RU2005118991A - Pyrazole [3, 4-B] Pyridine Compounds and Their Use as Phosphodiesterase Inhibitors - Google Patents

Claims (57)

1. The compound of formula (I) or its salt

where R ¹ represents C _1-4 alkyl, C _1-3 fluoroalkyl or - (CH ₂ ) ₂ OH; R ² represents a hydrogen atom (H), methyl or C ₁ fluoroalkyl; R ³ represents a possibly substituted branched C _3-6 alkyl, possibly substituted C _3-8 cycloalkyl, possibly substituted monounsaturated C _5-7 cycloalkenyl, possibly substituted phenyl or a possibly substituted heterocyclic group of sub-formula (aa), (bb) or ( cc)

or

or

where n ¹ and n ² independently represent 1 or 2; and Y represents O, S, SO ₂ or NR ⁴ ; where R ⁴ represents a hydrogen atom (H), C _1-2 alkyl, C _1-2 fluoroalkyl, CH ₂ C (O) NH ₂ , C (O) NH ₂ , C (O) -C _1-2 alkyl or C (O) -C ₁ fluoroalkyl; where in R ^{3 a} possibly substituted branched C _3-6 alkyl is optionally substituted with one or two substituents representing oxo (= O), OH, C _1-2 alkoxy or C _1-2 fluoroalkoxy, and where any such substituent is not a substituent at a carbon atom of the group R ³ , connected (bound) to the group —NH— of the formula (I); where in R ³ phenyl is optionally substituted with one substituent, which is fluoro, chloro, C _1-2 alkyl, C _1-2 fluoroalkyl, C _1-2 alkoxy, C _1-2 fluoroalkoxy or cyano, or two or three fluoro substituents; where in R ³ C _{3-8 a} cycloalkyl or heterocyclic group of a sub-formula (aa), (bb) or (cc) is optionally substituted with one or two substituents independently representing oxo (= O); IT; C _1-2 alkoxy; C _1-2 fluoroalkoxy; NHR ²¹ , where R ²¹ represents a hydrogen atom (H) or C _1-4 straight chain alkyl; C _1-2 alkyl; C _1-2 fluoroalkyl; -CH ₂ OH; -CH ₂ CH ₂ OH; —CH ₂ NHR ²² , wherein R ²² is H or C _1-2 alkyl; —C (O) OR ²³ where R ²³ represents H or C _1-2 alkyl; —C (O) NHR ²⁴ , wherein R ²⁴ is H or C _1-2 alkyl; —C (O) R ²⁵ , wherein R ²⁵ is C _1-2 alkyl; fluoro; hydroxyimino (= N-OH); or (C _1-4 alkoxy) imino (= N-OR ²⁶ where R ²⁶ represents C _1-4 alkyl); and where any substituent OH, alkoxy, fluoroalkoxy or NHR ^{21 is} not substituted at the R ³ ring carbon atom (linked) to the —NH— group of formula (I), and is not substituted at any R ³ ring carbon atom associated with group Y of a heterocyclic group (aa), (bb) or (cc); and where, if R ³ is optionally substituted with monounsaturated C _5-7 cycloalkenyl, then this cycloalkenyl is optionally substituted with one or two substituents independently representing fluoro or C _1-2 alkyl, provided that if there are two substituents, they both do not represent C ₂ alkyl, and the ring carbon atom R ³ bonded to the —NH— group of formula (I) is not involved in the cycloalkenyl double bond; and R ^3a represents a hydrogen atom (H) or C _1-3 straight chain alkyl; with the proviso that if R ^3a is C _1-3 alkyl, then R ³ is tetrahydro-2H-pyran-4-yl, cyclohexyl (i.e., unsubstituted), 3-hydroxy-cyclohexyl, 4-oxo-cyclohexyl or 4- (hydroxyimino) cyclohexyl; and where Het corresponds to subformula (i), (ii), (iii), (iv) or (v)

or

or

or

or

where W ¹ , W ² , W ⁴ and W ⁵ represents N; and W ³ represents NR ^W ; X ¹ , X ³ and X ⁴ represents N or CR ^X ; X ² represents O, S or NR ^X ; and X ⁵ represents CR ^X1 R ^X2 or CR ^X3 R ^X4 ; Y ¹ , Y ² and Y ³ represents CR ^Y or N; Y ⁴ represents O, S or NR ^Y ; and Y ⁵ represents CR ^Y1 R ^Y2 ; Z ¹ and Z ⁵ represents O, S or NR ^Z ; and Z ² , Z ³ and Z ⁴ represents N or CR ^z ; where R ^W represents a hydrogen atom (H) or C _1-2 alkyl; R ^X , R ^X2 , R ^Y and R ^Y2 independently represent a hydrogen atom (H); C _1-8 alkyl; C _3-6 cycloalkyl optionally substituted with one or two C _1-2 alkyl groups and / or one oxo group (= O); - (CH ₂ ) _n ^2a —C _3-6 cycloalkyl optionally substituted by —— (CH ₂ ) _n ^2a - or a C _3-6 cycloalkyl moiety With a _1-2 alkyl group or optionally substituted by a C _3-6 cycloalkyl moiety a group —CH ₂ C (O) NHC _1-2 alkyl, wherein n ^2a is 1, 2 or 3; - (CH ₂ ) _n ³ -S (O) ₂ -R ⁵ , -CH (C _1-2 alkyl) -S (O) ₂ -R ⁵ , -CMe ₂ -S (O) ₂ -R ⁵ or C _3-5 cycloalkyl substituted on the connecting carbon atom with a group —S (O) ₂ —R ⁵ , wherein n ³ is 1 or 2; and R ⁵ is C _1-4 alkyl, —NR ¹⁵ R ¹⁶ , phenyl, pyridinyl bonded to a carbon atom, or benzyl (where phenyl and benzyl are independently optionally substituted on the aromatic ring with one or two substituents independently representing fluoro, chloro C _1-2 alkyl, C ₁ fluoroalkyl, C _1-2 alkoxy, C ₁ fluoroalkoxy or OH, and where pyridinyl is optionally substituted with one methyl, methoxy or OH group (including any tautomer thereof); where R ¹⁵ represents H, C _1-4 alkyl, phenyl, benzyl (where phenyl and benzyl are independently possibly substituted on the aromatic ring by one or two substituents independently representing fluoro, chloro, C _1-2 alkyl, C ₁ fluoroalkyl, C _1-2 alkoxy or C ₁ fluoroalkoxy), CH (Me) Ph or pyridinyl bonded to a carbon atom, optionally substituted with one methyl, methoxy or OH group (including any tautomer thereof); and R ¹⁶ represents H or C _1-2 alkyl; or where R ¹⁵ and R ¹⁶ together represent - (CH ₂ ) _n ^3a —X ^3a - (CH ₂ ) _n ^3b -, where n ^3a and n ^3b independently represent 2 or 3, and X ^3a represents a bond, - CH ₂ -, O or NR ^8a , where R ^8a represents H or C _1-2 alkyl, acetyl, -S (O) ₂ Me or phenyl, and where the ring formed by NR ¹⁵ R ¹⁶ is optionally substituted at the ring carbon atom one or two substituents independently representing methyl or oxo (= O); - (CH ₂ ) _n ⁴ —NR ⁶ R ⁷ , —CH (C _1-2 alkyl) —NR ⁶ R ⁷ , —Cme ₂ —NR ⁶ R ⁷ or C _3-5 cycloalkyl substituted at the carbon atom by the group - NR ⁶ R ⁷ where n ⁴ represents 0, 1, 2 or 3; and R ⁶ and R ⁷ independently represent H, C _1-6 alkyl, C _3-6 cycloalkyl, —CH ₂ —C _3-6 cycloalkyl, —C (O) R ¹⁷ , —S (O) ₂ R ¹⁸ , phenyl, benzyl (where phenyl and benzyl are independently possibly substituted on the aromatic ring with one or two substituents independently representing fluoro, chloro, C _1-2 alkyl, C ₁ fluoroalkyl, C _1-2 alkoxy or C ₁ fluoroalkoxy) or pyridinyl, bound with a carbon atom, possibly substituted with one methyl, methoxy or OH group (including any tautomer thereof); and where R ¹⁷ and R ¹⁸ independently are C _1-6 alkyl, C _3-6 cycloalkyl, an optionally substituted 5-membered heteroaryl representing furyl (furanyl), or 1,3-oxazolyl, or isoxazolyl, or oxadiazolyl, or thienyl, or 1,3-thiazolyl, or isothiazolyl, or pyrrolyl, or imidazolyl, or pyrazolyl (all independently possibly substituted by one oxo group and / or one or two methyl groups), or phenyl, or benzyl (where phenyl and benzyl are independently possible substituted on the aromatic ring by one or two substituents independently representing ft ro, chloro, C _1-2 alkyl, C ₁ fluoroalkyl, C _1-2 alkoxy, C ₁ fluoroalkoxy or OH), or pyridinyl bonded to a carbon atom optionally substituted by one methyl, methoxy or OH (including any tautomer thereof) ; or R ⁶ and R ⁷ together represent - (CH ₂ ) _n ⁵ —X ⁵ - (CH ₂ ) _n ⁶ -, where n ⁵ and n ⁶ independently represent 2 or 3, and X ⁵ represents a bond, —CH ₂ -, O or NR ⁸ , where R ⁸ represents H, C _1-2 alkyl, acetyl, -S (O) ₂ Me or phenyl, and where the ring formed by NR ⁶ R ⁷ is optionally substituted at the ring carbon atom with one or two substituents independently representing methyl or oxo (= O); - (CH ₂ ) _n ⁷ -OR ⁹ ; where n ⁷ represents 0, 1, 2 or 3, and R ⁹ represents H, C _1-6 alkyl, C _3-6 cycloalkyl, —CH ₂ —C _3-6 cycloalkyl, —C (O) R ¹⁷ , phenyl or benzyl (where phenyl and benzyl are independently possibly substituted on the aromatic ring with one or two groups of fluoro, chloro, C _1-2 alkyl, C ₁ fluoroalkyl, C _1-2 alkoxy or C ₁ fluoroalkoxy); where n ⁷ represents 0 only when - (CH ₂ ) _n ⁷ -OR ⁹ is bonded to a carbon atom in the Het ring; and where n ^{7 is} not 0 when Het corresponds to the sub-formula (v) (that is, n ^{7 is} not 0 for R ^X2 and for R ^Y2 ); - (CH ₂ ) _n ¹¹ -C (O) -NR ¹⁰ R ¹¹ , -CH (C _1-2 alkyl) -C (O) -NR ¹⁰ R ¹¹ , -CMe ₂ -C (O) -NR ¹⁰ R ¹¹ or C _3-5 cycloalkyl substituted at the carbon atom by the group —C (O) —NR ¹⁰ R ¹¹ , where n ¹¹ is 0, 1 or 2; and where R ¹⁰ and R ¹¹ independently represent H; C _1-6 alkyl; C _1-4 fluoroalkyl; C _2-4 alkyl substituted with one OH group or —O— _1-2 alkyl at a position other than the point of attachment; C _3-6 cycloalkyl optionally substituted with one or two methyl groups; —CH ₂ —C _3-6 cycloalkyl optionally substituted with one methyl group, NH ₂ or NHMe; - (CH ₂ ) _n ¹⁷ -Het ² ; pyridinyl bonded to a carbon atom, optionally substituted with one methyl, methoxy or OH group (including any tautomer thereof); phenyl; benzyl; or —CH (C _1-2 alkyl) Ph [where phenyl, benzyl and —CH (C _1-2 alkyl) Ph are independently optionally substituted on the aromatic ring with one or two substituents independently representing fluoro, chloro, C _1-2 alkyl , C ₁ fluoroalkyl, C _1-2 alkoxy, C ₁ fluoroalkoxy, OH, -NR ^10a R ^10b (where R ^10a represents H or C _1-2 alkyl, and R ^10b represents H, C _1-2 alkyl, - C (O) —C _1-2 alkyl or —S (O) ₂ —C _1-2 alkyl), —C (O) —NR ^10c R ^10d (where R ^10c and R ^{10d are} independently H or C _{1- 2} alkyl) or —S (O) ₂ —R ^10e (where R ^10e represents C _1-2 alkyl, NH ₂ , NHMe or NMe ₂ )]; where n ¹⁷ represents 0, 1 or 2, and where Het ² represents a 4-, 5- or 6-membered saturated heterocyclic ring containing one O or S ring atom or one NR ²⁷ ring group, where R ²⁷ represents H , C _1-2 alkyl, —C (O) Me or —S (O) ₂ Me, where the Het ² ring is optionally substituted on the ring carbon atom with one or two substituents independently representing methyl or oxo (= O); and where, if n ¹⁷ is 2, then the Het ² ring may possibly contain one additional ring atom N at the position of the Het ² ring associated with the group - (CH ₂ ) _n ¹⁷ -; provided that if Het ² contains one (one) ring atom (s) of an O / S or NR ²⁷ atom / group and one additional N ring atom, then this (this) ring atom / group O / S / NR ²⁷ and this one additional ring atom N is not directly connected to each other and separated by more than one carbon atom; or R ¹⁰ and R ¹¹ together represent - (CH ₂ ) _n ⁸ —X ⁶ - (CH ₂ ) _n ⁹ -, where n ⁸ and n ⁹ independently represent 2 or 3, and X ⁶ represents a bond, —CH ₂ -, O or NR ¹² , where R ¹² represents H, C _1-2 alkyl, acetyl, -S (O) ₂ Me or phenyl, and where the ring formed by NR ¹⁰ R ¹¹ is optionally substituted on the ring carbon atom by one or two substituents independently representing methyl or oxo (= O); - (CH ₂ ) _n ¹² -C (O) -OR ¹³ where n ¹² represents 0, 1 or 2; and where R ¹³ represents H, C _1-6 alkyl, C _3-6 cycloalkyl, -CH ₂ -C _3-6 cycloalkyl, phenyl or benzyl (where phenyl and benzyl are independently optionally substituted on the aromatic ring by one or two groups (independently ) fluoro, chloro, C _1-2 alkyl, C ₁ fluoroalkyl, C _1-2 alkoxy or C ₁ fluoroalkoxy); - (CH ₂ ) _n ¹³ -C (O) -R ^13a , where n ¹³ represents 0, 1 or 2; and where R ^13a represents a hydrogen atom (H), C _1-6 alkyl, C _1-2 fluoroalkyl, C _3-6 cycloalkyl, —CH ₂ —C _3-6 cycloalkyl, benzyl or phenyl; where phenyl and benzyl are independently possibly substituted on the aromatic ring with one or two groups (independently) of fluoro, chloro, C _1-2 alkyl, C _1-2 fluoroalkyl, C _1-2 alkoxy or C ₁ fluoroalkoxy; - (CH ₂ ) ¹⁴ _n -Het ¹ , -CH (C _1-2 alkyl) -Het ¹ , -CMe ₂ -Het ¹ or C _3-5 cycloalkyl substituted at the carbon atom by the group Het ¹ , where n ¹⁴ represents represents 0, 1 or 2, and where Het ¹ represents a 4-, 5-, 6- or 7-membered saturated heterocyclic ring; where the specified heterocyclic ring Het ¹ contains one ring atom of O or S and / or one ring group NR ¹⁴ , where R ¹⁴ represents H, C _1-4 alkyl, C _3-6 cycloalkyl, benzyl, phenyl, -C (O) R ¹⁹ or -S (O) ₂ R ¹⁹ ; where R ¹⁹ , independently of any other R ¹⁹ , is C _1-6 alkyl, C _3-6 cycloalkyl, thienyl, furyl (furanyl) or phenyl or benzyl; wherein phenyl and benzyl are independently optionally substituted with one or two groups (independently) of fluoro, methyl or methoxy; and wherein said heterocyclic ring Het ^{1 is} optionally substituted (at a position or positions different from any position of NR ¹⁴ ) with one or two oxo substituents (= O) and / or one C _1-4 alkyl substituent; provided that if the heterocyclic ring Het ¹ contains one O or S ring atom and one NR ¹⁴ ring group, then: (a) this O / S ring atom and this NR ¹⁴ ring group are not directly connected to each other, and ( b) this O / S ring atom and this NR ¹⁴ ring group are separated by more than one carbon atom, unless Het ¹ contains the group —NR ¹⁴ —C (O) —O— or —NR ¹⁴ —C (O) —S - as part of a ring; or - (CH ₂ ) _n ¹⁰ —Ar, —CH (C _1-2 alkyl) —Ar, —CMe ₂ —Ar or C _3-5 cycloalkyl substituted at the carbon connecting atom with Ar group, where n ¹⁰ represents 0, 1 or 2, and (1) Ar is phenyl optionally substituted with one or two substituents independently representing fluoro, chloro, bromo, C _1-2 alkyl, C _1-2 fluoroalkyl, C _1-2 alkoxy, C _1-2 fluoroalkoxy, OH, —NR ^11a R ^11b (where R ^11a is H or C _1-2 alkyl, and R ^11b is H, C _1-2 alkyl, —C (O) —C _1-2 alkyl, or —S (O) ₂ —C _1-2 alkyl), cyano, —C (O) —NR ^11c R ^11d (where R ^11c and R ^{11d are} independently H or C _1-2 alkyl), —C (O) —OR ^11e , where R ^11e represents H or C _1-2 alkyl, or -S (O) ₂ -R ^11f (where R ^11f represents C _1-2 alkyl, NH ₂ , NHMe or NMe ₂ ); or phenyl Ar is optionally substituted at two adjacent ring Ar atoms with two ends of the chain, which is: - (CH ₂ ) ₄ -, - (CH ₂ ) ₃ - or —CH = CH — CH = CH—; or (2) Ar is an optionally substituted 5- or 6-membered heterocyclic aromatic ring containing 1, 2, 3 or 4 heteroatoms selected from O, N or S; and where, if the heterocyclic aromatic ring Ar contains 2, 3 or 4 heteroatoms, then one is selected from O, N and S, and the remaining heteroatom (s) is (are) N; and where the heterocyclic aromatic ring Ar is optionally substituted with one or two groups independently representing C _1-4 alkyl or OH (including any keto-tautomer of the OH-substituted aromatic ring), or the heterocyclic aromatic ring Ar is optionally substituted at two adjacent ring Ar atoms with two the ends of the chain, which is - (CH ₂ ) ₄ -, - (CH ₂ ) ₃ - or —CH = CH — CH═CH—; R ^X1 and R ^Y1 independently represent a hydrogen atom (H), C _1-2 alkyl or C ₁ fluoroalkyl; R ^X3 and R ^X4 together represent - (CH ₂ ) _n ¹⁵ —X ⁷ - (CH ₂ ) _n ¹⁶ -, where n ¹⁵ and n ¹⁶ independently represent 1 or 2, and X ⁷ represents a bond, —CH ₂ -, O or NR ^X5 , where R ^X5 is H, C _1-2 alkyl, acetyl or —S (O) ₂ Me; and R ² represents a hydrogen atom (H) or C _1-2 alkyl, provided that if R ³ represents a heterocyclic group of sub-formula (bb), n ¹ represents 1, and Y represents NR ⁴ , then R ⁴ does not represent C _1-2 alkyl, C _1-2 fluoroalkyl or CH ₂ C (O ) NH ₂ . 2. The compound of formula (IA) or its salt

where R ¹ represents C _1-4 alkyl, C _1-3 fluoroalkyl or - (CH ₂ ) ₂ OH; R ² represents a hydrogen atom (H), methyl or C ₁ fluoroalkyl; R ³ represents a possibly substituted branched C _3-6 alkyl, possibly substituted C _3-8 cycloalkyl, possibly substituted phenyl or possibly substituted heterocyclic group of subformula (aa), (bb) or (cc)

or

or

where n ¹ and n ² independently represent 1 or 2; and Y represents O, S, SO ₂ or NR ⁴ ; if R ⁴ represents a hydrogen atom (H), C _1-3 alkyl, C _1-2 fluoroalkyl, CH ₂ C (O) NH ₂ , C (O) NH ₂ , C (O) -C _1-2 alkyl or C (O) -C ₁ fluoroalkyl; where in R ^{3 a} possibly substituted branched C _3-6 alkyl is optionally substituted with one or two substituents representing oxo (= O), OH, C _1-2 alkoxy or C _1-2 fluoroalkoxy; and where any such substituent is not a substituent on the carbon atom of the group R ³ connected (linked) to the group —NH— of formula (IA); where in R ³ phenyl is optionally substituted with one substituent, which is fluoro, chloro, C _1-2 alkyl, C _1-2 fluoroalkyl, C _1-2 alkoxy, C _1-2 fluoroalkoxy or cyano; where in R ³ C _{3-8 a} cycloalkyl or heterocyclic group of a sub-formula (aa), (bb) or (cc) is possibly substituted (a) by one or two substituents representing oxo (= O), OH, C _1-2 alkoxy, C _1-2 fluoroalkoxy or C _1-2 alkyl; and where any substituent OH, alkoxy or fluoroalkoxy is not a substituent on the ring carbon atom of R ³ connected (linked) to the group-NH-formula (IA), and is not a substituent on any ring carbon atom of R ³ linked to the heterocyclic group Y groups (aa), (bb) or (cc); and where Het corresponds to the sub-formula (i), (ii), (iii), (iv) or (v):

or

or

or

or

where W ¹ , W ² , W ⁴ and W ⁵ represents N; and W ³ represents NR ^W ; X ¹ , X ³ and X ⁴ represents N or CR ^X ; X ² represents O, S or NR ^X ; and X ⁵ represents CR ^X1 R ^X2 ; Y ¹ , Y ² and Y ³ represents CR ^Y or N; Y ⁴ represents O, S or NR ^Y ; and Y ⁵ represents CR ^Y1 R ^Y2 ; Z ¹ and Z ⁵ represents O, S or NR ^z ; and Z ² , Z ³ and Z ⁴ represents N or CR ^z ; where R ^W represents a hydrogen atom (H) or C _1-2 alkyl; R ^X , R ^X2 , R ^Y and R ^Y2 independently represent a hydrogen atom (H); C _1-8 alkyl; C _3-6 cycloalkyl optionally substituted with a C _1-2 alkyl group; - (CH ₂ ) _n ^2a -C _3-6 cycloalkyl optionally substituted by the group - (CH ₂ ) _n ^2a - or by a C _3-6 cycloalkyl group by a C _1-2 alkyl group, where n ^2a represents 1, 2 or 3; - (CH ₂ ) _n ³ —SO ₂ —R ⁵ , where n ³ is 1 or 2, and R ⁵ is C _1-3 alkyl, or —NH — C _1-2 alkyl, or phenyl; - (CH ₂ ) _n ⁴ —NR ⁶ R ⁷ , where n ⁴ represents 0, 1, 2 or 3, and R ⁶ and R ⁷ independently represent H, C _1-6 alkyl, C _3-6 cycloalkyl, - CH ₂ -C _3-6 cycloalkyl, -C (O) -C _1-2 alkyl, -SO ₂ -C _1-2 alkyl, phenyl or benzyl (where phenyl or benzyl are independently possibly substituted on the aromatic ring with one fluoro, chloro group , C _1-2 alkyl, C ₁ fluoroalkyl, C _1-2 alkoxy or C ₁ fluoroalkoxy); or R ⁶ and R ⁷ together represent - (CH ₂ ) _n ⁵ —X ⁵ - (CH ₂ ) _n ⁶ -, where n ⁵ and n ⁶ independently represent 2 or 3, and X ⁵ represents a bond, —CH ₂ -, O or NR ⁸ , where R ⁸ represents H or C _1-2 alkyl; - (CH ₂ ) _n -OR ⁹ ; where n ⁷ represents 0, 1, 2 or 3, and R ⁹ represents H or C _1-6 alkyl; where n ⁷ represents 0 only when the group - (CH ₂ ) _n ⁷ -OR ⁹ is bonded to a carbon atom in the Het ring; and where n ^{7 is} not 0 when Het corresponds to the sub-formula (v) (that is, n ^{7 is} not 0 for R ^X2 and for R ^Y2 ); —C (O) —NR ¹⁰ R ¹¹ , where R ¹⁰ and R ¹¹ independently represent H, C _1-6 alkyl, C _3-6 cycloalkyl, —CH ₂ —C _3-6 cycloalkyl, phenyl or benzyl (where phenyl or benzyl is independently possibly substituted on the aromatic ring with one group of fluoro, chloro, C _1-2 alkyl, C ₁ fluoroalkyl, C _1-2 alkoxy or C ₁ fluoroalkoxy); or R ¹⁰ and R ¹¹ together represent - (CH ₂ ) _n ⁸ —X ⁶ - (CH ₂ ) _n ⁹ -, where n ⁸ and n ⁹ independently represent 2 or 3, and X ⁶ represents a bond, —CH ₂ -, O or NR ¹² , where R ¹² represents H or C _1-2 alkyl; —C (O) —OR ¹³ where R ¹³ is H, C _1-6 alkyl, C _3-6 cycloalkyl, —CH ₂ —C _3-6 cycloalkyl, phenyl or benzyl (where phenyl or benzyl are independently optionally substituted by an aromatic ring with one group fluoro, chloro, C _1-2 alkyl, C ₁ fluoroalkyl, C _1-2 alkoxy or C ₁ fluoroalkoxy); —C (O) —R ^13a , where R ^13a represents a hydrogen atom (H), C _1-6 alkyl, C _1-2 fluoroalkyl, C _3-6 cycloalkyl, —CH ₂ —C _3-6 cycloalkyl, benzyl or phenyl; where phenyl or benzyl are independently possibly substituted on the aromatic ring with one group of fluoro, chloro, C _1-2 alkyl, C ₁ fluoroalkyl, C _1-2 alkoxy or C ₁ fluoroalkoxy; A 4-, 5-, 6- or 7-membered saturated heterocyclic ring containing one O ring atom or one NR ¹⁴ ring group, where R ¹⁴ is H or C _1-4 alkyl, wherein said heterocyclic ring is optionally substituted (in position or to positions other than any position NR ¹⁴ ) with one oxo substituent (= O) and / or one C _1-4 alkyl substituent; or - (CH ₂ ) _n ¹⁰ -Ar, where n ¹⁰ represents 0, 1 or 2, and (1) Ar is phenyl, optionally substituted with one or two substituents representing fluoro, chloro, C _1-2 alkyl, C _1-2 fluoroalkyl, C _1-2 alkoxy, C _1-2 fluoroalkoxy or cyano; or (2) Ar is an optionally substituted 5- or 6-membered heterocyclic aromatic ring containing 1, 2 or 3 heteroatoms selected from O, N or S; and where, if the heterocyclic aromatic ring Ar contains 2 or 3 heteroatoms, then one is selected from O, N and S, and the remaining heteroatom (s) is (are) N; and wherein the heterocyclic aromatic ring Ar is optionally substituted with one or two C _1-4 alkyl groups; R ^X1 and R ^Y1 independently represent a hydrogen atom (H), C _1-2 alkyl or C ₁ fluoroalkyl; and R ^Z represents a hydrogen atom (H) or C _1-2 alkyl; provided that if R ³ is a heterocyclic group of the subformula (bb), n ¹ is 1, and Y is NR ⁴ , then R ^{4 is} not C _1-2 alkyl, C _1-2 fluoroalkyl or CH ₂ C (O) NH ₂ . 3. The compound or salt according to claim 1, where R ^3a represents a hydrogen atom (H). 4. The compound or salt according to claim 1 or 2, where R ² represents a hydrogen atom (H) or methyl. 5. The compound or salt according to claim 1 or 2, where R ¹ represents C _1-3 alkyl, C _1-2 fluoroalkyl or -CH ₂ CH ₂ OH. 6. The compound or salt according to claim 1 or 2, where R ¹ represents ethyl, n-propyl, C ₂ fluoroalkyl or —CH ₂ CH ₂ OH. 7. The compound or salt according to claim 1 or 2, where R ¹ represents ethyl. 8. The compound or salt according to claim 1 or 2, where in R ³ there is one substituent or not. 9. The compound or salt according to claim 1 or 2, where if R ³ is a possibly substituted branched C _3-6 alkyl, then said R ³ is isobutyl, sec-butyl, tert-butyl or 3-methylbutan-2- silt. 10. The compound or salt according to claim 1 or 2, where, if R ³ represents a possibly substituted phenyl, then said phenyl is possibly substituted by one substituent, which is fluoro, C ₁ alkyl, C ₁ fluoroalkyl, C ₁ alkoxy or C ₁ fluoroalkoxy . 11. The compound or salt according to claim 1 or 2, where, if R ³ is a possibly substituted C _3-8 cycloalkyl, then said R ³ is a possibly substituted C _6-8 cycloalkyl. 12. The compound or salt according to claim 11, where, if R ³ is a possibly substituted C _3-8 cycloalkyl, then said R ³ is a possibly substituted cyclohexyl. 13. The compound or salt according to claim 1 or 2, where, if R ³ represents a possibly substituted C _3-8 cycloalkyl, then one or two possible substituents represents or independently represent oxo (= O); IT; NHR ²¹ , where R ²¹ represents a hydrogen atom (H); methyl; -CH ₂ F; -CHF ₂ ; -C (O) OR ²³ where R ²³ represents H; fluoro; hydroxyimino (= N-OH); or (C _1-2 alkoxy) imino (= N-OR ²⁶ , where R ²⁶ represents C _1-2 alkyl). 14. The compound or salt according to claim 1 or 2, where, if R ³ is a possibly substituted C _3-8 cycloalkyl, then one or two possible substituents are or independently represent OH, oxo (= O) or hydroxyimino (= N-OH). 15. The compound or salt according to claim 1 or 2, where, if R ³ is a possibly substituted C _3-8 cycloalkyl, then one or two possible substituents, if present, are or represent a substituent (s) according to The 3rd, 4th or 5th position (s) of the cycloalkyl ring R ³ , (where it is believed that the 1st position of the cycloalkyl ring R ³ represents the point of attachment to —NH— in the formula (I) or (IA) or (IB)). 16. The compound or salt according to claim 1 or 2, where if R ³ is a possibly substituted C ₆ cycloalkyl, then said R ³ is cyclohexyl (that is, unsubstituted), 3-hydroxy-cyclohexyl (that is, 3-hydroxycyclohexane- 1-yl), 4-oxo-cyclohexyl (i.e. 4-oxocyclohexan-1-yl), 4- (hydroxyimino) cyclohexyl (i.e. 4- (hydroxyimino) cyclohexan-1-yl), 4- (C _1-2 alkoxyimino) cyclohexyl, 1-methylcyclohexyl or 3-methylcyclohexyl. 17. The compound or salt according to claim 1 or 2, where if R ³ is a possibly substituted mono-unsaturated C _5-7 cycloalkenyl, then said R ³ is a possibly substituted mono-unsaturated C ₆ cycloalkenyl (that is, a possibly substituted mono -unsaturated cyclohexenyl), and wherein cycloalkenyl R ^{3 is} optionally substituted with one or two substituents independently representing fluoro or methyl. 18. The compound or salt according to claim 1 or 2, where R ⁴ represents a hydrogen atom (H) or C (O) -Me. 19. The compound or salt according to claim 1 or 2, where, if R ³ represents a heterocyclic group of the sub-formula (aa), (bb) or (cc), then Y represents O. 20. The compound or salt according to claim 1 or 2, where, if R ³ represents a heterocyclic group of the sub-formula (aa), (bb) or (cc), then R ³ is a heterocyclic group of the sub-formula (bb), and n ¹ represents 1. 21. The compound or salt according to claim 1 or 2, where in R ^{3 the} heterocyclic group of the subformula (aa), (bb) or (cc) is not substituted (where, if Y represents NR ⁴ , then R ^{4 is} not classified as a substituent ) 22. The compound or salt according to claim 1 or 2, where in the heterocyclic group R ³ subformulas (aa), (bb) or (cc), one or two possible substituents are or represent oxo (= O). 23. The compound or salt according to claim 1 or 2, where, if R ³ represents a heterocyclic group of the subformula (aa), then Y does not represent NR ⁴ , and, if R ³ is a heterocyclic group of sub-formula (bb) and Y is NR ⁴ , then R ^{4 is} not C _1-2 alkyl, C _1-2 fluoroalkyl or CH ₂ C (O) NH ₂ . 24. The compound or salt according to claim 1 or 2, where NHR ³ or NR ³ R ^3a corresponds to the subformula (a), (a1), (b), (c), (c1), (c2), (c3), (c4), (c5), (d), (e), (f), (g), (g1), (g2), (g3), (g4), (h), (h1), (i ), (j), (k), (k1), (L), (m), (m1), (m2), (m3), (m5), (n), (o), (o1), (o2), (o3), (o4), (o5), (p), (p2), (p3), (p5), (p6), (p7), (p8), (q), (r ), (s), (t), (t1) or (t2)

25. The compound or salt according to paragraph 24, where NHR ³ or NR ³ R ^3a corresponds to the subformula (C), (C1), (C4), (C5), (h), (i), (j), (k ), (m1), (m2), (n), (o), (o2), (o3), (p2), (p5), (p6), (r), (s) or (t1). 26. The compound or salt according to paragraph 24, where NHR ³ or NR ³ R ^3a corresponds to the subformula (s), (h), (k), (n), (o), (o2) or (s). 27. The compound or salt according to paragraph 24, where NHR ³ or NR ³ R ^3a corresponds to the subformula (a), (b), (c), (d), (e), (f), (g), (h ), (i), (j), (k), (L), (m), (n), (o), (p), (q), (r), (s) or (t). 28. The compound or salt according to paragraph 24, where R ³ represents tetrahydro-2H-pyran-4-yl; that is, NHR ³ or NR ³ R ^3a corresponds to subformula (h). 29. The compound or salt according to claim 1 or 2, where Het corresponds to subformula (i), (ii) or (v). 30. The compound or salt according to clause 29, where Z ¹ and Z ⁵ represent O. 31. The compound or salt according to clause 29, where Het corresponds to the subformula (ia), (ib), (ic), (id), (ie), (if), (ig), (va), (vb) or (iia)

32. The compound or salt according to p, where Het corresponds to the subformula (ia), (ib), (ic), (id), (if), (ig), (va) or (iia). 33. The compound or salt according to p, where Het corresponds to the subformula (ia), (ic), (id) or (va). 34. The compound or salt according to claim 1 or 2, where R ^W and R ^Z represent a hydrogen atom (H). 35. The compound or salt according to claim 1 or 2, where for the Het group one of R ^X and R ^Y (or R ^X2 and R ^Y2 ) is as defined here, and the other is R ^X and R ^Y (or R ^X2 and R ^Y2 ) represents a hydrogen atom (H). 36. The compound or salt according to claim 1 or 2, where R ^X , R ^X2 , R ^Y and R ^Y2 independently represent a hydrogen atom (H); C _1-8 alkyl; optionally substituted C _3-6 cycloalkyl; optionally substituted - (CH ₂ ) _n ^2a —C _3-6 cycloalkyl; - (CH ₂ ) _n ³ -S (O) ₂ -R ⁵ , -CH (Me) -S (O) ₂ -R ⁵ or C ₃ cycloalkyl substituted at the carbon-connecting atom by the group -S (O) ₂ -R ⁵ ; - (CH ₂ ) _n ⁴ -NR ⁶ R ⁷ or -CH (Me) -NR ⁶ R ⁷ ; - (CH ₂ ) _n ⁷ -OR ⁹ ; - (CH ₂ ) _n ¹¹ -C (O) -NR ¹⁰ R ¹¹ or -CH (Me) -C (O) -NR ¹⁰ R ¹¹ ; - (CH ₂ ) _n ¹² -C (O) -OR ¹³ ; - (CH ₂ ) _n ¹³ -C (O) -R ^13a ; - (CH ₂ ) _n ¹⁴ -Het ¹ or -CH (Me) -Het ¹ ; or - (CH ₂ ) _n ¹⁰ —Ar or —CH (Me) —Ar. 37. The compound or salt according to claim 1 or 2, where one of R ^X and R ^Y and, for Het subformulas (v), one of R ^X2 and R ^Y2 is - (CH ₂ ) _n ⁴ -NR ⁶ R ⁷ , -CH (Me) -NR ⁶ R ⁷ , - (CH ₂ ) _n ¹¹ -C (O) -NR ¹⁰ R ¹¹ , - (CH ₂ ) _n ¹⁴ - Het ¹ or - (CH ₂ ) _n ¹⁰ -Ar. 38. The compound or salt according to claim 1 or 2, where R ^X , R ^X2 , R ^Y and R ^Y2 independently represent C _1-6 alkyl; optionally substituted C _3-6 cycloalkyl; - (CH ₂ ) _n ^2a —C _3-6 cycloalkyl optionally substituted with a C _1-2 alkyl group; where n ^2a represents 1; - (CH ₂ ) _n ³ -S (O) ₂ -R ⁵ or C ₃ cycloalkyl substituted on the carbon atom by the group -S (O) ₂ -Ph, where n ³ represents 1, and R ⁵ represents C _{1 -4} alkyl, -NR ¹⁵ R ¹⁶ , optionally substituted phenyl or optionally substituted benzyl; where R ¹⁶ represents H or methyl, and R ¹⁵ represents H, C _1-4 alkyl or optionally substituted phenyl; or R ¹⁵ and R ¹⁶ together represent - (CH ₂ ) _n ^3a —X ^3a - (CH ₂ ) _n ^3b -, where n ^3a and n ^3b are 2, and X ^3a is a bond, —CH ₂ -, O or NR ^8a , where R ^8a is C _1-2 alkyl or acetyl; and the ring formed by NR ¹⁵ R ¹⁶ is not substituted on the ring carbon atom or is substituted on the ring carbon atom with one methyl or oxo substituent (= O); - (CH ₂ ) _n ⁴ -NR ⁶ R ⁷ , -CH (Me) -NR ⁶ R ⁷ or -Cme ₂ -NR ⁶ R ⁷ , where n ⁴ represents 0 (if - (CH ₂ ) _n ⁴ -NR ⁶ R ⁷ is bonded to a carbon atom in the Het ring), or where n ⁴ is 1; and wherein R ⁶ is H or C _1-4 alkyl, and R ⁷ is H, C _1-4 alkyl, —C (O) R ¹⁷ or —S (O) ₂ R ¹⁸ ; or R ⁶ and R ⁷ together represent - (CH ₂ ) _n ⁵ —X ⁵ - (CH ₂ ) _n ⁶ -, where n ⁵ and n ⁶ represent 2, and X ⁵ represents a bond, —CH ₂ -, O or NR ⁸ , and wherein the ring formed by NR ⁶ R ⁷ is not substituted on the ring carbon atom or is substituted on the ring carbon atom with one methyl or oxo substituent (= O); - (CH ₂ ) _n ⁷ -OR ⁹ where n ⁷ represents 1 or 2, and R ⁹ represents H, C _1-4 alkyl or phenyl; - (CH ₂ ) _n ¹¹ -C (O) -NR ¹⁰ R ¹¹ , -CH (Me) -C (O) -NR ¹⁰ R ¹¹ or -CMe ₂ -C (O) -NR ¹⁰ R ¹¹ , where n ¹¹ represents 0 or 1, and R ¹⁰ represents H or C _1-6 alkyl, and R ¹¹ represents H; C _1-6 alkyl; C _3-6 cycloalkyl optionally substituted with one or two methyl groups; —CH ₂ —C _3-6 cycloalkyl (unsubstituted); - (CH ₂ ) _n ¹⁷ -Het ² ; optionally substituted pyridinyl bonded to a carbon atom; optionally substituted phenyl; optionally substituted benzyl; or optionally substituted —CH (C _1-2 alkyl) Ph; where phenyl, benzyl and —CH (C _1-2 alkyl) Ph are independently possibly substituted on the aromatic ring with one or two substituents independently representing fluoro, chloro, C _1-2 alkyl, C ₁ fluoroalkyl, C _1-2 alkoxy, C ₁ fluoroalkoxy, —NR ^10a R ^10b (where R ^10a represents H or methyl, and R ^10b represents H, C _1-2 alkyl, —C (O) Me or —S (O) ₂ Me), —C ( O) —NR ^10c R ^10d (where R ^10c and R ^{10d are} independently H or C _1-2 alkyl), or —S (O) ₂ —R ^10e (where R ^10e is C _1-2 alkyl, NH ₂ , NHMe or NMe ₂ ); and where the pyridinyl bonded to the carbon atom is preferably optionally substituted with one OH (including any keto-tautomer thereof); or R ¹⁰ and R ¹¹ together represent - (CH ₂ ) _n ⁸ —X ⁶ - (CH ₂ ) _n ⁹ -, where n ⁸ and n ⁹ represent 2, and X ⁶ represents a bond, —CH ₂ -, O or NR ¹² ; and where the ring formed by NR ¹⁰ R ¹¹ is not substituted on the ring carbon atom or substituted on the ring carbon atom with one methyl or oxo substituent (= O); - (CH ₂ ) _n ¹² —C (O) —OR ¹³ where n ¹² is 0 or 1 and R ¹³ is H or C _1-4 alkyl; - (CH ₂ ) _n ¹³ —C (O) —R ^13a , n ¹³ represents 0 or 1, and R ^13a represents C _1-3 alkyl, C _1-2 fluoroalkyl, C _3-6 cycloalkyl, —CH ₂ -C _3-6 cycloalkyl, benzyl or phenyl (where phenyl and benzyl are independently possibly substituted on the aromatic ring with one fluoro, chloro, C _1-2 alkyl, C ₁ fluoroalkyl, C _1-2 alkoxy or C ₁ fluoroalkoxy group); - (CH ₂ ) _n ¹⁴ -Het ¹ , -CH (Me) -Het ¹ or -Cme ₂ -Het ¹ , where n ¹⁴ is 0 or 1, and Het ¹ is 4-, 5- or 6-membered a heterocyclic ring, and R ¹⁴ represents C _1-4 alkyl, C (O) R ¹⁹ or S (O) ₂ R ¹⁹ , where R ¹⁹ represents C _1-4 alkyl, C _3-6 cycloalkyl, 2-thienyl, furan-2-yl, phenyl (unsubstituted) or benzyl (unsubstituted); - (CH ₂ ) ¹⁰ _n -Ar, where n ¹⁰ represents 0 or 1. 39. The compound or salt according to claim 1, which is a N-cyclopentyl-1-ethyl-5- (5-methyl-1,3,4-oxadiazol-2-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, N-cyclopentyl-1-ethyl-5- {5 - [(methylsulfonyl) methyl] -1,3,4-oxadiazol-2-yl} -1H-pyrazolo [3,4-b] pyridin-4-amine, N-cyclopentyl-1-ethyl-5- (5-isopropyl-1,3,4-oxadiazol-2-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, N-cyclopentyl-1-ethyl-5- (5-methyl-1,3,4-thiadiazol-2-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, N-cyclopentyl-1-ethyl-5- {5 - [(methylsulfonyl) methyl] -1,3,4-thiadiazol-2-yl} -1H-pyrazolo [3,4-b] pyridin-4-amine, N-cyclopentyl-1-ethyl-5- (5-isopropyl-1,3,4-thiadiazol-2-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-N- (4-fluorophenyl) -5- (3-methyl-1,2,4-oxadiazol-5-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, N-cyclopentyl-5- (1,3-dimethyl-1H-1,2,4-triazol-5-yl) -1-ethyl-1H-pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-5- (5-isopropyl-1,3,4-oxadiazol-2-yl) -N-tetrahydro-2H-pyran-4-yl-1H-pyrazolo [3,4-b] pyridin-4- amine, N-cyclohexyl-1-ethyl-5- (5-isopropyl-1,3,4-oxadiazol-2-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-N-isobutyl-5- (5-isopropyl-1,3,4-oxadiazol-2-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-N-isobutyl-5- (5-methyl-1,3,4-oxadiazol-2-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, N-cyclohexyl-1-ethyl-5- (5-methyl-1,3,4-oxadiazol-2-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-5- (5-methyl-1,3,4-oxadiazol-2-yl) -N-tetrahydro-2H-pyran-4-yl-1H-pyrazolo [3,4-b] pyridin-4- amine, N - [(1R) -1,2-dimethylpropyl] -1-ethyl-5- (5-methyl-1,3,4-oxadiazol-2-yl) -1H-pyrazolo [3,4-b] pyridine- 4-amine N - [(1S) -1,2-dimethylpropyl] -1-ethyl-5- (5-methyl-1,3,4-oxadiazol-2-yl) -1H-pyrazolo [3,4-b] pyridine- 4-amine 5- (5-tert-butyl-1,3,4-oxadiazol-2-yl) -1-ethyl-N-tetrahydro-2H-pyran-4-yl-1H-pyrazolo [3,4-b] pyridin- 4-amine 5- (5-tert-butyl-1,3,4-oxadiazol-2-yl) -N-cyclohexyl-1-ethyl-1H-pyrazolo [3,4-b] pyridin-4-amine, 5- (5-tert-butyl-1,3,4-oxadiazol-2-yl) -N-cyclopentyl-1-ethyl-1H-pyrazolo [3,4-b] pyridin-4-amine, 5- (5-tert-butyl-1,3,4-oxadiazol-2-yl) -1-ethyl-N-isobutyl-1H-pyrazolo [3,4-b] pyridin-4-amine, 5- (5-tert-butyl-1,3,4-oxadiazol-2-yl) -N - [(1S) -1,2-dimethylpropyl] -1-ethyl-1H-pyrazolo [3,4-b] pyridin-4-amine, 5- (5-tert-butyl-1,3,4-oxadiazol-2-yl) -N - [(1R) -1,2-dimethylpropyl] -1-ethyl-1H-pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-5- {5 - [(methylsulfonyl) methyl] -1,3,4-oxadiazol-2-yl} -N-tetrahydro-2H-pyran-4-yl-1H-pyrazolo [3,4-b ] pyridin-4-amine, N-cyclohexyl-1-ethyl-5- {5 - [(methylsulfonyl) methyl] -1,3,4-oxadiazol-2-yl} -1H-pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-N-isobutyl-5- {5 - [(methylsulfonyl) methyl] -1,3,4-oxadiazol-2-yl} -1H-pyrazolo [3,4-b] pyridin-4-amine, N - [(1S) -1,2-dimethylpropyl] -1-ethyl-5- {5 - [(methylsulfonyl) methyl] -1,3,4-oxadiazol-2-yl} -1H-pyrazolo [3,4 -b] pyridin-4-amine, N - [(1R) -1,2-dimethylpropyl] -1-ethyl-5- {5 - [(methylsulfonyl) methyl] -1,3,4-oxadiazol-2-yl} -1H-pyrazolo [3,4 -b] pyridin-4-amine, 1-ethyl-5- (3-methyl-1,2,4-oxadiazol-5-yl) -N-tetrahydro-2H-pyran-4-yl-1H-pyrazolo [3,4-b] pyridin-4- amine, 1-ethyl-5- [3- (methoxymethyl) -1,2,4-oxadiazol-5-yl] -N-tetrahydro-2H-pyran-4-yl-1H-pyrazolo [3,4-b] pyridin- 4-amine 5- {3 - [(dimethylamino) methyl] -1,2,4-oxadiazol-5-yl} -1-ethyl-N-tetrahydro-2H-pyran-4-yl-1H-pyrazolo [3,4-b ] pyridin-4-amine, 1-ethyl-5- [3- (morpholin-4-ylmethyl) -1,2,4-oxadiazol-5-yl] -N-tetrahydro-2H-pyran-4-yl-1H-pyrazolo [3,4- b] pyridin-4-amine, 5- (5-cyclopropyl-1,3,4-oxadiazol-2-yl) -1-ethyl-N-tetrahydro-2H-pyran-4-yl-1H-pyrazolo [3,4-b] pyridin-4- amine, N- (1-Acetylpiperidin-4-yl) -1-ethyl-5- (5-methyl-1,3,4-oxadiazol-2-yl) -1H-pyrazolo [3,4-b] pyridin-4- amine, 1-ethyl-5- [5- (3-methyloxetan-3-yl) -1,3,4-oxadiazol-2-yl] -N-tetrahydro-2H-pyran-4-yl-1H-pyrazolo [3, 4-b] pyridin-4-amine, 1-ethyl-5- {5 - [(4-methylpiperazin-1-yl) methyl] -1,3,4-oxadiazol-2-yl} -N-tetrahydro-2H-pyran-4-yl-1H-pyrazolo [3,4-b] pyridin-4-amine, 5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -N-isopropyl-1,3,4-oxadiazole- 2-carboxamide 4- {5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,3,4-oxadiazole-2 -yl} -1-methylpyrrolidin-2-one, 1-ethyl-N-tetrahydro-2H-pyran-4-yl-5- (5-tetrahydro-2H-pyran-4-yl-1,3,4-oxadiazol-2-yl) -1H-pyrazolo [3, 4-b] pyridin-4-amine, 1-ethyl-5- [5- (morpholin-4-ylmethyl) -1,3,4-oxadiazol-2-yl] -N-tetrahydro-2H-pyran-4-yl-1H-pyrazolo [3,4- b] pyridin-4-amine, 5- [5- (tert-butoxymethyl) -1,3,4-oxadiazol-2-yl] -1-ethyl-N-tetrahydro-2H-pyran-4-yl-1H-pyrazolo [3,4-b] pyridin-4-amine or methyl 2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,3-oxazole-4-carboxylate; or its salt. 40. The compound or salt according to claim 1, which is a methyl-2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -4,5-dihydro-1,3- oxazole-4-carboxylate, 1-ethyl-5- (4-methyl-4,5-dihydro-1,3-oxazol-2-yl) -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4- b] pyridin-4-amine, 1- (n-propyl) -5- (5-methyl-1,3,4-oxadiazol-2-yl) -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4- b] pyridin-4-amine, 1-ethyl-5- [5- (tetrahydrofuran-2-yl) -1,3,4-oxadiazol-2-yl] -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3, 4-b] pyridin-4-amine, 1-ethyl-5- [5- (dimethylamino) -1,3,4-oxadiazol-2-yl] -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-5- (5-methyl-1,2,4-triazol-3-yl) -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4-b] pyridin- 4-amine N- (1-Acetylpiperidin-4-yl) -1-ethyl-5- (3-methyl-1,2,4-oxadiazol-5-yl) -1H-pyrazolo [3,4-b] pyridin-4- amine or N- (1-acetylpiperidin-4-yl) -1-ethyl-5- [3- (morpholin-4-ylmethyl) -1,2,4-oxadiazol-5-yl] -1H-pyrazolo [3,4- b] pyridin-4-amine, or its salt. 41. The compound or salt according to claim 1, which is a 1-ethyl-5 - [(4R) -4-phenyl-4,5-dihydro-1,3-oxazol-2-yl] -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [ 3,4-b] pyridin-4-amine, 1-ethyl-5 - [(4S) -4-phenyl-4,5-dihydro-1,3-oxazol-2-yl] -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [ 3,4-b] pyridin-4-amine, 1-ethyl-5 - [(4S) -4- (phenylmethyl) -4,5-dihydro-1,3-oxazol-2-yl] -N- (tetrahydro-2H-pyran-4-yl) -1H- pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-5 - [(4R) -4- (phenylmethyl) -4,5-dihydro-1,3-oxazol-2-yl] -N- (tetrahydro-2H-pyran-4-yl) -1H- pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-5 - [(4S, 5R) -5-methyl-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl] -N- (tetrahydro-2H-pyran-4-yl ) -1H-pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-5 - [(5R) -5-phenyl-4,5-dihydro-1,3-oxazol-2-yl] -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [ 3,4-b] pyridin-4-amine, 1-ethyl-5 - [(5S) -5-phenyl-4,5-dihydro-1,3-oxazol-2-yl] -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [ 3,4-b] pyridin-4-amine, 5- (4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl) -1-ethyl-N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3, 4-b] pyridin-4-amine, 2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,3-oxazole-4-carboxylic acid, 2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -N- (1-methylethyl) -1,3- oxazole-4-carboxamide, 1-ethyl-5- [4- (4-morpholinylcarbonyl) -1,3-oxazol-2-yl] -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-N-methyl-5- (5-methyl-1,3,4-oxadiazol-2-yl) -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4- b] pyridin-4-amine, trans-4 - {[1-ethyl-5- (5-methyl-1,3,4-oxadiazol-2-yl) -1H-pyrazolo [3,4-b] pyridin-4-yl] amino} cyclohexanol, 1-ethyl-5- (5-methyl-1,3,4-oxadiazol-2-yl) -N- (tetrahydro-2H-pyran-3-yl) -1H-pyrazolo [3,4-b] pyridin- 4-amine 4 - {[1-ethyl-5- (5-methyl-1,3,4-oxadiazol-2-yl) -1H-pyrazolo [3,4-b] pyridin-4-yl] amino} cyclohexanone, 1-ethyl-5- (5-methyl-1,3,4-oxadiazol-2-yl) -N-n-propyl-N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3, 4-b] pyridin-4-amine, 5- [5- (1,1-dimethylethyl) -1,3,4-oxadiazol-2-yl] -1-ethyl-6-methyl-N- (tetrahydro-2H-pyran-4-yl) -1H- pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-6-methyl-N- (tetrahydro-2H-pyran-4-yl) -5- [5- (tetrahydro-2H-pyran-4-yl) -1,3,4-oxadiazol-2-yl ] -1H-pyrazolo [3,4-b] pyridin-4-amine, 5- (5-cyclobutyl-1,3,4-oxadiazol-2-yl) -1-ethyl-N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4-b] pyridin- 4-amine 5- {5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,3,4-oxadiazole-2 -yl} -2-pyrrolidinone, N - ({5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,3,4-oxadiazole- 2-yl} methyl) acetamide, 1-ethyl-5- [5- (1-methyl-2-piperidinyl) -1,3,4-oxadiazol-2-yl] -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [ 3,4-b] pyridin-4-amine, 1-ethyl-5- {5 - [(4-methyl-1,2,5-oxadiazol-3-yl) methyl] -1,3,4-oxadiazol-2-yl} -N- (tetrahydro-2H- pyran-4-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, 3- {5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,3,4-oxadiazole-2 -yl} cyclopentanone, 1-ethyl-5- [5- (tetrahydro-3-furanyl) -1,3,4-oxadiazol-2-yl] -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3, 4-b] pyridin-4-amine, (4S) -4- {5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,3,4 -oxadiazol-2-yl} -1,3-thiazolidin-2-one, 5- [5- (2,2-dimethylcyclopropyl) -1,3,4-oxadiazol-2-yl] -1-ethyl-N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3, 4-b] pyridin-4-amine, N - ({5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,3,4-oxadiazole- 2-yl} methyl) -N-methylacetamide, 1-ethyl-N- (tetrahydro-2H-pyran-4-yl) -5- [5- (tetrahydro-2H-pyran-4-ylmethyl) -1,3,4-oxadiazol-2-yl] -1H- pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-5- [5- (1-methylcyclobutyl) -1,3,4-oxadiazol-2-yl] -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4- b] pyridin-4-amine, 1-ethyl-5- [5- (3-methyl-5-isoxazolyl) -1,3,4-oxadiazol-2-yl] -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [ 3,4-b] pyridin-4-amine, 1-ethyl-5- [5- (1-methyl-1H-pyrazol-5-yl) -1,3,4-oxadiazol-2-yl] -N- (tetrahydro-2H-pyran-4-yl) - 1H-pyrazolo [3,4-b] pyridin-4-amine, 5- [5- (1-acetyl-4-piperidinyl) -1,3,4-oxadiazol-2-yl] -1-ethyl-N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [ 3,4-b] pyridin-4-amine, 1-ethyl-5- {3 - [(4-methyl-1-piperazinyl) methyl] -1,2,4-oxadiazol-5-yl} -N- (tetrahydro-2H-pyran-4-yl) -1H -pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-5- [3- (4-fluorophenyl) -1,2,4-oxadiazol-5-yl] -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4- b] pyridin-4-amine or 1-ethyl-5- {3- [2-oxo-2- (1-pyrrolidinyl) ethyl] -1,2,4-oxadiazol-5-yl} -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, or its salt. 42. The compound or salt according to claim 1, which is a 2- {5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,2,4-oxadiazole-3 -yl} -N-phenylacetamide, 2- {5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,2,4-oxadiazole-3 -yl} -N- (1-phenylethyl) acetamide, 1-ethyl-5- {3- [2-oxo-2- (1-piperidinyl) ethyl] -1,2,4-oxadiazol-5-yl} -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, 2- {5- {1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,2,4-oxadiazole-3 -yl} -N- (phenylmethyl) acetamide, 2- {5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,2,4-oxadiazole-3 -yl} -N, N-dimethylacetamide, N-ethyl-2- {5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,2,4 -oxadiazol-3-yl} acetamide, 1-ethyl-5- {3- [1- (4-morpholinyl) ethyl] -1,2,4-oxadiazol-5-yl} -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, 5- [3- (cyclohexylmethyl) -1,2,4-oxadiazol-5-yl] -1-ethyl-N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-5- {3- [2-oxo-2- (1-piperidinyl) ethyl] -1,2,4-oxadiazol-5-yl} -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-5- {3- [2- (4-methyl-1-piperazinyl) -2-oxoethyl] -1,2,4-oxadiazol-6-yl} -N- (tetrahydro-2H-pyran-4 -yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-N- (tetrahydro-2H-pyran-4-yl) -5- [5- (1H-1,2,3-triazol-1-ylmethyl) -1,3,4-oxadiazol-2-yl ] -1H-pyrazolo [3,4-b] pyridin-4-amine, 5- {5 - [(2,4-dimethyl-1,3-thiazol-5-yl) methyl] -1,3,4-oxadiazol-2-yl} -1-ethyl-N- (tetrahydro-2H- pyran-4-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-5- [5- (2-furanylmethyl) -1,3,4-oxadiazol-2-yl] -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4- b] pyridin-4-amine, 1-ethyl-5- [5- (3-isoxazolylmethyl) -1,3,4-oxadiazol-2-yl] -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4- b] pyridin-4-amine, 1-ethyl-5- (5 - {[4- (methyloxy) phenyl] methyl} -1,3,4-oxadiazol-2-yl) -N- (tetrahydro-2H-pyran-4-yl) -1H- pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-N- (tetrahydro-2H-pyran-4-yl) -5- [5- (1H-tetrazol-1-ylmethyl) -1,3,4-oxadiazol-2-yl] -1H-pyrazolo [ 3,4-b] pyridin-4-amine, 1-ethyl-5- [5- (5-isothiazolylmethyl) -1,3,4-oxadiazol-2-yl] -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4- b] pyridin-4-amine, 1-ethyl-5- {5 - [(3-methyl-5-isoxazolyl) methyl] -1,3,4-oxadiazol-2-yl} -N- (tetrahydro-2H-pyran-4-yl) -1H -pyrazolo [3,4-b] pyridin-4-amine, 5- (5 - {[4- (dimethylamino) phenyl] methyl} -1,3,4-oxadiazol-2-yl) -1-ethyl-N- (tetrahydro-2H-pyran-4-yl) -1H- pyrazolo [3,4-b] pyridin-4-amine (1: 1), 1-ethyl-5- {5 - [(2-methyl-1,3-thiazol-4-yl) methyl] -1,3,4-oxadiazol-2-yl} -N- (tetrahydro-2H-pyran- 4-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, 2- [1 - ({5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,3,4 -oxadiazol-2-yl} methyl) cyclopentyl] -N-methylacetamide, N - ({5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,3,4-oxadiazole- 2-yl) methyl) cyclopropanecarboxamide, 1-ethyl-5- {5 - [(5-methyl-3-isoxazolyl) methyl] -1,3,4-oxadiazol-2-yl} -N- (tetrahydro-2H-pyran-4-yl) -1H -pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-5- {5 - [(5-methyl-3-isoxazolyl) methyl] -1,3,4-oxadiazol-2-yl} -N- (tetrahydro-2H-pyran-4-yl) -1H -pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-5- {5- [2- (4-methyl-1,3-thiazol-5-yl) ethyl] -1,3,4-oxadiazol-2-yl} -N- (tetrahydro-2H- pyran-4-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, 5- {5 - [(3,5-dimethyl-4-isoxazolyl) methyl] -1,3,4-oxadiazol-2-yl} -1-ethyl-N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, N- (1- {5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,3,4- oxadiazol-2-yl} ethyl) acetamide, 5- {5 - [(1-acetyl-4-piperidinyl) methyl] -1,3,4-oxadiazol-2-yl} -1-ethyl-N- (tetrahydro-2H-pyran-4-yl) -1H -pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-5- {5 - [(4-methylphenyl) methyl] -1,3,4-oxadiazol-2-yl} -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3 , 4-b] pyridin-4-amine, 1-ethyl-5- [5- (4-methylphenyl) -1,3,4-oxadiazol-2-yl] -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4- b] pyridin-4-amine, 5- [5- (3,4-dimethylphenyl) -1,3,4-oxadiazol-2-yl] -1-ethyl-N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3, 4-b] pyridin-4-amine, 5- [5- (2,4-dimethylphenyl) -1,3,4-oxadiazol-2-yl] -1-ethyl-N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3, 4-b] pyridin-4-amine, 5- {5 - [(4-bromophenyl) methyl] -1,3,4-oxadiazol-2-yl} -1-ethyl-N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3 , 4-b] pyridin-4-amine, 2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -N- (phenylmethyl) -1,3-oxazol- 4-carboxamide 2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -N - {[4- (methyloxy) phenyl] methyl } -1,3-oxazole-4-carboxamide, 2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -N - [(2-methylphenyl) methyl] -1 3-oxazole-4-carboxamide, 2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -N - [(4-methylphenyl) methyl] -1 3-oxazole-4-carboxamide, 2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b)] pyridin-5-yl] -N - [(3-methylphenyl) methyl] - 1,3-oxazole-4-carboxamide, N - [(4-chlorophenyl) methyl] -2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1 3-oxazole-4-carboxamide, N - [(2,3-dimethylphenyl) methyl] -2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,3-oxazole-4-carboxamide, N - [(3,5-dimethylphenyl) methyl] -2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,3-oxazole-4-carboxamide, N - [(3,4-dimethylphenyl) methyl] -2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,3-oxazole-4-carboxamide, 2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -N- (1-phenylethyl) -1,3- oxazole-4-carboxamide, 2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -N - {(1R) -1- [4- (methyloxy) phenyl] ethyl} -1,3-oxazole-4-carboxamide, 2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -N - [(1R) -phenylpropyl] -1, 3-oxazole-4-carboxamide, 2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -N- (4-methylphenyl) -1,3- oxazole-4-carboxamide, 2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -N - ({4 - [(methylsulfonyl) amino] phenyl} methyl) -1,3-oxazole-4-carboxamide, 2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -N - {[4- (methylsulfonyl) phenyl] methyl } -1,3-oxazole-4-carboxamide, N- (1-acetyl-4-piperidinyl) -2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] - 1,3-oxazole-4-carboxamide, 2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -N- (tetrahydro-2H-pyran-4-yl ) -1,3-oxazole-4-carboxamide, 2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -N- (tetrahydro-2-furanylmethyl) -1, 3-oxazole-4-carboxamide, 2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -N- [2- (4-methyl-1- piperazinyl) ethyl] -1,3-oxazole-4-carboxamide, N- [1- (aminomethyl) cyclohexyl] -2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -N methyl-1,3-oxazole-4-carboxamide, N- (2,6-dimethylphenyl) -2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1, 3-oxazole-4-carboxamide, N - {[4- (aminocarbonyl) phenyl] methyl} -2- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl ] -1,3-oxazole-4-carboxamide, 2- {5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,2,4-oxadiazole-3 -yl} -N- (tetrahydro-2H-pyran-4-yl) acetamide, 5- {3- [2- (2,6-dimethyl-4-morpholinyl) -2-oxoethyl] -1,2,4-oxadiazol-5-yl} -1-ethyl-N- (tetrahydro-2H-pyran -4-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-5- {3- [2- (4-methyl-1-piperidinyl) -2-oxoethyl] -1,2,4-oxadiazol-6-yl} -N- (tetrahydro-2H-pyran-4 -yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, 2- {5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,2,4-oxadiazole-3 -yl} -N- [1-methyl-2- (methyloxy) ethyl] acetamide, 5- {3- [2- (3,5-dimethyl-1-piperidinyl) -2-oxoethyl] -1,2,4-oxadiazol-5-yl} -1-ethyl-N- (tetrahydro-2H-pyran -4-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-5- {3- [2- (3-methyl-1-piperidinyl) -2-oxoethyl] -1,2,4-oxadiazol-5-yl} -N- (tetrahydro-2H-pyran-4 -yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, 2- {5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,2,4-oxadiazole-3 -yl} -N-3-pyridinylacetamide, 6- {5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,3,4-oxadiazole-2 -yl} -2-piperidinone, 1-ethyl-5- {5 - [(3-methyl-1H-1,2,4-triazol-5-yl) methyl] -1,3,4-oxadiazol-2-yl} -N- (tetrahydro- 2H-pyran-4-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, N - ({5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,2,4-oxadiazole- 3-yl} methyl) acetamide, N - ({5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,2,4-oxadiazole- 3-yl} methyl) benzamide, N - ({5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,2,4-oxadiazole- 3-yl} methyl) -2-phenylacetamide, N - ({5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,2,4-oxadiazole- 3-yl} -methyl) -2-methylpropanamide, N - ({5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,2,4-oxadiazole- 3-yl} methyl) -3-methylbutanamide, N - ({5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,2,4-oxadiazole- 3-yl} methyl) cyclohexanecarboxamide, N - ({5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,2,4-oxadiazole- 3-yl} methyl) -2-furancarboxamide, N - ({5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,2,4-oxadiazole- 3-yl} methyl) methanesulfonamide, N - ({5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,2,4-oxadiazole- 3-yl} methyl) benzenesulfonamide, N - ({5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,2,4-oxadiazole- 3-yl} methyl) -1-phenylmethanesulfonamide, N - ({5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,2,4-oxadiazole- 3-yl} methyl) -2-propanesulfonamide, N - ({5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,2,4-oxadiazole- 3-yl} methyl) -1-propanesulfonamide, N - ({5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,2,4-oxadiazole- 3-yl} methyl) cyclopropanesulfonamide, N - ({5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,2,4-oxadiazole- 3-yl} methyl) -2-thiophenesulfonamide, 1 - ({5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,2,4-oxadiazole- 3-yl} methyl) -2-pyrrolidinone, 1 - ({5- [1-ethyl-4- (tetrahydro-2H-pyran-4-ylamino) -1H-pyrazolo [3,4-b] pyridin-5-yl] -1,2,4-oxadiazole- 3-yl} methyl) -2-piperidinone, 5- {3 - [(1-acetyl-4-piperidinyl) methyl] -1,2,4-oxadiazol-5-yl} -1-ethyl-N- (tetrahydro-2H-pyran-4-yl) -1H -pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-5- (3 - {[1- (3-methylbutanoyl) -4-piperidinyl] methyl} -1,2,4-oxadiazol-5-yl) -N- (tetrahydro-2H-pyran-4- il) -1H-pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-5- (3 - {[1- (methylsulfonyl) -4-piperidinyl] methyl} -1,2,4-oxadiazol-5-yl) -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-5- {3- [1- (phenylsulfonyl) cyclopropyl] -1,2,4-oxadiazol-5-yl} -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3 , 4-b] pyridin-4-amine, 1-ethyl-5- [3- (phenylmethyl) -1,2,4-oxadiazol-5-yl] -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-5- [3- (1-phenylethyl) -1,2,4-oxadiazol-5-yl] -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4- b] pyridin-4-amine, 1-ethyl-5- (3 - {[4- (methyloxy) phenyl] methyl} -1,2,4-oxadiazol-5-yl) -N- (tetrahydro-2H-pyran-4-yl) -1H- pyrazolo [3,4-b] pyridin-4-amine, 5- (3 - {[4- (dimethylamino) phenyl] methyl} -1,2,4-oxadiazol-5-yl) -1-ethyl-N- (tetrahydro-2H-pyran-4-yl) -1H- pyrazolo [3,4-b] pyridin-4-amine, 5- (3 - {[3- (dimethylamino) phenyl] methyl} -1,2,4-oxadiazol-5-yl) -1-ethyl-N- (tetrahydro-2H-pyran-4-yl) -1H- pyrazolo [3,4-b] pyridin-4-amine, 5- (3 - {[4- (dimethylamino) phenyl] methyl} -1,2,4-oxadiazol-5-yl) -1-ethyl-N- (tetrahydro-2H-pyran-4-yl) -1H- pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-5- {3 - [(phenyloxy) methyl] -1,2,4-oxadiazol-5-yl} -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4 -b] pyridin-4-amine, 1-ethyl-N- (tetrahydro-2H-pyran-4-yl) -5- [3- (5,6,7,8-tetrahydro [1,2,4] triazolo [4,3-a] pyridine- 3-ylmethyl) -1,2,4-oxadiazol-5-yl] -1H-pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-5- {3 - [(4-phenyl-1-piperazinyl) methyl] -1,2,4-oxadiazol-5-yl} -N- (tetrahydro-2H-pyran-4-yl) -1H -pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-5- (5-ethyl-1,2,4-oxadiazol-3-yl) -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4-b] pyridin- 4-amine 5- (5 - {[4- (dimethylamino) phenyl] methyl} -1,2,4-oxadiazol-3-yl) -1-ethyl-N- (tetrahydro-2H-pyran-4-yl) -1H- pyrazolo [3,4-b] pyridin-4-amine, 1-ethyl-5- (5 - {[4- (methyloxy) phenyl] methyl} -1,2,4-oxadiazol-3-yl) -N- (tetrahydro-2H-pyran-4-yl) -1H- pyrazolo [3,4-b] pyridin-4-amine or 5- (3,8-dioxa-1-azaspiro [4.5] dec-1-en-2-yl) -1-ethyl-N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3, 4-b] pyridin-4-amine, or its salt. 43. The compound or salt according to claim 1, which is a 1-ethyl-5- (5-methyl-1,3,4-oxadiazol-2-yl) -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4-b] pyridin- 4-amine (compound of Example 14), 5- (5-tert-butyl-1,3,4-oxadiazol-2-yl) -1-ethyl-N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine (compound of Example 17), 1-ethyl-5- {5 - [(methylsulfonyl) methyl] -1,3,4-oxadiazol-2-yl} -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4 -b] pyridin-4-amine (compound of Example 23), 1-ethyl-5- [5- (3-methyloxetan-3-yl) -1,3,4-oxadiazol-2-yl] -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [ 3,4-b] pyridin-4-amine (compound of Example 34), 1-ethyl-5- {5 - [(4-methylpiperazin-1-yl) methyl] -1,3,4-oxadiazol-2-yl} -N- (tetrahydro-2H-pyran-4-yl) -1H -pyrazolo [3,4-b] pyridin-4-amine (compound of Example 35), 1-ethyl-N- (tetrahydro-2H-pyran-4-yl) -5- [5- (tetrahydro-2H-pyran-4-yl) -1,3,4-oxadiazol-2-yl] -1H- pyrazolo [3,4-b] pyridin-4-amine (compound of Example 38), also called: 1-ethyl-5- [5- (morpholin-4-ylmethyl) -1,3,4-oxadiazol-2-yl] -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine (compound of Example 39), 1-ethyl-5- [5- (tetrahydrofuran-2-yl) -1,3,4-oxadiazol-2-yl] -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3, 4-b] pyridin-4-amine (compound of Example 44), 1-ethyl-N- (tetrahydro-2H-pyran-4-yl) -5- [5- (tetrahydro-2H-pyran-4-ylmethyl) -1,3,4-oxadiazol-2-yl] -1H- pyrazolo [3,4-b] pyridin-4-amine (compound of Example 77) or 1-ethyl-5- {3- [2-oxo-2- (1-pyrrolidinyl) ethyl] -1,2,4-oxadiazol-5-yl} -N- (tetrahydro-2H-pyran-4-yl) -1H-pyrazolo [3,4-b] pyridin-4-amine (compound of Example 84), or its salt. 44. The compound or salt according to claim 1 or 2, which is a compound or a pharmaceutically acceptable salt thereof. 45. The compound or salt according to claim 1 or 2 in the form of particles with a reduced size. 46. The compound or salt according to item 45, where the particle size (D50 value) of the specified compound or salt in the form of particles with a reduced size is from about 0.5 to about 10 microns. 47. The compound or salt according to claim 1 or 2 for use as an active therapeutic substance in a mammal, such as a human. 48. A pharmaceutical composition comprising a compound of formula (I) or (IA), as defined in any one of claims 1 to 46, or a pharmaceutically acceptable salt thereof and one or more pharmaceutically acceptable carriers and / or excipients. 49. The pharmaceutical composition according to p, which is suitable and / or adapted for inhalation. 50. The pharmaceutical composition according to p, which is suitable and / or adapted for oral administration. 51. The pharmaceutical composition according to any one of claims 48, 49, or 50 for treating and / or preventing an inflammatory and / or allergic disease or cognitive disorder in a mammal, such as a human. 52. The use of a compound of formula (I) or (IA) as defined in any one of claims 1 to 46, or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for the treatment and / or prophylaxis of an inflammatory and / or allergic disease or cognitive disorder a mammal such as a human. 53. A method of treating and / or preventing an inflammatory and / or allergic disease or cognitive disorder in a mammal, such as a person in need thereof, comprising administering to said mammal a therapeutically effective amount of a compound of formula (I) or (IA) as defined in any one of claims 1-46, or a pharmaceutically acceptable salt thereof. 54. The composition or application or method according to any one of paragraphs 51, 52 or 53, wherein said composition, or medicine, or method is intended for the treatment and / or prevention of chronic obstructive pulmonary disease (COPD), asthma, rheumatoid arthritis, or allergic rhinitis in a mammal, such as a human. 55. The composition, use or method of claim 54, wherein said composition, or drug, or method is intended for the treatment and / or prevention of chronic obstructive pulmonary disease (COPD) in a mammal, such as a human. 56. The composition, use or method according to item 54, where the specified composition, or drug, or method is intended for the treatment and / or prevention of asthma in a mammal, such as a human. 57. The composition, use or method according to any one of paragraphs 51-56, where the specified composition or drug is intended for oral administration and is a pharmaceutical composition as defined in paragraph 50, or where the method includes oral administration to a mammal a pharmaceutical composition suitable for oral administration and as defined in paragraph 50.