ZA200606551B - Additional heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists - Google Patents
Additional heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists Download PDFInfo
- Publication number
- ZA200606551B ZA200606551B ZA200606551A ZA200606551A ZA200606551B ZA 200606551 B ZA200606551 B ZA 200606551B ZA 200606551 A ZA200606551 A ZA 200606551A ZA 200606551 A ZA200606551 A ZA 200606551A ZA 200606551 B ZA200606551 B ZA 200606551B
- Authority
- ZA
- South Africa
- Prior art keywords
- disorder
- disorders
- group
- chiral
- pain
- Prior art date
Links
- 108010010914 Metabotropic glutamate receptors Proteins 0.000 title claims description 31
- 102000016193 Metabotropic glutamate receptors Human genes 0.000 title claims description 31
- 239000003825 glutamate receptor antagonist Substances 0.000 title description 2
- 125000004585 polycyclic heterocycle group Chemical group 0.000 title 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 32
- 208000035475 disorder Diseases 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 28
- 208000002193 Pain Diseases 0.000 claims description 16
- 102000005962 receptors Human genes 0.000 claims description 16
- 108020003175 receptors Proteins 0.000 claims description 16
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 8
- 208000012902 Nervous system disease Diseases 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 230000036407 pain Effects 0.000 claims description 6
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 208000000094 Chronic Pain Diseases 0.000 claims description 5
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 5
- 230000001154 acute effect Effects 0.000 claims description 5
- 208000005298 acute pain Diseases 0.000 claims description 5
- 206010015037 epilepsy Diseases 0.000 claims description 5
- 208000020016 psychiatric disease Diseases 0.000 claims description 5
- 230000001684 chronic effect Effects 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- 206010019196 Head injury Diseases 0.000 claims description 3
- 208000013016 Hypoglycemia Diseases 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 230000002218 hypoglycaemic effect Effects 0.000 claims description 3
- 208000037906 ischaemic injury Diseases 0.000 claims description 3
- 208000019695 Migraine disease Diseases 0.000 claims 6
- 206010027599 migraine Diseases 0.000 claims 6
- 208000019901 Anxiety disease Diseases 0.000 claims 4
- 230000036506 anxiety Effects 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 201000000980 schizophrenia Diseases 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 3
- 208000030507 AIDS Diseases 0.000 claims 2
- 208000004998 Abdominal Pain Diseases 0.000 claims 2
- 206010002383 Angina Pectoris Diseases 0.000 claims 2
- 206010003805 Autism Diseases 0.000 claims 2
- 208000020706 Autistic disease Diseases 0.000 claims 2
- 208000008035 Back Pain Diseases 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000002881 Colic Diseases 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- 206010012335 Dependence Diseases 0.000 claims 2
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 2
- 201000010374 Down Syndrome Diseases 0.000 claims 2
- 208000010412 Glaucoma Diseases 0.000 claims 2
- 201000005569 Gout Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 206010065390 Inflammatory pain Diseases 0.000 claims 2
- 208000008930 Low Back Pain Diseases 0.000 claims 2
- 208000036626 Mental retardation Diseases 0.000 claims 2
- 208000029726 Neurodevelopmental disease Diseases 0.000 claims 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 206010036376 Postherpetic Neuralgia Diseases 0.000 claims 2
- 208000004550 Postoperative Pain Diseases 0.000 claims 2
- 206010039966 Senile dementia Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 206010044688 Trisomy 21 Diseases 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 238000002512 chemotherapy Methods 0.000 claims 2
- 235000019788 craving Nutrition 0.000 claims 2
- 208000010643 digestive system disease Diseases 0.000 claims 2
- 208000018685 gastrointestinal system disease Diseases 0.000 claims 2
- 230000005906 menstruation Effects 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 230000002981 neuropathic effect Effects 0.000 claims 2
- 208000021722 neuropathic pain Diseases 0.000 claims 2
- 201000001119 neuropathy Diseases 0.000 claims 2
- 230000007823 neuropathy Effects 0.000 claims 2
- 206010044652 trigeminal neuralgia Diseases 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- -1 Co-salkylcyano Chemical group 0.000 description 44
- 229910052799 carbon Inorganic materials 0.000 description 42
- 229910052757 nitrogen Inorganic materials 0.000 description 40
- 229910052760 oxygen Inorganic materials 0.000 description 40
- 125000000217 alkyl group Chemical group 0.000 description 37
- 229910052717 sulfur Inorganic materials 0.000 description 33
- 125000004429 atom Chemical group 0.000 description 30
- 229910052739 hydrogen Inorganic materials 0.000 description 30
- 239000001257 hydrogen Substances 0.000 description 30
- 125000005843 halogen group Chemical group 0.000 description 28
- 150000002431 hydrogen Chemical class 0.000 description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 20
- 230000004913 activation Effects 0.000 description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- 125000003342 alkenyl group Chemical group 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 9
- 125000002541 furyl group Chemical group 0.000 description 8
- 125000004076 pyridyl group Chemical group 0.000 description 8
- 125000000168 pyrrolyl group Chemical group 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 125000001072 heteroaryl group Chemical group 0.000 description 7
- 125000000335 thiazolyl group Chemical group 0.000 description 7
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 210000003169 central nervous system Anatomy 0.000 description 6
- 210000002569 neuron Anatomy 0.000 description 6
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 230000005284 excitation Effects 0.000 description 5
- 229930195712 glutamate Natural products 0.000 description 5
- 125000002883 imidazolyl group Chemical group 0.000 description 5
- 210000000111 lower esophageal sphincter Anatomy 0.000 description 5
- 125000002098 pyridazinyl group Chemical group 0.000 description 5
- 229930192474 thiophene Natural products 0.000 description 5
- 125000001425 triazolyl group Chemical group 0.000 description 5
- 208000025966 Neurological disease Diseases 0.000 description 4
- 239000000556 agonist Substances 0.000 description 4
- 125000005872 benzooxazolyl group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 description 4
- 125000004043 oxo group Chemical group O=* 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- 125000002837 carbocyclic group Chemical group 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 125000005945 imidazopyridyl group Chemical group 0.000 description 3
- 230000003834 intracellular effect Effects 0.000 description 3
- 125000000842 isoxazolyl group Chemical group 0.000 description 3
- 238000001783 near-resonance Rayleigh scattering spectroscopy Methods 0.000 description 3
- 230000001537 neural effect Effects 0.000 description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 3
- 125000002971 oxazolyl group Chemical group 0.000 description 3
- 230000001242 postsynaptic effect Effects 0.000 description 3
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 3
- 125000003226 pyrazolyl group Chemical group 0.000 description 3
- 125000005494 pyridonyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 125000003831 tetrazolyl group Chemical group 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- 102000014384 Type C Phospholipases Human genes 0.000 description 2
- 108010079194 Type C Phospholipases Proteins 0.000 description 2
- 125000005213 alkyl heteroaryl group Chemical group 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- ZOOGRGPOEVQQDX-KHLHZJAASA-N cyclic guanosine monophosphate Chemical compound C([C@H]1O2)O[P@](O)(=O)O[C@@H]1[C@H](O)[C@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-KHLHZJAASA-N 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 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 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 210000003238 esophagus Anatomy 0.000 description 2
- 230000027119 gastric acid secretion Effects 0.000 description 2
- 125000002632 imidazolidinyl group Chemical group 0.000 description 2
- 125000002636 imidazolinyl group Chemical group 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000002757 morpholinyl group Chemical group 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000000926 neurological effect Effects 0.000 description 2
- 125000006574 non-aromatic ring group Chemical group 0.000 description 2
- 230000007170 pathology Effects 0.000 description 2
- 230000001991 pathophysiological effect Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 150000003906 phosphoinositides Chemical class 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 125000004928 piperidonyl group Chemical group 0.000 description 2
- 125000005936 piperidyl group Chemical group 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000003518 presynaptic effect Effects 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 2
- 125000002755 pyrazolinyl group Chemical group 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 125000001422 pyrrolinyl group Chemical group 0.000 description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 2
- 230000001052 transient effect Effects 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 description 1
- JJDNUCCDEXEKEM-UHFFFAOYSA-N 2-[5-(2,4-dibromophenyl)furan-2-yl]-5-[2-[5-[5-(2,4-dibromophenyl)furan-2-yl]-1,3,4-oxadiazol-2-yl]ethyl]-1,3,4-oxadiazole Chemical compound BrC1=CC(Br)=CC=C1C1=CC=C(C=2OC(CCC=3OC(=NN=3)C=3OC(=CC=3)C=3C(=CC(Br)=CC=3)Br)=NN=2)O1 JJDNUCCDEXEKEM-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- BFRGHHKUZKLBQA-UHFFFAOYSA-N 3-[5-[2-[5-(3-aminophenyl)-1,3,4-oxadiazol-2-yl]ethyl]-1,3,4-oxadiazol-2-yl]aniline Chemical compound NC1=CC=CC(C=2OC(CCC=3OC(=NN=3)C=3C=C(N)C=CC=3)=NN=2)=C1 BFRGHHKUZKLBQA-UHFFFAOYSA-N 0.000 description 1
- AJRGDQWFWJDYDP-UHFFFAOYSA-N 3-chloro-1,2-oxazole Chemical compound ClC=1C=CON=1 AJRGDQWFWJDYDP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102000000844 Cell Surface Receptors Human genes 0.000 description 1
- 108010001857 Cell Surface Receptors Proteins 0.000 description 1
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
- 108010078321 Guanylate Cyclase Proteins 0.000 description 1
- 102000014469 Guanylate cyclase Human genes 0.000 description 1
- 108090000862 Ion Channels Proteins 0.000 description 1
- 102000004310 Ion Channels Human genes 0.000 description 1
- 102000006541 Ionotropic Glutamate Receptors Human genes 0.000 description 1
- 108010008812 Ionotropic Glutamate Receptors Proteins 0.000 description 1
- 102100036834 Metabotropic glutamate receptor 1 Human genes 0.000 description 1
- 102100037636 Metabotropic glutamate receptor 8 Human genes 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 102000011420 Phospholipase D Human genes 0.000 description 1
- 108090000553 Phospholipase D Proteins 0.000 description 1
- 102000015439 Phospholipases Human genes 0.000 description 1
- 108010064785 Phospholipases Proteins 0.000 description 1
- 208000027520 Somatoform disease Diseases 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 102000030621 adenylate cyclase Human genes 0.000 description 1
- 108060000200 adenylate cyclase Proteins 0.000 description 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical group 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 230000001640 apoptogenic effect Effects 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 210000001638 cerebellum Anatomy 0.000 description 1
- 210000003710 cerebral cortex Anatomy 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 125000006006 difluoroethoxy group Chemical group 0.000 description 1
- 125000006001 difluoroethyl group Chemical group 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003596 drug target Substances 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000002964 excitative effect Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 230000000971 hippocampal effect Effects 0.000 description 1
- 210000001320 hippocampus Anatomy 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 230000001057 ionotropic effect Effects 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
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 230000020796 long term synaptic depression Effects 0.000 description 1
- 230000027928 long-term synaptic potentiation Effects 0.000 description 1
- 108010038448 metabotropic glutamate receptor 8 Proteins 0.000 description 1
- 108010014719 metabotropic glutamate receptor type 1 Proteins 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000010369 molecular cloning Methods 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 230000007472 neurodevelopment Effects 0.000 description 1
- 230000016273 neuron death Effects 0.000 description 1
- 239000004090 neuroprotective agent Substances 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 230000003957 neurotransmitter release Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 208000027753 pain disease Diseases 0.000 description 1
- 230000035778 pathophysiological process Effects 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 238000001050 pharmacotherapy Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 230000004044 response Effects 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
- 230000020341 sensory perception of pain Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 230000003956 synaptic plasticity Effects 0.000 description 1
- 230000005062 synaptic transmission Effects 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 210000001103 thalamus Anatomy 0.000 description 1
- 208000016752 upper digestive tract disease Diseases 0.000 description 1
- 230000004462 vestibulo-ocular reflex Effects 0.000 description 1
- 230000031836 visual learning Effects 0.000 description 1
- 230000002618 waking effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- 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
- C07D413/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- 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
- C07D413/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Ophthalmology & Optometry (AREA)
- Endocrinology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Obesity (AREA)
- Psychology (AREA)
- Hematology (AREA)
- Addiction (AREA)
- Immunology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60896004P | 2004-02-18 | 2004-02-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200606551B true ZA200606551B (en) | 2007-11-28 |
Family
ID=35447957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200606551A ZA200606551B (en) | 2004-02-18 | 2006-08-07 | Additional heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
Country Status (26)
| Country | Link |
|---|---|
| US (6) | US7585881B2 (es) |
| EP (2) | EP1723144B1 (es) |
| JP (1) | JP4912157B2 (es) |
| CN (2) | CN1984907A (es) |
| AT (1) | ATE483706T1 (es) |
| AU (1) | AU2005270208A1 (es) |
| BR (1) | BRPI0507497A (es) |
| CA (1) | CA2555566A1 (es) |
| CY (1) | CY1110965T1 (es) |
| DE (1) | DE602005023963D1 (es) |
| DK (1) | DK1723144T3 (es) |
| ES (1) | ES2352110T3 (es) |
| HR (1) | HRP20100654T1 (es) |
| IL (1) | IL177394A0 (es) |
| NO (1) | NO20063599L (es) |
| NZ (1) | NZ548954A (es) |
| PL (1) | PL1723144T3 (es) |
| PT (1) | PT1723144E (es) |
| RS (1) | RS51516B (es) |
| RU (1) | RU2370495C2 (es) |
| SG (1) | SG146657A1 (es) |
| SI (1) | SI1723144T1 (es) |
| UA (1) | UA84318C2 (es) |
| UY (1) | UY28766A1 (es) |
| WO (1) | WO2006014185A1 (es) |
| ZA (1) | ZA200606551B (es) |
Families Citing this family (77)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL166510A0 (en) * | 2002-08-09 | 2006-01-15 | Nps Pharma Inc | 1,2,4"oxadiazole as modulators of metabotropic glutamate receptor-5 |
| US7585881B2 (en) * | 2004-02-18 | 2009-09-08 | Astrazeneca Ab | Additional heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| CN1942457A (zh) * | 2004-04-20 | 2007-04-04 | 默克公司 | 作为β－促分泌酶抑制剂用于阿尔茨海默氏病的治疗中的1,3,5－取代的苯基衍生化合物 |
| JPWO2006080533A1 (ja) * | 2005-01-31 | 2008-06-19 | 持田製薬株式会社 | ３−アミノ−１，２，４−トリアゾール誘導体 |
| UY29796A1 (es) * | 2005-09-29 | 2007-04-30 | Astrazeneca Ab | Nuevos compuestos para el tratamiento de trastornos neurológicos, psiquiátricos o del dolor |
| TW200811157A (en) | 2006-05-05 | 2008-03-01 | Astrazeneca Ab | mGluR5 modulators I |
| TW200811179A (en) * | 2006-05-05 | 2008-03-01 | Astrazeneca Ab | mGluR5 modulators VI |
| TW200808800A (en) * | 2006-05-05 | 2008-02-16 | Astrazeneca Ab | MGluR5 modulators V |
| JP5448164B2 (ja) * | 2006-07-28 | 2014-03-19 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｂ２受容体を変調する化合物 |
| TW200821305A (en) * | 2006-10-05 | 2008-05-16 | Astrazeneca Ab | MGluR5 modulators |
| AU2008257559B2 (en) | 2007-05-25 | 2013-10-10 | AbbVie Deutschland GmbH & Co. KG | Heterocyclic compounds as positive modulators of metabotropic glutamate receptor 2 (MGLU2 receptor) |
| CA2696016A1 (en) | 2007-07-13 | 2009-01-22 | Addex Pharma S.A. | Novel heteroaromatic derivatives and their use as positive allosteric modulators of metabotropic glutamate receptors |
| CL2008003085A1 (es) * | 2007-10-19 | 2009-10-09 | Astrazeneca Ab | Compuestos derivados de 4-metil-5-[1-(2-(3-metilfenil)-2h-tetrazol-5-il)etoxi]-4h-1,2,4-triazol-3-il moduladores del receptor mglur5; composiciones farmceuticas que los contienen; compuestos intermediarios; y su uso en la preparacion de un medicamento util en el tratamiento de desordenes neurologicos, psiquiatricos o gastrointestinales. |
| WO2009054785A1 (en) * | 2007-10-26 | 2009-04-30 | Astrazeneca Ab | 1,2,4-triazole ether derivatives as modulators of mglur5 |
| WO2009054786A1 (en) * | 2007-10-26 | 2009-04-30 | Astrazeneca Ab | 1,2,4-triazole aryl n-oxides derivatives as modulators of mglur5 |
| WO2009061652A1 (en) * | 2007-11-07 | 2009-05-14 | Boehringer Ingelheim International Gmbh | Compounds which modulate the cb2 receptor |
| EP2255009A4 (en) * | 2008-03-03 | 2011-08-10 | Stiefel Laboratories | PROCESSES FOR THE PREPARATION OF ENANTIOMERICALLY PURE DIOL AND DIOXOLANE COMPOUNDS |
| DK2291080T3 (en) | 2008-05-14 | 2015-12-07 | Scripps Research Inst | Novel modulator of sphingosinphosphatreceptorer |
| WO2010005782A1 (en) * | 2008-07-10 | 2010-01-14 | Boehringer Ingelheim International Gmbh | Sulfone compounds which modulate the cb2 receptor |
| TW201011016A (en) * | 2008-08-12 | 2010-03-16 | Astrazeneca Ab | New compounds 501 |
| EP2323658A4 (en) * | 2008-08-12 | 2011-10-05 | Astrazeneca Ab | NEW CRYSTALLINE FORM OF (5- {(IR) -1- [5- (3-CHLOROPHENYL) ISOXAZOL-3-YL] ETHOXY} -4-METHYL-4H-L, 2, 4-TRIAZOL-3-YL) - PYRIDINE |
| AP2011005674A0 (en) * | 2008-09-25 | 2011-04-30 | Boehringer Ingelheim Int | Sulfonyl compounds which selectively modulate the CB2 receptor. |
| WO2010071559A1 (en) * | 2008-12-18 | 2010-06-24 | Astrazeneca Ab | Processes for the manufacture of 3-{4-methyl-5- [ (ir) -1- (2- (3-methylphenyl) -2h-tetrazol-5-yl) -ethoxy] -4h- [1,2, 4] triazol-3-yl} -pyridine, 4-methyl-3-methylthio-5- (3- pyridyl)-l,2,4-triazole, and (ir) -1- [2- (3-methylphenyl) -2h- tetrazol-5-yl] ethanol |
| US8349852B2 (en) | 2009-01-13 | 2013-01-08 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
| WO2010096371A2 (en) | 2009-02-18 | 2010-08-26 | Boehringer Ingelheim International Gmbh | Heterocyclic compounds which modulate the cb2 receptor |
| US20120029190A1 (en) * | 2009-04-03 | 2012-02-02 | Douglas Burdi | Compounds for treating disorders mediated by metabotropic glutamate receptor 5, and methods of use thereof |
| US20100273805A1 (en) * | 2009-04-23 | 2010-10-28 | Astrazeneca Ab | Sulphide bridged derivatives as modulators of mglur5 733 |
| CA2764339A1 (en) | 2009-06-05 | 2010-12-09 | Oslo University Hospital Hf | Azole derivatives as wtn pathway inhibitors |
| US8299103B2 (en) | 2009-06-15 | 2012-10-30 | Boehringer Ingelheim International Gmbh | Compounds which selectively modulate the CB2 receptor |
| US8383615B2 (en) | 2009-06-16 | 2013-02-26 | Boehringer Ingelheim International Gmbh | Azetidine 2-carboxamide derivatives which modulate the CB2 receptor |
| US8383651B2 (en) * | 2009-09-22 | 2013-02-26 | Boehringer Ingelheim International Gmbh | Compounds which selectively modulate the CB2 receptor |
| WO2011060389A1 (en) | 2009-11-13 | 2011-05-19 | Receptos, Inc. | Sphingosine 1 phosphate receptor modulators and methods of chiral synthesis |
| RS61829B1 (sr) * | 2009-11-13 | 2021-06-30 | Receptos Llc | Selektivni modulatori receptora sfingozin 1 fosfata i metode hiralne sinteze |
| KR101771755B1 (ko) * | 2009-11-13 | 2017-08-25 | 셀진 인터내셔널 Ii 에스에이알엘 | 선택적 헤테로시클릭 스핑고신 1 포스페이트 수용체 조절자 |
| CN101712641B (zh) * | 2009-12-29 | 2013-05-08 | 江苏工业学院 | 一种甲硫基苯甲酸的制备方法 |
| US8592590B2 (en) | 2009-12-29 | 2013-11-26 | Eli Lilly And Company | Tetrahydrotriazolopyridine compounds as selective MGLU5 receptor potentiators useful for the treatment of schizophrenia |
| EP2523936A1 (en) | 2010-01-15 | 2012-11-21 | Boehringer Ingelheim International GmbH | Compounds which modulate the cb2 receptor |
| AR080056A1 (es) | 2010-02-01 | 2012-03-07 | Novartis Ag | Derivados de ciclohexil-amida como antagonistas de los receptores de crf |
| EP2531510B1 (en) | 2010-02-01 | 2014-07-23 | Novartis AG | Pyrazolo[5,1b]oxazole derivatives as crf-1 receptor antagonists |
| US8835444B2 (en) | 2010-02-02 | 2014-09-16 | Novartis Ag | Cyclohexyl amide derivatives as CRF receptor antagonists |
| US8329735B2 (en) | 2010-03-05 | 2012-12-11 | Boehringer Ingelheim International Gmbh | Tetrazole compounds which selectively modulate the CB2 receptor |
| AR081331A1 (es) | 2010-04-23 | 2012-08-08 | Cytokinetics Inc | Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos |
| AR081626A1 (es) | 2010-04-23 | 2012-10-10 | Cytokinetics Inc | Compuestos amino-piridazinicos, composiciones farmaceuticas que los contienen y uso de los mismos para tratar trastornos musculares cardiacos y esqueleticos |
| US9133123B2 (en) | 2010-04-23 | 2015-09-15 | Cytokinetics, Inc. | Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use |
| EP2595959B1 (en) | 2010-07-22 | 2015-11-04 | Boehringer Ingelheim International GmbH | Sulfonyl compounds which modulate the cb2 receptor |
| US20130203735A1 (en) * | 2010-10-28 | 2013-08-08 | John T. Sisko | Caprolactam mglur5 receptor modulators |
| WO2012076898A1 (en) | 2010-12-08 | 2012-06-14 | Oslo University Hospital Hf | Triazole derivatives as wnt signaling pathway inhibitors |
| DE102010063974B4 (de) * | 2010-12-22 | 2021-10-07 | Thomas Rühl | Pharmakologische Wirkstoffe und Radiodiagnostika mit 18F-markierter 3-Aryl- oder 3-Heteroaryl-1,2,4-oxadiazoleinheit und Verfahren zu deren Herstellung |
| CA2830458A1 (en) | 2011-03-18 | 2012-09-27 | Novartis Ag | Combinations of alpha 7 nicotinic acetylcholine receptor activators and mglur5 antagonists for use in dopamine induced dyskinesia in parkinson's disease |
| US8759380B2 (en) * | 2011-04-22 | 2014-06-24 | Cytokinetics, Inc. | Certain heterocycles, compositions thereof, and methods for their use |
| JP6129159B2 (ja) | 2011-05-13 | 2017-05-17 | レセプトス エルエルシー | 選択的複素環式スフィンゴシン１−リン酸受容体モジュレーター |
| EP2545964A1 (en) | 2011-07-13 | 2013-01-16 | Phenex Pharmaceuticals AG | Novel FXR (NR1H4) binding and activity modulating compounds |
| US9199975B2 (en) | 2011-09-30 | 2015-12-01 | Asana Biosciences, Llc | Biaryl imidazole derivatives for regulating CYP17 |
| EP2803668A1 (en) | 2013-05-17 | 2014-11-19 | Boehringer Ingelheim International Gmbh | Novel (cyano-dimethyl-methyl)-isoxazoles and -[1,3,4]thiadiazoles |
| JP6521977B2 (ja) | 2013-09-06 | 2019-05-29 | オーリジーン ディスカバリー テクノロジーズ リミテッドＡｕｒｉｇｅｎｅ Ｄｉｓｃｏｖｅｒｙ Ｔｅｃｈｎｏｌｏｇｉｅｓ Ｌｉｍｉｔｅｄ | 免疫調節剤としての１，２，４−オキサジアゾール誘導体 |
| JP6858129B2 (ja) * | 2015-03-05 | 2021-04-14 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 置換されたフェニルイソオキサゾリン誘導体の製造方法 |
| SG11201706902SA (en) * | 2015-03-10 | 2017-09-28 | Aurigene Discovery Tech Ltd | 3-substituted-1,2,4-oxadiazole and thiadiazole compounds as immunomodulators |
| SMT202200163T1 (it) | 2015-03-10 | 2022-05-12 | Aurigene Discovery Tech Ltd | Composti di 1,2,4-0ssadiazolo e tiadiazolo come immunomodulatori |
| EP3468962A1 (en) | 2016-06-13 | 2019-04-17 | Gilead Sciences, Inc. | Fxr (nr1h4) modulating compounds |
| CA2968836C (en) | 2016-06-13 | 2025-09-02 | Gilead Sciences, Inc. | FXR MODULATING COMPOUNDS (NR1H4) |
| EP4424364A3 (en) | 2017-03-28 | 2024-11-27 | Gilead Sciences, Inc. | Methods of treating liver disease |
| WO2019061324A1 (en) | 2017-09-29 | 2019-04-04 | Curis Inc. | CRYSTALLINE FORMS OF IMMUNOMODULATORS |
| US11247987B2 (en) | 2017-10-06 | 2022-02-15 | Forma Therapeutics, Inc. | Inhibiting ubiquitin specific peptidase 30 |
| US11136300B2 (en) | 2017-10-11 | 2021-10-05 | Aurigene Discovery Technologies Limited | Crystalline forms of 3-substituted 1,2,4-oxadiazole |
| JP7378394B2 (ja) | 2017-11-03 | 2023-11-13 | オーリジーン オンコロジー リミテッド | Ｔｉｍ－３およびｐｄ－１経路の二重阻害剤 |
| WO2019087092A1 (en) | 2017-11-06 | 2019-05-09 | Aurigene Discovery Technologies Limited | Conjoint therapies for immunomodulation |
| EP3724161B1 (en) | 2017-11-16 | 2025-01-01 | Montdorex Inc. | Mono- and di-amidine endo-exonuclease inhibitors and methods for inhibiting endo-exonuclease activity |
| ES2988920T3 (es) | 2018-05-17 | 2024-11-22 | Forma Therapeutics Inc | Compuestos bicíclicos fusionados útiles como inhibidores de la peptidasa 30 específica de ubiquitina |
| MX2021002981A (es) | 2018-10-05 | 2021-05-14 | Forma Therapeutics Inc | Pirrolinas fusionadas que actuan como inhibidores de la proteasa 30 especifica de la ubiquitina (usp30). |
| AU2020209564B2 (en) | 2019-01-15 | 2022-12-01 | Gilead Sciences, Inc. | FXR (NR1H4) modulating compounds |
| CN118388474A (zh) | 2019-02-19 | 2024-07-26 | 吉利德科学公司 | Fxr激动剂的固体形式 |
| US20220259193A1 (en) * | 2019-05-03 | 2022-08-18 | Praxis Precision Medicines, Inc. | Kcnt1 inhibitors and methods of use |
| US20220387410A1 (en) * | 2019-11-05 | 2022-12-08 | Claes Thulin | 4-[5-[(rac)-1-[5-(3-Chlorophenyl)-3-isoxazolyl]ethoxy]-4-methyl-4H-1,2,4-triazol-3-yl]pyridine for use in prevention and/or treatment of surmenage in a mammal |
| CR20220375A (es) * | 2020-01-07 | 2022-09-22 | Disarm Therapeutics Inc | Inhibidores de sarm1 |
| TW202334117A (zh) | 2020-08-24 | 2023-09-01 | 美商達薩瑪治療公司 | Ｓａｒｍ１之抑制劑 |
| WO2022231872A1 (en) * | 2021-04-29 | 2022-11-03 | Praxis Precision Medicines, Inc. | Kcnt1 inhibitors and methods of use |
| FI4514782T3 (fi) | 2022-05-19 | 2025-12-10 | Astrazeneca Ab | Maksasairauksien hoitoon käyttökelpoisia amidoheteroaromaattisia yhdisteitä |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4538833A (en) * | 1983-12-08 | 1985-09-03 | P I E International Inc. | Publication |
| US5403138A (en) * | 1991-10-09 | 1995-04-04 | Fuji Photo Film Co., Ltd. | Booklet album including a double-sided photograph and a method of making the same |
| US5332265A (en) * | 1993-01-22 | 1994-07-26 | Minnesota Mining And Manufacturing Company | Advertising assembly |
| US6194410B1 (en) * | 1998-03-11 | 2001-02-27 | Hoffman-La Roche Inc. | Pyrazolopyrimidine and pyrazolines and process for preparation thereof |
| CZ2002599A3 (cs) | 1999-08-19 | 2002-06-12 | Nps Pharmaceuticals Inc. | Heteropolycyklické sloučeniny a jejich pouľití jako antagonistů metabotropního receptoru glutamátu |
| US20040259917A1 (en) | 2001-12-19 | 2004-12-23 | Cosford Nicholas D.P. | Heteroaryl substituted imidazole modulators of metabotropic glutamate receptor-5 |
| EP1581525A2 (en) * | 2002-08-09 | 2005-10-05 | AstraZeneca AB | Compounds having an activity at metabotropic glutamate receptors |
| IL166510A0 (en) | 2002-08-09 | 2006-01-15 | Nps Pharma Inc | 1,2,4"oxadiazole as modulators of metabotropic glutamate receptor-5 |
| JP2006506340A (ja) | 2002-08-09 | 2006-02-23 | アストラゼネカ アクチボラグ | 代謝調節型グルタミン酸受容体５のモジュレーターとしてのオキサジアゾール |
| US7585881B2 (en) * | 2004-02-18 | 2009-09-08 | Astrazeneca Ab | Additional heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| UY29796A1 (es) * | 2005-09-29 | 2007-04-30 | Astrazeneca Ab | Nuevos compuestos para el tratamiento de trastornos neurológicos, psiquiátricos o del dolor |
-
2005
- 2005-02-09 US US11/053,752 patent/US7585881B2/en not_active Expired - Fee Related
- 2005-02-15 CN CNA2005800043063A patent/CN1984907A/zh active Pending
- 2005-02-15 ES ES05802855T patent/ES2352110T3/es not_active Expired - Lifetime
- 2005-02-15 WO PCT/US2005/004774 patent/WO2006014185A1/en not_active Ceased
- 2005-02-15 RU RU2006128446/04A patent/RU2370495C2/ru not_active IP Right Cessation
- 2005-02-15 JP JP2006554165A patent/JP4912157B2/ja not_active Expired - Fee Related
- 2005-02-15 AU AU2005270208A patent/AU2005270208A1/en not_active Abandoned
- 2005-02-15 HR HR20100654T patent/HRP20100654T1/hr unknown
- 2005-02-15 PT PT05802855T patent/PT1723144E/pt unknown
- 2005-02-15 EP EP05802855A patent/EP1723144B1/en not_active Expired - Lifetime
- 2005-02-15 SI SI200531175T patent/SI1723144T1/sl unknown
- 2005-02-15 UA UAA200608867A patent/UA84318C2/ru unknown
- 2005-02-15 SG SG200806914-8A patent/SG146657A1/en unknown
- 2005-02-15 CN CNA2007101278476A patent/CN101096368A/zh active Pending
- 2005-02-15 DK DK05802855.6T patent/DK1723144T3/da active
- 2005-02-15 RS RSP-2010/0525A patent/RS51516B/sr unknown
- 2005-02-15 PL PL05802855T patent/PL1723144T3/pl unknown
- 2005-02-15 DE DE602005023963T patent/DE602005023963D1/de not_active Expired - Lifetime
- 2005-02-15 CA CA002555566A patent/CA2555566A1/en not_active Abandoned
- 2005-02-15 NZ NZ548954A patent/NZ548954A/xx unknown
- 2005-02-15 AT AT05802855T patent/ATE483706T1/de active
- 2005-02-15 EP EP10182161A patent/EP2311830A1/en not_active Withdrawn
- 2005-02-15 US US10/588,702 patent/US20070179188A1/en not_active Abandoned
- 2005-02-15 BR BRPI0507497-5A patent/BRPI0507497A/pt not_active IP Right Cessation
- 2005-02-18 UY UY28766A patent/UY28766A1/es not_active Application Discontinuation
-
2006
- 2006-08-07 ZA ZA200606551A patent/ZA200606551B/en unknown
- 2006-08-08 NO NO20063599A patent/NO20063599L/no not_active Application Discontinuation
- 2006-08-09 IL IL177394A patent/IL177394A0/en unknown
-
2007
- 2007-08-18 US US11/840,955 patent/US20080015204A1/en not_active Abandoned
- 2007-08-18 US US11/840,954 patent/US20070293545A1/en not_active Abandoned
- 2007-08-18 US US11/840,952 patent/US20080015234A1/en not_active Abandoned
- 2007-08-18 US US11/840,953 patent/US20080045571A1/en not_active Abandoned
-
2010
- 2010-12-03 CY CY20101101116T patent/CY1110965T1/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200606551B (en) | Additional heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists | |
| EP3405465B1 (en) | Irak4 inhibiting agents | |
| US8822478B2 (en) | Indazole inhibitors of the WNT signal pathway and therapeutic uses thereof | |
| TWI585084B (zh) | 麩醯胺酸酶的雜環抑制劑 | |
| CA2930060C (en) | Alkyl-amide-substituted pyridyl compounds useful as modulators of il-12, il-23 and/or ifnalpha responses | |
| ZA200606594B (en) | Tetrazole compounds and their use as metabotropic glutamate receptor antagonists | |
| US20190248787A1 (en) | Irak4 inhibiting agents | |
| AU2014346919B2 (en) | Compositions and methods for modulating Farnesoid X receptors | |
| US8119643B2 (en) | Benzoimidazolyl-pyrazine compounds for inflammation and immune-related uses | |
| ZA200606508B (en) | Fused heterocyclic compounds and their use as metabotro-pic receptor antagonists for the treatment of gastrointestinal disorders | |
| SG172152A1 (en) | 1, 2, 4 -oxadiazole derivatives and their therapeutic use | |
| AU2019385397B2 (en) | Macrocyclic inhibitors of DYRK1A | |
| TW200948809A (en) | Glucokinase activators | |
| AU2013341185A1 (en) | Alkyl-amide-substituted pyridyl compounds useful as modulators of IL-12, IL-23 and/or IFNalpha responses | |
| JP2010513560A (ja) | １−置換イミダゾール誘導体およびアルドステロン合成阻害剤としてのその使用 | |
| JP2003514762A (ja) | Ｓｒｃファミリーｓｈ２ドメインインヒビターとしてのピリドン | |
| CA2889697C (en) | Cannabinoid receptor mediating compounds | |
| CN101605776A (zh) | 4-咪唑基-1,2,3,4-四氢喹啉衍生物及其作为醛甾酮/11-β-羟化酶抑制剂的用途 | |
| CN101448832A (zh) | 醛固酮合酶和/或11β-羟化酶抑制剂 | |
| MXPA04007697A (es) | Compuestos de heteroarilo utiles como inhibidores de gsk-3. | |
| US20140066443A1 (en) | Aminomethyl biaryl benzotriazole derivatives | |
| WO2015115507A1 (ja) | 複素環スルホンアミド誘導体及びそれを含有する医薬 | |
| CN107835637A (zh) | 作为激酶抑制剂的杂环化合物 | |
| AU2008255815B2 (en) | Tetrahydroisoquinolin-1-one derivative or salt thereof | |
| KR20150036068A (ko) | 미네랄로코르티코이드 수용체 길항제 |