MX2007006125A - A composition comprising at least 3 different diols. - Google Patents
A composition comprising at least 3 different diols.Info
- Publication number
- MX2007006125A MX2007006125A MX2007006125A MX2007006125A MX2007006125A MX 2007006125 A MX2007006125 A MX 2007006125A MX 2007006125 A MX2007006125 A MX 2007006125A MX 2007006125 A MX2007006125 A MX 2007006125A MX 2007006125 A MX2007006125 A MX 2007006125A
- Authority
- MX
- Mexico
- Prior art keywords
- diol
- composition
- composition according
- diols
- pentan
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 100
- 150000002009 diols Chemical class 0.000 title claims abstract description 55
- 230000000845 anti-microbial effect Effects 0.000 claims abstract description 20
- 244000005700 microbiome Species 0.000 claims abstract description 18
- 239000003755 preservative agent Substances 0.000 claims abstract description 10
- 239000002537 cosmetic Substances 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 230000002335 preservative effect Effects 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 18
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 16
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 16
- 239000004599 antimicrobial Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- SVTBMSDMJJWYQN-RXMQYKEDSA-N (4r)-2-methylpentane-2,4-diol Chemical compound C[C@@H](O)CC(C)(C)O SVTBMSDMJJWYQN-RXMQYKEDSA-N 0.000 claims description 8
- 239000006071 cream Substances 0.000 claims description 8
- 241000894006 Bacteria Species 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 239000002674 ointment Substances 0.000 claims description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 6
- 241000222122 Candida albicans Species 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 6
- -1 allylamines Chemical compound 0.000 claims description 6
- 239000003242 anti bacterial agent Substances 0.000 claims description 6
- 239000006210 lotion Substances 0.000 claims description 6
- 239000006072 paste Substances 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
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- 239000000454 talc Substances 0.000 claims description 5
- 229910052623 talc Inorganic materials 0.000 claims description 5
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- 229940095731 candida albicans Drugs 0.000 claims description 4
- 239000000499 gel Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 241000233866 Fungi Species 0.000 claims description 3
- 230000000844 anti-bacterial effect Effects 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
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- MQHLMHIZUIDKOO-OKZBNKHCSA-N (2R,6S)-2,6-dimethyl-4-[(2S)-2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl]morpholine Chemical compound C1=CC(C(C)(C)CC)=CC=C1C[C@H](C)CN1C[C@@H](C)O[C@@H](C)C1 MQHLMHIZUIDKOO-OKZBNKHCSA-N 0.000 claims description 2
- UNVGBIALRHLALK-UHFFFAOYSA-N 1,5-Hexanediol Chemical compound CC(O)CCCCO UNVGBIALRHLALK-UHFFFAOYSA-N 0.000 claims description 2
- 229930183010 Amphotericin Natural products 0.000 claims description 2
- QGGFZZLFKABGNL-UHFFFAOYSA-N Amphotericin A Natural products OC1C(N)C(O)C(C)OC1OC1C=CC=CC=CC=CCCC=CC=CC(C)C(O)C(C)C(C)OC(=O)CC(O)CC(O)CCC(O)C(O)CC(O)CC(O)(CC(O)C2C(O)=O)OC2C1 QGGFZZLFKABGNL-UHFFFAOYSA-N 0.000 claims description 2
- 241000228197 Aspergillus flavus Species 0.000 claims description 2
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- 241000222120 Candida <Saccharomycetales> Species 0.000 claims description 2
- 241000282465 Canis Species 0.000 claims description 2
- 241001480035 Epidermophyton Species 0.000 claims description 2
- IECPWNUMDGFDKC-UHFFFAOYSA-N Fusicsaeure Natural products C12C(O)CC3C(=C(CCC=C(C)C)C(O)=O)C(OC(C)=O)CC3(C)C1(C)CCC1C2(C)CCC(O)C1C IECPWNUMDGFDKC-UHFFFAOYSA-N 0.000 claims description 2
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 claims description 2
- 229930182566 Gentamicin Natural products 0.000 claims description 2
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- 229930193140 Neomycin Natural products 0.000 claims description 2
- 241001631646 Papillomaviridae Species 0.000 claims description 2
- JNTOCHDNEULJHD-UHFFFAOYSA-N Penciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(CCC(CO)CO)C=N2 JNTOCHDNEULJHD-UHFFFAOYSA-N 0.000 claims description 2
- 241001045770 Trichophyton mentagrophytes Species 0.000 claims description 2
- 241000223229 Trichophyton rubrum Species 0.000 claims description 2
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims description 2
- 229960004150 aciclovir Drugs 0.000 claims description 2
- 229960003204 amorolfine Drugs 0.000 claims description 2
- 229940009444 amphotericin Drugs 0.000 claims description 2
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 claims description 2
- 230000000840 anti-viral effect Effects 0.000 claims description 2
- 229940121375 antifungal agent Drugs 0.000 claims description 2
- 239000003429 antifungal agent Substances 0.000 claims description 2
- 239000003443 antiviral agent Substances 0.000 claims description 2
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 claims description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 2
- SCKYRAXSEDYPSA-UHFFFAOYSA-N ciclopirox Chemical compound ON1C(=O)C=C(C)C=C1C1CCCCC1 SCKYRAXSEDYPSA-UHFFFAOYSA-N 0.000 claims description 2
- 229960004675 fusidic acid Drugs 0.000 claims description 2
- IECPWNUMDGFDKC-MZJAQBGESA-N fusidic acid Chemical compound O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C(O)=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C IECPWNUMDGFDKC-MZJAQBGESA-N 0.000 claims description 2
- 229960002518 gentamicin Drugs 0.000 claims description 2
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 claims description 2
- AVIYEYCFMVPYST-UHFFFAOYSA-N hexane-1,3-diol Chemical compound CCCC(O)CCO AVIYEYCFMVPYST-UHFFFAOYSA-N 0.000 claims description 2
- QVTWBMUAJHVAIJ-UHFFFAOYSA-N hexane-1,4-diol Chemical compound CCC(O)CCCO QVTWBMUAJHVAIJ-UHFFFAOYSA-N 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- QCIYAEYRVFUFAP-UHFFFAOYSA-N hexane-2,3-diol Chemical compound CCCC(O)C(C)O QCIYAEYRVFUFAP-UHFFFAOYSA-N 0.000 claims description 2
- TXGJTWACJNYNOJ-UHFFFAOYSA-N hexane-2,4-diol Chemical compound CCC(O)CC(C)O TXGJTWACJNYNOJ-UHFFFAOYSA-N 0.000 claims description 2
- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- 230000000813 microbial effect Effects 0.000 claims description 2
- 229960004927 neomycin Drugs 0.000 claims description 2
- 229960000988 nystatin Drugs 0.000 claims description 2
- VQOXZBDYSJBXMA-NQTDYLQESA-N nystatin A1 Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/CC/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 VQOXZBDYSJBXMA-NQTDYLQESA-N 0.000 claims description 2
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 claims description 2
- RUOPINZRYMFPBF-UHFFFAOYSA-N pentane-1,3-diol Chemical compound CCC(O)CCO RUOPINZRYMFPBF-UHFFFAOYSA-N 0.000 claims description 2
- GLOBUAZSRIOKLN-UHFFFAOYSA-N pentane-1,4-diol Chemical compound CC(O)CCCO GLOBUAZSRIOKLN-UHFFFAOYSA-N 0.000 claims description 2
- XLMFDCKSFJWJTP-UHFFFAOYSA-N pentane-2,3-diol Chemical compound CCC(O)C(C)O XLMFDCKSFJWJTP-UHFFFAOYSA-N 0.000 claims description 2
- GTCCGKPBSJZVRZ-UHFFFAOYSA-N pentane-2,4-diol Chemical compound CC(O)CC(C)O GTCCGKPBSJZVRZ-UHFFFAOYSA-N 0.000 claims description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 2
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- 241000555688 Malassezia furfur Species 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- POFSNPPXJUQANW-UHFFFAOYSA-N hexane-3,4-diol Chemical compound CCC(O)C(O)CC POFSNPPXJUQANW-UHFFFAOYSA-N 0.000 claims 1
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- 230000000415 inactivating effect Effects 0.000 abstract description 2
- 230000000694 effects Effects 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
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- 210000004027 cell Anatomy 0.000 description 5
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- OFBQJSOFQDEBGM-QDNHWIQGSA-N 1,5-dideuteriopentane Chemical compound C(CCCC[2H])[2H] OFBQJSOFQDEBGM-QDNHWIQGSA-N 0.000 description 4
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- ATUOYWHBWRKTHZ-SDTNDFKLSA-N 1,2-dideuteriopropane Chemical compound [2H]CC([2H])C ATUOYWHBWRKTHZ-SDTNDFKLSA-N 0.000 description 2
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- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
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- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
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- 230000002519 immonomodulatory effect Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 210000004379 membrane Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- AEIJTFQOBWATKX-UHFFFAOYSA-N octane-1,2-diol Chemical compound CCCCCCC(O)CO AEIJTFQOBWATKX-UHFFFAOYSA-N 0.000 description 1
- NELAVKWPGRMFEQ-UHFFFAOYSA-N octane-1,4-diol Chemical compound CCCCC(O)CCCO NELAVKWPGRMFEQ-UHFFFAOYSA-N 0.000 description 1
- ZKRNQSNKDPEUOH-UHFFFAOYSA-N octane-1,5-diol Chemical compound CCCC(O)CCCCO ZKRNQSNKDPEUOH-UHFFFAOYSA-N 0.000 description 1
- GDUWKVCUIFEAGC-UHFFFAOYSA-N octane-1,6-diol Chemical compound CCC(O)CCCCCO GDUWKVCUIFEAGC-UHFFFAOYSA-N 0.000 description 1
- QUADBKCRXGFGAX-UHFFFAOYSA-N octane-1,7-diol Chemical compound CC(O)CCCCCCO QUADBKCRXGFGAX-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- XMTUJCWABCYSIV-UHFFFAOYSA-N octane-2,3-diol Chemical compound CCCCCC(O)C(C)O XMTUJCWABCYSIV-UHFFFAOYSA-N 0.000 description 1
- HOWLAKMIIWUJEJ-UHFFFAOYSA-N octane-2,4-diol Chemical compound CCCCC(O)CC(C)O HOWLAKMIIWUJEJ-UHFFFAOYSA-N 0.000 description 1
- AZVKGHXATHHFRF-UHFFFAOYSA-N octane-2,5-diol Chemical compound CCCC(O)CCC(C)O AZVKGHXATHHFRF-UHFFFAOYSA-N 0.000 description 1
- ONGUKKAIGDNAGC-UHFFFAOYSA-N octane-2,6-diol Chemical compound CCC(O)CCCC(C)O ONGUKKAIGDNAGC-UHFFFAOYSA-N 0.000 description 1
- PAXWQLGKYISPNH-UHFFFAOYSA-N octane-2,7-diol Chemical compound CC(O)CCCCC(C)O PAXWQLGKYISPNH-UHFFFAOYSA-N 0.000 description 1
- UJWVPVVMYOBBIY-UHFFFAOYSA-N octane-3,4-diol Chemical compound CCCCC(O)C(O)CC UJWVPVVMYOBBIY-UHFFFAOYSA-N 0.000 description 1
- WYNVIVRXHYGNRT-UHFFFAOYSA-N octane-3,5-diol Chemical compound CCCC(O)CC(O)CC WYNVIVRXHYGNRT-UHFFFAOYSA-N 0.000 description 1
- BCKOQWWRTRBSGR-UHFFFAOYSA-N octane-3,6-diol Chemical compound CCC(O)CCC(O)CC BCKOQWWRTRBSGR-UHFFFAOYSA-N 0.000 description 1
- YOEZZCLQJVMZGY-UHFFFAOYSA-N octane-4,5-diol Chemical compound CCCC(O)C(O)CCC YOEZZCLQJVMZGY-UHFFFAOYSA-N 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 239000003381 stabilizer 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
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 210000000434 stratum corneum Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/02—Acyclic compounds
-
- 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
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/047—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates having two or more hydroxy groups, e.g. sorbitol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/345—Alcohols containing more than one hydroxy group
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Medicinal Chemistry (AREA)
- Emergency Medicine (AREA)
- Birds (AREA)
- Chemical & Material Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The present invention relates to a composition comprising at least 3 different diols, wherein said diols have the general structure (CH2)nH2O2, wherein n is the number of CH2 and being between 3 to 10, in a total amount of from about 0.1 to about 50 % (v/v), a method for producing the composition and its use, such as in therapy. The composition may be a pharmaceutical, cosmetic, antimicrobial or preservative composition. The composition is useful in inactivating microorganisms or preventing their growth.
Description
COMPOSITION COMPRISING AT LEAST 3 DIFFERENT DIOLES
FIELD OF THE INVENTION The present invention relates to a composition comprising at least 3 different diols, wherein the diols have the general structure (CH2) nH202, wherein n is the number of CH2 and is between 3 to 10, in one total amount from about 0.1 to about 50% (v / v), a method for producing the composition and its use, such as in therapy. The composition can be a pharmaceutical, cosmetic, antimicrobial or preservative composition. The composition is useful in inactivating microorganisms or preventing their growth. BACKGROUND OF THE INVENTION Microbes can be inactivated in different ways depending on the purpose to inactivate them. The procedure differs depending on whether the purpose is to prevent the growth of microorganisms, inhibit further growth or reduce and eliminate the microorganism. Additionally, the method differs depending on where the microorganism is located such as in a liquid, on a surface, within a mammalian body, etc. However, there are certain conditions that need to be met which are independent of the criteria mentioned R? F. 181730
previously. In addition to being highly effective, the composition to be used should be non-toxic, non-allergenic, environmentally friendly and possible to manufacture at a reasonable cost. An example of such an agent is propan-1,2-diol
(propylene glycol), which is the only diol widely used to inactivate microorganisms in dermatology. In addition, pentan-1,5-diol has been used as a component in topical pharmaceutical compositions, where it has been shown to increase the percutaneous absorption of active substances more efficiently than propan-1,2-diol. The water binding capacity of pentan-1, 5-diol is greatly comparable to that of propan-1,2-diol, but it penetrates more efficiently into the deeper parts of the stratum corneum of the skin. In addition, pentan-1,5-diol is cosmetically attractive, has a low risk of skin and eye irritation compared to other diols, has low toxicity and is odorless. WO 03/035021 describes a topical composition for skin care or administration of a pharmacologically active agent in the form of a lotion, cream or the like comprising from 5% to 70% by weight of pentan-1,5-diol in a cosmetically or pharmaceutically acceptable carrier. The multi-resistance of bacteria to antibiotics is becoming increasingly common. In the sector of
health there is now a high global interest regarding the future use of traditional antimicrobials. Alternative methods and procedures have been used to manufacture effective antimicrobial agents. PCT / SE2004 / 001001 describes the in vitro effect of pentan-1,5-diol against both gram-positive and gram-negative bacteria both sensitive and multi-resistant to antibiotics. Pentan-1,5-d? Ol was highly effective with minimal inhibitory concentrations (MIC) in the range of 5 to 12.5% against aerobic bacteria both sensitive and multi-resistant. The exact mechanism of the inhibitory action is unknown; possibly pentan-1, 5-d? ol removes water from the bacterial cytoplasm, which causes the cell to collapse. Importantly, it seems to be difficult for bacteria to develop resistance against pentan-1, 5-d-ol. The high antimicrobial activity against multi-resistant bacteria has made pentan-1,5-d? Ol an interesting agent for topical antimicrobial therapy in humans and animals. The use of 2-met? L-pentan-2, -d? Ol in pharmaceutical compositions for transdermal delivery is described in US 4855294 A, US 5026556 A, US 5041 439 A, 6271219 Bl. However, there is an increased medical need to identify new antimicrobial compositions, which can be effectively used to inactivate microorganisms. In particular there is a list
growing microorganisms, such as bacteria, viruses and fungi, which are becoming resistant to antibiotics. Additionally, there is an increased population of individuals that become allergenic against a variety of antibiotics or preservative components used in antibacterial preparations, which also demands the development of new compositions which can be used as alternatives to conventional technologies. BRIEF DESCRIPTION OF THE INVENTION The invention relates to a composition, such as an antimicrobial composition having improved properties such as being highly effective, non-toxic, non-allergenic, environmentally friendly and possible to manufacture at reasonable costs. By combining different specific diols, it has surprisingly been found that it is possible to reduce / inhibit the growth of microorganisms to a greater degree compared when using diols alone or combinations of similar diols. The present invention relates to a composition comprising at least 3 different diols, wherein the diols have the general structure (CH2) nH202, wherein n is the number of CH2 and is between 3 to 10, in a total amount from about 0.1 to approximately 50% (v / v), it is
say, the first OH group can be on the first carbon atom in all the diols and the second on different carbon atoms, such as on 2, 3, 4 or 5 carbon atoms. Additionally, the invention relates to a pharmaceutical composition comprising a pharmaceutically acceptable salt, diluent, excipient, carrier or adjuvant and the antimicrobial composition. Additionally, the invention relates to a cosmetic or preservative composition. Accordingly, the invention relates to the use of the composition, the pharmaceutical composition, the cosmetic composition, the antimicrobial composition or the preservative composition. Additionally, the invention relates to a method for manufacturing a composition comprising the steps of: providing at least 3 different diols, adding a liquid or solid agent, mixing and obtaining a composition having a total amount from about 0.1 to about 50% (v / v) of the diols. Finally, the invention relates to a method for treating an antimicrobial infection comprising administering to a patient a therapeutically effective amount of a pharmaceutical composition as mentioned above. Providing such a new composition, which has a
Wide use such as being an antimicrobial composition, the list of useful compounds to inactivate microorganisms will be increased. Additionally, due to the unique properties (i.e., being able to inactivate more than one microorganism) the new antimicrobial composition of the invention will be suitable in cases where there is a need to inactivate more than one microorganism. Accordingly, the composition of the invention shows an increased effect compared to other combinations of diols or when one and the same diol is used alone. It has also been found that by using the unique combination of diols as defined above it is possible to use a lower concentration of the different diols. DETAILED DESCRIPTION OF THE INVENTION In the context of the present invention the following definitions apply: The term "inactive" is proposed to mean that the antimicrobial composition is capable of preventing and / or inhibiting and / or eliminating and / or reducing the amount of living microorganism. The term "pharmaceutically active agent" is intended to mean any active agent, which may be used to treat a disorder or disease. Examples are cortisone, antimicrobial agents, immunomodulation agents and anti-acne agents.
ANTIMICROBIAL COMPOSITION The present invention relates to a composition comprising at least 3 different diols, wherein the diols have the general structure (CH2) nH2? 2, wherein n is the number of CH2 and is between 3 to 10, in a total amount from about 0.1 to about 50% (v / v), such as n being 3, 4, 5, 6, 7, 8, 9 or 10 or a mixture thereof. N may be different between the three different diols and at least one OH group may be on different carbon atoms in the different diols or both on different carbon atoms. The composition may contain diols having different length. In addition, the diols can be selected from the group consisting of propan-1,2-diol, propan-1,3-diol, butan-1,2-diol, butan-1,3-diol, butan-1,4- diol, 2-methylpropan-l, 2-diol, 2-methylpropan-l, 3-diol, pentan-1,2-diol, pentan-1,3-diol, pentan-1,4-diol, pentan-1, 5-diol, pentan-2, 3-diol, pentan-2,4-diol, 2-methyl-pentan-2, -diol, hexan-1,2-diol, hexane-1,3-diol, hexan-1 , 4-diol, hexane-1,5-diol, hexane-1,6-diol, hexane-2,3-diol, hexan-2,4-diol, hexan-2,5-diol, hexan-3, - diol, heptan-1, 2-diol, heptan-1,3-diol, heptan-1,4-diol, heptan-1,5-diol, heptan-1,6-diol, heptan-1,7-diol, heptan-2, 3-diol, heptan-2,4-diol, heptan-2, 5-diol, heptan-2, β-diol, heptan-3,4-diol, heptan-3,5-diol, octan- 1,2-diol, octan-1,3-diol, octan-1,4-diol, octan-1,5-diol, octane-1,6-diol, octan-1,7-diol, octan-1, 8-diol, octan-2, 3-diol,
octan-2, 4-diol, octan-2, 5-diol, octan-2, 6-diol, octan-2,7-diol, octan-3,4-diol, octan-3, 5-diol, octan- 3,6-diol and octan-4,5-diol such as a group consisting of diols having a length of from 3 to 6 carbon atoms, such as from the group consisting of 2-methyl-pentan-2, 4- diol, propan-1,2-diol, pentan-1,5-diol and butan-1,3-diol. An example is a mixture of 2-methyl-pentan-2,4-diol, propan-1,2-diol and pentan-1,5-diol. The composition may contain at least 4 or 5 different diols. The stereochemistry of the diols is not important for the present invention, and enantiomers, diastereomers, tautomers and racemic mixtures of diols can all be used with good results. Indeed, the requirement that the diols be "different" should be understood to mean that they differ in the connectivity of the atoms (regioisomerism) and not in whether they are, for example, R / S or +/-. Additionally, the composition may comprise at least 4 or 5 different diols. If the composition is used as an antimicrobial composition, the number of diols is dependent on which microbe will be inactivated. The diols may be present in an amount from about 0.25-50% v / v, such as from about 0.25 to about 20% v / v. For example, 0.25, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20%
v / v. The percentages given in this text should be understood as quantities calculated on a volume / volume basis. Additionally, the composition may comprise at least one additional component such as an alcohol, for example ethanol. Accordingly, the composition if it will be used as an antimicrobial composition, comprises an additional agent or mixture of agents, such as one or more anti-microbial agents. Examples of such agents are fusidic acid, gentamicin, neomycin, allylamines, cyclopirox, amorolfine, nystatin, amphotericin, ie antibacterial, antiviral and antifungal agents, such as imidazoles, acyclovir, and vectavir. The composition of the invention can take the form of a liquid, semi-liquid or solid disinfectant preparation, a bacteriostatic solution, lotion, cream, soup, shampoo, ointment, paste, wet towel, toilet bowl, patch, diaper or hygiene article similar staff. One form of the composition is a topical composition useful for all types of topical administration, including dry skin restoration, treatment of different disorders including microbial as well as applied to mucous membranes such as the membranes of the eye and the ear. The invention
it also relates to a pharmaceutical composition comprising the composition defined above, including a pharmaceutically acceptable salt, diluent, excipient, carrier or adjuvant. The pharmaceutical compositions of the invention are typically administered in a composition that includes one or more pharmaceutically acceptable adjuvants or excipients. Such pharmaceutical compositions can be prepared in a manner known in the art and are sufficiently stable in storage and suitable for administration to humans and animals. "Pharmaceutically acceptable" means an adjuvant or excipient which - in the dosage and concentrations employed - does not cause some undesired effects in the patients to whom it is administered. Such pharmaceutically acceptable carriers or excipients are well known in the art (see Remington's Pharmaceutical Sciences, 18th edition, AR Gennaro, Ed., Mack Publishing Company (1990) and manual of Pharmaceutical Excipients, 3rd edition, A. Kibbe, Ed., Pharmaceutical Press (2000) The pharmaceutical compositions can be subjected to conventional pharmaceutical operations such as sterilization and / or they can contain conventional adjuvants such as preservatives, stabilizers, agents
humectants, emulsifiers, buffers, fillers, etc., as described herein. The pharmaceutical composition according to the invention can be administered topically such as ointments, lotions, pastes, creams, gels, talc, aerosols, solutions and emulsions. Ointments, lotions, creams and gels may contain, in addition to the antimicrobial agent or agents, excipients such as animal and vegetable fats, waxes, paraffins, starch, tragacanth, cellulose derivatives, polyethylene glycols, silicones, bentonites, silicic acid, talc and rust. of zinc or mixtures of these substances. Talc and aerosols may contain, in addition to the antimicrobial agent or agents, excipients such as lactose, talc, silicic acid, aluminum hydroxide, calcium silicate and polyamide powders or mixtures thereof. The aerosols may also contain propellants such as florofluorohydrocarbons. The solutions and emulsions may contain excipients such as solvents, solubilizing agents and emulsifiers such as water, ethyl alcohol, isopropyl alcohol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene alcohol, d-methylformamide, oils such as oil cottonseed oil, peanut oil, corn germ oil, olive oil, castor oil and sesame oil, glycerol, glycerol formal, alcohol
tetrahydrofurfuryl, polyethylene glycols and fatty acid esters such as sorbitan and mixtures thereof. The pharmaceutical composition will be administered to a patient in a pharmaceutically effective dose. By "pharmaceutically effective dose" is meant a dose that is sufficient to produce the desired effects in relation to the condition for which it is administered. The exact dose is dependent on, the activity of the compound, the manner of administration, nature and severity of the disorder, age and body weight of the patient, and different doses may be necessary. Administration of the dose can be carried out by single administration in the form of a single dose unit or by various small dose units or by multiple administration of subdivided doses at specific intervals. The pharmaceutical composition of the invention can be administered alone or in combination with other therapeutic agents. These agents can be incorporated as part of the same pharmaceutical composition. The "patient" for the purposes of the present invention includes both humans and other mammals. Accordingly, the methods are applicable for both human therapy and veterinary applications. The invention also relates to a cosmetic composition or topical formulations comprising the
antimicrobial composition as defined above and a gel, cream, ointment, suspension, aerosol, paste, powder, lotion. The composition of the invention, pharmaceutical composition, cosmetic composition, antimicrobial composition or conversational composition can be used to inactivate microorganisms selected from the group consisting of gram positive and gram negative bacteria, fungi, including yeasts, molds and dermatophytes and viruses. Examples include, but are not limited to, Staphylococcus aureus, Streptococci, Gram negative bacilli, Candida albi cans, Candida glabra ta, Malassezia, M. fúrfur, Aspergillus flavus mold and Dermatophytes Tri chophyton rubrum, T. men tagrophytes, Epidermophyton floccusum, My crosporum canis, papilloma virus, herpes virus, and pox virus. Other useful uses are the restoration of dry skin. The invention also relates to a method for manufacturing a composition as defined above comprising the steps of: providing at least 3 different diols as mentioned above, adding a liquid or solid agent, blends and obtaining a composition, such as a composition antimicrobial having a total amount from about 0.1 to about 50 (v / v) of the diols. Accordingly, the invention relates to a
method for treating an antimicrobial infection comprising administering to a patient a therapeutically effective amount of a pharmaceutical composition as defined above. Finally, the invention relates to the use of the diols mentioned above as a preservative, without the use of other preservatives such as parabens, sodium lauryl sulfate, ascorbic acid, etc. A preservative may be used, for example, in contact lens solutions, shampoo, toothpaste, liquid soap, laundry solutions, creams, ointments, paste or cleaning solutions. The following examples are proposed to illustrate but not limit the invention in any way, aspect or form, either explicitly or implicitly. Material and Methods Microorganisms. Staphylococcus aureus number
515x6352 and Candida albicans H 29 were obtained from Collection in the Department of Microbiology, Sahlgrenska University Hospital, Gothenburg, Sweden. The isolates were kept on blood agar at 37 ° C. M.sympodíalis CBS 7222 and M. globosa CBS 7966 Compounds. Propan-1, 2-diol, pentan-1,5-diol and 2-methylpentan-2,4-diol and butan-1,3-diol were obtained from Merck
Schuchardt, Hohenbrum, Germany with a purity of 98 to 98.5%. Example 1 Bactepostatic effect test (MIC = minimum inhibitory concentration) Each of the diols and their combination (1: 1: 1 volume / volume) was diluted directly with the test culture medium:, Diagnostic Sensitivity Test (DST) agar (Oxoid, UK) to obtain concentrations, in the test medium, of 2, 3, 4, 6, 9, and 12% percent by volume of the respective diol and of 2.3, and 4% of the respective diol in the combination. S aureus cells were added to the agar medium at concentrations of 103 and 105 cells / ml while C cells. albicans were added in a concentration of
10fc cells / ml and M sympodialis and M. globosa at a concentration of 10 cells / ml The plates were incubated at 37 ° C and analyzed after 1 and 2 days. Each experiment was repeated. MIC (Minimum Inhibitory Concentration) was defined as the lowest concentration that totally inhibited growth. The MICs for propan-1, 2-d? Ol, pentan-1,5-diol, 2-met? Lpentan-2, 4-d? Ol and the combination of these 3 diols are shown in table 1. The table shows the effect (MIC in%) of propan-1,2-d? ol, pentan-1, 5-d? ol, 2-met? lpentan-2, 4-d? ol and its
combination on the growth of Staphylococcus aureus and Candida albicans in vitro. The combination of 3% of each of the 3 diols completely inhibited S growth. aureus and a combination of 2% completely inhibited the growth of C. albicans and a concentration of 0.5% completely inhibited the growth of M. sympodialis and M. globose With a combination of 4 diols a combination of 2% completely inhibited the growth of S aureus and a combination of 1% completely inhibited the growth of C. albicans and a concentration of 0.25% completely inhibited the growth of M. sympodial is and M. globosa. For
S. aureus, the same activity was obtained only with a total of 12% pentan-1, 5-diol and 2-me t ipentan-2,4-diol when tested alone. Propan-1,2-diol, butan-1,3-diol and ethanol were not able to inhibit the growth of S. aureus, still at 12%. EXAMPLE 2 Preparation of a topical pharmaceutical composition bac ter ios tica A mixture of equal amount of propan-1,2-diol + pentan-1,5-diol + 2-methyl pentan-2,4-diol was mixed with the Essex® cream base (Schering Plow) at a final concentration of 2 or 3%.
Example 3 Example 3 was carried out as example 1
+ indicates that the composition shows an effect - indicates that the composition shows less effect or no effect It is noted that in relation to this date, the best method known by the applicant to implement the aforementioned invention, is that which is clear of the present description of the invention.
Claims (23)
- CLAIMS Having described the invention as above, the content of the following claims is claimed as property: 1. Composition, characterized in that it comprises at least 3 different diols, wherein the diols have the general structure (CH2) nH2? 2, where n is the number of CH2 that is between 3 to 6, in a total amount from about 0.1 to about 50% (v / v).
- 2. Composition according to claim 1, characterized in that n is different among the 3 diols.
- 3. Composition according to any of the preceding claims, characterized in that at least one OH group is in different carbon atoms in the different diols. Composition according to any of the preceding claims, characterized in that the diols are selected from the group consisting of propan-1,2-diol, propan-1,3-diol, butan-1,2-diol, butan-1 , 3-diol, butan-1,4-diol, 2-methylpropan-l, 2-diol, 2-methylpropan-l, 3-diol, pentan-1,2-diol, pentan-1,3-diol, pentan -1,4-diol, pentan-1,5-diol, pentan-2,3-diol, pentan-2,4-diol, 2-methyl-pentan-2,4-diol, hexan-1,2-diol , hexan-1, 3-diol, hexane-1,4-diol, hexane-1,5-diol, hexane-1,6-diol, hexan-2, 3-diol, hexan-2,4-diol, hexan - 2,5-diol, and hexane-3,4-diol. Composition according to claim 1 to 4, characterized in that the diols are selected from the group consisting of 2-methyl-pentan-2,4-diol, propan-1,2-diol, pentan-1,5-diol and butan-1,3-diol. An example is a mixture of 2-methyl-pentan-2,4-diol, propan-1,2-diol and pentan-1,5-diol. The composition according to any of the preceding claims, wherein the diols are 2-methyl-pentan-2,4-diol, propan-1,2-diol and pentan-1,5-diol. 6. Composition according to any of the preceding claims, characterized in that the composition comprises at least 4 or 5 different diols. Composition according to any of the preceding claims, characterized in that the diols are present in an amount from about 0.25 to about 50% (v / v). 8. Composition in accordance with the claim 7, characterized in that the diols are present in an amount from about 0.25 to about 20%. 9. Composition in accordance with the claim 8, characterized in that the diols are present in an amount of 0.25, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20% v / v. 10. Composition according to any of the preceding claims, characterized in that the The composition comprises an additional antimicrobial agent selected from the group consisting of antibacterial, antiviral and antifungal agents. 11. Composition according to claim 10, characterized in that the agents are selected from the group consisting of fusidic acid, gentamicin, neomycin, allylamines, cyclopirox, amorolfine, nystatin, amphotericin, imidazoles, acyclovir, and vectavir. 12. Composition according to any of the preceding claims, characterized in that the composition comprises one or more alcohols. 13. Pharmaceutical composition, characterized in that it comprises a pharmaceutically acceptable salt, diluent, excipient, carrier or adjuvant and the composition according to any of the preceding claims. 14. Pharmaceutical composition according to claim 13, characterized in that the composition comprises a pharmaceutically active agent. 15. Cosmetic composition, characterized in that it comprises the composition according to any of claims 1-12. 16. Conservative composition, characterized in that it comprises the composition according to any of claims 1-12. 17. Antimicrobial composition, characterized in that it comprises the composition according to any of claims 1-12. 18. Composition according to any of the preceding claims, characterized because it is in some ointments, lotions, pastes, creams, gels, talc, sprays, solutions, an emulsion soap, shampoo, ointment, paste, wet wipe, hygienic container, patch or diaper. 19. Use of the composition according to claims 1-12, the pharmaceutical composition according to claims 13-14, the cosmetic composition according to claim 15 or the preservative composition according to claim 16 or the antimicrobial composition. according to claim 17 and the composition according to claim 18 for inactivation of microorganisms. 20. Use according to claim 19, wherein the microorganism is selected from the group consisting of gram positive and gram negative bacteria, viruses and fungi. 21. Use according to claim 20, wherein the microorganism is selected from the group consisting of Staphylococcus aureus, Streptococci, Gram negative bacilli, Candida albi cans, Candida glabra ta, Malassezia, M. furfur, Aspergillus flavus, Tri chophyton rubrum, T. men tagrophytes, Epidermophyton floccusum, My crosporum canis, papilloma virus, herpes virus, and pox virus. 22. A method for manufacturing a composition, characterized in that it comprises the steps of: i) providing at least 3 different diols according to any of claims 1-12, ii) adding a liquid or solid agent, m) mixing and iv) obtaining a composition having a total amount from about 0.1 to about 50% (v / v) of the diols. 23. Method for treating a microbial infection, characterized in that it comprises administering to a patient a therapeutically effective amount of a pharmaceutical composition according to claims 13-14.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US63114800P | 2000-11-29 | 2000-11-29 | |
SE0402890A SE528780C2 (en) | 2004-11-29 | 2004-11-29 | Composition useful for inactivation of microorganisms e.g. gram positive and gram negative bacteria, virus and fungi, comprises at least three different diols |
PCT/SE2005/001787 WO2006057616A1 (en) | 2004-11-29 | 2005-11-29 | A composition comprising at least 3 different diols |
Publications (1)
Publication Number | Publication Date |
---|---|
MX2007006125A true MX2007006125A (en) | 2007-07-13 |
Family
ID=33538392
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
MX2007006125A MX2007006125A (en) | 2000-11-29 | 2005-11-29 | A composition comprising at least 3 different diols. |
Country Status (4)
Country | Link |
---|---|
CN (1) | CN101065118B (en) |
DK (1) | DK1827433T4 (en) |
MX (1) | MX2007006125A (en) |
SE (1) | SE528780C2 (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2811526T3 (en) | 2010-12-30 | 2021-03-12 | Lab Francais Du Fractionnement | Glycols as pathogen inactivating agents |
CN108567579B (en) * | 2018-07-27 | 2021-08-03 | 广州世航生物科技有限公司 | Preservative composition and use thereof |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5369129A (en) * | 1989-06-13 | 1994-11-29 | Hydro Pharma Ab | Preparation of topical treatment of infections caused by virus, bacteria and fungi |
DE10206759A1 (en) * | 2002-02-19 | 2003-08-28 | Dragoco Gerberding Co Ag | Use of 1,2-alkanediol mixture as an antimicrobial agent, e.g. for treating body odor, acne or mycoses or preserving perishable products |
-
2004
- 2004-11-29 SE SE0402890A patent/SE528780C2/en unknown
-
2005
- 2005-11-29 DK DK05804731.7T patent/DK1827433T4/en active
- 2005-11-29 MX MX2007006125A patent/MX2007006125A/en not_active Application Discontinuation
- 2005-11-29 CN CN2005800405632A patent/CN101065118B/en active Active
Also Published As
Publication number | Publication date |
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DK1827433T3 (en) | 2013-03-04 |
CN101065118A (en) | 2007-10-31 |
SE528780C2 (en) | 2007-02-13 |
SE0402890L (en) | 2006-05-30 |
CN101065118B (en) | 2011-06-15 |
DK1827433T4 (en) | 2015-12-07 |
SE0402890D0 (en) | 2004-11-29 |
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