NL8202658A - Esters van 2-thenoylmercaptopropionylglycine met gesubstitueerde hydroxybenzenen, werkwijzen ter bereiding ervan en farmaceutische samenstellingen, die deze esters bevatten. - Google Patents
Esters van 2-thenoylmercaptopropionylglycine met gesubstitueerde hydroxybenzenen, werkwijzen ter bereiding ervan en farmaceutische samenstellingen, die deze esters bevatten. Download PDFInfo
- Publication number
- NL8202658A NL8202658A NL8202658A NL8202658A NL8202658A NL 8202658 A NL8202658 A NL 8202658A NL 8202658 A NL8202658 A NL 8202658A NL 8202658 A NL8202658 A NL 8202658A NL 8202658 A NL8202658 A NL 8202658A
- Authority
- NL
- Netherlands
- Prior art keywords
- group
- esters
- benzoate
- formula
- general formula
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 17
- OIJKSYBUWMYGCW-UHFFFAOYSA-N 2-[3-(thiophene-2-carbonylsulfanyl)propanoylamino]acetic acid Chemical compound OC(=O)CNC(=O)CCSC(=O)C1=CC=CS1 OIJKSYBUWMYGCW-UHFFFAOYSA-N 0.000 title claims description 11
- 238000000034 method Methods 0.000 title description 11
- 239000008194 pharmaceutical composition Substances 0.000 title description 4
- -1 p-acetamidophenyl Chemical group 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 230000000510 mucolytic effect Effects 0.000 claims description 7
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- 150000005204 hydroxybenzenes Chemical class 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 4
- 229960003742 phenol Drugs 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- YBPAYPRLUDCSEY-UHFFFAOYSA-N p-hydroxyphenylacetoamide Natural products NC(=O)CC1=CC=C(O)C=C1 YBPAYPRLUDCSEY-UHFFFAOYSA-N 0.000 claims description 3
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 claims description 3
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 claims description 3
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- RIJBKMCYKHLWRV-UHFFFAOYSA-N methyl 2-[2-[2-(thiophene-2-carbonylsulfanyl)propanoylamino]acetyl]oxybenzoate Chemical compound COC(=O)C1=CC=CC=C1OC(=O)CNC(=O)C(C)SC(=O)C1=CC=CS1 RIJBKMCYKHLWRV-UHFFFAOYSA-N 0.000 claims description 2
- KBCNTWWBYSUFLJ-UHFFFAOYSA-N propyl 4-[2-[2-(thiophene-2-carbonylsulfanyl)propanoylamino]acetyl]oxybenzoate Chemical compound C1=CC(C(=O)OCCC)=CC=C1OC(=O)CNC(=O)C(C)SC(=O)C1=CC=CS1 KBCNTWWBYSUFLJ-UHFFFAOYSA-N 0.000 claims description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 1
- 239000004471 Glycine Substances 0.000 claims 1
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims 1
- 229960001413 acetanilide Drugs 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 claims 1
- FKDAYYMVBAPGAQ-UHFFFAOYSA-N ethyl 2-[2-[2-(thiophene-2-carbonylsulfanyl)propanoylamino]acetyl]oxybenzoate Chemical compound CCOC(=O)C1=CC=CC=C1OC(=O)CNC(=O)C(C)SC(=O)C1=CC=CS1 FKDAYYMVBAPGAQ-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- WOMAZEJKVZLLFE-UHFFFAOYSA-N propionylglycine Chemical compound CCC(=O)NCC(O)=O WOMAZEJKVZLLFE-UHFFFAOYSA-N 0.000 claims 1
- XTYJVBOYAXETOD-UHFFFAOYSA-N propyl 2-[2-[2-(thiophene-2-carbonylsulfanyl)propanoylamino]acetyl]oxybenzoate Chemical compound CCCOC(=O)C1=CC=CC=C1OC(=O)CNC(=O)C(C)SC(=O)C1=CC=CS1 XTYJVBOYAXETOD-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 25
- 239000000243 solution Substances 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 241001465754 Metazoa Species 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 206010011224 Cough Diseases 0.000 description 7
- 230000001886 ciliary effect Effects 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000028327 secretion Effects 0.000 description 6
- 239000000829 suppository Substances 0.000 description 6
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 5
- 206010036790 Productive cough Diseases 0.000 description 5
- 229960004308 acetylcysteine Drugs 0.000 description 5
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 210000003802 sputum Anatomy 0.000 description 5
- 208000024794 sputum Diseases 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 4
- 229940001584 sodium metabisulfite Drugs 0.000 description 4
- 235000010262 sodium metabisulphite Nutrition 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LWKQXPGHHVOJAV-UHFFFAOYSA-N (4-acetamidophenyl) 2-[2-(thiophene-2-carbonylsulfanyl)propanoylamino]acetate Chemical compound C=1C=C(NC(C)=O)C=CC=1OC(=O)CNC(=O)C(C)SC(=O)C1=CC=CS1 LWKQXPGHHVOJAV-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus 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
- 239000003708 ampul Substances 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 210000000981 epithelium Anatomy 0.000 description 2
- 229960001867 guaiacol Drugs 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 230000004899 motility Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 239000002904 solvent Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 210000003437 trachea Anatomy 0.000 description 2
- FSCGLKWYHHSLST-UHFFFAOYSA-N 2-(3-sulfanylpropanoylamino)acetic acid Chemical compound OC(=O)CNC(=O)CCS FSCGLKWYHHSLST-UHFFFAOYSA-N 0.000 description 1
- PJFNNMFXEVADGK-UHFFFAOYSA-N 2-hydroxy-n-phenylacetamide Chemical compound OCC(=O)NC1=CC=CC=C1 PJFNNMFXEVADGK-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 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
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 108010058907 Tiopronin Proteins 0.000 description 1
- OUCXYSRPMBQONT-UHFFFAOYSA-N acetamide;phenol Chemical compound CC(N)=O.OC1=CC=CC=C1 OUCXYSRPMBQONT-UHFFFAOYSA-N 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000000954 anitussive effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000003172 expectorant agent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229940066491 mucolytics Drugs 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000007968 orange flavor Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 235000019615 sensations Nutrition 0.000 description 1
- 239000004460 silage Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229960004402 tiopronin Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000003799 water insoluble solvent Substances 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/10—Expectorants
-
- 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]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000431560A CA1193676A (en) | 1982-07-01 | 1983-06-30 | High-stability clock signal regenerator |
| AU16522/83A AU558292B2 (en) | 1982-07-01 | 1983-07-04 | High stability clock signal regenerator |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT4880781 | 1981-07-02 | ||
| IT48807/81A IT1143209B (it) | 1981-07-02 | 1981-07-02 | Esteri della 2-tenoilmercaptopropionil glicina con idrossibenzeni sostituiti procedimento per la loro preparazione e composizioni farmaceutiche che li contengono |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8202658A true NL8202658A (nl) | 1983-02-01 |
Family
ID=11268648
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8202658A NL8202658A (nl) | 1981-07-02 | 1982-07-01 | Esters van 2-thenoylmercaptopropionylglycine met gesubstitueerde hydroxybenzenen, werkwijzen ter bereiding ervan en farmaceutische samenstellingen, die deze esters bevatten. |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4472424A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS5810577A (cg-RX-API-DMAC7.html) |
| KR (1) | KR860001311B1 (cg-RX-API-DMAC7.html) |
| AT (1) | ATA255682A (cg-RX-API-DMAC7.html) |
| BE (1) | BE893712A (cg-RX-API-DMAC7.html) |
| CA (1) | CA1198735A (cg-RX-API-DMAC7.html) |
| CH (1) | CH651035A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE3224824A1 (cg-RX-API-DMAC7.html) |
| DK (1) | DK153760C (cg-RX-API-DMAC7.html) |
| ES (1) | ES514456A0 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2508907A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB2102797B (cg-RX-API-DMAC7.html) |
| GR (1) | GR76187B (cg-RX-API-DMAC7.html) |
| IE (1) | IE53190B1 (cg-RX-API-DMAC7.html) |
| IL (1) | IL66190A0 (cg-RX-API-DMAC7.html) |
| IT (1) | IT1143209B (cg-RX-API-DMAC7.html) |
| LU (1) | LU84245A1 (cg-RX-API-DMAC7.html) |
| NL (1) | NL8202658A (cg-RX-API-DMAC7.html) |
| SE (1) | SE8204116L (cg-RX-API-DMAC7.html) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1241415B (it) * | 1990-03-05 | 1994-01-14 | Yason Srl | Derivato dell'acido s-(2-tenoil)-tiolattico ad attivita' farmacologica |
| US5114963A (en) * | 1991-03-13 | 1992-05-19 | Medicis Corporation | Method of reducing serum levels of lipoprotein(A) |
| JP3765572B2 (ja) * | 2000-08-18 | 2006-04-12 | 有限会社ジャパン通商 | 床暖房装置、熱サイフォン式ヒートパイプおよびヒートパイプの製造方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1121825A (en) * | 1978-04-11 | 1982-04-13 | Franco Bolasco | 2-(2-thenoylthio)-propionylglycine: method for its preparation and pharmaceutical formulations containing said compound |
| IT1111384B (it) * | 1978-12-21 | 1986-01-13 | Sigma Tau Ind Farmaceuti | Guaiacil esteri di derivati dello acido mercaptopropionico procedimento per la loro preparazione e loro uso terapeutico |
| 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 |
| 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 |
-
1981
- 1981-07-02 IT IT48807/81A patent/IT1143209B/it active
-
1982
- 1982-06-22 IE IE1483/82A patent/IE53190B1/en unknown
- 1982-06-24 US US06/391,741 patent/US4472424A/en not_active Expired - Fee Related
- 1982-06-25 CA CA000405966A patent/CA1198735A/en not_active Expired
- 1982-06-28 GB GB08218672A patent/GB2102797B/en not_active Expired
- 1982-06-28 CH CH3964/82A patent/CH651035A5/it not_active IP Right Cessation
- 1982-06-30 KR KR8202936A patent/KR860001311B1/ko not_active Expired
- 1982-06-30 JP JP57114775A patent/JPS5810577A/ja active Pending
- 1982-06-30 LU LU84245A patent/LU84245A1/fr unknown
- 1982-06-30 DK DK294982A patent/DK153760C/da not_active IP Right Cessation
- 1982-06-30 BE BE0/208501A patent/BE893712A/fr not_active IP Right Cessation
- 1982-07-01 GR GR68614A patent/GR76187B/el unknown
- 1982-07-01 AT AT0255682A patent/ATA255682A/de not_active Application Discontinuation
- 1982-07-01 IL IL66190A patent/IL66190A0/xx unknown
- 1982-07-01 NL NL8202658A patent/NL8202658A/nl not_active Application Discontinuation
- 1982-07-01 ES ES514456A patent/ES514456A0/es active Granted
- 1982-07-02 FR FR8211684A patent/FR2508907A1/fr active Granted
- 1982-07-02 DE DE19823224824 patent/DE3224824A1/de not_active Ceased
- 1982-07-02 SE SE8204116A patent/SE8204116L/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| SE8204116L (sv) | 1983-01-03 |
| FR2508907B1 (cg-RX-API-DMAC7.html) | 1984-12-28 |
| DK153760B (da) | 1988-08-29 |
| KR860001311B1 (ko) | 1986-09-13 |
| IT1143209B (it) | 1986-10-22 |
| FR2508907A1 (fr) | 1983-01-07 |
| GB2102797A (en) | 1983-02-09 |
| DE3224824A1 (de) | 1983-01-27 |
| JPS5810577A (ja) | 1983-01-21 |
| ES8306369A1 (es) | 1983-06-01 |
| KR840000235A (ko) | 1984-02-18 |
| DK294982A (da) | 1983-01-03 |
| GR76187B (cg-RX-API-DMAC7.html) | 1984-08-03 |
| US4472424A (en) | 1984-09-18 |
| DK153760C (da) | 1989-01-09 |
| GB2102797B (en) | 1985-01-30 |
| IL66190A0 (en) | 1982-11-30 |
| IT8148807A0 (it) | 1981-07-02 |
| IE53190B1 (en) | 1988-08-17 |
| CH651035A5 (it) | 1985-08-30 |
| BE893712A (fr) | 1982-10-18 |
| IE821483L (en) | 1983-01-02 |
| CA1198735A (en) | 1985-12-31 |
| ES514456A0 (es) | 1983-06-01 |
| ATA255682A (de) | 1990-05-15 |
| LU84245A1 (fr) | 1983-01-20 |
| SE8204116D0 (sv) | 1982-07-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BV | The patent application has lapsed |