AP957A - Novel stable liquid paracetamol compositions, and method for preparing same. - Google Patents

Novel stable liquid paracetamol compositions, and method for preparing same. Download PDF

Info

Publication number: AP957A
Authority: AP; ARIPO
Prior art keywords: paracetamol; stable; liquid formulations; formulations according; solution
Prior art date: 1996-08-05

Application number

APAP/P/1998/001223A

Other languages

English (en)

Other versions

AP9801223A0 (en

Inventor

Francois Dietlin

Daniéle Fredj

Original Assignee

Scr Pharmatop

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.)

1996-08-05

Filing date

1997-08-05

Publication date

2001-04-12

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=9494820&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=AP957(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1997-08-05 Application filed by Scr Pharmatop filed Critical Scr Pharmatop

1998-06-30 Publication of AP9801223A0 publication Critical patent/AP9801223A0/xx

2001-04-12 Application granted granted Critical

2001-04-12 Publication of AP957A publication Critical patent/AP957A/en

Links

RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 title claims abstract description 131
229960005489 paracetamol Drugs 0.000 title claims abstract description 129
239000000203 mixture Substances 0.000 title claims abstract description 26
239000007788 liquid Substances 0.000 title description 5
238000000034 method Methods 0.000 title description 5
150000003254 radicals Chemical class 0.000 claims abstract description 10
239000003125 aqueous solvent Substances 0.000 claims abstract description 8
239000003795 chemical substances by application Substances 0.000 claims abstract description 4
239000011261 inert gas Substances 0.000 claims abstract description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
239000012669 liquid formulation Substances 0.000 claims description 27
-1 alkali metal ascorbates Chemical class 0.000 claims description 23
239000002516 radical scavenger Substances 0.000 claims description 23
229940123457 Free radical scavenger Drugs 0.000 claims description 22
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 22
OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 claims description 21
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 17
230000005587 bubbling Effects 0.000 claims description 17
150000001875 compounds Chemical class 0.000 claims description 16
OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 claims description 16
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 14
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 11
RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 claims description 11
235000003969 glutathione Nutrition 0.000 claims description 11
229960003180 glutathione Drugs 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 11
150000003573 thiols Chemical group 0.000 claims description 11
230000000202 analgesic effect Effects 0.000 claims description 10
235000010323 ascorbic acid Nutrition 0.000 claims description 10
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 8
150000000996 L-ascorbic acids Chemical group 0.000 claims description 8
229930195725 Mannitol Natural products 0.000 claims description 8
229960005070 ascorbic acid Drugs 0.000 claims description 8
239000000594 mannitol Substances 0.000 claims description 8
235000010355 mannitol Nutrition 0.000 claims description 8
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 7
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 7
239000005557 antagonist Substances 0.000 claims description 6
VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 claims description 6
239000008103 glucose Substances 0.000 claims description 6
238000010438 heat treatment Methods 0.000 claims description 6
229960005181 morphine Drugs 0.000 claims description 6
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
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 claims description 5
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 5
PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 claims description 5
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
239000008139 complexing agent Substances 0.000 claims description 5
239000000600 sorbitol Substances 0.000 claims description 5
229940121363 anti-inflammatory agent Drugs 0.000 claims description 4
239000002260 anti-inflammatory agent Substances 0.000 claims description 4
229960004126 codeine Drugs 0.000 claims description 4
238000007911 parenteral administration Methods 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
ZNEWHQLOPFWXOF-UHFFFAOYSA-N coenzyme M Chemical compound OS(=O)(=O)CCS ZNEWHQLOPFWXOF-UHFFFAOYSA-N 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 3
229960004635 mesna Drugs 0.000 claims description 3
150000002894 organic compounds Chemical group 0.000 claims description 3
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 3
SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 claims description 2
239000002211 L-ascorbic acid Substances 0.000 claims description 2
235000000069 L-ascorbic acid Nutrition 0.000 claims description 2
229940123445 Tricyclic antidepressant Drugs 0.000 claims description 2
239000001961 anticonvulsive agent Substances 0.000 claims description 2
239000002111 antiemetic agent Substances 0.000 claims description 2
239000012736 aqueous medium Substances 0.000 claims description 2
239000003246 corticosteroid Substances 0.000 claims description 2
CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 claims description 2
229960000367 inositol Drugs 0.000 claims description 2
DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical group OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 claims description 2
229960000991 ketoprofen Drugs 0.000 claims description 2
PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 claims description 2
229960003424 phenylacetic acid Drugs 0.000 claims description 2
239000003279 phenylacetic acid Substances 0.000 claims description 2
CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 claims description 2
239000003029 tricyclic antidepressant agent Substances 0.000 claims description 2
239000006172 buffering agent Substances 0.000 claims 3
PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 claims 2
125000004432 carbon atom Chemical group C* 0.000 claims 2
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims 2
CIWBSHSKHKDKBQ-MVHIGOERSA-N D-ascorbic acid Chemical compound OC[C@@H](O)[C@@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-MVHIGOERSA-N 0.000 claims 1
125000002723 alicyclic group Chemical group 0.000 claims 1
229940125683 antiemetic agent Drugs 0.000 claims 1
150000005846 sugar alcohols Polymers 0.000 claims 1
239000000872 buffer Substances 0.000 abstract description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 6
239000001301 oxygen Substances 0.000 abstract description 6
229910052760 oxygen Inorganic materials 0.000 abstract description 6
208000002193 Pain Diseases 0.000 abstract description 4
230000001225 therapeutic effect Effects 0.000 abstract description 3
239000000730 antalgic agent Substances 0.000 abstract 1
239000007972 injectable composition Substances 0.000 abstract 1
239000000243 solution Substances 0.000 description 151
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 48
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 45
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 38
229910052757 nitrogen Inorganic materials 0.000 description 29
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
239000011780 sodium chloride Substances 0.000 description 19
239000007864 aqueous solution Substances 0.000 description 17
239000004615 ingredient Substances 0.000 description 16
235000013772 propylene glycol Nutrition 0.000 description 16
229960004063 propylene glycol Drugs 0.000 description 15
229920001030 Polyethylene Glycol 4000 Polymers 0.000 description 13
239000008215 water for injection Substances 0.000 description 13
229920002565 Polyethylene Glycol 400 Polymers 0.000 description 12
238000002835 absorbance Methods 0.000 description 12
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
238000002347 injection Methods 0.000 description 11
239000007924 injection Substances 0.000 description 11
UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 10
238000011049 filling Methods 0.000 description 9
238000003860 storage Methods 0.000 description 9
239000002202 Polyethylene glycol Substances 0.000 description 8
239000011668 ascorbic acid Substances 0.000 description 8
238000009472 formulation Methods 0.000 description 8
229920001223 polyethylene glycol Polymers 0.000 description 8
239000000047 product Substances 0.000 description 8
238000010926 purge Methods 0.000 description 8
239000012299 nitrogen atmosphere Substances 0.000 description 7
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
230000015556 catabolic process Effects 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
210000003205 muscle Anatomy 0.000 description 6
239000011877 solvent mixture Substances 0.000 description 6
239000002253 acid Substances 0.000 description 5
KDQPSPMLNJTZAL-UHFFFAOYSA-L disodium hydrogenphosphate dihydrate Chemical compound O.O.[Na+].[Na+].OP([O-])([O-])=O KDQPSPMLNJTZAL-UHFFFAOYSA-L 0.000 description 5
239000012153 distilled water Substances 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
239000008194 pharmaceutical composition Substances 0.000 description 5
230000001954 sterilising effect Effects 0.000 description 5
238000004659 sterilization and disinfection Methods 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
229910019142 PO4 Inorganic materials 0.000 description 4
229920002556 Polyethylene Glycol 300 Polymers 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
239000004411 aluminium Substances 0.000 description 4
229910052782 aluminium Inorganic materials 0.000 description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
229920005557 bromobutyl Polymers 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
230000018109 developmental process Effects 0.000 description 4
229960005195 morphine hydrochloride Drugs 0.000 description 4
235000021317 phosphate Nutrition 0.000 description 4
239000002504 physiological saline solution Substances 0.000 description 4
PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 4
235000010378 sodium ascorbate Nutrition 0.000 description 4
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PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 4
230000006641 stabilisation Effects 0.000 description 4
238000011105 stabilization Methods 0.000 description 4
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
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102000004420 Creatine Kinase Human genes 0.000 description 3
108010042126 Creatine kinase Proteins 0.000 description 3
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical group [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
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239000011575 calcium Substances 0.000 description 3
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AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
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MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
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239000004698 Polyethylene Substances 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
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229960003871 codeine sulfate Drugs 0.000 description 2
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XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
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LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 2
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XELXKCKNPPSFNN-BJWPBXOKSA-N morphine hydrochloride trihydrate Chemical compound O.O.O.Cl.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O XELXKCKNPPSFNN-BJWPBXOKSA-N 0.000 description 2
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- 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]
- 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
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones

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Animal Behavior & Ethology (AREA)
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General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
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Pain & Pain Management (AREA)
Dermatology (AREA)
Organic Chemistry (AREA)
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Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Emergency Medicine (AREA)
Neurosurgery (AREA)
Rheumatology (AREA)
Bioinformatics & Cheminformatics (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Medicinal Preparation (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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APAP/P/1998/001223A 1996-08-05 1997-08-05 Novel stable liquid paracetamol compositions, and method for preparing same. AP957A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR9609858A FR2751875B1 (fr)	1996-08-05	1996-08-05	Nouvelles formulations liquides stables a base de paracetamol et leur mode de preparation

Publications (2)

Publication Number	Publication Date
AP9801223A0 AP9801223A0 (en)	1998-06-30
AP957A true AP957A (en)	2001-04-12

Family

ID=9494820

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
APAP/P/1998/001223A AP957A (en)	1996-08-05	1997-08-05	Novel stable liquid paracetamol compositions, and method for preparing same.

Country Status (23)

Country	Link
US (1)	US6028222A (fr)
EP (1)	EP0858329B1 (fr)
JP (2)	JP5060681B2 (fr)
KR (1)	KR100521235B1 (fr)
CN (1)	CN1133426C (fr)
AP (1)	AP957A (fr)
AT (1)	ATE241972T1 (fr)
AU (1)	AU742576B2 (fr)
BR (1)	BR9702362A (fr)
CA (1)	CA2233924C (fr)
CZ (1)	CZ298427B6 (fr)
DE (1)	DE69722580T2 (fr)
DK (1)	DK0858329T3 (fr)
ES (1)	ES2201316T3 (fr)
FR (1)	FR2751875B1 (fr)
HU (1)	HU226117B1 (fr)
MX (1)	MX9802734A (fr)
NZ (1)	NZ330136A (fr)
OA (1)	OA10678A (fr)
PL (1)	PL193104B1 (fr)
PT (1)	PT858329E (fr)
RU (1)	RU2192249C2 (fr)
WO (1)	WO1998005314A1 (fr)

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1996
- 1996-08-05 FR FR9609858A patent/FR2751875B1/fr not_active Expired - Fee Related
1997
- 1997-08-05 JP JP50768698A patent/JP5060681B2/ja not_active Expired - Lifetime
- 1997-08-05 NZ NZ330136A patent/NZ330136A/xx not_active IP Right Cessation
- 1997-08-05 AU AU39451/97A patent/AU742576B2/en not_active Expired
- 1997-08-05 WO PCT/FR1997/001452 patent/WO1998005314A1/fr not_active Ceased
- 1997-08-05 US US09/051,246 patent/US6028222A/en not_active Expired - Lifetime
- 1997-08-05 CN CNB971913714A patent/CN1133426C/zh not_active Expired - Lifetime
- 1997-08-05 DE DE69722580T patent/DE69722580T2/de not_active Expired - Lifetime
- 1997-08-05 HU HU9901893A patent/HU226117B1/hu unknown
- 1997-08-05 DK DK97936739T patent/DK0858329T3/da active
- 1997-08-05 KR KR1019980702453A patent/KR100521235B1/ko not_active Expired - Lifetime
- 1997-08-05 CZ CZ0104898A patent/CZ298427B6/cs not_active IP Right Cessation
- 1997-08-05 PL PL326069A patent/PL193104B1/pl unknown
- 1997-08-05 PT PT97936739T patent/PT858329E/pt unknown
- 1997-08-05 EP EP97936739A patent/EP0858329B1/fr not_active Expired - Lifetime
- 1997-08-05 CA CA2233924A patent/CA2233924C/fr not_active Expired - Lifetime
- 1997-08-05 AT AT97936739T patent/ATE241972T1/de active
- 1997-08-05 BR BR9702362-0A patent/BR9702362A/pt not_active IP Right Cessation
- 1997-08-05 RU RU98108032/14A patent/RU2192249C2/ru active
- 1997-08-05 AP APAP/P/1998/001223A patent/AP957A/en active
- 1997-08-05 ES ES97936739T patent/ES2201316T3/es not_active Expired - Lifetime
1998
- 1998-04-03 OA OA9800039A patent/OA10678A/fr unknown
- 1998-04-03 MX MX9802734A patent/MX9802734A/es unknown
2010
- 2010-04-28 JP JP2010104213A patent/JP5122604B2/ja not_active Expired - Lifetime

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US5474757A (en) *	1992-10-16	1995-12-12	Rutgers University	Prevention of acetaminophen overdose toxicity with organosulfur compounds

Also Published As

Publication number	Publication date
JP2010163462A (ja)	2010-07-29
DE69722580D1 (de)	2003-07-10
PL326069A1 (en)	1998-08-17
PL193104B1 (pl)	2007-01-31
NZ330136A (en)	2000-03-27
US6028222A (en)	2000-02-22
ES2201316T3 (es)	2004-03-16
FR2751875A1 (fr)	1998-02-06
PT858329E (pt)	2003-09-30
FR2751875B1 (fr)	1998-12-24
OA10678A (fr)	2002-11-20
HUP9901893A3 (en)	2000-06-28
JP5122604B2 (ja)	2013-01-16
AU3945197A (en)	1998-02-25
EP0858329A1 (fr)	1998-08-19
WO1998005314A1 (fr)	1998-02-12
KR19990063978A (ko)	1999-07-26
CA2233924C (fr)	2012-08-21
CZ104898A3 (cs)	1998-09-16
ATE241972T1 (de)	2003-06-15
JPH11514013A (ja)	1999-11-30
KR100521235B1 (ko)	2006-01-27
BR9702362A (pt)	1999-12-28
CZ298427B6 (cs)	2007-10-03
RU2192249C2 (ru)	2002-11-10
HU226117B1 (en)	2008-04-28
CN1133426C (zh)	2004-01-07
JP5060681B2 (ja)	2012-10-31
MX9802734A (es)	1998-11-30
AP9801223A0 (en)	1998-06-30
HUP9901893A2 (hu)	1999-09-28
AU742576B2 (en)	2002-01-10
CN1204960A (zh)	1999-01-13
EP0858329B1 (fr)	2003-06-04
CA2233924A1 (fr)	1998-02-12
DK0858329T3 (da)	2003-09-29
DE69722580T2 (de)	2004-04-29

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