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US 2026/0146034 A1Published application
1h-cyclopenta[b]benzofuran derivatives for the prevention and treatment of virus diseases
AssigneeSJP Biotec GmbH
InventorKrishnaraj Rajalingam
Life of this patent
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Abstract
The present invention relates to new therapeutic uses of 1 H-Cyclopenta[b]benzofuran derivatives, specifically new uses for the treatment or prevention of a disease caused by virus infections or a disease associated with virus infections. The invention further relates to a method of treatment or prevention of diseases caused by virus infections or diseases associated with virus infections. Moreover, the invention relates to a pharmaceutical composition for use in the treatment or prevention of diseases caused by virus infections or diseases associated with virus infections.
Claims20
A process for use in treatment or prevention of a disease caused by a virus infection in a subject in need thereof, wherein the disease results from a virus infection caused by a positive single-stranded RNA virus ((+) ssRNA) or a negative single-stranded RNA virus ((−) ssRNA), comprising administering to the subject a compound of formula (I)
- or a pharmaceutically acceptable salt thereof, wherein
- R1 is selected from C1-C4 alkyl, wherein alkyl is unsubstituted or substituted by 1, 2 or 3 substituents Ra;
- C3-C7 heterocyloalkyl, comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NRc, O, S, SO and SO2, and wherein the heterocyloalkyl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals Re and wherein the heterocyloalkyl is connected to the remaining molecule via a carbon atom;
- NR2R3, wherein R2 and R3 independently from each other are selected from hydrogen, C1-C4 alkyl, C3-C7 cycloalkyl and C3-C7 heterocyloalkyl, comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NRc, O, S, SO and SO2, and wherein the heterocyloalkyl is unsubstituted or substituted by 1, 2 or 3 substituents Rh and wherein alkyl is unsubstituted or substituted by 1, 2 or 3 substituents Ra, wherein cycloalkyl is unsubstituted or substituted by 1, 2 or 3 substituents Rb;
- R2 and R3 together with the nitrogen atom, which they are attached to, form a 3-, 4-, 5-, 6-, or 7-membered saturated or partly unsaturated heterocyclic ring, wherein the heterocyclic ring has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NRc, O, S, SO and SO2, and wherein the heterocyclic ring is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals Rd;
- R2 and R3 together with the nitrogen atom, which they are attached to, form a saturated or partly unsaturated bi-, tri- or tetracyclic ring system, comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NRc, O, S, SO and SO2, and wherein the heterocyclic ring is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R′;
- R2 and R3 together with the nitrogen atom, which they are attached to, form a saturated or partly unsaturated spiro moiety, comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NRc, O, S, SO and SO2, and wherein the heterocyclic ring is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals Rg;
- Ra is selected from halogen, OH, C3-C7 cycloalkyl, C1-C3 alkoxy, phenyl, NR5aR5b, C1-C4-alkylsulfonyl, C3-C7 heterocyloalkyl, comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NRc, O, S, SO and SO2, and wherein the heterocyloalkyl is unsubstituted or substituted by 1, 2 or 3 substituents selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl and wherein C3-C7 cycloalkyl and phenyl is unsubstituted or substituted by 1, 2 or 3 substituents selected from F, Cl, Br and OH;
- Rb is selected from halogen, OH and C1-C3 alkoxy;
- Rc is selected from hydrogen, C1-C4-alkyl, C3-C7 cycloalkyl, C1-C4-haloalkyl, C1-C4-cyanoalkyl, carbonyloxy-C1-C4-alkyl and C1-C4-hydroxyalkyl;
- Rd is selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, carboxy, carbonyloxy-C1-C4-alkyl and NR5aR5b;
- Re is selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy, carbonyloxy-C1-C4-alkyl and C1-C4-haloalkoxy;
- Rf is selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and NR5aR5b;
- R4 is selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
- Rh is selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
- R4 is selected from Cl, CN and C3-C7 cycloalkyl;
- R5a and R5b independently of each other are selected from hydrogen, C1-C4-alkyl and C3-C7 cycloalkyl;
- R6 is selected from hydrogen and F;
- R7 is selected from hydrogen and C1-C2-alkyl;
- with the proviso that, if R6 is H, R7 is C1-C2-alkyl and if Re is F, R7 is hydrogen;
- R& is selected from OCH3, OCD3;
- and
- R9 is selected from OCH3, OCD3.
20 more elements
A process of inhibiting virus activity in a subject in need thereof comprising administering to the subject a compound of formula (I)
- or a pharmaceutically acceptable salt thereof, wherein
- R1 is selected from C1-C4 alkyl, wherein alkyl is unsubstituted or substituted by 1, 2 or 3 substituents Ra;
- C3-C7 heterocyloalkyl, comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NRc, O, S, SO and SO2, and wherein the heterocyloalkyl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals Re and wherein the heterocyloalkyl is connected to the remaining molecule via a carbon atom;
- NR2R3, wherein R2 and R3 independently from each other are selected from hydrogen, C1-C4 alkyl. C3-C7 cycloalkyl and C3-C7 heterocyloalkyl, comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NRc, O, S, SO and SO2, and wherein the heterocyloalkyl is unsubstituted or substituted by 1, 2 or 3 substituents Rh and wherein alkyl is unsubstituted or substituted by 1, 2 or 3 substituents Ra, wherein cycloalkyl is unsubstituted or substituted by 1, 2 or 3 substituents Rb;
- R2 and R3 together with the nitrogen atom, which they are attached to, form a 3-, 4-, 5-, 6-, or 7-membered saturated or partly unsaturated heterocyclic ring, wherein the heterocyclic ring has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NRc, O, S, SO and SO2, and wherein the heterocyclic ring is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals Rd;
- R2 and R3 together with the nitrogen atom, which they are attached to, form a saturated or partly unsaturated bi-tr or tetracyclic ring system, comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NRc, O, S, SO and SO2, and wherein the heterocyclic ring is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals Rf;
- R2 and R3 together with the nitrogen atom, which they are attached to, form a saturated or partly unsaturated spiro moiety, comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NRc, O, S, SO and SO2, and wherein the heterocyclic ring is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals Rg;
- Ra is selected from halogen, OH, C3-C7 cycloalkyl, C1-C3 alkoxy, phenyl, NR5aR5b, C1-C4-alkylsulfonyl, C3-C7 heterocyloalkyl, comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NRc, O, S, SO and SO2, and wherein the heterocyloalkyl is unsubstituted or substituted by 1, 2 or 3 substituents selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl and wherein C3-C7 cycloalkyl and phenyl is unsubstituted or substituted by 1, 2 or 3 substituents selected from F, Cl, Br and OH;
- Rb is selected from halogen, OH and C1-C3 alkoxy;
- Rc is selected from hydrogen, C1-C4-alkyl, C3-C7 cycloalkyl, C1-C4-haloalkyl, C1-C4-cyanoalkyl, carbonyloxy-C1-C4-alkyl and C1-C4-hydroxyalkyl;
- Rd is selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, carboxy, carbonyloxy-C1-C4-alkyl and NR5aR5b;
- Re is selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy, carbonyloxy, C1-C4-alkyl and C1-C4-haloalkoxy;
- Rf is selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and NR5aR5b;
- Rg is selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
- Rh is selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
- R4 is selected from Cl, CN and C3-C7 cycloalkyl;
- R5a and R5b independently of each other are selected from hydrogen. C1-C4-alkyl and C3-C7 cycloalkyl:
- R8 is selected from hydrogen and F;
- R7 is selected from hydrogen and C1-C2-alkyl;
- with the proviso that, if R6 is H, R7 is C1-C2-alkyl and if R6 is F, R7 is hydrogen;
- R6 is selected from OCH3, OCD3, and
- R9 is selected from OCH3, OCD3.
19 more elements
(canceled)
A pharmaceutical composition comprising at least one compound of formula (I)
- wherein
- R1 is selected from C1-C4 alkyl, wherein alkyl is unsubstituted or substituted by 1, 2 or 3 substituents Ra;
- C3-C7 heterocyloalkyl, comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NRc, O, S, SO and SO2, and wherein the heterocyloalkyl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals Ra and wherein the heterocyloalkyl is connected to the remaining molecule via a carbon atom;
- NR2R3, wherein R2 and R3 independently from each other are selected from hydrogen, C1-C4 alkyl, C3-C7-cycloalkyl and C3-C7 heterocyloalkyl, comprising 1, 2 or 3 identical of different heteroatoms or hetercatom-containing groups as ring members, selected from N. NRc, O, S, SO and SO2, and wherein the heterocyclalkyl is unsubstituted or substituted by 1, 2 or 3 substituents Rh and wherein alkyl is unsubstituted or substituted by 1, 2 or 3 substituents Ra, wherein cycloalkyl is unsubstituted or substituted by 1, 2 or 3 substituents Rb;
- R2 and R3 together with the nitrogen atom, which they are attached to, form a 3-, 4-, 5-, 6-, or 7-membered saturated or partly unsaturated heterocyclic ring, wherein the heterocyclic ring has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NRcO, S, SO and SO2, and wherein the heterocyclic ring is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals Rd;
- R2 and R3 together with the nitrogen atom, which they are attached to, form a saturated or partly unsaturated bi-, tri- or tetracyclic ring system, comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NRc, O, S, SO and SO2, and wherein the heterocyclic ring is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals Rf;
- R2 and R3 together with the nitrogen atom, which they are attached to, form a saturated or partly unsaturated spiro moiety, comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NRc, O, S, SO and SO2, and wherein the heterocyclic ring is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicais Rg;
- Ra is selected from halogen, OH, C3-C7 cycloalkyl. C1-C3 alkoxy, phenyl, NR5aR5b, C1-C4-alkylsulfonyl, C3-C7 heterocyioalkyl, comprising 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, selected from N, NRc, O, S, SO, and SO2, and wherein the heterocyloalkyl is unsubstituted or substituted by 1, 2 or 3 substituents selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl and wherein C3-C7 cycloalkyl and phenyl is unsubstituted or substituted by 1, 2 or 3 substituents selected from F, Cl, Br and OH:
- Rb is selected from halogen, OH and C1-C3 alkoxy;
- Rc is selected from hydrogen, C1-C4-alkyl, C3-C7 cycloalkyl, C1-C4-haloalkyl, C1-C4-cyanoalkyl carbonyloxy-C1-C4-alkyl and C1-C4-hydroxyalkyl;
- Rd is selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, carboxy, carbonyloxy-C1-C4-alkyl and NR5aR5b;
- Re is selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy carbonyloxy-C1-C4-alkyl and C1-C4-haloalkoxy;
- Rf is selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and NR5aR5b.
- Rg is selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
- Rh is selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
- R4 is selected from Cl, CN and C3-C7 cycloalkyl;
- R5a and R5b independently of each other are selected from hydrogen, C1-C4-alkyl and C3-C7 cycloalkyl;
- R8 is selected from hydrogen and F;
- R7 is selected from hydrogen and C1-C2-alkyl;
- with the proviso that, if R6 is H, R7 is C1-C2-alkyl and if R6 is F, R7 is hydrogen;
- R8 is selected from OCH3, OCD3;
- and
- R9 is selected from OCH3, OCD3, pharmaceutically acceptable salts thereof and a pharmaceutically acceptable diluent or carrier.
20 more elements
Dependencies are inferred from the claim text.