ZA200207443B - Method for preparing 9-deoxo-8A-aza-(8a-alkyl)-8a-homoerythromycin a derivatives from 9-deoxo-9(Z)-hydroxyiminoertythromycin a. - Google Patents
Method for preparing 9-deoxo-8A-aza-(8a-alkyl)-8a-homoerythromycin a derivatives from 9-deoxo-9(Z)-hydroxyiminoertythromycin a. Download PDFInfo
- Publication number
- ZA200207443B ZA200207443B ZA200207443A ZA200207443A ZA200207443B ZA 200207443 B ZA200207443 B ZA 200207443B ZA 200207443 A ZA200207443 A ZA 200207443A ZA 200207443 A ZA200207443 A ZA 200207443A ZA 200207443 B ZA200207443 B ZA 200207443B
- Authority
- ZA
- South Africa
- Prior art keywords
- mixture
- process according
- solvent
- pyridine
- beckmann rearrangement
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 46
- 239000011541 reaction mixture Substances 0.000 claims description 37
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 27
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 238000006722 reduction reaction Methods 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 23
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 23
- 230000008569 process Effects 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 238000006237 Beckmann rearrangement reaction Methods 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- 230000009467 reduction Effects 0.000 claims description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 11
- 229930195733 hydrocarbon Natural products 0.000 claims description 11
- 150000002430 hydrocarbons Chemical class 0.000 claims description 11
- 239000000543 intermediate Substances 0.000 claims description 11
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 claims description 10
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 10
- 239000012279 sodium borohydride Substances 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 150000002463 imidates Chemical class 0.000 claims description 7
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000000707 stereoselective effect Effects 0.000 claims description 3
- YJUUZFWMKJBVFJ-UHFFFAOYSA-N 1,3-dimethylimidazolidin-4-one Chemical compound CN1CN(C)C(=O)C1 YJUUZFWMKJBVFJ-UHFFFAOYSA-N 0.000 claims description 2
- ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical compound OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 150000003839 salts Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000007787 solid Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 238000002955 isolation Methods 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229960003276 erythromycin Drugs 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000010981 drying operation Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 229930006677 Erythromycin A Natural products 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- AJSDVNKVGFVAQU-BIIVOSGPSA-N cladinose Chemical group O=CC[C@@](C)(OC)[C@@H](O)[C@H](C)O AJSDVNKVGFVAQU-BIIVOSGPSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000006345 epimerization reaction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0003807A FR2806724B1 (fr) | 2000-03-24 | 2000-03-24 | Procede pour la preparation de derives 9-deoxo-8a-aza- (8a-alkyl)-8a-homoerythromycine a a partir de la 9-deoxo-9 (z)-hydroxyiminoerythromycine a |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200207443B true ZA200207443B (en) | 2003-10-17 |
Family
ID=8848497
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200207443A ZA200207443B (en) | 2000-03-24 | 2002-09-17 | Method for preparing 9-deoxo-8A-aza-(8a-alkyl)-8a-homoerythromycin a derivatives from 9-deoxo-9(Z)-hydroxyiminoertythromycin a. |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP1265908B1 (ja) |
| JP (1) | JP4975933B2 (ja) |
| CN (1) | CN1174992C (ja) |
| AR (1) | AR027706A1 (ja) |
| AT (1) | ATE281463T1 (ja) |
| AU (2) | AU4663601A (ja) |
| BR (1) | BRPI0109413B8 (ja) |
| CA (1) | CA2399634C (ja) |
| DE (1) | DE60106882T2 (ja) |
| DK (1) | DK1265908T3 (ja) |
| ES (1) | ES2232609T3 (ja) |
| FR (1) | FR2806724B1 (ja) |
| NZ (1) | NZ520878A (ja) |
| PL (1) | PL206683B1 (ja) |
| PT (1) | PT1265908E (ja) |
| WO (1) | WO2001072763A1 (ja) |
| ZA (1) | ZA200207443B (ja) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2426124T3 (es) * | 2008-10-24 | 2013-10-21 | Merial Ltd. | Procedimiento para sintetizar compuestos macrólidos |
| CN103833807B (zh) * | 2012-11-21 | 2016-12-07 | 洛阳惠中兽药有限公司 | 一种加米霉素中间体的制备方法 |
| CN103965273B (zh) | 2013-08-23 | 2016-05-25 | 普莱柯生物工程股份有限公司 | 一种大环内酯类化合物 |
| KR102233327B1 (ko) * | 2013-12-26 | 2021-03-26 | 스미또모 가가꾸 가부시끼가이샤 | 할로겐 치환 프탈리드의 제조 방법 |
| CN109970827A (zh) * | 2017-12-27 | 2019-07-05 | 洛阳惠中兽药有限公司 | 加米霉素中间体化合物i的晶型及其制备方法和应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5912331A (en) * | 1991-03-15 | 1999-06-15 | Merck & Co., Inc. | Process for the preparation of 9-deoxo-9(Z)-hydroxyiminoerythromycin A |
| DE69227713D1 (de) * | 1991-03-15 | 1999-01-14 | Merck & Co Inc | 9-Deoxo-9(Z)-hydroxyiminoerythromycin A und O-Derivate hiervon |
| CA2064634C (en) * | 1991-04-04 | 1998-08-04 | James V. Heck | 9-deoxo-8a-aza-8a-homoerythromycin a derivatives modified at the 4"- and8a-positions |
| CA2064985A1 (en) * | 1991-04-05 | 1992-10-06 | Robert R. Wilkening | 8a-aza-8a-homoertyhromycin cyclic lactams |
| CA2065222A1 (en) * | 1991-04-09 | 1992-10-10 | Robert R. Wilkening | Process for the preparation of 8a-aza-8a-homoerythromycin cyclic iminoethers |
| EP0508795A1 (en) * | 1991-04-10 | 1992-10-14 | Merck & Co. Inc. | 8a-aza-8a-homoerythromycin cyclic iminoethers |
| CA2065218A1 (en) * | 1991-04-11 | 1992-10-12 | Robert R. Wilkening | Process for the preparation of 9-deoxo-8a-aza-8a-homoerythromycin a and its 8a-alkyl derivatives |
| EP0515141A1 (en) * | 1991-05-20 | 1992-11-25 | Merck & Co. Inc. | Novel process for the preparation of 8A-aza-8A-homoerythromycin cyclic lactams |
| EP0549040A1 (en) * | 1991-12-20 | 1993-06-30 | Merck & Co. Inc. | Methods of making 4" derivatives of 9-deoxo-8a-aza-8a-alkyl-8a-homoerythromycin A |
| PT102006B (pt) * | 1997-05-19 | 2000-06-30 | Hovione Sociedade Quimica S A | Novo processo de preparacao de azitromicina |
| FR2791680B1 (fr) * | 1999-03-29 | 2001-06-29 | Merial Sas | Procede utile pour reduire les intermediaires imidates issus d'un rearrangement de beckmann d'un macrocycle 8a-azalide |
-
2000
- 2000-03-24 FR FR0003807A patent/FR2806724B1/fr not_active Expired - Lifetime
-
2001
- 2001-03-23 BR BRPI0109413A patent/BRPI0109413B8/pt not_active IP Right Cessation
- 2001-03-23 EP EP01919556A patent/EP1265908B1/fr not_active Expired - Lifetime
- 2001-03-23 ES ES01919556T patent/ES2232609T3/es not_active Expired - Lifetime
- 2001-03-23 WO PCT/FR2001/000897 patent/WO2001072763A1/fr active IP Right Grant
- 2001-03-23 CA CA2399634A patent/CA2399634C/en not_active Expired - Lifetime
- 2001-03-23 CN CNB018064728A patent/CN1174992C/zh not_active Expired - Lifetime
- 2001-03-23 AR ARP010101371A patent/AR027706A1/es active IP Right Grant
- 2001-03-23 AT AT01919556T patent/ATE281463T1/de active
- 2001-03-23 AU AU4663601A patent/AU4663601A/xx active Pending
- 2001-03-23 AU AU2001246636A patent/AU2001246636C1/en not_active Expired
- 2001-03-23 DK DK01919556T patent/DK1265908T3/da active
- 2001-03-23 JP JP2001571694A patent/JP4975933B2/ja not_active Expired - Lifetime
- 2001-03-23 DE DE60106882T patent/DE60106882T2/de not_active Expired - Lifetime
- 2001-03-23 NZ NZ520878A patent/NZ520878A/en not_active IP Right Cessation
- 2001-03-23 PL PL361225A patent/PL206683B1/pl unknown
- 2001-03-23 PT PT01919556T patent/PT1265908E/pt unknown
-
2002
- 2002-09-17 ZA ZA200207443A patent/ZA200207443B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE60106882T2 (de) | 2005-12-01 |
| BR0109413A (pt) | 2002-12-10 |
| AU2001246636C1 (en) | 2006-02-23 |
| CN1425022A (zh) | 2003-06-18 |
| EP1265908B1 (fr) | 2004-11-03 |
| DE60106882D1 (de) | 2004-12-09 |
| CN1174992C (zh) | 2004-11-10 |
| PT1265908E (pt) | 2005-03-31 |
| AU2001246636B2 (en) | 2005-04-21 |
| BRPI0109413B1 (pt) | 2015-08-04 |
| FR2806724A1 (fr) | 2001-09-28 |
| AU4663601A (en) | 2001-10-08 |
| FR2806724B1 (fr) | 2003-12-05 |
| JP2003528882A (ja) | 2003-09-30 |
| EP1265908A1 (fr) | 2002-12-18 |
| ATE281463T1 (de) | 2004-11-15 |
| NZ520878A (en) | 2004-05-28 |
| WO2001072763A1 (fr) | 2001-10-04 |
| ES2232609T3 (es) | 2005-06-01 |
| JP4975933B2 (ja) | 2012-07-11 |
| DK1265908T3 (da) | 2005-03-14 |
| PL361225A1 (en) | 2004-09-20 |
| CA2399634A1 (en) | 2001-10-04 |
| AR027706A1 (es) | 2003-04-09 |
| CA2399634C (en) | 2011-05-24 |
| PL206683B1 (pl) | 2010-09-30 |
| BRPI0109413B8 (pt) | 2021-05-25 |
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