JPS60123472A - アミノピリジンカルボン酸誘導体ならびに医薬組成物 - Google Patents

アミノピリジンカルボン酸誘導体ならびに医薬組成物

Info

Publication number: JPS60123472A
Authority: JP; Japan
Prior art keywords: methyl; carbon atoms; hydrogen; propionamide; acetylthiomethyl
Prior art date: 1983-12-08
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.): Granted

Application number

JP23260483A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0441143B2 (fr

Inventor

ビツトリオ　ベクチエチ

ギオルギオ　フラリ

セサレ　カサグランデ

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.)

SIMES Societa Italiana Medicinali e Sintetici SpA

Original Assignee

SIMES Societa Italiana Medicinali e Sintetici SpA

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.)

1983-12-08

Filing date

1983-12-08

Publication date

1985-07-02

1983-12-08 Application filed by SIMES Societa Italiana Medicinali e Sintetici SpA filed Critical SIMES Societa Italiana Medicinali e Sintetici SpA

1983-12-08 Priority to JP23260483A priority Critical patent/JPS60123472A/ja

1985-07-02 Publication of JPS60123472A publication Critical patent/JPS60123472A/ja

1992-07-07 Publication of JPH0441143B2 publication Critical patent/JPH0441143B2/ja

Status Granted legal-status Critical Current

Links

239000008194 pharmaceutical composition Substances 0.000 title description 5
BOOMHTFCWOJWFO-UHFFFAOYSA-N 3-aminopyridine-2-carboxylic acid Chemical class NC1=CC=CN=C1C(O)=O BOOMHTFCWOJWFO-UHFFFAOYSA-N 0.000 title description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 64
150000001875 compounds Chemical class 0.000 claims description 31
125000004432 carbon atom Chemical group C* 0.000 claims description 27
229910052739 hydrogen Inorganic materials 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 10
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
238000002844 melting Methods 0.000 description 25
230000008018 melting Effects 0.000 description 25
238000000034 method Methods 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
239000003208 petroleum Substances 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
239000011664 nicotinic acid Substances 0.000 description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
229940080818 propionamide Drugs 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
239000000243 solution Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
-1 ketene imine Chemical class 0.000 description 6
229960003512 nicotinic acid Drugs 0.000 description 6
YFGBQHOOROIVKG-FKBYEOEOSA-N Met-enkephalin Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(O)=O)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=CC=C1 YFGBQHOOROIVKG-FKBYEOEOSA-N 0.000 description 5
108010042237 Methionine Enkephalin Proteins 0.000 description 5
239000002253 acid Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000003480 eluent Substances 0.000 description 5
235000019441 ethanol Nutrition 0.000 description 5
235000001968 nicotinic acid Nutrition 0.000 description 5
108090000790 Enzymes Proteins 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 4
102000003729 Neprilysin Human genes 0.000 description 4
108090000028 Neprilysin Proteins 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
NZZDEODTCXHCRS-UHFFFAOYSA-N methyl 2-aminopyridine-3-carboxylate Chemical compound COC(=O)C1=CC=CN=C1N NZZDEODTCXHCRS-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
BCAAXVOKLXDSPD-UHFFFAOYSA-N 2-(acetylsulfanylmethyl)-3-phenylpropanoic acid Chemical compound CC(=O)SCC(C(O)=O)CC1=CC=CC=C1 BCAAXVOKLXDSPD-UHFFFAOYSA-N 0.000 description 3
102000004400 Aminopeptidases Human genes 0.000 description 3
108090000915 Aminopeptidases Proteins 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
239000007810 chemical reaction solvent Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 3
229960002715 nicotine Drugs 0.000 description 3
239000000047 product Substances 0.000 description 3
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
BYIORJAACCWFPU-UHFFFAOYSA-N 5-aminonicotinic acid Chemical compound NC1=CN=CC(C(O)=O)=C1 BYIORJAACCWFPU-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
239000013256 coordination polymer Substances 0.000 description 2
238000001514 detection method Methods 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
HYFDELHMHRQVQU-UHFFFAOYSA-N methyl 2-[(3-acetylsulfanyl-2-methylpropanoyl)amino]pyridine-3-carboxylate Chemical compound COC(=O)C1=CC=CN=C1NC(=O)C(C)CSC(C)=O HYFDELHMHRQVQU-UHFFFAOYSA-N 0.000 description 2
OCARFFAPQGYGBP-UHFFFAOYSA-N methyl 4-aminopyridine-3-carboxylate Chemical compound COC(=O)C1=CN=CC=C1N OCARFFAPQGYGBP-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000000758 substrate Substances 0.000 description 2
238000010998 test method Methods 0.000 description 2
HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
LKUJXRWLKAJNOL-UHFFFAOYSA-N 1-chloro-3-(4-chlorobut-3-en-2-yloxy)but-1-ene Chemical compound ClC=CC(C)OC(C)C=CCl LKUJXRWLKAJNOL-UHFFFAOYSA-N 0.000 description 1
KMZHZAAOEWVPSE-UHFFFAOYSA-N 2,3-dihydroxypropyl acetate Chemical compound CC(=O)OCC(O)CO KMZHZAAOEWVPSE-UHFFFAOYSA-N 0.000 description 1
SMYTUBMIBZOXTH-UHFFFAOYSA-N 2-(methylamino)pyridine-3-carboxylic acid Chemical compound CNC1=NC=CC=C1C(O)=O SMYTUBMIBZOXTH-UHFFFAOYSA-N 0.000 description 1
GFPUTWNADSRASN-UHFFFAOYSA-N 2-[(2-methyl-3-sulfanylpropanoyl)amino]pyridine-4-carboxylic acid Chemical compound SCC(C)C(=O)NC1=CC(C(O)=O)=CC=N1 GFPUTWNADSRASN-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
VFVHNRJEYQGRGE-UHFFFAOYSA-N 3-acetylsulfanyl-2-methylpropanoic acid Chemical compound OC(=O)C(C)CSC(C)=O VFVHNRJEYQGRGE-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 description 1
LMYZQUNLYGJIHI-SPONXPENSA-N 4alpha-methyl-5alpha-cholest-7-en-3beta-ol Chemical compound C[C@@H]1[C@@H](O)CC[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@H](C)CCCC(C)C)CC[C@H]33)C)C3=CC[C@H]21 LMYZQUNLYGJIHI-SPONXPENSA-N 0.000 description 1
FORGVGUAIIMLPQ-UHFFFAOYSA-N 5-[(2-methyl-3-sulfanylpropanoyl)amino]pyridine-2-carboxylic acid Chemical compound SCC(C)C(=O)NC1=CC=C(C(O)=O)N=C1 FORGVGUAIIMLPQ-UHFFFAOYSA-N 0.000 description 1
TVSDWHXAESBBSF-UHFFFAOYSA-N 5-[methyl-(2-methyl-3-sulfanylpropanoyl)amino]pyridine-3-carboxylic acid Chemical compound SCC(C)C(=O)N(C)C1=CN=CC(C(O)=O)=C1 TVSDWHXAESBBSF-UHFFFAOYSA-N 0.000 description 1
BBGSDXSEZFCUFB-UHFFFAOYSA-N 6-[(2-methyl-3-sulfanylpropanoyl)amino]pyridine-3-carboxylic acid Chemical compound SCC(C)C(=O)NC1=CC=C(C(O)=O)C=N1 BBGSDXSEZFCUFB-UHFFFAOYSA-N 0.000 description 1
VGGGPCQERPFHOB-MCIONIFRSA-N Bestatin Chemical compound CC(C)C[C@H](C(O)=O)NC(=O)[C@@H](O)[C@H](N)CC1=CC=CC=C1 VGGGPCQERPFHOB-MCIONIFRSA-N 0.000 description 1
VGGGPCQERPFHOB-UHFFFAOYSA-N Bestatin Natural products CC(C)CC(C(O)=O)NC(=O)C(O)C(N)CC1=CC=CC=C1 VGGGPCQERPFHOB-UHFFFAOYSA-N 0.000 description 1
241000511343 Chondrostoma nasus Species 0.000 description 1
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
108010092674 Enkephalins Proteins 0.000 description 1
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
101000939500 Homo sapiens UBX domain-containing protein 11 Proteins 0.000 description 1
240000005979 Hordeum vulgare Species 0.000 description 1
235000007340 Hordeum vulgare Nutrition 0.000 description 1
URLZCHNOLZSCCA-VABKMULXSA-N Leu-enkephalin Chemical class C([C@@H](C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=CC=C1 URLZCHNOLZSCCA-VABKMULXSA-N 0.000 description 1
LMYZQUNLYGJIHI-UHFFFAOYSA-N Methostenol Natural products CC1C(O)CCC2(C)C(CCC3(C(C(C)CCCC(C)C)CCC33)C)C3=CCC21 LMYZQUNLYGJIHI-UHFFFAOYSA-N 0.000 description 1
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
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102000035195 Peptidases Human genes 0.000 description 1
241000700159 Rattus Species 0.000 description 1
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QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
102100029645 UBX domain-containing protein 11 Human genes 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
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229940030600 antihypertensive agent Drugs 0.000 description 1
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239000000164 antipsychotic agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
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CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
FIKVWPJKNMTBBD-UHFFFAOYSA-N ethyl 6-aminopyridine-3-carboxylate Chemical compound CCOC(=O)C1=CC=C(N)N=C1 FIKVWPJKNMTBBD-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
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JACPDLJUQLKABC-UHFFFAOYSA-N methyl 6-aminopyridine-3-carboxylate Chemical compound COC(=O)C1=CC=C(N)N=C1 JACPDLJUQLKABC-UHFFFAOYSA-N 0.000 description 1
JKRHDMPWBFBQDZ-UHFFFAOYSA-N n'-hexylmethanediimine Chemical compound CCCCCCN=C=N JKRHDMPWBFBQDZ-UHFFFAOYSA-N 0.000 description 1
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LUDPWTHDXSOXDX-UHFFFAOYSA-N s-(3-chloro-2-methyl-3-oxopropyl) ethanethioate Chemical compound ClC(=O)C(C)CSC(C)=O LUDPWTHDXSOXDX-UHFFFAOYSA-N 0.000 description 1
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229940124597 therapeutic agent Drugs 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
229950009811 ubenimex Drugs 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Landscapes

Pyridine Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP23260483A 1983-12-08 1983-12-08 アミノピリジンカルボン酸誘導体ならびに医薬組成物 Granted JPS60123472A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP23260483A JPS60123472A (ja)	1983-12-08	1983-12-08	アミノピリジンカルボン酸誘導体ならびに医薬組成物

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP23260483A JPS60123472A (ja)	1983-12-08	1983-12-08	アミノピリジンカルボン酸誘導体ならびに医薬組成物

Publications (2)

Publication Number	Publication Date
JPS60123472A true JPS60123472A (ja)	1985-07-02
JPH0441143B2 JPH0441143B2 (fr)	1992-07-07

Family

ID=16941951

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP23260483A Granted JPS60123472A (ja)	1983-12-08	1983-12-08	アミノピリジンカルボン酸誘導体ならびに医薬組成物

Country Status (1)

Country	Link
JP (1)	JPS60123472A (fr)

1983
- 1983-12-08 JP JP23260483A patent/JPS60123472A/ja active Granted

Also Published As

Publication number	Publication date
JPH0441143B2 (fr)	1992-07-07

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