MX2010012741A - Proceso para la sintesis de derivados de 3, 6- dihidro- 1, 3 , 5- triazina. - Google Patents
Proceso para la sintesis de derivados de 3, 6- dihidro- 1, 3 , 5- triazina.Info
- Publication number
- MX2010012741A MX2010012741A MX2010012741A MX2010012741A MX2010012741A MX 2010012741 A MX2010012741 A MX 2010012741A MX 2010012741 A MX2010012741 A MX 2010012741A MX 2010012741 A MX2010012741 A MX 2010012741A MX 2010012741 A MX2010012741 A MX 2010012741A
- Authority
- MX
- Mexico
- Prior art keywords
- process according
- formula
- compound
- base
- butanol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 24
- 230000015572 biosynthetic process Effects 0.000 title abstract description 11
- 238000003786 synthesis reaction Methods 0.000 title abstract description 11
- RMQOXNXLVICLNK-UHFFFAOYSA-N 1,4-dihydro-1,3,5-triazine Chemical class C1NC=NC=N1 RMQOXNXLVICLNK-UHFFFAOYSA-N 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 16
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical group 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 239000002798 polar solvent Substances 0.000 claims description 5
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- 230000007613 environmental effect Effects 0.000 claims description 3
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 3
- 235000017550 sodium carbonate Nutrition 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 1
- 235000015320 potassium carbonate Nutrition 0.000 claims 1
- 208000031773 Insulin resistance syndrome Diseases 0.000 abstract description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
- 208000035475 disorder Diseases 0.000 abstract description 2
- 239000002253 acid Substances 0.000 description 3
- 239000012453 solvate Substances 0.000 description 3
- OKGNMRKOGWTADH-UHFFFAOYSA-N 1,4-dihydropyrimidine Chemical class C1C=CNC=N1 OKGNMRKOGWTADH-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 2
- OETHQSJEHLVLGH-UHFFFAOYSA-N metformin hydrochloride Chemical compound Cl.CN(C)C(=N)N=C(N)N OETHQSJEHLVLGH-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- VXMDOKODOQETRU-UHFFFAOYSA-N 2-[(4-amino-2,5-dihydro-1H-1,3,5-triazin-6-ylidene)-methylazaniumyl]acetate Chemical compound C\[N+](CC([O-])=O)=C1\NCN=C(N)N1 VXMDOKODOQETRU-UHFFFAOYSA-N 0.000 description 1
- -1 2-amino-3,6-dihydro-4-dimethylamino-6- (4-hydroxyphenyl) triazine Chemical compound 0.000 description 1
- ZVXNZUBVDJPQDB-UHFFFAOYSA-N 4-[2-amino-6-(dimethylamino)-1,4-dihydro-1,3,5-triazin-4-yl]phenol Chemical compound N1=C(N)NC(N(C)C)=NC1C1=CC=C(O)C=C1 ZVXNZUBVDJPQDB-UHFFFAOYSA-N 0.000 description 1
- GFICWFZTBXUVIG-UHFFFAOYSA-N 6-n,6-n,4-trimethyl-1,4-dihydro-1,3,5-triazine-2,6-diamine Chemical compound CC1N=C(N)NC(N(C)C)=N1 GFICWFZTBXUVIG-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 102000015636 Oligopeptides Human genes 0.000 description 1
- 108010038807 Oligopeptides Proteins 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 150000002373 hemiacetals Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/10—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Endocrinology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08009483 | 2008-05-23 | ||
| PCT/EP2009/002997 WO2009141040A2 (en) | 2008-05-23 | 2009-04-24 | Process for the synthesis of 3,6-dihydro-1,3,5-triazine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2010012741A true MX2010012741A (es) | 2010-12-21 |
Family
ID=40791625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2010012741A MX2010012741A (es) | 2008-05-23 | 2009-04-24 | Proceso para la sintesis de derivados de 3, 6- dihidro- 1, 3 , 5- triazina. |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US20110124860A1 (enExample) |
| EP (1) | EP2300444B1 (enExample) |
| JP (1) | JP5458093B2 (enExample) |
| KR (1) | KR101618198B1 (enExample) |
| CN (1) | CN102036970A (enExample) |
| AU (1) | AU2009250149B2 (enExample) |
| BR (1) | BRPI0912512B1 (enExample) |
| CA (1) | CA2725011A1 (enExample) |
| CY (1) | CY1117855T1 (enExample) |
| DK (1) | DK2300444T3 (enExample) |
| EA (1) | EA018921B1 (enExample) |
| ES (1) | ES2571793T3 (enExample) |
| HR (1) | HRP20160414T1 (enExample) |
| HU (1) | HUE027532T2 (enExample) |
| IL (1) | IL209198A (enExample) |
| MX (1) | MX2010012741A (enExample) |
| PL (1) | PL2300444T3 (enExample) |
| RS (1) | RS54736B1 (enExample) |
| SI (1) | SI2300444T1 (enExample) |
| WO (1) | WO2009141040A2 (enExample) |
| ZA (1) | ZA201009160B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL2646422T3 (pl) | 2010-12-01 | 2015-12-31 | Poxel | Rozdział enancjomerów pochodnych triazyny z zastosowaniem kwasu winowego |
| CN105753801B (zh) * | 2016-03-25 | 2018-06-01 | 浙江工业大学 | 一种均三嗪类化合物的制备方法 |
| JP2020536121A (ja) | 2017-10-02 | 2020-12-10 | ポクセルＰｏｘｅｌ | 駆出率が保持された心不全を治療する方法 |
| CA3102412A1 (en) | 2018-06-06 | 2019-12-12 | Metavant Sciences Gmbh | Methods of treating subjects having diabetes with chronic kidney disease |
| WO2019238647A1 (en) | 2018-06-14 | 2019-12-19 | Poxel | Film-coated tablet comprising a triazine derivative for use in the treatment of diabetes |
| CN114681464B (zh) * | 2020-12-28 | 2024-07-09 | 南京理工大学 | 二甲双胍类似物在制备脑缺血再灌注损伤预防和治疗药物中的应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2804113B1 (fr) * | 2000-01-26 | 2004-06-18 | Lipha | Derives animes de dihydro-1,3,5-triazine et leurs applications en therapeutique |
| AU2003289375A1 (en) * | 2002-12-17 | 2004-07-09 | Hamari Chemicals, Ltd | Novel 2,4-diamino-1,3,5-triazine derivative |
| FR2853650B1 (fr) * | 2003-04-10 | 2006-07-07 | Merck Sante Sas | Procede de dedoublement d'amines utiles pour le traitement de desordres associes au syndrome d'insulino-resistance |
| DE102007054416A1 (de) * | 2007-11-13 | 2009-05-14 | Studiengesellschaft Kohle Mbh | Verfahren zur Herstellung von 3,6-Dihydro-1,3,5- Triazin-Derivaten für die Behandlungen von Erkrankungen, die mit dem Insulinresistenz-Syndrom assoziiert sind |
-
2009
- 2009-04-24 KR KR1020107028733A patent/KR101618198B1/ko not_active Expired - Fee Related
- 2009-04-24 PL PL09749530T patent/PL2300444T3/pl unknown
- 2009-04-24 ES ES09749530T patent/ES2571793T3/es active Active
- 2009-04-24 RS RS20160296A patent/RS54736B1/sr unknown
- 2009-04-24 WO PCT/EP2009/002997 patent/WO2009141040A2/en not_active Ceased
- 2009-04-24 JP JP2011509869A patent/JP5458093B2/ja not_active Expired - Fee Related
- 2009-04-24 EA EA201001828A patent/EA018921B1/ru not_active IP Right Cessation
- 2009-04-24 AU AU2009250149A patent/AU2009250149B2/en not_active Ceased
- 2009-04-24 HR HRP20160414TT patent/HRP20160414T1/hr unknown
- 2009-04-24 SI SI200931424A patent/SI2300444T1/sl unknown
- 2009-04-24 EP EP09749530.3A patent/EP2300444B1/en active Active
- 2009-04-24 US US12/736,856 patent/US20110124860A1/en not_active Abandoned
- 2009-04-24 MX MX2010012741A patent/MX2010012741A/es active IP Right Grant
- 2009-04-24 DK DK09749530.3T patent/DK2300444T3/en active
- 2009-04-24 CA CA2725011A patent/CA2725011A1/en not_active Abandoned
- 2009-04-24 CN CN2009801188956A patent/CN102036970A/zh active Pending
- 2009-04-24 HU HUE09749530A patent/HUE027532T2/en unknown
- 2009-04-24 BR BRPI0912512A patent/BRPI0912512B1/pt not_active IP Right Cessation
-
2010
- 2010-11-08 IL IL209198A patent/IL209198A/en active IP Right Grant
- 2010-12-21 ZA ZA2010/09160A patent/ZA201009160B/en unknown
-
2016
- 2016-05-11 CY CY20161100394T patent/CY1117855T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009141040A2 (en) | 2009-11-26 |
| PL2300444T3 (pl) | 2016-08-31 |
| JP2011520930A (ja) | 2011-07-21 |
| SI2300444T1 (sl) | 2016-10-28 |
| WO2009141040A3 (en) | 2010-01-21 |
| KR101618198B1 (ko) | 2016-05-04 |
| AU2009250149A1 (en) | 2009-11-26 |
| EA201001828A1 (ru) | 2011-04-29 |
| JP5458093B2 (ja) | 2014-04-02 |
| BRPI0912512B1 (pt) | 2018-09-11 |
| EP2300444A2 (en) | 2011-03-30 |
| DK2300444T3 (en) | 2016-05-23 |
| IL209198A0 (en) | 2011-01-31 |
| CN102036970A (zh) | 2011-04-27 |
| CA2725011A1 (en) | 2009-11-26 |
| KR20110013498A (ko) | 2011-02-09 |
| EA018921B1 (ru) | 2013-11-29 |
| US20110124860A1 (en) | 2011-05-26 |
| HUE027532T2 (en) | 2016-10-28 |
| EP2300444B1 (en) | 2016-04-13 |
| HRP20160414T1 (hr) | 2016-05-20 |
| CY1117855T1 (el) | 2017-05-17 |
| BRPI0912512A2 (pt) | 2015-07-28 |
| RS54736B1 (sr) | 2016-10-31 |
| ES2571793T3 (es) | 2016-05-26 |
| AU2009250149B2 (en) | 2013-05-23 |
| IL209198A (en) | 2013-11-28 |
| ZA201009160B (en) | 2011-10-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| MX2010012741A (es) | Proceso para la sintesis de derivados de 3, 6- dihidro- 1, 3 , 5- triazina. | |
| US7563792B2 (en) | Biguanide and dihydrotriazine derivatives | |
| CN105246878B (zh) | 制备4,6‑双(芳氧基)嘧啶衍生物的方法 | |
| TR201802913T4 (tr) | Yeni 4,6-çift ikameli aminopirimidin türevleri. | |
| KR20120098815A (ko) | 메틸-｛4,6-디아미노-2-［1-(2-플루오로벤질)-1ｈ-피라졸로［3,4-ｂ］피리디노-3-일］피리미디노-5-일｝카르바메이트의 제조 방법 및 제약 물질로서의 그의 사용을 위한 그의 정제 | |
| US10934289B2 (en) | Solid state forms of venetoclax and its process for the preparation there of | |
| CA2705682C (en) | Process for the synthesis of 3,6-dihydro-1,3,5-triazine derivatives | |
| NZ331735A (en) | Carboxylic acid derivatives as endothelin receptor antagonists | |
| CN103492360A (zh) | 由酯合成羟烷基酰胺 | |
| Correia et al. | Synthesis and in vitro activity of 6-amino-2, 9-diarylpurines for Mycobacterium tuberculosis | |
| AU2019229971B2 (en) | Process and intermidiates for the preparation of certain mesoionic pesticides | |
| EP1982983B1 (en) | Improved process for producing moxonidine | |
| GB2626517A (en) | Method for preparing ruxolitinib intermediate | |
| JP4636525B2 (ja) | トランス−４−アミノ−１−シクロヘキサンカルボン酸エチルエステルの塩およびその製造方法 | |
| Gosavi et al. | Design, Synthesis, Characterization and Biological Evaluation of Novel Thiazolidine-4-Ones | |
| US20100010233A1 (en) | Process for preparing imidazolidin-2,4-dione compound and method for acquiring solid state 4,5-dihydroxy-2-imidazolidinone compound | |
| SU1041031A3 (ru) | Способ получени замещенных бензонитрилов | |
| EP1115717B1 (en) | 3-(hydroxymethyl)chromen-4-ones and process for their preparation | |
| Wang et al. | An improved synthesis of reduced 9-arylacridine-1, 8-diones from 3-amino-5, 5-dimethylcyclohex-2-enone, arylaldehydes and 1, 3-dicarbonyl compounds in aqueous medium | |
| PL203260B1 (pl) | Jodowodorki 1-podstawione-2-metylotioimidazoliny i sposób ich otrzymywania |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant or registration |