ZA200206077B - Adenosine receptor modulators. - Google Patents
Adenosine receptor modulators. Download PDFInfo
- Publication number
- ZA200206077B ZA200206077B ZA200206077A ZA200206077A ZA200206077B ZA 200206077 B ZA200206077 B ZA 200206077B ZA 200206077 A ZA200206077 A ZA 200206077A ZA 200206077 A ZA200206077 A ZA 200206077A ZA 200206077 B ZA200206077 B ZA 200206077B
- Authority
- ZA
- South Africa
- Prior art keywords
- amino
- furan
- pyrimidine
- carbonitrile
- pyridin
- Prior art date
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- 102000009346 Adenosine receptors Human genes 0.000 title claims description 10
- 108050000203 Adenosine receptors Proteins 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 166
- 125000000217 alkyl group Chemical group 0.000 claims description 139
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 95
- -1 CFs Chemical group 0.000 claims description 79
- 229910052736 halogen Inorganic materials 0.000 claims description 78
- 150000002367 halogens Chemical class 0.000 claims description 76
- 125000003545 alkoxy group Chemical group 0.000 claims description 57
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 57
- 229910052757 nitrogen Inorganic materials 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 30
- 125000005605 benzo group Chemical group 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 102000005962 receptors Human genes 0.000 claims description 26
- 108020003175 receptors Proteins 0.000 claims description 26
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 25
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 25
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 25
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 24
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 24
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 150000002431 hydrogen Chemical group 0.000 claims description 16
- 239000001961 anticonvulsive agent Substances 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 206010021143 Hypoxia Diseases 0.000 claims description 9
- 208000018737 Parkinson disease Diseases 0.000 claims description 9
- 230000007954 hypoxia Effects 0.000 claims description 9
- 208000028867 ischemia Diseases 0.000 claims description 9
- 230000004112 neuroprotection Effects 0.000 claims description 9
- 206010010904 Convulsion Diseases 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 208000026935 allergic disease Diseases 0.000 claims description 8
- 208000006673 asthma Diseases 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 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 7
- 208000024827 Alzheimer disease Diseases 0.000 claims description 7
- 208000019901 Anxiety disease Diseases 0.000 claims description 7
- 208000002193 Pain Diseases 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 229940125681 anticonvulsant agent Drugs 0.000 claims description 7
- 239000000164 antipsychotic agent Substances 0.000 claims description 7
- 229940005529 antipsychotics Drugs 0.000 claims description 7
- 230000036506 anxiety Effects 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 229940035363 muscle relaxants Drugs 0.000 claims description 7
- 239000003158 myorelaxant agent Substances 0.000 claims description 7
- 230000036407 pain Effects 0.000 claims description 7
- 230000029058 respiratory gaseous exchange Effects 0.000 claims description 7
- 201000000980 schizophrenia Diseases 0.000 claims description 7
- 201000009032 substance abuse Diseases 0.000 claims description 7
- 231100000736 substance abuse Toxicity 0.000 claims description 7
- 208000011117 substance-related disease Diseases 0.000 claims description 7
- 206010039897 Sedation Diseases 0.000 claims description 6
- 230000003556 anti-epileptic effect Effects 0.000 claims description 6
- 229960003965 antiepileptics Drugs 0.000 claims description 6
- 230000006735 deficit Effects 0.000 claims description 6
- 230000036280 sedation Effects 0.000 claims description 6
- 230000001225 therapeutic effect Effects 0.000 claims description 6
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
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- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- 230000006742 locomotor activity Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 102000006240 membrane receptors Human genes 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 230000008062 neuronal firing Effects 0.000 description 1
- 230000003957 neurotransmitter release Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 108020001213 potassium channel Proteins 0.000 description 1
- 210000000063 presynaptic terminal Anatomy 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 239000000296 purinergic P1 receptor antagonist Substances 0.000 description 1
- AHRQYOSAXZQCIG-UHFFFAOYSA-N pyrimidine-5-carbonitrile Chemical compound N#CC1=C=NC=N[CH]1 AHRQYOSAXZQCIG-UHFFFAOYSA-N 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 230000008327 renal blood flow Effects 0.000 description 1
- 239000003169 respiratory stimulant agent Substances 0.000 description 1
- 229940066293 respiratory stimulants Drugs 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
Classifications
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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