SE517006C2 - Farmaceutisk komposition med förbättrad analgetisk aktivitet innehållande (S)-2-(6-metoxi-2-naftyl)propionsyra (naproxen) och arginin - Google Patents

Farmaceutisk komposition med förbättrad analgetisk aktivitet innehållande (S)-2-(6-metoxi-2-naftyl)propionsyra (naproxen) och arginin

Info

Publication number: SE517006C2
Authority: SE; Sweden
Prior art keywords: naproxen; arginine; pharmaceutical composition; sodium; pharmaceutical
Prior art date: 1993-03-26

Application number

SE9401005A

Other languages

English (en)

Swedish (sv)

Other versions

SE9401005L (sv

SE9401005D0 (sv

Inventor

Federico Stroppolo

Daniele Bonadeo

Luigi Vigano

Annibale Gazzaniga

Original Assignee

Zambon Spa

Priority date (The priority date 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 date listed.)

1993-03-26

Filing date

1994-03-25

Publication date

2002-04-02

1994-03-25 Application filed by Zambon Spa filed Critical Zambon Spa

1994-03-25 Publication of SE9401005D0 publication Critical patent/SE9401005D0/xx

1994-09-27 Publication of SE9401005L publication Critical patent/SE9401005L/xx

2002-04-02 Publication of SE517006C2 publication Critical patent/SE517006C2/sv

Links

CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 title claims abstract description 67
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 title claims abstract description 66
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 27
239000004475 Arginine Substances 0.000 title claims abstract description 21
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 title claims abstract description 21
229960002009 naproxen Drugs 0.000 title claims description 65
230000000202 analgesic effect Effects 0.000 title abstract description 16
238000002360 preparation method Methods 0.000 claims abstract description 25
239000000203 mixture Substances 0.000 claims description 75
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 32
235000009697 arginine Nutrition 0.000 claims description 19
235000017557 sodium bicarbonate Nutrition 0.000 claims description 18
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 18
229930064664 L-arginine Natural products 0.000 claims description 14
235000014852 L-arginine Nutrition 0.000 claims description 14
239000000546 pharmaceutical excipient Substances 0.000 claims description 12
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 8
239000007864 aqueous solution Substances 0.000 claims description 8
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 7
238000009472 formulation Methods 0.000 claims description 6
239000011736 potassium bicarbonate Substances 0.000 claims description 4
229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 4
235000015497 potassium bicarbonate Nutrition 0.000 claims description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 4
LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
238000004090 dissolution Methods 0.000 claims 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 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
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 2
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 2
MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims description 2
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 claims description 2
235000019797 dipotassium phosphate Nutrition 0.000 claims description 2
229910000396 dipotassium phosphate Inorganic materials 0.000 claims description 2
229910000397 disodium phosphate Inorganic materials 0.000 claims description 2
235000019800 disodium phosphate Nutrition 0.000 claims description 2
229960002442 glucosamine Drugs 0.000 claims description 2
AVTYONGGKAJVTE-OLXYHTOASA-L potassium L-tartrate Chemical compound [K+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O AVTYONGGKAJVTE-OLXYHTOASA-L 0.000 claims description 2
229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
235000011181 potassium carbonates Nutrition 0.000 claims description 2
239000001472 potassium tartrate Substances 0.000 claims description 2
229940111695 potassium tartrate Drugs 0.000 claims description 2
235000011005 potassium tartrates Nutrition 0.000 claims description 2
235000015424 sodium Nutrition 0.000 claims description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
239000001488 sodium phosphate Substances 0.000 claims description 2
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 2
125000002059 L-arginyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])C(=N[H])N([H])[H] 0.000 claims 1
239000001508 potassium citrate Substances 0.000 claims 1
229960002635 potassium citrate Drugs 0.000 claims 1
QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 claims 1
235000011082 potassium citrates Nutrition 0.000 claims 1
229910052708 sodium Inorganic materials 0.000 claims 1
239000001433 sodium tartrate Substances 0.000 claims 1
229960002167 sodium tartrate Drugs 0.000 claims 1
235000011004 sodium tartrates Nutrition 0.000 claims 1
239000004480 active ingredient Substances 0.000 abstract description 11
238000011282 treatment Methods 0.000 description 26
239000000243 solution Substances 0.000 description 18
239000008187 granular material Substances 0.000 description 16
ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 13
230000036470 plasma concentration Effects 0.000 description 13
150000001483 arginine derivatives Chemical class 0.000 description 10
108010011485 Aspartame Proteins 0.000 description 8
239000000605 aspartame Substances 0.000 description 8
235000010357 aspartame Nutrition 0.000 description 8
IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 8
229960003438 aspartame Drugs 0.000 description 8
230000000977 initiatory effect Effects 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
WINXNKPZLFISPD-UHFFFAOYSA-M Saccharin sodium Chemical compound [Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 WINXNKPZLFISPD-UHFFFAOYSA-M 0.000 description 7
230000001133 acceleration Effects 0.000 description 7
230000002496 gastric effect Effects 0.000 description 7
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 6
239000008280 blood Substances 0.000 description 6
210000004369 blood Anatomy 0.000 description 6
239000007938 effervescent tablet Substances 0.000 description 6
238000004128 high performance liquid chromatography Methods 0.000 description 6
239000000843 powder Substances 0.000 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 description 5
229930006000 Sucrose Natural products 0.000 description 5
229960001680 ibuprofen Drugs 0.000 description 5
CDBRNDSHEYLDJV-FVGYRXGTSA-M naproxen sodium Chemical compound [Na+].C1=C([C@H](C)C([O-])=O)C=CC2=CC(OC)=CC=C21 CDBRNDSHEYLDJV-FVGYRXGTSA-M 0.000 description 5
230000003068 static effect Effects 0.000 description 5
239000005720 sucrose Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 4
239000000796 flavoring agent Substances 0.000 description 4
238000000034 method Methods 0.000 description 4
239000008368 mint flavor Substances 0.000 description 4
239000003826 tablet Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
230000003110 anti-inflammatory effect Effects 0.000 description 3
230000008030 elimination Effects 0.000 description 3
238000003379 elimination reaction Methods 0.000 description 3
235000019634 flavors Nutrition 0.000 description 3
229940079502 naproxen 500 mg Drugs 0.000 description 3
235000011007 phosphoric acid Nutrition 0.000 description 3
QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 3
239000012086 standard solution Substances 0.000 description 3
238000005303 weighing Methods 0.000 description 3
238000005550 wet granulation Methods 0.000 description 3
NTJPVVKEZMOHNU-UHFFFAOYSA-N 6-(oxan-4-yl)-1h-indazole Chemical compound C1COCCC1C1=CC=C(C=NN2)C2=C1 NTJPVVKEZMOHNU-UHFFFAOYSA-N 0.000 description 2
LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 2
235000007265 Myrrhis odorata Nutrition 0.000 description 2
240000004760 Pimpinella anisum Species 0.000 description 2
235000012550 Pimpinella anisum Nutrition 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
239000002253 acid Substances 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
229960001948 caffeine Drugs 0.000 description 2
VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
229960002390 flurbiprofen Drugs 0.000 description 2
SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 2
238000005469 granulation Methods 0.000 description 2
230000003179 granulation Effects 0.000 description 2
150000007529 inorganic bases Chemical class 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
230000014759 maintenance of location Effects 0.000 description 2
HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 2
235000019321 monosodium tartrate Nutrition 0.000 description 2
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
-1 polyethylene Polymers 0.000 description 2
229920000573 polyethylene Polymers 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
229940119126 sodium bitartrate Drugs 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
239000000811 xylitol Substances 0.000 description 2
235000010447 xylitol Nutrition 0.000 description 2
HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 2
229960002675 xylitol Drugs 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
201000004624 Dermatitis Diseases 0.000 description 1
244000060234 Gmelina philippensis Species 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
244000018633 Prunus armeniaca Species 0.000 description 1
235000009827 Prunus armeniaca Nutrition 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000005056 compaction Methods 0.000 description 1
238000007906 compression Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
235000020937 fasting conditions Nutrition 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
230000006870 function Effects 0.000 description 1
230000003394 haemopoietic effect Effects 0.000 description 1
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
230000003907 kidney function Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000003908 liver function Effects 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000012528 membrane Substances 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000000144 pharmacologic effect Effects 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
AKEKKCGPLHMFCI-UHFFFAOYSA-L potassium sodium hydrogen carbonate Chemical compound [Na+].[K+].OC([O-])=O.OC([O-])=O AKEKKCGPLHMFCI-UHFFFAOYSA-L 0.000 description 1
MCXBMLBTPQEQJP-UHFFFAOYSA-N potassium;sodium;dinitrate Chemical compound [Na+].[K+].[O-][N+]([O-])=O.[O-][N+]([O-])=O MCXBMLBTPQEQJP-UHFFFAOYSA-N 0.000 description 1
239000000523 sample Substances 0.000 description 1
239000012488 sample solution Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Inorganic materials [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
230000003637 steroidlike Effects 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000000825 ultraviolet detection Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- 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
- A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/02—Inorganic compounds
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0002—Galenical forms characterised by the drug release technique; Application systems commanded by energy
- A61K9/0007—Effervescent
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1611—Inorganic compounds
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
- 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]

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Epidemiology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
Inorganic Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Molecular Biology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Organic Chemistry (AREA)
Biophysics (AREA)
Pain & Pain Management (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Oil, Petroleum & Natural Gas (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Rheumatology (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SE9401005A 1993-03-26 1994-03-25 Farmaceutisk komposition med förbättrad analgetisk aktivitet innehållande (S)-2-(6-metoxi-2-naftyl)propionsyra (naproxen) och arginin SE517006C2 (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
ITMI930582A IT1272149B (it)	1993-03-26	1993-03-26	Composizione farmeceutiche ad attivita' analgesica

Publications (3)

Publication Number	Publication Date
SE9401005D0 SE9401005D0 (sv)	1994-03-25
SE9401005L SE9401005L (sv)	1994-09-27
SE517006C2 true SE517006C2 (sv)	2002-04-02

Family

ID=11365508

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE9401005A SE517006C2 (sv)	1993-03-26	1994-03-25	Farmaceutisk komposition med förbättrad analgetisk aktivitet innehållande (S)-2-(6-metoxi-2-naftyl)propionsyra (naproxen) och arginin

Country Status (12)

Country	Link
US (1)	US5693312A (it)
JP (1)	JP3784843B2 (it)
BE (1)	BE1006718A3 (it)
CA (1)	CA2120048C (it)
CH (1)	CH686403A5 (it)
DE (1)	DE4410470A1 (it)
ES (1)	ES2109131B1 (it)
FR (1)	FR2703249B1 (it)
GB (1)	GB2276545B (it)
IT (1)	IT1272149B (it)
NL (1)	NL194390C (it)
SE (1)	SE517006C2 (it)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
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IT1301966B1 (it)	1998-07-30	2000-07-20	Zambon Spa	Composizioni farmaceutiche ad attivita' analgesica
GB9924636D0 (en) *	1999-10-18	1999-12-22	Norgine Bv	Laxative preparation
US20030235629A1 (en) *	1999-11-06	2003-12-25	Janmarie Hornack	Dietary supplement containing alkaline electrolyte buffers
JP5185488B2 (ja) *	2001-11-02	2013-04-17	カンバーランドファーマシューティカルズ，インコーポレーテッド	２−（４−イソブチルフェニル）プロピオン酸の医薬組成物
US6727286B2 (en)	2001-11-02	2004-04-27	Cumberland Pharmaceuticals Inc.	Pharmaceutical composition of 2-(4-isobutylphenyl) propionic acid
WO2004089365A1 (en) *	2003-04-11	2004-10-21	Pfizer Limited	Pharmaceutical combination comprising eletriptan and sodium bicarbonate
US20050008699A1 (en) *	2003-07-11	2005-01-13	Fred Wehling	Effervescent glucosamine composition
UY28583A1 (es) *	2003-10-30	2005-05-31	Roche Consumer Health Ag	Forma de presentación del naproxeno sodico
US20050137262A1 (en) *	2003-12-22	2005-06-23	Hu Patrick C.	Highly concentrated pourable aqueous solutions of potassium ibuprofen, their preparation and their uses
ATE489077T1 (de)	2006-09-28	2010-12-15	Losan Pharma Gmbh	Schnell lösliche formulierung von nichtsteroidalen antiphlogistika
EP2155214A1 (en) *	2007-05-22	2010-02-24	Glenn Abrahmsohn	Method for pain control
US8828452B2 (en) *	2007-05-22	2014-09-09	Glenn Abrahmsohn	Method for pain control
BRPI0800951A2 (pt) *	2008-04-09	2012-02-22	Ems Sa	novos compostos derivados de taurina e seus usos, processo de sua preparação e composições farmacêuticas contendo os mesmos
JP7163015B2 (ja) *	2016-10-31	2022-10-31	エスエス製薬株式会社	経口固形組成物
JP7163014B2 (ja) *	2016-10-31	2022-10-31	エスエス製薬株式会社	感冒薬
US11779541B2 (en)	2019-03-26	2023-10-10	Johnson & Johnson Consumer Inc.	Immediate release dosage form

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3904682A (en) *	1967-01-13	1975-09-09	Syntex Corp	2-(6{40 -Methoxy-2{40 -naphthyl)acetic acid
GB1497044A (en) *	1974-03-07	1978-01-05	Prodotti Antibiotici Spa	Salts of phenyl-alkanoic acids
US4344929A (en) *	1980-04-25	1982-08-17	Alza Corporation	Method of delivering drug with aid of effervescent activity generated in environment of use
US4587249A (en) *	1982-07-22	1986-05-06	Analgesic Associates	Analgesic and anti-inflammatory compositions comprising caffeine and methods of using same
US5053396A (en) *	1985-08-27	1991-10-01	Blass David H	Therapeutic composition
IT1209667B (it) *	1985-11-12	1989-08-30	Zambon Spa	Composizione effeverscente adattivita' analgesica.
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.
IT1197038B (it) *	1986-08-01	1988-11-25	Zambon Spa	Composizione farmaceutica ad attivita' analgesica
SE463541B (sv) *	1987-08-31	1990-12-10	Lejus Medical Ab	Granulaer produkt oeverdragen av en smaelta av sig sjaelv samt foerfarande foer dess framstaellning
GB8724763D0 (en) *	1987-10-22	1987-11-25	Aps Research Ltd	Sustained-release formulations
GB8813682D0 (en) *	1988-06-09	1988-07-13	Reckitt & Colmann Prod Ltd	Pharmaceutical compositions
KR920700613A (ko) *	1989-05-16	1992-08-10	지구르트 퓌터	약제제
US5262179A (en) *	1989-09-13	1993-11-16	Nicholas Kiwi Pty Ltd.	Non-effervescent ibuprofen compositions
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
HUT59692A (en) *	1990-11-15	1992-06-29	Puetter Medice Chem Pharm	Process for producing complexes containing s/+/-phenyl-alkanoic acids and aminosugars

1993
- 1993-03-26 IT ITMI930582A patent/IT1272149B/it active IP Right Grant
1994
- 1994-03-10 CH CH71194A patent/CH686403A5/it not_active IP Right Cessation
- 1994-03-15 FR FR9402977A patent/FR2703249B1/fr not_active Expired - Fee Related
- 1994-03-17 BE BE9400290A patent/BE1006718A3/fr not_active IP Right Cessation
- 1994-03-18 GB GB9405420A patent/GB2276545B/en not_active Expired - Fee Related
- 1994-03-25 DE DE4410470A patent/DE4410470A1/de not_active Withdrawn
- 1994-03-25 ES ES09400644A patent/ES2109131B1/es not_active Expired - Fee Related
- 1994-03-25 NL NL9400481A patent/NL194390C/nl not_active IP Right Cessation
- 1994-03-25 CA CA002120048A patent/CA2120048C/en not_active Expired - Fee Related
- 1994-03-25 SE SE9401005A patent/SE517006C2/sv not_active IP Right Cessation
- 1994-03-25 JP JP05571694A patent/JP3784843B2/ja not_active Expired - Fee Related
1995
- 1995-06-06 US US08/470,143 patent/US5693312A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
GB9405420D0 (en)	1994-05-04
IT1272149B (it)	1997-06-11
NL194390C (nl)	2002-03-04
ITMI930582A0 (it)	1993-03-26
BE1006718A3 (fr)	1994-11-22
GB2276545B (en)	1996-08-14
NL194390B (nl)	2001-11-01
US5693312A (en)	1997-12-02
FR2703249B1 (fr)	1995-07-13
DE4410470A1 (de)	1994-09-29
SE9401005L (sv)	1994-09-27
SE9401005D0 (sv)	1994-03-25
JPH06321777A (ja)	1994-11-22
NL9400481A (nl)	1994-10-17
GB2276545A (en)	1994-10-05
CA2120048A1 (en)	1994-09-27
ES2109131A1 (es)	1998-01-01
ES2109131B1 (es)	1998-08-16
JP3784843B2 (ja)	2006-06-14
FR2703249A1 (fr)	1994-10-07
CA2120048C (en)	2004-01-27
ITMI930582A1 (it)	1994-09-26
CH686403A5 (it)	1996-03-29

Legal Events

Date	Code	Title	Description
2009-11-17	NUG	Patent has lapsed

Publication	Publication Date	Title
US4834966A (en)	1989-05-30	Pharmaceutical composition with analgesic activity
NL193307C (nl)	1999-06-02	Bruispreparaat met analgetische werkzaamheid.
EP1086706B1 (en)	2003-11-26	Stabilized compositions containing nootropic drugs
EP3111929B1 (en)	2018-08-29	Oral disintegrating film formulation containing tadalafil and preparation method therefor
JP3784843B2 (ja)	2006-06-14	鎮痛作用を有する薬剤組成物
KR20210090179A (ko)	2021-07-19	경구 약제학적 제형용 공융용매 플랫폼
JPH072700A (ja)	1995-01-06	ジヒドロピリジンの飲料の形態の経口投与用製薬学的組成物
NL193820C (nl)	2000-12-04	Vaste farmaceutische doseringsvorm voor orale toediening van Ibuprofen.
JP3110794B2 (ja)	2000-11-20	１，４−ジヒドロピリジン誘導体を含有する製剤
EP1495759A1 (en)	2005-01-12	Solid dispersion composition
US12042491B1 (en)	2024-07-23	Pharmaceutical formulations of quinolines
JP2003055254A (ja)	2003-02-26	経口投与用シクロスポリン製剤
JP2001122779A (ja)	2001-05-08	経口投与用シクロスポリン含有ミクロエマルジョン濃縮液
JP3091913B2 (ja)	2000-09-25	光安定化したユビデカレノン含有組成物及びその製造方法
KR19980073629A (ko)	1998-11-05	투명액상 이부프로펜 조성물 및 이를 함유하는 연질캅셀제
JPH02268117A (ja)	1990-11-01	溶出性の改善された難溶性薬物製剤組成物
KR100398713B1 (ko)	2004-02-05	비페닐디메칠디카르복실레이트(ddb)제제
JP2002037745A (ja)	2002-02-06	水溶性の難・低吸収性薬物のバイオアベイラビリティ改善技術
KR100986531B1 (ko)	2010-10-07	액상의 아세클로페낙을 함유하는 캡슐제
JPH07100654B2 (ja)	1995-11-01	ジピリダモ−ルの易溶性固形製剤
GB2355406A (en)	2001-04-25	A sub-lingual dosage form comprising a morphine salt
HK1219424B (en)	2019-08-02	Oral disintegrating film formulation containing tadalafil and preparation method therefor