GB782067A - Novel pyridinium salts and a process for the manufacture of same - Google Patents
Novel pyridinium salts and a process for the manufacture of sameInfo
- Publication number
- GB782067A GB782067A GB8260/56A GB826056A GB782067A GB 782067 A GB782067 A GB 782067A GB 8260/56 A GB8260/56 A GB 8260/56A GB 826056 A GB826056 A GB 826056A GB 782067 A GB782067 A GB 782067A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- hydroxymethyl
- acetamido
- phenyl
- ethyl
- 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- 150000001450 anions Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- VBSTXRUAXCTZBQ-UHFFFAOYSA-N 1-hexyl-4-phenylpiperazine Chemical compound C1CN(CCCCCC)CCN1C1=CC=CC=C1 VBSTXRUAXCTZBQ-UHFFFAOYSA-N 0.000 abstract 1
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- IJAJTZPIESJLIR-UHFFFAOYSA-N C(C)(=O)[ClH]C(C(CO)C1=CC=CC=C1)=O Chemical compound C(C)(=O)[ClH]C(C(CO)C1=CC=CC=C1)=O IJAJTZPIESJLIR-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- JACRWUWPXAESPB-QMMMGPOBSA-N Tropic acid Natural products OC[C@H](C(O)=O)C1=CC=CC=C1 JACRWUWPXAESPB-QMMMGPOBSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 125000002015 acyclic group Chemical group 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 238000010531 catalytic reduction reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- -1 ethyl sulphate anion Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000003701 inert diluent Substances 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 abstract 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Abstract
The invention comprises compounds of the formula <FORM:0782067/IV (a)/1> wherein R is a hydrogen atom or an acyclic hydrocarbon group of up to four carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl or allyl, Q is a hydrocarbon radical of not more than eight carbon atoms such as a methyl, ethyl, allyl, benzyl or phenylethyl group and X is an anion, preferably a pharmaceutically acceptable anion such as a chloride, bromide, iodide, methyl sulphate or ethyl sulphate anion. The compounds are made by treating the corresponding a -hydroxymethyl-a -phenylacetyl-N-picolylamide with a quaternating agent QX, suitably by heating the reactants in an inert solvent or diluent. Examples describe the preparation of 1-methyl-3-(N-methyl-a -phenyl-a - hydroxymethyl - acetamido) - pyridinium iodide; 1 - methyl - 4 - (N - ethyl - a - phenyl - a - hydroxymethyl - acetamido) - pyridinium methyl sulphate; 1 - allyl - 3 - (N - allyl - a - phenyl - a - hydroxymethyl - acetamido) - pyridinium bromide; 1 - methyl - 4 - (N - ethyl - a - phenyl - a - hydroxymethyl - acetamido) - pyridinium iodide; 1 - methyl - 2 - (N - methyl - a - phenyl - a - hydroxymethyl - acetamido) - pyridinium iodide; 1 - benzyl - 2 - (a - phenyl - a - hydroxymethyl - acetamido) - pyridinium chloride and 1 - methyl - 4 - (N - ethyl - a - phenyl - a - hydroxymethyl - acetamido) - pyridinium bromide. Many other compounds obtainable according to the invention are specified. Intermediates. The a - hydroxymethyl - a - phenylacetyl - N - picolyl - amides used as starting materials such as tropic acid N-methyl-N-(a -picolyl)-amide and tropic acid-N(a -picolyl-amide are made by treating O-acetyl-tropic acid chloride with a pyridylmethylamine, the amino radical of which may contain a lower acyclic hydrocarbon radical "R" as a substituent and hydrolysing off the acetyl group from the resulting O-acetyl amide. Methyl a -picolyl amine is made by treating a -hydroxymethyl-pyridine with phosphorus pentachloride and reacting the resulting a -chloromethyl-pyridine with methylamine. a -Aminomethyl-pyridine is made by catalytic reduction of a -cyanopyridine.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH782067X | 1955-03-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB782067A true GB782067A (en) | 1957-08-28 |
Family
ID=4536303
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8260/56A Expired GB782067A (en) | 1955-03-21 | 1956-03-16 | Novel pyridinium salts and a process for the manufacture of same |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB782067A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007120729A2 (en) * | 2006-04-12 | 2007-10-25 | Merck & Co., Inc. | Pyridyl amide t-type calcium channel antagonists |
| US8637513B2 (en) | 2007-10-24 | 2014-01-28 | Merck Sharp & Dohme Corp. | Heterocycle phenyl amide T-type calcium channel antagonists |
-
1956
- 1956-03-16 GB GB8260/56A patent/GB782067A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007120729A2 (en) * | 2006-04-12 | 2007-10-25 | Merck & Co., Inc. | Pyridyl amide t-type calcium channel antagonists |
| WO2007120729A3 (en) * | 2006-04-12 | 2008-01-03 | Merck & Co Inc | Pyridyl amide t-type calcium channel antagonists |
| US7875636B2 (en) | 2006-04-12 | 2011-01-25 | Merck Sharp & Dohme Corp. | Pyridyl amide T-type calcium channel antagonists |
| AU2007238755B2 (en) * | 2006-04-12 | 2012-07-12 | Merck Sharp & Dohme Llc | Pyridyl amide T-type calcium channel antagonists |
| US8263627B2 (en) | 2006-04-12 | 2012-09-11 | Merck Sharp & Dohme Corp. | Pyridyl amide T-type calcium channel antagonists |
| US8637513B2 (en) | 2007-10-24 | 2014-01-28 | Merck Sharp & Dohme Corp. | Heterocycle phenyl amide T-type calcium channel antagonists |
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