DE4028906C2 - - Google Patents
Info
- Publication number
- DE4028906C2 DE4028906C2 DE4028906A DE4028906A DE4028906C2 DE 4028906 C2 DE4028906 C2 DE 4028906C2 DE 4028906 A DE4028906 A DE 4028906A DE 4028906 A DE4028906 A DE 4028906A DE 4028906 C2 DE4028906 C2 DE 4028906C2
- Authority
- DE
- Germany
- Prior art keywords
- flurbiprofen
- tablets
- enantiomers
- pain
- active ingredient
- 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 - Fee Related
Links
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000003814 drug Substances 0.000 claims abstract description 19
- SYTBZMRGLBWNTM-SNVBAGLBSA-N (R)-flurbiprofen Chemical compound FC1=CC([C@H](C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-SNVBAGLBSA-N 0.000 claims abstract description 16
- 229960002390 flurbiprofen Drugs 0.000 claims abstract description 16
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 4
- 238000011282 treatment Methods 0.000 claims abstract description 4
- SYTBZMRGLBWNTM-JTQLQIEISA-N (S)-flurbiprofen Chemical compound FC1=CC([C@@H](C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-JTQLQIEISA-N 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 9
- -1 amino acid salt Chemical class 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-M lysinate Chemical compound NCCCCC(N)C([O-])=O KDXKERNSBIXSRK-UHFFFAOYSA-M 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 206010037660 Pyrexia Diseases 0.000 abstract 1
- 239000012059 conventional drug carrier Substances 0.000 abstract 1
- 208000027866 inflammatory disease Diseases 0.000 abstract 1
- 239000003826 tablet Substances 0.000 description 17
- 230000036407 pain Effects 0.000 description 14
- 229940079593 drug Drugs 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 230000000202 analgesic effect Effects 0.000 description 9
- 241000700159 Rattus Species 0.000 description 7
- 230000037396 body weight Effects 0.000 description 7
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 229940124599 anti-inflammatory drug Drugs 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 206010030113 Oedema Diseases 0.000 description 5
- 230000003110 anti-inflammatory effect Effects 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 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 4
- 241001465754 Metazoa Species 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000829 suppository Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241000416162 Astragalus gummifer Species 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 229920001615 Tragacanth Polymers 0.000 description 3
- 208000025865 Ulcer Diseases 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 229940035676 analgesics Drugs 0.000 description 3
- 239000000730 antalgic agent Substances 0.000 description 3
- 235000010418 carrageenan Nutrition 0.000 description 3
- 229920001525 carrageenan Polymers 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 235000010980 cellulose Nutrition 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 239000008298 dragée Substances 0.000 description 3
- 210000002683 foot Anatomy 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 230000010534 mechanism of action Effects 0.000 description 3
- 229920000609 methyl cellulose Polymers 0.000 description 3
- 239000001923 methylcellulose Substances 0.000 description 3
- 235000010981 methylcellulose Nutrition 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003180 prostaglandins Chemical class 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 239000000196 tragacanth Substances 0.000 description 3
- 235000010487 tragacanth Nutrition 0.000 description 3
- 229940116362 tragacanth Drugs 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 2
- 235000019501 Lemon oil Nutrition 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 208000025747 Rheumatic disease Diseases 0.000 description 2
- 208000005392 Spasm Diseases 0.000 description 2
- 238000000692 Student's t-test Methods 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 230000003111 delayed effect Effects 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
- 229960003898 flurbiprofen sodium Drugs 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 238000005469 granulation Methods 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 229940116364 hard fat Drugs 0.000 description 2
- 229960001680 ibuprofen Drugs 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000010501 lemon oil Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- FJQXCDYVZAHXNS-UHFFFAOYSA-N methadone hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 FJQXCDYVZAHXNS-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 210000000813 small intestine Anatomy 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008174 sterile solution Substances 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000036269 ulceration Effects 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- 241001535291 Analges Species 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 208000035859 Drug effect increased Diseases 0.000 description 1
- 206010059024 Gastrointestinal toxicity Diseases 0.000 description 1
- 206010070840 Gastrointestinal tract irritation Diseases 0.000 description 1
- 239000001828 Gelatine Substances 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
- 206010061218 Inflammation Diseases 0.000 description 1
- 102000000589 Interleukin-1 Human genes 0.000 description 1
- 108010002352 Interleukin-1 Proteins 0.000 description 1
- 206010022714 Intestinal ulcer Diseases 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 238000011785 NMRI mouse Methods 0.000 description 1
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
- 206010050661 Platelet aggregation inhibition Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 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
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000001741 anti-phlogistic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000001174 ascending effect Effects 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
- 230000002146 bilateral effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000005422 blasting Methods 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007910 chewable tablet Substances 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 231100000414 gastrointestinal toxicity Toxicity 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 229960002009 naproxen Drugs 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229940100692 oral suspension Drugs 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 230000008058 pain sensation Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 210000004303 peritoneum Anatomy 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229940100467 polyvinyl acetate phthalate Drugs 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- ZLVSYODPTJZFMK-UHFFFAOYSA-M sodium 4-hydroxybenzoate Chemical compound [Na+].OC1=CC=C(C([O-])=O)C=C1 ZLVSYODPTJZFMK-UHFFFAOYSA-M 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000012353 t test Methods 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
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
-
- 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
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines Containing Plant Substances (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4028906A DE4028906A1 (de) | 1990-09-12 | 1990-09-12 | Arzneimittel sowie deren herstellung und deren verwendung bei der bekaempfung von schmerzen und/oder entzuendungen und/oder fieber an tieren und menschen |
| US07/700,798 US5206029A (en) | 1990-09-12 | 1991-05-16 | Medicament and its production and use in the treatment of pain, inflammation and fever in man and animals |
| US07/700,797 US5200198A (en) | 1990-09-12 | 1991-05-16 | Medicament and its production and use in the treatment of pain, inflammation and fever in man and animals |
| AT91914752T ATE158182T1 (de) | 1990-09-12 | 1991-08-19 | Arzneimittel sowie deren herstellung und deren verwendung bei der bekämpfung von schmerzen und/oder entzündungen an tieren und menschen |
| DK91914752T DK0607128T4 (da) | 1990-09-12 | 1991-08-19 | Lægemiddel samt fremstilling deraf og anvendelse deraf ved bekæmpelsen af smerter og/eller betændelser hos dyr og mennesker |
| RU9193005246A RU2080116C1 (ru) | 1990-09-12 | 1991-08-19 | Средство для лечения болей или воспалений |
| DE59108854T DE59108854D1 (de) | 1990-09-12 | 1991-08-19 | Arzneimittel sowie deren herstellung und deren verwendung bei der bekämpfung von schmerzen und/oder entzündungen an tieren und menschen |
| HU9300636A HU225887B1 (en) | 1990-09-12 | 1991-08-19 | Process for producing pharmaceutical compositions containing flurbiprofen having painkiller activity |
| CA002087723A CA2087723C (en) | 1990-09-12 | 1991-08-19 | Treatment with flurbiprofen of pain and inflammation in mammals |
| PCT/EP1991/001568 WO1992004018A1 (de) | 1990-09-12 | 1991-08-19 | Arzneimittel sowie deren herstellung und deren verwendung bei der bekämpfung von schmerzen und/oder entzündungen an tieren und menschen |
| JP51355291A JP3305315B2 (ja) | 1990-09-12 | 1991-08-19 | 動物及び人間の疼痛及び／又は炎症の抑制時における薬剤ならびにその製造及びその使用 |
| ES91914752T ES2106785T5 (es) | 1990-09-12 | 1991-08-19 | Medicamentos, su preparacion y empleo como analgesicos y/o antiinflamatorios para seres humanos y animales. |
| EP91914752A EP0607128B2 (de) | 1990-09-12 | 1991-08-19 | Arzneimittel sowie deren herstellung und deren verwendung bei der bekämpfung von schmerzen und/oder entzündungen an tieren und menschen |
| AU83352/91A AU654498B2 (en) | 1990-09-12 | 1991-08-19 | Drugs, their manufacture, and their use as painkillers and/or to treat inflammations in humans and animals |
| FI931097A FI103180B1 (fi) | 1990-09-12 | 1993-03-11 | Flurbiprofeenia sisältävien lääkkeiden valmistus kipujen ja/tai tulehdusten torjumiseksi eläimissä ja ihmisissä |
| GR970403151T GR3025502T3 (en) | 1990-09-12 | 1997-11-26 | Drugs, their manufacture, and their use as painkillers and/or to treat inflammations in humans and animals. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4028906A DE4028906A1 (de) | 1990-09-12 | 1990-09-12 | Arzneimittel sowie deren herstellung und deren verwendung bei der bekaempfung von schmerzen und/oder entzuendungen und/oder fieber an tieren und menschen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE4028906A1 DE4028906A1 (de) | 1992-03-19 |
| DE4028906C2 true DE4028906C2 (OSRAM) | 1992-10-29 |
Family
ID=6414093
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4028906A Granted DE4028906A1 (de) | 1990-09-12 | 1990-09-12 | Arzneimittel sowie deren herstellung und deren verwendung bei der bekaempfung von schmerzen und/oder entzuendungen und/oder fieber an tieren und menschen |
| DE59108854T Expired - Fee Related DE59108854D1 (de) | 1990-09-12 | 1991-08-19 | Arzneimittel sowie deren herstellung und deren verwendung bei der bekämpfung von schmerzen und/oder entzündungen an tieren und menschen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59108854T Expired - Fee Related DE59108854D1 (de) | 1990-09-12 | 1991-08-19 | Arzneimittel sowie deren herstellung und deren verwendung bei der bekämpfung von schmerzen und/oder entzündungen an tieren und menschen |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US5200198A (OSRAM) |
| EP (1) | EP0607128B2 (OSRAM) |
| JP (1) | JP3305315B2 (OSRAM) |
| AT (1) | ATE158182T1 (OSRAM) |
| AU (1) | AU654498B2 (OSRAM) |
| CA (1) | CA2087723C (OSRAM) |
| DE (2) | DE4028906A1 (OSRAM) |
| DK (1) | DK0607128T4 (OSRAM) |
| ES (1) | ES2106785T5 (OSRAM) |
| FI (1) | FI103180B1 (OSRAM) |
| GR (1) | GR3025502T3 (OSRAM) |
| HU (1) | HU225887B1 (OSRAM) |
| RU (1) | RU2080116C1 (OSRAM) |
| WO (1) | WO1992004018A1 (OSRAM) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4319438C1 (de) * | 1993-06-11 | 1994-06-01 | Gerd Dr Dr Geislinger | Arzneimittel auf der Grundlage von Ketoprofen zur Bekämpfung von Schmerzen und/oder Entzündungen und/oder Fieber an Menschen und Tieren |
| US8092829B2 (en) | 2000-09-25 | 2012-01-10 | Paz Arzneimittelentwicklungsgesellschaft Mbh | Use of R-arylpropionic acids for treating illnesses with a rheumatic nature |
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4140183C2 (de) * | 1991-12-05 | 1995-12-21 | Alfatec Pharma Gmbh | Retardform für ein Flurbiprofen enthaltendes Arzneimittel |
| DE4140184C2 (de) * | 1991-12-05 | 1995-12-21 | Alfatec Pharma Gmbh | Akutform für ein Flurbiprofen enthaltendes Arzneimittel |
| DE4140172C2 (de) * | 1991-12-05 | 1995-12-21 | Alfatec Pharma Gmbh | Retardform für ein Ibuprofen enthaltendes Arzneimittel |
| DE4140185C2 (de) * | 1991-12-05 | 1996-02-01 | Alfatec Pharma Gmbh | Ein 2-Arylpropionsäurederivat in Nanosolform enthaltendes Arzneimittel und seine Herstellung |
| DE4216756C2 (de) * | 1992-05-21 | 1994-08-25 | Pharmatrans Sanaq Ag | 2-Arylpropionsäure-Zubereitungen und Verfahren zu ihrer Herstellung |
| CA2150355C (en) * | 1992-12-02 | 2008-03-11 | Robert Hardy | Process of resolving phenylpropionic acids using alpha-methylbenzylamine |
| JP3782834B2 (ja) * | 1994-10-26 | 2006-06-07 | 株式会社トクホン | 鎮痛抗炎症貼付剤 |
| IT1271800B (it) * | 1994-12-27 | 1997-06-09 | Zambon Spa | Processo di preparazione degli enantiomeri dell'acido 2- (2-fluoro- 4-bifenil) propionico |
| US5955504A (en) * | 1995-03-13 | 1999-09-21 | Loma Linda University Medical Center | Colorectal chemoprotective composition and method of preventing colorectal cancer |
| US6160018A (en) * | 1995-03-13 | 2000-12-12 | Loma Linda University Medical Center | Prophylactic composition and method for alzheimer's Disease |
| US5981592A (en) * | 1995-03-13 | 1999-11-09 | Loma Linda University Medical Center | Method and composition for treating cystic fibrosis |
| AT408067B (de) * | 1995-03-17 | 2001-08-27 | Gebro Pharma Gmbh | Pharmazeutische zusammensetzung zur topischen applizierung und verfahren zu ihrer herstellung |
| GB9523833D0 (en) * | 1995-11-22 | 1996-01-24 | Boots Co Plc | Medical treatment |
| US5702720A (en) * | 1995-12-22 | 1997-12-30 | Minnesota Mining And Manufacturing Company | Transdermal device for the delivery of flurbiprofen |
| ES2253810T3 (es) * | 1997-03-10 | 2006-06-01 | Loma Linda University Medical Center | Uso de r-aines para la prevencion de la enfermedad de alzheimer. |
| GB9705989D0 (en) * | 1997-03-22 | 1997-05-07 | Boots Co Plc | Therapeutic composition |
| SE9704400D0 (sv) * | 1997-11-28 | 1997-11-28 | Astra Ab | Porous inorganic particles as carriers for drug substances |
| PT1143958E (pt) | 1998-09-03 | 2007-04-30 | Univ Loma Linda Med | Composição farmacêutica e utilização de rnsaid para o tratamento da inflamação. |
| AU2004222809B2 (en) * | 1998-09-03 | 2007-06-28 | Loma Linda University Medical Center | Pharmaceutical Composition and Method for Treatment of Inflammation |
| DE19907895A1 (de) * | 1999-02-24 | 2000-11-16 | Paz Arzneimittelentwicklung | Verwendung von R-Arylpropionsäuren zur Herstellung von Arzneimitteln zur Behandlung von Erkrankungen bei Mensch und Tier, welche durch die Hemmung der Aktivierung von NF-kB therapeutisch beeinflußt werden können |
| CA2406383A1 (en) * | 2000-04-13 | 2001-10-25 | Mayo Foundation For Medical Education And Research | A.beta.42 lowering agents |
| US20080021085A1 (en) * | 2000-04-13 | 2008-01-24 | Mayo Foundation For Medical Education And Research | Method of reducing abeta42 and treating diseases |
| US20060004086A1 (en) * | 2000-04-13 | 2006-01-05 | Mayo Foundation For Medical Education And Research | Method of reducing Abeta42 and treating diseases |
| US6497901B1 (en) * | 2000-11-02 | 2002-12-24 | Royer Biomedical, Inc. | Resorbable matrices for delivery of bioactive compounds |
| DK1393277T3 (da) | 2001-05-21 | 2006-10-30 | Alcon Inc | Anvendelse af NF-Kappa-B inhibitorer til behandling af öjentörhedslidelser |
| US20030027867A1 (en) * | 2001-06-29 | 2003-02-06 | Myriad Genetics, Incorporated | Use of R-NSAID compounds for anti-HIV treatment |
| US20030143165A1 (en) * | 2002-01-25 | 2003-07-31 | Allan Evans | NSAID-containing topical formulations that demonstrate chemopreventive activity |
| US7247328B2 (en) * | 2002-05-31 | 2007-07-24 | Zinpro Corporation | Chromium (III) alpha amino acid complexes |
| US7129375B2 (en) * | 2002-10-16 | 2006-10-31 | Zinpro Corporation | Metal complexes of α amino dicarboxylic acids |
| EP1603548A4 (en) * | 2003-02-05 | 2007-10-10 | Myriad Genetics Inc | METHOD AND COMPOSITION FOR THE TREATMENT OF NEURODEEGENERATIVE DISEASES |
| US6953507B2 (en) * | 2003-03-21 | 2005-10-11 | Ecolab Inc. | Low temperature cleaning |
| WO2005065069A2 (en) * | 2003-07-11 | 2005-07-21 | Myriad Genetics, Inc. | Pharmaceutical methods, dosing regimes and dosage forms for the treatment of alzheimer's disease |
| US20050171207A1 (en) * | 2003-09-26 | 2005-08-04 | Myriad Genetics, Incorporated | Method and composition for combination treatment of neurodegenerative disorders |
| FR2865648B1 (fr) * | 2004-02-03 | 2006-06-30 | Philippe Perovitch | Procede de diffusion de molecules insolubles en milieu aqueux et composition mettant en oeuvre ce procede |
| WO2006001877A2 (en) * | 2004-04-13 | 2006-01-05 | Myriad Genetics, Inc. | Combination treatment for neurodegenerative disorders comprising r-flurbiprofen |
| KR20070004036A (ko) * | 2004-04-29 | 2007-01-05 | 키스톤 리테이닝 월 시스템스, 아이엔씨 | 벽, 옹벽 및 그 외 유사한 것을 위한 베니어 |
| WO2006020850A2 (en) * | 2004-08-11 | 2006-02-23 | Myriad Genetics, Inc. | Pharmaceutical composition and method for treating neurodegenerative disorders |
| WO2006020852A2 (en) * | 2004-08-11 | 2006-02-23 | Myriad Genetics, Inc. | Pharmaceutical composition and method for treating neurodegenerative disorders |
| CA2618985A1 (en) * | 2004-08-11 | 2006-02-23 | Myriad Genetics, Inc. | Pharmaceutical composition and method for treating neurodegenerative disorders |
| CA2615063A1 (en) * | 2005-07-22 | 2007-02-01 | Myriad Genetics, Inc. | High drug load formulations and dosage forms |
| US20070042094A1 (en) | 2005-08-22 | 2007-02-22 | Alcide Corporation | Oxidation method and compositions therefor |
| EP2046119A2 (en) * | 2006-07-07 | 2009-04-15 | Myriad Genetics, Inc. | Treatment of psychiatric disorders |
| CA2710318A1 (en) * | 2007-12-21 | 2009-07-09 | Paz Arzneimittel-Entwicklungsgesellscaft Mbh | Drugs as well as their production and use in the treatment of pain-associated neuropathies |
| US20090162421A1 (en) * | 2007-12-21 | 2009-06-25 | Paz Arzneimittel-Entwicklungsgesellschaft Mbh | Drugs as well as their production and use in the treatment of pain-associated neuropathies |
| PT2387391T (pt) * | 2009-07-24 | 2017-04-20 | Mika Pharma Ges Für Die Entw Und Vermarktung Pharmazeutischer Produkte Mbh | Processo para o desenvolvimento de uma composição líquida a ser aplicada na forma de espuma sobre a pele e composição de aplicação tópica |
| EP2468270A1 (en) | 2010-12-21 | 2012-06-27 | GALENpharma GmbH | (R)-2-(3-fluoro-4-phenylphenyl)propionic acid for use in the treatment of skin diseases |
| US20150183737A1 (en) * | 2012-07-20 | 2015-07-02 | Vanderbilt University | Compositions and methods for substrate-selective inhibition of endocannabinoid oxygenation |
| US9578879B1 (en) | 2014-02-07 | 2017-02-28 | Gojo Industries, Inc. | Compositions and methods having improved efficacy against spores and other organisms |
| CN113262216A (zh) * | 2020-02-14 | 2021-08-17 | 北京泰德制药股份有限公司 | 一种用于消除皮表红肿镇痛的外用制剂 |
| CN115536525B (zh) * | 2022-09-23 | 2024-02-23 | 南京知和医药科技有限公司 | 一种s-（+）-氟比洛芬盐及其制备方法、药物组合物和用途 |
| CN119837880B (zh) * | 2024-12-18 | 2025-08-29 | 中南大学 | 一种含氟比洛芬的药物组合物及其应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3784705A (en) * | 1964-01-24 | 1974-01-08 | Boots Pure Drug Co Ltd | Therapeutically active phenylalkane derivatives |
| GR64816B (en) * | 1977-03-08 | 1980-06-03 | Boots Co Ltd | Resolution of flurbiprofen ii/iii |
| US4209638A (en) * | 1977-03-08 | 1980-06-24 | The Boots Company Limited | Preparation of therapeutic agents |
| ZA828453B (en) † | 1981-12-08 | 1983-12-28 | Boots Co Plc | Therapeutic agents |
| JPS6283885A (ja) † | 1985-10-08 | 1987-04-17 | Nitto Electric Ind Co Ltd | 酵素固定膜及びその製造方法 |
| US4927854A (en) * | 1987-12-24 | 1990-05-22 | Analgesic Associates | Sustained/enhanced analgesia |
| AU6758990A (en) † | 1989-11-06 | 1991-05-31 | Sepracor, Inc. | Analgesic composition containing optically pure s(+) flurbiprofen |
-
1990
- 1990-09-12 DE DE4028906A patent/DE4028906A1/de active Granted
-
1991
- 1991-05-16 US US07/700,797 patent/US5200198A/en not_active Expired - Lifetime
- 1991-05-16 US US07/700,798 patent/US5206029A/en not_active Expired - Lifetime
- 1991-08-19 AU AU83352/91A patent/AU654498B2/en not_active Ceased
- 1991-08-19 WO PCT/EP1991/001568 patent/WO1992004018A1/de not_active Ceased
- 1991-08-19 HU HU9300636A patent/HU225887B1/hu not_active IP Right Cessation
- 1991-08-19 ES ES91914752T patent/ES2106785T5/es not_active Expired - Lifetime
- 1991-08-19 EP EP91914752A patent/EP0607128B2/de not_active Expired - Lifetime
- 1991-08-19 JP JP51355291A patent/JP3305315B2/ja not_active Expired - Fee Related
- 1991-08-19 RU RU9193005246A patent/RU2080116C1/ru not_active IP Right Cessation
- 1991-08-19 DK DK91914752T patent/DK0607128T4/da active
- 1991-08-19 AT AT91914752T patent/ATE158182T1/de not_active IP Right Cessation
- 1991-08-19 CA CA002087723A patent/CA2087723C/en not_active Expired - Fee Related
- 1991-08-19 DE DE59108854T patent/DE59108854D1/de not_active Expired - Fee Related
-
1993
- 1993-03-11 FI FI931097A patent/FI103180B1/fi active
-
1997
- 1997-11-26 GR GR970403151T patent/GR3025502T3/el unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4319438C1 (de) * | 1993-06-11 | 1994-06-01 | Gerd Dr Dr Geislinger | Arzneimittel auf der Grundlage von Ketoprofen zur Bekämpfung von Schmerzen und/oder Entzündungen und/oder Fieber an Menschen und Tieren |
| US8092829B2 (en) | 2000-09-25 | 2012-01-10 | Paz Arzneimittelentwicklungsgesellschaft Mbh | Use of R-arylpropionic acids for treating illnesses with a rheumatic nature |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1992004018A1 (de) | 1992-03-19 |
| DK0607128T3 (da) | 1998-04-14 |
| AU654498B2 (en) | 1994-11-10 |
| ES2106785T5 (es) | 2007-10-16 |
| DK0607128T4 (da) | 2007-05-07 |
| JP3305315B2 (ja) | 2002-07-22 |
| CA2087723C (en) | 2002-07-23 |
| HU9300636D0 (en) | 1993-05-28 |
| ATE158182T1 (de) | 1997-10-15 |
| CA2087723A1 (en) | 1992-03-13 |
| US5200198A (en) | 1993-04-06 |
| DE59108854D1 (de) | 1997-10-23 |
| FI931097A0 (fi) | 1993-03-11 |
| HU225887B1 (en) | 2007-11-28 |
| EP0607128B1 (de) | 1997-09-17 |
| RU2080116C1 (ru) | 1997-05-27 |
| FI931097L (fi) | 1993-03-11 |
| DE4028906A1 (de) | 1992-03-19 |
| EP0607128A1 (de) | 1994-07-27 |
| AU8335291A (en) | 1992-03-30 |
| HUT63564A (en) | 1993-09-28 |
| GR3025502T3 (en) | 1998-02-27 |
| US5206029A (en) | 1993-04-27 |
| FI103180B (fi) | 1999-05-14 |
| EP0607128B2 (de) | 2007-02-21 |
| JPH06500313A (ja) | 1994-01-13 |
| ES2106785T3 (es) | 1997-11-16 |
| FI103180B1 (fi) | 1999-05-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE4028906C2 (OSRAM) | ||
| DE69916922T2 (de) | Ibuprofenhaltige Arzneizubereitung | |
| DE3852481T2 (de) | Pharmazeutische zusammensetzungen, enthaltend s(+)ibuprofen, das in der hauptsache frei von seinem r(-)antipoden ist. | |
| DE69623634T2 (de) | Pharmazeutische zusammensetzung von l-dopa ethyl ester | |
| DE69109286T2 (de) | Pharmazeutische zusammensetzung. | |
| DE69006684T2 (de) | Verwendung einer Zusammensetzung zur Herstellung eines Arzneimittels zur Behandlung der Symptome der Unenthaltsamkeit. | |
| DE69309492T2 (de) | Antipyretische und analgetische zusammensetzungen, die optisch reines r-ketorolac enthalten | |
| EP0979087B1 (de) | Analgetika-kombination | |
| DE69933049T2 (de) | Pharmazeutische zusammensetzung und verwendung von rnsaid zur behandlung der entzündung | |
| DE4137540A1 (de) | Verwendung von praeparaten der curcuma-pflanzen | |
| DE2551280A1 (de) | L-dopa-zubereitung | |
| AT401468B (de) | Pharmazeutische zusammensetzungen mit einem gehalt an ranitidinwismutcitrat | |
| DE4201903B4 (de) | Pharmazeutische Verwendung von Boswelliasäuren | |
| WO2000059508A1 (de) | Tolperison enthaltende, pharmazeutische zubereitung zur oralen verabreichung | |
| DE69817379T2 (de) | Pharmazeutische zubereitungen enthaltend ibuprofen und domperidon zur behandlung von migräne | |
| LU84892A1 (fr) | Komposition zur reduktion der sebumsekretion | |
| DD238920A5 (de) | Verfahren zur herstellung einer verbesserten entzuendungshemmend wirkenden zusammensetzung | |
| DE4319438C1 (de) | Arzneimittel auf der Grundlage von Ketoprofen zur Bekämpfung von Schmerzen und/oder Entzündungen und/oder Fieber an Menschen und Tieren | |
| DE69332947T2 (de) | Arzneimittel enthaltend 2-(3-benzoylphenyl)-propionsäure zur verwendung als analgetikum | |
| CH667592A5 (de) | 9,10-dihydrogenierte ergotalkaloide enthaltende pharmazeutische zusammensetzungen. | |
| DE3843324A1 (de) | Neue verwendung von brenzkatechin-0-methyl-transferase (comt)-inhibitoren und ihre physiologisch annehmbaren salze und ester | |
| DD209735A5 (de) | Verfahren zur herstellung eines neuen arzneimittelpraeparates | |
| DE19849737A1 (de) | Kombinationsmittel zur Behandlung entzündlicher Darmerkrankungen | |
| DE3306299C2 (OSRAM) | ||
| EP0513400B1 (de) | Verwendung von 2-Ethoxybenzoesäure zur Herstellung eines Arzneimittels als Analgetikum, Antipyretikum und/oder Antiphlogistikum |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |