CH627444A5 - Verfahren zur herstellung neuer cyanessigsaeureanilid-derivate. - Google Patents
Verfahren zur herstellung neuer cyanessigsaeureanilid-derivate. Download PDFInfo
- Publication number
- CH627444A5 CH627444A5 CH696376A CH696376A CH627444A5 CH 627444 A5 CH627444 A5 CH 627444A5 CH 696376 A CH696376 A CH 696376A CH 696376 A CH696376 A CH 696376A CH 627444 A5 CH627444 A5 CH 627444A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- acid
- carbon atoms
- compounds
- atoms
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 229910052731 fluorine Inorganic materials 0.000 description 10
- 239000011737 fluorine Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
- 229910052794 bromium Inorganic materials 0.000 description 9
- -1 methylenedioxy group Chemical group 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002545 isoxazoles Chemical class 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 150000002367 halogens 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
- SXLMKYWQRMFXBZ-UHFFFAOYSA-N 2-(ethoxymethylidene)-3-oxo-n-phenylbutanamide Chemical compound CCOC=C(C(C)=O)C(=O)NC1=CC=CC=C1 SXLMKYWQRMFXBZ-UHFFFAOYSA-N 0.000 description 3
- 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
- 241001465754 Metazoa Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000700159 Rattus Species 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
- 150000003931 anilides Chemical class 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 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 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
- 230000001562 ulcerogenic effect Effects 0.000 description 3
- UJBZHNQIBVHDDU-UHFFFAOYSA-N 2-cyano-3-hydroxy-n-[3-(trifluoromethyl)phenyl]but-2-enamide Chemical compound CC(O)=C(C#N)C(=O)NC1=CC=CC(C(F)(F)F)=C1 UJBZHNQIBVHDDU-UHFFFAOYSA-N 0.000 description 2
- RMPAZFSYXHPNDW-UHFFFAOYSA-N 2-cyano-3-hydroxy-n-phenylbut-2-enamide Chemical class CC(O)=C(C#N)C(=O)NC1=CC=CC=C1 RMPAZFSYXHPNDW-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
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 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
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 230000001760 anti-analgesic effect Effects 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
- 239000000543 intermediate Substances 0.000 description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 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 2
- 125000001624 naphthyl group Chemical group 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
- 229960002895 phenylbutazone Drugs 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
- 238000012453 sprague-dawley rat model Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- FUJSJWRORKKPAI-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)acetyl chloride Chemical compound ClC(=O)COC1=CC=C(Cl)C=C1Cl FUJSJWRORKKPAI-UHFFFAOYSA-N 0.000 description 1
- 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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000011785 NMRI mouse Methods 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 238000011047 acute toxicity test Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 125000004429 atom Chemical group 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
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 230000000694 effects Effects 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
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 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
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 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
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 231100000397 ulcer Toxicity 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)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (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)
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 (1)
| Publication Number | Publication Date |
|---|---|
| CH627444A5 true CH627444A5 (de) | 1982-01-15 |
Family
ID=5948272
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH696376A CH627444A5 (de) | 1975-06-05 | 1976-06-02 | Verfahren zur herstellung neuer cyanessigsaeureanilid-derivate. |
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) |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4173650A (en) * | 1978-11-03 | 1979-11-06 | American Cyanamid Company | Cis-2-benzoyl-3-hydroxy-2-alkenonitriles as anti-inflammatory agents |
| 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 |
| US4259256A (en) * | 1978-12-13 | 1981-03-31 | American Cyanamid Company | 2-Benzoyl-3-dimethylamino-2-alkenonitriles |
| EP0143142A3 (de) * | 1979-06-11 | 1985-07-17 | Ciba-Geigy Ag | Alphacarbamoyl-pyrrolpropionitrile, Verfahren zu ihrer Herstellung, pharmazeutische Präparate enthaltend diese Verbindungen, sowie ihre therapeutische Verwendung |
| 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 |
| 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 |
| 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 |
| 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 |
| DD297328A5 (de) | 1989-08-18 | 1992-01-09 | �������@���������k���Kk�� | 5-methyl-isoxalol-4-carbonsaeureanilide und 2 hydroxyethyliden-cyanoessigsaeureanilide zur behandlung von augenerkrankungen |
| US5034410A (en) * | 1989-10-11 | 1991-07-23 | Syntex (U.S.A.) Inc. | Anthelmintically active benzenepropanamide derivatives |
| RU2142937C1 (ru) * | 1990-05-18 | 1999-12-20 | Хехст АГ | Амиды органических кислот, способ их получения и фармацевтическая композиция |
| ZA913762B (en) | 1990-05-18 | 1992-01-29 | Hoechst Ag | Isoxazole-4-carboxamides and hydroxyalkylidenecyanoacetamides,pharmaceuticals containing these compounds and their use |
| DK0492497T3 (da) * | 1990-12-24 | 1997-01-06 | Hoechst Ag | Fremgangsmåde til acylering af alkoholer med en immobiliseret pseudomonas-lipase |
| US6133301A (en) * | 1991-08-22 | 2000-10-17 | Aventis Pharma Deutschland Gmbh | Pharmaceuticals for the treatment of rejection reactions in organ transplantations |
| DE4127737A1 (de) | 1991-08-22 | 1993-02-25 | Hoechst Ag | Arzneimittel zur behandlung von abstossungsreaktionen bei organverpflanzungen |
| IL102790A (en) * | 1991-09-17 | 1996-01-31 | Roussel Uclaf | 3-Cycloalkyl-prop-2- enamide derivatives |
| NZ244814A (en) * | 1991-10-23 | 1994-06-27 | Hoechst Ag | N-phenyl-2-cyano-3-hydroxycrotonamide derivatives and pharmaceutical compositions |
| GB9200275D0 (en) * | 1992-01-08 | 1992-02-26 | Roussel Lab Ltd | Chemical compounds |
| GB9209330D0 (en) * | 1992-04-30 | 1992-06-17 | Roussel Lab Ltd | Chemical compounds |
| GB9300083D0 (en) | 1993-01-05 | 1993-03-03 | Roussel Lab Ltd | Chemical compounds |
| TW314467B (enExample) * | 1993-03-31 | 1997-09-01 | Hoechst Ag | |
| AU6852594A (en) | 1993-06-03 | 1995-01-03 | Therapeutic Antibodies Inc. | Production of antibody fragments |
| GB9313365D0 (en) * | 1993-06-29 | 1993-08-11 | Roussel Lab Ltd | Chemical compounds |
| GB9322781D0 (en) * | 1993-11-04 | 1993-12-22 | Roussel Lab Ltd | Aromatic amides |
| LT3589B (en) | 1993-11-30 | 1995-12-27 | Hoechst Ag | Using of known combination for treatment of rejection reaction by transplantation of organs |
| US5700823A (en) * | 1994-01-07 | 1997-12-23 | Sugen, Inc. | Treatment of platelet derived growth factor related disorders such as cancers |
| US5519042A (en) * | 1994-01-13 | 1996-05-21 | Hoechst Aktiengesellschaft | Method of treating hyperproliferative vascular disease |
| US6331555B1 (en) | 1995-06-01 | 2001-12-18 | University Of California | Treatment of platelet derived growth factor related disorders such as cancers |
| DE19539638A1 (de) * | 1995-10-25 | 1997-04-30 | Hoechst Ag | Die Verwendung von Isoxazol- und Crotonsäureamidderivaten zur Behandlung von Krebserkrankungen |
| DE19547648A1 (de) * | 1995-12-20 | 1997-06-26 | Hoechst Ag | Zubereitung, enthaltend High Density Lipoproteine und Crotonsäureamidderivate |
| US5981536A (en) * | 1996-07-31 | 1999-11-09 | Hoechst Aktiengesellschaft | Use of xanthine derivatives for the modulation of apoptosis |
| US5856330A (en) * | 1996-07-31 | 1999-01-05 | Hoechst Aktiengesellschaft | Use of xanthine derivatives for the inhibition of dephosphorylation of cofilin |
| US6011051A (en) * | 1996-07-31 | 2000-01-04 | Hoechst Aktiengesellschaft | Use of isoxazole and crotonamide derivatives for the modulation of apoptosis |
| US6316479B1 (en) | 1997-05-19 | 2001-11-13 | Sugen, Inc. | Isoxazole-4-carboxamide compounds active against protein tryosine kinase related disorders |
| DE59800287D1 (de) * | 1997-08-08 | 2000-11-09 | Aventis Pharma Gmbh | Kristallform von 5-Methylisoxazol-4-carbonsäure-(4-trifluormethyl)-anilid |
| US6355678B1 (en) | 1998-06-29 | 2002-03-12 | Parker Hughes Institute | Inhibitors of the EGF-receptor tyrosine kinase and methods for their use |
| US20050255071A1 (en) * | 1998-12-10 | 2005-11-17 | Aventis Pharma Deutschland Gmbh | Preparation having improved therapeutic breadth comprising nucleotide synthesis inhibitors |
| GB0123571D0 (en) * | 2001-04-05 | 2001-11-21 | Aventis Pharm Prod Inc | Use of (Z)-2-cyano-3-hydroxy-but-2-enoic acid-(4'-trifluoromethylphenyl)-amide for treating multiple sclerosis |
| DE10132308A1 (de) * | 2001-07-06 | 2003-01-30 | Aventis Behring Gmbh | Kombinationspräparat zur Therapie von immunologischen Erkrankungen |
| MXPA04000224A (es) | 2001-07-10 | 2005-07-25 | 4Sc Ag | Novedosos compuestos como agentes antiinflamatorios, inmunomoduladores y antiproliferativos. |
| US20050158371A1 (en) * | 2002-02-12 | 2005-07-21 | Sumitomo Pharmaceuticals Co., Ltd. | Novel external agent |
| SI1578741T1 (sl) | 2002-12-23 | 2011-11-30 | 4Sc Ag | Aromatske spojine kot protivnetna imunomodulatorna in antiproliferativna sredstva |
| UA108760C2 (uk) | 2010-07-01 | 2015-06-10 | Кальцієві солі сполуки як протизапальні, імуномодулюючі та антипроліферативні засоби | |
| EA201691057A1 (ru) | 2013-11-22 | 2016-10-31 | Джензим Корпорейшн | Новые способы лечения нейродегенеративных заболеваний |
| EP3310755B1 (en) * | 2015-06-17 | 2021-02-24 | Biocon Limited | A novel process for the preparation of teriflunomide |
| FI3765439T3 (fi) | 2018-03-16 | 2024-05-23 | Immunic Ag | Uusia kalsiumsuolapolymorfeja tulehdusta estävinä, immunomodulatorisina ja lisääntymistä estävinä aineina |
| ES3010487T3 (en) | 2020-04-21 | 2025-04-03 | Immunic Ag | Vidofludimus for use in the treatment or prevention of viral diseases |
Family Cites Families (2)
| 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 IT IT23922/76A patent/IT1063593B/it active
- 1976-06-03 US US05/692,318 patent/US4061767A/en not_active Expired - Lifetime
- 1976-06-03 LU LU75075A patent/LU75075A1/xx unknown
- 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 DK DK248476A patent/DK157078C/da active
- 1976-06-04 CA CA254,136A patent/CA1082202A/en not_active Expired
- 1976-06-04 AT AT413576A patent/AT343641B/de not_active IP Right Cessation
- 1976-06-04 MX MX000269U patent/MX3170E/es unknown
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| FR2313031B1 (enExample) | 1979-10-12 |
| IE43004L (en) | 1976-12-05 |
| AT343641B (de) | 1978-06-12 |
| DE2524929A1 (de) | 1976-12-16 |
| BE842688A (fr) | 1976-12-08 |
| MX3170E (es) | 1980-06-05 |
| NL186239C (nl) | 1990-10-16 |
| DE2524929B2 (de) | 1980-01-31 |
| ATA413576A (de) | 1977-10-15 |
| DK157078C (da) | 1990-04-09 |
| IE43004B1 (en) | 1980-12-03 |
| DK248476A (da) | 1976-12-06 |
| LU75075A1 (enExample) | 1977-03-07 |
| IT1063593B (it) | 1985-02-11 |
| CA1082202A (en) | 1980-07-22 |
| JPS527929A (en) | 1977-01-21 |
| DE2524929C3 (de) | 1980-10-09 |
| US4061767A (en) | 1977-12-06 |
| NL7605845A (en) | 1976-12-07 |
| JPS6032620B2 (ja) | 1985-07-29 |
| NL186239B (nl) | |
| GB1555555A (en) | 1979-11-14 |
| FR2313031A1 (fr) | 1976-12-31 |
| DK157078B (da) | 1989-11-06 |
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| Date | Code | Title | Description |
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| PL | Patent ceased |