DE2041831C3 - alpha-Amino-beta-(N-Benzylthiocarbamoyl)-thiopropionsäure, Verfahren zu ihrer Herstellung, sowie diese enthaltende Arzneimittel - Google Patents
alpha-Amino-beta-(N-Benzylthiocarbamoyl)-thiopropionsäure, Verfahren zu ihrer Herstellung, sowie diese enthaltende ArzneimittelInfo
- Publication number
- DE2041831C3 DE2041831C3 DE2041831A DE2041831A DE2041831C3 DE 2041831 C3 DE2041831 C3 DE 2041831C3 DE 2041831 A DE2041831 A DE 2041831A DE 2041831 A DE2041831 A DE 2041831A DE 2041831 C3 DE2041831 C3 DE 2041831C3
- Authority
- DE
- Germany
- Prior art keywords
- cysteine
- mustard oil
- amino
- benzylthiocarbamoyl
- beta
- 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
- -1 Alpha-Amino-beta- (N-Benzylthiocarbamoyl) -thiopropionic acid Chemical compound 0.000 title description 10
- 239000003814 drug Substances 0.000 title description 5
- 238000000034 method Methods 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 230000008569 process Effects 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 3
- 239000008164 mustard oil Substances 0.000 description 29
- 229960002433 cysteine Drugs 0.000 description 25
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 23
- 235000018417 cysteine Nutrition 0.000 description 23
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- MDKCFLQDBWCQCV-UHFFFAOYSA-N benzyl isothiocyanate Chemical compound S=C=NCC1=CC=CC=C1 MDKCFLQDBWCQCV-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000000968 intestinal effect Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- QAADZYUXQLUXFX-UHFFFAOYSA-N N-phenylmethylthioformamide Natural products S=CNCC1=CC=CC=C1 QAADZYUXQLUXFX-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
- 206010037597 Pyelonephritis acute Diseases 0.000 description 2
- 206010037601 Pyelonephritis chronic Diseases 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 201000001555 acute pyelonephritis Diseases 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 201000006368 chronic pyelonephritis Diseases 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 210000001198 duodenum Anatomy 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- 238000011031 large-scale manufacturing process Methods 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
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229940032007 methylethyl ketone Drugs 0.000 description 2
- 235000019645 odor Nutrition 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 241000219198 Brassica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical group CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 1
- IFQSXNOEEPCSLW-DKWTVANSSA-N L-cysteine hydrochloride Chemical compound Cl.SC[C@H](N)C(O)=O IFQSXNOEEPCSLW-DKWTVANSSA-N 0.000 description 1
- 206010068319 Oropharyngeal pain Diseases 0.000 description 1
- 201000007100 Pharyngitis Diseases 0.000 description 1
- 206010037596 Pyelonephritis Diseases 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229960004308 acetylcysteine Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000001929 anti-hepatotoxic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- UXHQMSUJQLPRAW-UHFFFAOYSA-N benzene;isothiocyanic acid Chemical compound N=C=S.C1=CC=CC=C1 UXHQMSUJQLPRAW-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 229960001305 cysteine hydrochloride Drugs 0.000 description 1
- 201000003146 cystitis Diseases 0.000 description 1
- 238000007257 deesterification reaction Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 229940075894 denatured ethanol Drugs 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000008451 emotion Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000000918 epididymis Anatomy 0.000 description 1
- 201000010063 epididymitis Diseases 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
- 230000004992 fission Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 210000004347 intestinal mucosa Anatomy 0.000 description 1
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 231100000017 mucous membrane irritation Toxicity 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- KOODSCBKXPPKHE-UHFFFAOYSA-N propanethioic s-acid Chemical compound CCC(S)=O KOODSCBKXPPKHE-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 201000004537 pyelitis Diseases 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 108010058651 thioglucosidase Proteins 0.000 description 1
- 208000000143 urethritis Diseases 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 238000001291 vacuum drying 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)
Priority Applications (16)
| 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 |
| GB37507/71A GB1299037A (en) | 1970-08-22 | 1971-08-10 | Dithiocarbamic acid esters |
| CH1206771A CH565148A5 (enrdf_load_stackoverflow) | 1970-08-22 | 1971-08-17 | |
| NL717111400A NL145851B (nl) | 1970-08-22 | 1971-08-18 | Werkwijze ter bereiding van een geneesmiddel voor de perorale behandeling van bacteriele en mycotische aandoeningen van de uitscheidingssystemen. |
| BE771522A BE771522A (fr) | 1970-08-22 | 1971-08-19 | Dithiocarbamate dissociable en cysteine et isothiocyanate et son procede de preparation |
| FR7130255A FR2103445B1 (enrdf_load_stackoverflow) | 1970-08-22 | 1971-08-19 | |
| ES394344A ES394344A1 (es) | 1970-08-22 | 1971-08-19 | Procedimiento para la preparacion de un ester de acido di- tiocarbamico. |
| IT27675/71A IT1047889B (it) | 1970-08-22 | 1971-08-20 | Procedimento per la produzione di estere dell acido diticcarbammico scomponibile in cisteina acido peta sulfioril alfa amminopropionico ed isotiocianato |
| BR5436/71A BR7105436D0 (pt) | 1970-08-22 | 1971-08-20 | Processo para preparacao de acido alfa amino beta tiocarbamoil tio propionico substituido |
| AT730971A AT316578B (de) | 1970-08-22 | 1971-08-20 | Verfahren zur Herstellung von N-substituierten Dithiocarbaminsäureestern des Cysteins |
| DK411071A DK140139C (da) | 1970-08-22 | 1971-08-20 | Analogifremgangsmaade til fremstilling af benzyldithiocarbaminsyreester |
| LU63754D LU63754A1 (enrdf_load_stackoverflow) | 1970-08-22 | 1971-08-20 | |
| JP46063962A JPS5114493B1 (enrdf_load_stackoverflow) | 1970-08-22 | 1971-08-21 | |
| PL1971150132A PL81800B1 (enrdf_load_stackoverflow) | 1970-08-22 | 1971-08-21 | |
| CA121,251A CA992980A (en) | 1970-08-22 | 1971-08-23 | .alpha.-AMINO-.beta.-(N-BENZYLTHIOCARBAMOYLTHIO) PROPIONIC ACID AND THERAPEUTIC COMPOSITIONS |
| US05/438,975 US3998964A (en) | 1970-08-22 | 1974-02-04 | α-Amino-β-(N-benzylthiocarbamoylthio) propionic acid and therapeutic compositions |
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 (3)
| Publication Number | Publication Date |
|---|---|
| DE2041831A1 DE2041831A1 (de) | 1972-02-24 |
| DE2041831B2 DE2041831B2 (de) | 1973-10-18 |
| DE2041831C3 true DE2041831C3 (de) | 1974-05-09 |
Family
ID=5780532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2041831A Expired DE2041831C3 (de) | 1970-08-22 | 1970-08-22 | alpha-Amino-beta-(N-Benzylthiocarbamoyl)-thiopropionsäure, Verfahren zu ihrer Herstellung, sowie diese enthaltende Arzneimittel |
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 ES ES394344A patent/ES394344A1/es not_active Expired
- 1971-08-19 FR FR7130255A patent/FR2103445B1/fr not_active Expired
- 1971-08-19 BE BE771522A patent/BE771522A/xx not_active IP Right Cessation
- 1971-08-20 LU LU63754D patent/LU63754A1/xx unknown
- 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 IT IT27675/71A patent/IT1047889B/it active
- 1971-08-20 AT AT730971A patent/AT316578B/de active
- 1971-08-21 JP JP46063962A patent/JPS5114493B1/ja active Pending
- 1971-08-21 PL PL1971150132A patent/PL81800B1/pl unknown
- 1971-08-23 CA CA121,251A patent/CA992980A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE771522A (fr) | 1972-02-21 |
| JPS5114493B1 (enrdf_load_stackoverflow) | 1976-05-10 |
| FR2103445B1 (enrdf_load_stackoverflow) | 1975-08-01 |
| PL81800B1 (enrdf_load_stackoverflow) | 1975-08-30 |
| DK140139C (da) | 1979-11-19 |
| CH565148A5 (enrdf_load_stackoverflow) | 1975-08-15 |
| DK140139B (da) | 1979-06-25 |
| NL7111400A (enrdf_load_stackoverflow) | 1972-02-24 |
| DE2041831A1 (de) | 1972-02-24 |
| DE2041831B2 (de) | 1973-10-18 |
| LU63754A1 (enrdf_load_stackoverflow) | 1972-01-05 |
| AT316578B (de) | 1974-07-25 |
| ES394344A1 (es) | 1973-12-01 |
| BR7105436D0 (pt) | 1973-05-10 |
| GB1299037A (en) | 1972-12-06 |
| CA992980A (en) | 1976-07-13 |
| FR2103445A1 (enrdf_load_stackoverflow) | 1972-04-14 |
| NL145851B (nl) | 1975-05-15 |
| IT1047889B (it) | 1980-10-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |