SA06270314B1 - مشتقات 3- سلفونيل إندازول مستبدلة كربيطات 5- هيدروكسى تريبتامين-6 - Google Patents

Info

Publication number

SA06270314B1

SA06270314B1 SA6270314A SA06270314A SA06270314B1 SA 06270314 B1 SA06270314 B1 SA 06270314B1 SA 6270314 A SA6270314 A SA 6270314A SA 06270314 A SA06270314 A SA 06270314A SA 06270314 B1 SA06270314 B1 SA 06270314B1

Authority

SA

Saudi Arabia

Prior art keywords

indazol

naphthalene

mmol

sulfonyl

ethyl

Prior art date

2005-08-15

Links

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• Global Dossier
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• -1 Substituted-3-sulfonylindazole Chemical class 0.000 title description 95
• 239000003446 ligand Substances 0.000 title description 10
• 150000001875 compounds Chemical class 0.000 claims abstract description 288
• 210000003169 central nervous system Anatomy 0.000 claims abstract description 12
• 150000003839 salts Chemical class 0.000 claims description 42
• IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 19
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
• 239000003814 drug Substances 0.000 claims description 12
• 230000006735 deficit Effects 0.000 claims description 7
• 201000010099 disease Diseases 0.000 claims description 7
• 229940079593 drug Drugs 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 230000001149 cognitive effect Effects 0.000 claims description 4
• 208000011580 syndromic disease Diseases 0.000 claims description 3
• 206010003805 Autism Diseases 0.000 claims description 2
• 208000020706 Autistic disease Diseases 0.000 claims description 2
• 230000007547 defect Effects 0.000 claims description 2
• 208000020358 Learning disease Diseases 0.000 claims 1
• 208000014674 injury Diseases 0.000 claims 1
• 201000003723 learning disability Diseases 0.000 claims 1
• 230000008733 trauma Effects 0.000 claims 1
• 108091005435 5-HT6 receptors Proteins 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 339
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 287
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 240
• 239000000203 mixture Substances 0.000 description 206
• 239000007787 solid Substances 0.000 description 178
• 239000011541 reaction mixture Substances 0.000 description 157
• 239000000243 solution Substances 0.000 description 157
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 132
• 235000019439 ethyl acetate Nutrition 0.000 description 130
• HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 128
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 107
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 104
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 99
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 97
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 89
• 239000012267 brine Substances 0.000 description 85
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 85
• 238000000034 method Methods 0.000 description 73
• 238000001819 mass spectrum Methods 0.000 description 65
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 64
• 238000002844 melting Methods 0.000 description 63
• 230000008018 melting Effects 0.000 description 63
• 239000012074 organic phase Substances 0.000 description 63
• 239000002904 solvent Substances 0.000 description 60
• 238000001816 cooling Methods 0.000 description 57
• 239000006260 foam Substances 0.000 description 56
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 50
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 50
• 238000000921 elemental analysis Methods 0.000 description 50
• 229910052757 nitrogen Inorganic materials 0.000 description 50
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
• 238000003818 flash chromatography Methods 0.000 description 46
• 238000003756 stirring Methods 0.000 description 46
• 235000017557 sodium bicarbonate Nutrition 0.000 description 45
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 45
• 238000006243 chemical reaction Methods 0.000 description 43
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 37
• 238000004128 high performance liquid chromatography Methods 0.000 description 36
• 238000005984 hydrogenation reaction Methods 0.000 description 36
• 229960003390 magnesium sulfate Drugs 0.000 description 36
• 235000019341 magnesium sulphate Nutrition 0.000 description 36
• 150000001412 amines Chemical class 0.000 description 35
• 239000012141 concentrate Substances 0.000 description 35
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Substances [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 35
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 35
• 235000008504 concentrate Nutrition 0.000 description 34
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 31
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
• 239000000463 material Substances 0.000 description 29
• 102000005962 receptors Human genes 0.000 description 29
• 108020003175 receptors Proteins 0.000 description 29
• 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 28
• 238000001035 drying Methods 0.000 description 27
• 238000004458 analytical method Methods 0.000 description 25
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 24
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 23
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 23
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 22
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
• YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 22
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 21
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• 239000012043 crude product Substances 0.000 description 21
• ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 20
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 18
• 239000012071 phase Substances 0.000 description 18
• 239000000047 product Substances 0.000 description 18
• 239000011734 sodium Substances 0.000 description 18
• 239000000126 substance Substances 0.000 description 18
• 238000001291 vacuum drying Methods 0.000 description 17
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 16
• 125000003118 aryl group Chemical group 0.000 description 16
• 235000019441 ethanol Nutrition 0.000 description 16
• 125000001072 heteroaryl group Chemical group 0.000 description 16
• 229910052700 potassium Inorganic materials 0.000 description 16
• 239000011591 potassium Substances 0.000 description 16
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 16
• 239000000460 chlorine Substances 0.000 description 15
• 235000010288 sodium nitrite Nutrition 0.000 description 15
• 239000007788 liquid Substances 0.000 description 14
• 230000002829 reductive effect Effects 0.000 description 14
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 13
• 125000004429 atom Chemical group 0.000 description 13
• 229910052739 hydrogen Inorganic materials 0.000 description 13
• 229940073640 magnesium sulfate anhydrous Drugs 0.000 description 13
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
• 125000000217 alkyl group Chemical group 0.000 description 12
• 239000012298 atmosphere Substances 0.000 description 12
• HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 12
• 229910052799 carbon Inorganic materials 0.000 description 12
• 239000000706 filtrate Substances 0.000 description 12
• 238000001914 filtration Methods 0.000 description 12
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 12
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 11
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 11
• 239000000908 ammonium hydroxide Substances 0.000 description 11
• 125000000753 cycloalkyl group Chemical group 0.000 description 11
• 239000000284 extract Substances 0.000 description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 10
• 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 10
• 238000004587 chromatography analysis Methods 0.000 description 10
• LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 10
• 229910052708 sodium Inorganic materials 0.000 description 10
• 238000001228 spectrum Methods 0.000 description 10
• 239000007858 starting material Substances 0.000 description 10
• APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 9
• XHMLYFRREKIYDU-UHFFFAOYSA-N 1-(chloromethylsulfonyl)naphthalene Chemical compound C1=CC=C2C(S(=O)(=O)CCl)=CC=CC2=C1 XHMLYFRREKIYDU-UHFFFAOYSA-N 0.000 description 9
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 9
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 9
• 239000002253 acid Substances 0.000 description 9
• 239000004480 active ingredient Substances 0.000 description 9
• 239000000969 carrier Substances 0.000 description 9
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 9
• 230000004927 fusion Effects 0.000 description 9
• 239000012044 organic layer Substances 0.000 description 9
• 229960005235 piperonyl butoxide Drugs 0.000 description 9
• 229940002612 prodrug Drugs 0.000 description 9
• 239000000651 prodrug Substances 0.000 description 9
• 238000012360 testing method Methods 0.000 description 9
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 8
• 229910000024 caesium carbonate Inorganic materials 0.000 description 8
• 238000000354 decomposition reaction Methods 0.000 description 8
• 208000035475 disorder Diseases 0.000 description 8
• 150000002148 esters Chemical class 0.000 description 8
• 239000010410 layer Substances 0.000 description 8
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
• 229910052763 palladium Inorganic materials 0.000 description 8
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• LZIYAIRGDHSVED-UHFFFAOYSA-N 1-(bromomethyl)-3-chlorobenzene Chemical compound ClC1=CC=CC(CBr)=C1 LZIYAIRGDHSVED-UHFFFAOYSA-N 0.000 description 7
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 7
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 description 7
• 125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 description 7
• 230000001225 therapeutic effect Effects 0.000 description 7
• VVGINBYPKXZHDE-UHFFFAOYSA-N 3-naphthalen-1-ylsulfonyl-2h-indazole-5-carbaldehyde Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)C=O)=CC=CC2=C1 VVGINBYPKXZHDE-UHFFFAOYSA-N 0.000 description 6
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
• LRHPLDYGYMQRHN-UHFFFAOYSA-N Butanol Natural products CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
• HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
• 239000007864 aqueous solution Substances 0.000 description 6
• 239000003795 chemical substances by application Substances 0.000 description 6
• 238000009472 formulation Methods 0.000 description 6
• 125000005842 heteroatom Chemical group 0.000 description 6
• 235000011167 hydrochloric acid Nutrition 0.000 description 6
• 239000001257 hydrogen Substances 0.000 description 6
• 238000004949 mass spectrometry Methods 0.000 description 6
• 239000003208 petroleum Substances 0.000 description 6
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 6
• 239000002244 precipitate Substances 0.000 description 6
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
• GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
• 239000012258 stirred mixture Substances 0.000 description 6
• 125000000547 substituted alkyl group Chemical group 0.000 description 6
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 6
• JBZMHOYHEYMIJB-UHFFFAOYSA-N 1-naphthalen-1-ylsulfonylindazole Chemical compound N1=CC2=CC=CC=C2N1S(=O)(=O)C1=CC=CC2=CC=CC=C12 JBZMHOYHEYMIJB-UHFFFAOYSA-N 0.000 description 5
• KZMAWJRXKGLWGS-UHFFFAOYSA-N 2-chloro-n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-n-(3-methoxypropyl)acetamide Chemical compound S1C(N(C(=O)CCl)CCCOC)=NC(C=2C=CC(OC)=CC=2)=C1 KZMAWJRXKGLWGS-UHFFFAOYSA-N 0.000 description 5
• JGMZQHZCMQDYQE-UHFFFAOYSA-N 3-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]propan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCCN)=CC=CC2=C1 JGMZQHZCMQDYQE-UHFFFAOYSA-N 0.000 description 5
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 5
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
• 125000002619 bicyclic group Chemical group 0.000 description 5
• 230000027455 binding Effects 0.000 description 5
• 238000009833 condensation Methods 0.000 description 5
• 230000005494 condensation Effects 0.000 description 5
• 239000000039 congener Substances 0.000 description 5
• 239000012458 free base Substances 0.000 description 5
• 230000006870 function Effects 0.000 description 5
• 239000011777 magnesium Substances 0.000 description 5
• 239000012299 nitrogen atmosphere Substances 0.000 description 5
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 5
• 239000000377 silicon dioxide Substances 0.000 description 5
• 125000001424 substituent group Chemical group 0.000 description 5
• 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 4
• KHBLKVSJKHHJJP-UHFFFAOYSA-N 1-(2-chloroethoxy)-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1OCCCl KHBLKVSJKHHJJP-UHFFFAOYSA-N 0.000 description 4
• ZPBLPPYZKOXAQL-UHFFFAOYSA-N 1-[(5-fluoro-2-nitrophenyl)methylsulfonyl]naphthalene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1CS(=O)(=O)C1=CC=CC2=CC=CC=C12 ZPBLPPYZKOXAQL-UHFFFAOYSA-N 0.000 description 4
• UGZYQDUVEDXGHV-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-(2-pyrrolidin-1-ylethoxy)-2h-indazole Chemical compound C=1C=CC=CC=1S(=O)(=O)C(C1=C2)=NNC1=CC=C2OCCN1CCCC1 UGZYQDUVEDXGHV-UHFFFAOYSA-N 0.000 description 4
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• 229960000583 acetic acid Drugs 0.000 description 4
• 125000000304 alkynyl group Chemical group 0.000 description 4
• 229940024606 amino acid Drugs 0.000 description 4
• 235000001014 amino acid Nutrition 0.000 description 4
• 229910021529 ammonia Inorganic materials 0.000 description 4
• 239000005557 antagonist Substances 0.000 description 4
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 description 4
• 210000004556 brain Anatomy 0.000 description 4
• JPOXNPPZZKNXOV-UHFFFAOYSA-N bromochloromethane Chemical compound ClCBr JPOXNPPZZKNXOV-UHFFFAOYSA-N 0.000 description 4
• 125000004432 carbon atom Chemical group C* 0.000 description 4
• 210000004027 cell Anatomy 0.000 description 4
• NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 4
• 238000004090 dissolution Methods 0.000 description 4
• 235000019253 formic acid Nutrition 0.000 description 4
• 210000001035 gastrointestinal tract Anatomy 0.000 description 4
• 239000011521 glass Substances 0.000 description 4
• 239000003292 glue Substances 0.000 description 4
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
• 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 description 4
• 229910052749 magnesium Inorganic materials 0.000 description 4
• 229940091250 magnesium supplement Drugs 0.000 description 4
• 239000000546 pharmaceutical excipient Substances 0.000 description 4
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
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