GB1197054A - Derivatives of 1-Aminofluorene and 1-Aminofluorenone - Google Patents

Derivatives of 1-Aminofluorene and 1-Aminofluorenone

Info

Publication number
GB1197054A
GB1197054A GB46131/66A GB4613166A GB1197054A GB 1197054 A GB1197054 A GB 1197054A GB 46131/66 A GB46131/66 A GB 46131/66A GB 4613166 A GB4613166 A GB 4613166A GB 1197054 A GB1197054 A GB 1197054A
Authority
GB
United Kingdom
Prior art keywords
aminofluorenone
formula
reacting
aminofluorene
fluorenone
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
GB46131/66A
Inventor
Rene Rachel De Rider
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.)
MANUF PROD PHARMA
Original Assignee
MANUF PROD PHARMA
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 GB46131/65A priority Critical patent/GB1163422A/en
Application filed by MANUF PROD PHARMA filed Critical MANUF PROD PHARMA
Priority to GB46131/66A priority patent/GB1197054A/en
Priority to US587649A priority patent/US3459784A/en
Priority to NL6615189A priority patent/NL6615189A/xx
Priority to DE19661568887 priority patent/DE1568887A1/en
Priority to FR82080A priority patent/FR1501159A/en
Priority to BE689114D priority patent/BE689114A/xx
Priority to CH1569566A priority patent/CH478750A/en
Priority to BE704785D priority patent/BE704785A/xx
Priority to LU54626D priority patent/LU54626A1/xx
Priority to DE19671668413 priority patent/DE1668413A1/en
Priority to CH1416467A priority patent/CH489463A/en
Priority to FR124174A priority patent/FR7059M/fr
Priority to ES346014A priority patent/ES346014A1/en
Priority to US675076A priority patent/US3646038A/en
Priority to NL6713943A priority patent/NL6713943A/xx
Publication of GB1197054A publication Critical patent/GB1197054A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • 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
    • C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,197,054. Derivatives of 1-aminofluorenone and 1-aminofluorene. MANUFACTURE DE PRODUITS PHARMACEUTIQUES A. CHRISTIAENS S.A. 2 Oct., 1967 [14 Oct., 1966], No. 46131/66. Heading C2C. Novel derivatives of 1-aminofluorenone and 1-aminofluorene of the Formula I wherein A is -CH 2 -, -CH 2 .CH 2 -, or -CH(CH 3 )-; R 1 and R 2 , which may be the same or different, each represent H, C 1-4 alkyl or C 2-4 (2-hydroxyalkyl), or R 1 and R 2 together with the adjacent nitrogen atom, form a heterocyclic ring which may, if desired, be substituted by C 1-4 alkyl, HOCH 2 CH 2 - benzyl, and may, if desired contain a further hetero atom; R 3 is H or C 1-4 alkyl; R 4 is H or C 1 or Br in the 2- or 4-position; and B is C = O or CH 2 and acid addition salts thereof are prepared by reacting amines of the formula HN(R 1 )R 2 with a compound of the Formula II above in which X is Cl, Br or I, which are obtained either by reacting the appropriate 1-aminofluorenone or 1-aminofluorene with a compound of the formula X<SP>1</SP>-CO-A-X in which X and X<SP>1</SP>, which may be the same or different, each are Cl or Br, or compounds of Formula II above in which X is I, by iodinating the corresponding compounds in which X is Cl or Br. Alternatively compounds of Formula I in which R 1 and R 2 are both H may be prepared by hydrolysing in the presence of hydrobromic and acetic acids compounds of the Formula V above, which are made by reacting the appropriate 1-aminofluorenone or 1-aminofluorene with N-benzyloxycarbonylglycine, N - benzyloxycarbonyl - alanine or N-benzyloxycarbonyl-2-alanine respectively. 1 - Methylaminofluorenone is obtained by hydrolysing 1 - (N - methyl - p - toluene sulphonamido) fluorenone, resulting from the alkylation of 1/p-toluenesulphonamido) fluorenone, which is made by reacting 1-aminofluorenone with p-toluenesulphonyl chloride. 4 - Chloro - 1 - methylaminofluorenone is obtained either by alkylating 4-chloro-1- (N- aminofluorenone or by hydrolysing 4-choro-1- methyl-p-toluenesulphonamido) fluorenone, resulting from the alkylation of 4-chloro-1-(p-toluenesulphonamido) fluorenone, which is made by reacting 4-chloro-1-aminofluorenone with ptoluenesulphoxyl chloride. - 2 - (and 4 -) bromo - 1 - aminofluorenone are prepared by treating 1-aminofluorenone with N-bromosuccinimide. Pharmaceutical compositions, having hypnosedative, anticonvulsant, tranquilizing, relaxing, and sympathetic activities, contain at least one compound of Formula I above or non- toxic acid addition salts thereof, in association with pharmaceutical carriers or excipients.
GB46131/66A 1965-11-01 1966-10-14 Derivatives of 1-Aminofluorene and 1-Aminofluorenone Expired GB1197054A (en)

Priority Applications (16)

Application Number Priority Date Filing Date Title
GB46131/65A GB1163422A (en) 1965-11-01 1965-11-01 Amalgam Hydrodimerisation of Unsaturated Compounds
GB46131/66A GB1197054A (en) 1966-10-14 1966-10-14 Derivatives of 1-Aminofluorene and 1-Aminofluorenone
US587649A US3459784A (en) 1965-11-01 1966-10-19 Amalgam hydrodimerisation of unsaturated compounds
NL6615189A NL6615189A (en) 1965-11-01 1966-10-27
DE19661568887 DE1568887A1 (en) 1965-11-01 1966-10-28 Process for the reductive dimerization of alpha, ss-olefinically unsaturated esters or nitriles
FR82080A FR1501159A (en) 1965-11-01 1966-10-28 Reductive dimerization of unsaturated compounds
CH1569566A CH478750A (en) 1965-11-01 1966-10-31 Process for amalgam hydrodimerization of unsaturated compounds
BE689114D BE689114A (en) 1965-11-01 1966-10-31
BE704785D BE704785A (en) 1966-10-14 1967-10-06
LU54626D LU54626A1 (en) 1966-10-14 1967-10-09
DE19671668413 DE1668413A1 (en) 1966-10-14 1967-10-10 New derivatives of 1-amino-fluorene and 1-aminofluorenone
CH1416467A CH489463A (en) 1966-10-14 1967-10-11 Process for the preparation of 1-aminofluorene and 1-aminofluorenone derivatives
FR124174A FR7059M (en) 1966-10-14 1967-10-12
ES346014A ES346014A1 (en) 1966-10-14 1967-10-13 Derivatives of 1-Aminofluorene and 1-Aminofluorenone
US675076A US3646038A (en) 1966-10-14 1967-10-13 1-(n-methylpiperazineacetyl)aminofluorene
NL6713943A NL6713943A (en) 1966-10-14 1967-10-13

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB46131/66A GB1197054A (en) 1966-10-14 1966-10-14 Derivatives of 1-Aminofluorene and 1-Aminofluorenone

Publications (1)

Publication Number Publication Date
GB1197054A true GB1197054A (en) 1970-07-01

Family

ID=10439973

Family Applications (1)

Application Number Title Priority Date Filing Date
GB46131/66A Expired GB1197054A (en) 1965-11-01 1966-10-14 Derivatives of 1-Aminofluorene and 1-Aminofluorenone

Country Status (2)

Country Link
ES (1) ES346014A1 (en)
GB (1) GB1197054A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0005288A1 (en) * 1978-04-21 1979-11-14 Chimac Societe Anonyme Derivatives of 1-amino-fluoren-9-one and their use as herbicides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0005288A1 (en) * 1978-04-21 1979-11-14 Chimac Societe Anonyme Derivatives of 1-amino-fluoren-9-one and their use as herbicides

Also Published As

Publication number Publication date
ES346014A1 (en) 1968-12-01

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees