GB1210848A - 2-imino-methyleneimines - Google Patents

2-imino-methyleneimines

Info

Publication number
GB1210848A
GB1210848A GB3125368A GB3125368A GB1210848A GB 1210848 A GB1210848 A GB 1210848A GB 3125368 A GB3125368 A GB 3125368A GB 3125368 A GB3125368 A GB 3125368A GB 1210848 A GB1210848 A GB 1210848A
Authority
GB
United Kingdom
Prior art keywords
activity
compound
compounds
reaction
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
GB3125368A
Inventor
George Ireland Poos
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.)
Janssen Pharmaceuticals Inc
Original Assignee
McNeilab Inc
McNeil Laboratories Inc
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 McNeilab Inc, McNeil Laboratories Inc filed Critical McNeilab Inc
Priority to GB3125368A priority Critical patent/GB1210848A/en
Publication of GB1210848A publication Critical patent/GB1210848A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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

Abstract

1,210,848. 2 - Iminomethyleneimines. McNEIL LABORATORIES Inc. 1 July, 1968, No. 31253/68. Heading C2C. Novel compounds of the formula the pharmaceutically acceptable salts thereof, wherein Z is (a) -CH(C 6 H 5 ) 2 or (b) -A-lk-R wherein Alk is or a C 1-3 alkylene; R is phenyl, optionally substituted with halogen, C 1-7 alkyl, C 1-7 alkoxy, hydroxy or methylenedioxy; R 1 is C 1-7 alkyl or benzyl; and n is an integer between 3 and 5 are prepared by (a) reacting a compound of formula with NH 2 Z in an organic solvent followed by the liberation of the free compound from the product of this reaction by treatment with a base; or (b) reaction of 1 - R 1 - methyleneimine - 2 - one - lower acetal or a 1-R 1 -2-lower alkylthiomethyleneiminium salt or the phosphorus oxychloride adduct a chloride of 1-R 1 -methyleneimine-2-one with NH 2 Z. Hydroxy containing compounds may be prepared by hydrolysis of the corresponding alkoxy compounds or a hydroxy compound may be alkylated to give the alkoxy compound. Triethyl oxonium fluoroborate is prepared as an intermediate by reaction of BF 3 etherate and epichlorohydrin in ether. The compounds of the invention may be used in oral and parenteral preparations and are found to have anti-inflammatory activity, CNS depressant activity, hypotensive and cardiac stimulating activity, pressor activity and ganglion blocking activity and are found to decrease heart rate without reduction of cardiac output or mechanical work.
GB3125368A 1968-07-01 1968-07-01 2-imino-methyleneimines Expired GB1210848A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3125368A GB1210848A (en) 1968-07-01 1968-07-01 2-imino-methyleneimines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3125368A GB1210848A (en) 1968-07-01 1968-07-01 2-imino-methyleneimines

Publications (1)

Publication Number Publication Date
GB1210848A true GB1210848A (en) 1970-11-04

Family

ID=10320335

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3125368A Expired GB1210848A (en) 1968-07-01 1968-07-01 2-imino-methyleneimines

Country Status (1)

Country Link
GB (1) GB1210848A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3963701A (en) * 1972-04-17 1976-06-15 Richardson-Merrell Inc. Substituted benzhydryl lactamimide derivatives
US4126612A (en) * 1973-08-09 1978-11-21 Eugene O. Retter Substituted cycloalkyl lactamimides
US4126613A (en) * 1971-05-13 1978-11-21 Richardson-Merrell Inc. Substituted cycloalkyl lactamimides
EP0179254A1 (en) * 1984-09-24 1986-04-30 Pennwalt Corporation 4,5-Dihydro-4-oxo-2- [(2-trans-phenylcyclopropyl)amino]-3-furancarboxylic acids and derivatives thereof
US4699918A (en) * 1983-01-28 1987-10-13 Laboratoires Jacques Logeais 2-imino-pyrrolidines, process for their preparation, and therapeutic compositions containing same

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4126613A (en) * 1971-05-13 1978-11-21 Richardson-Merrell Inc. Substituted cycloalkyl lactamimides
US3963701A (en) * 1972-04-17 1976-06-15 Richardson-Merrell Inc. Substituted benzhydryl lactamimide derivatives
US4126612A (en) * 1973-08-09 1978-11-21 Eugene O. Retter Substituted cycloalkyl lactamimides
US4126611A (en) * 1973-08-09 1978-11-21 Richardson-Merrell Inc. Substituted cycloalkyl lactamimides
US4153235A (en) * 1973-08-09 1979-05-08 Richardson-Merrell Inc. Substituted cycloalkyl lactamimides
US4699918A (en) * 1983-01-28 1987-10-13 Laboratoires Jacques Logeais 2-imino-pyrrolidines, process for their preparation, and therapeutic compositions containing same
EP0179254A1 (en) * 1984-09-24 1986-04-30 Pennwalt Corporation 4,5-Dihydro-4-oxo-2- [(2-trans-phenylcyclopropyl)amino]-3-furancarboxylic acids and derivatives thereof

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Legal Events

Date Code Title Description
PS Patent sealed
429A Application made for amendment of specification (sect. 29/1949)
429H Application (made) for amendment of specification now open to opposition (sect. 29/1949)
429D Case decided by the comptroller ** specification amended (sect. 29/1949)
PCNP Patent ceased through non-payment of renewal fee