[go: up one dir, main page]

FR2174771A1 - 9-hydroxy 10,9-iminomethano anthracenes - sedatives or stimulants - Google Patents

9-hydroxy 10,9-iminomethano anthracenes - sedatives or stimulants

Info

Publication number
FR2174771A1
FR2174771A1 FR7208391A FR7208391A FR2174771A1 FR 2174771 A1 FR2174771 A1 FR 2174771A1 FR 7208391 A FR7208391 A FR 7208391A FR 7208391 A FR7208391 A FR 7208391A FR 2174771 A1 FR2174771 A1 FR 2174771A1
Authority
FR
France
Prior art keywords
mixt
hrs
alkyl
degrees
product
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.)
Granted
Application number
FR7208391A
Other languages
French (fr)
Other versions
FR2174771B1 (en
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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 Roussel Uclaf SA filed Critical Roussel Uclaf SA
Priority to FR7208391A priority Critical patent/FR2174771A1/en
Publication of FR2174771A1 publication Critical patent/FR2174771A1/en
Application granted granted Critical
Publication of FR2174771B1 publication Critical patent/FR2174771B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/06—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing isoquinuclidine ring systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)

Abstract

Compounds of formula (I) and their acid addn. salts are new: (whwere R=H, alkyl or a group -(CH2)n.NHalkyl, n= 2-5; R1 and R2= H, Cl, Br, alkyl, alkoxy, CF3 or dialkylamino R3 = O or H2; all the alkyl and alkoxy grps. contain 1-6C). The compounds are either sedatives or stimulants, and are therefor useful in psychiatry as psychoregulators. EXAMPLE 5.4 g. (II, R=CH3, R1=R2=H) were suspended in 54cc. N.NaOH and heated under reflux for 20 mins. The mixt. was cooled and 100 cc. water added. The product was extracted into CH2Cl2, washed, dried, and evapd. The residue was triturated with ether and filtered to give 4.9 g. (I, R3= O, R=CH3, R1=R2=H), m.pt. 218 degrees C. 6.7 g. of this product in 120 cc. THF were added to 75cc. of soln. of diborane in THF contg. 14.58 g./litre of diborane. The mixt. was stirred for 18 hrs. at ambient temp. then heated at 40 degrees C for 4 hrs. After cooling 70 cc. 2N NaOH were added and the mixt. refluxed for 4 hrs. The product was extracted into ethyl acetate, chromatographed on silica gel, eluting with chloroform-acetone-triethylamine (70-20-10) to give (I, R3=H2, R=CH3, R1=R2=H) m.p. 226 degrees C.
FR7208391A 1972-03-10 1972-03-10 9-hydroxy 10,9-iminomethano anthracenes - sedatives or stimulants Granted FR2174771A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR7208391A FR2174771A1 (en) 1972-03-10 1972-03-10 9-hydroxy 10,9-iminomethano anthracenes - sedatives or stimulants

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7208391A FR2174771A1 (en) 1972-03-10 1972-03-10 9-hydroxy 10,9-iminomethano anthracenes - sedatives or stimulants

Publications (2)

Publication Number Publication Date
FR2174771A1 true FR2174771A1 (en) 1973-10-19
FR2174771B1 FR2174771B1 (en) 1975-06-13

Family

ID=9094987

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7208391A Granted FR2174771A1 (en) 1972-03-10 1972-03-10 9-hydroxy 10,9-iminomethano anthracenes - sedatives or stimulants

Country Status (1)

Country Link
FR (1) FR2174771A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114929235A (en) * 2020-01-03 2022-08-19 布鲁奥科制药有限公司 Compounds and compositions for treating CNS disorders

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6166344A (en) 1999-03-23 2000-12-26 General Electric Company Circuit breaker handle block

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3426015A (en) * 1966-04-04 1969-02-04 American Home Prod Substituted 10,5-(iminomethano)-10,11-dihydro - 5h - dibenzo(a,d)cyclohepten-13-one derivatives
US3466288A (en) * 1966-09-09 1969-09-09 Warner Lambert Pharmaceutical 9,4alpha-iminoethanoanthracenes and indeno(2,1-j)isoquinolines
US3539557A (en) * 1968-10-08 1970-11-10 Ayerst Mckenna & Harrison 9,10 - dihydro - 13 - hydroxy - 9,10(methanoiminomethano) anthracen - 11 - one and its preparation

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3426015A (en) * 1966-04-04 1969-02-04 American Home Prod Substituted 10,5-(iminomethano)-10,11-dihydro - 5h - dibenzo(a,d)cyclohepten-13-one derivatives
US3466288A (en) * 1966-09-09 1969-09-09 Warner Lambert Pharmaceutical 9,4alpha-iminoethanoanthracenes and indeno(2,1-j)isoquinolines
US3539557A (en) * 1968-10-08 1970-11-10 Ayerst Mckenna & Harrison 9,10 - dihydro - 13 - hydroxy - 9,10(methanoiminomethano) anthracen - 11 - one and its preparation

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114929235A (en) * 2020-01-03 2022-08-19 布鲁奥科制药有限公司 Compounds and compositions for treating CNS disorders

Also Published As

Publication number Publication date
FR2174771B1 (en) 1975-06-13

Similar Documents

Publication Publication Date Title
ES431056A1 (en) N-{8 (Methoxymethyl-furyl)-methyl{9 -morphinans or -6,7-benzomorphans and salts thereof
ES474232A1 (en) Production of 2,6-diaminonebularines
US3184457A (en) 2-aminobenzofuran(2h)-5-ols and a process of making them
FR2174771A1 (en) 9-hydroxy 10,9-iminomethano anthracenes - sedatives or stimulants
GB1468913A (en) Sulphamoylbenzoic acid amides
JPS57175188A (en) 2-aryl-2,1-h-azoyl(alkyl)-gamma-butyllactones
FR2208671A1 (en) N-substd. 2-anilino-imidazolines - with hypotensive, sedative, secretion-inhibiting and analgesic activity
ES450382A1 (en) Indaneacetic acid derivatives
ES8500910A1 (en) Process for producing antifungal pyridazinone derivatives and certain novel compounds produced by such a process.
ES395193A1 (en) A PROCEDURE FOR THE PREPARATION OF NEW INDAMINAS SALTS
KR840002821A (en) Method for preparing N- (2,3-epoxypropylene) -N-aralkylsulfonamide derivative
ES442710A1 (en) A procedure for preparing new piperazine derivatives. (Machine-translation by Google Translate, not legally binding)
DE3165495D1 (en) Derivatives of fluorophenacyl amines and their therapeutic use
ATE2435T1 (en) GLYCOLIPID COMPOUND USEFUL AS IMMUNOLOGICAL ADJUVANTS AND ITS PRODUCTION.
ES8205006A1 (en) Process for the manufacture of alkylhydrazone cationic dyes and their dyestuff bases.
ES301710A1 (en) Procedure for the preparation of new 1,2-diaril-4-alkyl-3,5-dioxo-pirazolidines (Machine-translation by Google Translate, not legally binding)
KR850006177A (en) Method for preparing cinnamic acid derivatives
GB1066300A (en) Process for the preparation of phenyl-cyclohexyl-alkylamines
KR830001839B1 (en) Process for preparing phenyl quinolizidines
GB807750A (en) Improvements in or relating to piperazine derivatives
ES446105A1 (en) A procedure for the production of an aminoalkilic ester of a 2,6-dialkyl (bottom) -4-phenyl substitute-1,4-dihydropyridin-3-carboxylic acid. (Machine-translation by Google Translate, not legally binding)
Eremeev et al. Acetylenic α-aziridinocarbinols and the mechanism of their conversion to β-aziridinoacroleins
ES417884A1 (en) Substituted 4-biphenylyl-butenoic acids esters and amides and pharmaceutical compositions containing them
GB1378403A (en) Process for the preparation of 3-2h-isoquinolones
ES390646A1 (en) 2,3-alkylidene-rhamnopyranosides and process for preparing them

Legal Events

Date Code Title Description
ST Notification of lapse