TW201210582A

TW201210582A - Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy

Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy Download PDF

Info

Publication number: TW201210582A
Authority: TW; Taiwan
Prior art keywords: methyl; alkyl; group; fluoro; sulfonamide
Prior art date: 2010-08-13

Application number

TW100128727A

Other languages

English (en)

Chinese (zh)

Inventor

Udo Lange

Wilhelm Amberg

Michael Ochse

Berthold Behl

Frauke Pohlki

Charles W Hutchins

Original Assignee

Abbott Gmbh & Amp Co Kg

Abbott Lab

Priority date

2010-08-13

Filing date

2011-08-11

Publication date

2012-03-16

2011-08-11 Application filed by Abbott Gmbh & Amp Co Kg, Abbott Lab filed Critical Abbott Gmbh & Amp Co Kg

2012-03-16 Publication of TW201210582A publication Critical patent/TW201210582A/zh

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 16
125000003392 indanyl group Chemical class C1(CCC2=CC=CC=C12)* 0.000 title claims abstract 9
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 title abstract description 39
238000002560 therapeutic procedure Methods 0.000 title description 4
150000003839 salts Chemical class 0.000 claims abstract description 21
-1 C3_Ci2^ Chemical group 0.000 claims description 386
150000001875 compounds Chemical class 0.000 claims description 292
125000000217 alkyl group Chemical group 0.000 claims description 274
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 214
229910052739 hydrogen Inorganic materials 0.000 claims description 179
239000001257 hydrogen Substances 0.000 claims description 160
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 150
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 148
125000004432 carbon atom Chemical group C* 0.000 claims description 112
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 104
125000001041 indolyl group Chemical group 0.000 claims description 95
125000003545 alkoxy group Chemical group 0.000 claims description 93
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 82
125000000623 heterocyclic group Chemical group 0.000 claims description 79
208000002193 Pain Diseases 0.000 claims description 71
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 70
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 70
150000001412 amines Chemical class 0.000 claims description 67
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 64
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 59
229940124530 sulfonamide Drugs 0.000 claims description 59
HYMXQESPSIAYCN-UHFFFAOYSA-N cyclobutanesulfonamide Chemical compound NS(=O)(=O)C1CCC1 HYMXQESPSIAYCN-UHFFFAOYSA-N 0.000 claims description 55
239000003814 drug Substances 0.000 claims description 50
230000036407 pain Effects 0.000 claims description 49
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 46
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 46
125000003118 aryl group Chemical group 0.000 claims description 44
229910052799 carbon Inorganic materials 0.000 claims description 33
125000002947 alkylene group Chemical group 0.000 claims description 27
229910052736 halogen Inorganic materials 0.000 claims description 27
125000004429 atom Chemical group 0.000 claims description 25
125000003277 amino group Chemical group 0.000 claims description 24
125000000753 cycloalkyl group Chemical group 0.000 claims description 24
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
125000003282 alkyl amino group Chemical group 0.000 claims description 23
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
229910052757 nitrogen Inorganic materials 0.000 claims description 23
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 23
239000007789 gas Substances 0.000 claims description 22
150000002367 halogens Chemical class 0.000 claims description 22
125000003342 alkenyl group Chemical group 0.000 claims description 19
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 18
239000000126 substance Substances 0.000 claims description 18
150000003456 sulfonamides Chemical class 0.000 claims description 18
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 17
125000000547 substituted alkyl group Chemical group 0.000 claims description 17
125000003396 thiol group Chemical group [H]S* 0.000 claims description 16
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 15
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 14
125000000304 alkynyl group Chemical group 0.000 claims description 14
VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 13
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 12
PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 11
125000004430 oxygen atom Chemical group O* 0.000 claims description 11
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
150000002431 hydrogen Chemical group 0.000 claims description 10
MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 9
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 9
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
230000000926 neurological effect Effects 0.000 claims description 7
238000006467 substitution reaction Methods 0.000 claims description 7
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 6
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 6
150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 6
125000005129 aryl carbonyl group Chemical group 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
125000006413 ring segment Chemical group 0.000 claims description 6
239000005864 Sulphur Substances 0.000 claims description 5
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
125000004653 anthracenylene group Chemical group 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
GTPINKYWKTZDBU-UHFFFAOYSA-N cyclopropylmethanesulfonamide Chemical compound NS(=O)(=O)CC1CC1 GTPINKYWKTZDBU-UHFFFAOYSA-N 0.000 claims description 4
125000001207 fluorophenyl group Chemical group 0.000 claims description 4
125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 4
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 4
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 4
HNQIVZYLYMDVSB-NJFSPNSNSA-N methanesulfonamide Chemical compound [14CH3]S(N)(=O)=O HNQIVZYLYMDVSB-NJFSPNSNSA-N 0.000 claims description 4
125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 4
OBVMQILFZAYMMI-UHFFFAOYSA-N 1,3-oxazole-4-sulfonamide Chemical compound NS(=O)(=O)C1=COC=N1 OBVMQILFZAYMMI-UHFFFAOYSA-N 0.000 claims description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 3
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 3
125000006323 alkenyl amino group Chemical group 0.000 claims description 3
125000005128 aryl amino alkyl group Chemical group 0.000 claims description 3
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 3
239000000796 flavoring agent Substances 0.000 claims description 3
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 3
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 2
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 2
125000005844 heterocyclyloxy group Chemical group 0.000 claims description 2
JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 claims description 2
229910021653 sulphate ion Inorganic materials 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims 2
ARHOUOIHKWELMD-UHFFFAOYSA-N 1-ethenyl-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(C=C)=C1 ARHOUOIHKWELMD-UHFFFAOYSA-N 0.000 claims 1
WEBBAOGRCDKLTH-UHFFFAOYSA-N 1-methylpyrazole-4-sulfonamide Chemical compound CN1C=C(S(N)(=O)=O)C=N1 WEBBAOGRCDKLTH-UHFFFAOYSA-N 0.000 claims 1
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims 1
125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims 1
125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 1
125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 1
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
UQFQONCQIQEYPJ-UHFFFAOYSA-N N-methylpyrazole Chemical compound CN1C=CC=N1 UQFQONCQIQEYPJ-UHFFFAOYSA-N 0.000 claims 1
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 1
125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
229910052786 argon Inorganic materials 0.000 claims 1
125000001691 aryl alkyl amino group Chemical group 0.000 claims 1
125000004657 aryl sulfonyl amino group Chemical group 0.000 claims 1
OVIZSQRQYWEGON-UHFFFAOYSA-N butane-1-sulfonamide Chemical compound CCCCS(N)(=O)=O OVIZSQRQYWEGON-UHFFFAOYSA-N 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 1
125000006286 dichlorobenzyl group Chemical group 0.000 claims 1
125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 claims 1
LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims 1
XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims 1
BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 1
IMGPVVZAPHSXNW-UHFFFAOYSA-N n-[[2-(azetidin-1-ylmethyl)-3-benzyl-6-fluoro-2,3-dihydro-1h-inden-5-yl]methyl]cyclobutanesulfonamide Chemical compound C=1C=CC=CC=1CC1C=2C=C(CNS(=O)(=O)C3CCC3)C(F)=CC=2CC1CN1CCC1 IMGPVVZAPHSXNW-UHFFFAOYSA-N 0.000 claims 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
229960003732 tyramine Drugs 0.000 claims 1
230000001225 therapeutic effect Effects 0.000 abstract description 47
239000003112 inhibitor Substances 0.000 abstract description 21
102100023145 Sodium- and chloride-dependent glycine transporter 1 Human genes 0.000 abstract description 9
101710083171 Sodium- and chloride-dependent glycine transporter 1 Proteins 0.000 abstract description 9
239000002585 base Substances 0.000 description 121
238000011282 treatment Methods 0.000 description 70
238000000034 method Methods 0.000 description 61
125000001424 substituent group Chemical group 0.000 description 51
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 47
201000010099 disease Diseases 0.000 description 37
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 36
239000003795 chemical substances by application Substances 0.000 description 34
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 34
230000008569 process Effects 0.000 description 27
208000015122 neurodegenerative disease Diseases 0.000 description 24
230000036961 partial effect Effects 0.000 description 24
150000001721 carbon Chemical group 0.000 description 22
208000024827 Alzheimer disease Diseases 0.000 description 21
239000004471 Glycine Substances 0.000 description 21
229940079593 drug Drugs 0.000 description 21
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 20
125000004093 cyano group Chemical group *C#N 0.000 description 20
238000004519 manufacturing process Methods 0.000 description 20
208000020016 psychiatric disease Diseases 0.000 description 20
208000024891 symptom Diseases 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000164 antipsychotic agent Substances 0.000 description 18
150000002476 indolines Chemical class 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
239000000543 intermediate Substances 0.000 description 17
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 16
125000005843 halogen group Chemical group 0.000 description 15
125000004433 nitrogen atom Chemical group N* 0.000 description 15
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 14
238000002360 preparation method Methods 0.000 description 14
125000006239 protecting group Chemical group 0.000 description 14
230000000694 effects Effects 0.000 description 13
102000010726 Glycine Plasma Membrane Transport Proteins Human genes 0.000 description 12
108010063380 Glycine Plasma Membrane Transport Proteins Proteins 0.000 description 12
229940126214 compound 3 Drugs 0.000 description 12
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 11
208000000094 Chronic Pain Diseases 0.000 description 10
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239000000460 chlorine Substances 0.000 description 10
208000035475 disorder Diseases 0.000 description 10
201000000980 schizophrenia Diseases 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
208000019901 Anxiety disease Diseases 0.000 description 9
241000700159 Rattus Species 0.000 description 9
125000001769 aryl amino group Chemical group 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
229910052731 fluorine Inorganic materials 0.000 description 9
125000003107 substituted aryl group Chemical group 0.000 description 9
229940124597 therapeutic agent Drugs 0.000 description 9
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 8
102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 8
108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 8
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 8
SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 8
239000011737 fluorine Substances 0.000 description 8
125000001188 haloalkyl group Chemical group 0.000 description 8
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
229910052707 ruthenium Inorganic materials 0.000 description 8
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206010036790 Productive cough Diseases 0.000 description 7
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238000010521 absorption reaction Methods 0.000 description 7
238000005804 alkylation reaction Methods 0.000 description 7
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
210000004027 cell Anatomy 0.000 description 7
125000001072 heteroaryl group Chemical group 0.000 description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
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VHSUHSBTEGHGTG-UHFFFAOYSA-N 1-cyclopropylindole Chemical compound C1CC1N1C2=CC=CC=C2C=C1 VHSUHSBTEGHGTG-UHFFFAOYSA-N 0.000 description 6
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 6
229910052801 chlorine Inorganic materials 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
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JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
208000025966 Neurological disease Diseases 0.000 description 4
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WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
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239000000935 antidepressant agent Substances 0.000 description 4
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