EP0000152A1 - Oxamin-Säuren und Ester hiervon, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Gemische - Google Patents
Oxamin-Säuren und Ester hiervon, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Gemische Download PDFInfo
- Publication number
- EP0000152A1 EP0000152A1 EP78100167A EP78100167A EP0000152A1 EP 0000152 A1 EP0000152 A1 EP 0000152A1 EP 78100167 A EP78100167 A EP 78100167A EP 78100167 A EP78100167 A EP 78100167A EP 0000152 A1 EP0000152 A1 EP 0000152A1
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 150000002148 esters Chemical class 0.000 title abstract description 3
- 239000002253 acid Substances 0.000 title description 4
- 150000007513 acids Chemical class 0.000 title description 2
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 24
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 16
- 239000000460 chlorine Substances 0.000 claims abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 150000003839 salts Chemical group 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 206010027654 Allergic conditions Diseases 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001412 amines Chemical class 0.000 abstract description 2
- 238000011282 treatment Methods 0.000 abstract description 2
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 abstract 2
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229960001340 histamine Drugs 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 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
- 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 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- 206010003557 Asthma exercise induced Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 208000004657 Exercise-Induced Asthma Diseases 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 201000009961 allergic asthma Diseases 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- ALZUBQQDOOIRIN-UHFFFAOYSA-N azulen-1-amine Chemical compound C1=CC=CC=C2C(N)=CC=C21 ALZUBQQDOOIRIN-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 208000024695 exercise-induced bronchoconstriction Diseases 0.000 description 1
- 210000003630 histaminocyte Anatomy 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 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 an 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 O°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, 0 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-1H-benz[c,d]-azulen-3yl-amine employed as starting material can be prepared as follows:
- a solution of 0.95 g 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 CH 2 Cl 2 .
- the aqueous phase is acidified with hydrochloric acid and the title compound filtered off. M.P. 191-192°.
- 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
- 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 about 1 to about 100 mg, suitably administered in divided doses of from about 0.25 to about 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)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH7913/77 | 1977-06-28 | ||
| CH791377 | 1977-06-28 | ||
| CH791477 | 1977-06-28 | ||
| CH7914/77 | 1977-06-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0000152A1 true EP0000152A1 (de) | 1979-01-10 |
| EP0000152B1 EP0000152B1 (de) | 1981-09-09 |
Family
ID=25702447
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP78100167A Expired EP0000152B1 (de) | 1977-06-28 | 1978-06-15 | Oxamin-Säuren und Ester hiervon, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Gemische |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4148916A (de) |
| EP (1) | EP0000152B1 (de) |
| JP (1) | JPS5412360A (de) |
| AU (1) | AU519473B2 (de) |
| CA (1) | CA1130307A (de) |
| DE (1) | DE2861051D1 (de) |
| DK (1) | DK275378A (de) |
| FI (1) | FI781946A7 (de) |
| IE (1) | IE47627B1 (de) |
| IL (1) | IL55006A (de) |
| IT (1) | IT1097293B (de) |
| NZ (1) | NZ187677A (de) |
| PH (1) | PH14995A (de) |
| PT (1) | PT68216A (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0013726A1 (de) * | 1978-12-22 | 1980-08-06 | Sandoz Ag | Indanyloxaminsäure-Derivate, ihre Herstellung und diese enthaltende pharmazeutische Zusammensetzungen |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2926271A1 (de) * | 1979-06-29 | 1981-01-08 | Behringwerke Ag | Mittel zum nachweis peroxidatisch wirksamer substanzen |
| 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 |
Citations (1)
| 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 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH485485A (de) * | 1966-02-07 | 1970-02-15 | Ciba Geigy | Verwendung von Oxalsäure-esteramiden als Ultraviolettschutzmittel ausserhalb der Textilindustrie |
| US3993679A (en) * | 1972-12-20 | 1976-11-23 | The Upjohn Company | Cyano phenylene dioxamic molecules |
| US3966965A (en) * | 1973-03-23 | 1976-06-29 | American Home Products Corporation | Oxamic acid derivatives for the prevention of immediate type hypersensitivity reactions |
| US4069343A (en) * | 1973-03-23 | 1978-01-17 | 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 EP EP78100167A patent/EP0000152B1/de not_active Expired
- 1978-06-15 DE DE7878100167T patent/DE2861051D1/de not_active Expired
- 1978-06-19 DK DK275378A patent/DK275378A/da not_active Application Discontinuation
- 1978-06-19 FI FI781946A patent/FI781946A7/fi not_active Application Discontinuation
- 1978-06-22 US US05/917,949 patent/US4148916A/en not_active Expired - Lifetime
- 1978-06-26 IL IL55006A patent/IL55006A/xx unknown
- 1978-06-26 IE IE1272/78A patent/IE47627B1/en unknown
- 1978-06-26 PH PH21307A patent/PH14995A/en unknown
- 1978-06-26 PT PT68216A patent/PT68216A/pt unknown
- 1978-06-26 NZ NZ187677A patent/NZ187677A/xx unknown
- 1978-06-26 AU AU37469/78A patent/AU519473B2/en not_active Expired
- 1978-06-27 IT IT25028/78A patent/IT1097293B/it active
- 1978-06-27 JP JP7708478A patent/JPS5412360A/ja active Pending
- 1978-06-27 CA CA306,275A patent/CA1130307A/en not_active Expired
Patent Citations (1)
| 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 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0013726A1 (de) * | 1978-12-22 | 1980-08-06 | Sandoz Ag | Indanyloxaminsäure-Derivate, ihre Herstellung und diese enthaltende pharmazeutische Zusammensetzungen |
Also Published As
| Publication number | Publication date |
|---|---|
| US4148916A (en) | 1979-04-10 |
| NZ187677A (en) | 1981-01-23 |
| DK275378A (da) | 1978-12-29 |
| IL55006A (en) | 1981-11-30 |
| IE781272L (en) | 1978-12-28 |
| PH14995A (en) | 1982-03-22 |
| IE47627B1 (en) | 1984-05-16 |
| IT1097293B (it) | 1985-08-31 |
| EP0000152B1 (de) | 1981-09-09 |
| AU519473B2 (en) | 1981-12-03 |
| IL55006A0 (en) | 1978-08-31 |
| PT68216A (fr) | 1978-07-01 |
| FI781946A7 (fi) | 1978-12-29 |
| IT7825028A0 (it) | 1978-06-27 |
| CA1130307A (en) | 1982-08-24 |
| JPS5412360A (en) | 1979-01-30 |
| AU3746978A (en) | 1980-01-03 |
| DE2861051D1 (en) | 1981-11-26 |
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