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US 3,946,025 AGranted
Process for preparing 6H-pyrido[1,2-c][1,3,5]benzothiadiazepines and benzooxadiazepines and derivatives
AssigneeE. R. Squibb & Sons, Inc.
InventorsHarry Louis Yale, Ramesh B. Petigara
Life of this patent
Estimating the term…
Abstract
Compounds of the formula ##SPC1## Exhibit central nervous system stimulating properties and act as muscle relaxants.
Claims3
A method of preparing a compound of the formula ##SPC18##
- wherein m is 1 or 2;
- R is the same or different and is hydrogen, halogen (F, Cl, or Br), alkyl of from 1 to 4 carbons, alkoxy of from 1 to 4 carbons, alkylthio of from 1 to 4 carbons, benzyl, phenethyl, phenyl, phenoxy, phenylthio or mono-substituted phenyl wherein the substituent may be halogen (F, Cl, Br or I), alkyl of from 1 to 4 carbons, alkoxy of from 1 to 4 carbons, or trifluoromethyl;
- provided that when R is halogen, R occupies only the 3- or 5-position in the original 2-aminopyridine;
- R' is hydrogen, halogen (F, Cl or Br), alkyl of from 1 to 4 carbons, phenyl, dialkylamidosulfonyl wherein each alkyl radical is from 1 to 4 carbons or trifluoromethyl;
- n is 0 or 1;
- R" is hydrogen or alkyl of from 1 to 4 carbons and Z is S or SO.sub.2, comprising treating a compound of the formula ##SPC19##
- wherein R, m, R", Z and R' are as defined above with a water miscible alcohol and an alkali metal alkoxide of up to 3 carbon atoms in the presence of copper at a temperature of from about 60.degree.C to about 120.degree.C.
4 more elements
A method of preparing a compound of the formula ##SPC20##
- wherein m is 1 or 2;
- R is the same or different and is hydrogen, halogen (F, Cl, or Br), alkyl of from 1 to 4 carbons, alkoxy of from 1 to 4 carbons, alkylthio of from 1 to 4 carbons, benzyl, phenethyl, phenyl, phenoxy, phenylthio or mono-substituted phenyl wherein the substituent may be halogen (F, Cl, Br or I), alkyl of from 1 to 4 carbons, alkoxy of from 1 to 4 carbons, or trifluoromethyl;
- provided that when R is halogen, R occupies only the 3- or 5-position in the original 2-aminopyridine;
- R' is hydrogen, halogen (F, Cl or Br), alkyl of from 1 to 4 carbons, phenyl, dialkylamidosulfonyl wherein each alkyl radical is from 1 to 4 carbons or trifluoromethyl;
- n is 0 or 1;
- R" is hydrogen or alkyl of from 1 to 4 carbons and Z is S or SO.sub.2,
- comprising heating a compound of the formula ##SPC21##
- wherein R, m, R", n, R' and Z are as defined above and X is Cl or Br at a temperature of from about 60.degree.C to about 120.degree.C in the presence of K.sub.2 CO.sub.3 and Cu.
5 more elements
A method of preparing a compound of the formula ##SPC22##
- wherein m is 1 or 2;
- R is the same or different and is hydrogen, halogen (F, Cl, or Br), alkyl of from 1 to 4 carbons, alkoxy of from 1 to 4 carbons, alkylthio of from 1 to 4 carbons, benzyl, phenethyl, phenyl, phenoxy, phenylthio or mono-substituted phenyl wherein the substituent may be halogen (F, Cl, Br or I), alkyl of from 1 to 4 carbons, alkoxy of from 1 to 4 carbons, or trifluoromethyl;
- provided that when R is halogen, R occupies only the 3- or 5-position in the original 2-aminopyridine;
- R' is hydrogen, halogen (F, Cl or Br), alkyl of from 1 to 4 carbons, phenyl, dialkylamidosulfonyl wherein each alkyl radical is from 1 to 4 carbons or trifluoromethyl;
- n is 0 or 1;
- R" is hydrogen or alkyl of from 1 to 4 carbons and Z is S or SO.sub.2,
- comprising heating a compound of the formula ##SPC23##
- wherein R, m, R", R', n and Z are as defined above and X is Cl or Br at a temperature of from about 60.degree.C to about 120.degree.C in the presence of an alkali metal hydroxide, carbonate, phosphate, metaborate or tetraborate in an anhydrous alcohol of from 1 to about 5 carbon atoms in the presence of copper.
5 more elements
Dependencies are inferred from the claim text.