US3835156A - Acyl derivatives of 4-hydroxy-2h-1-benzothiopyran-3-carboxamide 1,1-dioxide - Google Patents

Acyl derivatives of 4-hydroxy-2h-1-benzothiopyran-3-carboxamide 1,1-dioxide Download PDF

Info

Publication number
US3835156A
US3835156A US00344380A US34438073A US3835156A US 3835156 A US3835156 A US 3835156A US 00344380 A US00344380 A US 00344380A US 34438073 A US34438073 A US 34438073A US 3835156 A US3835156 A US 3835156A
Authority
US
United States
Prior art keywords
dioxide
benzothiopyran
hydroxy
carboxamide
acyl derivatives
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 - Lifetime
Application number
US00344380A
Other languages
English (en)
Inventor
H Zinnes
N Lindo
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Warner Lambert Co LLC
Original Assignee
Warner Lambert Co LLC
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Warner Lambert Co LLC filed Critical Warner Lambert Co LLC
Priority to US00344380A priority Critical patent/US3835156A/en
Priority to DE2412138A priority patent/DE2412138A1/de
Priority to GB1257374A priority patent/GB1407185A/en
Priority to AU67038/74A priority patent/AU472179B2/en
Priority to DK159374AA priority patent/DK133949B/da
Priority to CA195,701A priority patent/CA1019737A/en
Priority to FR7410110A priority patent/FR2222101B1/fr
Application granted granted Critical
Publication of US3835156A publication Critical patent/US3835156A/en
Priority to DK578275A priority patent/DK578275A/da
Priority to DK578375A priority patent/DK578375A/da
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans

Definitions

  • These compounds are useful as anti-inflammatory agents.
  • a compound of l structure I is successivel treated with a base such as con y R2 R sodium hydride and an acid chloride in a solvent such 1 as dimethylformamide to form a monoacyl derivative so; of formula II.
  • Diacyl derivatives such as III are formed In by heating I with an acid anhydride.
  • the cyclic derivatives of formula IV are formed as a ll result of an internal diacylation reaction. This is 0 achieved by the treatment of I with a base such as so- I :0 R1 dium hydride followed by the addition of either phosgene (COCl or an alkylor aralkylchloroformate so. "(5 .59 1.) IV in a solvent such as dimethylformamide.
  • the starting material I is prepared as described in cowherein R and R are hydrogen, alkyl, aryl, aralkyl, pending application Ser. No. 163,076 filed July 15, alkoxy, halogen, cyano, nitro, trifluoromethyl, and the 1971, now abandoned.
  • R, R and R alkyl and The compounds of this invention are useful as antialkoxy have 1 to 7 carbon atoms such as methyl, inflammatory agents for mammals, i.e. cats, dogs, monethyl, propyl, isopropyl and the like, aryl has 6 to 8 keys and the like.
  • aryl has 6 to 8 keys and the like.
  • aryl when they are adminiscarbon atoms such as phenyl or tolyl, and aralkyl is tered orally or intraperitoneally to laboratory animals aryl as defined substituted by an alkyl group as defined.
  • rats at a dose of 25-200 mg/kg, they reduce the swelling in the paw which has been previously induced
  • an irritant such as carrageenin. following examples are included:
  • R and R are hydrogen, alkyl of 1 to 7 carbon atoms, aryl of 6 to 8 carbon atoms, aralkyl in which alkyl is as defined and substituted by an alkyl group as defined, alkoxy of l to 7 carbon atoms, halogen, cyano, nitro and trifluoromethyl.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
US00344380A 1973-03-23 1973-03-23 Acyl derivatives of 4-hydroxy-2h-1-benzothiopyran-3-carboxamide 1,1-dioxide Expired - Lifetime US3835156A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
US00344380A US3835156A (en) 1973-03-23 1973-03-23 Acyl derivatives of 4-hydroxy-2h-1-benzothiopyran-3-carboxamide 1,1-dioxide
DE2412138A DE2412138A1 (de) 1973-03-23 1974-03-13 Acylderivate von 4-hydroxy-2h-1-benzothiopyran-3-carboxamid-1,1-dioxiden
GB1257374A GB1407185A (en) 1973-03-23 1974-03-21 Benzothiopyran derivatives
DK159374AA DK133949B (da) 1973-03-23 1974-03-22 Analogifremgangsmåde til fremstilling af 4-acyloxy-2H-1-benzothiopyran-3-carboxanilid-1,1-dioxid-forbindelser.
AU67038/74A AU472179B2 (en) 1973-03-23 1974-03-22 Acyl derivativs of -hydroxy-2h-1-benzothiopyran -3-carboxamide 1,1-dioxide
CA195,701A CA1019737A (en) 1973-03-23 1974-03-22 Acyl derivatives of 4-hydroxy-2h-1-benzothiopyran-3-carboxamide 1,1-dioxide
FR7410110A FR2222101B1 (da) 1973-03-23 1974-03-25
DK578275A DK578275A (da) 1973-03-23 1975-12-18 Analogifremgangsmade til fremstilling af en 3,4-dihydro-3-phenyl-2h,5h-1-bensothiopyrano-(3,4-2)(1,3)-oxazin-2,4-dion-6,6-dioxid-forbindelse
DK578375A DK578375A (da) 1973-03-23 1975-12-18 Analogifremgangsmade til fremstilling af n-acyl-4-acyloxy-2h-1-benzothiopyran-3-carboxanilid-1,1-dioxid-forbindelser

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US00344380A US3835156A (en) 1973-03-23 1973-03-23 Acyl derivatives of 4-hydroxy-2h-1-benzothiopyran-3-carboxamide 1,1-dioxide

Publications (1)

Publication Number Publication Date
US3835156A true US3835156A (en) 1974-09-10

Family

ID=23350305

Family Applications (1)

Application Number Title Priority Date Filing Date
US00344380A Expired - Lifetime US3835156A (en) 1973-03-23 1973-03-23 Acyl derivatives of 4-hydroxy-2h-1-benzothiopyran-3-carboxamide 1,1-dioxide

Country Status (7)

Country Link
US (1) US3835156A (da)
AU (1) AU472179B2 (da)
CA (1) CA1019737A (da)
DE (1) DE2412138A1 (da)
DK (3) DK133949B (da)
FR (1) FR2222101B1 (da)
GB (1) GB1407185A (da)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3769292A (en) * 1972-04-28 1973-10-30 Warner Lambert Co N-(pyridyl)2h 1-benzothiopyran-3-carboxamide-4-hydroxy 1,1-dioxides

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3769292A (en) * 1972-04-28 1973-10-30 Warner Lambert Co N-(pyridyl)2h 1-benzothiopyran-3-carboxamide-4-hydroxy 1,1-dioxides

Also Published As

Publication number Publication date
DK133949B (da) 1976-08-16
AU6703874A (en) 1975-09-25
FR2222101A1 (da) 1974-10-18
DE2412138A1 (de) 1974-10-10
DK578375A (da) 1975-12-18
AU472179B2 (en) 1976-05-20
DK578275A (da) 1975-12-18
CA1019737A (en) 1977-10-25
FR2222101B1 (da) 1978-01-06
DK133949C (da) 1977-01-17
GB1407185A (en) 1975-09-24

Similar Documents

Publication Publication Date Title
US4185109A (en) 1-Benzothiepin-4-carboxamides
US3678077A (en) 9-oxoxanthen-2-yl-alkanoic acids
US3927023A (en) Imidazolyl benzofurans
US4025552A (en) 3-(4'-Alkoxy-benzoyl)-1,2,2-trimethylcyclopentane-carboxylic acids, methods of use and compositions containing such compounds
US5449783A (en) Diphenylthiazole derivative
US3991194A (en) Heterocyclic esters of benzopyranopyridines
US3720674A (en) 4-amino-1h-pyrazolo(3,4-d)pyrimidine derivatives
US3835156A (en) Acyl derivatives of 4-hydroxy-2h-1-benzothiopyran-3-carboxamide 1,1-dioxide
US3646020A (en) 4-acyloxy-3-phenylcarbamyl-2h-1 2-benzothiazine 1 1-dioxides
US3957782A (en) Pyrazolo [3,4-b]pyrazine-5-carboxylic acids, esters, nitriles and amides
US4154734A (en) Amides of 4-hydroxy-6H-thieno[2,3-b]thiopyran-5-carboxylic acid-7,7-dioxide
US3876655A (en) Anti-inflammatory acyl imidazoles
MATHES Some mercaptothiadiazines and their intermediate compounds
US3923801A (en) Oxazinobenzothiazine 6,6-dioxides
US3987038A (en) Process for the preparation of {1-[5-(4-hydroxy-2H-1,2-benzothiazin-3-yl)-1,2,4-oxadiazol-3-yl]methyl}ethanone S,S-dioxide
US3828073A (en) 4-hydroxy-2h-1-benzothiopyran-3-carboxamides and their corresponding s-oxides
US3697505A (en) Aromatic substituted amidines
US3676463A (en) Oxobenzofuran carboxamides
US3564008A (en) Process for preparing 1-acyl-2-phenyl-3-indolylaliphatic acid derivatives
US3646021A (en) 4 - hydroxy - 3 - furylcarbamyl - 2h - 1 2-benzothiazine 1 1-dioxides and process thereof
US3303191A (en) Novel 4-ketodihydro-2, 1-benzothiazine-2, 2-dioxides
US3984441A (en) Chromonealdehyde compounds and process for the production thereof
STEFANYE et al. ACYLATION OF 3, 6-PYRIDAZINEDIONES
US3729487A (en) 2-halo-3-aminothietane and 2h-thiete-1,1-dioxides
SU1235867A1 (ru) 2-(0-Карбоксифениламино)-6 @ -пиримидо (2,1- @ )хиназолон-6 сол нокислый,про вл ющий противовоспалительную активность