JPS5810577A - ２−セノイルメルカプトプロピオニルグリシンのエステル、その製造法およびそれを有効成分とする医薬組成物 - Google Patents
２−セノイルメルカプトプロピオニルグリシンのエステル、その製造法およびそれを有効成分とする医薬組成物Info
- Publication number
- JPS5810577A JPS5810577A JP57114775A JP11477582A JPS5810577A JP S5810577 A JPS5810577 A JP S5810577A JP 57114775 A JP57114775 A JP 57114775A JP 11477582 A JP11477582 A JP 11477582A JP S5810577 A JPS5810577 A JP S5810577A
- Authority
- JP
- Japan
- Prior art keywords
- group
- ester
- benzoic acid
- alkyloxycarbophenyl
- general formula
- 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.)
- Pending
Links
- 150000002148 esters Chemical class 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000000203 mixture Substances 0.000 title description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 18
- 239000005711 Benzoic acid Substances 0.000 claims description 9
- 235000010233 benzoic acid Nutrition 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 8
- 230000000510 mucolytic effect Effects 0.000 claims description 7
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical class CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims description 2
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000005429 oxyalkyl group Chemical group 0.000 claims 2
- -1 p-acetamidophenyl Chemical group 0.000 claims 2
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 150000005204 hydroxybenzenes Chemical class 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 206010036790 Productive cough Diseases 0.000 description 7
- 230000001886 ciliary effect Effects 0.000 description 7
- 210000003802 sputum Anatomy 0.000 description 7
- 208000024794 sputum Diseases 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 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
- 229960004308 acetylcysteine Drugs 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000028327 secretion Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000010171 animal model Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- 239000003172 expectorant agent Substances 0.000 description 3
- 230000003419 expectorant effect Effects 0.000 description 3
- 241000411851 herbal medicine Species 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 241000700198 Cavia Species 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 101000610640 Homo sapiens U4/U6 small nuclear ribonucleoprotein Prp3 Proteins 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 101001110823 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-A Proteins 0.000 description 2
- 101000712176 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-B Proteins 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 102100040374 U4/U6 small nuclear ribonucleoprotein Prp3 Human genes 0.000 description 2
- 230000000954 anitussive effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 210000000981 epithelium Anatomy 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([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
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
- 235000010262 sodium metabisulphite Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 210000005062 tracheal ring Anatomy 0.000 description 2
- PJFNNMFXEVADGK-UHFFFAOYSA-N 2-hydroxy-n-phenylacetamide Chemical compound OCC(=O)NC1=CC=CC=C1 PJFNNMFXEVADGK-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-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
- 206010011224 Cough Diseases 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 208000018569 Respiratory Tract disease Diseases 0.000 description 1
- 235000010586 Sophora japonica Nutrition 0.000 description 1
- 244000046101 Sophora japonica Species 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 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 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 238000011047 acute toxicity test Methods 0.000 description 1
- 239000002386 air freshener Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229940124584 antitussives Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 238000002224 dissection Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- AEDIXYWIVPYNBI-UHFFFAOYSA-N heptanamide Chemical compound CCCCCCC(N)=O AEDIXYWIVPYNBI-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 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
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 230000032258 transport Effects 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
| IT48807A/81 | 1981-07-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5810577A true JPS5810577A (ja) | 1983-01-21 |
Family
ID=11268648
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57114775A Pending JPS5810577A (ja) | 1981-07-02 | 1982-06-30 | ２−セノイルメルカプトプロピオニルグリシンのエステル、その製造法およびそれを有効成分とする医薬組成物 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4472424A (OSRAM) |
| JP (1) | JPS5810577A (OSRAM) |
| KR (1) | KR860001311B1 (OSRAM) |
| AT (1) | ATA255682A (OSRAM) |
| BE (1) | BE893712A (OSRAM) |
| CA (1) | CA1198735A (OSRAM) |
| CH (1) | CH651035A5 (OSRAM) |
| DE (1) | DE3224824A1 (OSRAM) |
| DK (1) | DK153760C (OSRAM) |
| ES (1) | ES8306369A1 (OSRAM) |
| FR (1) | FR2508907A1 (OSRAM) |
| GB (1) | GB2102797B (OSRAM) |
| GR (1) | GR76187B (OSRAM) |
| IE (1) | IE53190B1 (OSRAM) |
| IL (1) | IL66190A0 (OSRAM) |
| IT (1) | IT1143209B (OSRAM) |
| LU (1) | LU84245A1 (OSRAM) |
| NL (1) | NL8202658A (OSRAM) |
| SE (1) | SE8204116L (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002016832A1 (en) * | 2000-08-18 | 2002-02-28 | Hokko Sohgoh Kaihatsu K.K. | Floor heater, thermal siphon heat pipe, and method of manufacturing heat pipe |
Families Citing this family (2)
| 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) |
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 BE BE0/208501A patent/BE893712A/fr not_active IP Right Cessation
- 1982-06-30 JP JP57114775A patent/JPS5810577A/ja active Pending
- 1982-06-30 KR KR8202936A patent/KR860001311B1/ko not_active Expired
- 1982-06-30 DK DK294982A patent/DK153760C/da not_active IP Right Cessation
- 1982-06-30 LU LU84245A patent/LU84245A1/fr unknown
- 1982-07-01 ES ES514456A patent/ES8306369A1/es not_active Expired
- 1982-07-01 IL IL66190A patent/IL66190A0/xx unknown
- 1982-07-01 NL NL8202658A patent/NL8202658A/nl not_active Application Discontinuation
- 1982-07-01 GR GR68614A patent/GR76187B/el unknown
- 1982-07-01 AT AT0255682A patent/ATA255682A/de not_active Application Discontinuation
- 1982-07-02 DE DE19823224824 patent/DE3224824A1/de not_active Ceased
- 1982-07-02 SE SE8204116A patent/SE8204116L/xx not_active Application Discontinuation
- 1982-07-02 FR FR8211684A patent/FR2508907A1/fr active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002016832A1 (en) * | 2000-08-18 | 2002-02-28 | Hokko Sohgoh Kaihatsu K.K. | Floor heater, thermal siphon heat pipe, and method of manufacturing heat pipe |
Also Published As
| Publication number | Publication date |
|---|---|
| KR840000235A (ko) | 1984-02-18 |
| US4472424A (en) | 1984-09-18 |
| CH651035A5 (it) | 1985-08-30 |
| IL66190A0 (en) | 1982-11-30 |
| BE893712A (fr) | 1982-10-18 |
| CA1198735A (en) | 1985-12-31 |
| IE821483L (en) | 1983-01-02 |
| DK294982A (da) | 1983-01-03 |
| GB2102797B (en) | 1985-01-30 |
| SE8204116L (sv) | 1983-01-03 |
| ES514456A0 (es) | 1983-06-01 |
| LU84245A1 (fr) | 1983-01-20 |
| ES8306369A1 (es) | 1983-06-01 |
| GR76187B (OSRAM) | 1984-08-03 |
| DK153760B (da) | 1988-08-29 |
| IT1143209B (it) | 1986-10-22 |
| GB2102797A (en) | 1983-02-09 |
| DK153760C (da) | 1989-01-09 |
| SE8204116D0 (sv) | 1982-07-02 |
| KR860001311B1 (ko) | 1986-09-13 |
| ATA255682A (de) | 1990-05-15 |
| FR2508907A1 (fr) | 1983-01-07 |
| FR2508907B1 (OSRAM) | 1984-12-28 |
| IE53190B1 (en) | 1988-08-17 |
| IT8148807A0 (it) | 1981-07-02 |
| NL8202658A (nl) | 1983-02-01 |
| DE3224824A1 (de) | 1983-01-27 |
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