JPH11506441A - Hydrogel containing sorbic acid - Google Patents
Hydrogel containing sorbic acidInfo
- Publication number
- JPH11506441A JPH11506441A JP8536180A JP53618096A JPH11506441A JP H11506441 A JPH11506441 A JP H11506441A JP 8536180 A JP8536180 A JP 8536180A JP 53618096 A JP53618096 A JP 53618096A JP H11506441 A JPH11506441 A JP H11506441A
- Authority
- JP
- Japan
- Prior art keywords
- sorbic acid
- weight
- polyhydric
- ethers
- hydrogels
- 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.)
- Pending
Links
- 239000000017 hydrogel Substances 0.000 title claims abstract description 15
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 229940075582 sorbic acid Drugs 0.000 title claims abstract description 13
- 235000010199 sorbic acid Nutrition 0.000 title claims abstract description 13
- 239000004334 sorbic acid Substances 0.000 title claims abstract description 13
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 9
- 150000002170 ethers Chemical class 0.000 claims abstract description 8
- 150000005846 sugar alcohols Polymers 0.000 claims abstract description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 229920002125 Sokalan® Polymers 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- BJHIKXHVCXFQLS-OTWZMJIISA-N keto-L-sorbose Chemical class OC[C@H](O)[C@@H](O)[C@H](O)C(=O)CO BJHIKXHVCXFQLS-OTWZMJIISA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 208000002874 Acne Vulgaris Diseases 0.000 description 3
- 206010000496 acne Diseases 0.000 description 3
- -1 cyclic polyols Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003974 emollient agent Substances 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- MEJYDZQQVZJMPP-ULAWRXDQSA-N (3s,3ar,6r,6ar)-3,6-dimethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical compound CO[C@H]1CO[C@@H]2[C@H](OC)CO[C@@H]21 MEJYDZQQVZJMPP-ULAWRXDQSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002674 ointment Substances 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
- 230000035515 penetration Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- 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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Inorganic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
(57)【要約】 ヒドロゲルの形の薬剤学的製剤が記載されており、該製剤は、単独の作用物質として、ソルビン酸を、場合により多価アルコールおよび／または多価エーテルと組み合わせて含有することを特徴とする。 (57) [Summary] Pharmaceutical preparations in the form of hydrogels are described, which preparations are characterized in that they contain, as the sole active substance, sorbic acid, optionally in combination with polyhydric alcohols and / or polyhydric ethers.
Description
【発明の詳細な説明】 ソルビン酸含有ヒドロゲル 本発明は、単独の作用物質として、ソルビン酸を、場合により多価アルコール および／または多価エーテルと組み合わせて含有することを特徴とする、ヒドロ ゲルの形の薬剤学的製剤に関する。 例えば軟膏またはクリームのような局所的適用を目的とするヒドロゲルの形の 薬剤学的製剤が式Ｉ： ＣＨ3−ＣＨ＝ＣＨ−ＣＨ＝ＣＨ−ＣＯＯＨ （Ｉ） で表されるソルビン酸（２，４−ヘキサジエン酸）を含有することができ、該ソ ルビン酸が前記製剤を保存するために用いられることは周知である（Ullmann’s Encyclopedia of Industrial Chemistry 5th Ed.VCH Verlagsgesellschaft mbH D-69451 Weinheim（DE）1993,VolA24 507頁以下）。 更に、この製剤が例えばエチレングリコール、プロピレングリコール、グリセ リンまたはポリオキシアルキレンのような多価アルコールおよび／または多価エ ーテルを含有することができ、これらが皮膚を乾燥から保護し、柔軟性を保つた めに用いられる（湿潤剤、皮膚軟化剤および軟化剤）ことは周知である（Ullman n’s Encyclopedia of Industrial Chemistry 5th Ed.VCH Verlagsgesellschaft mbH D-69451 Weinheim（D E）1993,VolA10 101頁以下、VolA21 579頁以下、A22163頁）。作用物質含有製剤 の場合に、これらの添加剤は、場合により作用物質の浸透を強化する薬剤（エン ハンサー）として用いることができる。 単独の作用物質として有利には多価アルコールおよび／または多価エーテルと 組み合わせてソルビン酸を含有するヒドロゲルの形の薬剤学的製剤が、意想外に も、以下の実施例に詳細に説明されるように、局所的適用においてにきび患者の 炎症性発疹に著しい治療効果を示すことが判明した。 本発明による薬剤学的製剤に関しては、多価アルコールおよび／または多価エ ーテルとして、有利にはこの種の製剤に一般に使用されるようなこれらの物質種 類の生理学的に認容される液状の物質が適している。これらの化合物は、例えば 一般式ＩＩ： Ｈ−（Ｏ−ＣＨＲ−ＣＨ2）n−ＯＨ （ＩＩ） （式中のｎは１〜１２、有利には１〜８の数を表し、Ｒは水素原子、メチル基を 表すかまたはｎが１の数である場合はヒドロキシメチル基を表す）で表される化 合物である。 一般式Ｉの適当なアルコールまたはエーテルは、例えばエチレングリコール、 プロピレングリコール、グリセリン、ジエチレングリコール、トリエチレングリ コール、ジプロピレングリコールまたはトリプロピレングリコールである。これ らは、局所的適用を目的と する薬剤学的製剤中に、該製剤に使用される作用物質のためのエンハンサーとし て使用される物質である（例えば欧州特許出願公開第０１６５６９６号明細書、 国際特許ＷＯ８８／０１４９６号明細書およびドイツ特許出願公開第２５１５５ ９４号明細書参照）。 他方で、本発明による薬剤学的製剤は、多価アルコールまたは多価エーテルと して、例えばジメチルイソソルバイドのような環状ポリオールまたはポリエーテ ルまたはジグリコールジメチルエーテルのようなグリコールエーテルを含有する ことができる。従来実施された研究においてプロピレングリコールが特に適して いることが示された。 本発明によるヒドロゲルの形の薬剤学的製剤は、例えばソルビン酸０.０５〜 ２.５重量％、有利には０.１〜１.０重量％および多価アルコールおよび／また は多価エーテル０〜３０重量％、有利には５〜２０重量％を含有することができ る。 ヒドロゲルを形成するために、常用の増粘剤を使用することができる（Ullman n’s Encyclopedia of Industrial Chemistry 5th Ed.,VolA24 220頁以下）。適 当な増粘剤は、例えばゲル形成多糖類およびプロテイン、例えばゼラチン、寒天 、ペクチン、およびデキストリンまたは特にポリアクリレート、例えばカルボポ ール（Carbopol（登録商標）、Goodrich Chem.Clevel and 米国）タイプのポリ アクリレートである。 ヒドロゲルの形の適当な製剤は本発明により、例えば以下の組成を有すること ができる。 ソルビン酸 ０.１５〜 ０.５０％ プロピレングリコール １０.０ 〜１５.０％ カルボポール９８０ ０.５ 〜 ２.０％ 水酸化ナトリウム ０.２ 〜 ０.５％ 洗浄水 合わせて１００％ （％表示は重量％） 以下の実施例により本発明を詳細に説明する。 例 ソルビン酸０.２ｇ、プロピレングリコール１２.０ｇおよび洗浄水７６.５５ ｇを混合し、３５℃に加温し、ソルビン酸を撹拌しながら溶かす。その後溶液を ２０℃に冷却し、カルボポール１.０ｇと混合し、均質化する。引き続き混合物 に洗浄水１０.２５ｇ中の水酸化ナトリウム１０.０ｇの溶液を添加し、ゲル骨格 が完全に形成されるまで混合物を均質化する。 １０個の試験センターからの最終的な医師の意見は、試験したソルビン酸を有 するヒドロゲル基剤が平均して中程度の症状のにきびを治療するために良好から きわめて良好までの適性を有すると評価した。 従って、開発されたソルビン酸を有するヒドロゲル基剤は強い抗菌作用および にきびの炎症の進行に及ぼす明らかな影響を示し、これは保存されたヒドロゲル 基剤の期待された賦形剤効果よりはるかに優れている。DETAILED DESCRIPTION OF THE INVENTION Sorbic acid-containing hydrogels The present invention relates to hydrogels, characterized in that they contain sorbic acid as the sole active substance, optionally in combination with polyhydric alcohols and / or polyhydric ethers. The present invention relates to a pharmaceutical preparation of Pharmaceutical preparations in the form of hydrogels intended for topical application such as, for example, ointments or creams, comprise sorbic acid (2,2) of the formula I: CH 3 —CH ＝ CH—CH ＝ CH—COOH (I) 4-hexadienoic acid) and it is well known that sorbic acid is used to preserve the formulation (Ullmann's Encyclopedia of Industrial Chemistry 5th Ed. VCH Verlagsgesellschaft mbH D-69451 Weinheim (DE) 1993 , VolA24, 507 pages). In addition, the formulation may contain polyhydric alcohols and / or polyethers such as, for example, ethylene glycol, propylene glycol, glycerin or polyoxyalkylene, which protect the skin from drying and keep it soft. (Wetting agents, emollients and emollients) are well known (Ullman's Encyclopedia of Industrial Chemistry 5th Ed. VCH Verlagsgesellschaft mbH D-69451 Weinheim (DE) 1993, VolA10 page 101 and below, VolA21 page 579 and below , A22163). In the case of active substance-containing preparations, these additives can optionally be used as agents (enhancers) which enhance the penetration of the active substance. Pharmaceutical preparations in the form of hydrogels containing sorbic acid, advantageously in combination with polyhydric alcohols and / or polyhydric ethers as the sole active substance, are unexpectedly described in detail in the following examples. Thus, topical application has been found to have a significant therapeutic effect on inflammatory rash in acne patients. As regards the pharmaceutical preparations according to the invention, the polyhydric alcohols and / or polyhydric ethers are preferably physiologically tolerable liquid substances of these substance types, such as are generally used for such preparations. Are suitable. These compounds are, for example, the general formula II: H- (O-CHR- CH 2) n-OH (II) (n in the formula is 1-12, preferably represents a number from 1 to 8, R is hydrogen Which represents an atom, a methyl group or, when n is a number 1, represents a hydroxymethyl group). Suitable alcohols or ethers of the general formula I are, for example, ethylene glycol, propylene glycol, glycerin, diethylene glycol, triethylene glycol, dipropylene glycol or tripropylene glycol. These are substances used as enhancers in pharmaceutical preparations intended for topical application for the active substances used in said preparations (for example EP-A-0165696, International Patent WO 88/01496 and DE-A 25 155 94). On the other hand, the pharmaceutical preparations according to the invention can contain, as polyhydric alcohols or ethers, cyclic polyols such as, for example, dimethyl isosorbide or glycol ethers, such as polyethers or diglycol dimethyl ether. Previously conducted studies have shown that propylene glycol is particularly suitable. Pharmaceutical preparations in the form of hydrogels according to the invention comprise, for example, 0.05 to 2.5% by weight, preferably 0.1 to 1.0% by weight, of sorbic acid and 0 to 0 polyhydric alcohols and / or polyhydric ethers. It can contain 30% by weight, preferably 5-20% by weight. Conventional thickeners can be used to form the hydrogel (Ullman's Encyclopedia of Industrial Chemistry 5th Ed., Vol A24, p. 220 et seq.). Suitable thickeners are, for example, gel-forming polysaccharides and proteins such as gelatin, agar, pectin and dextrin or especially polyacrylates, such as polyacrylates of the Carbopol®, Goodrich Chem. Clevel and US type It is. A suitable formulation in the form of a hydrogel can have, for example, the following composition according to the invention: Sorbic acid 0.15 to 0.50% Propylene glycol 10.0 to 15.0% Carbopol 980 0.5 to 2.0% Sodium hydroxide 0.2 to 0.5% Wash water Total 100% (% The present invention will be described in detail with reference to the following examples. Example 0.2 g of sorbic acid, 12.0 g of propylene glycol and 76.55 g of washing water are mixed, heated to 35 ° C. and dissolved with stirring. The solution is then cooled to 20 ° C., mixed with 1.0 g of Carbopol and homogenized. Subsequently, a solution of 10.0 g of sodium hydroxide in 10.25 g of washing water is added to the mixture and the mixture is homogenized until the gel skeleton is completely formed. Final physician opinion from 10 test centers rates hydrogel base with tested sorbic acid as having good to very good aptitude for treating on average moderate to moderate acne did. Thus, the developed hydrogel base with sorbic acid shows strong antibacterial activity and a clear effect on the progression of acne inflammation, which is much better than the expected excipient effect of the preserved hydrogel base ing.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19520838.2 | 1995-05-31 | ||
| DE19520838 | 1995-05-31 | ||
| PCT/EP1996/002300 WO1996038135A1 (en) | 1995-05-31 | 1996-05-30 | Sorbic-acid-containing hydrogels |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH11506441A true JPH11506441A (en) | 1999-06-08 |
Family
ID=7763859
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8536180A Pending JPH11506441A (en) | 1995-05-31 | 1996-05-30 | Hydrogel containing sorbic acid |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0831803A1 (en) |
| JP (1) | JPH11506441A (en) |
| KR (1) | KR19990022143A (en) |
| CN (1) | CN1185735A (en) |
| AU (1) | AU6002796A (en) |
| CA (1) | CA2222566A1 (en) |
| CZ (1) | CZ374797A3 (en) |
| HU (1) | HUP9801745A3 (en) |
| IS (1) | IS4606A (en) |
| PL (1) | PL323598A1 (en) |
| TR (1) | TR199701463T1 (en) |
| WO (1) | WO1996038135A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2019526229A (en) * | 2016-06-30 | 2019-09-19 | ユン エンヴェー | Preservation of microorganisms |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9826656D0 (en) | 1998-12-03 | 1999-01-27 | Novartis Ag | Organic compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6333314A (en) * | 1986-07-29 | 1988-02-13 | Sansho Seiyaku Kk | External preparation |
| US5013769A (en) * | 1988-08-22 | 1991-05-07 | Medipro Sciences Limited | Method of making a hydrogel-forming wound dressing or skin coating material |
-
1996
- 1996-05-30 JP JP8536180A patent/JPH11506441A/en active Pending
- 1996-05-30 EP EP96917458A patent/EP0831803A1/en not_active Withdrawn
- 1996-05-30 CN CN96194272A patent/CN1185735A/en active Pending
- 1996-05-30 HU HU9801745A patent/HUP9801745A3/en unknown
- 1996-05-30 TR TR97/01463T patent/TR199701463T1/en unknown
- 1996-05-30 KR KR1019970708622A patent/KR19990022143A/en not_active Withdrawn
- 1996-05-30 CZ CZ973747A patent/CZ374797A3/en unknown
- 1996-05-30 AU AU60027/96A patent/AU6002796A/en not_active Abandoned
- 1996-05-30 CA CA002222566A patent/CA2222566A1/en not_active Abandoned
- 1996-05-30 WO PCT/EP1996/002300 patent/WO1996038135A1/en not_active Ceased
- 1996-05-30 PL PL96323598A patent/PL323598A1/en unknown
-
1997
- 1997-10-31 IS IS4606A patent/IS4606A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2019526229A (en) * | 2016-06-30 | 2019-09-19 | ユン エンヴェー | Preservation of microorganisms |
Also Published As
| Publication number | Publication date |
|---|---|
| PL323598A1 (en) | 1998-04-14 |
| IS4606A (en) | 1997-10-31 |
| CA2222566A1 (en) | 1996-12-05 |
| KR19990022143A (en) | 1999-03-25 |
| AU6002796A (en) | 1996-12-18 |
| CZ374797A3 (en) | 1998-04-15 |
| TR199701463T1 (en) | 1998-02-21 |
| HUP9801745A2 (en) | 1998-12-28 |
| EP0831803A1 (en) | 1998-04-01 |
| HUP9801745A3 (en) | 2000-04-28 |
| CN1185735A (en) | 1998-06-24 |
| WO1996038135A1 (en) | 1996-12-05 |
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