HRP20150295T1 - Postupak za pripravu 4-{4-[({[4-kloro-3-(trifluorometil)fenil]amino}karbonil)amino]fenioksi}n-metilpiridin-2-karboksamida - Google Patents
Postupak za pripravu 4-{4-[({[4-kloro-3-(trifluorometil)fenil]amino}karbonil)amino]fenioksi}n-metilpiridin-2-karboksamida Download PDFInfo
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- HRP20150295T1 HRP20150295T1 HRP20150295TT HRP20150295T HRP20150295T1 HR P20150295 T1 HRP20150295 T1 HR P20150295T1 HR P20150295T T HRP20150295T T HR P20150295TT HR P20150295 T HRP20150295 T HR P20150295T HR P20150295 T1 HRP20150295 T1 HR P20150295T1
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- 238000000034 method Methods 0.000 title claims 14
- 238000002360 preparation method Methods 0.000 title claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title 1
- -1 {[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 40
- 238000006243 chemical reaction Methods 0.000 claims 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 12
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 8
- NBJZEUQTGLSUOB-UHFFFAOYSA-N 1-chloro-4-isocyanato-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(N=C=O)=CC=C1Cl NBJZEUQTGLSUOB-UHFFFAOYSA-N 0.000 claims 7
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- 239000003960 organic solvent Substances 0.000 claims 6
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 238000002156 mixing Methods 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 239000002798 polar solvent Substances 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 2
- 150000005323 carbonate salts Chemical class 0.000 claims 2
- 239000012948 isocyanate Substances 0.000 claims 2
- 150000002513 isocyanates Chemical class 0.000 claims 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Developing Agents For Electrophotography (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Plant Substances (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Claims (13)
1. Postupak za pripravu spoja s formulom (I)
[image]
naznačen time da sadrži, u prvom koraku, reakciju spoja s formulom (V)
[image]
s 4-kloro-3-trifluorometilfenil izocijanatom u nekloriranom organskom otapalu, inertnom prema izocijanatima, uz početno držanje spoja s formulom (V) na temperaturi od 20°C do 60°C i miješanjem s 4-kloro-3-trifluorometilfenil izocijanatom na takav način da temperatura reakcije ne prelazi 70°C da se dobije spoj s formulom (II)
[image]
te, u drugom koraku, miješanje spoja s formulom (II) s p-toluensulfonskom kiselinom u polarnom otapalu, na temperaturi reakcije od 40°C do temperature refluksa otapala koje se koristi.
2. Postupak za pripravu spoja s formulom (II)
[image]
naznačen time da sadrži reakciju spoja s formulom (V)
[image]
s 4-kloro-3-trifluorometilfenil izocijanatom u nekloriranom organskom otapalu, inertnom prema izocijanatima, uz početno držanje spoja s formulom (V) na temperaturi od 20°C do 60°C i miješanjem s 4-kloro-3-trifluorometilfenil izocijanatom na takav način da temperatura reakcije ne prelazi 70°C da se dobije spoj s formulom (II).
3. Postupak prema bilo kojem zahtjevu 1 do 2, naznačen time da je neklorirano organsko otapalo odabrano is skupine koja sadrži tetrahidrofuran, etil acetat, dioksan, metil tert-butil eter, dimetoksietan ili njihove mješavine.
4. Postupak prema bilo kojem zahtjevu 1 do 2, naznačen time da je neklorirano organsko otapalo etil acetat.
5. Postupak prema bilo kojem zahtjevu 1, 3, 4, naznačen time da je polarno otapalo odabrano is skupine koja sadrži organska otapala koja sadrže najmanje jednu hidroksilnu skupinu, tetrahidrofuran, etil acetat ili njihove mješavine.
6. Postupak prema bilo kojem zahtjevu 1, 3, 4, naznačen time da je polarno otapalo odabrano is skupine koja sadrži organska otapala koja sadrže metanol, etanol, n-propanol, izopropanol, n-butanol, sek-butanol, n-pentanol, glicerol, etilen glikol, dioksan, dimetoksietan, tetrahidrofuran, etil acetat ili njihove mješavine.
7. Postupak prema bilo kojem zahtjevu od 1 do 6, naznačen time da se spoj s formulom (V) priprema reakcijom spoja s formulom (IV)
[image]
s 4-aminofenolom bez dodavanja soli karbonata.
8. Postupak prema bilo kojem zahtjevu od 1 do 7, naznačen time da, kod priprave spoja s formulom (V), najprije taloži kisela sol spoja s formulom (V), izolira, ponovno otapa, miješa s bazom, te se zatim kristalizacijom izolira spoj s formulom (V).
9. Postupak prema zahtjevu 7 ili 8, naznačen time da se spoj s formulom (IV) priprema reakcijom spoja s formulom (III)
[image]
s vodenom otopinom metilamina.
10. Postupak prema zahtjevu 9, naznačen time da se spoj s formulom (III) pripravlja upotrebom otapala inertnog prema tionil kloridu, dodavanjem tionil klorida u 2-pikolinsku kiselinu i bez upotrebe dimetilformamida.
11. Postupak prema bilo kojem zahtjevu od 1 do 10 za pripravu spoja s formulom (I) ili spoja s formulom (II) pomoću
a) reakcije spoja s formulom (IV) s 4-aminofenolom bez dodavanja soli karbonata da se dobije spoj s formulom (V),
b) reakcije spoja s formulom (V) s 4-kloro-3-trifluorometil-fenil izocijanatom da se dobije spoj s formulom (II).
12. Postupak prema bilo kojem zahtjevu od 1 do 10 za pripravu spoja s formulom (I) ili spoja s formulom (II) pomoću
a) reakcije spoja s formulom (III) s vodenom otopinom metilamina da se dobije spoj s formulom (IV),
b) reakcije spoja s formulom (IV) s 4-aminofenolom da se dobije spoj s formulom (V),
c) reakcije spoja s formulom (V) s 4-kloro-3-trifluorometil-fenil izocijanatom da se dobije spoj s formulom (II).
13. Postupak prema bilo kojem zahtjevu od 1 do 10 za pripravu spoja s formulom (I) ili spoja s formulom (II) pomoću
a) dodavanja tionil klorida u 2-pikolinsku kiselinu u otapalu koje je inertno prema tionil kloridu bez upotrebe dimetilformamida uz reakciju da se dobije spoj s formulom (III),
b) reakcije spoja s formulom (III) s metilaminom da se dobije spoj s formulom (IV),
c) reakcije spoja s formulom (IV) s 4-aminofenolom da se dobije spoj s formulom (V),
d) reakcijom spoja s formulom (V) s 4-kloro-3-trifluorometil-fenil izocijanatom da se dobije spoj s formulom (II).
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04023131 | 2004-09-29 | ||
| PCT/EP2005/010118 WO2006034796A1 (en) | 2004-09-29 | 2005-09-20 | Process for the preparation of 4-{4-[({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenoxy}-n-methylpyridine-2-carboxamide |
| EP05794785.5A EP1797037B1 (en) | 2004-09-29 | 2005-09-20 | Process for the preparation of 4-{4-[({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenyoxy}n-methylpyridine-2-carboxamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20150295T1 true HRP20150295T1 (hr) | 2015-05-22 |
Family
ID=35457568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20150295TT HRP20150295T1 (hr) | 2004-09-29 | 2015-03-16 | Postupak za pripravu 4-{4-[({[4-kloro-3-(trifluorometil)fenil]amino}karbonil)amino]fenioksi}n-metilpiridin-2-karboksamida |
Country Status (35)
| Country | Link |
|---|---|
| US (1) | US8124782B2 (hr) |
| EP (1) | EP1797037B1 (hr) |
| JP (2) | JP2008514657A (hr) |
| KR (1) | KR101263032B1 (hr) |
| CN (1) | CN101052619B (hr) |
| AR (1) | AR053973A1 (hr) |
| AU (1) | AU2005289099B2 (hr) |
| BR (1) | BRPI0515944B1 (hr) |
| CA (1) | CA2581835C (hr) |
| CU (1) | CU23754B7 (hr) |
| CY (1) | CY1116126T1 (hr) |
| DK (1) | DK1797037T3 (hr) |
| DO (1) | DOP2005000183A (hr) |
| EC (1) | ECSP077357A (hr) |
| ES (1) | ES2532377T3 (hr) |
| GT (1) | GT200500269A (hr) |
| HK (1) | HK1113484A1 (hr) |
| HN (1) | HN2005000768A (hr) |
| HR (1) | HRP20150295T1 (hr) |
| IL (1) | IL182046A0 (hr) |
| MA (1) | MA28883B1 (hr) |
| MY (1) | MY149873A (hr) |
| NO (1) | NO339647B1 (hr) |
| NZ (1) | NZ554119A (hr) |
| PE (5) | PE20091586A1 (hr) |
| PL (1) | PL1797037T3 (hr) |
| PT (1) | PT1797037E (hr) |
| SG (1) | SG155997A1 (hr) |
| SI (1) | SI1797037T1 (hr) |
| SV (1) | SV2006002243A (hr) |
| TW (1) | TWI382973B (hr) |
| UA (1) | UA90691C2 (hr) |
| UY (1) | UY29143A1 (hr) |
| WO (1) | WO2006034796A1 (hr) |
| ZA (1) | ZA200702511B (hr) |
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| US8124630B2 (en) | 1999-01-13 | 2012-02-28 | Bayer Healthcare Llc | ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| CA2359244C (en) | 1999-01-13 | 2013-10-08 | Bayer Corporation | .omega.-carboxy aryl substituted diphenyl ureas as p38 kinase inhibitors |
| DK1478358T3 (da) | 2002-02-11 | 2013-10-07 | Bayer Healthcare Llc | Sorafenibtosylat til behandling af sygdomme kendetegnet ved unormal angiogenese |
| PT1626714E (pt) | 2003-05-20 | 2007-08-24 | Bayer Pharmaceuticals Corp | Diarilureias para doenças mediadas por pdgfr |
| ES2297490T3 (es) | 2003-07-23 | 2008-05-01 | Bayer Pharmaceuticals Corporation | Omega-carboxiarildifenilurea fluoro sustituida para el tratamiento y prevencion de enfermadades y afecciones. |
| BRPI0515946A (pt) * | 2004-09-29 | 2008-08-12 | Bayer Healthcare Ag | sal de tosilato, sua preparação e uso, bem como composição farmacêutica compreendendo o mesmo |
| WO2006034796A1 (en) | 2004-09-29 | 2006-04-06 | Bayer Healthcare Ag | Process for the preparation of 4-{4-[({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenoxy}-n-methylpyridine-2-carboxamide |
| JP5304241B2 (ja) | 2005-03-07 | 2013-10-02 | バイエル・ヘルスケア・エルエルシー | 癌の処置用のオメガ−カルボキシアリール置換ジフェニルウレアを含む医薬組成物 |
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| CN103254126A (zh) * | 2008-09-19 | 2013-08-21 | 苏州泽璟生物制药有限公司 | 氘代的ω-二苯基脲及衍生物以及包含该化合物的药物组合物 |
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| WO2011058522A1 (en) | 2009-11-12 | 2011-05-19 | Ranbaxy Laboratories Limited | Sorafenib ethylsulfonate salt, process for preparation and use |
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| CN105181844A (zh) * | 2015-09-11 | 2015-12-23 | 江苏嘉逸医药有限公司 | 一种高效液相色谱法测定甲苯磺酸索拉非尼含量和有关物质的方法 |
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