SE444940B - 2-(2-tenoyltio)-propionylglycin samt forfarande for framstellning derav - Google Patents
2-(2-tenoyltio)-propionylglycin samt forfarande for framstellning deravInfo
- Publication number
- SE444940B SE444940B SE7903105A SE7903105A SE444940B SE 444940 B SE444940 B SE 444940B SE 7903105 A SE7903105 A SE 7903105A SE 7903105 A SE7903105 A SE 7903105A SE 444940 B SE444940 B SE 444940B
- Authority
- SE
- Sweden
- Prior art keywords
- compound
- animals
- treatment
- propionylglycine
- tenoylthio
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 43
- GSAJFWKHLRVDRB-UHFFFAOYSA-N 2-amino-3-sulfanylidenepentanoic acid Chemical compound CCC(=S)C(N)C(O)=O GSAJFWKHLRVDRB-UHFFFAOYSA-N 0.000 claims description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 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 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 241001465754 Metazoa Species 0.000 description 28
- 238000011282 treatment Methods 0.000 description 27
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 21
- 241000700159 Rattus Species 0.000 description 17
- 208000005374 Poisoning Diseases 0.000 description 12
- 231100000572 poisoning Toxicity 0.000 description 12
- 230000000607 poisoning effect Effects 0.000 description 12
- 239000000443 aerosol Substances 0.000 description 9
- 230000037396 body weight Effects 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 6
- 210000004185 liver Anatomy 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000700198 Cavia Species 0.000 description 5
- 230000034994 death Effects 0.000 description 5
- 231100000517 death Toxicity 0.000 description 5
- 210000004072 lung Anatomy 0.000 description 5
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 5
- 230000000510 mucolytic effect Effects 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 238000012453 sprague-dawley rat model Methods 0.000 description 5
- 238000010186 staining Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 229960004308 acetylcysteine Drugs 0.000 description 4
- 206010006451 bronchitis Diseases 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 230000002008 hemorrhagic effect Effects 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 3
- YTGJWQPHMWSCST-UHFFFAOYSA-N Tiopronin Chemical compound CC(S)C(=O)NCC(O)=O YTGJWQPHMWSCST-UHFFFAOYSA-N 0.000 description 3
- 108010058907 Tiopronin Proteins 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000007918 intramuscular administration Methods 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 3
- 229940001584 sodium metabisulfite Drugs 0.000 description 3
- 235000010262 sodium metabisulphite Nutrition 0.000 description 3
- 238000002798 spectrophotometry method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 206010011224 Cough Diseases 0.000 description 2
- 208000000059 Dyspnea Diseases 0.000 description 2
- 206010013975 Dyspnoeas Diseases 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- 101150054854 POU1F1 gene Proteins 0.000 description 2
- 229920005372 Plexiglas® Polymers 0.000 description 2
- 206010036790 Productive cough Diseases 0.000 description 2
- 241000978776 Senegalia senegal Species 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 102000001999 Transcription Factor Pit-1 Human genes 0.000 description 2
- 108010040742 Transcription Factor Pit-1 Proteins 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000002443 hepatoprotective effect Effects 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- 208000019423 liver disease Diseases 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
- 229940081974 saccharin Drugs 0.000 description 2
- 235000019204 saccharin Nutrition 0.000 description 2
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 230000004622 sleep time Effects 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 1
- 208000030090 Acute Disease Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- 208000001378 Carbon Tetrachloride Poisoning Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 201000003883 Cystic fibrosis Diseases 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- XRYVAQQLDYTHCL-UHFFFAOYSA-N Marini Chemical compound O1C=2C(CC(CC=C(C)C)C(C)=C)=C(O)C=C(O)C=2C(=O)CC1C1=CC=C(O)C=C1O XRYVAQQLDYTHCL-UHFFFAOYSA-N 0.000 description 1
- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 1
- 206010057190 Respiratory tract infections Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- JQGGPAQTWOUTAP-UHFFFAOYSA-M [Na+].CCC([O-])=NCC(O)=O Chemical compound [Na+].CCC([O-])=NCC(O)=O JQGGPAQTWOUTAP-UHFFFAOYSA-M 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000002555 auscultation Methods 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- PPZMYIBUHIPZOS-UHFFFAOYSA-N histamine dihydrochloride Chemical compound Cl.Cl.NCCC1=CN=CN1 PPZMYIBUHIPZOS-UHFFFAOYSA-N 0.000 description 1
- 229960000645 histamine hydrochloride Drugs 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 229940105631 nembutal Drugs 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- WOMAZEJKVZLLFE-UHFFFAOYSA-N propionylglycine Chemical compound CCC(=O)NCC(O)=O WOMAZEJKVZLLFE-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000011421 subcutaneous treatment Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- FIPGEHJAIBQQOO-UHFFFAOYSA-N thiophen-2-yl hydrogen carbonate Chemical compound OC(=O)OC1=CC=CS1 FIPGEHJAIBQQOO-UHFFFAOYSA-N 0.000 description 1
- 229960004402 tiopronin Drugs 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000048 toxicity data Toxicity 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/10—Expectorants
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pulmonology (AREA)
- Gastroenterology & Hepatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT22175/78A IT1095386B (it) | 1978-04-11 | 1978-04-11 | 2-(2-tenciltio)-propionilglicina,metodo per la sua preparazione e composizioni farmaceutiche che la contengono |
| IT2011179A IT1166627B (it) | 1979-02-12 | 1979-02-12 | Impiego della 2-(2-tenoiltio)-propionilglicina in qualita' di agente mucolitico e antibroncospastico |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7903105L SE7903105L (sv) | 1979-10-12 |
| SE444940B true SE444940B (sv) | 1986-05-20 |
Family
ID=26327401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7903105A SE444940B (sv) | 1978-04-11 | 1979-04-06 | 2-(2-tenoyltio)-propionylglycin samt forfarande for framstellning derav |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4242354A (de) |
| JP (1) | JPS5910673B2 (de) |
| AR (1) | AR219379A1 (de) |
| AT (1) | AT374194B (de) |
| CA (1) | CA1121825A (de) |
| CH (1) | CH639380A5 (de) |
| DE (1) | DE2913211C2 (de) |
| DK (1) | DK148117C (de) |
| ES (1) | ES479423A1 (de) |
| FR (1) | FR2422657A1 (de) |
| GB (1) | GB2018756B (de) |
| IE (1) | IE47946B1 (de) |
| LU (1) | LU81132A1 (de) |
| NL (1) | NL7902700A (de) |
| NO (1) | NO149312C (de) |
| SE (1) | SE444940B (de) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1149884B (it) * | 1980-06-03 | 1986-12-10 | Btb Ind Chimica | Prozedimento per la preparazione della n-(2-tenoil)tiopropionil)-glicina |
| IT1148890B (it) * | 1980-07-22 | 1986-12-03 | Neopharmed Spa | Derivato della teonil tiopropionil glicina e procedimento per la sua preparazione |
| US4415681A (en) * | 1980-10-23 | 1983-11-15 | Ford Motor Company | Stabilized crosslinked dispersion |
| FR2502627A1 (fr) * | 1981-02-02 | 1982-10-01 | Refarmed Sa | Derives thioliques de l'erythromycine a activite therapeutique, procede de preparation et produits pharmaceutiques dans lesquels ils apparaissent |
| IT1143209B (it) * | 1981-07-02 | 1986-10-22 | Sigma Tau Ind Farmaceuti | Esteri della 2-tenoilmercaptopropionil glicina con idrossibenzeni sostituiti procedimento per la loro preparazione e composizioni farmaceutiche che li contengono |
| IE52884B1 (en) * | 1981-05-11 | 1988-03-30 | Sigma Tau Ind Farmaceuti | 2-methoxyphenyl esters of n-substituted amino acids, their preparation and pharmaceutical use |
| FR2521146B1 (fr) * | 1983-02-02 | 1985-10-25 | Sigma Tau Ind Farmaceuti | Derives thioliques de l'erythromycine a activite therapeutique, procede de preparation, et produits pharmaceutiques dans lesquels ils apparaissent |
| IT1212723B (it) * | 1983-03-23 | 1989-11-30 | Medea Res Srl | Derivato dell'acido tiolattico ad attivita'broncosecretogoga. |
| JPS59191971U (ja) * | 1983-06-08 | 1984-12-20 | 有限会社 沢田久商店 | 枕 |
| US4595700A (en) * | 1984-12-21 | 1986-06-17 | G. D. Searle & Co. | Thiol based collagenase inhibitors |
| ATE63912T1 (de) * | 1987-02-05 | 1991-06-15 | Caber Farmaceutici | 4-oxo-1,3-benzodioxan-derivat. |
| JPS63199669U (de) * | 1987-05-22 | 1988-12-22 | ||
| US6192882B1 (en) * | 1997-02-24 | 2001-02-27 | Aradigm Corporation | Formulation and devices for monitoring the efficacy of the delivery of aerosols |
| US6349719B2 (en) | 1997-02-24 | 2002-02-26 | Aradigm Corporation | Formulation and devices for monitoring the efficacy of the delivery of aerosols |
| TWI598347B (zh) | 2009-07-13 | 2017-09-11 | 基利科學股份有限公司 | 調節細胞凋亡信號之激酶的抑制劑 |
| PL2588475T3 (pl) * | 2010-07-02 | 2015-10-30 | Gilead Sciences Inc | Inhibitory kinazy regulującej sygnał apoptozy |
| CN106008456A (zh) * | 2016-06-27 | 2016-10-12 | 山东川成医药股份有限公司 | 一种司替罗宁的制备方法 |
| WO2022250957A2 (en) * | 2021-05-10 | 2022-12-01 | Altibio, Inc. | Thioester prodrugs for the treatment of renal anomalies |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2510773A (en) * | 1946-05-18 | 1950-06-06 | Sterling Drug Inc | Process for preparing a tertiary amino-alkyl thiol-ester hydrochloride |
| US2632735A (en) * | 1951-03-01 | 1953-03-24 | Standard Oil Dev Co | Lubricating oil additives |
| US2669564A (en) * | 1951-03-17 | 1954-02-16 | Sterling Drug Inc | Tertiary-aminoalkyl 4-amino-2-alkoxy-thiolbenzoates and their preparation |
| FR2338701A1 (fr) * | 1976-01-23 | 1977-08-19 | Blum Jean | Nouveaux derives de la cysteine |
-
1979
- 1979-03-26 CA CA000324110A patent/CA1121825A/en not_active Expired
- 1979-03-27 FR FR7907633A patent/FR2422657A1/fr active Granted
- 1979-04-03 DE DE2913211A patent/DE2913211C2/de not_active Expired
- 1979-04-04 AT AT0249879A patent/AT374194B/de not_active IP Right Cessation
- 1979-04-04 CH CH318279A patent/CH639380A5/it not_active IP Right Cessation
- 1979-04-04 US US06/026,933 patent/US4242354A/en not_active Expired - Lifetime
- 1979-04-05 NL NL7902700A patent/NL7902700A/xx not_active Application Discontinuation
- 1979-04-05 AR AR276092A patent/AR219379A1/es active
- 1979-04-06 SE SE7903105A patent/SE444940B/sv not_active IP Right Cessation
- 1979-04-09 LU LU81132A patent/LU81132A1/xx unknown
- 1979-04-09 ES ES479423A patent/ES479423A1/es not_active Expired
- 1979-04-10 NO NO791205A patent/NO149312C/no unknown
- 1979-04-11 GB GB7912768A patent/GB2018756B/en not_active Expired
- 1979-04-11 JP JP54044827A patent/JPS5910673B2/ja not_active Expired
- 1979-04-11 DK DK153179A patent/DK148117C/da not_active IP Right Cessation
- 1979-08-08 IE IE788/79A patent/IE47946B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2422657B1 (de) | 1981-10-23 |
| ATA249879A (de) | 1983-08-15 |
| GB2018756A (en) | 1979-10-24 |
| CH639380A5 (it) | 1983-11-15 |
| IE790788L (en) | 1979-10-11 |
| DK148117C (da) | 1985-08-26 |
| CA1121825A (en) | 1982-04-13 |
| JPS54141761A (en) | 1979-11-05 |
| NO149312C (no) | 1984-03-28 |
| NO791205L (no) | 1979-10-12 |
| US4242354A (en) | 1980-12-30 |
| DE2913211C2 (de) | 1982-05-06 |
| NO149312B (no) | 1983-12-19 |
| DE2913211A1 (de) | 1979-10-25 |
| AT374194B (de) | 1984-03-26 |
| AR219379A1 (es) | 1980-08-15 |
| FR2422657A1 (fr) | 1979-11-09 |
| DK148117B (da) | 1985-03-11 |
| IE47946B1 (en) | 1984-07-25 |
| JPS5910673B2 (ja) | 1984-03-10 |
| DK153179A (da) | 1979-10-12 |
| LU81132A1 (fr) | 1979-06-19 |
| NL7902700A (nl) | 1979-10-15 |
| SE7903105L (sv) | 1979-10-12 |
| GB2018756B (en) | 1982-10-13 |
| ES479423A1 (es) | 1979-11-01 |
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