CA2725011A1 - Process for the synthesis of 3,6-dihydro-1,3,5-triazine derivatives - Google Patents
Process for the synthesis of 3,6-dihydro-1,3,5-triazine derivatives Download PDFInfo
- Publication number
- CA2725011A1 CA2725011A1 CA2725011A CA2725011A CA2725011A1 CA 2725011 A1 CA2725011 A1 CA 2725011A1 CA 2725011 A CA2725011 A CA 2725011A CA 2725011 A CA2725011 A CA 2725011A CA 2725011 A1 CA2725011 A1 CA 2725011A1
- Authority
- CA
- Canada
- Prior art keywords
- process according
- formula
- compound
- base
- butanol
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 22
- 230000015572 biosynthetic process Effects 0.000 title abstract description 10
- 238000003786 synthesis reaction Methods 0.000 title abstract description 10
- 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 25
- 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 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 238000002360 preparation method Methods 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
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 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 6
- 239000000203 mixture 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 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
- 235000015320 potassium carbonate Nutrition 0.000 claims description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 4
- 235000017550 sodium carbonate Nutrition 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 2
- 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
- 208000031773 Insulin resistance syndrome Diseases 0.000 abstract description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 208000035475 disorder Diseases 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 3
- 239000012453 solvate Substances 0.000 description 3
- 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 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-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
- 229940002612 prodrug Drugs 0.000 description 2
- 239000000651 prodrug Substances 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 group C\[N+](CC([O-])=O)=C1\NCN=C(N)N1 VXMDOKODOQETRU-UHFFFAOYSA-N 0.000 description 1
- -1 3,6-Dihydro-1,3,5-Triazine Derivatives 3,6-Dihydro-1,3,5-triazine derivatives Chemical class 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
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 102000015636 Oligopeptides Human genes 0.000 description 1
- 108010038807 Oligopeptides Proteins 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
- LFVVNPBBFUSSHL-UHFFFAOYSA-N alexidine Chemical class CCCCC(CC)CNC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NCC(CC)CCCC LFVVNPBBFUSSHL-UHFFFAOYSA-N 0.000 description 1
- 229950010221 alexidine Drugs 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
- 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08009483.2 | 2008-05-23 | ||
| 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 |
|---|---|
| CA2725011A1 true CA2725011A1 (en) | 2009-11-26 |
Family
ID=40791625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2725011A Abandoned CA2725011A1 (en) | 2008-05-23 | 2009-04-24 | Process for the synthesis of 3,6-dihydro-1,3,5-triazine derivatives |
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 |
| MX2010012741A (es) | 2010-12-21 |
| 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 |
| 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 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20140305 |
|
| FZDE | Discontinued |
Effective date: 20170206 |