DE422566T1 - Verfahren zur herstellung von 3-(l-pyroglutamyl)-l-thiazolidin-4-carbonsaeure-derivaten. - Google Patents
Verfahren zur herstellung von 3-(l-pyroglutamyl)-l-thiazolidin-4-carbonsaeure-derivaten.Info
- Publication number
- DE422566T1 DE422566T1 DE199090119271T DE90119271T DE422566T1 DE 422566 T1 DE422566 T1 DE 422566T1 DE 199090119271 T DE199090119271 T DE 199090119271T DE 90119271 T DE90119271 T DE 90119271T DE 422566 T1 DE422566 T1 DE 422566T1
- Authority
- DE
- Germany
- Prior art keywords
- thiazolidine
- pyroglutamyl
- producing
- acid derivatives
- carbonic acid
- 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
- -1 L-PYROGLUTAMYL Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical group C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims 1
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 abstract 2
- ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical class OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 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
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Claims (3)
1. Verfahren zur Herstellung von 3-(L-Pyroglutamyl)-L-thiazolidin-4-carbonsäure
und ihren Derivaten, umfassend die Umsetzung einer Verbindung der Formel (I)
ö-
/r
COX
in der:
R1 ein Wasserstoff atom, einen C1-C6-Al]CyI-, C3-C7-Cycloalkyl-,
C4 -C10-CyClOaHCyIaIlCyI-, Aryl- oder
substituierten Aryl-, C3-C5-Alkoxycarbonyl-, C3-C10-Alkylcarbonyl-,
Arylcarbonyl- oder Arälkylcarbonyl-, C8-C13-Aralkoxycarbonyl- oder einen substituierten
Aralkoxycarbonylrest bedeutet; und X eine Hydroxylgruppe oder die Gruppe OR2 (in der R3 eine aktivierende Gruppe
darstellt) oder ein Chloratom bedeutet mit einer Verbindung der Formel (II)
CO OC2H5
in der R3 ein Wasserstoffatom oder einen C3-C9-Trialkylsilylrest
bedeutet.
2. Verfahren nach Anspruch 1, wobei, falls X = OH, die
-1-Umsetzung in Gegenwart eines Kondensationsmittels
durchgeführt wird.
3. Verfahren nach Anspruch 2, wobei das Kondensationsmittel Dicyclohexylcarbodiimid oder Carbonyldiimidazol ist.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT22003A IT1239029B (it) | 1989-10-12 | 1989-10-12 | Processo per la preparazione dell'acido 3-(l-piroglutamil)-l- tiazolidin-4-carbossilico e suoi derivati. |
Publications (1)
Publication Number | Publication Date |
---|---|
DE422566T1 true DE422566T1 (de) | 1991-09-05 |
Family
ID=11190043
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE69018755T Expired - Fee Related DE69018755T2 (de) | 1989-10-12 | 1990-10-08 | Verfahren zur Herstellung von 3-(L-Pyroglutamyl)-L-thiazolidin-4-carbonsäure-Derivaten. |
DE199090119271T Pending DE422566T1 (de) | 1989-10-12 | 1990-10-08 | Verfahren zur herstellung von 3-(l-pyroglutamyl)-l-thiazolidin-4-carbonsaeure-derivaten. |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE69018755T Expired - Fee Related DE69018755T2 (de) | 1989-10-12 | 1990-10-08 | Verfahren zur Herstellung von 3-(L-Pyroglutamyl)-L-thiazolidin-4-carbonsäure-Derivaten. |
Country Status (18)
Country | Link |
---|---|
US (1) | US5110936A (de) |
EP (1) | EP0422566B1 (de) |
JP (1) | JP2813450B2 (de) |
KR (1) | KR100195895B1 (de) |
AT (1) | ATE121420T1 (de) |
AU (1) | AU644379B2 (de) |
CA (1) | CA2027341C (de) |
DE (2) | DE69018755T2 (de) |
DK (1) | DK0422566T3 (de) |
ES (1) | ES2028766T3 (de) |
FI (1) | FI95271C (de) |
GR (1) | GR910300072T1 (de) |
HU (1) | HU210213B (de) |
IE (1) | IE67047B1 (de) |
IL (1) | IL95949A (de) |
IT (1) | IT1239029B (de) |
NO (1) | NO178028C (de) |
ZA (1) | ZA908097B (de) |
Families Citing this family (11)
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. |
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 |
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" |
EP0929535A4 (de) * | 1996-09-06 | 2001-05-23 | Lilly Co Eli | Verfahren und neue zwischenprodukte |
JP2010537984A (ja) * | 2007-08-28 | 2010-12-09 | イプセン ファルマ ソシエテ パール アクシオン サンプリフィエ | ポリペプチドおよび蛋白質の化学合成のための方法および中間体 |
CN102167727B (zh) * | 2011-01-29 | 2013-05-15 | 浙江金立源药业有限公司 | 一种匹多莫德的合成方法 |
WO2016112977A1 (en) | 2015-01-15 | 2016-07-21 | Polichem S.A. | Di-pidotimod benzathine and solid forms thereof |
KR101642445B1 (ko) * | 2016-01-11 | 2016-07-26 | (주)남양통신 | 수상태양광 발전장치용 계류장치 |
CN107383162A (zh) * | 2017-07-06 | 2017-11-24 | 成都美域高制药有限公司 | 一种匹多莫德的制备方法 |
CN108640912A (zh) * | 2018-06-19 | 2018-10-12 | 广州大光制药有限公司 | 一种匹多莫德的工业化规模制备方法 |
CN111233854A (zh) * | 2019-12-30 | 2020-06-05 | 常州寅盛药业有限公司 | 一种匹多莫德杂质的制备方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1202426B (it) * | 1987-01-26 | 1989-02-09 | Poli Ind Chimica Spa | Derivato di acido tiazolidin-4-carbossilico,sua preparazione e composizioni farmaceutiche che lo contengono |
-
1989
- 1989-10-12 IT IT22003A patent/IT1239029B/it active IP Right Grant
-
1990
- 1990-10-08 DE DE69018755T patent/DE69018755T2/de not_active Expired - Fee Related
- 1990-10-08 DK DK90119271.6T patent/DK0422566T3/da active
- 1990-10-08 DE DE199090119271T patent/DE422566T1/de active Pending
- 1990-10-08 ES ES90119271T patent/ES2028766T3/es not_active Expired - Lifetime
- 1990-10-08 AT AT90119271T patent/ATE121420T1/de not_active IP Right Cessation
- 1990-10-08 EP EP90119271A patent/EP0422566B1/de not_active Expired - Lifetime
- 1990-10-08 IE IE359990A patent/IE67047B1/en not_active IP Right Cessation
- 1990-10-09 US US07/594,313 patent/US5110936A/en not_active Expired - Lifetime
- 1990-10-09 ZA ZA908097A patent/ZA908097B/xx unknown
- 1990-10-10 IL IL9594990A patent/IL95949A/en not_active IP Right Cessation
- 1990-10-10 KR KR1019900015999A patent/KR100195895B1/ko not_active IP Right Cessation
- 1990-10-11 CA CA002027341A patent/CA2027341C/en not_active Expired - Fee Related
- 1990-10-11 FI FI905011A patent/FI95271C/fi active IP Right Grant
- 1990-10-11 AU AU64521/90A patent/AU644379B2/en not_active Ceased
- 1990-10-11 NO NO904404A patent/NO178028C/no unknown
- 1990-10-11 HU HU906417A patent/HU210213B/hu not_active IP Right Cessation
- 1990-10-12 JP JP2275100A patent/JP2813450B2/ja not_active Expired - Fee Related
-
1991
- 1991-11-15 GR GR91300072T patent/GR910300072T1/el unknown
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