JPS60224662A - 置換α‐アミノ酸類、それらの製法および医薬用途 - Google Patents

置換α‐アミノ酸類、それらの製法および医薬用途

Info

Publication number: JPS60224662A
Authority: JP; Japan
Prior art keywords: alkyl; group; formula; phenyl; compound
Prior art date: 1984-03-29
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

Application number

JP60062213A

Other languages

English (en)

Japanese (ja)

Inventor

ベルナー・ミユラー

パウル・リヌス・ヘルリング

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sandoz AG

Original Assignee

Sandoz AG

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.)

1984-03-29

Filing date

1985-03-28

Publication date

1985-11-09

1985-03-28 Application filed by Sandoz AG filed Critical Sandoz AG

1985-11-09 Publication of JPS60224662A publication Critical patent/JPS60224662A/ja

Status Pending legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 4
150000001371 alpha-amino acids Chemical class 0.000 title 1
235000008206 alpha-amino acids Nutrition 0.000 title 1
125000000217 alkyl group Chemical group 0.000 claims description 151
150000001875 compounds Chemical class 0.000 claims description 130
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 73
125000001624 naphthyl group Chemical group 0.000 claims description 60
239000001257 hydrogen Substances 0.000 claims description 35
229910052739 hydrogen Inorganic materials 0.000 claims description 35
125000003545 alkoxy group Chemical group 0.000 claims description 28
238000000034 method Methods 0.000 claims description 28
125000004076 pyridyl group Chemical group 0.000 claims description 28
150000003839 salts Chemical class 0.000 claims description 26
239000002253 acid Substances 0.000 claims description 20
-1 alicyclic group ester Chemical class 0.000 claims description 18
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 17
229910052736 halogen Inorganic materials 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
125000003277 amino group Chemical group 0.000 claims description 14
150000002367 halogens Chemical class 0.000 claims description 14
229910052717 sulfur Inorganic materials 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
125000001841 imino group Chemical group [H]N=* 0.000 claims description 12
239000011593 sulfur Substances 0.000 claims description 12
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
150000002431 hydrogen Chemical group 0.000 claims description 9
125000004185 ester group Chemical group 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 8
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
150000002148 esters Chemical class 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
125000006242 amine protecting group Chemical group 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000002843 carboxylic acid group Chemical group 0.000 claims description 6
125000001183 hydrocarbyl group Chemical group 0.000 claims description 6
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 5
125000003368 amide group Chemical group 0.000 claims description 5
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 5
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
125000003831 tetrazolyl group Chemical group 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
125000002270 phosphoric acid ester group Chemical group 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
229910052698 phosphorus Inorganic materials 0.000 claims description 3
230000008569 process Effects 0.000 claims description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
125000005907 alkyl ester group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
230000015572 biosynthetic process Effects 0.000 claims description 2
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
230000001590 oxidative effect Effects 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 2
239000011574 phosphorus Substances 0.000 claims description 2
150000003463 sulfur Chemical class 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
125000002723 alicyclic group Chemical group 0.000 claims 1
125000005090 alkenylcarbonyl group Chemical group 0.000 claims 1
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 1
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239000003937 drug carrier Substances 0.000 claims 1
239000008024 pharmaceutical diluent Substances 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
238000012360 testing method Methods 0.000 description 16
239000000203 mixture Substances 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
229940079593 drug Drugs 0.000 description 11
239000003814 drug Substances 0.000 description 11
239000000243 solution Substances 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000005557 antagonist Substances 0.000 description 9
230000008018 melting Effects 0.000 description 9
238000002844 melting Methods 0.000 description 9
230000000694 effects Effects 0.000 description 8
241000699670 Mus sp. Species 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
230000008485 antagonism Effects 0.000 description 5
239000002552 dosage form Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
ASNFTDCKZKHJSW-REOHCLBHSA-N Quisqualic acid Chemical compound OC(=O)[C@@H](N)CN1OC(=O)NC1=O ASNFTDCKZKHJSW-REOHCLBHSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
230000002860 competitive effect Effects 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
239000012730 sustained-release form Substances 0.000 description 4
206010021143 Hypoxia Diseases 0.000 description 3
208000008238 Muscle Spasticity Diseases 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 3
108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
230000001773 anti-convulsant effect Effects 0.000 description 3
239000001961 anticonvulsive agent Substances 0.000 description 3
229960003965 antiepileptics Drugs 0.000 description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
229960000623 carbamazepine Drugs 0.000 description 3
FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 3
210000003169 central nervous system Anatomy 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
231100000673 dose–response relationship Toxicity 0.000 description 3
206010015037 epilepsy Diseases 0.000 description 3
238000007327 hydrogenolysis reaction Methods 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
238000011084 recovery Methods 0.000 description 3
230000028327 secretion Effects 0.000 description 3
208000018198 spasticity Diseases 0.000 description 3
239000007858 starting material Substances 0.000 description 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 2
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 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
206010010904 Convulsion Diseases 0.000 description 2
ASNFTDCKZKHJSW-UHFFFAOYSA-N DL-Quisqualic acid Natural products OC(=O)C(N)CN1OC(=O)NC1=O ASNFTDCKZKHJSW-UHFFFAOYSA-N 0.000 description 2
241000006869 Halone Species 0.000 description 2
XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 2
HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 2
HOKKHZGPKSLGJE-UHFFFAOYSA-N N-methyl-D-aspartic acid Natural products CNC(C(O)=O)CC(O)=O HOKKHZGPKSLGJE-UHFFFAOYSA-N 0.000 description 2
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
DRUIESSIVFYOMK-UHFFFAOYSA-N Trichloroacetonitrile Chemical compound ClC(Cl)(Cl)C#N DRUIESSIVFYOMK-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000000556 agonist Substances 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
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229910052794 bromium Inorganic materials 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229960003067 cystine Drugs 0.000 description 2
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238000010511 deprotection reaction Methods 0.000 description 2
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
230000001146 hypoxic effect Effects 0.000 description 2
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230000033001 locomotion Effects 0.000 description 2
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239000012074 organic phase Substances 0.000 description 2
230000001575 pathological effect Effects 0.000 description 2
ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
201000000980 schizophrenia Diseases 0.000 description 2
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150000003457 sulfones Chemical class 0.000 description 2
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DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
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OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
XUJNEKJLAYXESH-UWTATZPHSA-N D-Cysteine Chemical compound SC[C@@H](N)C(O)=O XUJNEKJLAYXESH-UWTATZPHSA-N 0.000 description 1
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PEIKTSJIUKYDPC-UHFFFAOYSA-N Diethyl 3-Bromopropylphosphonate Chemical compound CCOP(=O)(OCC)CCCBr PEIKTSJIUKYDPC-UHFFFAOYSA-N 0.000 description 1
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
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LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 description 1
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239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
TWRAJPCQPHBABR-UHFFFAOYSA-N magnesium;diazide Chemical compound [Mg+2].[N-]=[N+]=[N-].[N-]=[N+]=[N-] TWRAJPCQPHBABR-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
125000004437 phosphorous atom Chemical group 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
210000000278 spinal cord Anatomy 0.000 description 1
238000012289 standard assay Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
230000000946 synaptic effect Effects 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
230000001256 tonic effect Effects 0.000 description 1
208000028500 tonic seizure Diseases 0.000 description 1
238000013519 translation Methods 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
238000005406 washing Methods 0.000 description 1
230000037303 wrinkles Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP60062213A 1984-03-29 1985-03-28 置換α‐アミノ酸類、それらの製法および医薬用途 Pending JPS60224662A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB8408059		1984-03-29
GB848408059A GB8408059D0 (en)	1984-03-29	1984-03-29	Organic compounds
GB8421091		1984-08-20

Publications (1)

Publication Number	Publication Date
JPS60224662A true JPS60224662A (ja)	1985-11-09

Family

ID=10558835

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP60062213A Pending JPS60224662A (ja)	1984-03-29	1985-03-28	置換α‐アミノ酸類、それらの製法および医薬用途

Country Status (4)

Country	Link
JP (1)	JPS60224662A (de)
AT (1)	AT385995B (de)
GB (1)	GB8408059D0 (de)
ZA (1)	ZA852423B (de)

1984
- 1984-03-29 GB GB848408059A patent/GB8408059D0/en active Pending
1985
- 1985-03-28 AT AT0091885A patent/AT385995B/de not_active IP Right Cessation
- 1985-03-28 JP JP60062213A patent/JPS60224662A/ja active Pending
- 1985-03-29 ZA ZA852423A patent/ZA852423B/xx unknown

Also Published As

Publication number	Publication date
ZA852423B (en)	1986-11-26
GB8408059D0 (en)	1984-05-10
AT385995B (de)	1988-06-10
ATA91885A (de)	1987-11-15

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