Claims
- 1. A compound of Formula I
- wherein X is CZ where Z is H, C.sub.1 -C.sub.5 alkyl, amino (-NH.sub.2) or a halogen atom;
- Y is -(CH.sub.2).sub.n -(4-morpholine) optionally substituted with one or two members selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl;
- R.sub.5, R.sub.6, R.sub.7 and R.sub.8, being the same or different, are selected from the group consisting of hydrogen, C.sub.1 -C.sub.8 alkyl, -(CH.sub.2).sub.n phenyl, -(CH.sub.2).sub.n naphthyl, -(CH.sub.2).sub.n pyridinyl, -(CH.sub.2).sub.q NR.sub.9 R.sub.10, -CH.dbd.CH-phenyl, -CH.sub.2 -CH.dbd.CH.sub.2, -CH.dbd.CH-CH.sub.3, -CH.dbd.CH.sub.2, -O-CH.sub.2 -CH.dbd.CH.sub.2, -C.ident.C-phenyl, -O(CH.sub.2).sub.p (N-methylpiperdin-3-yl), -O-(CH.sub.2).sub.p NR.sub.9 R.sub.10,-O-(CH.sub.2).sub.p -4-(C.sub.1 -C.sub.4 alkyl)-1-piperazine, -O-(CH.sub.2).sub.p (1-piperidinyl), -O-(CH.sub.2).sub.p (1-pyrrolidinyl), -O-(CH.sub.2).sub.2 -4-methyl-1-piperazine, -O-CH.sub.2 CH(OCH.sub.3).sub.2, -O-(CH.sub.2).sub.p OR.sub.15, -O-(CH.sub.2).sub.p -O-(CH.sub.2).sub.p -OR.sub.15, -O-(CH.sub.2).sub.p -S-R.sub.15, -O-(CH.sub.2).sub.p -O-(CH.sub.2).sub.p NR.sub.9 R.sub.10,-O-(CH.sub.2).sub.p -S-(CH.sub.2).sub.p NR.sub.9 R.sub.10, -O-(CH.sub.2).sub.p -S-(CH.sub.2).sub.p -OR.sub.15, -O-(CH.sub.2).sub.p -S(O)-R.sub.15, -O-(CH.sub.2).sub.p -S(O.sub.2)-R.sub.15, -O-(CH.sub.2).sub.p -S(O)-(CH.sub.2).sub.p NR.sub.9 R.sub.10,-O-(CH.sub.2).sub.p -S(O)-(CH.sub.2).sub.p -OR.sub.15, -O-(CH.sub.2).sub.p -S(O.sub.2) -(CH.sub.2).sub.p NR.sub.9 R.sub.10,-O-(CH.sub.2).sub.p -S(O.sub.2)-(CH.sub.2).sub.p -OR.sub.15, -O-(CH.sub.2).sub.p -�4-�(CH.sub.2).sub.p OR.sub.15 !-1-piperazine!, -O-(CH.sub.2).sub.p -�4-(CH)(phenyl).sub.2 -1-piperazine!, -O-(CH.sub.2).sub.p -�4-(CH.sub.2).sub.q phenyl-1-piperazine !, -O-(CH.sub.2).sub.p -�4-(CH.sub.2).sub.q pyridinyl-1-piperazine!, -O-(CH.sub.2).sub.p -�4-(NR.sub.9 R.sub.10 substituted pyridinyl)-1-piperazine!, -O-(CH.sub.2).sub.p -(OH substituted 1-piperidine, -O-(CH.sub.2).sub.p -1-pyrrolidin-2-one, -(CH.sub.2).sub.n C(O)-(CH.sub.2).sub.n R.sub.9, -(CH.sub.2).sub.n C(O)O-(CH.sub.2).sub.p R.sub.9, -(CH.sub.)n C(O)O-(CH.sub.2).sub.p NR.sub.9 R.sub.10, -(CH.sub.2).sub.n C(O)(CH.sub.2).sub.n NR.sub.9 R.sub.10, NO.sub.2, -O-(CH.sub.2).sub.n C(O)-(CH.sub.2).sub.p R.sub.9, -O-(CH.sub.2).sub.n C(O)O-(CH.sub.2).sub.p R.sub.9, -O-(CH.sub.2).sub.n C(O)-(CH.sub.2).sub.n NR.sub.9 R.sub.10,-NR.sub.9 R.sub.10,-N(R.sub.9)(CH.sub.2).sub.n C(O)-(CH.sub.2).sub.n R.sub.10,-N(R.sub.9)-(CH.sub.2).sub.n C(O)O-(CH.sub.2).sub.n R.sub.10,N(R.sub.9)(CH.sub.2).sub.n C(O)-(CH.sub.2).sub.n NR.sub.9 R.sub.10,-O-(CH.sub.2).sub.n phenyl, -O-(CH.sub.2).sub.n pyridine, -O(CH.sub.2).sub.n C(O)-(CH.sub.2).sub.n pyridine, -O-(CH.sub.2).sub.n C(O)O-(CH.sub.2).sub.n pyridine, -O(CH.sub.2).sub.n C(O)-N(R.sub.9)(CH.sub.2).sub.n pyridine, -O-(CH.sub.2).sub.n quinoxalinyl, -O-(CH.sub.2).sub.n quinolinyl, -O-(CH.sub.2).sub.n pyrazinyl, -O-(CH.sub.2).sub.n naphthyl, -O-(CH.sub.2).sub.n C(O)-(CH.sub.2).sub.n naphthyl, -O-(CH.sub.2).sub.n C(O)O-(CH.sub.2).sub.n naphthyl, -O-(CH.sub.2).sub.n C(O)NR.sub.9 -(CH.sub.2).sub.n naphthyl, halo (fluoro, chloro, bromo, iodo), OH, -(CH.sub.2).sub.q -OH, -(CH.sub.2).sub.q OC(O)R.sub.9, -(CH.sub.2).sub.q OC(O)-NR.sub.9 R.sub.10,-(1-cyclohexyl-1H-tetrazol-5-yl)C.sub.1 -C.sub.4 alkoxy, �1-(C.sub.1 -C.sub.5 alkyl)-1H-tetrazol-5-yl!-C.sub.1 -C.sub.4 alkoxy, �1-(phenyl)-1H-tetrazol-5-yl!C.sub.1 -C.sub.4 alkoxy, -�1-(pyridinyl)-1H-tetrazol-5-yl!C.sub.1 -C.sub.4 alkoxy, -�1-(1-phenylethyl)-1H-tetrazol-5-yl!C.sub.1 -C.sub.4 alkoxyl, -C.sub.1 -C.sub.4 alkoxyl, a group of Formula II ##STR3## wherein R' is methyl or carboxy, R" is hydrogen and R'" is selected from benzyl, C.sub.1 -C.sub.5 alkyl, -(CH.sub.2).sub.n CO.sub.2 H, -CH.sub.2 SH, -CH.sub.2 SCH.sub.3, imidazolinylmethylene, indolinylmethylene, CH.sub.3 CH(OH), CH.sub.2 OH, H.sub.2 N(CH.sub.2).sub.4 -(optionally in protected form) or H.sub.2 NC(NH)NH(CH.sub.2).sub.3 (optionally in protected form); with the proviso that when Y is 4-morpholinyl, the compound is other than:
- 6. 7-dimethoxy-2-(4-morpholinyl)-4H-1-benzopyran-4-one,
- 7,8-(Bis)-(3-trifluoromethyl)phenylmethoxy-2-(4-morpholinyl)-4H-1-benzopyran-4-one,
- N-cyclohexyl -2-��8-methyl -2-(4-morpholinyl)-4-oxo-4H-1-benzopyran-7-yl!oxy!-acetamide,
- 2-��8-methyl-2-(4-morpholinyl)-4-oxo-4H-1-benzopyran-7-yl!oxy!-N-phenyl-acetamide,
- 6-�(1-cyclohexyl -1H-tetrazol -5-yl)methoxy!-2-(4-morpholinyl)-4H-1-Benzopyran-4-one,
- 2-��8-methyl -2-(4-morpholinyl)-4-oxo-4H-1-benzopyran-7-yl!oxy!-N-(1-phenylethyl)-acetamide;
- R.sub.9 and R.sub.10,being the same or different, are selected from the group consisting of (a) hydrogen, with the provisio that R.sub.9 and R.sub.10 are not both hydrogen; (b) C.sub.1 -C.sub.12 alkyl; (c) phenyl optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo, OH, trifluoromethyl or -CO.sub.2 (C.sub.1 -C.sub.4 alkyl); (d)-(CH.sub.2).sub.n phenyl, (e)-(CH.sub.2).sub.n pyridinyl or (f) wherein R.sub.9 and R.sub.10, taken together with N, form a saturated or unsaturated heterocyclic amine ring selected from the group consisting of
- (aa) 4-morpholine optionally substituted with one or two members selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl,
- (bb) 4-thiomorpholine optionally substituted with one or two members selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl,
- (cc) 3-amino-1-pyrrolidine,
- (dd) 1-pyrrolidine optionally substituted with one or two members selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo, OH, -CH.sub.2 OH, or trifluoromethyl,
- (ee) 1-piperidine optionally substituted with one or two members selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo, trifluoromethyl, -(CH.sub.2).sub.q OH, -CO.sub.2 H, -CO.sub.2 CH.sub.3, -CO.sub.2 CH.sub.2 CH.sub.3 or phenyl (wherein phenyl is optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl),
- (ff) 1-piperazine, 4-(C.sub.1 -C.sub.4 alkyl)-1-piperazine, 4-phenyl-1-piperazine (wherein phenyl is optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl) or 4-pyridinyl-1-piperazine optionally substituted with one or two members selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo, trifluoromethyl, -CH.sub.2 OH, -CO.sub.2 H, -CO.sub.2 CH.sub.3 or -CO.sub.2 CH.sub.2 CH.sub.3, and
- (gg) thiazolidine, thiazolidine-4-carboxylic acid, pipecolinic acid, p-piperazinacetophenone, 1-homopiperazine, 1-methylhomopiperazine, 4-phenyl-1,2-3,6-tetrahydropyridine, proline, tetrahydrofurylamine, 1-(3-hydroxy)pyrrolidine, nipecotamide, 1,2,3,4-tetrahydroisoquinoline or imidazole;
- R.sub.15 is selected from H, C.sub.1 -C.sub.5 alkyl, -(CH.sub.2).sub.n phenyl, -(CH.sub.2).sub.n pyridin-1-yl, -(CH.sub.2).sub.n pyridin-2-yl, -(CH.sub.2).sub.n pyridin-3-yl, -(CH.sub.2).sub.n pyridin-4-yl, -CH.sub.2).sub.n -1-(C.sub.1 -C.sub.4 alkyl)-1H-5-tetrazole, -(CH.sub.2).sub.n -pyrimidine, -(CH.sub.2).sub.n -2-benzoxazole, -(CH.sub.2).sub.n -2-benzothiazole, -(CH.sub.2).sub.n -(C.sub.1 -C.sub.4 alkyl)-triazole, -(CH.sub.2).sub.n -(C.sub.1 -C.sub.4 alkyl)-imidazole;
- n is 0-5;
- p is 2-5;
- q is 1-5;
- and pharmaceutically acceptable salts and hydrates thereof; and with the overall proviso that when R.sub.5, R.sub.6 and R.sub.8 are selected from: H, C.sub.1 -C.sub.8 alkyl, or halogen and Z is H or C.sub.1 -C.sub.5 alkyl, or halogen, then R.sub.7 is other than -OH, -OCH.sub.3, -((CH.sub.2).sub.n C(O)O-(CH.sub.2).sub.p R.sub.9 or -O-(CH.sub.2).sub.n C(O)-NR.sub.9 R.sub.10 wherein n is other than 0, and R.sub.9 and R.sub.10 are selected from H or C.sub.1 -C.sub.12 alkyl.
- 2. A compound according to claim 1 wherein Z is H or C.sub.1 -C.sub.5 alkyl.
- 3. A compound according to claim 2 wherein Y is -(4-morpholine) or -CH.sub.2 -(4-morpholine).
- 4. A compound according to claim 3 wherein Z is H.
- 5. A compound according to claim 4 wherein Y is -(4-morpholine).
- 6. A compound according to claim 3 wherein R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are selected from the following groups:
- (i) R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are each hydrogen; or
- (ii) R.sub.5, R.sub.6, and R.sub.8 are each hydrogen, and R.sub.7 is selected from:
- -O-(CH.sub.2).sub.n phenyl (wherein phenyl is optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl), -C.ident.C-phenyl (wherein phenyl is optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl), or -(CH.sub.2).sub.n phenyl (wherein phenyl is optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl); or
- (iii) R.sub.5 and R.sub.6 are hydrogen, R.sub.8 is hydrogen, halo or C.sub.1 -C.sub.5 alkyl, and R.sub.7 is selected from: -O-(CH.sub.2).sub.n phenyl (wherein phenyl is optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl), -O-(CH.sub.2).sub.n pyridinyl (wherein pyridinyl is optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl), -O-(CH.sub.2).sub.n naphthyl, -(CH.sub.2).sub.n phenyl (wherein phenyl is optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl), -(CH.sub.2).sub.p pyridinyl (wherein pyridinyl is optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl), -(CH.sub.2).sub.p (1-piperidinyl), -(CH.sub.2).sub.p (1-pyrrolidinyl), -O-(CH.sub.2).sub.p NR.sub.9 R.sub.10,-O-(CH.sub.2).sub.p -O-R.sub.15, -O-(CH.sub.2).sub.p -S-R.sub.15, or -�(1-cyclohexyl-1H-tetrazol-5-yl)C.sub.1 -C.sub.4 alkoxy; or
- (iv) R.sub.5, R.sub.7 and R.sub.8 are each hydrogen, and R.sub.6 is -NH-C(O)-O-CH.sub.2 phenyl.
- 7. A compound according to claim 5 wherein R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are selected from the following groups:
- (i) R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are each hydrogen; or
- (ii) R.sub.5, R.sub.6, and R.sub.8 are each hydrogen, and R.sub.7 is selected from:
- -O-(CH.sub.2).sub.n phenyl (wherein phenyl is optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl), -C.ident.C-phenyl (wherein phenyl is optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl), or -(CH.sub.2).sub.n phenyl (wherein phenyl is optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl); or
- (iii) R.sub.5 and R.sub.6 are hydrogen, R.sub.8 is hydrogen, halo or C.sub.1 -C.sub.5 alkyl, and R.sub.7 is selected from: -O-(CH.sub.2).sub.n phenyl (wherein phenyl is optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl), -O-(CH.sub.2).sub.n pyridinyl (wherein pyridinyl is optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl), -O-(CH.sub.2).sub.n naphthyl, -(CH.sub.2).sub.n phenyl (wherein phenyl is optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl), -(CH.sub.2).sub.p pyridinyl (wherein pyridinyl is optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl), -(CH.sub.2).sub.p (1-piperidinyl), -(CH.sub.2).sub.p (1-pyrrolidinyl),-O-(CH.sub.2).sub.p NR.sub.9 R.sub.10,-O-(CH.sub.2).sub.p -O-R.sub.15, -O-(CH.sub.2).sub.p -S-R.sub.15, or -�(1-cyclohexyl-1H-tetrazol-5-yl)C.sub.1 -C.sub.4 alkoxy; or
- (iv) R.sub.5, R.sub.7 and R.sub.8 are each hydrogen, and R.sub.6 is -NH-C(O)-O-CH.sub.2 phenyl; or
- (v) R.sub.5 and R.sub.6 are hydrogen, R.sub.8 is hydrogen, -CH.dbd.CH.sub.2, halo or C.sub.1 -C.sub.5 alkyl, and R.sub.7 is selected from: -O-(CH.sub.2).sub.n phenyl (wherein phenyl is optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl), -O-(CH.sub.2).sub.n pyridinyl (wherein pyridinyl is optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl), -O-(CH.sub.2).sub.n naphthyl, -(CH.sub.2).sub.n phenyl (wherein phenyl is optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl), -(CH.sub.2).sub.p pyridinyl (wherein pyridinyl is optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl), -(CH.sub.2).sub.p (1-piperidinyl), -(CH.sub.2).sub.p (1-pyrrolidinyl),-O-(CH.sub.2).sub.p -4-(C.sub.1 -C.sub.4 alkyl)-1-piperazine, -O-(CH.sub.2).sub.p (1-piperidinyl), -O-(CH.sub.2).sub.p (1-pyrrolidinyl), -O-(CH.sub.2).sub.p -O-R.sub.15, -O-(CH.sub.2).sub.p -S-R.sub.15, -�1-(C.sub.1 -C.sub.5 alkyl)-1H-tetrazol-5-yl!-C.sub.1 -C.sub.4 alkoxy, or -�(1-cyclohexyl-1H-tetrazol-5-yl)C.sub.1 -C.sub.4 alkoxy; or
- (vi) R.sub.5, R.sub.6 and R.sub.7 are hydrogen, and R.sub.8 is selected from: -C.ident.-C-phenyl (wherein phenyl is optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl), -O-(CH.sub.2).sub.n phenyl (wherein phenyl is optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl), -O-(CH.sub.2).sub.n pyridinyl (wherein pyridinyl is optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl), -O-(CH.sub.2).sub.n naphthyl, -(CH.sub.2).sub.n phenyl (wherein phenyl is optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl), -(CH.sub.2).sub.p pyridinyl (wherein pyridinyl is optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo or trifluoromethyl), -(CH.sub.2).sub.p (1-piperidinyl), -(CH.sub.2).sub.p (1-pyrrolidinyl), -O-(CH.sub.2).sub.p -4-(C.sub.1 -C.sub.4 alkyl)-1-piperazine, -O-(CH.sub.2).sub.p (1-piperidinyl), -O-(CH.sub.2).sub.p (1-pyrrolidinyl), -O-(CH.sub.2).sub.p -O-R.sub.15, -O-(CH.sub.2).sub.p -S-R.sub.15, -!1-C.sub.1 -C.sub.5 alkyl)-1H-tetrazol-5-yl)!-C.sub.1 -C.sub.4 alkoxy, or -�(1-cyclohexyl-1H-tetrazol-5-yl)C.sub.1 -C.sub.4 alkoxy.
- 8. A compound according to claim 1 selected from the group consisting of:
- Cpd 1 6-Chloro-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 2 2-(4-morpholinyl)-4H-benzopyran-4-one;
- Cpd 3 8-Methyl-2-(4-morpholinyl)-(7-phenylmethoxy)-4H-benzopyran-4-one;
- Cpd 4 7-Chloro-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 5 8-Chloro-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 6 6-Bromo-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 7 6-Fluoro-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 8 6-Methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 9 7-Methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 10 8-Methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 11 6-Methoxy-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 12 7-Methoxy-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 13 6-(Phenylmethoxy)-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 14 8-(Phenylmethoxy)-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 15 �2-(4-morpholinyl)-4-oxo-4H-1-benzopyran-6-yl!-1,1-dimethylethyl carbamic acid ester;
- Cpd 16 6-(3-pyridinecarboxamide)-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 17 2-(4-Morpholinyl)-6-nitro-4H-1-benzopyran-4-one;
- Cpd 19 6-(��Phenylmethoxy!carbonyl!amino)-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 20 8-Methoxy-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 21 3-Amino-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 22 3-Chloro-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 23 3-Bromo-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 24 8-Methyl-2-(4-morpholinyl)-7-(phenylmethoxy)-4H-1-benzopyran-4-one;
- Cpd 25 2-(4-Morpholinyl)-5-(phenylmethoxy)-4H-1-benzopyran-4-one;
- Cpd 26 7,8-Dimethoxy-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 39 7-Hydroxy-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 40 6-Hydroxy-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 41 7-Hydroxy-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 42 5-Hydroxy-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 43 8-Hydroxy-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 44 7-Methoxy-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 47 7-�(4-Methoxyphenyl)methoxy!-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 48 8-Methyl-7-�(4-methylphenyl)methoxy!-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 49 7-�(4-Chlorophenyl)methoxy!-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 50 7-�(3,4-Dichlorophenyl)methoxy!-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 51 8-Methyl-2-(4-morpholinyl)-7-(2-pyridinylmethoxy)-4H-1-benzopyran-4-one;
- Cpd 52 8-Methyl-7-��(phenyl)carbonyl!oxy!-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 53 7-Methoxy-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 54 7-��4-(1,1-Dimethylethyl)phenyl!methoxy!-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 55 8-Methyl-2-(4-morpholinyl)-7-��4-phenylmethoxy)-phenyl!methoxy!-4H-1-benzopyran-4-one;
- Cpd 56 7-�(3-Methoxyphenyl)methoxy!-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 57 7-�(4-Nitrophenyl)methoxy!-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 58 7-�(2-Phenylethyl)methoxy!-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 59 7-�(2-Methoxyphenyl)methoxy!-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 60 7-�(4-Ethoxyphenyl)methoxy!-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 61 8-(4-Ethoxy-benzyloxy)-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 62 2-(4-Morpholinyl)-8-(4-nitro-benzyloxy)-4H-1-benzopyran-4-one;
- Cpd 63 8-(2-Methoxy-benzyloxy)-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 64 2-(4-Morpholinyl)-8-(2-phenyl-ethoxy)-4H-1-benzopyran-4-one;
- Cpd 66 8-(4-Benzyloxy-benzyloxy)-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 67 8-(4-Chloro-benzyloxy)-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 68 8-(4-t-Butyl-benzyloxy)-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 69 8-(3-Methoxy-benzyloxy)-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 70 8-(3,4-Dichloro-benzyloxy)-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 71 8-(4-Methyl-benzyloxy)-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 72 8-(4-Methoxy-benzyloxy)-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 73 2-(4-Morpholinyl)-8-(naphthyl-2-methyloxy)-4H-1-benzopyran-4-one;
- Cpd 74 2-(4-Morpholinyl)-8-(naphthyl-1-methyloxy)-4H-1-benzopyran-4-one;
- Cpd 75 8-Methyl-2-(4-morpholinyl)-7-(naphthyl-2-methyloxy)-4H-1-benzopyran-4-one;
- Cpd 76 8-Methyl-2-(4-morpholinyl)-7-(naphthyl-1-methyloxy)-4H-1-benzopyran-4-one;
- Cpd 101 2-(4-morpholinyl)-7-(phenylmethoxy)-4H-1-benzopyran-4-one;
- Cpd 102 8-Methyl-2-(4-morpholinyl)-7-(2-oxo-2-phenylethoxy)-4H-1-benzopyran-4-one;
- Cpd 103 6-Chloro-8-methyl-2-(4-morpholinyl)-7-phenylmethoxy)-4H-1-benzopyran-4-one;
- Cpd 104 ��2-(4-Morpholinyl)-4-oxo-4H-1-benzopyran-8-yl!oxy!-acetic acid methyl ester;
- Cpd 105 4-���8-Methyl-2-(4-morpholinyl)-4-oxo-4H-1-benzopyran-7-yl!oxy!methyl!-benzoic acid methyl ester;
- Cpd 106 4-���2-(4-Morpholinyl)-4-oxo-4H-1-benzopyran-8-yl!oxy!methyl!-benzoic acid methyl ester;
- Cpd 107 8-Methyl-2-(4-morpholinyl)-7-��3-(trifluoromethyl)phenyl!methoxy!-4H-1-benzopyran-4-one;
- Cpd 108 2-(4-Morpholinyl)-8-��3-(trifluoromethyl)phenyl!methoxy!-4H -1-benzopyran-4-one;
- Cpd 109 7-(Cyclohexylmethoxy)-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 110 8-Methyl-2-(4-morpholinyl)-7-(2-propenyloxy)-4H-1-benzopyran-4-one;
- Cpd 111 2-(4-Morpholinyl)-7-(1-naphthalenylmethoxy)-4H-1-benzopyran-4-one;
- Cpd 112 8-Methyl-2-(4-morpholinyl)-7-(3-pyrindinylmethoxy)-4H-1-benzopyran-4-one;
- Cpd 113 8-Methyl-2-(4-morpholinyl)-7-(4-pyrindinylmethoxy)-4H-1-benzopyran-4-one;
- Cpd 115 8-methyl-2-(4-morpholinyl)-7-(2-quinoxalinylmethoxy)-4H-1-benzopyran-4-one;
- Cpd 116 8-methyl-2-(4-morpholinyl)-7-(pyrazinlymethoxy)-4H-1-benzopyran-4-one;
- Cpd 117 8-methyl-2-(4-morpholinyl)-7-(2-pyridinylmethoxy)-4H-1-benzopyran-4-one N-oxide;
- Cpd 118 8-methyl-2-(4-morpholinyl)-7-(3-pyridinylmethoxy)-4H-1-benzopyran-4-one N-oxide;
- Cpd 119 8-Iodo-2-(4-morpholinyl)-7-(3-pyrindinylmethoxy)-4H-1-benzopyran-4-one;
- Cpd 120 3,3-Dimethyl-1-��8-methyl-2-(4-morpholinyl)-4-oxo-4H-1-benzopyran-7-yl!oxy!-butan-2-one;
- Cpd 121 1-��8-Methyl-2-(4-morpholinyl)-4-oxo-4H-1-benzopyran-7-yl!oxy!-propan-2-one;
- Cpd 122 1-��8-Methyl-2-(4-morpholinyl)-4-oxo-4H-1-benzopyran-7-yl!oxy!-butan-2-one;
- Cpd 123 8-Methyl-2-(4-morpholinyl)-7-(2-oxo-2-(2-naphthyl)ethoxy)-4H-1-benzopyran-4-one;
- Cpd 125 2-(4-Morpholinyl)-7-(2-pyrindinylmethoxy)-4H-1-benzopyran-4-one;
- Cpd 126 2-(4-Morpholinyl)-7-(3-pyrindinylmethoxy)-4H-1-benzopyran-4-one;
- Cpd 127 2-(4-Morpholinyl)-8-(2-pyrindinylmethoxy)-4H-1-benzopyran-4-one;
- Cpd 128 2-(4-Morpholinyl)-8-(3-pyrindinylmethoxy)-4H-1-benzopyran-4-one;
- Cpd 129 8-methyl-2-(4-morpholinyl)-7-(2-quinolinylmethoxy)-4H-1-benzopyran-4-one;
- Cpd 130 7,8-(Bis)-phenylmethoxy-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 131 7,8-(Bis)-acetyloxy-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 132 7,8-(Bis)-hydroxy-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 133 7-Hydroxy-2-(4-morpholinyl)-8-phenylmethoxy-4H-1-benzopyran-4-one;
- Cpd 135 8-Hydroxy-2-(4-morpholinyl)-7-(3-trifluoromethyl)phenylmethoxy-4H-1-benzopyran-4-one;
- Cpd 136 7-Hydroxy-2-(4-morpholinyl)-8-(3-trifluoromethyl)phenylmethoxy-4H-1-benzopyran-4-one;
- Cpd 137 7-�3-(1-cyclohexyl-1H-tetrazol-5-yl)propoxyl-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 138 8-�3-(1-cyclohexyl-1H-tetrazol-5-yl)propoxy!-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 139 7-�(1-cyclohexyl-1H-tetrazol-5-yl)methoxy!-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 140 8-�(1-cyclohexyl-1H-tetrazol-5-yl)methoxy!-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 141 2-(4-morpholinyl)-8-�(1-phenyl-1H-tetrazol-5-yl)oxy!-4H-1-benzopyran-4-one;
- Cpd 142 N-cyclohexyl-2-��2-(4-morpholinyl)-4-oxo-4H-1-benzopyran-8-yl!oxy!-acetamide;
- Cpd 143 N-(1,1-dimethylethyl)-2-��2-(4-morpholinyl)-4-oxo-4H-1-benzopyran-8-yl!oxy!-acetamide;
- Cpd 144 2-��2-(4-morpholinyl)-4-oxo-4H-1-benzopyran-8-yl!-N-phenyl-acetamide;
- Cpd 145 2-��2-(4-morpholinyl)-4-oxo-4H-1-benzopyran-8-yl!oxy!-N-(1-phenylethyl)-acetamide;
- Cpd 147 N-���8-methyl-2-(4-morpholinyl)-4-oxo-4H-1-benzopyran-7-yl!oxy!acetyl!-phenyalanine, ethyl ester;
- Cpd 149 8-methyl-2-(4-morpholinyl)-7-�(1-phenyl-1H-tetrazol-5-yl)oxy!-4H-1-Benzopyran-4-one;
- Cpd 152 2-��8-methyl-2-(4-morpholinyl)-4-oxo-4H-1-benzopyran-7-yl!oxy!-N-3-pyridinyl-acetamide;
- Cpd 153 N-���8-methyl-2-(4-morpholinyl)-4-oxo-4H-1-benzopyran-7-yl!oxy!acetyl!-Phenylalanine;
- Cpd 154 7-(2,2-dimethoxyethoxy)-8-methyl-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 155 2-(4-Morpholinyl)-8-(2-propenyl)-4H-1-benzopyran-4-one;
- Cpd 156 2-(4-Morpholinyl)-8-(1-propenyl)-4H-1-benzopyran-4-one;
- Cpd 157 8-Formyl-2-(4-Morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 158 2-(4-morpholinyl)-8-(phenylamino)methyl-4H-1-benzopyran-4-one;
- Cpd 159 2-(4-morpholinyl)-8-(2E-phenyl)ethenyl-4H-1-benzopyran-4-one;
- Cpd 160 8-Hydroxymethyl-2-(4-Morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 162 8-methyl-7-�(1-methyl-3-piperidinyl)methoxy!-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 163 8-Methyl-2-(4-morpholinyl)-7-(2-(1-piperidinyl)ethyl)oxy-4H-1-benzopyran-4-one;
- Cpd 164 8-Methyl-2-(4-morpholinyl)-7-(2-(1-pyrrolidinyl)ethyl)oxy-4H-1-benzopyran-4-one;
- Cpd 165 8-Methyl-2-(4-morpholinyl)-7-(2-(4-morpholinyl)ethyl)oxy-4H-1-benzopyran-4-one;
- Cpd 166 8-Methyl-2-(4-morpholinyl)-7-(3-(1-piperidino)propyl)oxy-4H-1-benzopyran-4-one;
- Cpd 167 7-(2-Diethylaminoethyl)oxy-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 168 7-�2-(ethylphenylamino)ethoxy!-8-methyl-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 169 7-(2-Diisopropylaminoethyl)oxy-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 172 7-(2-(4-Benzyl-(1-piperizinyl))ethyl)oxy-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 173 7-Acetoxy-3,8-dimethyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 174 3,8-dimethyl-7-hydroxy-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 175 7-benzyloxy-3,8-dimethyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 176 3,8-Dimethyl-2-(4-morpholinyl)-7-(naphthyl-1-methyloxy)-4H-1-benzopyran-4-one;
- Cpd 177 3,8-Dimethyl-7-(4-methoxy-benzyloxy)-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 178 3,8-Dimethyl-2-(4-morpholinyl)-7-(2-phenyl-ethyloxy)-4H-1-benzopyran-4-one;
- Cpd 179 3,8-Dimethyl-7-(4-chlorobenzyloxy)-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 180 3,8-Dimethyl-2-(4-morpholinyl)-7-(3-trifluoromethyl-benzyloxy)-4H-1-benzopyran-4-one;
- Cpd 181 7-(Carbomethoxy-methoxyl)-3,8-dimethyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 182 8-Hydroxy-3-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 183 8-Benzyloxy-3-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 184 3-methyl-2-(4-morpholinyl)-8-(m-trifluoromethyl-benzyloxy)-4H-1-benzopyran-4-one;
- Cpd 185 8-methyl-7-(2-phenyl)ethynyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 186 8-methyl-2-(4-morpholinyl)-7-(2-phenyl)ethyl-4H-1-benzopyran-4-one;
- Cpd 187 2-(4-Morpholinyl)-8-(2-phenyl)ethynyl-4H-1-benzopyran-4-one;
- Cpd 188 2-(4-Morpholinyl)-8-(2-phenyl)ethyl-4H-1-benzopyran-4-one;
- Cpd 189 2-(4-Morpholinyl)-8-(2-(3-trifluoromethyl)phenyl)ethynyl-4H-1-benzopyran-4-one;
- Cpd 190 2-(4-Morpholinyl)-8-(2-(3-trifluoromethyl)phenyl)ethyl-4H-1-benzopyran-4-one;
- Cpd 192 8-Methyl-2-(4-morpholinyl)-7-(2-(1-naphthyl) )ethyl-4H-1-benzopyran-4-one;
- Cpd 193 8-Methyl-2-(4-morpholinyl)-7-phenyl-4H-1-benzopyran-4-one;
- Cpd 194 7-acetyloxy-8-iodo-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 195 8-ethyl-2-(4-morpholinyl)-7-(3-pyrindinylmethoxy)-4H-1-benzopyran-4-one;
- Cpd 196 8-Ethyl-2-(4-morpholinyl)-7-phenylmethoxy-4H-1-benzopyran-4-one;
- Cpd 197 8-Iodo-2-(4-morpholinyl)-7-phenylmethoxy-4H-1-benzopyran-4-one;
- Cpd 198 8-Ethyl-2-(4-morpholinyl)-7-(2-(1-piperidinyl)ethyl)oxy-4H-1-benzopyran-4-one;
- Cpd 199 8-Iodo-2-(4-morpholinyl)-7-(3-pyrindinylmethoxy)-4H-1-benzopyran-4-one;
- Cpd 200 8-Iodo-7-hydroxy-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 204 8-Methyl-2-(4-morpholinylmethyl)-7-(phenylmethoxy)-4H-1-benzopyran-4-one;
- Cpd 205 7-hydroxy-2-(4-morpholinylmethyl)-8-methyl-4H-1-benzopyran-4-one;
- Cpd 206 7-�(1-cyclohexyl-1H-tetrazol-5-yl)methyoxy!-8-methyl-2-(4-morpholinylmethyl)-4H-1-benzopyran-4-one;
- Cpd 207 8-Methyl-2-(4-morpholinylmethyl)-7-(3-pyridinylmethoxy)-4H-1-benzopyran-4-one;
- Cpd 208 7-�2-(4-Methyl-1-piperazinyl)ethyl!oxy-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 209 7-(2-(2-Hydroxymethylpiperidin-1-yl)ethyl)oxy-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 210 7-(2-(3-Hydroxymethylpiperidin-1-yl)ethyl)oxy-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 211 7-(2-(2-Carboethoxypiperidin-1-yl)ethyl)oxy-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 212 7-(2-(3-Carboethoxypiperidin-1-yl)ethyl)oxy-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 213 8-Methyl-7-(2-(2-methylpiperidin-1-yl)ethyl)oxy-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 214 7-(2-(3-Carboxypiperidin-1-yl)ethyl)oxy-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 215 8-Methyl-2-(4-morpholinyl)-7-�2-(1-piperazinyl)ethyl!oxy-4H-1-benzopyran-4-one;
- Cpd 216 8-Methyl-7-�(2-methoxy)ethyl!oxy-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 217 2-(4-Morpholinyl)-7-phenylmethoxy-8-vinyl-4H-1-benzopyran-4-one;
- Cpd 218 2-(4-Morpholinyl)-8-phenyl-7-phenylmethoxy-4H-1-benzopyran-4-one;
- Cpd 219 8-Methyl-7-�(2-thiomethyl)ethyl!oxy-2-(4-Morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 220 8-Methyl-2-(4-morpholinyl)-7-�2-(4-(2-hydroxy)ethyl-1-piperazinyl)ethyl!oxy-4H-1-benzopyran-4-one;
- Cpd 222 7-�2-(Hydroxy)ethyl!oxy-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 223 8-Methyl-2-(4-morpholinyl)-7-�2-(2-thiopyrindinyl)ethyl!oxy-4H-1-benzopyran-4-one;
- Cpd 225 7-�2-(4-(2-Ethoxyphenyl)-1-piperazinyl)ethyl!oxy-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 226 8-Methyl-7-�2-((1-Methyl-1,3-imidazol-2-yl)thio)ethyl!oxy-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 227 7-�2-((Bis-N,N'-(2-methoxy)ethoxy)amino)-ethyl!oxy-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 228 8-Methyl-7-�2-((4-Methyl-1,2,4-triazol-3-yl)thio)ethyl!oxy-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 229 7-�2-(N-Ethyl-N'-((2-hydroxy)ethyl)amino)-ethyl!oxy-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 230 8-Methyl-7-�2-((1-Methyl-5-tetrazoyl)thio)-ethyl!oxy-2-(4-morpholinyl)-4H -1-benzopyran-4-one;
- Cpd 231 8-Methyl-2-(4-morpholinyl)-7-�2-((2-pyrimidinyl)thio)ethyl!oxy-4H-1-benzopyran-4-one;
- Cpd 232 8-Methyl-2-(4-morpholinyl)-7-�2-(4-(2-pyridinyl)-1-piperazinyl)-ethyl!oxy-4H-1-benzopyran-4-one;
- Cpd 233 8-Methyl-2-(4-morpholinyl)-7-�2-(4-thio-morpholinyl)ethyl!oxy-4H-1-benzopyran-4-one;
- Cpd 234 7-�2-((2-(Bis-N,N'-diethylamino)ethyl)-thio)ethyl!oxy-8-Methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 235 8-Methyl-7-�2-((2-benzoxazolyl)thio)ethyl!oxy-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 236 8-Methyl-7-�2-((2-benzothiazolyl)thio)ethyl!-oxy-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 237 7-�2-(4-(3-Ethylamino-pyridin-2-yl)-1-piperazinyl)ethyl!oxy-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one; and
- Cpd 238 8-Methyl-2-(4-morpholinyl)-7-�2-(pyrrolidinone-1-yl)ethyl!oxy-4H-1-benzopyran-4-one;
- or a pharmaceutically acceptable salt or hydrate thereof.
- 9. A compound according to claim 1 selected from the group consisting of:
- Cpd 2 2-(4-morpholinyl)-4H-benzopyran-4-one;
- Cpd 3 8-Methyl-2-(4-morpholinyl)-(7-phenylmethoxy)-4H-benzopyran-4-one;
- Cpd 19 6-(��Phenylmethoxy!carbonyl!amino)-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 51 8-Methyl-2-(4-morpholinyl)-7-(2-pyridinylmethoxy)-4H-1-benzopyran-4-one;
- Cpd 72 8-(4-Methoxy-benzyloxy)-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 76 8-Methyl-2-(4-morpholinyl)-7-(naphthyl-1-methyloxy)-4H-1-benzopyran-4-one;
- Cpd 112 8-Methyl-2-(4-morpholinyl)-7-(3-pyrindinylmethoxy)-4H-1-benzopyran-4-one;
- Cpd 139 7-�(1-cyclohexyl-1H-tetrazol-5-yl)methoxy!-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- Cpd 163 8-Methyl-2-(4-morpholinyl)-7-(2-(1-piperidinyl)ethyl)oxy-4H-1-benzopyran-4-one;
- Cpd 164 8-Methyl-2-(4-morpholinyl)-7-(2-(1-pyrrolidinyl)ethyl)oxy-4H-1-benzopyran-4-one;
- Cpd 171 8-Methyl-2-(1-piperidinyl)-7-(3-pyrindinylmethoxy)-4H-1-benzopyran-4-one;
- Cpd 204 8-Methyl-2-(4-morpholinylmethyl)-7-(phenylmethoxy)-4H-1-benzopyran-4-one;
- Cpd 208 7-�2-(4-Methyl-1-piperazinyl)ethyl!oxy-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-one;
- or a pharmaceutically acceptable salt or hydrate thereof.
- 10. A compound according to claim 1 selected from the group consisting of:
- Cpd 242 2-(4-morpholinyl)-8-�2-(2-pyridinylthio)-ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 244 8-�2-�4-�3-(ethylamino)-2-pyridinyl!-1-piperazinyl!ethoxy!-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 246 8-methyl-2-(4-morpholinyl)-7-�2-(phenylsulfinyl)ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 253 7-�2-�(2-methoxyphenyl)thio!ethoxy!-8-methyl-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 296 2-(4-morpholinyl)-8-�2-�4-(phenylmethyl)-1-piperazinyl!ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 326 8-ethenyl-7-�2-(4-methyl-1-piperazinyl)ethoxy!-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 327 8-ethenyl-2-(4-morpholinyl)-7-�2-(1-piperidinyl)ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 329 8-ethenyl-2-(4-morpholinyl)-7-�2-(1-pyrrolidinyl)ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 330 8-ethenyl-2-(4-morpholinyl)-7-�2-(4-thiomorpholinyl)ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 331 (R)-8-ethenyl-7-�2-�2-(hydroxymethyl)-1-pyrrolidinyl!ethoxy!-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 333 7-�2-(2-methoxyethoxy)ethoxy!-8-methyl-2-(4-morpholinyl)-4H-1-Benzopyran-4-one; and
- Cpd 335 8-methyl-2-(4-morpholinyl)-7-�2-(phenylthio)-ethoxy!-4H-1-Benzopyran-4-one;
- or a pharmaceutically acceptable salt or hydrate thereof.
- 11. A compound selected from the group consisting of:
- Cpd 243 8-�2-�4-(2-ethoxyphenyl)-1-piperazinyl!ethoxy!-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 245 2-(4-morpholinyl)-8-�2-(1-piperidinyl)ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 247 7-�2-�bis(2-pyridinylmethyl)amino!ethoxy!-8-methyl-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 248 (S)-7-�2-�2-(hydroxymethyl)-1-pyrrolidinyl!-ethoxy!-8-methyl-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 249 7-�2-�bis�(4-methoxyphenyl)methyl!amino!-ethoxy!-8-methyl-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 250 8-methyl-2-(4-morpholinyl)-7-�2-(3-thiazolindinyl)ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 251 N-cyclohexyl-N-methyl-2-��2-(4-morpholinyl)-4-oxo-4H-1-benzopyran-6-yl!oxy!-Acetamide;
- Cpd 252 2-(4-morpholinyl)-6-(1-naphthalenylmethoxy)-4H-1-Benzopyran-4-one;
- Cpd 255 7-�2-(hexahydro-1H-azepin-1-yl)ethoxy!-8-methyl-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 256 8-methyl-2-(4-morpholinyl)-7-�2-(4-phenyl-1-piperazinyl)ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 257 8-methyl-2-(4-morpholinyl)-7-�2-(4-phenyl-1-piperidinyl)ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 258 (R)-7-�2-�2-(hydroxymethyl)-1-pyrrolidinyl!-ethoxy!-8-methyl-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 259 7-�2-(3-hydroxy-1-pyrrolidinyl)ethoxy!-8-methyl-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 260 7-�2-�4-(2-chlorophenyl)-1-piperazinyl!ethoxy!-8-methyl-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 261 2-(4-morpholinyl)-8-�2-(4-phenyl-1-piperidinyl)ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 262 8-methyl-2-(4-morpholinyl)-7-�(1-phenyl-1H-tetrazol-5-yl)methoxy!-4H-1-Benzopyran-4-one;
- Cpd 263 5-���8-methyl-2-(4-morpholinyl)-4-oxo-4H-1-benzopyran-7-yl!oxy!methyl!-.alpha.-(phenylmethyl)-1H-Tetrazole-1-acetic acid ethyl ester;
- Cpd 264 8-methyl-2-(4-morpholinylmethyl)-7-��1-(1-phenylethyl)-1H-tetrazol-5-yl!methoxy!-4H-1-Benzopyran-4-one;
- Cpd 265 8-methyl-2-(4-morpholinylmethyl)-7-�(1-phenyl-1H-tetrazol-5-yl)methoxy!-4H-1-Benzopyran-4-one;
- Cpd 266 7-��1-(1,1-dimethylethyl)-1H-tetrazol-5-yl!methoxy!-8-methyl-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 268 8-methyl-7-�2-�methyl �2-(2-pyridinyl)ethyl!-amino!ethoxy!-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 269 8-methyl-2-(4-morpholinyl)-7-�2-(2-pyridinyloxy)ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 270 5-���8-methyl-2-(4-morpholinylmethyl)-4-oxo-4H-1-benzopyran-7-yl!oxy!methyl!-.alpha.-(phenylmethyl)-1H-Tetrazole-1-acetic acid ethyl ester;
- Cpd 272 6-chloro-8-methyl-7-�2-(4-methyl-1-piperazinyl)ethoxy!-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 273 8-butyl-2-(4-morpholinyl)-7-(phenylmethoxy)-4H-1-Benzopyran-4-one;
- Cpd 274 8-Hydroxy-2-(4-morpholinylmethylene)-4H-1-benzopyran-4-one;
- Cpd 275 8-Benzyloxy-2-(4-morpholinylmethylene)-4H-1-benzopyran-4-one;
- Cpd 276 2-(4-morpholinylmethyl)-8-��3-(trifluoro-methyl)pehnyl!methoxy!-4H-1-Benzopyran-4-one;
- Cpd 277 8-�2-(4-methyl-1-piperazinyl)ethoxy!-2-(4-morpholinylmethyl)-4H-1-Benzopyran-4-one;
- Cpd 278 8-�2-�4-(2-ethoxyphenyl)-1-piperazinyl!ethoxy!-2-(4-morpholinylmethyl)-4H-1-Benzopyran-4-one;
- Cpd 279 8-ethyl-2-(4-morpholinyl)-7-�2-(1-pyrrolidinyl)ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 280 8-ethyl-2-(4-morpholinyl)-7-�2-(4-phenyl-1-piperidinyl)ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 281 (R)-8-ethyl-7-�2-�2-(hydroxymethyl)-1-pyrrolidinyl!ethoxy!-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 282 8-ethyl-2-(4-morpholinyl)-7-�2-(4-thiomorpholinyl)ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 283 8-ethyl-7-�2-(4-methyl-1-piperazinyl)ethoxy!-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 285 7-�2-(3,4-dihydro-2(1H)-isoquinolinyl)ethoxy!-8-methyl-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 286 7-(acetyloxy)-2-(4-morpholinyl)-8-(2-propenyl)-4H-1-Benzopyran-4-one;
- Cpd 287 7-(acetyloxy)-2-(4-morpholinyl)-8-propyl-4H-1-Benzopyran-4-one;
- Cpd 288 7-hydroxy-2-(4-morpholinyl)-8-propyl-4H-1-Benzopyran-4-one;
- Cpd 289 7-�2-(4-methyl -1-piperazinyl)ethoxy!-2-(4-morpholinyl)-8-propyl-4H-1-Benzopyran-4-one;
- Cpd 290 2-(4-morpholinyl)-8-propyl-7-�2-(1-pyrrolindinyl)ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 291 2-(4-morpholinyl)-7-�2-(1-piperidinyl)ethoxy!-8-propyl-4H-1-Benzopyran-4-one;
- Cpd 292 2-(4-morpholinyl)-7-�2-(4-phenyl-1-piperidinyl)ethoxy!-8-propyl-4H-1-Benzopyran-4-one;
- Cpd 293 2-(4-morpholinyl)-8-propyl-7-�2-(4-thiomorpholinyl)ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 294 (R)-7-�2-�2-(hydroxymethyl)-1-pyrrolidinyl!-ethoxy!-2-(4-morpholinyl)-8-propyl-4H-1-Benzopyran-4-one;
- Cpd 295 8-�2-(3,4-dihydro-2(1H)-isoquinolinyl)ethoxy!-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 298 7-(acetyloxy)-6-bromo-8-methyl-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 299 7-(acetyloxy)-6,8-dimethyl-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 300 7-hydroxy-6,8-dimethyl-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 301 7-(acetyloxy)-6-iodo-8-methyl-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 302 7-hydroxy-6-iodo-8-methyl-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 303 6-bromo-7-hydroxy-8-methyl-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 304 8-�2-(ethylphenylamino)ethoxyl!-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 305 2-(4-morpholinyl)-8-(2-quinolinylmethoxy)-4H-1-Benzopyran-4-one;
- Cpd 306 1-�2-��2-(4-morpholinyl)-4-oxo-4H-1-benzopyran-8-yl!oxy!ethyl!-3-Piperidinecarboxylic acid ethyl ester;
- Cpd 307 1-�2-��2-(4-morpholinyl)-4-oxo-4H -1-benzopyran-8-yl!oxy!ethyl!-2-Piperidinecarboxylic acid ethyl ester;
- Cpd 308 2-(4-morpholinyllmethyl)-8-��1-(1-phenylethyl)-1H-tetrazol-5-yl!methoxy!-4H-1-Benzopyran-4-one;
- Cpd 309 6,8-dimethyl-7-�2-(4-methyl-1-piperazinyl)-ethoxy!-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 310 6,8-dimethyl-2-(4-morpholinyl)-7-�2-(1-piperidinyl)ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 311 6,8-dimethyl-2-(4-morpholinyl)-7-�2-(1-pyrrolindinyl)ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 312 2-(4-morpholinyl)-8-(2-propenyloxy)-4H-1-Benzopyran-4-one;
- Cpd 314 6-iodo-8-methyl-2-(4-morpholinyl)-7-�2-(1-pyrrolidinyl)ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 315 6-iodo-8-methyl-2-(4-morpholinyl)-7-�2-(1-piperidinyl)ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 316 6-iodo-8-methyl-7-�2-(4-methyl-1-piperazinyl)-ethoxy!-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 317 6-bromo-8-methyl-2-(4-morpholinyl)-7-�2-(1-pyrrolidinyl)ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 318 6-bromo-8-methyl-2-(4-morpholinyl)-7-�2-(1-piperidinyl)ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 319 6-bromo-8-methyl-7-�2-(4-methyl-1-piperazinyl)-ethoxy!-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 320 7-�2-(4-methyl-1-piperazinyl)ethoxy!-2-2(4-morpholinyl)-8-(2-propenyl)-4H-1-Benzopyran-4-one;
- Cpd 321 2-(4-morpholinyl)-8-(2-propenyl)-7-�2-(1-pyrrolidinyl)ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 322 2-(4-morpholinyl)-7-�2-(1-piperidinyl)ethoxy!-8-(2-propenyl)-4H-1-Benzopyran-4-one;
- Cpd 323 2-(4-morpholinyl)-7-�2-(4-phenyl-1-piperidinyl)ethoxy!-8-(2-propenyl)-4H-1-Benzopyran-4-one;
- Cpd 324 2-(4-morpholinyl)-8-(2-propenyl)-7-�2-(4-thiomorpholinyl)ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 325 (R)-7-�2-�-(hydroxymethoxy)-1-pyrrolidinyl!-ethoxy!-2-(4-morpholinyl)-8-(2-propenyl)-4H-1-Benzopyran-4-one;
- Cpd 332 2-(4-morpholinyl)-8-�2-(4-thiomorophlinyl)-ethoxy!-4H-1-Benzopyran-4-one;
- Cpd 334 8-methyl-2-(4-morpholinyl)-7-(2-phenoxyethoxy)-4H-1-Benzopyran-4-one;
- Cpd 348 7-�(1-cyclopropyl-1H-tetrazol-5-yl) methoxy!-8-methyl-2-4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 349 7-�(1-cyclobutyl-1H-tetrazol-5-yl) methoxy!-8-methyl-2-(4-morpholinyl)-4H-1-Benzopyran-4-one;
- Cpd 350 8-�(1-cyclopropyl-1H-tetrazol-5-yl) methoxy!-2-(4-morpholinylmethyl)-4H-1-Benzopyran-4-one;
- Cpd 351 7-�(1-cyclobutyl-1H-tetrazol-5-yl) methoxy!-8-methyl-2-(4-morpholinylmethyl)-4H-1-Benzopyran-4-one;
- Cpd 352 7-�(1-cyclopropyl-1H-tetrazol-5-yl) methoxy!-8-methyl-2-(4-morpholinylmethyl)-4H-1-Benzopyran-4-one;
- or a pharmaceutically acceptable salt or hydrate thereof.
- 12. A compound according to claim 1, namely 2-(4-morpholinyl)-4H-1-Benzopyran-4-one.
Parent Case Info
This application is a continuation of U.S. Ser. No. 08/292,316, filed Aug. 19, 1994; which is a continuation of U.S. Ser. No. 08/106,965, filed Aug. 16, 1993; which is a continuation of U.S. Ser. No. 08/718,391, filed Jun. 19, 1991, now abandoned; which is a continuation-in-part of PCT application No. PCT/US91/04140, fled Jun. 18, 1991; which is a continuation-in-part of U.S. Ser. No. 07/541326, filed Jun. 20, 1990, now abandoned, which is a continuation-in-part of Application No. PCT/US89/05526, filed Dec. 15, 1989; which is a continuation-in-part of U.S. Ser. No. 07/287,796, filed Dec. 21, 1988, now abandoned.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
3491092 |
Grigat et al. |
Jan 1970 |
|
4092416 |
Winter et al. |
May 1978 |
|
Foreign Referenced Citations (1)
Number |
Date |
Country |
B-7381587 |
Oct 1987 |
AUX |
Continuations (3)
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Number |
Date |
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Parent |
292316 |
Aug 1994 |
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Parent |
106965 |
Aug 1993 |
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Parent |
718391 |
Jun 1991 |
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Continuation in Parts (2)
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Number |
Date |
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Parent |
541126 |
Jun 1990 |
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Parent |
287796 |
Dec 1988 |
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