JPH0136819B2 - - Google Patents
Info
- Publication number
- JPH0136819B2 JPH0136819B2 JP57226685A JP22668582A JPH0136819B2 JP H0136819 B2 JPH0136819 B2 JP H0136819B2 JP 57226685 A JP57226685 A JP 57226685A JP 22668582 A JP22668582 A JP 22668582A JP H0136819 B2 JPH0136819 B2 JP H0136819B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group represented
- bistrifluoromethylphenyl
- aminocarbonyl
- compound
- 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
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- 201000010099 disease Diseases 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 206010010904 Convulsion Diseases 0.000 claims description 6
- 230000036461 convulsion Effects 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 3
- -1 carboximide compound Chemical class 0.000 description 43
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- 238000000921 elemental analysis Methods 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- 230000000704 physical effect Effects 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- CDIDGWDGQGVCIB-UHFFFAOYSA-N 3,5-bis(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CDIDGWDGQGVCIB-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- SPUOPTCIVFNKFX-NWDGAFQWSA-N (1r,2s)-2-[[3,5-bis(trifluoromethyl)phenyl]carbamoyl]cyclohexane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCC[C@@H]1C(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 SPUOPTCIVFNKFX-NWDGAFQWSA-N 0.000 description 5
- 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 5
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- KOODXLCUAZRPCI-UHFFFAOYSA-N 2-[[3,5-bis(trifluoromethyl)phenyl]carbamoyl]cyclohexene-1-carboxylic acid Chemical compound C1CCCC(C(=O)O)=C1C(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 KOODXLCUAZRPCI-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 208000026139 Memory disease Diseases 0.000 description 3
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- SPUOPTCIVFNKFX-VXGBXAGGSA-N (1r,2r)-2-[[3,5-bis(trifluoromethyl)phenyl]carbamoyl]cyclohexane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCC[C@H]1C(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 SPUOPTCIVFNKFX-VXGBXAGGSA-N 0.000 description 2
- KFJCLBNTNXRHIN-TXEJJXNPSA-N (3as,7ar)-2-[3,5-bis(trifluoromethyl)phenyl]-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(N2C([C@@H]3CCCC[C@@H]3C2=O)=O)=C1 KFJCLBNTNXRHIN-TXEJJXNPSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 208000022540 Consciousness disease Diseases 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- 230000003627 anti-cholesterol Effects 0.000 description 2
- 230000001773 anti-convulsant effect Effects 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 229960003965 antiepileptics Drugs 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 229940099112 cornstarch Drugs 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 2
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- 238000002347 injection Methods 0.000 description 2
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- 239000000314 lubricant Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
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- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- PWEKCCPUQNOPFO-UHFFFAOYSA-N 2-oxaspiro[3.3]heptane-1,3-dione Chemical compound O=C1OC(=O)C11CCC1 PWEKCCPUQNOPFO-UHFFFAOYSA-N 0.000 description 1
- QUGUPCGKQWUAPF-UHFFFAOYSA-N 2-oxaspiro[3.5]non-6-ene-1,3-dione Chemical compound O=C1OC(=O)C11CC=CCC1 QUGUPCGKQWUAPF-UHFFFAOYSA-N 0.000 description 1
- QTDXSEZXAPHVBI-UHFFFAOYSA-N 4-methylcyclohexane-1-carboxylic acid Chemical compound CC1CCC(C(O)=O)CC1 QTDXSEZXAPHVBI-UHFFFAOYSA-N 0.000 description 1
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- 241000416162 Astragalus gummifer Species 0.000 description 1
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- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
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- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
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- 230000000949 anxiolytic effect Effects 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- BFAKENXZKHGIGE-UHFFFAOYSA-N bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene Chemical compound FC1=C(C(=C(C(=C1F)I)F)F)N=NC1=C(C(=C(C(=C1F)F)I)F)F BFAKENXZKHGIGE-UHFFFAOYSA-N 0.000 description 1
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- FNAQSUUGMSOBHW-UHFFFAOYSA-H calcium citrate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O FNAQSUUGMSOBHW-UHFFFAOYSA-H 0.000 description 1
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- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
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- 238000010253 intravenous injection Methods 0.000 description 1
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- 239000011777 magnesium Substances 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/59—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Anesthesiology (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pulmonology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57226685A JPS59118750A (ja) | 1982-12-27 | 1982-12-27 | カルボン酸アミド化合物およびその誘導体 |
| AU22531/83A AU2253183A (en) | 1982-12-27 | 1983-12-19 | Carboxylic acid amides and carboximides |
| GB08333713A GB2133006B (en) | 1982-12-27 | 1983-12-19 | Bis (trifluoromethyl) aniline derivatives |
| CA000443811A CA1202312A (en) | 1982-12-27 | 1983-12-20 | Carboxylic acid amides and their derivatives |
| NL8304406A NL8304406A (nl) | 1982-12-27 | 1983-12-22 | Carbonzuuramiden en derivaten ervan, werkwijzen voor de bereiding ervan en farmaceutische preparaten, die deze verbindingen bevatten. |
| SE8307119A SE8307119L (sv) | 1982-12-27 | 1983-12-22 | Karboxylsyraamider och derivat derav |
| PH30020A PH19459A (en) | 1982-12-27 | 1983-12-22 | Carboxylic acid amides and their derivatives |
| ZA839546A ZA839546B (en) | 1982-12-27 | 1983-12-22 | Carboxylic acid amides and their derivatives |
| DK596083A DK596083A (da) | 1982-12-27 | 1983-12-23 | Carboxylsyreamidderivat, fremgangsmaade til fremstilling deraf samt laegemiddel indeholdende en saadan forbindelse |
| HU834462A HU189799B (en) | 1982-12-27 | 1983-12-23 | Process for preparing carboxylic acid amides and derivatives thereof further pharmaceutical compositions containing such compounds |
| DE19833346814 DE3346814A1 (de) | 1982-12-27 | 1983-12-23 | Carbonsaeureamidderivate, verfahren zu deren herstellung und arzneimittel, welche diese enthalten |
| IT24351/83A IT1170275B (it) | 1982-12-27 | 1983-12-23 | Ammidi di acidi carbossilici e loro derivati |
| CH6912/83A CH656875A5 (de) | 1982-12-27 | 1983-12-23 | Amide von carbonsaeuren und ihre derivate. |
| ES528409A ES528409A0 (es) | 1982-12-27 | 1983-12-26 | Un procedimiento para preparar compuestos de amida de acido carboxilico |
| KR1019830006180A KR840007714A (ko) | 1982-12-27 | 1983-12-26 | 카르복실산 아마이드류의 제조방법 |
| BE0/212130A BE898570A (fr) | 1982-12-27 | 1983-12-27 | Nouveaux amides et imides carboxyliques, procédés pour leur préparation et composition pharmaceutique les contenant. |
| FR8320864A FR2538386B1 (fr) | 1982-12-27 | 1983-12-27 | Nouveaux amides et imides carboxyliques procedes pour leur preparation et composition pharmaceutique les contenant |
| ES543810A ES8608486A1 (es) | 1982-12-27 | 1985-06-01 | Un procedimiento para preparar un compuesto de carboximida |
| US06/803,526 US4661630A (en) | 1982-12-27 | 1985-12-02 | Carboxylic acid amides and their derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57226685A JPS59118750A (ja) | 1982-12-27 | 1982-12-27 | カルボン酸アミド化合物およびその誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59118750A JPS59118750A (ja) | 1984-07-09 |
| JPH0136819B2 true JPH0136819B2 (US20030220297A1-20031127-C00074.png) | 1989-08-02 |
Family
ID=16849045
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57226685A Granted JPS59118750A (ja) | 1982-12-27 | 1982-12-27 | カルボン酸アミド化合物およびその誘導体 |
Country Status (18)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4057782A1 (en) | 2021-03-12 | 2022-09-14 | Atotech Deutschland GmbH & Co. KG | Method for increasing adhesion strength between copper and an organic material and reducing halo and wedge void formation by modifying the copper surface and/or by using heteroaromatic silane compounds |
| EP4056285A1 (en) | 2021-03-12 | 2022-09-14 | Atotech Deutschland GmbH & Co. KG | Triazine silane compound and its usage as adhesion promotor |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59231057A (ja) * | 1983-06-14 | 1984-12-25 | Eisai Co Ltd | カルボン酸アミド化合物およびその誘導体 |
| DE3334822A1 (de) * | 1983-09-26 | 1985-04-04 | Bayer Ag, 5090 Leverkusen | Neue flammschutzmittel, ihre herstellung und ihre verwendung zur flammfestausruestung von polycarbonaten |
| EP1854798A3 (en) | 2000-09-19 | 2007-11-28 | Bristol-Myers Squibb Company | Fused heterocyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function |
| KR20090090406A (ko) * | 2000-12-18 | 2009-08-25 | 가부시키가이샤 이야쿠 분지 셋케이 겐쿠쇼 | 염증성 사이토카인 생산 유리 억제제 |
| US20040087548A1 (en) | 2001-02-27 | 2004-05-06 | Salvati Mark E. | Fused cyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function |
| MXPA04000224A (es) | 2001-07-10 | 2005-07-25 | 4Sc Ag | Novedosos compuestos como agentes antiinflamatorios, inmunomoduladores y antiproliferativos. |
| DE10222895A1 (de) * | 2002-05-23 | 2003-12-11 | Bosch Gmbh Robert | Hochdruckspeicher für Kraftstoffeinspritzsysteme mit integriertem Druckregelventil |
| CA2487891A1 (en) * | 2002-06-05 | 2003-12-18 | Institute Of Medicinal Molecular Design, Inc. | Inhibitors against the activation of ap-1 and nfat |
| CA2487900A1 (en) * | 2002-06-05 | 2003-12-18 | Institute Of Medicinal Molecular Design, Inc. | Immunity-related protein kinase inhibitors |
| EA008769B1 (ru) * | 2002-06-05 | 2007-08-31 | Инститьют Оф Медисинал Молекьюлар Дизайн. Инк. | Лекарственное средство для лечения диабета |
| EP1514544A4 (en) * | 2002-06-06 | 2009-01-07 | Inst Med Molecular Design Inc | HYPO-ALLERGENIC |
| EA009051B1 (ru) * | 2002-06-06 | 2007-10-26 | Инститьют Оф Медисинал Молекьюлар Дизайн. Инк. | О-замещенные гидроксиарильные производные |
| CA2489091A1 (en) * | 2002-06-10 | 2003-12-18 | Institute Of Medicinal Molecular Design, Inc. | Inhibitors against activation of nf-kappab |
| AU2003242108B2 (en) * | 2002-06-10 | 2008-09-11 | Institute Of Medicinal Molecular Design, Inc. | Medicament for treatment of cancer |
| CN100490793C (zh) * | 2002-06-11 | 2009-05-27 | 株式会社医药分子设计研究所 | 神经变性疾病治疗药 |
| KR20050074949A (ko) * | 2002-11-12 | 2005-07-19 | 엔오케이 가부시키가이샤 | 고무형상 탄성부품 |
| US7365094B2 (en) | 2002-12-23 | 2008-04-29 | 4Sc Ag | Compounds as anti-inflammatory, immunomodulatory and anti-proliferatory agents |
| WO2004056746A1 (en) * | 2002-12-23 | 2004-07-08 | 4Sc Ag | Cycloalkene dicarboxylic acid compounds as anti-inflammatory, immunomodulatory and anti-proliferatory agents |
| EP1581478A1 (en) * | 2002-12-23 | 2005-10-05 | 4Sc Ag | Dhodh-inhibitors and method for their identification |
| US7247736B2 (en) * | 2002-12-23 | 2007-07-24 | 4Sc Ag | Method of identifying inhibitors of DHODH |
| EP1541198A1 (en) * | 2003-12-05 | 2005-06-15 | 4Sc Ag | Cycloalkyl compounds as anti-inflammatory, immunomodulatory and anti-proliferatory agents |
| EP2585054A1 (en) * | 2010-06-24 | 2013-05-01 | Allergan, Inc. | Derivatives of cycloalkyl- and cycloalkenyl-1,2-dicarboxylic acid compounds having formyl peptide receptor like-1 (fprl-1) agonist or antagonist activity |
| UA108760C2 (uk) | 2010-07-01 | 2015-06-10 | Кальцієві солі сполуки як протизапальні, імуномодулюючі та антипроліферативні засоби | |
| RS65563B1 (sr) | 2018-03-16 | 2024-06-28 | Immunic Ag | Novi polimorfi kalcijumove soli kao anti-inflamatorni, imunomodulatorni i anti-proliferativni agensi |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5379871A (en) * | 1976-12-22 | 1978-07-14 | Monsanto Co | Aromatic system acid compounds |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2794811A (en) * | 1954-06-03 | 1957-06-04 | Allied Chem & Dye Corp | Production of cis-cyclohexane-1, 2-dicarboxylic anhydride |
| US2959599A (en) * | 1956-11-19 | 1960-11-08 | Allied Chem | Isomerization of cyclohexene-1, 2-dicarboxylic anhydrides |
| US3085096A (en) * | 1961-05-31 | 1963-04-09 | Petro Tex Chem Corp | Preparation of cis-4-cyclohexene-1, 2-di-carboxylic acid anhydride |
| US3507904A (en) * | 1966-04-01 | 1970-04-21 | Herbert Schwartz | Novel tetrahydrophthalamic acids and derivatives thereof |
| CH489993A (de) * | 1967-12-19 | 1970-05-15 | Ciba Geigy | Das Pflanzenwachstum regulierendes und phytocides Mittel |
| US3922158A (en) * | 1967-12-19 | 1975-11-25 | Ciba Geigy Ag | Method for inhibiting the growth of dicotyledonous plants |
| US3549655A (en) * | 1967-12-21 | 1970-12-22 | Dow Chemical Co | N-(substituted phenyl) cyclobutanedicarboximides |
| US3745170A (en) * | 1969-03-19 | 1973-07-10 | Sumitomo Chemical Co | Novel n-(3,5-dihalophenyl)-imide compounds |
| FR2059977A1 (US20030220297A1-20031127-C00074.png) * | 1969-08-14 | 1971-06-11 | Socibre | |
| US3825594A (en) * | 1970-01-20 | 1974-07-23 | Sandoz Ag | Bis(trifluoromethyl)benzamides |
| US3654302A (en) * | 1970-01-30 | 1972-04-04 | Herbert Schwartz | Tetrahydrophthalanils |
| US3987056A (en) * | 1973-05-07 | 1976-10-19 | Phillips Petroleum Company | Disproportionation of n-aryl-1,2,3,6-tetrahydrophthalimides |
| US4002460A (en) * | 1974-03-13 | 1977-01-11 | Stauffer Chemical Company | Triazine-antidote compositions and methods of use for cotton |
| US4025505A (en) * | 1975-02-04 | 1977-05-24 | Ciba-Geigy Corporation | Aromatic dicarboxamides |
| CH615912A5 (US20030220297A1-20031127-C00074.png) * | 1975-06-18 | 1980-02-29 | Ciba Geigy Ag | |
| FR2369252B1 (fr) * | 1976-10-29 | 1979-02-23 | Inst Nat Rech Chimique | Composes a,a-difluoroalkylbenzenes substitues et leur fabricationÿ |
| JPS5524127A (en) * | 1978-08-08 | 1980-02-21 | Morishita Seiyaku Kk | 3,6-endomethylene-delta4-1,2,3,6-tetrahydrophtalimide derivative |
| EP0017994A3 (de) * | 1979-04-20 | 1981-01-14 | Ciba-Geigy Ag | Cyclobutandicarbonsäureimide, Verfahren zu deren Herstellung und deren Verwendung als Fungizid; Zwischenprodukte |
| JPS56169669A (en) * | 1980-05-30 | 1981-12-26 | Takeda Chem Ind Ltd | Hexahydroisoindole derivative, its preparation and herbicide |
| JPS59231057A (ja) * | 1983-06-14 | 1984-12-25 | Eisai Co Ltd | カルボン酸アミド化合物およびその誘導体 |
-
1982
- 1982-12-27 JP JP57226685A patent/JPS59118750A/ja active Granted
-
1983
- 1983-12-19 GB GB08333713A patent/GB2133006B/en not_active Expired
- 1983-12-19 AU AU22531/83A patent/AU2253183A/en not_active Abandoned
- 1983-12-20 CA CA000443811A patent/CA1202312A/en not_active Expired
- 1983-12-22 ZA ZA839546A patent/ZA839546B/xx unknown
- 1983-12-22 SE SE8307119A patent/SE8307119L/xx not_active Application Discontinuation
- 1983-12-22 PH PH30020A patent/PH19459A/en unknown
- 1983-12-22 NL NL8304406A patent/NL8304406A/nl not_active Application Discontinuation
- 1983-12-23 DE DE19833346814 patent/DE3346814A1/de not_active Withdrawn
- 1983-12-23 CH CH6912/83A patent/CH656875A5/de not_active IP Right Cessation
- 1983-12-23 IT IT24351/83A patent/IT1170275B/it active
- 1983-12-23 HU HU834462A patent/HU189799B/hu unknown
- 1983-12-23 DK DK596083A patent/DK596083A/da not_active Application Discontinuation
- 1983-12-26 KR KR1019830006180A patent/KR840007714A/ko not_active Application Discontinuation
- 1983-12-26 ES ES528409A patent/ES528409A0/es active Granted
- 1983-12-27 BE BE0/212130A patent/BE898570A/fr not_active IP Right Cessation
- 1983-12-27 FR FR8320864A patent/FR2538386B1/fr not_active Expired
-
1985
- 1985-06-01 ES ES543810A patent/ES8608486A1/es not_active Expired
- 1985-12-02 US US06/803,526 patent/US4661630A/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5379871A (en) * | 1976-12-22 | 1978-07-14 | Monsanto Co | Aromatic system acid compounds |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4057782A1 (en) | 2021-03-12 | 2022-09-14 | Atotech Deutschland GmbH & Co. KG | Method for increasing adhesion strength between copper and an organic material and reducing halo and wedge void formation by modifying the copper surface and/or by using heteroaromatic silane compounds |
| EP4056285A1 (en) | 2021-03-12 | 2022-09-14 | Atotech Deutschland GmbH & Co. KG | Triazine silane compound and its usage as adhesion promotor |
| WO2022189644A1 (en) | 2021-03-12 | 2022-09-15 | Atotech Deutschland GmbH & Co. KG | Method for increasing adhesion strength between copper and an organic material and reducing halo and wedge void formation by modifying the copper surface and/or by using heteroaromatic silane compounds |
| WO2022189646A1 (en) | 2021-03-12 | 2022-09-15 | Atotech Deutschland GmbH & Co. KG | Triazine silane compound and its usage as adhesion promotor |
Also Published As
| Publication number | Publication date |
|---|---|
| SE8307119L (sv) | 1984-06-28 |
| FR2538386B1 (fr) | 1986-04-18 |
| ES8608486A1 (es) | 1986-06-16 |
| CH656875A5 (de) | 1986-07-31 |
| BE898570A (fr) | 1984-06-27 |
| ES543810A0 (es) | 1986-06-16 |
| GB8333713D0 (en) | 1984-01-25 |
| GB2133006B (en) | 1986-10-22 |
| DK596083D0 (da) | 1983-12-23 |
| HU189799B (en) | 1986-07-28 |
| GB2133006A (en) | 1984-07-18 |
| DE3346814A1 (de) | 1984-06-28 |
| PH19459A (en) | 1986-04-18 |
| ZA839546B (en) | 1984-08-29 |
| IT1170275B (it) | 1987-06-03 |
| ES8601859A1 (es) | 1985-11-01 |
| AU2253183A (en) | 1984-07-05 |
| FR2538386A1 (fr) | 1984-06-29 |
| US4661630A (en) | 1987-04-28 |
| ES528409A0 (es) | 1985-11-01 |
| DK596083A (da) | 1984-06-28 |
| NL8304406A (nl) | 1984-07-16 |
| CA1202312A (en) | 1986-03-25 |
| JPS59118750A (ja) | 1984-07-09 |
| IT8324351A0 (it) | 1983-12-23 |
| SE8307119D0 (sv) | 1983-12-22 |
| KR840007714A (ko) | 1984-12-10 |
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