GB1286554A - 5-alkyl indenopyridine derivatives - Google Patents

5-alkyl indenopyridine derivatives

Info

Publication number
GB1286554A
GB1286554A GB6286869A GB6286869A GB1286554A GB 1286554 A GB1286554 A GB 1286554A GB 6286869 A GB6286869 A GB 6286869A GB 6286869 A GB6286869 A GB 6286869A GB 1286554 A GB1286554 A GB 1286554A
Authority
GB
United Kingdom
Prior art keywords
compounds
alkyl
benzyl
tetrahydropyridine
cyclizing
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
GB6286869A
Inventor
Jean-Michel Bastian
Anton Ebnother
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
Priority claimed from CH94969A external-priority patent/CH510028A/en
Application filed by Sandoz AG filed Critical Sandoz AG
Publication of GB1286554A publication Critical patent/GB1286554A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/02—Preparation by ring-closure or hydrogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered

Landscapes

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

Abstract

1286554 lndeno[1,2-c]pyridine derivatives SANDOZ Ltd 24 Dec 1969 [23 Jan 1969 20 May 1969 31 Oct 1969 (2)] 62868/69 Heading C2C The invention comprises compounds of formula and their acid addition salts, wherein R 1 is H, C 1-10 alkyl, C 3-6 alkenyl or alkinyl, or benzyl, R 2 is primary or secondary C 1-5 alkyl, and R 3 is H, halogen or C 1-4 alkyl (except the compound in which R 1 = R 2 = Me, and R 3 = H), and processes for preparing them by (a) cyclizing a 1-R 1 -4- (R 3 C 6 H 4 CR 2 O)H) - 1,2,3,6 - tetrahydropyridine (II) or 1 - R 1 - 4 - (R 3 C 6 H 4 C: CR 4 R 5 ) - 1,2,3,6- tetrahydropyridine (in which compounds R 1 # H and R 4 , R 5 = H or C 1-5 alkyl), (b) splitting off R 1 from compounds of the above formula (R 1 = Me or benzyl), to give the corresponding compounds where R 1 = H, by (eg) forming the intermediates where R 1 =CO 2 R (R = C 1-5 alkyl, Ph or benzyl) by reaction with ClCO 2 R and hydrolysing the intermediates, (c) replacing the N-attached H atom in the above compounds (R 1 = H) to give such compounds where R 1 # H, (d) (R<SP>1</SP> = Me or benzyl) reacting the corresponding indeno[1,2-c]- pyridin-5-one with Rz-Mg-halide or R 2 -Li, followed by dehydration of the resulting indeno- [1,2-c]pyridin-5-ol, the starting material being formed by cyclizing, e.g. with polyphosphoric acid, an ester of 1-R 1 -2-R 3 C 6 H 4 -hexahydroisonicotinic acid. Starting materials otherwise prepared are 3-(p-toluyl)pyridine, and the unsaturated-ring analogues of II and their alkiodides. Therapeutic compositions, preferably administered orally, comprise compounds of the above formula, which in animal tests show salidiuretic activity and inhibit aggressiveness induced by isolation.
GB6286869A 1969-01-23 1969-12-24 5-alkyl indenopyridine derivatives Expired GB1286554A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CH94969A CH510028A (en) 1969-01-23 1969-01-23 Indeno-pyridines
CH765569 1969-05-20
CH1624869 1969-10-31
CH1624769 1969-10-31

Publications (1)

Publication Number Publication Date
GB1286554A true GB1286554A (en) 1972-08-23

Family

ID=27428036

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6286869A Expired GB1286554A (en) 1969-01-23 1969-12-24 5-alkyl indenopyridine derivatives

Country Status (6)

Country Link
BE (1) BE744740A (en)
DE (1) DE2002499A1 (en)
FR (1) FR2034482B1 (en)
GB (1) GB1286554A (en)
NL (1) NL7000409A (en)
SE (1) SE369304B (en)

Also Published As

Publication number Publication date
FR2034482B1 (en) 1974-04-12
NL7000409A (en) 1970-07-27
FR2034482A1 (en) 1970-12-11
SE369304B (en) 1974-08-19
BE744740A (en) 1970-07-22
DE2002499A1 (en) 1970-07-30

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Legal Events

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