JPS6257619B2 - - Google Patents

Info

Publication number: JPS6257619B2
Authority: JP; Japan
Prior art keywords: formula; tiopronin; compound; title compound; groups
Prior art date: 1979-04-04
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.): Expired

Application number

JP54041319A

Other languages

English (en)

Japanese (ja)

Other versions

JPS55133343A (en

Inventor

Junichi Iwao

Masayuki Ooya

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.)

Santen Pharmaceutical Co Ltd

Original Assignee

Santen Pharmaceutical Co Ltd

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.)

1979-04-04

Filing date

1979-04-04

Publication date

1987-12-02

1979-04-04 Application filed by Santen Pharmaceutical Co Ltd filed Critical Santen Pharmaceutical Co Ltd

1979-04-04 Priority to JP4131979A priority Critical patent/JPS55133343A/ja

1980-10-17 Publication of JPS55133343A publication Critical patent/JPS55133343A/ja

1987-12-02 Publication of JPS6257619B2 publication Critical patent/JPS6257619B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 31
RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 5
108010024636 Glutathione Proteins 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
229960003180 glutathione Drugs 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
YTGJWQPHMWSCST-UHFFFAOYSA-N Tiopronin Chemical compound CC(S)C(=O)NCC(O)=O YTGJWQPHMWSCST-UHFFFAOYSA-N 0.000 description 18
229960004402 tiopronin Drugs 0.000 description 17
108010058907 Tiopronin Proteins 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
238000004519 manufacturing process Methods 0.000 description 10
238000000034 method Methods 0.000 description 9
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
-1 sulfide compound Chemical class 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
238000010828 elution Methods 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000004471 Glycine Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000003814 drug Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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 2
235000001014 amino acid Nutrition 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
150000003946 cyclohexylamines Chemical class 0.000 description 2
229960003067 cystine Drugs 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
VHJLVAABSRFDPM-ZXZARUISSA-N dithioerythritol Chemical compound SC[C@H](O)[C@H](O)CS VHJLVAABSRFDPM-ZXZARUISSA-N 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
239000003456 ion exchange resin Substances 0.000 description 2
229920003303 ion-exchange polymer Polymers 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 2
239000012266 salt solution Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 description 1
MXBCRXQYFIPNMH-UHFFFAOYSA-N 2-[2-[[1-(carboxymethylamino)-1-oxopropan-2-yl]disulfanyl]propanoylamino]acetic acid Chemical compound OC(=O)CNC(=O)C(C)SSC(C)C(=O)NCC(O)=O MXBCRXQYFIPNMH-UHFFFAOYSA-N 0.000 description 1
MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical compound CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
208000002177 Cataract Diseases 0.000 description 1
108010053070 Glutathione Disulfide Proteins 0.000 description 1
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
235000019393 L-cystine Nutrition 0.000 description 1
239000004158 L-cystine Substances 0.000 description 1
206010067125 Liver injury Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
ABRJVLRUVDJIJJ-UHFFFAOYSA-N OC(=O)CNC(=O)C(C)SSCC(N)C(O)=O Chemical compound OC(=O)CNC(=O)C(C)SSCC(N)C(O)=O ABRJVLRUVDJIJJ-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
238000003436 Schotten-Baumann reaction Methods 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
MBRZVWSXTLBVNY-UHFFFAOYSA-N acetic acid;chloroform;ethanol Chemical compound CCO.CC(O)=O.ClC(Cl)Cl MBRZVWSXTLBVNY-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical group 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
230000003356 anti-rheumatic effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
ZYZWOSIRFVIBRH-UHFFFAOYSA-N chloroform;cyclohexane Chemical compound ClC(Cl)Cl.C1CCCCC1 ZYZWOSIRFVIBRH-UHFFFAOYSA-N 0.000 description 1
239000007979 citrate buffer Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 1
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
235000018417 cysteine Nutrition 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
PLVPMKWGXOOSKL-RGVONZFCSA-L disodium;(2r)-2-amino-3-[[(2r)-2-amino-2-carboxylatoethyl]disulfanyl]propanoate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CSSC[C@H](N)C([O-])=O PLVPMKWGXOOSKL-RGVONZFCSA-L 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000007429 general method Methods 0.000 description 1
YPZRWBKMTBYPTK-BJDJZHNGSA-N glutathione disulfide Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@H](C(=O)NCC(O)=O)CSSC[C@@H](C(=O)NCC(O)=O)NC(=O)CC[C@H](N)C(O)=O YPZRWBKMTBYPTK-BJDJZHNGSA-N 0.000 description 1
231100000234 hepatic damage Toxicity 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000008818 liver damage Effects 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
YPZRWBKMTBYPTK-UHFFFAOYSA-N oxidized gamma-L-glutamyl-L-cysteinylglycine Natural products OC(=O)C(N)CCC(=O)NC(C(=O)NCC(O)=O)CSSCC(C(=O)NCC(O)=O)NC(=O)CCC(N)C(O)=O YPZRWBKMTBYPTK-UHFFFAOYSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229960001639 penicillamine Drugs 0.000 description 1
125000005543 phthalimide group Chemical group 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
HLLMICMHTKJPJM-UHFFFAOYSA-M sodium;ethoxy-oxido-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound [Na+].CCOS([O-])(=O)=S HLLMICMHTKJPJM-UHFFFAOYSA-M 0.000 description 1
HLZPPBJQBJXVNG-UHFFFAOYSA-M sodium;methoxy-oxido-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound [Na+].COS([O-])(=O)=S HLZPPBJQBJXVNG-UHFFFAOYSA-M 0.000 description 1
WAEFQZYNSITAQT-UHFFFAOYSA-M sodium;octoxy-oxido-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound [Na+].CCCCCCCCOS([O-])(=O)=S WAEFQZYNSITAQT-UHFFFAOYSA-M 0.000 description 1
NRCOBPBOOMYKGU-UHFFFAOYSA-M sodium;oxido-oxo-(oxolan-2-ylmethoxy)-sulfanylidene-$l^{6}-sulfane Chemical compound [Na+].[O-]S(=O)(=S)OCC1CCCO1 NRCOBPBOOMYKGU-UHFFFAOYSA-M 0.000 description 1
GJNRIGCZVXQSHN-UHFFFAOYSA-M sodium;oxido-oxo-propoxy-sulfanylidene-$l^{6}-sulfane Chemical compound [Na+].CCCOS([O-])(=O)=S GJNRIGCZVXQSHN-UHFFFAOYSA-M 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Landscapes

Furan Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Peptides Or Proteins (AREA)

JP4131979A 1979-04-04 1979-04-04 Thiopronine derivative Granted JPS55133343A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP4131979A JPS55133343A (en)	1979-04-04	1979-04-04	Thiopronine derivative

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP4131979A JPS55133343A (en)	1979-04-04	1979-04-04	Thiopronine derivative

Publications (2)

Publication Number	Publication Date
JPS55133343A JPS55133343A (en)	1980-10-17
JPS6257619B2 true JPS6257619B2 (de)	1987-12-02

Family

ID=12605186

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP4131979A Granted JPS55133343A (en)	1979-04-04	1979-04-04	Thiopronine derivative

Country Status (1)

Country	Link
JP (1)	JPS55133343A (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN1305845C (zh) *	2005-05-16	2007-03-21	河南省新谊药业股份有限公司	用于治疗急慢性肝病的无水硫普罗宁钠及其制备方法
CN100383521C (zh) *	2005-09-23	2008-04-23	复旦大学	一种测定硫普罗宁浓度的方法
JP6762094B2 (ja) *	2013-02-28	2020-09-30	タフツユニバーシティー	薬剤のデリバリーのためのジスルフィド化合物

1979
- 1979-04-04 JP JP4131979A patent/JPS55133343A/ja active Granted

Also Published As

Publication number	Publication date
JPS55133343A (en)	1980-10-17

Publication	Publication Date	Title
JPS643870B2 (de)	1989-01-23
CH622800A5 (de)	1981-04-30
JPS6059226B2 (ja)	1985-12-24	プロリン誘導体および関連化合物
WO2004101597A2 (en)	2004-11-25	Methods for the reduction of disulfide bonds
CA2060209A1 (en)	1991-10-27	Glutathione-s-lower fatty acid derivative
JPS6257619B2 (de)	1987-12-02
JPS6030666B2 (ja)	1985-07-17	光学活性メルカプトカルボン酸の製造法
CA1162188A (en)	1984-02-14	Intra-or intermolecular disulfide of cysteine derivatives
ES2198389T3 (es)	2004-02-01	Procedimiento para la sintesis de derivados n-(mercaptoacil)-aminoacidos a partir de acidos alfa-substituidos.
PT94347B (pt)	1997-01-31	Processo para a preparacao de sais cristalinos de adicao a acidos da cefalosporina
EP0026307A1 (de)	1981-04-08	Organische Sulfoxide, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Enzym-blockierende Zusammensetzungen
BONVICINO et al.	1959	Studies on Some Oxidation and Reduction Products of Thiamine. II. 1 Thiamine Disulfide-Thioglycolic Acid Reaction. 2-4
CA2776833A1 (fr)	2011-04-14	Procede de synthese de la 2-thiohistidine et analogues
DE69614508T2 (de)	2002-04-11	Thiol derivate mit metallopeptidase inhibierender aktivitat
DE69626846T2 (de)	2003-12-24	Phosphonsäurederivate mit metallopeptidase inhibierender aktivität
JP3773064B2 (ja)	2006-05-10	フェノキシアルキルカルボン酸誘導体の製造法
JP2007509161A (ja)	2007-04-12	ベンゾヒドリルチオアセトアミドの改良型製造方法
FI73976C (fi)	1987-12-10	Foerfarande foer foerdelning av racematet s-(karboximetyl)-(r,s)-cystein i isomerer.
JPS61145187A (ja)	1986-07-02	セフアロスポリン類
JPH05213990A (ja)	1993-08-24	トリペプチド誘導体
US6017959A (en)	2000-01-25	Forms of organic salts of N,N'-diacetylcystine
JP3598131B2 (ja)	2004-12-08	新規なアルキルスルフィン酸無置換アンモニウム塩
JPH01246257A (ja)	1989-10-02	３―チオプロピオン酸誘導体の製造法
CA1118419A (en)	1982-02-16	Hexahydro-1-mercaptoacyl-1h-azepine-2- carboxylic acids and esters
JPH0219116B2 (de)	1990-04-27