HRP20110644T1 - Postupak proizvodnje derivata 3, 6-dihidro-l, 3, 5-triazina iz derivata metformina i paraldehida - Google Patents
Postupak proizvodnje derivata 3, 6-dihidro-l, 3, 5-triazina iz derivata metformina i paraldehida Download PDFInfo
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- HRP20110644T1 HRP20110644T1 HR20110644T HRP20110644T HRP20110644T1 HR P20110644 T1 HRP20110644 T1 HR P20110644T1 HR 20110644 T HR20110644 T HR 20110644T HR P20110644 T HRP20110644 T HR P20110644T HR P20110644 T1 HRP20110644 T1 HR P20110644T1
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- 238000000034 method Methods 0.000 title claims abstract 11
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical class C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 title 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 title 1
- 229960003105 metformin Drugs 0.000 title 1
- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical class CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 4
- 125000005843 halogen group Chemical group 0.000 claims abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 235000010290 biphenyl Nutrition 0.000 claims abstract 2
- 239000004305 biphenyl Substances 0.000 claims abstract 2
- 229910052794 bromium Inorganic materials 0.000 claims abstract 2
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 229910052740 iodine Inorganic materials 0.000 claims abstract 2
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 2
- 125000004434 sulfur atom Chemical group 0.000 claims abstract 2
- 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 abstract 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 239000003729 cation exchange resin Substances 0.000 claims 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 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
- A61P3/06—Antihyperlipidemics
-
- 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
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Diabetes (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Obesity (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Cephalosporin Compounds (AREA)
Abstract
Postupak pripreme spojeva formule IgdjeR1, R2 svaki, nezavisno jedan od drugog, predstavljaju H ili A, R3, R4 svaki, nezavisno jedan od drugog, predstavljaju H, A, alkenil s 2-6 C atoma, alkinil s 2-6 C atoma, Ar ili Het, R5 i R6 zajedno također predstavljaju alkilen s 2, 3, 4 ili 5 C atoma, R5, R6 svaki, nezavisno jedan od drugog, predstavljaju H, A, (CH2)nAr, (CH2)mOAr, (CH2)mOA ili (CH2)mOH, R5 i R6 zajedno također predstavljaju alkilen s 2, 3, 4 ili 5 C atoma, gdje se jedna CH2 skupina može zamijeniti s O, NH ili NA i/ili gdje se 1 H atom može zamijeniti s OH, Ar predstavlja fenil, naftil ili bifenil, od kojih je svaki nesupstituiran ili je mono-, di- ili trisupstituiran halogenom, A, OA, OH, COOH, COOA, CN, NH2, NHA, NA2, SO2A i/ili COA, Het predstavlja mono-, bi- ili triciklički zasićeni, nezasićeni ili aromatski heterocikl s 1 do 4 N, O i/ili S atoma, koji može biti nesupstituiran ili je mono-, di- ili trisupstituiran halogenom, A, OH, OA, NH2, (CH2)nAr, NHA, NA2, COOH, COOA i/ili =O (karbonil kisik), A predstavlja nerazgranati ili razgranati alkil s 1-10 C atoma, gdje se 1-7 H atoma može zamijeniti s F, ili ciklički alkil s 3-7 C atoma, halogen predstavlja F, Cl, Br ili I, m predstavlja 1, 2, 3, 4, 5 ili 6, n predstavlja 0, 1 ili 2, i njegovih kiselih-adicijskih soli, koji obuhvaća reakciju spoja formule IIgdjeR1, R2, R3, R4 predstavljaju kako je gore naznačeno, sa spojem formule IIIgdjeR5, R6 predstavljaju kako je gore naznačeno. Patent sadrži još 8 patentnih zahtjeva.
Claims (9)
1. Postupak pripreme spojeva formule I
[image]
gdje
R1, R2 svaki, nezavisno jedan od drugog, predstavljaju H ili A,
R3, R4 svaki, nezavisno jedan od drugog, predstavljaju H, A, alkenil s 2- atoma, alkinil s 2- atoma, Ar ili Het,
R5 i R6 zajedno također predstavljaju alkilen s 2, 3, 4 ili atoma,
R5, R6 svaki, nezavisno jedan od drugog, predstavljaju H, A, (CH2)nAr, (CH2)mOAr, (CH2)mOA ili (CH2)mOH,
R5 i R6 zajedno također predstavljaju alkilen s 2, 3, 4 ili atoma, gdje se jedna CH2 skupina može zamijeniti s O, NH ili NA i/ili gdje se 1 H atom može zamijeniti s OH,
Ar predstavlja fenil, naftil ili bifenil, od kojih je svaki nesupstituiran ili je mono-, di- ili trisupstituiran halogenom,
A, OA, OH, COOH, COOA, CN, NH2, NHA, NA2, SO2A i/ili COA,
Het predstavlja mono-, bi- ili triciklički zasićeni, nezasićeni ili aromatski heterocikl s 1 do 4 N, O i/ili S atoma, koji može biti nesupstituiran ili je mono-, di- ili trisupstituiran halogenom, A, OH, OA, NH2, (CH2)nAr, NHA, NA2, COOH, COOA i/ili =O (karbonil kisik),
A predstavlja nerazgranati ili razgranati alkil s 1- atoma, gdje se 1-7 H atoma može zamijeniti s F, ili ciklički alkil s 3- atoma,
halogen predstavlja F, Cl, Br ili I,
m predstavlja 1, 2, 3, 4, 5 ili 6,
n predstavlja 0, 1 ili 2,
i njegovih kiselih-adicijskih soli,
koji obuhvaća reakciju spoja formule II
[image]
gdje
R1, R2, R3, R4 predstavljaju kako je gore naznačeno,
sa spojem formule III
[image]
gdje
R5, R6 predstavljaju kako je gore naznačeno.
2. Postupak prema zahtjevu 1, gdje se reakcija izvodi u prisutnosti organske ili anorganske kiseline ili kisele kationske izmjenjivačke smole.
3. Postupak prema zahtjevu 1 ili 2, gdje se reakcija izvodi u prisutnosti para-toluensulfonske kiseline ili kisele kationske izmjenjivačke smole.
4. Postupak prema jednom ili više od zahtjeva 1-3, gdje se reakcija izvodi u polarnom otapalu.
5. Postupak prema jednom ili više od zahtjeva 1-4, gdje se reakcija izvodi u izobutanolu.
6. Postupak prema jednom ili više od zahtjeva 1-5 za pripremu spojeva formule I gdje R1, R2 predstavljaju A.
7. Postupak prema jednom ili više od zahtjeva 1-6 za pripremu spojeva formule I gdje R3, R4 predstavljaju H.
8. Postupak prema jednom ili više od zahtjeva 1-7 za pripremu spojeva formule I gdje
R5 predstavlja H,
R6 predstavlja A.
9. Postupak prema jednom ili više od zahtjeva 1-8 za pripremu spojeva formule I gdje
R1, R2 predstavljaju metil,
R3, R4 predstavljaju H,
R5 predstavlja H,
R6 predstavlja metil.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102008007314A DE102008007314A1 (de) | 2008-02-02 | 2008-02-02 | Verfahren zur Herstellung von 3,6-Dihydro-1,3,5-triazinderivaten |
| PCT/EP2009/000212 WO2009095159A1 (de) | 2008-02-02 | 2009-01-15 | Verfahren zur herstellung von 3, 6-dihydro-l, 3, 5-triazinderivaten aus metformin- und paraldehydderivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110644T1 true HRP20110644T1 (hr) | 2011-10-31 |
Family
ID=40459622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20110644T HRP20110644T1 (hr) | 2008-02-02 | 2011-09-07 | Postupak proizvodnje derivata 3, 6-dihidro-l, 3, 5-triazina iz derivata metformina i paraldehida |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US8461331B2 (hr) |
| EP (1) | EP2240456B1 (hr) |
| JP (1) | JP5542066B2 (hr) |
| KR (1) | KR101553568B1 (hr) |
| CN (1) | CN101932566B (hr) |
| AR (1) | AR070329A1 (hr) |
| AT (1) | ATE519752T1 (hr) |
| AU (1) | AU2009210293B2 (hr) |
| BR (1) | BRPI0907052B8 (hr) |
| CA (1) | CA2713236C (hr) |
| CY (1) | CY1111837T1 (hr) |
| DE (1) | DE102008007314A1 (hr) |
| DK (1) | DK2240456T3 (hr) |
| EA (1) | EA017062B1 (hr) |
| ES (1) | ES2368116T3 (hr) |
| HR (1) | HRP20110644T1 (hr) |
| IL (1) | IL206816A (hr) |
| MX (1) | MX2010008282A (hr) |
| PL (1) | PL2240456T3 (hr) |
| PT (1) | PT2240456E (hr) |
| RS (1) | RS51968B (hr) |
| SI (1) | SI2240456T1 (hr) |
| WO (1) | WO2009095159A1 (hr) |
| ZA (1) | ZA201006211B (hr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA022300B1 (ru) | 2010-12-01 | 2015-12-30 | Поксел | Разделение энантиомеров 2-амино-3,6-дигидро-4-диметиламино-6-метил-1,3,5-триазина с использованием винной кислоты |
| KR20200102982A (ko) | 2017-10-02 | 2020-09-01 | 폭셀 | 보존된 박출률을 갖는 심부전의 치료 방법 |
| MX2020013210A (es) | 2018-06-06 | 2021-02-26 | Metavant Sciences Gmbh | Metodos de tratamiento de sujetos que padecen diabetes con enfermedad renal cronica. |
| CA3103324A1 (en) | 2018-06-14 | 2019-12-19 | Poxel | Film-coated tablet comprising a triazine derivative for use in the treatment of diabetes |
| CN109655544B (zh) * | 2018-12-25 | 2022-08-12 | 广东华南药业集团有限公司 | 一种盐酸二甲双胍及其制剂的质量控制方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1537604A (fr) | 1966-09-26 | 1968-08-23 | Sandoz Sa | Procédé de préparation de biguanides |
| GB1250531A (hr) * | 1969-01-01 | 1971-10-20 | ||
| DE2117015A1 (de) | 1971-04-02 | 1972-10-26 | Schering Ag | 1,2-Biguanide |
| SU458538A1 (ru) * | 1973-06-14 | 1975-01-30 | Уфимский Нефтяной Институт | Способ совместного получени 1,3диеновых углеводородов и гексаметилентетрамина |
| JPH061779A (ja) * | 1992-02-06 | 1994-01-11 | Wakamoto Pharmaceut Co Ltd | ベンズオキサジノン誘導体 |
| US5767294A (en) * | 1993-02-17 | 1998-06-16 | Hoechst Celanese Corporation | Process for the production of trioxane from formaldehyde |
| US5627282A (en) * | 1996-01-03 | 1997-05-06 | Yukong Limited | Process for the preparation of optically pure 1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid and its derivatives |
| FR2804113B1 (fr) * | 2000-01-26 | 2004-06-18 | Lipha | Derives animes de dihydro-1,3,5-triazine et leurs applications en therapeutique |
| CN100551916C (zh) * | 2002-12-17 | 2009-10-21 | 浜理药品工业株式会社 | 新的2,4-二氨基-1,3,5-三嗪衍生物 |
| JP4391422B2 (ja) | 2002-12-17 | 2009-12-24 | 浜理薬品工業株式会社 | 新規２，４−ジアミノ−１，３，５−トリアジン誘導体 |
| 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 |
| TWI410413B (zh) * | 2006-04-26 | 2013-10-01 | Sumitomo Seika Chemicals | Preparation method of methylene disulfonate compound |
-
2008
- 2008-02-02 DE DE102008007314A patent/DE102008007314A1/de not_active Withdrawn
-
2009
- 2009-01-15 EP EP09705420A patent/EP2240456B1/de active Active
- 2009-01-15 BR BRPI0907052A patent/BRPI0907052B8/pt not_active IP Right Cessation
- 2009-01-15 US US12/735,608 patent/US8461331B2/en active Active
- 2009-01-15 CA CA2713236A patent/CA2713236C/en active Active
- 2009-01-15 SI SI200930069T patent/SI2240456T1/sl unknown
- 2009-01-15 PL PL09705420T patent/PL2240456T3/pl unknown
- 2009-01-15 EA EA201001252A patent/EA017062B1/ru not_active IP Right Cessation
- 2009-01-15 AU AU2009210293A patent/AU2009210293B2/en not_active Ceased
- 2009-01-15 WO PCT/EP2009/000212 patent/WO2009095159A1/de active Application Filing
- 2009-01-15 MX MX2010008282A patent/MX2010008282A/es active IP Right Grant
- 2009-01-15 ES ES09705420T patent/ES2368116T3/es active Active
- 2009-01-15 PT PT09705420T patent/PT2240456E/pt unknown
- 2009-01-15 RS RS20110409A patent/RS51968B/en unknown
- 2009-01-15 JP JP2010544612A patent/JP5542066B2/ja active Active
- 2009-01-15 AT AT09705420T patent/ATE519752T1/de active
- 2009-01-15 CN CN2009801039472A patent/CN101932566B/zh active Active
- 2009-01-15 DK DK09705420.9T patent/DK2240456T3/da active
- 2009-01-15 KR KR1020107018199A patent/KR101553568B1/ko active IP Right Grant
- 2009-01-30 AR ARP090100299A patent/AR070329A1/es unknown
-
2010
- 2010-07-05 IL IL206816A patent/IL206816A/en active IP Right Grant
- 2010-08-31 ZA ZA2010/06211A patent/ZA201006211B/en unknown
-
2011
- 2011-09-07 HR HR20110644T patent/HRP20110644T1/hr unknown
- 2011-09-13 CY CY20111100879T patent/CY1111837T1/el unknown
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