RU2001128229A - Новый синтез и кристаллизация соединений, содержащих пиперазиновое кольцо - Google Patents
Новый синтез и кристаллизация соединений, содержащих пиперазиновое кольцо Download PDFInfo
- Publication number
- RU2001128229A RU2001128229A RU2001128229/04A RU2001128229A RU2001128229A RU 2001128229 A RU2001128229 A RU 2001128229A RU 2001128229/04 A RU2001128229/04 A RU 2001128229/04A RU 2001128229 A RU2001128229 A RU 2001128229A RU 2001128229 A RU2001128229 A RU 2001128229A
- Authority
- RU
- Russia
- Prior art keywords
- mirtazapine
- methyl
- phenylpiperazine
- chloride
- cyanopyridyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 5
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000002425 crystallisation Methods 0.000 title 1
- 230000008025 crystallization Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims 27
- RONZAEMNMFQXRA-UHFFFAOYSA-N mirtazapine Chemical compound C1C2=CC=CN=C2N2CCN(C)CC2C2=CC=CC=C21 RONZAEMNMFQXRA-UHFFFAOYSA-N 0.000 claims 14
- 229960001785 mirtazapine Drugs 0.000 claims 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 10
- 239000002585 base Substances 0.000 claims 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 239000003153 chemical reaction reagent Substances 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- 230000007062 hydrolysis Effects 0.000 claims 5
- 238000006460 hydrolysis reaction Methods 0.000 claims 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims 4
- 238000010438 heat treatment Methods 0.000 claims 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 4
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- XDJWZONZDVNKDU-UHFFFAOYSA-N 1314-24-5 Chemical compound O=POP=O XDJWZONZDVNKDU-UHFFFAOYSA-N 0.000 claims 2
- 229910015900 BF3 Inorganic materials 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- 239000002841 Lewis acid Substances 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 2
- PYZPABZGIRHQTA-UHFFFAOYSA-N [2-(4-methyl-2-phenylpiperazin-1-yl)pyridin-3-yl]methanol Chemical compound C1N(C)CCN(C=2C(=CC=CN=2)CO)C1C1=CC=CC=C1 PYZPABZGIRHQTA-UHFFFAOYSA-N 0.000 claims 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 2
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 claims 2
- 150000007517 lewis acids Chemical class 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000011574 phosphorus Substances 0.000 claims 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- VSAISIQCTGDGPU-UHFFFAOYSA-N phosphorus trioxide Inorganic materials O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 claims 2
- 229920000137 polyphosphoric acid Polymers 0.000 claims 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims 2
- 239000011592 zinc chloride Substances 0.000 claims 2
- 235000005074 zinc chloride Nutrition 0.000 claims 2
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 claims 2
- FEIACFYXEWBKHU-UHFFFAOYSA-N (2-aminopyridin-3-yl)methanol Chemical compound NC1=NC=CC=C1CO FEIACFYXEWBKHU-UHFFFAOYSA-N 0.000 claims 1
- KUSNCWLQRVMIRN-UHFFFAOYSA-N 2-chloro-n-(2-chloroethyl)-n-methyl-2-phenylethanamine Chemical compound ClCCN(C)CC(Cl)C1=CC=CC=C1 KUSNCWLQRVMIRN-UHFFFAOYSA-N 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000005997 bromomethyl group Chemical group 0.000 claims 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 230000008021 deposition Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- -1 iodomethyl Chemical group 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 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
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13004799P | 1999-04-19 | 1999-04-19 | |
| US60/130047 | 1999-04-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2001128229A true RU2001128229A (ru) | 2003-07-10 |
Family
ID=22442814
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2001128229/04A RU2001128229A (ru) | 1999-04-19 | 2000-04-18 | Новый синтез и кристаллизация соединений, содержащих пиперазиновое кольцо |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JP2004500324A (enExample) |
| KR (1) | KR20020019902A (enExample) |
| CN (4) | CN1679586A (enExample) |
| CA (1) | CA2368815A1 (enExample) |
| CZ (1) | CZ20013658A3 (enExample) |
| HK (1) | HK1044116A1 (enExample) |
| HR (1) | HRP20010747A2 (enExample) |
| HU (1) | HUP0200839A3 (enExample) |
| IL (1) | IL146023A0 (enExample) |
| PL (1) | PL366289A1 (enExample) |
| RU (1) | RU2001128229A (enExample) |
| SK (1) | SK14672001A3 (enExample) |
| TR (1) | TR200103028T2 (enExample) |
| WO (1) | WO2000062782A1 (enExample) |
| YU (1) | YU74101A (enExample) |
| ZA (1) | ZA200108220B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2352566C2 (ru) * | 2003-07-10 | 2009-04-20 | Н.В.Органон | Способ получения энантиомерно чистого миртазапина |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001038329A1 (en) * | 1999-11-24 | 2001-05-31 | Sumika Fine Chemicals Co., Ltd. | Anhydrous mirtazapine crystals and process for producing the same |
| WO2001042239A1 (en) * | 1999-12-13 | 2001-06-14 | Sumika Fine Chemicals Co., Ltd. | Process for the preparation of a pyridinemethanol compound |
| US6660730B2 (en) * | 2000-11-27 | 2003-12-09 | Sumika Fine Chemicals Co., Ltd. | Anhydrous mirtazapine and process for preparing the same |
| ES2246161B1 (es) * | 2004-07-22 | 2007-04-01 | Medichem, S.A. | Proceso mejorado para la fabricacion de mirtazapina. |
| JP4848704B2 (ja) * | 2004-08-24 | 2011-12-28 | 住友化学株式会社 | ２−（４−メチル−２−フェニルピペラジン−１−イル）−３−シアノピリジンの製造方法 |
| JP5192707B2 (ja) | 2007-03-22 | 2013-05-08 | 住友化学株式会社 | ミルタザピンの製造方法 |
| US7994314B2 (en) | 2007-04-11 | 2011-08-09 | N.V. Organon | Method for the preparation of an enantiomerically pure benzazepine |
| WO2008125578A2 (en) | 2007-04-11 | 2008-10-23 | N.V. Organon | A method for the preparation of mirtazapine |
| KR101485418B1 (ko) | 2013-05-29 | 2015-01-26 | 주식회사 메디켐코리아 | 고순도 미르타자핀의 제조방법 |
| JP2017088564A (ja) * | 2015-11-13 | 2017-05-25 | 株式会社トクヤマ | ミルタザピンの製造方法 |
| JP6571497B2 (ja) * | 2015-11-13 | 2019-09-04 | 株式会社トクヤマ | ミルタザピンの製造方法 |
| CN108191873B (zh) * | 2018-01-08 | 2021-09-24 | 山东省食品药品检验研究院 | 一种盐酸米安色林的纯化方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL189199C (nl) * | 1975-04-05 | 1993-02-01 | Akzo Nv | Werkwijze ter bereiding van farmaceutische preparaten met werking op het centraal zenuwstelsel op basis van benz(aryl)azepinederivaten, de verkregen gevormde farmaceutische preparaten, alsmede werkwijze ter bereiding van de toe te passen benz(aryl)azepinederivaten. |
-
2000
- 2000-04-18 HK HK02105027.4A patent/HK1044116A1/zh unknown
- 2000-04-18 CN CNA2005100042880A patent/CN1679586A/zh active Pending
- 2000-04-18 KR KR1020017013267A patent/KR20020019902A/ko not_active Abandoned
- 2000-04-18 HU HU0200839A patent/HUP0200839A3/hu unknown
- 2000-04-18 CA CA002368815A patent/CA2368815A1/en not_active Abandoned
- 2000-04-18 SK SK1467-2001A patent/SK14672001A3/sk unknown
- 2000-04-18 CN CNA2005100042895A patent/CN1680374A/zh active Pending
- 2000-04-18 YU YU74101A patent/YU74101A/sh unknown
- 2000-04-18 IL IL14602300A patent/IL146023A0/xx unknown
- 2000-04-18 CZ CZ20013658A patent/CZ20013658A3/cs unknown
- 2000-04-18 TR TR2001/03028T patent/TR200103028T2/xx unknown
- 2000-04-18 HR HR20010747A patent/HRP20010747A2/hr not_active Application Discontinuation
- 2000-04-18 WO PCT/US2000/010357 patent/WO2000062782A1/en not_active Ceased
- 2000-04-18 RU RU2001128229/04A patent/RU2001128229A/ru not_active Application Discontinuation
- 2000-04-18 CN CN00807574A patent/CN1356903A/zh active Pending
- 2000-04-18 JP JP2000611918A patent/JP2004500324A/ja not_active Withdrawn
- 2000-04-18 PL PL00366289A patent/PL366289A1/xx unknown
- 2000-04-18 CN CNA2005100042908A patent/CN1680365A/zh active Pending
-
2001
- 2001-10-05 ZA ZA200108220A patent/ZA200108220B/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2352566C2 (ru) * | 2003-07-10 | 2009-04-20 | Н.В.Органон | Способ получения энантиомерно чистого миртазапина |
Also Published As
| Publication number | Publication date |
|---|---|
| CZ20013658A3 (cs) | 2002-08-14 |
| CN1680374A (zh) | 2005-10-12 |
| HRP20010747A2 (en) | 2002-12-31 |
| CA2368815A1 (en) | 2000-10-26 |
| CN1679586A (zh) | 2005-10-12 |
| ZA200108220B (en) | 2006-02-26 |
| WO2000062782A1 (en) | 2000-10-26 |
| HUP0200839A3 (en) | 2003-05-28 |
| JP2004500324A (ja) | 2004-01-08 |
| HUP0200839A2 (en) | 2002-08-28 |
| SK14672001A3 (sk) | 2002-11-06 |
| PL366289A1 (en) | 2005-01-24 |
| IL146023A0 (en) | 2002-07-25 |
| YU74101A (sh) | 2004-09-03 |
| CN1356903A (zh) | 2002-07-03 |
| TR200103028T2 (tr) | 2002-01-21 |
| CN1680365A (zh) | 2005-10-12 |
| KR20020019902A (ko) | 2002-03-13 |
| HK1044116A1 (zh) | 2002-10-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20050915 |