# US 5,703,075 A · Antiatherosclerotic and antithrombotic 1-benzopyran-4-ones and 2-amino-1,3-benzoxazine-4-ones

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- Number: US 5,703,075 A
- Document ID: US5703075A
- Status: Granted
- Kind: A
- Application number: 08/484,584
- Filed: 1995-06-07
- Granted: 1997-12-30
- Earliest claimed: 1988-12-21
- Assignees: Pharmacia & Upjohn Company
- Inventors: Ronald B. Gammill; Thomas M. Judge; Joel Morris
- Web page: https://patentgrep.com/patent/US5703075A

## CPC

- C07D 265/22: Oxygen atoms
- C07D 311/22: with oxygen or sulfur atoms directly attached in position 4
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C07D 405/14: containing three or more hetero rings
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- C07D 417/12: linked by a chain containing hetero atoms as chain links
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

This invention relates to compounds of Formula I ##STR1## which are useful in association with a pharmaceutical carrier as antiatherosclerotic agents. In addition, various compounds of Formula I are useful inhibitors of cell proliferation.

## Claims

### Claim 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-benzopyra n-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-ace tamide,
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)-aceta mide;
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.

### Claim 2 (depends on 1)

A compound according to claim 1 wherein Z is H or C.sub.1 -C.sub.5 alkyl.

### Claim 3 (depends on 2)

A compound according to claim 2 wherein Y is -(4-morpholine) or -CH.sub.2 -(4-morpholine).

### Claim 4 (depends on 3)

A compound according to claim 3 wherein Z is H.

### Claim 5 (depends on 4)

A compound according to claim 4 wherein Y is -(4-morpholine).

### Claim 6 (depends on 3)

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.

### Claim 7 (depends on 5)

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.

### Claim 8 (depends on 1)

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-o ne;
Cpd 49 7-›(4-Chlorophenyl)methoxy!-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-o ne;
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-b enzopyran-4-one;
Cpd 55 8-Methyl-2-(4-morpholinyl)-7-››4-phenylmethoxy)-phenyl!methoxy!-4H-1-benzo pyran-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-on e;
Cpd 58 7-›(2-Phenylethyl)methoxy!-8-methyl-2-(4-morpholinyl)-4H-1-benzopyran-4-on e;
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-o ne;
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!-ben zoic 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-ben zopyran-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-on e;
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-benzop yran-4-one;
Cpd 136 7-Hydroxy-2-(4-morpholinyl)-8-(3-trifluoromethyl)phenylmethoxy-4H-1-benzop yran-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-benzop yran-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-benzopyr an-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!-acetami de;
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)-ac etamide;
Cpd 147 N-›››8-methyl-2-(4-morpholinyl)-4-oxo-4H-1-benzopyran-7-yl!oxy!acetyl!-phe nyalanine, ethyl ester;
Cpd 149 8-methyl-2-(4-morpholinyl)-7-›(1-phenyl-1H-tetrazol-5-yl)oxy!-4H-1-Benzopy ran-4-one;
Cpd 152 2-››8-methyl-2-(4-morpholinyl)-4-oxo-4H-1-benzopyran-7-yl!oxy!-N-3-pyridin yl-acetamide;
Cpd 153 N-›››8-methyl-2-(4-morpholinyl)-4-oxo-4H-1-benzopyran-7-yl!oxy!acetyl!-Phe nylalanine;
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-Benzop yran-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-on e;
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-b enzopyran-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-o ne;
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-benzop yran-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-o ne;
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-morpholinylmethy l)-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-ben zopyran-4-one;
Cpd 209 7-(2-(2-Hydroxymethylpiperidin-1-yl)ethyl)oxy-8-methyl-2-(4-morpholinyl)-4 H-1-benzopyran-4-one;
Cpd 210 7-(2-(3-Hydroxymethylpiperidin-1-yl)ethyl)oxy-8-methyl-2-(4-morpholinyl)-4 H-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-ben zopyran-4-one;
Cpd 214 7-(2-(3-Carboxypiperidin-1-yl)ethyl)oxy-8-methyl-2-(4-morpholinyl)-4H-1-be nzopyran-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-on e;
Cpd 220 8-Methyl-2-(4-morpholinyl)-7-›2-(4-(2-hydroxy)ethyl-1-piperazinyl)ethyl!ox y-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-benzopyra n-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-morpholin yl)-4H-1-benzopyran-4-one;
Cpd 228 8-Methyl-7-›2-((4-Methyl-1,2,4-triazol-3-yl)thio)ethyl!oxy-2-(4-morpholiny l)-4H-1-benzopyran-4-one;
Cpd 229 7-›2-(N-Ethyl-N'-((2-hydroxy)ethyl)amino)-ethyl!oxy-8-methyl-2-(4-morpholi nyl)-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-benzop yran-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-benzopy ran-4-one;
Cpd 234 7-›2-((2-(Bis-N,N'-diethylamino)ethyl)-thio)ethyl!oxy-8-Methyl-2-(4-morpho linyl)-4H-1-benzopyran-4-one;
Cpd 235 8-Methyl-7-›2-((2-benzoxazolyl)thio)ethyl!oxy-2-(4-morpholinyl)-4H-1-benzo pyran-4-one;
Cpd 236 8-Methyl-7-›2-((2-benzothiazolyl)thio)ethyl!-oxy-2-(4-morpholinyl)-4H-1-be nzopyran-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-benzopy ran-4-one;
or a pharmaceutically acceptable salt or hydrate thereof.

### Claim 9 (depends on 1)

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-ben zopyran-4-one;
or a pharmaceutically acceptable salt or hydrate thereof.

### Claim 10 (depends on 1)

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-morpholiny l)-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-Benzop yran-4-one;
Cpd 296 2-(4-morpholinyl)-8-›2-›4-(phenylmethyl)-1-piperazinyl!ethoxy!-4H-1-Benzop yran-4-one;
Cpd 326 8-ethenyl-7-›2-(4-methyl-1-piperazinyl)ethoxy!-2-(4-morpholinyl)-4H-1-Benz opyran-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-Benzopyra n-4-one;
Cpd 331 (R)-8-ethenyl-7-›2-›2-(hydroxymethyl)-1-pyrrolidinyl!ethoxy!-2-(4-morpholi nyl)-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.

### Claim 11

A compound selected from the group consisting of:
Cpd 243 8-›2-›4-(2-ethoxyphenyl)-1-piperazinyl!ethoxy!-2-(4-morpholinyl)-4H-1-Benz opyran-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-morpholi nyl)-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-Ben zopyran-4-one;
Cpd 256 8-methyl-2-(4-morpholinyl)-7-›2-(4-phenyl-1-piperazinyl)ethoxy!-4H-1-Benzo pyran-4-one;
Cpd 257 8-methyl-2-(4-morpholinyl)-7-›2-(4-phenyl-1-piperidinyl)ethoxy!-4H-1-Benzo pyran-4-one;
Cpd 258 (R)-7-›2-›2-(hydroxymethyl)-1-pyrrolidinyl!-ethoxy!-8-methyl-2-(4-morpholi nyl)-4H-1-Benzopyran-4-one;
Cpd 259 7-›2-(3-hydroxy-1-pyrrolidinyl)ethoxy!-8-methyl-2-(4-morpholinyl)-4H-1-Ben zopyran-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-o ne;
Cpd 262 8-methyl-2-(4-morpholinyl)-7-›(1-phenyl-1H-tetrazol-5-yl)methoxy!-4H-1-Ben zopyran-4-one;
Cpd 263 5-›››8-methyl-2-(4-morpholinyl)-4-oxo-4H-1-benzopyran-7-yl!oxy!methyl!-.al pha.-(phenylmethyl)-1H-Tetrazole-1-acetic acid ethyl ester;
Cpd 264 8-methyl-2-(4-morpholinylmethyl)-7-››1-(1-phenylethyl)-1H-tetrazol-5-yl!me thoxy!-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-morpholi nyl)-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-o ne;
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!methy l!-.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)-4 H-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-Benzo pyran-4-one;
Cpd 277 8-›2-(4-methyl-1-piperazinyl)ethoxy!-2-(4-morpholinylmethyl)-4H-1-Benzopyr an-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-o ne;
Cpd 280 8-ethyl-2-(4-morpholinyl)-7-›2-(4-phenyl-1-piperidinyl)ethoxy!-4H-1-Benzop yran-4-one;
Cpd 281 (R)-8-ethyl-7-›2-›2-(hydroxymethyl)-1-pyrrolidinyl!ethoxy!-2-(4-morpholiny l)-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-Benzop yran-4-one;
Cpd 285 7-›2-(3,4-dihydro-2(1H)-isoquinolinyl)ethoxy!-8-methyl-2-(4-morpholinyl)-4 H-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-o ne;
Cpd 292 2-(4-morpholinyl)-7-›2-(4-phenyl-1-piperidinyl)ethoxy!-8-propyl-4H-1-Benzo pyran-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-pr opyl-4H-1-Benzopyran-4-one;
Cpd 295 8-›2-(3,4-dihydro-2(1H)-isoquinolinyl)ethoxy!-2-(4-morpholinyl)-4H-1-Benzo pyran-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-Piperidin ecarboxylic 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!-4 H-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-Benzopyr an-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-Benzop yran-4-one;
Cpd 315 6-iodo-8-methyl-2-(4-morpholinyl)-7-›2-(1-piperidinyl)ethoxy!-4H-1-Benzopy ran-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-Benzo pyran-4-one;
Cpd 318 6-bromo-8-methyl-2-(4-morpholinyl)-7-›2-(1-piperidinyl)ethoxy!-4H-1-Benzop yran-4-one;
Cpd 319 6-bromo-8-methyl-7-›2-(4-methyl-1-piperazinyl)-ethoxy!-2-(4-morpholinyl)-4 H-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-Benzopy ran-4-one;
Cpd 322 2-(4-morpholinyl)-7-›2-(1-piperidinyl)ethoxy!-8-(2-propenyl)-4H-1-Benzopyr an-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-Benz opyran-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.

### Claim 12 (depends on 1)

A compound according to claim 1, namely 2-(4-morpholinyl)-4H-1-Benzopyran-4-one.