GB1267433A - Novel imidazoline derivatives, the preparation thereof, and compositions containing the same - Google Patents

Novel imidazoline derivatives, the preparation thereof, and compositions containing the same

Info

Publication number
GB1267433A
GB1267433A GB5580469A GB5580469A GB1267433A GB 1267433 A GB1267433 A GB 1267433A GB 5580469 A GB5580469 A GB 5580469A GB 5580469 A GB5580469 A GB 5580469A GB 1267433 A GB1267433 A GB 1267433A
Authority
GB
United Kingdom
Prior art keywords
general formula
amino
prepared
acid addition
reaction
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
GB5580469A
Inventor
David Miller
Charles Sylvester Fake
Robert Howard Poyser
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.)
Beecham Group PLC
Original Assignee
Beecham Group PLC
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 BE754832D priority Critical patent/BE754832A/en
Application filed by Beecham Group PLC filed Critical Beecham Group PLC
Priority to GB5580469A priority patent/GB1267433A/en
Priority to ZA705540A priority patent/ZA705540B/en
Priority to DE19702040374 priority patent/DE2040374A1/en
Priority to ES382731A priority patent/ES382731A1/en
Priority to AT740670A priority patent/AT296975B/en
Priority to NL7012086A priority patent/NL7012086A/xx
Priority to FR7029979A priority patent/FR2068499B1/fr
Publication of GB1267433A publication Critical patent/GB1267433A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/73—Unsubstituted amino or imino radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/20—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D261/14—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D277/82—Nitrogen atoms

Landscapes

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

Abstract

1,267,433. 2 - Amino - 2 - imidazolines. BEECHAM GROUP Ltd. 13 Aug., 1970 [14 Aug., 1969; 14 Nov., 1969], Nos. 40666/69 and 55804/69. Heading C2C. Novel 2-amino-2-imidazolines of the general formula wherein X is a 2-pyridyl group optionally substituted by one or two halogen atoms and/or C 1-4 alkyl groups, a 2-benzothiazolyl group optionally substituted by a halogen atom or a 3-pyridyl, 2-pyrimidyl, 2-pyrazinyl or 3,5-di- (C 1-4 alkyl)-4-isoxazolyl group, and acid addition salts thereof, are prepared (a) by reaction of an amine of the general formula XNH 2 with an acid addition salt of 2-methylthio-2-imidazoline or (b) by reaction of an isothiourea of the general formula XNH(C=NH)S-Alkyl (in the form of a thiouronium salt) or a thiourea of the general formula XNHCSNH 2 , with ethylenediamine; followed optionally by interconversion of resulting free bases and acid addition salts thereof. Isothioureas of the third general formula above are prepared by alkylation of a thiourea of the fourth general formula above, which is prepared by reaction of an amine of the second general formula above with benzoyl isothiocyanate and hydrolysis of the resulting benzoylthiourea of the general formula with an aqueous alkali metal hydroxide. 1,2 - Bis - (N - X - N<SP>1</SP> - guanidino) - ethane acid addition salts are obtained as by-products in process (b) above. Chlorinated 2-amino-picolines are prepared by treatment of 2-amino-picolines with concentrated hydrochloric acid and 15% hydrogen peroxide. Pharmaceutical compositions having antihypertensive activity comprise, as active ingredient, a 2-amino-2-imidazoline of the first general formula above, together with a pharmaceutically acceptable carrier.
GB5580469A 1969-08-14 1969-08-14 Novel imidazoline derivatives, the preparation thereof, and compositions containing the same Expired GB1267433A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
BE754832D BE754832A (en) 1969-08-14 IMINAZOLINES
GB5580469A GB1267433A (en) 1969-08-14 1969-08-14 Novel imidazoline derivatives, the preparation thereof, and compositions containing the same
ZA705540A ZA705540B (en) 1969-11-14 1970-08-11 "organic compounds"
DE19702040374 DE2040374A1 (en) 1969-08-14 1970-08-13 Imidazolines, their acid addition salts and process for their preparation
ES382731A ES382731A1 (en) 1969-08-14 1970-08-13 Novel imidazoline derivatives, the preparation thereof, and compositions containing the same
AT740670A AT296975B (en) 1969-08-14 1970-08-14 Process for the preparation of new imidazoline derivatives and their salts
NL7012086A NL7012086A (en) 1969-08-14 1970-08-14
FR7029979A FR2068499B1 (en) 1969-08-14 1970-08-14

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB5580469A GB1267433A (en) 1969-08-14 1969-08-14 Novel imidazoline derivatives, the preparation thereof, and compositions containing the same
GB4066669 1969-08-14

Publications (1)

Publication Number Publication Date
GB1267433A true GB1267433A (en) 1972-03-22

Family

ID=26264467

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5580469A Expired GB1267433A (en) 1969-08-14 1969-08-14 Novel imidazoline derivatives, the preparation thereof, and compositions containing the same

Country Status (7)

Country Link
AT (1) AT296975B (en)
BE (1) BE754832A (en)
DE (1) DE2040374A1 (en)
ES (1) ES382731A1 (en)
FR (1) FR2068499B1 (en)
GB (1) GB1267433A (en)
NL (1) NL7012086A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0008881A1 (en) * 1978-08-31 1980-03-19 Eli Lilly And Company 1-Benzoyl-3-pyridinyl ureas, their use as insecticides, their preparation and formulations containing them
EP0008880A1 (en) * 1978-08-31 1980-03-19 Eli Lilly And Company 1-(2,6-Dichlorobenzoyl)-3-(5-substituted-2-pyridinyl) ureas, their preparation, formulations and use as insecticides
US4203988A (en) 1975-11-12 1980-05-20 Merck & Co., Inc. Pyridinyl ureas and pharmaceutical use
US4323570A (en) 1978-11-15 1982-04-06 Beiersdorf Aktiengesellschaft Substituted aminopyrimidines
US4434167A (en) 1979-11-07 1984-02-28 Beiersdorf Aktiengesellschaft Pyrimidyl thioureas useful for the treatment of hypertension and hyperlipidemia
EP0121082A1 (en) * 1983-03-04 1984-10-10 Bayer Ag Guanidin derivatives

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH570401A5 (en) * 1972-05-09 1975-12-15 Wander Ag Dr A
GB1444558A (en) * 1973-02-17 1976-08-04 Beecham Group Ltd Pyridylthioureas
GB1408362A (en) * 1973-05-25 1975-10-01 Lepetit Spa 2-pyrrol-1-yl amino 4,5-dihydro-1-h-imidazole derivatives
FR2358890A1 (en) * 1976-05-24 1978-02-17 Science Union & Cie NEW ARYL TRIFLUOROETHYLAMINES, THEIR METHODS OF OBTAINING AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING
CH632268A5 (en) 1977-01-14 1982-09-30 Sandoz Ag Method for producing new heterocyclylaminoderivaten.
DE2816627A1 (en) * 1978-04-17 1979-10-25 Beiersdorf Ag Antihypertensive isoindolinyl-amino-imidazoline - prepd. by reacting 2-amino-isoindoline with 2-alkylthio-2-imidazoline
DE2905501A1 (en) * 1979-02-14 1980-08-28 Beiersdorf Ag Heterocyclic amine(s) with long lasting antihypertensive activity - e.g. 2-N-amino-iso:indolinyl-imidazoline
DE2849537C2 (en) * 1978-11-15 1983-03-17 Beiersdorf Ag, 2000 Hamburg Substituted 5- (2-imidazolin-2-yl) aminopyrimidines, processes for their preparation and pharmaceuticals containing them
MA18829A1 (en) * 1979-05-18 1980-12-31 Ciba Geigy Ag PYRIMIDINE DERIVATIVES, METHODS FOR THEIR PREPARATION, PHARMACEUTICAL COMPOSITIONS CONTAINING THESE COMPOUNDS AND THEIR THERAPEUTIC USE
FR2462436A1 (en) * 1979-07-31 1981-02-13 Abbott Lab Antiinflammatory pyrazolyl amino imidazoline derivatives - which stop progress of rheumatism
AU5433898A (en) * 1996-11-25 1998-06-22 Procter & Gamble Company, The 2-imidazolinylaminobenzothiazole compounds useful as alpha-2 adrenoceptor agonists

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1211341A (en) * 1955-12-19 1960-03-15 A Wander Dr Process for the preparation of 2-amino-imidazolines
NL123037C (en) * 1963-10-04

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4203988A (en) 1975-11-12 1980-05-20 Merck & Co., Inc. Pyridinyl ureas and pharmaceutical use
EP0008881A1 (en) * 1978-08-31 1980-03-19 Eli Lilly And Company 1-Benzoyl-3-pyridinyl ureas, their use as insecticides, their preparation and formulations containing them
EP0008880A1 (en) * 1978-08-31 1980-03-19 Eli Lilly And Company 1-(2,6-Dichlorobenzoyl)-3-(5-substituted-2-pyridinyl) ureas, their preparation, formulations and use as insecticides
US4323570A (en) 1978-11-15 1982-04-06 Beiersdorf Aktiengesellschaft Substituted aminopyrimidines
US4434167A (en) 1979-11-07 1984-02-28 Beiersdorf Aktiengesellschaft Pyrimidyl thioureas useful for the treatment of hypertension and hyperlipidemia
EP0121082A1 (en) * 1983-03-04 1984-10-10 Bayer Ag Guanidin derivatives
US4602938A (en) * 1983-03-04 1986-07-29 Bayer Aktiengesellschaft N'-(substituted-pyrimidin-2-yl)-N"-substituted-N",N"'-bis-(substituted-benzenesulphonyl)-guanidines as herbicides

Also Published As

Publication number Publication date
BE754832A (en) 1971-02-15
AT296975B (en) 1972-03-10
FR2068499A1 (en) 1971-08-27
NL7012086A (en) 1971-02-16
FR2068499B1 (en) 1974-08-30
DE2040374A1 (en) 1971-02-25
ES382731A1 (en) 1973-04-16

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