HRP20170390T1 - Postupak za pripremu derivata feniloksimetil-nitro-imidazola i njihovo korištenje - Google Patents
Postupak za pripremu derivata feniloksimetil-nitro-imidazola i njihovo korištenje Download PDFInfo
- Publication number
- HRP20170390T1 HRP20170390T1 HRP20170390TT HRP20170390T HRP20170390T1 HR P20170390 T1 HRP20170390 T1 HR P20170390T1 HR P20170390T T HRP20170390T T HR P20170390TT HR P20170390 T HRP20170390 T HR P20170390T HR P20170390 T1 HRP20170390 T1 HR P20170390T1
- Authority
- HR
- Croatia
- Prior art keywords
- formula
- compound
- organic solvent
- reaction mixture
- nitro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 9
- PQWRORAEWZRLNZ-UHFFFAOYSA-N 2-nitro-5-(phenoxymethyl)-1h-imidazole Chemical class N1C([N+](=O)[O-])=NC=C1COC1=CC=CC=C1 PQWRORAEWZRLNZ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 5
- 239000003960 organic solvent Substances 0.000 claims 5
- 239000011541 reaction mixture Substances 0.000 claims 5
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- 239000012429 reaction media Substances 0.000 claims 3
- JSAQDPJIVQMBAY-UHFFFAOYSA-N (1-methyl-5-nitroimidazol-2-yl)methanol Chemical compound CN1C(CO)=NC=C1[N+]([O-])=O JSAQDPJIVQMBAY-UHFFFAOYSA-N 0.000 claims 2
- QASBCTGZKABPKX-UHFFFAOYSA-N 4-(methylsulfanyl)phenol Chemical compound CSC1=CC=C(O)C=C1 QASBCTGZKABPKX-UHFFFAOYSA-N 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims 2
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical group OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims 2
- 238000012544 monitoring process Methods 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 238000006471 dimerization reaction Methods 0.000 claims 1
- MIWWSGDADVMLTG-UHFFFAOYSA-N fexinidazole Chemical compound C1=CC(SC)=CC=C1OCC1=NC=C([N+]([O-])=O)N1C MIWWSGDADVMLTG-UHFFFAOYSA-N 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000012038 nucleophile Substances 0.000 claims 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims 1
- 230000021962 pH elevation Effects 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 230000000750 progressive effect Effects 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 229930000044 secondary metabolite Natural products 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
- C07D233/94—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to other ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Claims (8)
1. Postupak za pripremanje 1-metil-2-(4-metilmerkapto-feniloksimetil)-5-nitro-imidazola koji ima formulu
[image]
naznačen time da sadrži korake
a) reakciju 1-metil-2-hidroksimetil-5-nitro-imidazola s metansulfonil kloridom u prisutnosti suspenzije praškastog alkalijskog karbonata u bezvodnom organskom otapalu prikladnom za provedbu reakcija supstitucije s nukleofilom uz praćenje reakcijskih uvjeta na takav način da se dobije manje od 3 postotnog područja svakog od sljedećih sekundarnih spojeva formule
[image]
b) dodavanje u dobiveni reakcijski medij otopine 4-metilmerkapto-fenola u organskom otapalu iz koraka a), uz praćenje reakcijskih uvjeta na takav način da se izbjegne dimerizacija spoja I u spoj s formulom
[image]
c) odvajanje spoja formule I iz reakcijske smjese u obliku njegove hidrokloridne soli i
d) pretvaranje navedene hidrokloridne soli u spoj s formulom I, te proizvoljno, pročišćavanje potonje.
2. Postupak prema zahtjevu 1 naznačen time da organsko otapalo koje je prikladno za provedbu reakcija nukleofilne supstitucije je polarno neprotonsko organsko otapalo.
3. Postupak prema zahtjevu 2 naznačen time da polarno neprotonsko organsko otapalo je alifatski keton, naročito C3 do C5 alifatski keton i poželjno aceton, ili acetonitril.
4. Postupak prema bilo kojem od zahtjeva 1 do 3 naznačen time da praškasti alkalijski karbonat je kalijev karbonat.
5. Postupak prema bilo kojem od zahtjeva 1 do 4 naznačen time da sadrži progresivno dodavanje metansulfonil klorida, u obliku otopine u istom otapalu kao što je navedeno u koraku a) u 1-metil-2-hidroksimetil-5-nitro-imidazol uz održavanje reakcijskog medija na temperaturi koja ne prelazi 20° C.
6. Postupak prema bilo kojem od zahtjeva 1 do 5 naznačen time da sadrži dodavanje 4-metil-merkapto-fenola, u obliku otopine u istom otapalu kao što je navedeno u koraku a), u reakcijsku smjesu nastalu u koraku a) uz održavanje reakcijskog medija na temperaturi koja ne prelazi 25° C i nakon toga zagrijavanje nastale reakcijske smjese do 40° C.
7. Postupak prema bilo kojem od zahtjeva 1 do 6 naznačen time da sadrži dodavanje predgrijane vode u reakcijsku smjesu nastalu u koraku b) prije pretvaranja spoja s formulom I u njegovu hidrokloridnu sol prema koraku c).
8. Postupak prema bilo kojem od zahtjeva 1 do 7 naznačen time da sadrži filtriranje navedenog hidroklorida iz reakcijske smjese nastale iz koraka c) i zatim podvrgavanje navedene soli hidroklorida alkalinizaciji pomoću amonijaka u vodenom organskom mediju.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12790895.2A EP2922822B1 (en) | 2012-11-22 | 2012-11-22 | Method for preparing phenyloxymethyl-nitro-imidazole derivatives and use of same |
| PCT/EP2012/073321 WO2014079497A1 (en) | 2012-11-22 | 2012-11-22 | Method for preparing phenyloxymethyl-nitro-imidazole derivatives and use of same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20170390T1 true HRP20170390T1 (hr) | 2017-05-05 |
Family
ID=47222105
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20170390TT HRP20170390T1 (hr) | 2012-11-22 | 2017-03-08 | Postupak za pripremu derivata feniloksimetil-nitro-imidazola i njihovo korištenje |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US9758488B2 (hr) |
| EP (1) | EP2922822B1 (hr) |
| CN (1) | CN104797562B (hr) |
| AP (1) | AP3759A (hr) |
| BR (1) | BR112015011446A2 (hr) |
| CA (1) | CA2892334C (hr) |
| CR (1) | CR20150286A (hr) |
| CY (1) | CY1118983T1 (hr) |
| EC (1) | ECSP15025960A (hr) |
| ES (1) | ES2618800T3 (hr) |
| HR (1) | HRP20170390T1 (hr) |
| HU (1) | HUE032160T2 (hr) |
| IL (1) | IL238934A (hr) |
| MX (1) | MX365587B (hr) |
| PL (1) | PL2922822T3 (hr) |
| SG (1) | SG11201504047TA (hr) |
| SI (1) | SI2922822T1 (hr) |
| WO (1) | WO2014079497A1 (hr) |
| ZA (1) | ZA201503063B (hr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2673910C2 (ru) * | 2012-11-21 | 2018-12-03 | Ипсен Байоинновейшн Лимитед | Способ производства протеолитически процессированного полипептида |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3299090A (en) | 1964-03-27 | 1967-01-17 | Merck & Co Inc | Nitroimidazoles |
| EG11928A (en) * | 1974-12-16 | 1979-03-31 | Hoechst Ag | Process for preparing of 1-alkyl-2-(phenoxy-methyl)-5-nitro-imidazoles |
| DE2459395C2 (de) * | 1974-12-16 | 1982-03-04 | Hoechst Ag, 6000 Frankfurt | 1-Alkyl-2-(phenoxymethyl)-5-nitro-imidazole, Verfahren zu ihrer Herstellung und pharmazeutische Mittel |
| EG12284A (en) | 1975-07-12 | 1978-09-30 | Hoechst Ag | Process for the preparation of 1-methyl-2-(phenyl 6 oxymethyl)-5-nitro-imidazoles |
| WO2005040127A1 (en) * | 2003-10-27 | 2005-05-06 | Lg Life Sciences Ltd. | Novel compounds as agonist for ppar gamma and ppar alpha, method for preparation of the same, and pharmaceutical composition containing the same |
| WO2011151651A1 (en) * | 2010-06-03 | 2011-12-08 | Arrow Therapeutics Limited | Benzodiazepine compounds useful for the treatment of hepatitis c |
-
2012
- 2012-11-22 BR BR112015011446A patent/BR112015011446A2/pt not_active Application Discontinuation
- 2012-11-22 PL PL12790895T patent/PL2922822T3/pl unknown
- 2012-11-22 SI SI201230891A patent/SI2922822T1/sl unknown
- 2012-11-22 EP EP12790895.2A patent/EP2922822B1/en active Active
- 2012-11-22 MX MX2015006519A patent/MX365587B/es active IP Right Grant
- 2012-11-22 US US14/647,017 patent/US9758488B2/en active Active
- 2012-11-22 CN CN201280077219.0A patent/CN104797562B/zh not_active Expired - Fee Related
- 2012-11-22 WO PCT/EP2012/073321 patent/WO2014079497A1/en active Application Filing
- 2012-11-22 SG SG11201504047TA patent/SG11201504047TA/en unknown
- 2012-11-22 HU HUE12790895A patent/HUE032160T2/en unknown
- 2012-11-22 ES ES12790895.2T patent/ES2618800T3/es active Active
- 2012-11-22 AP AP2015008475A patent/AP3759A/en active
- 2012-11-22 CA CA2892334A patent/CA2892334C/en not_active Expired - Fee Related
-
2015
- 2015-05-04 ZA ZA2015/03063A patent/ZA201503063B/en unknown
- 2015-05-20 IL IL238934A patent/IL238934A/en active IP Right Grant
- 2015-05-28 CR CR20150286A patent/CR20150286A/es unknown
- 2015-06-17 EC ECIEPI201525960A patent/ECSP15025960A/es unknown
-
2017
- 2017-03-08 HR HRP20170390TT patent/HRP20170390T1/hr unknown
- 2017-03-28 CY CY20171100384T patent/CY1118983T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL2922822T3 (pl) | 2017-06-30 |
| CA2892334A1 (en) | 2014-05-30 |
| ECSP15025960A (es) | 2016-01-29 |
| WO2014079497A1 (en) | 2014-05-30 |
| IL238934A0 (en) | 2015-07-30 |
| EP2922822A1 (en) | 2015-09-30 |
| AP3759A (en) | 2016-07-31 |
| CR20150286A (es) | 2015-10-19 |
| MX2015006519A (es) | 2015-07-21 |
| SI2922822T1 (sl) | 2017-04-26 |
| SG11201504047TA (en) | 2015-06-29 |
| HUE032160T2 (en) | 2017-09-28 |
| CY1118983T1 (el) | 2018-01-10 |
| AP2015008475A0 (en) | 2015-05-31 |
| US20150291536A1 (en) | 2015-10-15 |
| CA2892334C (en) | 2019-10-08 |
| CN104797562B (zh) | 2017-10-03 |
| ZA201503063B (en) | 2016-01-27 |
| IL238934A (en) | 2017-12-31 |
| US9758488B2 (en) | 2017-09-12 |
| ES2618800T3 (es) | 2017-06-22 |
| EP2922822B1 (en) | 2016-12-28 |
| BR112015011446A2 (pt) | 2017-07-11 |
| CN104797562A (zh) | 2015-07-22 |
| MX365587B (es) | 2019-06-07 |
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