2-Substituted 3,4A,5,7,8,8A-hexahydro-4H-thiopyrano[4,3-D]pyrimidin-4-ones for wound healing

Claims

1. Compound of Formula (I): (I) or its single stereoisomer or mixture of stereoisomers; its single tautomer or mixture of tautomers; and / or its pharmaceutically acceptable salt; Where R 1 represents hydrogen, deuterium, C1-C3 alkyl, -OH, -O-C1-C3 alkyl, -CH2OH, or -B(OH)2; R 1a represents hydrogen, deuterium or C1-C3 alkyl; R 2 represents (a) phenyl substituted with R 3 and further optionally substituted with 1, 2 or 3 R groups 3a ; (b) phenyl substituted with 5- or 6-membered heteroaryl, wherein the 5- or 6-membered heteroaryl is substituted with R 3 and further optionally substituted with 1, 2 or 3 R groups 3a , and phenyl is further optionally substituted with 1, 2 or 3 R groups 3a , (c) phenyl optionally substituted with 1, 2 or 3 R groups 3aand additionally substituted with the -phenyl-R fragment 3 , where the phenyl in the fragment is -phenyl-R 3 optionally substituted with 1, 2, or 3 R groups 3a ; (d) 5- or 6-membered heteroaryl substituted with R 3 and further optionally substituted with 1, 2 or 3 R groups 3a ; (e) 5- or 6-membered heteroaryl optionally substituted with 1, 2 or 3 R groups 3a and additionally substituted with the -phenyl-R fragment 3 wherein phenyl is further optionally substituted with 1, 2 or 3 R groups 3a ; (f) 5- or 6-membered heteroaryl optionally substituted with 1, 2 or 3 R groups 3a and further substituted with the fragment -(5- or 6-membered heteroaryl)-R 3 where the 5- or 6-membered heteroaryl in the -(5- or 6-membered heteroaryl)-R fragment 3 optionally substituted with 1, 2, or 3 R groups 3a ; (g) C3-C6cycloalkyl substituted with R 3and further optionally substituted with 1 or 2 R groups 3a ; (h) C3-C6cycloalkyl substituted with 5- or 6-membered heteroaryl wherein the 5- or 6-membered heteroaryl is substituted with R 3 and further optionally substituted with 1, 2 or 3 R groups 3a , and where cycloalkyl is optionally substituted with 1 or 2 R groups 3a ; (i) C3-C6cycloalkyl substituted with phenyl, wherein phenyl is substituted with R 3 and further optionally substituted with 1, 2 or 3 R groups 3a , and where cycloalkyl is optionally substituted with 1 or 2 R groups 3a ; (j) 3-8-membered heterocycloalkyl substituted with phenyl or substituted with 5- or 6-membered heteroaryl, wherein phenyl and 5-6-membered heteroaryl are substituted with R 3 and further optionally substituted with 1, 2 or 3 R groups 3a ; (k) -CH=CH-R 5 where R 5 is phenyl or 5- or 6-membered heteroaryl, wherein phenyl and 5- or 6-membered heteroaryl are substituted with R 3and further optionally substituted with 1, 2 or 3 R groups 3a ; R 3 independently selected from -B(OH)2, cyano, halo, halo-C1-C6 alkyl, -(C0-C6 alkylene)-OR 4 or a 5-10-membered heterocycle, wherein the 5-10-membered heterocycle is optionally substituted with cyano; or when R 2 represents (a), then R 3 and one R 3a , if they are located at adjacent carbon atoms, then together with the carbon atoms to which they are connected, they form (a-1) where the * sign indicates the carbon atoms common with the carbon atoms of the phenyl ring, and where the remaining optional R 3a at the phenyl part of the compound are defined below, and each R 7a independently represents hydrogen or C1-C6 alkyl; each R 3a independently selected from cyano, halo, -OH, C1-C6 alkyl, halo-C1-C6 alkyl, and C1-C6 alkoxy; R 4is hydroxy-C1-C6 alkyl, C1-C6 alkoxy-C1-C6 alkyl, or C1-C6 alkoxycarbonyl-NH-C1-C6 alkyl; and in this case the connection does not represent: 2-(4-(trifluoromethyl)phenyl)-3,5,7,8-tetrahydro-4H-thiopyrano[4,3-d]pyrimidin-4-one or its single stereoisomer or mixture of stereoisomers; its single tautomer or mixture of tautomers; and / or a pharmaceutically acceptable salt thereof; 2-(4-(4-methoxyphenyl)piperazin-1-yl)-3,5,7,8-tetrahydro-4H-thiopyrano[4,3-d]pyrimidin-4-one or its single stereoisomer or mixture of stereoisomers; its single tautomer or mixture of tautomers; and / or a pharmaceutically acceptable salt thereof; 2-(4-(3-methoxyphenyl)piperazin-1-yl)-3,5,7,8-tetrahydro-4H-thiopyrano[4,3-d]pyrimidin-4-one or its single stereoisomer or mixture of stereoisomers; its single tautomer or mixture of tautomers; and / or a pharmaceutically acceptable salt thereof; 2-(4-(2-methoxyphenyl)piperazin-1-yl)-3,5,7,8-tetrahydro-4H-thiopyrano[4,3-d]pyrimidin-4-one or its single stereoisomer or mixture of stereoisomers; its single tautomer or mixture of tautomers; and / or a pharmaceutically acceptable salt thereof; 2-(4-chlorophenyl)-3,5,7,8-tetrahydro-4H-thiopyrano[4,3-d]pyrimidin-4-one or its single stereoisomer or mixture of stereoisomers; its single tautomer or mixture of tautomers; and / or a pharmaceutically acceptable salt thereof; 2-(5-(trifluoromethyl)pyridin-2-yl)-3,5,7,8-tetrahydro-4H-thiopyrano[4,3-d]pyrimidin-4-one or its single stereoisomer or mixture of stereoisomers; its single tautomer or mixture of tautomers; and / or a pharmaceutically acceptable salt thereof; 2-(3-(trifluoromethyl)phenyl)-3,5,7,8-tetrahydro-4H-thiopyrano[4,3-d]pyrimidin-4-one or its single stereoisomer or mixture of stereoisomers; its single tautomer or mixture of tautomers; and / or a pharmaceutically acceptable salt thereof; 2-(3-(trifluoromethyl)phenyl)-3,5,7,8-tetrahydro-4H-thiopyrano[4,3-d]pyrimidin-4-one or its single stereoisomer or mixture of stereoisomers; its single tautomer or mixture of tautomers; and / or a pharmaceutically acceptable salt thereof; or 2-(5-chlorothiophen-3-yl)-3,5,7,8-tetrahydro-4H-thiopyrano[4,3-d]pyrimidin-4-one or its single stereoisomer or mixture of stereoisomers; its single tautomer or mixture of tautomers; and / or a pharmaceutically acceptable salt thereof.

2. The compound according to claim 1 or its single stereoisomer, or a mixture of stereoisomers, or its single tautomer, or a mixture of tautomers; and / or its pharmaceutically acceptable salt, where R 1 and R 1a independently selected from hydrogen and deuterium.

3. The compound according to claim 1 or 2, or its single stereoisomer, or a mixture of stereoisomers, or its single tautomer, or a mixture of tautomers; and / or a pharmaceutically acceptable salt thereof, wherein ring A is or , and where denotes the attachment to the rest of the compound of Formula (I).

4. The compound according to any one of claims 1-3, or its single stereoisomer, or a mixture of stereoisomers, or its single tautomer, or a mixture of tautomers; and / or its pharmaceutically acceptable salt, where R 2 is phenyl substituted with R 3 and further optionally substituted with 1, 2 or 3 R groups 3a .

5. The compound according to claim 4 or its single stereoisomer or mixture of stereoisomers or its single tautomer or mixture of tautomers; and / or its pharmaceutically acceptable salt, where R 3 attached to the phenyl ring at the para position; or R 3 and one R 3a , if they are located at adjacent carbon atoms, then together with the carbon atoms to which they are connected, they form a ring (a-1) and where the phenyl moiety is optionally substituted by the remaining R groups 3a .

6. A compound according to any one of claims 1-5, or its single stereoisomer or mixture of stereoisomers, its single tautomer or mixture of tautomers, and / or its pharmaceutically acceptable salt, where R 2 selected from a group including , , , And .

7. A compound according to any one of claims 1 to 6, or its single stereoisomer, or a mixture of stereoisomers, or its single tautomer, or a mixture of tautomers; and / or a pharmaceutically acceptable salt thereof, where R 2 selected from a group including , , , , , , , , , , , , And .

8. A compound according to any one of claims 1 to 7, or its single stereoisomer, or a mixture of stereoisomers, or its single tautomer, or a mixture of tautomers; and / or a pharmaceutically acceptable salt thereof, where R 2 selected from a group including , , , , , , , , , , , , , , , , , , And .

9. The compound according to any one of claims 1-3, or its single stereoisomer, or a mixture of stereoisomers, or its single tautomer, or a mixture of tautomers; and / or its pharmaceutically acceptable salt, where R 2 is phenyl substituted with a 5- or 6-membered heteroaryl, where the 5- or 6-membered heteroaryl is substituted with R 3 and further optionally substituted with 1, 2 or 3 R groups 3a , and wherein phenyl is further optionally substituted with 1, 2 or 3 R groups 3a .

10. The compound according to claim 9 or its single stereoisomer or mixture of stereoisomers or its single tautomer or mixture of tautomers; and / or its pharmaceutically acceptable salt, where R 2is phenyl substituted at the para position with a 5- or 6-membered heteroaryl, where the 5- or 6-membered heteroaryl is substituted with R 3 and further optionally substituted with 1, 2 or 3 R groups 3a , and wherein phenyl is further optionally substituted with 1, 2 or 3 R groups 3a ; and when the 5- or 6-membered heteroaryl is a 6-membered heteroaryl, then R 3 substituted at the para-position of the 6-membered heteroaryl.

11. The compound according to any one of claims 1-3, 9, and 10, or its single stereoisomer or a mixture of stereoisomers, and / or its pharmaceutically acceptable salt, where R 2 selected from a group including , , , , , , And .

12. A compound according to any one of paragraphs 1-3 and 9-11, or its single stereoisomer, or a mixture of stereoisomers, or its single tautomer, or a mixture of tautomers; and / or a pharmaceutically acceptable salt thereof, where R 2selected from a group including , , , , , , And .

13. The compound according to any one of claims 1-3, or its single stereoisomer, or a mixture of stereoisomers, or its single tautomer, or a mixture of tautomers; and / or its pharmaceutically acceptable salt, where R 2 is phenyl optionally substituted with 1, 2 or 3 R groups 3a and additionally substituted with the -phenyl-R fragment 3 , where the phenyl in the fragment is -phenyl-R 3 optionally substituted with 1, 2, or 3 R groups 3a .

14. The compound according to claim 13, or its single stereoisomer, or a mixture of stereoisomers, or its single tautomer, or a mixture of tautomers; and / or its pharmaceutically acceptable salt, where R 2 is phenyl optionally substituted with 1, 2 or 3 R groups 3a and additionally substituted in the para-position by the -phenyl-R fragment 3, where the phenyl in the fragment is -phenyl-R 3 optionally substituted with 1, 2, or 3 R groups 3a , and where R 3 is located in the para-position of phenyl in the -phenyl-R fragment 3 .

15. The compound according to any one of claims 1-3 and 13, 14, or its single stereoisomer, or a mixture of stereoisomers, or its single tautomer, or a mixture of tautomers; and / or its pharmaceutically acceptable salt, where R 2 selected from a group including , , , , And .

16. A compound according to any one of paragraphs 1-3 and 13-15, or its single stereoisomer, or a mixture of stereoisomers, or its single tautomer, or a mixture of tautomers; and / or a pharmaceutically acceptable salt thereof, where R 2 selected from a group including , , , , , , And .

17. The compound according to any one of claims 1-3, or its single stereoisomer, or a mixture of stereoisomers, or its single tautomer, or a mixture of tautomers; and / or its pharmaceutically acceptable salt, where R 2 is a 5-6-membered heteroaryl substituted with R 3 and further optionally substituted with 1, 2 or 3 R groups 3a ; where R 3 is not necessarily located in the para position of the 6-membered heteroaryl.

18. The compound according to any one of claims 1-3, or its single stereoisomer, or a mixture of stereoisomers, or its single tautomer, or a mixture of tautomers; and / or its pharmaceutically acceptable salt, where R 2 is a 5- or 6-membered heteroaryl optionally substituted with 1, 2, or 3 R groups 3a and additionally substituted with the -phenyl-R fragment 3 , wherein phenyl is further optionally substituted with 1, 2 or 3 R groups 3a ; where the fragment is -phenyl-R 3optionally located in the para position of a 6-membered heteroaryl; and where R 3 is not necessarily located in the para position of phenyl.

19. The compound according to any one of claims 1-3, or its single stereoisomer, or a mixture of stereoisomers, or its single tautomer, or a mixture of tautomers; and / or its pharmaceutically acceptable salt, where R 2 is a 5- or 6-membered heteroaryl optionally substituted with 1, 2, or 3 R groups 3a and further substituted with the fragment -(5- or 6-membered heteroaryl)-R 3 , where the 5- or 6-membered heteroaryl in the fragment is -(5- or 6-membered heteroaryl)-R 3 optionally substituted with 1, 2, or 3 R groups 3a ; where the fragment is -(6-membered heteroaryl)-R 3 optionally located at the para-position of the first 6-membered heteroaryl; and where R 3 is optionally located in the para position of the 6-membered heteroaryl to which it is attached.

20. The compound according to any one of claims 1-3 and 19, or its single stereoisomer, or a mixture of stereoisomers, or its single tautomer, or a mixture of tautomers; and / or its pharmaceutically acceptable salt, where R 2 represents .

21. The compound according to any one of claims 1-3, or its single stereoisomer, or a mixture of stereoisomers, or its single tautomer, or a mixture of tautomers; and / or its pharmaceutically acceptable salt, where R 2 is C3-C6cycloalkyl substituted with R 3 and further optionally substituted with 1 or 2 R groups 3a .

22. The compound according to any one of claims 1-3 and 21, or its single stereoisomer, or a mixture of stereoisomers, or its single tautomer, or a mixture of tautomers; and / or its pharmaceutically acceptable salt, where R 2 represents , R 3 optionally represents a 5- to 10-membered heterocycle, optionally substituted with cyano.

23. The compound according to any one of claims 1-3, or its single stereoisomer, or a mixture of stereoisomers, or its single tautomer, or a mixture of tautomers; and / or its pharmaceutically acceptable salt, where R 2 is a C3-C6 cycloalkyl substituted with a 5- or 6-membered heteroaryl where the 5- or 6-membered heteroaryl is substituted with R 3 and further optionally substituted with 1, 2 or 3 R groups 3a , and where cycloalkyl is optionally substituted with 1 or 2 R groups 3a .

24. The compound according to any one of claims 1-3, or its single stereoisomer, or a mixture of stereoisomers, or its single tautomer, or a mixture of tautomers; and / or its pharmaceutically acceptable salt, where R 2 is a C3-C6 cycloalkyl substituted with phenyl, where phenyl is substituted with R 3 and further optionally substituted with 1, 2 or 3 R groups 3a , and where cycloalkyl is optionally substituted with 1 or 2 R groups 3a .

25. The compound according to any one of claims 1-3, or its single stereoisomer, or a mixture of stereoisomers, or its single tautomer, or a mixture of tautomers; and / or its pharmaceutically acceptable salt, where R 2 is a 3- to 8-membered heterocycloalkyl substituted by phenyl or 5- or 6-membered heteroaryl, wherein the phenyl and 5- to 6-membered heteroaryl are substituted by R 3 and further optionally substituted with 1, 2 or 3 R groups 3a .

26. The compound according to any one of paragraphs 1-3 and 25, or its single stereoisomer, or a mixture of stereoisomers, or its single tautomer, or a mixture of tautomers; and / or its pharmaceutically acceptable salt, where R 2 selected from a group including , , And .

27. The compound according to any one of claims 1-3, or its single stereoisomer, or a mixture of stereoisomers, or its single tautomer, or a mixture of tautomers; and / or its pharmaceutically acceptable salt, where R 2represents -CH=CH-R 5 and R 5 is phenyl or a 5- or 6-membered heteroaryl, wherein the phenyl and 5- or 6-membered heteroaryl are substituted with R 3 and further optionally substituted with 1, 2 or 3 R groups 3a .

28. The compound according to any one of claims 1-3 and 27, or its single stereoisomer, or a mixture of stereoisomers, or its single tautomer, or a mixture of tautomers; and / or its pharmaceutically acceptable salt, where R 2 selected from a group including And .

29. The compound according to any one of claims 1 to 28, or its single stereoisomer, or a mixture of stereoisomers, or its single tautomer, or a mixture of tautomers; and / or its pharmaceutically acceptable salt; where R 3 is cyano, -B(OH)2, or -(C0-C6alkylene)-OR 4 .

30. A compound according to any one of claims 1-7, 9-11, and 13-29, or its single stereoisomer or mixture of stereoisomers, or its single tautomer or mixture of tautomers; and / or its pharmaceutically acceptable salt; where R 3 is cyano.

31. A compound according to any one of claims 1-7, 9-11, and 13-29, or its single stereoisomer or mixture of stereoisomers, or its single tautomer or mixture of tautomers; and / or a pharmaceutically acceptable salt thereof; where R 3 is -B(OH)2.

32. The compound according to any one of paragraphs 1-7, 9-11, and 13-29, or its single stereoisomer or mixture of stereoisomers, or its single tautomer or mixture of tautomers; and / or its pharmaceutically acceptable salt; where R 3 is -(C0-C6alkylene)-OR 4 .

33. The compound according to any one of claims 1-7, 9-11, 13-29, and 32, or its single stereoisomer or mixture of stereoisomers, or its single tautomer or mixture of tautomers; and / or its pharmaceutically acceptable salt; where R 3 is -(C1-6alkylene)-OR 4 .

34. The compound according to any one of claims 1-7, 9-11, 13-29, 32, and 33, or its single stereoisomer or mixture of stereoisomers, or its single tautomer or mixture of tautomers; and / or its pharmaceutically acceptable salt; where R 4 is hydroxy-C1-C6 alkyl.

35. The compound according to any one of claims 1-7, 9-11, 13-29, 32, and 33, or its single stereoisomer or mixture of stereoisomers, or its single tautomer or mixture of tautomers; and / or its pharmaceutically acceptable salt; where R 4 is C1-C6alkoxy-C1-C6alkyl.

36. The compound according to any one of claims 1-7, 9-11, 13-29, 32, and 33, or its single stereoisomer or mixture of stereoisomers, or its single tautomer or mixture of tautomers; and / or its pharmaceutically acceptable salt; where R 4 is C1-C6alkoxycarbonyl-NH-C1-C6alkyl.

37. The compound according to any one of claims 1-3, 9-11, 13-16, and 18-20, or its single stereoisomer or mixture of stereoisomers, or its single tautomer or mixture of tautomers; and / or its pharmaceutically acceptable salt; where R 2 is (b), (c), (e), or (f), and R 3 is halo, cyano, -B(OH)2, or -(C0-C6alkylene)-OR 4 .

38. The compound of claim 1, or its single stereoisomer or mixture of stereoisomers, or its single tautomer or mixture of tautomers; and / or its pharmaceutically acceptable salt; selected from the group consisting of Compounds 1-44 shown in Table 1.

39. A pharmaceutical composition comprising a compound according to any one of claims 1-38, or its single stereoisomer or mixture of stereoisomers, or its single tautomer or mixture of tautomers; and / or its pharmaceutically acceptable salt; and containing a pharmaceutically acceptable carrier.

40. The pharmaceutical composition according to claim 39, wherein the pharmaceutical carrier contains: a matrix component containing a conjugate of graphene oxide (GO) and hyaluronic acid (HA), i.e. (GO-HA), where GO and HA are covalently linked via a linker; polyethylene glycol (PEG), although the presence of PEG is not required; a thickening agent, although the presence of a thickening agent is not mandatory; and water, wherein the content of the compound is from about 0.001 wt.% to about 5 wt.% of the total weight of the composition.

41. A method for inhibiting Wnt signaling pathway activity in a subject, comprising contacting the subject with an effective amount of a compound according to any one of claims 1-38, or a single stereoisomer or mixture of stereoisomers thereof, a single tautomer or mixture of tautomers thereof, and / or a pharmaceutically acceptable salt thereof.

42. A method for treating a disease, disorder or condition associated with Wnt signaling pathway activity, comprising administering a compound according to any one of claims 1-38, or its single stereoisomer or mixture of stereoisomers, its single tautomer or mixture of tautomers, and / or a pharmaceutically acceptable salt thereof; or administering a pharmaceutical composition according to claim 39 or 40 to a mammal in need of such treatment.

43. The method according to claim 42, wherein the method is intended to stimulate tissue regeneration in the area of ​​a wound in a mammal in need of such stimulation, and wherein the wound is in contact with an effective amount of the compound (or its single stereoisomer or mixture of stereoisomers, its single tautomer or mixture of tautomers, and / or its pharmaceutically acceptable salt) or with a pharmaceutical composition.

44. The method of claim 42, wherein the disease, disorder, or condition is selected from a chronic wound, an acute wound, an alkali-induced corneal burn wound, a burn, a lesion (including lesions caused by HPV and / or a virus selected from the Poxviridae family of viruses), a disease that is inflammatory dermatitis (including acne, psoriasis, rosacea, and scleroderma), a cartilage disease (including osteoarthritis, rheumatoid arthritis, joint disease, and degenerative cartilage disease), a bone disease (including osteoporosis), an organ fibrosis (including pulmonary fibrosis, cardiac fibrosis, liver fibrosis, and renal fibrosis), cancer (including melanoma, breast cancer, and prostate cancer), a denervated body part in need of reinnervation, tissue in need of regeneration (including damaged elastic cartilage), bacterial growth requiring suppression, fungal growth requiring suppression, tissue requiring neovascularization, osteoclast differentiation requiring suppression,osteoblast differentiation disorders (in which osteoblast differentiation must be suppressed) and / or bone destruction in breast cancer.

45. A method for stimulating bacteriostasis associated with Wnt signaling pathway activity, comprising administering XAV939 or a tautomer thereof and / or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier; administering a compound according to any one of claims 1-38 or a single stereoisomer or mixture of stereoisomers thereof, a single tautomer or mixture of tautomers thereof, and / or a pharmaceutically acceptable salt thereof; or administering a pharmaceutical composition according to claim 39 or 40 to a mammal in need of such stimulation.

46. ​​A compound, or its salt, and / or its stereoisomer or mixture of stereoisomers according to one of the following formulas: Formula (A): ; Formula (B): ; Formula (C): ; or Formula (D): ; And Where LG 1 is a leaving group such as fluorine, chlorine, bromine, iodine, triflate, mesylate, triazole, pyrazole, boronic acid, boronic ester, or aryl trifluoroborate; R 1 represents hydrogen, deuterium, C1-C3 alkyl, -OH, -O-C1-C3 alkyl, -CH2OH, or -B(OH)2; R 1a represents hydrogen, deuterium or C1-C3 alkyl; R 20 is alkyl, preferably methyl or ethyl, or CD3; R 2′ represents (b1) phenyl substituted with 5- or 6-membered heteroaryl, wherein the 5- or 6-membered heteroaryl is substituted with LG 1 and further optionally substituted with 1, 2 or 3 R groups 3a , and wherein phenyl is further optionally substituted with 1, 2 or 3 R groups 3a , (c1) phenyl optionally substituted with 1, 2 or 3 R groups 3aand additionally substituted with the -phenyl- LG fragment 1 , where phenyl in the fragment -phenyl- LG 1 optionally substituted with 1, 2, or 3 R groups 3a ; (e1) 5- or 6-membered heteroaryl optionally substituted with 1, 2 or 3 R groups 3a and additionally substituted with the -phenyl- LG fragment 1 , wherein phenyl is further optionally substituted with 1, 2 or 3 R groups 3a ; (f1) 5- or 6-membered heteroaryl optionally substituted with 1, 2 or 3 R groups 3a and additionally substituted with the fragment -(5- or 6-membered heteroaryl)- LG 1 , where the 5- or 6-membered heteroaryl in the fragment -(5- or 6-membered heteroaryl)- LG 1 optionally substituted with 1, 2, or 3 R groups 3a ; (h1) C3-C6cycloalkyl substituted with NH2 or OH and further optionally substituted with 1 or 2 R groups 3a ; or (i1) C3-C6cycloalkyl substituted with phenyl, wherein phenyl is substituted with LG 1and phenyl is further optionally substituted with 1, 2 or 3 R groups 3a , and where cycloalkyl is optionally substituted with 1 or 2 R groups 3a ; And in this case the connection does not represent: methyl 4-oxotetrahydro-2H-thiopyran-3-carboxylate ; or its salt and / or stereoisomer or mixture of stereoisomers.

47. A method for producing a compound of Formula (I) according to any one of paragraphs 1-37, comprising: a) reduction of the compound of Formula (A): in contact with R 2' -C(O)H; or b) reduction of the compound of Formula (B): in contact with R 2' -C(NH)NH2, where R 20 is Me or CD3; or c) reduction of the compound of Formula (C): in contact with R 2' -H, where is LG 1 is fluorine, chlorine, bromine, iodine, triflate, mesylate, triazole, pyrazole, boronic acid, boronic ester, or aryl trifluoroborate; and optionally isolating the Compound of Formula (I); where R 2' represents (b1) phenyl substituted with 5- or 6-membered heteroaryl, wherein the 5- or 6-membered heteroaryl is substituted with LG 1 and further optionally substituted with 1, 2 or 3 R groups 3a , and wherein phenyl is further optionally substituted with 1, 2 or 3 R groups 3a , (c1) phenyl optionally substituted with 1, 2 or 3 R groups 3a and additionally substituted with the -phenyl- LG fragment 1 , where phenyl in the fragment -phenyl- LG 1 optionally substituted with 1, 2, or 3 R groups 3a ; (e1) 5- or 6-membered heteroaryl optionally substituted with 1, 2 or 3 R groups 3a and additionally substituted with the -phenyl- LG fragment 1 , wherein phenyl is further optionally substituted with 1, 2 or 3 R groups 3a ; (f1) 5- or 6-membered heteroaryl optionally substituted with 1, 2 or 3 R groups 3aand additionally substituted with the fragment -(5- or 6-membered heteroaryl)- LG 1 , where the 5- or 6-membered heteroaryl in the fragment -(5- or 6-membered heteroaryl)- LG 1 optionally substituted with 1, 2, or 3 R groups 3a ; (h1) C3-C6cycloalkyl substituted with NH2 or OH and further optionally substituted with 1 or 2 R groups 3a ; or (i1) C3-C6cycloalkyl substituted with phenyl, wherein phenyl is substituted with LG 1 , and phenyl is further optionally substituted with 1, 2 or 3 R groups 3a , and where cycloalkyl is optionally substituted with 1 or 2 R groups 3a ; And in this case the connection does not represent: methyl 4-oxotetrahydro-2H-thiopyran-3-carboxylate ; or its salt and / or stereoisomer or mixture of stereoisomers.

48. The method according to claim 47, wherein the contacting is carried out in an alkaline medium.