GB1351557A - 1,4-methano-and ethano-tetrahydronaphthyloxy-propanols and process for their preparation - Google Patents

1,4-methano-and ethano-tetrahydronaphthyloxy-propanols and process for their preparation

Info

Publication number
GB1351557A
GB1351557A GB4447572A GB4447572A GB1351557A GB 1351557 A GB1351557 A GB 1351557A GB 4447572 A GB4447572 A GB 4447572A GB 4447572 A GB4447572 A GB 4447572A GB 1351557 A GB1351557 A GB 1351557A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
propanols
pharmaceutically acceptable
ethano
prepared
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
GB4447572A
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.)
Pfizer Italia SRL
Original Assignee
Carlo Erba SpA
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
Application filed by Carlo Erba SpA filed Critical Carlo Erba SpA
Publication of GB1351557A publication Critical patent/GB1351557A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A61K31/138—Aryloxyalkylamines, e.g. propranolol, tamoxifen, phenoxybenzamine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
    • C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
    • C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
    • C07C217/32—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
    • C07C217/34—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by halogen atoms, by trihalomethyl, nitro or nitroso groups, or by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
    • C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
    • C07C217/38—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/52—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups or amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

1351557 Substituted propanols CARLO ERBA SpA 26 Sept 1972 [21 Oct 1971] 44475/72 Addition to 1263035 Heading C2C Novel propanols of the formula wherein x is 1 or 2, R<SP>1</SP> is hydroxy or acyloxy, and R<SP>2</SP> and R<SP>3</SP> are each hydrogen, benzyl or C 1-4 alkyl and pharmaceutically acceptable salts thereof are prepared by (a) de-etherifying a corresponding compound wherein R<SP>1</SP> is an alkoxy or aralkyloxy group to form R<SP>1</SP> is hydroxy and, if required acylating to form R<SP>1</SP> is acyloxy, and (b) reacting a compound of one of the general formulae wherein x is 1 or 2, Z is halo and R<SP>5</SP> is acyl, with HNR<SP>2</SP>R<SP>3</SP> and, if required saponifying to form a compound where R<SP>1</SP> is hydroxy. The product of the above processes may be converted into a pharmaceutically acceptable salt and/or a mixture of optically active isomers obtained by the said processes separated into separate isomers. 5 - Hydroxy - 8 - acetoxy - 1,4 - ethano - 1,2,3,4- tetrahydronaphthalene is prepared by treating 5,8 - diacetoxy - 1,2,3,4 - tetrahydroethanenaphthalene with diethylamine and is then converted to 3-chloro-(8<SP>1</SP>-acetoxy-1<SP>1</SP>,4<SP>1</SP>-ethano- 1<SP>1</SP>,2<SP>1</SP>,3<SP>1</SP>,4<SP>1</SP> - tetrahydronaphth - 5<SP>1</SP> - yloxy) - 2- propanol by reacting with epichlorhydrin. 5- Hydroxy - 8 - acetoxybenzonorbornane is prepared by a similar method and is then reacted with epichlorhydrin. Pharmaceutical compositions contain the above novel propanols and pharmaceutically acceptable salts thereof and a carrier or diluent. The compositions may be in a form for oral or parenteral administration such as capsules, tablets, pills, drops, vials or suppositories and may be used in the treatment of tachycardia, angina pectoris, mycocardiac ischaemia, arterial hypertension and anxiety conditions. The propanols also have local anaesthetic activity.
GB4447572A 1971-10-21 1972-09-26 1,4-methano-and ethano-tetrahydronaphthyloxy-propanols and process for their preparation Expired GB1351557A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT3012471 1971-10-21

Publications (1)

Publication Number Publication Date
GB1351557A true GB1351557A (en) 1974-05-01

Family

ID=11229158

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4447572A Expired GB1351557A (en) 1971-10-21 1972-09-26 1,4-methano-and ethano-tetrahydronaphthyloxy-propanols and process for their preparation

Country Status (21)

Country Link
JP (1) JPS515379B2 (en)
AT (1) AT318563B (en)
AU (1) AU471732B2 (en)
BE (1) BE790188R (en)
CA (1) CA992983A (en)
CH (1) CH565741A5 (en)
CS (1) CS161064B2 (en)
DE (1) DE2251095C3 (en)
DK (1) DK135576B (en)
FR (1) FR2157897B2 (en)
GB (1) GB1351557A (en)
HK (1) HK9377A (en)
HU (1) HU165185B (en)
IL (1) IL40610A (en)
KE (1) KE2693A (en)
MY (1) MY7700158A (en)
NL (1) NL153516B (en)
NO (1) NO130643C (en)
SE (1) SE389103B (en)
SU (1) SU496722A3 (en)
ZA (1) ZA727459B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1436860A (en) * 1972-12-18 1976-05-26 Syntex Inc 5,8-dihydro-5,8-methanonaphthalene cardiovascular agents
JPS52120690A (en) * 1976-04-02 1977-10-11 Fujitsu Ltd Radiation semi-conductor device

Also Published As

Publication number Publication date
FR2157897B2 (en) 1975-06-20
CS161064B2 (en) 1975-05-04
FR2157897A2 (en) 1973-06-08
CH565741A5 (en) 1975-08-29
KE2693A (en) 1977-02-11
SU496722A3 (en) 1975-12-25
NO130643B (en) 1974-10-07
DE2251095B2 (en) 1975-05-07
AU4707772A (en) 1974-04-04
AU471732B2 (en) 1976-04-29
IL40610A (en) 1975-04-25
DK135576C (en) 1977-10-31
DK135576B (en) 1977-05-23
ZA727459B (en) 1974-05-29
NL7214106A (en) 1973-04-25
SE389103B (en) 1976-10-25
JPS515379B2 (en) 1976-02-19
NL153516B (en) 1977-06-15
IL40610A0 (en) 1972-12-29
HK9377A (en) 1977-02-25
BE790188R (en) 1973-04-17
AT318563B (en) 1974-10-25
DE2251095A1 (en) 1973-05-10
MY7700158A (en) 1977-12-31
CA992983A (en) 1976-07-13
JPS4849750A (en) 1973-07-13
DE2251095C3 (en) 1976-01-02
NO130643C (en) 1975-01-15
HU165185B (en) 1974-07-27

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee