GB998835A - (ª‡-alkylideneacyl)-phenyl compounds - Google Patents

(ª‡-alkylideneacyl)-phenyl compounds

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Publication number
GB998835A
GB998835A GB1619/62A GB161962A GB998835A GB 998835 A GB998835 A GB 998835A GB 1619/62 A GB1619/62 A GB 1619/62A GB 161962 A GB161962 A GB 161962A GB 998835 A GB998835 A GB 998835A
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United Kingdom
Prior art keywords
aliphatic
substituted
acid
groups
mononuclear
Prior art date
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Expired
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GB1619/62A
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Merck and Co Inc
Original Assignee
Merck and Co Inc
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Filing date
Publication date
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB998835A publication Critical patent/GB998835A/en
Expired legal-status Critical Current

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    • 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid 
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/373—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in doubly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
    • C07C65/40—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups containing singly bound oxygen-containing groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Paper (AREA)

Abstract

The invention comprises compounds of the general formula <PICT:0998835/C2/1> wherein each of R, R1 and R2 is a hydrogen or halogen atom or a halomethyl, hydroxy, C1- 5 aliphatic, C1- 5 aliphatic oxy, C1- 5 aliphatic-thio, alicyclic, mononuclear aryl, mononuclear aryl substituted - C1- 5 - aliphatic, mononuclear arylsubstituted C1- 5 aliphatic thio, mononuclear aryloxy, or mononuclear aryl-thio radical with the proviso that not all of R, R1 and R2 are hydrogen atoms, or R and R2 are joined to form with the carbon atoms to which they are attached a 5- or 6-membered carbocyclic ring; each of R3, R4, R5 and R6 is a hydrogen atom or a halomethyl, C1- 5-aliphatic, mononuclear aryl, C1- 5 aliphatic-oxy, hydroxy, acylamino or nitroradical or R3 and R4 are joined to form with the ring carbons to which they are attached a 5- or 6-membered carbocyclic ring; A is an oxygen or sulphur atom; B is a divalent C1- 5 aliphatic, divalent C1- 5 alkylene oxy or divalent C1- 5-aliphatic-mono-nuclear aryl radical; and X is a hydroxyl or a salt of a hydroxyl radical or is an alkoxy, amino or hydrazino radical, (in the above definitions the aliphatic, aliphatic-oxy and aliphatic-thio groups may be straight-chain or branched-chain, saturated or unsaturated, and may have amino, halomethyl, carboxyl, substituted carboxyl, hydroxyl, alkylthio, arylthio or nitro substituents; the alicyclic groups may also be substituted as for the aliphatic groups; the aryl, aryloxy, arylthio, and arylaliphatic groups may be substituted by C1-5-alkyl, C1-5 alkoxy, C1-5 alkylthio, hydroxy, or halomethyl groups or halogen atoms; and amides include substituted amides containing the group NR7R8, where R7 and R8 are aliphatic or aromatic groups either substituted or unsubstituted or R7 and R8 are joined to form a heterocyclic ring) and the preparation thereof (a) by reacting an appropriate aliphatic acylphenyl compound with a salt of a secondary amine in the presence of paraformaldehyde and treating the Mannich base so formed with a weak base; (b) by brominating an appropriate a ,b -dialiphatic acetylphenyl derivative and treating the resulting product with a dehydrohalogenating agent, (c) by condensing an appropriate aliphatic acyl phenyl compound in alkaline medium with an arylaldehyde and if desired, (d) by converting the product of any of the above processes into an acid, ester, amide or hydrazide thereof. Saturated acylphenoxy- and acylphenylthioderivatives of monocarboxylic acids used as starting materials are prepared by Friedel-Craft reaction or by hydrogenation of the a -alkylideneacyl)phenyl derivatives of the invention; acylphenoxyacetic acid and other acylphenoxy derivatives of monocarboxylic acids from the acylphenol and a haloacetate or other ester; acylphenols from the phenol and a carboxylic acid in the presence of boron trifluoride; orthoacylphenols by the Fries arrangement by esterifying a phenol with an acid halide and heating the ester with aluminium chloride; 4-chloro-3-propionylphenol by nitration of 2-chloropropiophenone to 2 - chloro - 5 - nitropropiophenone, reduction of this to 2-chloro-5-aminopropiophenone and diazotization; 2,4-dimethyl-5-butyrylphenol by diazotization of the amine; methyl 3-(bromomethyl)-benzoate and 2-(bromomethyl)-benzoate by bromination of the methylbenzoyl chloride in methanol; 21,61-dichloro-31 -hydroxybutyrophenone by Grignard reaction between 2,6-dichloro-3-methoxy benzaldehyde and propyl magnesium bromide to give 2,6-dichloro - 3 - methoxy - a - propylbenzyl alcohol, oxidation to 21,61 - dichloro - 31 - methoxy - butyrophenone and hydrolysis; ethyl 4-chloromethylbenzoate by chlorination of p-tolunitrile to 4-chloromethylbenzonitrile, hydrolysis to 4-chloromethylbenzoic acid and esterification; and 3 - methyl - 4 - phenoxyacetylphenoxyacetic acid from phenol and the 4-chloroacetyl-3-methylphenoxyacetic acid. 3 - Chloro - 4 - (2 - methylene - butyryl)-phenoxyacetic acid and ethyl mercaptan gave 3 - chloro - 4 - [2 - (ethylmercaptomethyl) - butyryl] - phenoxyacetic acid; 4 - methacryloyl - 3 - chlorophenoxy acetic acid and thioglycollic acid gave 4-[2-(carboxymethylmercaptomethyl) - propionyl] - 3 - chlorophenoxyacetic acid and similarly 3-chloro-4-[2-(carbomethylmercaptomethyl) - butyryl] - phenoxyacetic acid.ALSO:Pharmaceutical compositions having diuretic, saluretic, natriuretic and chloruretic properties comprise compounds of the formula <FORM:0998835/A5-A6/1> wherein each of R, R1 and R2 is a hydrogen or halogen atom or a halomethyl, hydroxy, C1-5-aliphatic, C1-5-aliphatic-oxy, C1-5-aliphatic-thio, alicyclic, mononuclear aryl, mononuclear aryl substituted - C1-5 - aliphatic, mononuclear aryl substituted C1-5-aliphatic-thio, mononuclear acyloxy, or mononuclear arylthio radical with the proviso that not all of R, R1 and R2 are hydrogen atoms, or R and R2 are joined to form with the carbon atoms to which they are attached a 5- or 6-membered carbocyclic ring; each of R3, R4, R5 and R6 is a hydrogen atom or a halomethyl; C1-5 aliphatic, mononuclear aryl, C1-5 aliphatic-oxy, hydroxy, acylamino, or nitro radical or R3 and R4 are joined to form with the ring carbons to which they are attached a 5- or 6-membered carbocyclic ring; A is an oxygen or sulphur atom; B is a divalent C1-5-aliphatic, divalent C1-5 alkylene-oxy or divalent, C1-5-aliphatic-mononuclear aryl radical; and X is a hydroxyl or a salt of a hydroxyl radical or is an alkoxy, amino or hydrazino radical (in the above definitions the aliphatic residues may be straight- or branched-chain, saturated or unsaturated and may contain amino halomethyl, carboxyl, substituted carboxyl, hydroxyl, alkylthio, arylthio or nitro substituents; the alicyclic groups may also be substituted as for the aliphatic groups; the aryl, aryloxy, arythio and arylaliphatic groups may be substituted by C1-5 alkyl, C1-5 alkoxy, C1-5 alkylthio, hydroxy, or halomethyl groups or halogen atoms; and amides include substituted amides containing the group -NR7R8, where R7 and R8 are aliphatic or aromatic groups, either substituted or unsubstituted or R7 and R8 together with the adjacent N-atom form a heterocyclic ring) together with an inert, non-toxic pharmaceutical carrier. The compositions may also contain other diuretic or hypotensive agents or other therapeutic and/or nutritive agents and may be formulated as pills, capsules or tablets or in other forms suitable for oral administration.
GB1619/62A 1961-01-19 1962-01-16 (ª‡-alkylideneacyl)-phenyl compounds Expired GB998835A (en)

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Application Number Priority Date Filing Date Title
US8363561A 1961-01-19 1961-01-19

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GB998835A true GB998835A (en) 1965-07-21

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AT (1) AT245558B (en)
BE (1) BE612755A (en)
CH (2) CH454830A (en)
CY (1) CY360A (en)
DE (1) DE1468201C2 (en)
DK (2) DK111445B (en)
ES (1) ES273990A1 (en)
FI (2) FI41548B (en)
FR (1) FR6189M (en)
GB (1) GB998835A (en)
MY (1) MY6700039A (en)
NL (3) NL6918625A (en)
NO (1) NO115029B (en)
OA (1) OA01269A (en)
SE (2) SE318865B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4699926A (en) * 1986-04-04 1987-10-13 Merck & Co., Inc. Compounds useful in treating sickle cell anemia
US4731381A (en) * 1986-04-04 1988-03-15 Merck & Co., Inc. Method of treating a person for sickle cell anemia
US4731473A (en) * 1986-04-04 1988-03-15 Merck & Co., Inc. Compounds useful in treating sickle cell anemia

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3320306A (en) * 1964-01-29 1967-05-16 Merck & Co Inc Process for the preparation of 4-(2-methylenealkanoyl)phenoxy alkanoic acids by decarboxylation
GB1108575A (en) * 1964-06-16 1968-04-03 Merck & Co Inc Preparation of substituted phenoxyacetic acids
US4887995A (en) * 1985-01-22 1989-12-19 University Of Pittsburgh Method of treating sickle cell anemia
DE3512179A1 (en) * 1985-04-03 1986-12-04 Merck Patent Gmbh, 6100 Darmstadt PHOTO INITIATORS FOR PHOTOPOLYMERIZATION IN AQUEOUS SYSTEMS
US5741818A (en) 1995-06-07 1998-04-21 University Of Saskatchewan Semicarbazones having CNS activity and pharmaceutical preparations containing same
KR20010020201A (en) 1997-04-22 2001-03-15 코센시스 인크 Carbocyclic and heterocyclic substituted semicarbazones and thiosemicarbazones and the use thereof
EP0947494A1 (en) * 1998-03-30 1999-10-06 F. Hoffmann-La Roche Ag Derivatives of phenoxy acetic acid and phenoxymethyltetrazole having antitumor activity

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH211822A (en) * 1937-09-18 1940-10-15 Chem Ind Basel Process for the preparation of an azo dye.
CH211819A (en) * 1937-09-18 1940-10-15 Chem Ind Basel Process for the preparation of an azo dye.
CH291376A (en) * 1950-02-13 1953-06-15 Lilly Co Eli Process for the preparation of o- (N-2- (B-oxy-ethoxy) -3-oxymerkuri-propyl-carbamido) -phenoxyacetic acid.
US2694069A (en) * 1952-10-24 1954-11-09 Searle & Co Basic esters of hydroxy-and alkoxy-substituted phenyloxoalkenoic acids and their salts

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4699926A (en) * 1986-04-04 1987-10-13 Merck & Co., Inc. Compounds useful in treating sickle cell anemia
US4731381A (en) * 1986-04-04 1988-03-15 Merck & Co., Inc. Method of treating a person for sickle cell anemia
US4731473A (en) * 1986-04-04 1988-03-15 Merck & Co., Inc. Compounds useful in treating sickle cell anemia

Also Published As

Publication number Publication date
SE332168B (en) 1971-02-01
DE1468201B1 (en) 1971-11-11
CY360A (en) 1967-01-13
DE1468201C2 (en) 1972-06-08
AT245558B (en) 1966-03-10
MY6700039A (en) 1967-12-31
CH454830A (en) 1968-04-30
NO115029B (en) 1968-07-08
ES273990A1 (en) 1962-06-16
FI41548B (en) 1969-09-01
OA01269A (en) 1969-02-15
DK111445B (en) 1968-08-26
CH452500A (en) 1968-05-31
NL273765A (en)
NL129087C (en)
FR6189M (en) 1968-07-22
NL6918625A (en) 1970-02-23
SE318865B (en) 1969-12-22
BE612755A (en) 1962-07-17
DK113286B (en) 1969-03-10
FI42539B (en) 1970-06-01

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