CH651035A5 - Estere della 2-tenoilmercaptopropionil glicina con idrossibenzeni sostituiti, procedimento per la sua preparazione e composizioni farmaceutiche che lo contengono. - Google Patents
Estere della 2-tenoilmercaptopropionil glicina con idrossibenzeni sostituiti, procedimento per la sua preparazione e composizioni farmaceutiche che lo contengono. Download PDFInfo
- Publication number
- CH651035A5 CH651035A5 CH3964/82A CH396482A CH651035A5 CH 651035 A5 CH651035 A5 CH 651035A5 CH 3964/82 A CH3964/82 A CH 3964/82A CH 396482 A CH396482 A CH 396482A CH 651035 A5 CH651035 A5 CH 651035A5
- Authority
- CH
- Switzerland
- Prior art keywords
- glycine
- ester according
- carbon atoms
- radical
- benzoate
- Prior art date
Links
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 title claims description 24
- 239000004471 Glycine Substances 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000005204 hydroxybenzenes Chemical class 0.000 title claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 150000002148 esters Chemical class 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 230000000510 mucolytic effect Effects 0.000 claims description 9
- -1 p-propyloxycarbonyl phenyl Chemical group 0.000 claims description 9
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 229960003742 phenol Drugs 0.000 claims description 4
- UHKCHIWCWLESKM-UHFFFAOYSA-N acetamide benzene Chemical compound CC(N)=O.C1=CC=CC=C1.C1=CC=CC=C1 UHKCHIWCWLESKM-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 claims description 3
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 229940095102 methyl benzoate Drugs 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- UDEWPOVQBGFNGE-UHFFFAOYSA-N benzoic acid n-propyl ester Natural products CCCOC(=O)C1=CC=CC=C1 UDEWPOVQBGFNGE-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 claims 1
- 125000005429 oxyalkyl group Chemical group 0.000 claims 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 27
- 239000000243 solution Substances 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
- 241001465754 Metazoa Species 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 230000001886 ciliary effect Effects 0.000 description 7
- 230000028327 secretion Effects 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- 239000000203 mixture Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000829 suppository Substances 0.000 description 6
- 206010036790 Productive cough Diseases 0.000 description 5
- 210000003802 sputum Anatomy 0.000 description 5
- 208000024794 sputum Diseases 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229940086542 triethylamine Drugs 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 229960004308 acetylcysteine Drugs 0.000 description 4
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-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
- 239000004296 sodium metabisulphite Substances 0.000 description 4
- 235000010262 sodium metabisulphite Nutrition 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229910001868 water Inorganic materials 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 206010011224 Cough Diseases 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
- 239000000443 aerosol Substances 0.000 description 3
- 230000000954 anitussive effect Effects 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
- 239000012895 dilution Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000003172 expectorant agent Substances 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 210000000981 epithelium Anatomy 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 230000003419 expectorant effect Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229960001867 guaiacol Drugs 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- YBPAYPRLUDCSEY-UHFFFAOYSA-N p-hydroxyphenylacetoamide Natural products NC(=O)CC1=CC=C(O)C=C1 YBPAYPRLUDCSEY-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 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
- 239000005720 sucrose Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 231100000033 toxigenic Toxicity 0.000 description 2
- 230000001551 toxigenic effect Effects 0.000 description 2
- 210000005062 tracheal ring Anatomy 0.000 description 2
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-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
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- YTGJWQPHMWSCST-UHFFFAOYSA-N Tiopronin Chemical class CC(S)C(=O)NCC(O)=O YTGJWQPHMWSCST-UHFFFAOYSA-N 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
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 1
- 239000003708 ampul Substances 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
- 238000001816 cooling 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
- 239000000686 essence Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 229940066491 mucolytics Drugs 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 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
- 239000000600 sorbitol Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 239000003643 water by type 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 (1)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH651035A5 true CH651035A5 (it) | 1985-08-30 |
Family
ID=11268648
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH3964/82A CH651035A5 (it) | 1981-07-02 | 1982-06-28 | Estere della 2-tenoilmercaptopropionil glicina con idrossibenzeni sostituiti, procedimento per la sua preparazione e composizioni farmaceutiche che lo contengono. |
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 |
| BE893712A (fr) | 1982-10-18 |
| NL8202658A (nl) | 1983-02-01 |
| 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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