JPWO2020014246A5 - - Google Patents

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Publication number

JPWO2020014246A5

JPWO2020014246A5 JP2021500411A JP2021500411A JPWO2020014246A5 JP WO2020014246 A5 JPWO2020014246 A5 JP WO2020014246A5 JP 2021500411 A JP2021500411 A JP 2021500411A JP 2021500411 A JP2021500411 A JP 2021500411A JP WO2020014246 A5 JPWO2020014246 A5 JP WO2020014246A5

Authority

JP

Japan

Prior art keywords

trifluoromethyl

carboxamide

phenoxy

pyridin

alkyl

Prior art date

2022-04-12

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Pending

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• -1 cyano, amino Chemical group 0.000 claims description 824
• 150000001875 compounds Chemical class 0.000 claims description 296
• 125000000217 alkyl group Chemical group 0.000 claims description 252
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 170
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 167
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 153
• 239000000203 mixture Substances 0.000 claims description 124
• 229910052757 nitrogen Inorganic materials 0.000 claims description 98
• 229910052739 hydrogen Inorganic materials 0.000 claims description 92
• 229910052799 carbon Inorganic materials 0.000 claims description 90
• 229910052736 halogen Inorganic materials 0.000 claims description 89
• 150000002367 halogens Chemical class 0.000 claims description 88
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 86
• 201000006417 multiple sclerosis Diseases 0.000 claims description 75
• 125000003545 alkoxy group Chemical group 0.000 claims description 66
• 239000011734 sodium Substances 0.000 claims description 65
• 125000003118 aryl group Chemical group 0.000 claims description 55
• 125000001072 heteroaryl group Chemical group 0.000 claims description 54
• 239000011780 sodium chloride Substances 0.000 claims description 53
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 50
• 150000003839 salts Chemical class 0.000 claims description 50
• 125000001424 substituent group Chemical group 0.000 claims description 43
• 239000001257 hydrogen Substances 0.000 claims description 42
• 125000004076 pyridyl group Chemical group 0.000 claims description 42
• 208000002193 Pain Diseases 0.000 claims description 41
• 125000004432 carbon atoms Chemical group C* 0.000 claims description 41
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 37
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 36
• 230000002401 inhibitory effect Effects 0.000 claims description 36
• 230000036407 pain Effects 0.000 claims description 36
• OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 35
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
• 201000010099 disease Diseases 0.000 claims description 35
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 31
• 239000003814 drug Substances 0.000 claims description 30
• 125000002757 morpholinyl group Chemical group 0.000 claims description 25
• 102000018674 Sodium Channels Human genes 0.000 claims description 24
• 108010052164 Sodium Channels Proteins 0.000 claims description 24
• 125000004043 oxo group Chemical group O=* 0.000 claims description 21
• 125000000623 heterocyclic group Chemical group 0.000 claims description 19
• DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 19
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 18
• 125000004104 aryloxy group Chemical group 0.000 claims description 17
• 230000000694 effects Effects 0.000 claims description 17
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 16
• 125000005418 aryl aryl group Chemical group 0.000 claims description 16
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 16
• 230000014509 gene expression Effects 0.000 claims description 16
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
• 125000002971 oxazolyl group Chemical group 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 12
• 230000001965 increased Effects 0.000 claims description 12
• ILVXOBCQQYKLDS-UHFFFAOYSA-N Pyridine-N-oxide Chemical group [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 11
• 229940079593 drugs Drugs 0.000 claims description 11
• 239000011570 nicotinamide Substances 0.000 claims description 10
• 235000005152 nicotinamide Nutrition 0.000 claims description 10
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 10
• 208000004296 Neuralgia Diseases 0.000 claims description 9
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 8
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
• 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 8
• 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 8
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 7
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
• 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims description 6
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
• 125000005360 alkyl sulfoxide group Chemical group 0.000 claims description 6
• 125000005018 aryl alkenyl group Chemical group 0.000 claims description 6
• 201000011384 erythromelalgia Diseases 0.000 claims description 6
• 230000001105 regulatory Effects 0.000 claims description 6
• 206010065390 Inflammatory pain Diseases 0.000 claims description 5
• 206010029331 Neuropathy peripheral Diseases 0.000 claims description 5
• 229940005483 OPIOID ANALGESICS Drugs 0.000 claims description 5
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
• 201000001119 neuropathy Diseases 0.000 claims description 5
• 239000000014 opioid analgesic Substances 0.000 claims description 5
• 201000010874 syndrome Diseases 0.000 claims description 5
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 4
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 4
• 206010003119 Arrhythmia Diseases 0.000 claims description 4
• 206010007521 Cardiac arrhythmias Diseases 0.000 claims description 4
• 208000000094 Chronic Pain Diseases 0.000 claims description 4
• 229940093912 Gynecological Sulfonamides Drugs 0.000 claims description 4
• 206010019233 Headache Diseases 0.000 claims description 4
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
• 229940079867 intestinal antiinfectives Sulfonamides Drugs 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 229940005938 ophthalmologic antiinfectives Sulfonamides Drugs 0.000 claims description 4
• RZVAJINKPMORJF-UHFFFAOYSA-N p-acetaminophenol Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 4
• 229960005489 paracetamol Drugs 0.000 claims description 4
• 230000002093 peripheral Effects 0.000 claims description 4
• 150000003456 sulfonamides Chemical group 0.000 claims description 4
• 229940026752 topical Sulfonamides Drugs 0.000 claims description 4
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
• 229940022659 Acetaminophen Drugs 0.000 claims description 3
• 241000580858 Simian-Human immunodeficiency virus Species 0.000 claims description 3
• 208000009935 Visceral Pain Diseases 0.000 claims description 3
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 2
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
• 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims description 2
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 2
• 206010002855 Anxiety Diseases 0.000 claims description 2
• 206010057666 Anxiety disease Diseases 0.000 claims description 2
• 206010003210 Arteriosclerosis Diseases 0.000 claims description 2
• 206010003246 Arthritis Diseases 0.000 claims description 2
• 206010003658 Atrial fibrillation Diseases 0.000 claims description 2
• 206010004939 Bipolar I disease Diseases 0.000 claims description 2
• 206010004938 Bipolar disease Diseases 0.000 claims description 2
• 206010011401 Crohn's disease Diseases 0.000 claims description 2
• 208000001636 Diabetic Neuropathy Diseases 0.000 claims description 2
• 206010012680 Diabetic neuropathy Diseases 0.000 claims description 2
• 208000010118 Dystonia Diseases 0.000 claims description 2
• 208000001640 Fibromyalgia Diseases 0.000 claims description 2
• 208000007514 Herpes Zoster Diseases 0.000 claims description 2
• 206010020751 Hypersensitivity Diseases 0.000 claims description 2
• 206010020844 Hyperthermia malignant Diseases 0.000 claims description 2
• 208000003532 Hypothyroidism Diseases 0.000 claims description 2
• 206010022114 Injury Diseases 0.000 claims description 2
• 102100017700 LGI1 Human genes 0.000 claims description 2
• 101700058968 LGI1 Proteins 0.000 claims description 2
• 208000007914 Labor Pain Diseases 0.000 claims description 2
• 206010059204 Labour pain Diseases 0.000 claims description 2
• 206010052313 Liddle's syndrome Diseases 0.000 claims description 2
• 206010027599 Migraine Diseases 0.000 claims description 2
• 208000008085 Migraine Disorders Diseases 0.000 claims description 2
• 206010028372 Muscular weakness Diseases 0.000 claims description 2
• 208000000693 Neurogenic Urinary Bladder Diseases 0.000 claims description 2
• 206010029279 Neurogenic bladder Diseases 0.000 claims description 2
• 208000001293 Peripheral Nervous System Disease Diseases 0.000 claims description 2
• 206010034606 Peripheral neuropathy Diseases 0.000 claims description 2
• 206010056238 Phantom pain Diseases 0.000 claims description 2
• 208000004550 Postoperative Pain Diseases 0.000 claims description 2
• 208000000399 Procedural Pain Diseases 0.000 claims description 2
• 208000003251 Pruritus Diseases 0.000 claims description 2
• 206010037113 Pseudoaldosteronism Diseases 0.000 claims description 2
• 206010039073 Rheumatoid arthritis Diseases 0.000 claims description 2
• FDDDEECHVMSUSB-UHFFFAOYSA-N Sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 2
• 206010043269 Tension headache Diseases 0.000 claims description 2
• 208000008548 Tension-Type Headache Diseases 0.000 claims description 2
• 206010043994 Tonic convulsion Diseases 0.000 claims description 2
• 208000004371 Toothache Diseases 0.000 claims description 2
• 231100000765 Toxin Toxicity 0.000 claims description 2
• 210000003901 Trigeminal Nerve Anatomy 0.000 claims description 2
• 208000003663 Ventricular Fibrillation Diseases 0.000 claims description 2
• 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 2
• 201000005794 allergic hypersensitivity disease Diseases 0.000 claims description 2
• 230000036506 anxiety Effects 0.000 claims description 2
• 201000001320 atherosclerosis Diseases 0.000 claims description 2
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
• 201000011510 cancer Diseases 0.000 claims description 2
• 238000002512 chemotherapy Methods 0.000 claims description 2
• 201000003883 cystic fibrosis Diseases 0.000 claims description 2
• 229910052731 fluorine Inorganic materials 0.000 claims description 2
• 239000011737 fluorine Substances 0.000 claims description 2
• 231100000869 headache Toxicity 0.000 claims description 2
• 230000009610 hypersensitivity Effects 0.000 claims description 2
• 230000002989 hypothyroidism Effects 0.000 claims description 2
• 230000000302 ischemic Effects 0.000 claims description 2
• 201000010901 lateral sclerosis Diseases 0.000 claims description 2
• 201000007004 malignant hyperthermia Diseases 0.000 claims description 2
• 230000036473 myasthenia Effects 0.000 claims description 2
• 230000004112 neuroprotection Effects 0.000 claims description 2
• 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 2
• 201000008482 osteoarthritis Diseases 0.000 claims description 2
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
• 230000001314 paroxysmal Effects 0.000 claims description 2
• 230000002085 persistent Effects 0.000 claims description 2
• 201000000980 schizophrenia Diseases 0.000 claims description 2
• 201000009890 sinusitis Diseases 0.000 claims description 2
• 229960001663 sulfanilamide Drugs 0.000 claims description 2
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
• 239000003053 toxin Substances 0.000 claims description 2
• 230000000472 traumatic Effects 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 8
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 7
• 206010009887 Colitis Diseases 0.000 claims 1
• 210000003414 Extremities Anatomy 0.000 claims 1
• CBOIHMRHGLHBPB-UHFFFAOYSA-N Hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
• 101710006116 IL31RA Proteins 0.000 claims 1
• 210000003205 Muscles Anatomy 0.000 claims 1
• 208000005010 Paroxysmal Extreme Pain Disorder Diseases 0.000 claims 1
• 206010011302 Peripheral nerve injury Diseases 0.000 claims 1
• 206010039020 Rhabdomyolysis Diseases 0.000 claims 1
• YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
• 230000000541 pulsatile Effects 0.000 claims 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 93
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N DMSO-d6 Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 88
• XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
• 238000003786 synthesis reaction Methods 0.000 description 63
• 230000015572 biosynthetic process Effects 0.000 description 62
• 230000002194 synthesizing Effects 0.000 description 62
• 239000007787 solid Substances 0.000 description 60
• 239000000243 solution Substances 0.000 description 60
• 238000005160 1H NMR spectroscopy Methods 0.000 description 51
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 38
• HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
• 239000002904 solvent Substances 0.000 description 38
• WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
• 239000002244 precipitate Substances 0.000 description 33
• 238000001914 filtration Methods 0.000 description 28
• VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
• 235000019439 ethyl acetate Nutrition 0.000 description 27
• YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
• 239000003795 chemical substances by application Substances 0.000 description 24
• FJDQFPXHSGXQBY-UHFFFAOYSA-L Caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 22
• 125000004435 hydrogen atoms Chemical class [H]* 0.000 description 22
• 238000003756 stirring Methods 0.000 description 22
• 101710032460 SCN10A Proteins 0.000 description 21
• 102100010564 SCN10A Human genes 0.000 description 20
• 239000003112 inhibitor Substances 0.000 description 20
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
• UQYZFNUUOSSNKT-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium;hexafluorophosphate Chemical compound F[P-](F)(F)(F)(F)F.C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 UQYZFNUUOSSNKT-UHFFFAOYSA-N 0.000 description 19
• 239000002253 acid Substances 0.000 description 19
• 210000004027 cells Anatomy 0.000 description 18
• 125000004404 heteroalkyl group Chemical group 0.000 description 17
• 125000005842 heteroatoms Chemical group 0.000 description 17
• 229910052708 sodium Inorganic materials 0.000 description 17
• MBNPJRQKQLLRIS-UHFFFAOYSA-N 3-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC=CC(N)=C1 MBNPJRQKQLLRIS-UHFFFAOYSA-N 0.000 description 16
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
• 238000001816 cooling Methods 0.000 description 15
• 238000000746 purification Methods 0.000 description 15
• 125000002947 alkylene group Chemical group 0.000 description 14
• 238000004166 bioassay Methods 0.000 description 14
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
• IMNFDUFMRHMDMM-UHFFFAOYSA-N n-heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
• OULGLTLTWBZBLO-UHFFFAOYSA-N 4-fluoro-2-methoxyphenol Chemical compound COC1=CC(F)=CC=C1O OULGLTLTWBZBLO-UHFFFAOYSA-N 0.000 description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
• 125000004429 atoms Chemical group 0.000 description 13
• 230000000051 modifying Effects 0.000 description 13
• 229910052717 sulfur Inorganic materials 0.000 description 13
• 125000004122 cyclic group Chemical group 0.000 description 12
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
• 102000004310 Ion Channels Human genes 0.000 description 11
• 108090000862 Ion Channels Proteins 0.000 description 11
• 238000007792 addition Methods 0.000 description 11
• 239000012267 brine Substances 0.000 description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
• 125000000524 functional group Chemical group 0.000 description 11
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• 125000006239 protecting group Chemical group 0.000 description 11
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• 125000000547 substituted alkyl group Chemical group 0.000 description 11
• 230000002195 synergetic Effects 0.000 description 11
• 150000002430 hydrocarbons Chemical class 0.000 description 10
• 239000000047 product Substances 0.000 description 10
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• ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
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• 102000016913 Voltage-Gated Sodium Channels Human genes 0.000 description 9
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• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
• 125000002252 acyl group Chemical group 0.000 description 8
• 230000003042 antagnostic Effects 0.000 description 8
• LKYXEULZVGJVTG-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH] LKYXEULZVGJVTG-UHFFFAOYSA-N 0.000 description 8
• 238000004587 chromatography analysis Methods 0.000 description 8
• CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 description 8
• CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
• NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
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• KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
• CTSLXHKWHWQRSH-UHFFFAOYSA-N Oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
• 230000002378 acidificating Effects 0.000 description 6
• 125000000304 alkynyl group Chemical group 0.000 description 6
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
• HEDRZPFGACZZDS-MICDWDOJSA-N cdcl3 Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
• 238000006243 chemical reaction Methods 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
• 239000002552 dosage form Substances 0.000 description 6
• GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical compound [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 6
• 235000001968 nicotinic acid Nutrition 0.000 description 6
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• 125000003107 substituted aryl group Chemical group 0.000 description 6
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• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
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