Cyclin-dependent kinase (CDK2) inhibitors

Abstract

This invention provides compounds that can be used to treat conditions, diseases, and disorders mediated by CDK2, such as cancer; a method for preparing the compounds; a pharmaceutical composition containing the compounds; and the use of the compounds in the treatment of conditions, diseases, and disorders mediated by CDK2. [Solution] The compound is represented by the following formula (I). JPEG2026102718000734.jpg36170

Claims

1. Compounds relating to formula (I), 【Chemistry 1】 [In the formula, Y １ is a bond or CH ２ (For example, Y １ (is a combination); Y ２ is bond, O, NR ５ or CR ６ R ７ (For example, Y ２ (is a combination); R １ and R ２ each independently is H, halo, C １ to C ６ alkyl and C １ to C ６ haloalkyl Selected from the group consisting of R, or R １ and R ２ Together, they form C ３ ~C ４ Cycloalkyl or C ３ ~C ４ It forms a cyclohaloalkyl group; Each R ３ These are independently hydroxyl, halo, and C. １ ~C ６ Alkyl and C １ ~C ６ Hello Walk Selected from a group consisting of; R ４ H, Halo, C １ ~C ６ Alkyl and C １ ~C ６ Select from the group consisting of haloalkyls. And; R ５ H, C １ ~C ６ Alkyl, C(=O)-C １ ~C ６ Alkyl or C(=O)-O -C １ ~C ６ Selected from the group consisting of alkyl groups; R ６ and R ７ They come together as a group, along with the carbon atoms to which they are bonded. , C ３ ~C ６ 1 to 3 independently selected from the group consisting of cycloalkyl or O, N, and S It forms a 3- to 6-membered heterocycline containing a number of heteroatoms, and the C ３ ~C ６ Cycloa Lukyl or 3-6 membered heterocyclyl has 0-3 substituents R ８ It has been replaced with; Each R ８ Independently, C １ ~C ６ Alkyl, C(=O)C １ ~C ６ Alkyl, Halo, C １ ~ C ６ Haloalkyl, S-C １ ~C ６ Alkyl, SO-C １ ~C ６ Alkyl, SO ２ -C １ ~C ６ Selected from the group consisting of alkyl, cyano, and hydroxyl, or the same ring atom The two R's above ８ The substituents together form an O molecule. n is between 0 and 3; m is between 1 and 5; 【Chemistry 2】 This is a five-membered heteroaryl compound containing one to three heteroatoms independently selected from N, O, and S. The 5-membered heteroaryl has 0 to 3 substituents R Ａ It has been replaced with; Each R Ａ *L １ -X １ And in the formula, * represents, 【Transformation 3】 It refers to the point where each L is joined. １ The bonds are O, S, SO, SO ２ , C≡C, C(=O), * C(=O)-O**, C １ ~C ６ Alkylene, C １ ~C ６ Haloalkylene, *O-C １ ~ C ６ Alkylene**, *O-C １ ~C ６ Haloalkylene**, *O-C １ ~C ６ Hydroxy Sialquilen**, C １ ~C ６ Alkylene-OC １ ~C ６ Alkylene, *O-C ３ ~C ６ Cycloalkylene**, *O-3 to 6-membered heterocyclylene**, C １ ~C ６ hydroxy Alkylene, C ３ ~C ６ Cycloalkylenes, 3-6 member heterocyclenes (for example, O) (Contains one heteroatom), O-C １ ~C ６ Alkylene-O, *O-C １ ~C ６ Alchile -O-C ３ -C ６ cycloalkylene ** and ** -O-C １ -C ６ alkylene -O- 3-6 Independently selected from member heterocyclylenes**, where * is, 【Chemistry 4】 It refers to the point where they join, and ** is X １ It refers to the point of bonding; and each X １ is H, halo, cyano, hydroxyl, C １ to C ６ alkyl, C(=O)-C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, 0-3 R groups ８ Substituted by the group C ３ ~C ６ Cycloalkyl, O-C １ ~C ６ Alkyl, S-C １ ~C ６ Alkyl, S(O )-C １ ~C ６ Alkyl, S(O) ２ -C １ ~C ６ Alkyl, N(C) １ ~C ６ Alkyl) ２ , C(=O)N(C １ ~C ６ Alkyl) ２ , C １ ~C ６ Hydroxyalkyl groups, 0-3 R ８ 3- to 6-membered heterocyclines substituted with a group (e.g., from O, N, and S) (Containing one or two heteroatoms selected vertically), 0 to 3 R ８ Substituted by the group A 5-10 member heteroatom containing 1-4 heteroatoms independently selected from O, N, and S. Aryl (e.g., 5, 6, 9, or 10-membered heteroaryl), 0 to 3 R ８ Based on One to four heteroatoms independently selected from the group consisting of O, N, and S are substituted. Contains 5-10 membered partially saturated heterocyclyl, 0-3 R ８ Substituted by the group, O N and S A 7-10 member spiroheterocycline containing one or two heteroatoms independently selected from, 0 ~3 R's ８ C substituted by a group ７ ~C １０ Selected independently from spirocycloalkyl Will it be selected? or Two R atoms located in adjacent ring atoms Ａ The substituents, together, form the adjacent ring Along with atoms, a 4-6 member containing 1-3 heteroatoms independently selected from N, O, and S It forms a telocycline, wherein at least one heteroatom is nitrogen. ］； or pharmaceutically acceptable salts and / or tautomers thereof.

2. Y １ The compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein the bond is a compound or / or Tautomers.

3. Y ２ The compound according to claim 1 or 2, or a pharmaceutically acceptable salt thereof, wherein the bond is / or tautomers.

4. A compound according to any one of claims 1 to 3, wherein m is 4, or a pharmaceutically acceptable salt thereof. bi / or tautomers.

5. The compound according to any one of claims 1 to 4, wherein n is 1 to 3, for example, n is 1. A substance or its pharmaceutically acceptable salts and / or tautomers.

6. at least one R ３ The compound according to claim 5, wherein the OH group is or the pharmaceutically acceptable compound thereof. Possible salts and / or tautomers.

7. The compound of formula (I) is the compound of formula (Ia): 【Transformation 5】 (In the formula, R １ , R ２ , R ３ , R ４ and 【Transformation 6】 The compound or its pharmaceutical (as defined in claim 1) A generally acceptable salt and / or tautomer.

8. The compound of formula (I) is the compound of formula (Ib): 【Transformation 7】 (In the formula, R １ , R ２ , R ３ , R ４ and 【Transformation 8】 The compound or its pharmaceutical (as defined in claim 1) A generally acceptable salt and / or tautomer.

9. The compound of formula (I) is the compound of formula (Ic): 【Chemistry 9】 (In the formula, R １ , R ２ , R ３ , R ４ and 【Chemistry 10】 The compound or its pharmaceutical (as defined in claim 1) A generally acceptable salt and / or tautomer.

10. The compound of formula (I) is the compound of formula (Id): 【Chemistry 11】 (In the formula, R １ , R ２ , R ４ and 【Chemistry 12】 The compound or its pharmaceutical (as defined in claim 1) A generally acceptable salt and / or tautomer.

11. R １ and R ２ But together, C ３ ~C ４ Cycloalkyl or C ３ ~C ４ C A compound or agent according to any one of claims 1 to 10 that forms a chlorohaloalkyl group. Scientifically acceptable salts and / or tautomers.

12. R １ and R ２ But together, C ３ ~C ４ Forms a cycloalkyl group, claim The compounds described in item 11 or their pharmaceutically acceptable salts and / or tautomers.

13. R １ and R ２ But together, C ３ Forming a cycloalkyl group, claim 12 The compounds described herein or their pharmaceutically acceptable salts and / or tautomers.

14. R ４ A compound according to any one of claims 1 to 13, wherein H is present, or a pharmaceutically acceptable compound thereof. Possible salts and / or tautomers. 【Request Item 15】 【Chemistry 13】 However, it is a five-membered heteroaryl compound containing two heteroatoms independently selected from N, O, and S. Furthermore, the five-membered heteroaryl has 0 to 3 substituents R Ａ It is substituted with, in the formula, R Ａ teeth , as defined in any one of claims 1 to 14, any one of claims 1 to 14 The compounds described in item 1, or their pharmaceutically acceptable salts and / or tautomers. 【Request Item 16】 【Chemistry 14】 However, it is a five-membered heteroaryl compound containing two heteroatoms independently selected from N and O. The aforementioned five-membered heteroaryl has 0 to 3 substituents R Ａ It is substituted with, in the formula, R Ａ Please The compound according to claim 15, as defined in any one of claims 1 to 15 or The pharmaceutically acceptable salts and / or tautomers thereof. 【Request Item 17】 【Chemistry 15】 However, each is a 5-membered heteroaryl compound containing 1 to 3 heteroatoms, which are N. Roaryl has 0 to 3 substituents R Ａ It is substituted with, in the formula, R Ａ Claims 1 to 16 The compound according to any one of claims 1 to 14, as defined in any one of the claims A substance or its pharmaceutically acceptable salts and / or tautomers. 【Request Item 18】 【Chemistry 16】 However, it is a 5-membered heteroaryl compound containing two heteroatoms, each of which is N, and the 5-membered heteroaryl The reel has 0 to 3 substituents R Ａ It is substituted with, in the formula, R Ａ The following are claims 1 to 17 The compound according to any one of claims 1 to 17, as defined in any one of the claims. The pharmaceutically acceptable salts and / or tautomers thereof. 【Request Item 19】 【Chemistry 17】 However, it is a 5-membered heteroaryl compound containing two heteroatoms, each of which is N, and the 5-membered heteroaryl The reel has 0 to 2 substituents R Ａ It is substituted with, in the formula, R Ａ The following are claims 1 to 18. The compound according to any one of claims 1 to 18, as defined in any one of the claims. The pharmaceutically acceptable salts and / or tautomers thereof. 【Request Item 20】 【Chemistry 18】 However, it is a 5-membered heteroaryl compound containing two heteroatoms, each of which is N, and the 5-membered heteroaryl The reel has 0 or 1 substituent R Ａ It is substituted with, in the formula, R Ａ *L １ -X １ and , L １ and X １ Claim 1 is defined as any one of claims 1 to 19. Compounds described in any one of items 19 or therein pharmaceutically acceptable salts and / or tautomers body. 【Request Item 21】 【Chemistry 19】 but, 【Chemistry 20】 A compound or pharmaceutically thereof selected from the group consisting of any one of claims 1 to 14. A generally acceptable salt and / or tautomer. 【Request Item 22】 【Chemistry 21】 but, 【Chemistry 22】 A compound selected from the group consisting of any one of claims 1 to 14 and 21 or The pharmaceutically acceptable salts and / or tautomers thereof. 【Request Item 23】 【Chemistry 23】 but, 【Chemistry 24】 【Chemistry 25】 X is selected from the group consisting of O, NH and S (for example, X is NH and (i) the compound or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 14 and / or tautomers.

24. but, 【Chemistry 26】 but, 【Chemistry 27】 【Chemistry 28】 A compound selected from the group consisting of any one of claims 1 to 14 and 22 or The pharmaceutically acceptable salts and / or tautomers thereof. 【Request Item 25】 【Chemistry 29】 but, 【Transformation 30】 A group consisting of is selected, and X is selected from O, NH and S, claims 1 to 14 and 2 A compound described in any one of item 3, or a pharmaceutically acceptable salt and / or tautomer thereof. 【Request Item 26】 【Chemistry 31】 but, 【Chemistry 32】 A compound selected from the group consisting of any one of claims 1 to 14 and 25 or The pharmaceutically acceptable salts and / or tautomers thereof.

27. i) 【Transformation 33】 but, 【Transformation 34】 Selected from a group consisting of (for example, 【Chemistry 35】 teeth 【Transformation 36】 (is), R Ａ but, a) Hello, b) Cyano, c) C １ ~C ６ Alkyl, d) C １ ~C ６ Haloalkyl, e) C １ ~C ６ Hydroxyalkyl, f) O-C １ ~C ６ Alkyl, g) C(=O)-OC １ ~C ６ Alkyl, h) C １ ~C ６ Alkylene-OC １ ~C ６ Alkyl, i) O-C １ ~C ６ Alkylene-OC １ ~C ６ Alkyl, j) 0 to 3 R ８ C substituted by a group ３ ~C ６ Cycloalkyl, k) 0 to 3 R ８ Substituted by a group, 1 to 1, independently selected from N, O, and S A 5- to 10-membered heteroaryl compound containing four heteroatoms. l) 0 to 3 R ８ Substituted by a group, 1 to 1, independently selected from N, O, and S A 5-10 membered partially saturated heterocycline containing four heteroatoms, m) 0 to 3 R ８ O-C substituted by a group ３ ~C ６ Cycloalkyl, n) 0 to 3 R ８ Substituted by a group, 1 to 1, independently selected from N, O, and S C≡C-5 to 10-membered heteroaryls containing four heteroatoms, o) 0 to 3 R ８ Substituted by a group, 1 to 1, independently selected from N, O, and S S-5 to 10-membered heteroaryl compounds containing four heteroatoms, p) 0 to 3 R ８ Substituted by a group, 1 to 1, independently selected from N, O, and S C containing four heteroatoms １ ~C ６ Alkylene-5 to 10-membered heteroaryl, q) O-C １ ~C ６ Haloalkyl, r) O-C １ ~C ６ Alkylene-N(C) １ ~C ６ Alkyl) ２ , s) O-C １ ~C ６ Hydroxyalkylene-O-C １ ~C ６ Alkyl, t) 0 to 3 R ８ O-C substituted by a group １ ~C ６ Alkylene-C ３ ~C ６ C Chloalkyl, u) 0 to 3 R ８ A single element, independently selected from O, N, and S, which is substituted by the element O-C contains two heteroatoms １ ~C ６ Alkilen-3 to 6-membered heterocycline, v) O-C １ ~C ６ Alkylene-C(=O)-N(C) １ ~C ６ Alkyl) ２ , w) 0 to 3 R ８ Substituted by a group, 1 to 1, independently selected from N, O, and S C containing four heteroatoms １ ~C ６ Alkylene-5 to 10-membered partially saturated heterocycline, x) 0 to 3 R ８ A single element, independently selected from O, N, and S, which is substituted by the element O-C contains two heteroatoms １ ~C ６ Alkilen-7-10 member spiroheterocycline 、 y) O-C １ ~C ６ Alkylene-S(O) ２ -C １ ~C ６ Alkyl, z) O-C １ ~C ６ Hydroxyalkyl, aa) 0 to 3 R ８ One independently selected from N, O, and S, which is substituted by the group O-C containing 4 heteroatoms １ ~C ６ Alkylene-5 to 10-membered heteroaryl, bb) 0 to 3 R ８ One independently selected from N, O, and S, which is substituted by the group ~O-5 to 10-membered heteroaryls containing 4 heteroatoms, cc) 0 to 3 R ８ A compound independently selected from O, N, and S, which is substituted by a group. Or an O-3 to 6-membered heterocycline containing two heteroatoms, dd) 0 to 3 R ８ C≡C-C substituted by the group ３ ~C ６ Cycloalkyl, ee) S-C １ ~C ６ Haloalkyl, ff) 0 to 3 R ８ A compound independently selected from O, N, and S, which is substituted by a group. or O-C containing two heteroatoms １ ~C ６ Alkilen-O-3 to 6-membered heterocycline gg) and 0 to 3 R ８ A single element selected from N, O, and S is substituted by a base. These are 3- to 6-membered heterocyclines containing two heteroatoms. Selected from; or ii) 【Chemistry 37】 but, 【Transformation 38】 And the R Ａ The substituents, together, along with the ring atom to which they are bonded , 4-6 membered heterocycline containing 1-3 heteroatoms independently selected from N, O, and S Forming a circle A compound according to any one of claims 1 to 14 and 26 or a pharmaceutically acceptable salt thereof bi / or tautomers.

28. Each R ８ However, independently, halo (for example, fluoro), C １ ~C ６ Alkyl (for example, methyl ), hydroxyl, cyano, S(O ２ )-C １ ~C ６ Alkyl (for example, S(O) ２ )CH ３ ), C(=O)-C １ ~C ６ Alkyl (e.g., C(=O)CH ３ ), O-C １ ~C ６ Alkyl (e.g., OCH ３ ) and C １ ~C ６ Haloalkyl (for example, C １ Haloalkyl For example, CHF ２ ) selected from the group consisting of or two R on the same ring atom ８ The compound according to claim 27, or the substituents together form an O group. pharmaceutically acceptable salts and / or tautomers thereof.

29. i) 【Chemistry 39】 but, 【Chemistry 40】 Selected from the group consisting of R Ａ However, halo, cyano, C １ ~C ６ Alkyl, C １ ~C ６ Hello Alkyl, C １ ~C ６ Hydroxyalkyl, O-C １ ~C ６ Alkyl, C(=O)-O- C １ ~C ６ Alkyl, C １ ~C ６ Alkylene-OC １ ~C ６ Alkyl, O-C １ ~C ６ Alkylene-OC １ ~C ６ Alkyl, C ３ ~C ６ From cycloalkyl and N, O and S Selected from 3- to 6-membered heterocyclines containing one or two selected heteroatoms; or teeth ii) 【Chemistry 41】 but, 【Chemistry 42】 And the R Ａ The substituents, together, along with the ring atom to which they are bonded , 4-6 membered heterocycline containing 1-3 heteroatoms independently selected from N, O, and S Forming a circle The compound according to claim 27 or a pharmaceutically acceptable salt and / or tautomer thereof. 【Request Item 30】 【Chemistry 43】 but, 【Chemistry 44】 And R Ａ However, CH ３ , OCH ３ or OCH ２ CH ３ Claims 1 to 14, 28 and The compounds described in any one of paragraphs 29 or their pharmaceutically acceptable salts and / or tautomers body.

31. Each L １ However, the bond is O, C (=O), *C (=O) - O**, C １ ~C ６ Alkylene, C １ ~C ６ Haloalkylene, *O-C １ ~C ６ Alkylene**, C １ ~C ６ Alkylene-O -C １ ~C ６ Alkylene, C １ ~C ６ Hydroxyalkylene, C ３ ~C ６ Cyclo Alkile N, 3-6 member heterocyclene (for example, containing one heteroatom which is O), and O-C １ ~C ６ Independently selected from alkylene-O, where * represents, 【Chemistry 45】 It refers to the point where they join, and ** is X １ It refers to the point of bonding; and each X １ However, H, halo, cyano, hydroxyl, C １ ~C ６ Alkyl, C １ ~C ６ Hello Alkyl, C ３ ~C ６ Cycloalkyl, O-C １ ~C ６ Alkyl, C １ ~C ６ hydroxy From alkyl and 3-6 membered heterocyclines (for example, containing one heteroatom which is oxygen) Independently selected, The compound according to any one of claims 1 to 27 or a pharmaceutically acceptable salt thereof and / or Tautomers.

32. R Ａ However, C １ ~C ６ Alkyl, C １ ~C ６ Alkylene-OC １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C(=O)-O-C １ ~C ６ Alkyl, C １ ~C ６ Hydroxyl Kill, a 3- to 6-membered heteroatom containing one heteroatom that is oxygen, halo, O-C １ ~C ６ Al Kill, C ３ ~C ６ Cycloalkyl, cyano, and O-C １ ~C ６ Alkylene-OC １ ~C ６ Selected from a list of alkyl groups, as described in any one of claims 1 to 27 and 31. The listed compounds or their pharmaceutically acceptable salts and / or tautomers.

33. 1) 7'-((1R,3R)-3-hydroxycyclohexyl)-2'-((1-meth Lu-1H-pyrazole-4-yl)amino)spiro[cyclopropane-1,5'-pyrrolo [2,3-d]pyrimidine]-6'(7'H)-one; 2) 7'-((1R,3R)-3-hydroxycyclohexyl)-2'-((3-meth Lu-1H-pyrazole-4-yl)amino)spiro[cyclopropane-1,5'-pyrrolo [2,3-d]pyrimidine]-6'(7'H)-one; 3) 2'-((3-(difluoromethyl)-1H-pyrazole-4-yl)amino)- 7'-((1R,3R)-3-hydroxycyclohexyl)spiro[cyclopropane-1 ,5'-pyrrolo[2,3-d]pyrimidine]-6'(7'H)-one; 4) 4-((7'-((1R,3R)-3-hydroxycyclohexyl)-6'-Oxy So-6',7'-dihydrospiro[cyclopropane-1,5'-pyrrolo[2,3-d]pi Limidine-2'-yl)amino)-1H-pyrazole-3-methyl carboxylate; 5) 7'-((1R,3R)-3-hydroxycyclohexyl)-2'-((3-meth Lu-1H-pyrazole-5-yl)amino)spiro[cyclopropane-1,5'-pyrrolo [2,3-d]pyrimidine]-6'(7'H)-one; 6) 7'-((1R,3R)-3-hydroxycyclohexyl)-2'-((3-(H (Droxymethyl)-1H-pyrazole-4-yl)amino)spiro[cyclopropane-1 ,5'-pyrrolo[2,3-d]pyrimidine]-6'(7'H)-one; 7) 7'-((1R,5R)-5-hydroxy-3,3-dimethylcyclohexyl)- 2'-((3-methyl-1H-pyrazole-4-yl)amino)spiro[cyclopropane -1,5'-pyrrolo[2,3-d]pyrimidine]-6'(7'H)-one; 8) 7'-((1R,3R)-3-hydroxycyclohexyl)-2'-((3-(T Trahydrofuran-3-yl)-1H-pyrazole-4-yl)amino)spiro[cyclo Propan-1,5'-pyrrolo[2,3-d]pyrimidine]-6'(7'H)-one; 9) 7'-((1R,3R)-3-hydroxycyclohexyl)-2'-((4,5, 6,7-tetrahydropyrazolo[1,5-a]pyrazine-3-yl)amino)spiro[cy Clopropane-1,5'-pyrrolo[2,3-d]pyrimidine]-6'(7'H)-one; 10) 7'-((1R,3R)-3-hydroxycyclohexyl)-2'-((3-( Tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-yl)amino)spi Ro[cyclopropane-1,5'-pyrrolo[2,3-d]pyrimidine]-6'(7'H)- on; 11) 7'-((1R,3R)-3-hydroxycyclohexyl)-2'-((2-( Methoxymethyl)-1H-imidazole-5-yl)amino)spiro[cyclopropane- 1,5'-pyrrolo[2,3-d]pyrimidine]-6'(7'H)-one; 12) 7'-((1R,3R)-3-hydroxycyclohexyl)-2'-((3-Me Toxy-1H-pyrazole-4-yl)amino)spiro[cyclopropane-1,5'-py lol[2,3-d]pyrimidine]-6'(7'H)-one; 13) 2'-((3-chloro-1H-pyrazole-4-yl)amino)-7'-((1 R,3R)-3-hydroxycyclohexyl)spiro[cyclopropane-1,5'-pyro Ro[2,3-d]pyrimidine]-6'(7'H)-one; 14) 2'-((3-cyclopropyl-1H-pyrazole-4-yl)amino)-7' -((1R,3R)-3-hydroxycyclohexyl)spiro[cyclopropane-1,5 '-pyrrolo[2,3-d]pyrimidine]-6'(7'H)-one; 15) 7'-((1R,3R)-3-hydroxycyclohexyl)-2'-((3-( (Trifluoromethyl)-1H-pyrazole-4-yl)amino)spiro[cyclopropane -1,5'-pyrrolo[2,3-d]pyrimidine]-6'(7'H)-one; 16) 7'-((1R,3R)-3-hydroxycyclohexyl)-2'-((1-( 2-Methoxyethyl)-1H-pyrazole-4-yl)amino)spiro[cyclopropane -1,5'-pyrrolo[2,3-d]pyrimidine]-6'(7'H)-one; 17) 7'-(3-hydroxycycloheptyl)-2'-((3-methyl-1H-pyra Zole-4-yl)amino)spiro[cyclopropane-1,5'-pyrrolo[2,3-d] Pyrimidine-6'(7'H)-one; 18) 7'-((1R,3R)-3-hydroxycycloheptyl)-2'-((3-Me (Tyl-1H-pyrazole-4-yl)amino)spiro[cyclopropane-1,5'-pyro [2,3-d]pyrimidine]-6'(7'H)-one; 19)2'-((3-chloro- 1H-pyrazole-4-yl)amino)-7'-((1R,3R)-3-hydroxycycline (roheptyl)spiro[cyclopropane-1,5'-pyrrolo[2,3-d]pyrimidine]- 6' (7' H) - On; 20) 4-((7'-((1R,3R)-3-hydroxycyclohexyl)-6'-O Kiso-6',7'-dihydrospiro[cyclopropane-1,5'-pyrrolo[2,3-d] Pyrimidine]-2'-yl)amino)-1H-pyrazole-3-carbonitrile; 21) 7'-((1R,3R)-3-hydroxycyclohexyl)-2'-((3-( Methoxymethyl)-1H-pyrazole-4-yl)amino)spiro[cyclopropane-1 ,5'-pyrrolo[2,3-d]pyrimidine]-6'(7'H)-one; 22) 7'-((1R,3R)-3-hydroxycyclohexyl)-2'-((3-( 2-Methoxyethoxy)-1H-pyrazole-4-yl)amino)spiro[cyclopropane n-1,5'-pyrrolo[2,3-d]pyrimidine]-6'(7'H)-one; 23) 2'-((3-ethoxy-1H-pyrazole-4-yl)amino)-7'-(( (1R,3R)-3-hydroxycyclohexyl)spiro[cyclopropane-1,5'-pi lol[2,3-d]pyrimidine]-6'(7'H)-one; A compound selected from any one of the following, or a pharmaceutically acceptable salt thereof, and / or tautomer. body. 【Request Item 34】 【Transformation 46】 The compound according to claim 1, or a pharmaceutically acceptable salt and / or tautomer thereof. 。 【Request Item 35】 【Chemistry 47】 The compound according to claim 1, or a pharmaceutically acceptable salt and / or tautomer thereof. 。 【Request Item 36】 【Transformation 48】 The compound according to claim 1, or a pharmaceutically acceptable salt and / or tautomer thereof. 。 【Request Item 37】 【Chemistry 49】 The compound according to claim 1, or a pharmaceutically acceptable salt and / or tautomer thereof. 。 【Request Item 38】 【Chemistry 50】 The compound according to claim 1, or a pharmaceutically acceptable salt and / or tautomer thereof. 。 【Request Item 39】 【Chemistry 51】 The compound according to claim 1, or a pharmaceutically acceptable salt and / or tautomer thereof. 。

40. A compound according to any one of claims 1 to 39 or a pharmaceutically acceptable salt thereof and / or A pharmaceutical composition comprising a tautomer and one or more pharmaceutically acceptable carriers.

41. A compound according to any one of claims 1 to 39 or a pharmaceutically acceptable salt thereof and / or This refers to a combination of a tautomer and one or more therapeutically active drugs.

42. A method for adjusting the CDK2 activity of a target, wherein the target is given a therapeutically effective amount, according to claims 1 to 39. A compound described in any one of the items or a pharmaceutically acceptable salt and / or tautomer thereof can be administered. A method that includes giving in.

43. A method for treating cancer, wherein a therapeutically effective amount is administered to a subject in need of the treatment (Claim 1-39) A compound described in any one of the items or a pharmaceutically acceptable salt and / or tautomer thereof can be administered. A method that includes giving in.

44. A compound or the compound described in any one of claims 1 to 39 for use as a pharmaceutical product. pharmaceutically acceptable salts and / or tautomers.

45. For use in the treatment of cancer, the compound or the compound according to any one of claims 1 to 39 pharmaceutically acceptable salts and / or tautomers thereof.

46. A compound according to any one of claims 1 to 39 or a pharmaceutically acceptable compound thereof in the treatment of cancer Use of acceptable salts and / or tautomers.

47. In the manufacture of a drug for the treatment of cancer, the compound described in any one of claims 1 to 39 or Use of the pharmaceutically acceptable salt and / or tautomer.

48. The aforementioned cancers include ovarian cancer, gastric cancer, uterine cancer, and breast cancer (e.g., ER+ breast cancer, e.g., ER+ / He). The method according to claim 43, selected from r2-breast cancer, lung cancer and endometrial cancer, claim 4 The compound for use described in 5, or the use described in claim 46 or claim 47.

49. The method according to claim 43 or claim 48, wherein the cancer is cyclin E-amplifying carcinoma. A compound for use as described in item 45 or 48, or as described in any one of claims 46 to 48. Use on a vehicle.

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