FR2508907A1 - Esters d'hydroxybenzenes substitues de 2-thenoylmercaptopropionylglycine utiles notamment comme mucolytiques, procede pour leur preparation et compositions pharmaceutiques les contenant - Google Patents
Esters d'hydroxybenzenes substitues de 2-thenoylmercaptopropionylglycine utiles notamment comme mucolytiques, procede pour leur preparation et compositions pharmaceutiques les contenant Download PDFInfo
- Publication number
- FR2508907A1 FR2508907A1 FR8211684A FR8211684A FR2508907A1 FR 2508907 A1 FR2508907 A1 FR 2508907A1 FR 8211684 A FR8211684 A FR 8211684A FR 8211684 A FR8211684 A FR 8211684A FR 2508907 A1 FR2508907 A1 FR 2508907A1
- Authority
- FR
- France
- Prior art keywords
- acetamidophenyl
- compounds
- preparation
- thenoylmercaptopropionylglycin
- useful
- 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.)
- Granted
Links
- 239000003172 expectorant agent Substances 0.000 title abstract description 7
- 238000002360 preparation method Methods 0.000 title abstract description 6
- OIJKSYBUWMYGCW-UHFFFAOYSA-N 2-[3-(thiophene-2-carbonylsulfanyl)propanoylamino]acetic acid Chemical group OC(=O)CNC(=O)CCSC(=O)C1=CC=CS1 OIJKSYBUWMYGCW-UHFFFAOYSA-N 0.000 title abstract description 5
- 229940066491 mucolytics Drugs 0.000 title abstract description 5
- 238000000034 method Methods 0.000 title description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical group OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title description 3
- 239000008194 pharmaceutical composition Substances 0.000 title description 3
- 230000000510 mucolytic effect Effects 0.000 abstract description 8
- 239000003814 drug Substances 0.000 abstract description 4
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract description 2
- 239000002260 anti-inflammatory agent Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 27
- 239000000243 solution Substances 0.000 description 17
- -1 chloro- Chemical class 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 15
- 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 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 8
- 230000001886 ciliary effect Effects 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 230000028327 secretion Effects 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000008064 anhydrides Chemical class 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
- 239000000829 suppository Substances 0.000 description 6
- 206010036790 Productive cough Diseases 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
- 206010011224 Cough Diseases 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 group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 229960004308 acetylcysteine Drugs 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 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
- 238000012360 testing method Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000004471 Glycine Substances 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
- 238000010171 animal model Methods 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
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 3
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 3
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- 241001331845 Equus asinus x caballus Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
- 238000002474 experimental method Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 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
- 239000000047 product Substances 0.000 description 2
- WOMAZEJKVZLLFE-UHFFFAOYSA-N propionylglycine Chemical compound CCC(=O)NCC(O)=O WOMAZEJKVZLLFE-UHFFFAOYSA-N 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N pyrocatechol monomethyl ether Natural products COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 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
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 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
- 229930192474 thiophene Natural products 0.000 description 2
- 210000003437 trachea Anatomy 0.000 description 2
- FSCGLKWYHHSLST-UHFFFAOYSA-N 2-(3-sulfanylpropanoylamino)acetic acid Chemical class 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
- XYGFNIWMWPGSGI-UHFFFAOYSA-N C(C)(=O)SC(C(=O)NCC(=O)O)C Chemical compound C(C)(=O)SC(C(=O)NCC(=O)O)C XYGFNIWMWPGSGI-UHFFFAOYSA-N 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 208000018569 Respiratory Tract disease Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 150000005204 hydroxybenzenes Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 239000002244 precipitate Substances 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
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 210000005062 tracheal ring Anatomy 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 (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 (2)
| Publication Number | Publication Date |
|---|---|
| FR2508907A1 true FR2508907A1 (fr) | 1983-01-07 |
| FR2508907B1 FR2508907B1 (OSRAM) | 1984-12-28 |
Family
ID=11268648
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8211684A Granted FR2508907A1 (fr) | 1981-07-02 | 1982-07-02 | Esters d'hydroxybenzenes substitues de 2-thenoylmercaptopropionylglycine utiles notamment comme mucolytiques, procede pour leur preparation et compositions pharmaceutiques les contenant |
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 |
|---|---|---|---|---|
| WO1991013883A1 (en) * | 1990-03-05 | 1991-09-19 | Yason S.R.L. | S-(2-thenoyl)-thiolactic acid derivative having pharmacological activity |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2422657A1 (fr) * | 1978-04-11 | 1979-11-09 | Mediolanum Farmaceutici Srl | 2-(2-thenoylthio)-propionylglycine, procede pour sa preparation et compositions pharmaceutiques la contenant |
| EP0013261A1 (en) * | 1978-12-21 | 1980-07-09 | Sigma-Tau Industrie Farmaceutiche Riunite S.p.A. | Guaiacol esters of alpha- and beta-mercaptopropionylalanine and alpha- and beta-mercaptopropionylglycine, process for their preparation and pharmaceutical compositions containing same |
| EP0044504A1 (en) * | 1980-07-22 | 1982-01-27 | NEOPHARMED S.p.A. | A derivative of theonyl thio-propionyl-glycine and process for the preparation thereof |
Family Cites Families (2)
| 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 |
| 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
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2422657A1 (fr) * | 1978-04-11 | 1979-11-09 | Mediolanum Farmaceutici Srl | 2-(2-thenoylthio)-propionylglycine, procede pour sa preparation et compositions pharmaceutiques la contenant |
| EP0013261A1 (en) * | 1978-12-21 | 1980-07-09 | Sigma-Tau Industrie Farmaceutiche Riunite S.p.A. | Guaiacol esters of alpha- and beta-mercaptopropionylalanine and alpha- and beta-mercaptopropionylglycine, process for their preparation and pharmaceutical compositions containing same |
| EP0044504A1 (en) * | 1980-07-22 | 1982-01-27 | NEOPHARMED S.p.A. | A derivative of theonyl thio-propionyl-glycine and process for the preparation thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991013883A1 (en) * | 1990-03-05 | 1991-09-19 | Yason S.R.L. | S-(2-thenoyl)-thiolactic acid derivative having pharmacological activity |
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 |
| JPS5810577A (ja) | 1983-01-21 |
| SE8204116D0 (sv) | 1982-07-02 |
| KR860001311B1 (ko) | 1986-09-13 |
| ATA255682A (de) | 1990-05-15 |
| 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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