US 5,220,042 AGranted

1,4-benzoquinone derivatives and benzene derivatives, and process for preparing the same

AssigneeOtsuka Pharmaceutical Co., Ltd.

InventorsHideyuki Iwaki, Yoshiyasu Fukuyama, Kuniaki Matsui

Life of this patent

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Abstract

1,4-Benzoquinone derivatives and benzene derivatives having cerebral- and cardiac-blood flow improving activities and preventive activities of cerebral ischema with low toxicities, and thus are useful as activators for cardiac and cebral metabolisms, curing agents for heart failure, cardiac and cerebral blood flow improving agents, as well as anti-allergic agents for slow reacting allergy (IV-type allergy).

Claims11

Dependent claims

1,4-benzoquinone compounds or pharmaceutically acceptable salts thereof of the formula ##STR54## wherein R.sup.1 is a lower alkyl group, a lower alkoxy group, an amino group, a hydroxyl group or a lower alkanoyloxy group;

R.sup.2 is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxycarbonyl group, or a hydroxy-lower alkyl group;
R.sup.3 is a hydroxyl group, a lower alkyl group, a lower alkoxy group, an amino group or a lower alkanoyloxy group, A and D are each an alkylene group having 1 to 10 carbon atoms;
B is a group of the formula --CH.dbd.CH--, ##STR55## --C.tbd.C-- or --CH(OH)--CH(OH)--;
l and m are each zero or 1;
and E is a group of the formula, ##STR56## wherein R.sup.4 is a lower alkyl group, a lower alkoxy group, an amino group, a hydroxyl group or a lower alkanoyloxy group;
R.sup.5 is a hydrogen atoms, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy-carbonyl group, or a hydroxy-lower alkyl group;
and R.sup.6 is a lower alkyl group, a hydroxyl group, a lower alkoxy group, an amino group or a lower alkanoyloxy group;
furthermore, when m is 1, then l is zero or 1;
and when m is zero then l is zero, provided that,
(i)
(a) when l is zero and m is zero or 1, then the sum of the number of the carbon atoms in the alkylene groups of A and D is 3 to 12;
(b) when R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each a methyl group at the same time, l is zero and m is zero or 1;
then the sum of the number of the carbon atoms, in the alkylene groups of A and D should not be 3;
(ii) when B is a group of the formula --C.tbd.C--, then
(a) R.sup.1 and R.sup.4 should not be lower alkoxy groups,
(b) R.sup.2, R.sup.3, R.sup.5 and R.sup.6 should not be hydrogen atoms, and
(c) A and D should not be heptamethylene groups, respectively;
(iii) when B is a group of the formula --CH.dbd.CH--, then
(a) R.sup.1 and R.sup.4 should not both be a hydroxyl group at the same time and in the case of either of R.sup.1 or R.sup.4 being a lower alkoxy group, then the other one should not be a lower alkoxy group, a hydroxyl group or a lower alkanoyloxy group,
(b) in the case of either of R.sup.2 or R.sup.5 being a hydrogen atom or a lower alkyl group, then the other one should not be hydrogen atom,
(c) R.sup.3 and R.sup.6 should not both be a hydroxyl group at the same time, a hydrogen atom at the same time, or a lower alkanoyloxy group at the same time and in the case of either of R.sup.3 or R.sup.6 being a hydroxyl group, then the other one should not be a lower alkanoyloxy group, and,
(d) A and D should not be heptamethylene groups, respectively.

19 more elements

Dependencies are inferred from the claim text.

Facts

Application: 07/439,002Filed 21 Nov 1989 · continuation
Priority: JP 59-1303726 Jan 1984
Granted: 15 Jun 1993
Term ends: Not estimatedThe source records don’t support an estimate.

Classification18 codes

C07D 303/32
With hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms: by aldehydo- or ketonic radicals
C07C 43/315
Compounds having [IMAGE cpc-sch-C07C-0958.gif] groups: containing oxygen atoms singly bound to carbon atoms not being acetal carbon atoms
C07C 45/00
Preparation of compounds having >c = o groups bound only to carbon
C07C 45/305
With halogen containing compounds, e.g. hypohalogenation: with halogenochromate reagents, e.g. pyridinium chlorochromate

Family

Serial694,800Parent of this continuation · filed 25 Jan 1985
US 5,220,042 AThis patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

R.sup.2 is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxycarbonyl group, or a hydroxy-lower alkyl group;
R.sup.3 is a hydroxyl group, a lower alkyl group, a lower alkoxy group, an amino group or a lower alkanoyloxy group, A and D are each an alkylene group having 1 to 10 carbon atoms;
B is a group of the formula --CH.dbd.CH--, ##STR55## --C.tbd.C-- or --CH(OH)--CH(OH)--;
l and m are each zero or 1;
and E is a group of the formula, ##STR56## wherein R.sup.4 is a lower alkyl group, a lower alkoxy group, an amino group, a hydroxyl group or a lower alkanoyloxy group;
R.sup.5 is a hydrogen atoms, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy-carbonyl group, or a hydroxy-lower alkyl group;
and R.sup.6 is a lower alkyl group, a hydroxyl group, a lower alkoxy group, an amino group or a lower alkanoyloxy group;
furthermore, when m is 1, then l is zero or 1;
and when m is zero then l is zero, provided that,
(i)
(a) when l is zero and m is zero or 1, then the sum of the number of the carbon atoms in the alkylene groups of A and D is 3 to 12;
(b) when R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each a methyl group at the same time, l is zero and m is zero or 1;
then the sum of the number of the carbon atoms, in the alkylene groups of A and D should not be 3;
(ii) when B is a group of the formula --C.tbd.C--, then
(a) R.sup.1 and R.sup.4 should not be lower alkoxy groups,
(b) R.sup.2, R.sup.3, R.sup.5 and R.sup.6 should not be hydrogen atoms, and
(c) A and D should not be heptamethylene groups, respectively;
(iii) when B is a group of the formula --CH.dbd.CH--, then
(a) R.sup.1 and R.sup.4 should not both be a hydroxyl group at the same time and in the case of either of R.sup.1 or R.sup.4 being a lower alkoxy group, then the other one should not be a lower alkoxy group, a hydroxyl group or a lower alkanoyloxy group,
(b) in the case of either of R.sup.2 or R.sup.5 being a hydrogen atom or a lower alkyl group, then the other one should not be hydrogen atom,
(c) R.sup.3 and R.sup.6 should not both be a hydroxyl group at the same time, a hydrogen atom at the same time, or a lower alkanoyloxy group at the same time and in the case of either of R.sup.3 or R.sup.6 being a hydroxyl group, then the other one should not be a lower alkanoyloxy group, and,
(d) A and D should not be heptamethylene groups, respectively.

19 more elements

Facts

Application

07/439,002Filed 21 Nov 1989 · continuation

Priority

JP 59-1303726 Jan 1984

Granted

15 Jun 1993

Term ends

Not estimatedThe source records don’t support an estimate.

Classification18 codes

C07D 303/32
With hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms: by aldehydo- or ketonic radicals
C07C 43/315
Compounds having [IMAGE cpc-sch-C07C-0958.gif] groups: containing oxygen atoms singly bound to carbon atoms not being acetal carbon atoms
C07C 45/00
Preparation of compounds having >c = o groups bound only to carbon
C07C 45/305
With halogen containing compounds, e.g. hypohalogenation: with halogenochromate reagents, e.g. pyridinium chlorochromate