CA1083602A - Preparation industrielle d'cetylsalicylate de sodium stable. - Google Patents

Preparation industrielle d'cetylsalicylate de sodium stable.

Info

Publication number: CA1083602A
Authority: CA; Canada
Prior art keywords: crystals; sodium; sodium acetylsalicylate; dihydrate; acetylsalicylate
Prior art date: 1976-08-03
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

Application number

CA258,344A

Other languages

English (en)

Inventor

Alexander Galat

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Individual

Original Assignee

Individual

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.)

1976-08-03

Filing date

1976-08-03

Publication date

1980-08-12

1976-08-03 Application filed by Individual filed Critical Individual

1976-08-03 Priority to CA258,344A priority Critical patent/CA1083602A/fr

1980-08-12 Application granted granted Critical

1980-08-12 Publication of CA1083602A publication Critical patent/CA1083602A/fr

Status Expired legal-status Critical Current

Links

JZLOKWGVGHYBKD-UHFFFAOYSA-M sodium;2-acetyloxybenzoate Chemical compound [Na+].CC(=O)OC1=CC=CC=C1C([O-])=O JZLOKWGVGHYBKD-UHFFFAOYSA-M 0.000 title claims abstract description 78
238000000034 method Methods 0.000 title claims abstract description 30
238000004519 manufacturing process Methods 0.000 title claims description 10
238000003860 storage Methods 0.000 claims abstract description 12
230000001376 precipitating effect Effects 0.000 claims abstract description 5
239000013078 crystal Substances 0.000 claims description 40
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 33
239000000243 solution Substances 0.000 claims description 15
239000002904 solvent Substances 0.000 claims description 14
239000007864 aqueous solution Substances 0.000 claims description 13
150000004683 dihydrates Chemical class 0.000 claims description 13
230000015572 biosynthetic process Effects 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 8
239000003960 organic solvent Substances 0.000 claims description 7
230000036571 hydration Effects 0.000 claims description 6
238000006703 hydration reaction Methods 0.000 claims description 6
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 5
239000003795 chemical substances by application Substances 0.000 claims description 5
230000018044 dehydration Effects 0.000 claims description 5
238000006297 dehydration reaction Methods 0.000 claims description 5
239000011734 sodium Substances 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
230000001747 exhibiting effect Effects 0.000 claims description 4
238000001556 precipitation Methods 0.000 claims description 4
OLHYKIWATWEPAT-UHFFFAOYSA-M sodium;2-acetyloxybenzoate;dihydrate Chemical compound O.O.[Na+].CC(=O)OC1=CC=CC=C1C([O-])=O OLHYKIWATWEPAT-UHFFFAOYSA-M 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 2
239000000126 substance Substances 0.000 claims 3
-1 sodium aspirin dihydrate Chemical class 0.000 abstract description 8
230000000704 physical effect Effects 0.000 abstract 1
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 26
229960001138 acetylsalicylic acid Drugs 0.000 description 23
239000000047 product Substances 0.000 description 23
229960004592 isopropanol Drugs 0.000 description 14
150000001875 compounds Chemical class 0.000 description 13
150000003839 salts Chemical class 0.000 description 13
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
238000007792 addition Methods 0.000 description 9
238000003756 stirring Methods 0.000 description 9
238000000354 decomposition reaction Methods 0.000 description 6
238000004821 distillation Methods 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
239000002244 precipitate Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
208000005156 Dehydration Diseases 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
238000013019 agitation Methods 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
239000011575 calcium Chemical class 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
238000001816 cooling Methods 0.000 description 2
PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000009472 formulation Methods 0.000 description 2
230000008014 freezing Effects 0.000 description 2
238000007710 freezing Methods 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052744 lithium Inorganic materials 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
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
230000003472 neutralizing effect Effects 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000011084 recovery Methods 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
235000017550 sodium carbonate Nutrition 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
229940001593 sodium carbonate Drugs 0.000 description 2
239000007858 starting material Substances 0.000 description 2
230000009967 tasteless effect Effects 0.000 description 2
230000000007 visual effect Effects 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
RBNPOMFGQQGHHO-UWTATZPHSA-N D-glyceric acid Chemical compound OC[C@@H](O)C(O)=O RBNPOMFGQQGHHO-UWTATZPHSA-N 0.000 description 1
208000018522 Gastrointestinal disease Diseases 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
150000001243 acetic acids Chemical class 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
235000010210 aluminium Nutrition 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
TZIHFWKZFHZASV-UHFFFAOYSA-N anhydrous methyl formate Natural products COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000013329 compounding Methods 0.000 description 1
238000007906 compression Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000011109 contamination Methods 0.000 description 1
230000008094 contradictory effect Effects 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
238000000227 grinding Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000000887 hydrating effect Effects 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229940035429 isobutyl alcohol Drugs 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000001055 magnesium Nutrition 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
235000014380 magnesium carbonate Nutrition 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
229960001708 magnesium carbonate Drugs 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229940091250 magnesium supplement Drugs 0.000 description 1
239000000463 material Substances 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
235000019629 palatability Nutrition 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
150000003870 salicylic acids Chemical class 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA258,344A 1976-08-03 1976-08-03 Preparation industrielle d'cetylsalicylate de sodium stable. Expired CA1083602A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA258,344A CA1083602A (fr)	1976-08-03	1976-08-03	Preparation industrielle d'cetylsalicylate de sodium stable.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA258,344A CA1083602A (fr)	1976-08-03	1976-08-03	Preparation industrielle d'cetylsalicylate de sodium stable.

Publications (1)

Publication Number	Publication Date
CA1083602A true CA1083602A (fr)	1980-08-12

Family

ID=4106568

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA258,344A Expired CA1083602A (fr)	1976-08-03	1976-08-03	Preparation industrielle d'cetylsalicylate de sodium stable.

Country Status (1)

Country	Link
CA (1)	CA1083602A (fr)

1976
- 1976-08-03 CA CA258,344A patent/CA1083602A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-08-12	MKEX	Expiry

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