919524B2 (en)	2002-04-17	2011-04-05	Cytokinetics, Inc.	Compounds, compositions and methods
US8119678B2 (en)	2002-04-17	2012-02-21	Cytokinetics, Incorporated	Compounds, compositions and methods
US8329928B2 (en)	2002-04-17	2012-12-11	Cytokinetics, Incorporated	Compounds, compositions and methods
US8633236B2 (en)	2002-04-17	2014-01-21	Cytokinetics, Inc.	Compounds, compositions and methods
JPWO2009038064A1 (ja) *	2007-09-19	2011-01-06	株式会社医薬分子設計研究所	Ｉ型１１βヒドロキシステロイド脱水素酵素阻害活性を有する複素環誘導体
JP2012504148A (ja) *	2008-09-29	2012-02-16	サートリスファーマシューティカルズ，インコーポレイテッド	サーチュインモジュレーターとしてのクロメノンアナログ
JP2015134809A (ja) *	2008-09-29	2015-07-27	サートリスファーマシューティカルズ，インコーポレイテッド	サーチュインモジュレーターとしてのクロメノンアナログ
JPWO2013111850A1 (ja) *	2012-01-26	2015-05-11	第一三共株式会社	骨形成促進作用を有するクロモン誘導体
WO2014030688A1 (fr) *	2012-08-24	2014-02-27	第一三共株式会社	Chromone à chaîne latérale linéaire

Also Published As

Publication number	Publication date
DK118791A (da)	1991-06-19
FI912995A0 (fi)	1991-06-19
HUT58310A (en)	1992-02-28
DK118791D0 (da)	1991-06-19
FI912995A7 (fi)	1991-06-19
EP0459983A1 (fr)	1991-12-11
HU211339A9 (en)	1995-11-28
RU2118321C1 (ru)	1998-08-27
AU634994B2 (en)	1993-03-11
WO1990006921A1 (fr)	1990-06-28
AU4807190A (en)	1990-07-10
HU900394D0 (en)	1991-09-30

Publication	Publication Date	Title
JPH04502322A (ja)	1992-04-23	抗アテローム性動脈硬化症性および抗血栓性１―ベンゾピラン―４―オン類および２―アミノ―１，３―ベンゾオキサジン―４―オン類
US5703075A (en)	1997-12-30	Antiatherosclerotic and antithrombotic 1-benzopyran-4-ones and 2-amino-1,3-benzoxazine-4-ones
KR910007970B1 (ko)	1991-10-05	4h-1-벤조피란-4-온 유도체 또는 이의 염, 이의 제조방법 및 활성 성분으로서 이를 함유하는 약제학적 조성물
Huang et al.	1998	Synthesis and antiplatelet activity of phenyl quinolones
AU2002362385B2 (en)	2008-07-31	DNA-PK inhibitors
JP2793195B2 (ja)	1998-09-03	ベンゾチアゾール誘導体
US5482967A (en)	1996-01-09	Condensed heterocyclic compounds, their production and use
AU782647B2 (en)	2005-08-18	Bicyclic androgen and progesterone receptor modulator compounds and methods
KR900007780B1 (ko)	1990-10-20	축합된 피롤리논 유도체의 제조방법
EP0525123B1 (fr)	1997-09-17	1-benzopyran-4-ones et 2-amino-1,3-benzoxazine-4-ones antiathero sclerotiques et antithrombotiques
JPH05112531A (ja)	1993-05-07	ヒドロキシキノロン誘導体
JPH04253961A (ja)	1992-09-09	Ｈｉｖ逆転写酵素の阻害物質
DK3164393T3 (en)	2019-01-21	Flavagline derivatives
WO1999042442A1 (fr)	1999-08-26	Derives d'aminoguanidine hydrazone, procedes de production, et medicaments a base de ces derives
CZ302792A3 (en)	1993-10-13	Intima atherosclerotic concretion inhibitor
CA2598216C (fr)	2014-04-08	Composes modulateurs du recepteur des androgenes et procedes associes
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AU639337B2 (en)	1993-07-22	Dioxo-tetrahydroquinoline derivatives
JPS6236382A (ja)	1987-02-17	チエノピリドン治療薬及びその製法
CN113544129A (zh)	2021-10-22	三环类化合物制备方法及其在医药领域的应用
EP2880023A1 (fr)	2015-06-10	Derives de griseofulvine
WO1986001510A1 (fr)	1986-03-13	Agents anti-inflammatoires a l'oxindole tricyclique
JPS62126180A (ja)	1987-06-08	７−アシルベンゾオキサジノン及びその誘導体並びにそれらの製法及びそれらを含有する薬剤
HU185329B (en)	1985-01-28	Process for preparing quinolone derivatives and pharmaceutical compositions containing such compounds
WO2001014384A1 (fr)	2001-03-01	Derives dihydrobenzofuran tricycliques, leur procede de preparation et agents