CA2768832A1 - Substituted benzoimidazolesulfonamides and substituted indolesulfonamides as mglur4 potentiators - Google Patents

Info

Publication number

CA2768832A1

CA2768832A1 CA2768832A CA2768832A CA2768832A1 CA 2768832 A1 CA2768832 A1 CA 2768832A1 CA 2768832 A CA2768832 A CA 2768832A CA 2768832 A CA2768832 A CA 2768832A CA 2768832 A1 CA2768832 A1 CA 2768832A1

Authority

CA

Canada

Prior art keywords

optionally substituted

hydrogen

compound

mglur4

organic residue

Prior art date

2009-07-23

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• XRGHQBXKSHAQRB-UHFFFAOYSA-N 1h-benzimidazole-2-sulfonamide Chemical class C1=CC=C2NC(S(=O)(=O)N)=NC2=C1 XRGHQBXKSHAQRB-UHFFFAOYSA-N 0.000 title abstract description 3
• RYMYQAMZUWJAEO-UHFFFAOYSA-N 1h-indole-2-sulfonamide Chemical class C1=CC=C2NC(S(=O)(=O)N)=CC2=C1 RYMYQAMZUWJAEO-UHFFFAOYSA-N 0.000 title abstract description 3
• 102100038354 Metabotropic glutamate receptor 4 Human genes 0.000 claims abstract description 57
• 108010038422 metabotropic glutamate receptor 4 Proteins 0.000 claims abstract 54
• 150000001875 compounds Chemical class 0.000 claims description 362
• -1 i-pentyl Chemical group 0.000 claims description 331
• 229910052739 hydrogen Inorganic materials 0.000 claims description 253
• 239000001257 hydrogen Substances 0.000 claims description 253
• 238000000034 method Methods 0.000 claims description 235
• 150000002431 hydrogen Chemical class 0.000 claims description 161
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 132
• 229910052757 nitrogen Inorganic materials 0.000 claims description 127
• 125000003545 alkoxy group Chemical group 0.000 claims description 123
• 150000004820 halides Chemical group 0.000 claims description 116
• 230000000694 effects Effects 0.000 claims description 115
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 108
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 107
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 106
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 106
• 125000005518 carboxamido group Chemical group 0.000 claims description 105
• DYMRYCZRMAHYKE-UHFFFAOYSA-N n-diazonitramide Chemical group [O-][N+](=O)N=[N+]=[N-] DYMRYCZRMAHYKE-UHFFFAOYSA-N 0.000 claims description 105
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 105
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 97
• 241000124008 Mammalia Species 0.000 claims description 90
• 208000035475 disorder Diseases 0.000 claims description 81
• 239000000203 mixture Substances 0.000 claims description 73
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 70
• 239000003814 drug Substances 0.000 claims description 65
• 125000004122 cyclic group Chemical group 0.000 claims description 62
• 230000004064 dysfunction Effects 0.000 claims description 62
• 238000011282 treatment Methods 0.000 claims description 60
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 58
• 229940079593 drug Drugs 0.000 claims description 55
• 201000010099 disease Diseases 0.000 claims description 51
• 150000003839 salts Chemical class 0.000 claims description 48
• 239000000556 agonist Substances 0.000 claims description 43
• 108010010914 Metabotropic glutamate receptors Proteins 0.000 claims description 42
• 102000016193 Metabotropic glutamate receptors Human genes 0.000 claims description 42
• 125000003118 aryl group Chemical group 0.000 claims description 39
• 239000008194 pharmaceutical composition Substances 0.000 claims description 39
• 230000003389 potentiating effect Effects 0.000 claims description 39
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 37
• 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 37
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 37
• KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 36
• 125000001072 heteroaryl group Chemical group 0.000 claims description 36
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
• 210000004027 cell Anatomy 0.000 claims description 33
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 32
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 28
• 229930195712 glutamate Natural products 0.000 claims description 28
• 239000003795 chemical substances by application Substances 0.000 claims description 27
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 24
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 24
• 230000005062 synaptic transmission Effects 0.000 claims description 24
• 208000028017 Psychotic disease Diseases 0.000 claims description 23
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 23
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 23
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 22
• 239000003937 drug carrier Substances 0.000 claims description 21
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 21
• 208000018737 Parkinson disease Diseases 0.000 claims description 19
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 19
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 19
• 201000000980 schizophrenia Diseases 0.000 claims description 19
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 18
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 18
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 18
• KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 18
• 208000019901 Anxiety disease Diseases 0.000 claims description 18
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 18
• 208000020016 psychiatric disease Diseases 0.000 claims description 18
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 18
• 230000001965 increasing effect Effects 0.000 claims description 17
• 208000012902 Nervous system disease Diseases 0.000 claims description 15
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
• 230000000926 neurological effect Effects 0.000 claims description 15
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
• 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 13
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 11
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 11
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 11
• 208000010877 cognitive disease Diseases 0.000 claims description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 11
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
• OYWRDHBGMCXGFY-UHFFFAOYSA-N 1,2,3-triazinane Chemical compound C1CNNNC1 OYWRDHBGMCXGFY-UHFFFAOYSA-N 0.000 claims description 10
• CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical compound C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 claims description 10
• UPNNXUSUOSTIIM-UHFFFAOYSA-N 1,2-dithietane Chemical compound C1CSS1 UPNNXUSUOSTIIM-UHFFFAOYSA-N 0.000 claims description 10
• DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical compound C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 claims description 10
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 10
• IMLSAISZLJGWPP-UHFFFAOYSA-N 1,3-dithiolane Chemical compound C1CSCS1 IMLSAISZLJGWPP-UHFFFAOYSA-N 0.000 claims description 10
• OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 10
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 10
• JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 claims description 10
• NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 10
• BVTJGGGYKAMDBN-UHFFFAOYSA-N Dioxetane Chemical compound C1COO1 BVTJGGGYKAMDBN-UHFFFAOYSA-N 0.000 claims description 10
• WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 10
• WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 10
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical class C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 10
• YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 claims description 10
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical class C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
• 230000036506 anxiety Effects 0.000 claims description 10
• ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 10
• QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 claims description 10
• QPMLSUSACCOBDK-UHFFFAOYSA-N diazepane Chemical compound C1CCNNCC1 QPMLSUSACCOBDK-UHFFFAOYSA-N 0.000 claims description 10
• YRTMEEURRDTMST-UHFFFAOYSA-N diazetidine Chemical compound C1CNN1 YRTMEEURRDTMST-UHFFFAOYSA-N 0.000 claims description 10
• DIXBSCZRIZDQGC-UHFFFAOYSA-N diaziridine Chemical compound C1NN1 DIXBSCZRIZDQGC-UHFFFAOYSA-N 0.000 claims description 10
• KJGHYQZXEYTDSW-UHFFFAOYSA-N diazocane Chemical compound C1CCCNNCC1 KJGHYQZXEYTDSW-UHFFFAOYSA-N 0.000 claims description 10
• HGGNZMUHOHGHBJ-UHFFFAOYSA-N dioxepane Chemical compound C1CCOOCC1 HGGNZMUHOHGHBJ-UHFFFAOYSA-N 0.000 claims description 10
• ASQQEOXYFGEFKQ-UHFFFAOYSA-N dioxirane Chemical compound C1OO1 ASQQEOXYFGEFKQ-UHFFFAOYSA-N 0.000 claims description 10
• WXIXHCWLYVANJA-UHFFFAOYSA-N dioxocane Chemical compound C1CCCOOCC1 WXIXHCWLYVANJA-UHFFFAOYSA-N 0.000 claims description 10
• LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 claims description 10
• KUSGATRNQCYALG-UHFFFAOYSA-N dithiepane Chemical compound C1CCSSCC1 KUSGATRNQCYALG-UHFFFAOYSA-N 0.000 claims description 10
• XJLXLCWHYSPAJZ-UHFFFAOYSA-N dithiirane Chemical compound C1SS1 XJLXLCWHYSPAJZ-UHFFFAOYSA-N 0.000 claims description 10
• LMBQHCNXCQCXGQ-UHFFFAOYSA-N dithiocane Chemical compound C1CCCSSCC1 LMBQHCNXCQCXGQ-UHFFFAOYSA-N 0.000 claims description 10
• 238000004519 manufacturing process Methods 0.000 claims description 10
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 10
• IVMHDOBGNQOUHO-UHFFFAOYSA-N oxathiane Chemical compound C1CCSOC1 IVMHDOBGNQOUHO-UHFFFAOYSA-N 0.000 claims description 10
• OXUZCBDDXOMZAM-UHFFFAOYSA-N oxathiepane Chemical compound C1CCOSCC1 OXUZCBDDXOMZAM-UHFFFAOYSA-N 0.000 claims description 10
• CTFDXEOXCVVOJI-UHFFFAOYSA-N oxathietane Chemical compound C1CSO1 CTFDXEOXCVVOJI-UHFFFAOYSA-N 0.000 claims description 10
• FAIFRTLETMUYIX-UHFFFAOYSA-N oxathiirane Chemical compound C1OS1 FAIFRTLETMUYIX-UHFFFAOYSA-N 0.000 claims description 10
• SMYLNBXMZBBQLG-UHFFFAOYSA-N oxathiocane Chemical compound C1CCCSOCC1 SMYLNBXMZBBQLG-UHFFFAOYSA-N 0.000 claims description 10
• OOFGXDQWDNJDIS-UHFFFAOYSA-N oxathiolane Chemical compound C1COSC1 OOFGXDQWDNJDIS-UHFFFAOYSA-N 0.000 claims description 10
• AQNQGBUEVCAVML-UHFFFAOYSA-N oxazepane Chemical compound C1CCNOCC1 AQNQGBUEVCAVML-UHFFFAOYSA-N 0.000 claims description 10
• XHWNEBDUPVMPKI-UHFFFAOYSA-N oxazetidine Chemical compound C1CON1 XHWNEBDUPVMPKI-UHFFFAOYSA-N 0.000 claims description 10
• SJGALSBBFTYSBA-UHFFFAOYSA-N oxaziridine Chemical compound C1NO1 SJGALSBBFTYSBA-UHFFFAOYSA-N 0.000 claims description 10
• KKHNAVZYZJMXFV-UHFFFAOYSA-N oxazocane Chemical compound C1CCCONCC1 KKHNAVZYZJMXFV-UHFFFAOYSA-N 0.000 claims description 10
• UHHKSVZZTYJVEG-UHFFFAOYSA-N oxepane Chemical compound C1CCCOCC1 UHHKSVZZTYJVEG-UHFFFAOYSA-N 0.000 claims description 10
• AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims description 10
• HZIVRQOIUMAXID-UHFFFAOYSA-N oxocane Chemical compound C1CCCOCCC1 HZIVRQOIUMAXID-UHFFFAOYSA-N 0.000 claims description 10
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 10
• RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims description 10
• PGAZQSBUJDVGIX-UHFFFAOYSA-N thiazepane Chemical compound C1CCNSCC1 PGAZQSBUJDVGIX-UHFFFAOYSA-N 0.000 claims description 10
• MNFSSEUNEZGWRS-UHFFFAOYSA-N thiazetidine Chemical compound C1CSN1 MNFSSEUNEZGWRS-UHFFFAOYSA-N 0.000 claims description 10
• DSXQWLYNLIETTE-UHFFFAOYSA-N thiaziridine Chemical compound C1NS1 DSXQWLYNLIETTE-UHFFFAOYSA-N 0.000 claims description 10
• VZYZKDFMQQEERI-UHFFFAOYSA-N thiazocane Chemical compound C1CCCSNCC1 VZYZKDFMQQEERI-UHFFFAOYSA-N 0.000 claims description 10
• JWCVYQRPINPYQJ-UHFFFAOYSA-N thiepane Chemical compound C1CCCSCC1 JWCVYQRPINPYQJ-UHFFFAOYSA-N 0.000 claims description 10
• XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 claims description 10
• VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 claims description 10
• AMIGYDGSJCJWSD-UHFFFAOYSA-N thiocane Chemical compound C1CCCSCCC1 AMIGYDGSJCJWSD-UHFFFAOYSA-N 0.000 claims description 10
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 10
• 208000020925 Bipolar disease Diseases 0.000 claims description 9
• 208000008589 Obesity Diseases 0.000 claims description 9
• 235000020824 obesity Nutrition 0.000 claims description 9
• 208000031091 Amnestic disease Diseases 0.000 claims description 8
• 206010012218 Delirium Diseases 0.000 claims description 8
• 206010012289 Dementia Diseases 0.000 claims description 8
• 235000019640 taste Nutrition 0.000 claims description 8
• 208000030814 Eating disease Diseases 0.000 claims description 7
• 208000019454 Feeding and Eating disease Diseases 0.000 claims description 7
• 208000016285 Movement disease Diseases 0.000 claims description 7
• 235000014632 disordered eating Nutrition 0.000 claims description 7
• 206010015037 epilepsy Diseases 0.000 claims description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical class COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 7
• 206010028980 Neoplasm Diseases 0.000 claims description 6
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
• 125000000623 heterocyclic group Chemical group 0.000 claims description 6
• 208000000172 Medulloblastoma Diseases 0.000 claims description 5
• 208000019022 Mood disease Diseases 0.000 claims description 5
• 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 claims description 5
• 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims description 5
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical class C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 5
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical class C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 5
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
• 125000005872 benzooxazolyl group Chemical group 0.000 claims description 5
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 5
• 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 claims description 5
• 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 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
• 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims description 5
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 5
• 125000004090 cyclononenyl group Chemical group C1(=CCCCCCCC1)* 0.000 claims description 5
• 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
• 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 claims description 5
• 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 claims description 5
• 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 5
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 5
• ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 5
• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
• 125000001041 indolyl group Chemical group 0.000 claims description 5
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical class C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 5
• 208000024714 major depressive disease Diseases 0.000 claims description 5
• 125000001624 naphthyl group Chemical group 0.000 claims description 5
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 5
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
• 125000003107 substituted aryl group Chemical group 0.000 claims description 5
• 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• 229930192474 thiophene Chemical class 0.000 claims description 5
• 125000004306 triazinyl group Chemical group 0.000 claims description 5
• FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical class C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 4
• MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical class C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 4
• 230000000848 glutamatergic effect Effects 0.000 claims description 4
• 208000030159 metabolic disease Diseases 0.000 claims description 4
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