GB1435755A - 2-phenoxy alkyl sulphonalides - Google Patents
2-phenoxy alkyl sulphonalidesInfo
- Publication number
- GB1435755A GB1435755A GB3145473A GB3145473A GB1435755A GB 1435755 A GB1435755 A GB 1435755A GB 3145473 A GB3145473 A GB 3145473A GB 3145473 A GB3145473 A GB 3145473A GB 1435755 A GB1435755 A GB 1435755A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- hydrogen
- nitro
- amino
- reacting
- 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
- -1 nitro, amino Chemical group 0.000 abstract 9
- 150000001875 compounds Chemical class 0.000 abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract 8
- 239000001257 hydrogen Substances 0.000 abstract 8
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 229910052736 halogen Inorganic materials 0.000 abstract 5
- 150000002367 halogens Chemical group 0.000 abstract 5
- 150000002431 hydrogen Chemical group 0.000 abstract 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 3
- 150000001768 cations Chemical class 0.000 abstract 3
- 229910052801 chlorine Chemical group 0.000 abstract 3
- 239000000460 chlorine Chemical group 0.000 abstract 3
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 abstract 1
- 230000003213 activating effect Effects 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000001347 alkyl bromides Chemical class 0.000 abstract 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 230000000845 anti-microbial effect Effects 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- 239000002221 antipyretic Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 abstract 1
- 230000002363 herbicidal effect Effects 0.000 abstract 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 125000006682 monohaloalkyl group Chemical group 0.000 abstract 1
- 230000000802 nitrating effect Effects 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 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)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (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)
Abstract
1435755 2 - Phenoxyalkylsulphonanilides RIKER LABORATORIES Inc 2 July 1973 [3 July 1972] 31454/73 Heading C2C Novel compounds of the Formula I wherein R x is C 1-2 alkyl or monohaloalkyl; R is hydrogen, cyano, alkyl, alkylsulphonyl, haloalkylsulphonyl, a cation or -COAR<SP>1</SP> where R<SP>1</SP> is alkyl and A is oxygen or a bond between the carbonyl carbon and the alkyl group; X is alkoxyl, alkyl, halogen, acetamido, nitro, hydrogen, amino, alkoxycarbamoyl or dialkylamino; Y is nitro, amino, alkoxycarbamoyl, dialkylamino or hydrogen, provided that one of X and Y is nitro, amino, alkoxycarbamoyl, or dialkylamino; Z is halogen, nitro or hydrogen; Z<SP>1</SP> is halogen, alkyl, alkoxy, nitro, amino, alkanamido, haloalkyl, hydroxy dialkylamino, alkoxycarbamoyl, alkylthio, alkyl sulphonyl, alkanoyl or alkylsulphinyl and n is 0, 1 or 2 in which aliphatic moieties in R, X, Y and Z<SP>1</SP> contain one to four carbon atoms may be prepared (1) where X and Y are not NH 2 , Z<SP>1</SP> is not hydroxy or amino and R is hydrogen, by reacting a compound R x SO 2 Q where Q is fluorine or chlorine with a compound of the Formula II (ii) where R is hydrogen, reacting compounds III and IV wherein D is chlorine, bromine or iodine, providing that when D is chlorine X is an activating group and M is an alkali metal or copper provided that if Z or Z<SP>1</SP> is halogen, Z or Z<SP>1</SP> is a lower atomic weight halogen than D; (iii) reacting a compound I wherein R is hydrogen with a base to introduce a cation; (iv) reacting a product of III where R 1 is a metal cation with an alkyl bromide or iodide dialkylsulphate; (v) reacting a product of (i), (ii) or (iii) with cyanogen halide, alkylsulphonyl or haloalkylsulphonyl halide, alkanoyl halide, or alkyl chloroformic acid to introduce the appropriate group at R; (vi) nitrating a compound I in which Y is hydrogen to introduce an NO 2 group at Y; (vii) modifying the substituents X, Y, Z and Z<SP>1</SP> by known methods. Pharmaceutical compositions of the compounds I show anti-inflammatory activity when administered orally, topically, parenterally or rectally with the usual excipients. Selected compounds also show analgesic, antipyretic, antimicrobial and herbicidal activity.
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 (1)
| Publication Number | Publication Date |
|---|---|
| GB1435755A true GB1435755A (en) | 1976-05-12 |
Family
ID=23023726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3145473A Expired GB1435755A (en) | 1972-07-03 | 1973-07-02 | 2-phenoxy alkyl sulphonalides |
Country Status (21)
| Country | Link |
|---|---|
| JP (4) | JPS5850984B2 (en) |
| AR (1) | AR206496A1 (en) |
| AT (1) | AT330740B (en) |
| AU (1) | AU5758673A (en) |
| BE (1) | BE801812A (en) |
| CA (1) | CA1009663A (en) |
| CH (2) | CH586667A5 (en) |
| DD (1) | DD110262A5 (en) |
| DE (1) | DE2333643A1 (en) |
| ES (2) | ES416223A1 (en) |
| FI (1) | FI61877C (en) |
| FR (1) | FR2190460B1 (en) |
| GB (1) | GB1435755A (en) |
| HU (1) | HU168676B (en) |
| IE (1) | IE38157B1 (en) |
| IL (1) | IL42640A (en) |
| NL (1) | NL7308661A (en) |
| OA (1) | OA04433A (en) |
| PL (1) | PL90016B1 (en) |
| SE (1) | SE417089B (en) |
| ZA (1) | ZA733807B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0273369A2 (en) * | 1986-12-31 | 1988-07-06 | Fujisawa Pharmaceutical Co., Ltd. | New alkanesulfonanilide derivatives, processes for preparation thereof and pharmaceutical composition comprising the same |
| EP0292979A2 (en) * | 1987-05-29 | 1988-11-30 | Fujisawa Pharmaceutical Co., Ltd. | New alkanesulfonanilide derivatives, processes for preparation thereof and pharmaceutical composition comprising the same |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2965279D1 (en) * | 1978-07-27 | 1983-06-01 | Schering Ag | Indanyl derivatives, process for their preparation and pharmaceutical compositions containing these compounds |
| DE2845996A1 (en) * | 1978-10-23 | 1980-04-30 | Bayer Ag | HERBICIDAL AGENTS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR CONTROLLING WEEDS |
| JPH0813759B2 (en) * | 1986-09-01 | 1996-02-14 | 富士写真フイルム株式会社 | Method for producing alkoxybenzene derivative |
| JPH0611747B2 (en) * | 1987-11-19 | 1994-02-16 | 大正製薬株式会社 | Sulfone anilide compound |
| JPH0717594B2 (en) * | 1989-01-25 | 1995-03-01 | 久光製薬株式会社 | Novel sulfone anilide derivative |
| IT1248475B (en) * | 1990-05-22 | 1995-01-19 | Angeli Inst Spa | INCLUSION COMPOUNDS OF NIMESULIDE WITH CYCLODESTRINE |
| ES2023552A6 (en) * | 1990-05-22 | 1992-01-16 | Leetrim Limited | Nimesulid inclusion cpds. with cyclodextrin - more water-soluble with improved bio-availability than nimesulid alone |
| BE1008307A3 (en) * | 1994-06-16 | 1996-04-02 | Europharmaceuticals Sa | Nimesulide soluble salt, aqueous solution containing same, preparation and use. |
| FR2724654B1 (en) * | 1994-09-16 | 1997-12-12 | Roussel Uclaf | NEW GALLIC ACID DERIVATIVES, THEIR PREPARATION PROCESS, THE NEW INTERMEDIATES OBTAINED, THEIR APPLICATION AS MEDICAMENTS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| WO1997047594A1 (en) * | 1996-06-13 | 1997-12-18 | Taisho Pharmaceutical Co., Ltd. | 4-nitrosulfonanilide derivatives |
| IT1291278B1 (en) * | 1996-07-05 | 1999-01-07 | Errekappa Euroterapici S P A | NIMESULIDE-BASED PHARMACEUTICAL PREPARATION FOR TOPICAL USE |
| IT1291895B1 (en) | 1997-04-24 | 1999-01-21 | Errekappa Euroterapici S P A | FLUID PHARMACEUTICAL PREPARATION BASED ON NIMESULIDE FOR ORAL AND RHINOPHARYNGAL USE |
| NZ504045A (en) | 1997-11-19 | 2001-06-29 | Kowa Co | Pyridazine derivatives with inhibitory action against interleukin-1-beta production |
| JP2000247959A (en) | 1999-02-26 | 2000-09-12 | Kowa Co | Pyridazin-3-one derivatives and pharmaceuticals containing the same |
| CN1511828A (en) * | 2002-12-31 | 2004-07-14 | �й������ž�����ҽѧ��ѧԺ����ҽ | Sufonic aniline derivatives and their medicinal use |
| CA2518227A1 (en) | 2003-03-18 | 2004-09-30 | Kowa Co., Ltd | Water-soluble phenylpyridazine derivative and medicine containing the same |
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/en active
- 1973-06-05 ZA ZA733807A patent/ZA733807B/en unknown
- 1973-06-21 NL NL7308661A patent/NL7308661A/xx unknown
- 1973-06-23 ES ES416223A patent/ES416223A1/en not_active Expired
- 1973-06-25 OA OA54947A patent/OA04433A/en unknown
- 1973-06-25 SE SE7308862A patent/SE417089B/en unknown
- 1973-06-25 FI FI2024/73A patent/FI61877C/en active
- 1973-06-29 CA CA175,343A patent/CA1009663A/en not_active Expired
- 1973-07-02 AT AT583473A patent/AT330740B/en not_active IP Right Cessation
- 1973-07-02 DD DD172003A patent/DD110262A5/xx unknown
- 1973-07-02 CH CH1032776A patent/CH586667A5/xx not_active IP Right Cessation
- 1973-07-02 FR FR7324207A patent/FR2190460B1/fr not_active Expired
- 1973-07-02 GB GB3145473A patent/GB1435755A/en not_active Expired
- 1973-07-02 IL IL42640A patent/IL42640A/en unknown
- 1973-07-02 CH CH961173A patent/CH585705A5/xx not_active IP Right Cessation
- 1973-07-02 IE IE1094/73A patent/IE38157B1/en unknown
- 1973-07-02 JP JP48074666A patent/JPS5850984B2/en not_active Expired
- 1973-07-02 AU AU57586/73A patent/AU5758673A/en not_active Expired
- 1973-07-02 DE DE19732333643 patent/DE2333643A1/en active Pending
- 1973-07-02 BE BE133036A patent/BE801812A/en unknown
- 1973-07-03 HU HURI512A patent/HU168676B/hu unknown
- 1973-07-03 PL PL1973163799A patent/PL90016B1/en unknown
-
1975
- 1975-09-16 ES ES440989A patent/ES440989A1/en not_active Expired
-
1982
- 1982-01-06 JP JP57000830A patent/JPS57140712A/en active Pending
- 1982-01-06 JP JP57000831A patent/JPS5835989B2/en not_active Expired
- 1982-09-03 JP JP57153797A patent/JPS5944311B2/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0273369A2 (en) * | 1986-12-31 | 1988-07-06 | Fujisawa Pharmaceutical Co., Ltd. | New alkanesulfonanilide derivatives, processes for preparation thereof and pharmaceutical composition comprising the same |
| EP0273369A3 (en) * | 1986-12-31 | 1989-10-18 | Fujisawa Pharmaceutical Co., Ltd. | New alkanesulfonanilide derivatives, processes for preparation thereof and pharmaceutical composition comprising the same |
| EP0292979A2 (en) * | 1987-05-29 | 1988-11-30 | Fujisawa Pharmaceutical Co., Ltd. | New alkanesulfonanilide derivatives, processes for preparation thereof and pharmaceutical composition comprising the same |
| EP0292979A3 (en) * | 1987-05-29 | 1989-11-23 | Fujisawa Pharmaceutical Co., Ltd. | New alkanesulfonanilide derivatives, processes for preparation thereof and pharmaceutical composition comprising the same |
Also Published As
| Publication number | Publication date |
|---|---|
| AT330740B (en) | 1976-07-12 |
| CH586667A5 (en) | 1977-04-15 |
| JPS5931755A (en) | 1984-02-20 |
| IL42640A (en) | 1977-10-31 |
| CA1009663A (en) | 1977-05-03 |
| BE801812A (en) | 1974-01-02 |
| FR2190460A1 (en) | 1974-02-01 |
| FI61877B (en) | 1982-06-30 |
| ES416223A1 (en) | 1976-09-01 |
| DD110262A5 (en) | 1974-12-12 |
| JPS4942640A (en) | 1974-04-22 |
| ES440989A1 (en) | 1977-07-01 |
| JPS57140712A (en) | 1982-08-31 |
| IE38157B1 (en) | 1978-01-04 |
| JPS5944311B2 (en) | 1984-10-29 |
| JPS57136560A (en) | 1982-08-23 |
| SE417089B (en) | 1981-02-23 |
| IE38157L (en) | 1974-01-03 |
| OA04433A (en) | 1980-03-15 |
| ZA733807B (en) | 1974-04-24 |
| PL90016B1 (en) | 1976-12-31 |
| AR206496A1 (en) | 1976-07-30 |
| CH585705A5 (en) | 1977-03-15 |
| JPS5850984B2 (en) | 1983-11-14 |
| NL7308661A (en) | 1974-01-07 |
| ATA583473A (en) | 1975-10-15 |
| AU5758673A (en) | 1975-01-09 |
| FR2190460B1 (en) | 1977-01-28 |
| HU168676B (en) | 1976-06-28 |
| FI61877C (en) | 1982-10-11 |
| DE2333643A1 (en) | 1974-01-24 |
| JPS5835989B2 (en) | 1983-08-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |