PL81800B1 - - Google Patents
Download PDFInfo
- Publication number
- PL81800B1 PL81800B1 PL1971150132A PL15013271A PL81800B1 PL 81800 B1 PL81800 B1 PL 81800B1 PL 1971150132 A PL1971150132 A PL 1971150132A PL 15013271 A PL15013271 A PL 15013271A PL 81800 B1 PL81800 B1 PL 81800B1
- Authority
- PL
- Poland
- Prior art keywords
- cysteine
- isothiocyanate
- solution
- amount
- benzyl isothiocyanate
- Prior art date
Links
- MDKCFLQDBWCQCV-UHFFFAOYSA-N benzyl isothiocyanate Chemical compound S=C=NCC1=CC=CC=C1 MDKCFLQDBWCQCV-UHFFFAOYSA-N 0.000 claims description 39
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 22
- QAADZYUXQLUXFX-UHFFFAOYSA-N N-phenylmethylthioformamide Natural products S=CNCC1=CC=CC=C1 QAADZYUXQLUXFX-UHFFFAOYSA-N 0.000 claims description 20
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 18
- 229960002433 cysteine Drugs 0.000 claims description 18
- 235000018417 cysteine Nutrition 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- -1 β - [(N-benzylthiocarbamoyl) -thio] -propionic acid Chemical compound 0.000 claims description 7
- 239000012153 distilled water Substances 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- QIJRTFXNRTXDIP-UHFFFAOYSA-N (1-carboxy-2-sulfanylethyl)azanium;chloride;hydrate Chemical compound O.Cl.SCC(N)C(O)=O QIJRTFXNRTXDIP-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 229960001305 cysteine hydrochloride Drugs 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 1
- 150000002540 isothiocyanates Chemical class 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 230000000968 intestinal effect Effects 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 230000000843 anti-fungal effect Effects 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000007794 irritation Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000008164 mustard oil Substances 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 210000001198 duodenum Anatomy 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OHBNAOAQQKJIBG-UHFFFAOYSA-N 2-(benzylcarbamothioylsulfanyl)propanoic acid Chemical compound OC(=O)C(C)SC(=S)NCC1=CC=CC=C1 OHBNAOAQQKJIBG-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 206010007134 Candida infections Diseases 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000007027 Oral Candidiasis Diseases 0.000 description 1
- 241000287411 Turdidae Species 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229960004308 acetylcysteine Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000001929 anti-hepatotoxic effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- WIJRMGQOERPOJA-UHFFFAOYSA-N benzyl cyanate Chemical compound N#COCC1=CC=CC=C1 WIJRMGQOERPOJA-UHFFFAOYSA-N 0.000 description 1
- 201000003984 candidiasis Diseases 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 201000003146 cystitis Diseases 0.000 description 1
- 238000007257 deesterification reaction Methods 0.000 description 1
- 238000001784 detoxification Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 210000004347 intestinal mucosa Anatomy 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 108010058651 thioglucosidase Proteins 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/04—Five-membered rings having the hetero atoms in positions 1 and 2, e.g. lipoic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/16—Isothiocyanates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2041831A DE2041831C3 (de) | 1970-08-22 | 1970-08-22 | alpha-Amino-beta-(N-Benzylthiocarbamoyl)-thiopropionsäure, Verfahren zu ihrer Herstellung, sowie diese enthaltende Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL81800B1 true PL81800B1 (enrdf_load_stackoverflow) | 1975-08-30 |
Family
ID=5780532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1971150132A PL81800B1 (enrdf_load_stackoverflow) | 1970-08-22 | 1971-08-21 |
Country Status (15)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52170492U (enrdf_load_stackoverflow) * | 1976-06-17 | 1977-12-24 | ||
| JPS5318795U (enrdf_load_stackoverflow) * | 1976-07-27 | 1978-02-17 | ||
| JPS57121989A (en) * | 1981-01-23 | 1982-07-29 | Mitsubishi Heavy Ind Ltd | Coal carrier |
-
1970
- 1970-08-22 DE DE2041831A patent/DE2041831C3/de not_active Expired
-
1971
- 1971-08-10 GB GB37507/71A patent/GB1299037A/en not_active Expired
- 1971-08-17 CH CH1206771A patent/CH565148A5/xx not_active IP Right Cessation
- 1971-08-18 NL NL717111400A patent/NL145851B/xx not_active IP Right Cessation
- 1971-08-19 BE BE771522A patent/BE771522A/xx not_active IP Right Cessation
- 1971-08-19 ES ES394344A patent/ES394344A1/es not_active Expired
- 1971-08-19 FR FR7130255A patent/FR2103445B1/fr not_active Expired
- 1971-08-20 AT AT730971A patent/AT316578B/de active
- 1971-08-20 DK DK411071A patent/DK140139C/da not_active IP Right Cessation
- 1971-08-20 BR BR5436/71A patent/BR7105436D0/pt unknown
- 1971-08-20 LU LU63754D patent/LU63754A1/xx unknown
- 1971-08-20 IT IT27675/71A patent/IT1047889B/it active
- 1971-08-21 PL PL1971150132A patent/PL81800B1/pl unknown
- 1971-08-21 JP JP46063962A patent/JPS5114493B1/ja active Pending
- 1971-08-23 CA CA121,251A patent/CA992980A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| LU63754A1 (enrdf_load_stackoverflow) | 1972-01-05 |
| FR2103445B1 (enrdf_load_stackoverflow) | 1975-08-01 |
| BR7105436D0 (pt) | 1973-05-10 |
| CA992980A (en) | 1976-07-13 |
| FR2103445A1 (enrdf_load_stackoverflow) | 1972-04-14 |
| DE2041831A1 (de) | 1972-02-24 |
| DE2041831C3 (de) | 1974-05-09 |
| CH565148A5 (enrdf_load_stackoverflow) | 1975-08-15 |
| NL7111400A (enrdf_load_stackoverflow) | 1972-02-24 |
| BE771522A (fr) | 1972-02-21 |
| DK140139B (da) | 1979-06-25 |
| NL145851B (nl) | 1975-05-15 |
| GB1299037A (en) | 1972-12-06 |
| AT316578B (de) | 1974-07-25 |
| ES394344A1 (es) | 1973-12-01 |
| DK140139C (da) | 1979-11-19 |
| DE2041831B2 (de) | 1973-10-18 |
| IT1047889B (it) | 1980-10-20 |
| JPS5114493B1 (enrdf_load_stackoverflow) | 1976-05-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| USRE42645E1 (en) | Nutritional or therapeutic compositions and methods to increase bodily glutathione levels | |
| US9492551B2 (en) | Orally administrable gallium compositions and methods of use | |
| BR0014179A (pt) | Modernos derivados de ácido aminodicarboxìlico com propriedades farmacêuticas | |
| US8093374B2 (en) | Bismuth hyaluronate, the preparation method and the use thereof | |
| CN120078763B (zh) | 一种治疗幽门螺旋杆菌感染的药物 | |
| CN103747784B (zh) | 败血症的预防剂和/或治疗剂 | |
| US4455305A (en) | Composition for the treatment of colitis ulcerosa, enteritis regionalis crohn (morbus crohn), chronic nonspecific colitis and diverticulitis and the use of salicylazobenzoic acid for the preparation of such compositions | |
| PL81800B1 (enrdf_load_stackoverflow) | ||
| JP2015509105A (ja) | リファキシミン誘導体及びその使用 | |
| RU2124888C1 (ru) | Средство для коррекции патологических состояний, связанных с нарушением метаболических процессов | |
| US3998964A (en) | α-Amino-β-(N-benzylthiocarbamoylthio) propionic acid and therapeutic compositions | |
| US6077838A (en) | Method of treating hangover | |
| US4001231A (en) | Process for making a methenamine salt of an optically active acid | |
| RU2590980C2 (ru) | Фармацевтическая композиция для местного применения, обладающая антибактериальным, противовоспалительным и иммуномодулирующим действием, и ее применения | |
| US6034126A (en) | Method for treating glycol poisoning | |
| EP0623623B1 (en) | 2-aminoethanesulfonic acid/zinc complex | |
| DE1543733C3 (de) | Aluminium-bis-alpha-(p-chlorphenoxy) isobutyrat und diese Verbindung als Wirkstoff enthaltende Hellmittel | |
| CH652923A5 (it) | Composizione farmaceutica per la terapia di calcolosi renale infetta. | |
| US2602085A (en) | Method of producing calcium salts of sulfanilamides | |
| US4466978A (en) | Bodyweight reducing method | |
| RU2135185C1 (ru) | Противовоспалительное средство | |
| CA1301776C (en) | Compound of choline, a process for its preparation and therapeutic composition containing it | |
| TW202308626A (zh) | 降脂促進劑 | |
| JPS6289664A (ja) | ノルフロキサシン塩、その製法および組成物 | |
| SU1029451A1 (ru) | Антибактериальное средство |