EA025517B1 - Соли n-(тетразол-5-ил)- и n-(триазол-5-ил)арилкарбоксамида и способ их применения в качестве гербицидов - Google Patents
Соли n-(тетразол-5-ил)- и n-(триазол-5-ил)арилкарбоксамида и способ их применения в качестве гербицидов Download PDFInfo
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- EA025517B1 EA025517B1 EA201401205A EA201401205A EA025517B1 EA 025517 B1 EA025517 B1 EA 025517B1 EA 201401205 A EA201401205 A EA 201401205A EA 201401205 A EA201401205 A EA 201401205A EA 025517 B1 EA025517 B1 EA 025517B1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- 239000004476 plant protection product Substances 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
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- 230000032361 posttranscriptional gene silencing Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
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- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
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- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/62—Quaternary ammonium compounds
- C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/40—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton with quaternised nitrogen atoms bound to carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12166621 | 2012-05-03 | ||
| PCT/EP2013/058964 WO2013164331A1 (de) | 2012-05-03 | 2013-04-30 | Salze von n-(tetrazol-5-yl)- und n-(triazol-5-yl)arylcarbonsäureamiden und ihre verwendung als herbizide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201401205A1 EA201401205A1 (ru) | 2015-04-30 |
| EA025517B1 true EA025517B1 (ru) | 2016-12-30 |
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| EA201401205A EA025517B1 (ru) | 2012-05-03 | 2013-04-30 | Соли n-(тетразол-5-ил)- и n-(триазол-5-ил)арилкарбоксамида и способ их применения в качестве гербицидов |
Country Status (19)
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2014184074A1 (en) * | 2013-05-15 | 2014-11-20 | Basf Se | Substituted n-(tetrazol-5-yl)- and n-(triazol-5-yl)hetarylcarboxamide compounds and their use as herbicides |
| ES2651491T3 (es) | 2013-05-31 | 2018-01-26 | Nissan Chemical Industries, Ltd. | Compuesto de amida heterocíclico |
| MX2016006624A (es) * | 2013-11-28 | 2016-12-02 | Bayer Cropscience Ag | Uso de 2-cloro-3-(metilsulfanil)-n-(1-metil-1h-tetrazol-5-il)-4-(t rifluorometil)benzamida o sus sales para controlar plantas no deseadas en areas de plantas de cultivo transgenico que son tolerantes a herbicidas inhibidores de hppd. |
| CN106458909B (zh) * | 2014-05-19 | 2020-03-17 | 先正达参股股份有限公司 | 具有硫取代的苯基或吡啶基团的具杀虫活性的酰胺衍生物 |
| EP3160946B1 (de) * | 2014-06-30 | 2018-06-06 | Bayer CropScience Aktiengesellschaft | Herbizid wirksame benzoesäureamide |
| AR100918A1 (es) * | 2014-06-30 | 2016-11-09 | Bayer Cropscience Ag | Amidas de ácido arilcarboxílico con actividad herbicida |
| HUE047821T2 (hu) | 2015-03-17 | 2020-05-28 | Bayer Cropscience Ag | N-(l,3,4-oxadiazol-2-il)aril-karbonsav-amidok sói és ezek alkalmazása herbicidként |
| US10597674B2 (en) | 2015-09-11 | 2020-03-24 | Basf Agricultural Solutions Seed, Us Llc | HPPD variants and methods of use |
| JP2020504115A (ja) | 2016-12-22 | 2020-02-06 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 置換アゾリルピロロンおよびアゾリルヒダントインならびにその塩ならびに除草活性物質としてのその使用 |
| WO2018125983A1 (en) | 2016-12-30 | 2018-07-05 | Mitobridge, Inc. | Oxopyridine derivatives useful as aminocarboxymuconate semialdehyde decarboxylase (acmsd) inhibitors |
| CA3055389A1 (en) | 2017-03-07 | 2018-09-13 | BASF Agricultural Solutions Seed US LLC | Hppd variants and methods of use |
| MX2019012981A (es) * | 2017-05-04 | 2019-12-18 | Bayer Cropscience Ag | 4-difluorometilbenzoilamidas de accion herbicida. |
| WO2021080330A1 (ko) * | 2019-10-21 | 2021-04-29 | 한국화학연구원 | 니코틴아마이드 화합물 및 이 화합물을 포함하는 제초제 조성물 |
| CA3179394A1 (en) * | 2020-04-07 | 2021-10-14 | Bayer Aktiengesellschaft | Substituted isophthalic acid diamides |
| WO2024074126A1 (zh) * | 2022-10-05 | 2024-04-11 | 江苏中旗科技股份有限公司 | 一种4-甲磺酰基苯甲酰胺类化合物、制备方法、除草组合物及用途 |
| KR20250091222A (ko) * | 2022-10-05 | 2025-06-20 | 지앙수 플래그 케미컬 인더스트리 컴퍼니 리미티드 | 4-메틸설포닐벤즈아미드류 화합물, 제조방법, 제초 조성물 및 용도 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004101532A1 (en) * | 2003-05-13 | 2004-11-25 | Bayer Cropscience Ag | Substituted triazolecarboxamides |
| WO2012028579A1 (de) * | 2010-09-01 | 2012-03-08 | Bayer Cropscience Ag | N-(tetrazol-5-yl)- und n-(triazol-5-yl)arylcarbonsäureamide und ihre verwendung als herbizide |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MA19269A1 (fr) * | 1980-09-16 | 1982-04-01 | Lilly Co Eli | Perfectionnement relatif a des derives de n-arylbenzamides . |
| EP0131624B1 (en) | 1983-01-17 | 1992-09-16 | Monsanto Company | Plasmids for transforming plant cells |
| BR8404834A (pt) | 1983-09-26 | 1985-08-13 | Agrigenetics Res Ass | Metodo para modificar geneticamente uma celula vegetal |
| BR8600161A (pt) | 1985-01-18 | 1986-09-23 | Plant Genetic Systems Nv | Gene quimerico,vetores de plasmidio hibrido,intermediario,processo para controlar insetos em agricultura ou horticultura,composicao inseticida,processo para transformar celulas de plantas para expressar uma toxina de polipeptideo produzida por bacillus thuringiensis,planta,semente de planta,cultura de celulas e plasmidio |
| ATE80182T1 (de) | 1985-10-25 | 1992-09-15 | Monsanto Co | Pflanzenvektoren. |
| EP0242236B2 (en) | 1986-03-11 | 1996-08-21 | Plant Genetic Systems N.V. | Plant cells resistant to glutamine synthetase inhibitors, made by genetic engineering |
| EP0305398B1 (en) | 1986-05-01 | 1991-09-25 | Honeywell Inc. | Multiple integrated circuit interconnection arrangement |
| US5013659A (en) | 1987-07-27 | 1991-05-07 | E. I. Du Pont De Nemours And Company | Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase |
| IL83348A (en) | 1986-08-26 | 1995-12-08 | Du Pont | Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase |
| DE3733017A1 (de) | 1987-09-30 | 1989-04-13 | Bayer Ag | Stilbensynthase-gen |
| ATE241007T1 (de) | 1990-03-16 | 2003-06-15 | Calgene Llc | Dnas, die für pflanzliche desaturasen kodieren und deren anwendungen |
| EP0536293B1 (en) | 1990-06-18 | 2002-01-30 | Monsanto Technology LLC | Increased starch content in plants |
| WO1992000377A1 (en) | 1990-06-25 | 1992-01-09 | Monsanto Company | Glyphosate tolerant plants |
| DE4107396A1 (de) | 1990-06-29 | 1992-01-02 | Bayer Ag | Stilbensynthase-gene aus weinrebe |
| SE467358B (sv) | 1990-12-21 | 1992-07-06 | Amylogene Hb | Genteknisk foeraendring av potatis foer bildning av staerkelse av amylopektintyp |
| DE4104782B4 (de) | 1991-02-13 | 2006-05-11 | Bayer Cropscience Gmbh | Neue Plasmide, enthaltend DNA-Sequenzen, die Veränderungen der Karbohydratkonzentration und Karbohydratzusammensetzung in Pflanzen hervorrufen, sowie Pflanzen und Pflanzenzellen enthaltend dieses Plasmide |
| US8822378B2 (en) | 2011-08-03 | 2014-09-02 | Bayer Intellectual Property Gmbh | N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamides and use thereof as herbicides |
| EP2589598A1 (de) * | 2011-11-03 | 2013-05-08 | Bayer CropScience AG | 5-Phenylsubstituierte N-(Tetrazol-5-yl)- und N-(Triazol-5-yl)arylcarbonsäureamide und ihre Verwendung als Herbizide |
| EP2589293A1 (de) * | 2011-11-03 | 2013-05-08 | Bayer CropScience AG | Herbizid-Safener-Zusammensetzungen enthaltend N-(Tetrazol-5-yl)- und N-(Triazol-5-yl)arylcarbonsäureamide |
| AU2013206392B2 (en) * | 2012-04-27 | 2016-05-12 | Basf Se | Substituted N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamide compounds and their use as herbicides |
-
2013
- 2013-04-30 EP EP16179944.0A patent/EP3121172B1/de not_active Not-in-force
- 2013-04-30 CA CA 2872374 patent/CA2872374A1/en not_active Abandoned
- 2013-04-30 HU HUE16179944A patent/HUE042768T2/hu unknown
- 2013-04-30 UA UAA201412738A patent/UA113545C2/uk unknown
- 2013-04-30 JP JP2015509414A patent/JP6104368B2/ja not_active Expired - Fee Related
- 2013-04-30 PL PL16179944T patent/PL3121172T3/pl unknown
- 2013-04-30 KR KR20147030768A patent/KR20150003784A/ko not_active Ceased
- 2013-04-30 IN IN8150DEN2014 patent/IN2014DN08150A/en unknown
- 2013-04-30 US US14/397,677 patent/US9371315B2/en not_active Expired - Fee Related
- 2013-04-30 MX MX2014013159A patent/MX363987B/es active IP Right Grant
- 2013-04-30 ES ES16179944T patent/ES2705618T3/es active Active
- 2013-04-30 EP EP13719550.9A patent/EP2844649A1/de not_active Withdrawn
- 2013-04-30 EA EA201401205A patent/EA025517B1/ru not_active IP Right Cessation
- 2013-04-30 AU AU2013255929A patent/AU2013255929B2/en not_active Ceased
- 2013-04-30 BR BR112014027185A patent/BR112014027185B1/pt not_active IP Right Cessation
- 2013-04-30 WO PCT/EP2013/058964 patent/WO2013164331A1/de active Application Filing
- 2013-04-30 CN CN201380023321.7A patent/CN104271563B/zh not_active Expired - Fee Related
- 2013-05-03 AR ARP130101526 patent/AR090939A1/es unknown
-
2014
- 2014-10-28 CO CO14238494A patent/CO7180218A2/es unknown
- 2014-12-02 ZA ZA2014/08836A patent/ZA201408836B/en unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004101532A1 (en) * | 2003-05-13 | 2004-11-25 | Bayer Cropscience Ag | Substituted triazolecarboxamides |
| WO2012028579A1 (de) * | 2010-09-01 | 2012-03-08 | Bayer Cropscience Ag | N-(tetrazol-5-yl)- und n-(triazol-5-yl)arylcarbonsäureamide und ihre verwendung als herbizide |
Non-Patent Citations (2)
| Title |
|---|
| BERGE S. M., BIGHLEY L. D., MONKHOUSE D. C.: "PHARMACEUTICALS SALTS.", JOURNAL OF PHARMACEUTICAL SCIENCES, AMERICAN PHARMACEUTICAL ASSOCIATION., WASHINGTON, US, vol. 66., no. 01., 1 January 1977 (1977-01-01), WASHINGTON, US, pages 01 - 19., XP000562636, ISSN: 0022-3549, DOI: 10.1002/jps.2600660104 * |
| STAHL PETER HEINRICH ; WERMUTH CAMILLE G.: "HANDBOOK OF PHARMACEUTICAL SALTS : PROPERTIES, SELECTION, AND USE.", 1 January 2002, ZÜRICH : VERL. HELVETICA CHIMICA ACTA ; WEINHEIM [U.A.] : WILEY-VCH, DE, ISBN: 978-3-906390-26-0, article C.G. WERMUTH, P.H. STAHL: "Handbook of Pharmaceutical Salts passsage", pages: 1 - 7, XP002421267, 031641 * |
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| IN2014DN08150A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2015-05-01 |
| JP6104368B2 (ja) | 2017-03-29 |
| MX363987B (es) | 2019-04-10 |
| CA2872374A1 (en) | 2013-11-07 |
| PL3121172T3 (pl) | 2019-04-30 |
| JP2015517456A (ja) | 2015-06-22 |
| ZA201408836B (en) | 2017-09-27 |
| CN104271563B (zh) | 2017-10-17 |
| AU2013255929B2 (en) | 2017-02-16 |
| CO7180218A2 (es) | 2015-02-09 |
| HUE042768T2 (hu) | 2019-07-29 |
| WO2013164331A1 (de) | 2013-11-07 |
| EP2844649A1 (de) | 2015-03-11 |
| BR112014027185B1 (pt) | 2019-10-22 |
| US20150105253A1 (en) | 2015-04-16 |
| ES2705618T3 (es) | 2019-03-26 |
| UA113545C2 (xx) | 2017-02-10 |
| EA201401205A1 (ru) | 2015-04-30 |
| EP3121172A1 (de) | 2017-01-25 |
| AU2013255929A1 (en) | 2014-11-20 |
| AR090939A1 (es) | 2014-12-17 |
| CN104271563A (zh) | 2015-01-07 |
| KR20150003784A (ko) | 2015-01-09 |
| MX2014013159A (es) | 2015-01-19 |
| BR112014027185A2 (pt) | 2017-06-27 |
| US9371315B2 (en) | 2016-06-21 |
| EP3121172B1 (de) | 2018-10-17 |
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