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GeMigliptin

Product Name
GeMigliptin
CAS No.
911637-19-9
Chemical Name
GeMigliptin
Synonyms
LC15-0444;GeMigliptin;GeMigliptin WS;Gemigliptin - G10587;GeMigliptin Tartarate;Gemigliptin Hydrochloride;Product name:-Gemigliptintartarate;Inhibitor,DPP,Gemigliptin,Dipeptidyl Peptidase,inhibit;(S)-1-(2-Amino-4-(2,4-bis(trifluoromethyl)-5,6-dihydropyrido[3,4-d]pyrimidin-7(8H)-yl)-4-oxobutyl)-5,5-difluoropiperidin-2-one;1-[(2S)-2-amino-4-[2,4-bis(trifluoromethyl)-6,8-dihydro-5H-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-5,5-difluoropiperidin-2-one
CBNumber
CB82627898
Molecular Formula
C18H19F8N5O2
Formula Weight
489.36
MOL File
911637-19-9.mol
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GeMigliptin Property

Boiling point:
539.1±50.0 °C(Predicted)
Density 
1.54±0.1 g/cm3(Predicted)
storage temp. 
Store at -20°C
solubility 
DMSO:74.0(Max Conc. mg/mL);151.21(Max Conc. mM)
Ethanol:7.0(Max Conc. mg/mL);14.3(Max Conc. mM)
Water:12.0(Max Conc. mg/mL);24.52(Max Conc. mM)
pka
7.33±0.10(Predicted)
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

TRC
Product number
G337000
Product name
GemigliptinHydrochloride
Packaging
25mg
Price
$13125
Updated
2021/12/16
Matrix Scientific
Product number
122479
Product name
Gemigliptin
Purity
97.0%
Packaging
1g
Price
$2655
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0013914
Product name
GEMIGLIPTIN
Purity
95.00%
Packaging
10MG
Price
$1582.35
Updated
2021/12/16
ChemScene
Product number
CS-0003618
Product name
Gemigliptin
Packaging
10mg
Price
$110
Updated
2021/12/16
ChemScene
Product number
CS-0003618
Product name
Gemigliptin
Packaging
50mg
Price
$330
Updated
2021/12/16
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GeMigliptin Chemical Properties,Usage,Production

Description

Gemigliptin is a prolyl-specific dipeptidyl aminopeptidase IV (DPP IV, DPP-4, CD26) inhibitor approved for the treatment of type 2 diabetes mellitus by the Korean Food and Drug Administration in 2012. Gemigliptin was discovered and developed by LG Life Sciences and is now the sixth DPP-4 inhibitor approved for the treatment of type 2 diabetes. At the time this review was prepared, there were no publications describing the discovery strategy and preclinical data that led to the advancement of gemigliptin to the clinic.

Uses

Gemigliptin Hydrochloride is used in biological studies as a novel dipeptidyl peptidase IV (DPP-IV) inhibitors and potential antidiabetic drug.

Definition

ChEBI: Gemigliptin is an organonitrogen compound and an organooxygen compound. It is functionally related to a beta-amino acid.

Synthesis

Commercial N-Boc-3-piperidone (71) was treated with LHMDS followed by ethyl trifluoroacetate to effect a Claisen condensation, producing diketone 72 in 81% yield. Cyclization of 72 with 2,2,2-trifluoroacetamide (73) gave bis-trifluoromethyl dihydropyridopyrimidine 74 in 23% yield. Removal of the Boc protecting group efficiently provided amine 75 in 96% yield.
1,4-Addition of ethyl bromodifluoroacetate (76) to ethyl acrylate (77) in the presence of copper powder and tetramethylethylenediamine (TMEDA) gave diester 78, which was selectively reduced with sodium borohydride (NaBH4) to give alcohol 79 in 90% overall yield for the two-step procedure. Alcohol 79 was then treated with perfluorobutanesulfonyl chloride and triethylamine to give activated alcohol 80 in 75% yield. Boc-L-aspartic acid 4-tert-butyl ester (81) was treated with ammonium bicarbonate and pyridine in the presence of di-tert-butyl dicarbonate to give formamide 82. Dehydration of 82 to give nitrile 83 was accomplished through reaction with cyanuric chloride in 95% overall yield for the two-step sequence. Hydrogenation of 83 in the presence of Pearlman?ˉs catalyst provided butyl amine 84. Alkylation of 84 with activated alcohol 80 in triethylamine followed by cyclization in acetic acid afforded difluoropyridone 85. Acidic hydrolysis of the ester proceeded with concomitant removal of the Boc protecting group, and was followed by reprotection of the amine with di-tert-butyl dicarbonate to give acid 86 in 84% overall yield for the three-step procedure in >97% ee. Coupling of 86 with fragment 75 in the presence of 1-hydroxybenzotriazole (HOBT) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC) gave amide 87 in 51% yield. Removal of the Boc group with thionyl chloride in ethanol followed by neutralization with aqueous sodium hydroxide and salt formation with L-tartaric acid provided gemigliptin L-tartrate hydrate (X) in 97.5% yield.

GeMigliptin Preparation Products And Raw materials

Raw materials

Preparation Products

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GeMigliptin Suppliers

Shanghai Hekang Biotechnology Co., Ltd.
Tel
18939837085
Fax
2880152141(QQ)
Email
youchemicals@gmail.com
Country
China
ProdList
1813
Advantage
55
Chembest Research Laboratories Limited
Tel
021-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6011
Advantage
61
Sichuan Wei Keqi Biological Technology Co., Ltd.
Tel
028-81700200 18116577057
Fax
028-81705658
Email
3003855609@qq.com
Country
China
ProdList
7892
Advantage
56
SPIRO PHARMA
Tel
Fax
-
Email
eric_feng1954@126.com
Country
China
ProdList
9254
Advantage
55
Chengdu DingDang Pharmaceutical Co., Ltd.
Tel
028-86040038 13980902949;
Fax
028-85149890
Email
market@dingdangchem.com
Country
China
ProdList
1745
Advantage
55
Pharmacodia (Beijing) Co.,Ltd
Tel
+86-400-851-9921
Fax
+86-10-82826195
Email
sales@pharmacodia.com
Country
China
ProdList
2317
Advantage
55
Artis Biotech Co. Ltd.
Tel
19138486554 18582380095
Fax
0575-89298961
Email
sales@artisbio.com
Country
China
ProdList
2964
Advantage
58
Amadis Chemical Company Limited
Tel
571-89925085
Fax
0086-571-89925065
Email
sales@amadischem.com
Country
China
ProdList
131981
Advantage
58
Lynnchem
Tel
86-(0)29-85992781 17792393971
Email
info@lynnchem.com
Country
China
ProdList
4587
Advantage
58
Novachemistry
Tel
44-20819178-90 02081917890
Fax
(0)2080432064
Email
info@novachemistry.com
Country
United Kingdom
ProdList
4381
Advantage
58

911637-19-9, GeMigliptinRelated Search:


  • GeMigliptin
  • GeMigliptin Tartarate
  • Gemigliptin - G10587
  • (S)-1-(2-Amino-4-(2,4-bis(trifluoromethyl)-5,6-dihydropyrido[3,4-d]pyrimidin-7(8H)-yl)-4-oxobutyl)-5,5-difluoropiperidin-2-one
  • (S)-1-(2-amino-4-(2,4-bis(trifluoromethyl)-5,8-dihydropyrido[3,4-d]pyrimidin-7(6H)-yl)-4-oxobutyl)-5,5-difluoropiperidin-2-one hydrochloride
  • GeMigliptin WS
  • LC15-0444
  • Gemigliptin Hydrochloride
  • Product name:-Gemigliptintartarate
  • 2-Piperidinone, 1-[(2S)-2-amino-4-[5,8-dihydro-2,4-bis(trifluoromethyl)pyrido[3,4-d]pyrimidin-7(6H)-yl]-4-oxobutyl]-5,5-difluoro-
  • 1-[(2S)-2-amino-4-[2,4-bis(trifluoromethyl)-6,8-dihydro-5H-pyrido[3,4-d]pyrimidin-7-yl]-4-oxobutyl]-5,5-difluoropiperidin-2-one
  • Inhibitor,DPP,Gemigliptin,Dipeptidyl Peptidase,inhibit
  • 911637-19-9
  • C18H19F8N5O2