HRP20020673A2 - Adenosine receptor modulators - Google Patents
Adenosine receptor modulatorsInfo
- Publication number
- HRP20020673A2 HRP20020673A2 HRP20020673A HRP20020673A2 HR P20020673 A2 HRP20020673 A2 HR P20020673A2 HR P20020673 A HRP20020673 A HR P20020673A HR P20020673 A2 HRP20020673 A2 HR P20020673A2
- Authority
- HR
- Croatia
- Prior art keywords
- amino
- furan
- pyrimidine
- carbonitrile
- pyridin
- Prior art date
Links
- 108050000203 Adenosine receptors Proteins 0.000 title claims description 10
- 102000009346 Adenosine receptors Human genes 0.000 title claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 432
- 150000001875 compounds Chemical class 0.000 claims description 416
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 411
- -1 carbonyl-phenyl Chemical group 0.000 claims description 294
- 125000003545 alkoxy group Chemical group 0.000 claims description 260
- 229910052736 halogen Inorganic materials 0.000 claims description 240
- 150000002367 halogens Chemical class 0.000 claims description 238
- 229910052757 nitrogen Inorganic materials 0.000 claims description 209
- 238000002360 preparation method Methods 0.000 claims description 153
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 124
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 116
- 125000005605 benzo group Chemical group 0.000 claims description 116
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 114
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 114
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 113
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 113
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims description 109
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 106
- 229910052739 hydrogen Inorganic materials 0.000 claims description 103
- 239000001257 hydrogen Substances 0.000 claims description 103
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 91
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 91
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 91
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 91
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 87
- 150000002431 hydrogen Chemical group 0.000 claims description 62
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 101150051188 Adora2a gene Proteins 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- LTGGOXVBFSHBCH-UHFFFAOYSA-N 6-amino-2-(furan-2-yl)-4-(pyridin-2-ylmethylamino)pyridine-3-carbonitrile Chemical compound N#CC=1C(C=2OC=CC=2)=NC(N)=CC=1NCC1=CC=CC=N1 LTGGOXVBFSHBCH-UHFFFAOYSA-N 0.000 claims description 8
- 239000001961 anticonvulsive agent Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 206010021143 Hypoxia Diseases 0.000 claims description 6
- 208000018737 Parkinson disease Diseases 0.000 claims description 6
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 6
- 230000007954 hypoxia Effects 0.000 claims description 6
- 208000028867 ischemia Diseases 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 208000026935 allergic disease Diseases 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 5
- 229940045200 cardioprotective agent Drugs 0.000 claims description 5
- 239000012659 cardioprotective agent Substances 0.000 claims description 5
- 239000003446 ligand Substances 0.000 claims description 5
- 230000004112 neuroprotection Effects 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- ADWVQEURVRQVCR-UHFFFAOYSA-N 2-amino-4-(1,3-benzodioxol-5-ylmethylamino)-6-(furan-2-yl)pyrimidine-5-carbonitrile Chemical compound N=1C(N)=NC(NCC=2C=C3OCOC3=CC=2)=C(C#N)C=1C1=CC=CO1 ADWVQEURVRQVCR-UHFFFAOYSA-N 0.000 claims description 4
- VKNINZJBKJPTBX-UHFFFAOYSA-N 2-amino-4-(2,3-dihydro-1,4-benzodioxin-6-yl)-6-methylsulfanylpyrimidine-5-carbonitrile Chemical compound CSC1=NC(N)=NC(C=2C=C3OCCOC3=CC=2)=C1C#N VKNINZJBKJPTBX-UHFFFAOYSA-N 0.000 claims description 4
- OTFJEMCTGJYMJE-UHFFFAOYSA-N 2-amino-4-(2,3-dihydrofuran-5-yl)-6-[(4-methylpyridin-2-yl)methylamino]pyrimidine-5-carbonitrile Chemical compound CC1=CC=NC(CNC=2C(=C(C=3OCCC=3)N=C(N)N=2)C#N)=C1 OTFJEMCTGJYMJE-UHFFFAOYSA-N 0.000 claims description 4
- TXDNLRTXKGXXMP-UHFFFAOYSA-N 2-amino-4-(2-anilinoethoxy)-6-(furan-2-yl)pyrimidine-5-carbonitrile Chemical compound N#CC=1C(C=2OC=CC=2)=NC(N)=NC=1OCCNC1=CC=CC=C1 TXDNLRTXKGXXMP-UHFFFAOYSA-N 0.000 claims description 4
- YEIDLRWYTKRALT-UHFFFAOYSA-N 2-amino-4-(2-anilinoethylamino)-6-(furan-2-yl)pyrimidine-5-carbonitrile Chemical compound N#CC=1C(C=2OC=CC=2)=NC(N)=NC=1NCCNC1=CC=CC=C1 YEIDLRWYTKRALT-UHFFFAOYSA-N 0.000 claims description 4
- HTINGMNYSWDCHV-UHFFFAOYSA-N 2-amino-4-(2-pyridin-2-ylethylsulfanyl)-6-thiophen-2-ylpyrimidine-5-carbonitrile Chemical compound N#CC=1C(C=2SC=CC=2)=NC(N)=NC=1SCCC1=CC=CC=N1 HTINGMNYSWDCHV-UHFFFAOYSA-N 0.000 claims description 4
- PCIKUURTLDQTOM-UHFFFAOYSA-N 2-amino-4-(3,4-dihydro-1h-isoquinolin-2-yl)-6-(furan-2-yl)pyrimidine-5-carbonitrile Chemical compound N=1C(N)=NC(N2CC3=CC=CC=C3CC2)=C(C#N)C=1C1=CC=CO1 PCIKUURTLDQTOM-UHFFFAOYSA-N 0.000 claims description 4
- FPZNIKIYLFQUGZ-UHFFFAOYSA-N 2-amino-4-(3-fluorophenyl)-6-(2-pyridin-2-ylethoxy)pyrimidine-5-carbonitrile Chemical compound N#CC=1C(C=2C=C(F)C=CC=2)=NC(N)=NC=1OCCC1=CC=CC=N1 FPZNIKIYLFQUGZ-UHFFFAOYSA-N 0.000 claims description 4
- PZSLCZLNKBFUQO-UHFFFAOYSA-N 2-amino-4-(4-bromofuran-2-yl)-6-[(3-methylpyridin-2-yl)methoxy]pyrimidine-5-carbonitrile Chemical compound CC1=CC=CN=C1COC1=NC(N)=NC(C=2OC=C(Br)C=2)=C1C#N PZSLCZLNKBFUQO-UHFFFAOYSA-N 0.000 claims description 4
- QPAPAMATEKAURM-UHFFFAOYSA-N 2-amino-4-(4-bromofuran-2-yl)-6-[(5-methylpyridin-2-yl)methoxy]pyrimidine-5-carbonitrile Chemical compound N1=CC(C)=CC=C1COC1=NC(N)=NC(C=2OC=C(Br)C=2)=C1C#N QPAPAMATEKAURM-UHFFFAOYSA-N 0.000 claims description 4
- IONRJCGQFOGVHG-UHFFFAOYSA-N 2-amino-4-(4-cyanofuran-2-yl)-6-(2-pyridin-2-ylethylsulfanyl)pyrimidine-5-carbonitrile Chemical compound N#CC=1C(C=2OC=C(C=2)C#N)=NC(N)=NC=1SCCC1=CC=CC=N1 IONRJCGQFOGVHG-UHFFFAOYSA-N 0.000 claims description 4
- RVHJFTNUZXXRDF-UHFFFAOYSA-N 2-amino-4-(4-methylfuran-2-yl)-6-(2-pyridin-2-ylethoxy)pyrimidine-5-carbonitrile Chemical compound CC1=COC(C=2C(=C(OCCC=3N=CC=CC=3)N=C(N)N=2)C#N)=C1 RVHJFTNUZXXRDF-UHFFFAOYSA-N 0.000 claims description 4
- PBHVZEWVLRODIV-UHFFFAOYSA-N 2-amino-4-(4-methylfuran-2-yl)-6-(2-pyridin-2-ylethylsulfanyl)pyrimidine-5-carbonitrile Chemical compound CC1=COC(C=2C(=C(SCCC=3N=CC=CC=3)N=C(N)N=2)C#N)=C1 PBHVZEWVLRODIV-UHFFFAOYSA-N 0.000 claims description 4
- BGBYXRGRJMDMFL-UHFFFAOYSA-N 2-amino-4-(5-bromofuran-2-yl)-6-(2-pyridin-2-ylethoxy)pyrimidine-5-carbonitrile Chemical compound N#CC=1C(C=2OC(Br)=CC=2)=NC(N)=NC=1OCCC1=CC=CC=N1 BGBYXRGRJMDMFL-UHFFFAOYSA-N 0.000 claims description 4
- BRQZWATYAJZSCP-UHFFFAOYSA-N 2-amino-4-(5-bromofuran-2-yl)-6-(2-pyridin-2-ylethylsulfanyl)pyrimidine-5-carbonitrile Chemical compound N#CC=1C(C=2OC(Br)=CC=2)=NC(N)=NC=1SCCC1=CC=CC=N1 BRQZWATYAJZSCP-UHFFFAOYSA-N 0.000 claims description 4
- JNOJCZZULAHVAO-UHFFFAOYSA-N 2-amino-4-(5-bromofuran-2-yl)-6-[(2-bromophenyl)methylamino]pyrimidine-5-carbonitrile Chemical compound N#CC=1C(C=2OC(Br)=CC=2)=NC(N)=NC=1NCC1=CC=CC=C1Br JNOJCZZULAHVAO-UHFFFAOYSA-N 0.000 claims description 4
- JBZOYUBODQIILV-UHFFFAOYSA-N 2-amino-4-(5-chlorofuran-2-yl)-6-(2-pyridin-2-ylethoxy)pyrimidine-5-carbonitrile Chemical compound N#CC=1C(C=2OC(Cl)=CC=2)=NC(N)=NC=1OCCC1=CC=CC=N1 JBZOYUBODQIILV-UHFFFAOYSA-N 0.000 claims description 4
- BWEODSZBTBQLLX-UHFFFAOYSA-N 2-amino-4-(5-chlorofuran-2-yl)-6-(2-pyridin-2-ylethylsulfanyl)pyrimidine-5-carbonitrile Chemical compound N#CC=1C(C=2OC(Cl)=CC=2)=NC(N)=NC=1SCCC1=CC=CC=N1 BWEODSZBTBQLLX-UHFFFAOYSA-N 0.000 claims description 4
- LHARAAKUEUOCMR-UHFFFAOYSA-N 2-amino-4-(5-chlorofuran-2-yl)-6-[(3,5-dimethylpyridin-2-yl)methoxy]pyrimidine-5-carbonitrile Chemical compound CC1=CC(C)=CN=C1COC1=NC(N)=NC(C=2OC(Cl)=CC=2)=C1C#N LHARAAKUEUOCMR-UHFFFAOYSA-N 0.000 claims description 4
- BZGJIIQUOLMETK-UHFFFAOYSA-N 2-amino-4-(5-chlorofuran-2-yl)-6-[(3-methylpyridin-2-yl)methoxy]pyrimidine-5-carbonitrile Chemical compound CC1=CC=CN=C1COC1=NC(N)=NC(C=2OC(Cl)=CC=2)=C1C#N BZGJIIQUOLMETK-UHFFFAOYSA-N 0.000 claims description 4
- UKMGOVGNLLPTAM-UHFFFAOYSA-N 2-amino-4-(5-chlorofuran-2-yl)-6-[(5-methylpyridin-2-yl)methoxy]pyrimidine-5-carbonitrile Chemical compound N1=CC(C)=CC=C1COC1=NC(N)=NC(C=2OC(Cl)=CC=2)=C1C#N UKMGOVGNLLPTAM-UHFFFAOYSA-N 0.000 claims description 4
- REIDOBQYMTYZKR-UHFFFAOYSA-N 2-amino-4-(5-methylfuran-2-yl)-6-(pyridin-2-ylmethoxy)pyrimidine-5-carbonitrile Chemical compound O1C(C)=CC=C1C1=NC(N)=NC(OCC=2N=CC=CC=2)=C1C#N REIDOBQYMTYZKR-UHFFFAOYSA-N 0.000 claims description 4
- BFMGZMJFOQVBBK-UHFFFAOYSA-N 2-amino-4-(5-methylfuran-2-yl)-6-[(6-methylpyridin-2-yl)methoxy]pyrimidine-5-carbonitrile Chemical compound O1C(C)=CC=C1C1=NC(N)=NC(OCC=2N=C(C)C=CC=2)=C1C#N BFMGZMJFOQVBBK-UHFFFAOYSA-N 0.000 claims description 4
- NQOOBUGSBLONSU-UHFFFAOYSA-N 2-amino-4-(benzylamino)-6-(5-methylfuran-2-yl)pyrimidine-5-carbonitrile Chemical compound O1C(C)=CC=C1C1=NC(N)=NC(NCC=2C=CC=CC=2)=C1C#N NQOOBUGSBLONSU-UHFFFAOYSA-N 0.000 claims description 4
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- UUONCRGMPGAKOM-UHFFFAOYSA-N 2-amino-4-(furan-2-yl)-6-(1,2,3,4-tetrahydroquinolin-2-ylmethylamino)pyrimidine-5-carbonitrile Chemical compound N=1C(N)=NC(NCC2NC3=CC=CC=C3CC2)=C(C#N)C=1C1=CC=CO1 UUONCRGMPGAKOM-UHFFFAOYSA-N 0.000 claims description 4
- SMHFIBFCYIHFQZ-UHFFFAOYSA-N 2-amino-4-(furan-2-yl)-6-(2-phenoxyethylamino)pyrimidine-5-carbonitrile Chemical compound N#CC=1C(C=2OC=CC=2)=NC(N)=NC=1NCCOC1=CC=CC=C1 SMHFIBFCYIHFQZ-UHFFFAOYSA-N 0.000 claims description 4
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- WTWFIHBBIXYAEE-UHFFFAOYSA-N 2-amino-4-(furan-2-yl)-6-(2-phenylethylsulfanyl)pyrimidine-5-carbonitrile Chemical compound N#CC=1C(C=2OC=CC=2)=NC(N)=NC=1SCCC1=CC=CC=C1 WTWFIHBBIXYAEE-UHFFFAOYSA-N 0.000 claims description 4
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- QPANELQPZUDJPD-UHFFFAOYSA-N 2-amino-4-(furan-2-yl)-6-(2-pyridin-2-ylethylsulfanyl)pyrimidine-5-carbonitrile Chemical compound N#CC=1C(C=2OC=CC=2)=NC(N)=NC=1SCCC1=CC=CC=N1 QPANELQPZUDJPD-UHFFFAOYSA-N 0.000 claims description 4
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- AHYHMFBHALSKDK-UHFFFAOYSA-N 2-amino-4-(furan-2-yl)-6-(3-phenylpropylamino)pyrimidine-5-carbonitrile Chemical compound N#CC=1C(C=2OC=CC=2)=NC(N)=NC=1NCCCC1=CC=CC=C1 AHYHMFBHALSKDK-UHFFFAOYSA-N 0.000 claims description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
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- A—HUMAN NECESSITIES
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/443—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with oxygen as a ring hetero atom
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
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