JPS5589257A - New easily-absorbable sulfur-containing prodrug of non- steroidal antiphlogistic, and their drug compositions - Google Patents
New easily-absorbable sulfur-containing prodrug of non- steroidal antiphlogistic, and their drug compositionsInfo
- Publication number
- JPS5589257A JPS5589257A JP16746179A JP16746179A JPS5589257A JP S5589257 A JPS5589257 A JP S5589257A JP 16746179 A JP16746179 A JP 16746179A JP 16746179 A JP16746179 A JP 16746179A JP S5589257 A JPS5589257 A JP S5589257A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compounds
- drug compositions
- containing prodrug
- steroidal
- 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.)
- Pending
Links
- 230000001741 anti-phlogistic effect Effects 0.000 title abstract 3
- 230000003637 steroidlike Effects 0.000 title abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title 1
- 239000002260 anti-inflammatory agent Substances 0.000 title 1
- 239000003814 drug Substances 0.000 title 1
- 229940079593 drug Drugs 0.000 title 1
- 239000000203 mixture Substances 0.000 title 1
- 229940002612 prodrug Drugs 0.000 title 1
- 239000000651 prodrug Substances 0.000 title 1
- 229910052717 sulfur Inorganic materials 0.000 title 1
- 239000011593 sulfur Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 210000004400 mucous membrane Anatomy 0.000 abstract 2
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 230000002496 gastric effect Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000002085 irritant Substances 0.000 abstract 1
- 231100000021 irritant Toxicity 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 210000004379 membrane Anatomy 0.000 abstract 1
- 239000012528 membrane Substances 0.000 abstract 1
- KBFOBMYHWKFFLX-UHFFFAOYSA-N methylsulfanylmethyl 2-hydroxybenzoate Chemical compound CSCOC(=O)C1=CC=CC=C1O KBFOBMYHWKFFLX-UHFFFAOYSA-N 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 239000012466 permeate Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Furan Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
NEW MATERIAL:Compounds of formula I [R-CCO is acyloxy residue of arbitrary non-steroidal antiphlogistics containing carboxylic acid part; R1 is H, 1W8C alkyl, 3W7C cycloalkyl, 1W8C alkoxyalkyl, etc.; R2 is same as defined in R1, excepting H; R1 and R2 may together form (CH2)n, etc.; n is 3 or 4; X is S, SO, etc.] or non-toxic acid addition salt.
EXAMPLE: (Methylthio)methyl 2-hydroxybenzoate.
USE: Non-steroidal antiphlogistics. Active by oral or local administration. Low irritant. Permeate easily through the mucous membranes, e.g. the mucous membranes of eyes and the gastric mecous membrane.
PROCESS: Compounds of formula I are obtained by reacting compounds of formula R-COOH with compounds of formula II (Z is halogen) in a solvent such as acetonitrile in the presence of an acid acceptor such as triethylamine.
COPYRIGHT: (C)1980,JPO&Japio
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US97224378A | 1978-12-22 | 1978-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5589257A true JPS5589257A (en) | 1980-07-05 |
Family
ID=25519402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16746179A Pending JPS5589257A (en) | 1978-12-22 | 1979-12-21 | New easily-absorbable sulfur-containing prodrug of non- steroidal antiphlogistic, and their drug compositions |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5589257A (en) |
| DK (1) | DK551579A (en) |
| NO (1) | NO148595C (en) |
| SE (1) | SE7910590L (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS572252A (en) * | 1980-04-21 | 1982-01-07 | Merck & Co Inc | Novel precursor drug of biological activator containing mercapto group |
| CN106957251A (en) * | 2017-04-06 | 2017-07-18 | 武汉大学 | A kind of method for preparing alkyl thiomethyl ester type compound |
-
1979
- 1979-12-21 JP JP16746179A patent/JPS5589257A/en active Pending
- 1979-12-21 DK DK551579A patent/DK551579A/en not_active Application Discontinuation
- 1979-12-21 NO NO794244A patent/NO148595C/en unknown
- 1979-12-21 SE SE7910590A patent/SE7910590L/en not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS572252A (en) * | 1980-04-21 | 1982-01-07 | Merck & Co Inc | Novel precursor drug of biological activator containing mercapto group |
| CN106957251A (en) * | 2017-04-06 | 2017-07-18 | 武汉大学 | A kind of method for preparing alkyl thiomethyl ester type compound |
Also Published As
| Publication number | Publication date |
|---|---|
| NO148595C (en) | 1983-11-09 |
| NO148595B (en) | 1983-08-01 |
| NO794244L (en) | 1980-06-24 |
| SE7910590L (en) | 1980-06-23 |
| DK551579A (en) | 1980-06-23 |
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