Evermectin derivatives

Abstract

A compound represented by general formula (I): [in formula (I), n represents an integer of 0 to 2; X represents CH, CF, CCl, N, CHCH=N, CHCH=CH, or CHCH=CF; Y represents O, NH, or a single bond; Z represents a hydroxy group or an oxo group; R1 represents a hydrogen atom, a C1 to C6 alkyl group, a three- to six-membered cycloalkyl group, a four- to eight-membered heterocycloalkyl group, a six- to ten-membered aryl group, a five- to ten-membered heteroaryl group, a C2 to C6 alkenyl group, a C2 to C6 alkynyl group, a group represented by -CO-R2, a group represented by -COO-R2, a group represented by -CONH-R2, or a group represented by -B(OR4)OR5, and these groups may be substituted; R2, R4, and R5 each represent a hydrogen atom, alkyl group, etc.] or a pharmaceutically acceptable salt thereof.

Claims

1. The following general formula (I): 【Chemistry 1】 [In the above formula (I), n represents an integer of 0, 1, or 2. X represents N, Y represents O, Z represents a hydroxyl group or an oxo group. R １ is a hydrogen atom; a halogen atom; a C1-C6 alkyl group; a 3- to 6-membered cycloalkyl group; a 4- to 8-membered heterocycloalkyl group; a 6- to 10-membered aryl group; a 5- to 10-membered heteroaryl group; a C2-C6 alkenyl group; a C2-C6 alkynyl group; -CO-R ２ The base represented by: -COO-R ２ The base represented by: -CONH-R ２ The base indicated by; or -B (OR ４ ) OR ５ The base shown is represented by, where, R １ When R is other than a hydrogen atom and a C1-C6 alkyl group, the said R １ is a halogen atom, a hydroxy group, an amino group, a cyano group, a nitro group, a formyl group, a sulfanyl group, an oxo group, a C1-C3 alkyl group, a C1-C3 hydroxyalkyl group, a C1-C6 alkoxy group, a C1-C3 aminoalkyl group, a C1-C3 haloalkyl group, -N-R ２ R ３ group represented by, -COO-R ２ group represented by, -CONH-R ２ group represented by, -NHCO-R ２ group represented by, -NHSO ２ -R ２ group represented by, and -NHSO ２ NH-R ２ group represented by, and may be substituted with one or more substituents selected from R １ If the C1-C6 alkyl group is a halogen atom; hydroxyl group; amino group; nitro group; cyano group; oxo group; hydroxyl group, amino group, -CONH-R ２ The base shown by -NHCO-R ２ The group indicated by, or -NHSO ２ -R ２ 3- to 6-membered cycloalkyl groups which may be substituted with the group shown; 4- to 8-membered heterocycloalkyl groups which may be substituted with an oxo group; 6- to 10-membered aryl groups which may be substituted with a halogen atom or a C1-C3 alkyl group; 5- to 10-membered heteroaryl groups; -O-R ２ The group represented by: -O-CO-R ２ The group represented by: -O-CONH-R ２ The group represented by: -N-R ２ R ３ The group represented by: -S-R ２ The base represented by: -CONH-R ２ The base indicated by: -NHCO-R ２ The base represented by: -COO-R ２ The base indicated by; -NHCOO-R ２ The base represented by: -NHCONH-R ２ The base indicated by; -NHSO ２ -R ２ The group represented by: -CO-R ２ The group represented by: -SO ２ -R ２ The group indicated by; and -NHSO ２ NH-R ２ The group may be substituted with one or more substituents selected from the groups shown, R ２ R represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C3 haloalkyl group, a hydroxyl group, a C1-C3 hydroxyalkyl group, a C1-C6 alkoxy group, a C1-C3 haloalkoxy group, a 3- to 6-membered cycloalkyl group, a 3- to 6-membered cycloalkyl C1-C3 alkyl group, a 4- to 8-membered heterocycloalkyl group, a 6- to 10-membered aryl group, a 6- to 10-membered aryl C1-C3 alkyl group, a 5- to 10-membered heteroaryl group, a 5- to 10-membered heteroaryl C1-C3 alkyl group, a C1-C3 alkoxy C1-C3 alkyl group, an amino group, a C1-C6 alkylamino group, a C1-C6 dialkylamino group, a sulfanyl group, or a C1-C6 trialkylsilyl group, where R ２ The 5- to 10-membered heteroaryl groups shown are halogen atoms, hydroxyl groups, amino groups, cyano groups, C1-C3 alkyl groups, C1-C3 hydroxyalkyl groups, C1-C6 alkoxy groups, C1-C3 aminoalkyl groups, C1-C3 haloalkyl groups, and -N-R groups. ２ R ３ (This R2 represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C3 haloalkyl group, a hydroxyl group, a C1-C3 hydroxyalkyl group, a C1-C6 alkoxy group, a C1-C3 haloalkoxy group, a 3- to 6-membered cycloalkyl group, a 3- to 6-membered cycloalkyl C1-C3 alkyl group, a 4- to 8-membered heterocycloalkyl group, a 6- to 10-membered aryl group, a 6- to 10-membered aryl C1-C3 alkyl group, a 5- to 10-membered heteroaryl group, a 5- to 10-membered heteroaryl C1-C3 alkyl group, a C1-C3 alkoxy C1-C3 alkyl group, an amino group, a C1-C6 alkylamino group, a C1-C6 dialkylamino group, a sulfanyl group, or a C1-C6 trialkylsilyl group) and -CONH-R ２ (This R2 may be further substituted with one or more substituents selected from the groups represented by (H1-C6 alkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, C1-C3 haloalkyl group, hydroxyl group, C1-C3 hydroxyalkyl group, C1-C6 alkoxy group, C1-C3 haloalkoxy group, 3- to 6-membered cycloalkyl group, 3- to 6-membered cycloalkyl C1-C3 alkyl group, 4- to 8-membered heterocycloalkyl group, 6- to 10-membered aryl group, 6- to 10-membered aryl C1-C3 alkyl group, 5- to 10-membered heteroaryl group, 5- to 10-membered heteroaryl C1-C3 alkyl group, C1-C3 alkoxy C1-C3 alkyl group, amino group, C1-C6 alkylamino group, C1-C6 dialkylamino group, sulfanyl group, or C1-C6 trialkylsilyl group), ２ The heteroaryl group of the 5- to 10-membered heteroaryl C1-C3 alkyl group shown may be further substituted with an amino group or a C1-C3 alkyl group. R ３ This represents a hydrogen atom or a C1-C6 alkyl group. R ４ and R ５ These represent C1-C10 alkyl groups, each of which is either a hydrogen atom or may independently bond to each other to form a ring structure. The numbers 3, 4, 22, and 23 indicate the position numbers of carbon atoms, respectively. The bond between positions 3 and 4 represents a single bond, while the bond between positions 22 and 23 may be either a single or double bond. A compound represented by or a pharmaceutically acceptable salt thereof.

2. In the above formula (I), R １ The compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein the C1-C6 alkyl group may be substituted.

3. In the above formula (I), R １ However, 5-membered to 10-membered heteroaryl groups, -CONH-R ２ The group indicated by -CO-R ２ The compound according to claim 2, or a pharmaceutically acceptable salt thereof, which is a C1-C6 alkyl group substituted with the group shown.

4. Formulas (1) to (94) below: 【Chemistry 2】 【Transformation 3】 【Chemistry 4】 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 A compound represented by any of the above, or a pharmaceutically acceptable salt thereof.

5. The following general formula (I): [Chemistry 18] [In the above formula (I), n represents an integer of 0, 1, or 2. X represents CH, CF, or CHCH=CH. Y represents O, NH, or a single bond. Z represents a hydroxyl group or an oxo group. R １ is a hydrogen atom; a halogen atom; a C1-C6 alkyl group; a 3- to 6-membered cycloalkyl group; a 4- to 8-membered heterocycloalkyl group; a 6- to 10-membered aryl group; a 5- to 10-membered heteroaryl group; a C2-C6 alkenyl group; a C2-C6 alkynyl group; -CO-R ２ The base represented by: -COO-R ２ The base represented by: -CONH-R ２ The base indicated by; or -B (OR ４ ) OR ５ The base shown is represented by, where, R １ If R is other than a hydrogen atom and a C1-C6 alkyl group, １ This includes halogen atoms, hydroxyl groups, amino groups, cyano groups, nitro groups, formyl groups, sulfanyl groups, oxo groups, C1-C3 alkyl groups, C1-C3 hydroxyalkyl groups, C1-C6 alkoxy groups, C1-C3 aminoalkyl groups, C1-C3 haloalkyl groups, and -N-R groups. ２ R ３ The base shown by -COO-R ２ The group represented by -CONH-R ２ The base shown by -NHCO-R ２ The base shown by -NHSO ２ -R ２ The group shown by, and -NHSO ２ NH-R ２ The group may be substituted with one or more substituents selected from the groups shown, R １ When R is a C1-C6 alkyl group, the C1-C6 alkyl group may be a halogen atom; a hydroxy group; an amino group; a nitro group; a cyano group; an oxo group; a hydroxy group, an amino group, -CONH-R ２ a group represented by, -NHCO-R ２ a group represented by, or -NHSO ２ -R ２ a 3- to 6-membered cycloalkyl group optionally substituted with a group represented by; a 4- to 8-membered heterocycloalkyl group optionally substituted with an oxo group; a 6- to 10-membered aryl group optionally substituted with a halogen atom or a C1-C3 alkyl group; a 5- to 10-membered heteroaryl group; -O-R ２ a group represented by; -O-CO-R ２ a group represented by; -O-CONH-R ２ a group represented by; -N-R ２ R ３ a group represented by; -S-R ２ a group represented by; -CONH-R ２ a group represented by; -NHCO-R ２ a group represented by; -COO-R ２ a group represented by; -NHCOO-R ２ a group represented by; -NHCONH-R ２ a group represented by; -NHSO ２ -R ２ a group represented by; -CO-R ２ a group represented by; -SO ２ -R ２ a group represented by; and -NHSO ２ NH-R ２ is optionally substituted with one or more substituents selected from the groups represented by, R ２ represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C3 haloalkyl group, a hydroxy group, a C1-C3 hydroxyalkyl group, a C1-C6 alkoxy group, a C1-C3 haloalkoxy group, a 3- to 6-membered cycloalkyl group, a 3- to 6-membered cycloalkyl C1-C3 alkyl group, a 4- to 8-membered heterocycloalkyl group, a 6- to 10-membered aryl group, a 6- to 10-membered aryl C1-C3 alkyl group, a 5- to 10-membered heteroaryl group, a 5- to 10-membered heteroaryl C1-C3 alkyl group, a C1-C3 alkoxy C1-C3 alkyl group, an amino group, a C1-C6 alkylamino group, a C1-C6 dialkylamino group, a sulfanyl group, or a C1-C6 trialkylsilyl group, where R ２ The 5- to 10-membered heteroaryl group represented by R ２ R ３ (This R2 represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C3 haloalkyl group, a hydroxy group, a C1-C3 hydroxyalkyl group, a C1-C6 alkoxy group, a C1-C3 haloalkoxy group, a 3- to 6-membered cycloalkyl group, a 3- to 6-membered cycloalkyl C1-C3 alkyl group, a 4- to 8-membered heterocycloalkyl group, a 6- to 10-membered aryl group, a 6- to 10-membered aryl C1-C3 alkyl group, a 5- to 10-membered heteroaryl group, a 5- to 10-membered heteroaryl C1-C3 alkyl group, a C1-C3 alkoxy C1-C3 alkyl group, an amino group, a C1-C6 alkylamino group, a C1-C6 dialkylamino group, a sulfanyl group, or a C1-C6 trialkylsilyl group) and a group represented by -CONH-R ２ (This R2 may be further substituted with one or more substituents selected from the groups represented by (H1-C6 alkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, C1-C3 haloalkyl group, hydroxyl group, C1-C3 hydroxyalkyl group, C1-C6 alkoxy group, C1-C3 haloalkoxy group, 3- to 6-membered cycloalkyl group, 3- to 6-membered cycloalkyl C1-C3 alkyl group, 4- to 8-membered heterocycloalkyl group, 6- to 10-membered aryl group, 6- to 10-membered aryl C1-C3 alkyl group, 5- to 10-membered heteroaryl group, 5- to 10-membered heteroaryl C1-C3 alkyl group, C1-C3 alkoxy C1-C3 alkyl group, amino group, C1-C6 alkylamino group, C1-C6 dialkylamino group, sulfanyl group, or C1-C6 trialkylsilyl group), ２ The heteroaryl group of the 5- to 10-membered heteroaryl C1-C3 alkyl group shown may be further substituted with an amino group or a C1-C3 alkyl group. R ３ This represents a hydrogen atom or a C1-C6 alkyl group. R ４ and R ５ These represent C1-C10 alkyl groups, each of which is either a hydrogen atom or may independently bond to each other to form a ring structure. The numbers 3, 4, 22, and 23 indicate the position numbers of carbon atoms, respectively. The bond between positions 3 and 4 represents a single bond, while the bond between positions 22 and 23 may be either a single or double bond. A compound represented by or a pharmaceutically acceptable salt thereof.

6. The following general formula (I): 【Chemistry 19】 [In the above formula (I), n represents an integer of 0, 1, or 2. X represents CH, CF, or CHCH=CH. Y represents a single bond. Z represents a hydroxyl group or an oxo group. R １ -COO-R ２ Groups represented by: halogen atom, hydroxyl group, amino group, cyano group, formyl group, oxo group, C1-C3 alkyl group, C1-C3 hydroxyalkyl group, C1-C6 alkoxy group, C1-C3 haloalkyl group, -N-R ２ R ３ The base shown by -NHCO-R ２ The group shown by, and -CONH-R ２ A 5- to 10-membered heteroaryl group which may be substituted with one or more substituents selected from the groups represented by ; or a hydroxyl group, an amino group, a nitro group, an oxo group, -CONH-R ２ The group shown by, and -COO-R ２ This represents a C1-C6 alkyl group which may be substituted with one or more substituents selected from the groups shown, where, R ２ R represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C3 haloalkyl group, a hydroxyl group, a C1-C3 hydroxyalkyl group, a C1-C6 alkoxy group, a C1-C3 haloalkoxy group, a 3- to 6-membered cycloalkyl group, a 3- to 6-membered cycloalkyl C1-C3 alkyl group, a 4- to 8-membered heterocycloalkyl group, a 6- to 10-membered aryl group, a 6- to 10-membered aryl C1-C3 alkyl group, a 5- to 10-membered heteroaryl group, a 5- to 10-membered heteroaryl C1-C3 alkyl group, a C1-C3 alkoxy C1-C3 alkyl group, an amino group, a C1-C6 alkylamino group, a C1-C6 dialkylamino group, a sulfanyl group, or a C1-C6 trialkylsilyl group, where R ２ The 5- to 10-membered heteroaryl groups shown are halogen atoms, hydroxyl groups, amino groups, cyano groups, C1-C3 alkyl groups, C1-C3 hydroxyalkyl groups, C1-C6 alkoxy groups, C1-C3 aminoalkyl groups, C1-C3 haloalkyl groups, and -N-R groups. ２ R ３ (This R2 represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C3 haloalkyl group, a hydroxyl group, a C1-C3 hydroxyalkyl group, a C1-C6 alkoxy group, a C1-C3 haloalkoxy group, a 3- to 6-membered cycloalkyl group, a 3- to 6-membered cycloalkyl C1-C3 alkyl group, a 4- to 8-membered heterocycloalkyl group, a 6- to 10-membered aryl group, a 6- to 10-membered aryl C1-C3 alkyl group, a 5- to 10-membered heteroaryl group, a 5- to 10-membered heteroaryl C1-C3 alkyl group, a C1-C3 alkoxy C1-C3 alkyl group, an amino group, a C1-C6 alkylamino group, a C1-C6 dialkylamino group, a sulfanyl group, or a C1-C6 trialkylsilyl group) and -CONH-R ２ (This R2 may be further substituted with one or more substituents selected from the groups represented by (H1-C6 alkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, C1-C3 haloalkyl group, hydroxyl group, C1-C3 hydroxyalkyl group, C1-C6 alkoxy group, C1-C3 haloalkoxy group, 3- to 6-membered cycloalkyl group, 3- to 6-membered cycloalkyl C1-C3 alkyl group, 4- to 8-membered heterocycloalkyl group, 6- to 10-membered aryl group, 6- to 10-membered aryl C1-C3 alkyl group, 5- to 10-membered heteroaryl group, 5- to 10-membered heteroaryl C1-C3 alkyl group, C1-C3 alkoxy C1-C3 alkyl group, amino group, C1-C6 alkylamino group, C1-C6 dialkylamino group, sulfanyl group, or C1-C6 trialkylsilyl group), ２ The heteroaryl group of the 5- to 10-membered heteroaryl C1-C3 alkyl group shown may be further substituted with an amino group or a C1-C3 alkyl group. R ３ This represents a hydrogen atom or a C1-C6 alkyl group. The numbers 3, 4, 22, and 23 indicate the position numbers of carbon atoms, and the bonds between positions 3 and 4, and between positions 22 and 23, can be either single or double bonds, independently of each other. A compound represented by or a pharmaceutically acceptable salt thereof.

7. Formulas (201) to (271) below: 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemistry 27】 【Chemistry 28】 【Chemistry 29】 【Transformation 30】 【Chemistry 31】 A compound represented by any of the above, or a pharmaceutically acceptable salt thereof.

8. The following general formula (I): 【Chemistry 32】 [In the above formula (I), n represents an integer of 0, 1, or 2. X represents N, Y represents NH, Z represents a hydroxyl group or an oxo group. R １ is, -CO-R ２ The base shown is represented by, where, R ２ R represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C3 haloalkyl group, a hydroxyl group, a C1-C3 hydroxyalkyl group, a C1-C6 alkoxy group, a C1-C3 haloalkoxy group, a 3- to 6-membered cycloalkyl group, a 3- to 6-membered cycloalkyl C1-C3 alkyl group, a 4- to 8-membered heterocycloalkyl group, a 6- to 10-membered aryl group, a 6- to 10-membered aryl C1-C3 alkyl group, a 5- to 10-membered heteroaryl group, a 5- to 10-membered heteroaryl C1-C3 alkyl group, a C1-C3 alkoxy C1-C3 alkyl group, an amino group, a C1-C6 alkylamino group, a C1-C6 dialkylamino group, a sulfanyl group, or a C1-C6 trialkylsilyl group, where R ２ The 5- to 10-membered heteroaryl groups shown are halogen atoms, hydroxyl groups, amino groups, cyano groups, C1-C3 alkyl groups, C1-C3 hydroxyalkyl groups, C1-C6 alkoxy groups, C1-C3 aminoalkyl groups, C1-C3 haloalkyl groups, and -N-R groups. ２ R ３ (This R2 represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C3 haloalkyl group, a hydroxyl group, a C1-C3 hydroxyalkyl group, a C1-C6 alkoxy group, a C1-C3 haloalkoxy group, a 3- to 6-membered cycloalkyl group, a 3- to 6-membered cycloalkyl C1-C3 alkyl group, a 4- to 8-membered heterocycloalkyl group, a 6- to 10-membered aryl group, a 6- to 10-membered aryl C1-C3 alkyl group, a 5- to 10-membered heteroaryl group, a 5- to 10-membered heteroaryl C1-C3 alkyl group, a C1-C3 alkoxy C1-C3 alkyl group, an amino group, a C1-C6 alkylamino group, a C1-C6 dialkylamino group, a sulfanyl group, or a C1-C6 trialkylsilyl group) and -CONH-R ２ (This R2 may be further substituted with one or more substituents selected from the groups represented by (H1-C6 alkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, C1-C3 haloalkyl group, hydroxyl group, C1-C3 hydroxyalkyl group, C1-C6 alkoxy group, C1-C3 haloalkoxy group, 3- to 6-membered cycloalkyl group, 3- to 6-membered cycloalkyl C1-C3 alkyl group, 4- to 8-membered heterocycloalkyl group, 6- to 10-membered aryl group, 6- to 10-membered aryl C1-C3 alkyl group, 5- to 10-membered heteroaryl group, 5- to 10-membered heteroaryl C1-C3 alkyl group, C1-C3 alkoxy C1-C3 alkyl group, amino group, C1-C6 alkylamino group, C1-C6 dialkylamino group, sulfanyl group, or C1-C6 trialkylsilyl group), ２ The heteroaryl group of the 5- to 10-membered heteroaryl C1-C3 alkyl group shown may be further substituted with an amino group or a C1-C3 alkyl group. R ３ This represents a hydrogen atom or a C1-C6 alkyl group. The numbers 3, 4, 22, and 23 indicate the position numbers of carbon atoms, and the bonds between positions 3 and 4, and between positions 22 and 23, can be either single or double bonds, independently of each other. A compound represented by or a pharmaceutically acceptable salt thereof.

9. A compound according to any one of claims 1 to 8, or a pharmaceutically acceptable salt thereof, having antiviral activity against coronavirus.

10. The compound according to claim 9 or a pharmaceutically acceptable salt thereof, wherein the coronavirus is a coronavirus classified under the genus Betacoronavirus.

11. The compound according to claim 9 or a pharmaceutically acceptable salt thereof, wherein the coronavirus is at least one selected from the group consisting of human coronavirus (HCoV), severe acute respiratory syndrome coronavirus (SARS-CoV), novel coronavirus (SARS-CoV-2), and Middle East respiratory syndrome coronavirus (MERS-CoV).

12. The following general formula (I): 【Transformation 33】 [In the above formula (I), n represents an integer of 0, 1, or 2. X represents CH, CF, CCl, N, CHCH=N, CHCH=CH, or CHCH=CF, Y represents O, NH, or a single bond. Z represents a hydroxyl group or an oxo group. R １ is a hydrogen atom; a halogen atom; a C1-C6 alkyl group; a 3- to 6-membered cycloalkyl group; a 4- to 8-membered heterocycloalkyl group; a 6- to 10-membered aryl group; a 5- to 10-membered heteroaryl group; a C2-C6 alkenyl group; a C2-C6 alkynyl group; -CO-R ２ The base represented by: -COO-R ２ The base represented by: -CONH-R ２ The base indicated by; or -B (OR ４ ) OR ５ The base shown is represented by, where, R １ If R is other than a hydrogen atom and a C1-C6 alkyl group, １ This includes halogen atoms, hydroxyl groups, amino groups, cyano groups, nitro groups, formyl groups, sulfanyl groups, oxo groups, C1-C3 alkyl groups, C1-C3 hydroxyalkyl groups, C1-C6 alkoxy groups, C1-C3 aminoalkyl groups, C1-C3 haloalkyl groups, and -N-R groups. ２ R ３ The base shown by -COO-R ２ The group represented by -CONH-R ２ The base shown by -NHCO-R ２ The base shown by -NHSO ２ -R ２ The group indicated by, and -NHSO ２ NH-R ２ The group may be substituted with one or more substituents selected from the groups shown, R １ If the C1-C6 alkyl group is a halogen atom; hydroxyl group; amino group; nitro group; cyano group; oxo group; hydroxyl group, amino group, -CONH-R ２ The base shown by -NHCO-R ２ The group indicated by, or -NHSO ２ -R ２ 3- to 6-membered cycloalkyl groups which may be substituted with the group shown; 4- to 8-membered heterocycloalkyl groups which may be substituted with an oxo group; 6- to 10-membered aryl groups which may be substituted with a halogen atom or a C1-C3 alkyl group; 5- to 10-membered heteroaryl groups; -O-R ２ The group represented by: -O-CO-R ２ The group represented by: -O-CONH-R ２ The group represented by: -N-R ２ R ３ The group represented by: -S-R ２ The base represented by: -CONH-R ２ The base indicated by: -NHCO-R ２ The base represented by: -COO-R ２ The base indicated by; -NHCOO-R ２ The base represented by: -NHCONH-R ２ The base indicated by; -NHSO ２ -R ２ The group represented by: -CO-R ２ The group represented by: -SO ２ -R ２ The group indicated by; and -NHSO ２ NH-R ２ The group may be substituted with one or more substituents selected from the groups shown, R ２ R represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C3 haloalkyl group, a hydroxyl group, a C1-C3 hydroxyalkyl group, a C1-C6 alkoxy group, a C1-C3 haloalkoxy group, a 3- to 6-membered cycloalkyl group, a 3- to 6-membered cycloalkyl C1-C3 alkyl group, a 4- to 8-membered heterocycloalkyl group, a 6- to 10-membered aryl group, a 6- to 10-membered aryl C1-C3 alkyl group, a 5- to 10-membered heteroaryl group, a 5- to 10-membered heteroaryl C1-C3 alkyl group, a C1-C3 alkoxy C1-C3 alkyl group, an amino group, a C1-C6 alkylamino group, a C1-C6 dialkylamino group, a sulfanyl group, or a C1-C6 trialkylsilyl group, where R ２ The 5- to 10-membered heteroaryl groups shown are halogen atoms, hydroxyl groups, amino groups, cyano groups, C1-C3 alkyl groups, C1-C3 hydroxyalkyl groups, C1-C6 alkoxy groups, C1-C3 aminoalkyl groups, C1-C3 haloalkyl groups, and -N-R groups. ２ R ３ (This R2 represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C3 haloalkyl group, a hydroxyl group, a C1-C3 hydroxyalkyl group, a C1-C6 alkoxy group, a C1-C3 haloalkoxy group, a 3- to 6-membered cycloalkyl group, a 3- to 6-membered cycloalkyl C1-C3 alkyl group, a 4- to 8-membered heterocycloalkyl group, a 6- to 10-membered aryl group, a 6- to 10-membered aryl C1-C3 alkyl group, a 5- to 10-membered heteroaryl group, a 5- to 10-membered heteroaryl C1-C3 alkyl group, a C1-C3 alkoxy C1-C3 alkyl group, an amino group, a C1-C6 alkylamino group, a C1-C6 dialkylamino group, a sulfanyl group, or a C1-C6 trialkylsilyl group) and -CONH-R ２ (This R2 may be further substituted with one or more substituents selected from the groups represented by (H1-C6 alkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, C1-C3 haloalkyl group, hydroxyl group, C1-C3 hydroxyalkyl group, C1-C6 alkoxy group, C1-C3 haloalkoxy group, 3- to 6-membered cycloalkyl group, 3- to 6-membered cycloalkyl C1-C3 alkyl group, 4- to 8-membered heterocycloalkyl group, 6- to 10-membered aryl group, 6- to 10-membered aryl C1-C3 alkyl group, 5- to 10-membered heteroaryl group, 5- to 10-membered heteroaryl C1-C3 alkyl group, C1-C3 alkoxy C1-C3 alkyl group, amino group, C1-C6 alkylamino group, C1-C6 dialkylamino group, sulfanyl group, or C1-C6 trialkylsilyl group), ２ The heteroaryl group of the 5- to 10-membered heteroaryl C1-C3 alkyl group shown may be further substituted with an amino group or a C1-C3 alkyl group. R ３ This represents a hydrogen atom or a C1-C6 alkyl group. R ４ and R ５ These represent C1-C10 alkyl groups, each of which is either a hydrogen atom or may independently bond to each other to form a ring structure. The numbers 3, 4, 22, and 23 indicate the position numbers of carbon atoms, and the bonds between positions 3 and 4, and between positions 22 and 23, can be either single or double bonds, independently of each other. A composition for the treatment or prevention of a disease or condition involving coronavirus, comprising a compound represented by or a pharmaceutically acceptable salt thereof as an active ingredient.

13. The composition according to claim 12, wherein the coronavirus is a coronavirus classified under the genus Betacoronavirus.

14. The composition according to claim 12, wherein the coronavirus is at least one selected from the group consisting of human coronavirus (HCoV), severe acute respiratory syndrome coronavirus (SARS-CoV), novel coronavirus (SARS-CoV-2), and Middle East respiratory syndrome coronavirus (MERS-CoV).

15. For the manufacture of compositions for the treatment or prevention of diseases or conditions involving coronavirus, The following general formula (I): 【Transformation 34】 [In the above formula (I), n represents an integer of 0, 1, or 2. X represents CH, CF, CCl, N, CHCH=N, CHCH=CH, or CHCH=CF, Y represents O, NH, or a single bond. Z represents a hydroxyl group or an oxo group. R １ is a hydrogen atom; a halogen atom; a C1-C6 alkyl group; a 3- to 6-membered cycloalkyl group; a 4- to 8-membered heterocycloalkyl group; a 6- to 10-membered aryl group; a 5- to 10-membered heteroaryl group; a C2-C6 alkenyl group; a C2-C6 alkynyl group; -CO-R ２ The base represented by: -COO-R ２ The base represented by: -CONH-R ２ The base indicated by; or -B (OR ４ ) OR ５ The base shown is represented by, where, R １ If R is other than a hydrogen atom and a C1-C6 alkyl group, １ This includes halogen atoms, hydroxyl groups, amino groups, cyano groups, nitro groups, formyl groups, sulfanyl groups, oxo groups, C1-C3 alkyl groups, C1-C3 hydroxyalkyl groups, C1-C6 alkoxy groups, C1-C3 aminoalkyl groups, C1-C3 haloalkyl groups, and -N-R groups. ２ R ３ The base shown by -COO-R ２ The group represented by -CONH-R ２ The base shown by -NHCO-R ２ The base shown by -NHSO ２ -R ２ The group indicated by, and -NHSO ２ NH-R ２ The group may be substituted with one or more substituents selected from the groups shown, R １ If the C1-C6 alkyl group is a halogen atom; hydroxyl group; amino group; nitro group; cyano group; oxo group; hydroxyl group, amino group, -CONH-R ２ The base shown by -NHCO-R ２ The group indicated by, or -NHSO ２ -R ２ 3- to 6-membered cycloalkyl groups which may be substituted with the group shown; 4- to 8-membered heterocycloalkyl groups which may be substituted with an oxo group; 6- to 10-membered aryl groups which may be substituted with a halogen atom or a C1-C3 alkyl group; 5- to 10-membered heteroaryl groups; -O-R ２ The group represented by: -O-CO-R ２ The group represented by: -O-CONH-R ２ The group represented by: -N-R ２ R ３ The group represented by: -S-R ２ The base represented by: -CONH-R ２ The base indicated by: -NHCO-R ２ The base represented by: -COO-R ２ The base indicated by; -NHCOO-R ２ The base represented by: -NHCONH-R ２ The base indicated by; -NHSO ２ -R ２ The group represented by: -CO-R ２ The group represented by: -SO ２ -R ２ The group indicated by; and -NHSO ２ NH-R ２ The group may be substituted with one or more substituents selected from the groups shown, R ２ R represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C3 haloalkyl group, a hydroxyl group, a C1-C3 hydroxyalkyl group, a C1-C6 alkoxy group, a C1-C3 haloalkoxy group, a 3- to 6-membered cycloalkyl group, a 3- to 6-membered cycloalkyl C1-C3 alkyl group, a 4- to 8-membered heterocycloalkyl group, a 6- to 10-membered aryl group, a 6- to 10-membered aryl C1-C3 alkyl group, a 5- to 10-membered heteroaryl group, a 5- to 10-membered heteroaryl C1-C3 alkyl group, a C1-C3 alkoxy C1-C3 alkyl group, an amino group, a C1-C6 alkylamino group, a C1-C6 dialkylamino group, a sulfanyl group, or a C1-C6 trialkylsilyl group, where R ２ The 5- to 10-membered heteroaryl groups shown are halogen atoms, hydroxyl groups, amino groups, cyano groups, C1-C3 alkyl groups, C1-C3 hydroxyalkyl groups, C1-C6 alkoxy groups, C1-C3 aminoalkyl groups, C1-C3 haloalkyl groups, and -N-R groups. ２ R ３ (This R2 represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C3 haloalkyl group, a hydroxyl group, a C1-C3 hydroxyalkyl group, a C1-C6 alkoxy group, a C1-C3 haloalkoxy group, a 3- to 6-membered cycloalkyl group, a 3- to 6-membered cycloalkyl C1-C3 alkyl group, a 4- to 8-membered heterocycloalkyl group, a 6- to 10-membered aryl group, a 6- to 10-membered aryl C1-C3 alkyl group, a 5- to 10-membered heteroaryl group, a 5- to 10-membered heteroaryl C1-C3 alkyl group, a C1-C3 alkoxy C1-C3 alkyl group, an amino group, a C1-C6 alkylamino group, a C1-C6 dialkylamino group, a sulfanyl group, or a C1-C6 trialkylsilyl group) and -CONH-R ２ (This R2 may be further substituted with one or more substituents selected from the groups represented by (H1-C6 alkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, C1-C3 haloalkyl group, hydroxyl group, C1-C3 hydroxyalkyl group, C1-C6 alkoxy group, C1-C3 haloalkoxy group, 3- to 6-membered cycloalkyl group, 3- to 6-membered cycloalkyl C1-C3 alkyl group, 4- to 8-membered heterocycloalkyl group, 6- to 10-membered aryl group, 6- to 10-membered aryl C1-C3 alkyl group, 5- to 10-membered heteroaryl group, 5- to 10-membered heteroaryl C1-C3 alkyl group, C1-C3 alkoxy C1-C3 alkyl group, amino group, C1-C6 alkylamino group, C1-C6 dialkylamino group, sulfanyl group, or C1-C6 trialkylsilyl group), ２ The heteroaryl group of the 5- to 10-membered heteroaryl C1-C3 alkyl group shown may be further substituted with an amino group or a C1-C3 alkyl group. R ３ This represents a hydrogen atom or a C1-C6 alkyl group. R ４ and R ５ These represent C1-C10 alkyl groups, each of which is either a hydrogen atom or may independently bond to each other to form a ring structure. The numbers 3, 4, 22, and 23 indicate the position numbers of carbon atoms, and the bonds between positions 3 and 4, and between positions 22 and 23, can be either single or double bonds, independently of each other. The use of a compound represented by or a pharmaceutically acceptable salt thereof.

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