GB1378241A - Amines and processes for their manufacture - Google Patents

Amines and processes for their manufacture

Info

Publication number
GB1378241A
GB1378241A GB814172A GB814172A GB1378241A GB 1378241 A GB1378241 A GB 1378241A GB 814172 A GB814172 A GB 814172A GB 814172 A GB814172 A GB 814172A GB 1378241 A GB1378241 A GB 1378241A
Authority
GB
United Kingdom
Prior art keywords
compound
radical
group
converted
propyl
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
GB814172A
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.)
Novartis AG
Original Assignee
Ciba Geigy AG
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 claimed from CH257871A external-priority patent/CH548364A/en
Priority claimed from CH66972A external-priority patent/CH561685A5/en
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Priority claimed from AT335873A external-priority patent/AT323726B/en
Publication of GB1378241A publication Critical patent/GB1378241A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic 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
    • C07D295/04Heterocyclic 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
    • C07D295/08Heterocyclic 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 singly bound oxygen or sulfur atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/13Amines
    • A61K31/135Amines having aromatic rings, e.g. ketamine, nortriptyline

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1378241 Ethanoanthracene derivatives CIBA-GEIGY AG 22 Feb 1972 [23 Feb 1971 17 Jan 1972] 8141/72 Heading C2C Novel 9-(2-A-3-R-propyl)-9,10-dihydro-9,10- ethanoanthracenes wherein R denotes a secondary or tertiary amino group and A denotes a free, etherified or acylated hydroxyl group, are prepared by a process in which a 9-X-9,10-dihydro-9,10-ethano-anthracene X is converted into a 2-A-3-R-propyl group and, if desired, free hydroxyl groups are converted into etherified or acylated hydroxyl groups, X denoting a 2,3- epoxy-propyl radical, which can be opened by an amine HR, or in which X is a radical corresponding to the 2-A-3-R-propyl group possessing at least one oxo group which can be reduced, or in which X is a radical corresponding to the 2-A-3-R-propyl group in which the nitrogen is bonded by one of its substituents to a double bond and optionally carries a positive charge or wherein one of the carbon atoms bonded to the nitrogen atom carries a hydroxy group which can be converted into a 2-A-3-R-propyl group by reduction, or in which X is a N-monosubstituted 2-A-3-amino-propyl radical which additionally carries, on the nitrogen atom, a radical Y<SP>1</SP> which can be split off by reduction, or in which X is a radical which can be converted into a 2-A-3-R-propyl group by hydrolysis. Intermediates are prepared from 9-(chlorocarbonylmethyl) - 9,10 - dihydro - 9,10 - ethano anthracene, e.g. (a) partial hydrogenation yields the acetaldehyde derivative which on reaction with trimethyloxosulphonium iodide yields the 9-(2,3-epoxypropyl) compound, (b) reduction in the presence of HCN yields the 9-(2- hydroxy-2-cyanoethyl) compound which on reduction with LiAlH 4 give the 9-(2-hydroxy-3- aminopropyl)-compound which may be converted to the following three derivatives, the 9- [(3-methyl-5-oxazolidinyl)methyl]-compound, the N-(p-toluenesulphonyl - 9 - (2 - hydroxy - 3- methylaminopropyl) compound and the 9-(2- oxo-5-oxazolidinylmethyl) compound. Pharmaceutical compositions in conventional forms for rectal, oral or parenteral administration and having anti-depressant activity comprises an above novel compound and a carrier or excipient.
GB814172A 1971-02-23 1972-02-22 Amines and processes for their manufacture Expired GB1378241A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH257871A CH548364A (en) 1971-02-23 1971-02-23 Substd 9-(2-hydroxy-3-aminoprop-1-enyl) -9,10-dihydro-9,10-ethano - anthracenes - antidepressants
CH66972A CH561685A5 (en) 1972-01-17 1972-01-17 Substd 9-(2-hydroxy-3-aminoprop-1-enyl) -9,10-dihydro-9,10-ethano - anthracenes - antidepressants
AT335873A AT323726B (en) 1971-02-23 1972-02-22 METHOD OF PREPARING NEW 9- (2-HYDROXY-3-AMINOPROPYL-9,10-DIHYDRO-9,10-ETHANOANTHRACENE

Publications (1)

Publication Number Publication Date
GB1378241A true GB1378241A (en) 1974-12-27

Family

ID=32329363

Family Applications (1)

Application Number Title Priority Date Filing Date
GB814172A Expired GB1378241A (en) 1971-02-23 1972-02-22 Amines and processes for their manufacture

Country Status (17)

Country Link
JP (1) JPS5817740B1 (en)
AR (5) AR204070A1 (en)
AU (1) AU476863B2 (en)
BE (1) BE779665A (en)
CA (1) CA993892A (en)
DE (1) DE2207097C2 (en)
DK (1) DK141508B (en)
ES (1) ES400022A1 (en)
FR (1) FR2126353B1 (en)
GB (1) GB1378241A (en)
HK (1) HK61377A (en)
HU (1) HU164585B (en)
KE (1) KE2795A (en)
MY (1) MY7800117A (en)
NL (1) NL174826C (en)
SE (1) SE387110B (en)
YU (6) YU36288B (en)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL127069C (en) * 1961-10-10
US3706765A (en) * 1969-01-03 1972-12-19 Ciba Geigy Corp Hydroxyethano-anthracenes
BE759571A (en) * 1969-11-28 1971-05-27 Ciba Geigy NEW AMINES AND PROCESS FOR THEIR PREPARATION

Also Published As

Publication number Publication date
YU41642B (en) 1987-12-31
YU143079A (en) 1982-10-31
HK61377A (en) 1977-12-16
FR2126353A1 (en) 1972-10-06
YU143179A (en) 1983-01-21
YU40752B (en) 1986-04-30
YU36363B (en) 1983-06-30
YU143279A (en) 1982-10-31
MY7800117A (en) 1978-12-31
YU43172A (en) 1981-08-31
YU40843B (en) 1986-06-30
DK141508B (en) 1980-04-08
AR204070A1 (en) 1975-11-20
JPS5817740B1 (en) 1983-04-09
BE779665A (en) 1972-08-22
YU41867B (en) 1988-02-29
NL174826C (en) 1984-08-16
KE2795A (en) 1978-01-06
AU3917472A (en) 1973-08-23
AR201551A1 (en) 1975-03-31
DK141508C (en) 1980-09-29
YU142979A (en) 1983-02-28
AR202178A1 (en) 1975-05-23
SE387110B (en) 1976-08-30
NL174826B (en) 1984-03-16
CA993892A (en) 1976-07-27
YU36288B (en) 1982-06-18
DE2207097C2 (en) 1987-02-05
HU164585B (en) 1974-03-28
DE2207097A1 (en) 1972-09-07
AU476863B2 (en) 1976-10-07
FR2126353B1 (en) 1975-10-31
ES400022A1 (en) 1974-12-16
NL7202326A (en) 1972-08-25
AR204309A1 (en) 1975-12-22
AR202284A1 (en) 1975-05-30
YU126180A (en) 1981-11-13

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Legal Events

Date Code Title Description
PS Patent sealed
PE20 Patent expired after termination of 20 years