HUT59692A - Process for producing complexes containing s/+/-phenyl-alkanoic acids and aminosugars - Google Patents
Process for producing complexes containing s/+/-phenyl-alkanoic acids and aminosugars Download PDFInfo
- Publication number
- HUT59692A HUT59692A HU913572A HU357291A HUT59692A HU T59692 A HUT59692 A HU T59692A HU 913572 A HU913572 A HU 913572A HU 357291 A HU357291 A HU 357291A HU T59692 A HUT59692 A HU T59692A
- Authority
- HU
- Hungary
- Prior art keywords
- complex
- amino sugar
- ibuprofen
- solution
- amino
- Prior art date
Links
- 150000002337 glycosamines Chemical class 0.000 title claims description 28
- 239000002253 acid Substances 0.000 title claims description 27
- 150000007513 acids Chemical class 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 28
- 239000000243 solution Substances 0.000 claims description 23
- -1 altrosamine Chemical compound 0.000 claims description 21
- HEFNNWSXXWATRW-JTQLQIEISA-N dexibuprofen Chemical compound CC(C)CC1=CC=C([C@H](C)C(O)=O)C=C1 HEFNNWSXXWATRW-JTQLQIEISA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 238000010668 complexation reaction Methods 0.000 claims description 6
- 229960001680 ibuprofen Drugs 0.000 claims description 6
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims description 5
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 5
- 230000000845 anti-microbial effect Effects 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000011521 glass Substances 0.000 claims description 5
- 229960002009 naproxen Drugs 0.000 claims description 5
- 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 claims description 5
- 239000002244 precipitate Substances 0.000 claims description 5
- MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 claims description 4
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000001754 anti-pyretic effect Effects 0.000 claims description 4
- 239000002221 antipyretic Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 239000000730 antalgic agent Substances 0.000 claims description 3
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 3
- 239000004599 antimicrobial Substances 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000007911 parenteral administration Methods 0.000 claims description 3
- 238000011200 topical administration Methods 0.000 claims description 3
- IKXCHOUDIPZROZ-LXGUWJNJSA-N (2r,3r,4r,5s)-6-(ethylamino)hexane-1,2,3,4,5-pentol Chemical compound CCNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO IKXCHOUDIPZROZ-LXGUWJNJSA-N 0.000 claims description 2
- RNZJRDIKDNXKIJ-LMVFSUKVSA-N (2r,3s,4r)-2-amino-3,4,5-trihydroxypentanal Chemical compound O=C[C@H](N)[C@H](O)[C@H](O)CO RNZJRDIKDNXKIJ-LMVFSUKVSA-N 0.000 claims description 2
- RNHXWPCUJTZBAR-LMVFSUKVSA-N (2r,3s,4s)-5-aminopentane-1,2,3,4-tetrol Chemical compound NC[C@H](O)[C@H](O)[C@H](O)CO RNHXWPCUJTZBAR-LMVFSUKVSA-N 0.000 claims description 2
- MSWZFWKMSRAUBD-QTVWNMPRSA-N (3r,4s,5r,6r)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@H]1O MSWZFWKMSRAUBD-QTVWNMPRSA-N 0.000 claims description 2
- MSWZFWKMSRAUBD-RSVSWTKNSA-N (3r,4s,5s,6r)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@H]1O MSWZFWKMSRAUBD-RSVSWTKNSA-N 0.000 claims description 2
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims description 2
- MSWZFWKMSRAUBD-CBPJZXOFSA-N 2-amino-2-deoxy-D-mannopyranose Chemical compound N[C@@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-CBPJZXOFSA-N 0.000 claims description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 230000000202 analgesic effect Effects 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229960002442 glucosamine Drugs 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000008273 hexosamines Chemical class 0.000 claims description 2
- 150000002401 hexose derivatives Chemical class 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 239000012452 mother liquor Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 150000008278 pentosamines Chemical class 0.000 claims description 2
- 125000001805 pentosyl group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 238000007710 freezing Methods 0.000 claims 2
- 230000008014 freezing Effects 0.000 claims 2
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims 1
- 235000008206 alpha-amino acids Nutrition 0.000 claims 1
- 230000036760 body temperature Effects 0.000 claims 1
- 238000009792 diffusion process Methods 0.000 claims 1
- 238000006073 displacement reaction Methods 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims 1
- 230000003204 osmotic effect Effects 0.000 claims 1
- 239000005518 polymer electrolyte Substances 0.000 claims 1
- 239000006104 solid solution Substances 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 208000002193 Pain Diseases 0.000 description 7
- 230000000699 topical effect Effects 0.000 description 7
- 238000009472 formulation Methods 0.000 description 6
- 230000036407 pain Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 235000000346 sugar Nutrition 0.000 description 5
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- HEFNNWSXXWATRW-SNVBAGLBSA-N levibuprofen Chemical compound CC(C)CC1=CC=C([C@@H](C)C(O)=O)C=C1 HEFNNWSXXWATRW-SNVBAGLBSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- SDOFMBGMRVAJNF-SLPGGIOYSA-N (2r,3r,4r,5s)-6-aminohexane-1,2,3,4,5-pentol Chemical compound NC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO SDOFMBGMRVAJNF-SLPGGIOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 208000025747 Rheumatic disease Diseases 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 239000008187 granular material Substances 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
- 150000002500 ions Chemical class 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 230000000552 rheumatic effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- CBOJBBMQJBVCMW-BTVCFUMJSA-N (2r,3r,4s,5r)-2-amino-3,4,5,6-tetrahydroxyhexanal;hydrochloride Chemical compound Cl.O=C[C@H](N)[C@@H](O)[C@H](O)[C@H](O)CO CBOJBBMQJBVCMW-BTVCFUMJSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920002785 Croscarmellose sodium Polymers 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 208000019255 Menstrual disease Diseases 0.000 description 1
- 206010036030 Polyarthritis Diseases 0.000 description 1
- 208000004550 Postoperative Pain Diseases 0.000 description 1
- 238000001069 Raman spectroscopy Methods 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 208000005298 acute pain Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- MSWZFWKMSRAUBD-DVKNGEFBSA-N alpha-D-galactosamine Chemical compound N[C@H]1[C@@H](O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-DVKNGEFBSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000002266 amputation Methods 0.000 description 1
- 230000003324 anti-retinal effect Effects 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000008033 biological extinction Effects 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
- 229960001631 carbomer Drugs 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 description 1
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229960001911 glucosamine hydrochloride Drugs 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229940082151 ibuprofen 100 mg Drugs 0.000 description 1
- 239000005414 inactive ingredient Substances 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229960005285 mofebutazone Drugs 0.000 description 1
- REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical compound O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7004—Monosaccharides having only carbon, hydrogen and oxygen atoms
-
- 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
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/12—Acyclic radicals, not substituted by cyclic structures attached to a nitrogen atom of the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
- C07H5/06—Aminosugars
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Crystallography & Structural Chemistry (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Rheumatology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4036460 | 1990-11-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HU913572D0 HU913572D0 (en) | 1992-01-28 |
| HUT59692A true HUT59692A (en) | 1992-06-29 |
Family
ID=6418341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU913572A HUT59692A (en) | 1990-11-15 | 1991-11-14 | Process for producing complexes containing s/+/-phenyl-alkanoic acids and aminosugars |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5604206A (OSRAM) |
| EP (1) | EP0486046B1 (OSRAM) |
| JP (1) | JP2542765B2 (OSRAM) |
| KR (1) | KR920009838A (OSRAM) |
| CN (1) | CN1061415A (OSRAM) |
| AT (1) | ATE137486T1 (OSRAM) |
| AU (1) | AU642309B2 (OSRAM) |
| BG (1) | BG95489A (OSRAM) |
| BR (1) | BR9104997A (OSRAM) |
| CA (1) | CA2055681A1 (OSRAM) |
| CS (1) | CS346591A3 (OSRAM) |
| DE (2) | DE4137683A1 (OSRAM) |
| HU (1) | HUT59692A (OSRAM) |
| MX (1) | MX9102086A (OSRAM) |
| NZ (1) | NZ240616A (OSRAM) |
| PL (1) | PL292415A1 (OSRAM) |
| ZA (1) | ZA919075B (OSRAM) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUT59653A (en) * | 1990-11-15 | 1992-06-29 | Puetter Medice Chem Pharm | Process for producing complexes containing s/+/-phenyl-alcanoic acids and alpha-hydroxy-alcanoic acids and pharmaceutical compositions containing them as active components |
| EP0577725A4 (en) * | 1991-03-29 | 1996-04-17 | Univ Florida | Targeted drug delivery via mixed phosphate derivatives |
| WO1994012460A1 (en) * | 1992-12-02 | 1994-06-09 | The Boots Company Plc | Process for preparing substantially pure enantiomers of phenylpropionic acids |
| IT1272149B (it) * | 1993-03-26 | 1997-06-11 | Zambon Spa | Composizione farmeceutiche ad attivita' analgesica |
| US6399093B1 (en) | 1999-05-19 | 2002-06-04 | Advanced Medical Instruments | Method and composition to treat musculoskeletal disorders |
| EP1328278A4 (en) | 2000-09-26 | 2004-06-16 | Univ Temple | GLUCOSAMINE ANALGESIC AND COMPOSITIONS |
| GB0201400D0 (en) * | 2002-01-22 | 2002-03-13 | Glaxo Group Ltd | Novel apparatus and process |
| IL152397A (en) * | 2002-10-21 | 2009-02-11 | Hadasit Med Res Service | Compositions and compounds for the treatment of hyperglycemia |
| US7662803B2 (en) * | 2004-09-17 | 2010-02-16 | Gluconova, LLC | Method for treating warm-blooded vertebrates with halide-free glucosamine-acidic drug complexes |
| US20070259043A1 (en) * | 2004-09-17 | 2007-11-08 | Jame Fine Chemicals, Inc. | Halide-free glucosamine-therapeutic drug salt compositions |
| US7662802B2 (en) * | 2004-09-17 | 2010-02-16 | Gluconova, LLC | Halide-free glucosamine-acidic drug complexes |
| CN1300159C (zh) * | 2005-02-24 | 2007-02-14 | 华东理工大学 | 一种布洛芬糖衍生物及其制备方法和应用 |
| US20070237816A1 (en) * | 2006-04-06 | 2007-10-11 | David Finkelstein | Acetaminophen formulation for joint pain relief |
| EP2190853A4 (en) * | 2007-06-22 | 2011-08-31 | Gluconova Llc | HALOGENIDE-FREE COMPLEXES FROM GLUCOSAMINE AND AN ACIDIC ACID |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2103387C3 (de) * | 1971-01-26 | 1982-05-06 | Johann G.W. Opfermann & Sohn, 5070 Bergisch-Gladbach | Verwendung des Hydrochlorids von Glukosamin zur Herstellung von pharmazeutischen Präparaten |
| LU83138A1 (de) * | 1981-02-16 | 1981-09-11 | T Eckert | Topische pharmazeutische praeparate,enthaltend salze von alkancarbonsaeuren sowie neue carbonsaeuresalze und verfahren zu ihrer herstellung |
| ZA828453B (en) * | 1981-12-08 | 1983-12-28 | Boots Co Plc | Therapeutic agents |
| IT1207994B (it) * | 1986-01-03 | 1989-06-01 | Therapicon Srl | Sali idrosulubili di composti adattivita' antiinfiammatoria ed analgesica, loro preparazione ed utilizzo in composizioni farmaceutiche. |
| DE3669103D1 (de) * | 1986-11-14 | 1990-04-05 | Puetter Medice Chem Pharm | Ibuprofen enthaltendes arzneimittel. |
| US4800162A (en) * | 1987-04-01 | 1989-01-24 | Sepracor, Inc. | Method for resolution of steroisomers in multiphase and extractive membrane reactors |
| US4851444A (en) * | 1987-07-10 | 1989-07-25 | Analgesic Associates | Onset-hastened/enhanced analgesia |
| US5380927A (en) * | 1989-05-16 | 1995-01-10 | Medice Chem.-Pharm. Fabrik Putter Gmbh & Co. Kg | Process for preparing optically active 2-aryl-alkanoic acids, in particular 2-aryl-propionic acids |
| HUT59656A (en) * | 1990-11-15 | 1992-06-29 | Puetter Medice Chem Pharm | Process for producing s/+/-phenyl-alkanoic acids and alpha-amino-acids containing complexes and pharmaceutical compositions containing them as active components |
| HUT59653A (en) * | 1990-11-15 | 1992-06-29 | Puetter Medice Chem Pharm | Process for producing complexes containing s/+/-phenyl-alcanoic acids and alpha-hydroxy-alcanoic acids and pharmaceutical compositions containing them as active components |
-
1991
- 1991-11-14 HU HU913572A patent/HUT59692A/hu unknown
- 1991-11-15 DE DE4137683A patent/DE4137683A1/de not_active Withdrawn
- 1991-11-15 BG BG095489A patent/BG95489A/bg unknown
- 1991-11-15 CN CN91110740A patent/CN1061415A/zh active Pending
- 1991-11-15 CA CA002055681A patent/CA2055681A1/en not_active Abandoned
- 1991-11-15 PL PL29241591A patent/PL292415A1/xx unknown
- 1991-11-15 EP EP91119523A patent/EP0486046B1/de not_active Expired - Lifetime
- 1991-11-15 CS CS913465A patent/CS346591A3/cs unknown
- 1991-11-15 AT AT91119523T patent/ATE137486T1/de active
- 1991-11-15 MX MX9102086A patent/MX9102086A/es unknown
- 1991-11-15 DE DE59107759T patent/DE59107759D1/de not_active Expired - Fee Related
- 1991-11-15 KR KR1019910020370A patent/KR920009838A/ko not_active Withdrawn
- 1991-11-15 AU AU87904/91A patent/AU642309B2/en not_active Ceased
- 1991-11-15 JP JP3354100A patent/JP2542765B2/ja not_active Expired - Lifetime
- 1991-11-15 NZ NZ240616A patent/NZ240616A/en unknown
- 1991-11-15 ZA ZA919075A patent/ZA919075B/xx unknown
- 1991-11-18 BR BR919104997A patent/BR9104997A/pt not_active Application Discontinuation
-
1994
- 1994-02-18 US US08/328,722 patent/US5604206A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CS346591A3 (en) | 1992-06-17 |
| BG95489A (bg) | 1993-12-24 |
| DE59107759D1 (de) | 1996-06-05 |
| EP0486046A2 (de) | 1992-05-20 |
| DE4137683A1 (de) | 1992-05-21 |
| CN1061415A (zh) | 1992-05-27 |
| NZ240616A (en) | 1993-10-26 |
| AU642309B2 (en) | 1993-10-14 |
| ZA919075B (en) | 1992-08-26 |
| MX9102086A (es) | 1993-01-01 |
| CA2055681A1 (en) | 1992-05-16 |
| JP2542765B2 (ja) | 1996-10-09 |
| HU913572D0 (en) | 1992-01-28 |
| EP0486046B1 (de) | 1996-05-01 |
| EP0486046A3 (en) | 1992-12-09 |
| PL292415A1 (OSRAM) | 1993-02-08 |
| US5604206A (en) | 1997-02-18 |
| AU8790491A (en) | 1992-05-21 |
| BR9104997A (pt) | 1992-06-23 |
| KR920009838A (ko) | 1992-06-25 |
| JPH06184003A (ja) | 1994-07-05 |
| ATE137486T1 (de) | 1996-05-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| DFC9 | Refusal of application |