WO2008129288A3 - Disulfonamides useful in the treatment of inflammation - Google Patents

Disulfonamides useful in the treatment of inflammation Download PDF

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Publication number
WO2008129288A3
WO2008129288A3 PCT/GB2008/001397 GB2008001397W WO2008129288A3 WO 2008129288 A3 WO2008129288 A3 WO 2008129288A3 GB 2008001397 W GB2008001397 W GB 2008001397W WO 2008129288 A3 WO2008129288 A3 WO 2008129288A3
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WO
WIPO (PCT)
Prior art keywords
treatment
inflammation
useful
disulfonamides
compounds
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Application number
PCT/GB2008/001397
Other languages
French (fr)
Other versions
WO2008129288A2 (en
Inventor
Benjamin Pelcman
Kristofer Olofsson
Edgars Suna
Ivars Kalvins
Vita Ozola
Andrejs Krasikovs
Original Assignee
Boehringer Ingelheim Int
Biolipox Ab
Benjamin Pelcman
Kristofer Olofsson
Edgars Suna
Ivars Kalvins
Vita Ozola
Andrejs Krasikovs
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Filing date
Publication date
Application filed by Boehringer Ingelheim Int, Biolipox Ab, Benjamin Pelcman, Kristofer Olofsson, Edgars Suna, Ivars Kalvins, Vita Ozola, Andrejs Krasikovs filed Critical Boehringer Ingelheim Int
Publication of WO2008129288A2 publication Critical patent/WO2008129288A2/en
Publication of WO2008129288A3 publication Critical patent/WO2008129288A3/en

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    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/18—Sulfonamides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
    • C07C311/44—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • 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
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/42—Radicals substituted by singly-bound nitrogen atoms having hetero atoms attached to the substituent nitrogen atom
    • 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
    • C07D213/60—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 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
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C07D213/60—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 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
    • C07D213/72—Nitrogen atoms
    • C07D213/76—Nitrogen atoms to which a second hetero atom is attached
    • 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
    • C07D295/12—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 singly or doubly bound nitrogen atoms
    • C07D295/125—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 singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—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 singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C07D295/12—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 singly or doubly bound nitrogen atoms
    • C07D295/135—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 singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • 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
    • C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Cardiology (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Epidemiology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (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)

Abstract

There is provided compounds of formula (I), wherein Y1, Y2, Y3, Y4, T1, T2, W1, W2, R1 and R2 have meanings given in the description, and pharmaceutically-acceptable salts thereof, which compounds are useful in the treatment of diseases in which inhibition of the activity of a member of the MAPEG family is desired and/or required, and particularly in the treatment of inflammation.
PCT/GB2008/001397 2007-04-19 2008-04-21 Disulfonamides useful in the treatment of inflammation WO2008129288A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US90785507P 2007-04-19 2007-04-19
US60/907,855 2007-04-19

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WO2008129288A3 true WO2008129288A3 (en) 2008-12-31

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Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW200930369A (en) * 2007-11-15 2009-07-16 Astrazeneca Ab Bis-(sulfonylamino) derivatives in therapy
JP5507257B2 (en) * 2007-11-30 2014-05-28 イハラケミカル工業株式会社 (1H-1,2,4-triazol-1-yl) aryl compound and method for producing the same
US20090163586A1 (en) * 2007-12-20 2009-06-25 Astrazeneca Ab Bis-(Sulfonylamino) Derivatives in Therapy 205
UA103319C2 (en) 2008-05-06 2013-10-10 Глаксосмитклайн Ллк Thiazole- and oxazole-benzene sulfonamide compounds
EP2297103B1 (en) * 2008-06-09 2012-01-04 Bristol-Myers Squibb Company Hydroxyphenylsulfonamides as antiapoptotic bcl inhibitors
WO2010132016A1 (en) * 2009-05-14 2010-11-18 Astrazeneca Ab Bis-(sulfonylamino) derivatives for treatment of pain and inflammation
JP6649538B2 (en) 2014-11-27 2020-02-19 ジェシンタ・ファーマ・アーベー Bis (sulfonamide) derivatives and their use as mPGES inhibitors
CN107001251A (en) 2014-11-27 2017-08-01 埃克杜鲁姆房地产有限公司 Double (sulfonamide) derivatives and its purposes as MPGES inhibitor
CN106588711B (en) * 2016-12-05 2018-08-14 天津理工大学 A kind of compound of platelet aggregation inhibitory activity and application thereof
CN108003144A (en) * 2017-12-15 2018-05-08 刘双伟 A kind of sulfamide derivative and its application in medicine for treating osteoporosis
US11701334B2 (en) 2018-01-10 2023-07-18 Cura Therapeutics, Llc Pharmaceutical compositions comprising phenylsulfonamides, and their therapeutic applications

Citations (4)

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US2947742A (en) * 1959-06-15 1960-08-02 Bristol Myers Co 4-amino-6-trifluoromethyl-n, n'-di-2-pyridyl-m-benzenedisulfonamide
DE2459394A1 (en) * 1974-12-16 1976-06-24 Hoechst Ag BASIC SUBSTITUTED BENZENE-1,3-DISULFONAMIDE AND PROCESS FOR THEIR PRODUCTION
WO2001016096A2 (en) * 1999-09-01 2001-03-08 Aventis Pharma Deutschland Gmbh Use of bis-sulfonamides for producing medicaments used for preventing or treating hyperlipidaemia
WO2001019390A1 (en) * 1999-09-14 2001-03-22 Pfizer Products Inc. Combination treatment with il-1ra and diaryl sulphonyl urea compounds

Patent Citations (5)

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US2947742A (en) * 1959-06-15 1960-08-02 Bristol Myers Co 4-amino-6-trifluoromethyl-n, n'-di-2-pyridyl-m-benzenedisulfonamide
DE2459394A1 (en) * 1974-12-16 1976-06-24 Hoechst Ag BASIC SUBSTITUTED BENZENE-1,3-DISULFONAMIDE AND PROCESS FOR THEIR PRODUCTION
WO2001016096A2 (en) * 1999-09-01 2001-03-08 Aventis Pharma Deutschland Gmbh Use of bis-sulfonamides for producing medicaments used for preventing or treating hyperlipidaemia
DE19941559A1 (en) * 1999-09-01 2001-03-15 Aventis Pharma Gmbh Use of bissulfonamides for the preparation of medicaments for the prophylaxis or treatment of hyperlipidemia
WO2001019390A1 (en) * 1999-09-14 2001-03-22 Pfizer Products Inc. Combination treatment with il-1ra and diaryl sulphonyl urea compounds

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Title
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BADAWI A ET AL: "DIHYDROXYBENZENE DERIVATIVES OF ANTIMICROBIAL ACTIVITY DIHYDROBENZENDERIVATE MIT ANTIMIKROBIELLER WIRKSAMKEIT", PHARMAZIE, DIE, GOVI VERLAG, ESCHBORN, DE, vol. 35, no. 12, 1980, pages 748 - 751, XP001108983, ISSN: 0031-7144 *
BADAWI, A. M. ET AL: "Disulfonamides derived from cresols of insecticidal and bactericidal activity", ORIENTAL JOURNAL OF CHEMISTRY , 2(2), 103-10 CODEN: OJCHEG; ISSN: 0970-020X, 1986, XP008086311 *
BADAWI, A. M. ET AL: "Studies on amebicidal agents: II. Synthesis and amebicidal activity of toluene-2,4-bis-sulfon-N-anilides", ORIENTAL JOURNAL OF CHEMISTRY , 2(1), 40-4 CODEN: OJCHEG; ISSN: 0970-020X, 1986, XP008086305 *
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EL-MAGHRABY, A. A. ET AL: "Synthesis of some new methyl-N-acetylaminobenzenedisulfonanilides, disulfonic esters and benzothiadiazine 1,1-dioxides", EGYPTIAN JOURNAL OF CHEMISTRY , VOLUME DATE 1985, 28(2), 163-70 CODEN: EGJCA3; ISSN: 0367-0422, 1986, XP008086318 *
HANNOUT I B ET AL: "Synthesis of some new disulphonamides active against cotton leaf worm", JOURNAL FUER PRAKTISCHE CHEMIE, LEIPZIG, DE, vol. 316, no. 5, 1974, pages 866 - 874, XP000926672, ISSN: 0021-8383 *
HANNOUT, I. B. ET AL: "Some alkylated and chlorinated benzenesulfonamides with expected insecticidal and bactericidal activities", EGYPTIAN JOURNAL OF PHARMACEUTICAL SCIENCES , VOLUME DATE 1985, 26(1-4), 213-23 CODEN: EJPSBZ; ISSN: 0301-5068, 1986, XP008086319 *
KATSCHER, ERNST ET AL: "Derivatives of symmetrical and unsymmetrical m-xylenols", MONATSHEFTE FUER CHEMIE , 64, 236-46 CODEN: MOCMB7; ISSN: 0026-9247, 1934, XP008086309 *
RIESZ, EUGEN ET AL: "Phenol and cresolsulfonyl chlorides", MONATSHEFTE FUER CHEMIE , 50, 328-34 CODEN: MOCMB7; ISSN: 0026-9247, 1928, XP008086310 *
SHI, YU ET AL: "Synthesis and insecticidal activity of novel hydroxybenzenedisulfonanilide compounds", YAOXUE XUEBAO , 37(9), 700-704 CODEN: YHHPAL; ISSN: 0513-4870, 2002, XP008086312 *
WADKINS RANDY M ET AL: "Discovery of novel selective inhibitors of human intestinal carboxylesterase for the amelioration of irinotecan-induced diarrhea: synthesis, quantitative structure-activity relationship analysis, and biological activity", MOLECULAR PHARMACOLOGY, BALTIMORE, MD, US, vol. 65, no. 6, June 2004 (2004-06-01), pages 1336 - 1343, XP002431184, ISSN: 0026-895X *

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