UA80559C2 - The derivatives of r(+)-2-amino-3-hydroxypropanoic acid having the glycinergic action - Google Patents

The derivatives of r(+)-2-amino-3-hydroxypropanoic acid having the glycinergic action Download PDF

Info

Publication number: UA80559C2
Authority: UA; Ukraine
Prior art keywords: amino; pharmaceutically acceptable; hydroxypropionic acid; acceptable salts; alkyl
Prior art date: 2002-08-14

Application number

UAA200501927A

Other languages

English (en)

Ukrainian (uk)

Inventor

Camille Georges Wermuth

Priority date (The priority date 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 date listed.)

2002-08-14

Filing date

2003-01-08

Publication date

2007-10-10

2003-01-08 Application filed filed Critical

2007-10-10 Publication of UA80559C2 publication Critical patent/UA80559C2/uk

Links

230000000575 glycinergic effect Effects 0.000 title 1
150000003839 salts Chemical class 0.000 claims abstract description 66
125000000217 alkyl group Chemical group 0.000 claims abstract description 44
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 42
239000004305 biphenyl Substances 0.000 claims abstract description 41
125000003342 alkenyl group Chemical group 0.000 claims abstract description 20
125000001118 alkylidene group Chemical group 0.000 claims abstract description 17
230000027682 synaptic transmission, glycinergic Effects 0.000 claims abstract description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
201000000980 schizophrenia Diseases 0.000 claims abstract description 9
201000010099 disease Diseases 0.000 claims abstract description 8
208000024827 Alzheimer disease Diseases 0.000 claims abstract description 6
238000002360 preparation method Methods 0.000 claims abstract description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 59
229910052739 hydrogen Inorganic materials 0.000 claims description 39
239000001257 hydrogen Substances 0.000 claims description 38
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 14
229910052700 potassium Inorganic materials 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 12
150000002431 hydrogen Chemical class 0.000 claims description 12
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
239000013543 active substance Substances 0.000 claims description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
210000003169 central nervous system Anatomy 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
GZRGHDIUPMPHCB-UHFFFAOYSA-N 1-[4-(4-acetylphenoxy)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OC1=CC=C(C(C)=O)C=C1 GZRGHDIUPMPHCB-UHFFFAOYSA-N 0.000 claims description 6
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
206010003805 Autism Diseases 0.000 claims description 5
208000020706 Autistic disease Diseases 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
230000001149 cognitive effect Effects 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
ZRVBMNHMJLBKSY-UHFFFAOYSA-N 2-phenacyloxy-1-phenylethanone Chemical compound C=1C=CC=CC=1C(=O)COCC(=O)C1=CC=CC=C1 ZRVBMNHMJLBKSY-UHFFFAOYSA-N 0.000 claims description 2
ZUVAACFIEPYYOP-UHFFFAOYSA-N methoxycyclopropane Chemical compound COC1CC1 ZUVAACFIEPYYOP-UHFFFAOYSA-N 0.000 claims description 2
208000015114 central nervous system disease Diseases 0.000 claims 3
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
150000001555 benzenes Chemical class 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
-1 N,N'-disubstituted lysinoyl Chemical group 0.000 abstract description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 7
239000003814 drug Substances 0.000 abstract description 3
230000002829 reductive effect Effects 0.000 abstract description 3
125000001980 alanyl group Chemical class 0.000 abstract description 2
125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 2
125000005862 (C1-C6)alkanoyl group Chemical group 0.000 abstract 1
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 32
239000000047 product Substances 0.000 description 23
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
150000001875 compounds Chemical class 0.000 description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
239000004471 Glycine Substances 0.000 description 16
239000000243 solution Substances 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 14
239000012074 organic phase Substances 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
238000005481 NMR spectroscopy Methods 0.000 description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
150000002148 esters Chemical class 0.000 description 10
239000000706 filtrate Substances 0.000 description 10
230000008018 melting Effects 0.000 description 10
238000002844 melting Methods 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
239000000843 powder Substances 0.000 description 9
239000007787 solid Substances 0.000 description 9
239000003921 oil Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000012047 saturated solution Substances 0.000 description 7
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
238000004587 chromatography analysis 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
239000000377 silicon dioxide Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000000556 agonist Substances 0.000 description 4
125000001589 carboacyl group Chemical group 0.000 description 4
LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 4
125000004494 ethyl ester group Chemical group 0.000 description 4
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
GWCPTZNOWFHMER-UHFFFAOYSA-N (4-bromo-1-phenylbut-1-enyl)benzene Chemical compound C=1C=CC=CC=1C(=CCCBr)C1=CC=CC=C1 GWCPTZNOWFHMER-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
239000002585 base Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
208000010877 cognitive disease Diseases 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000002243 precursor Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
208000024891 symptom Diseases 0.000 description 3
DJQUGRJFLXSMHS-UHFFFAOYSA-N (4-bromo-1-phenylbutyl)benzene Chemical compound C=1C=CC=CC=1C(CCCBr)C1=CC=CC=C1 DJQUGRJFLXSMHS-UHFFFAOYSA-N 0.000 description 2
JBQWQBSRIAGTJT-UHFFFAOYSA-N 3-ethylmorpholine Chemical compound CCC1COCCN1 JBQWQBSRIAGTJT-UHFFFAOYSA-N 0.000 description 2
TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 2
HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 2
MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
208000026139 Memory disease Diseases 0.000 description 2
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 2
208000002193 Pain Diseases 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
229940024606 amino acid Drugs 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000000919 ceramic Substances 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
229940079593 drug Drugs 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000000034 method Methods 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
239000002808 molecular sieve Substances 0.000 description 2
230000037023 motor activity Effects 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
230000036407 pain Effects 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 1
229960000549 4-dimethylaminophenol Drugs 0.000 description 1
229940073735 4-hydroxy acetophenone Drugs 0.000 description 1
QNAYBMKLOCPYGJ-UWTATZPHSA-N D-alanine Chemical compound C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 1
IPWKGIFRRBGCJO-QWWZWVQMSA-N D-alanyl-D-serine zwitterion Chemical compound C[C@@H](N)C(=O)N[C@H](CO)C(O)=O IPWKGIFRRBGCJO-QWWZWVQMSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
239000002262 Schiff base Substances 0.000 description 1
150000004753 Schiff bases Chemical class 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
239000004473 Threonine Substances 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
150000003862 amino acid derivatives Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
230000000561 anti-psychotic effect Effects 0.000 description 1
229940009098 aspartate Drugs 0.000 description 1
230000003542 behavioural effect Effects 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
239000012965 benzophenone Substances 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
239000002775 capsule Substances 0.000 description 1
MFKPHBJFWOOEDT-UHFFFAOYSA-N cyclopropyl(diphenyl)methanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1CC1 MFKPHBJFWOOEDT-UHFFFAOYSA-N 0.000 description 1
GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical compound OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
201000003723 learning disability Diseases 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
BLQBVPNQNGGJEG-UHFFFAOYSA-N methoxycyclopropane;hydrochloride Chemical compound Cl.COC1CC1 BLQBVPNQNGGJEG-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
125000000160 oxazolidinyl group Chemical group 0.000 description 1
JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000005062 synaptic transmission Effects 0.000 description 1
230000007593 synaptic transmission, glutaminergic Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
- A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/22—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Organic Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Neurosurgery (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Epidemiology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Psychiatry (AREA)
Hospice & Palliative Care (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Peptides Or Proteins (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

UAA200501927A 2002-08-14 2003-01-08 The derivatives of r(+)-2-amino-3-hydroxypropanoic acid having the glycinergic action UA80559C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR0210306A FR2843590B1 (fr)	2002-08-14	2002-08-14	Derives de l'acide r(+)-2-amino-3-hydroxypropanoique a action glycinergique
PCT/FR2003/002447 WO2004016580A2 (fr)	2002-08-14	2003-08-01	Derives de l'acide r(+)-2-amino-3-hydroxypropanoique a action glycinergique

Publications (1)

Publication Number	Publication Date
UA80559C2 true UA80559C2 (en)	2007-10-10

Family

ID=30775996

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UAA200501927A UA80559C2 (en)	2002-08-14	2003-01-08	The derivatives of r(+)-2-amino-3-hydroxypropanoic acid having the glycinergic action

Country Status (19)

Country	Link
US (1)	US7488755B2 (fr)
EP (1)	EP1529030A2 (fr)
JP (1)	JP2005535715A (fr)
KR (2)	KR100890674B1 (fr)
CN (1)	CN1675169A (fr)
AU (1)	AU2003274213B2 (fr)
BR (1)	BR0313740A (fr)
CA (1)	CA2497347A1 (fr)
CR (1)	CR7736A (fr)
EA (1)	EA010417B1 (fr)
FR (1)	FR2843590B1 (fr)
GE (1)	GEP20074194B (fr)
IL (1)	IL166778A0 (fr)
MX (1)	MXPA05001761A (fr)
NO (1)	NO20050961L (fr)
NZ (1)	NZ538633A (fr)
PL (1)	PL375413A1 (fr)
UA (1)	UA80559C2 (fr)
WO (1)	WO2004016580A2 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2776388A4 (fr) *	2011-11-10	2015-07-08	Davuluri Ramamohan Rao	Procédé inédit de préparation de (r)-n-benzyl-2-acétamido-3-méthoxypropionamide

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH03236315A (ja) *	1989-12-05	1991-10-22	Nippon Oil & Fats Co Ltd	抗精神病薬
US5332758A (en) *	1990-07-13	1994-07-26	Kanebo, Ltd.	Collagen metabolism ameliorant and its use
ES2036926B1 (es) *	1991-08-08	1994-01-16	Uriach & Cia Sa J	"procedimiento para la obtencion de derivados de la (2-alquil-3-piridil)metilpiperazina".
GB9425730D0 (en)	1994-12-20	1995-02-22	Nycomed Pharma As	Compounds
PT871440E (pt) *	1995-12-07	2006-07-31	Daniel C Javitt	Tratamento de sintomas negativos e cognitivos de esquizofrenia com antagonistas da captacao de glicina
IT1283489B1 (it) *	1996-07-23	1998-04-21	Chiesi Farma Spa	Ammidi di alfa-amminoacidi,loro preparazione e loro impiego terapeutico
AU765603C (en) *	1998-04-14	2004-08-05	General Hospital Corporation, The	Methods for treating neuropsychiatric disorders
GB2410947B (en)	2004-02-11	2008-09-17	Cambridge Lab Ltd	Pharmaceutical compounds

2002
- 2002-08-14 FR FR0210306A patent/FR2843590B1/fr not_active Expired - Fee Related
2003
- 2003-01-08 UA UAA200501927A patent/UA80559C2/uk unknown
- 2003-08-01 EP EP03758195A patent/EP1529030A2/fr not_active Withdrawn
- 2003-08-01 KR KR1020077013426A patent/KR100890674B1/ko not_active Expired - Fee Related
- 2003-08-01 MX MXPA05001761A patent/MXPA05001761A/es active IP Right Grant
- 2003-08-01 BR BR0313740-6A patent/BR0313740A/pt not_active IP Right Cessation
- 2003-08-01 CN CNA038188481A patent/CN1675169A/zh active Pending
- 2003-08-01 US US10/524,869 patent/US7488755B2/en not_active Expired - Fee Related
- 2003-08-01 AU AU2003274213A patent/AU2003274213B2/en not_active Ceased
- 2003-08-01 WO PCT/FR2003/002447 patent/WO2004016580A2/fr not_active Ceased
- 2003-08-01 NZ NZ538633A patent/NZ538633A/en not_active IP Right Cessation
- 2003-08-01 PL PL03375413A patent/PL375413A1/xx unknown
- 2003-08-01 KR KR1020057002073A patent/KR100756138B1/ko not_active Expired - Fee Related
- 2003-08-01 JP JP2004528582A patent/JP2005535715A/ja active Pending
- 2003-08-01 GE GEAP8683A patent/GEP20074194B/en unknown
- 2003-08-01 CA CA002497347A patent/CA2497347A1/fr not_active Abandoned
- 2003-08-01 EA EA200500333A patent/EA010417B1/ru not_active IP Right Cessation
2005
- 2005-02-09 IL IL16677805A patent/IL166778A0/xx unknown
- 2005-02-23 NO NO20050961A patent/NO20050961L/no not_active Application Discontinuation
- 2005-03-11 CR CR7736A patent/CR7736A/es unknown

Also Published As

Publication number	Publication date
KR100890674B1 (ko)	2009-03-26
CN1675169A (zh)	2005-09-28
KR20070067250A (ko)	2007-06-27
NZ538633A (en)	2007-10-26
PL375413A1 (en)	2005-11-28
WO2004016580A2 (fr)	2004-02-26
IL166778A0 (en)	2006-01-15
MXPA05001761A (es)	2005-04-25
CR7736A (es)	2008-10-10
CA2497347A1 (fr)	2004-02-26
WO2004016580A3 (fr)	2004-04-08
NO20050961L (no)	2005-04-28
KR20050055697A (ko)	2005-06-13
AU2003274213A1 (en)	2004-03-03
EA200500333A1 (ru)	2005-08-25
AU2003274213B2 (en)	2008-03-13
JP2005535715A (ja)	2005-11-24
EP1529030A2 (fr)	2005-05-11
FR2843590B1 (fr)	2007-10-05
KR100756138B1 (ko)	2007-09-05
US7488755B2 (en)	2009-02-10
EA010417B1 (ru)	2008-08-29
BR0313740A (pt)	2005-07-19
FR2843590A1 (fr)	2004-02-20
GEP20074194B (en)	2007-09-10
US20050261372A1 (en)	2005-11-24

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