GB976829A - Phenanthridine derivatives and a process for the manufacture thereof - Google Patents

Phenanthridine derivatives and a process for the manufacture thereof

Info

Publication number
GB976829A
GB976829A GB5441/63A GB544163A GB976829A GB 976829 A GB976829 A GB 976829A GB 5441/63 A GB5441/63 A GB 5441/63A GB 544163 A GB544163 A GB 544163A GB 976829 A GB976829 A GB 976829A
Authority
GB
United Kingdom
Prior art keywords
compound
general formula
substituted
phenyl
acid addition
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
GB5441/63A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche 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
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB976829A publication Critical patent/GB976829A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2013—Organic compounds, e.g. phospholipids, fats
    • A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/473—Quinolines; Isoquinolines ortho- or peri-condensed with carbocyclic ring systems, e.g. acridines, phenanthridines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2009—Inorganic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/10—Aza-phenanthrenes
    • C07D221/12—Phenanthridines

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Organic Chemistry (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Inorganic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises substituted octahydrophenanthridines of the general formula <FORM:0976829/C1/1> wherein R1 represents a hydrogen atom or an alkyl, alkenyl or acyl group, R2 represents an alkyl group and S represents a methoxy group at the 8- and/or 9-position or an 8, 9-methylenedioxy grouping, and acid addition salts thereof, and the preparation thereof by reducing substituted hexahydrophenanthridines of the general formula <FORM:0976829/C1/2> wherein R2 and S have the above significance, and acid addition salts thereof, with hydrogen in the presence of a hydrogenation catalyst or with an alkali-metal aluminium hydride or an alkalimetal borohydride and, if desired, submitting the reduction products to alkylation, alkenylation or acylation and/or conversion into acid addition salts. Therapeutic compositions having analgesic, anti-inflammatory and antipyretic activity and which may be administered enterally or parenterally contain as the active ingredient octahydrophenanthridines of the first general formula above. Substituted hexahydrophenanthridines of the second general formula above are prepared by reacting benzaldehyde or a suitably substituted benzaldehyde with nitromethane to form the corresponding o -nitro-styrene, reacting this compound with butadiene-1, 3 at an elevated temperature to form a 2-phenyl-1-nitro-cyclohexene-4, hydrogenating this compound to form a 2-phenyl-cyclohexylamine, acylating this compound to form a 2-phenyl-N-acyl-cyclohexylamine, and cyclizing this compound, for example with phosphorus oxychloride.
GB5441/63A 1962-02-23 1963-02-11 Phenanthridine derivatives and a process for the manufacture thereof Expired GB976829A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH223062A CH418336A (en) 1962-02-23 1962-02-23 Process for the preparation of octahydrophenanthridine compounds

Publications (1)

Publication Number Publication Date
GB976829A true GB976829A (en) 1964-12-02

Family

ID=4228900

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5441/63A Expired GB976829A (en) 1962-02-23 1963-02-11 Phenanthridine derivatives and a process for the manufacture thereof

Country Status (5)

Country Link
BR (1) BR6346877D0 (en)
CH (1) CH418336A (en)
ES (1) ES285360A1 (en)
FR (1) FR2439M (en)
GB (1) GB976829A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0787493A1 (en) * 1996-02-03 1997-08-06 F. Hoffmann-La Roche Ag Tetrahydroisoquinoline derivatives
FR2744447A1 (en) * 1996-02-03 1997-08-08 Hoffmann La Roche USE OF TETRAHYDROISOQUINOLINE DERIVATIVES

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0787493A1 (en) * 1996-02-03 1997-08-06 F. Hoffmann-La Roche Ag Tetrahydroisoquinoline derivatives
FR2744447A1 (en) * 1996-02-03 1997-08-08 Hoffmann La Roche USE OF TETRAHYDROISOQUINOLINE DERIVATIVES
ES2124672A1 (en) * 1996-02-03 1999-02-01 Hoffmann La Roche Tetrahydroisoquinoline derivatives
US5952344A (en) * 1996-02-03 1999-09-14 Hoffmann-La Roche Inc. Tetrahydroisoquinoline derivatives

Also Published As

Publication number Publication date
CH418336A (en) 1966-08-15
FR2439M (en) 1964-03-31
BR6346877D0 (en) 1973-06-14
ES285360A1 (en) 1963-08-01

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