NO340743B1 - Fremgangsmåte for syntese av organiske forbindelser - Google Patents
Fremgangsmåte for syntese av organiske forbindelser Download PDFInfo
- Publication number
- NO340743B1 NO340743B1 NO20080157A NO20080157A NO340743B1 NO 340743 B1 NO340743 B1 NO 340743B1 NO 20080157 A NO20080157 A NO 20080157A NO 20080157 A NO20080157 A NO 20080157A NO 340743 B1 NO340743 B1 NO 340743B1
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- alkyl
- alkylamino
- formula
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- 230000015572 biosynthetic process Effects 0.000 title description 5
- 238000003786 synthesis reaction Methods 0.000 title description 5
- 150000002894 organic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- -1 bulky alkyllithium Inorganic materials 0.000 claims description 3
- 229960005235 piperonyl butoxide Drugs 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- ZWWWLCMDTZFSOO-UHFFFAOYSA-N diethoxyphosphorylformonitrile Chemical compound CCOP(=O)(C#N)OCC ZWWWLCMDTZFSOO-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WEVYNIUIFUYDGI-UHFFFAOYSA-N 3-[6-[4-(trifluoromethoxy)anilino]-4-pyrimidinyl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N=CN=C(NC=3C=CC(OC(F)(F)F)=CC=3)C=2)=C1 WEVYNIUIFUYDGI-UHFFFAOYSA-N 0.000 description 1
- 101100335081 Mus musculus Flt3 gene Proteins 0.000 description 1
- 108091008606 PDGF receptors Proteins 0.000 description 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
- 102000016971 Proto-Oncogene Proteins c-kit Human genes 0.000 description 1
- 108010014608 Proto-Oncogene Proteins c-kit Proteins 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
- HHZIURLSWUIHRB-UHFFFAOYSA-N nilotinib Chemical compound C1=NC(C)=CN1C1=CC(NC(=O)C=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 HHZIURLSWUIHRB-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68897705P | 2005-06-09 | 2005-06-09 | |
| US70559005P | 2005-08-04 | 2005-08-04 | |
| PCT/US2006/022155 WO2006135641A2 (en) | 2005-06-09 | 2006-06-07 | PROCESS FOR THE SYNTHESIS OF 5- (METHYL-lH-IMIDAZOL-l-YL) -3- (TRI FLUOROME TH YL) -BENZENEAMINE |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20080157L NO20080157L (no) | 2008-01-09 |
| NO340743B1 true NO340743B1 (no) | 2017-06-12 |
Family
ID=37091153
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20080157A NO340743B1 (no) | 2005-06-09 | 2008-01-09 | Fremgangsmåte for syntese av organiske forbindelser |
Country Status (31)
| Country | Link |
|---|---|
| US (2) | US8124763B2 (enExample) |
| EP (1) | EP1924574B1 (enExample) |
| JP (1) | JP5118024B2 (enExample) |
| KR (3) | KR20120066067A (enExample) |
| AR (1) | AR053890A1 (enExample) |
| AT (1) | ATE487709T1 (enExample) |
| AU (1) | AU2006258051B2 (enExample) |
| BR (1) | BRPI0611663A2 (enExample) |
| CA (1) | CA2610105C (enExample) |
| CY (1) | CY1111428T1 (enExample) |
| DE (1) | DE602006018156D1 (enExample) |
| DK (1) | DK1924574T3 (enExample) |
| EC (1) | ECSP077982A (enExample) |
| EG (1) | EG25039A (enExample) |
| GT (1) | GT200600217A (enExample) |
| IL (1) | IL187421A (enExample) |
| JO (1) | JO2636B1 (enExample) |
| MA (1) | MA29599B1 (enExample) |
| MX (1) | MX2007015423A (enExample) |
| MY (1) | MY147436A (enExample) |
| NO (1) | NO340743B1 (enExample) |
| NZ (1) | NZ563740A (enExample) |
| PE (1) | PE20070015A1 (enExample) |
| PL (1) | PL1924574T3 (enExample) |
| PT (1) | PT1924574E (enExample) |
| RU (1) | RU2444520C2 (enExample) |
| SA (1) | SA06270147B1 (enExample) |
| SI (1) | SI1924574T1 (enExample) |
| TN (1) | TNSN07463A1 (enExample) |
| TW (1) | TWI430999B (enExample) |
| WO (1) | WO2006135641A2 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GT200600316A (es) * | 2005-07-20 | 2007-04-02 | Sales de 4-metilo-n-(3-(4-metilo-imidazol-1-ilo)-5-trifluorometilo-fenilo)-3-(4-piridina-3-ilo-pirimidina-2-iloamino)- benzamida. | |
| TWI433677B (zh) | 2007-06-04 | 2014-04-11 | Avila Therapeutics Inc | 雜環化合物及其用途 |
| US20100016590A1 (en) * | 2008-07-17 | 2010-01-21 | Teva Pharmaceutical Industries Ltd. | Nilotinib intermediates and preparation thereof |
| EP2530081A3 (en) | 2008-11-05 | 2013-04-10 | Teva Pharmaceutical Industries, Ltd. | Nilotinib HCI crystalline forms |
| WO2010060074A1 (en) * | 2008-11-24 | 2010-05-27 | Teva Pharmaceutical Industries Ltd. | Preparation of nilotinib and intermediates thereof |
| US20110053968A1 (en) | 2009-06-09 | 2011-03-03 | Auspex Pharmaceuticals, Inc. | Aminopyrimidine inhibitors of tyrosine kinase |
| JO3634B1 (ar) | 2009-11-17 | 2020-08-27 | Novartis Ag | طريقة لعلاج اضطرابات تكاثرية وحالات مرضية أخرى متوسطة بنشاط كيناز bcr-abl، c-kit، ddr1، ddr2، أو pdgf-r |
| WO2012135651A1 (en) | 2011-03-31 | 2012-10-04 | The Procter & Gamble Company | Systems, models and methods for identifying and evaluating skin-active agents effective for treating dandruff/seborrheic dermatitis |
| AR086913A1 (es) * | 2011-06-14 | 2014-01-29 | Novartis Ag | 4-metil-3-[[4-(3-piridinil)-2-pirimidinil]-amino]-n-[5-(4-metil-1h-imidazol-1-il)-3-(trifluoro-metil)-fenil]-benzamida amorfa, forma de dosificacion que la contiene y metodo para prepararlas |
| WO2013120852A1 (en) | 2012-02-13 | 2013-08-22 | Grindeks, A Joint Stock Company | Intermediates for a novel process of preparing imatinib and related tyrosine kinase inhibitors |
| US9920357B2 (en) | 2012-06-06 | 2018-03-20 | The Procter & Gamble Company | Systems and methods for identifying cosmetic agents for hair/scalp care compositions |
| WO2015092624A1 (en) | 2013-12-16 | 2015-06-25 | Ranbaxy Laboratories Limited | Nilotinib mono-oxalate and its crystalline form |
| CN103694176B (zh) | 2014-01-07 | 2015-02-18 | 苏州立新制药有限公司 | 尼洛替尼中间体的制备方法 |
| EP3095782A1 (en) | 2015-05-18 | 2016-11-23 | Esteve Química, S.A. | New method for preparing 3-(4-methyl-1h-imidazol-1-yl)-5-(trifluoromethyl)benzenamine |
| EP3749697A4 (en) | 2018-02-05 | 2021-11-03 | Bio-Rad Laboratories, Inc. | CHROMATOGRAPHY RESIN WITH LIGAND MIXED MODE ANIONIC / HYDROPHOBIC EXCHANGE |
| EP3806858A4 (en) | 2018-06-15 | 2022-03-09 | Handa Pharmaceuticals, Inc. | KINA INHIBITOR SALTS AND COMPOSITIONS THEREOF |
| JP2020007240A (ja) * | 2018-07-04 | 2020-01-16 | 住友化学株式会社 | ベンズアミド化合物の製造方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004005281A1 (en) * | 2002-07-05 | 2004-01-15 | Novartis Ag | Inhibitors of tyrosine kinases |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5136082A (en) * | 1990-08-03 | 1992-08-04 | Himont Incorporated | Process for preparing organic esters and amides and catalyst system therefor |
| AU5539294A (en) | 1992-12-24 | 1994-07-19 | Hemagen/Pfc | Fluorocarbon emulsions |
| TW406020B (en) | 1993-09-29 | 2000-09-21 | Bristol Myers Squibb Co | Stabilized pharmaceutical composition and its method for preparation and stabilizing solvent |
| US5597829A (en) | 1994-05-09 | 1997-01-28 | Bionumerik Pharmaceuticals, Inc. | Lactone stable formulation of camptothecin and methods for uses thereof |
| US5726181A (en) | 1995-06-05 | 1998-03-10 | Bionumerik Pharmaceuticals, Inc. | Formulations and compositions of poorly water soluble camptothecin derivatives |
| US6323366B1 (en) | 1997-07-29 | 2001-11-27 | Massachusetts Institute Of Technology | Arylamine synthesis |
| AR013261A1 (es) | 1997-08-01 | 2000-12-13 | Smithkline Beecham Corp | Formulaciones farmaceuticas para analogos de camptotecina en capsula de gelatina |
| US20030059465A1 (en) | 1998-05-11 | 2003-03-27 | Unger Evan C. | Stabilized nanoparticle formulations of camptotheca derivatives |
| US6395916B1 (en) * | 1998-07-10 | 2002-05-28 | Massachusetts Institute Of Technology | Ligands for metals and improved metal-catalyzed processes based thereon |
| EP1044977B1 (en) | 1999-03-09 | 2002-05-02 | Sigma-Tau Industrie Farmaceutiche Riunite S.p.A. | Camptothecin derivatives having antitumor activity |
| IT1306129B1 (it) | 1999-04-13 | 2001-05-30 | Sigma Tau Ind Farmaceuti | Esteri della l-carnitina o di alcanoil l-carnitine utilizzabili comelipidi cationici per l'immissione intracellulare di composti |
| DE19926056B4 (de) | 1999-06-08 | 2004-03-25 | Gkss-Forschungszentrum Geesthacht Gmbh | Einrichtung zur Analyse atomarer und/oder molekularer Elemente mittels wellenlängendispersiver, röntgenspektrometrischer Einrichtungen |
| GB9918885D0 (en) | 1999-08-10 | 1999-10-13 | Pharmacia & Upjohn Spa | Pharmaceutical formulations in hydroxypropymethycellulose capsules |
| GB9925127D0 (en) | 1999-10-22 | 1999-12-22 | Pharmacia & Upjohn Spa | Oral formulations for anti-tumor compounds |
| US20040009229A1 (en) | 2000-01-05 | 2004-01-15 | Unger Evan Charles | Stabilized nanoparticle formulations of camptotheca derivatives |
| US20020150615A1 (en) | 2001-02-12 | 2002-10-17 | Howard Sands | Injectable pharmaceutical composition comprising microdroplets of a camptothecin |
| US6629598B2 (en) | 2001-08-10 | 2003-10-07 | Vinod K. Narula | Flexible ribbed splint system |
| US6653319B1 (en) | 2001-08-10 | 2003-11-25 | University Of Kentucky Research Foundation | Pharmaceutical formulation for poorly water soluble camptothecin analogues |
| WO2003032906A2 (en) | 2001-10-15 | 2003-04-24 | Crititech, Inc. | Delivery of poorly soluble drugs |
| AU2002353118A1 (en) | 2001-12-11 | 2003-07-24 | Dor Biopharma, Inc. | Lipid particles and suspensions and uses thereof |
| JP2003267891A (ja) | 2002-03-13 | 2003-09-25 | Mitsubishi-Kagaku Foods Corp | Ｗ／ｏ／ｗ型エマルション製剤 |
| FR2840303B1 (fr) * | 2002-05-31 | 2005-07-15 | Rhodia Chimie Sa | Procede d'arylation ou de vinylation ou d'alcylynation d'un compose nucleophile |
| CZ294371B6 (cs) | 2002-06-10 | 2004-12-15 | Pliva - Lachema, A. S. | Stabilizovaná farmaceutická kompozice na bázi polyoxyethylovaného ricinového oleje a způsob její přípravy |
| EP1393719A1 (en) | 2002-08-23 | 2004-03-03 | Munich Biotech AG | Camptothecin-carboxylate formulations |
| JP4426749B2 (ja) | 2002-07-11 | 2010-03-03 | 株式会社産学連携機構九州 | Ｏ／ｗ型エマルション製剤 |
| US20040171560A1 (en) | 2002-12-23 | 2004-09-02 | Dabur Research Foundation | Stabilized pharmaceutical composition |
| JP2006199590A (ja) | 2003-09-04 | 2006-08-03 | Nano Career Kk | 水溶性の塩基性薬物内包ナノ粒子含有組成物 |
| CA2543722C (en) | 2003-10-29 | 2011-01-04 | Sonus Pharmaceuticals, Inc. | Tocopherol-modified therapeutic drug compounds |
| CA2548078C (en) | 2003-12-17 | 2009-05-12 | Bionumerik Pharmaceuticals, Inc. | Pharmaceutical formulations of camptothecins and process for making same |
| GT200500310A (es) | 2004-11-19 | 2006-06-19 | Compuestos organicos |
-
2006
- 2006-05-23 SA SA06270147A patent/SA06270147B1/ar unknown
- 2006-05-24 GT GT200600217A patent/GT200600217A/es unknown
- 2006-05-31 MY MYPI20062507A patent/MY147436A/en unknown
- 2006-06-06 JO JO2006166A patent/JO2636B1/en active
- 2006-06-07 AT AT06772448T patent/ATE487709T1/de active
- 2006-06-07 JP JP2008515881A patent/JP5118024B2/ja active Active
- 2006-06-07 WO PCT/US2006/022155 patent/WO2006135641A2/en not_active Ceased
- 2006-06-07 MX MX2007015423A patent/MX2007015423A/es active IP Right Grant
- 2006-06-07 PT PT06772448T patent/PT1924574E/pt unknown
- 2006-06-07 US US11/915,671 patent/US8124763B2/en active Active
- 2006-06-07 KR KR1020127011980A patent/KR20120066067A/ko not_active Ceased
- 2006-06-07 SI SI200630903T patent/SI1924574T1/sl unknown
- 2006-06-07 DE DE602006018156T patent/DE602006018156D1/de active Active
- 2006-06-07 PL PL06772448T patent/PL1924574T3/pl unknown
- 2006-06-07 CA CA2610105A patent/CA2610105C/en active Active
- 2006-06-07 AR ARP060102369A patent/AR053890A1/es not_active Application Discontinuation
- 2006-06-07 KR KR1020137025659A patent/KR101514593B1/ko active Active
- 2006-06-07 BR BRPI0611663-9A patent/BRPI0611663A2/pt not_active Application Discontinuation
- 2006-06-07 EP EP06772448A patent/EP1924574B1/en active Active
- 2006-06-07 NZ NZ563740A patent/NZ563740A/en not_active IP Right Cessation
- 2006-06-07 RU RU2007148231/04A patent/RU2444520C2/ru active
- 2006-06-07 KR KR1020077028638A patent/KR101216249B1/ko active Active
- 2006-06-07 PE PE2006000631A patent/PE20070015A1/es not_active Application Discontinuation
- 2006-06-07 DK DK06772448.4T patent/DK1924574T3/da active
- 2006-06-07 AU AU2006258051A patent/AU2006258051B2/en active Active
- 2006-06-08 TW TW095120302A patent/TWI430999B/zh not_active IP Right Cessation
-
2007
- 2007-11-15 IL IL187421A patent/IL187421A/en active IP Right Grant
- 2007-12-05 EC EC2007007982A patent/ECSP077982A/es unknown
- 2007-12-07 TN TNP2007000463A patent/TNSN07463A1/en unknown
- 2007-12-09 EG EGNA2007001382 patent/EG25039A/xx active
- 2007-12-26 MA MA30505A patent/MA29599B1/fr unknown
-
2008
- 2008-01-09 NO NO20080157A patent/NO340743B1/no unknown
-
2011
- 2011-02-04 CY CY20111100134T patent/CY1111428T1/el unknown
-
2012
- 2012-01-19 US US13/353,434 patent/US8946416B2/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004005281A1 (en) * | 2002-07-05 | 2004-01-15 | Novartis Ag | Inhibitors of tyrosine kinases |
| EP1532138B1 (en) * | 2002-07-05 | 2008-11-19 | Novartis AG | Inhibitors of tyrosine kinases |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO340743B1 (no) | Fremgangsmåte for syntese av organiske forbindelser | |
| CN104540807B (zh) | 用于制备吡唑甲酸衍生物的方法 | |
| DK161966B (da) | Fremgangsmaade til fremstilling af 5-aroylerede 1,2-dihydro-3h-pyrrolooe1,2-aaapyrrol-1-carboxylsyrer eller estere eller farmaceutisk acceptable salte deraf | |
| CN105541844A (zh) | 一种高纯度利拉利汀的简易制备方法 | |
| JP2005526049A (ja) | ベンゾイソキサゾールメタンスルホニルクロリドの調製及びゾニスアミドを形成するためのそのアミド化の方法 | |
| US20080188667A1 (en) | Azlactone compound and method for preparation thereof | |
| JP2007246396A (ja) | ５−ジフルオロメトキシ−４−チオメチルピラゾール化合物の製造方法 | |
| KR100686695B1 (ko) | 프란루카스트 또는 그의 수화물의 제조방법 및 그의 합성중간체 | |
| CA2194119C (en) | Process for the preparation of 2-substituted 5-chloroimidazole-4-carbaldehydes | |
| JP4501015B2 (ja) | アミノピリミジン化合物の製造方法 | |
| JP4152353B2 (ja) | 殺菌性ピリジン化合物 | |
| JP3031279B2 (ja) | ２−アルコキシ−６−（トリフルオロメチル）ピリミジン−４−オルの製造方法 | |
| CA2431821C (en) | Method for the production of 2-(2-ethoxyphenyl)-substituted imidazotriazinones | |
| CN103772308B (zh) | 5-氨基-3-(1-乙基-1-甲基丙基)异噁唑中间体的制备方法和异噁草胺的制备方法 | |
| JP6389513B2 (ja) | ３−クロロ−４−メトキシベンジルアミン塩酸塩含有組成物およびその製造方法 | |
| CN116768853A (zh) | 一种由吡啶基吡唑醛制备吡啶基吡唑酰氯的方法及其应用 | |
| JP4165110B2 (ja) | ４−オキシピリミジン誘導体の製法 | |
| CN105601585B (zh) | 一种含噻唑环的羧酰胺类化合物及其制备与应用 | |
| CN105541753B (zh) | 一种含有噻唑环的羧酰胺衍生物及其制备与应用 | |
| JP2003517029A (ja) | トリフルオロメチルアセトフェノンの製造方法 | |
| CN120457110A (zh) | 制备异噁唑啉羧酸衍生物的方法 | |
| JP4752121B2 (ja) | ニトリル誘導体の製造方法、その中間体および中間体の製造方法 | |
| TW202316967A (zh) | 製備異㗁唑啉羧酸衍生物的方法 | |
| JP2005126389A (ja) | ２，４−ジクロロ−５−フルオロピリミジンの製造方法 | |
| JP2007070362A (ja) | ２−（５−クロロ−２−ニトロフェニル）−２−置換酢酸エステル誘導体の製造法 |