IL125671A - Crystal form of n-(4-trifluoromethylphenyl)-5-methylisoxazole-4-carboxamide - Google Patents
Crystal form of n-(4-trifluoromethylphenyl)-5-methylisoxazole-4-carboxamideInfo
- Publication number
- IL125671A IL125671A IL12567198A IL12567198A IL125671A IL 125671 A IL125671 A IL 125671A IL 12567198 A IL12567198 A IL 12567198A IL 12567198 A IL12567198 A IL 12567198A IL 125671 A IL125671 A IL 125671A
- Authority
- IL
- Israel
- Prior art keywords
- cancer
- modification
- compound
- formula
- lines
- Prior art date
Links
- 239000013078 crystal Substances 0.000 title claims abstract description 25
- VHOGYURTWQBHIL-UHFFFAOYSA-N leflunomide Chemical compound O1N=CC(C(=O)NC=2C=CC(=CC=2)C(F)(F)F)=C1C VHOGYURTWQBHIL-UHFFFAOYSA-N 0.000 title description 7
- 238000012986 modification Methods 0.000 claims abstract description 67
- 230000004048 modification Effects 0.000 claims abstract description 67
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 238000002441 X-ray diffraction Methods 0.000 claims abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 5
- 238000005169 Debye-Scherrer Methods 0.000 claims abstract description 4
- 230000005540 biological transmission Effects 0.000 claims abstract description 4
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 3
- 208000003174 Brain Neoplasms Diseases 0.000 claims abstract description 3
- 206010006187 Breast cancer Diseases 0.000 claims abstract description 3
- 208000026310 Breast neoplasm Diseases 0.000 claims abstract description 3
- 201000003883 Cystic fibrosis Diseases 0.000 claims abstract description 3
- 206010012438 Dermatitis atopic Diseases 0.000 claims abstract description 3
- 206010020751 Hypersensitivity Diseases 0.000 claims abstract description 3
- 208000005016 Intestinal Neoplasms Diseases 0.000 claims abstract description 3
- 208000007766 Kaposi sarcoma Diseases 0.000 claims abstract description 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims abstract description 3
- 206010033128 Ovarian cancer Diseases 0.000 claims abstract description 3
- 206010061535 Ovarian neoplasm Diseases 0.000 claims abstract description 3
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims abstract description 3
- 206010060862 Prostate cancer Diseases 0.000 claims abstract description 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims abstract description 3
- 201000004681 Psoriasis Diseases 0.000 claims abstract description 3
- 206010039491 Sarcoma Diseases 0.000 claims abstract description 3
- 206010040047 Sepsis Diseases 0.000 claims abstract description 3
- 208000000453 Skin Neoplasms Diseases 0.000 claims abstract description 3
- 208000024780 Urticaria Diseases 0.000 claims abstract description 3
- 206010046851 Uveitis Diseases 0.000 claims abstract description 3
- 230000001154 acute effect Effects 0.000 claims abstract description 3
- 230000007815 allergy Effects 0.000 claims abstract description 3
- 208000006673 asthma Diseases 0.000 claims abstract description 3
- 201000008937 atopic dermatitis Diseases 0.000 claims abstract description 3
- 201000011510 cancer Diseases 0.000 claims abstract description 3
- 208000019425 cirrhosis of liver Diseases 0.000 claims abstract description 3
- 206010009887 colitis Diseases 0.000 claims abstract description 3
- 230000001900 immune effect Effects 0.000 claims abstract description 3
- 201000002313 intestinal cancer Diseases 0.000 claims abstract description 3
- 208000032839 leukemia Diseases 0.000 claims abstract description 3
- 201000005202 lung cancer Diseases 0.000 claims abstract description 3
- 208000020816 lung neoplasm Diseases 0.000 claims abstract description 3
- 230000001926 lymphatic effect Effects 0.000 claims abstract description 3
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims abstract description 3
- 206010027191 meningioma Diseases 0.000 claims abstract description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims abstract description 3
- 201000002528 pancreatic cancer Diseases 0.000 claims abstract description 3
- 208000008443 pancreatic carcinoma Diseases 0.000 claims abstract description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 3
- 206010039083 rhinitis Diseases 0.000 claims abstract description 3
- 201000000849 skin cancer Diseases 0.000 claims abstract description 3
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims abstract description 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000007900 aqueous suspension Substances 0.000 claims 2
- 239000000243 solution Substances 0.000 description 11
- 238000009472 formulation Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 239000002775 capsule Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000010899 nucleation Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- 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 2
- 241001465754 Metazoa Species 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 230000002596 correlated effect Effects 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 229960000681 leflunomide Drugs 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 1
- 229920000936 Agarose Polymers 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- 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
- 239000004605 External Lubricant Substances 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- -1 paraffins Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Physical Education & Sports Medicine (AREA)
- Emergency Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Obesity (AREA)
- Rheumatology (AREA)
- Neurology (AREA)
- Oncology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Communicable Diseases (AREA)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Reproductive Health (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL13943898A IL139438A (en) | 1997-08-08 | 1998-08-05 | Crystal form of n-(4-trifluoromethylphenyl)-4-methylisoxazole-4-carboxamide |
| IL13943800A IL139438A0 (en) | 1997-08-08 | 2000-11-02 | Crystal form of n- (4-trifluoromethylphenyl)-5-methylisoxazole-4-carboxamide |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19734438A DE19734438A1 (de) | 1997-08-08 | 1997-08-08 | Kristallform von N-(4-Trifluormethylphenyl)-5-methyl-isoxazole-4-carboxamid |
| DE1997156093 DE19756093A1 (de) | 1997-12-17 | 1997-12-17 | Verfahren zur Herstellung einer Kristallform von N-(4-Trifluormethylphenyl)-5-methyl-isoxazole-4-carboxamid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL125671A0 IL125671A0 (en) | 1999-04-11 |
| IL125671A true IL125671A (en) | 2002-11-10 |
Family
ID=26038983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL12567198A IL125671A (en) | 1997-08-08 | 1998-08-05 | Crystal form of n-(4-trifluoromethylphenyl)-5-methylisoxazole-4-carboxamide |
Country Status (28)
| Country | Link |
|---|---|
| US (5) | US6060494A (no) |
| EP (2) | EP0903345B1 (no) |
| JP (2) | JPH11124372A (no) |
| KR (2) | KR100544041B1 (no) |
| CN (2) | CN1089759C (no) |
| AR (1) | AR015418A1 (no) |
| AT (2) | ATE207065T1 (no) |
| AU (1) | AU752764B2 (no) |
| BR (1) | BR9806568A (no) |
| CA (1) | CA2245267C (no) |
| CZ (3) | CZ301514B6 (no) |
| DE (2) | DE59800287D1 (no) |
| DK (2) | DK0903345T3 (no) |
| ES (2) | ES2166205T3 (no) |
| GR (1) | GR3034814T3 (no) |
| HK (2) | HK1017681A1 (no) |
| HU (2) | HU229232B1 (no) |
| ID (1) | ID20667A (no) |
| IL (1) | IL125671A (no) |
| NO (1) | NO310871B1 (no) |
| NZ (1) | NZ331270A (no) |
| PL (1) | PL192126B1 (no) |
| PT (2) | PT987256E (no) |
| RU (1) | RU2224753C2 (no) |
| SK (2) | SK282641B6 (no) |
| TR (2) | TR200600582A1 (no) |
| TW (1) | TW593288B (no) |
| UA (1) | UA54411C2 (no) |
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| EP0903345B1 (de) * | 1997-08-08 | 2000-10-04 | Aventis Pharma Deutschland GmbH | Kristallform von 5-Methylisoxazol-4-carbonsäure-(4-trifluormethyl)-anilid |
| DE19908527C2 (de) | 1999-02-26 | 2001-08-30 | Aventis Pharma Gmbh | Verfahren zur Kristallisation von N-(4-Trifluormethylphenyl)-5-methyl-isoxazol-4-carboxamid |
| HUP0204069A3 (en) * | 1999-12-16 | 2005-01-28 | Teva Pharma | Novel processes for making- and a new crystalline form of- leflunomide and pharmaceutical composition containing it |
| AU2001234943A1 (en) * | 2000-02-15 | 2001-08-27 | Teva Pharmaceutical Industries Ltd. | A method for synthesizing leflunomide |
| CA2429426A1 (en) * | 2000-11-17 | 2002-05-23 | Takeda Chemical Industries, Ltd. | Isoxazole derivatives |
| 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 |
| US7429593B2 (en) | 2001-09-14 | 2008-09-30 | Shionogi & Co., Ltd. | Utilities of amide compounds |
| US20050158371A1 (en) * | 2002-02-12 | 2005-07-21 | Sumitomo Pharmaceuticals Co., Ltd. | Novel external agent |
| WO2003068239A1 (fr) * | 2002-02-12 | 2003-08-21 | Sumitomo Pharmaceuticals Co., Ltd. | Nouveaux medicaments d'usage externe |
| US20040229896A1 (en) * | 2003-03-12 | 2004-11-18 | Toth Zoltan G. | Stable pharmaceutical compositions of desloratadine |
| US20060135547A1 (en) * | 2003-03-12 | 2006-06-22 | Toth Zoltan G | Stable pharmaceutical compositions of desloratadine and processes for preparation of polymorphic forms of desloratadine |
| JP4223428B2 (ja) * | 2004-03-31 | 2009-02-12 | 富士通メディアデバイス株式会社 | フィルタおよびその製造方法 |
| WO2007067710A1 (en) * | 2005-12-08 | 2007-06-14 | Amphora Discovery Corporation | Certain chemical entities, compositions, and methods for modulating trpv1 |
| CN101143834B (zh) * | 2006-09-15 | 2010-09-08 | 欣凯医药化工中间体（上海）有限公司 | N-(4-三氟甲基苯)-2-氰基-3-羟基丁烯酰胺钠盐的多晶型及其制备方法 |
| PE20091680A1 (es) * | 2008-03-10 | 2009-11-16 | Takeda Pharmaceutical | Cristal de compuestos de bencimidazol |
| PE20152031A1 (es) | 2009-09-18 | 2016-01-14 | Sanofi Sa | Formulaciones en comprimido de la (4'-trifluorometilfenil)amida del acido (z)-2-ciano-3-hidroxibut-2-enoico con estabilidad mejorada |
| CN103977594B (zh) * | 2014-06-03 | 2016-02-17 | 江苏九九久科技股份有限公司 | 一种结晶方法 |
| US9895370B2 (en) * | 2015-11-19 | 2018-02-20 | Pharmedix.Co., Ltd | Pharmaceutical composition for preventing or treating of cirrhosis of liver comprising G protein coupled receptor 119 ligand as an active ingredient |
| CN109180599A (zh) * | 2018-09-03 | 2019-01-11 | 深圳市新阳唯康科技有限公司 | 一种来氟米特新晶型化合物及其制备方法 |
| CN112898215B (zh) * | 2021-02-04 | 2022-11-08 | 美罗药业股份有限公司 | 一种来氟米特晶型i的制备方法 |
| CN114716388B (zh) * | 2021-11-04 | 2024-02-13 | 江苏冠军科技集团股份有限公司 | 一种磺胺-银化合物及其制备方法 |
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| NL178596C (nl) * | 1975-06-05 | 1986-04-16 | Hoechst Ag | Werkwijze voor het bereiden van een geneesmiddel met antiflogistische en/of analgetische werking, alsmede werkwijze voor het bereiden van daarin als geneeskrachtige verbindingen te gebruiken 5-methylisoxazool-4-carbonzuuraniliden. |
| DE2524959C2 (de) * | 1975-06-05 | 1983-02-10 | Hoechst Ag, 6000 Frankfurt | 5-Methyl-isoxazol-4-carbonsäureanilide, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende Mittel |
| NL186239B (nl) * | 1975-06-05 | Hoechst Ag | 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. | |
| DE2525959A1 (de) * | 1975-06-11 | 1977-02-10 | Focke Pfuhl Verpack Automat | Verpackung fuer zigaretten, zigarillos etc. |
| DE2854439A1 (de) * | 1978-12-16 | 1980-07-03 | Hoechst Ag | Ein isoxazolderivat, verfahren zu seiner herstellung, diese verbindung enthaltende mittel und verwendung |
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-
1998
- 1998-07-31 EP EP98114373A patent/EP0903345B1/de not_active Expired - Lifetime
- 1998-07-31 EP EP99117098A patent/EP0987256B1/de not_active Expired - Lifetime
- 1998-07-31 AT AT99117098T patent/ATE207065T1/de active
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- 1998-07-31 PT PT99117098T patent/PT987256E/pt unknown
- 1998-07-31 DK DK98114373T patent/DK0903345T3/da active
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- 1998-07-31 DK DK99117098T patent/DK0987256T3/da active
- 1998-07-31 AT AT98114373T patent/ATE196764T1/de active
- 1998-07-31 PT PT98114373T patent/PT903345E/pt unknown
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- 1998-08-06 UA UA98084307A patent/UA54411C2/uk unknown
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- 1998-08-06 SK SK1058-98A patent/SK282641B6/sk not_active IP Right Cessation
- 1998-08-06 ID IDP981098A patent/ID20667A/id unknown
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- 1998-08-06 TW TW087112927A patent/TW593288B/zh not_active IP Right Cessation
- 1998-08-07 JP JP10224015A patent/JPH11124372A/ja active Pending
- 1998-08-07 PL PL327901A patent/PL192126B1/pl unknown
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- 1998-08-07 KR KR1019980032110A patent/KR100544041B1/ko not_active IP Right Cessation
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1999
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2000
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2001
- 2001-01-19 US US09/764,258 patent/US6552202B2/en not_active Expired - Lifetime
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2002
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