JP2011526251A5

JP2011526251A5 -

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Publication number: JP2011526251A5
Authority: JP; Japan
Prior art keywords: optionally substituted; acid; chr; compound; alkyl
Prior art date: 2009-07-03
Legal status : Granted

Application number

JP2011515041A

Other languages

English (en)

Japanese (ja)

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JP5572157B2 (ja

JP2011526251A (ja

Filing date

2009-07-03

Publication date

2012-08-16

2009-07-03 Application filed filed Critical

2009-07-03 Priority claimed from PCT/CA2009/000923 external-priority patent/WO2010000073A1/en

2011-10-06 Publication of JP2011526251A publication Critical patent/JP2011526251A/ja

2012-08-16 Publication of JP2011526251A5 publication Critical patent/JP2011526251A5/ja

2014-08-13 Application granted granted Critical

2014-08-13 Publication of JP5572157B2 publication Critical patent/JP5572157B2/ja

Status Expired - Fee Related legal-status Critical Current

2029-07-03 Anticipated expiration legal-status Critical

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-1 NR 7 Inorganic materials 0.000 claims 25
150000001875 compounds Chemical class 0.000 claims 18
208000004454 Hyperalgesia Diseases 0.000 claims 12
125000000217 alkyl group Chemical group 0.000 claims 12
125000000623 heterocyclic group Chemical group 0.000 claims 11
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims 10
125000002877 alkyl aryl group Chemical group 0.000 claims 9
239000008194 pharmaceutical composition Substances 0.000 claims 8
150000003839 salts Chemical class 0.000 claims 7
208000035154 Hyperesthesia Diseases 0.000 claims 6
208000002193 Pain Diseases 0.000 claims 6
239000000556 agonist Substances 0.000 claims 6
206010053552 allodynia Diseases 0.000 claims 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 6
239000004036 potassium channel stimulating agent Substances 0.000 claims 6
206010064012 Central pain syndrome Diseases 0.000 claims 5
125000003545 alkoxy group Chemical group 0.000 claims 5
125000005309 thioalkoxy group Chemical group 0.000 claims 5
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
206010019233 Headaches Diseases 0.000 claims 4
208000019695 Migraine disease Diseases 0.000 claims 4
229940079593 drug Drugs 0.000 claims 4
239000003814 drug Substances 0.000 claims 4
206010013663 drug dependence Diseases 0.000 claims 4
125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
206010027599 migraine Diseases 0.000 claims 4
229960005181 morphine Drugs 0.000 claims 4
208000004296 neuralgia Diseases 0.000 claims 4
208000021722 neuropathic pain Diseases 0.000 claims 4
239000002767 noradrenalin uptake inhibitor Substances 0.000 claims 4
229940127221 norepinephrine reuptake inhibitor Drugs 0.000 claims 4
229910052760 oxygen Inorganic materials 0.000 claims 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
208000011117 substance-related disease Diseases 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
102000009346 Adenosine receptors Human genes 0.000 claims 3
108050000203 Adenosine receptors Proteins 0.000 claims 3
208000000094 Chronic Pain Diseases 0.000 claims 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 claims 3
239000005557 antagonist Substances 0.000 claims 3
239000000935 antidepressant agent Substances 0.000 claims 3
229940005513 antidepressants Drugs 0.000 claims 3
125000003118 aryl group Chemical group 0.000 claims 3
230000001684 chronic effect Effects 0.000 claims 3
231100000869 headache Toxicity 0.000 claims 3
229910052739 hydrogen Inorganic materials 0.000 claims 3
239000003112 inhibitor Substances 0.000 claims 3
229960000600 milnacipran Drugs 0.000 claims 3
230000004770 neurodegeneration Effects 0.000 claims 3
229910052757 nitrogen Inorganic materials 0.000 claims 3
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 3
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims 3
229960001158 nortriptyline Drugs 0.000 claims 3
229960002702 piroxicam Drugs 0.000 claims 3
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 3
229940002612 prodrug Drugs 0.000 claims 3
239000000651 prodrug Substances 0.000 claims 3
229910052717 sulfur 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
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 2
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 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
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 2
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 2
102100028661 Amine oxidase [flavin-containing] A Human genes 0.000 claims 2
101710185917 Amine oxidase [flavin-containing] A Proteins 0.000 claims 2
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-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
206010012335 Dependence Diseases 0.000 claims 2
HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 claims 2
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 2
102100029111 Fatty-acid amide hydrolase 1 Human genes 0.000 claims 2
UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 claims 2
208000018522 Gastrointestinal disease Diseases 0.000 claims 2
206010019196 Head injury Diseases 0.000 claims 2
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims 2
206010065390 Inflammatory pain Diseases 0.000 claims 2
ALFGKMXHOUSVAD-UHFFFAOYSA-N Ketobemidone Chemical compound C=1C=CC(O)=CC=1C1(C(=O)CC)CCN(C)CC1 ALFGKMXHOUSVAD-UHFFFAOYSA-N 0.000 claims 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 2
XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 claims 2
229940123685 Monoamine oxidase inhibitor Drugs 0.000 claims 2
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 2
206010029350 Neurotoxicity Diseases 0.000 claims 2
102000008299 Nitric Oxide Synthase Human genes 0.000 claims 2
108010021487 Nitric Oxide Synthase Proteins 0.000 claims 2
208000018737 Parkinson disease Diseases 0.000 claims 2
206010063837 Reperfusion injury Diseases 0.000 claims 2
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 2
206010044221 Toxic encephalopathy Diseases 0.000 claims 2
229960001138 acetylsalicylic acid Drugs 0.000 claims 2
239000002253 acid Substances 0.000 claims 2
125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 2
229960000959 amineptine Drugs 0.000 claims 2
229960000836 amitriptyline Drugs 0.000 claims 2
KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical group C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 claims 2
206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
230000001430 anti-depressive effect Effects 0.000 claims 2
230000003110 anti-inflammatory effect Effects 0.000 claims 2
239000001961 anticonvulsive agent Substances 0.000 claims 2
229960003965 antiepileptics Drugs 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
229960000590 celecoxib Drugs 0.000 claims 2
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 2
208000015114 central nervous system disease Diseases 0.000 claims 2
238000002512 chemotherapy Methods 0.000 claims 2
229960004606 clomipramine Drugs 0.000 claims 2
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 2
229960003914 desipramine Drugs 0.000 claims 2
229960004193 dextropropoxyphene Drugs 0.000 claims 2
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 2
229960003075 dibenzepin Drugs 0.000 claims 2
229960000616 diflunisal Drugs 0.000 claims 2
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 2
208000010643 digestive system disease Diseases 0.000 claims 2
XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 claims 2
230000009977 dual effect Effects 0.000 claims 2
230000002526 effect on cardiovascular system Effects 0.000 claims 2
206010015037 epilepsy Diseases 0.000 claims 2
108010046094 fatty-acid amide hydrolase Proteins 0.000 claims 2
229960001419 fenoprofen Drugs 0.000 claims 2
208000018685 gastrointestinal system disease Diseases 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
OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 claims 2
229960001680 ibuprofen Drugs 0.000 claims 2
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 2
229960002844 iprindole Drugs 0.000 claims 2
PLIGPBGDXASWPX-UHFFFAOYSA-N iprindole Chemical compound C1CCCCCC2=C1N(CCCN(C)C)C1=CC=CC=C12 PLIGPBGDXASWPX-UHFFFAOYSA-N 0.000 claims 2
229960003029 ketobemidone Drugs 0.000 claims 2
229960004090 maprotiline Drugs 0.000 claims 2
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 2
229960003464 mefenamic acid Drugs 0.000 claims 2
229960001929 meloxicam Drugs 0.000 claims 2
229960001785 mirtazapine Drugs 0.000 claims 2
RONZAEMNMFQXRA-UHFFFAOYSA-N mirtazapine Chemical compound C1C2=CC=CN=C2N2CCN(C)CC2C2=CC=CC=C21 RONZAEMNMFQXRA-UHFFFAOYSA-N 0.000 claims 2
239000002899 monoamine oxidase inhibitor Substances 0.000 claims 2
239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 claims 2
229960002009 naproxen Drugs 0.000 claims 2
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 2
208000015122 neurodegenerative disease Diseases 0.000 claims 2
231100000228 neurotoxicity Toxicity 0.000 claims 2
230000007135 neurotoxicity Effects 0.000 claims 2
229960000482 pethidine Drugs 0.000 claims 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
229960002895 phenylbutazone Drugs 0.000 claims 2
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 2
125000003386 piperidinyl group Chemical group 0.000 claims 2
125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
230000002441 reversible effect Effects 0.000 claims 2
229940124834 selective serotonin reuptake inhibitor Drugs 0.000 claims 2
239000012896 selective serotonin reuptake inhibitor Substances 0.000 claims 2
229940076279 serotonin Drugs 0.000 claims 2
229940126570 serotonin reuptake inhibitor Drugs 0.000 claims 2
239000003772 serotonin uptake inhibitor Substances 0.000 claims 2
125000000446 sulfanediyl group Chemical group *S* 0.000 claims 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 2
229960000894 sulindac Drugs 0.000 claims 2
208000024891 symptom Diseases 0.000 claims 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 2
229960004394 topiramate Drugs 0.000 claims 2
229960002431 trimipramine Drugs 0.000 claims 2
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 2
ZISSAWUMDACLOM-UHFFFAOYSA-N triptane Chemical compound CC(C)C(C)(C)C ZISSAWUMDACLOM-UHFFFAOYSA-N 0.000 claims 2
AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 claims 1
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 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
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 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
WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical group C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-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
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 1
ZEUITGRIYCTCEM-KRWDZBQOSA-N (S)-duloxetine Chemical group 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
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 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
XNLOOYJBLRHTMX-UHFFFAOYSA-N 2-(6-chloro-9-methyl-2,3-dioxo-1,4-dihydroindeno[2,3-b]pyrazin-9-yl)acetic acid Chemical compound N1C(=O)C(=O)NC2=C1C1=CC(Cl)=CC=C1C2(CC(O)=O)C XNLOOYJBLRHTMX-UHFFFAOYSA-N 0.000 claims 1
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JP2011515041A 2008-07-03 2009-07-03 Ｎｏｓ阻害活性を有するベンゾオキサジン類、ベンゾチアジン類、および関係化合物 Expired - Fee Related JP5572157B2 (ja)