GB1210519A - Benzylpyridinium compounds and a process for their production - Google Patents
Benzylpyridinium compounds and a process for their productionInfo
- Publication number
- GB1210519A GB1210519A GB57747/67A GB5774767A GB1210519A GB 1210519 A GB1210519 A GB 1210519A GB 57747/67 A GB57747/67 A GB 57747/67A GB 5774767 A GB5774767 A GB 5774767A GB 1210519 A GB1210519 A GB 1210519A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- benzyl
- ether
- compounds
- hbr
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- NDZFNTHGIIQMQI-UHFFFAOYSA-N 1-benzylpyridin-1-ium Chemical class C=1C=CC=C[N+]=1CC1=CC=CC=C1 NDZFNTHGIIQMQI-UHFFFAOYSA-N 0.000 title 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- 229910004373 HOAc Inorganic materials 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical class BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- 230000001590 oxidative effect Effects 0.000 abstract 2
- -1 oxime ethers Chemical class 0.000 abstract 2
- WGQMUABRZGUAOS-UHFFFAOYSA-N (2,5-dimethoxyphenyl)methanol Chemical compound COC1=CC=C(OC)C(CO)=C1 WGQMUABRZGUAOS-UHFFFAOYSA-N 0.000 abstract 1
- WSQCPEYUHYGRJY-UHFFFAOYSA-N 1,2-diethoxy-3-methylbenzene Chemical compound CCOC1=CC=CC(C)=C1OCC WSQCPEYUHYGRJY-UHFFFAOYSA-N 0.000 abstract 1
- KRLRXJANBUGNSF-UHFFFAOYSA-N 1,2-dimethoxy-4-propan-2-ylbenzene Chemical compound COC1=CC=C(C(C)C)C=C1OC KRLRXJANBUGNSF-UHFFFAOYSA-N 0.000 abstract 1
- KQNBRMUBPRGXSL-UHFFFAOYSA-N 1-(bromomethyl)-4-chlorobenzene Chemical compound ClC1=CC=C(CBr)C=C1 KQNBRMUBPRGXSL-UHFFFAOYSA-N 0.000 abstract 1
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 abstract 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical compound CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-UHFFFAOYSA-N 0.000 abstract 1
- KNCHDRLWPAKSII-UHFFFAOYSA-N 5-ethyl-2-methylpyridine Natural products CCC1=CC=NC(C)=C1 KNCHDRLWPAKSII-UHFFFAOYSA-N 0.000 abstract 1
- PPUYLXOFOVDYKU-UHFFFAOYSA-N 5-ethylpyridine-2-carbaldehyde Chemical compound CCC1=CC=C(C=O)N=C1 PPUYLXOFOVDYKU-UHFFFAOYSA-N 0.000 abstract 1
- 208000024172 Cardiovascular disease Diseases 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- FXMRZDRMLWRQJG-UHFFFAOYSA-M [Br-].COC1=C(OC)C(C)=C(C[N+]2=C(C=O)C=CC=C2)C=C1 Chemical compound [Br-].COC1=C(OC)C(C)=C(C[N+]2=C(C=O)C=CC=C2)C=C1 FXMRZDRMLWRQJG-UHFFFAOYSA-M 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- 230000036772 blood pressure Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000002923 oximes Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 150000007659 semicarbazones Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- WMIPJSLGMSZSFE-UHFFFAOYSA-N tert-butylborane Chemical compound BC(C)(C)C WMIPJSLGMSZSFE-UHFFFAOYSA-N 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 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
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen 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
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/48—Aldehydo 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
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/51—Acetal 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,210,519. Oximes, oxime ethers and semicarbazones of 1-benzyl-C-acyl-pyridinium salts. J. R. GEIGY A.G. 20 Dec., 1967 [21 Dec., 1966; 24 Nov., 1967], No. 57747/67. Heading C2C. The invention comprises compounds of formula wherein X is Cl or Br; R 1 is H or R(=C 1-6 alkyl) or in the 3- or 5-positions OH, OR, aralkoxy or aryloxy; R 2 is H, R, OR, F, Cl, Br, NO2, OH, CF 3 , CO 2 alkyl or CN; R 3 is as R 2 except OH; R 4 is as R 3 except R; R 6 is H, OR, F, Cl, Br or NO 2 ; R 6 is H or (when R 2 = R 3 = R 4 = R 5 = F) F; R 7 is H, R, Ph (optionally R- or halogen-substituted), aralkyl, carboalkoxy or 2-pyridyl, and R 8 is OH, OR, aralkoxy or -NHCONH 2 , with the provisos that (1) at least one of R 2 -R 5 is not H; (2) when R 2 is Me, at least one of R 2 -R 5 is not H; (3) when -CR 7 =NR 8 is in the 2-position and (a) if R 3 is OR, at least one of R 2 , R 4 and R 5 is not H, and (b) if R 2 and R 5 are both OR, at least R 3 or R 4 is not H. These compounds are prepared by reacting together the corresponding (i) 1- benzylacylpyridinium salt and NH 2 OH, its O- ether or NH 2 NHCONH 2 ; or (ii) benzyl halide and acylpyridine-oxime (or it O-ether) or -semicarbazone. Starting materials.-Alkoxy-substituted benzyl bromides are prepared by reacting the alkoxysubstituted benzene with CH 2 O/HBr or with MeOCH 2 Br (made from MeOH, CH 2 O and HBr), or the benzyl alcohol with HBr; 4- chlorobenzyl bromide is prepared similarly. 5-Ethyl-2-formylpyridine is prepared by oxidizing 5-ethyl-2-methylpyridine with H 2 O 2 /HOAc, reacting the product with Ac 2 O and again oxidizing with H 2 O 2 /HOAc. 3-Methylcatechol diethyl ether is prepared from the phenol with Et 2 SO 4 ; 4-isopropylcatechol dimethyl ether is prepared analogously. 2,5-Dimethoxybenzyl alcohol is prepared by reducing the aldehyde with t - butylborane. 1 - (2 - Methyl - 3,4 - dimethoxybenzyl) -2-formylpyridinium bromide is made from the benzyl bromide and 2-formylpyridine. Therapeutic compositions for treating cardiovascular disorders, particularly for lowering blood pressure, comprise compounds of the above general formula, and may be administered orally, rectally or parenterally.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60341866A | 1966-12-21 | 1966-12-21 | |
| US68531767A | 1967-11-24 | 1967-11-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1210519A true GB1210519A (en) | 1970-10-28 |
Family
ID=27084423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB57747/67A Expired GB1210519A (en) | 1966-12-21 | 1967-12-20 | Benzylpyridinium compounds and a process for their production |
Country Status (13)
| Country | Link |
|---|---|
| AT (1) | AT278783B (en) |
| BE (1) | BE708316A (en) |
| CH (1) | CH487154A (en) |
| DE (1) | DE1695101A1 (en) |
| DK (1) | DK118876B (en) |
| ES (1) | ES348464A1 (en) |
| FR (2) | FR1550578A (en) |
| GB (1) | GB1210519A (en) |
| GR (1) | GR37786B (en) |
| IL (1) | IL29176A (en) |
| NL (2) | NL6717412A (en) |
| NO (1) | NO123894B (en) |
| SE (1) | SE337373B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4352810A (en) | 1979-07-26 | 1982-10-05 | Nederlandse Centrale Organisatie Voor Toegepast-Natuurwetenschappelijkond erzoek | 1-Substituted hydroxyiminomethyl-pyridinium salts, with an activity against organophosphate poisonings |
| EP0643697A1 (en) * | 1992-06-02 | 1995-03-22 | Georgia Tech Research Corporation | Quaternary pyridinium compounds |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1600969A (en) * | 1977-01-07 | 1981-10-21 | Acf Chemiefarma Nv | Heterocyclic compounds |
-
1967
- 1967-12-20 DE DE19671695101 patent/DE1695101A1/en active Pending
- 1967-12-20 ES ES348464A patent/ES348464A1/en not_active Expired
- 1967-12-20 FR FR1550578D patent/FR1550578A/fr not_active Expired
- 1967-12-20 NL NL6717412A patent/NL6717412A/xx unknown
- 1967-12-20 BE BE708316D patent/BE708316A/xx unknown
- 1967-12-20 AT AT1152067A patent/AT278783B/en not_active IP Right Cessation
- 1967-12-20 NO NO17107867A patent/NO123894B/no unknown
- 1967-12-20 GB GB57747/67A patent/GB1210519A/en not_active Expired
- 1967-12-20 IL IL2917667A patent/IL29176A/en unknown
- 1967-12-20 SE SE1747767A patent/SE337373B/xx unknown
- 1967-12-20 CH CH1788967A patent/CH487154A/en not_active IP Right Cessation
- 1967-12-20 GR GR670137786A patent/GR37786B/en unknown
- 1967-12-20 DK DK638267A patent/DK118876B/en unknown
- 1967-12-20 NL NL6717413A patent/NL6717413A/xx unknown
-
1968
- 1968-03-19 FR FR144357A patent/FR7308M/fr not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4352810A (en) | 1979-07-26 | 1982-10-05 | Nederlandse Centrale Organisatie Voor Toegepast-Natuurwetenschappelijkond erzoek | 1-Substituted hydroxyiminomethyl-pyridinium salts, with an activity against organophosphate poisonings |
| EP0643697A1 (en) * | 1992-06-02 | 1995-03-22 | Georgia Tech Research Corporation | Quaternary pyridinium compounds |
| EP0643697A4 (en) * | 1992-06-02 | 1995-04-12 | Georgia Tech Research Corporation | Quaternary pyridinium compounds. |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6717413A (en) | 1968-06-24 |
| FR1550578A (en) | 1968-12-20 |
| CH487154A (en) | 1970-03-15 |
| IL29176A (en) | 1972-08-30 |
| NL6717412A (en) | 1968-06-24 |
| FR7308M (en) | 1969-09-29 |
| DE1695101A1 (en) | 1971-03-18 |
| GR37786B (en) | 1969-07-15 |
| BE708316A (en) | 1968-06-20 |
| NO123894B (en) | 1972-01-31 |
| AT278783B (en) | 1970-02-10 |
| ES348464A1 (en) | 1969-06-16 |
| SE337373B (en) | 1971-08-09 |
| DK118876B (en) | 1970-10-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1132082A (en) | The manufacture of pyrimidine derivatives | |
| GB1226344A (en) | ||
| GB1409656A (en) | Tetrazole derivatives | |
| GB1210519A (en) | Benzylpyridinium compounds and a process for their production | |
| GB1451410A (en) | Process for the manufacture of 2- 2-hydroxyphenyl-benzotriazole-1 oxides | |
| IE31926L (en) | Dibenzazepine derivatives | |
| GB1481161A (en) | 5-(substituted-benzoyloxy)pyrazoles and a process for their conversion to 4-benzoyl-pyrazole derivatives | |
| GB1439151A (en) | Process for the production of diazepine derivatives | |
| GB1221712A (en) | Novel trifluoromethyl-phenyl compounds and a process for the manufacture thereof | |
| GB1170098A (en) | New 1,2-Nitranilines and their production | |
| GB1208195A (en) | Process for producing benzodiazepine derivatives | |
| GB1419243A (en) | Dimorpholinomethyl cyclohexenes and their use in a process for the manufacture of aldehydes | |
| GB1210602A (en) | New furazan derivatives, processes for their production and compositions containing them | |
| GB1472767A (en) | Process for the preparation of cinnoline derivatives | |
| GB1346378A (en) | 2-stilbenyl-4-styryl-v-triazoles their use for the optical brightening of organic materials and processes for their manufacture | |
| Murata | The Structure of 4-(α-Ethylenedioxy) ethyltropolone Methyl Ether | |
| GB1183968A (en) | A Process for the Production of Substituted Phenyl Acetic Acids | |
| ES379871A1 (en) | Certain 2-alkoxymethyl-3-chloro-delta 3-1,2,4-thiadiazolin-5-ones and their preparation | |
| FR2015456A1 (en) | Use of organic disulphides as fog inhibitors - for silver halide photographic emulsions | |
| GB1344957A (en) | 3-aryl-2-halothiopropionic acid derivatives their preparation and their use as herbicides as herbicides | |
| ES307270A1 (en) | Procedure for the production of heterociclic compounds. (Machine-translation by Google Translate, not legally binding) | |
| Wheeler et al. | The Chlorination of 2-Nitro-p-cymene. I. Monosubstitution1 | |
| GB1130909A (en) | New 3-[2-(5-nitrofuryl-2)-vinyl]-s-triazolo-[4.3-a]-pyridine derivatives and process for the preparation thereof | |
| GB1223569A (en) | Azidocinnamic aldehydes and process for their manufacture | |
| ES341311A1 (en) | Dehydration process for forming benzodiazepines |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |