JPS5850984B2 - チカンジフエニルエ−テルルイ - Google Patents
チカンジフエニルエ−テルルイInfo
- Publication number
- JPS5850984B2 JPS5850984B2 JP48074666A JP7466673A JPS5850984B2 JP S5850984 B2 JPS5850984 B2 JP S5850984B2 JP 48074666 A JP48074666 A JP 48074666A JP 7466673 A JP7466673 A JP 7466673A JP S5850984 B2 JPS5850984 B2 JP S5850984B2
- Authority
- JP
- Japan
- Prior art keywords
- nitro
- formula
- hydrogen
- compounds
- compound
- 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
Links
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 43
- 229910052739 hydrogen Chemical group 0.000 claims description 25
- 239000001257 hydrogen Chemical group 0.000 claims description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- -1 sulfonamide aryl compound Chemical class 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 150000004982 aromatic amines Chemical class 0.000 claims description 5
- 239000000460 chlorine Chemical group 0.000 claims description 5
- 229910052801 chlorine Chemical group 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229940124530 sulfonamide Drugs 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 description 21
- 238000000034 method Methods 0.000 description 17
- 150000001768 cations Chemical class 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000002260 anti-inflammatory agent Substances 0.000 description 6
- 230000003110 anti-inflammatory effect Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229940121363 anti-inflammatory agent Drugs 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 4
- 125000004422 alkyl sulphonamide group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 206010015150 Erythema Diseases 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 231100000321 erythema Toxicity 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 239000002221 antipyretic Substances 0.000 description 2
- 229940125716 antipyretic agent Drugs 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 150000008050 dialkyl sulfates Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
- JLDQORDBQQXPCI-UHFFFAOYSA-N 5-nitro-2-phenoxyaniline Chemical compound NC1=CC([N+]([O-])=O)=CC=C1OC1=CC=CC=C1 JLDQORDBQQXPCI-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 208000009386 Experimental Arthritis Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010018691 Granuloma Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- 206010030124 Oedema peripheral Diseases 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229960004977 anhydrous lactose Drugs 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000002037 dichloromethane fraction Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 150000002337 glycosamines Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910001385 heavy metal Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- HYWYRSMBCFDLJT-UHFFFAOYSA-N nimesulide Chemical compound CS(=O)(=O)NC1=CC=C([N+]([O-])=O)C=C1OC1=CC=CC=C1 HYWYRSMBCFDLJT-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
-
- 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
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
-
- 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]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00268606A US3840597A (en) | 1971-02-24 | 1972-07-03 | Substituted 2-phenoxy alkane-sulfonanilides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS4942640A JPS4942640A (cs) | 1974-04-22 |
| JPS5850984B2 true JPS5850984B2 (ja) | 1983-11-14 |
Family
ID=23023726
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP48074666A Expired JPS5850984B2 (ja) | 1972-07-03 | 1973-07-02 | チカンジフエニルエ−テルルイ |
| JP57000831A Expired JPS5835989B2 (ja) | 1972-07-03 | 1982-01-06 | 置換ジフエニルエ−テル類 |
| JP57000830A Pending JPS57140712A (en) | 1972-07-03 | 1982-01-06 | Substituted diphenyl ethers as antiinflammatory |
| JP57153797A Expired JPS5944311B2 (ja) | 1972-07-03 | 1982-09-03 | 置換ジフエニルエ−テル類 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57000831A Expired JPS5835989B2 (ja) | 1972-07-03 | 1982-01-06 | 置換ジフエニルエ−テル類 |
| JP57000830A Pending JPS57140712A (en) | 1972-07-03 | 1982-01-06 | Substituted diphenyl ethers as antiinflammatory |
| JP57153797A Expired JPS5944311B2 (ja) | 1972-07-03 | 1982-09-03 | 置換ジフエニルエ−テル類 |
Country Status (21)
| Country | Link |
|---|---|
| JP (4) | JPS5850984B2 (cs) |
| AR (1) | AR206496A1 (cs) |
| AT (1) | AT330740B (cs) |
| AU (1) | AU5758673A (cs) |
| BE (1) | BE801812A (cs) |
| CA (1) | CA1009663A (cs) |
| CH (2) | CH585705A5 (cs) |
| DD (1) | DD110262A5 (cs) |
| DE (1) | DE2333643A1 (cs) |
| ES (2) | ES416223A1 (cs) |
| FI (1) | FI61877C (cs) |
| FR (1) | FR2190460B1 (cs) |
| GB (1) | GB1435755A (cs) |
| HU (1) | HU168676B (cs) |
| IE (1) | IE38157B1 (cs) |
| IL (1) | IL42640A (cs) |
| NL (1) | NL7308661A (cs) |
| OA (1) | OA04433A (cs) |
| PL (1) | PL90016B1 (cs) |
| SE (1) | SE417089B (cs) |
| ZA (1) | ZA733807B (cs) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0009554B1 (de) * | 1978-07-27 | 1983-04-27 | Schering Aktiengesellschaft | Indanyl-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Präparate |
| DE2845996A1 (de) * | 1978-10-23 | 1980-04-30 | Bayer Ag | Herbizide mittel, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von unkraeutern |
| JPH0813759B2 (ja) * | 1986-09-01 | 1996-02-14 | 富士写真フイルム株式会社 | アルコキシベンゼン誘導体の製造方法 |
| PT86407B (pt) * | 1986-12-31 | 1990-11-20 | Fujisawa Pharmaceutical Co | Processo para a preparacao de novos derivados de alcano-sulfonanilida, e de composicoes farmaceuticas compreendendo os mesmos |
| IL86462A (en) * | 1987-05-29 | 1992-12-01 | Fujisawa Pharmaceutical Co | Alkanesulfonanilide derivatives, processes for preparation thereof and pharmaceutical compositions comprising the same |
| JPH0611747B2 (ja) * | 1987-11-19 | 1994-02-16 | 大正製薬株式会社 | スルホンアニリド化合物 |
| JPH0717594B2 (ja) * | 1989-01-25 | 1995-03-01 | 久光製薬株式会社 | 新規なスルホンアニリド誘導体 |
| IT1248475B (it) * | 1990-05-22 | 1995-01-19 | Angeli Inst Spa | Composti di inclusione di nimesulide con ciclodestrine |
| ES2023552A6 (es) * | 1990-05-22 | 1992-01-16 | Leetrim Limited | Procedimiento para la preparacion de compuestos de inclusion de nimesulida con ciclodextrina. |
| BE1008307A3 (fr) * | 1994-06-16 | 1996-04-02 | Europharmaceuticals Sa | Sel de nimesulide hydrosoluble, solution aqueuse le contenant, sa preparation et son utilisation. |
| FR2724654B1 (fr) * | 1994-09-16 | 1997-12-12 | Roussel Uclaf | Nouveaux derives de l'acide gallique, leur procede de preparation, les nouveaux intermediaires obtenus, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant |
| WO1997047594A1 (fr) * | 1996-06-13 | 1997-12-18 | Taisho Pharmaceutical Co., Ltd. | Derives de 4-nitrosulfonanilide |
| IT1291278B1 (it) * | 1996-07-05 | 1999-01-07 | Errekappa Euroterapici S P A | Preparazione farmaceutica a base di nimesulide per uso topico |
| IT1291895B1 (it) | 1997-04-24 | 1999-01-21 | Errekappa Euroterapici S P A | Preparazione farmaceutica fluida a base di nimesulide per uso orale e rinofaringeo |
| EP2017266A1 (en) | 1997-11-19 | 2009-01-21 | Kowa Co., Ltd. | Pyridazine derivatives and medicines containing the same as effective ingredients |
| JP2000247959A (ja) | 1999-02-26 | 2000-09-12 | Kowa Co | ピリダジン−３−オン誘導体及びこれを含有する医薬 |
| CN1511828A (zh) * | 2002-12-31 | 2004-07-14 | �й������ž�����ҽѧ��ѧԺ����ҽ | 磺酰苯胺类衍生物及其医药用途 |
| MXPA05009972A (es) | 2003-03-18 | 2005-11-04 | Kowa Co | Derivado de fenilpiridazina soluble en agua y medicina que contiene el mismo. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2097745A5 (en) * | 1970-04-13 | 1972-03-03 | Minnesota Mining & Mfg | Fluoroalkyl sulphonamido-diaryl-(thio)-ethers and derivs - herbicides antiinflamma |
-
1973
- 1973-01-01 AR AR248872A patent/AR206496A1/es active
- 1973-06-05 ZA ZA733807A patent/ZA733807B/xx unknown
- 1973-06-21 NL NL7308661A patent/NL7308661A/xx unknown
- 1973-06-23 ES ES416223A patent/ES416223A1/es not_active Expired
- 1973-06-25 FI FI2024/73A patent/FI61877C/fi active
- 1973-06-25 SE SE7308862A patent/SE417089B/xx unknown
- 1973-06-25 OA OA54947A patent/OA04433A/xx unknown
- 1973-06-29 CA CA175,343A patent/CA1009663A/en not_active Expired
- 1973-07-02 CH CH961173A patent/CH585705A5/xx not_active IP Right Cessation
- 1973-07-02 IL IL42640A patent/IL42640A/en unknown
- 1973-07-02 AT AT583473A patent/AT330740B/de not_active IP Right Cessation
- 1973-07-02 DD DD172003A patent/DD110262A5/xx unknown
- 1973-07-02 BE BE133036A patent/BE801812A/xx unknown
- 1973-07-02 CH CH1032776A patent/CH586667A5/xx not_active IP Right Cessation
- 1973-07-02 IE IE1094/73A patent/IE38157B1/xx unknown
- 1973-07-02 GB GB3145473A patent/GB1435755A/en not_active Expired
- 1973-07-02 DE DE19732333643 patent/DE2333643A1/de active Pending
- 1973-07-02 AU AU57586/73A patent/AU5758673A/en not_active Expired
- 1973-07-02 FR FR7324207A patent/FR2190460B1/fr not_active Expired
- 1973-07-02 JP JP48074666A patent/JPS5850984B2/ja not_active Expired
- 1973-07-03 PL PL1973163799A patent/PL90016B1/pl unknown
- 1973-07-03 HU HURI512A patent/HU168676B/hu unknown
-
1975
- 1975-09-16 ES ES440989A patent/ES440989A1/es not_active Expired
-
1982
- 1982-01-06 JP JP57000831A patent/JPS5835989B2/ja not_active Expired
- 1982-01-06 JP JP57000830A patent/JPS57140712A/ja active Pending
- 1982-09-03 JP JP57153797A patent/JPS5944311B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| HU168676B (cs) | 1976-06-28 |
| AU5758673A (en) | 1975-01-09 |
| AT330740B (de) | 1976-07-12 |
| JPS5835989B2 (ja) | 1983-08-05 |
| DD110262A5 (cs) | 1974-12-12 |
| NL7308661A (cs) | 1974-01-07 |
| JPS5944311B2 (ja) | 1984-10-29 |
| SE417089B (sv) | 1981-02-23 |
| FI61877C (fi) | 1982-10-11 |
| BE801812A (fr) | 1974-01-02 |
| ATA583473A (de) | 1975-10-15 |
| GB1435755A (en) | 1976-05-12 |
| JPS5931755A (ja) | 1984-02-20 |
| FR2190460B1 (cs) | 1977-01-28 |
| PL90016B1 (en) | 1976-12-31 |
| ES440989A1 (es) | 1977-07-01 |
| CH586667A5 (cs) | 1977-04-15 |
| IE38157B1 (en) | 1978-01-04 |
| FR2190460A1 (cs) | 1974-02-01 |
| ZA733807B (en) | 1974-04-24 |
| CA1009663A (en) | 1977-05-03 |
| FI61877B (fi) | 1982-06-30 |
| DE2333643A1 (de) | 1974-01-24 |
| JPS4942640A (cs) | 1974-04-22 |
| CH585705A5 (cs) | 1977-03-15 |
| JPS57140712A (en) | 1982-08-31 |
| ES416223A1 (es) | 1976-09-01 |
| JPS57136560A (en) | 1982-08-23 |
| IL42640A (en) | 1977-10-31 |
| OA04433A (fr) | 1980-03-15 |
| AR206496A1 (es) | 1976-07-30 |
| IE38157L (en) | 1974-01-03 |
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