UA76616C2 - Process for the preparation of olanzapine and intermediary product thereof - Google Patents
Process for the preparation of olanzapine and intermediary product thereof Download PDFInfo
- Publication number
- UA76616C2 UA76616C2 UA20041109317A UA20041109317A UA76616C2 UA 76616 C2 UA76616 C2 UA 76616C2 UA 20041109317 A UA20041109317 A UA 20041109317A UA 20041109317 A UA20041109317 A UA 20041109317A UA 76616 C2 UA76616 C2 UA 76616C2
- Authority
- UA
- Ukraine
- Prior art keywords
- differs
- borohydride
- chemical formula
- methyl
- benzodiazepine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 53
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 229960005017 olanzapine Drugs 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 238000007069 methylation reaction Methods 0.000 claims abstract description 22
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 37
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 229940049706 benzodiazepine Drugs 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 18
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 12
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 12
- 230000002829 reductive effect Effects 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 238000006722 reduction reaction Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 239000012279 sodium borohydride Substances 0.000 claims description 9
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 9
- 239000003638 chemical reducing agent Substances 0.000 claims description 8
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 235000019253 formic acid Nutrition 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 6
- FHPIXVHJEIZKJW-UHFFFAOYSA-N 4'-N-desmethylolanzapine Chemical compound S1C(C)=CC2=C1NC1=CC=CC=C1N=C2N1CCNCC1 FHPIXVHJEIZKJW-UHFFFAOYSA-N 0.000 abstract 1
- SFWJCBPXQCTXTO-UHFFFAOYSA-N 4-(2-methyl-10H-thieno[2,3-b][1,5]benzodiazepin-4-yl)piperazine-1-carbaldehyde Chemical compound S1C(C)=CC2=C1NC1=CC=CC=C1N=C2N1CCN(C=O)CC1 SFWJCBPXQCTXTO-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical class IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- -1 for example Substances 0.000 description 3
- 230000001035 methylating effect Effects 0.000 description 3
- 230000011987 methylation Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000012022 methylating agents Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000001172 regenerating effect Effects 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- SETMGIIITGNLAS-UHFFFAOYSA-N spizofurone Chemical compound O=C1C2=CC(C(=O)C)=CC=C2OC21CC2 SETMGIIITGNLAS-UHFFFAOYSA-N 0.000 description 2
- 229950001870 spizofurone Drugs 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZVAPWJGRRUHKGP-UHFFFAOYSA-N 1h-1,5-benzodiazepine Chemical compound N1C=CC=NC2=CC=CC=C12 ZVAPWJGRRUHKGP-UHFFFAOYSA-N 0.000 description 1
- VBCKYDVWOPZOBA-UHFFFAOYSA-N 2-(oxolan-2-ylmethoxymethyl)oxolane Chemical compound C1CCOC1COCC1CCCO1 VBCKYDVWOPZOBA-UHFFFAOYSA-N 0.000 description 1
- JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 description 1
- NPXUFPFFHANGDL-UHFFFAOYSA-N 5-methyl-2-(2-nitroanilino)thiophene-3-carbonitrile Chemical compound S1C(C)=CC(C#N)=C1NC1=CC=CC=C1[N+]([O-])=O NPXUFPFFHANGDL-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL354642A PL199016B1 (pl) | 2002-06-20 | 2002-06-20 | Sposób wytwarzania olanzapiny |
| PCT/IB2003/002181 WO2004000847A1 (en) | 2002-06-20 | 2003-06-10 | A process for the preparation of olanzapine and an intermediate therefor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA76616C2 true UA76616C2 (en) | 2006-08-15 |
Family
ID=29997625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20041109317A UA76616C2 (en) | 2002-06-20 | 2003-10-06 | Process for the preparation of olanzapine and intermediary product thereof |
Country Status (17)
| Country | Link |
|---|---|
| EP (2) | EP1513845B2 (de) |
| CN (1) | CN100338069C (de) |
| AT (2) | ATE373664T1 (de) |
| AU (1) | AU2003240167A1 (de) |
| BR (1) | BR0305100A (de) |
| DE (2) | DE60316047T2 (de) |
| ES (2) | ES2291644T5 (de) |
| HR (1) | HRP20041075B1 (de) |
| MX (1) | MXPA04012200A (de) |
| NO (1) | NO328873B1 (de) |
| PL (1) | PL199016B1 (de) |
| PT (2) | PT1513845E (de) |
| RU (1) | RU2005101324A (de) |
| SI (2) | SI1669359T1 (de) |
| TN (1) | TNSN04226A1 (de) |
| UA (1) | UA76616C2 (de) |
| WO (1) | WO2004000847A1 (de) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1575962A1 (de) | 2002-12-24 | 2005-09-21 | Teva Pharmaceutical Industries Limited | Neue kristallformen von olanzapin, verfahren zu deren herstellung und verfahren zur herstellung bekannter kristallformen von olanzapin |
| EP1711503A1 (de) * | 2004-01-27 | 2006-10-18 | Synthon B.V. | Synthese von olanzapin und zwischenprodukten davon |
| AR047459A1 (es) | 2004-01-27 | 2006-01-18 | Synthon Bv | Sales estables de 2-metil-4-(4-metil-1-piperazinil)-10h-tieno[2,3-b][1,5]benzodiazepina (olanzapina) |
| AR048272A1 (es) * | 2004-03-18 | 2006-04-12 | Lek Pharmaceuticals | Sintesis de 2 metil - 4- (4- metil -1- piperazinil) - 10 h- tieno ( 2,3-b) (1,5) benzodiazepina y sus sales, metodos para su preparacion, composiciones farmaceuticas que la contienen y su uso en la fabricacion de medicamentos para el tratamiento de enfermedades mentales. |
| US8044196B2 (en) | 2004-07-14 | 2011-10-25 | Jubilant Organosys Limited | Process for producing pure form of 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine |
| PL198589B1 (pl) | 2004-11-22 | 2008-06-30 | Adamed Sp Z Oo | Sposób wytwarzania N-demetyloolanzapiny |
| CN100383144C (zh) * | 2006-09-11 | 2008-04-23 | 杭州盛美医药科技开发有限公司 | 一种奥氮平的中间体及其制备与应用 |
| EP2292624A1 (de) | 2009-07-20 | 2011-03-09 | LEK Pharmaceuticals d.d. | Olanzapinreinigungsverfahren |
| CN102234285B (zh) * | 2010-04-19 | 2013-06-12 | 江苏豪森药业股份有限公司 | 奥氮平的制备方法 |
| CN102924470B (zh) * | 2011-08-31 | 2014-12-03 | 江苏豪森药业股份有限公司 | 新颖的奥氮平的制备方法 |
| CN102942573B (zh) * | 2011-10-09 | 2015-03-25 | 连云港恒运医药科技有限公司 | 奥氮平的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7306069A (de) † | 1973-05-02 | 1974-11-05 | ||
| US4115568A (en) † | 1974-11-26 | 1978-09-19 | Lilly Industries Limited | Thieno[3,2-b]-[1,5]benzodiazepines |
| SU629879A3 (ru) * | 1974-11-26 | 1978-10-25 | Лилли Индастриз Лимитед, (Фирма) | Способ получени тиено(1,5) бензодиазепинов или их солей |
| US5239071A (en) † | 1989-11-21 | 1993-08-24 | The B. F. Goodrich Company | Process for methylating a hindered nitrogen atom in an inert non-aqueous solvent |
| GB9009229D0 (en) * | 1990-04-25 | 1990-06-20 | Lilly Industries Ltd | Pharmaceutical compounds |
| DK55192D0 (da) † | 1992-04-28 | 1992-04-28 | Lundbeck & Co As H | 1-piperazino-1,2-dihydroindenderivater |
| US6348455B1 (en) | 1998-11-23 | 2002-02-19 | Sepracor Inc. | Desmetylolanzapine compositions and methods |
-
2002
- 2002-06-20 PL PL354642A patent/PL199016B1/pl unknown
-
2003
- 2003-06-10 EP EP03732782A patent/EP1513845B2/de not_active Expired - Lifetime
- 2003-06-10 PT PT03732782T patent/PT1513845E/pt unknown
- 2003-06-10 SI SI200330985T patent/SI1669359T1/sl unknown
- 2003-06-10 MX MXPA04012200A patent/MXPA04012200A/es not_active Application Discontinuation
- 2003-06-10 AT AT03732782T patent/ATE373664T1/de not_active IP Right Cessation
- 2003-06-10 WO PCT/IB2003/002181 patent/WO2004000847A1/en active IP Right Grant
- 2003-06-10 BR BR0305100-5A patent/BR0305100A/pt not_active IP Right Cessation
- 2003-06-10 CN CNB038141655A patent/CN100338069C/zh not_active Ceased
- 2003-06-10 RU RU2005101324/04A patent/RU2005101324A/ru not_active Application Discontinuation
- 2003-06-10 EP EP06100356A patent/EP1669359B1/de not_active Expired - Lifetime
- 2003-06-10 ES ES03732782T patent/ES2291644T5/es not_active Expired - Lifetime
- 2003-06-10 DE DE60316047T patent/DE60316047T2/de not_active Expired - Fee Related
- 2003-06-10 AT AT06100356T patent/ATE371660T1/de not_active IP Right Cessation
- 2003-06-10 PT PT06100356T patent/PT1669359E/pt unknown
- 2003-06-10 SI SI200330991T patent/SI1513845T2/sl unknown
- 2003-06-10 AU AU2003240167A patent/AU2003240167A1/en not_active Abandoned
- 2003-06-10 ES ES06100356T patent/ES2289730T3/es not_active Expired - Lifetime
- 2003-06-10 DE DE60316439T patent/DE60316439T3/de not_active Expired - Lifetime
- 2003-10-06 UA UA20041109317A patent/UA76616C2/uk unknown
-
2004
- 2004-02-13 NO NO20040658A patent/NO328873B1/no not_active IP Right Cessation
- 2004-11-17 HR HR20041075A patent/HRP20041075B1/xx not_active IP Right Cessation
- 2004-11-17 TN TNP2004000226A patent/TNSN04226A1/en unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US10100044B2 (en) | Methods for preparing brexpiprazole, key intermediates thereof and salts thereof | |
| UA76616C2 (en) | Process for the preparation of olanzapine and intermediary product thereof | |
| US20060069085A1 (en) | Preparation of 4,5-dihydro-pyrazolo[3,4-c]pyrid-2-ones | |
| US20060069260A1 (en) | Preparation of N-aryl pyridones | |
| JP2009007273A (ja) | ジアミノピリミジン化合物の製造方法 | |
| US20090247755A1 (en) | Process for Preparing a Substituted Imidazopyridine Compound | |
| EP1945605B1 (de) | Verfahren zur herstellung substituierter anisidine | |
| JP4888840B2 (ja) | ピラゾール−ｏ−グリコシド誘導体の調製方法及び前記方法の新規中間体 | |
| EP2264016A2 (de) | Verfahren zur Herstellung einer reinen Form von 2-Methyl-4-(4-Methyl-1-Piperazinyl)-10H-thieno[2,3-B][1,5]-Benzodiazepin | |
| CN101405267A (zh) | 制备1-卤代-2,7-萘啶基衍生物的方法 | |
| JP2010024173A (ja) | ９−アミノシンコナアルカロイドの製造法 | |
| RU2503655C2 (ru) | N-(5-АЦЕТИЛ-2-ФТОРФЕНИЛ)-N-МЕТИЛАЦЕТАМИД, СПОСОБ ПОЛУЧЕНИЯ N-[5-(3-ДИМЕТИЛАМИНО-АКРИЛОИЛ)-2-ФТОРФЕНИЛ]-N-МЕТИЛАЦЕТАМИДА И СПОСОБ ПОЛУЧЕНИЯ N-{2-ФТОР-5-[3-ТИОФЕН-2-КАРБОНИЛ-ПИРАЗОЛО [1,5-а]ПИРИМИДИН-7-ИЛ]ФЕНИЛ}-N-МЕТИЛАЦЕТАМИДА | |
| WO2006010079A2 (en) | Process for preparing naratriptan hydrochloride | |
| US6900324B2 (en) | Process for preparing a substituted imidazopyridine compound | |
| RU2274635C1 (ru) | Способ получения тербинафина или его гидрохлорида | |
| JP2024509995A (ja) | リスジプラムを調製するための方法 | |
| JPH01125377A (ja) | ３−メチルチオフエン−２−カルボキサルデヒド製造のための中間体 | |
| JPS6217591B2 (de) | ||
| JPS62192361A (ja) | ピラゾ−ル類とその製法 | |
| JPH09227548A (ja) | 新規なγ−ヒドロキシカルボン酸誘導体 |