GB1381482A - Ureidophenoxyalkanolamine derivatives - Google Patents

Ureidophenoxyalkanolamine derivatives

Info

Publication number
GB1381482A
GB1381482A GB5295771A GB5295771A GB1381482A GB 1381482 A GB1381482 A GB 1381482A GB 5295771 A GB5295771 A GB 5295771A GB 5295771 A GB5295771 A GB 5295771A GB 1381482 A GB1381482 A GB 1381482A
Authority
GB
United Kingdom
Prior art keywords
reacting
hydroxy
phenoxy
formula
phenyl
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
Application number
GB5295771A
Inventor
R Eckardt
E Carstens
K Femmer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
AWD Pharma GmbH and Co KG
Original Assignee
Arzneimittelwerk Dresden GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to NL7115581A priority Critical patent/NL7115581A/xx
Priority to BE776050A priority patent/BE776050A/en
Application filed by Arzneimittelwerk Dresden GmbH filed Critical Arzneimittelwerk Dresden GmbH
Priority to GB3444174A priority patent/GB1383899A/en
Priority to GB5295771A priority patent/GB1381482A/en
Publication of GB1381482A publication Critical patent/GB1381482A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
    • C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

1381482 Urea derivatives ARZNEIMITTELWERK DRESDEN VEB 15 Dec 1971 52957/71 Heading C2C The invention comprises urea derivatives of the Formula I wherein R 1 is an unbranched C 1-6 alkyl radical, a branched C 3-8 alkyl, C 3-6 alkenyl, C 3-6 alkynyl, or C 3-7 cycloalkyl, and R 2 is C 3-7 cycloalkyl, C 3-6 alkenyl, or C 3-6 alkynyl, the acid addition salts thereof and their preparation. They are prepared by (a) reacting the appropriate 1- (ureidophenoxy) - 2,3 - epoxypropanes with amines of the formula R 1 NH 2 , (b) by reacting the appropriate l-[alkoxy-(or phenoxy)-carbonylaminophenoxy]-2 -hydroxy - 3 - (R 1 -amino) propanes with amines of the formula R 2 NH 2 , (c) by reacting N-R 2 -N<SP>1</SP>-(hydroxyphenyl)- ureas with the corresponding (2,3-epoxypropyl)- R 1 -amines, (d) reacting 1-(amino-phenoxy)-2- hydroxy-3-(R 1 -amino) propanes with isocyanates of the formula R 2 NCO, (e) by reacting compounds of the above Formula I in which R 2 is H with amines of the formula R 2 NH 2 , (f) by hydrogenolysis of the appropriate 1-[(3- R2 - ureido)phenoxy] - 2 - hydroxy - 3 - (N- benzyl - N - R 1 - amino)propane, (g) reacting carbonyl compounds of the formula R 10 -COR 11 , wherein R 10 and R 11 , together with the connecting carbon atom represent a radical which can be converted by hydrogenation into an R 1 group, under reducing conditions with the appropriate 1-[(3-R 2 -ureido)phenoxy]-2-hydroxy - 3 - aminopropanes, (h) reacting the appropriate 1-[(3 - R 2 - ureido) - phenoxy] - 2- hydroxy - 3 - chloropropanes with amines of the formula R 1 NH 2 , (j) reacting the corresponding 1 - [(3 - R 2 - ureido)phenoxy] - 2 - hydroxy- 3-aminopropanes with halides of the formula R 1 X wherein X is Cl, Br or I, or (j) reacting the appropriate N - R 2 - N<SP>1</SP> - (hydroxyphenyl)ureas with 2 - phenyl - 3 - R 1 - 5 - chloromethyloxazolidine. Other methods are described in general terms. 2 - Phenyl - 3 - butyl - 5 - chloromethyloxazolidine is obtained by reacting benzal-butylamine and epichlorohydrin in the presence of anhydrous zinc chloride. 1 - (4 - Phenoxycarbonylaminophenoxy)- 2- hydroxy - 3 - t. - butylaminopropane hydrochloride is prepared by reacting phenyl chloroformate with 1-(4-aminophenoxy)-2-hydroxy-3- t. - butylaminopropane hydrochloride. N - R 2 - N<SP>1</SP> - [(2,3 - epoxypropoxy)phenyl]- ureas are obtained by reacting epichlorhydrin with the corresponding N-R 2 -N<SP>1</SP>-(hydroxyphenyl)ureas. 1 - [4 - (3 - Cyclohexylureido)phenoxy] - 2- hydroxy - 3 - (N - benzyl - N - t. - butylamino)- propane is prepared by reacting N-cyclohexyl- N<SP>1</SP> - [4 - (2,3 - epoxy - propoxy)phenyl]urea with N-benzyl-N-t.-butylamine. 1 - [4 - (3 - Cyclohexylureido)phenoxy- 2 - hydroxy - 3 - aminopropane hydrochloride is made by reacting ammonia with N-cyclohexyl-N<SP>1</SP>- [4-(2,3-epoxypropoxy)phenyl]urea. 1 - [4 - (3 - Cycloherylureido)phenoxy] - 2- hydroxy - 3 - chloropropane is obtained by reacting N - cyclohexy - N<SP>1</SP> - [4 - (2,3 - epoxypropoxy)phenyl]urea with hydrochloric acid. Pharmaceutical compositions having #-adrenergic blocking action, contain the above novel compound or acid addition salts thereof in admixture with solid or liquid pharmaceutical diluents or carriers.
GB5295771A 1970-11-13 1971-12-15 Ureidophenoxyalkanolamine derivatives Expired GB1381482A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
NL7115581A NL7115581A (en) 1970-11-13 1971-11-12
BE776050A BE776050A (en) 1970-11-13 1971-11-30 PROCESS FOR PREPARING UREIDOPHENOXY-ALCANOLAMINE DERIVATIVES.
GB3444174A GB1383899A (en) 1970-11-13 1971-12-15 Ureidophenoxyalkanolamine derivatives
GB5295771A GB1381482A (en) 1970-11-13 1971-12-15 Ureidophenoxyalkanolamine derivatives

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DD15123670 1970-11-13
BE776050A BE776050A (en) 1970-11-13 1971-11-30 PROCESS FOR PREPARING UREIDOPHENOXY-ALCANOLAMINE DERIVATIVES.
GB3444174A GB1383899A (en) 1970-11-13 1971-12-15 Ureidophenoxyalkanolamine derivatives
GB5295771A GB1381482A (en) 1970-11-13 1971-12-15 Ureidophenoxyalkanolamine derivatives

Publications (1)

Publication Number Publication Date
GB1381482A true GB1381482A (en) 1975-01-22

Family

ID=27424990

Family Applications (2)

Application Number Title Priority Date Filing Date
GB3444174A Expired GB1383899A (en) 1970-11-13 1971-12-15 Ureidophenoxyalkanolamine derivatives
GB5295771A Expired GB1381482A (en) 1970-11-13 1971-12-15 Ureidophenoxyalkanolamine derivatives

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB3444174A Expired GB1383899A (en) 1970-11-13 1971-12-15 Ureidophenoxyalkanolamine derivatives

Country Status (3)

Country Link
BE (1) BE776050A (en)
GB (2) GB1383899A (en)
NL (1) NL7115581A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999067231A1 (en) * 1998-06-19 1999-12-29 Nicox S.A. Nitrate salts of antihypertensive medicines

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT334385B (en) * 1973-12-20 1976-01-10 Chemie Linz Ag PROCESS FOR THE PREPARATION OF NEW PHENOXYPROPYLAMINE DERIVATIVES AND THEIR SALTS
US4145363A (en) * 1975-02-05 1979-03-20 Yamanouchi Pharmaceutical Co., Ltd. 4-Carbamoylamino-α-aminomethylbenzyl alcohol derivatives
DE3544172A1 (en) * 1985-12-13 1987-06-19 Lentia Gmbh NEW CRYSTALLINE SALTS OF ARYLOXY PROPANOLAMINES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999067231A1 (en) * 1998-06-19 1999-12-29 Nicox S.A. Nitrate salts of antihypertensive medicines
KR100460714B1 (en) * 1998-06-19 2004-12-09 니콕스 에스. 에이. Nitrate salts of antihypertensive medicines

Also Published As

Publication number Publication date
NL7115581A (en) 1972-05-16
BE776050A (en) 1972-05-30
GB1383899A (en) 1974-02-12

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee