SE409860B - En ny mellanprodukt for framstellning av terapeutiskt aktiva pyridinforeningar - Google Patents
En ny mellanprodukt for framstellning av terapeutiskt aktiva pyridinforeningarInfo
- Publication number
- SE409860B SE409860B SE7707708A SE7707708A SE409860B SE 409860 B SE409860 B SE 409860B SE 7707708 A SE7707708 A SE 7707708A SE 7707708 A SE7707708 A SE 7707708A SE 409860 B SE409860 B SE 409860B
- Authority
- SE
- Sweden
- Prior art keywords
- solution
- water
- added
- preparation
- hours
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title 1
- 239000013067 intermediate product Substances 0.000 title 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 11
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- 239000008346 aqueous phase Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 6
- 229910021529 ammonia Inorganic materials 0.000 claims 3
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000012043 crude product Substances 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000012044 organic layer Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 238000006748 scratching Methods 0.000 claims 1
- 230000002393 scratching effect Effects 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- IJMWREDHKRHWQI-UHFFFAOYSA-M magnesium;ethene;chloride Chemical compound [Mg+2].[Cl-].[CH-]=C IJMWREDHKRHWQI-UHFFFAOYSA-M 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- RMGJCSHZTFKPNO-UHFFFAOYSA-M magnesium;ethene;bromide Chemical compound [Mg+2].[Br-].[CH-]=C RMGJCSHZTFKPNO-UHFFFAOYSA-M 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003509 tertiary alcohols Chemical class 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- IDGVUIHZWDVXOQ-UHFFFAOYSA-N (4-bromophenyl)-pyridin-3-ylmethanone Chemical compound C1=CC(Br)=CC=C1C(=O)C1=CC=CN=C1 IDGVUIHZWDVXOQ-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- OYPPVKRFBIWMSX-UHFFFAOYSA-N Cis-zimelidine Chemical compound C=1C=CN=CC=1C(=CCN(C)C)C1=CC=C(Br)C=C1 OYPPVKRFBIWMSX-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- LJHIEJTWMRHBFW-UHFFFAOYSA-N O=C(C1=C(CBr)C=CN=C1)C1=C(CBr)C=CN=C1 Chemical compound O=C(C1=C(CBr)C=CN=C1)C1=C(CBr)C=CN=C1 LJHIEJTWMRHBFW-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- NJSUFZNXBBXAAC-UHFFFAOYSA-N ethanol;toluene Chemical compound CCO.CC1=CC=CC=C1 NJSUFZNXBBXAAC-UHFFFAOYSA-N 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical class II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000004794 vinyl magnesium halides Chemical class 0.000 description 1
- 210000002268 wool Anatomy 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Priority Applications (24)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7707708A SE409860B (sv) | 1977-07-04 | 1977-07-04 | En ny mellanprodukt for framstellning av terapeutiskt aktiva pyridinforeningar |
| IL54973A IL54973A (en) | 1977-07-04 | 1978-06-22 | Process for the preparation of n,n-dimethyl(or n-methyl)-3-(p-bromophenyl)3-(3-pyridyl)allylamine and novel 3-(p-bromophenyl)-3-(3-pyridyl)3-hydroxyprop-1-ene intermediate therefor |
| US05/918,724 US4216328A (en) | 1977-07-04 | 1978-06-26 | Novel intermediate for preparation of therapeutically active compounds |
| PCT/SE1978/000010 WO1979000024A1 (en) | 1977-07-04 | 1978-06-26 | A novel intermediate for preparation of therapeutically active pyridine compounds |
| GB7920315A GB2036002B (en) | 1977-07-04 | 1978-06-26 | Intermediate for preparation of therapeutically active pyridine compounds |
| EP78900032A EP0006864B1 (de) | 1977-07-04 | 1978-06-26 | Neues zwischenprodukt für die herstellung therapeutisch wirksamer pyridinverbindungen und verfahren zu dessen herstellung |
| DE19782857020 DE2857020A1 (de) | 1977-07-04 | 1978-06-26 | A novel intermediate for preparation of therapeutically active pyridine compounds |
| CH330079A CH642354A5 (de) | 1977-07-04 | 1978-06-26 | Neues chemisches verbindungszwischenprodukt fuer die herstellung von therapeutisch aktiven verbindungen. |
| DK782952A DK295278A (da) | 1977-07-04 | 1978-06-29 | Mellemprodukt til fremstilling af terapeutisk virksomme aminer |
| AU37613/78A AU520374B2 (en) | 1977-07-04 | 1978-06-29 | 3-(4-bromophenyl)-3-(3-pyridyl)-3-hydroxy-prop-(1)-ene and to processes employing it |
| CA306,599A CA1099725A (en) | 1977-07-04 | 1978-06-30 | 3-(4-bromophenyl)-3-(3-pyridyl)-3-hydroxy-prop-(1)- ene |
| NL7807121A NL7807121A (nl) | 1977-07-04 | 1978-06-30 | Tussenprodukt voor de bereiding van therapeutisch werk- zame verbindingen. |
| FI782116A FI64579C (fi) | 1977-07-04 | 1978-06-30 | Som mellanprodukt anvaendbar 3-(4-bromfenyl)-3-(3-pyridyl)-3-hydroxi-prop-(1)-en foerfarande foer framstaellning daerav oc foerfarande foer framstaellning av terapeutiskt aktiva 3 -(-bromfenyl)-3-(3-pyridyl)-allylaminderivat |
| IE1334/78A IE47017B1 (en) | 1977-07-04 | 1978-07-03 | 3-(4-bromophenyl)-3-(3-pyridyl)-3-hydroxy-prop-1-ene and its use to prepare pharmaceutically active compounds |
| NO782303A NO150604C (no) | 1977-07-04 | 1978-07-03 | Fremgangsmaate for fremstilling av n-monometyl- og n,n-dimetyl-3-(4-bromfenyl)-3-(3-pyridyl)-allylamin samt salter og isomerer derav |
| IT50141/78A IT1105249B (it) | 1977-07-04 | 1978-07-03 | Procedimento per la preparazione di intermedi per la produzione di composti terapeuticamente attivi |
| ES471365A ES471365A1 (es) | 1977-07-04 | 1978-07-03 | Un procedimiento para la preparacion de derivados de 3-(4- bromofenil)-3-(3-piridil)-alilamina terapeuticamente activos |
| AT0483678A AT364825B (de) | 1977-07-04 | 1978-07-04 | Verfahren zur herstellung des neuen 3-(4-bromphenyl)-3-(3-pyridyl)-3-hydroxyprop-1-en und dessen saeureadditionssalzen |
| BE189041A BE868701A (fr) | 1977-07-04 | 1978-07-04 | Nouveau produit intermediaire pour la preparation de composes therapeutiquement actifs |
| JP53081819A JPS607981B2 (ja) | 1977-07-04 | 1978-07-04 | 新規な化合物およびその製法 |
| SE7905429A SE418742B (sv) | 1977-07-04 | 1979-06-20 | Nytt forfarande for framstellning av n-metyl-(eller n,n-dimetyl)-3-4(bromfenyl)-3-(3-pyridyl)-alkylamin |
| SU792800303A SU927113A3 (ru) | 1977-07-04 | 1979-08-03 | Способ получени производных пиридиламина |
| AT27481A AT366667B (de) | 1977-07-04 | 1981-01-23 | Verfahren zur herstellung von substituierten allylaminen sowie von deren stereoisomeren, hydraten und pharmazeutisch akzeptablen salzen |
| JP57066429A JPS609024B2 (ja) | 1977-07-04 | 1982-04-22 | 治療活性化合物の新規な製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7707708A SE409860B (sv) | 1977-07-04 | 1977-07-04 | En ny mellanprodukt for framstellning av terapeutiskt aktiva pyridinforeningar |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7707708L SE7707708L (sv) | 1979-01-05 |
| SE409860B true SE409860B (sv) | 1979-09-10 |
Family
ID=20331765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7707708A SE409860B (sv) | 1977-07-04 | 1977-07-04 | En ny mellanprodukt for framstellning av terapeutiskt aktiva pyridinforeningar |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4216328A (de) |
| EP (1) | EP0006864B1 (de) |
| JP (2) | JPS607981B2 (de) |
| AT (1) | AT364825B (de) |
| AU (1) | AU520374B2 (de) |
| BE (1) | BE868701A (de) |
| CA (1) | CA1099725A (de) |
| CH (1) | CH642354A5 (de) |
| DK (1) | DK295278A (de) |
| ES (1) | ES471365A1 (de) |
| FI (1) | FI64579C (de) |
| GB (1) | GB2036002B (de) |
| IE (1) | IE47017B1 (de) |
| IL (1) | IL54973A (de) |
| IT (1) | IT1105249B (de) |
| NL (1) | NL7807121A (de) |
| NO (1) | NO150604C (de) |
| SE (1) | SE409860B (de) |
| SU (1) | SU927113A3 (de) |
| WO (1) | WO1979000024A1 (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1981001407A1 (en) * | 1979-11-16 | 1981-05-28 | Astra Laekemedel Ab | Novel halophenyl-pyridyl-allylamine derivatives |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0354870Y2 (de) * | 1985-10-28 | 1991-12-04 | ||
| DE4036216C1 (de) * | 1990-11-14 | 1992-01-30 | Voest-Alpine Industrieanlagenbau Ges.M.B.H., Linz, At |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB850298A (en) * | 1956-10-30 | 1960-10-05 | Maggioni & C Societa Per Azion | ª‡,ª‡[(p-chlorophenyl)-(4-pyridyl)] carbinols and method of preparing same |
| DE1468359A1 (de) * | 1963-10-23 | 1968-11-28 | Merck & Co Inc | Verfahren zur Herstellung von Dibenzocycloheptehderivaten |
| US3396224A (en) * | 1965-09-09 | 1968-08-06 | Lilly Co Eli | Controlling phytopathogenic fungi on plants with 3-pyridyl methane derivatives |
| US3471505A (en) * | 1967-02-01 | 1969-10-07 | Ciba Geigy Corp | 1-(alkoxyphenyl)-1-(3-pyridyl)-carbinols |
| US3928369A (en) * | 1971-04-28 | 1975-12-23 | Haessle Ab | Compounds useful as antidepressive agents, and a process for their preparation |
| US4094908A (en) * | 1973-08-15 | 1978-06-13 | Richter Gedeon Vegyeszeti Gyar Rt. | Alpha-substituted benzhydrol derivatives |
| GB1480593A (en) * | 1973-11-30 | 1977-07-20 | Kefalas As | Xanthene and thioxanthene derivatives having pharmaceutical activity |
| SE388854B (sv) * | 1974-11-21 | 1979-03-26 | Astra Laekemedel Ab | Forfarande for framstellning av fenylpyridylaminderivat |
-
1977
- 1977-07-04 SE SE7707708A patent/SE409860B/sv unknown
-
1978
- 1978-06-22 IL IL54973A patent/IL54973A/xx unknown
- 1978-06-26 CH CH330079A patent/CH642354A5/de not_active IP Right Cessation
- 1978-06-26 EP EP78900032A patent/EP0006864B1/de not_active Expired
- 1978-06-26 WO PCT/SE1978/000010 patent/WO1979000024A1/en unknown
- 1978-06-26 GB GB7920315A patent/GB2036002B/en not_active Expired
- 1978-06-26 US US05/918,724 patent/US4216328A/en not_active Expired - Lifetime
- 1978-06-29 AU AU37613/78A patent/AU520374B2/en not_active Expired
- 1978-06-29 DK DK782952A patent/DK295278A/da not_active Application Discontinuation
- 1978-06-30 NL NL7807121A patent/NL7807121A/xx not_active Application Discontinuation
- 1978-06-30 FI FI782116A patent/FI64579C/fi not_active IP Right Cessation
- 1978-06-30 CA CA306,599A patent/CA1099725A/en not_active Expired
- 1978-07-03 ES ES471365A patent/ES471365A1/es not_active Expired
- 1978-07-03 NO NO782303A patent/NO150604C/no unknown
- 1978-07-03 IE IE1334/78A patent/IE47017B1/en unknown
- 1978-07-03 IT IT50141/78A patent/IT1105249B/it active
- 1978-07-04 AT AT0483678A patent/AT364825B/de not_active IP Right Cessation
- 1978-07-04 JP JP53081819A patent/JPS607981B2/ja not_active Expired
- 1978-07-04 BE BE189041A patent/BE868701A/xx not_active IP Right Cessation
-
1979
- 1979-08-03 SU SU792800303A patent/SU927113A3/ru active
-
1982
- 1982-04-22 JP JP57066429A patent/JPS609024B2/ja not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1981001407A1 (en) * | 1979-11-16 | 1981-05-28 | Astra Laekemedel Ab | Novel halophenyl-pyridyl-allylamine derivatives |
| US4418065A (en) | 1979-11-16 | 1983-11-29 | Astra Lakemedel Aktiebolag | Halophenyl-pyridyl-allylamine derivatives and use |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS609024B2 (ja) | 1985-03-07 |
| AT364825B (de) | 1981-11-25 |
| IT1105249B (it) | 1985-10-28 |
| EP0006864B1 (de) | 1981-12-30 |
| JPS607981B2 (ja) | 1985-02-28 |
| SE7707708L (sv) | 1979-01-05 |
| ES471365A1 (es) | 1979-10-01 |
| BE868701A (fr) | 1979-01-04 |
| GB2036002A (en) | 1980-06-25 |
| CA1099725A (en) | 1981-04-21 |
| AU520374B2 (en) | 1982-01-28 |
| ATA483678A (de) | 1981-04-15 |
| GB2036002B (en) | 1982-04-21 |
| IT7850141A0 (it) | 1978-07-03 |
| FI64579B (fi) | 1983-08-31 |
| IL54973A0 (en) | 1978-08-31 |
| EP0006864A1 (de) | 1980-01-23 |
| FI64579C (fi) | 1983-12-12 |
| CH642354A5 (de) | 1984-04-13 |
| NO150604B (no) | 1984-08-06 |
| AU3761378A (en) | 1980-01-03 |
| NO150604C (no) | 1984-11-14 |
| SU927113A3 (ru) | 1982-05-07 |
| DK295278A (da) | 1979-01-05 |
| NL7807121A (nl) | 1979-01-08 |
| IE781334L (en) | 1979-01-04 |
| WO1979000024A1 (en) | 1979-01-25 |
| NO782303L (no) | 1979-01-05 |
| FI782116A (fi) | 1979-01-05 |
| JPS5414975A (en) | 1979-02-03 |
| JPS57183759A (en) | 1982-11-12 |
| US4216328A (en) | 1980-08-05 |
| IE47017B1 (en) | 1983-11-30 |
| IL54973A (en) | 1981-12-31 |
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