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Sulfonanilide Compounds

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~" ' Nil II II II Nil 1 1 Nil II MINI II J European Patent Office o «i -» © Publication number: 0 31/ 332 B1 Office europeen* des.. brevets , © EUROPEAN PATENT SPECIFICATION © Date of publication of patent specification: 19.05.93 © Int. CI.5: C07C 311/08, C07D 309/12, C07D 211/46, C07C 317/14, © Application number: 88310899.5 C07C 323/18, C07D 335/02, A61K 31/18, A61K 31/33 (5)nn, Date of filing: 18.11.88AOAAOO ' © Sulfonanilide compounds. ® Priority: 19.11.87 JP 292856/87 Urawa-shi(JP) Inventor: Ohuchi, Yutaka @ Date of publication of application: Azumaso 101, 12-11 Oyaba-2-chome 24.05.89 Bulletin 89/21 Urawa-shl(JP) Inventor: Sekluchl, Kazuto © Publication of the grant of the patent: 2716-4-1-204 Oaza Kawarabukl 19.05.93 Bulletin 93/20 Ageo-shl(JP) Inventor: Salto, Shlujl © Designated Contracting States: Pakusaldo Maehara 202 31-12, Torocho- AT BE CH DE FR GB IT LI LU NL SE 1 - chome Omlya-shl(JP) © References cited: Inventor: Hatayama, Katsuo EP-A- 0 093 591 Danchl 35-3 1200-215, Horlsaklcho FR- A- 2 244 473 Omlya- shl(JP) US- A- 3 725 451 Inventor: Sota, Kaoru US-A- 3840 597 1158- 11, Shlmotoml US- A- 3 856 859 Tokorozawa- shl(JP) © Proprietor: TAISHO PHARMACEUTICAL CO. LTD © Representative: Colelro, Raymond et al 00 24- 1 Takata 3- chome Toshlma- ku MEWBURN ELLIS & CO. 2/3 Cursltor Street CM Tokyo 1 71 (JP) London EC4A 1BQ (GB) CO CO @ Inventor: Yoshlkawa, Kensel IV 2878, Dalmon CO Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid (Art. 99(1) European patent convention). Rank Xerox (UK) Business Services (3. 10/3.6/3.3. 1) EP 0 317 332 B1 Description The present invention relates to sulfonanilide compounds and more particularly sulfonanilide com - pounds and the pharmaceutical^ acceptable salts thereof having anti - inflammatory effect. 5 In U.S. Patents Nos. 3,840,597, 3,856,859 and 3,906,024 and Japanese Patent Kokai No. 10,584 (1986), there are disclosed sulfonamide compounds having substituted phenyl groups via an oxygen atom or a sulfur atom and showing anti - inflammatory effect [e.g., N-(4-nitro-2-phenoxy-phenyl)- methanesulfonamide]. However, there is a problem that drugs showing anti - inflammatory effect have gastrointestinal injuries io as clinical side effects. SUMMARY OF THE INVENTION As a result of the earnest research for the purpose of the above, the present inventors have found the 75 compounds showing anti - inflammatory, antipyretic and analgesic effects and further showing the decrease of side effects such as gastrointestinal injuries, and accomplished the present invention. According to the present invention, there is provided sulfonanilide compounds represented by the formula 20 NHS02R1 I R2 25 I N02 30 wherein R1 is a lower alkyl group or a trifluoromethyl group, R2 is a cycloalkylidenemethyl group, a group of the formula -A-R3 (wherein A is an oxygen atom, a sulfur atom, a sulfinyl group or a sulfonyl group and R3 is a cycloalkyl group having 5-8 carbon atoms; a cycloalkyl group having 5-8 carbon atoms 35 substituted by one or two of a lower alkyl group, an oxo group, a hydroxyl group or a methanesulfonyloxy group; a tetrahydropyranyl group; a tetrahydrothiopyranyl group; or a 1 - methylpiperidyl group) or a group of the formula - B - R+ (wherein B is a carbonyl group, a hydroxymethylene group or a methylene group, R+ is a cycloalkyl group having 5-8 carbon atoms) and the pharmaceutically acceptable salts thereof. 40 BRIEF DESCRIPTION OF THE DRAWING Figure 1 shows the body weight change in Experiment 2. DETAILED DESCRIPTION OF THE INVENTION 45 In the present invention, the cycloalkylidenemethyl group refers to a cyclopentylidenemethyl group, a cyclohexylidenemethyl group and the like. The lower alkyl group refers to a lower alkyl group having 1 to 4 carbon atoms such as, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert- butyl group and the like, and the cycloalkyl group having 5-8 carbon atoms refers to 50 a cyclopentyl group, a cyclohexyl group, a cycloheptyl group and a cyclooctyl group. The pharmaceutically acceptable salt refers to inorganic salts such as a lithium salt, a sodium salt, a potassium salt, a calcium salt and the like, and salts with organic amines such as triethylamine, ethanolamine and the like. Among the preferred compounds of the present invention are compounds of Formula I wherein R1 is a 55 methyl group or a trifluoromethyl group, R2 is a cyclopentyloxy group, a cyclohexyloxy group, a cyclopen - tylthio group and a tetrahydro-4H-thiopyranyloxy group. The compounds of Formula I can be prepared, for example, from known compounds according to the following methods. 2 EP 0 317 332 B1 (1) A compound of Formula I wherein R2 is -A-R3 (wherein A is an oxygen atom or a sulfur atom) can be prepared from a 2 - halonitrobenzene as a starting material. Namely, a 2 - halonitrobenzene is reacted with a compound of the formula R3-YH (wherein R3 is as defined above, and Y is an oxygen atom or a sulfur atom) in the presence of a base and/or copper to 5 give a compound of the formula N02 I Y-R3 10 II 15 (wherein Y and R3 are as defined above). Examples of the base used in the reaction are alkali hydroxides such as sodium hydroxide, potassium hydroxide and the like, alkali hydrides such as sodium hydride, potassium hydride and the like, alkali carbonates such as sodium carbonate, potassium carbonate and the like, and alkoxides such as sodium ethoxide, potassium tert - butoxide and the like. 20 Next, the compound of Formula II is reduced to give an amino form. The reduction may be an ordinary reduction by which a nitro group is reduced to an amino group, for example, catalytic reduction using palladium or platinum, or reduction using iron, tin, sodium sulfide -ammonium chloride, sodium borohydride or lithium alminum hydride. Subsequently, the amino form obtained above is reacted with a compound of the formula R1S02X or 25 (R1S02)20 (wherein R1 is as defined above, and X is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom) to give a sulfonanilide form, which is then nitrated to give a compound of the present invention represented by the formula NHSO2R1 I Y-R3 III 35 NO 2 40 wherein R1, R3 and Y are as defined above. (2) A compound of Formula I wherein R2 is - 0 - R3 can be also obtained from 2 - hydroxy - 4 - nitroaniline as a starting material. Namely, 2-hydroxy-4-nitroaniline is reacted with a compound of the formula R3-X (wherein R3 and X are as defined above ) in the presence of a base and followed by reacting with a compound of the formula R1S02X or (R1S02)20 (wherein R1 and X are as defined above 45 ) to give a compound of Formula I. (3) A compound of Formula I wherein R2 is -A-R3 (wherein A is as defined above, and R3 is a cycloalkyl group substituted by a hydroxyl group) can be prepared according to the following method. That is, this compound can be prepared by reducing the compound of Formula I wherein R3 is an oxocycloalkyl group, obtained in the method of item (1). The reduction used in this reaction may be an 50 ordinary reduction by which a ketone is converted to an alcohol, for example, a reduction using sodium borohydride, lithium alminum hydride, diborane, lithium, sodium and the like. (4) A compound of Formula I wherein R2 is -A-R3 (wherein A is as defined above, and R3 is an oxocycloalkyl group) can be also prepared according to the following method. More particularly, this compound can be prepared by oxidizing a compound represented by the 55 formula 3 EP 0 317 332 B1 NHSO2R1 I A-R5 IV 70 wherein R1 and A are as defined above, R5 is a cycloalkyl group substituted by a hydroxyl group, obtained in the item (1), and then subjecting to a nitration similar to that of the item (1). The oxidation used in this reaction may be an ordinary oxidation by which an alcohol is converted to a ketone, for example, methods using chromium trioxide (Jones reagent, Collins reagent and the like), potassium permanganate, manganese dioxide, dimethyl sulfoxide and the like. 75 (5) A compound of Formula I wherein R2 is -A-R3 (wherein A is a sulfinyl group or a sulfonyl group) can be prepared by oxidizing the compound of Formula I wherein R2 is - S - R3 obtained in the above item (1) in accordance with an ordinary oxidation, for example, methods using hydrogen peroxide, peracetic acid, m -chloroperbenzoic acid, potassium permanganate, sodium periodate and the like. (6) A compound of Formula I wherein B is a carbonyl group can be prepared from 2-aminobenzonitrile 20 as a starting material. More specially, 2-aminobenzonitrile is reacted with an organometallic compound containing the group R+, and hydrolyzed to give a 2-cycloalkylcarbonylaniline compound. Examples of the organometallic compound containing the group R+ in this reaction are Grignard reagents, or- ganolithium compounds or organocopper compounds such as cyclopentyl magnesium bromide, cyclohexylmagnesium chloride, cyclohexylmagnesium bromide, cyclopentyllithium, cyclohexyllithium, 25 lithium dicyclohexyl cuprate and the like.
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    US008298.992B2 (12) United States Patent (10) Patent No.: US 8,298,992 B2 Stern et al. (45) Date of Patent: Oct. 30, 2012 (54) LOW ODOR, LOW VOLATILITY SOLVENT (56) References Cited FOR AGRICULTURAL CHEMICALS U.S. PATENT DOCUMENTS (75) Inventors: Alan J. Stern, Magnolia, TX (US); 2,778,826 A * 1/1957 Schmidle ...................... 546,192 David Ferguson, Spring, TX (US); 3,074,940 A * 1/1963 Benzing ............. ... 544,178 Howard Stridde, George West, TX (US) 3,342,673 A * 9, 1967 Kaufman et al. ............. 514,443 5,283,229 A 2/1994 Narayanan et al. (73) Assignee: Huntsman Petrochemical LLC. The 2005, 0137091 A1 6, 2005 Herold et al. Woodlands, TX (US) 2005/0215433 A1 9, 2005 Benitez et al. (*) Notice: Subject to any disclaimer, the term of this OTHER PUBLICATIONS patent is extended or adjusted under 35 Masuyama A. Preparation and Surface Active Properties of Terminal U.S.C. 154(b) by 743 days. Amide Type of Alcohol Ethoxylates, Jun. 1989, JAOCS, vol. 66, No. (21) Appl. No.: 12/300,482 6, pppp. 834-837.* * cited by examiner (22) PCT Filed: May 25, 2007 86) PCT No.: PCT/US2007/069793 Primary Examiner — Brian-Yong S Kwon (86) O Assistant Examiner — Andriae M Holt S371 (c)(1), (74) Attorney, Agent, or Firm — Huntsman International (2), (4) Date: Nov. 12, 2008 LLC (87) PCT Pub. No.: WO2007/140332 (57) ABSTRACT PCT Pub. Date: Dec. 6, 2007 A composition includes an agricultural component in an (65) Prior Publication Data amount of at least about 27% by weight and a solvent com position in an amount not greater than about 55% by weight.