JP2008521799A - 組成物 - Google Patents
組成物 Download PDFInfo
- Publication number
- JP2008521799A JP2008521799A JP2007542986A JP2007542986A JP2008521799A JP 2008521799 A JP2008521799 A JP 2008521799A JP 2007542986 A JP2007542986 A JP 2007542986A JP 2007542986 A JP2007542986 A JP 2007542986A JP 2008521799 A JP2008521799 A JP 2008521799A
- Authority
- JP
- Japan
- Prior art keywords
- diol
- composition
- octane
- pentane
- composition according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 97
- 150000002009 diols Chemical class 0.000 claims abstract description 54
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- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 31
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims description 24
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims description 18
- 230000000845 anti-microbial effect Effects 0.000 claims description 15
- 235000013772 propylene glycol Nutrition 0.000 claims description 15
- 229960004063 propylene glycol Drugs 0.000 claims description 15
- 239000004146 Propane-1,2-diol Substances 0.000 claims description 14
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 12
- 239000004599 antimicrobial Substances 0.000 claims description 12
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- 229940079593 drug Drugs 0.000 claims description 8
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- 229910052623 talc Inorganic materials 0.000 claims description 5
- BTVWZWFKMIUSGS-UHFFFAOYSA-N 2-methylpropane-1,2-diol Chemical compound CC(C)(O)CO BTVWZWFKMIUSGS-UHFFFAOYSA-N 0.000 claims description 4
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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
- DCTMXCOHGKSXIZ-UHFFFAOYSA-N (R)-1,3-Octanediol Chemical compound CCCCCC(O)CCO DCTMXCOHGKSXIZ-UHFFFAOYSA-N 0.000 claims description 2
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- 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
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- 241000192125 Firmicutes 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
- 241000555688 Malassezia furfur Species 0.000 claims description 2
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- 241001631646 Papillomaviridae Species 0.000 claims description 2
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- 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
- 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
- 208000032343 candida glabrata infection Diseases 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
- 229960003749 ciclopirox Drugs 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
- GCXZDAKFJKCPGK-UHFFFAOYSA-N heptane-1,2-diol Chemical compound CCCCCC(O)CO GCXZDAKFJKCPGK-UHFFFAOYSA-N 0.000 claims description 2
- HTXVEEVTGGCUNC-UHFFFAOYSA-N heptane-1,3-diol Chemical compound CCCCC(O)CCO HTXVEEVTGGCUNC-UHFFFAOYSA-N 0.000 claims description 2
- OGRCRHSHBFQRKO-UHFFFAOYSA-N heptane-1,4-diol Chemical compound CCCC(O)CCCO OGRCRHSHBFQRKO-UHFFFAOYSA-N 0.000 claims description 2
- NNYOSLMHXUVJJH-UHFFFAOYSA-N heptane-1,5-diol Chemical compound CCC(O)CCCCO NNYOSLMHXUVJJH-UHFFFAOYSA-N 0.000 claims description 2
- UQGLNXPQGUMNRU-UHFFFAOYSA-N heptane-1,6-diol Chemical compound CC(O)CCCCCO UQGLNXPQGUMNRU-UHFFFAOYSA-N 0.000 claims description 2
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 claims description 2
- VUVZASHBYYMLRC-UHFFFAOYSA-N heptane-2,3-diol Chemical compound CCCCC(O)C(C)O VUVZASHBYYMLRC-UHFFFAOYSA-N 0.000 claims description 2
- XVEOUOTUJBYHNL-UHFFFAOYSA-N heptane-2,4-diol Chemical compound CCCC(O)CC(C)O XVEOUOTUJBYHNL-UHFFFAOYSA-N 0.000 claims description 2
- XTVHTJKQKUOEQA-UHFFFAOYSA-N heptane-2,5-diol Chemical compound CCC(O)CCC(C)O XTVHTJKQKUOEQA-UHFFFAOYSA-N 0.000 claims description 2
- OZIMXLFSRSPFAS-UHFFFAOYSA-N heptane-2,6-diol Chemical compound CC(O)CCCC(C)O OZIMXLFSRSPFAS-UHFFFAOYSA-N 0.000 claims description 2
- ZNZZFXONMYVVGZ-UHFFFAOYSA-N heptane-3,4-diol Chemical compound CCCC(O)C(O)CC ZNZZFXONMYVVGZ-UHFFFAOYSA-N 0.000 claims description 2
- BQWORYKVVNTRAW-UHFFFAOYSA-N heptane-3,5-diol Chemical compound CCC(O)CC(O)CC BQWORYKVVNTRAW-UHFFFAOYSA-N 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
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- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 claims description 2
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- 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
- AEIJTFQOBWATKX-UHFFFAOYSA-N octane-1,2-diol Chemical compound CCCCCCC(O)CO AEIJTFQOBWATKX-UHFFFAOYSA-N 0.000 claims description 2
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Abstract
Description
本発明は、改善された特性を有する、例えば高度に効果的、非毒性、非アレルギー性、環境に優しく、且つ適切なコストで製造することが可能な組成物、例えば抗菌組成物に関する。特定の異なるジオールを混合することにより、驚くべきことに、ジオールを単独又は類似のジオールとの組み合わせで用いる場合と比較して、より高い程度で微生物の成長を減少/阻害することができることを見出した。
本発明との関連においては、以下の定義を適用する:
本発明は、約0.1〜約50%(v/v)の総量において、少なくとも3つの異なるジオールを含んで成り、当該ジオールが一般構造(CH2)nH2O2を有し、nがCH2の数であって3〜10、例えばnが3、4、5、6、7、8、9又は10、或いはそれらの混合である組成物に関する。Nは、3つ異なるジオールの間で異なることができ、少なくとも1つのOH基は、異なるジオール中の異なる炭素原子に存在し、或いは両方とも異なる炭素原子に存在することができる。組成物は、異なる長さを有するジオールを含むことができる。更に、ジオールは、プロパン−1,2−ジオール、プロパン−1,3−ジオール、ブタン−1,2−ジオール、ブタン−1,3−ジオール、ブタン−1,4−ジオール、2−メチルプロパン−1,2−ジオール、2−メチルプロパン−1,3−ジオール、ペンタン−1,2−ジオール、ペンタン−1,3−ジオール、ペンタン−1,4−ジオール、ペンタン−1,5−ジオール、ペンタン−2,3−ジオール、ペンタン−2,4−ジオール、2−メチル−ペンタン−2,4−ジオール、ヘキサン−1,2−ジオール、ヘキサン−1,3−ジオール、ヘキサン−1,4−ジオール、ヘキサン−1,5−ジオール、ヘキサン−1,6−ジオール、ヘキサン−2,3−ジオール、ヘキサン−2,4−ジオール、ヘキサン−2,5−ジオール、ヘキサン−3,4−ジオール、ヘプタン−1,2−ジオール、ヘプタン−1,3−ジオール、ヘプタン−1,4−ジオール、ヘプタン−1,5−ジオール、ヘプタン−1,6−ジオール、ヘプタン−1,7−ジオール、ヘプタン−2,3−ジオール、ヘプタン−2,4−ジオール、ヘプタン−2、5−ジオール、ヘプタン−2,6−ジオール、ヘプタン−3,4−ジオール、ヘプタン−3,5−ジオール、オクタン−1,2−ジオール、オクタン−1,3−ジオール、オクタン−1,4−ジオール、オクタン−1,5−ジオール、オクタン−1,6−ジオール、オクタン−1,7−ジオール、オクタン−1,8−ジオール、オクタン−2,3−ジオール、オクタン−2,4−ジオール、オクタン−2、5−ジオール、オクタン−2、6−ジオール、オクタン−2、7−ジオール、オクタン−3,4−ジオール、オクタン−3、5−ジオール、オクタン−3,6−ジオール及びオクタン−4、5−ジオールから成る群、例えば3〜6の炭素原子を有するジオールから成る群、例えば2−メチル−ペンタン−2,4−ジオール、プロパン−1,2−ジオール、ペンタン−1,5−ジオール及びブタン−1,3−ジオールから成る群から選択することができる。1つの例は、2−メチル−ペンタン−2,4−ジオール、プロパン−1,2−ジオール及びペンタン−1,5−ジオールの混合物である。
微生物。黄色ブドウ球菌(Staphylococcus aureus)番号515x6352及びカンジダ・アルビカンス(Candida albicans)H29は、Collection in the Department of Microbiology(Sahlgrenska University Hospital, Gothenburg,Sweden)から得た。単離物は、血液寒天上で37℃において保持した。
静菌効果に関する試験(MIC=最小発育阻止濃度)。
各ジオール及びそれらの組み合わせ(1:1:1 体積/体積)を、試験培地、診断鋭敏度試験寒天(DST)(Oxoid、UK)で直接的に希釈し、試験培地中で、2、3、4、6、9及び12%体積パーセントの各ジオールの濃度、並びに2、3、及び4%の組み合わせにおける各ジオールの濃度を得た。
静菌性局所医薬組成物の調製
プロパン−1,2−ジオール+ペンタン−1,5−ジオール+2−メチルペンタン−2,4−ジオールの等量の混合物を、Essex(登録商標)クリーム基剤(Schering Plough)と混合し、2又は3%の最終濃度とした。
実施例3は、実施例1のように実施した。
Claims (26)
- 約0.1〜約50%(v/v)の総量において、少なくとも3つの異なるジオールを含んで成り、当該ジオールが一般構造(CH2)nH2O2を有し、nがCH2の数であって3〜10である組成物。
- nが3、4、5、6、7、8、9又は10、或いはそれらの混合である、請求項1に記載の組成物。
- nが3つのジオールの間で異なる、請求項2に記載の組成物。
- 少なくとも1つのOH基が、異なるジオール中の異なる炭素原子に存在する、請求項1〜3のいずれか一項に記載の組成物。
- ジオールが、プロパン−1,2−ジオール、プロパン−1,3−ジオール、ブタン−1,2−ジオール、ブタン−1,3−ジオール、ブタン−1,4−ジオール、2−メチルプロパン−1,2−ジオール、2−メチルプロパン−1,3−ジオール、ペンタン−1,2−ジオール、ペンタン−1,3−ジオール、ペンタン−1,4−ジオール、ペンタン−1,5−ジオール、ペンタン−2,3−ジオール、ペンタン−2,4−ジオール、2−メチル−ペンタン−2,4−ジオール、ヘキサン−1,2−ジオール、ヘキサン−1,3−ジオール、ヘキサン−1,4−ジオール、ヘキサン−1,5−ジオール、ヘキサン−1,6−ジオール、ヘキサン−2,3−ジオール、ヘキサン−2,4−ジオール、ヘキサン−2,5−ジオール、ヘキサン−3,4−ジオール、ヘプタン−1,2−ジオール、ヘプタン−1,3−ジオール、ヘプタン−1,4−ジオール、ヘプタン−1,5−ジオール、ヘプタン−1,6−ジオール、ヘプタン−1,7−ジオール、ヘプタン−2,3−ジオール、ヘプタン−2,4−ジオール、ヘプタン−2,5−ジオール、ヘプタン−2,6−ジオール、ヘプタン−3,4−ジオール、ヘプタン−3,5−ジオール、オクタン−1,2−ジオール、オクタン−1,3−ジオール、オクタン−1,4−ジオール、オクタン−1,5−ジオール、オクタン−1,6−ジオール、オクタン−1,7−ジオール、オクタン−1,8−ジオール、オクタン−2,3−ジオール、オクタン−2,4−ジオール、オクタン−2,5−ジオール、オクタン−2,6−ジオール、オクタン−2,7−ジオール、オクタン−3,4−ジオール、オクタン−3,5−ジオール、オクタン−3,6−ジオール及びオクタン−4,5−ジオールから成る群から選択される、請求項1〜4のいずれか一項に記載の組成物。
- nが3〜6である、請求項1〜5のいずれか一項に記載の組成物。
- ジオールが、2−メチル−ペンタン−2,4−ジオール、プロパン−1,2−ジオール、ペンタン−1,5−ジオール及びブタン−1,3−ジオールから成る群から選択される、請求項6に記載の組成物。
- ジオールが、2−メチル−ペンタン−2,4−ジオール、プロパン−1,2−ジオール及びペンタン−1,5−ジオールである、請求項1〜7のいずれか一項に記載の組成物。
- 組成物が、少なくとも4又は5つの異なるジオールを含んで成る、請求項1〜8のいずれか一項に記載の組成物。
- ジオールが、約0.25〜約50%(v/v)の量で存在する、請求項1〜9のいずれか一項に記載の組成物。
- ジオールが、約0.25〜約20%の量で存在する、請求項10に記載の組成物。
- ジオールが、0.25、0.5、1 、2、3、4、5、6、7、8、9、10、11 、12、13、14、15、16、17、18、19又は20%v/vの量で存在する、請求項11に記載の組成物。
- 組成物が、抗細菌剤、抗ウイルス剤及び抗真菌剤から成る群から選択される、追加の抗菌剤を含んで成る、請求項1〜12のいずれか一項に記載の組成物。
- 薬剤が、フシジン酸、ゲンタマイシン、ネオマイシン、アリルアミン、シクロピロックス、アモロルフィン、ナイスタチン、アンフォテリシン、イミダゾール、アイクロビル、及びベクタビル(vectavir)から成る群から選択される、請求項13に記載の組成物。
- 組成物が1つ以上のアルコールを含んで成る、請求項1〜14のいずれか一項に記載の組成物。
- 医薬として許容される塩、希釈剤、賦形剤、担体又はアジュバント及び請求項1〜15のいずれか一項に記載の組成物を含んで成る、医薬組成物。
- 組成物が医薬活性剤を含んで成る、請求項16に記載の医薬組成物。
- 請求項1〜15のいずれか一項に記載の組成物を含んで成る化粧組成物。
- 請求項1〜15のいずれか一項に記載の組成物を含んで成る防腐組成物。
- 請求項1〜15のいずれか一項に記載の組成物を含んで成る抗菌組成物。
- 組成物が、軟膏、ローション、ペースト、クリーム、ゲル、タルク、スプレー、溶液、エマルジョンせっけん、シャンプー、軟膏、ペースト、ウェットタオル、衛生皿、パッチ又はおむつ中に存在する、請求項1〜20のいずれか一項に記載の組成物。
- 微生物の不活性化のための、請求項1〜15に記載の組成物、請求項16〜17に記載の医薬組成物、請求項18に記載の化粧組成物、又は請求項19に記載の防腐組成物、又は請求項20に記載の抗菌組成物、及び請求項21に記載の組成物の使用。
- 微生物が、グラム陽性細菌、グラム陰性細菌、ウイルス及び真菌から成る群から選択される、請求項22に記載の使用。
- 微生物が、黄色ブドウ球菌(Staphylococcus aureus)、連鎖球菌(Streptococci)、グラム陰性桿菌(gram negative rod)、カンジダ・アルビカンス(Candida albicans)、カンジダ・グラブラタ(Candida glabrata)、マラセジア属(Malassezia)、M.フラフール(M.furfur)、カビ黄色コウジ菌(Aspergillus flavus)、皮膚糸状菌紅色白癬菌(Trichophyton rubrum)、毛瘡白癬菌(T.mentagrophytes)、エピデルモフィトン・フロクサム(Epidermophyton floccusum)、犬小胞子菌(Microsporum canis)、乳頭腫ウイルス、ヘルペスウイルス及びポックス・ウイルスから成る群から選択される、請求項23に記載の使用。
- i)請求項1〜15のいずれか一項に記載の少なくとも3つの異なるジオールを調製する段階、
ii)液体又は固形薬剤を添加する段階
iii)混合する段階、及び
iv)約0.1〜約50%(v/v)のジオールの総量を有する組成物を得る段階
を含んで成る、組成物を製造する方法。 - 治療有効量の請求項16〜17に記載の医薬組成物を患者に投与することを含んで成る、微生物感染を処置する方法。
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US63114804P | 2004-11-29 | 2004-11-29 | |
SE0402890-8 | 2004-11-29 | ||
SE0402890A SE528780C2 (sv) | 2004-11-29 | 2004-11-29 | Antimikrobiell beredning omfattande 3 eller 4 dioler och en metod för att framställa den |
US60/631,148 | 2004-11-29 | ||
PCT/SE2005/001787 WO2006057616A1 (en) | 2004-11-29 | 2005-11-29 | A composition comprising at least 3 different diols |
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EP (1) | EP1827433B2 (ja) |
JP (1) | JP5179879B2 (ja) |
KR (1) | KR20070093079A (ja) |
AU (1) | AU2005310072B2 (ja) |
BR (1) | BRPI0518676A2 (ja) |
CA (1) | CA2586815A1 (ja) |
RU (1) | RU2389481C2 (ja) |
WO (1) | WO2006057616A1 (ja) |
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JP2011527347A (ja) * | 2008-07-07 | 2011-10-27 | アンブリア ダーマトロジイ エイビー | 抗菌組成物 |
JP2021500319A (ja) * | 2017-10-18 | 2021-01-07 | シュルケウント マイヤー ゲーエムベーハー | 防腐用液体濃縮物 |
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JP4621897B2 (ja) | 2007-08-31 | 2011-01-26 | 独立行政法人産業技術総合研究所 | 固体メモリ |
US9533479B2 (en) | 2008-09-18 | 2017-01-03 | Medline Industries, Inc. | Absorbent articles having antimicrobial properties and methods of manufacturing the same |
KR101381903B1 (ko) * | 2011-03-10 | 2014-04-10 | 주식회사 엘지생활건강 | 3-부톡시-1,2-프로판다이올을 함유하는 항균 또는 보존용 조성물 |
US8853189B2 (en) | 2012-05-31 | 2014-10-07 | Prima Innovations, Llc | Antispasmodic 1,2-Diols and 1,2,3-triols |
WO2018157936A1 (en) * | 2017-03-02 | 2018-09-07 | Essity Hygiene And Health Aktiebolag | Wipe with skin beneficial effect |
WO2021198285A1 (en) * | 2020-03-31 | 2021-10-07 | Minasolve Sas | Homogeneous liquid composition comprising 1,2-octanediol and use thereof |
WO2021250155A1 (en) * | 2020-06-12 | 2021-12-16 | Dsm Ip Assets B.V. | Novel use |
EP4178356A1 (en) * | 2020-07-09 | 2023-05-17 | Symrise AG | Compositions with virucidal and/or antiviral activity |
WO2022122132A1 (en) * | 2020-12-09 | 2022-06-16 | Symrise Ag | Compositions comprising natural polymers and one or more (bio)-alkanediols |
WO2022122138A1 (en) * | 2020-12-09 | 2022-06-16 | Symrise Ag | Multifunctional compound mixtures comprising multiple (bio)-alkanediols |
KR102530593B1 (ko) * | 2022-09-27 | 2023-05-10 | 한국콜마주식회사 | 방부 상승 효과를 갖는 방부시스템 |
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- 2005-11-29 CA CA002586815A patent/CA2586815A1/en not_active Abandoned
- 2005-11-29 JP JP2007542986A patent/JP5179879B2/ja active Active
- 2005-11-29 KR KR1020077015125A patent/KR20070093079A/ko not_active Application Discontinuation
- 2005-11-29 EP EP05804731.7A patent/EP1827433B2/en active Active
- 2005-11-29 AU AU2005310072A patent/AU2005310072B2/en not_active Ceased
- 2005-11-29 RU RU2007124367/15A patent/RU2389481C2/ru active
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Also Published As
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EP1827433A1 (en) | 2007-09-05 |
JP5179879B2 (ja) | 2013-04-10 |
US20090221716A1 (en) | 2009-09-03 |
US9757596B2 (en) | 2017-09-12 |
WO2006057616A1 (en) | 2006-06-01 |
RU2007124367A (ru) | 2009-01-10 |
AU2005310072B2 (en) | 2011-06-02 |
BRPI0518676A2 (pt) | 2008-12-02 |
KR20070093079A (ko) | 2007-09-17 |
CA2586815A1 (en) | 2006-06-01 |
RU2389481C2 (ru) | 2010-05-20 |
EP1827433B1 (en) | 2012-11-21 |
AU2005310072A1 (en) | 2006-06-01 |
EP1827433B2 (en) | 2015-08-26 |
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