JP2010521527A5

JP2010521527A5 -

Download PDF

Info

Publication number: JP2010521527A5
Authority: JP; Japan
Prior art keywords: optionally substituted; acid; methyl; antagonist; phenyl
Prior art date: 2008-03-25
Legal status : Pending

Application number

JP2010500037A

Other languages

English (en)

Japanese (ja)

Other versions

JP2010521527A (ja

Filing date

2008-03-25

Publication date

2011-05-12

2008-03-25 Application filed filed Critical

2008-03-25 Priority claimed from PCT/CA2008/000569 external-priority patent/WO2008116308A1/en

2010-06-24 Publication of JP2010521527A publication Critical patent/JP2010521527A/ja

2011-05-12 Publication of JP2010521527A5 publication Critical patent/JP2010521527A5/ja

Status Pending legal-status Critical Current

Links

-1 NR 7 Inorganic materials 0.000 claims description 54
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
150000001875 compounds Chemical class 0.000 claims description 28
239000000203 mixture Substances 0.000 claims description 27
208000004454 Hyperalgesia Diseases 0.000 claims description 20
150000003839 salts Chemical class 0.000 claims description 15
238000000034 method Methods 0.000 claims description 14
239000000556 agonist Substances 0.000 claims description 12
208000035154 Hyperesthesia Diseases 0.000 claims description 10
208000002193 Pain Diseases 0.000 claims description 10
206010053552 allodynia Diseases 0.000 claims description 10
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 10
239000005557 antagonist Substances 0.000 claims description 9
206010013663 drug dependence Diseases 0.000 claims description 9
208000011117 substance-related disease Diseases 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 8
239000003112 inhibitor Substances 0.000 claims description 8
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 8
239000004036 potassium channel stimulating agent Substances 0.000 claims description 8
102000009346 Adenosine receptors Human genes 0.000 claims description 6
108050000203 Adenosine receptors Proteins 0.000 claims description 6
206010064012 Central pain syndrome Diseases 0.000 claims description 6
208000019695 Migraine disease Diseases 0.000 claims description 6
206010029350 Neurotoxicity Diseases 0.000 claims description 6
206010044221 Toxic encephalopathy Diseases 0.000 claims description 6
206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 6
239000001961 anticonvulsive agent Substances 0.000 claims description 6
206010015037 epilepsy Diseases 0.000 claims description 6
206010027599 migraine Diseases 0.000 claims description 6
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 6
208000004296 neuralgia Diseases 0.000 claims description 6
208000021722 neuropathic pain Diseases 0.000 claims description 6
231100000228 neurotoxicity Toxicity 0.000 claims description 6
230000007135 neurotoxicity Effects 0.000 claims description 6
241000124008 Mammalia Species 0.000 claims description 5
XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 claims description 5
229960004193 dextropropoxyphene Drugs 0.000 claims description 5
230000004770 neurodegeneration Effects 0.000 claims description 5
208000015122 neurodegenerative disease Diseases 0.000 claims description 5
229960002702 piroxicam Drugs 0.000 claims description 5
QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 claims description 5
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 4
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 4
UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 claims description 4
206010019233 Headaches Diseases 0.000 claims description 4
XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 claims description 4
208000018737 Parkinson disease Diseases 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
230000003110 anti-inflammatory effect Effects 0.000 claims description 4
239000000935 antidepressant agent Substances 0.000 claims description 4
229940005513 antidepressants Drugs 0.000 claims description 4
OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 claims description 4
XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 claims description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
229940079593 drug Drugs 0.000 claims description 4
OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims description 4
229960005181 morphine Drugs 0.000 claims description 4
239000002767 noradrenalin uptake inhibitor Substances 0.000 claims description 4
229940005483 opioid analgesics Drugs 0.000 claims description 4
229960000482 pethidine Drugs 0.000 claims description 4
229960002431 trimipramine Drugs 0.000 claims description 4
ZSCDBOWYZJWBIY-UHFFFAOYSA-N trimipramine Chemical compound C1CC2=CC=CC=C2N(CC(CN(C)C)C)C2=CC=CC=C21 ZSCDBOWYZJWBIY-UHFFFAOYSA-N 0.000 claims description 4
ZISSAWUMDACLOM-UHFFFAOYSA-N triptane Chemical compound CC(C)C(C)(C)C ZISSAWUMDACLOM-UHFFFAOYSA-N 0.000 claims description 4
MDKGKXOCJGEUJW-VIFPVBQESA-N (2s)-2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C(=O)C1=CC=CS1 MDKGKXOCJGEUJW-VIFPVBQESA-N 0.000 claims description 3
WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 claims description 3
ULFYMTMZNITFSB-UHFFFAOYSA-N 2-(3,5-difluorophenyl)-3-(4-methylsulfonylphenyl)cyclopent-2-en-1-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(F)C=C(F)C=2)C(=O)CC1 ULFYMTMZNITFSB-UHFFFAOYSA-N 0.000 claims description 3
QPGGEKPRGVJKQB-UHFFFAOYSA-N 5-[2-(dimethylamino)ethyl]-11-methyl-6-benzo[b][1,4]benzodiazepinone Chemical compound O=C1N(CCN(C)C)C2=CC=CC=C2N(C)C2=CC=CC=C21 QPGGEKPRGVJKQB-UHFFFAOYSA-N 0.000 claims description 3
206010065040 AIDS dementia complex Diseases 0.000 claims description 3
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 3
208000000094 Chronic Pain Diseases 0.000 claims description 3
206010012289 Dementia Diseases 0.000 claims description 3
HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 claims description 3
206010019196 Head injury Diseases 0.000 claims description 3
208000023105 Huntington disease Diseases 0.000 claims description 3
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 3
ALFGKMXHOUSVAD-UHFFFAOYSA-N Ketobemidone Chemical compound C=1C=CC(O)=CC=1C1(C(=O)CC)CCN(C)CC1 ALFGKMXHOUSVAD-UHFFFAOYSA-N 0.000 claims description 3
229940123685 Monoamine oxidase inhibitor Drugs 0.000 claims description 3
KTDZCOWXCWUPEO-UHFFFAOYSA-N NS-398 Chemical compound CS(=O)(=O)NC1=CC=C([N+]([O-])=O)C=C1OC1CCCCC1 KTDZCOWXCWUPEO-UHFFFAOYSA-N 0.000 claims description 3
CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims description 3
PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 claims description 3
206010063837 Reperfusion injury Diseases 0.000 claims description 3
206010043269 Tension headache Diseases 0.000 claims description 3
208000008548 Tension-Type Headache Diseases 0.000 claims description 3
KJADKKWYZYXHBB-XBWDGYHZSA-N Topiramic acid Chemical compound C1O[C@@]2(COS(N)(=O)=O)OC(C)(C)O[C@H]2[C@@H]2OC(C)(C)O[C@@H]21 KJADKKWYZYXHBB-XBWDGYHZSA-N 0.000 claims description 3
229960001138 acetylsalicylic acid Drugs 0.000 claims description 3
229960000959 amineptine Drugs 0.000 claims description 3
KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 claims description 3
229960000590 celecoxib Drugs 0.000 claims description 3
RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 claims description 3
208000015114 central nervous system disease Diseases 0.000 claims description 3
238000002512 chemotherapy Methods 0.000 claims description 3
230000001684 chronic effect Effects 0.000 claims description 3
229960001653 citalopram Drugs 0.000 claims description 3
229960003914 desipramine Drugs 0.000 claims description 3
SSQJFGMEZBFMNV-PMACEKPBSA-N dexanabinol Chemical compound C1C(CO)=CC[C@@H]2C(C)(C)OC3=CC(C(C)(C)CCCCCC)=CC(O)=C3[C@H]21 SSQJFGMEZBFMNV-PMACEKPBSA-N 0.000 claims description 3
229960003075 dibenzepin Drugs 0.000 claims description 3
229960000616 diflunisal Drugs 0.000 claims description 3
HUPFGZXOMWLGNK-UHFFFAOYSA-N diflunisal Chemical compound C1=C(O)C(C(=O)O)=CC(C=2C(=CC(F)=CC=2)F)=C1 HUPFGZXOMWLGNK-UHFFFAOYSA-N 0.000 claims description 3
208000035475 disorder Diseases 0.000 claims description 3
229960005426 doxepin Drugs 0.000 claims description 3
ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 claims description 3
230000002526 effect on cardiovascular system Effects 0.000 claims description 3
229960001680 ibuprofen Drugs 0.000 claims description 3
229960004801 imipramine Drugs 0.000 claims description 3
BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 claims description 3
208000027866 inflammatory disease Diseases 0.000 claims description 3
229960003029 ketobemidone Drugs 0.000 claims description 3
DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 claims description 3
229960000991 ketoprofen Drugs 0.000 claims description 3
229960002813 lofepramine Drugs 0.000 claims description 3
SAPNXPWPAUFAJU-UHFFFAOYSA-N lofepramine Chemical compound C12=CC=CC=C2CCC2=CC=CC=C2N1CCCN(C)CC(=O)C1=CC=C(Cl)C=C1 SAPNXPWPAUFAJU-UHFFFAOYSA-N 0.000 claims description 3
229960004090 maprotiline Drugs 0.000 claims description 3
QSLMDECMDJKHMQ-GSXCWMCISA-N maprotiline Chemical compound C12=CC=CC=C2[C@@]2(CCCNC)C3=CC=CC=C3[C@@H]1CC2 QSLMDECMDJKHMQ-GSXCWMCISA-N 0.000 claims description 3
229960003464 mefenamic acid Drugs 0.000 claims description 3
YXVZOBVWVRFPTE-UHFFFAOYSA-N metapramine Chemical compound CNC1CC2=CC=CC=C2N(C)C2=CC=CC=C12 YXVZOBVWVRFPTE-UHFFFAOYSA-N 0.000 claims description 3
229950006180 metapramine Drugs 0.000 claims description 3
RONZAEMNMFQXRA-UHFFFAOYSA-N mirtazapine Chemical compound C1C2=CC=CN=C2N2CCN(C)CC2C2=CC=CC=C21 RONZAEMNMFQXRA-UHFFFAOYSA-N 0.000 claims description 3
YHXISWVBGDMDLQ-UHFFFAOYSA-N moclobemide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCCN1CCOCC1 YHXISWVBGDMDLQ-UHFFFAOYSA-N 0.000 claims description 3
229960004644 moclobemide Drugs 0.000 claims description 3
239000002899 monoamine oxidase inhibitor Substances 0.000 claims description 3
230000003551 muscarinic effect Effects 0.000 claims description 3
229960002009 naproxen Drugs 0.000 claims description 3
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 3
229940127221 norepinephrine reuptake inhibitor Drugs 0.000 claims description 3
229960001158 nortriptyline Drugs 0.000 claims description 3
229960002895 phenylbutazone Drugs 0.000 claims description 3
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 claims description 3
239000000018 receptor agonist Substances 0.000 claims description 3
229940044601 receptor agonist Drugs 0.000 claims description 3
229960000371 rofecoxib Drugs 0.000 claims description 3
RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 claims description 3
229940076279 serotonin Drugs 0.000 claims description 3
229960004492 suprofen Drugs 0.000 claims description 3
229960004394 topiramate Drugs 0.000 claims description 3
IGLYMJRIWWIQQE-QUOODJBBSA-N (1S,2R)-2-phenylcyclopropan-1-amine (1R,2S)-2-phenylcyclopropan-1-amine Chemical compound N[C@H]1C[C@@H]1C1=CC=CC=C1.N[C@@H]1C[C@H]1C1=CC=CC=C1 IGLYMJRIWWIQQE-QUOODJBBSA-N 0.000 claims description 2
TVYLLZQTGLZFBW-ZBFHGGJFSA-N (R,R)-tramadol Chemical compound COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-ZBFHGGJFSA-N 0.000 claims description 2
FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 claims description 2
XNTLXAUHLBBEKP-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(3-hydroxy-3-methylbutoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCCC(C)(O)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 XNTLXAUHLBBEKP-UHFFFAOYSA-N 0.000 claims description 2
KRQUFUKTQHISJB-YYADALCUSA-N 2-[(E)-N-[2-(4-chlorophenoxy)propoxy]-C-propylcarbonimidoyl]-3-hydroxy-5-(thian-3-yl)cyclohex-2-en-1-one Chemical compound CCC\C(=N/OCC(C)OC1=CC=C(Cl)C=C1)C1=C(O)CC(CC1=O)C1CCCSC1 KRQUFUKTQHISJB-YYADALCUSA-N 0.000 claims description 2
XILVEPYQJIOVNB-UHFFFAOYSA-N 2-[3-(trifluoromethyl)anilino]benzoic acid 2-(2-hydroxyethoxy)ethyl ester Chemical compound OCCOCCOC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 XILVEPYQJIOVNB-UHFFFAOYSA-N 0.000 claims description 2
YNZFUWZUGRBMHL-UHFFFAOYSA-N 2-[4-[3-(11-benzo[b][1]benzazepinyl)propyl]-1-piperazinyl]ethanol Chemical compound C1CN(CCO)CCN1CCCN1C2=CC=CC=C2C=CC2=CC=CC=C21 YNZFUWZUGRBMHL-UHFFFAOYSA-N 0.000 claims description 2
WKAVKKUXZAWHDM-UHFFFAOYSA-N 2-acetamidopentanedioic acid;2-(dimethylamino)ethanol Chemical compound CN(C)CCO.CC(=O)NC(C(O)=O)CCC(O)=O WKAVKKUXZAWHDM-UHFFFAOYSA-N 0.000 claims description 2
VPIXQGUBUKFLRF-UHFFFAOYSA-N 3-(2-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N-methyl-1-propanamine Chemical compound C1CC2=CC=C(Cl)C=C2N(CCCNC)C2=CC=CC=C21 VPIXQGUBUKFLRF-UHFFFAOYSA-N 0.000 claims description 2
239000003412 4 aminobutyric acid B receptor blocking agent Substances 0.000 claims description 2
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 2
USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 claims description 2
208000030507 AIDS Diseases 0.000 claims description 2
239000000775 AMPA receptor antagonist Substances 0.000 claims description 2
229940098747 AMPA receptor antagonist Drugs 0.000 claims description 2
OIRDTQYFTABQOQ-KQYNXXCUSA-N Adenosine Natural products C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims description 2
229940080778 Adenosine deaminase inhibitor Drugs 0.000 claims description 2
108010076278 Adenosine kinase Proteins 0.000 claims description 2
102100032534 Adenosine kinase Human genes 0.000 claims description 2
208000019901 Anxiety disease Diseases 0.000 claims description 2
208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 2
206010005949 Bone cancer Diseases 0.000 claims description 2
208000018084 Bone neoplasm Diseases 0.000 claims description 2
239000002126 C01EB10 - Adenosine Substances 0.000 claims description 2
208000022497 Cocaine-Related disease Diseases 0.000 claims description 2
MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 claims description 2
MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 claims description 2
208000007342 Diabetic Nephropathies Diseases 0.000 claims description 2
208000032131 Diabetic Neuropathies Diseases 0.000 claims description 2
206010012735 Diarrhoea Diseases 0.000 claims description 2
208000008279 Dumping Syndrome Diseases 0.000 claims description 2
208000010496 Heart Arrest Diseases 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
102000007008 Intermediate-Conductance Calcium-Activated Potassium Channels Human genes 0.000 claims description 2
108010033149 Intermediate-Conductance Calcium-Activated Potassium Channels Proteins 0.000 claims description 2
108010006746 KCNQ2 Potassium Channel Proteins 0.000 claims description 2
229940122282 L-type calcium channel antagonist Drugs 0.000 claims description 2
JAQUASYNZVUNQP-USXIJHARSA-N Levorphanol Chemical compound C1C2=CC=C(O)C=C2[C@]23CCN(C)[C@H]1[C@@H]2CCCC3 JAQUASYNZVUNQP-USXIJHARSA-N 0.000 claims description 2
SBDNJUWAMKYJOX-UHFFFAOYSA-N Meclofenamic Acid Chemical compound CC1=CC=C(Cl)C(NC=2C(=CC=CC=2)C(O)=O)=C1Cl SBDNJUWAMKYJOX-UHFFFAOYSA-N 0.000 claims description 2
ZRVUJXDFFKFLMG-UHFFFAOYSA-N Meloxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=C(C)S1 ZRVUJXDFFKFLMG-UHFFFAOYSA-N 0.000 claims description 2
UEQUQVLFIPOEMF-UHFFFAOYSA-N Mianserin Chemical compound C1C2=CC=CC=C2N2CCN(C)CC2C2=CC=CC=C21 UEQUQVLFIPOEMF-UHFFFAOYSA-N 0.000 claims description 2
GNJCUHZOSOYIEC-GAROZEBRSA-N Morphine-6-glucuronide Chemical compound O([C@H]1C=C[C@H]2[C@H]3CC=4C5=C(C(=CC=4)O)O[C@@H]1[C@]52CCN3C)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O GNJCUHZOSOYIEC-GAROZEBRSA-N 0.000 claims description 2
IDBPHNDTYPBSNI-UHFFFAOYSA-N N-(1-(2-(4-Ethyl-5-oxo-2-tetrazolin-1-yl)ethyl)-4-(methoxymethyl)-4-piperidyl)propionanilide Chemical compound C1CN(CCN2C(N(CC)N=N2)=O)CCC1(COC)N(C(=O)CC)C1=CC=CC=C1 IDBPHNDTYPBSNI-UHFFFAOYSA-N 0.000 claims description 2
QSQQPMHPCBLLGX-UHFFFAOYSA-N N-methyl-4-[2-(phenylmethyl)phenoxy]-1-butanamine Chemical compound CNCCCCOC1=CC=CC=C1CC1=CC=CC=C1 QSQQPMHPCBLLGX-UHFFFAOYSA-N 0.000 claims description 2
229940123579 N-type calcium channel antagonist Drugs 0.000 claims description 2
BLXXJMDCKKHMKV-UHFFFAOYSA-N Nabumetone Chemical compound C1=C(CCC(C)=O)C=CC2=CC(OC)=CC=C21 BLXXJMDCKKHMKV-UHFFFAOYSA-N 0.000 claims description 2
208000028389 Nerve injury Diseases 0.000 claims description 2
208000036110 Neuroinflammatory disease Diseases 0.000 claims description 2
206010057852 Nicotine dependence Diseases 0.000 claims description 2
102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims description 2
108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims description 2
JZFPYUNJRRFVQU-UHFFFAOYSA-N Niflumic acid Chemical compound OC(=O)C1=CC=CN=C1NC1=CC=CC(C(F)(F)F)=C1 JZFPYUNJRRFVQU-UHFFFAOYSA-N 0.000 claims description 2
BRUQQQPBMZOVGD-XFKAJCMBSA-N Oxycodone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C BRUQQQPBMZOVGD-XFKAJCMBSA-N 0.000 claims description 2
UQCNKQCJZOAFTQ-ISWURRPUSA-N Oxymorphone Chemical compound O([C@H]1C(CC[C@]23O)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O UQCNKQCJZOAFTQ-ISWURRPUSA-N 0.000 claims description 2
229940124047 P/Q-type calcium channel antagonist Drugs 0.000 claims description 2
229930012538 Paclitaxel Natural products 0.000 claims description 2
PWRPUAKXMQAFCJ-UHFFFAOYSA-N Perlapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2CC2=CC=CC=C12 PWRPUAKXMQAFCJ-UHFFFAOYSA-N 0.000 claims description 2
RMUCZJUITONUFY-UHFFFAOYSA-N Phenelzine Chemical compound NNCCC1=CC=CC=C1 RMUCZJUITONUFY-UHFFFAOYSA-N 0.000 claims description 2
CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 claims description 2
208000032395 Post gastric surgery syndrome Diseases 0.000 claims description 2
102100034354 Potassium voltage-gated channel subfamily KQT member 2 Human genes 0.000 claims description 2
208000028017 Psychotic disease Diseases 0.000 claims description 2
ZTVQQQVZCWLTDF-UHFFFAOYSA-N Remifentanil Chemical compound C1CN(CCC(=O)OC)CCC1(C(=O)OC)N(C(=O)CC)C1=CC=CC=C1 ZTVQQQVZCWLTDF-UHFFFAOYSA-N 0.000 claims description 2
SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 claims description 2
102000002582 Small-Conductance Calcium-Activated Potassium Channels Human genes 0.000 claims description 2
108010093479 Small-Conductance Calcium-Activated Potassium Channels Proteins 0.000 claims description 2
108010025083 TRPV1 receptor Proteins 0.000 claims description 2
208000025569 Tobacco Use disease Diseases 0.000 claims description 2
RUJBDQSFYCKFAA-UHFFFAOYSA-N Tofisopam Chemical compound N=1N=C(C)C(CC)C2=CC(OC)=C(OC)C=C2C=1C1=CC=C(OC)C(OC)=C1 RUJBDQSFYCKFAA-UHFFFAOYSA-N 0.000 claims description 2
201000004810 Vascular dementia Diseases 0.000 claims description 2
208000027418 Wounds and injury Diseases 0.000 claims description 2
HLAFSNJRKZLMPT-UHFFFAOYSA-N [2-[2-(aminomethyl)phenyl]sulfanylphenyl]methanol Chemical compound NCC1=CC=CC=C1SC1=CC=CC=C1CO HLAFSNJRKZLMPT-UHFFFAOYSA-N 0.000 claims description 2
229960004892 acemetacin Drugs 0.000 claims description 2
FSQKKOOTNAMONP-UHFFFAOYSA-N acemetacin Chemical compound CC1=C(CC(=O)OCC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 FSQKKOOTNAMONP-UHFFFAOYSA-N 0.000 claims description 2
230000001154 acute effect Effects 0.000 claims description 2
208000005298 acute pain Diseases 0.000 claims description 2
229960005305 adenosine Drugs 0.000 claims description 2
239000002487 adenosine deaminase inhibitor Substances 0.000 claims description 2
229960001391 alfentanil Drugs 0.000 claims description 2
ONNOFKFOZAJDHT-UHFFFAOYSA-N amineptine Chemical compound C1CC2=CC=CC=C2C(NCCCCCCC(=O)O)C2=CC=CC=C21 ONNOFKFOZAJDHT-UHFFFAOYSA-N 0.000 claims description 2
229940042749 amitriptyline / chlordiazepoxide Drugs 0.000 claims description 2
230000003556 anti-epileptic effect Effects 0.000 claims description 2
239000003416 antiarrhythmic agent Substances 0.000 claims description 2
229960003965 antiepileptics Drugs 0.000 claims description 2
239000003963 antioxidant agent Substances 0.000 claims description 2
230000036506 anxiety Effects 0.000 claims description 2
HSWPZIDYAHLZDD-UHFFFAOYSA-N atipamezole Chemical compound C1C2=CC=CC=C2CC1(CC)C1=CN=CN1 HSWPZIDYAHLZDD-UHFFFAOYSA-N 0.000 claims description 2
229960003002 atipamezole Drugs 0.000 claims description 2
IALVDLPLCLFBCF-CHWSQXEVSA-N befloxatone Chemical compound O=C1O[C@@H](COC)CN1C1=CC=C(OCC[C@@H](O)C(F)(F)F)C=C1 IALVDLPLCLFBCF-CHWSQXEVSA-N 0.000 claims description 2
229950000017 befloxatone Drugs 0.000 claims description 2
229960004933 bifemelane Drugs 0.000 claims description 2
229950009454 bipenamol Drugs 0.000 claims description 2
RMRJXGBAOAMLHD-IHFGGWKQSA-N buprenorphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]11CC[C@]3([C@H](C1)[C@](C)(O)C(C)(C)C)OC)CN2CC1CC1 RMRJXGBAOAMLHD-IHFGGWKQSA-N 0.000 claims description 2
229960001736 buprenorphine Drugs 0.000 claims description 2
IFKLAQQSCNILHL-QHAWAJNXSA-N butorphanol Chemical compound N1([C@@H]2CC3=CC=C(C=C3[C@@]3([C@]2(CCCC3)O)CC1)O)CC1CCC1 IFKLAQQSCNILHL-QHAWAJNXSA-N 0.000 claims description 2
229960001113 butorphanol Drugs 0.000 claims description 2
206010007625 cardiogenic shock Diseases 0.000 claims description 2
KYCBWEZLKCTALM-UHFFFAOYSA-N caroxazone Chemical compound C1=CC=C2OC(=O)N(CC(=O)N)CC2=C1 KYCBWEZLKCTALM-UHFFFAOYSA-N 0.000 claims description 2
229950006044 caroxazone Drugs 0.000 claims description 2
239000003743 cholecystokinin B receptor antagonist Substances 0.000 claims description 2
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 2
229960004316 cisplatin Drugs 0.000 claims description 2
201000006145 cocaine dependence Diseases 0.000 claims description 2
229960004126 codeine Drugs 0.000 claims description 2
210000004351 coronary vessel Anatomy 0.000 claims description 2
229960004544 cortisone Drugs 0.000 claims description 2
230000006378 damage Effects 0.000 claims description 2
229960002887 deanol Drugs 0.000 claims description 2
229960003314 deracoxib Drugs 0.000 claims description 2
WAZQAZKAZLXFMK-UHFFFAOYSA-N deracoxib Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(C(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 WAZQAZKAZLXFMK-UHFFFAOYSA-N 0.000 claims description 2
INUNXTSAACVKJS-OAQYLSRUSA-N dextromoramide Chemical compound C([C@@H](C)C(C(=O)N1CCCC1)(C=1C=CC=CC=1)C=1C=CC=CC=1)N1CCOCC1 INUNXTSAACVKJS-OAQYLSRUSA-N 0.000 claims description 2
229960003701 dextromoramide Drugs 0.000 claims description 2
229960003461 dezocine Drugs 0.000 claims description 2
VTMVHDZWSFQSQP-VBNZEHGJSA-N dezocine Chemical compound C1CCCC[C@H]2CC3=CC=C(O)C=C3[C@]1(C)[C@H]2N VTMVHDZWSFQSQP-VBNZEHGJSA-N 0.000 claims description 2
208000033679 diabetic kidney disease Diseases 0.000 claims description 2
229960001259 diclofenac Drugs 0.000 claims description 2
DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims description 2
RBOXVHNMENFORY-DNJOTXNNSA-N dihydrocodeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC RBOXVHNMENFORY-DNJOTXNNSA-N 0.000 claims description 2
229960000920 dihydrocodeine Drugs 0.000 claims description 2
229960003524 dimetacrine Drugs 0.000 claims description 2
RYQOGSFEJBUZBX-UHFFFAOYSA-N dimetacrine Chemical compound C1=CC=C2N(CCCN(C)C)C3=CC=CC=C3C(C)(C)C2=C1 RYQOGSFEJBUZBX-UHFFFAOYSA-N 0.000 claims description 2
HYPPXZBJBPSRLK-UHFFFAOYSA-N diphenoxylate Chemical compound C1CC(C(=O)OCC)(C=2C=CC=CC=2)CCN1CCC(C#N)(C=1C=CC=CC=1)C1=CC=CC=C1 HYPPXZBJBPSRLK-UHFFFAOYSA-N 0.000 claims description 2
229960004192 diphenoxylate Drugs 0.000 claims description 2
229960004679 doxorubicin Drugs 0.000 claims description 2
229960001104 droxidopa Drugs 0.000 claims description 2
SBNKFTQSBPKMBZ-UHFFFAOYSA-N ethenzamide Chemical compound CCOC1=CC=CC=C1C(N)=O SBNKFTQSBPKMBZ-UHFFFAOYSA-N 0.000 claims description 2
229960001493 etofenamate Drugs 0.000 claims description 2
CAHCBJPUTCKATP-FAWZKKEFSA-N etorphine Chemical compound O([C@H]1[C@@]2(OC)C=C[C@@]34C[C@@H]2[C@](C)(O)CCC)C2=C5[C@]41CCN(C)[C@@H]3CC5=CC=C2O CAHCBJPUTCKATP-FAWZKKEFSA-N 0.000 claims description 2
229950004155 etorphine Drugs 0.000 claims description 2
229960002428 fentanyl Drugs 0.000 claims description 2
PJMPHNIQZUBGLI-UHFFFAOYSA-N fentanyl Chemical compound C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 PJMPHNIQZUBGLI-UHFFFAOYSA-N 0.000 claims description 2
229960004369 flufenamic acid Drugs 0.000 claims description 2
LPEPZBJOKDYZAD-UHFFFAOYSA-N flufenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 LPEPZBJOKDYZAD-UHFFFAOYSA-N 0.000 claims description 2
229960002390 flurbiprofen Drugs 0.000 claims description 2
SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 claims description 2
229960002870 gabapentin Drugs 0.000 claims description 2
231100000869 headache Toxicity 0.000 claims description 2
LLPOLZWFYMWNKH-CMKMFDCUSA-N hydrocodone Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)CC(=O)[C@@H]1OC1=C2C3=CC=C1OC LLPOLZWFYMWNKH-CMKMFDCUSA-N 0.000 claims description 2
229960000240 hydrocodone Drugs 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
WVLOADHCBXTIJK-YNHQPCIGSA-N hydromorphone Chemical compound O([C@H]1C(CC[C@H]23)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O WVLOADHCBXTIJK-YNHQPCIGSA-N 0.000 claims description 2
229960001410 hydromorphone Drugs 0.000 claims description 2
230000002631 hypothermal effect Effects 0.000 claims description 2
238000007455 ileostomy Methods 0.000 claims description 2
229960003441 imipramine oxide Drugs 0.000 claims description 2
QZIQORUGXBPDSU-UHFFFAOYSA-N imipramine oxide Chemical compound C1CC2=CC=CC=C2N(CCC[N+](C)([O-])C)C2=CC=CC=C21 QZIQORUGXBPDSU-UHFFFAOYSA-N 0.000 claims description 2
229960000905 indomethacin Drugs 0.000 claims description 2
208000014674 injury Diseases 0.000 claims description 2
PLIGPBGDXASWPX-UHFFFAOYSA-N iprindole Chemical compound C1CCCCCC2=C1N(CCCN(C)C)C1=CC=CC=C12 PLIGPBGDXASWPX-UHFFFAOYSA-N 0.000 claims description 2
229960004752 ketorolac Drugs 0.000 claims description 2
OZWKMVRBQXNZKK-UHFFFAOYSA-N ketorolac Chemical compound OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 claims description 2
229960001848 lamotrigine Drugs 0.000 claims description 2
PYZRQGJRPPTADH-UHFFFAOYSA-N lamotrigine Chemical compound NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl PYZRQGJRPPTADH-UHFFFAOYSA-N 0.000 claims description 2
USSIQXCVUWKGNF-QGZVFWFLSA-N levomethadone Chemical compound C=1C=CC=CC=1C(C[C@@H](C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-QGZVFWFLSA-N 0.000 claims description 2
229960002710 levomethadone Drugs 0.000 claims description 2
229960003406 levorphanol Drugs 0.000 claims description 2
RDOIQAHITMMDAJ-UHFFFAOYSA-N loperamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)N(C)C)CCN(CC1)CCC1(O)C1=CC=C(Cl)C=C1 RDOIQAHITMMDAJ-UHFFFAOYSA-N 0.000 claims description 2
229960001571 loperamide Drugs 0.000 claims description 2
229960002202 lornoxicam Drugs 0.000 claims description 2
OXROWJKCGCOJDO-JLHYYAGUSA-N lornoxicam Chemical compound O=C1C=2SC(Cl)=CC=2S(=O)(=O)N(C)\C1=C(\O)NC1=CC=CC=N1 OXROWJKCGCOJDO-JLHYYAGUSA-N 0.000 claims description 2
229960003803 meclofenamic acid Drugs 0.000 claims description 2
229960004794 melitracen Drugs 0.000 claims description 2
GWWLWDURRGNSRS-UHFFFAOYSA-N melitracen Chemical compound C1=CC=C2C(=CCCN(C)C)C3=CC=CC=C3C(C)(C)C2=C1 GWWLWDURRGNSRS-UHFFFAOYSA-N 0.000 claims description 2
229960001929 meloxicam Drugs 0.000 claims description 2
JLICHNCFTLFZJN-HNNXBMFYSA-N meptazinol Chemical compound C=1C=CC(O)=CC=1[C@@]1(CC)CCCCN(C)C1 JLICHNCFTLFZJN-HNNXBMFYSA-N 0.000 claims description 2
229960000365 meptazinol Drugs 0.000 claims description 2
229960001797 methadone Drugs 0.000 claims description 2
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims description 2
229960001252 methamphetamine Drugs 0.000 claims description 2
GVXBHSBKKJRBMS-UHFFFAOYSA-N metralindole Chemical compound C1CN(C)C2=NCCC3=C2N1C1=CC=C(OC)C=C13 GVXBHSBKKJRBMS-UHFFFAOYSA-N 0.000 claims description 2
229950006787 metralindole Drugs 0.000 claims description 2
229960003955 mianserin Drugs 0.000 claims description 2
229960004758 minaprine Drugs 0.000 claims description 2
LDMWSLGGVTVJPG-UHFFFAOYSA-N minaprine Chemical compound CC1=CC(C=2C=CC=CC=2)=NN=C1NCCN1CCOCC1 LDMWSLGGVTVJPG-UHFFFAOYSA-N 0.000 claims description 2
229960005285 mofebutazone Drugs 0.000 claims description 2
REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical compound O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 claims description 2
201000006417 multiple sclerosis Diseases 0.000 claims description 2
239000003681 muscarinic M3 receptor antagonist Substances 0.000 claims description 2
239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 claims description 2
229960004270 nabumetone Drugs 0.000 claims description 2
NETZHAKZCGBWSS-CEDHKZHLSA-N nalbuphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]1(O)CC[C@@H]3O)CN2CC1CCC1 NETZHAKZCGBWSS-CEDHKZHLSA-N 0.000 claims description 2
229960000805 nalbuphine Drugs 0.000 claims description 2
UZHSEJADLWPNLE-GRGSLBFTSA-N naloxone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4CC=C UZHSEJADLWPNLE-GRGSLBFTSA-N 0.000 claims description 2
229960004127 naloxone Drugs 0.000 claims description 2
LCAFGJGYCUMTGS-UHFFFAOYSA-N nebracetam Chemical compound O=C1CC(CN)CN1CC1=CC=CC=C1 LCAFGJGYCUMTGS-UHFFFAOYSA-N 0.000 claims description 2
229950010963 nebracetam Drugs 0.000 claims description 2
230000008764 nerve damage Effects 0.000 claims description 2
230000003959 neuroinflammation Effects 0.000 claims description 2
201000001119 neuropathy Diseases 0.000 claims description 2
230000007823 neuropathy Effects 0.000 claims description 2
229960000916 niflumic acid Drugs 0.000 claims description 2
229960001073 nomifensine Drugs 0.000 claims description 2
XXPANQJNYNUNES-UHFFFAOYSA-N nomifensine Chemical compound C12=CC=CC(N)=C2CN(C)CC1C1=CC=CC=C1 XXPANQJNYNUNES-UHFFFAOYSA-N 0.000 claims description 2
WIQRCHMSJFFONW-UHFFFAOYSA-N norfluoxetine Chemical compound C=1C=CC=CC=1C(CCN)OC1=CC=C(C(F)(F)F)C=C1 WIQRCHMSJFFONW-UHFFFAOYSA-N 0.000 claims description 2
239000002777 nucleoside Substances 0.000 claims description 2
229960005290 opipramol Drugs 0.000 claims description 2
229960001816 oxcarbazepine Drugs 0.000 claims description 2
CTRLABGOLIVAIY-UHFFFAOYSA-N oxcarbazepine Chemical compound C1C(=O)C2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 CTRLABGOLIVAIY-UHFFFAOYSA-N 0.000 claims description 2
229960002085 oxycodone Drugs 0.000 claims description 2
229960005118 oxymorphone Drugs 0.000 claims description 2
229960000649 oxyphenbutazone Drugs 0.000 claims description 2
HFHZKZSRXITVMK-UHFFFAOYSA-N oxyphenbutazone Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=C(O)C=C1 HFHZKZSRXITVMK-UHFFFAOYSA-N 0.000 claims description 2
229960001592 paclitaxel Drugs 0.000 claims description 2
208000005877 painful neuropathy Diseases 0.000 claims description 2
229960005489 paracetamol Drugs 0.000 claims description 2
229960004662 parecoxib Drugs 0.000 claims description 2
TZRHLKRLEZJVIJ-UHFFFAOYSA-N parecoxib Chemical compound C1=CC(S(=O)(=O)NC(=O)CC)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 TZRHLKRLEZJVIJ-UHFFFAOYSA-N 0.000 claims description 2
239000004031 partial agonist Substances 0.000 claims description 2
VOKSWYLNZZRQPF-GDIGMMSISA-N pentazocine Chemical compound C1C2=CC=C(O)C=C2[C@@]2(C)[C@@H](C)[C@@H]1N(CC=C(C)C)CC2 VOKSWYLNZZRQPF-GDIGMMSISA-N 0.000 claims description 2
229960005301 pentazocine Drugs 0.000 claims description 2
208000033808 peripheral neuropathy Diseases 0.000 claims description 2
229950009253 perlapine Drugs 0.000 claims description 2
229960000964 phenelzine Drugs 0.000 claims description 2
CMCWWLVWPDLCRM-UHFFFAOYSA-N phenidone Chemical compound N1C(=O)CCN1C1=CC=CC=C1 CMCWWLVWPDLCRM-UHFFFAOYSA-N 0.000 claims description 2
229960002036 phenytoin Drugs 0.000 claims description 2
150000003109 potassium Chemical class 0.000 claims description 2
229960005205 prednisolone Drugs 0.000 claims description 2
OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims description 2
QTGAJCQTLIRCFL-UHFFFAOYSA-N propacetamol Chemical compound CCN(CC)CC(=O)OC1=CC=C(NC(C)=O)C=C1 QTGAJCQTLIRCFL-UHFFFAOYSA-N 0.000 claims description 2
229960003192 propacetamol Drugs 0.000 claims description 2
PXWLVJLKJGVOKE-UHFFFAOYSA-N propyphenazone Chemical compound O=C1C(C(C)C)=C(C)N(C)N1C1=CC=CC=C1 PXWLVJLKJGVOKE-UHFFFAOYSA-N 0.000 claims description 2
229960002189 propyphenazone Drugs 0.000 claims description 2
229960003394 remifentanil Drugs 0.000 claims description 2
230000002441 reversible effect Effects 0.000 claims description 2
HJORMJIFDVBMOB-UHFFFAOYSA-N rolipram Chemical compound COC1=CC=C(C2CC(=O)NC2)C=C1OC1CCCC1 HJORMJIFDVBMOB-UHFFFAOYSA-N 0.000 claims description 2
229950005741 rolipram Drugs 0.000 claims description 2
229960000581 salicylamide Drugs 0.000 claims description 2
UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 claims description 2
229960004425 sibutramine Drugs 0.000 claims description 2
239000003195 sodium channel blocking agent Substances 0.000 claims description 2
AEQFSUDEHCCHBT-UHFFFAOYSA-M sodium valproate Chemical compound [Na+].CCCC(C([O-])=O)CCC AEQFSUDEHCCHBT-UHFFFAOYSA-M 0.000 claims description 2
239000003890 substance P antagonist Substances 0.000 claims description 2
GGCSSNBKKAUURC-UHFFFAOYSA-N sufentanil Chemical group C1CN(CCC=2SC=CC=2)CCC1(COC)N(C(=O)CC)C1=CC=CC=C1 GGCSSNBKKAUURC-UHFFFAOYSA-N 0.000 claims description 2
229960004739 sufentanil Drugs 0.000 claims description 2
MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 claims description 2
229960000894 sulindac Drugs 0.000 claims description 2
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 2
229960002871 tenoxicam Drugs 0.000 claims description 2
MIMJSJSRRDZIPW-UHFFFAOYSA-N tilmacoxib Chemical compound C=1C=C(S(N)(=O)=O)C(F)=CC=1C=1OC(C)=NC=1C1CCCCC1 MIMJSJSRRDZIPW-UHFFFAOYSA-N 0.000 claims description 2
229960002501 tofisopam Drugs 0.000 claims description 2
229960004380 tramadol Drugs 0.000 claims description 2
TVYLLZQTGLZFBW-GOEBONIOSA-N tramadol Natural products COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GOEBONIOSA-N 0.000 claims description 2
LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 0.000 claims description 2
229960003741 tranylcypromine Drugs 0.000 claims description 2
206010044652 trigeminal neuralgia Diseases 0.000 claims description 2
229940102566 valproate Drugs 0.000 claims description 2
208000009935 visceral pain Diseases 0.000 claims description 2
KNJNGVKTAFTUFL-OCMUWRIYSA-N ω-conotoxin Chemical compound N([C@@H](CO)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H]1C(N[C@@H](CSSC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H]1C(N[C@@H](CCCN=C(N)N)C(=O)N[C@H](CO)C(=O)NCC(=O)N[C@H](CCCCN)C(=O)N[C@H](CSSC1)C(N)=O)=O)=O)C(=O)[C@@H]1CSSC[C@@H](N)C(=O)N[C@H](CCCCN)C(=O)NCC(=O)N[C@H](CCCCN)C(=O)NCC(=O)N[C@H](C)C(=O)N[C@@H](CCCCN)C(=O)N1 KNJNGVKTAFTUFL-OCMUWRIYSA-N 0.000 claims description 2
108091058550 ω-conotoxin Proteins 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 11
125000002877 alkyl aryl group Chemical group 0.000 claims 7
125000000623 heterocyclic group Chemical group 0.000 claims 6
125000003118 aryl group Chemical group 0.000 claims 5
229940002612 prodrug Drugs 0.000 claims 5
239000000651 prodrug Substances 0.000 claims 5
125000005309 thioalkoxy group Chemical group 0.000 claims 4
GJJFMKBJSRMPLA-HIFRSBDPSA-N (1R,2S)-2-(aminomethyl)-N,N-diethyl-1-phenyl-1-cyclopropanecarboxamide Chemical compound C=1C=CC=CC=1[C@@]1(C(=O)N(CC)CC)C[C@@H]1CN GJJFMKBJSRMPLA-HIFRSBDPSA-N 0.000 claims 3
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
125000003545 alkoxy group Chemical group 0.000 claims 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
229960000600 milnacipran Drugs 0.000 claims 3
229910052757 nitrogen Inorganic materials 0.000 claims 3
229910052760 oxygen Inorganic materials 0.000 claims 3
RDJGLLICXDHJDY-NSHDSACASA-N (2s)-2-(3-phenoxyphenyl)propanoic acid Chemical compound OC(=O)[C@@H](C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-NSHDSACASA-N 0.000 claims 2
PJJGZPJJTHBVMX-UHFFFAOYSA-N 5,7-Dihydroxyisoflavone Chemical compound C=1C(O)=CC(O)=C(C2=O)C=1OC=C2C1=CC=CC=C1 PJJGZPJJTHBVMX-UHFFFAOYSA-N 0.000 claims 2
GDLIGKIOYRNHDA-UHFFFAOYSA-N Clomipramine Chemical compound C1CC2=CC=C(Cl)C=C2N(CCCN(C)C)C2=CC=CC=C21 GDLIGKIOYRNHDA-UHFFFAOYSA-N 0.000 claims 2
102100029111 Fatty-acid amide hydrolase 1 Human genes 0.000 claims 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
229960003148 adinazolam Drugs 0.000 claims 2
GJSLOMWRLALDCT-UHFFFAOYSA-N adinazolam Chemical compound C12=CC(Cl)=CC=C2N2C(CN(C)C)=NN=C2CN=C1C1=CC=CC=C1 GJSLOMWRLALDCT-UHFFFAOYSA-N 0.000 claims 2
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims 2
229960000836 amitriptyline Drugs 0.000 claims 2
230000001430 anti-depressive effect Effects 0.000 claims 2
230000000561 anti-psychotic effect Effects 0.000 claims 2
239000000939 antiparkinson agent Substances 0.000 claims 2
229960002430 atomoxetine Drugs 0.000 claims 2
VHGCDTVCOLNTBX-QGZVFWFLSA-N atomoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=CC=C1C VHGCDTVCOLNTBX-QGZVFWFLSA-N 0.000 claims 2
229960004606 clomipramine Drugs 0.000 claims 2
230000001079 digestive effect Effects 0.000 claims 2
108010046094 fatty-acid amide hydrolase Proteins 0.000 claims 2
229960001419 fenoprofen Drugs 0.000 claims 2
239000003825 glutamate receptor antagonist Substances 0.000 claims 2
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims 2
229960001785 mirtazapine Drugs 0.000 claims 2
239000008194 pharmaceutical composition Substances 0.000 claims 2
239000000546 pharmaceutical excipient Substances 0.000 claims 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
229910052717 sulfur Inorganic materials 0.000 claims 2
229960002004 valdecoxib Drugs 0.000 claims 2
LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 claims 2
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 claims 1
UCKHICKHGAOGAP-UONOGXRCSA-N (2R,4S)-4-[[anilino(oxo)methyl]amino]-5,7-dichloro-1,2,3,4-tetrahydroquinoline-2-carboxylic acid Chemical compound N([C@H]1C[C@@H](NC2=CC(Cl)=CC(Cl)=C21)C(=O)O)C(=O)NC1=CC=CC=C1 UCKHICKHGAOGAP-UONOGXRCSA-N 0.000 claims 1
YWPHCCPCQOJSGZ-LLVKDONJSA-N (2r)-2-[(2-ethoxyphenoxy)methyl]morpholine Chemical compound CCOC1=CC=CC=C1OC[C@@H]1OCCNC1 YWPHCCPCQOJSGZ-LLVKDONJSA-N 0.000 claims 1
QXWYKJLNLSIPIN-YUMQZZPRSA-N (2s,3s)-2-azaniumyl-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoate Chemical compound [O-]C(=O)[C@@H]([NH3+])[C@@H](O)C1=CC=C(O)C(O)=C1 QXWYKJLNLSIPIN-YUMQZZPRSA-N 0.000 claims 1
JQQWDYJWDCIVKQ-QUCCMNQESA-N (3r,4s)-3-(4-benzyl-4-hydroxypiperidin-1-yl)-3,4-dihydro-2h-chromene-4,7-diol Chemical compound C1CN([C@H]2[C@H](C3=CC=C(O)C=C3OC2)O)CCC1(O)CC1=CC=CC=C1 JQQWDYJWDCIVKQ-QUCCMNQESA-N 0.000 claims 1
DQNMZSIJHFEYTM-LEWJYISDSA-N (4s,5r)-3-[3-(azepan-1-yl)propyl]-4-(2-methylpropyl)-5-phenyl-1,3-oxazolidin-2-one Chemical compound O([C@@H]([C@@H]1CC(C)C)C=2C=CC=CC=2)C(=O)N1CCCN1CCCCCC1 DQNMZSIJHFEYTM-LEWJYISDSA-N 0.000 claims 1
RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 claims 1
BGRJTUBHPOOWDU-NSHDSACASA-N (S)-(-)-sulpiride Chemical compound CCN1CCC[C@H]1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-NSHDSACASA-N 0.000 claims 1
ZEUITGRIYCTCEM-KRWDZBQOSA-N (S)-duloxetine Chemical compound C1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCNC)=CC=CS1 ZEUITGRIYCTCEM-KRWDZBQOSA-N 0.000 claims 1
WSPOMRSOLSGNFJ-AUWJEWJLSA-N (Z)-chlorprothixene Chemical compound C1=C(Cl)C=C2C(=C/CCN(C)C)\C3=CC=CC=C3SC2=C1 WSPOMRSOLSGNFJ-AUWJEWJLSA-N 0.000 claims 1
ZEFQYTSQDVUMEU-GQCTYLIASA-N (e)-2-amino-4-(phosphonomethyl)hept-3-enoic acid Chemical compound CCC\C(CP(O)(O)=O)=C/C(N)C(O)=O ZEFQYTSQDVUMEU-GQCTYLIASA-N 0.000 claims 1
VKMFDKYCIKEDMR-UHFFFAOYSA-N 1-[2-(4-hydroxyphenoxy)ethyl]-4-[(4-methylphenyl)methyl]-4-piperidinol Chemical compound C1=CC(C)=CC=C1CC1(O)CCN(CCOC=2C=CC(O)=CC=2)CC1 VKMFDKYCIKEDMR-UHFFFAOYSA-N 0.000 claims 1
NILQLFBWTXNUOE-UHFFFAOYSA-N 1-aminocyclopentanecarboxylic acid Chemical compound OC(=O)C1(N)CCCC1 NILQLFBWTXNUOE-UHFFFAOYSA-N 0.000 claims 1
FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 claims 1
FDLWTGJOICYQBK-UHFFFAOYSA-N 2-(1,4-diazatricyclo[7.3.1.05,13]trideca-3,5,7,9(13),10-pentaen-12-yl)acetamide Chemical compound N1=CCN2C(CC(=O)N)C=CC3=CC=CC1=C32 FDLWTGJOICYQBK-UHFFFAOYSA-N 0.000 claims 1
JHVHEDNLONERHY-UHFFFAOYSA-N 2-(2-chloro-5-methylsulfanylphenyl)-1-methyl-1-(3-methylsulfanylphenyl)guanidine Chemical compound CSC1=CC=CC(N(C)C(N)=NC=2C(=CC=C(SC)C=2)Cl)=C1 JHVHEDNLONERHY-UHFFFAOYSA-N 0.000 claims 1
RODJWDCTFWIGQR-HSZRJFAPSA-N 2-(2-chloro-5-methylsulfanylphenyl)-1-methyl-1-[3-[(r)-methylsulfinyl]phenyl]guanidine Chemical compound CSC1=CC=C(Cl)C(NC(=N)N(C)C=2C=C(C=CC=2)[S@@](C)=O)=C1 RODJWDCTFWIGQR-HSZRJFAPSA-N 0.000 claims 1
FGWCGTHNUZKAKL-UHFFFAOYSA-N 2-(3-hydroxy-3-methylbutoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1N(OCCC(C)(O)C)N=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=C1 FGWCGTHNUZKAKL-UHFFFAOYSA-N 0.000 claims 1
JNZBIEKQOFEXIO-UHFFFAOYSA-N 2-amino-2-[4-(phosphonomethyl)phenyl]acetic acid Chemical compound OC(=O)C(N)C1=CC=C(CP(O)(O)=O)C=C1 JNZBIEKQOFEXIO-UHFFFAOYSA-N 0.000 claims 1
DHJQWBSZKBDBFP-UHFFFAOYSA-N 2-amino-3-[2-(2-phosphonoethyl)cyclohexyl]propanoic acid Chemical compound OC(=O)C(N)CC1CCCCC1CCP(O)(O)=O DHJQWBSZKBDBFP-UHFFFAOYSA-N 0.000 claims 1
CFWRDBDJAOHXSH-SECBINFHSA-N 2-azaniumylethyl [(2r)-2,3-diacetyloxypropyl] phosphate Chemical compound CC(=O)OC[C@@H](OC(C)=O)COP(O)(=O)OCCN CFWRDBDJAOHXSH-SECBINFHSA-N 0.000 claims 1
HXBCOTBMAZLVFL-UHFFFAOYSA-N 2-hydroxy-5-[(2,3,4,5,6-pentafluorophenyl)methylamino]benzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(NCC=2C(=C(F)C(F)=C(F)C=2F)F)=C1 HXBCOTBMAZLVFL-UHFFFAOYSA-N 0.000 claims 1
NEWKHUASLBMWRE-UHFFFAOYSA-N 2-methyl-6-(phenylethynyl)pyridine Chemical compound CC1=CC=CC(C#CC=2C=CC=CC=2)=N1 NEWKHUASLBMWRE-UHFFFAOYSA-N 0.000 claims 1
LPWVUDLZUVBQGP-DHZHZOJOSA-N 3-[(e)-2-carboxy-2-phenylethenyl]-4,6-dichloro-1h-indole-2-carboxylic acid Chemical compound OC(=O)C=1NC2=CC(Cl)=CC(Cl)=C2C=1/C=C(C(=O)O)\C1=CC=CC=C1 LPWVUDLZUVBQGP-DHZHZOJOSA-N 0.000 claims 1
VDIRQCDDCGAGET-DHZHZOJOSA-N 4,6-dichloro-3-[(e)-(2-oxo-1-phenylpyrrolidin-3-ylidene)methyl]-1h-indole-2-carboxylic acid Chemical compound OC(=O)C=1NC2=CC(Cl)=CC(Cl)=C2C=1\C=C(C1=O)/CCN1C1=CC=CC=C1 VDIRQCDDCGAGET-DHZHZOJOSA-N 0.000 claims 1
CXSBVUAWHYXWQZ-UHFFFAOYSA-N 4-benzyl-1-[4-(1h-imidazol-5-yl)but-3-ynyl]piperidine Chemical compound C=1NC=NC=1C#CCCN(CC1)CCC1CC1=CC=CC=C1 CXSBVUAWHYXWQZ-UHFFFAOYSA-N 0.000 claims 1
FCBQJNCAKZSIAH-UHFFFAOYSA-N 6-[2-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]ethylsulfinyl]-3h-1,3-benzoxazol-2-one Chemical compound C1=CC(F)=CC=C1CC1CCN(CCS(=O)C=2C=C3OC(=O)NC3=CC=2)CC1 FCBQJNCAKZSIAH-UHFFFAOYSA-N 0.000 claims 1
ZIHZRNXJNHFWHN-UHFFFAOYSA-N 6-methyl-5-(methylaminomethyl)-7-nitro-1,4-dihydroquinoxaline-2,3-dione Chemical compound N1C(=O)C(=O)NC2=C1C=C([N+]([O-])=O)C(C)=C2CNC ZIHZRNXJNHFWHN-UHFFFAOYSA-N 0.000 claims 1
JICJBGPOMZQUBB-UHFFFAOYSA-N 7-[(3-chloro-6-methyl-5,5-dioxido-6,11-dihydrodibenzo[c,f][1,2]thiazepin-11-yl)amino]heptanoic acid Chemical compound O=S1(=O)N(C)C2=CC=CC=C2C(NCCCCCCC(O)=O)C2=CC=C(Cl)C=C21 JICJBGPOMZQUBB-UHFFFAOYSA-N 0.000 claims 1
229940122578 Acetylcholine receptor agonist Drugs 0.000 claims 1
CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 claims 1
102000015554 Dopamine receptor Human genes 0.000 claims 1
108050004812 Dopamine receptor Proteins 0.000 claims 1
PLDUPXSUYLZYBN-UHFFFAOYSA-N Fluphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 PLDUPXSUYLZYBN-UHFFFAOYSA-N 0.000 claims 1
239000004471 Glycine Substances 0.000 claims 1
NYMGNSNKLVNMIA-UHFFFAOYSA-N Iproniazid Chemical compound CC(C)NNC(=O)C1=CC=NC=C1 NYMGNSNKLVNMIA-UHFFFAOYSA-N 0.000 claims 1
229940123572 Kainate receptor antagonist Drugs 0.000 claims 1
YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 claims 1
WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical group OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims 1
WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims 1
MKXZASYAUGDDCJ-SZMVWBNQSA-N LSM-2525 Chemical compound C1CCC[C@H]2[C@@]3([H])N(C)CC[C@]21C1=CC(OC)=CC=C1C3 MKXZASYAUGDDCJ-SZMVWBNQSA-N 0.000 claims 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
229940091512 Monoamine oxidase A inhibitor Drugs 0.000 claims 1
BATFHSIVMJJJAF-UHFFFAOYSA-N Morindone Chemical compound OC1=CC=C2C(=O)C3=C(O)C(C)=CC=C3C(=O)C2=C1O BATFHSIVMJJJAF-UHFFFAOYSA-N 0.000 claims 1
JUUFBMODXQKSTD-UHFFFAOYSA-N N-[2-amino-6-[(4-fluorophenyl)methylamino]-3-pyridinyl]carbamic acid ethyl ester Chemical compound N1=C(N)C(NC(=O)OCC)=CC=C1NCC1=CC=C(F)C=C1 JUUFBMODXQKSTD-UHFFFAOYSA-N 0.000 claims 1
DPWPWRLQFGFJFI-UHFFFAOYSA-N Pargyline Chemical compound C#CCN(C)CC1=CC=CC=C1 DPWPWRLQFGFJFI-UHFFFAOYSA-N 0.000 claims 1
RGCVKNLCSQQDEP-UHFFFAOYSA-N Perphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 RGCVKNLCSQQDEP-UHFFFAOYSA-N 0.000 claims 1
ZGUGWUXLJSTTMA-UHFFFAOYSA-N Promazinum Chemical compound C1=CC=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZGUGWUXLJSTTMA-UHFFFAOYSA-N 0.000 claims 1
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 1
208000006011 Stroke Diseases 0.000 claims 1
KLBQZWRITKRQQV-UHFFFAOYSA-N Thioridazine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C KLBQZWRITKRQQV-UHFFFAOYSA-N 0.000 claims 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
229960000276 acetophenazine Drugs 0.000 claims 1
WNTYBHLDCKXEOT-UHFFFAOYSA-N acetophenazine Chemical compound C12=CC(C(=O)C)=CC=C2SC2=CC=CC=C2N1CCCN1CCN(CCO)CC1 WNTYBHLDCKXEOT-UHFFFAOYSA-N 0.000 claims 1
239000000048 adrenergic agonist Substances 0.000 claims 1
229940126157 adrenergic receptor agonist Drugs 0.000 claims 1
102000030484 alpha-2 Adrenergic Receptor Human genes 0.000 claims 1
108020004101 alpha-2 Adrenergic Receptor Proteins 0.000 claims 1
DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims 1
229960003805 amantadine Drugs 0.000 claims 1
VDPUXONTAVMIKZ-UHFFFAOYSA-N amineptine hydrochloride Chemical compound [Cl-].C1CC2=CC=CC=C2C([NH2+]CCCCCCC(=O)O)C2=CC=CC=C21 VDPUXONTAVMIKZ-UHFFFAOYSA-N 0.000 claims 1
229960002519 amoxapine Drugs 0.000 claims 1
QWGDMFLQWFTERH-UHFFFAOYSA-N amoxapine Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2N=C1N1CCNCC1 QWGDMFLQWFTERH-UHFFFAOYSA-N 0.000 claims 1
230000003078 antioxidant effect Effects 0.000 claims 1
235000006708 antioxidants Nutrition 0.000 claims 1
229940125688 antiparkinson agent Drugs 0.000 claims 1
BFNCJMURTMZBTE-UHFFFAOYSA-N aptiganel Chemical compound CCC1=CC=CC(N(C)C(N)=NC=2C3=CC=CC=C3C=CC=2)=C1 BFNCJMURTMZBTE-UHFFFAOYSA-N 0.000 claims 1
229950001180 aptiganel Drugs 0.000 claims 1
229960004372 aripiprazole Drugs 0.000 claims 1
QIHLUZAFSSMXHQ-UHFFFAOYSA-N budipine Chemical compound C1CN(C(C)(C)C)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 QIHLUZAFSSMXHQ-UHFFFAOYSA-N 0.000 claims 1
229960002452 budipine Drugs 0.000 claims 1
229960001058 bupropion Drugs 0.000 claims 1
SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 claims 1
239000003554 cannabinoid 1 receptor agonist Substances 0.000 claims 1
239000003556 cannabinoid 2 receptor agonist Substances 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
QPWYZQIIZHEABR-IRWQIABSSA-N chembl100429 Chemical compound C1C2=CC(O)=CC=C2[C@]2(C)CCN(C[C@H](C)OC)[C@@]1([H])C2(C)C QPWYZQIIZHEABR-IRWQIABSSA-N 0.000 claims 1
229960001076 chlorpromazine Drugs 0.000 claims 1
ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 claims 1
229960001552 chlorprothixene Drugs 0.000 claims 1
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims 1
NJMYODHXAKYRHW-DVZOWYKESA-N cis-flupenthixol Chemical compound C1CN(CCO)CCN1CC\C=C\1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C2/1 NJMYODHXAKYRHW-DVZOWYKESA-N 0.000 claims 1
229960004170 clozapine Drugs 0.000 claims 1
QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 claims 1
WDEFBBTXULIOBB-WBVHZDCISA-N dextilidine Chemical compound C=1C=CC=CC=1[C@@]1(C(=O)OCC)CCC=C[C@H]1N(C)C WDEFBBTXULIOBB-WBVHZDCISA-N 0.000 claims 1
USSIQXCVUWKGNF-KRWDZBQOSA-N dextromethadone Chemical compound C=1C=CC=CC=1C(C[C@H](C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-KRWDZBQOSA-N 0.000 claims 1
229960001985 dextromethorphan Drugs 0.000 claims 1
201000010099 disease Diseases 0.000 claims 1
229950010344 donitriptan Drugs 0.000 claims 1
SOHCKWZVTCTQBG-UHFFFAOYSA-N donitriptan Chemical compound C1=C2C(CCN)=CNC2=CC=C1OCC(=O)N(CC1)CCN1C1=CC=C(C#N)C=C1 SOHCKWZVTCTQBG-UHFFFAOYSA-N 0.000 claims 1
229960000394 droperidol Drugs 0.000 claims 1
RMEDXOLNCUSCGS-UHFFFAOYSA-N droperidol Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CC=C(N2C(NC3=CC=CC=C32)=O)CC1 RMEDXOLNCUSCGS-UHFFFAOYSA-N 0.000 claims 1
230000009977 dual effect Effects 0.000 claims 1
229960002866 duloxetine Drugs 0.000 claims 1
229960002472 eletriptan Drugs 0.000 claims 1
OTLDLQZJRFYOJR-LJQANCHMSA-N eletriptan Chemical group CN1CCC[C@@H]1CC1=CN=C2[C]1C=C(CCS(=O)(=O)C=1C=CC=CC=1)C=C2 OTLDLQZJRFYOJR-LJQANCHMSA-N 0.000 claims 1
229960004341 escitalopram Drugs 0.000 claims 1
WSEQXVZVJXJVFP-FQEVSTJZSA-N escitalopram Chemical compound C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-FQEVSTJZSA-N 0.000 claims 1
229960002336 estazolam Drugs 0.000 claims 1
CDCHDCWJMGXXRH-UHFFFAOYSA-N estazolam Chemical compound C=1C(Cl)=CC=C(N2C=NN=C2CN=2)C=1C=2C1=CC=CC=C1 CDCHDCWJMGXXRH-UHFFFAOYSA-N 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
229960005437 etoperidone Drugs 0.000 claims 1
IZBNNCFOBMGTQX-UHFFFAOYSA-N etoperidone Chemical compound O=C1N(CC)C(CC)=NN1CCCN1CCN(C=2C=C(Cl)C=CC=2)CC1 IZBNNCFOBMGTQX-UHFFFAOYSA-N 0.000 claims 1
PCOBBVZJEWWZFR-UHFFFAOYSA-N ezogabine Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=CC=C(F)C=C1 PCOBBVZJEWWZFR-UHFFFAOYSA-N 0.000 claims 1
229960003472 felbamate Drugs 0.000 claims 1
WKGXYQFOCVYPAC-UHFFFAOYSA-N felbamate Chemical compound NC(=O)OCC(COC(N)=O)C1=CC=CC=C1 WKGXYQFOCVYPAC-UHFFFAOYSA-N 0.000 claims 1
229960002464 fluoxetine Drugs 0.000 claims 1
229960002419 flupentixol Drugs 0.000 claims 1
229960002690 fluphenazine Drugs 0.000 claims 1
229960003667 flupirtine Drugs 0.000 claims 1
229960004038 fluvoxamine Drugs 0.000 claims 1
CJOFXWAVKWHTFT-XSFVSMFZSA-N fluvoxamine Chemical compound COCCCC\C(=N/OCCN)C1=CC=C(C(F)(F)F)C=C1 CJOFXWAVKWHTFT-XSFVSMFZSA-N 0.000 claims 1
229960002284 frovatriptan Drugs 0.000 claims 1
SIBNYOSJIXCDRI-SECBINFHSA-N frovatriptan Chemical compound C1=C(C(N)=O)[CH]C2=C(C[C@H](NC)CC3)C3=NC2=C1 SIBNYOSJIXCDRI-SECBINFHSA-N 0.000 claims 1
DKFAAPPUYWQKKF-GOEBONIOSA-N gacyclidine Chemical compound C[C@H]1CCCC[C@@]1(C=1SC=CC=1)N1CCCCC1 DKFAAPPUYWQKKF-GOEBONIOSA-N 0.000 claims 1
229950003638 gacyclidine Drugs 0.000 claims 1
229960002449 glycine Drugs 0.000 claims 1
229960003878 haloperidol Drugs 0.000 claims 1
125000001072 heteroaryl group Chemical group 0.000 claims 1
125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
229960003162 iloperidone Drugs 0.000 claims 1
XMXHEBAFVSFQEX-UHFFFAOYSA-N iloperidone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(C=2C3=CC=C(F)C=C3ON=2)CC1 XMXHEBAFVSFQEX-UHFFFAOYSA-N 0.000 claims 1
MNLULKBKWKTZPE-UHFFFAOYSA-N indantadol Chemical compound C1=CC=C2CC(NCC(=O)N)CC2=C1 MNLULKBKWKTZPE-UHFFFAOYSA-N 0.000 claims 1
229950010499 ipenoxazone Drugs 0.000 claims 1
229960002844 iprindole Drugs 0.000 claims 1
229940070023 iproniazide Drugs 0.000 claims 1
229950002252 isoxicam Drugs 0.000 claims 1
YYUAYBYLJSNDCX-UHFFFAOYSA-N isoxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC=1C=C(C)ON=1 YYUAYBYLJSNDCX-UHFFFAOYSA-N 0.000 claims 1
239000002873 kainic acid receptor antagonist Substances 0.000 claims 1
229960003299 ketamine Drugs 0.000 claims 1
229960004502 levodopa Drugs 0.000 claims 1
229910052744 lithium Inorganic materials 0.000 claims 1
229960000423 loxapine Drugs 0.000 claims 1
XJGVXQDUIWGIRW-UHFFFAOYSA-N loxapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2OC2=CC=C(Cl)C=C12 XJGVXQDUIWGIRW-UHFFFAOYSA-N 0.000 claims 1
STIRHCNEGQQBOY-QEYWKRMJSA-N ly-235,959 Chemical compound C1[C@@H](CP(O)(O)=O)CC[C@H]2CN[C@H](C(=O)O)C[C@H]21 STIRHCNEGQQBOY-QEYWKRMJSA-N 0.000 claims 1
BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 claims 1
229960004640 memantine Drugs 0.000 claims 1
229960000300 mesoridazine Drugs 0.000 claims 1
SLVMESMUVMCQIY-UHFFFAOYSA-N mesoridazine Chemical compound CN1CCCCC1CCN1C2=CC(S(C)=O)=CC=C2SC2=CC=CC=C21 SLVMESMUVMCQIY-UHFFFAOYSA-N 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
239000000359 muscarinic M1 receptor agonist Substances 0.000 claims 1
229960005254 naratriptan Drugs 0.000 claims 1
UNHGSHHVDNGCFN-UHFFFAOYSA-N naratriptan Chemical compound C=12[CH]C(CCS(=O)(=O)NC)=CC=C2N=CC=1C1CCN(C)CC1 UNHGSHHVDNGCFN-UHFFFAOYSA-N 0.000 claims 1
229960001800 nefazodone Drugs 0.000 claims 1
VRBKIVRKKCLPHA-UHFFFAOYSA-N nefazodone Chemical compound O=C1N(CCOC=2C=CC=CC=2)C(CC)=NN1CCCN(CC1)CCN1C1=CC=CC(Cl)=C1 VRBKIVRKKCLPHA-UHFFFAOYSA-N 0.000 claims 1
OGZQTTHDGQBLBT-UHFFFAOYSA-N neramexane Chemical compound CC1(C)CC(C)(C)CC(C)(N)C1 OGZQTTHDGQBLBT-UHFFFAOYSA-N 0.000 claims 1
229950004543 neramexane Drugs 0.000 claims 1
210000005036 nerve Anatomy 0.000 claims 1
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 1
229940126569 noradrenaline reuptake inhibitor Drugs 0.000 claims 1
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 claims 1
229960005017 olanzapine Drugs 0.000 claims 1
KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 claims 1
QVYRGXJJSLMXQH-UHFFFAOYSA-N orphenadrine Chemical compound C=1C=CC=C(C)C=1C(OCCN(C)C)C1=CC=CC=C1 QVYRGXJJSLMXQH-UHFFFAOYSA-N 0.000 claims 1
229960003941 orphenadrine Drugs 0.000 claims 1
201000008482 osteoarthritis Diseases 0.000 claims 1
229960001779 pargyline Drugs 0.000 claims 1
230000001717 pathogenic effect Effects 0.000 claims 1
229960000762 perphenazine Drugs 0.000 claims 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
229960005190 phenylalanine Drugs 0.000 claims 1
YVUQSNJEYSNKRX-UHFFFAOYSA-N pimozide Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1CCC(N2C(NC3=CC=CC=C32)=O)CC1 YVUQSNJEYSNKRX-UHFFFAOYSA-N 0.000 claims 1
229960003634 pimozide Drugs 0.000 claims 1
FCTRVTQZOUKUIV-MCDZGGTQSA-M potassium;[[[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound [K+].C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)([O-])=O)[C@@H](O)[C@H]1O FCTRVTQZOUKUIV-MCDZGGTQSA-M 0.000 claims 1
FASDKYOPVNHBLU-ZETCQYMHSA-N pramipexole Chemical compound C1[C@@H](NCCC)CCC2=C1SC(N)=N2 FASDKYOPVNHBLU-ZETCQYMHSA-N 0.000 claims 1
229960003089 pramipexole Drugs 0.000 claims 1
229960003598 promazine Drugs 0.000 claims 1
YFLBETLXDPBWTD-UHFFFAOYSA-N propizepine Chemical compound O=C1N(CC(C)N(C)C)C2=CC=CC=C2NC2=NC=CC=C21 YFLBETLXDPBWTD-UHFFFAOYSA-N 0.000 claims 1
229950003857 propizepine Drugs 0.000 claims 1
229960002601 protriptyline Drugs 0.000 claims 1
BWPIARFWQZKAIA-UHFFFAOYSA-N protriptyline Chemical compound C1=CC2=CC=CC=C2C(CCCNC)C2=CC=CC=C21 BWPIARFWQZKAIA-UHFFFAOYSA-N 0.000 claims 1
229960004431 quetiapine Drugs 0.000 claims 1
URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 claims 1
229960003770 reboxetine Drugs 0.000 claims 1
CBQGYUDMJHNJBX-RTBURBONSA-N reboxetine Chemical compound CCOC1=CC=CC=C1O[C@H](C=1C=CC=CC=1)[C@@H]1OCCNC1 CBQGYUDMJHNJBX-RTBURBONSA-N 0.000 claims 1
229960003312 retigabine Drugs 0.000 claims 1
229960003471 retinol Drugs 0.000 claims 1
235000020944 retinol Nutrition 0.000 claims 1
239000011607 retinol Substances 0.000 claims 1
229960001534 risperidone Drugs 0.000 claims 1
RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 claims 1
229960000425 rizatriptan Drugs 0.000 claims 1
TXHZXHICDBAVJW-UHFFFAOYSA-N rizatriptan Chemical compound C=1[C]2C(CCN(C)C)=CN=C2C=CC=1CN1C=NC=N1 TXHZXHICDBAVJW-UHFFFAOYSA-N 0.000 claims 1
229940124834 selective serotonin reuptake inhibitor Drugs 0.000 claims 1
239000012896 selective serotonin reuptake inhibitor Substances 0.000 claims 1
229940126570 serotonin reuptake inhibitor Drugs 0.000 claims 1
239000003772 serotonin uptake inhibitor Substances 0.000 claims 1
229960000652 sertindole Drugs 0.000 claims 1
GZKLJWGUPQBVJQ-UHFFFAOYSA-N sertindole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C(C2CCN(CCN3C(NCC3)=O)CC2)=C1 GZKLJWGUPQBVJQ-UHFFFAOYSA-N 0.000 claims 1
229960002073 sertraline Drugs 0.000 claims 1
VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 claims 1
229940125794 sodium channel blocker Drugs 0.000 claims 1
208000020431 spinal cord injury Diseases 0.000 claims 1
201000009032 substance abuse Diseases 0.000 claims 1
231100000736 substance abuse Toxicity 0.000 claims 1
229960003211 sulbutiamine Drugs 0.000 claims 1
CKHJPWQVLKHBIH-ZDSKVHJSSA-N sulbutiamine Chemical compound C=1N=C(C)N=C(N)C=1CN(C=O)C(/C)=C(/CCOC(=O)C(C)C)SS\C(CCOC(=O)C(C)C)=C(\C)N(C=O)CC1=CN=C(C)N=C1N CKHJPWQVLKHBIH-ZDSKVHJSSA-N 0.000 claims 1
125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
229960004940 sulpiride Drugs 0.000 claims 1
229960003708 sumatriptan Drugs 0.000 claims 1
KQKPFRSPSRPDEB-UHFFFAOYSA-N sumatriptan Chemical compound CNS(=O)(=O)CC1=CC=C2NC=C(CCN(C)C)C2=C1 KQKPFRSPSRPDEB-UHFFFAOYSA-N 0.000 claims 1
OILWWIVKIDXCIB-UHFFFAOYSA-N teniloxazine Chemical compound C1NCCOC1COC1=CC=CC=C1CC1=CC=CS1 OILWWIVKIDXCIB-UHFFFAOYSA-N 0.000 claims 1
229950003014 teniloxazine Drugs 0.000 claims 1
LZNWYQJJBLGYLT-UHFFFAOYSA-N tenoxicam Chemical compound OC=1C=2SC=CC=2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 LZNWYQJJBLGYLT-UHFFFAOYSA-N 0.000 claims 1
229960002784 thioridazine Drugs 0.000 claims 1
JJSHYECKYLDYAR-UHFFFAOYSA-N thozalinone Chemical compound O1C(N(C)C)=NC(=O)C1C1=CC=CC=C1 JJSHYECKYLDYAR-UHFFFAOYSA-N 0.000 claims 1
229960005138 tianeptine Drugs 0.000 claims 1
229950008817 tiflucarbine Drugs 0.000 claims 1
BNKIWXODDDABSJ-UHFFFAOYSA-N tiflucarbine Chemical compound N1C2=CC(F)=C3SC=C(C)C3=C2C2=C1CCN(CC)C2 BNKIWXODDDABSJ-UHFFFAOYSA-N 0.000 claims 1
229960001402 tilidine Drugs 0.000 claims 1
238000011200 topical administration Methods 0.000 claims 1
229950007145 tozalinone Drugs 0.000 claims 1
229960003991 trazodone Drugs 0.000 claims 1
PHLBKPHSAVXXEF-UHFFFAOYSA-N trazodone Chemical compound ClC1=CC=CC(N2CCN(CCCN3C(N4C=CC=CC4=N3)=O)CC2)=C1 PHLBKPHSAVXXEF-UHFFFAOYSA-N 0.000 claims 1
NAUWTFJOPJWYOT-UHFFFAOYSA-N vanoxerine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)OCCN1CCN(CCCC=2C=CC=CC=2)CC1 NAUWTFJOPJWYOT-UHFFFAOYSA-N 0.000 claims 1
229950007136 vanoxerine Drugs 0.000 claims 1
229960004688 venlafaxine Drugs 0.000 claims 1
PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 claims 1
229960001255 viloxazine Drugs 0.000 claims 1
229960000607 ziprasidone Drugs 0.000 claims 1
MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 claims 1
229960001360 zolmitriptan Drugs 0.000 claims 1
UTAZCRNOSWWEFR-ZDUSSCGKSA-N zolmitriptan Chemical compound C=1[C]2C(CCN(C)C)=CN=C2C=CC=1C[C@H]1COC(=O)N1 UTAZCRNOSWWEFR-ZDUSSCGKSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 132
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
239000000243 solution Substances 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 19
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
238000005481 NMR spectroscopy Methods 0.000 description 14
239000007787 solid Substances 0.000 description 14
235000019439 ethyl acetate Nutrition 0.000 description 12
239000010410 layer Substances 0.000 description 12
239000012267 brine Substances 0.000 description 11
239000012044 organic layer Substances 0.000 description 11
239000011734 sodium Substances 0.000 description 11
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
239000000725 suspension Substances 0.000 description 11
238000005160 1H NMR spectroscopy Methods 0.000 description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
238000004440 column chromatography Methods 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 8
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000002904 solvent Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
0 N=C=*N(C(C=CC([N+]([O-])=O)=CC1)=C1N1)C1=O Chemical compound N=C=*N(C(C=CC([N+]([O-])=O)=CC1)=C1N1)C1=O 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
102000008299 Nitric Oxide Synthase Human genes 0.000 description 5
108010021487 Nitric Oxide Synthase Proteins 0.000 description 5
229910000564 Raney nickel Inorganic materials 0.000 description 5
238000000605 extraction Methods 0.000 description 5
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 5
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 5
LQLJZSJKRYTKTP-UHFFFAOYSA-N 2-dimethylaminoethyl chloride hydrochloride Chemical compound Cl.CN(C)CCCl LQLJZSJKRYTKTP-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
102000004257 Potassium Channel Human genes 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
229910052786 argon Inorganic materials 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000003818 flash chromatography Methods 0.000 description 4
108020001213 potassium channel Proteins 0.000 description 4
229940124597 therapeutic agent Drugs 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
208000024827 Alzheimer disease Diseases 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
230000005587 bubbling Effects 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
238000010992 reflux Methods 0.000 description 3
VYJGBXLKIBTOGV-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-2,3,4,5-tetrahydro-1-benzazepin-7-amine Chemical compound CN(C)CCN1CCCCC2=CC(N)=CC=C12 VYJGBXLKIBTOGV-UHFFFAOYSA-N 0.000 description 2
DPCBQEZRQXVNJH-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-3,4-dihydroquinolin-2-one Chemical compound C1=CC=C2N(CCN(C)C)C(=O)CCC2=C1 DPCBQEZRQXVNJH-UHFFFAOYSA-N 0.000 description 2
SIMNCQMLXCJICW-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-7-nitro-4,5-dihydro-3h-1-benzazepin-2-one Chemical compound C1CCC(=O)N(CCN(C)C)C2=CC=C([N+]([O-])=O)C=C21 SIMNCQMLXCJICW-UHFFFAOYSA-N 0.000 description 2
IVHOSOFUEVLNPA-UHFFFAOYSA-N 2-(3,4-dihydro-2h-quinolin-1-yl)-n,n-dimethylethanamine Chemical compound C1=CC=C2N(CCN(C)C)CCCC2=C1 IVHOSOFUEVLNPA-UHFFFAOYSA-N 0.000 description 2
IEKMZJOUZZJZCE-UHFFFAOYSA-N 2-(8-fluoro-6-nitro-3,4-dihydro-2h-quinolin-1-yl)-n,n-dimethylethanamine Chemical compound [O-][N+](=O)C1=CC(F)=C2N(CCN(C)C)CCCC2=C1 IEKMZJOUZZJZCE-UHFFFAOYSA-N 0.000 description 2
GCJPQUDHCRAKEU-UHFFFAOYSA-N 6-amino-1-(3-morpholin-4-ylpropyl)-3,4-dihydroquinolin-2-one Chemical compound O=C1CCC2=CC(N)=CC=C2N1CCCN1CCOCC1 GCJPQUDHCRAKEU-UHFFFAOYSA-N 0.000 description 2
NPXJHBRRVHEMLZ-UHFFFAOYSA-N 6-amino-1-(3-pyrrolidin-1-ylpropyl)-3,4-dihydroquinolin-2-one Chemical compound O=C1CCC2=CC(N)=CC=C2N1CCCN1CCCC1 NPXJHBRRVHEMLZ-UHFFFAOYSA-N 0.000 description 2
RGGXDRUJXNAJKT-UHFFFAOYSA-N 6-amino-1-[2-(dimethylamino)ethyl]-3,4-dihydroquinolin-2-one Chemical compound NC1=CC=C2N(CCN(C)C)C(=O)CCC2=C1 RGGXDRUJXNAJKT-UHFFFAOYSA-N 0.000 description 2
FNXLRNBWPJATDK-UHFFFAOYSA-N 6-amino-1-[3-(diethylamino)propyl]-3,4-dihydroquinolin-2-one Chemical compound NC1=CC=C2N(CCCN(CC)CC)C(=O)CCC2=C1 FNXLRNBWPJATDK-UHFFFAOYSA-N 0.000 description 2
HRXAQFFFDRLNCS-UHFFFAOYSA-N 7-amino-1-[2-(dimethylamino)ethyl]-4,5-dihydro-3h-1-benzazepin-2-one Chemical compound C1CCC(=O)N(CCN(C)C)C2=CC=C(N)C=C21 HRXAQFFFDRLNCS-UHFFFAOYSA-N 0.000 description 2
PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
BXNJHAXVSOCGBA-UHFFFAOYSA-N Harmine Chemical compound N1=CC=C2C3=CC=C(OC)C=C3NC2=C1C BXNJHAXVSOCGBA-UHFFFAOYSA-N 0.000 description 2
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
229910010082 LiAlH Inorganic materials 0.000 description 2
HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
150000001409 amidines Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229960000623 carbamazepine Drugs 0.000 description 2
FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
238000007865 diluting Methods 0.000 description 2
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
238000009472 formulation Methods 0.000 description 2
229930195712 glutamate Natural products 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
PIDPVVACBPWXLJ-UHFFFAOYSA-N methyl thiophene-2-carboximidothioate;hydroiodide Chemical compound I.CSC(=N)C1=CC=CS1 PIDPVVACBPWXLJ-UHFFFAOYSA-N 0.000 description 2
NYNBGYGTGNMACA-UHFFFAOYSA-N n'-[1-(3-morpholin-4-ylpropyl)-2-oxo-3,4-dihydroquinolin-6-yl]thiophene-2-carboximidamide Chemical compound C=1C=CSC=1C(=N)NC(C=C1CCC2=O)=CC=C1N2CCCN1CCOCC1 NYNBGYGTGNMACA-UHFFFAOYSA-N 0.000 description 2
NQCSVPBYGIUXDI-UHFFFAOYSA-N n'-[1-(3-morpholin-4-ylpropyl)-3,4-dihydro-2h-quinolin-6-yl]thiophene-2-carboximidamide Chemical compound C=1C=CSC=1C(=N)NC(C=C1CCC2)=CC=C1N2CCCN1CCOCC1 NQCSVPBYGIUXDI-UHFFFAOYSA-N 0.000 description 2
PGXXUVBLRCDDNC-UHFFFAOYSA-N n'-[1-[3-(diethylamino)propyl]-2-oxo-3,4-dihydroquinolin-6-yl]thiophene-2-carboximidamide Chemical compound C=1C=C2N(CCCN(CC)CC)C(=O)CCC2=CC=1NC(=N)C1=CC=CS1 PGXXUVBLRCDDNC-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000002002 slurry Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
230000003637 steroidlike Effects 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
QSELGEUCFNFITD-UHFFFAOYSA-N thiophene-2-carboximidamide Chemical compound NC(=N)C1=CC=CS1 QSELGEUCFNFITD-UHFFFAOYSA-N 0.000 description 2
LAUWCWCSEOWJMQ-QRJSTWQJSA-N (e,2s)-2-amino-4-fluoro-3-(3-hydroxyphenyl)but-3-enoic acid Chemical compound OC(=O)[C@@H](N)C(=C\F)\C1=CC=CC(O)=C1 LAUWCWCSEOWJMQ-QRJSTWQJSA-N 0.000 description 1
JZFSLMDLIPKTAO-UHFFFAOYSA-N 1,3-dihydroazepin-2-one Chemical compound O=C1CC=CC=CN1 JZFSLMDLIPKTAO-UHFFFAOYSA-N 0.000 description 1
JJUGUQRXPTVMCE-UHFFFAOYSA-N 1-(1-methylpyrrolidin-3-yl)-3,4-dihydro-2h-quinolin-6-amine Chemical compound C1N(C)CCC1N1C2=CC=C(N)C=C2CCC1 JJUGUQRXPTVMCE-UHFFFAOYSA-N 0.000 description 1
LVLYKBQJJGZYPW-UHFFFAOYSA-N 1-(3-chloropropyl)-6-nitro-3,4-dihydroquinolin-2-one;1-[3-(dimethylamino)propyl]-6-nitro-3,4-dihydroquinolin-2-one Chemical compound ClCCCN1C(=O)CCC2=CC([N+](=O)[O-])=CC=C21.[O-][N+](=O)C1=CC=C2N(CCCN(C)C)C(=O)CCC2=C1 LVLYKBQJJGZYPW-UHFFFAOYSA-N 0.000 description 1
WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
HQSRQKBSOOZLHH-UHFFFAOYSA-N 1-ethylphenoxathiine 10,10-dioxide Chemical compound O1C2=CC=CC=C2S(=O)(=O)C2=C1C=CC=C2CC HQSRQKBSOOZLHH-UHFFFAOYSA-N 0.000 description 1
FOELAEMGIPZAST-UHFFFAOYSA-N 1-nitro-3,4-dihydroquinolin-2-one Chemical compound C1=CC=C2N([N+](=O)[O-])C(=O)CCC2=C1 FOELAEMGIPZAST-UHFFFAOYSA-N 0.000 description 1
XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical compound CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 description 1
XFDXQLJFMLWWJA-YVMONPNESA-N 3-[(e)-3-amino-1-fluoroprop-1-en-2-yl]phenol Chemical compound NC\C(=C\F)C1=CC=CC(O)=C1 XFDXQLJFMLWWJA-YVMONPNESA-N 0.000 description 1
KIWUOCZHZROUNT-BTQNPOSSSA-N 4-chloro-2-[(2r)-2-hydroxy-3-morpholin-4-ylpropyl]-5-phenyl-1,2-oxazol-3-one;hydrochloride Chemical compound Cl.C([C@@H](O)CN1C(C(Cl)=C(O1)C=1C=CC=CC=1)=O)N1CCOCC1 KIWUOCZHZROUNT-BTQNPOSSSA-N 0.000 description 1
102100027493 5-hydroxytryptamine receptor 1D Human genes 0.000 description 1
101710138068 5-hydroxytryptamine receptor 1D Proteins 0.000 description 1
XKFPYPQQHFEXRZ-UHFFFAOYSA-N 5-methyl-N'-(phenylmethyl)-3-isoxazolecarbohydrazide Chemical compound O1C(C)=CC(C(=O)NNCC=2C=CC=CC=2)=N1 XKFPYPQQHFEXRZ-UHFFFAOYSA-N 0.000 description 1
APNNEYDBEVFVNM-UHFFFAOYSA-N 6-amino-1-(2-pyrrolidin-1-ylethyl)-3,4-dihydroquinolin-2-one Chemical compound O=C1CCC2=CC(N)=CC=C2N1CCN1CCCC1 APNNEYDBEVFVNM-UHFFFAOYSA-N 0.000 description 1
LRSCOIHGAYSLMZ-UHFFFAOYSA-N 6-bromo-1-(1-methylpyrrolidin-3-yl)-3,4-dihydro-2h-quinoline Chemical compound C1N(C)CCC1N1C2=CC=C(Br)C=C2CCC1 LRSCOIHGAYSLMZ-UHFFFAOYSA-N 0.000 description 1
YNEYZHMJQZEPKG-UHFFFAOYSA-N 6-nitro-1-(2-pyrrolidin-1-ylethyl)-3,4-dihydroquinolin-2-one Chemical compound O=C1CCC2=CC([N+](=O)[O-])=CC=C2N1CCN1CCCC1 YNEYZHMJQZEPKG-UHFFFAOYSA-N 0.000 description 1
ASVGSXZZZWXPRE-UHFFFAOYSA-N 7-nitro-1,3,4,5-tetrahydro-1-benzazepin-2-one Chemical compound N1C(=O)CCCC2=CC([N+](=O)[O-])=CC=C21 ASVGSXZZZWXPRE-UHFFFAOYSA-N 0.000 description 1
PAVUSVAGRKGNOW-UHFFFAOYSA-N 8-fluoro-6-nitro-1,2,3,4-tetrahydroquinoline Chemical compound N1CCCC2=CC([N+](=O)[O-])=CC(F)=C21 PAVUSVAGRKGNOW-UHFFFAOYSA-N 0.000 description 1
GDMWZTBOBNMXTL-UHFFFAOYSA-N CCN(C)CCN(CCC1)c(cc2)c1cc2NC(c1ccc[s]1)=N Chemical compound CCN(C)CCN(CCC1)c(cc2)c1cc2NC(c1ccc[s]1)=N GDMWZTBOBNMXTL-UHFFFAOYSA-N 0.000 description 1
BWBRCXGPEHCZGI-UHFFFAOYSA-N CCN(CC)CCN(C(CCc1c2)=O)c1ccc2NC(c1ccc[s]1)=N Chemical compound CCN(CC)CCN(C(CCc1c2)=O)c1ccc2NC(c1ccc[s]1)=N BWBRCXGPEHCZGI-UHFFFAOYSA-N 0.000 description 1
JXLXJNSICOMGMX-UHFFFAOYSA-N CCN(CC)CCN(CCCc1c2)c1ccc2NC(c1ccc[s]1)=N Chemical compound CCN(CC)CCN(CCCc1c2)c1ccc2NC(c1ccc[s]1)=N JXLXJNSICOMGMX-UHFFFAOYSA-N 0.000 description 1
ZGZGDXYLUSYXLN-UHFFFAOYSA-N CN(C)CCCN(C(CCc1c2)=O)c1ccc2NC(c1ccc[s]1)=N Chemical compound CN(C)CCCN(C(CCc1c2)=O)c1ccc2NC(c1ccc[s]1)=N ZGZGDXYLUSYXLN-UHFFFAOYSA-N 0.000 description 1
RBIQXPSMYHWBRG-UHFFFAOYSA-N CN(C)CCN(C(CC1)=O)c(c(F)c2)c1cc2NC(c1ccc[s]1)=N Chemical compound CN(C)CCN(C(CC1)=O)c(c(F)c2)c1cc2NC(c1ccc[s]1)=N RBIQXPSMYHWBRG-UHFFFAOYSA-N 0.000 description 1
XGNLBYKIAXNPTG-UHFFFAOYSA-N CN(CC1)CC1N(CCCc1c2)c1ccc2NC(c1ccc[s]1)=N Chemical compound CN(CC1)CC1N(CCCc1c2)c1ccc2NC(c1ccc[s]1)=N XGNLBYKIAXNPTG-UHFFFAOYSA-N 0.000 description 1
KZBNCBVKXLOIJL-UHFFFAOYSA-N CN(CC1)CC1N(CCc1c2)c1ccc2NC(c1ccc[s]1)=N Chemical compound CN(CC1)CC1N(CCc1c2)c1ccc2NC(c1ccc[s]1)=N KZBNCBVKXLOIJL-UHFFFAOYSA-N 0.000 description 1
AISRYOMXDOUVTL-UHFFFAOYSA-N CN(CC1)CCC1C(CCCCCC1)c(cc2)c1cc2NC(c1ccc[s]1)=N Chemical compound CN(CC1)CCC1C(CCCCCC1)c(cc2)c1cc2NC(c1ccc[s]1)=N AISRYOMXDOUVTL-UHFFFAOYSA-N 0.000 description 1
CTXVBQLVJSTMSQ-UHFFFAOYSA-N CN(CC1)CCC1N(CCc1c2)c1ccc2NC(c1ccc[s]1)=N Chemical compound CN(CC1)CCC1N(CCc1c2)c1ccc2NC(c1ccc[s]1)=N CTXVBQLVJSTMSQ-UHFFFAOYSA-N 0.000 description 1
OEOITMQUSUAXHN-UHFFFAOYSA-N CN(CCN(CCCc1cc(NC(c2ccc[s]2)=N)c2)c1c2F)I Chemical compound CN(CCN(CCCc1cc(NC(c2ccc[s]2)=N)c2)c1c2F)I OEOITMQUSUAXHN-UHFFFAOYSA-N 0.000 description 1
SCXDPWFTCCNXNE-UHFFFAOYSA-N CN1C(CCN(CCCC2)c(cc3)c2cc3NC(c2ccc[s]2)=N)CCC1 Chemical compound CN1C(CCN(CCCC2)c(cc3)c2cc3NC(c2ccc[s]2)=N)CCC1 SCXDPWFTCCNXNE-UHFFFAOYSA-N 0.000 description 1
PQXUODYKHUTQHC-UHFFFAOYSA-N CNCCN(C(CCc1c2)=O)c1ccc2NC(c1ccc[s]1)=N Chemical compound CNCCN(C(CCc1c2)=O)c1ccc2NC(c1ccc[s]1)=N PQXUODYKHUTQHC-UHFFFAOYSA-N 0.000 description 1
NGGYAZQXNBASMG-UHFFFAOYSA-N CNCCN(CCC1)c(c(F)c2)c1cc2NC(c1ccc[s]1)=N Chemical compound CNCCN(CCC1)c(c(F)c2)c1cc2NC(c1ccc[s]1)=N NGGYAZQXNBASMG-UHFFFAOYSA-N 0.000 description 1
FXDUNZXAROAWNT-UHFFFAOYSA-N CNCCN1c2cc(NC(c3ccc[s]3)=N)ccc2CCC1 Chemical compound CNCCN1c2cc(NC(c3ccc[s]3)=N)ccc2CCC1 FXDUNZXAROAWNT-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
101710132601 Capsid protein Proteins 0.000 description 1
101710094648 Coat protein Proteins 0.000 description 1
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
206010013654 Drug abuse Diseases 0.000 description 1
208000018522 Gastrointestinal disease Diseases 0.000 description 1
102100021181 Golgi phosphoprotein 3 Human genes 0.000 description 1
RERZNCLIYCABFS-UHFFFAOYSA-N Harmaline hydrochloride Natural products C1CN=C(C)C2=C1C1=CC=C(OC)C=C1N2 RERZNCLIYCABFS-UHFFFAOYSA-N 0.000 description 1
241000546188 Hypericum Species 0.000 description 1
235000017309 Hypericum perforatum Nutrition 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
229940127492 Kainate Receptor Antagonists Drugs 0.000 description 1
229910010084 LiAlH4 Inorganic materials 0.000 description 1
101710125418 Major capsid protein Proteins 0.000 description 1
QENGPZGAWFQWCZ-UHFFFAOYSA-N Methylthiophene Natural products CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 1
102000010909 Monoamine Oxidase Human genes 0.000 description 1
108010062431 Monoamine oxidase Proteins 0.000 description 1
KCWZGJVSDFYRIX-YFKPBYRVSA-N N(gamma)-nitro-L-arginine methyl ester Chemical compound COC(=O)[C@@H](N)CCCN=C(N)N[N+]([O-])=O KCWZGJVSDFYRIX-YFKPBYRVSA-N 0.000 description 1
HOKKHZGPKSLGJE-UHFFFAOYSA-N N-methyl-D-aspartic acid Natural products CNC(C(O)=O)CC(O)=O HOKKHZGPKSLGJE-UHFFFAOYSA-N 0.000 description 1
AIUQVYSHWAXCKK-UHFFFAOYSA-N N=C(c1ccc[s]1)Nc(cc1)cc(CCC2)c1N(CCN1CCCCC1)C2=O Chemical compound N=C(c1ccc[s]1)Nc(cc1)cc(CCC2)c1N(CCN1CCCCC1)C2=O AIUQVYSHWAXCKK-UHFFFAOYSA-N 0.000 description 1
QOPUQHFOHQNUNW-UHFFFAOYSA-N N=C(c1ccc[s]1)Nc(cc1)cc(CCCC2)c1N2C1CNCC1 Chemical compound N=C(c1ccc[s]1)Nc(cc1)cc(CCCC2)c1N2C1CNCC1 QOPUQHFOHQNUNW-UHFFFAOYSA-N 0.000 description 1
TZSSPPPATLBEEG-UHFFFAOYSA-N N=C(c1ccc[s]1)Nc(cc1)cc2c1N(CCN1CCCCC1)CCCC2 Chemical compound N=C(c1ccc[s]1)Nc(cc1)cc2c1N(CCN1CCCCC1)CCCC2 TZSSPPPATLBEEG-UHFFFAOYSA-N 0.000 description 1
HABOGBIBNBLABP-UHFFFAOYSA-N N=C(c1ccc[s]1)Nc(cc1C2C3CNCC3)ccc1NC2=O Chemical compound N=C(c1ccc[s]1)Nc(cc1C2C3CNCC3)ccc1NC2=O HABOGBIBNBLABP-UHFFFAOYSA-N 0.000 description 1
KZTNTEZFJOCUGU-UHFFFAOYSA-N N=C(c1ccc[s]1)Nc(cc1CC2)ccc1N(CCCN1CCCCC1)C2=O Chemical compound N=C(c1ccc[s]1)Nc(cc1CC2)ccc1N(CCCN1CCCCC1)C2=O KZTNTEZFJOCUGU-UHFFFAOYSA-N 0.000 description 1
NSXQCPBYTLDFBY-UHFFFAOYSA-N N=C(c1ccc[s]1)Nc(cc1CC2)ccc1N(CCN1CCCC1)C2=O Chemical compound N=C(c1ccc[s]1)Nc(cc1CC2)ccc1N(CCN1CCCC1)C2=O NSXQCPBYTLDFBY-UHFFFAOYSA-N 0.000 description 1
HWSJKPFDKFYFPU-UHFFFAOYSA-N N=C(c1ccc[s]1)Nc(cc1CC2)ccc1N(CCN1CCCCC1)C2=O Chemical compound N=C(c1ccc[s]1)Nc(cc1CC2)ccc1N(CCN1CCCCC1)C2=O HWSJKPFDKFYFPU-UHFFFAOYSA-N 0.000 description 1
BLZNLOLTHDUEOL-UHFFFAOYSA-N N=C(c1ccc[s]1)Nc(cc1CC2)ccc1N2C1CCNCC1 Chemical compound N=C(c1ccc[s]1)Nc(cc1CC2)ccc1N2C1CCNCC1 BLZNLOLTHDUEOL-UHFFFAOYSA-N 0.000 description 1
BRSFLOUTQGEAHB-UHFFFAOYSA-N N=C(c1ccc[s]1)Nc(cc1CC2)ccc1N2C1CNCC1 Chemical compound N=C(c1ccc[s]1)Nc(cc1CC2)ccc1N2C1CNCC1 BRSFLOUTQGEAHB-UHFFFAOYSA-N 0.000 description 1
NBSOQAZGWMLSSH-UHFFFAOYSA-N N=C(c1ccc[s]1)Nc(cc1CCC2)ccc1N2C1CCNCC1 Chemical compound N=C(c1ccc[s]1)Nc(cc1CCC2)ccc1N2C1CCNCC1 NBSOQAZGWMLSSH-UHFFFAOYSA-N 0.000 description 1
RGPDEAGGEXEMMM-UHFFFAOYSA-N Nefopam Chemical compound C12=CC=CC=C2CN(C)CCOC1C1=CC=CC=C1 RGPDEAGGEXEMMM-UHFFFAOYSA-N 0.000 description 1
102100022397 Nitric oxide synthase, brain Human genes 0.000 description 1
101710111444 Nitric oxide synthase, brain Proteins 0.000 description 1
101710141454 Nucleoprotein Proteins 0.000 description 1
101710083689 Probable capsid protein Proteins 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
241000700159 Rattus Species 0.000 description 1
239000000384 adrenergic alpha-2 receptor agonist Substances 0.000 description 1
VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 1
229960002980 amitriptyline oxide Drugs 0.000 description 1
210000004727 amygdala Anatomy 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
229940125681 anticonvulsant agent Drugs 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000003557 cannabinoid Substances 0.000 description 1
229930003827 cannabinoid Natural products 0.000 description 1
JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
YCWROMXNZZIJDQ-UHFFFAOYSA-N chembl174697 Chemical compound C1=2C(C)=NN(C)C=2NCCN=C1C1=CC=CC(Cl)=C1 YCWROMXNZZIJDQ-UHFFFAOYSA-N 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000011260 co-administration Methods 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000001054 cortical effect Effects 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
229940120889 dipyrone Drugs 0.000 description 1
QXWYKJLNLSIPIN-SFYZADRCSA-N droxidopa Chemical compound OC(=O)[C@H](N)[C@@H](O)C1=CC=C(O)C(O)=C1 QXWYKJLNLSIPIN-SFYZADRCSA-N 0.000 description 1
229960004945 etoricoxib Drugs 0.000 description 1
MNJVRJDLRVPLFE-UHFFFAOYSA-N etoricoxib Chemical compound C1=NC(C)=CC=C1C1=NC=C(Cl)C=C1C1=CC=C(S(C)(=O)=O)C=C1 MNJVRJDLRVPLFE-UHFFFAOYSA-N 0.000 description 1
230000002461 excitatory amino acid Effects 0.000 description 1
239000003257 excitatory amino acid Substances 0.000 description 1
230000003492 excitotoxic effect Effects 0.000 description 1
231100000063 excitotoxicity Toxicity 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000003940 fatty acid amidase inhibitor Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
VJHLDRVYTQNASM-UHFFFAOYSA-N harmine Natural products CC1=CN=CC=2NC3=CC(=CC=C3C=21)OC VJHLDRVYTQNASM-UHFFFAOYSA-N 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
229960002672 isocarboxazid Drugs 0.000 description 1
230000001535 kindling effect Effects 0.000 description 1
239000012280 lithium aluminium hydride Substances 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
230000007246 mechanism Effects 0.000 description 1
HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 description 1
LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
230000004065 mitochondrial dysfunction Effects 0.000 description 1
QROVMZITPYYMOP-UHFFFAOYSA-N n'-(1-pyrrolidin-3-yl-3,4-dihydro-2h-quinolin-6-yl)thiophene-2-carboximidamide;dihydrochloride Chemical compound Cl.Cl.C=1C=CSC=1C(=N)NC(C=C1CCC2)=CC=C1N2C1CCNC1 QROVMZITPYYMOP-UHFFFAOYSA-N 0.000 description 1
GNLOSZJZFXIEKT-UHFFFAOYSA-N n'-[1-[2-(dimethylamino)ethyl]-2-oxo-3,4-dihydroquinolin-6-yl]thiophene-2-carboximidamide Chemical compound C=1C=C2N(CCN(C)C)C(=O)CCC2=CC=1NC(=N)C1=CC=CS1 GNLOSZJZFXIEKT-UHFFFAOYSA-N 0.000 description 1
XXFKDMTZCZDTMA-UHFFFAOYSA-N n'-[1-[2-(methylamino)ethyl]-2,3,4,5-tetrahydro-1-benzazepin-7-yl]thiophene-2-carboximidamide Chemical compound C=1C=C2N(CCNC)CCCCC2=CC=1NC(=N)C1=CC=CS1 XXFKDMTZCZDTMA-UHFFFAOYSA-N 0.000 description 1
FPGQSNDORJTZCV-UHFFFAOYSA-N n'-[2-oxo-1-(3-pyrrolidin-1-ylpropyl)-3,4-dihydroquinolin-6-yl]thiophene-2-carboximidamide Chemical compound C=1C=CSC=1C(=N)NC(C=C1CCC2=O)=CC=C1N2CCCN1CCCC1 FPGQSNDORJTZCV-UHFFFAOYSA-N 0.000 description 1
MLPSDBJCWIYSEA-UHFFFAOYSA-N n-methyl-9,10,10-trioxothioxanthene-3-carboxamide Chemical compound C1=CC=C2S(=O)(=O)C3=CC(C(=O)NC)=CC=C3C(=O)C2=C1 MLPSDBJCWIYSEA-UHFFFAOYSA-N 0.000 description 1
229960000751 nefopam Drugs 0.000 description 1
210000002569 neuron Anatomy 0.000 description 1
239000004090 neuroprotective agent Substances 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229940053544 other antidepressants in atc Drugs 0.000 description 1
230000004792 oxidative damage Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229960002034 pinazepam Drugs 0.000 description 1
MFZOSKPPVCIFMT-UHFFFAOYSA-N pinazepam Chemical compound C12=CC(Cl)=CC=C2N(CC#C)C(=O)CN=C1C1=CC=CC=C1 MFZOSKPPVCIFMT-UHFFFAOYSA-N 0.000 description 1
229960004572 pizotifen Drugs 0.000 description 1
FIADGNVRKBPQEU-UHFFFAOYSA-N pizotifen Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2CCC2=C1C=CS2 FIADGNVRKBPQEU-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000001696 purinergic effect Effects 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
JUQLTPCYUFPYKE-UHFFFAOYSA-N ritanserin Chemical compound CC=1N=C2SC=CN2C(=O)C=1CCN(CC1)CCC1=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 JUQLTPCYUFPYKE-UHFFFAOYSA-N 0.000 description 1
229950009626 ritanserin Drugs 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical compound C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 description 1
229960003946 selegiline Drugs 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
210000000278 spinal cord Anatomy 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
WZWYJBNHTWCXIM-UHFFFAOYSA-N tenoxicam Chemical compound O=C1C=2SC=CC=2S(=O)(=O)N(C)C1=C(O)NC1=CC=CC=N1 WZWYJBNHTWCXIM-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
CIDVAIFYIMPWNG-UHFFFAOYSA-N thiophene-2-carboximidamide;dihydrochloride Chemical compound Cl.Cl.NC(=N)C1=CC=CS1 CIDVAIFYIMPWNG-UHFFFAOYSA-N 0.000 description 1
PNYKGCPSFKLFKA-UHFFFAOYSA-N tofenacin Chemical compound C=1C=CC=C(C)C=1C(OCCNC)C1=CC=CC=C1 PNYKGCPSFKLFKA-UHFFFAOYSA-N 0.000 description 1
229950010076 tofenacin Drugs 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1

JP2010500037A 2007-03-23 2008-03-25 キノロンおよびテトラヒドロキノリンならびにｎｏｓ阻害活性を有する関連化合物 Pending JP2010521527A (ja)