JP2008535908A5 - - Google Patents
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- JP2008535908A5 JP2008535908A5 JP2008505999A JP2008505999A JP2008535908A5 JP 2008535908 A5 JP2008535908 A5 JP 2008535908A5 JP 2008505999 A JP2008505999 A JP 2008505999A JP 2008505999 A JP2008505999 A JP 2008505999A JP 2008535908 A5 JP2008535908 A5 JP 2008535908A5
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- Prior art keywords
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- Prior art date
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- 239000000203 mixture Substances 0.000 claims 61
- 125000000217 alkyl group Chemical group 0.000 claims 41
- 150000001875 compounds Chemical class 0.000 claims 31
- 125000002877 alkyl aryl group Chemical group 0.000 claims 24
- 125000000623 heterocyclic group Chemical group 0.000 claims 23
- 125000003118 aryl group Chemical group 0.000 claims 22
- -1 1-methyl - pyrrolidin-2-yl Chemical group 0.000 claims 19
- 229910052799 carbon Inorganic materials 0.000 claims 18
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000000935 antidepressant agent Substances 0.000 claims 10
- 229940005513 antidepressants Drugs 0.000 claims 10
- 230000001430 anti-depressive effect Effects 0.000 claims 9
- 239000002767 noradrenalin uptake inhibitor Substances 0.000 claims 8
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 125000005309 thioalkoxy group Chemical group 0.000 claims 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- 239000005557 antagonist Substances 0.000 claims 6
- 229940127221 norepinephrine reuptake inhibitor Drugs 0.000 claims 6
- 208000019695 Migraine disease Diseases 0.000 claims 5
- 206010027599 migraine Diseases 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 208000004454 Hyperalgesia Diseases 0.000 claims 4
- 208000002193 Pain Diseases 0.000 claims 4
- 102000004257 Potassium Channel Human genes 0.000 claims 4
- 208000006011 Stroke Diseases 0.000 claims 4
- 239000000556 agonist Substances 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 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 4
- 108020001213 potassium channel Proteins 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
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- YTQQIHUQLOZOJI-UHFFFAOYSA-N 2,3-dihydro-1,2-thiazole Chemical compound C1NSC=C1 YTQQIHUQLOZOJI-UHFFFAOYSA-N 0.000 claims 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 3
- 102000006538 Nitric Oxide Synthase Type I Human genes 0.000 claims 3
- 108010008858 Nitric Oxide Synthase Type I Proteins 0.000 claims 3
- 102000011779 Nitric Oxide Synthase Type II Human genes 0.000 claims 3
- 108010076864 Nitric Oxide Synthase Type II Proteins 0.000 claims 3
- 102000008052 Nitric Oxide Synthase Type III Human genes 0.000 claims 3
- 108010075520 Nitric Oxide Synthase Type III Proteins 0.000 claims 3
- 206010043269 Tension headache Diseases 0.000 claims 3
- 208000008548 Tension-Type Headache Diseases 0.000 claims 3
- VHGCDTVCOLNTBX-QGZVFWFLSA-N atomoxetine Chemical group O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=CC=C1C VHGCDTVCOLNTBX-QGZVFWFLSA-N 0.000 claims 3
- 229960002430 atomoxetine Drugs 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 230000001684 chronic effect Effects 0.000 claims 3
- 229960004193 dextropropoxyphene Drugs 0.000 claims 3
- 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 3
- 206010015037 epilepsy Diseases 0.000 claims 3
- 239000003112 inhibitor Substances 0.000 claims 3
- 229960000600 milnacipran Drugs 0.000 claims 3
- RONZAEMNMFQXRA-UHFFFAOYSA-N mirtazapine Chemical compound C1C2=CC=CN=C2N2CCN(C)CC2C2=CC=CC=C21 RONZAEMNMFQXRA-UHFFFAOYSA-N 0.000 claims 3
- 229960005181 morphine Drugs 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
- 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
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 3
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-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
- 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 2
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 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
- 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 2
- 102000009346 Adenosine receptors Human genes 0.000 claims 2
- 108050000203 Adenosine receptors Proteins 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
- 208000000094 Chronic Pain Diseases 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 claims 2
- 206010019196 Head injury Diseases 0.000 claims 2
- 208000035154 Hyperesthesia 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
- 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
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-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
- KTDZCOWXCWUPEO-UHFFFAOYSA-N NS-398 Chemical compound CS(=O)(=O)NC1=CC=C([N+]([O-])=O)C=C1OC1CCCCC1 KTDZCOWXCWUPEO-UHFFFAOYSA-N 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
- 208000028389 Nerve injury Diseases 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
- PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 claims 2
- 206010063837 Reperfusion injury Diseases 0.000 claims 2
- 208000007271 Substance Withdrawal Syndrome Diseases 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
- 206010053552 allodynia Diseases 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
- 230000003110 anti-inflammatory effect Effects 0.000 claims 2
- 239000011575 calcium Substances 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
- 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
- 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
- XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 claims 2
- 229960005426 doxepin Drugs 0.000 claims 2
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 125000001475 halogen functional group Chemical group 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
- 229960004801 imipramine Drugs 0.000 claims 2
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 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
- 229960003464 mefenamic acid Drugs 0.000 claims 2
- 229960001929 meloxicam Drugs 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- 229960001785 mirtazapine Drugs 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
- ZPYXFXHKINDFBM-UHFFFAOYSA-N n'-[1-[2-(1-methylpyrrolidin-2-yl)ethyl]indol-6-yl]thiophene-2-carboximidamide Chemical compound CN1CCCC1CCN1C2=CC(NC(=N)C=3SC=CC=3)=CC=C2C=C1 ZPYXFXHKINDFBM-UHFFFAOYSA-N 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
- 230000008764 nerve damage Effects 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 208000021722 neuropathic pain Diseases 0.000 claims 2
- 231100000228 neurotoxicity Toxicity 0.000 claims 2
- 230000007135 neurotoxicity Effects 0.000 claims 2
- 229940126569 noradrenaline reuptake inhibitor Drugs 0.000 claims 2
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 claims 2
- 229960001158 nortriptyline Drugs 0.000 claims 2
- 229960000482 pethidine Drugs 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 229960003770 reboxetine Drugs 0.000 claims 2
- 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 2
- 229940044551 receptor antagonist Drugs 0.000 claims 2
- 239000002464 receptor antagonist Substances 0.000 claims 2
- 230000002441 reversible effect Effects 0.000 claims 2
- 150000003839 salts Chemical class 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
- 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
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 229960005138 tianeptine Drugs 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
- 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
- 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
- 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
- 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 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
- 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
- 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
- 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
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- 2006-04-13 AU AU2006321284A patent/AU2006321284B2/en not_active Ceased
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- 2006-04-13 DK DK06831851.8T patent/DK1883451T3/da active
- 2006-04-13 KR KR1020137031374A patent/KR20130136010A/ko not_active Ceased
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