ES2637245T3 - Nuevas 4-(amino sustituido)-7H-pirrolo[2,3-d]pirimidinas como inhibidores de LRRK2 - Google Patents

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Publication number

ES2637245T3

ES2637245T3 ES13752678.6T ES13752678T ES2637245T3 ES 2637245 T3 ES2637245 T3 ES 2637245T3 ES 13752678 T ES13752678 T ES 13752678T ES 2637245 T3 ES2637245 T3 ES 2637245T3

Authority

ES

Spain

Prior art keywords

pyrrolo

pyrimidin

procedure

morpholin

pyrimidine

Prior art date

2012-06-29

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• -1 4- (substituted amino) -7H-pyrrolo [2,3-d] pyrimidines Chemical class 0.000 title abstract description 47
• 229940124786 LRRK2 inhibitor Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 abstract description 80
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 23
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract description 14
• 125000005842 heteroatom Chemical group 0.000 abstract description 13
• 229910052757 nitrogen Inorganic materials 0.000 abstract description 12
• 229910052760 oxygen Inorganic materials 0.000 abstract description 12
• 229910052717 sulfur Inorganic materials 0.000 abstract description 11
• 125000001072 heteroaryl group Chemical group 0.000 abstract description 7
• 125000000592 heterocycloalkyl group Chemical group 0.000 abstract description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 6
• 239000001257 hydrogen Substances 0.000 abstract description 6
• 229910052739 hydrogen Inorganic materials 0.000 abstract description 6
• 125000000753 cycloalkyl group Chemical group 0.000 abstract description 5
• 125000005843 halogen group Chemical group 0.000 abstract description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 3
• 150000003839 salts Chemical class 0.000 abstract description 3
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract description 2
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
• 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
• 238000000034 method Methods 0.000 description 210
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 110
• 238000005160 1H NMR spectroscopy Methods 0.000 description 95
• 238000001819 mass spectrum Methods 0.000 description 82
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 55
• 238000002360 preparation method Methods 0.000 description 52
• 238000004128 high performance liquid chromatography Methods 0.000 description 44
• 239000007858 starting material Substances 0.000 description 43
• 230000014759 maintenance of location Effects 0.000 description 42
• 150000002500 ions Chemical class 0.000 description 41
• 238000003786 synthesis reaction Methods 0.000 description 36
• 230000015572 biosynthetic process Effects 0.000 description 35
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 34
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
• 239000002904 solvent Substances 0.000 description 29
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 26
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
• 239000011541 reaction mixture Substances 0.000 description 24
• 238000006243 chemical reaction Methods 0.000 description 23
• 239000000243 solution Substances 0.000 description 23
• 239000007787 solid Substances 0.000 description 22
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
• 150000004675 formic acid derivatives Chemical class 0.000 description 19
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 19
• 239000000203 mixture Substances 0.000 description 18
• 238000000746 purification Methods 0.000 description 18
• 229920006395 saturated elastomer Polymers 0.000 description 18
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 18
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• BHTWDJBVZQBRKP-UHFFFAOYSA-N 3-(4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2C3=C(N4CCOCC4)N=CN=C3NC=2)=C1 BHTWDJBVZQBRKP-UHFFFAOYSA-N 0.000 description 13
• 239000007864 aqueous solution Substances 0.000 description 13
• 239000003208 petroleum Substances 0.000 description 12
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 12
• 125000001424 substituent group Chemical group 0.000 description 12
• 102000009784 Leucine-Rich Repeat Serine-Threonine Protein Kinase-2 Human genes 0.000 description 11
• 108010020246 Leucine-Rich Repeat Serine-Threonine Protein Kinase-2 Proteins 0.000 description 11
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
• 102200092160 rs34637584 Human genes 0.000 description 11
• 229910052938 sodium sulfate Inorganic materials 0.000 description 11
• 235000011152 sodium sulphate Nutrition 0.000 description 11
• XXGYVFAKVLKYMQ-UHFFFAOYSA-N 2-[(4-chloro-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)methoxy]ethyl-trimethylsilane Chemical compound N1=CN=C2N(COCC[Si](C)(C)C)C=C(I)C2=C1Cl XXGYVFAKVLKYMQ-UHFFFAOYSA-N 0.000 description 10
• 239000012044 organic layer Substances 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• 239000011780 sodium chloride Substances 0.000 description 10
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
• 238000004587 chromatography analysis Methods 0.000 description 9
• 239000000741 silica gel Substances 0.000 description 9
• 229910002027 silica gel Inorganic materials 0.000 description 9
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
• FALGNGIGJAIJGO-UHFFFAOYSA-N [3-[4-(dimethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]phenyl]methanol Chemical compound C1=2C(N(C)C)=NC=NC=2NC=C1C1=CC=CC(CO)=C1 FALGNGIGJAIJGO-UHFFFAOYSA-N 0.000 description 8
• 239000003480 eluent Substances 0.000 description 8
• 125000006413 ring segment Chemical group 0.000 description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
• 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 description 7
• 125000004429 atom Chemical group 0.000 description 7
• 229910052799 carbon Inorganic materials 0.000 description 7
• 125000006239 protecting group Chemical group 0.000 description 7
• 238000011282 treatment Methods 0.000 description 7
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• 125000004432 carbon atom Chemical group C* 0.000 description 6
• 238000005859 coupling reaction Methods 0.000 description 6
• 125000004122 cyclic group Chemical group 0.000 description 6
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
• QNXXNOAXMRJFPK-UHFFFAOYSA-N formic acid 4-[5-(1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]morpholine Chemical compound OC=O.C1CN(CCO1)c1ncnc2[nH]cc(-c3cn[nH]c3)c12 QNXXNOAXMRJFPK-UHFFFAOYSA-N 0.000 description 6
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
• 238000002953 preparative HPLC Methods 0.000 description 6
• 230000035484 reaction time Effects 0.000 description 6
• 239000011734 sodium Substances 0.000 description 6
• ONPUDLCOMXVDQL-UHFFFAOYSA-N 3-[6-(difluoromethyl)-4-morpholin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C=12C(C=3C=C(C=CC=3)C#N)=C(C(F)F)NC2=NC=NC=1N1CCOCC1 ONPUDLCOMXVDQL-UHFFFAOYSA-N 0.000 description 5
• 238000006069 Suzuki reaction reaction Methods 0.000 description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
• YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 5
• 239000003054 catalyst Substances 0.000 description 5
• 239000003112 inhibitor Substances 0.000 description 5
• 239000000543 intermediate Substances 0.000 description 5
• 239000001301 oxygen Substances 0.000 description 5
• 229910000027 potassium carbonate Inorganic materials 0.000 description 5
• 238000003756 stirring Methods 0.000 description 5
• 239000003826 tablet Substances 0.000 description 5
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
• UEQUQVLFIPOEMF-UHFFFAOYSA-N Mianserin Chemical compound C1C2=CC=CC=C2N2CCN(C)CC2C2=CC=CC=C21 UEQUQVLFIPOEMF-UHFFFAOYSA-N 0.000 description 4
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
• LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 4
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• 150000001721 carbon Chemical group 0.000 description 4
• 230000008878 coupling Effects 0.000 description 4
• 238000010168 coupling process Methods 0.000 description 4
• VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 4
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• IRCWCVKNJVCQJS-UHFFFAOYSA-N 2-[(5-iodo-2-methyl-4-morpholin-4-ylpyrrolo[2,3-d]pyrimidin-7-yl)methoxy]ethyl-trimethylsilane Chemical compound C=12C(I)=CN(COCC[Si](C)(C)C)C2=NC(C)=NC=1N1CCOCC1 IRCWCVKNJVCQJS-UHFFFAOYSA-N 0.000 description 3
• DEDJDGOXYKQVAP-UHFFFAOYSA-N 2-[(5-iodo-4-morpholin-4-ylpyrrolo[2,3-d]pyrimidin-7-yl)methoxy]ethyl-trimethylsilane Chemical compound N1=CN=C2N(COCC[Si](C)(C)C)C=C(I)C2=C1N1CCOCC1 DEDJDGOXYKQVAP-UHFFFAOYSA-N 0.000 description 3
• GTPYPGWTKZAMCX-UHFFFAOYSA-N 2-fluoro-3-[4-[2-(3-methyl-1,2,4-oxadiazol-5-yl)morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound CC1=NOC(C2OCCN(C2)C=2C=3C(C=4C(=C(C#N)C=CC=4)F)=CNC=3N=CN=2)=N1 GTPYPGWTKZAMCX-UHFFFAOYSA-N 0.000 description 3
• SAOVTENLRUIQAM-UHFFFAOYSA-N 3-[4-[2-(5-methyl-1,2,4-oxadiazol-3-yl)morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound O1C(C)=NC(C2OCCN(C2)C=2C=3C(C=4C=C(C=CC=4)C#N)=CNC=3N=CN=2)=N1 SAOVTENLRUIQAM-UHFFFAOYSA-N 0.000 description 3
• PPIDYHAZFFBKOT-UHFFFAOYSA-N 3-[4-[2-(methoxymethyl)morpholin-4-yl]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C1COC(COC)CN1C1=NC=NC2=C1C(C=1C=C(C=CC=1)C#N)=CN2 PPIDYHAZFFBKOT-UHFFFAOYSA-N 0.000 description 3
• NNOQAGZHQSZVEV-UHFFFAOYSA-N 3-[4-chloro-7-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C12=C(Cl)N=CN=C2N(COCC[Si](C)(C)C)C=C1C1=CC=CC(C#N)=C1 NNOQAGZHQSZVEV-UHFFFAOYSA-N 0.000 description 3
• HCUDUGCVOIKARC-UHFFFAOYSA-N 3-[4-chloro-7-(hydroxymethyl)pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile Chemical compound C12=C(Cl)N=CN=C2N(CO)C=C1C1=CC=CC(C#N)=C1 HCUDUGCVOIKARC-UHFFFAOYSA-N 0.000 description 3
• PLKRSMDMXVKCAM-UHFFFAOYSA-N 4-chloro-5-iodo-2-methyl-7h-pyrrolo[2,3-d]pyrimidine Chemical compound CC1=NC(Cl)=C2C(I)=CNC2=N1 PLKRSMDMXVKCAM-UHFFFAOYSA-N 0.000 description 3
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• 238000005481 NMR spectroscopy Methods 0.000 description 3
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• 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 3
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