IE37942B1 - Carbazoles - Google Patents
CarbazolesInfo
- Publication number
- IE37942B1 IE37942B1 IE1252/73A IE125273A IE37942B1 IE 37942 B1 IE37942 B1 IE 37942B1 IE 1252/73 A IE1252/73 A IE 1252/73A IE 125273 A IE125273 A IE 125273A IE 37942 B1 IE37942 B1 IE 37942B1
- Authority
- IE
- Ireland
- Prior art keywords
- amino
- group
- lower alkyl
- formula
- lower alkoxy
- Prior art date
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
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles 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 carbon atoms of the ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1385620 Carbazoles F HOFFMANN-LA ROCHE & CO AG 23 July 1973 [24 July 1972] 34968/73 Heading C2C The invention comprises compounds of the formula wherein R represents a hydrogen or halogen atom or a hydroxy, cyano, lower alkyl, hydroxy-(lower alkyl), lower alkoxy, acyl, benzyloxy, lower alkylthio, trifluoromethyl, carboxy, carbo-(lower alkoxy), nitro, amino, mono- (lower alkyl)amino, di(lower alkyl)amino, sulphamoyl, di(lower alkyl)sulphamoyl or difluoromethylsulphonyl group and R 1 represents a halogen atom or a hydroxy, cyano, lower alkyl, hydroxy-(lower alkyl), lower alkoxy, acyl, acylamido, benzyloxy, lower alkylthio, trifluoromethyl, carboxy, carbo-(lower alkoxy), nitro, amino, mono(lower alkyl)amino, di- (lower alkyl)amino, sulphamoyl, di(lower alkyl) - sulphamoyl or difluoromethylsulphonyl group or R and R 1 together represent a lower alkylenedioxy group, R 2 represents the grouping in which A represents a cyano, hydroxy, lower alkoxy, amino(lower alkoxy), mono(lower alkyl)- amino-(lower alkoxy), di(lower alkyl)amino- (lower alkoxy) group or the grouping wherein B represents a hydroxy, carboxy, lower alkoxy, amino, hydroxyamino, mono(lower alkyl)amino, di(lower alkyl)amino, amino-(lower alkoxy), mono(lower alkyl)amino-(lower alkoxy), di(lower alkyl)amino - (lower alkoxy) group, Y and X each represent a hydrogen atom or a lower alkyl group and n stands for 1 to 7, and R 3 represents a hydrogen atom or a lower alkyl, acyl, halo-substituted acyl, carboxy- (lower alkyl), (lower alkoxycarbonyl)-(lower alkyl), aralkyl or haloaralkyl group, or R 1 represents a hydrogen atom when R, X and R 3 each represent a hydrogen atom, Y represents a lower alkyl group and B represents a hydroxy or lower alkoxy group, and, when R or R 1 represents a carboxy and/or when B represents a hydroxy or carboxy group, salts thereof with bases and, when R or R 1 represents an amino or mono (lower alkyl)amino or di(lower alkyl)amino group and/or when B or A represents an amino- (lower alkoxy) or mono(lower alkyl)amino- (lower alkoxy) or di(lower alkyl)amino-(lower alkoxy) group, addition salts thereof with acids. The term lower alkyl means an alkyl group of 1-7 carbon atoms, acyl means alkanoyl derived from a carboxylic acid containing 1-7 carbon atoms and aryl means phenyl optionally substituted by halogen, trifluoromethyl, lower alkyl, lower alkoxy, nitro, amino, lower alkylamino and di(lower alkyl)amino. The compounds may be prepared by reacting a compound of the formula with an aromatizing agent, for the manufacture of an ester of Formula I in which R or R 1 represents a carbo-(lower alkoxy) group or B represents a lower alkoxy group esterifying an acid of Formula I in which R or R 1 represents a carboxy group or B represents a hydroxy group, for the manufacture of an acid of Formula I in which R or R 1 represents a carboxy group, R 3 represents a carboxy-(lower alkyl) group or B represents a hydroxy group hydrolysing an ester of Formula I in which R or R 1 represents a carbo-(lower alkoxy) group, R 3 represents a (lower alkoxycarbonyl)-(lower alkyl) group or B represents a lower alkoxy group, for the manufacture of a compound of Formula I in which R 1 represents an amino group reacting a compound of Formula I in which R 1 represents an acylamido group with an inorganic acid, if desired replacing a hydrogen atom denoted by R 3 in a compound of Formula I by an acyl or (lower alkoxycarbonyl)-(lower alkyl) group, for the manufacture of a compound of Formula I in which R or R 1 represents a di(lower alkyl)amino group alkylating a compound of Formula I in which R or R 1 represents an amino group, for the manufacture of a compound of Formula I in which R, R 1 or A represents a hydroxy group hydrolysing an ether of Formula I in which R, R 1 or A represents a lower alkoxy group, if desired converting a compound of Formula I in which A represents a hydroxy group into a compound of Formula I in which A represents a lower alkoxy, amino-(lower alkoxy), mono(lower alkyl)amino- (lower alkoxy) or di(lower alkyl)amino-(lower alkoxy) group, for the manufacture of an alcohol of Formula I in which A represents a hydroxy group reducing an ester of Formula I in which B represents a lower alkoxy group, if desired converting a hydroxy group denoted by B in an acid of Formula I or in a salt of such an acid with a base into an amino-(lower alkoxy), mono(lower alkyl)amino-(lower alkoxy) or di- (lower alkyl)amino-(lower alkoxy) group, for the manufacture of an optically active isomer of a compound of Formula I resolving a racemate of Formula I into its optically active isomers and isolating the desired isomer and for the manufacture of a salt of a compound of Formula I in which R or R 1 represents a carboxy group and/or B represents a hydroxy or carboxy group or in which R or R 1 represents an amino, mono(lower alkyl)amino or di(lower alkyl)amino group and/or B or A represents an amino-(lower alkoxy), mono(lower alkyl)amino- (lower alkoxy) or di(lower alkyl)amino-(lower alkoxy) group reacting such a compound of Formula I with a base or an acid. The compounds may be used as anti-inflammatory, analgesic and anti-rheumatic agents.
[GB1385620A]
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US27414272A | 1972-07-24 | 1972-07-24 |
Publications (2)
Publication Number | Publication Date |
---|---|
IE37942L IE37942L (en) | 1974-01-24 |
IE37942B1 true IE37942B1 (en) | 1977-11-23 |
Family
ID=23046965
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IE1252/73A IE37942B1 (en) | 1972-07-24 | 1973-07-23 | Carbazoles |
Country Status (26)
Country | Link |
---|---|
JP (1) | JPS5740144B2 (en) |
KR (1) | KR780000289B1 (en) |
AR (1) | AR205331A1 (en) |
AT (1) | AT325607B (en) |
AU (1) | AU475534B2 (en) |
BE (1) | BE802596A (en) |
CA (1) | CA1026348A (en) |
CH (1) | CH587819A5 (en) |
DD (1) | DD107681A5 (en) |
DE (1) | DE2337340C2 (en) |
DK (1) | DK138537B (en) |
FI (1) | FI59244C (en) |
FR (1) | FR2193611B1 (en) |
GB (1) | GB1385620A (en) |
HK (1) | HK49878A (en) |
HU (1) | HU167611B (en) |
IE (1) | IE37942B1 (en) |
IL (1) | IL42799A (en) |
KE (1) | KE2847A (en) |
LU (1) | LU68071A1 (en) |
MY (1) | MY7800315A (en) |
NL (1) | NL169877C (en) |
NO (1) | NO142865C (en) |
SE (2) | SE402283B (en) |
SU (1) | SU509220A3 (en) |
ZA (1) | ZA734047B (en) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4146542A (en) * | 1978-06-12 | 1979-03-27 | Hoffmann-La Roche Inc. | Dihydrocarbazole acetic acid and esters thereof |
US4150031A (en) * | 1978-06-26 | 1979-04-17 | Hoffmann-La Roche Inc. | Hydroxy methyl carbazole acetic acid and esters |
US4158007A (en) * | 1978-08-21 | 1979-06-12 | Hoffmann-La Roche Inc. | Carbazole methyl malonates |
US4501908A (en) * | 1981-03-12 | 1985-02-26 | Hoffmann-La Roche Inc. | 2,3-Isopropylidene ribonic acid, 1,4-lactones |
JPS6040256U (en) * | 1983-08-25 | 1985-03-20 | 伊東 璋 | Container cleaning machine |
EP0234708B1 (en) * | 1986-01-23 | 1991-02-27 | Merck Frosst Canada Inc. | Tetrahydrocarbazole 1-alkanoic acids |
EP0239306B1 (en) | 1986-03-27 | 1993-06-02 | Merck Frosst Canada Inc. | Tetrahydrocarbazole esters |
CA1326030C (en) * | 1987-07-21 | 1994-01-11 | John W. Gillard | Cyclohept[b]indolealkanoic acids |
EP0307077A1 (en) * | 1987-07-21 | 1989-03-15 | Merck Frosst Canada Inc. | Tetrahydrocarbazoles for the improvement of cyclosporin therapy |
PT95692A (en) * | 1989-10-27 | 1991-09-13 | American Home Prod | PROCESS FOR THE PREPARATION OF INDOLE-, INDENO-, PYRANOINDOLE- AND TETRA-HYDROCARBAZOLE-ALCANOIC ACID DERIVATIVES, OR WHICH ARE USEFUL AS PLA2 INHIBITORS AND LIPOXIGENASE |
JP2004010601A (en) * | 2002-06-11 | 2004-01-15 | Nippon Steel Chem Co Ltd | Method for producing indole derivative and intermediate useful for the same |
US7332516B2 (en) | 2003-01-14 | 2008-02-19 | Merck + Co., Inc. | Geminally di-substituted NSAID derivatives as Aβ42 lowering agents |
MXPA05011850A (en) * | 2003-05-06 | 2006-05-25 | Air Prod & Chem | Hydrogen storage reversible hydrogenated of pi-conjugated substrates. |
WO2005016882A1 (en) * | 2003-08-15 | 2005-02-24 | Universite Laval | Monomers, oligomers and polymers of 2-functionalized and 2,7-difunctionalized carbazoles |
US7662831B2 (en) | 2006-07-27 | 2010-02-16 | Wyeth Llc | Tetracyclic indoles as potassium channel modulators |
SI2802320T1 (en) * | 2011-11-15 | 2019-08-30 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd., | Tricyclic compounds, compositions comprising them and uses thereof |
JP5940036B2 (en) * | 2013-10-08 | 2016-06-29 | テックフィールズ バイオケム カンパニー リミテッド | Positively charged water-soluble prodrugs of aryl- and heteroarylpropionic acids with very fast skin permeability |
CN114787130A (en) * | 2020-03-25 | 2022-07-22 | 捷恩智株式会社 | Compound, liquid crystal composition and liquid crystal display element |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DD70880A (en) * | ||||
US3580926A (en) * | 1969-11-10 | 1971-05-25 | Parke Davis & Co | Carbazole-4-alkanoic acids and tetrahydrocarbazole-4-alkanoic acids |
ZA715217B (en) * | 1970-08-20 | 1972-04-26 | Org Nv | Anti-inflammatory preparations |
-
1973
- 1973-01-01 AR AR249230A patent/AR205331A1/en active
- 1973-06-14 ZA ZA734047A patent/ZA734047B/en unknown
- 1973-06-15 CH CH871673A patent/CH587819A5/xx not_active IP Right Cessation
- 1973-07-20 HU HUHO1597A patent/HU167611B/hu unknown
- 1973-07-20 IL IL42799A patent/IL42799A/en unknown
- 1973-07-20 BE BE133691A patent/BE802596A/en not_active IP Right Cessation
- 1973-07-20 KR KR7301174A patent/KR780000289B1/en active
- 1973-07-23 IE IE1252/73A patent/IE37942B1/en unknown
- 1973-07-23 GB GB3496873A patent/GB1385620A/en not_active Expired
- 1973-07-23 NO NO2975/73A patent/NO142865C/en unknown
- 1973-07-23 JP JP48081008A patent/JPS5740144B2/ja not_active Expired
- 1973-07-23 AU AU58390/73A patent/AU475534B2/en not_active Expired
- 1973-07-23 DD DD172456A patent/DD107681A5/xx unknown
- 1973-07-23 DK DK405973AA patent/DK138537B/en not_active IP Right Cessation
- 1973-07-23 AT AT649773A patent/AT325607B/en not_active IP Right Cessation
- 1973-07-23 DE DE2337340A patent/DE2337340C2/en not_active Expired
- 1973-07-23 CA CA177,061A patent/CA1026348A/en not_active Expired
- 1973-07-23 FI FI2311/73A patent/FI59244C/en active
- 1973-07-23 LU LU68071A patent/LU68071A1/xx unknown
- 1973-07-23 SE SE7310244A patent/SE402283B/en unknown
- 1973-07-24 FR FR7327020A patent/FR2193611B1/fr not_active Expired
- 1973-07-24 SU SU1950151A patent/SU509220A3/en active
- 1973-07-24 NL NLAANVRAGE7310275,A patent/NL169877C/en not_active IP Right Cessation
-
1976
- 1976-05-21 SE SE7605813A patent/SE7605813L/en unknown
-
1978
- 1978-06-13 KE KE2847A patent/KE2847A/en unknown
- 1978-08-31 HK HK498/78A patent/HK49878A/en unknown
- 1978-12-30 MY MY315/78A patent/MY7800315A/en unknown
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