HRP20171166T1 - Postupak za pripravu intermedijera pirimidina - Google Patents
Postupak za pripravu intermedijera pirimidina Download PDFInfo
- Publication number
- HRP20171166T1 HRP20171166T1 HRP20171166TT HRP20171166T HRP20171166T1 HR P20171166 T1 HRP20171166 T1 HR P20171166T1 HR P20171166T T HRP20171166T T HR P20171166TT HR P20171166 T HRP20171166 T HR P20171166T HR P20171166 T1 HRP20171166 T1 HR P20171166T1
- Authority
- HR
- Croatia
- Prior art keywords
- compound
- formula
- ethylene glycol
- reaction
- mixture
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 41
- 150000001875 compounds Chemical class 0.000 claims 26
- 229940093476 ethylene glycol Drugs 0.000 claims 13
- 238000000034 method Methods 0.000 claims 13
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 7
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 7
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 6
- 239000012074 organic phase Substances 0.000 claims 5
- 239000003513 alkali Substances 0.000 claims 4
- 239000008346 aqueous phase Substances 0.000 claims 3
- 238000000622 liquid--liquid extraction Methods 0.000 claims 3
- 238000000638 solvent extraction Methods 0.000 claims 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- 238000002425 crystallisation Methods 0.000 claims 2
- 230000008025 crystallization Effects 0.000 claims 2
- 230000008020 evaporation Effects 0.000 claims 2
- 238000001704 evaporation Methods 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 239000006104 solid solution Substances 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000012071 phase Substances 0.000 claims 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/30—Halogen atoms or nitro radicals
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Detergent Compositions (AREA)
- Magnetic Heads (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Manufacturing Cores, Coils, And Magnets (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Extraction Or Liquid Replacement (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Saccharide Compounds (AREA)
Claims (15)
1. Postupak za proizvodnju spoja sljedeće formule I-2:
[image]
I-2
pri čemu navedeni postupak obuhvaća reakciju spoja sljedeće formule I1:
[image]
I-1
gdje G1 predstavlja halogen, ili soli navedenog spoja,
s etilen-glikolom u prisutnosti lužine, naznačen time, da se nakon što se dobije spoj formule I2, provodi ekstrakcija tekućina-tekućina, te se pritom upotrebljava metil-izobutil-keton za ekstrakciju spoja formule I2 iz vodene faze koja sadrži produkte reakcije spoja formule I1 s etilen-glikolom.
2. Postupak prema zahtjevu 1, naznačen time, da je spoj formule I-1 takav, da G1 predstavlja klor.
3. Postupak prema zahtjevu 1 ili 2, naznačen time, da lužina je kalijev tert-butilat.
4. Postupak prema bilo kojem od zahtjeva 1 do 3, naznačen time, da se upotrebljava od 20 do 50 ekvivalenata od etilen-glikola po ekvivalentu spoja formule I-1.
5. Postupak prema bilo kojem od zahtjeva 1 do 4, naznačen time, da pH-vrijednost vodene faze iz koje se ekstrahira spoj formule I2, iznosi od 3 do 5.
6. Postupak prema bilo kojem od zahtjeva 1 do 5, naznačen time, da se reakcija spoja formule I1 s etilen-glikolom izvodi u metil-izobutil-ketonu.
7. Postupak prema zahtjevu 6, naznačen time, da volumen metil-izobutil-ketona koji se koristi za izvođenje reakcije spoja formule I1 s etilen-glikolom, iznosi od 3 do 7 puta vrijednosti volumena etilen-glikola.
8. Postupak prema zahtjevu 6 ili 7, naznačen time, da se upotrebljava od 5 do 20 ekvivalenata etilen-glikola po ekvivalentu spoja formule I-1.
9. Postupak prema bilo kojem od zahtjeva 1 do 8, naznačen time, da se mješavina vodene faze i organske faze zagrijava na temperaturu od 35 do 60°C, prije nego što se faze razdvoje.
10. Postupak prema bilo kojem od zahtjeva 1 do 9, naznačen time, da se spoj formule I2 koji se dobiva nakon reakcije spoja formule I1 s etilen-glikolom i ekstrakcije tekućina-tekućina, kristalizira pomoću djelomične evaporacije metil-izobutil-ketona iz sakupljene organske faze, pri čemu se dodaje nepolarno aprotonsko organsko otapalo ili smjesa nepolarnih aprotonskih organskih otapala u navedenu organsku fazu, a tako dobivena smjesa se zagrijava sve dok se ne dobije potpuno kruta otopina, te se potom smjesa rashlađuje kako bi se dobila kristalizacija spoja formule I2.
11. Postupak prema zahtjevu 10, naznačen time, da se spoj formule I2 koji se dobiva nakon reakcije spoja formule I1 s etilen-glikolom i ekstrakcije tekućina-tekućina, kristalizira pomoću djelomične evaporacije metil-izobutil-ketona iz sakupljene organske faze, zatim se dodaje heptan u navedenu organsku fazu, a tako dobivena smjesa se zagrijava sve dok se ne dobije potpuno kruta otopina, te se potom smjesa rashlađuje kako bi se dobila kristalizacija spoja formule I2.
12. Postupak prema bilo kojem od zahtjeva 1 do 11, naznačen time, da udio ostatka etilen-glikola u dobivenom spoju formule I2, iznosi ispod 500 ppm.
13. Uporaba metil-izo-butil-ketona, naznačena time, da je za odstranjivanje etilen-glikola iz spoja formule I2 kako je definirano u zahtjevu 1, kada se navedeni spoj dobiva pomoću reakcije spoja formule I1 s etilen-glikolom u prisutnosti lužine, kako je definirano u zahtjevu 1.
14. Uporaba metil-izo-butil-ketona, naznačena time, da je za odstranjivanje etilen-glikola iz spoja formule I2 kako je definirano u zahtjevu 1, kada se navedeni spoj dobiva pomoću reakcije spoja formule I1 s etilen-glikolom u prisutnosti lužine, kako je definirano u zahtjevu 2.
15. Uporaba prema zahtjevu 13 ili 14, naznačena time, da udio ostatka etilen-glikola u spoju formule I2 koji se dobiva nakon navedene uporabe, iznosi ispod 500 ppm.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13176374 | 2013-07-12 | ||
| EP14737272.6A EP3019479B1 (en) | 2013-07-12 | 2014-07-11 | Process for preparing a pyrimidine intermediate |
| PCT/EP2014/064904 WO2015004265A1 (en) | 2013-07-12 | 2014-07-11 | Process for preparing a pyrimidine intermediate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20171166T1 true HRP20171166T1 (hr) | 2017-10-06 |
Family
ID=48790244
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20171166TT HRP20171166T1 (hr) | 2013-07-12 | 2017-07-31 | Postupak za pripravu intermedijera pirimidina |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US9556125B2 (hr) |
| EP (1) | EP3019479B1 (hr) |
| JP (1) | JP6375374B2 (hr) |
| KR (1) | KR102305298B1 (hr) |
| CN (1) | CN105636940B (hr) |
| AR (1) | AR096865A1 (hr) |
| CA (1) | CA2915736C (hr) |
| DK (1) | DK3019479T3 (hr) |
| ES (1) | ES2636937T3 (hr) |
| HR (1) | HRP20171166T1 (hr) |
| HU (1) | HUE034071T2 (hr) |
| IL (1) | IL243477B (hr) |
| MX (1) | MX360768B (hr) |
| PL (1) | PL3019479T3 (hr) |
| PT (1) | PT3019479T (hr) |
| TW (1) | TWI643848B (hr) |
| WO (1) | WO2015004265A1 (hr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA201605808B (en) | 2015-08-26 | 2017-08-30 | Cipla Ltd | Process for preparing an endothelin receptor antagonist |
| CN105461638A (zh) * | 2015-12-10 | 2016-04-06 | 合肥久诺医药科技有限公司 | 一种马西替坦晶型及其制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7094781B2 (en) * | 2000-12-18 | 2006-08-22 | Actelion Pharmaceuticals Ltd. | Sulfamides and their use as endothelin receptor antagonists |
| CN103724281A (zh) * | 2013-12-03 | 2014-04-16 | 镇江圣安医药有限公司 | N-[5-（4-溴苯基）-6-[2-[（5-溴-2-嘧啶基）氧基]乙氧基]-4-嘧啶基]-n′-丙基磺酰胺的新型衍生物及其应用 |
| CN103819411A (zh) * | 2014-03-14 | 2014-05-28 | 成都克莱蒙医药科技有限公司 | 一种马西替坦中间体新的制备方法 |
-
2014
- 2014-07-10 AR ARP140102549A patent/AR096865A1/es active IP Right Grant
- 2014-07-11 MX MX2016000386A patent/MX360768B/es active IP Right Grant
- 2014-07-11 PL PL14737272T patent/PL3019479T3/pl unknown
- 2014-07-11 KR KR1020167003201A patent/KR102305298B1/ko active IP Right Grant
- 2014-07-11 TW TW103124052A patent/TWI643848B/zh not_active IP Right Cessation
- 2014-07-11 DK DK14737272.6T patent/DK3019479T3/en active
- 2014-07-11 ES ES14737272.6T patent/ES2636937T3/es active Active
- 2014-07-11 EP EP14737272.6A patent/EP3019479B1/en active Active
- 2014-07-11 CN CN201480039832.2A patent/CN105636940B/zh active Active
- 2014-07-11 CA CA2915736A patent/CA2915736C/en active Active
- 2014-07-11 PT PT147372726T patent/PT3019479T/pt unknown
- 2014-07-11 HU HUE14737272A patent/HUE034071T2/en unknown
- 2014-07-11 WO PCT/EP2014/064904 patent/WO2015004265A1/en active Application Filing
- 2014-07-11 JP JP2016524837A patent/JP6375374B2/ja active Active
- 2014-07-11 US US14/904,657 patent/US9556125B2/en active Active
-
2016
- 2016-01-06 IL IL243477A patent/IL243477B/en active IP Right Grant
-
2017
- 2017-07-31 HR HRP20171166TT patent/HRP20171166T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX360768B (es) | 2018-11-15 |
| KR102305298B1 (ko) | 2021-09-27 |
| CA2915736C (en) | 2021-07-27 |
| JP6375374B2 (ja) | 2018-08-15 |
| AR096865A1 (es) | 2016-02-03 |
| EP3019479B1 (en) | 2017-05-10 |
| US20160145215A1 (en) | 2016-05-26 |
| MX2016000386A (es) | 2016-04-29 |
| EP3019479A1 (en) | 2016-05-18 |
| JP2016525094A (ja) | 2016-08-22 |
| PT3019479T (pt) | 2017-08-11 |
| US9556125B2 (en) | 2017-01-31 |
| PL3019479T3 (pl) | 2017-10-31 |
| HUE034071T2 (en) | 2018-01-29 |
| KR20160030972A (ko) | 2016-03-21 |
| TW201536759A (zh) | 2015-10-01 |
| CN105636940A (zh) | 2016-06-01 |
| CA2915736A1 (en) | 2015-01-15 |
| IL243477B (en) | 2018-06-28 |
| TWI643848B (zh) | 2018-12-11 |
| WO2015004265A1 (en) | 2015-01-15 |
| DK3019479T3 (en) | 2017-07-17 |
| ES2636937T3 (es) | 2017-10-10 |
| CN105636940B (zh) | 2018-02-27 |
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