RU2344121C2 - Способы лечения заболеваний у млекопитающих - Google Patents

Info

Publication number

RU2344121C2

RU2344121C2 RU2006107650/04A RU2006107650A RU2344121C2 RU 2344121 C2 RU2344121 C2 RU 2344121C2 RU 2006107650/04 A RU2006107650/04 A RU 2006107650/04A RU 2006107650 A RU2006107650 A RU 2006107650A RU 2344121 C2 RU2344121 C2 RU 2344121C2

Authority

RU

Russia

Prior art keywords

methyl

acid

amino

aminomethyl

dimethyl

Prior art date

2003-09-25

Links

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• Global Dossier
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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 28
• 241000124008 Mammalia Species 0.000 title claims abstract description 17
• 201000010099 disease Diseases 0.000 title claims abstract description 8
• 238000000034 method Methods 0.000 title claims description 78
• 208000002193 Pain Diseases 0.000 claims abstract description 50
• 150000003839 salts Chemical class 0.000 claims abstract description 50
• 230000036407 pain Effects 0.000 claims abstract description 44
• 108090000312 Calcium Channels Proteins 0.000 claims abstract description 6
• 102000003922 Calcium Channels Human genes 0.000 claims abstract description 6
• 206010019233 Headaches Diseases 0.000 claims abstract description 5
• 206010036376 Postherpetic Neuralgia Diseases 0.000 claims abstract description 5
• 206010015037 epilepsy Diseases 0.000 claims abstract description 4
• 150000001875 compounds Chemical class 0.000 claims description 174
• 229910052739 hydrogen Inorganic materials 0.000 claims description 28
• 239000001257 hydrogen Substances 0.000 claims description 25
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
• 238000001356 surgical procedure Methods 0.000 claims description 4
• 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 1
• 206010007710 Cartilage injury Diseases 0.000 claims 1
• 208000008930 Low Back Pain Diseases 0.000 claims 1
• 239000003814 drug Substances 0.000 abstract description 28
• 230000006378 damage Effects 0.000 abstract description 11
• 150000001576 beta-amino acids Chemical class 0.000 abstract description 9
• 239000000126 substance Substances 0.000 abstract description 5
• 230000000694 effects Effects 0.000 abstract description 4
• 210000000845 cartilage Anatomy 0.000 abstract description 3
• 238000011477 surgical intervention Methods 0.000 abstract 2
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 106
• 239000000243 solution Substances 0.000 description 75
• 239000000203 mixture Substances 0.000 description 68
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 61
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 61
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 53
• 238000005481 NMR spectroscopy Methods 0.000 description 47
• -1 chloro, fluoro, amino Chemical group 0.000 description 40
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
• 239000000460 chlorine Substances 0.000 description 35
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 31
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
• 239000003921 oil Substances 0.000 description 30
• 235000019198 oils Nutrition 0.000 description 30
• 235000019439 ethyl acetate Nutrition 0.000 description 28
• 238000002360 preparation method Methods 0.000 description 26
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
• 239000012074 organic phase Substances 0.000 description 25
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• 229940079593 drug Drugs 0.000 description 24
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 23
• 201000006417 multiple sclerosis Diseases 0.000 description 23
• 239000007787 solid Substances 0.000 description 22
• 239000011541 reaction mixture Substances 0.000 description 20
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
• 208000035475 disorder Diseases 0.000 description 19
• 238000010992 reflux Methods 0.000 description 19
• 239000012267 brine Substances 0.000 description 18
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
• 238000006243 chemical reaction Methods 0.000 description 17
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
• 239000002904 solvent Substances 0.000 description 15
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
• 125000001153 fluoro group Chemical group F* 0.000 description 14
• 230000003993 interaction Effects 0.000 description 14
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
• 239000002253 acid Substances 0.000 description 12
• 239000010410 layer Substances 0.000 description 12
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 12
• 239000012071 phase Substances 0.000 description 12
• 239000007864 aqueous solution Substances 0.000 description 11
• 239000000706 filtrate Substances 0.000 description 11
• 238000000746 purification Methods 0.000 description 11
• 238000010898 silica gel chromatography Methods 0.000 description 11
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 10
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
• 230000015572 biosynthetic process Effects 0.000 description 10
• 208000004296 neuralgia Diseases 0.000 description 10
• 239000000651 prodrug Substances 0.000 description 10
• 229940002612 prodrug Drugs 0.000 description 10
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
• 150000002148 esters Chemical class 0.000 description 9
• 238000003818 flash chromatography Methods 0.000 description 9
• 230000007062 hydrolysis Effects 0.000 description 9
• 238000006460 hydrolysis reaction Methods 0.000 description 9
• 229920006395 saturated elastomer Polymers 0.000 description 9
• 238000003786 synthesis reaction Methods 0.000 description 9
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
• VCOJPHSIBVJVDU-UHFFFAOYSA-N 2-(aminomethyl)-4,4,8-trimethylnonanoic acid Chemical compound CC(C)CCCC(C)(C)CC(CN)C(O)=O VCOJPHSIBVJVDU-UHFFFAOYSA-N 0.000 description 8
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
• 230000001154 acute effect Effects 0.000 description 8
• 239000002775 capsule Substances 0.000 description 8
• 208000021722 neuropathic pain Diseases 0.000 description 8
• LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 8
• 239000011734 sodium Substances 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• 239000003826 tablet Substances 0.000 description 8
• 208000020401 Depressive disease Diseases 0.000 description 7
• 208000028017 Psychotic disease Diseases 0.000 description 7
• 239000000463 material Substances 0.000 description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
• 239000000843 powder Substances 0.000 description 7
• 239000000047 product Substances 0.000 description 7
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• 206010012335 Dependence Diseases 0.000 description 6
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
• 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 6
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
• 235000019270 ammonium chloride Nutrition 0.000 description 6
• 239000002585 base Substances 0.000 description 6
• ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 6
• 239000002552 dosage form Substances 0.000 description 6
• 206010022437 insomnia Diseases 0.000 description 6
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
• WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 6
• 125000004076 pyridyl group Chemical group 0.000 description 6
• 208000011580 syndromic disease Diseases 0.000 description 6
• KAOWNNSKQZBPBP-RRQHEKLDSA-N (2s)-2-amino-3,5-dimethylheptanoic acid Chemical compound CCC(C)CC(C)[C@H](N)C(O)=O KAOWNNSKQZBPBP-RRQHEKLDSA-N 0.000 description 5
• 208000020925 Bipolar disease Diseases 0.000 description 5
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
• 238000010521 absorption reaction Methods 0.000 description 5
• 125000000217 alkyl group Chemical group 0.000 description 5
• 230000000561 anti-psychotic effect Effects 0.000 description 5
• 238000013459 approach Methods 0.000 description 5
• SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 5
• 239000003085 diluting agent Substances 0.000 description 5
• 239000000543 intermediate Substances 0.000 description 5
• 239000007788 liquid Substances 0.000 description 5
• 239000007937 lozenge Substances 0.000 description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
• 210000005036 nerve Anatomy 0.000 description 5
• 201000008482 osteoarthritis Diseases 0.000 description 5
• 229910052763 palladium Inorganic materials 0.000 description 5
• 208000019116 sleep disease Diseases 0.000 description 5
• WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 5
• 238000003756 stirring Methods 0.000 description 5
• BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 5
• ZYZHMSJNPCYUTB-ZDUSSCGKSA-N (1s)-n-benzyl-1-phenylethanamine Chemical compound N([C@@H](C)C=1C=CC=CC=1)CC1=CC=CC=C1 ZYZHMSJNPCYUTB-ZDUSSCGKSA-N 0.000 description 4
• IVYDEZGCXPEAHO-HTQZYQBOSA-N (2r,4r)-2-(aminomethyl)-4-methylheptanoic acid Chemical compound CCC[C@@H](C)C[C@H](CN)C(O)=O IVYDEZGCXPEAHO-HTQZYQBOSA-N 0.000 description 4
• XKWDZEJCUWTBOM-BDAKNGLRSA-N (3s,5r)-3-amino-5-methylnonanoic acid Chemical compound CCCC[C@@H](C)C[C@H](N)CC(O)=O XKWDZEJCUWTBOM-BDAKNGLRSA-N 0.000 description 4
• CFMZXQJDAJXNHS-WLYNEOFISA-N (3s,5r)-3-amino-5-methyloctanoic acid;hydrochloride Chemical compound Cl.CCC[C@@H](C)C[C@H](N)CC(O)=O CFMZXQJDAJXNHS-WLYNEOFISA-N 0.000 description 4
• LXHFVSWWDNNDPW-SSDOTTSWSA-N (4r)-4-methylheptanoic acid Chemical compound CCC[C@@H](C)CCC(O)=O LXHFVSWWDNNDPW-SSDOTTSWSA-N 0.000 description 4
• FZVVRHWEJSBBDM-CKEIUWERSA-N (4r,5s)-4-methyl-3-[(4r)-4-methylheptanoyl]-5-phenyl-1,3-oxazolidin-2-one Chemical compound O1C(=O)N(C(=O)CC[C@H](C)CCC)[C@H](C)[C@@H]1C1=CC=CC=C1 FZVVRHWEJSBBDM-CKEIUWERSA-N 0.000 description 4
• JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 4
• WCTDVPDUYQPJRQ-UHFFFAOYSA-N 2-(aminomethyl)-4,8-dimethylnonanoic acid Chemical compound CC(C)CCCC(C)CC(CN)C(O)=O WCTDVPDUYQPJRQ-UHFFFAOYSA-N 0.000 description 4
• ZIJSPJLGYVZLDP-UHFFFAOYSA-N 2-(aminomethyl)-8-methylnonanoic acid Chemical compound CC(C)CCCCCC(CN)C(O)=O ZIJSPJLGYVZLDP-UHFFFAOYSA-N 0.000 description 4
• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 4
• MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 4
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• 208000004454 Hyperalgesia Diseases 0.000 description 4
• 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 4
• 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 4
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
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• 239000004480 active ingredient Substances 0.000 description 4
• 239000000443 aerosol Substances 0.000 description 4
• 150000001299 aldehydes Chemical class 0.000 description 4
• 150000001412 amines Chemical class 0.000 description 4
• 239000012298 atmosphere Substances 0.000 description 4
• 229910052799 carbon Inorganic materials 0.000 description 4
• 239000000969 carrier Substances 0.000 description 4
• 230000002490 cerebral effect Effects 0.000 description 4
• 208000026106 cerebrovascular disease Diseases 0.000 description 4
• 238000004587 chromatography analysis Methods 0.000 description 4
• 239000003086 colorant Substances 0.000 description 4
• 239000012230 colorless oil Substances 0.000 description 4
• AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 4
• MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 4
• 239000003937 drug carrier Substances 0.000 description 4
• 238000001914 filtration Methods 0.000 description 4
• 239000000796 flavoring agent Substances 0.000 description 4
• 238000007327 hydrogenolysis reaction Methods 0.000 description 4
• JXEHXYFSIOYTAH-SFYZADRCSA-N imagabalin Chemical compound CCC[C@@H](C)C[C@H](N)CC(O)=O JXEHXYFSIOYTAH-SFYZADRCSA-N 0.000 description 4
• AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
• 230000007935 neutral effect Effects 0.000 description 4
• 239000012044 organic layer Substances 0.000 description 4
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
• 125000006239 protecting group Chemical group 0.000 description 4
• 230000007958 sleep Effects 0.000 description 4
• GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
• 239000008107 starch Substances 0.000 description 4
• 235000019698 starch Nutrition 0.000 description 4
• 125000001424 substituent group Chemical group 0.000 description 4
• ZYZHMSJNPCYUTB-CYBMUJFWSA-N (1r)-n-benzyl-1-phenylethanamine Chemical compound N([C@H](C)C=1C=CC=CC=1)CC1=CC=CC=C1 ZYZHMSJNPCYUTB-CYBMUJFWSA-N 0.000 description 3
• RCYIBFNZRWQGNB-SECBINFHSA-N (2R)-2,6-dimethylheptan-1-ol Chemical compound CC(C)CCC[C@@H](C)CO RCYIBFNZRWQGNB-SECBINFHSA-N 0.000 description 3
• TVLKZPKESPWMLL-SECBINFHSA-N (2r)-1-iodo-2,6-dimethylheptane Chemical compound CC(C)CCC[C@@H](C)CI TVLKZPKESPWMLL-SECBINFHSA-N 0.000 description 3
• DQZWXDKUALGTBI-RTBKNWGFSA-N (2s)-2-amino-3,5-dimethylnonanoic acid Chemical compound CCCCC(C)CC(C)[C@H](N)C(O)=O DQZWXDKUALGTBI-RTBKNWGFSA-N 0.000 description 3
• YDFXGYXAYDURTF-MNOVXSKESA-N (2s,4r)-4-methyl-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]heptanoic acid Chemical compound CCC[C@@H](C)C[C@H](C(O)=O)CC(=O)OC(C)(C)C YDFXGYXAYDURTF-MNOVXSKESA-N 0.000 description 3
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
• MGKJIAFHRWWQMB-UHFFFAOYSA-N 2,2,6-trimethylheptanal Chemical compound CC(C)CCCC(C)(C)C=O MGKJIAFHRWWQMB-UHFFFAOYSA-N 0.000 description 3
• KFUYJCLUBOFHHM-UHFFFAOYSA-N 2-(aminomethyl)-3-(1-methylcyclopropyl)propanoic acid Chemical compound NCC(C(O)=O)CC1(C)CC1 KFUYJCLUBOFHHM-UHFFFAOYSA-N 0.000 description 3
• BJIZVOAKFOHTPR-UHFFFAOYSA-N 2-(aminomethyl)-4-ethylhexanoic acid Chemical compound CCC(CC)CC(CN)C(O)=O BJIZVOAKFOHTPR-UHFFFAOYSA-N 0.000 description 3
• IYWIMUAQVYROEC-UHFFFAOYSA-N 2-(aminomethyl)-4-ethyloctanoic acid Chemical compound CCCCC(CC)CC(CN)C(O)=O IYWIMUAQVYROEC-UHFFFAOYSA-N 0.000 description 3
• 208000024827 Alzheimer disease Diseases 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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• 206010012289 Dementia Diseases 0.000 description 3
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
• 208000007590 Disorders of Excessive Somnolence Diseases 0.000 description 3
• 208000012661 Dyskinesia Diseases 0.000 description 3
• UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 3
• 108010010803 Gelatin Proteins 0.000 description 3
• 206010019196 Head injury Diseases 0.000 description 3
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• 229960000583 acetic acid Drugs 0.000 description 3
• 150000007513 acids Chemical class 0.000 description 3
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• OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 3
• 150000001408 amides Chemical class 0.000 description 3
• 150000001413 amino acids Chemical class 0.000 description 3
• 239000007900 aqueous suspension Substances 0.000 description 3
• 125000004429 atom Chemical group 0.000 description 3
• AMEWIQLMDPIPRK-UHFFFAOYSA-N benzyl 2-cyano-4,4,8-trimethylnon-2-enoate Chemical compound CC(C)CCCC(C)(C)C=C(C#N)C(=O)OCC1=CC=CC=C1 AMEWIQLMDPIPRK-UHFFFAOYSA-N 0.000 description 3
• 235000019445 benzyl alcohol Nutrition 0.000 description 3
• PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
• 239000003054 catalyst Substances 0.000 description 3
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