WO2000007628A1 - Preparations stabilisees de beta-lactamine - Google Patents
Preparations stabilisees de beta-lactamine Download PDFInfo
- Publication number
- WO2000007628A1 WO2000007628A1 PCT/JP1999/003233 JP9903233W WO0007628A1 WO 2000007628 A1 WO2000007628 A1 WO 2000007628A1 JP 9903233 W JP9903233 W JP 9903233W WO 0007628 A1 WO0007628 A1 WO 0007628A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oil
- mother nucleus
- phosphate
- stabilized
- antibiotic
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
-
- 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
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula, e.g. penicillins, penems
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
-
- 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
- A61K47/02—Inorganic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
Definitions
- the present invention relates to a stabilized lactam antibiotic having an esterified carboxy group directly bonded to a mother nucleus.
- -Ratatum antibiotics especially penicillin antibiotics, generally have the property of causing allergies, and to prevent scattering, for example, granulation is performed. Therefore, the present inventors have studied the use of an oil-containing preparation. However, they generally have esterified carboxyl groups directly attached to the mother nucleus—the problem is that lactam antibiotics are thermally unstable in oleaginous formulations.
- the present invention has been made to solve the above problems, and has an esterified carboxy group directly bonded to a heat stable mother nucleus even in an oil-containing preparation. Stabilization of lactam antibiotics It is to provide a formulation.
- the present inventors have conducted intensive studies to solve the problem of stability of lactam antibiotics having an esterified carboxyl group directly linked to the mother nucleus. We have obtained a new finding that kneading phosphates and oils with lactam antibiotics containing a carboxyl group improves the stability dramatically.
- the present invention is carried out by kneading a phosphate and an oil with a 9-lactam antibiotic having an esterified carboxyl group directly linked to the mother nucleus.
- the kneading is carried out, for example, using a grinding machine.
- the kneaded material obtained in this manner is generally obtained in the form of a paste, and the paste can be used as it is. However, it is preferably used in the form of various dosage forms according to a conventional method.
- ester moiety has the formula:
- R 1 is hydrogen or a C 6 -C 6 lower alkyl group such as methyl, ethyl, etc.
- n is an integer of 0-3
- R 2 is an alkanol group (acetyl, propionyl, butyric) ! Li Le, i Sobuchi Li Le etc.
- C ⁇ C 6 lower alkanol i le, etc. means, respectively) in a group represented by or the formula:
- R 3 is hydrogen or a lower alkyl group such as methyl or ethyl
- R 4 is a C 6 to C 6 chain or branched lower alkyl group such as methyl or ethyl. Each means) Carboxymethyl group or formula shown:
- the parent nucleus used in the present invention has a directly esterified carboxyl group./? — Lactam antibiotics include penicillin estenole canolebonate and cephalospori. Carboxylate esters include, for example, tobici 11 in, talampici 11 in, and pi vamp ici 11 in.
- cefotiam hexetil cefotiam hexeti 1
- cefetat hibokinore ceie tame t pi voxi 1
- cefpodoximproxetinore ceipo dox i me proxetil
- Cephalosporin antibiotics such as ceinoram (ceiteram pi voxi 1) and cefuroxime axetinole (ceiuroxime axetil).
- oils examples include fish oil and vegetable oil derived from natural products.
- a synthetic oil such as silicone oil may be used.
- vegetable oils include soybean oil, linseed oil, sesame oil, corn oil, rapeseed oil, olive oil, castor oil, and fallen oil.
- Oils, coconut oil, etc. are fish oils, such as sardine oil, salmon oil, mackerel oil, saury oil, liver oil (eg, shark, cod, bonito, squid, pulp).
- whale oil can also be used.
- soybean oil having the component composition described in the Japanese Pharmacopoeia is preferred.
- phosphates include aluminum phosphate, barium phosphate (first, second and third), and calcium phosphate (first, second and third).
- alkaline earth metal salts of phosphoric acid such as (iii) and alkali metal salts of phosphoric acid such as sodium phosphate (first, second and third).
- the stabilized preparation of the present invention may be in the form of a paste as described above, but is preferably a powder, fine granules, granules, tablets, dragees, capsules, liquids, emulsions, etc. Used in the form of conventional pharmaceutical preparations.
- diluents excipients
- disintegrants eg, sucrose, lactose, starch, glucose, bran, dextrin, crystalline cellulose, low-substituted hydroxypropyl cellulose
- Synthetic aluminum silicate etc.
- binders for example, cellulose, methinoresenolose, hydroxypropyl propylenolose, hydroxypropyl propylmenorcerolero
- Polypropylpyrrolidone Polyvininolepyrrolidone, Gelatin, Arabia Gum, Sodium Anoreginate, Polyethylene glycol What )
- Coloring agents sweetening agents, lubricants (eg, magnesium stearate, etc.) and the like.
- the stabilized preparation of the present invention when obtaining the stabilized preparation of the present invention, after mixing a phosphate having an esterified carboxyl group directly attached to the mother nucleus with a phosphate and a phosphate, The resulting mixture is kneaded with an oil and a surfactant (a paste-like preparation obtained in this way), and further a diluent (excipient) such as lactose is added. It is recommended to add powder.
- examples of the surfactant include polyglycerin fatty acid ester, sucrose fatty acid ester, polyoxyethylene sonolevitan fatty acid ester, polyethylene glycol fatty acid ester, and polyester.
- the stabilized preparation of this invention has an esterified carboxyl group directly linked to the mother nucleus-the blending ratio of lactam antibiotics, oils and phosphates is directly linked to the mother nucleus. 5-50% (wt%, the same applies hereinafter) of lactam antibiotics, 1.5-60% of oil and 1.5 of phosphate
- Tween 20 or Tween 80 (Polysorbet 20 or Polysodium manufactured by Kao Corporation) was used. Prescriptions using Nolevate 80)
- the oil-containing preparation containing phosphate of the present invention is more excellent in heat stability than the oil-containing preparation containing no phosphate.
- the stabilized preparation obtained according to the present invention can be used, for example, by directly adding it to a live feed, or by dissolving it in water in a fish feed such as a dry pellet and then mixing it. For example, it can be effectively used as a marine medicine.
- soybean oil soybean oil, manufactured by Toho Pharmaceutical Co., Ltd .; same hereafter
- soybean oil soybean oil, manufactured by Toho Pharmaceutical Co., Ltd .; same hereafter
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Organic Chemistry (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Cephalosporin Compounds (AREA)
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK99925357T DK1101497T3 (da) | 1998-08-04 | 1999-06-16 | Stabiliserende olieagtige præparationer af tobicillin (beta-lactam antibiotikum) |
DE69938184T DE69938184T2 (de) | 1998-08-04 | 1999-06-16 | Stabilisierte ölige zubereitung von tobicillin (beta-lactam-antibiotika) |
EP99925357A EP1101497B1 (en) | 1998-08-04 | 1999-06-16 | Stabilized oily preparations of tobicillin (beta-lactam antibiotic) |
US09/774,186 US6514962B1 (en) | 1998-08-04 | 1999-06-16 | Stabilized preparations of β-lactam antibiotic |
CA002339147A CA2339147C (en) | 1998-08-04 | 1999-06-16 | Stabilized preparations of .beta.-lactam antibiotic |
JP56296699A JP3531648B2 (ja) | 1998-08-04 | 1999-06-16 | β−ラクタム抗生物質の安定化製剤 |
HK02102937.0A HK1041217A1 (zh) | 1998-08-04 | 2002-04-18 | β-內酰胺抗生素的穩定化製劑 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP22016198 | 1998-08-04 | ||
JP10/220161 | 1998-08-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000007628A1 true WO2000007628A1 (fr) | 2000-02-17 |
Family
ID=16746851
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP1999/003233 WO2000007628A1 (fr) | 1998-08-04 | 1999-06-16 | Preparations stabilisees de beta-lactamine |
Country Status (14)
Country | Link |
---|---|
US (1) | US6514962B1 (ja) |
EP (1) | EP1101497B1 (ja) |
JP (1) | JP3531648B2 (ja) |
KR (1) | KR100412231B1 (ja) |
CN (1) | CN1149102C (ja) |
AT (1) | ATE386546T1 (ja) |
CA (1) | CA2339147C (ja) |
DE (1) | DE69938184T2 (ja) |
DK (1) | DK1101497T3 (ja) |
ES (1) | ES2297925T3 (ja) |
HK (1) | HK1041217A1 (ja) |
PT (1) | PT1101497E (ja) |
TW (1) | TW550081B (ja) |
WO (1) | WO2000007628A1 (ja) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AR025976A1 (es) | 1999-10-08 | 2002-12-26 | Affinium Pharm Inc | Inhibidores de fab i. |
ES2320984T3 (es) * | 2001-04-06 | 2009-06-01 | Affinium Pharmaceuticals, Inc. | Inhibidores de fab i. |
WO2004052890A1 (en) | 2002-12-06 | 2004-06-24 | Affinium Pharmaceuticals, Inc. | Heterocyclic compounds, methods of making them and their use in therapy |
ATE409485T1 (de) * | 2003-03-17 | 2008-10-15 | Affinium Pharm Inc | Pharmazeutische zusammensetzungen inhibitoren von fab i und weitere antibiotika enthaltend |
KR101299399B1 (ko) * | 2004-06-04 | 2013-08-22 | 아피늄 파마슈티컬스, 인크. | 치료제, 및 그의 제조 및 사용 방법 |
JP2009518399A (ja) * | 2005-12-05 | 2009-05-07 | アフィニウム ファーマシューティカルズ, インク. | Fabi阻害剤および抗菌剤としてのヘテロ環アクリルアミド化合物 |
CA2658506C (en) * | 2006-07-20 | 2016-01-26 | Affinium Pharmaceuticals, Inc. | Acrylamide derivatives as fab 1 inhibitors |
US8263613B2 (en) * | 2007-02-16 | 2012-09-11 | Affinium Pharmaceuticals, Inc. | Salts, prodrugs and polymorphs of fab I inhibitors |
BR122021020778B1 (pt) | 2012-06-19 | 2022-07-12 | Debiopharm International Sa | Derivados de pró-fármaco de (e)-n-metil-n-((3-metilbenzofuran-2-il) metil)-3-(7-oxo-5,6,7,8-tetraidro- 1, 8- naftirindin-3-il) acrilamida |
LT3419628T (lt) | 2016-02-26 | 2021-01-25 | Debiopharm International Sa | Medikamentas diabetinėms pėdų infekcijoms gydyti |
CA3069004A1 (en) | 2017-07-07 | 2019-01-10 | Epicentrx, Inc. | Compositions for parenteral administration of therapeutic agents |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61115031A (ja) * | 1984-11-09 | 1986-06-02 | アストラ・レーケメデル・アクチエボラーグ | 塩酸バカンピシリンの安定化法 |
JPS6289619A (ja) * | 1985-08-13 | 1987-04-24 | フア−マコントロ−ル コ−ポレ−シヨン | 安定なナトリウムアスピリン錠剤組成物 |
JPH06298769A (ja) * | 1993-04-13 | 1994-10-25 | Fujisawa Pharmaceut Co Ltd | アンピシリンフェニルエステルおよびその塩 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS59176209A (ja) * | 1983-03-28 | 1984-10-05 | Sankyo Co Ltd | β−ラクタム環を有する化合物の直腸投与用組成物 |
US4731362A (en) * | 1985-08-05 | 1988-03-15 | Shionogi & Co., Ltd. | Alkylcarbamoyloxymethylcephem compounds |
US5063074A (en) * | 1990-01-30 | 1991-11-05 | Rich Products Corporation | Low fat low cholesterol milk products |
JP3233434B2 (ja) * | 1992-04-01 | 2001-11-26 | 塩野義製薬株式会社 | カルバペネム誘導体 |
FR2698560B1 (fr) * | 1992-11-30 | 1995-02-03 | Virbac Laboratoires | Principes actifs pulvérulents stabilisés, compositions les contenant, leur procédé d'obtention et leurs applications. |
US5602118A (en) * | 1993-03-16 | 1997-02-11 | American Cyanamid Company | 2-thiosubstituted carbapenems |
-
1999
- 1999-06-16 CA CA002339147A patent/CA2339147C/en not_active Expired - Fee Related
- 1999-06-16 DE DE69938184T patent/DE69938184T2/de not_active Expired - Fee Related
- 1999-06-16 EP EP99925357A patent/EP1101497B1/en not_active Expired - Lifetime
- 1999-06-16 AT AT99925357T patent/ATE386546T1/de not_active IP Right Cessation
- 1999-06-16 DK DK99925357T patent/DK1101497T3/da active
- 1999-06-16 KR KR10-2001-7000769A patent/KR100412231B1/ko not_active IP Right Cessation
- 1999-06-16 US US09/774,186 patent/US6514962B1/en not_active Expired - Fee Related
- 1999-06-16 PT PT99925357T patent/PT1101497E/pt unknown
- 1999-06-16 CN CNB998117463A patent/CN1149102C/zh not_active Expired - Fee Related
- 1999-06-16 ES ES99925357T patent/ES2297925T3/es not_active Expired - Lifetime
- 1999-06-16 WO PCT/JP1999/003233 patent/WO2000007628A1/ja active IP Right Grant
- 1999-06-16 JP JP56296699A patent/JP3531648B2/ja not_active Expired - Lifetime
- 1999-06-24 TW TW088110651A patent/TW550081B/zh not_active IP Right Cessation
-
2002
- 2002-04-18 HK HK02102937.0A patent/HK1041217A1/zh unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61115031A (ja) * | 1984-11-09 | 1986-06-02 | アストラ・レーケメデル・アクチエボラーグ | 塩酸バカンピシリンの安定化法 |
JPS6289619A (ja) * | 1985-08-13 | 1987-04-24 | フア−マコントロ−ル コ−ポレ−シヨン | 安定なナトリウムアスピリン錠剤組成物 |
JPH06298769A (ja) * | 1993-04-13 | 1994-10-25 | Fujisawa Pharmaceut Co Ltd | アンピシリンフェニルエステルおよびその塩 |
Also Published As
Publication number | Publication date |
---|---|
CA2339147A1 (en) | 2000-02-17 |
DK1101497T3 (da) | 2008-03-31 |
TW550081B (en) | 2003-09-01 |
ES2297925T3 (es) | 2008-05-01 |
HK1041217A1 (zh) | 2002-07-05 |
PT1101497E (pt) | 2008-04-23 |
ATE386546T1 (de) | 2008-03-15 |
CA2339147C (en) | 2009-04-21 |
DE69938184T2 (de) | 2009-03-26 |
CN1322140A (zh) | 2001-11-14 |
JP3531648B2 (ja) | 2004-05-31 |
US6514962B1 (en) | 2003-02-04 |
EP1101497A1 (en) | 2001-05-23 |
KR100412231B1 (ko) | 2003-12-24 |
CN1149102C (zh) | 2004-05-12 |
EP1101497B1 (en) | 2008-02-20 |
EP1101497A4 (en) | 2002-03-06 |
KR20010071964A (ko) | 2001-07-31 |
DE69938184D1 (de) | 2008-04-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
AU783077B2 (en) | Clear oil-containing pharmaceutical compositions | |
WO2000007628A1 (fr) | Preparations stabilisees de beta-lactamine | |
EP0064283B1 (en) | Stabilization of 1-substituted imidazole derivatives in talc | |
CA2071345C (en) | Feed additive for livestock and feed for livestock | |
EP1965764B1 (en) | Self-emulsifying formulations of cetp inhibitors | |
JP4209467B2 (ja) | 経口投与用製剤組成物 | |
JPH03240444A (ja) | 脂肪飼料添加剤の製造方法 | |
JP2006206615A (ja) | 経口投与用シクロスポリン含有新規製剤 | |
JPH0249719A (ja) | 易水分散・可溶性能を有する油溶性ビタミン粉末 | |
JP2001505910A (ja) | 改良医薬組成物 | |
FR2740357A1 (fr) | Granules redispersables dans l'eau comprenant une matiere active sous forme liquide et un tensio-actif non ionique du type alcoxyles | |
JPS60204739A (ja) | エイコサポリエン酸系化合物含有粉体 | |
JP2000095676A (ja) | ビタミンb12含有ソフトカプセル剤 | |
JPH10330250A (ja) | メナテトレノン油性製剤 | |
JPH0570793A (ja) | 脂質の粒状組成物 | |
JP2004115758A (ja) | 酸化防止剤組成物 | |
JP2711635B2 (ja) | ペレット状養魚飼料 | |
WO2022131082A1 (ja) | 外用医薬組成物 | |
CA1132906A (en) | Low volume equine anthelmintic feed additive | |
WO2022131083A1 (ja) | 外用医薬組成物 | |
JP4575705B2 (ja) | 損傷皮膚修復用組成物 | |
GB2041749A (en) | Suppository containing sulphamethoxazole/trimethoprim complex and process for preparing the same | |
JP2023040841A (ja) | 酸化防止剤製剤 | |
JP2024104102A (ja) | 医薬組成物及びその製造方法 | |
JPS60163819A (ja) | 肝油軟カプセル |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 99811746.3 Country of ref document: CN |
|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): CA CN JP KR US |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE |
|
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 1020017000769 Country of ref document: KR |
|
ENP | Entry into the national phase |
Ref document number: 2339147 Country of ref document: CA Ref document number: 2339147 Country of ref document: CA Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 09774186 Country of ref document: US |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1999925357 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: 1999925357 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: 1020017000769 Country of ref document: KR |
|
WWG | Wipo information: grant in national office |
Ref document number: 1020017000769 Country of ref document: KR |
|
WWG | Wipo information: grant in national office |
Ref document number: 1999925357 Country of ref document: EP |