CA2769251C - 5-fluoro-2-oxopyrimidine- 1(2h)-carboxylate derivatives - Google Patents
5-fluoro-2-oxopyrimidine- 1(2h)-carboxylate derivatives Download PDFInfo
- Publication number
- CA2769251C CA2769251C CA2769251A CA2769251A CA2769251C CA 2769251 C CA2769251 C CA 2769251C CA 2769251 A CA2769251 A CA 2769251A CA 2769251 A CA2769251 A CA 2769251A CA 2769251 C CA2769251 C CA 2769251C
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- CA
- Canada
- Prior art keywords
- optionally substituted
- compound
- ring system
- benzyl
- phenyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims abstract description 108
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 34
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
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- 150000003839 salts Chemical class 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
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- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
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- 125000003545 alkoxy group Chemical group 0.000 description 5
- MMNNNCCLKAWPPZ-UHFFFAOYSA-N ethyl 4-amino-5-fluoro-2-oxopyrimidine-1-carboxylate Chemical compound CCOC(=O)N1C=C(F)C(N)=NC1=O MMNNNCCLKAWPPZ-UHFFFAOYSA-N 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- KLCNYAYHZWWOSN-UHFFFAOYSA-N 2,2-dimethylpropyl 4-(dimethylaminomethylideneamino)-5-fluoro-2-oxopyrimidine-1-carboxylate Chemical compound CN(C)C=NC1=NC(=O)N(C(=O)OCC(C)(C)C)C=C1F KLCNYAYHZWWOSN-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
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- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- JWXZLCFGVKMEEK-UHFFFAOYSA-N triarathene Chemical compound C1=CC(Cl)=CC=C1C1=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)S1 JWXZLCFGVKMEEK-UHFFFAOYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- LTQZKHRCYAXPAZ-UHFFFAOYSA-N triazin-4-ylsulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=NN=N1 LTQZKHRCYAXPAZ-UHFFFAOYSA-N 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23223209P | 2009-08-07 | 2009-08-07 | |
| US61/232,232 | 2009-08-07 | ||
| PCT/US2010/044585 WO2011017544A1 (en) | 2009-08-07 | 2010-08-05 | 5-fluoro-2-oxopyrimidine- 1(2h)-carboxylate derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2769251A1 CA2769251A1 (en) | 2011-02-10 |
| CA2769251C true CA2769251C (en) | 2018-05-15 |
Family
ID=43535293
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2769251A Expired - Fee Related CA2769251C (en) | 2009-08-07 | 2010-08-05 | 5-fluoro-2-oxopyrimidine- 1(2h)-carboxylate derivatives |
Country Status (28)
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102574831B (zh) * | 2009-08-07 | 2014-12-10 | 陶氏益农公司 | N1-磺酰基-5-氟代嘧啶酮衍生物 |
| RU2656101C2 (ru) * | 2012-12-28 | 2018-05-31 | Адама Мактешим Лтд. | Производные 1-(замещенный бензоил)-5-фтор-4-имино-3-метил-3,4-дигидропиримидин-2(1h)-она |
| UA115462C2 (uk) * | 2012-12-28 | 2017-11-10 | Адама Махтешім Лтд. | Похідні n-(заміщеного)-5-фтор-4-іміно-3-метил-2-оксо-3,4-дигідропіримідин-1(2h)-карбоксилату |
| MX2015008444A (es) | 2012-12-28 | 2015-09-23 | Dow Agrosciences Llc | Derivados de n-(sustituido)-5-flouro-4-imino-3-metil-2-oxo-3,4-dih idropirimidin-1 (2h)-carboximida. |
| ES2874475T3 (es) | 2012-12-31 | 2021-11-05 | Adama Makhteshim Ltd | Derivados de la 3,4-dihidropirimidin-2(1h)-ona 3-alquil-5-fluoro-4-iminosustituida como fungicidas |
| AU2014373959B2 (en) | 2013-12-31 | 2017-10-26 | Adama Makhteshim Ltd. | 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1- (arylsulfonyl)-3,4-dihydropyrimidin-2(1H)-one and processes for their preparation |
| NZ722418A (en) | 2013-12-31 | 2018-01-26 | Adama Makhteshim Ltd | Synergistic fungicidal mixtures and compositions for fungal control |
| WO2016040193A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(1h-imidazo[4,5-c]pyridin-2-yl)-1h-pyrazolo[3,4-b]pyridine and therapeutic uses thereof |
| BR112018009252A2 (pt) | 2015-11-06 | 2018-11-06 | Samumed Llc | tratamento da osteoartrite |
| RS63813B1 (sr) | 2016-06-01 | 2023-01-31 | Biosplice Therapeutics Inc | Postupak pripreme n-(5-(3-(7-(3-fluorofenil)-3h-imidazo[4,5-c]piridin-2-il)-1h-indazol-5-il)piridin-3-il)-3-metilbutanamida |
| EP3655396A1 (en) | 2017-07-17 | 2020-05-27 | Adama Makhteshim Ltd. | Polymorphs of 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2-one |
| EA202191250A1 (ru) | 2018-11-05 | 2021-08-20 | Адама Мактешим Лтд. | Смеси и композиции, включающие 5-фтор-4-имино-3-метил-1-тозил-3,4-дигидропиримидин-2-он, и способы их применения |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3368938A (en) * | 1966-01-13 | 1968-02-13 | Hoffmann La Roche | Controlling fungi with 5-fluorocytosine |
| PL328777A1 (en) * | 1996-03-11 | 1999-02-15 | Novartis Ag | Pesticides |
| WO2004037159A2 (en) * | 2002-10-23 | 2004-05-06 | Obetherapy Biotechnology | Compounds, compositions and methods for modulating fat metabolism |
| BRPI0810821A8 (pt) * | 2007-04-27 | 2015-09-15 | Asubio Pharma Co Ltd | Derivados de anéis aromáticos de seis membros contendo nitrogênio e produtos farmacêuticos contendo os mesmos |
| CN102215691B (zh) | 2008-08-01 | 2015-02-04 | 陶氏益农公司 | 5-氟胞嘧啶作为杀真菌剂的用途 |
-
2010
- 2010-08-05 MX MX2012001623A patent/MX2012001623A/es active IP Right Grant
- 2010-08-05 NZ NZ597638A patent/NZ597638A/en unknown
- 2010-08-05 RS RS20140630A patent/RS53658B1/en unknown
- 2010-08-05 DK DK10807174.7T patent/DK2462133T3/en active
- 2010-08-05 KR KR1020127005932A patent/KR101792286B1/ko not_active Expired - Fee Related
- 2010-08-05 UA UAA201202680A patent/UA106086C2/uk unknown
- 2010-08-05 AU AU2010279408A patent/AU2010279408B2/en not_active Ceased
- 2010-08-05 WO PCT/US2010/044585 patent/WO2011017544A1/en active Application Filing
- 2010-08-05 CA CA2769251A patent/CA2769251C/en not_active Expired - Fee Related
- 2010-08-05 BR BR112012002807-3A patent/BR112012002807B1/pt active IP Right Grant
- 2010-08-05 IN IN695DEN2012 patent/IN2012DN00695A/en unknown
- 2010-08-05 JP JP2012523954A patent/JP5818791B2/ja active Active
- 2010-08-05 US US12/851,304 patent/US8318758B2/en active Active
- 2010-08-05 PT PT108071747T patent/PT2462133E/pt unknown
- 2010-08-05 PE PE2012000170A patent/PE20120689A1/es not_active Application Discontinuation
- 2010-08-05 ES ES10807174.7T patent/ES2506169T3/es active Active
- 2010-08-05 CN CN201080045339.3A patent/CN102548979B/zh active Active
- 2010-08-05 EP EP10807174.7A patent/EP2462133B1/en active Active
- 2010-08-05 PL PL10807174T patent/PL2462133T3/pl unknown
- 2010-08-05 EA EA201270255A patent/EA022930B1/ru not_active IP Right Cessation
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2012
- 2012-01-18 CR CR20120033A patent/CR20120033A/es unknown
- 2012-01-27 CO CO12012413A patent/CO6491089A2/es active IP Right Grant
- 2012-02-02 HN HN2012000261A patent/HN2012000261A/es unknown
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- 2012-02-05 IL IL217954A patent/IL217954A/en active IP Right Grant
- 2012-02-06 CL CL2012000314A patent/CL2012000314A1/es unknown
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2013
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| MKLA | Lapsed |
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