GB1174419A - Spiro Condensed Aromatic Compounds - Google Patents

Spiro Condensed Aromatic Compounds

Info

Publication number
GB1174419A
GB1174419A GB5823666A GB5823666A GB1174419A GB 1174419 A GB1174419 A GB 1174419A GB 5823666 A GB5823666 A GB 5823666A GB 5823666 A GB5823666 A GB 5823666A GB 1174419 A GB1174419 A GB 1174419A
Authority
GB
United Kingdom
Prior art keywords
reacting
derivative
formula
radical
converting
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
GB5823666A
Inventor
Carl Dalton Lunsford
Albert Duncan Cale
Norman David Dawson
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.)
AH Robins Co Inc
Original Assignee
AH Robins Co 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 AH Robins Co Inc filed Critical AH Robins Co Inc
Publication of GB1174419A publication Critical patent/GB1174419A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/96—Spiro-condensed ring systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1,174,419. Dibenzo[a,d]cycloheptene derivatives. A. H. ROBINS CO. Inc. 29 Dec., 1966 [30 Dec., 1965], No. 58236/66. Heading C2C. The invention comprises compounds of the formula I, wherein X represents a methylene or ethylene radical, a single bond joining the benzene rings or an oxygen or sulphur atom; R represents a C 1-8 alkyl, C 3-9 cycloalkyl or a free or substituted benzene ring; R<SP>1</SP> represents a chlorine, bromine or fluorine atom or a trifluoromethyl, C 1-8 alkyl or C 1-8 alkoxy radical and A represents a halogen atom or a C 1-8 alkoxy, cyano or amino radical and pharmaceutically acceptable acid addition and quaternary ammonium salts thereof and their preparation by heating the acid halide produced by reacting a compound of the Formula II with a thionyl or phosphorus halide and, if desired, converting the resultant compound of the Formula I where A represents a halogen atom (derived from the acid halide) into the corresponding alkoxy, cyano or amino derivative; and, if desired, converting a resultant free base into an acid addition or quaternary ammonium salt thereof. Carboxylic acids of the Formula II, where X represents a direct link, may be prepared by reacting the corresponding R<SP>1</SP>-substituted fluorene, unsubstituted in the 9-position, with sodamide, reacting the resultant 9-sodio derivative with the appropriate 3-chloropyrrolidine to give the 9-pyrrolidin-3-yl derivative and reacting the latter with butyl-lithium, reacting the resulting 9-lithio derivative with carbon dioxide and hydrolysing the product; and where X represents an ethylene or methylene radical or an oxygen or sulphur atom by reacting the appropriate nitrile of the Formula VIII with sodamide converting the resulting sodio derivative to the appropriate pyrrolidin-3-yl derivative and hydrolysing the latter to the free acid, via the corresponding carboxylic amide. Therapeutic compositions in forms suitable for oral or parenteral administration and having sedative analeptic and hypotensive properties comprise the compounds of the invention or their acid addition or quaternary ammonium salts together with a suitable carrier.
GB5823666A 1965-12-30 1966-12-29 Spiro Condensed Aromatic Compounds Expired GB1174419A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US51784265A 1965-12-30 1965-12-30

Publications (1)

Publication Number Publication Date
GB1174419A true GB1174419A (en) 1969-12-17

Family

ID=24061452

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5823666A Expired GB1174419A (en) 1965-12-30 1966-12-29 Spiro Condensed Aromatic Compounds

Country Status (5)

Country Link
BR (1) BR6685618D0 (en)
CH (1) CH512463A (en)
DE (1) DE1620240A1 (en)
FR (2) FR1602631A (en)
GB (1) GB1174419A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5760246A (en) * 1996-12-17 1998-06-02 Biller; Scott A. Conformationally restricted aromatic inhibitors of microsomal triglyceride transfer protein and method

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05255089A (en) * 1991-12-18 1993-10-05 Sanwa Kagaku Kenkyusho Co Ltd Antiviral agent

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5760246A (en) * 1996-12-17 1998-06-02 Biller; Scott A. Conformationally restricted aromatic inhibitors of microsomal triglyceride transfer protein and method
US6472414B1 (en) 1996-12-17 2002-10-29 Bristol-Myers Squibb Company Conformationally restricted aromatic inhibitors of microsomal triglyceride transfer protein and method

Also Published As

Publication number Publication date
FR6361M (en) 1968-10-07
FR1602631A (en) 1971-01-04
DE1620240A1 (en) 1970-02-12
CH512463A (en) 1971-09-15
BR6685618D0 (en) 1973-12-27

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Legal Events

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