DE2524929C3 - 2-Hydroxyäthylidencyanessigsäureanilide, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Mittel - Google Patents
2-Hydroxyäthylidencyanessigsäureanilide, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende MittelInfo
- Publication number
- DE2524929C3 DE2524929C3 DE2524929A DE2524929A DE2524929C3 DE 2524929 C3 DE2524929 C3 DE 2524929C3 DE 2524929 A DE2524929 A DE 2524929A DE 2524929 A DE2524929 A DE 2524929A DE 2524929 C3 DE2524929 C3 DE 2524929C3
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compounds
- preparation
- acid
- hydroxyäthylidenidenidenessigsäureanilide
- 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
- 150000001875 compounds Chemical class 0.000 title description 17
- 238000002360 preparation method Methods 0.000 title description 8
- 239000000203 mixture Substances 0.000 title description 4
- 238000000034 method Methods 0.000 title description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 19
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002545 isoxazoles Chemical class 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 3
- 150000003868 ammonium compounds Chemical class 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- -1 methylenedioxy group Chemical group 0.000 description 3
- 229960002895 phenylbutazone Drugs 0.000 description 3
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- SXLMKYWQRMFXBZ-UHFFFAOYSA-N 2-(ethoxymethylidene)-3-oxo-n-phenylbutanamide Chemical class CCOC=C(C(C)=O)C(=O)NC1=CC=CC=C1 SXLMKYWQRMFXBZ-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 208000009386 Experimental Arthritis Diseases 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 230000001760 anti-analgesic effect Effects 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- ODRMLQDLKQZGQR-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-2-(ethoxymethylidene)-3-oxobutanamide Chemical compound CCOC=C(C(C)=O)C(=O)NC1=CC=C(Cl)C(Cl)=C1 ODRMLQDLKQZGQR-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003791 organic solvent mixture Substances 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- VQBXUKGMJCPBMF-UHFFFAOYSA-N 5-methyl-1,2-oxazole-4-carboxylic acid Chemical compound CC=1ON=CC=1C(O)=O VQBXUKGMJCPBMF-UHFFFAOYSA-N 0.000 description 1
- KBFQQKBZIFSAMY-UHFFFAOYSA-N 5-methyl-n-[3-(trifluoromethyl)phenyl]-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2C=C(C=CC=2)C(F)(F)F)=C1C KBFQQKBZIFSAMY-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical compound OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 238000011047 acute toxicity test Methods 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011694 lewis rat Methods 0.000 description 1
- BPAFBORSRKBCPI-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(Cl)C(Cl)=C1 BPAFBORSRKBCPI-UHFFFAOYSA-N 0.000 description 1
- RIFXXMYHOTWSEC-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2C=C(Cl)C(Cl)=CC=2)=C1C RIFXXMYHOTWSEC-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001562 ulcerogenic effect Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/66—Nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NLAANVRAGE7605845,A NL186239B (nl) | 1975-06-05 | Werkwijze voor de bereiding van een geneesmiddel met antiflogistische en/of analgetische werking, alsmede werkwijze voor de bereiding van een 2-hydroxyethylideencyaanazijnzuuranilide geschikt voor toepassing bij deze werkwijze. | |
| DE2524929A DE2524929C3 (de) | 1975-06-05 | 1975-06-05 | 2-Hydroxyäthylidencyanessigsäureanilide, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Mittel |
| NLAANVRAGE7605845,A NL186239C (nl) | 1975-06-05 | 1976-05-31 | Werkwijze voor de bereiding van een geneesmiddel met antiflogistische en/of analgetische werking, alsmede werkwijze voor de bereiding van een 2-hydroxyethylideencyaanazijnzuuranilide geschikt voor toepassing bij deze werkwijze. |
| CH696376A CH627444A5 (de) | 1975-06-05 | 1976-06-02 | Verfahren zur herstellung neuer cyanessigsaeureanilid-derivate. |
| IT23922/76A IT1063593B (it) | 1975-06-05 | 1976-06-03 | Derivati anilidici dello acido cianacetico processo per la loro preparazione e mezzi che contengono tali composti |
| US05/692,318 US4061767A (en) | 1975-06-05 | 1976-06-03 | Cyano acetic acid anilide derivatives, process for their manufacture and compositions containing these compounds |
| LU75075A LU75075A1 (enExample) | 1975-06-05 | 1976-06-03 | |
| DK248476A DK157078C (da) | 1975-06-05 | 1976-06-04 | Fremgangsmaade til fremstilling af 2-hydroxyethylidencyaneddikesyreanilid-derivater |
| MX000269U MX3170E (es) | 1975-06-05 | 1976-06-04 | Procedimiento para la preparacion de anilidas de acido 2 - hidroxi etil idenciano acetico |
| CA254,136A CA1082202A (en) | 1975-06-05 | 1976-06-04 | Cyano acetic acid anilide derivatives, process for their manufacture and compositions containing these compounds |
| JP51065477A JPS6032620B2 (ja) | 1975-06-05 | 1976-06-04 | 新規なシアン酢酸アニリド誘導体およびその製法 |
| AT413576A AT343641B (de) | 1975-06-05 | 1976-06-04 | Verfahren zur herstellung von neuen 2-hydroxyathylidencyanessigsaureaniliden |
| FR7617042A FR2313031A1 (fr) | 1975-06-05 | 1976-06-04 | Derives d'anilides de l'acide cyanoacetique, leur procede de preparation et leur application |
| IE1203/76A IE43004B1 (en) | 1975-06-05 | 1976-06-04 | Cyano acetic acid anilide derivatives, processes for their manufacture and compositions containing them |
| GB23437/76A GB1555555A (en) | 1975-06-05 | 1976-06-07 | Cyano acetic acid anilide derivatives process for their manufacture and compositions containing them |
| BE167706A BE842688A (fr) | 1975-06-05 | 1976-06-08 | Derives d'anilides de l'acide cyanoacetique, leur procede de preparation et leur application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2524929A DE2524929C3 (de) | 1975-06-05 | 1975-06-05 | 2-Hydroxyäthylidencyanessigsäureanilide, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Mittel |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2524929A1 DE2524929A1 (de) | 1976-12-16 |
| DE2524929B2 DE2524929B2 (de) | 1980-01-31 |
| DE2524929C3 true DE2524929C3 (de) | 1980-10-09 |
Family
ID=5948272
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2524929A Expired DE2524929C3 (de) | 1975-06-05 | 1975-06-05 | 2-Hydroxyäthylidencyanessigsäureanilide, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Mittel |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4061767A (enExample) |
| JP (1) | JPS6032620B2 (enExample) |
| AT (1) | AT343641B (enExample) |
| BE (1) | BE842688A (enExample) |
| CA (1) | CA1082202A (enExample) |
| CH (1) | CH627444A5 (enExample) |
| DE (1) | DE2524929C3 (enExample) |
| DK (1) | DK157078C (enExample) |
| FR (1) | FR2313031A1 (enExample) |
| GB (1) | GB1555555A (enExample) |
| IE (1) | IE43004B1 (enExample) |
| IT (1) | IT1063593B (enExample) |
| LU (1) | LU75075A1 (enExample) |
| MX (1) | MX3170E (enExample) |
| NL (2) | NL186239C (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3247454A1 (de) * | 1982-12-22 | 1984-06-28 | Laboratorios Bago S.A., Buenos Aires | Substituierte 3-phenyl-5-methyl-isoxazol-4-carboxy-anilide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Families Citing this family (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1980000964A1 (en) * | 1978-11-03 | 1980-05-15 | American Cyanamid Co | Anti-inflammatory agents including 2-carbonyl-3-hydroxy-2-alkenonitriles |
| US4181677A (en) * | 1978-12-13 | 1980-01-01 | American Cyanamid Company | 2-Benzoyl-3-alkoxy-2-alkenonitriles |
| US4173650A (en) * | 1978-11-03 | 1979-11-06 | American Cyanamid Company | Cis-2-benzoyl-3-hydroxy-2-alkenonitriles as anti-inflammatory agents |
| US4259256A (en) * | 1978-12-13 | 1981-03-31 | American Cyanamid Company | 2-Benzoyl-3-dimethylamino-2-alkenonitriles |
| IL60269A (en) * | 1979-06-11 | 1983-12-30 | Ciba Geigy | Alpha-carbamoyl-pyrrolpropionitriles,their preparation and pharmaceutical compositions containing them |
| US4256759A (en) * | 1979-06-11 | 1981-03-17 | Ciba-Geigy Corporation | Alphacarbamoyl-pyrrolpropionitriles |
| US4277420A (en) * | 1979-09-24 | 1981-07-07 | Monsanto Company | Ephedrine and pseudoephedrine precursors |
| US4254049A (en) * | 1979-12-17 | 1981-03-03 | American Cyanamid Company | Substituted phenyl-2-cyano-2-alkenoic acid esters |
| US4254047A (en) * | 1979-12-17 | 1981-03-03 | American Cyanamid Company | Substituted phenyl-2-cyano-2-thioalkenoic acid esters |
| US4254048A (en) * | 1979-12-17 | 1981-03-03 | American Cyanamid Company | Substituted phenyl alkylidene acetoacetonitriles |
| US4435407A (en) | 1982-01-07 | 1984-03-06 | Ciba-Geigy Corporation | Certain substituted β-oxo-α-carbamoylpyrrolepropionitriles |
| US4644010A (en) * | 1982-09-28 | 1987-02-17 | Ciba-Geigy Corporation | Certain β-oxo-α-carbamoylpyrrolepropionitriles |
| DE3534440A1 (de) * | 1985-09-27 | 1987-04-02 | Hoechst Ag | Arzneimittel gegen chronische graft-versus-host-krankheiten sowie gegen autoimmunerkrankungen, insbesondere systemischen lupus erythematodes |
| US5268382A (en) * | 1985-09-27 | 1993-12-07 | Hoechst Aktiengesellschaft | Medicaments to combat autoimmune diseases, in particular systemic lupus erythematosus |
| GB8619432D0 (en) * | 1986-08-08 | 1986-09-17 | Lilly Industries Ltd | Pharmaceutical compounds |
| GB8619433D0 (en) * | 1986-08-08 | 1986-09-17 | Lilly Industries Ltd | Pharmaceutical compounds |
| US4888357A (en) * | 1988-01-26 | 1989-12-19 | Bristol-Myers Company | Antiarthritic β-cycloalkyl-β-oxopropionitriles |
| US4975462A (en) * | 1988-07-29 | 1990-12-04 | Bristol-Myers Company | Antiarthritic α-arylcarbamoyl cyanoacetic acid derivatives |
| DD297328A5 (de) | 1989-08-18 | 1992-01-09 | �������@���������k���Kk�� | 5-methyl-isoxalol-4-carbonsaeureanilide und 2 hydroxyethyliden-cyanoessigsaeureanilide zur behandlung von augenerkrankungen |
| US5583150A (en) * | 1989-08-18 | 1996-12-10 | Alcon Laboratories, Inc. | 5-methyl-isoxazole-4-carboxylic acid anilides and 2-hydroxyethylidene-cyano acetic anilides for the treatment of ocular diseases |
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| US20050158371A1 (en) * | 2002-02-12 | 2005-07-21 | Sumitomo Pharmaceuticals Co., Ltd. | Novel external agent |
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| UA108760C2 (uk) | 2010-07-01 | 2015-06-10 | Кальцієві солі сполуки як протизапальні, імуномодулюючі та антипроліферативні засоби | |
| WO2015077535A2 (en) | 2013-11-22 | 2015-05-28 | Genzyme Corporation | Novel methods for treating neurodegenerative diseases |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2288863A (en) * | 1940-02-27 | 1942-07-07 | Hoffmann La Roche | Process for the manufacture of substituted amides of 3,5-dimethylisoxazole-4-carboxylic acid |
| BE506549A (enExample) * | 1950-10-19 |
-
0
- NL NLAANVRAGE7605845,A patent/NL186239B/xx unknown
-
1975
- 1975-06-05 DE DE2524929A patent/DE2524929C3/de not_active Expired
-
1976
- 1976-05-31 NL NLAANVRAGE7605845,A patent/NL186239C/xx not_active IP Right Cessation
- 1976-06-02 CH CH696376A patent/CH627444A5/de not_active IP Right Cessation
- 1976-06-03 LU LU75075A patent/LU75075A1/xx unknown
- 1976-06-03 US US05/692,318 patent/US4061767A/en not_active Expired - Lifetime
- 1976-06-03 IT IT23922/76A patent/IT1063593B/it active
- 1976-06-04 MX MX000269U patent/MX3170E/es unknown
- 1976-06-04 DK DK248476A patent/DK157078C/da active
- 1976-06-04 CA CA254,136A patent/CA1082202A/en not_active Expired
- 1976-06-04 JP JP51065477A patent/JPS6032620B2/ja not_active Expired
- 1976-06-04 IE IE1203/76A patent/IE43004B1/en unknown
- 1976-06-04 FR FR7617042A patent/FR2313031A1/fr active Granted
- 1976-06-04 AT AT413576A patent/AT343641B/de not_active IP Right Cessation
- 1976-06-07 GB GB23437/76A patent/GB1555555A/en not_active Expired
- 1976-06-08 BE BE167706A patent/BE842688A/xx not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3247454A1 (de) * | 1982-12-22 | 1984-06-28 | Laboratorios Bago S.A., Buenos Aires | Substituierte 3-phenyl-5-methyl-isoxazol-4-carboxy-anilide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Also Published As
| Publication number | Publication date |
|---|---|
| BE842688A (fr) | 1976-12-08 |
| LU75075A1 (enExample) | 1977-03-07 |
| AT343641B (de) | 1978-06-12 |
| NL186239B (nl) | |
| NL186239C (nl) | 1990-10-16 |
| JPS6032620B2 (ja) | 1985-07-29 |
| FR2313031B1 (enExample) | 1979-10-12 |
| NL7605845A (en) | 1976-12-07 |
| IE43004L (en) | 1976-12-05 |
| US4061767A (en) | 1977-12-06 |
| DE2524929B2 (de) | 1980-01-31 |
| DK157078C (da) | 1990-04-09 |
| IT1063593B (it) | 1985-02-11 |
| MX3170E (es) | 1980-06-05 |
| ATA413576A (de) | 1977-10-15 |
| DE2524929A1 (de) | 1976-12-16 |
| IE43004B1 (en) | 1980-12-03 |
| CH627444A5 (de) | 1982-01-15 |
| DK248476A (da) | 1976-12-06 |
| FR2313031A1 (fr) | 1976-12-31 |
| CA1082202A (en) | 1980-07-22 |
| GB1555555A (en) | 1979-11-14 |
| JPS527929A (en) | 1977-01-21 |
| DK157078B (da) | 1989-11-06 |
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