CA1311683C - Procede de preparation d'une composition inhibitrice ou destructive d'aumoins un etre vivant unicellulaire renfermant un fluorure d'ammonium quaternaire et procede de preparation de ce sel - Google Patents

Procede de preparation d'une composition inhibitrice ou destructive d'aumoins un etre vivant unicellulaire renfermant un fluorure d'ammonium quaternaire et procede de preparation de ce sel

Info

Publication number: CA1311683C
Authority: CA; Canada
Prior art keywords: composition; fluoride; use according; benzalkonium; quaternary ammonium
Prior art date: 1987-09-23
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 - Lifetime

Application number

CA000577935A

Other languages

English (en)

French (fr)

Inventor

Pierre Bourbon

Pierre Lagny

Pierre Billot

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.)

Aromafarm Ltd

Original Assignee

Atlantic Pharmaceutical Products Ltd

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.)

1987-09-23

Filing date

1988-09-20

Publication date

1992-12-22

1987-09-23 Priority claimed from FR8713156A external-priority patent/FR2620698B1/fr

1988-09-20 Application filed by Atlantic Pharmaceutical Products Ltd filed Critical Atlantic Pharmaceutical Products Ltd

1992-12-22 Application granted granted Critical

1992-12-22 Publication of CA1311683C publication Critical patent/CA1311683C/fr

2009-12-22 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 62
230000002401 inhibitory effect Effects 0.000 title claims abstract description 11
125000001453 quaternary ammonium group Chemical group 0.000 title claims description 21
238000000034 method Methods 0.000 title description 22
238000002360 preparation method Methods 0.000 title description 15
150000003839 salts Chemical class 0.000 title description 5
241000700605 Viruses Species 0.000 claims abstract description 17
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 4
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 97
PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 claims description 25
JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 claims description 16
230000003115 biocidal effect Effects 0.000 claims description 13
239000003755 preservative agent Substances 0.000 claims description 13
230000002335 preservative effect Effects 0.000 claims description 13
230000003612 virological effect Effects 0.000 claims description 12
230000000844 anti-bacterial effect Effects 0.000 claims description 10
230000000855 fungicidal effect Effects 0.000 claims description 10
230000003253 viricidal effect Effects 0.000 claims description 10
241000282414 Homo sapiens Species 0.000 claims description 8
241001465754 Metazoa Species 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
239000003242 anti bacterial agent Substances 0.000 claims description 7
238000004659 sterilization and disinfection Methods 0.000 claims description 7
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
239000004480 active ingredient Substances 0.000 claims description 5
210000004392 genitalia Anatomy 0.000 claims description 5
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150000003863 ammonium salts Chemical class 0.000 claims description 4
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XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 claims description 3
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DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 claims description 2
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
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150000003242 quaternary ammonium salts Chemical class 0.000 abstract description 4
241000894006 Bacteria Species 0.000 abstract description 3
230000001066 destructive effect Effects 0.000 abstract description 3
229960001716 benzalkonium Drugs 0.000 description 96
CYDRXTMLKJDRQH-UHFFFAOYSA-N benzododecinium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 CYDRXTMLKJDRQH-UHFFFAOYSA-N 0.000 description 94
230000002421 anti-septic effect Effects 0.000 description 34
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
239000000546 pharmaceutical excipient Substances 0.000 description 32
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 29
229960000686 benzalkonium chloride Drugs 0.000 description 23
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 23
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
239000008213 purified water Substances 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
-1 quaternary ammonium halides Chemical class 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 12
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239000003963 antioxidant agent Substances 0.000 description 12
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239000006071 cream Substances 0.000 description 11
235000019441 ethanol Nutrition 0.000 description 11
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 10
230000003078 antioxidant effect Effects 0.000 description 10
239000012153 distilled water Substances 0.000 description 10
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CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
238000001914 filtration Methods 0.000 description 8
229910052731 fluorine Inorganic materials 0.000 description 8
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 7
UDHXJZHVNHGCEC-UHFFFAOYSA-N Chlorophacinone Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)C(=O)C1C(=O)C2=CC=CC=C2C1=O UDHXJZHVNHGCEC-UHFFFAOYSA-N 0.000 description 7
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239000011737 fluorine Substances 0.000 description 7
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239000003381 stabilizer Substances 0.000 description 7
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 6
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 description 6
238000010790 dilution Methods 0.000 description 6
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239000002674 ointment Substances 0.000 description 6
239000000600 sorbitol Substances 0.000 description 6
235000010356 sorbitol Nutrition 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
229920002678 cellulose Polymers 0.000 description 5
238000009472 formulation Methods 0.000 description 5
LWGJTAZLEJHCPA-UHFFFAOYSA-N n-(2-chloroethyl)-n-nitrosomorpholine-4-carboxamide Chemical compound ClCCN(N=O)C(=O)N1CCOCC1 LWGJTAZLEJHCPA-UHFFFAOYSA-N 0.000 description 5
239000003921 oil Substances 0.000 description 5
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150000003254 radicals Chemical class 0.000 description 5
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
HJQDKKIKGDXACL-UHFFFAOYSA-N benzyl(dimethyl)azanium;methyl carbonate Chemical compound COC([O-])=O.C[NH+](C)CC1=CC=CC=C1 HJQDKKIKGDXACL-UHFFFAOYSA-N 0.000 description 4
229960003237 betaine Drugs 0.000 description 4
239000000872 buffer Substances 0.000 description 4
239000001913 cellulose Substances 0.000 description 4
235000010980 cellulose Nutrition 0.000 description 4
238000000338 in vitro Methods 0.000 description 4
239000003112 inhibitor Substances 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
239000008274 jelly Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
238000000746 purification Methods 0.000 description 4
PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 4
239000002904 solvent Substances 0.000 description 4
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230000002195 synergetic effect Effects 0.000 description 4
241000203233 Aspergillus versicolor Species 0.000 description 3
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WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
239000004166 Lanolin Substances 0.000 description 3
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RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 2
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
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NBVZMBLJRHUOJR-UHFFFAOYSA-N [amino-[4-[6-[4-[amino(azaniumylidene)methyl]phenoxy]hexoxy]phenyl]methylidene]azanium;2-hydroxyethanesulfonate Chemical compound OCCS(O)(=O)=O.OCCS(O)(=O)=O.C1=CC(C(=N)N)=CC=C1OCCCCCCOC1=CC=C(C(N)=N)C=C1 NBVZMBLJRHUOJR-UHFFFAOYSA-N 0.000 description 2
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238000010908 decantation Methods 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
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IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
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WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 description 1
230000001333 moisturizer Effects 0.000 description 1
230000003020 moisturizing effect Effects 0.000 description 1
210000004877 mucosa Anatomy 0.000 description 1
229960004927 neomycin Drugs 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229960000625 oxytetracycline Drugs 0.000 description 1
IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 description 1
235000019366 oxytetracycline Nutrition 0.000 description 1
229960004368 oxytetracycline hydrochloride Drugs 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
239000013612 plasmid Substances 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
238000004321 preservation Methods 0.000 description 1
239000004017 serum-free culture medium Substances 0.000 description 1
239000002453 shampoo Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
238000004088 simulation Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
239000004753 textile Substances 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 1
238000007738 vacuum evaporation Methods 0.000 description 1
239000010497 wheat germ oil Substances 0.000 description 1
NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
229960001763 zinc sulfate Drugs 0.000 description 1
229910000368 zinc sulfate Inorganic materials 0.000 description 1

Landscapes

Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CA000577935A 1987-09-23 1988-09-20 Procede de preparation d'une composition inhibitrice ou destructive d'aumoins un etre vivant unicellulaire renfermant un fluorure d'ammonium quaternaire et procede de preparation de ce sel Expired - Lifetime CA1311683C (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
FR8713156A FR2620698B1 (fr)	1987-09-23	1987-09-23	Fluorure d'ammonium quaternaire et son application dans une substance inhibitrice ou destructrice d'etres vivants unicellulaires
FR8713156		1987-09-23
EP87402632.1		1987-11-23
EP87402632A EP0308564B1 (de)	1987-09-23	1987-11-23	Zusammensetzung zur Hemmung oder Vernichtung mindestens eines einzelligen Lebewesens, enthaltend ein quaternäres Ammoniumfluorid, und Verfahren zur Herstellung dieses Salzes

Publications (1)

Publication Number	Publication Date
CA1311683C true CA1311683C (fr)	1992-12-22

Family

ID=26112105

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000577935A Expired - Lifetime CA1311683C (fr)	1987-09-23	1988-09-20	Procede de preparation d'une composition inhibitrice ou destructive d'aumoins un etre vivant unicellulaire renfermant un fluorure d'ammonium quaternaire et procede de preparation de ce sel

Country Status (5)

Country	Link
JP (1)	JP2634871B2 (de)
AT (1)	ATE78396T1 (de)
CA (1)	CA1311683C (de)
IL (1)	IL87829A (de)
MC (1)	MC1978A1 (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL9500216A (nl) *	1995-02-06	1996-09-02	Bio Pharma Sciences Bv	Farmaceutische samenstelling voor de behandeling van herpes.
JP2012219069A (ja) *	2011-04-11	2012-11-12	Neos Co Ltd	カビの防除方法及び液状カビ防除剤組成物

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3277118A (en) *	1958-05-29	1966-10-04	Gaba Ag	Quaternary ammonium fluorides
IT1082339B (it) *	1977-02-07	1985-05-21	Zambelletti Dr L Spa	Composto ad attivita disinfettante e composizioni farmaceutiche che lo contengono
ATE64854T1 (de) *	1986-05-22	1991-07-15	Atlantic Pharma Prod	Zusammensetzung mit hemmender wirkung auf zumindest ein einzelliges lebewesen und/oder virus, herstellungsverfahren und anwendungen dieser zusammensetzung.

1987
- 1987-11-23 AT AT87402632T patent/ATE78396T1/de active
1988
- 1988-09-19 JP JP63232726A patent/JP2634871B2/ja not_active Expired - Fee Related
- 1988-09-19 MC MC882006A patent/MC1978A1/fr unknown
- 1988-09-20 CA CA000577935A patent/CA1311683C/fr not_active Expired - Lifetime
- 1988-09-22 IL IL8782988A patent/IL87829A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
JP2634871B2 (ja)	1997-07-30
MC1978A1 (fr)	1989-11-23
JPH01163119A (ja)	1989-06-27
IL87829A0 (en)	1989-03-31
ATE78396T1 (de)	1992-08-15
IL87829A (en)	1995-03-15

Legal Events

Date	Code	Title	Description
2009-12-22	MKLA	Lapsed
2012-12-05	MKEC	Expiry (correction)	Effective date: 20121205

Publication	Publication Date	Title
EP0308564B1 (de)	1992-07-22	Zusammensetzung zur Hemmung oder Vernichtung mindestens eines einzelligen Lebewesens, enthaltend ein quaternäres Ammoniumfluorid, und Verfahren zur Herstellung dieses Salzes
US12295366B2 (en)	2025-05-13	Preservation of personal care compositions
EP0402266B1 (de)	1994-02-02	N-substituierte Lauramide, ihre Herstellung und sie enthaltende Zusammensetzungen
IL276129B1 (en)	2023-12-01	Antimicrobial preservative compositions
KR20170086019A (ko)	2017-07-25	감염증 및 염증의 예방 및/또는 치료에 유용한 조성물
US11590187B2 (en)	2023-02-28	Antimicrobial compositions
EP0253037B1 (de)	1991-07-03	Zusammensetzung mit hemmender Wirkung auf zumindest ein einzelliges Lebewesen und/oder Virus, Herstellungsverfahren und Anwendungen dieser Zusammensetzung
EP3644733A1 (de)	2020-05-06	Antimikrobielle mischung mit 4-(3-ethoxy-4-hydroxyphenyl)butan-2-on und einer organischen säureverbindung und kosmetische zusammensetzung damit
US7429396B2 (en)	2008-09-30	Antifungal composition, its fungicidal effect on pathogenic dermatophytes, and process for inhibiting growth of fungi
CA2080820C (fr)	2003-11-25	Derives azoiques, compositions pharmaceutiques et desinfectantes les contenant et leurs utilisations
EP0310476B1 (de)	1992-03-04	Für mindestens einzellige Lebewesen inhibitierende oder zerstörende F- und Li+ enthaltende Zusammensetzung
JP2559735B2 (ja)	1996-12-04	抗ー微生物組成物
MC1978A1 (fr)	1989-11-23	Procede de preparation d'une composition inhibitrice ou destructrice d'au moins un etre vivant unicellulaire renfermant un fluorure d'ammonium quaternaire et procede de preparation de ce sel
EP0387314B1 (de)	1994-05-04	Anwendung von gegen retroviren aktiven wirkstoffen und so erhaltene produkte
EP0524873B1 (de)	1995-10-11	Harpagophytonwurzelextrakt enthaltende, antipruriginöse kosmetische Zusammensetzung
FR2652001A1 (fr)	1991-03-22	Composition dermato-cosmetique a base d'acide rosmarinique presentant des proprietes de filtre solaire et d'agent anti-inflammatoire.
EP0520865A1 (de)	1992-12-30	Verwendung von Säurederivaten zur Herstellung eines Medikamentes gegen Läuse
EP0309533B1 (de)	1991-10-02	Butylhydroxyanisole zur behandlung von retrovirus-krankheiten
RU2780109C1 (ru)	2022-09-19	Противовоспалительные глазные капли для домашних и сельскохозяйственных животных
FR2616065A1 (fr)	1988-12-09	Aerosol pharmaceutique a base d'ammonium quaternaires
US20200069630A1 (en)	2020-03-05	Compositions for sexually transmitted diseases
FR2541114A1 (fr)	1984-08-24	Compositions pharmaceutiques antifongiques utilisables par voie orale contenant de l'omoconazole
BE670235A (de)	1966-01-17
BE618722A (de)
EP0240391A1 (de)	1987-10-07	Naphtyridinderivat-Silbersalz, brauchbar als Bakterizid, Verfahren zur Herstellung und dieses enthaltende Zubereitungen