JPWO2019122065A5 - - Google Patents
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- JPWO2019122065A5 JPWO2019122065A5 JP2020534447A JP2020534447A JPWO2019122065A5 JP WO2019122065 A5 JPWO2019122065 A5 JP WO2019122065A5 JP 2020534447 A JP2020534447 A JP 2020534447A JP 2020534447 A JP2020534447 A JP 2020534447A JP WO2019122065 A5 JPWO2019122065 A5 JP WO2019122065A5
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又はその薬学的に許容される塩により表すことができる
(式中、
R1は、水素原子又はC1~C3アルキル、シクロプロピル又はアシル基を表し;
R2及びR3は、互いに独立して、水素原子、Cl及びFから選択されるハロゲン原子、直鎖状若しくは分枝鎖状のC1~C6アルキル基を表し、C
1
~C
6
アルキル基は、任意選択でヘテロ原子O、S又は-NR
7
で中断され、且つ、非置換であるか、又はC
3
~C
5
シクロアルキル若しくはC
3
~C
5
ヘテロシクロアルキル若しくは芳香族環/複素環で置換されており、C
3
~C
5
シクロアルキル若しくはC
3
~C
5
ヘテロシクロアルキル若しくは芳香族環/複素環は、非置換であるか、又はCl及びFから選択されるハロゲン原子若しくは-OH、メチル(Me)若しくは-OMe基で一置換若しくは多置換され、或いは、R2及びR3は、一緒になってC3~C6環又はヘテロシクロアルキルを形成し;
R2及びR3は、両方がハロゲン原子を表さないことが理解され;
R7は、水素原子又はC1~C3アルキル、アシル若しくはC1~C4カルボキシアルキル基を表し;
R4は、水素原子、F、Cl及びBrから選択されるハロゲン原子、又は-OR8、C1~C3アルキル及びシクロプロピルの中からの基を表し;
R8は、水素原子又はC1~C3アルキル、シクロプロピル若しくはアシル基を表し;
R5及びR6は、互いに独立して、水素原子、C1~C3アルキル若しくはシクロプロピル基を表すか、又は一緒になってカルボニル若しくはC3~C4環を形成し;
Xは、水素原子又は-NH2、-OH若しくはメチル基を表す)。
or a pharmaceutically acceptable salt thereof
(In the formula,
R 1 represents a hydrogen atom or a C 1 -C 3 alkyl, cyclopropyl or acyl group;
R 2 and R 3 independently of each other represent a hydrogen atom, a halogen atom selected from Cl and F, a linear or branched C 1 -C 6 alkyl group , C 1 -C 6 alkyl The group is optionally interrupted by a heteroatom O, S or —NR 7 and is unsubstituted or C 3 -C 5 cycloalkyl or C 3 -C 5 heterocycloalkyl or aromatic ring/hetero The ring-substituted C 3 -C 5 cycloalkyl or C 3 -C 5 heterocycloalkyl or aromatic/heterocyclic ring is unsubstituted or has a halogen atom selected from Cl and F or - mono- or polysubstituted with OH, methyl (Me) or -OMe groups, or R 2 and R 3 together form a C 3 -C 6 ring or heterocycloalkyl;
It is understood that R2 and R3 do not both represent a halogen atom;
R 7 represents a hydrogen atom or a C 1 -C 3 alkyl, acyl or C 1 -C 4 carboxyalkyl group;
R 4 represents a hydrogen atom, a halogen atom selected from F, Cl and Br, or a group selected from —OR 8 , C 1 -C 3 alkyl and cyclopropyl;
R 8 represents a hydrogen atom or a C 1 -C 3 alkyl, cyclopropyl or acyl group;
R 5 and R 6 independently represent a hydrogen atom, a C 1 -C 3 alkyl or cyclopropyl group, or together form a carbonyl or a C 3 -C 4 ring;
X represents a hydrogen atom, -NH2 , -OH or a methyl group).
本発明の文脈に当てはまる式(I)の化合物の中でも、以下の化合物がとりわけ言及されうる。
・ 5-(4-アミノ-7-イソブチル-7-メチル-6,7-ジヒドロ-5H-ピロロ[3,2-d]ピリミジン-5-イル)ベンゾ[d]オキサゾール-2-アミン(エナンチオマー1);
・ 5-(4-アミノ-7-イソブチル-7-メチル-6,7-ジヒドロ-5H-ピロロ[3,2-d]ピリミジン-5-イル)ベンゾ[d]オキサゾール-2-アミン(エナンチオマー2);
・ 5-(2-アミノベンゾオキサゾール-5-イル)-7-イソブチル-6,7-ジヒドロ-5H-ピロロ[3,2-d]ピリミジン-4-イルアミン;
・ 5-(2-アミノベンゾオキサゾール-5-イル)-7-メチル-7-メチルスルファニルメチル-6,7-ジヒドロ-5H-ピロロ[3,2-d]ピリミジン-4-イルアミン;
・ 5-(4-アミノ-7,7-ジエチル-6,7-ジヒドロ-5H-ピロロ[3,2-d]ピリミジン-5-イル)ベンゾ[d]オキサゾール-2-アミン;
・ 5-(2-アミノベンゾオキサゾール-5-イル)-7,7-ジメチル-6,7-ジヒドロ-5H-ピロロ[3,2-d]ピリミジン-4-イルアミン;
・ 5-(2-アミノベンゾオキサゾール-5-イル)-7-メチル-7-プロピル-6,7-ジヒドロ-5H-ピロロ[3,2-d]ピリミジン-4-イルアミン;
・ 5-(2-アミノベンゾオキサゾール-5-イル)-7,7-ジエチル-6-メチル-6,7-ジヒドロ-5H-ピロロ[3,2-d]ピリミジン-4-イルアミン;
・ 4-アミノ-5-(2-アミノベンゾオキサゾール-5-イル)-7,7-ジメチル-5,7-ジヒドロ-ピロロ[3,2-d]ピリミジン-6-オン;
・ 1-アセチル-4'-アミノ-5'-(2-アミノベンゾ[d]オキサゾール-5-イル)スピロ[アゼチジン-3,7'-ピロロ[3,2-d]ピリミジン]-6'(5'H)-オン;
・ tert-ブチル4'-アミノ-5'-(2-アミノベンゾ[d]オキサゾール-5-イル)-6'-オキソ-5',6'-ジヒドロスピロ[アゼチジン-3,7'-ピロロ[3,2-d]ピリミジン]-1-カルボキシレート;
・ tert-ブチル4'-アミノ-5'-(2-アミノベンゾ[d]オキサゾール-5-イル)-5',6'-ジヒドロスピロ[アゼチジン-3,7'-ピロロ[3,2-d]ピリミジン]-1-カルボキシレート。
Among the compounds of formula (I) that apply in the context of the present invention, the following compounds may be mentioned in particular.
5-(4-amino-7-isobutyl-7-methyl-6,7-dihydro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)benzo[d]oxazol-2-amine (enantiomer 1 );
5-(4-amino-7-isobutyl-7-methyl-6,7-dihydro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)benzo[d]oxazol-2-amine (enantiomer 2 );
5-(2-aminobenzoxazol-5-yl)-7-isobutyl-6,7-dihydro-5H-pyrrolo[3,2-d]pyrimidin-4-ylamine;
5-(2-aminobenzoxazol-5-yl)-7-methyl-7-methylsulfanylmethyl-6,7-dihydro-5H-pyrrolo[3,2-d]pyrimidin-4-ylamine;
5-(4-amino-7,7-diethyl-6,7-dihydro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)benzo[d]oxazol-2-amine;
5-(2-aminobenzoxazol-5-yl)-7,7-dimethyl-6,7-dihydro-5H-pyrrolo[3,2-d]pyrimidin-4-ylamine;
5-(2-aminobenzoxazol-5-yl)-7-methyl-7-propyl-6,7-dihydro-5H-pyrrolo[3,2-d]pyrimidin-4-ylamine;
5-(2-aminobenzoxazol-5-yl)-7,7-diethyl-6-methyl-6,7-dihydro-5H-pyrrolo[3,2-d]pyrimidin-4-ylamine;
4-amino-5-(2-aminobenzoxazol-5-yl)-7,7-dimethyl-5,7-dihydro-pyrrolo[3,2-d]pyrimidin-6-one;
1-acetyl-4'-amino-5'-(2-aminobenzo[d]oxazol-5-yl)spiro[azetidine-3,7'- pyrrolo[3,2-d] pyrimidine]-6'(5 'H) - on;
- tert-butyl 4'-amino-5'-(2-aminobenzo[d]oxazol-5-yl)-6'-oxo-5',6'-dihydrospiro[azetidine-3,7'-pyrrolo[3 ,2-d]pyrimidine]-1-carboxylate;
・ tert-butyl 4'-amino-5'-(2-aminobenzo[d]oxazol-5-yl)-5',6'-dihydrospiro[azetidine-3,7'-pyrrolo[3,2-d] pyrimidine]-1-carboxylate.
(実施例10、実施例11及び実施例12)
図2で例示する、化合物1-アセチル-4'-アミノ-5'-(2-アミノベンゾ[d]オキサゾール-5-イル)スピロ[アゼチジン-3,7'-ピロロ[3,2-d]ピリミジン]-6'(5'H)-オン(15-実施例10)、tert-ブチル4'-アミノ-5'-(2-アミノベンゾ[d]オキサゾール-5-イル)-6'-オキソ-5',6'-ジヒドロスピロ[アゼチジン-3,7'-ピロロ[3,2-d]ピリミジン]-1-カルボキシレート(14-実施例11)及びtert-ブチル4'-アミノ-5'-(2-アミノベンゾ[d]オキサゾール-5-イル)-5',6'-ジヒドロスピロ[アゼチジン-3,7'-ピロロ[3,2-d]ピリミジン]-1-カルボキシレート(16-実施例12)を合成するための経路
(Example 10, Example 11 and Example 12)
The compound 1-acetyl-4'-amino-5'-(2-aminobenzo[d]oxazol-5-yl)spiro[azetidine-3,7'- pyrrolo[3,2-d] pyrimidine, exemplified in FIG. ]-6'(5'H)-one (15-Example 10), tert-butyl 4'-amino-5'-(2-aminobenzo[d]oxazol-5-yl)-6'-oxo-5 ',6'-Dihydrospiro[azetidine-3,7'-pyrrolo[3,2-d]pyrimidine]-1-carboxylate (14-Example 11) and tert-butyl 4'-amino-5'-( 2-Aminobenzo[d]oxazol-5-yl)-5′,6′-dihydrospiro[azetidine-3,7′-pyrrolo[3,2-d]pyrimidine]-1-carboxylate (16-Example 12 ) to synthesize
h) 1-アセチル-4'-アミノ-5'-(2-アミノベンゾ[d]オキサゾール-5-イル)スピロ[アゼチジン-3,7'-ピロロ[3,2-d]ピリミジン]-6'(5'H)-オン(15-実施例10)
4℃、N2下の、DCM(1ml)中のtert-ブチル4'-アミノ-5'-(2-アミノベンゾ[d]オキサゾール-5-イル)-6'-オキソ-5',6'-ジヒドロスピロ[アゼチジン-3,7'-ピロロ[3,2-d]ピリミジン]-1-カルボキシレート(48.0mg、0.11mmol、1.0当量)(14-実施例11)の溶液に、トリフルオロ酢酸(0.5ml)を滴下添加した。4時間後、反応混合物を真空下で濃縮した。残留物をDCM/MeOH(9/1)に溶解し、DCM/MeOH混合物(9/1)を溶出液として使用して、塩基性アルミナプレートを通過させた。予期される化合物を含有する画分を蒸発させ、粗生成物を次の工程において直接使用した。
h) 1-acetyl-4'-amino-5'-(2-aminobenzo[d]oxazol-5-yl)spiro[azetidine-3,7'- pyrrolo[3,2-d] pyrimidine]-6'( 5'H)-one (15-Example 10)
tert-Butyl 4'-amino-5'-(2-aminobenzo[d]oxazol-5-yl)-6'-oxo-5',6'- in DCM (1 ml) at 4°C under N2 To a solution of dihydrospiro[azetidine-3,7′-pyrrolo[3,2-d]pyrimidine]-1-carboxylate (48.0 mg, 0.11 mmol, 1.0 equiv) (14-Example 11) was added trifluoroacetic acid ( 0.5 ml) was added dropwise. After 4 hours, the reaction mixture was concentrated under vacuum. The residue was dissolved in DCM/MeOH (9/1) and passed through basic alumina plates using a DCM/MeOH mixture (9/1) as eluent. Fractions containing the expected compound were evaporated and the crude product used directly in the next step.
N2下で、-78℃に冷却した、DCM(2ml)中の4'-アミノ-5'-(2-アミノ-1,3-ベンゾオキサゾール-5-イル)スピロ[アゼチジン-3,7'-ピロロ[3,2-d]ピリミジン]-6'-オン(38.0mg、0.12mmol、1.0当量)の溶液に、トリエチルアミン(18.2μl、0.13mmol、1.1当量)及び塩化アセチル(8.43μL、0.12mmol、1.0当量)を、それぞれ添加した。反応混合物を-78℃で2時間保持し、その後、ゆっくりと室温へと戻した。その後、冷水(4℃)の溶液を添加し、2相混合物を5分間撹拌した。その後、それを分液漏斗に移し、有機層を収集し、水性相をDCMで2回抽出した。合わせた有機層を硫酸ナトリウムで脱水し、真空下で濾過して乾燥させた。固体の残留物を、98/2から9/1の勾配のDCM/MeOHを使用して、塩基性アルミナのカラム上でクロマトグラフィーにより精製した。純粋な画分を合わせ、予期される化合物(1-アセチル-4'-アミノ-5'-(2-アミノベンゾ[d]オキサゾール-5-イル)スピロ[アゼチジン-3,7'-ピロロ[3,2-d]ピリミジン]-6'(5'H)-オン(15-実施例10))を、白色の粉末の形態で得た(2.2mg、5%収率)。
1H NMR (DMSO-d6) δ: 1.86 (s, 3H), 4.09 (b, 2H), 4.38 (b, 2H), 5.51 (b, 2H), 7.03 (dd, J = 2.12, 8.20 Hz, 1H), 7.27 (d, J = 2.12 Hz, 1H), 7.45 (d, J = 8.20 Hz, 1H), 7.61 (s, 2H), 8.33 (s, 1H).
MS (ESI) m/z = 366 [M+H]+
4′-Amino-5′-(2-amino-1,3-benzoxazol-5-yl)spiro[azetidine-3,7′ in DCM (2 ml) cooled to −78° C. under N 2 To a solution of -pyrrolo[3,2-d]pyrimidin]-6'-one (38.0 mg, 0.12 mmol, 1.0 eq) was added triethylamine (18.2 μl, 0.13 mmol, 1.1 eq) and acetyl chloride (8.43 μL, 0.12 mmol). , 1.0 equivalent) were added respectively. The reaction mixture was kept at −78° C. for 2 hours and then slowly allowed to warm to room temperature. A solution of cold water (4° C.) was then added and the biphasic mixture was stirred for 5 minutes. After that it was transferred to a separatory funnel, the organic layer was collected and the aqueous phase was extracted twice with DCM. The combined organic layers were dried over sodium sulfate, filtered and dried under vacuum. The solid residue was purified by chromatography on a column of basic alumina using a gradient of DCM/MeOH from 98/2 to 9/1. Pure fractions were combined and the expected compound (1-acetyl-4'-amino-5'-(2-aminobenzo[d]oxazol-5-yl)spiro[azetidine-3,7'- pyrrolo[3, 2-d] pyrimidin]-6'(5'H)-one (15-Example 10)) was obtained in the form of a white powder (2.2 mg, 5% yield).
1H NMR (DMSO-d6) δ: 1.86 (s, 3H), 4.09 (b, 2H), 4.38 (b, 2H), 5.51 (b, 2H), 7.03 (dd, J = 2.12, 8.20 Hz, 1H) , 7.27 (d, J = 2.12 Hz, 1H), 7.45 (d, J = 8.20 Hz, 1H), 7.61 (s, 2H), 8.33 (s, 1H).
MS (ESI) m/z = 366 [M+H]+
Claims (16)
(式中、
R1は、水素原子又はC1~C3アルキル、シクロプロピル又はアシル基を表し;
R2及びR3は、互いに独立して、水素原子、Cl及びFから選択されるハロゲン原子、又は直鎖状若しくは分枝鎖状のC 1 ~C 6 アルキル基を表し、C 1 ~C 6 アルキル基は、任意選択でヘテロ原子O、S又は-NR 7 で中断され、且つ、非置換であるか、又はC 3 ~C 5 シクロアルキル、C 3 ~C 5 ヘテロシクロアルキル、芳香族環若しくは芳香族複素環で置換されており、C 3 ~C 5 シクロアルキル、C 3 ~C 5 ヘテロシクロアルキル、芳香族環及び芳香族複素環のそれぞれは、非置換であるか、又はCl及びFから選択されるハロゲン原子若しくは-OH、メチル(Me)若しくは-OMe基で一置換若しくは多置換され、或いは、R2及びR3は、一緒になって置換又は非置換のC3~C 6 ヘテロシクロアルキルを形成し;
ヘテロシクロアルキル及び芳香族複素環におけるヘテロ原子は、1つ又は複数のN及びOであり、
R2及びR3は、両方がハロゲン原子を表さないことが理解され;
R7は、水素原子又はC1~C3アルキル、アシル若しくはC1~C4カルボキシアルキル基を表し;
R4は、水素原子、F、Cl及びBrから選択されるハロゲン原子、又は-OR8、C1~C3アルキル及びシクロプロピルの中からの基を表し;
R8は、水素原子又はC1~C3アルキル、シクロプロピル若しくはアシル基を表し;
R5及びR6は、互いに独立して、水素原子、C1~C3アルキル若しくはシクロプロピル基を表すか、又は一緒になってカルボニルを形成し;
Xは、水素原子又は-NH2、-OH若しくはメチル基を表す)。 General formula (I)
(In the formula,
R 1 represents a hydrogen atom or a C 1 -C 3 alkyl, cyclopropyl or acyl group;
R 2 and R 3 independently of each other represent a hydrogen atom, a halogen atom selected from Cl and F, or a linear or branched C 1 -C 6 alkyl group, and C 1 -C 6 The alkyl group is optionally interrupted by a heteroatom O, S or —NR 7 and is unsubstituted or C 3 -C 5 cycloalkyl, C 3 -C 5 heterocycloalkyl, aromatic ring or substituted with an aromatic heterocycle, wherein each of C 3 -C 5 cycloalkyl, C 3 -C 5 heterocycloalkyl, aromatic ring and heteroaromatic ring is unsubstituted or from Cl and F mono- or polysubstituted with selected halogen atoms or —OH, methyl (Me) or —OMe groups, or R 2 and R 3 together are a substituted or unsubstituted C 3 -C 6 hetero forming a cycloalkyl;
heteroatoms in heterocycloalkyl and heteroaromatic rings are one or more of N and O;
It is understood that R2 and R3 do not both represent a halogen atom;
R 7 represents a hydrogen atom or a C 1 -C 3 alkyl, acyl or C 1 -C 4 carboxyalkyl group;
R 4 represents a hydrogen atom, a halogen atom selected from F, Cl and Br, or a group selected from —OR 8 , C 1 -C 3 alkyl and cyclopropyl;
R 8 represents a hydrogen atom or a C 1 -C 3 alkyl, cyclopropyl or acyl group;
R 5 and R 6 independently of each other represent a hydrogen atom, a C 1 -C 3 alkyl or cyclopropyl group, or together form a carbonyl ;
X represents a hydrogen atom, -NH2 , -OH or a methyl group).
R2及びR3は、互いに独立して、水素原子、任意選択でヘテロ原子S若しくは-NR7で中断された、直鎖状若しくは分枝鎖状のC1~C4アルキル基を表し、又は、R 2 及びR 3 は、一緒になってC4ヘテロシクロアルキルを形成し、C 4 ヘテロシクロアルキルにおけるヘテロ原子は、Nであり、ヘテロシクロアルキルは、C(O)CH 3 又はC(O)CH 2 C(CH 3 ) 3 で置換されており;
R7は、アシル又はカルボキシ-tert-ブチル基を表し;
R4は、水素原子を表し;
R5及びR6は、互いに独立して、水素原子、メチル基を表すか、又は一緒になってカルボニルを形成し;
Xは、水素原子を表す、
請求項1に記載の式(I)のmTOR阻害化合物又はその薬学的に許容される塩。 R 1 represents a hydrogen atom;
R 2 and R 3 independently of each other represent a hydrogen atom, a linear or branched C 1 -C 4 alkyl group optionally interrupted by a heteroatom S or —NR 7 , or , R2 and R3 together form a C4heterocycloalkyl , the heteroatom in the C4heterocycloalkyl is N, and the heterocycloalkyl is C(O)CH3 or C( O ) is substituted with CH2C (CH3 ) 3 ;
R7 represents an acyl or carboxy-tert-butyl group;
R 4 represents a hydrogen atom;
R 5 and R 6 independently represent a hydrogen atom, a methyl group, or together form a carbonyl;
X represents a hydrogen atom,
2. An mTOR inhibitory compound of formula (I) according to claim 1 or a pharmaceutically acceptable salt thereof.
R2は、メチル基を表し;
R3は、任意選択でSヘテロ原子で中断された、直鎖状又は分枝鎖状のC1~C4アルキル基を表し;
R4は、水素原子を表し;
R5及びR6は、水素原子を表し;
Xは、水素原子を表す、
請求項1又は2に記載の式(I)のmTOR阻害化合物又はその薬学的に許容される塩。 R 1 represents a hydrogen atom;
R 2 represents a methyl group;
R 3 represents a linear or branched C 1 -C 4 alkyl group optionally interrupted by an S heteroatom;
R 4 represents a hydrogen atom;
R5 and R6 represent a hydrogen atom;
X represents a hydrogen atom,
3. The mTOR inhibitory compound of formula (I) according to claim 1 or 2, or a pharmaceutically acceptable salt thereof.
以下の式e1若しくは式e2
5-(2-アミノベンゾオキサゾール-5-イル)-7-イソブチル-6,7-ジヒドロ-5H-ピロロ[3,2-d]ピリミジン-4-イルアミン;
5-(2-アミノベンゾオキサゾール-5-イル)-7-メチル-7-メチルスルファニルメチル-6,7-ジヒドロ-5H-ピロロ[3,2-d]ピリミジン-4-イルアミン;
5-(4-アミノ-7,7-ジエチル-6,7-ジヒドロ-5H-ピロロ[3,2-d]ピリミジン-5-イル)ベンゾ[d]オキサゾール-2-アミン;
5-(2-アミノベンゾオキサゾール-5-イル)-7,7-ジメチル-6,7-ジヒドロ-5H-ピロロ[3,2-d]ピリミジン-4-イルアミン;
5-(2-アミノベンゾオキサゾール-5-イル)-7-メチル-7-プロピル-6,7-ジヒドロ-5H-ピロロ[3,2-d]ピリミジン-4-イルアミン;
5-(2-アミノベンゾオキサゾール-5-イル)-7,7-ジエチル-6-メチル-6,7-ジヒドロ-5H-ピロロ[3,2-d]ピリミジン-4-イルアミン;
4-アミノ-5-(2-アミノベンゾオキサゾール-5-イル)-7,7-ジメチル-5,7-ジヒドロ-ピロロ[3,2-d]ピリミジン-6-オン;
1-アセチル-4'-アミノ-5'-(2-アミノベンゾ[d]オキサゾール-5-イル)スピロ[アゼチジン-3,7'-シクロペンタ[d]ピリミジン]-6'(5'H)-オン;
tert-ブチル4'-アミノ-5'-(2-アミノベンゾ[d]オキサゾール-5-イル)-6'-オキソ-5',6'-ジヒドロスピロ[アゼチジン-3,7'-ピロロ[3,2-d]ピリミジン]-1-カルボキシレート;又は
tert-ブチル4'-アミノ-5'-(2-アミノベンゾ[d]オキサゾール-5-イル)-5',6'-ジヒドロスピロ[アゼチジン-3,7'-ピロロ[3,2-d]ピリミジン]-1-カルボキシレート
から選択される、
請求項1に記載の化合物又はその薬学的に許容される塩。 The following compounds:
Formula e1 or formula e2 below
5-(2-aminobenzoxazol-5-yl)-7-isobutyl-6,7-dihydro-5H-pyrrolo[3,2-d]pyrimidin-4-ylamine;
5-(2-aminobenzoxazol-5-yl)-7-methyl-7-methylsulfanylmethyl-6,7-dihydro-5H-pyrrolo[3,2-d]pyrimidin-4-ylamine;
5-(4-amino-7,7-diethyl-6,7-dihydro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)benzo[d]oxazol-2-amine;
5-(2-aminobenzoxazol-5-yl)-7,7-dimethyl-6,7-dihydro-5H-pyrrolo[3,2-d]pyrimidin-4-ylamine;
5-(2-aminobenzoxazol-5-yl)-7-methyl-7-propyl-6,7-dihydro-5H-pyrrolo[3,2-d]pyrimidin-4-ylamine;
5-(2-aminobenzoxazol-5-yl)-7,7-diethyl-6-methyl-6,7-dihydro-5H-pyrrolo[3,2-d]pyrimidin-4-ylamine;
4-amino-5-(2-aminobenzoxazol-5-yl)-7,7-dimethyl-5,7-dihydro-pyrrolo[3,2-d]pyrimidin-6-one;
1-Acetyl-4'-amino-5'-(2-aminobenzo[d]oxazol-5-yl)spiro[azetidin-3,7'-cyclopenta[d]pyrimidin]-6'(5'H)-one ;
tert-butyl 4'-amino-5'-(2-aminobenzo[d]oxazol-5-yl)-6'-oxo-5',6'-dihydrospiro[azetidine-3,7'-pyrrolo[3, 2-d]pyrimidine]-1-carboxylate; or
tert-butyl 4'-amino-5'-(2-aminobenzo[d]oxazol-5-yl)-5',6'-dihydrospiro[azetidine-3,7'-pyrrolo[3,2-d]pyrimidine ]-1-carboxylates,
A compound according to claim 1 or a pharmaceutically acceptable salt thereof.
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