JPS6313993B2 - - Google Patents
Info
- Publication number
- JPS6313993B2 JPS6313993B2 JP54081043A JP8104379A JPS6313993B2 JP S6313993 B2 JPS6313993 B2 JP S6313993B2 JP 54081043 A JP54081043 A JP 54081043A JP 8104379 A JP8104379 A JP 8104379A JP S6313993 B2 JPS6313993 B2 JP S6313993B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- hydroxyphenyl
- general formula
- dithiobis
- propanoyl
- Prior art date
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- -1 disulfide compound Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- APAUAYLVDHNFBF-UHFFFAOYSA-N 2-(2-hydroxyphenyl)-1,3-thiazolidine-4-carboxylic acid Chemical compound N1C(C(=O)O)CSC1C1=CC=CC=C1O APAUAYLVDHNFBF-UHFFFAOYSA-N 0.000 description 10
- 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 10
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 10
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VURCJRMYKFUQSW-UHFFFAOYSA-N 3-[(3-chloro-3-oxopropyl)disulfanyl]propanoyl chloride Chemical compound ClC(=O)CCSSCCC(Cl)=O VURCJRMYKFUQSW-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- YVKSGVDJQXLXDV-BYPYZUCNSA-N ethyl (2r)-2-amino-3-sulfanylpropanoate Chemical compound CCOC(=O)[C@@H](N)CS YVKSGVDJQXLXDV-BYPYZUCNSA-N 0.000 description 2
- VFUHEWBBJAYHNQ-FTNKSUMCSA-N ethyl (4r)-2-(2-hydroxyphenyl)-1,3-thiazolidine-4-carboxylate Chemical compound N1[C@H](C(=O)OCC)CSC1C1=CC=CC=C1O VFUHEWBBJAYHNQ-FTNKSUMCSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- APAUAYLVDHNFBF-JAVCKPHESA-N (4r)-2-(2-hydroxyphenyl)-1,3-thiazolidine-4-carboxylic acid Chemical compound N1[C@H](C(=O)O)CSC1C1=CC=CC=C1O APAUAYLVDHNFBF-JAVCKPHESA-N 0.000 description 1
- UUSLLECLCKTJQF-UHFFFAOYSA-N 2-(bromomethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CBr)C(=O)C2=C1 UUSLLECLCKTJQF-UHFFFAOYSA-N 0.000 description 1
- RYIVRLWJRCHUCL-UHFFFAOYSA-N 2-phenyl-1,3-thiazolidin-2-ol Chemical group C=1C=CC=CC=1C1(O)NCCS1 RYIVRLWJRCHUCL-UHFFFAOYSA-N 0.000 description 1
- HOCPDSKONPQIQM-UHFFFAOYSA-N 4-(2-bromoethyl)isoindole-1,3-dione Chemical compound BrCCC1=CC=CC2=C1C(=O)NC2=O HOCPDSKONPQIQM-UHFFFAOYSA-N 0.000 description 1
- 239000005541 ACE inhibitor Substances 0.000 description 1
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 1
- 230000004531 blood pressure lowering effect Effects 0.000 description 1
- CYJYHSYAYORDLU-LURJTMIESA-N butyl (2r)-2-amino-3-sulfanylpropanoate Chemical compound CCCCOC(=O)[C@@H](N)CS CYJYHSYAYORDLU-LURJTMIESA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 1
- GGRHYQCXXYLUTL-UHFFFAOYSA-N chloromethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCl GGRHYQCXXYLUTL-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 125000005543 phthalimide group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003548 thiazolidines Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8104379A JPS565415A (en) | 1979-06-26 | 1979-06-26 | Ester-type hypotensor |
| US06/104,970 US4347371A (en) | 1978-12-30 | 1979-12-18 | Disulfide compounds |
| AU54024/79A AU536307B2 (en) | 1978-12-30 | 1979-12-19 | Disulphide derivatives of pyrrolidine and thiazolidine |
| CA342,420A CA1128517A (en) | 1978-12-30 | 1979-12-20 | Disulfide compounds |
| SE7910554A SE446864B (sv) | 1978-12-30 | 1979-12-20 | Disulfidforeningar, forfaranden for framstellning derav samt farmaceutisk komposition innehallande nemnda disulfidforeningar som aktiv komponent |
| DE19792952594 DE2952594A1 (de) | 1978-12-30 | 1979-12-28 | Disulfidverbindungen |
| CH11528/79A CH647769A5 (de) | 1978-12-30 | 1979-12-28 | Disulfidverbindungen. |
| IT28440/79A IT1127323B (it) | 1978-12-30 | 1979-12-28 | Composti costituiti da disolfuri |
| NL7909334A NL7909334A (nl) | 1978-12-30 | 1979-12-28 | Werkwijze voor het bereiden van een bloeddruk ver- lagend middel op basis van disulfideverbindingen, het aldus bereide geneesmiddel en een werkwijze voor de bereiding van de actieve component. |
| GB7944544A GB2042517B (en) | 1978-12-30 | 1979-12-28 | Disulphide compounds |
| ES487373A ES487373A0 (es) | 1978-12-30 | 1979-12-28 | Un procedimiento para la preparacion de disulfoderivados |
| FR7932060A FR2445324A1 (fr) | 1978-12-30 | 1979-12-28 | Nouveaux derives disulfures contenant un cycle pyrrolidine ou thiazolidine utiles comme antihypertenseurs et pour prevenir et traiter les complications du diabete et procedes pour leur preparation |
| AT0820179A AT377516B (de) | 1978-12-30 | 1979-12-28 | Verfahren zur herstellung von disulfidverbindungen und von deren salzen |
| ES494657A ES8106497A1 (es) | 1978-12-30 | 1980-08-29 | Un procedimiento para la preparacion de disulfoderivados |
| ES494654A ES8106494A1 (es) | 1978-12-30 | 1980-08-29 | Un procedimiento para la preparacion de disulfoderivados |
| ES494655A ES494655A0 (es) | 1978-12-30 | 1980-08-29 | Un procedimiento para la preparacion de disulfoderivados |
| ES494656A ES494656A0 (es) | 1978-12-30 | 1980-08-29 | Un procedimiento para la preparacion de disulfoderivados |
| US06/186,271 US4410542A (en) | 1978-12-30 | 1980-09-11 | Disulfide compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8104379A JPS565415A (en) | 1979-06-26 | 1979-06-26 | Ester-type hypotensor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS565415A JPS565415A (en) | 1981-01-20 |
| JPS6313993B2 true JPS6313993B2 (sv) | 1988-03-29 |
Family
ID=13735401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8104379A Granted JPS565415A (en) | 1978-12-30 | 1979-06-26 | Ester-type hypotensor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS565415A (sv) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5382778A (en) * | 1976-12-03 | 1978-07-21 | Squibb & Sons Inc | Thiazolidinecarboxylate derivative and related compounds thereof process for preparing same and application thereof |
| JPS5432466A (en) * | 1977-08-15 | 1979-03-09 | Yoshitomi Pharmaceut Ind Ltd | Thiazolidine derivatives and their preparation |
| JPS5466675A (en) * | 1977-09-28 | 1979-05-29 | Science Union & Cie | Omegaamercaptopropionamido*its manufacture and medical composition |
-
1979
- 1979-06-26 JP JP8104379A patent/JPS565415A/ja active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5382778A (en) * | 1976-12-03 | 1978-07-21 | Squibb & Sons Inc | Thiazolidinecarboxylate derivative and related compounds thereof process for preparing same and application thereof |
| JPS5432466A (en) * | 1977-08-15 | 1979-03-09 | Yoshitomi Pharmaceut Ind Ltd | Thiazolidine derivatives and their preparation |
| JPS5466675A (en) * | 1977-09-28 | 1979-05-29 | Science Union & Cie | Omegaamercaptopropionamido*its manufacture and medical composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS565415A (en) | 1981-01-20 |
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