GB1145544A - New tetrahydroindazoles - Google Patents

New tetrahydroindazoles

Info

Publication number
GB1145544A
GB1145544A GB2818367A GB2818367A GB1145544A GB 1145544 A GB1145544 A GB 1145544A GB 2818367 A GB2818367 A GB 2818367A GB 2818367 A GB2818367 A GB 2818367A GB 1145544 A GB1145544 A GB 1145544A
Authority
GB
United Kingdom
Prior art keywords
cyclohexene
alkyl
benzoyl
morpholino
moiety
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
GB2818367A
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.)
Polichimica Sap SpA
Original Assignee
Polichimica Sap SpA
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 CH1052566A external-priority patent/CH481935A/en
Application filed by Polichimica Sap SpA filed Critical Polichimica Sap SpA
Publication of GB1145544A publication Critical patent/GB1145544A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
    • C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
    • C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D265/16—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with only hydrogen or carbon atoms directly attached in positions 2 and 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic 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
    • C07D295/04—Heterocyclic 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
    • C07D295/14—Heterocyclic 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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic 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
    • C07D295/04—Heterocyclic 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
    • C07D295/14—Heterocyclic 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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/155—Heterocyclic 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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,145,544. Tetrahydroindazoles. POLICHIMICA SAP S.p.A. 19 June, 1967 [16 July, 1966; 4 April, 1967], No. 28183/67. Heading C2C. Novel tetrahydroindazoles (and salts thereof) showing analgesic and anti-inflammatory activity of the general formula wherein R represents hydrogen or alkyl (C 1 to C 4 ), R 1 represents hydrogen, alkyl (C 1 to C 4 ), #- hydroxyethyl, -CH 2 -CHOH.CH 2 .SCH 3 , phenyl, halophenyl, (C 1 to C 4 alkoxy) phenyl, -CO 2 Et, -CH 2 .CO 2 Et, benzoyl, halobenzoyl, or (C 1 to C 4 alkoxy) benzoyl and R 1 when a benzoyl, halobenzoyl or alkoxybenzoyl group is alternatively in the 1-position of the indazole ring, R 2 represents hydrogen, alkyl (C 1 to C 4 ), carboxyl, or -CSNHCH 3 and R 3 represents alkyl (C 1 to C 4 ), alkenyl (C 1 to C 4 ) or aralkyl, are prepared by reacting a 1-morpholino- (or 1-pyrrolidino or 1 - piperidino) - 2 - thiocarbamoyl (i.e. the -CSNHR 3 moiety)-6-substituted (by the R 2 moiety)-1-cyclohexene or a 2-thiocarbamoyl (i.e. the -CSNHR 3 moiety)-6-substituted (by the R 2 moiety)-1-cyclohexanone with a hydrazine of the formula R 1 NHNH 2 and optionally alkylating on the amino nitrogen atom in order to produce compounds wherein R is alkyl, and, when R 1 is hydrogen, optionally acylating the ring nitrogen atom in the 1- or 2- position with benzoyl chloride, halo-benzoyl chloride or alkoxy-benzoyl chloride. 1 - Morpholino - 2 - (N - methylthiocarbamoyl)- 1 - cyclohexene is prepared by the interaction of methyl isothiocyanate and 1-morpholino-cyclohexene. 1 - Morpholino - 2 - (N - methylthiocarbamoyl) - 6 - methyl - 1 - cyclohexene is similarly prepared. 2,6 - Di - (N - methylthiocarbamoyl) - 1 - cyclohexanone is obtained by reacting methyl isothiocyanate with 1-pyrrolidino-1-cyclohexene followed by treatment of the reaction product with hydrochloric acid.
GB2818367A 1966-07-16 1967-06-19 New tetrahydroindazoles Expired GB1145544A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IT1656266 1966-07-16
IT2036266 1966-07-16
CH1052566A CH481935A (en) 1966-07-20 1966-07-20 Process for the preparation of N-acyl-3,4-dihydrooxazinen- (1,3)
IT1455667 1967-04-04

Publications (1)

Publication Number Publication Date
GB1145544A true GB1145544A (en) 1969-03-19

Family

ID=27429293

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2818367A Expired GB1145544A (en) 1966-07-16 1967-06-19 New tetrahydroindazoles

Country Status (2)

Country Link
FR (1) FR1555544A (en)
GB (1) GB1145544A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010034657A1 (en) 2008-09-25 2010-04-01 F. Hoffmann-La Roche Ag 3-amino-indazole or 3-amino-4,5,6,7-tetrahydro-indazole derivatives
JP2019516770A (en) * 2016-05-23 2019-06-20 ザ ロックフェラー ユニバーシティー Aminoacyl indazole immunomodulators for treating autoimmune diseases

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH508343A (en) * 1969-04-29 1971-06-15 Ciba Geigy Ag Use of oxazine derivatives for combating phytopathogenic fungi
DE3339351A1 (en) * 1983-10-29 1985-05-09 Bayer Ag, 5090 Leverkusen IODACETAMIDE

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010034657A1 (en) 2008-09-25 2010-04-01 F. Hoffmann-La Roche Ag 3-amino-indazole or 3-amino-4,5,6,7-tetrahydro-indazole derivatives
JP2012503618A (en) * 2008-09-25 2012-02-09 エフ．ホフマン−ラ ロシュ アーゲー 3-amino-indazole or 3-amino-4,5,6,7-tetrahydroindazole derivatives
US8153663B2 (en) 2008-09-25 2012-04-10 Hoffmann-La Roche Inc. 3-amino-indazole or 3-amino-4,5,6,7-tetrahydro-indazole derivatives
JP2019516770A (en) * 2016-05-23 2019-06-20 ザ ロックフェラー ユニバーシティー Aminoacyl indazole immunomodulators for treating autoimmune diseases

Also Published As

Publication number Publication date
FR1555544A (en) 1969-01-31

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