EP0000152B1 - Oxaminic acids and esters, process for their preparation and pharmaceutical compositions containing them - Google Patents
Oxaminic acids and esters, process for their preparation and pharmaceutical compositions containing them Download PDFInfo
- Publication number
- EP0000152B1 EP0000152B1 EP78100167A EP78100167A EP0000152B1 EP 0000152 B1 EP0000152 B1 EP 0000152B1 EP 78100167 A EP78100167 A EP 78100167A EP 78100167 A EP78100167 A EP 78100167A EP 0000152 B1 EP0000152 B1 EP 0000152B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- compound
- carbon atoms
- formula
- alkoxy
- compounds
- 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
- 0 C*C(C1)c2c(*)ccc(N**)*2[N+]1[O-] Chemical compound C*C(C1)c2c(*)ccc(N**)*2[N+]1[O-] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Definitions
- This invention relates to oxaminic acids and esters thereof, a process for the preparation of said compounds and pharmaceutical compositions containing these compounds.
- R 1 is alkyl of 1 to 10 carbon atoms, this preferably contains 1 to 5 carbon atoms, especially 2 or 3 carbon atoms.
- R 1 can also be hydrogen.
- R 2 can be chlorine.
- R 2 can also be alkoxy of 1 to 4 carbon atoms.
- R 1 and R 2 together can also be ⁇ (CH 2 ) m wherein m is 3 or 4, preferably 3.
- R 3 can be OH.
- R 3 can also be alkoxy of 1 to 4 carbon atoms.
- the invention also provides a process for the production of compounds of formula I comprising,
- Process variant a) can be effected according to known methods.
- the reaction may conveniently be effected in the presence of an inert solvent such as a hydrocarbon, chlorinated hydrocarbon, an ether or a tertiary amine, or in excess of the compound of formula III.
- the reaction may suitably be effected at a temperature of from -5° to 200°C.
- a basic catalyst such as a tertiary amine, for example pyridine or triethylamine may be employed.
- R 4 is alkoxy of 1 to 4 carbon atoms, this preferably has the same significance as R 3 .
- Process variant b) can be effected according to known methods.
- the reaction is preferably effected in the presence of a base, for example in the presence of a dilute, alkali metal hydroxide or a tertiary amine.
- the reaction may suitably be effected at a temperature of from 0°C to the boiling temperature of the reaction mixture, conveniently in the presence of an inert organic solvent which is miscible with water, such as a lower alcohol, dimethyl sulphoxide or dimethoxy ethane.
- the resulting compounds of formula I may be isolated and purified using conventional techniques.
- the compounds of formula I wherein R 3 is OH may be converted into salt forms in conventional manner and vice versa.
- Suitable salt forms include those with alkali metals, for example sodium and potasium, alkaline earth metals, for example calcium and magnesium, and with organic bases such as amines.
- the compounds of formula II can be prepared by nitrating a compound of formula IV, for example in a mixture of sulphuric and nitric acids, and reducing the resulting nitro derivative, according to known methods, to yield the compounds of formula II.
- the reduction may conveniently be effected by catalytic hydrogenation or by using iron filings in an aqueous acid.
- the 2,6,7,8,9,9a-hexahydro-2-oxo-1 H-benz[c,d]azulen-3yl-amine employed as starting material can be prepared as follows:
- the compounds of formula I exhibit pharmacological activity.
- the compounds exhibit disodium chromoglycate (DSCG)-like activity, in particular histamine release inhibiting activity, and are therefore indicated for use in the treatment and prophylaxis of allergic conditions, such as allergic asthma, exercise induced asthma and allergic gastrointestinal disorders, as indicated in the passive cutaneous anaphylaxis (PCA) test in the rat, based on the principles of Mota, J. Immunology, (1964), 7, 681.
- DSCG disodium chromoglycate
- PCA passive cutaneous anaphylaxis
- the (DSCG)-like activity in particular histamine release inhibiting activity, can be confirmed by inhibition of histamine release in the rat peritoneal mast cell test, basically as described by Kusner et al., J. Pharmacol. Exp. Therap. (1973) 184, 41-46.
- An indicated suitable daily dosage is from 1 to 100 mg, suitably administered in divided doses of from 0.25 to 50 mg, 2 to 4 times daily or in retard form.
- the compounds of formula I wherein R 3 is OH may be administered in free form or in pharmaceutically acceptable salt form.
- Such salt forms possess the same order of activity as the free forms and are readily prepared in conventional manner. Examples of suitable salt forms are those of sodium and potassium.
- the invention also provides a pharmaceutical composition
- a pharmaceutical composition comprising a compound of formula I, and in the case of compounds wherein R 3 is OH, in free form or in pharmaceutically acceptable salt form, in association with a pharmaceutically acceptable diluent or carrier.
- Such compositions may, for example be in the form of a solution or capsule.
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)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
- This invention relates to oxaminic acids and esters thereof, a process for the preparation of said compounds and pharmaceutical compositions containing these compounds.
-
- R1 is hydrogen or alkyl of 1 to 10 carbon atoms,
- R2 is chlorine or alkoxy of 1 to 4 carbon atoms, or
- R1 and R2 together are ―(CH)-m
- m is 3 or 4, and
- R3 is OH or alkoxy of 1 to 4 carbon atoms.
- When R1 is alkyl of 1 to 10 carbon atoms, this preferably contains 1 to 5 carbon atoms, especially 2 or 3 carbon atoms. R1 can also be hydrogen.
- R2 can be chlorine. R2 can also be alkoxy of 1 to 4 carbon atoms. R1 and R2 together can also be ―(CH2)m wherein m is 3 or 4, preferably 3.
- R3 can be OH. R3 can also be alkoxy of 1 to 4 carbon atoms.
- The invention also provides a process for the production of compounds of formula I comprising,
- a) producing a compound of formula la,
- R1 and R2 are as previously defined and
- R' 3 is alkoxy of 1 to 4 carbon atoms, by reacting a compound of formula II,
- R1 and R2 are as previously defined, with a compound of formula III,
- R' 3 is as previously defined and
- R4 is chlorine, bromine, alkoxy of 1 to 4 carbon atoms, phenoxy, or phenoxy monosubstituted by chlorine, bromine, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms.
or - b) producing a compound of formula Ib,
- Process variant a) can be effected according to known methods. For example, the reaction may conveniently be effected in the presence of an inert solvent such as a hydrocarbon, chlorinated hydrocarbon, an ether or a tertiary amine, or in excess of the compound of formula III. The reaction may suitably be effected at a temperature of from -5° to 200°C. A basic catalyst, such as a tertiary amine, for example pyridine or triethylamine may be employed. When R4 is alkoxy of 1 to 4 carbon atoms, this preferably has the same significance as R3.
- Process variant b) can be effected according to known methods. The reaction is preferably effected in the presence of a base, for example in the presence of a dilute, alkali metal hydroxide or a tertiary amine. The reaction may suitably be effected at a temperature of from 0°C to the boiling temperature of the reaction mixture, conveniently in the presence of an inert organic solvent which is miscible with water, such as a lower alcohol, dimethyl sulphoxide or dimethoxy ethane.
- The resulting compounds of formula I may be isolated and purified using conventional techniques. The compounds of formula I wherein R3 is OH may be converted into salt forms in conventional manner and vice versa. Suitable salt forms include those with alkali metals, for example sodium and potasium, alkaline earth metals, for example calcium and magnesium, and with organic bases such as amines.
- The compounds of formula II can be prepared by nitrating a compound of formula IV,
- Insofar as the production of the starting materials has not been described, these are either known or may be produced in conventional manner from available materials, or by methods analogous to those described herein.
- In the following Examples, all temperatures are in degrees Celsius.
- A solution of 5.0 g of 2,6,7,8,9,9a-hexahydro-2-oxo-1H-benz[c,d]azulen-3yl-amine in 26 ml of diethyl oxalate is refluxed for 2 hours and then cooled to room temperature. The reaction mixture is then distilled in a bulb tube at 90-1001/11 mm to remove the excess of diethyl oxalate, and the residue is purified by chromatography on 300 g of silica gel. The title compound is recrystallised from ether, m.p. 115-117°.
- The 2,6,7,8,9,9a-hexahydro-2-oxo-1 H-benz[c,d]azulen-3yl-amine employed as starting material can be prepared as follows:
- a) A solution of 20 g of potassium nitrate in 100 ml of conc. sulphuric acid is added dropwise, with stirring, to a solution of 36 g of 2,6,7,8,9,9a-hexahydro-2-oxo-1H-benz[c,djazuien-2-one in 200 ml of conc. sulphuric acid at 5° and then stirred for 1 hour at 0-5°. the reaction mixture is poured onto ice, extracted with chloroform, the extract washed with water, dried over sodium sulphate and concentrated. The raw product is dissolved in methylene chloride and filtered through 400 g of silica gel. After reducing the volume of the solvent, raw 2,6,7,8,9,9a-hexahydro-3-nitro-1 H-benz[c,d]azulen-2-one (containing 2,6,7,8,9,9a-hexahydro-4-nitro-1 H-benz[c,d]azulen-2-one) is crystallized from methanol, m.p. 107-110°.
- b) 20g of 2,6,7,8,9,9a-hexahydro-3-nitro-1 H-benz[c,d]azulen-2-one are added to 135 ml of acetic acid and 6 g of iron filings and 18 ml of water added whilst stirring. Further charges of 6 g of iron filings and 18 ml of water are added over intervals of 15, 30, 45 and 60 minutes. The mixture is stirred for a further 30 minutes, diluted, with 900 ml of water and extracted with methylene chloride. After reducing the volume of the methylene chloride extract, the remaining 2,6,7,8,9,9a-hexahydro-2-oxo-1H-benz[c,d]azulen-3yl-amine is purified by chromatography on silica gel. M.p. 135-138°.
-
- A solution of 0.95 of potassium hydroxide in 2 ml of water is added to a solution of 4 g of the title compound of Example 1 in 150 ml of methanol and the mixture refluxed for 1 hour. The solution is concentrated, diluted with water and the neutral side products extracted with CH2CI2. The aqueous phase is acidified with hydrochloric acid and the title compound filtered off. M.P. 191-1920.
-
- The compounds of formula I exhibit pharmacological activity. In particular, the compounds exhibit disodium chromoglycate (DSCG)-like activity, in particular histamine release inhibiting activity, and are therefore indicated for use in the treatment and prophylaxis of allergic conditions, such as allergic asthma, exercise induced asthma and allergic gastrointestinal disorders, as indicated in the passive cutaneous anaphylaxis (PCA) test in the rat, based on the principles of Mota, J. Immunology, (1964), 7, 681.
- The (DSCG)-like activity, in particular histamine release inhibiting activity, can be confirmed by inhibition of histamine release in the rat peritoneal mast cell test, basically as described by Kusner et al., J. Pharmacol. Exp. Therap. (1973) 184, 41-46.
- An indicated suitable daily dosage is from 1 to 100 mg, suitably administered in divided doses of from 0.25 to 50 mg, 2 to 4 times daily or in retard form.
- The compounds of formula I wherein R3 is OH may be administered in free form or in pharmaceutically acceptable salt form. Such salt forms possess the same order of activity as the free forms and are readily prepared in conventional manner. Examples of suitable salt forms are those of sodium and potassium.
- The invention also provides a pharmaceutical composition comprising a compound of formula I, and in the case of compounds wherein R3 is OH, in free form or in pharmaceutically acceptable salt form, in association with a pharmaceutically acceptable diluent or carrier. Such compositions may, for example be in the form of a solution or capsule.
wherein
Claims (10)
wherein
or
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH7914/77 | 1977-06-28 | ||
CH7913/77 | 1977-06-28 | ||
CH791377 | 1977-06-28 | ||
CH791477 | 1977-06-28 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0000152A1 EP0000152A1 (en) | 1979-01-10 |
EP0000152B1 true EP0000152B1 (en) | 1981-09-09 |
Family
ID=25702447
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP78100167A Expired EP0000152B1 (en) | 1977-06-28 | 1978-06-15 | Oxaminic acids and esters, process for their preparation and pharmaceutical compositions containing them |
Country Status (14)
Country | Link |
---|---|
US (1) | US4148916A (en) |
EP (1) | EP0000152B1 (en) |
JP (1) | JPS5412360A (en) |
AU (1) | AU519473B2 (en) |
CA (1) | CA1130307A (en) |
DE (1) | DE2861051D1 (en) |
DK (1) | DK275378A (en) |
FI (1) | FI781946A (en) |
IE (1) | IE47627B1 (en) |
IL (1) | IL55006A (en) |
IT (1) | IT1097293B (en) |
NZ (1) | NZ187677A (en) |
PH (1) | PH14995A (en) |
PT (1) | PT68216A (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE1606T1 (en) * | 1978-12-22 | 1982-10-15 | Sandoz Ag | INDANYLOXAMIC ACID DERIVATIVES, THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM. |
DE2926271A1 (en) * | 1979-06-29 | 1981-01-08 | Behringwerke Ag | AGENT FOR DETECTING PEROXIDATICALLY EFFECTIVE SUBSTANCES |
US4290773A (en) * | 1979-11-13 | 1981-09-22 | Miles Laboratories, Inc. | Stabilization of benzidine-type indicators with various enhancers |
US4579869A (en) * | 1985-08-02 | 1986-04-01 | Merck & Co., Inc. | Substituted [(2,3-dihydro-1-oxo-1H-inden-5-yl)amino]alkanoic acids, their derivatives and their salts |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2589934A (en) * | 1950-08-24 | 1952-03-18 | Abbott Lab | 2-aminomethyl-tetrahydroacenapthones-1 and their preparation |
CH485485A (en) * | 1966-02-07 | 1970-02-15 | Ciba Geigy | Use of oxalic acid ester amides as an ultraviolet protection agent outside the textile industry |
US3993679A (en) * | 1972-12-20 | 1976-11-23 | The Upjohn Company | Cyano phenylene dioxamic molecules |
US4069343A (en) * | 1973-03-23 | 1978-01-17 | American Home Products Corporation | Oxamic acid derivatives for the prevention of immediate type hypersensitivity reactions |
US3966965A (en) * | 1973-03-23 | 1976-06-29 | American Home Products Corporation | Oxamic acid derivatives for the prevention of immediate type hypersensitivity reactions |
US4011337A (en) * | 1975-07-07 | 1977-03-08 | The Upjohn Company | Oxamide-oxamic compounds, compositions and methods of use |
US4017538A (en) * | 1975-10-01 | 1977-04-12 | The Upjohn Company | Alkyl thio sulfinyl and sulfonyl oxamic compounds, compositions and methods of use |
US4061791A (en) * | 1975-12-29 | 1977-12-06 | The Upjohn Company | Anti-allergic oxanilate compounds |
-
1978
- 1978-06-15 DE DE7878100167T patent/DE2861051D1/en not_active Expired
- 1978-06-15 EP EP78100167A patent/EP0000152B1/en not_active Expired
- 1978-06-19 DK DK275378A patent/DK275378A/en not_active Application Discontinuation
- 1978-06-19 FI FI781946A patent/FI781946A/en not_active Application Discontinuation
- 1978-06-22 US US05/917,949 patent/US4148916A/en not_active Expired - Lifetime
- 1978-06-26 PT PT68216A patent/PT68216A/en unknown
- 1978-06-26 IE IE1272/78A patent/IE47627B1/en unknown
- 1978-06-26 PH PH21307A patent/PH14995A/en unknown
- 1978-06-26 IL IL55006A patent/IL55006A/en unknown
- 1978-06-26 AU AU37469/78A patent/AU519473B2/en not_active Expired
- 1978-06-26 NZ NZ187677A patent/NZ187677A/en unknown
- 1978-06-27 IT IT25028/78A patent/IT1097293B/en active
- 1978-06-27 CA CA306,275A patent/CA1130307A/en not_active Expired
- 1978-06-27 JP JP7708478A patent/JPS5412360A/en active Pending
Also Published As
Publication number | Publication date |
---|---|
DE2861051D1 (en) | 1981-11-26 |
IE781272L (en) | 1978-12-28 |
JPS5412360A (en) | 1979-01-30 |
NZ187677A (en) | 1981-01-23 |
IT1097293B (en) | 1985-08-31 |
PH14995A (en) | 1982-03-22 |
IL55006A0 (en) | 1978-08-31 |
IE47627B1 (en) | 1984-05-16 |
CA1130307A (en) | 1982-08-24 |
IT7825028A0 (en) | 1978-06-27 |
FI781946A (en) | 1978-12-29 |
PT68216A (en) | 1978-07-01 |
IL55006A (en) | 1981-11-30 |
DK275378A (en) | 1978-12-29 |
AU3746978A (en) | 1980-01-03 |
US4148916A (en) | 1979-04-10 |
EP0000152A1 (en) | 1979-01-10 |
AU519473B2 (en) | 1981-12-03 |
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