CA2440760C - Substituted pyrazolopyrimidines and thiazolopyrimidines used as analgesics - Google Patents

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Publication number

CA2440760C

CA2440760C CA2440760A CA2440760A CA2440760C CA 2440760 C CA2440760 C CA 2440760C CA 2440760 A CA2440760 A CA 2440760A CA 2440760 A CA2440760 A CA 2440760A CA 2440760 C CA2440760 C CA 2440760C

Authority

CA

Canada

Prior art keywords

compound

denotes

alkyl

pyrimidine

compound according

Prior art date

2001-03-14

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.)

Expired - Fee Related

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• APXRHPDHORGIEB-UHFFFAOYSA-N 1H-pyrazolo[4,3-d]pyrimidine Chemical class N1=CN=C2C=NNC2=C1 APXRHPDHORGIEB-UHFFFAOYSA-N 0.000 title abstract description 6
• 150000008634 thiazolopyrimidines Chemical class 0.000 title abstract description 5
• 229940035676 analgesics Drugs 0.000 title description 2
• 239000000730 antalgic agent Substances 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 481
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 36
• 208000002193 Pain Diseases 0.000 claims abstract description 31
• 238000000034 method Methods 0.000 claims abstract description 27
• 239000000126 substance Substances 0.000 claims abstract description 22
• 208000018737 Parkinson disease Diseases 0.000 claims abstract description 20
• 201000000980 schizophrenia Diseases 0.000 claims abstract description 20
• 208000023105 Huntington disease Diseases 0.000 claims abstract description 19
• 206010015037 epilepsy Diseases 0.000 claims abstract description 19
• 201000010099 disease Diseases 0.000 claims abstract description 15
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 15
• 206010021143 Hypoxia Diseases 0.000 claims abstract description 13
• 208000004296 neuralgia Diseases 0.000 claims abstract description 13
• 208000021722 neuropathic pain Diseases 0.000 claims abstract description 13
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 12
• 208000010412 Glaucoma Diseases 0.000 claims abstract description 11
• 201000004681 Psoriasis Diseases 0.000 claims abstract description 11
• 208000006011 Stroke Diseases 0.000 claims abstract description 11
• 208000007536 Thrombosis Diseases 0.000 claims abstract description 11
• 206010046543 Urinary incontinence Diseases 0.000 claims abstract description 11
• 206010003119 arrhythmia Diseases 0.000 claims abstract description 11
• 201000011510 cancer Diseases 0.000 claims abstract description 11
• 210000003169 central nervous system Anatomy 0.000 claims abstract description 11
• 230000002490 cerebral effect Effects 0.000 claims abstract description 11
• 230000004968 inflammatory condition Effects 0.000 claims abstract description 11
• 208000014674 injury Diseases 0.000 claims abstract description 11
• 230000008733 trauma Effects 0.000 claims abstract description 11
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 10
• 206010048962 Brain oedema Diseases 0.000 claims abstract description 10
• 206010008120 Cerebral ischaemia Diseases 0.000 claims abstract description 10
• 206010028923 Neonatal asphyxia Diseases 0.000 claims abstract description 10
• 208000037212 Neonatal hypoxic and ischemic brain injury Diseases 0.000 claims abstract description 10
• 208000028017 Psychotic disease Diseases 0.000 claims abstract description 10
• 208000009205 Tinnitus Diseases 0.000 claims abstract description 10
• 208000000323 Tourette Syndrome Diseases 0.000 claims abstract description 10
• 208000016620 Tourette disease Diseases 0.000 claims abstract description 10
• 150000001413 amino acids Chemical class 0.000 claims abstract description 10
• 206010008118 cerebral infarction Diseases 0.000 claims abstract description 10
• 201000002491 encephalomyelitis Diseases 0.000 claims abstract description 10
• 208000033300 perinatal asphyxia Diseases 0.000 claims abstract description 10
• 231100000886 tinnitus Toxicity 0.000 claims abstract description 10
• 230000007954 hypoxia Effects 0.000 claims abstract description 8
• -1 stereoisomer Substances 0.000 claims description 348
• 125000003118 aryl group Chemical group 0.000 claims description 129
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 79
• 125000004429 atom Chemical group 0.000 claims description 59
• 239000000203 mixture Substances 0.000 claims description 51
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 44
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 43
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 43
• 150000003839 salts Chemical class 0.000 claims description 43
• 229910052739 hydrogen Inorganic materials 0.000 claims description 42
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 42
• 108020003175 receptors Proteins 0.000 claims description 42
• 125000000217 alkyl group Chemical group 0.000 claims description 40
• 229910052794 bromium Inorganic materials 0.000 claims description 39
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 39
• 238000011282 treatment Methods 0.000 claims description 38
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
• 239000002253 acid Substances 0.000 claims description 32
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 31
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 30
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 30
• 125000000623 heterocyclic group Chemical group 0.000 claims description 29
• 229910052731 fluorine Inorganic materials 0.000 claims description 28
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 27
• 239000000460 chlorine Substances 0.000 claims description 27
• 229910052801 chlorine Inorganic materials 0.000 claims description 27
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 27
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 25
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 24
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 23
• 230000000626 neurodegenerative effect Effects 0.000 claims description 23
• 239000012453 solvate Substances 0.000 claims description 22
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 21
• 239000002585 base Substances 0.000 claims description 21
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 21
• 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 20
• 230000002265 prevention Effects 0.000 claims description 20
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 19
• 102000019055 Nucleoside Transport Proteins Human genes 0.000 claims description 19
• 108010012315 Nucleoside Transport Proteins Proteins 0.000 claims description 19
• 239000011737 fluorine Substances 0.000 claims description 19
• 125000001424 substituent group Chemical group 0.000 claims description 19
• 101710169336 5'-deoxyadenosine deaminase Proteins 0.000 claims description 18
• OOXNYFKPOPJIOT-UHFFFAOYSA-N 5-(3-bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-amine;dihydrochloride Chemical compound Cl.Cl.C=12C(N)=NC=NC2=NC(C=2C=NC(=CC=2)N2CCOCC2)=CC=1C1=CC=CC(Br)=C1 OOXNYFKPOPJIOT-UHFFFAOYSA-N 0.000 claims description 18
• 102000055025 Adenosine deaminases Human genes 0.000 claims description 18
• 102100032534 Adenosine kinase Human genes 0.000 claims description 18
• 108010076278 Adenosine kinase Proteins 0.000 claims description 18
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
• 210000000987 immune system Anatomy 0.000 claims description 18
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 17
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 17
• 101100240518 Caenorhabditis elegans nhr-12 gene Proteins 0.000 claims description 16
• 238000002360 preparation method Methods 0.000 claims description 16
• 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 claims description 15
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 15
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 14
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 14
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 14
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 14
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 14
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 14
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• 239000003446 ligand Substances 0.000 claims description 14
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 14
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 13
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 12
• 150000001336 alkenes Chemical class 0.000 claims description 12
• 229910003204 NH2 Inorganic materials 0.000 claims description 11
• 238000006243 chemical reaction Methods 0.000 claims description 11
• 230000005764 inhibitory process Effects 0.000 claims description 11
• 229910052740 iodine Inorganic materials 0.000 claims description 11
• JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 11
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 11
• 206010050081 Neonatal hypoxia Diseases 0.000 claims description 10
• 208000001647 Renal Insufficiency Diseases 0.000 claims description 10
• 206010040070 Septic Shock Diseases 0.000 claims description 10
• 201000006370 kidney failure Diseases 0.000 claims description 10
• 230000007257 malfunction Effects 0.000 claims description 10
• 230000037361 pathway Effects 0.000 claims description 10
• 230000000241 respiratory effect Effects 0.000 claims description 10
• 230000036303 septic shock Effects 0.000 claims description 10
• 208000019116 sleep disease Diseases 0.000 claims description 10
• 208000022925 sleep disturbance Diseases 0.000 claims description 10
• 208000030507 AIDS Diseases 0.000 claims description 9
• 206010012289 Dementia Diseases 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
• 208000028867 ischemia Diseases 0.000 claims description 9
• BFKYQYMHJANOTR-UHFFFAOYSA-N 2h-pyrimidine-1-carbonitrile Chemical compound N#CN1CN=CC=C1 BFKYQYMHJANOTR-UHFFFAOYSA-N 0.000 claims description 8
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 5
• 238000011321 prophylaxis Methods 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• NNJXJEANZPCXEB-UHFFFAOYSA-N 3-bromo-7-(3,4-dimethoxyphenyl)-5-(5-nitrofuran-2-yl)-2-phenyl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(C=2OC(=CC=2)[N+]([O-])=O)=NC2N1NC(C=1C=CC=CC=1)C2Br NNJXJEANZPCXEB-UHFFFAOYSA-N 0.000 claims description 4
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 229910052717 sulfur Inorganic materials 0.000 claims description 4
• JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 claims description 3
• ONMSTJPALRFZAG-UHFFFAOYSA-N 2,5,7-trimethyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine Chemical compound N1C(C)CC(C)N2N=C(C)C=C21 ONMSTJPALRFZAG-UHFFFAOYSA-N 0.000 claims description 3
• QRSPKYHTPGGZAH-UHFFFAOYSA-N 3-bromo-7-(3,4-dimethoxyphenyl)-2-phenyl-5-pyridin-2-yl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(C=2N=CC=CC=2)=NC2N1NC(C=1C=CC=CC=1)C2Br QRSPKYHTPGGZAH-UHFFFAOYSA-N 0.000 claims description 3
• XTSMYJXQALSHRE-UHFFFAOYSA-N 3-cyano-7-(2,4-dimethylphenyl)-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylic acid Chemical compound CC1=CC(C)=CC=C1C1=CC(C(O)=O)=NC2N1NCC2C#N XTSMYJXQALSHRE-UHFFFAOYSA-N 0.000 claims description 3
• QYIWGAOXEPSWQS-UHFFFAOYSA-N 3-phenyldiazenyl-7-phenylsulfanyl-5-pyridin-2-yl-3,5,6,7-tetrahydro-1h-pyrazolo[1,5-a]pyrimidin-2-one Chemical compound OC1=NN2C(SC=3C=CC=CC=3)CC(C=3N=CC=CC=3)N=C2C1N=NC1=CC=CC=C1 QYIWGAOXEPSWQS-UHFFFAOYSA-N 0.000 claims description 3
• UVZIQHQSQAMQMA-UHFFFAOYSA-N 5,7-dimethyl-2-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine Chemical compound C1=C2NC(C)CC(C)N2N=C1C1=CC=CC=C1 UVZIQHQSQAMQMA-UHFFFAOYSA-N 0.000 claims description 3
• AORVUAURQOBBCB-UHFFFAOYSA-N 5,7-dimethyl-3-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine Chemical compound C=12NC(C)CC(C)N2N=CC=1C1=CC=CC=C1 AORVUAURQOBBCB-UHFFFAOYSA-N 0.000 claims description 3
• FULUEAGFTYHPAG-UHFFFAOYSA-N 7-(3,4-dimethoxyphenyl)-5-(5-nitrothiophen-2-yl)-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(C=2SC(=CC=2)[N+]([O-])=O)=NC2N1NCC2C#N FULUEAGFTYHPAG-UHFFFAOYSA-N 0.000 claims description 3
• RWDOREPNMHBEFB-UHFFFAOYSA-N 7-cyclopropyl-10-phenyldiazenyl-3-oxa-1,8,12-triazatricyclo[7.3.0.02,6]dodec-9-en-11-one Chemical compound OC1=NN2C3OCCC3C(C3CC3)NC2=C1N=NC1=CC=CC=C1 RWDOREPNMHBEFB-UHFFFAOYSA-N 0.000 claims description 3
• ZGADVYMSJZOLEF-UHFFFAOYSA-N 8-(4-hydroxybutyl)-2,3,7-triazatetracyclo[7.7.0.02,6.011,16]hexadeca-3,5,11,13,15-pentaene-5-carbonitrile Chemical compound C1=CC=C2C3N4N=CC(C#N)=C4NC(CCCCO)C3CC2=C1 ZGADVYMSJZOLEF-UHFFFAOYSA-N 0.000 claims description 3
• HIRDXZLQYKQAON-UHFFFAOYSA-N C1=C(O)C(OC)=CC(C2C3C(C4=CC=CC=C4C3)N3N=C(SC)C(C#N)C3=N2)=C1 Chemical compound C1=C(O)C(OC)=CC(C2C3C(C4=CC=CC=C4C3)N3N=C(SC)C(C#N)C3=N2)=C1 HIRDXZLQYKQAON-UHFFFAOYSA-N 0.000 claims description 3
• 101100294104 Caenorhabditis elegans nhr-34 gene Proteins 0.000 claims description 3
• JKTBVSCLKWWZPD-UHFFFAOYSA-N diethyl 1,8,12-triazatricyclo[7.3.0.02,6]dodeca-3,9,11-triene-7,10-dicarboxylate Chemical compound CCOC(=O)C1NC2=C(C(=O)OCC)C=NN2C2C=CCC12 JKTBVSCLKWWZPD-UHFFFAOYSA-N 0.000 claims description 3
• GNQOEDIBOLTTKB-UHFFFAOYSA-N diethyl 2,3,7-triazatetracyclo[7.7.0.02,6.011,16]hexadeca-3,5,11,13,15-pentaene-5,8-dicarboxylate Chemical compound C1=CC=C2C3N4N=CC(C(=O)OCC)=C4NC(C(=O)OCC)C3CC2=C1 GNQOEDIBOLTTKB-UHFFFAOYSA-N 0.000 claims description 3
• KMMPRDWQWXXTEU-UHFFFAOYSA-N ethyl 10-bromo-11-phenyl-1,8,12-triazatricyclo[7.3.0.02,6]dodeca-3,9,11-triene-7-carboxylate Chemical compound N=1N2C3C=CCC3C(C(=O)OCC)NC2=C(Br)C=1C1=CC=CC=C1 KMMPRDWQWXXTEU-UHFFFAOYSA-N 0.000 claims description 3
• OEQROHSOZGVEJL-UHFFFAOYSA-N ethyl 4-oxo-5-phenyldiazenyl-2,3,7-triazatetracyclo[7.7.0.02,6.011,16]hexadeca-5,11,13,15-tetraene-8-carboxylate Chemical compound OC1=NN2C(C3=CC=CC=C3C3)C3C(C(=O)OCC)NC2=C1N=NC1=CC=CC=C1 OEQROHSOZGVEJL-UHFFFAOYSA-N 0.000 claims description 3
• JJKPGPACAOVIIC-UHFFFAOYSA-N ethyl 7-cyclohexyl-3-oxa-1,8,12-triazatricyclo[7.3.0.02,6]dodeca-9,11-diene-10-carboxylate Chemical compound N1C2=C(C(=O)OCC)C=NN2C2OCCC2C1C1CCCCC1 JJKPGPACAOVIIC-UHFFFAOYSA-N 0.000 claims description 3
• NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 3
• 239000003960 organic solvent Substances 0.000 claims description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• SYBNTJUJVKJEDU-UHFFFAOYSA-N 2,5-dimethyl-7-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine Chemical compound N12N=C(C)C=C2NC(C)CC1C1=CC=CC=C1 SYBNTJUJVKJEDU-UHFFFAOYSA-N 0.000 claims description 2
• WNPGOPBNWXEXAD-UHFFFAOYSA-N 3-(5-cyano-2,3,7-triazatetracyclo[7.7.0.02,6.011,16]hexadeca-3,5,11,13,15-pentaen-8-yl)-2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(C2C3C(C4=CC=CC=C4C3)N3N=CC(=C3N2)C#N)=C1O WNPGOPBNWXEXAD-UHFFFAOYSA-N 0.000 claims description 2
• GQVBNDFWHMONSS-UHFFFAOYSA-N 3-[3-cyano-7-(4-hydroxyphenyl)-6-methyl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-2-hydroxybenzoic acid Chemical compound CC1=C(C=2C=CC(O)=CC=2)N2NCC(C#N)C2N=C1C1=CC=CC(C(O)=O)=C1O GQVBNDFWHMONSS-UHFFFAOYSA-N 0.000 claims description 2
• IPJINLLNRCMBSV-UHFFFAOYSA-N 3-bromo-5-cyclopropyl-7-(3,4-dimethoxyphenyl)-2-phenyl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(C2CC2)=NC2N1NC(C=1C=CC=CC=1)C2Br IPJINLLNRCMBSV-UHFFFAOYSA-N 0.000 claims description 2
• FNANXDCOTZQWMD-UHFFFAOYSA-N 3-bromo-7-(2,4-dimethylphenyl)-2-phenyl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylic acid Chemical compound CC1=CC(C)=CC=C1C1=CC(C(O)=O)=NC2N1NC(C=1C=CC=CC=1)C2Br FNANXDCOTZQWMD-UHFFFAOYSA-N 0.000 claims description 2
• WLUXDPLEGABCTA-UHFFFAOYSA-N 3-bromo-7-(2,4-dimethylphenyl)-2-phenyl-5-pyridin-2-yl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine Chemical compound CC1=CC(C)=CC=C1C1=CC(C=2N=CC=CC=2)=NC2N1NC(C=1C=CC=CC=1)C2Br WLUXDPLEGABCTA-UHFFFAOYSA-N 0.000 claims description 2
• GQCOXXJMGFBZCB-UHFFFAOYSA-N 3-bromo-7-(2,4-dimethylphenyl)-5-(4-phenoxyphenyl)-2-phenyl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine Chemical compound CC1=CC(C)=CC=C1C1=CC(C=2C=CC(OC=3C=CC=CC=3)=CC=2)=NC2N1NC(C=1C=CC=CC=1)C2Br GQCOXXJMGFBZCB-UHFFFAOYSA-N 0.000 claims description 2
• KEVRDWFZUYXLHN-UHFFFAOYSA-N 3-bromo-7-(2,4-dimethylphenyl)-5-(5-nitrofuran-2-yl)-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine Chemical compound CC1=CC(C)=CC=C1C1=CC(C=2OC(=CC=2)[N+]([O-])=O)=NC2N1NCC2Br KEVRDWFZUYXLHN-UHFFFAOYSA-N 0.000 claims description 2
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• KTDJFVSINALPTJ-UHFFFAOYSA-N OC(=O)C1=CC=CC(C2C3C(C4=CC=CC=C4C3)N3N=CC(C3=N2)C#N)=C1O Chemical compound OC(=O)C1=CC=CC(C2C3C(C4=CC=CC=C4C3)N3N=CC(C3=N2)C#N)=C1O KTDJFVSINALPTJ-UHFFFAOYSA-N 0.000 claims description 2
• LZMSCOOAVVUPKJ-UHFFFAOYSA-N OC1=NN2C3C=CCC3C(C(=O)OCC)N=C2C1N=NC1=CC=CC=C1 Chemical compound OC1=NN2C3C=CCC3C(C(=O)OCC)N=C2C1N=NC1=CC=CC=C1 LZMSCOOAVVUPKJ-UHFFFAOYSA-N 0.000 claims description 2
• XNAVBLMMFWPBEN-UHFFFAOYSA-N [3-bromo-7-(2,4-dimethylphenyl)-5-(5-nitrofuran-2-yl)-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidin-2-yl]-phenyldiazene Chemical compound CC1=CC(C)=CC=C1C1=CC(C=2OC(=CC=2)[N+]([O-])=O)=NC2N1NC(N=NC=1C=CC=CC=1)C2Br XNAVBLMMFWPBEN-UHFFFAOYSA-N 0.000 claims description 2
• FVSFWJRHCGLYIU-UHFFFAOYSA-N [3-bromo-7-(3,4-dimethoxyphenyl)-2-phenyl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-phenylmethanone Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(C(=O)C=2C=CC=CC=2)=NC2N1NC(C=1C=CC=CC=1)C2Br FVSFWJRHCGLYIU-UHFFFAOYSA-N 0.000 claims description 2
• QFMRQUWUPQHJNL-UHFFFAOYSA-N [3-bromo-7-(3-bromophenyl)-2-phenyl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-phenylmethanone Chemical compound BrC1C(C=2C=CC=CC=2)NN2C1N=C(C(=O)C=1C=CC=CC=1)C=C2C1=CC=CC(Br)=C1 QFMRQUWUPQHJNL-UHFFFAOYSA-N 0.000 claims description 2
• DXEIVEWCMYWSDI-UHFFFAOYSA-N [3-bromo-7-(3-fluorophenyl)-2-phenyl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]-phenylmethanone Chemical compound FC1=CC=CC(C=2N3NC(C(Br)C3N=C(C=2)C(=O)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 DXEIVEWCMYWSDI-UHFFFAOYSA-N 0.000 claims description 2
• GVXIGYMWZUEEMI-UHFFFAOYSA-N diethyl 7-(2,3,4-trimethoxyphenyl)-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-3,5-dicarboxylate Chemical compound CCOC(=O)C1CNN2C1N=C(C(=O)OCC)C=C2C1=CC=C(OC)C(OC)=C1OC GVXIGYMWZUEEMI-UHFFFAOYSA-N 0.000 claims description 2
• BQHZWNCLLCVFMA-UHFFFAOYSA-N diethyl 7-phenylsulfanyl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-3,5-dicarboxylate Chemical compound CCOC(=O)C1CNN2C1N=C(C(=O)OCC)C=C2SC1=CC=CC=C1 BQHZWNCLLCVFMA-UHFFFAOYSA-N 0.000 claims description 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
• NKZTUORUYUOGMX-UHFFFAOYSA-N ethyl 11-oxo-10-phenyldiazenyl-1,8,12-triazatricyclo[7.3.0.02,6]dodeca-3,9-diene-7-carboxylate Chemical compound OC1=NN2C3C=CCC3C(C(=O)OCC)NC2=C1N=NC1=CC=CC=C1 NKZTUORUYUOGMX-UHFFFAOYSA-N 0.000 claims description 2
• DALBYYALKQKKEV-UHFFFAOYSA-N ethyl 2-(3-bromo-7-naphthalen-2-yl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl)cyclopropane-1-carboxylate Chemical compound CCOC(=O)C1CC1C(C=C1C=2C=C3C=CC=CC3=CC=2)=NC2N1NCC2Br DALBYYALKQKKEV-UHFFFAOYSA-N 0.000 claims description 2
• KSIDANUAZYLAHC-UHFFFAOYSA-N ethyl 2-[3-bromo-7-(2,4-dimethylphenyl)-2-phenyl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]cyclopropane-1-carboxylate Chemical compound CCOC(=O)C1CC1C(C=C1C=2C(=CC(C)=CC=2)C)=NC2N1NC(C=1C=CC=CC=1)C2Br KSIDANUAZYLAHC-UHFFFAOYSA-N 0.000 claims description 2
• MOBLKXVCSMSERI-UHFFFAOYSA-N ethyl 2-[3-bromo-7-(3-bromophenyl)-2-phenyl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]cyclopropane-1-carboxylate Chemical compound CCOC(=O)C1CC1C(C=C1C=2C=C(Br)C=CC=2)=NC2N1NC(C=1C=CC=CC=1)C2Br MOBLKXVCSMSERI-UHFFFAOYSA-N 0.000 claims description 2
• VPWKGRJDOXBEQP-UHFFFAOYSA-N ethyl 2-[3-bromo-7-(3-methylphenyl)-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]cyclopropane-1-carboxylate Chemical compound CCOC(=O)C1CC1C(C=C1C=2C=C(C)C=CC=2)=NC2N1NCC2Br VPWKGRJDOXBEQP-UHFFFAOYSA-N 0.000 claims description 2
• BPUCGEOUUDXRTH-UHFFFAOYSA-N ethyl 2-[3-bromo-7-(4-bromophenyl)-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]cyclopropane-1-carboxylate Chemical compound CCOC(=O)C1CC1C(C=C1C=2C=CC(Br)=CC=2)=NC2N1NCC2Br BPUCGEOUUDXRTH-UHFFFAOYSA-N 0.000 claims description 2
• JPMYHYTZYUNMTF-UHFFFAOYSA-N ethyl 2-[3-cyano-6,7-bis(4-methoxyphenyl)-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]cyclopropane-1-carboxylate Chemical compound CCOC(=O)C1CC1C(C(=C1C=2C=CC(OC)=CC=2)C=2C=CC(OC)=CC=2)=NC2N1NCC2C#N JPMYHYTZYUNMTF-UHFFFAOYSA-N 0.000 claims description 2
• LLPGTYCNRPAYKY-UHFFFAOYSA-N ethyl 2-[3-cyano-7-(2,4-dimethylphenyl)-2-methylsulfanyl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]cyclopropane-1-carboxylate Chemical compound CCOC(=O)C1CC1C(C=C1C=2C(=CC(C)=CC=2)C)=NC2N1NC(SC)C2C#N LLPGTYCNRPAYKY-UHFFFAOYSA-N 0.000 claims description 2
• QJQHNMWDPOCCKD-UHFFFAOYSA-N ethyl 2-[7-(2,4-dimethylphenyl)-2-hydroxy-3-phenyldiazenyl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]cyclopropane-1-carboxylate Chemical compound CCOC(=O)C1CC1C(C=C1C=2C(=CC(C)=CC=2)C)=NC2N1NC(O)C2N=NC1=CC=CC=C1 QJQHNMWDPOCCKD-UHFFFAOYSA-N 0.000 claims description 2
• PRNZPLBZGJVWKJ-UHFFFAOYSA-N ethyl 2-[7-(3-bromophenyl)-3-cyano-2-methylsulfanyl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidin-5-yl]cyclopropane-1-carboxylate Chemical compound CCOC(=O)C1CC1C(C=C1C=2C=C(Br)C=CC=2)=NC2N1NC(SC)C2C#N PRNZPLBZGJVWKJ-UHFFFAOYSA-N 0.000 claims description 2
• AXMLXRIRHBZXDD-UHFFFAOYSA-N ethyl 2-hydroxy-7-(4-hydroxyphenyl)-6-methyl-3-phenyldiazenyl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylate Chemical compound OC1NN2C(C=3C=CC(O)=CC=3)=C(C)C(C(=O)OCC)=NC2C1N=NC1=CC=CC=C1 AXMLXRIRHBZXDD-UHFFFAOYSA-N 0.000 claims description 2
• JYUSNBPLPCLXRC-UHFFFAOYSA-N ethyl 3-bromo-7-(3,4-dimethoxyphenyl)-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylate Chemical compound C=1C(C(=O)OCC)=NC2C(Br)CNN2C=1C1=CC=C(OC)C(OC)=C1 JYUSNBPLPCLXRC-UHFFFAOYSA-N 0.000 claims description 2
• KNIPECZYKOHLLK-UHFFFAOYSA-N ethyl 3-bromo-7-(4-hydroxyphenyl)-6-methyl-2-phenyl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylate Chemical compound CC=1C(C(=O)OCC)=NC2C(Br)C(C=3C=CC=CC=3)NN2C=1C1=CC=C(O)C=C1 KNIPECZYKOHLLK-UHFFFAOYSA-N 0.000 claims description 2
• LUARVMRUAJRPHZ-UHFFFAOYSA-N ethyl 3-bromo-7-(4-methoxyphenyl)-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylate Chemical compound C=1C(C(=O)OCC)=NC2C(Br)CNN2C=1C1=CC=C(OC)C=C1 LUARVMRUAJRPHZ-UHFFFAOYSA-N 0.000 claims description 2
• GSAIQNQOXPFYAP-UHFFFAOYSA-N ethyl 3-cyano-2-methylsulfanyl-7-(2,3,4-trimethoxyphenyl)-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylate Chemical compound C=1C(C(=O)OCC)=NC2C(C#N)C(SC)NN2C=1C1=CC=C(OC)C(OC)=C1OC GSAIQNQOXPFYAP-UHFFFAOYSA-N 0.000 claims description 2
• YOQQUGCRJIOBRW-UHFFFAOYSA-N ethyl 3-cyano-2-methylsulfanyl-7-phenylsulfanyl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylate Chemical compound C=1C(C(=O)OCC)=NC2C(C#N)C(SC)NN2C=1SC1=CC=CC=C1 YOQQUGCRJIOBRW-UHFFFAOYSA-N 0.000 claims description 2
• YWYPITKRNVEOKL-UHFFFAOYSA-N ethyl 3-cyano-7-(2,4-dimethylphenyl)-2-methylsulfanyl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-5-carboxylate Chemical compound C=1C(C(=O)OCC)=NC2C(C#N)C(SC)NN2C=1C1=CC=C(C)C=C1C YWYPITKRNVEOKL-UHFFFAOYSA-N 0.000 claims description 2
• GOFADMXUQVOZFL-UHFFFAOYSA-N ethyl 5-(2-hydroxy-3-methoxyphenyl)-7-phenylsulfanyl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound CCOC(=O)C1CNN2C1N=C(C=1C(=C(OC)C=CC=1)O)C=C2SC1=CC=CC=C1 GOFADMXUQVOZFL-UHFFFAOYSA-N 0.000 claims description 2
• CUZIBEIXINEFSV-UHFFFAOYSA-N ethyl 5-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-6-methyl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound CCOC(=O)C1CNN2C1N=C(C=1C=C(OC)C(O)=CC=1)C(C)=C2C1=CC=C(O)C=C1 CUZIBEIXINEFSV-UHFFFAOYSA-N 0.000 claims description 2
• RWJDXBSBYOYYIO-UHFFFAOYSA-N ethyl 5-(4-hydroxy-3-methoxyphenyl)-7-phenylsulfanyl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound CCOC(=O)C1CNN2C1N=C(C=1C=C(OC)C(O)=CC=1)C=C2SC1=CC=CC=C1 RWJDXBSBYOYYIO-UHFFFAOYSA-N 0.000 claims description 2
• ONFXINQPVJQPRN-UHFFFAOYSA-N ethyl 5-benzoyl-7-(2,4-dimethylphenyl)-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound CCOC(=O)C1CNN2C1N=C(C(=O)C=1C=CC=CC=1)C=C2C1=CC=C(C)C=C1C ONFXINQPVJQPRN-UHFFFAOYSA-N 0.000 claims description 2
• QSJDZVJOFBHAAR-UHFFFAOYSA-N ethyl 5-benzoyl-7-(3,4-dimethoxyphenyl)-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound CCOC(=O)C1CNN2C1N=C(C(=O)C=1C=CC=CC=1)C=C2C1=CC=C(OC)C(OC)=C1 QSJDZVJOFBHAAR-UHFFFAOYSA-N 0.000 claims description 2
• GVGCDHFBWGHAPY-UHFFFAOYSA-N ethyl 5-benzoyl-7-(3-fluorophenyl)-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound CCOC(=O)C1CNN2C1N=C(C(=O)C=1C=CC=CC=1)C=C2C1=CC=CC(F)=C1 GVGCDHFBWGHAPY-UHFFFAOYSA-N 0.000 claims description 2
• WRQMSJDKWUCEED-UHFFFAOYSA-N ethyl 5-benzoyl-7-(4-methoxyphenyl)-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound CCOC(=O)C1CNN2C1N=C(C(=O)C=1C=CC=CC=1)C=C2C1=CC=C(OC)C=C1 WRQMSJDKWUCEED-UHFFFAOYSA-N 0.000 claims description 2
• NWIOPEMNNUSOHQ-UHFFFAOYSA-N ethyl 5-cyclohexyl-7-(2-hydroxyethoxy)-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound CCOC(=O)C1CNN(C(=C2)OCCO)C1N=C2C1CCCCC1 NWIOPEMNNUSOHQ-UHFFFAOYSA-N 0.000 claims description 2
• IQHCBLYGESICGG-UHFFFAOYSA-N ethyl 5-cyclohexyl-7-cyclohexyloxy-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound CCOC(=O)C1CNN2C1N=C(C1CCCCC1)C=C2OC1CCCCC1 IQHCBLYGESICGG-UHFFFAOYSA-N 0.000 claims description 2
• GDRJAPAXJNSCGJ-UHFFFAOYSA-N ethyl 5-cyclopropyl-7-(2-hydroxyethoxy)-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound CCOC(=O)C1CNN(C(=C2)OCCO)C1N=C2C1CC1 GDRJAPAXJNSCGJ-UHFFFAOYSA-N 0.000 claims description 2
• PQYUYABCPZUJNW-UHFFFAOYSA-N ethyl 7-(2,4-dimethylphenyl)-5-(2-ethoxycarbonylcyclopropyl)-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound CCOC(=O)C1CC1C(C=C1C=2C(=CC(C)=CC=2)C)=NC2N1NCC2C(=O)OCC PQYUYABCPZUJNW-UHFFFAOYSA-N 0.000 claims description 2
• ZZWOPFJQPAGZPW-UHFFFAOYSA-N ethyl 7-(2,4-dimethylphenyl)-5-(5-nitrofuran-2-yl)-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound CCOC(=O)C1CNN2C1N=C(C=1OC(=CC=1)[N+]([O-])=O)C=C2C1=CC=C(C)C=C1C ZZWOPFJQPAGZPW-UHFFFAOYSA-N 0.000 claims description 2
• RBZFBMPHPJAPEF-UHFFFAOYSA-N ethyl 7-(2,4-dimethylphenyl)-5-pyridin-2-yl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound CCOC(=O)C1CNN2C1N=C(C=1N=CC=CC=1)C=C2C1=CC=C(C)C=C1C RBZFBMPHPJAPEF-UHFFFAOYSA-N 0.000 claims description 2
• NXZMNSLHIKYAQQ-UHFFFAOYSA-N ethyl 7-(3,4-dimethoxyphenyl)-5-(4-phenoxyphenyl)-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound CCOC(=O)C1CNN2C1N=C(C=1C=CC(OC=3C=CC=CC=3)=CC=1)C=C2C1=CC=C(OC)C(OC)=C1 NXZMNSLHIKYAQQ-UHFFFAOYSA-N 0.000 claims description 2
• POKUPSSLFPDTHI-UHFFFAOYSA-N ethyl 7-(3,4-dimethoxyphenyl)-5-(5-nitrothiophen-2-yl)-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound CCOC(=O)C1CNN2C1N=C(C=1SC(=CC=1)[N+]([O-])=O)C=C2C1=CC=C(OC)C(OC)=C1 POKUPSSLFPDTHI-UHFFFAOYSA-N 0.000 claims description 2
• BHNDPXJAJWQVKR-UHFFFAOYSA-N ethyl 7-(3,4-dimethoxyphenyl)-5-pyridin-2-yl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound N1C2=C(C(=O)OCC)C=NN2C(C=2C=C(OC)C(OC)=CC=2)CC1C1=CC=CC=N1 BHNDPXJAJWQVKR-UHFFFAOYSA-N 0.000 claims description 2
• GCICGPCNDJRVCD-UHFFFAOYSA-N ethyl 7-(4-chlorophenyl)-5-(2-hydroxy-3-methoxyphenyl)-7-methyl-2,3,3a,4-tetrahydro-1h-pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound CCOC(=O)C1CNN2C1NC(C=1C(=C(OC)C=CC=1)O)=CC2(C)C1=CC=C(Cl)C=C1 GCICGPCNDJRVCD-UHFFFAOYSA-N 0.000 claims description 2
• LKELDFNROFQYSO-UHFFFAOYSA-N ethyl 7-(4-methoxyphenyl)-5-(5-nitrothiophen-2-yl)-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound CCOC(=O)C1CNN2C1N=C(C=1SC(=CC=1)[N+]([O-])=O)C=C2C1=CC=C(OC)C=C1 LKELDFNROFQYSO-UHFFFAOYSA-N 0.000 claims description 2
• JWHQGCULFXMFFM-UHFFFAOYSA-N ethyl 7-cyclohexyl-3-oxa-1,8,12-triazatricyclo[7.3.0.02,6]dodeca-8,11-diene-10-carboxylate Chemical compound N1=C2C(C(=O)OCC)C=NN2C2OCCC2C1C1CCCCC1 JWHQGCULFXMFFM-UHFFFAOYSA-N 0.000 claims description 2
• FKQXAXCVBTVUDR-UHFFFAOYSA-N ethyl 7-cyclohexyloxy-5-cyclopropyl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound CCOC(=O)C1CNN2C1N=C(C1CC1)C=C2OC1CCCCC1 FKQXAXCVBTVUDR-UHFFFAOYSA-N 0.000 claims description 2
• SPSMBUPGPMHVGS-UHFFFAOYSA-N ethyl 7-cyclopropyl-3-oxa-1,8,12-triazatricyclo[7.3.0.02,6]dodeca-8,11-diene-10-carboxylate Chemical compound N1=C2C(C(=O)OCC)C=NN2C2OCCC2C1C1CC1 SPSMBUPGPMHVGS-UHFFFAOYSA-N 0.000 claims description 2
• SWXOQGDHLOCARI-UHFFFAOYSA-N ethyl 7-cyclopropyl-3-oxa-1,8,12-triazatricyclo[7.3.0.02,6]dodeca-9,11-diene-10-carboxylate Chemical compound N1C2=C(C(=O)OCC)C=NN2C2OCCC2C1C1CC1 SWXOQGDHLOCARI-UHFFFAOYSA-N 0.000 claims description 2
• UMMBKXVIDBFKJH-UHFFFAOYSA-N ethyl 7-phenylsulfanyl-5-pyridin-2-yl-3,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound N1=C2C(C(=O)OCC)C=NN2C(SC=2C=CC=CC=2)CC1C1=CC=CC=N1 UMMBKXVIDBFKJH-UHFFFAOYSA-N 0.000 claims description 2
• ANWZLSLJQBOCNK-UHFFFAOYSA-N ethyl 8-(4-hydroxy-3-methoxyphenyl)-2,3,7-triazatetracyclo[7.7.0.02,6.011,16]hexadeca-3,5,11,13,15-pentaene-5-carboxylate Chemical compound N1C2=C(C(=O)OCC)C=NN2C(C2=CC=CC=C2C2)C2C1C1=CC=C(O)C(OC)=C1 ANWZLSLJQBOCNK-UHFFFAOYSA-N 0.000 claims description 2
• UIESCIGUKUTARD-UHFFFAOYSA-N ethyl 8-(4-hydroxy-3-methoxyphenyl)-2,3,7-triazatetracyclo[7.7.0.02,6.011,16]hexadeca-3,6,11,13,15-pentaene-5-carboxylate Chemical compound N1=C2C(C(=O)OCC)C=NN2C(C2=CC=CC=C2C2)C2C1C1=CC=C(O)C(OC)=C1 UIESCIGUKUTARD-UHFFFAOYSA-N 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• 238000005580 one pot reaction Methods 0.000 claims description 2
• 230000035484 reaction time Effects 0.000 claims description 2
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 24
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 23
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 19
• 241000525154 Micrathena beta Species 0.000 claims 14
• 101150007969 ADORA1 gene Proteins 0.000 claims 11
• 208000027866 inflammatory disease Diseases 0.000 claims 8
• 230000000638 stimulation Effects 0.000 claims 8
• DVFIRCGWBCEMRO-UHFFFAOYSA-N ethyl 11-tert-butyl-1,8,12-triazatricyclo[7.3.0.02,6]dodeca-3,8,11-triene-7-carboxylate Chemical compound CCOC(=O)C1N=C2CC(C(C)(C)C)=NN2C2C=CCC12 DVFIRCGWBCEMRO-UHFFFAOYSA-N 0.000 claims 2
• QIZGCOGNAZZPHF-UHFFFAOYSA-N 11-cyclopropyl-12,16,17-triazatetracyclo[8.7.0.02,7.013,17]heptadeca-2,4,6,12,15-pentaene-14-carbonitrile Chemical compound N1=C2C(C#N)C=NN2C(C2=CC=CC=C2CC2)C2C1C1CC1 QIZGCOGNAZZPHF-UHFFFAOYSA-N 0.000 claims 1
• FYFQRPMJHBIASN-UHFFFAOYSA-N 2,5-ditert-butyl-7-(3,4-dimethoxyphenyl)-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidine Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(C(C)(C)C)=NC2N1NC(C(C)(C)C)C2 FYFQRPMJHBIASN-UHFFFAOYSA-N 0.000 claims 1
• GDMMHFDAAJPEGF-UHFFFAOYSA-N 2-[(2-tert-butyl-5-cyclopropyl-1,2,3,3a-tetrahydropyrazolo[1,5-a]pyrimidin-7-yl)oxy]ethanol Chemical compound C1=C(OCCO)N2NC(C(C)(C)C)CC2N=C1C1CC1 GDMMHFDAAJPEGF-UHFFFAOYSA-N 0.000 claims 1
• RRUGGIXQTXGKHI-UHFFFAOYSA-N 2-methyl-5,7-diphenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine Chemical compound N12N=C(C)C=C2NC(C=2C=CC=CC=2)CC1C1=CC=CC=C1 RRUGGIXQTXGKHI-UHFFFAOYSA-N 0.000 claims 1
• HBBDYBGRGJFMAM-UHFFFAOYSA-N 2-methyl-5,7-dipropyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile Chemical compound N1C(CCC)CC(CCC)N2N=C(C)C(C#N)=C21 HBBDYBGRGJFMAM-UHFFFAOYSA-N 0.000 claims 1
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