DE276752T1 - Thiazolidin-4-carbonsaeurederivat, seine herstellung und pharmazeutische zusammensetzungen, die dieses enthalten. - Google Patents
Thiazolidin-4-carbonsaeurederivat, seine herstellung und pharmazeutische zusammensetzungen, die dieses enthalten.Info
- Publication number
- DE276752T1 DE276752T1 DE198888100825T DE88100825T DE276752T1 DE 276752 T1 DE276752 T1 DE 276752T1 DE 198888100825 T DE198888100825 T DE 198888100825T DE 88100825 T DE88100825 T DE 88100825T DE 276752 T1 DE276752 T1 DE 276752T1
- Authority
- DE
- Germany
- Prior art keywords
- pharmaceutical compositions
- compound
- thiazolidin
- contain
- production
- 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
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000008194 pharmaceutical composition Substances 0.000 title claims 2
- 150000002148 esters Chemical class 0.000 claims abstract 4
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims abstract 3
- ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 claims abstract 3
- DZLNHFMRPBPULJ-GSVOUGTGSA-N D-thioproline Chemical compound OC(=O)[C@H]1CSCN1 DZLNHFMRPBPULJ-GSVOUGTGSA-N 0.000 claims abstract 2
- 230000003712 anti-aging effect Effects 0.000 claims abstract 2
- 230000003110 anti-inflammatory effect Effects 0.000 claims abstract 2
- 230000001147 anti-toxic effect Effects 0.000 claims abstract 2
- 230000003078 antioxidant effect Effects 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 claims 2
- LHJGJYXLEPZJPM-UHFFFAOYSA-N 2,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1Cl LHJGJYXLEPZJPM-UHFFFAOYSA-N 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims 1
- ODHCTXKNWHHXJC-GSVOUGTGSA-N Pyroglutamic acid Natural products OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 239000008298 dragée Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000008187 granular material Substances 0.000 claims 1
- 230000002519 immonomodulatory effect Effects 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000007940 sugar coated tablet Substances 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 239000003963 antioxidant agent Substances 0.000 abstract 1
- 229960001438 immunostimulant agent Drugs 0.000 abstract 1
- 239000003022 immunostimulating agent Substances 0.000 abstract 1
- 230000003308 immunostimulating effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- C07K5/06173—Dipeptides with the first amino acid being heterocyclic and Glp-amino acid; Derivatives thereof
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Rheumatology (AREA)
- Toxicology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
Claims (8)
- Patentansprüche:and deren pharmazeutisch annehmbaren Salze.
- 2. Verfahren zur Herstellung von Verbindung I, gekennzeichnet durch Umsetzen eines aktivierten Esters der L-Pyroglutaminsäure oder deren Säurechlorid mit L-Thiazolidin-4-carbonsäure.
- 3. Verfahren nach Anspruch 2, dadurch gekennzeichnet, daß die Reaktion in inerten Lösungsmittelnjausgewählt aus der Gruppe von Dimethylsulfoxid, Dimethylformamid und aliphatischen Dialkylamiden, in Gegenwart von Basen oder in Wasser bei 0 C in Gegenwart von NaOH durchgeführt wird.
- 4. Verfahren nach den Ansprüchen 2 oder 3, dadurch gekennzeichnet, daß der aktivierte Ester der Pyroglutaminsäure der Ester mit Pentachlorphenol, 2,4,5-Trichlorphenol, N-Hydroxysuccinimid ist.
- 5. Pharmazeutische Zusammensetzungen enthaltend als aktiven Bestandteil die Verbindung nach Anspruch 1 oder ein Salz davon im Gemisch mit eine-i pharmazeutisch annehmbaren Träger.
- 6. Zusammensetzungen nach Anspruch 5( in Form von Tabletten, Kapseln, mit Zucker überzogenen Tabletten, Granula oder Lösungen zur parenteralen oder oralen Verabreichung.
- 7. Verbindung nach Anspruch 1 zur Verwendung als ein Medikament.
- 8. Verwendung der Verbindung nach Anspruch 1 oder eines Salzes davon zur Herstellung eines Medikamentes mit immunmodulierenden, antitoxischen, entzündungshemmenden, oxidationshemmenden und anti-alternden Aktivitäten.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT19165/87A IT1202426B (it) | 1987-01-26 | 1987-01-26 | Derivato di acido tiazolidin-4-carbossilico,sua preparazione e composizioni farmaceutiche che lo contengono |
Publications (1)
Publication Number | Publication Date |
---|---|
DE276752T1 true DE276752T1 (de) | 1989-01-05 |
Family
ID=11155438
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE8888100825T Expired - Lifetime DE3864691D1 (de) | 1987-01-26 | 1988-01-21 | Thiazolidin-4-carbonsaeurederivat, seine herstellung und pharmazeutische zusammensetzungen, die dieses enthalten. |
DE198888100825T Pending DE276752T1 (de) | 1987-01-26 | 1988-01-21 | Thiazolidin-4-carbonsaeurederivat, seine herstellung und pharmazeutische zusammensetzungen, die dieses enthalten. |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE8888100825T Expired - Lifetime DE3864691D1 (de) | 1987-01-26 | 1988-01-21 | Thiazolidin-4-carbonsaeurederivat, seine herstellung und pharmazeutische zusammensetzungen, die dieses enthalten. |
Country Status (19)
Country | Link |
---|---|
US (1) | US4839387A (de) |
EP (1) | EP0276752B1 (de) |
JP (1) | JPS63201187A (de) |
KR (1) | KR960005167B1 (de) |
AT (1) | ATE67212T1 (de) |
AU (1) | AU613890B2 (de) |
CA (1) | CA1326029C (de) |
DE (2) | DE3864691D1 (de) |
DK (1) | DK171789B1 (de) |
ES (1) | ES2003856T3 (de) |
FI (1) | FI89369C (de) |
GR (2) | GR880300151T1 (de) |
HU (1) | HU202867B (de) |
IE (1) | IE60185B1 (de) |
IL (1) | IL85102A (de) |
IT (1) | IT1202426B (de) |
NO (1) | NO170686C (de) |
NZ (1) | NZ223287A (de) |
ZA (1) | ZA88379B (de) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1230706B (it) * | 1989-02-10 | 1991-10-29 | Poli Ind Chimica Spa | Derivati dell'acido 3 piroglutamoil tiazolidin 4 carbossilico e loro proprieta' farmacologiche. |
IT1239029B (it) * | 1989-10-12 | 1993-09-20 | Poli Ind Chimica Spa | Processo per la preparazione dell'acido 3-(l-piroglutamil)-l- tiazolidin-4-carbossilico e suoi derivati. |
IT1237998B (it) * | 1990-01-23 | 1993-06-21 | Poli Ind Chimica Spa | Acido 3-l-(5-tioxo-l-prolil)tiazolidin-4-carbossilico e derivati, loro preparazione e composizioni farmaceutiche che li contengono |
IT1240353B (it) * | 1990-03-30 | 1993-12-07 | Poli Ind Chimica Spa | Formulazioni liposomiali di farmaci immunomodulatori per applicazionelocale ed aerosolica |
DE69214467T3 (de) * | 1991-01-10 | 2000-09-28 | Transcend Therapeutics, Inc. | Verwendung von L-2-oxo Thiazolidin-4-carboxylat zur Behandlung von Atemnotsyndrom |
US5747459A (en) * | 1991-02-04 | 1998-05-05 | Nestec, Ltd. | Method for insuring adequate intracellular glutathione in tissue |
IT1244548B (it) * | 1991-02-06 | 1994-07-15 | Poli Ind Chimica Spa | Derivati della 5-oxo-l-prolina e loro applicazioni farmaceutiche |
FR2675692A1 (fr) * | 1991-04-24 | 1992-10-30 | Oreal | Systeme anti-oxydant contenant du pyrrolidone carboxylate de lysine et/ou du pyrrolidone carboxylate d'arginine soit seul soit associe a un derive phenolique et son utilisation en cosmetique. |
US5430045A (en) * | 1992-04-23 | 1995-07-04 | Free Radical Sciences, Inc. | Method of reducing or preventing bone marrow hypoplasia |
IT1264446B1 (it) * | 1993-05-14 | 1996-09-23 | Yason Srl | Acido 3 (n-(2-mercapto-propionil-ammino-acetil))-tetraidrotiazolil-4- carbossilico come agente antiinfiammatorio e immunostimolante |
US5447712A (en) * | 1993-12-09 | 1995-09-05 | Free Radical Sciences | Method of reducing cyclophosphamide induced hemorrhagic cystitis |
IT1270017B (it) * | 1994-09-27 | 1997-04-16 | Poli Ind Chimica Spa | "sintesi quantitativa dell'acido 3-(l-piroglutamil)-l-tiazolidin-4- carbossilico e suoi derivati" |
DE19711053C2 (de) * | 1997-03-03 | 1999-09-02 | Rommelspacher | Kombinationspräparat aus 2-Methyl-thiazolidin-2,4-dicarbonsäure und Paracetamol |
CN104059106B (zh) * | 2014-06-27 | 2017-02-15 | 魏景芬 | 一种磷酸糖醇类四氢噻唑‑4‑羧酸化合物的制备方法 |
CN104059107A (zh) * | 2014-06-27 | 2014-09-24 | 魏景芬 | 一种磷酸糖醇类四氢噻唑-4-羧酸化合物及其应用 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3959248A (en) * | 1974-04-03 | 1976-05-25 | Merck & Co., Inc. | Analogs of thyrotropin-releasing hormone |
US4085954A (en) * | 1974-06-03 | 1978-04-25 | Thompson Omer A | Slat assembly for chain link fence |
GB1492640A (en) * | 1975-07-08 | 1977-11-23 | Ucb Sa | L-pyroglutamyl-l-prolinamide |
HU180926B (en) * | 1979-06-28 | 1983-05-30 | Richter Gedeon Vegyeszet | Process for preparing trh analogues,tripeptide amides infectives on the central nerve sysrhem |
-
1987
- 1987-01-26 IT IT19165/87A patent/IT1202426B/it active
-
1988
- 1988-01-11 CA CA000556249A patent/CA1326029C/en not_active Expired - Lifetime
- 1988-01-14 IL IL85102A patent/IL85102A/xx not_active IP Right Cessation
- 1988-01-15 US US07/144,528 patent/US4839387A/en not_active Expired - Lifetime
- 1988-01-20 ZA ZA880379A patent/ZA88379B/xx unknown
- 1988-01-21 AU AU10673/88A patent/AU613890B2/en not_active Expired
- 1988-01-21 EP EP88100825A patent/EP0276752B1/de not_active Expired - Lifetime
- 1988-01-21 DE DE8888100825T patent/DE3864691D1/de not_active Expired - Lifetime
- 1988-01-21 DE DE198888100825T patent/DE276752T1/de active Pending
- 1988-01-21 ES ES198888100825T patent/ES2003856T3/es not_active Expired - Lifetime
- 1988-01-21 AT AT88100825T patent/ATE67212T1/de not_active IP Right Cessation
- 1988-01-22 NZ NZ223287A patent/NZ223287A/xx unknown
- 1988-01-25 KR KR1019880000537A patent/KR960005167B1/ko not_active IP Right Cessation
- 1988-01-25 IE IE17888A patent/IE60185B1/en not_active IP Right Cessation
- 1988-01-25 FI FI880324A patent/FI89369C/fi not_active IP Right Cessation
- 1988-01-25 HU HU88278A patent/HU202867B/hu unknown
- 1988-01-25 DK DK032288A patent/DK171789B1/da not_active IP Right Cessation
- 1988-01-25 JP JP63012762A patent/JPS63201187A/ja active Granted
- 1988-01-26 NO NO880332A patent/NO170686C/no not_active IP Right Cessation
-
1989
- 1989-01-31 GR GR88300151T patent/GR880300151T1/el unknown
-
1991
- 1991-11-04 GR GR91401668T patent/GR3003060T3/el unknown
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