SK14672001A3 - Spôsob syntézy a kryštalizácie zlúčenín obsahujúcich piperazínový kruh - Google Patents
Spôsob syntézy a kryštalizácie zlúčenín obsahujúcich piperazínový kruh Download PDFInfo
- Publication number
- SK14672001A3 SK14672001A3 SK1467-2001A SK14672001A SK14672001A3 SK 14672001 A3 SK14672001 A3 SK 14672001A3 SK 14672001 A SK14672001 A SK 14672001A SK 14672001 A3 SK14672001 A3 SK 14672001A3
- Authority
- SK
- Slovakia
- Prior art keywords
- mirtazapine
- methyl
- phenylpiperazine
- cyanopyridyl
- base
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 20
- 125000004193 piperazinyl group Chemical group 0.000 title abstract description 4
- 238000002425 crystallisation Methods 0.000 title description 3
- 230000008025 crystallization Effects 0.000 title description 3
- 230000015572 biosynthetic process Effects 0.000 title description 2
- 238000003786 synthesis reaction Methods 0.000 title description 2
- RONZAEMNMFQXRA-UHFFFAOYSA-N mirtazapine Chemical compound C1C2=CC=CN=C2N2CCN(C)CC2C2=CC=CC=C21 RONZAEMNMFQXRA-UHFFFAOYSA-N 0.000 claims abstract description 84
- 229960001785 mirtazapine Drugs 0.000 claims abstract description 82
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 65
- 238000000034 method Methods 0.000 claims abstract description 60
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 27
- 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 abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- FEIACFYXEWBKHU-UHFFFAOYSA-N (2-aminopyridin-3-yl)methanol Chemical compound NC1=NC=CC=C1CO FEIACFYXEWBKHU-UHFFFAOYSA-N 0.000 claims abstract description 6
- 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 abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 56
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 42
- 239000002904 solvent Substances 0.000 claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 28
- 239000002585 base Substances 0.000 claims description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 13
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 8
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 8
- 230000007062 hydrolysis Effects 0.000 claims description 7
- -1 iodomethyl Chemical group 0.000 claims description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 229910015900 BF3 Inorganic materials 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 3
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000005997 bromomethyl group Chemical group 0.000 claims description 3
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 3
- 150000007517 lewis acids Chemical class 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 3
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 3
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 3
- 239000011592 zinc chloride Substances 0.000 claims description 3
- 235000005074 zinc chloride Nutrition 0.000 claims description 3
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- HBBBDGWCSBWWKP-UHFFFAOYSA-J tetrachloroantimony Chemical compound Cl[Sb](Cl)(Cl)Cl HBBBDGWCSBWWKP-UHFFFAOYSA-J 0.000 claims 2
- 239000002798 polar solvent Substances 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 abstract description 5
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 4
- 238000010992 reflux Methods 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 19
- 150000002825 nitriles Chemical class 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 230000035484 reaction time Effects 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 6
- 238000006798 ring closing metathesis reaction Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 208000020401 Depressive disease Diseases 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000013505 freshwater Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000003017 phosphorus Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- IRMBVBDXXYXPEW-UHFFFAOYSA-N 1-methyl-3-phenylpiperazine Chemical compound C1N(C)CCNC1C1=CC=CC=C1 IRMBVBDXXYXPEW-UHFFFAOYSA-N 0.000 description 1
- YYXDQRRDNPRJFL-UHFFFAOYSA-N 2-aminopyridine-3-carbonitrile Chemical compound NC1=NC=CC=C1C#N YYXDQRRDNPRJFL-UHFFFAOYSA-N 0.000 description 1
- HTCVSFZWADPKPB-UHFFFAOYSA-N 2-piperazin-1-yl-1h-azepine Chemical group C1CNCCN1C1=CC=CC=CN1 HTCVSFZWADPKPB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 102000010909 Monoamine Oxidase Human genes 0.000 description 1
- 108010062431 Monoamine oxidase Proteins 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- XEKAUTDWPYQNFU-UHFFFAOYSA-N chlorane Chemical compound Cl.Cl.Cl XEKAUTDWPYQNFU-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229940023942 remeron Drugs 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000002699 waste material Substances 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
- 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 | |
| PCT/US2000/010357 WO2000062782A1 (en) | 1999-04-19 | 2000-04-18 | Novel synthesis and crystallization of piperazine ring-containing compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK14672001A3 true SK14672001A3 (sk) | 2002-11-06 |
Family
ID=22442814
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1467-2001A SK14672001A3 (sk) | 1999-04-19 | 2000-04-18 | Spôsob syntézy a kryštalizácie zlúčenín obsahujúcich piperazínový kruh |
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) |
Families Citing this family (13)
| 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 |
| UA83666C2 (ru) * | 2003-07-10 | 2008-08-11 | Н.В. Органон | Способ получения энантиомерно чистого миртазапина |
| 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
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 |
| RU2001128229A (ru) | 2003-07-10 |
| 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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