GB1323302A - N-substituted-cycloalkano-indoles - Google Patents

N-substituted-cycloalkano-indoles

Info

Publication number
GB1323302A
GB1323302A GB4687070A GB4687070A GB1323302A GB 1323302 A GB1323302 A GB 1323302A GB 4687070 A GB4687070 A GB 4687070A GB 4687070 A GB4687070 A GB 4687070A GB 1323302 A GB1323302 A GB 1323302A
Authority
GB
United Kingdom
Prior art keywords
compounds
oct
derivatives
alkyl
amino group
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
GB4687070A
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.)
Sandoz AG
Original Assignee
Sandoz 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 Sandoz AG filed Critical Sandoz AG
Publication of GB1323302A publication Critical patent/GB1323302A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
    • 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
    • C07D209/80—[b, c]- or [b, d]-condensed
    • 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
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/04—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members

Landscapes

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

Abstract

1323302 Cycloalkano[b]indoles SANDOZ Ltd 2 Oct 1970 [13 Oct 1969 18 May 1970] 46870/70 Heading C2C The invention comprises compounds of formula their derivatives in which the amino group is substituted by 1 or 2 C 1-4 alkyl or hydroxyalkyl radicals or is replaced by a morpholino, piperidino, pyrrolidino or C 1-4 alkylpiperazino radical, and acid addition salts thereof, wherein R 1 is H, F, Cl or C 1-3 alkyl or alkoxy, m is 0 or 1, and either (a) n is 3, R 3 is H and R 2 is H or Me, or (b) n is 3-13, R 2 is H and R 3 is Me, provided that (i) when m is 1, R 2 is H, and (ii) when R 1 is Cl or F, R 2 and R 3 are H. These compounds, as well as those where R 3 is H, R 2 is H or Me, and n is 4-13, are prepared by (1) reacting a 1-(p-R 1 - phenyl)-3-R 3 -4-R 2 -pyrazolidine (m=0) or -hexahydropyridazine (m = 1) with a cycloalkanone containing (n+2) C atoms, or (2) (m=0) reducing with B 2 H 6 in an inert organic solvent, the corresponding N-(3-aminoalkanoyl) cyclopolymethylene[b] indole (II), (which are also claimed per se), and in either case optionally converting the amino group to the said derivatives. Therapeutic compositions for oral or parenteral administration comprise the above compounds I, which have C.N.S. depressant activity and are stated to be of use as sedatives and/or tranquillizers; or the above compounds II, which have sedative-hypnotic and in some cases antidepressant activity.
GB4687070A 1969-10-13 1970-10-02 N-substituted-cycloalkano-indoles Expired GB1323302A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US86602069A 1969-10-13 1969-10-13
US3856770A 1970-05-18 1970-05-18

Publications (1)

Publication Number Publication Date
GB1323302A true GB1323302A (en) 1973-07-11

Family

ID=26715331

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4687070A Expired GB1323302A (en) 1969-10-13 1970-10-02 N-substituted-cycloalkano-indoles

Country Status (6)

Country Link
JP (1) JPS4831108B1 (en)
AU (1) AU2094070A (en)
BE (1) BE757404A (en)
DE (1) DE2049559A1 (en)
FR (1) FR2070120B1 (en)
GB (1) GB1323302A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7662831B2 (en) 2006-07-27 2010-02-16 Wyeth Llc Tetracyclic indoles as potassium channel modulators

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5350762A (en) * 1993-03-08 1994-09-27 Hoechst-Roussel Pharmaceuticals Incorporated Tetrahydrocyclopent[B]indole methanamines and related compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7662831B2 (en) 2006-07-27 2010-02-16 Wyeth Llc Tetracyclic indoles as potassium channel modulators

Also Published As

Publication number Publication date
FR2070120B1 (en) 1975-04-18
FR2070120A1 (en) 1971-09-10
DE2049559A1 (en) 1971-04-22
AU2094070A (en) 1972-04-13
JPS4831108B1 (en) 1973-09-26
BE757404A (en) 1971-04-13

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Legal Events

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