2-Aminomethyl-3,4-dihydronaphthalenes

• US 4,022,791 A
• Filed: 06/03/1975
• Issued: 05/10/1977
• Est. Priority Date: 06/03/1975
• Status: Expired due to Term

• Current Assignee: Pfizer Inc.
• Original Assignee: Pfizer Inc.
• Inventors: Welch, Willard M. Jr.
• Primary Examiner(s): Todd, G. Thomas
• Application Number:
  US05/583,420
• Time in Patent Office: 707 Days
• Field of Search: 260/247.2 A, 260/247.2 B, 260/247.7 C, 260/268 BC, 260/293.62, 260/306.7 E, 260/326.33, 260/326.5 M
• US Class Current: 546/20
• CPC Class Codes: C07C 45/46 Friedel-Crafts reactions
• CPC Class Codes: C07C 45/673 by change of size of the carbon skeleton
• CPC Class Codes: C07C 45/71 being hydroxy groups
• CPC Class Codes: C07C 49/747 containing six-membered aromatic rings
• CPC Class Codes: C07C 49/755 a keto group being part of a condensed ring system with two or three rings, at least one ring being a six-membered aromatic ring
• CPC Class Codes: C07C 59/90 containing singly bound oxygen-containing groups
• CPC Class Codes: C07D 207/12 Oxygen or sulfur atoms
• CPC Class Codes: C07D 211/14 with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
• CPC Class Codes: C07D 211/18 with substituted hydrocarbon radicals attached to ring carbon atoms
• CPC Class Codes: C07D 211/32 by oxygen atoms
• CPC Class Codes: C07D 211/42 attached in position 3 or 5
• CPC Class Codes: C07D 211/46 having a hydrogen atom as the second substituent in position 4
• CPC Class Codes: C07D 211/52 having an aryl radical as the second substituent in position 4
• CPC Class Codes: C07D 211/58 attached in position 4
• CPC Class Codes: C07D 211/60 Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
• CPC Class Codes: C07D 211/62 attached in position 4
• CPC Class Codes: C07D 211/66 having a hetero atom as the second substituent in position 4
• CPC Class Codes: C07D 211/70 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 277/04 having no double bonds between ring members or between ring members and non-ring members
• CPC Class Codes: C07D 295/096 with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
• CPC Class Codes: C07D 295/116 : with the doubly bound oxygen or sulfur atoms directly attached to a carbocyclic ring
• CPC Class Codes: C07D 295/13 : to an acyclic saturated chain
• CPC Class Codes: C07D 295/205 : Radicals derived from carbonic acid
• CPC Class Codes: C07D 295/26 : Sulfur atoms

Abstract

Compounds of the formula ##STR1## and pharmaceutically acceptable salts thereof, wherein X and Y are independently H, F, Cl, Br, alkyl having up to four carbons, or alkoxy having up to four carbons, but X and Y are not both H, and Z is a secondary or tertiary amino group, are useful as analgesics and tranquillizing agents for mammals.

Claims

1. A compound having the formula ##STR113## wherein the nitrogen containing ring is selected from the group consisting of morpholino, thiazolidino, pyrrolidino, piperidino, piperazino and 3,4-[dihydropiperidino] dehydropiperidino;

R³, when taken separately, is a member selected from the group consisting of hydrogen, hydrocarbyl having up to six carbon atoms and free of triple bonds, pyrrolidino, piperidino, phenyl and phenyl substituted by Cl, Br or CF₃ ;

R⁴, when taken separately, is a member selected from the group consisting of hydrogen, hydroxyl, alkoxy having up to four carbon atoms, alkanoyloxy having up to six carbon atoms, acetoacetoxy, alkylcarbonyl having up to four carbon atoms, carboxamido, N-alkylcarboxamido having up to seven carbon atoms and the moiety ##STR114## with the proviso that when R⁴ is said moiety, said nitrogen containing ring is piperidino or 3,4-dehydropiperidino and R³ and R⁴, when taken together, are ##STR115## with the proviso that said nitrogen containing ring is piperidino.

2. A compound of claim 1 wherein the ring containing the nitrogen atom is piperidino, R³ is 4-p-chlorophenyl and R⁴ is 4-hydroxy.

3. A compound of claim 1 wherein the ring containing the nitrogen atom is piperidino, R³ is 4-phenyl and R⁴ is 4-ethoxy.

4. A compound of claim 1 wherein the ring containing the nitrogen atom is piperidino and R³ and R⁴ taken together are ##STR116##

5. A compound of claim 1 wherein the ring containing the nitrogen atom is piperidino, R³ is 4-phenyl and R⁴ is 4-acetoxy.

6. A compound of claim 1 wherein the ring containing the nitrogen atom is pyrrolidino, R³ is hydrogen and R⁴ is hydrogen.

7. A compound having the formula ##STR117## in which Z is a member of a group consisting of pyrrolidino, 3-hydroxy-3-phenylpyrrolidino, 4-carboxamidopiperidino, 4-acetoxy-4-phenylpiperidino, 4-ethoxy-4-phenylpiperidino, 4-hydroxy-4-(4-chlorophenyl)-piperidino, 4-methylpiperazino, 4-(2-hydroxyethyl)-piperazino and ##STR118##

8. 1-(2-[8-chloro-5-methoxy-3,4-dihydronaphthyl]methyl)pyrrolidine.