CA2570606A1 - Novel sulfamate and sulfamide derivatives useful for the treatment of epilepsy and related disorders - Google Patents

Novel sulfamate and sulfamide derivatives useful for the treatment of epilepsy and related disorders Download PDF

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Publication number
CA2570606A1
CA2570606A1 CA002570606A CA2570606A CA2570606A1 CA 2570606 A1 CA2570606 A1 CA 2570606A1 CA 002570606 A CA002570606 A CA 002570606A CA 2570606 A CA2570606 A CA 2570606A CA 2570606 A1 CA2570606 A1 CA 2570606A1
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CA
Canada
Prior art keywords
benzo
dihydro
dioxinyl
group
compound
Prior art date
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Granted
Application number
CA002570606A
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French (fr)
Other versions
CA2570606C (en
Inventor
David F. Mccomsey
Michael H. Parker
Allen B. Reitz
Bruce E. Maryanoff
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Janssen Pharmaceutica NV
Original Assignee
Janssen Pharmaceutica, N.V.
David F. Mccomsey
Michael H. Parker
Allen B. Reitz
Bruce E. Maryanoff
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Application filed by Janssen Pharmaceutica, N.V., David F. Mccomsey, Michael H. Parker, Allen B. Reitz, Bruce E. Maryanoff filed Critical Janssen Pharmaceutica, N.V.
Publication of CA2570606A1 publication Critical patent/CA2570606A1/en
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Publication of CA2570606C publication Critical patent/CA2570606C/en
Expired - Fee Related legal-status Critical Current
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
    • C07D321/02—Seven-membered rings
    • C07D321/10—Seven-membered rings condensed with carbocyclic rings or ring systems

Abstract

The present invention is directed to novel sulfamide and sulfamate derivatives, pharmaceutical composlons containing them and their use in the treatment of epilepsy and related disorders.

Claims (15)

1. A compound of formula (II) IMG>
wherein R1 and R2 are each independently selected from the group consisting of hydrogen and lower alkyl;
R4 is selected from the group consisting of hydrogen and lower alkyl;
a is an integer from 1 to 2;

is selected from the group consisting of wherein b is an integer from 0 to 4; and wherein c is an integer from 0 to 2;

each R5 is independently selected from the group consisting of halogen, lower alkyl and nitro;

provided that when then a is 1;
or a pharmaceutically acceptable salt thereof.
2. A compound as in Claim 1 wherein R1 and R2 are each independently selected from the group consisting of hydrogen and lower alkyl;
R4 is selected from the group consisting of hydrogen and lower alkyl;
a is an integer from 1 to 2;

is selected from the group consisting of wherein b is an integer from 0 to 2; and wherein c is an integer from 0 to 1;
each R5 is independently selected from the group consisting of halogen, lower alkyl and nitro;

provided that when then a is 1;
or a pharmaceutically acceptable salt thereof.
3. A compound as in Claim 2 wherein R1 and R2 are each independently selected from the group consisting of hydrogen and lower alkyl;
R4 is selected from the group consisting of hydrogen and lower alkyl;
a is an integer from 1 to 2;

is selected from the group consisting of wherein b is an integer from 0 to 2; and wherein c is 0;
each R5 is independently selected from the group consisting of halogen, lower alkyl and nitro;

provided that when then a is 1;
or a pharmaceutically acceptable salt thereof.
4. A compound as in Claim 3 wherein R' and R2 are each independently selected from the group consisting of hydrogen and lower alkyl;
R4 is selected from the group consisting of hydrogen and methyl;
a is an integer from 1 to 2;

<1MG>
is selected from the group consisting of 2-(2,3-dihydro-benzo[1,4]dioxinyl), 2-(benzo[1,3]dioxolyl), 3-(3,4-dihydro-2H-benzo[1,4]dioxepinyl), 2-(2,3-dihydro-benzo[1,4]dioxinyl), 2-(6-chloro-2,3-dihydro-benzo[1,4]dioxinyl), 2-(6-fluoro-2,3-dihydro-benzo[1,4]dioxinyl), 2-(chromanyl), 2-(5-fluoro-2,3-dihydro-benzo[1,4]dioxinyl), 2-(7-chloro-2,3-dihydro-benzo[1,4]dioxinyl), 2-(6-chloro-benzo[1,3]dioxolyl), 2-(7-nitro-2,3-dihydro-benzo[1,4]dioxinyl), 2-(7-methyl-2,3-dihydro-benzo[1,4]dioxinyl), 2-(5-chloro-2,3-dihydro-benzo[1,4]dioxinyl), 2-(6-bromo-2,3-dihydro-benzo[1,4]dioxinyl), 2-(6,7-dichloro-2,3-dihydro-benzo[1,4]dioxinyl), 2-(3-chloro-2,3-dihydro-benzo[1,4]dioxinyl), 2-(2,3-dihydro-naphtho[2,3-b][1,4]dioxinyl) and 2-(4-methyl-benzo[1,3]dioxolyl);

provided that when is 3-(3,4-dihydro-2H-benzo[1,4]dioxepinyl), then a is 1;
or a pharmaceutically acceptable salt thereof.
5. A compound as in Claim 4 wherein R1 and R2 are each independently selected from the group consisting of hydrogen and methyl;
R4 is selected from the group consisting of hydrogen and methyl;
a is an integer from 1 to 2;

is selected from the group consisting of 2-(benzo[1,3]dioxolyl), 2-(2,3-dihydro-benzo[1,4]dioxinyl), 2-(2,3-dihydro-benzo[1,4]dioxinyl), 2-(6-chloro-2,3-dihydro-benzo[1,4]dioxinyl), 2-(7-chloro-2,3-dihydro-benzo[1,4]dioxinyl), 2-(7-methyl-2,3-dihydro-benzo[1,4]dioxinyl), 2-(6-bromo-2,3-dihydro-benzo[1,4]dioxinyl) and 2-(6,7-dichloro-2,3-dihydro-benzo[1,4]dioxinyl);
or a pharmaceutically acceptable salt thereof.
6. A compound selected from the group consisting of N-[(6-chloro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-sulfamide and pharmaceutically acceptable salts thereof.
7. A compound selected from the group consisting of and pharmaceutically acceptable salts thereof.
8. A compound of the formula (III) or a pharmaceutically acceptable salt thereof.
9. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound of Claim 1.
10. A pharmaceutical composition made by mixing a compound of Claim I
and a pharmaceutically acceptable carrier.
11. A process for making a pharmaceutical composition comprising mixing a compound of Claim 1 and a pharmaceutically acceptable carrier.
12. A method of treating epilepsy or a related disorder, in a subject in need thereof comprising administering to the subject a therapeutically effective amount of the compound of Claim 1.
13. A method of treating epilepsy, in a subject in need thereof comprising administering to the subject a therapeutically effective amount of the compound of Claim 1.
14. A method as in Claim 12, wherein the disorder is selected from essential tremor or restless limb syndrome.
15. The use of compound as in Claim 1 in the preparation of a medicament for treating epilepsy or a related disorder, in a subject in need thereof.
CA2570606A 2004-06-16 2005-06-16 Novel sulfamate and sulfamide derivatives useful for the treatment of epilepsy and related disorders Expired - Fee Related CA2570606C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US58017804P 2004-06-16 2004-06-16
US60/580,178 2004-06-16
PCT/US2005/021513 WO2006007435A1 (en) 2004-06-16 2005-06-16 Sulfamate and sulfamide derivatives for the treatment of epilepsy and related disorders

Publications (2)

Publication Number Publication Date
CA2570606A1 true CA2570606A1 (en) 2006-01-19
CA2570606C CA2570606C (en) 2013-04-30

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CA2570606A Expired - Fee Related CA2570606C (en) 2004-06-16 2005-06-16 Novel sulfamate and sulfamide derivatives useful for the treatment of epilepsy and related disorders

Country Status (22)

Country Link
US (1) US8084490B2 (en)
EP (1) EP1768970B1 (en)
JP (2) JP4884378B2 (en)
CN (1) CN101006072B (en)
AR (2) AR049398A1 (en)
AU (1) AU2005262496B2 (en)
BR (1) BRPI0512242A (en)
CA (1) CA2570606C (en)
CR (1) CR8858A (en)
EA (1) EA013685B1 (en)
EC (1) ECSP067093A (en)
ES (1) ES2573844T3 (en)
IL (1) IL180108A (en)
MX (1) MXPA06014934A (en)
MY (1) MY147767A (en)
NI (1) NI200600306A (en)
NO (1) NO20070081L (en)
NZ (1) NZ552056A (en)
TW (1) TWI361691B (en)
UA (1) UA91680C2 (en)
WO (1) WO2006007435A1 (en)
ZA (1) ZA200700430B (en)

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