GB1296112A - - Google Patents

Info

Publication number
GB1296112A
GB1296112A GB1296112DA GB1296112A GB 1296112 A GB1296112 A GB 1296112A GB 1296112D A GB1296112D A GB 1296112DA GB 1296112 A GB1296112 A GB 1296112A
Authority
GB
United Kingdom
Prior art keywords
alkyl
prepared
compounds
propiothienone
reacting
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
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 filed Critical
Publication of GB1296112A publication Critical patent/GB1296112A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1296112 Basic dithienyl derivatives DEUTSCHE GOLD UND SILBER SCHEIDEANSTALT 17 April 1970 [26 April 1969] 18438/70 Heading C2C Novel compounds I in which the two thienyl radicals may each be substituted by one or more 1-6C alkyl; A-B is either =C(OH)-CHR<SP>6</SP>- or =C=CR<SP>6</SP>-; R<SP>5</SP> and R<SP>6</SP> are H or one is 1-6C alkyl and the other H; R<SP>1</SP>is H or 1-6C alkyl; R<SP>2</SP> is H or OH; and R<SP>3</SP> and B<SP>4</SP> are H, halo, OH, or 1-6C alkyl, haloalkyl or alkoxy and their optically active or diastereomeric forms and salts are prepared by reacting compounds II in which Y is Cl, Br, alkoxy or thienyl with a thienyl metal compound and optionally converting compounds I in which A-B is =C(OH)-CHR<SP>6</SP> with a dehydrating agent into compounds I where A-B is =C=C(R<SP>6</SP>)-. Ethyl l - # - (1 - phenyl - 1 - hydroxy - 2 - proplylamino) - propionate is prepared by reacting l-norephedrine with ethyl acrylate in ethanol. # - (1 - Phenyl - 1 - hydroxy - 2 - -propylamino)- 3 - propiothienone hydrochloride is prepared by boiling 3-acetyl thiophene, paraformaldehyde and l-norephedrine HCl in isopropanol. dl -# - [2 - (4 - t - Butylphenyl) - 2 - hydroxyethylamino] - 3 - propiothienone is prepared by reacting #-dimethylamino-3-propiothienone with 2- ( 4-t-butylphenyl)-2-hydroxyethylamine. Pharmaceutical compositions used in treating cardiac and circulatory disorders comprise a compound I together with a suitable excipient for oral or parenteral administration.
GB1296112D 1969-04-26 1970-04-17 Expired GB1296112A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19691921453 DE1921453C3 (en) 1969-04-26 1969-04-26 Basic dithienyl derivatives

Publications (1)

Publication Number Publication Date
GB1296112A true GB1296112A (en) 1972-11-15

Family

ID=5732538

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1296112D Expired GB1296112A (en) 1969-04-26 1970-04-17

Country Status (16)

Country Link
AT (2) AT307399B (en)
BE (1) BE749296A (en)
CH (1) CH539645A (en)
DE (1) DE1921453C3 (en)
DK (1) DK126001B (en)
EG (1) EG10650A (en)
ES (2) ES377719A1 (en)
FI (1) FI50125C (en)
FR (1) FR2042377B1 (en)
GB (1) GB1296112A (en)
IT (1) IT1043819B (en)
NL (1) NL149174B (en)
NO (2) NO131675C (en)
SE (1) SE369305B (en)
SU (1) SU457221A3 (en)
TR (1) TR17649A (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE394280B (en) * 1970-04-17 1977-06-20 Degussa PROCEDURE FOR THE PRODUCTION OF BASIC SUBSTITUTED DITIENYL DERIVATIVES
JPS5033063B1 (en) * 1971-01-19 1975-10-27
GB1579541A (en) * 1977-01-12 1980-11-19 Degussa Process for the production of (1,1 - dithien - (3)-yl - 1 - hydroxy - (3) - propyl) - (1-phenyl - 1 - hydroxy - (2) - propyl)-amine and (1,1 - dithien - (3) - yl-(1) - propen - (3) - yl) - (1 - phenyl-1 - hydroxy - (2) - propyl)- amine
GB1597591A (en) * 1977-01-12 1981-09-09 Degussa Dithienyl alkylamines and alkenylamines and a process for their production
US4278687A (en) 1980-01-31 1981-07-14 Shell Oil Company Inhibition of biosynthesis of triglycerides by certain N-β-phenethyl-N-thienylalkylamines

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2561899A (en) * 1948-02-25 1951-07-24 Burroughs Wellcome Co Dithienyl allyl amines
DE874914C (en) * 1950-04-28 1953-04-27 Wellcome Found Process for the preparation of thienyl compounds
DE964056C (en) * 1955-09-25 1957-05-16 Basf Ag Process for the preparation of thiophene derivatives
DE1219038B (en) * 1962-12-08 1966-06-16 Degussa Process for the preparation of thiophene compounds
DE1199783B (en) * 1962-11-30 1965-09-02 Degussa Process for the preparation of basic thiophene derivatives
DE1194424B (en) * 1961-11-10 1965-06-10 Degussa Process for the preparation of basic thiophene derivatives
DE1217967B (en) * 1962-12-08 1966-06-02 Degussa Process for the preparation of basic thiophene derivatives
DE1217396B (en) * 1963-07-04 1966-05-26 Laboratorie Roger Bellon, Neuilly-sur-Seine (Frankreich) Process for the preparation of 1 - (thienyl-21) - l-oxo-2-aminopropanes
AT255400B (en) * 1965-03-22 1967-07-10 Chemie Linz Ag Process for the production of new basic ethers
FR1462206A (en) * 1965-06-08 1966-04-15 Innothera Lab Sa Gem-bithienyl compounds and their preparation

Also Published As

Publication number Publication date
NO131675C (en) 1975-07-09
CH539645A (en) 1973-07-31
DE1921453B2 (en) 1972-09-28
AT307399B (en) 1973-05-25
FR2042377B1 (en) 1974-02-01
EG10650A (en) 1976-03-31
SE369305B (en) 1974-08-19
NO131675B (en) 1975-04-01
SU457221A3 (en) 1975-01-15
FR2042377A1 (en) 1971-02-12
BE749296A (en) 1970-10-01
ES398738A1 (en) 1974-08-16
NL149174B (en) 1976-04-15
NO132593C (en) 1975-12-03
FI50125C (en) 1975-12-10
ES377719A1 (en) 1972-10-16
AT303716B (en) 1972-12-11
IT1043819B (en) 1980-02-29
DE1921453A1 (en) 1970-11-12
NL7004410A (en) 1970-10-28
FI50125B (en) 1975-09-01
TR17649A (en) 1975-07-23
DK126001B (en) 1973-05-28
DE1921453C3 (en) 1973-04-19
NO132593B (en) 1975-08-25

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Legal Events

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