SE447379B - Vissa disulfider - Google Patents
Vissa disulfiderInfo
- Publication number
- SE447379B SE447379B SE8203053A SE8203053A SE447379B SE 447379 B SE447379 B SE 447379B SE 8203053 A SE8203053 A SE 8203053A SE 8203053 A SE8203053 A SE 8203053A SE 447379 B SE447379 B SE 447379B
- Authority
- SE
- Sweden
- Prior art keywords
- compound according
- methyl
- compounds
- preparation
- cysteine
- Prior art date
Links
- 150000002019 disulfides Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000004158 L-cystine Substances 0.000 claims description 3
- 229960003067 cystine Drugs 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- IDIDJDIHTAOVLG-UHFFFAOYSA-N S-methyl-L-cysteine Natural products CSCC(N)C(O)=O IDIDJDIHTAOVLG-UHFFFAOYSA-N 0.000 claims description 2
- IDIDJDIHTAOVLG-VKHMYHEASA-N S-methylcysteine Chemical compound CSC[C@H](N)C(O)=O IDIDJDIHTAOVLG-VKHMYHEASA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 2
- 208000002177 Cataract Diseases 0.000 claims 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010067125 Liver injury Diseases 0.000 claims 1
- 208000025747 Rheumatic disease Diseases 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000001944 cysteine derivatives Chemical class 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 231100000234 hepatic damage Toxicity 0.000 claims 1
- 210000000987 immune system Anatomy 0.000 claims 1
- 230000008818 liver damage Effects 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- -1 2-methylpropanoyl Chemical group 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- NRHMXMBVLXSSAX-UHFFFAOYSA-N 3-methylsulfanylpropanoyl chloride Chemical compound CSCCC(Cl)=O NRHMXMBVLXSSAX-UHFFFAOYSA-N 0.000 description 1
- VUAFHZCUKUDDBC-BYPYZUCNSA-N Bucillamine Chemical compound CC(C)(S)C(=O)N[C@@H](CS)C(O)=O VUAFHZCUKUDDBC-BYPYZUCNSA-N 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 1
- 125000001664 diethylamino group Chemical class [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- SDNJNDFHCODQDQ-UHFFFAOYSA-N n-(2-ethylphenyl)-2-[[2-[(2-ethylphenyl)carbamoyl]phenyl]disulfanyl]benzamide Chemical compound CCC1=CC=CC=C1NC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(=O)NC1=CC=CC=C1CC SDNJNDFHCODQDQ-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
- C07C319/12—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols by reactions not involving the formation of mercapto groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/12—Ophthalmic agents for cataracts
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/12—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms
- C07C321/14—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/36—Seven-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Ophthalmology & Optometry (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Gastroenterology & Hepatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Description
i447 379 12, HZN-CH-COOH I 6 (IV) CH2-S-R där R6 betecknar väte, lågalkyl eller den grupp som erhålles efter avlägsnande av R6 från formeln IV. _ ' De enligt de ovan angivna metoderna framställda föreningarna enligt föreliggande uppfinning kan omvandlas till vanliga salter som är acceptabla i läkemedel, såsom natriumsalt, kaliumsalt, magnesium- Sfilfi, kfilßíumsfllü, aluminflmsalt, ammoniumsalt, dietylaminsalt, tri- etanolaminsalt etc.
Föreningarna enligt föreliggande uppfinning omfattar stereoiso- mer, eftersom de innehåller en eller flera asymmetriska kolatomer.
Stereoisomererna omfattas också av föreliggande uppfinning.
Uppfinningen illusteras genom följande, icke begränsande exempel.
Exempel l N,N'-bislÉ-metyl-2-(metyltio)propanoyl7-L-cystin.
Till en omrörd lösning av 3,1 g (l3mM) L-cystin i 105 ml 0,5N natrium- hydroxidlösning sattes droppvis U,0 g (26mM) 2-metyl-2f(metvltio) propanoylklorid vid 5-l0°C. Efter avslutad tillsättning omfihes reak- tionsblandningen under H5 minuter vid samma temperatur och sedan under ytterligare 20 minuter vid rumstemperatur.
Reaktionsblandningen tvättas med eter, surgöres med 6N saltsyra och extraheras med etylacetat. Det organiska skiktet tvättas med vatten och torkas. Etylacetat avdestílleras, och återstoden renas gener kolonn-kromatografi på silikagel. Härvid erhålles 5,1 g (85%) av titel» föreningen.
Smp. 128-12900 (etylacetat-n-hexan); fii/É" - 157,9° (c= o,9;mecanp1); 1R(nujo1, cm'1) = 3320, 1730, 1625, 1515; NMR (nmso-d6,¿): 1,58 (12H, S, (cH3)2c-), 2,00 (ön, S, cH3s-), 3,13(uH, a, J=5,o H:_ -CHZS-), Ä,2T-Ü:ö;(2H, m, QÉCOOH), 7,93 (2H, d, J=8,0 HZ, -COQQ-É, 12,75 (en, S, cooH); Elementaranalys _1b16H28N206SH): Beräknat; c, flo,65; H, 5,98; N, 5,93 Funnet:~ c, Mo,88;_H, 5,98; N, 5,69 447 379 Exempel 2 'N,N“-(2,2'-ditiobis(2-metylpropanoyl)]bis(S-metyl-L-cysbein).
Man arbetar på samma sätt som i exempel 1 men utgår från 5,0 g (37mM) S~metyl-L-cystein oqp 2,9 g (l9mM) 2,2'~dítíobis(2-mety1propanoyl)dí- klorid. Härvid erhå1leš'bitelföreníngen i en mängd av 7,0 g (80%).
Smp. 81-8500 (kloroform); /ÉIÉU + U,3° (c=l,0;metanol); 10 (nujøl, cm'l)= 3510, 1725, 1610; NMR (0Mso~D6, í): ' 1,H3 (12H§ S, (cH3)2c-), 2,05 (60, S, -cnpscflš), 2,87(uH, 0, J: 6,oHz, -cuzs-), -C0§§-), 8:ÉÜ(2H, s, COQ§); Elementaranalys (C16H28N2O6Su); Beräknat: C, U0,65; H, 5,98; N, 5,95 Funnet: C, 00,20; H, 5,71; N, 5,69 Exempel 3 "_" 0,17-u,55(2H, m, -ggcoóHïï"7,83(2H, 0, J=8,0Hz, (UR)-7,7-dimetyl-6-oxo-3,0,6,7-tetrahydro-1,2,5-ditíazepín-H-karhoxylsyra 1,0 g (U,5mM) N-(2-merkapto-2-metylpropanoyl)-L-cystein och 0,25 g (1,0mM) kopparsulfat-pentahydrat löses i 0,01 M fosfatbuffert (DH 710).
Den erhållna lösningen omröres under ZN timmar, varvid luft buhb1nr genom lösningen. Reaktíonsblandningen mnyñres med saltsyra och extrw- heras med etylacetat. Det organiska skiktet tvättas med mättad natrí- umkloridlösning och torkas över magnesiumsulfat. Etylacetat avdestíl- leras, och återstoden renas genom kolonn-kromatografí på silikagel.
Härvid erhålles titelföreningen i en mängd av 0,35 E (55%)- smp. 173-175°c (ener); In (xßr, cm'1)= 3260, 1750, 1708, 1615; NMR (c0c13{ó'); l,5}(3H, S, CH3-), l,66(}H, S, CH3-), 2,65(lH, dd, J=l2,0, 12,0 Hz, 03-HA), 3,38(1Hz, da, J=u,o 12,0 Hz, c3-HB), 5,3l(1H,ddd, J = U,0, 8,0, 12,0 Hz, Cu-H), 8,h3(1H, 0, J= 8,0 Hz, gg-), l3,0(1H, S, c00g); czms (1-0,010) m/Z = 222 (MH*).
Claims (4)
1. Intra- eller intermolekylär disulfid av en eller två molekyler av en förening med formeln A-CO-NH-CH-COOH I s-R1 CHZ-s-Rz där var och en av symbolerna R1 och R2 betecknar väte eller lâgal- kyl,och där symbolen A betecknar -C(CH3)2-.
2. Förening enligt krav 1, k ä n n e t e c k n a d av att den är (4R)-7,7-dimetyl-6-oxo-3,4,6,7-tetrahydro-1,2,5-ditiazepin-4- (I) karboxylsyra.
3. Förening enligt krav 1, k ä n n e t e c k n a'd av att den är N,N'-bis[2-mety1-2-(metyltio)propanoyl]-L-cystin.
4. Förening enligt krav 1, k ä n n e t e c k n a d av att den är N,N'-12,2'-ditiobis(2-metylpropanoylL7bis(S-metyl-L-cystein).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55131349A JPS5756454A (en) | 1980-09-20 | 1980-09-20 | Disulfide type cysteine derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8203053L SE8203053L (sv) | 1982-05-14 |
| SE447379B true SE447379B (sv) | 1986-11-10 |
Family
ID=15055849
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8203053A SE447379B (sv) | 1980-09-20 | 1982-05-14 | Vissa disulfider |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4517123A (sv) |
| JP (1) | JPS5756454A (sv) |
| KR (1) | KR880000041B1 (sv) |
| AU (1) | AU7590081A (sv) |
| BE (1) | BE890399A (sv) |
| CA (1) | CA1162188A (sv) |
| DE (1) | DE3152362C2 (sv) |
| ES (1) | ES8303316A1 (sv) |
| FR (1) | FR2490637A1 (sv) |
| GB (1) | GB2096145B (sv) |
| IT (1) | IT1138226B (sv) |
| SE (1) | SE447379B (sv) |
| WO (1) | WO1982001000A1 (sv) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE84303T1 (de) * | 1988-01-25 | 1993-01-15 | Santen Pharmaceutical Co Ltd | Cysteinderivate. |
| US5041435A (en) * | 1988-08-13 | 1991-08-20 | Santen Pharmaceutical Co., Ltd. | Cyclic sulfur-containing compounds |
| US5081307A (en) * | 1989-07-14 | 1992-01-14 | Kawaguchi Chemical Co., Ltd. | Process for preparing 2,2-dimethoxy-2-phenylacetophenone |
| JP2720217B2 (ja) * | 1989-12-05 | 1998-03-04 | 参天製薬株式会社 | 含硫黄アミノ酸誘導体 |
| US5175256A (en) * | 1990-09-28 | 1992-12-29 | Neorx Corporation | Protein labeling reagents |
| JP2843955B2 (ja) * | 1992-08-01 | 1999-01-06 | 参天製薬株式会社 | 抗白内障剤 |
| US5670545A (en) * | 1996-02-09 | 1997-09-23 | Board Of Regents Of The University Of Colorado | Method for the treatment of ischemic disease and reperfusion injury and the prevention of the adverse effects of reactive oxygen species |
| US10655227B2 (en) | 2017-10-06 | 2020-05-19 | Rohm And Haas Electronic Materials Llc | Stable electroless copper plating compositions and methods for electroless plating copper on substrates |
| US10294569B2 (en) | 2017-10-06 | 2019-05-21 | Rohm And Haas Electronic Materials Llc | Stable electroless copper plating compositions and methods for electroless plating copper on substrates |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5271928A (en) * | 1975-12-11 | 1977-06-15 | Sony Corp | Receiving and recording unit of tv signals |
| JPS535112A (en) * | 1976-03-08 | 1978-01-18 | Santen Pharmaceutical Co Ltd | New cysteine derivatives |
| JPS545916A (en) * | 1977-06-17 | 1979-01-17 | Santen Pharmaceutical Co Ltd | Novel cystein derivative |
| JPS6058908B2 (ja) * | 1978-10-11 | 1985-12-23 | 参天製薬株式会社 | システイン誘導体 |
| JPS6011888B2 (ja) * | 1978-10-11 | 1985-03-28 | 参天製薬株式会社 | リウマチ疾患治療薬 |
-
1980
- 1980-09-20 JP JP55131349A patent/JPS5756454A/ja active Granted
-
1981
- 1981-09-18 BE BE2/59362A patent/BE890399A/fr not_active IP Right Cessation
- 1981-09-18 CA CA000386241A patent/CA1162188A/en not_active Expired
- 1981-09-18 DE DE19813152362 patent/DE3152362C2/de not_active Expired
- 1981-09-18 ES ES505628A patent/ES8303316A1/es not_active Expired
- 1981-09-18 WO PCT/JP1981/000235 patent/WO1982001000A1/ja active Application Filing
- 1981-09-18 GB GB8214992A patent/GB2096145B/en not_active Expired
- 1981-09-18 AU AU75900/81A patent/AU7590081A/en not_active Abandoned
- 1981-09-18 US US06/380,665 patent/US4517123A/en not_active Expired - Lifetime
- 1981-09-19 KR KR1019810003505A patent/KR880000041B1/ko active
- 1981-09-21 FR FR8117808A patent/FR2490637A1/fr active Granted
- 1981-09-21 IT IT24057/81A patent/IT1138226B/it active
-
1982
- 1982-05-14 SE SE8203053A patent/SE447379B/sv not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE3152362C2 (de) | 1986-08-28 |
| IT1138226B (it) | 1986-09-17 |
| US4517123A (en) | 1985-05-14 |
| GB2096145A (en) | 1982-10-13 |
| ES505628A0 (es) | 1983-02-01 |
| AU7590081A (en) | 1982-04-14 |
| ES8303316A1 (es) | 1983-02-01 |
| JPS5756454A (en) | 1982-04-05 |
| JPS6143350B2 (sv) | 1986-09-26 |
| CA1162188A (en) | 1984-02-14 |
| SE8203053L (sv) | 1982-05-14 |
| DE3152362T1 (sv) | 1982-10-07 |
| FR2490637A1 (fr) | 1982-03-26 |
| WO1982001000A1 (en) | 1982-04-01 |
| BE890399A (fr) | 1982-01-18 |
| KR880000041B1 (ko) | 1988-02-20 |
| FR2490637B1 (sv) | 1984-12-14 |
| IT8124057A0 (it) | 1981-09-21 |
| GB2096145B (en) | 1984-05-02 |
| KR830007539A (ko) | 1983-10-21 |
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