NO860825L - Fremgangsmaate til fremstilling av 2-amino-3-nitro-6-(4-fluor-benzylamino)-pyridin samt 2-amino-3-karbetoksyamino-6-(4-fluor-benzylamino)-pyridin. - Google Patents
Fremgangsmaate til fremstilling av 2-amino-3-nitro-6-(4-fluor-benzylamino)-pyridin samt 2-amino-3-karbetoksyamino-6-(4-fluor-benzylamino)-pyridin.Info
- Publication number
- NO860825L NO860825L NO860825A NO860825A NO860825L NO 860825 L NO860825 L NO 860825L NO 860825 A NO860825 A NO 860825A NO 860825 A NO860825 A NO 860825A NO 860825 L NO860825 L NO 860825L
- Authority
- NO
- Norway
- Prior art keywords
- amino
- pyridine
- nitro
- benzylamino
- acid
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- ZVCIIRBNNSUNCH-UHFFFAOYSA-N 6-n-[(4-fluorophenyl)methyl]-3-nitropyridine-2,6-diamine Chemical compound C1=C([N+]([O-])=O)C(N)=NC(NCC=2C=CC(F)=CC=2)=C1 ZVCIIRBNNSUNCH-UHFFFAOYSA-N 0.000 title claims abstract description 6
- IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 9
- RDJILYVRVOTMTQ-UHFFFAOYSA-N 6-methoxy-3-nitropyridin-2-amine Chemical compound COC1=CC=C([N+]([O-])=O)C(N)=N1 RDJILYVRVOTMTQ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- -1 2-amino-3-nitro-(4-fluoro-benzylamino)-pyridine Chemical compound 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- JUUFBMODXQKSTD-UHFFFAOYSA-N N-[2-amino-6-[(4-fluorophenyl)methylamino]-3-pyridinyl]carbamic acid ethyl ester Chemical compound N1=C(N)C(NC(=O)OCC)=CC=C1NCC1=CC=C(F)C=C1 JUUFBMODXQKSTD-UHFFFAOYSA-N 0.000 claims description 4
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
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- 239000000203 mixture Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- 239000002904 solvent Substances 0.000 description 4
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- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- XUEZMHGLLYOBIT-UHFFFAOYSA-N phenylmethanamine;hydrate Chemical compound [OH-].[NH3+]CC1=CC=CC=C1 XUEZMHGLLYOBIT-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical class NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L sodium sulphate Substances [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3510623 | 1985-03-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
NO860825L true NO860825L (no) | 1986-09-24 |
Family
ID=6266157
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO860825A NO860825L (no) | 1985-03-23 | 1986-03-05 | Fremgangsmaate til fremstilling av 2-amino-3-nitro-6-(4-fluor-benzylamino)-pyridin samt 2-amino-3-karbetoksyamino-6-(4-fluor-benzylamino)-pyridin. |
Country Status (24)
Country | Link |
---|---|
US (1) | US4785110A (fr) |
EP (1) | EP0199951B1 (fr) |
JP (1) | JPS61221172A (fr) |
KR (1) | KR860007214A (fr) |
AT (1) | ATE60322T1 (fr) |
AU (1) | AU579922B2 (fr) |
BR (1) | BR8601283A (fr) |
CA (1) | CA1273343A (fr) |
CS (1) | CS259887B2 (fr) |
DD (1) | DD246761A5 (fr) |
DE (1) | DE3677042D1 (fr) |
DK (1) | DK162215C (fr) |
ES (1) | ES8702893A1 (fr) |
FI (1) | FI84819C (fr) |
GR (1) | GR860745B (fr) |
HU (1) | HU206679B (fr) |
IE (1) | IE58560B1 (fr) |
IL (1) | IL78218A (fr) |
NO (1) | NO860825L (fr) |
PL (1) | PL146631B1 (fr) |
PT (1) | PT82235B (fr) |
TR (1) | TR22924A (fr) |
YU (1) | YU45086A (fr) |
ZA (1) | ZA862138B (fr) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FI855016A (fi) * | 1985-06-28 | 1986-12-29 | Degussa | Synergistisk kombination av flupirtin och 4-acetamido-fenol. |
DE4327516A1 (de) * | 1993-08-17 | 1995-02-23 | Asta Medica Ag | Primäre und sekundäre neuroprotektive Wirkung bei neurodegenerativen Erkrankungen von Flupirtin |
JPWO2004069802A1 (ja) * | 2003-02-06 | 2006-05-25 | 塩野義製薬株式会社 | 2−アミノ−3−置換ピリジンの製造方法 |
US20080279930A1 (en) * | 2007-05-07 | 2008-11-13 | Bernd Terhaag | Controlled-Release Flupirtine Compositions, Compacts, Kits and Methods of Making and Use Thereof |
EP2206700A1 (fr) | 2008-12-24 | 2010-07-14 | AWD.pharma GmbH & Co.KG | Forme cristalline de flupirtine (ester éthyl d'acide carbamique 2-amino-6-(4-fluoro-benzylamino)-pyridin-3-yl) |
EP2206701A1 (fr) | 2008-12-24 | 2010-07-14 | AWD.pharma GmbH & Co.KG | Forme cristalline de flupirtine (ester éthyl d'acide carbamique 2-amino-6-(4-fluoro-benzylamino)-pyridin-3-yl) |
EP2206699A1 (fr) | 2008-12-24 | 2010-07-14 | AWD.pharma GmbH & Co.KG | Forme cristalline de flupirtine (ester éthyl d'acide carbamique 2-amino-6-(4-fluoro-benzylamino)-pyridin-3-yl) |
DE102009023162B4 (de) * | 2009-05-29 | 2011-07-07 | Corden PharmaChem GmbH, 68305 | Verfahren zur Herstellung von Flupirtin |
CN102140077A (zh) * | 2010-01-28 | 2011-08-03 | 范扶民 | 氟吡汀a晶型及其制备方法 |
WO2013080215A1 (fr) | 2011-11-30 | 2013-06-06 | Arch Pharmalabs Limited | Procédé amélioré pour la préparation de flupirtine et des sels pharmaceutiquement acceptables de celle-ci |
CN104083335B (zh) * | 2013-07-31 | 2015-11-11 | 成都苑东药业有限公司 | 一种马来酸氟吡汀胶囊组合物及其制备方法 |
DE102017007385A1 (de) | 2017-08-02 | 2019-02-07 | Christoph Hoock | Maleatfreie feste Arzneimittelformen |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE764362R (fr) * | 1966-05-12 | 1971-09-16 | Degussa | Procedes de preparation de nouvelles diaminopyridines |
DE1670522C3 (de) * | 1966-05-12 | 1978-08-31 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Neue Benzylaminopyridine |
US4481205A (en) * | 1980-09-13 | 1984-11-06 | Degussa Aktiengesellschaft | 2-Amino-3-carbethoxyamino-6-(p-fluoro-benzylamino)-pyridine-maleate |
EP0110091B1 (fr) * | 1982-10-27 | 1987-01-21 | Degussa Aktiengesellschaft | Dérivés de la 2-amino-3-acylamino-6-benzylamino-pyridine à activité antiépileptique |
-
1986
- 1986-03-05 NO NO860825A patent/NO860825L/no unknown
- 1986-03-15 AT AT86103517T patent/ATE60322T1/de not_active IP Right Cessation
- 1986-03-15 DE DE8686103517T patent/DE3677042D1/de not_active Expired - Lifetime
- 1986-03-15 EP EP86103517A patent/EP0199951B1/fr not_active Expired - Lifetime
- 1986-03-19 DK DK126886A patent/DK162215C/da not_active IP Right Cessation
- 1986-03-20 FI FI861183A patent/FI84819C/fi not_active IP Right Cessation
- 1986-03-20 GR GR860745A patent/GR860745B/el unknown
- 1986-03-21 IE IE74686A patent/IE58560B1/en not_active IP Right Cessation
- 1986-03-21 CS CS861986A patent/CS259887B2/cs unknown
- 1986-03-21 AU AU54997/86A patent/AU579922B2/en not_active Expired
- 1986-03-21 YU YU00450/86A patent/YU45086A/xx unknown
- 1986-03-21 DD DD86288169A patent/DD246761A5/de unknown
- 1986-03-21 BR BR8601283A patent/BR8601283A/pt not_active IP Right Cessation
- 1986-03-21 ZA ZA862138A patent/ZA862138B/xx unknown
- 1986-03-21 CA CA000504732A patent/CA1273343A/fr not_active Expired - Lifetime
- 1986-03-21 PT PT82235A patent/PT82235B/pt unknown
- 1986-03-21 ES ES553222A patent/ES8702893A1/es not_active Expired
- 1986-03-21 IL IL78218A patent/IL78218A/xx unknown
- 1986-03-21 PL PL1986258543A patent/PL146631B1/pl unknown
- 1986-03-22 TR TR163/86A patent/TR22924A/xx unknown
- 1986-03-22 KR KR1019860002142A patent/KR860007214A/ko not_active Application Discontinuation
- 1986-03-24 HU HU861216A patent/HU206679B/hu unknown
- 1986-03-24 JP JP61064292A patent/JPS61221172A/ja active Granted
- 1986-03-24 US US06/843,253 patent/US4785110A/en not_active Expired - Lifetime
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