CA1070299A - Stabilized solid form choline salicylate compositions - Google Patents
Stabilized solid form choline salicylate compositionsInfo
- Publication number
- CA1070299A CA1070299A CA260,766A CA260766A CA1070299A CA 1070299 A CA1070299 A CA 1070299A CA 260766 A CA260766 A CA 260766A CA 1070299 A CA1070299 A CA 1070299A
- Authority
- CA
- Canada
- Prior art keywords
- salicylate
- choline
- carboxy
- choline salicylate
- metal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229960002688 choline salicylate Drugs 0.000 title claims abstract description 84
- UDKCHVLMFQVBAA-UHFFFAOYSA-M Choline salicylate Chemical compound C[N+](C)(C)CCO.OC1=CC=CC=C1C([O-])=O UDKCHVLMFQVBAA-UHFFFAOYSA-M 0.000 title claims abstract description 81
- 239000000203 mixture Substances 0.000 title claims abstract description 60
- 239000007787 solid Substances 0.000 title abstract description 29
- 239000001768 carboxy methyl cellulose Substances 0.000 claims abstract description 66
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims abstract description 65
- 229940105329 carboxymethylcellulose Drugs 0.000 claims abstract description 65
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims abstract description 57
- 229910052751 metal Inorganic materials 0.000 claims abstract description 21
- 239000002184 metal Substances 0.000 claims abstract description 21
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims abstract description 19
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 18
- 229960001860 salicylate Drugs 0.000 claims abstract description 17
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000011575 calcium Substances 0.000 claims abstract description 12
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 11
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 10
- 229910052797 bismuth Inorganic materials 0.000 claims abstract description 9
- 238000001035 drying Methods 0.000 claims abstract description 3
- 239000000243 solution Substances 0.000 claims description 29
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 22
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 20
- 229910021645 metal ion Inorganic materials 0.000 claims description 18
- 229960001231 choline Drugs 0.000 claims description 13
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 229920013820 alkyl cellulose Polymers 0.000 claims description 10
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 10
- 229960004889 salicylic acid Drugs 0.000 claims description 10
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 9
- DQKGOGJIOHUEGK-UHFFFAOYSA-M hydron;2-hydroxyethyl(trimethyl)azanium;carbonate Chemical compound OC([O-])=O.C[N+](C)(C)CCO DQKGOGJIOHUEGK-UHFFFAOYSA-M 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 239000011777 magnesium Substances 0.000 claims description 7
- 229910052749 magnesium Inorganic materials 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- RVDLHGSZWAELAU-UHFFFAOYSA-N 5-tert-butylthiophene-2-carbonyl chloride Chemical compound CC(C)(C)C1=CC=C(C(Cl)=O)S1 RVDLHGSZWAELAU-UHFFFAOYSA-N 0.000 claims description 4
- KKMOSYLWYLMHAL-UHFFFAOYSA-N 2-bromo-6-nitroaniline Chemical compound NC1=C(Br)C=CC=C1[N+]([O-])=O KKMOSYLWYLMHAL-UHFFFAOYSA-N 0.000 claims description 3
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 3
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims description 3
- SFOQXWSZZPWNCL-UHFFFAOYSA-K bismuth;phosphate Chemical compound [Bi+3].[O-]P([O-])([O-])=O SFOQXWSZZPWNCL-UHFFFAOYSA-K 0.000 claims description 3
- NKWPZUCBCARRDP-UHFFFAOYSA-L calcium bicarbonate Chemical compound [Ca+2].OC([O-])=O.OC([O-])=O NKWPZUCBCARRDP-UHFFFAOYSA-L 0.000 claims description 3
- 229910000020 calcium bicarbonate Inorganic materials 0.000 claims description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 3
- 239000000920 calcium hydroxide Substances 0.000 claims description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 3
- 239000000347 magnesium hydroxide Substances 0.000 claims description 3
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 3
- 239000008247 solid mixture Substances 0.000 claims description 3
- 229940049676 bismuth hydroxide Drugs 0.000 claims description 2
- TZSXPYWRDWEXHG-UHFFFAOYSA-K bismuth;trihydroxide Chemical compound [OH-].[OH-].[OH-].[Bi+3] TZSXPYWRDWEXHG-UHFFFAOYSA-K 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims 1
- 235000010980 cellulose Nutrition 0.000 claims 1
- 229940106135 cellulose Drugs 0.000 claims 1
- MQHWFIOJQSCFNM-UHFFFAOYSA-L Magnesium salicylate Chemical compound [Mg+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O MQHWFIOJQSCFNM-UHFFFAOYSA-L 0.000 abstract description 10
- 229940072082 magnesium salicylate Drugs 0.000 abstract description 10
- 239000002775 capsule Substances 0.000 abstract description 6
- 239000007909 solid dosage form Substances 0.000 abstract description 6
- 239000003826 tablet Substances 0.000 abstract description 6
- 241001465754 Metazoa Species 0.000 abstract description 4
- 239000008187 granular material Substances 0.000 abstract description 4
- 230000000536 complexating effect Effects 0.000 abstract description 3
- 238000002560 therapeutic procedure Methods 0.000 abstract description 2
- 230000036765 blood level Effects 0.000 abstract 1
- 238000009740 moulding (composite fabrication) Methods 0.000 abstract 1
- 230000006641 stabilisation Effects 0.000 abstract 1
- 238000011105 stabilization Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 35
- 239000000843 powder Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- -1 as for example Chemical compound 0.000 description 16
- 238000003756 stirring Methods 0.000 description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- 150000001455 metallic ions Chemical class 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229910001451 bismuth ion Inorganic materials 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- 238000005755 formation reaction Methods 0.000 description 5
- 229910001425 magnesium ion Inorganic materials 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000000829 suppository Substances 0.000 description 5
- GQSZLMMXKNYCTP-UHFFFAOYSA-K aluminum;2-carboxyphenolate Chemical compound [Al+3].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O GQSZLMMXKNYCTP-UHFFFAOYSA-K 0.000 description 4
- 229910001424 calcium ion Inorganic materials 0.000 description 4
- 125000004181 carboxyalkyl group Chemical group 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 229910001414 potassium ion Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 229910001415 sodium ion Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 2
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 229940024545 aluminum hydroxide Drugs 0.000 description 2
- REKWPXFKNZERAA-UHFFFAOYSA-K bismuth;2-carboxyphenolate Chemical compound [Bi+3].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O REKWPXFKNZERAA-UHFFFAOYSA-K 0.000 description 2
- AVVIDTZRJBSXML-UHFFFAOYSA-L calcium;2-carboxyphenolate;dihydrate Chemical compound O.O.[Ca+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O AVVIDTZRJBSXML-UHFFFAOYSA-L 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 229960002900 methylcellulose Drugs 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- ZZJFIXMCLZTHQV-UHFFFAOYSA-O 2-carboxyoxyethyl(trimethyl)azanium Chemical compound C[N+](C)(C)CCOC(O)=O ZZJFIXMCLZTHQV-UHFFFAOYSA-O 0.000 description 1
- WQIAKSRYDHIZDB-UHFFFAOYSA-N 2-hydroxybenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1O WQIAKSRYDHIZDB-UHFFFAOYSA-N 0.000 description 1
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 1
- 235000019743 Choline chloride Nutrition 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- 229920002230 Pectic acid Polymers 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- 241000011102 Thera Species 0.000 description 1
- GABGQSDEEYHFNK-UHFFFAOYSA-O [Ca+2].C[N+](C)(C)CCOC(=O)C1=CC=CC=C1O Chemical compound [Ca+2].C[N+](C)(C)CCOC(=O)C1=CC=CC=C1O GABGQSDEEYHFNK-UHFFFAOYSA-O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- 150000001621 bismuth Chemical class 0.000 description 1
- JHXKRIRFYBPWGE-UHFFFAOYSA-K bismuth chloride Chemical compound Cl[Bi](Cl)Cl JHXKRIRFYBPWGE-UHFFFAOYSA-K 0.000 description 1
- 150000001622 bismuth compounds Chemical class 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229960004424 carbon dioxide Drugs 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229960003178 choline chloride Drugs 0.000 description 1
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000007580 dry-mixing Methods 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 229960004667 ethyl cellulose Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000010318 polygalacturonic acid Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000011240 wet gel Substances 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
- A61K31/60—Salicylic acid; Derivatives thereof
- A61K31/618—Salicylic acid; Derivatives thereof having the carboxyl group in position 1 esterified, e.g. salsalate
- A61K31/621—Salicylic acid; Derivatives thereof having the carboxyl group in position 1 esterified, e.g. salsalate having the hydroxy group in position 2 esterified, e.g. benorylate
-
- 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
- A61K31/60—Salicylic acid; Derivatives thereof
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65111076A | 1976-01-21 | 1976-01-21 | |
| US05/705,056 US4067974A (en) | 1976-01-21 | 1976-07-14 | Stabilized solid form choline salicylate compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1070299A true CA1070299A (en) | 1980-01-22 |
Family
ID=27096002
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA260,766A Expired CA1070299A (en) | 1976-01-21 | 1976-09-08 | Stabilized solid form choline salicylate compositions |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS6051449B2 (en, 2012) |
| AR (1) | AR217249A1 (en, 2012) |
| AU (1) | AU511510B2 (en, 2012) |
| CA (1) | CA1070299A (en, 2012) |
| CH (1) | CH635816A5 (en, 2012) |
| DD (1) | DD128908A5 (en, 2012) |
| DE (2) | DE2760284C2 (en, 2012) |
| DK (1) | DK149804C (en, 2012) |
| EG (1) | EG12511A (en, 2012) |
| ES (1) | ES454712A1 (en, 2012) |
| FI (1) | FI56770C (en, 2012) |
| FR (1) | FR2338705A1 (en, 2012) |
| GB (2) | GB1575977A (en, 2012) |
| GR (1) | GR62110B (en, 2012) |
| HU (1) | HU175973B (en, 2012) |
| IL (1) | IL50992A (en, 2012) |
| MX (1) | MX5920E (en, 2012) |
| NL (1) | NL183821C (en, 2012) |
| NO (1) | NO145295C (en, 2012) |
| NZ (1) | NZ182810A (en, 2012) |
| RO (1) | RO71764A (en, 2012) |
| SE (1) | SE418799B (en, 2012) |
| YU (1) | YU40159B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5043168A (en) * | 1990-04-26 | 1991-08-27 | Sidmak Laboratories, Inc. | Solid choline magnesium salicylate composition and method of preparing same |
| US5217965A (en) * | 1991-06-17 | 1993-06-08 | Euroceltique, S.A. | Stabilized solid dosage forms of choline metal carboxymethylcellulose salicylate compositions |
| USD863685S1 (en) | 2017-11-27 | 2019-10-15 | Mary Kay Inc. | Cosmetic compact |
| USD843660S1 (en) | 2017-11-27 | 2019-03-19 | Mary Kay Inc. | Cosmetic compact |
| USD850006S1 (en) | 2017-11-27 | 2019-05-28 | Mary Kay Inc. | Cosmetic compact |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3347744A (en) * | 1963-10-25 | 1967-10-17 | Smith Kline French Lab | Magnesium hydroxide suspensions |
| US3297529A (en) * | 1964-11-25 | 1967-01-10 | Sutton Lab Inc | Magnesium sulfate stabilized choline salicylate |
| US3326760A (en) * | 1966-05-17 | 1967-06-20 | Synergistics Inc | Choline salicylate polygalacturonate therapy |
| US3759980A (en) * | 1969-05-26 | 1973-09-18 | Stockton Chemicals Inc | Salicylates |
-
1976
- 1976-09-08 CA CA260,766A patent/CA1070299A/en not_active Expired
- 1976-11-25 IL IL50992A patent/IL50992A/xx unknown
- 1976-12-06 NZ NZ182810A patent/NZ182810A/xx unknown
- 1976-12-07 GR GR52348A patent/GR62110B/el unknown
- 1976-12-22 AR AR265966A patent/AR217249A1/es active
- 1976-12-23 SE SE7614538A patent/SE418799B/xx not_active IP Right Cessation
- 1976-12-30 ES ES454712A patent/ES454712A1/es not_active Expired
- 1976-12-30 FI FI763741A patent/FI56770C/fi not_active IP Right Cessation
-
1977
- 1977-01-10 CH CH25977A patent/CH635816A5/de not_active IP Right Cessation
- 1977-01-12 YU YU69/77A patent/YU40159B/xx unknown
- 1977-01-14 RO RO7789053A patent/RO71764A/ro unknown
- 1977-01-15 DE DE2760284A patent/DE2760284C2/de not_active Expired - Lifetime
- 1977-01-15 DE DE19772701553 patent/DE2701553A1/de active Granted
- 1977-01-18 AU AU21419/77A patent/AU511510B2/en not_active Expired
- 1977-01-19 EG EG36/77A patent/EG12511A/xx active
- 1977-01-19 NL NLAANVRAGE7700514,A patent/NL183821C/xx not_active IP Right Cessation
- 1977-01-20 FR FR7701571A patent/FR2338705A1/fr active Granted
- 1977-01-20 NO NO770172A patent/NO145295C/no unknown
- 1977-01-20 DK DK021677A patent/DK149804C/da not_active IP Right Cessation
- 1977-01-20 HU HU77MU577A patent/HU175973B/hu unknown
- 1977-01-21 DD DD7700197041A patent/DD128908A5/xx unknown
- 1977-01-21 MX MX775373U patent/MX5920E/es unknown
- 1977-01-21 GB GB2512/77A patent/GB1575977A/en not_active Expired
- 1977-01-21 JP JP52006319A patent/JPS6051449B2/ja not_active Expired
- 1977-01-21 GB GB9401/79A patent/GB1575978A/en not_active Expired
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