US 2004/0023973 A1Published application

1,2-Dihydropyridine compounds, process for preparation of the same and use thereof

AssigneeEisai Co., Ltd.

InventorsSatoshi Nagato, Kohshi Ueno, Koki Kawano, Yoshihiko Norimine, Koichi Ito, Takahisa Hanada, Masataka Ueno, Hiroyuki Amino, Makoto Ogo, Shinji Hatakeyama, Yoshio Urawa, Hiroyuki Naka, Anthony John Groom, Leanne Rivers

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Abstract

The present invention provides a novel compound having an excellent AMPA receptor inhibitory action and/or kainate inhibitory action. A compound represented by the following formula, a salt thereof or hydrates thereof. 1 In the formula, Q indicates NH, O or S; and R1, R2, R3, R4 and R5 are the same as or different from each other and each indicates hydrogen atom, a halogen atom, a C1-6 alkyl group or a group represented by the formula —X-A (wherein X indicates a single bond, an optionally sbutituted C1-6 alkylene group etc.; and A indicates an optionally substituted C6-14 aromatic hydrocarbocyclic group or 5- to 14-membered aromatic heterocyclic group etc.).

Claims99

Dependent claims

A compound represented by the following formula, a salt thereof or hydrates thereof.

1319
In the formula, Q indicates NH, O or S;
and R1, R2, R3, R4 and R5 are the same as or different from each other and each indicates hydrogen atom, a halogen atom, a C1-6 alkyl group or a group represented by the formula —X-A (wherein X indicates a single bond, an optionally substituted C1-6 alkylene group an optionally substituted C2-6 alkenylene group, an optionally substituted C2-6alkynylene group, —O—, —S—, —CO—, —SO—, —SO2—, —N(R6)—, —N(R7)—CO—, —CO—N(R8)—, —N(R9)—CH2—, —CH2—N(R10)—, —CH2—CO—, —CO—CH2—, —N(R11)—S(O)m—, —S(On—N(R12)—, —CH2—S(O)p—, —S(O)q—CH2—, —CH2—O—, —O—CH2—, —N(R13)—CO—N(R14)— or —N(R15)—CS—N(R16)— (wherein R6, R7, R8, R9, R10, R11, R12 R13 R14 R15 and R16 indicate hydrogen atom, a C1-6 alkyl group or a C1-6 alkoxy group;
and m, n, p and q indicates an integer of 0, 1 or 2 independently);
and A indicates a C3-8 cycloalkyl group, a C3-8 cycloalkenyl group, a 5 to 14 membered non-aromatic heterocyclic group, a C6-4 aromatic hydrocarbocyclic group, or a 5 to 14 membered aromatic heterocyclic group which may be substituted respectively, provided that 3 groups among R1, R2, R3, R4 and R5 are always the same as or different from each other and each indicates —X-A;
and the residual 2 groups always indicate hydrogen atom, a halogen atom or a C1-6 alkyl group), provided that in the above-mentioned definition, the cases where (1) Q is O;
R1 and R5 are hydrogen atoms;
and R2, R3 and R4 are phenyl groups, (2) Q is O;
R1 and R4 are hydrogen atoms;
and R2, R3 and R5 are phenyl groups, and (3) Q is O;
R1 and R2 are hydrogen atoms;
and R3, R4 and R5 are phenyl groups, are excluded.

9 more elements

A process for producing a compound represented by the formula:

1326
(wherein A1a and A3a have the same meanings as defined above) or a salt thereof, which comprises subjecting the compound represented by the formula:
1327
(wherein A3a has the same meaning as defined above) or a salt thereof and a boronic acid derivative represneted by the formula A1aB(OH)2 (wherein A1a represents optionally substituted C6-14 aromatic hydrocarbon ring or 5- to 14-membered aromatic heteroring) to a coupling reaction in the presence of a copper compound.

1 more element

A process for producing a compound represented by the formula:

1334
(wherein, the ring D and the ring E have the same meanings as defined above) or a salt thereof, which comprises subjecting the compound represented by the formula:
1335
(wherein the ring D has the same meaning as defined above) or a salt thereof and a boronic acid derivative represented by the formula PhB(OH)2 (wherein Ph indicates an optionally substituted phenyl group) to a coupling reaction in the presence of a copper compound.

1 more element

A pharmaceutical composition comprising a compound represented by the following formula, a salt thereof or hydrates thereof.

1341
In the formula, Q indicates NH, O or S;
and R1, R2, R3, R4 and R5 are the same as or different from each other and each indicates hydrogen atom, a halogen atom, a C1-6 alkyl group or the formula —X-A (wherein X indicates a single bond, a C1-6 alkylene group which may optionally have substituents, a C2-6 alkenylene group which may optionally have substituents, a C2-6 alkynylene group which may optionally have substituents, —O—, —S—, —CO—, —SO—, —SO2—, —N(R6)—, —N(R7)—CO—, —CO—N(R8)—, —N(R9)—CH2—, —CH2—N(R10)—, —CH2—CO—, —CO—CH2—, —N(R11)—S(O)m—, —S(O)n—N(R12)—, —CH2—S(O)p—, —S(O)qCH2—, —CH2—O—, —O—CH2—, —N(R3)—CO—N(R4)— or —N(R5)—CS—N(R16)— (wherein R6, R7, R8, R9, R10, R11, R12, R13, R14, R15 and R16 indicates hydrogen atom, a C1-6alkyl group or a C1-6 alkoxy group;
and m, n, p and q are independent of each other and each indicates an integer of 0, 1 or 2);
and A indicates optionally substituted C3-8 cycloalkyl group, C3-8 cycloalkenyl group, 5- to 14-membered non-aromatic heterocyclic group, C6-14 aromatic hydrocarbocyclic group or 5-to 14-membered aromatic heterocyclic group), provided that 3 groups among R1, R2, R3, R4 and R5 are always the same as or different from each other and each indicates —X-A;
and the residual 2 groups always indicate hydrogen atom, a halogen atom or a C1-6alkyl group.

3 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/296,719Filed 26 Nov 2002
Priority: JP 2000-17596612 Jun 2000
Published: 5 Feb 2004
Term ends: Not estimatedThe source records don’t support an estimate.

Classification49 codes

C07D 213/70
Oxygen or sulfur atoms: sulfur atoms
A61P 1/08
Drugs for disorders of the alimentary tract or the digestive system: for nausea, cinetosis or vertigo; Antiemetics
A61P 9/10
Drugs for disorders of the cardiovascular system: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary…
A61P 13/00
Drugs for disorders of the urinary system