GB1383899A - Ureidophenoxyalkanolamine derivatives - Google Patents

Ureidophenoxyalkanolamine derivatives

Info

Publication number
GB1383899A
GB1383899A GB3444174A GB3444174A GB1383899A GB 1383899 A GB1383899 A GB 1383899A GB 3444174 A GB3444174 A GB 3444174A GB 3444174 A GB3444174 A GB 3444174A GB 1383899 A GB1383899 A GB 1383899A
Authority
GB
United Kingdom
Prior art keywords
urea
reacting
formula
amines
alkyl radical
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
GB3444174A
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 GB1383899A publication Critical patent/GB1383899A/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

1383899 Urea derivatives ARZNEIMITTELWERK DRESDEN VEB 15 Dec 1971 34441/74 Divided out of 1381482 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 radical, C 3-6 alkenyl, C 3-6 alkynyl or C 3-7 cycloalkyl, and R 2 is an unbranched C 1-6 alkyl radical, a branched C 3-8 alkyl radical, C 3-6 alkenyl or C 3-6 alkynyl, the acid addition salts thereof and their preparation. The compounds are prepared by (a) reacting the appropriate 1-(ureidophenoxy)-2,3-epoxy propanes with amines of the formula R 2 NH 2 ; (b) reacting the appropriate N-R 2 -N<SP>1</SP>- (hydroxyphenyl)ureas with the corresponding (2,3-epoxy propyl)amines; (c) reacting compounds of the above Formula I in which R 2 is H with amines of the formula R 2 NH 2 ; or (d) reacting the appropriate 1-[alkoxy-(or phenoxy)- carbonylaminophenoxy] 2 - hydroxy - 3- (R 1 -amino)propanes with amines of the formula R 2 NH 2 . Other methods are described in general terms. N - Methyl - N<SP>1</SP> - [4 - (2,3 - epoxypropoxy) phenyl]urea and N-ethyl-N<SP>1</SP>-[4-(2,3-epoxypropoxy) phenyl]urea are prepared by epichlorohydrin with N-methyl-N<SP>1</SP>-(4-hydroxyphenyl)urea and N-ethyl-N<SP>1</SP>-(4-hydroxyphenyl)urea respectively. 1 - (4 - Phenoxycarbonylaminophenoxy) - 2- hydroxy - 3 - isopropylaminopropane hydrochloride is made by reacting phenyl chloroformate with 1-(4-aminophenoxy)-2-hydroxy- 3-isopropylaminopropane. Pharmaceutical compositions, having #-adrenergic blocking action, contain the above compounds or acid addition salts thereof in admixture with solid or liquid pharmaceutical diluents or carriers. Reference has been directed by the Comptroller to Specification 1,260,893.
GB3444174A 1970-11-13 1971-12-15 Ureidophenoxyalkanolamine derivatives Expired GB1383899A (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
GB1383899A true GB1383899A (en) 1974-02-12

Family

ID=27424990

Family Applications (2)

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

Family Applications Before (1)

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

Country Status (3)

Country Link
BE (1) BE776050A (en)
GB (2) GB1381482A (en)
NL (1) NL7115581A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4034009A (en) * 1973-12-20 1977-07-05 Chemie Linz Aktiengesellschaft 4-Ureido-2-acyl phenoxypropanolamine
US4145363A (en) * 1975-02-05 1979-03-20 Yamanouchi Pharmaceutical Co., Ltd. 4-Carbamoylamino-α-aminomethylbenzyl alcohol derivatives
US4767784A (en) * 1985-12-13 1988-08-30 Zoelss Gerhard Novel crystalline salts of aryloxy-propanolamines, a process for their preparation and their use

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1301759B1 (en) * 1998-06-19 2000-07-07 Nicox Sa NITRATED SALTS OF ANTI-HYPERTENSIVE DRUGS

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4034009A (en) * 1973-12-20 1977-07-05 Chemie Linz Aktiengesellschaft 4-Ureido-2-acyl phenoxypropanolamine
US4145363A (en) * 1975-02-05 1979-03-20 Yamanouchi Pharmaceutical Co., Ltd. 4-Carbamoylamino-α-aminomethylbenzyl alcohol derivatives
US4767784A (en) * 1985-12-13 1988-08-30 Zoelss Gerhard Novel crystalline salts of aryloxy-propanolamines, a process for their preparation and their use
US4849530A (en) * 1985-12-13 1989-07-18 Rorer Pharmaceutical Corporation Process for the preparation of crystalline salts or aryloxy-propanolamines

Also Published As

Publication number Publication date
GB1381482A (en) 1975-01-22
NL7115581A (en) 1972-05-16
BE776050A (en) 1972-05-30

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Legal Events

Date Code Title Description
PS Patent sealed
48R Reference inserted (sect. 8/1949)
PCNP Patent ceased through non-payment of renewal fee