BRPI0608073A8 - Formas polimorfas de rifaximina, processos para sua produção e uso das mesmas em composições medicinais - Google Patents
Formas polimorfas de rifaximina, processos para sua produção e uso das mesmas em composições medicinaisInfo
- Publication number
- BRPI0608073A8 BRPI0608073A8 BRPI0608073A BRPI0608073A BRPI0608073A8 BR PI0608073 A8 BRPI0608073 A8 BR PI0608073A8 BR PI0608073 A BRPI0608073 A BR PI0608073A BR PI0608073 A BRPI0608073 A BR PI0608073A BR PI0608073 A8 BRPI0608073 A8 BR PI0608073A8
- Authority
- BR
- Brazil
- Prior art keywords
- rifaximin
- production
- medicinal compositions
- processes
- polymorphous forms
- Prior art date
Links
- NZCRJKRKKOLAOJ-XRCRFVBUSA-N rifaximin Chemical compound OC1=C(C(O)=C2C)C3=C4N=C5C=C(C)C=CN5C4=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O NZCRJKRKKOLAOJ-XRCRFVBUSA-N 0.000 title abstract 7
- 229960003040 rifaximin Drugs 0.000 title abstract 7
- 238000004519 manufacturing process Methods 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- 239000000203 mixture Substances 0.000 title abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 abstract 1
- 239000012467 final product Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
-
- 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
-
- 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
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic 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; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/21—Heterocyclic 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; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
- C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical
- C07D499/58—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical
- C07D499/64—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Nutrition Science (AREA)
- Physiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicinal Preparation (AREA)
Abstract
FORMAS POLIMORFAS DE RIFAXIMINA, PROCESSOS PARA SUA PRODUÇÃO E USO DAS MESMAS EM COMPOSIÇÕES MEDICINAIS. A presente invenção refere-se a formas polimórficas cristalinas do antibiótico rifaximina (INN), denominadas de rifaximina (Delta) e rifaximina (Épsilon), de utilidade na produção de composições medicinais contendo rifaximina para uso tópico e oral, obtidas através de um processo de cristalização efetivado mediante dissolução a quente da rifaximina bruta em álcool etílico, provocando a cristalização do produto através da adição de água a uma determinada temperatura e por um determinado período de tempo, seguido de secagem efetuada sob condições controladas, até se alcançar um teor de água estabelecido para o produto final.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05004695.2A EP1698630B1 (en) | 2005-03-03 | 2005-03-03 | New polymorphous forms of rifaximin, processes for their production and use thereof in the medicinal preparations |
| PCT/EP2006/001755 WO2006094662A1 (en) | 2005-03-03 | 2006-02-27 | New polymorphous forms of rifaximin, processes for their production and use thereof in the medicinal |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BRPI0608073A2 BRPI0608073A2 (pt) | 2009-11-03 |
| BRPI0608073A8 true BRPI0608073A8 (pt) | 2017-12-26 |
Family
ID=34934045
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0608073A BRPI0608073A8 (pt) | 2005-03-03 | 2006-02-27 | Formas polimorfas de rifaximina, processos para sua produção e uso das mesmas em composições medicinais |
Country Status (27)
| Country | Link |
|---|---|
| US (9) | US8193196B2 (pt) |
| EP (1) | EP1698630B1 (pt) |
| JP (2) | JP5737825B2 (pt) |
| KR (1) | KR100885755B1 (pt) |
| CN (1) | CN1900077B (pt) |
| AU (1) | AU2006222312B8 (pt) |
| BR (1) | BRPI0608073A8 (pt) |
| CA (1) | CA2594789C (pt) |
| DK (1) | DK1698630T3 (pt) |
| ES (1) | ES2522895T3 (pt) |
| HR (1) | HRP20070433B1 (pt) |
| IL (1) | IL184694A0 (pt) |
| MA (1) | MA29345B1 (pt) |
| MD (1) | MD4081G2 (pt) |
| ME (1) | ME00272B (pt) |
| MX (1) | MX2007010742A (pt) |
| NO (1) | NO342197B1 (pt) |
| NZ (1) | NZ556737A (pt) |
| PL (1) | PL1698630T3 (pt) |
| PT (1) | PT1698630E (pt) |
| RS (1) | RS54570B1 (pt) |
| RU (1) | RU2397985C2 (pt) |
| SI (1) | SI1698630T1 (pt) |
| TN (1) | TNSN07292A1 (pt) |
| UA (1) | UA89809C2 (pt) |
| WO (1) | WO2006094662A1 (pt) |
| ZA (1) | ZA200707397B (pt) |
Families Citing this family (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7048906B2 (en) | 1995-05-17 | 2006-05-23 | Cedars-Sinai Medical Center | Methods of diagnosing and treating small intestinal bacterial overgrowth (SIBO) and SIBO-related conditions |
| US6861053B1 (en) | 1999-08-11 | 2005-03-01 | Cedars-Sinai Medical Center | Methods of diagnosing or treating irritable bowel syndrome and other disorders caused by small intestinal bacterial overgrowth |
| US7906542B2 (en) | 2004-11-04 | 2011-03-15 | Alfa Wassermann, S.P.A. | Pharmaceutical compositions comprising polymorphic forms α, β, and γ of rifaximin |
| US7902206B2 (en) | 2003-11-07 | 2011-03-08 | Alfa Wassermann, S.P.A. | Polymorphic forms α, β and γ of rifaximin |
| ITMI20032144A1 (it) | 2003-11-07 | 2005-05-08 | Alfa Wassermann Spa | Forme polimorfe di rifaximina, processi per ottenerle e |
| PT1698630E (pt) * | 2005-03-03 | 2014-09-15 | Alfa Wassermann Spa | Novas formas polimorfas de rifaximina, processos para a sua produção e a sua utilização nas preparações medicinais |
| ITBO20050123A1 (it) | 2005-03-07 | 2005-06-06 | Alfa Wassermann Spa | Formulazioni farmaceutiche gastroresistenti contenenti rifaximina |
| ITMI20061692A1 (it) | 2006-09-05 | 2008-03-06 | Alfa Wassermann Spa | Uso di polioli per ottenere forme polimorfe stabili di rifaximina |
| EP2069363B1 (en) | 2006-09-22 | 2013-03-20 | Cipla Ltd. | Rifaximin in an amorphous form |
| ITMI20071241A1 (it) * | 2007-06-20 | 2008-12-21 | Solmag S P A | Processo per la preparazione di rifaximina amorfa e rifaximina amorfa cosi' ottenuta |
| US7709634B2 (en) | 2007-09-20 | 2010-05-04 | Apotex Pharmachem Inc. | Amorphous form of rifaximin and processes for its preparation |
| US8486956B2 (en) * | 2008-02-25 | 2013-07-16 | Salix Pharmaceuticals, Ltd | Forms of rifaximin and uses thereof |
| US8067429B2 (en) * | 2008-02-25 | 2011-11-29 | Salix Pharmaceuticals, Ltd. | Forms of rifaximin and uses thereof |
| US11779571B2 (en) | 2008-02-26 | 2023-10-10 | Salix Pharmaceuticals, Inc. | Methods for treating irritable bowel syndrome (IBS) |
| PT2252148T (pt) | 2008-02-26 | 2020-01-23 | Salix Pharmaceuticals Ltd | Métodos de tratamento da síndrome do intestino irritável |
| HRP20140939T1 (hr) | 2008-05-07 | 2014-11-21 | Salix Pharmaceuticals, Ltd. | Davanje preparata za äśišä†enje crijeva i antibiotika za lijeäśenje bolesti crijeva |
| AU2009297562B2 (en) | 2008-09-26 | 2015-04-23 | Alfasigma S.P.A. | Agent for preventing and/or treating functional gastrointestinal disorder |
| US20110035232A1 (en) | 2008-10-02 | 2011-02-10 | Salix Pharmaceuticals, Ltd. | Methods of treating hepatic encephalopathy |
| US12285414B2 (en) | 2008-10-02 | 2025-04-29 | Salix Pharmaceuticals, Inc. | Methods of treating hepatic encephalopathy |
| BRPI0920465A2 (pt) | 2008-10-02 | 2018-03-20 | Salix Pharmaceuticals, Inc. | metodo de tratamento de encefalopatia hepática |
| US7928115B2 (en) | 2008-10-02 | 2011-04-19 | Salix Pharmaceuticals, Ltd. | Methods of treating travelers diarrhea and hepatic encephalopathy |
| US8916193B2 (en) | 2008-12-10 | 2014-12-23 | Cipla Limited | Rifaximin complexes |
| NZ598671A (en) | 2009-09-13 | 2014-02-28 | Salix Pharmaceuticals Ltd | Methods for treating irritable bowel syndrome (ibs) |
| EP2503989A2 (en) | 2009-11-23 | 2012-10-03 | Cipla Limited | Topical foam composition |
| US8952159B2 (en) | 2009-12-28 | 2015-02-10 | Silvio Massimo Lavagna | Method for the production of amorphous rifaximin |
| AU2011218129A1 (en) | 2010-02-18 | 2012-08-23 | Board Of Regents Of The University Of Texas System | Methods for treating infection |
| IT1398550B1 (it) | 2010-03-05 | 2013-03-01 | Alfa Wassermann Spa | Formulazioni comprendenti rifaximina utili per ottenere un effetto prolungato nel tempo |
| CN101836959A (zh) * | 2010-05-20 | 2010-09-22 | 山东达因海洋生物制药股份有限公司 | 一种制备几乎无苦味利福昔明干混悬剂的方法 |
| CA2802874A1 (en) * | 2010-06-16 | 2011-12-22 | Apotex Pharmachem Inc. | Polymorphic forms of rifaximin |
| SMT202000390T1 (it) | 2010-07-12 | 2020-09-10 | Salix Pharmaceuticals Inc | Formulazioni di rifaximina e loro usi |
| WO2012035544A2 (en) | 2010-09-13 | 2012-03-22 | Sequent Scientific Ltd. | A novel polymorphic form of rifaximin and process for its preparation |
| IT1403847B1 (it) | 2010-09-22 | 2013-11-08 | Alfa Wassermann Spa | Composizioni farmaceutiche comprendenti rifaximina e loro uso. |
| WO2012109605A2 (en) | 2011-02-11 | 2012-08-16 | Salix Pharmaceuticals, Ltd. | Forms of rifaximin and uses thereof |
| CA2834829A1 (en) | 2011-05-02 | 2012-11-08 | Ranbaxy Laboratories Limited | Rifaximin dimethylformamide solvate |
| ITMI20110890A1 (it) * | 2011-05-19 | 2012-11-20 | A M S A Anonima Materie Sint & Affini S P A | Polimorfo di rifaximina e processo per la sua preparazione |
| WO2013027227A1 (en) * | 2011-07-20 | 2013-02-28 | Ind-Swift Laboratories Limited | Novel polymorphic form i of rifaximin |
| ITBO20110461A1 (it) | 2011-07-29 | 2013-01-30 | Alfa Wassermann Spa | Composizioni farmaceutiche comprendenti rifaximina, processi per la loro preparazione e loro uso nel trattamento di infezioni vaginali. |
| US20130184302A1 (en) * | 2011-11-02 | 2013-07-18 | Enoch Bortey | Methods for treating irritable bowel syndrome (ibs) and infections |
| US9359374B2 (en) | 2012-06-13 | 2016-06-07 | Apotex Pharmachem Inc. | Polymorphic forms of rifaximin |
| ITBO20120368A1 (it) | 2012-07-06 | 2014-01-07 | Alfa Wassermann Spa | Composizioni comprendenti rifaximina e amminoacidi, cristalli di rifaximina derivanti da tali composizioni e loro uso. |
| US9849090B2 (en) | 2012-12-12 | 2017-12-26 | Sun Pharmaceutical Industries Limited | Pharmaceutical compositions of rifaximin |
| US20160038468A1 (en) | 2013-03-15 | 2016-02-11 | Alfa Wassermann S.P.A. | Rifaximin for use in the treating of vaginal infections |
| US20160047819A1 (en) | 2013-03-15 | 2016-02-18 | Alfa Wassermann S.P.A. | Method for diagnosing vaginal infections |
| CN105324109A (zh) | 2013-04-12 | 2016-02-10 | 意大利阿尔法韦士曼制药公司 | Nsaid施用和相关的组合物、方法和系统 |
| US9018225B1 (en) | 2013-07-26 | 2015-04-28 | Novel Laboratories | Rifaximin crystalline forms and methods of preparation thereof |
| US20150103715A1 (en) * | 2013-10-14 | 2015-04-16 | Qualcomm Incorporated | Downlink control format indicator |
| EP2927235B1 (en) | 2014-03-31 | 2017-02-08 | Euticals S.P.A. | Polymorphic mixture of rifaximin and its use for the preparation of solid formulations |
| US9765088B2 (en) | 2014-04-19 | 2017-09-19 | Granules India Limited | Process for the preparation of rifamycin derivatives |
| CA2947962C (en) | 2014-05-04 | 2024-01-16 | Salix Pharmaceuticals, Inc. | Ibs microbiota and uses thereof |
| AU2015260837B2 (en) | 2014-05-12 | 2019-02-28 | Alfasigma S.P.A. | New solvated crystal form of rifaximin, production, compositions and uses thereof |
| EP2982764A1 (en) | 2014-08-05 | 2016-02-10 | ALFA WASSERMANN S.p.A. | Identification of vaginal bacteria |
| EP3325100A4 (en) | 2015-07-17 | 2019-02-20 | Memorial Sloan-Kettering Cancer Center | COMBINATION THERAPY WITH PDK1 AND PI3K INHIBITORS |
| HUE040253T2 (hu) | 2016-03-24 | 2019-02-28 | Sandoz Ag | Rifaximin alfa&deltát tartalmazó gyógyászati készítmény |
| HUE044432T2 (hu) | 2016-03-24 | 2019-10-28 | Sandoz Ag | Rifaximin alfá-t tartalmazó, hosszan eltartható kompozíció |
| US9988398B2 (en) | 2016-06-07 | 2018-06-05 | Cadila Healthcare Limited | Crystalline form of rifaximin and process for its preparation |
| CA3038312A1 (en) | 2016-09-30 | 2018-04-05 | Salix Pharmaceuticals, Inc. | Solid dispersion forms of rifaximin |
| CA3013161C (en) | 2017-04-26 | 2020-03-24 | Sandoz Ag | Oral dosage form comprising rifaximin in form beta |
| IT201700091912A1 (it) * | 2017-08-08 | 2019-02-08 | Biofer Spa | Nuove pirido-imidazo rifamicine |
| RU2020102511A (ru) | 2017-06-26 | 2021-07-27 | Биофер С.П.А. | Соединения пиридо-имидазо рифамицина в качестве антибактериального средства |
| CA3142214A1 (en) | 2019-06-03 | 2020-12-10 | Bausch Health Ireland Limited | Use of methylnaltrexone and rifaximin for treatment of increased gut permeability or associated disorders |
| MX427410B (es) | 2019-09-24 | 2025-10-13 | Bausch Health Ireland Ltd | Formulaciones liquidas de rifaximina |
| WO2021191312A1 (en) | 2020-03-24 | 2021-09-30 | Bausch Health Ireland Limited | Methods of treating covid-19 with rifaximin |
| CA3184054A1 (en) | 2020-06-26 | 2021-12-30 | Jacob Cole | Targeted release rifaximin compositions |
| KR20230088761A (ko) * | 2020-10-13 | 2023-06-20 | 베링거 인겔하임 인터내셔날 게엠베하 | 재가공하는 방법 |
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