1-Phenoxy-2-hydroxy-3-alkynylamino-propanes and salts thereof
Patent 4016202 Issued on April 5, 1977. Estimated Expiration Date: 
April 5, 1994. Estimated Expiration Date is calculated based on simple USPTO term provisions. It does not account for terminal disclaimers, term adjustments, failure to pay maintenance fees, or other factors which might affect the term of a patent.
April 5, 1994. Estimated Expiration Date is calculated based on simple USPTO term provisions. It does not account for terminal disclaimers, term adjustments, failure to pay maintenance fees, or other factors which might affect the term of a patent.Patent References 3459782 3541130 3712927 InventorsAssigneeApplicationNo. 05/609998 filed on 09/03/1975US Classes:562/597, Oxalic acid per se or salt thereof564/164, The substituent nitrogen is an amino nitrogen attached indirectly to a ring by acyclic nonionic bonding564/165, Hydroxy, bonded directly to carbon, or ether in substituent Q (H of -OH may be replaced by a substituted or unsubstituted ammonium ion or a Group IA or IIA light metal)564/219, A ring or polycyclo ring system in a substituent E is attached indirectly to the carboxamide nitrogen or to an amino nitrogen in substituent E by acyclic nonionic bonding564/272, Benzylidene imines (i.e., Q-benzene-CH=NH, wherein Q is a substituent or hydrogen and substitution may be made for hydrogen only)564/349, Alkanol group only between the amino nitrogen and the ether oxygen which is bonded directly to the aryl ring or ring system (i.e., aryloxy alkanol amines)564/350, Nitrogen bonded directly to the aryl ring or ring system564/351, Halogen bonded directly to the aryl ring oring system564/50, The benzene ring is part of a substituent which contains nitrogen564/51The substituent nitrogen is attached indirectly to the benzene ring by acyclic nonionic bondingExaminersPrimary: Torrence, Dolph H.Attorney, Agent or FirmForeign Application Priority Data1973-02-28 DTAbstractRacemic and optically active compounds of the formula ##STR1## wherein R1 is hydrogen; halogen; nitro; alkyl of 1 to 5 carbon atoms; alkoxy of 1 to 4 carbon atoms; alkenyl of 2 to 5 carbon atoms; alkynyl of 2 to 5 carbon atoms; alkylamino of 1 to 5 carbon atoms; dialkylamino of 1 to 5 carbon atoms in each alkyl; alkoxyalkyl of 2 to 6 carbon atoms; alkylamino-alkyl of 2 to 6 carbon atoms; dialkylaminoalkyl of 3 to 12 carbon atoms; --(CH2)x --NH2, --(CH2)x -- OH, all where x is an integer from 0 to 3; --COOH; --COOR6, where R6 is alkyl of 1 to 4 carbon atoms; alkynyloxy of 3 to 6 carbon atoms; alkenyloxy of 3 to 6 carbon atoms; --CO--R9, --OCO--R9, --NH--CO--R9, all where R9 is alkyl of 1 to 6 carbon atoms, phenylalkyl of 7 to 10 carbon atoms or phenyl; cycloalkyl of 3 to 7 carbon atoms; --Q--CO--NR7 R8, where Q is a single bond, oxygen, --NH--, -- CH2 -- or --CH2 --NH--, and R7 and R8 are hydrogen, lower alkyl or, taken together with the nitrogen, pyrrolidino, piperidino or morpholino; phenyl; phenyl substituted with a substituent selected from the group consisting of halogen, lower alkyl, lower alkoxy, nitro, cyano and carboxyl; phenoxy; or phenoxy substituted with a substituent selected from the group consisting of halogen, lower alkyl, lower alkoxy, nitro, cyano and carboxyl;R2 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkanoyl of 2 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, amino, nitro or, together with R1, 3,4-methylenedioxy;R3 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or, together with R2 in the ortho-position, --CH=CH--CH=CH-- or --(CH2)n--, where n is an integer from 3 to 5;R4 is hyddrogen or alkyl of 1 to 3 carbon atoms; andR5 is alkyl of 1 to 3 carbon atoms or, together with R4, --(CH2)p -- where p is an integer from 4 to 6; and physiologically compatible acid addition salts thereof. The compounds as well as their salts are useful as adrenolytics and hypotensives. |
| ||||||||||||||
