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Details for Patent: 7,563,811

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Details for Patent: 7,563,811

Title:1,2-dihydropyridine compounds, manufacturing method thereof and use thereof
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. ##STR00001## In the formula, Q indicates NH, O or S; and R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are the same as or different from each other and each indicates hydrogen atom, a halogen atom, a C.sub.1-6 alkyl group or a group represented by the formula --X-A (wherein X indicates a single bond, an optionally substituted C.sub.1-6 alkylene group etc.; and A indicates an optionally substituted C.sub.6-14 aromatic hydrocarbocyclic group or 5- to 14-membered aromatic heterocyclic group etc.).
Inventor(s): Nagato; Satoshi (Chiba, JP), Ueno; Kohshi (Ibaraki, JP), Kawano; Koki (Ibaraki, JP), Norimine; Yoshihiko (Ibaraki, JP), Ito; Koichi (Chiba, JP), Hanada; Takahisa (Ibaraki, JP), Ueno; Masataka (Ibaraki, JP), Amino; Hiroyuki (Ibaraki, JP), Ogo; Makoto (Ibaraki, JP), Hatakeyama; Shinji (Ibaraki, JP), Urawa; Yoshio (Ibaraki, JP), Naka; Hiroyuki (Ibaraki, JP), Groom; Anthony John (Wiltshire, GB), Rivers; Leanne (Kent, GB), Smith; Terence (Cambridgeshire, GB)
Assignee: Eisai R&D Management Co., Ltd. (Bunkyo-ku, JP)
Filing Date:Jul 06, 2005
Application Number:11/174,514
Claims:1. A compound as represented by the following formula (I): ##STR01319## wherein one of X.sup.1, X.sup.2 and X.sup.3 indicates a single bond and the others independently indicate a single bond or an optionally substituted C.sub.1-6 alkylene group, an optionally substituted C.sub.2-6 alkenylene group, an optionally substituted C.sub.2-6 alkynylene group, --O--, --S--, --CO--, --SO--, --SO.sub.2--, --N(R.sup.6)--, --N(R.sup.7)--CO--, --CO--N(R.sup.8)--, --N(R.sup.9)--CH.sub.2--, --CH.sub.2--N(R.sup.10)--, --CH.sub.2--CO--, --CO--CH.sub.2--, --N(R.sup.11)--S(O).sub.m--, --S(O).sub.n--N(R.sup.12)--, --CH.sub.2--S(O).sub.p--, --S(O).sub.q--CH.sub.2--, --CH.sub.2--O--, --O--CH.sub.2--, --N(R.sup.13)--CO--N(R.sup.14)-- or --N(R.sup.15)--CS--N(R.sup.16)-- wherein R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.12, R.sup.13, R.sup.14, R.sup.15 and R.sup.16 independently indicate a hydrogen atom, a C.sub.1-6 alkyl group or a C.sub.1-6 alkoxy group; and m, n, p and q are independent of each other and each independently indicates an integer of 0, 1 or 2, provided that X.sup.1, X.sup.2 and X.sup.3 do not indicate a single bond at the same time; A.sup.1, A.sup.2 and A.sup.3 are the same as or different from each other and each independently indicates an optionally substituted C.sub.3-8 cycloalkyl group, an optionally substituted C.sub.3-8 cycloalkenyl group, an optionally substituted 5 to 14-membered non-aromatic heterocyclic group selected from the group consisting of pyrrolidinyl groups, piperidinyl groups, piperazinyl groups, and morpholinyl groups, an optionally substituted C.sub.6-14 aromatic hydrocarbocyclic group selected from the group consisting of phenyl groups and naphthyl groups, an optionally substituted 5 to 14-membered aromatic heterocyclic group selected from the group consisting of pyrrolyl groups, pyridyl groups, pyrimidinyl groups, pyraziny groups, thienyl groups, thiazolyl groups, furyl groups, guinolyl groups, isoquinolyl groups, indolyl groups, benzimidazolyl groups, benzothiazolyl groups, benzoxazolyl groups, imidazopyridyl groups, carbazolyl groups, and dioxinyl groups, or an adamantyl group; and R.sup.17 and R.sup.18 are the same as or different from each other and each independently indicates a hydrogen atom, a halogen atom or a C.sub.1-6 alkyl group, or a salt thereof.

2. The compound according to claim 1, which is represented by the formula (I), wherein two of X.sup.1, X.sup.2 and X.sup.3 indicate a single bond and the other indicates an optionally substituted C.sub.1-6 alkylene group, an optionally substituted C.sub.2-6 alkenylene group, an optionally substituted C.sub.2-6 alkynylene group, --O--, --S--, --CO--, --SO--, --SO.sub.2--, --N(R.sup.6)--, --N(R.sup.7)--CO--, --CO--N(R.sup.8)--, --N(R.sup.9)--CH.sub.2--, --CH.sub.2--N(R.sup.10)--, --CH.sub.2--CO--, --CO--CH.sub.2--, --N(R.sup.11)--S(O).sub.m--, --S(O).sub.n--N(R.sup.12)--, --CH.sub.2--S(O).sub.p, --S(O).sub.q--CH.sub.2--, --CH.sub.2--O--, --O--CH.sub.2--, --N(R.sup.13)--CO--N(R.sup.14)-- or --N(R.sup.15)--CS--N(R.sup.16)--wherein R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.12, R.sup.13, R.sup.14, R.sup.15 and R.sup.16 indicate a hydrogen atom, a C.sub.1-6 alkyl group or a C.sub.1-6 alkoxy group; and m, n, p and q are independent of each other and each indicates an integer of 0, 1 or 2, or a salt thereof.

3. The compound according to claim 1, or a salt thereof, wherein A.sup.1, A.sup.2 and A.sup.3 are the same as or different from each other and each independently indicates C.sub.3-8 cycloalkyl group, C.sub.3-8 cycloalkenyl group, 5 to 14-membered non-aromatic heterocyclic group, C.sub.6-14 aromatic hydrocarbocyclic group or 5 to 14-membered aromatic heterocyclic group, each of which may be substituted with one or more groups selected from the following substituent group b: <Substituent group b>: the group consisting of(1) hydroxy group, (2) a halogen atom, (3) nitrile group, (4) nitro group, (5) a C.sub.1-6 alkyl group, a C.sub.2-6 alkenyl group or a C.sub.2-6 alkynyl group which may be optionally substituted respectively with one or more groups selected from the group consisting of hydroxy group, nitrile group, a halogen atom, a C.sub.1-6 alkylamino group, a di-(C.sub.1-6 alkyl)amino group, a C.sub.2-6 alkenylamino group, a di(C.sub.2-6 alkenylamino) group, a C.sub.2-6 alkynylamino group, a di(C.sub.2-6 alkynylamino) group, an N--C.sub.1-6 alkyl-N--C.sub.2-6 alkenylamino group, an N--C.sub.1-6 alkyl-N--C.sub.2-6 alkynylamino group, an N--C.sub.2-6 alkenyl-N--C.sub.2-6 alkynylamino group, an aralkyloxy group, a TBDMS oxy group, a C.sub.1-6 alkylsulfonylamino group, a C.sub.1-6 alkylcarbonyloxy group, a C.sub.2-6 alkenylcarbonyloxy group, a C.sub.2-6 alkynylcarbonyloxy group, an N--C.sub.1-6 alkylcarbamoyl group, an N--C.sub.2-6 alkenylcarbanoyl group and an N--C.sub.1-6 alkynylcarbamoyl group, (6) a C.sub.1-6 alkoxy group, a C.sub.2-6 alkenyloxy group or a C.sub.2-6 alkynyloxy group which may be optionally substituted respectively with one or more groups selected from the group consisting of a C.sub.1-6 alkylamino group, an aralkyloxy group and hydroxy group, (7) a C.sub.1-6 alkylthio group, a C.sub.2-6 alkenylthio group or a C.sub.2-6 alkynylthio group which may be optionally substituted respectively with one or more groups selected from the group consisting of hydroxy group, nitrile group, a halogen atom, a C.sub.1-6 alkylamino group, an aralkyloxy group, a TBDMS oxy group, a C.sub.1-6 alkylsulfonylamino group, a C.sub.1-6 alkylcarbonyloxy group and a C.sub.1-6 alkylcarbamoyl group, (8) a carbonyl group substituted with a group selected from the group consisting of a C.sub.1-6 alkoxy group, amino group, a C.sub.1-6 alkylamino group, a di(C.sub.1-6 alkyl)amino group, a C.sub.2-6 alkenylamino group, a di(C.sub.2-6 alkenyl)amino group, a C.sub.2-6 alkynylamino group, a di(C.sub.2-6 alkynyl)amino group, an N--C.sub.1-6 alkyl-N--C.sub.2-6 alkenylamino group, an N--C.sub.1-6 alkyl-N--C.sub.2-6 alkynylamino group and an N--C.sub.2-6 alkenyl-N--C.sub.2-6 alkynylamino group, (9) amino group which may be optionally substituted with one or two groups selected from the group consisting of a C.sub.1-6 alkyl group, a C.sub.2-6 alkenyl group, a C.sub.2-6 alkynyl group, a C.sub.1-6 alkylsulfonyl group, a C.sub.2-6 alkenylsulfonyl group, a C.sub.2-6 alkynylsulfonyl group, a C.sub.1-6 alkylcarbonyl group, a C.sub.2-6 alkenylcarbonyl group and a C.sub.2-6 alicynylcarbonyl group, (10) a C.sub.1-6 alkylsulfonyl group, (11) a C.sub.2-6 alkenylsulfonyl group, (12) a C.sub.2-6 alkynylsulfonyl group, (13) a C.sub.1-6 alkylsulfinyl group, (14) a C.sub.2-6 alkenylsulfinyl group, (15) a C.sub.2-6 alkynylsulfmyl group, (16) a formyl group, (17) a C.sub.3-8 cycloalkyl group or a C.sub.3-8 cycloalkenyl group which may be optionally substituted respectively with one or more groups selected from the group consisting of hydroxy group, a halogen atom, nitrile group, a C.sub.1-6 alkyl group, a C.sub.1-6 alkyloxy group, a C.sub.1-6 alkyloxy C.sub.1-6 alkyl group and an aralkyl group, (18) a 5- to 14-membered non-aromatic heterocyclic group which may be optionally substituted with one or more groups selected from the group consisting of hydroxy group, a halogen atom, nitrile group, a C.sub.1-6 alkyl group, a C.sub.1-6 alkyloxy group, a C.sub.1-6 alkyloxy C.sub.1-6 alkyl group and an aralkyl group, (19) a C.sub.6-14 aromatic hydrocarbocyclic group which may be optionally substituted with one or more groups selected from the group consisting of hydroxy group, a halogen atom, nitrile group, a C.sub.1-6 alkyl group, a C.sub.1-6 alkyloxy group, a C.sub.1-6 alkyloxy C.sub.1-6 alkyl group and an aralkyl group, and (20) a 5- to 14-membered aromatic heterocyclic group which may be optionally substituted with one or more groups selected from the group consisting of hydroxy group, a halogen atom, nitrile group, a C.sub.1-6 alkyl group, a C.sub.1-6 alkyloxy group, a C.sub.1-6 alkyloxy C.sub.1-6 alkyl group and an aralkyl group.

4. The compound according to claim 1, or a salt thereof, wherein A.sup.1, A.sup.2 and A.sup.3 are the same as or different from each other and each indicates an optionally substituted C.sub.6-14 aromatic hydrocarbocyclic group or 5 to 14-membered aromatic heterocyclic group.

5. The compound according to claim 1, or a salt thereof, wherein A.sup.1,A.sup.2 and A.sup.3 are the same as or different from each other and each represents a phenyl group or a pyridyl group, each of which may be substituted.

6. The compound according to claim 1, or a salt thereof, wherein the compound is 3-(2-cyanophenyl)-5-(2-pyridyl)- 1 -benzyl- 1 ,2-dihydropyridin-2-one.

7. A compound as represented by the following formula (I): ##STR01320## wherein one of X.sup.1, X.sup.2 and X.sup.3 indicates a single bond and the others independently indicate a single bond or an optionally substituted C.sub.1-6 alkylene group, an optionally substituted C.sub.2-6 alkenylene group, an optionally substituted C.sub.2-6 alkynylene group, --O--, --S--, --CO--, --SO--, --SO.sub.2--, --N(R.sup.6)--, --N(R.sup.7)--CO--, --CO--N(R.sup.8)--, --N(R.sup.9)--CH.sub.2--, --CH.sub.2--N(R.sup.10)--, --CH .sub.2--CO--, --CO--CH.sub.2--, --N(R.sup.11)--S(O).sub.m--, --S(O).sub.n--N(R.sup.12)--, --CH.sub.2--S(O).sub.p--, --S(O).sub.q--CH.sub.2--, --CH.sub.2--O--, --O--CH.sub.2--, --N(R.sup.13)--CO--N(R.sup.14)-- or --N(R.sup.15)--CS--N(R.sup.16)-- wherein R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.12, R.sup.13, R.sup.14, R.sup.15 and R.sup.16 independently indicate a hydrogen atom, a C.sub.1-6 alkyl group or a C.sub.1-6 alkoxy group; and m, n, p and q are independent of each other and each independently indicates an integer of 0. 1 or 2 provided that X.sup.1, X.sup.2 and X.sup.3 do not indicate a single bond at the same time; A.sup.1,A.sup.2 and A.sup.3 are the same as or different from each other and each indicates an optionally substituted phenyl group, pyrrolyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, thienyl group, thiazolyl group, furyl group, naphthyl group, quinolyl group, iso-quinolyl group, indolyl group, benzimidazolyl group, benzothiazolyl group, benzoxazolyl group, imidazopyridyl group, carbazolyl group, cyclopentyl group, cyclohexyl group, cyclohexenyl group, dioxinyl group, adamantyl group, pyrrolidinyl group, piperidinyl group, piperazinyl group or morpholinyl group; R.sup.17 and R.sup.18 are the same as or different from each other and each independently indicates a hydrogen atom, a halogen atom or a C.sub.1-6 alkyl group, or a salt thereof.

8. A pharmaceutical composition comprising an effective amount of a compound as claimed in claim 1 in combination with a pharmaceutically acceptable carrier.

9. A process for treating Parkinson's disease, Parkinson's syndrome, epilepsy, or multiple sclerosis, by dosing a pharmacologically effective dose of the compound as represented by the following formula(I): ##STR01321## wherein one of X.sup.1, X.sup.2 and X.sup.3 indicates a single bond and the others independently indicate a single bond or an optionally substituted C.sub.1-6 alkylene group, an optionally substituted C.sub.2-6 alkenylene group, an optionally substituted C.sub.2-6 alkynylene group, --O--, --S--, --CO--, --SO--, --SO.sub.2--, --N(R.sup.6)--, --N(R.sup.7)--CO--, --CO--N(R.sup.8)--, --N(R.sup.9)--CH.sub.2--, --CH.sub.2--N(R.sup.10)--, --CH.sub.2--CO--, --CO--CH.sub.2--, --N(R.sup.11)--S(O).sub.m--, --S(O).sub.n--N(R.sup.12)--, --CH.sub.2--S(O).sub.p--, --S(O).sub.q--CH.sub.2--, --CH.sub.2--O--, --O--CH.sub.2--, --N(R.sup.13)--CO--N(R.sup.14)-- or --N(R.sup.15)--CS--N(R.sup.16)-- wherein R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.12, R.sup.13, R.sup.14, R.sup.15 and R.sup.16 independently indicate a hydrogen atom, a C.sub.1-6 alkyl group or a C.sub.1-6 alkoxy group; and m, n, p and q are independent of each other and each independently indicates an integer of 0, 1 or 2, provided that X.sup.1, X.sup.2 and X.sup.3 do not indicate a single bond at the same time; A.sup.1, A.sup.2 and A.sup.3 are the same as or different from each other and each independently indicates an optionally substituted C.sub.3-8 cycloalkyl group, an optionally substituted C.sub.3-8cycloalkenyl group, an optionally substituted 5 to 14-membered non-aromatic heterocyclic group, an optionally substituted C.sub.6-14 aromatic hydrocarbocyclic group or an optionally substituted 5 to 14-membered aromatic heterocyclic group; and R.sup.17 and R.sup.18 are the same as or different from each other and each independently indicates a hydrogen atom, a halogen atom or a C.sub.1-6 alkyl group, or a salt thereof to a patient afflicted by the stated condition.
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