CA2952443C - Dimeric 1-arylpyrazole derivatives - Google Patents
Dimeric 1-arylpyrazole derivatives Download PDFInfo
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- CA2952443C CA2952443C CA2952443A CA2952443A CA2952443C CA 2952443 C CA2952443 C CA 2952443C CA 2952443 A CA2952443 A CA 2952443A CA 2952443 A CA2952443 A CA 2952443A CA 2952443 C CA2952443 C CA 2952443C
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- independently selected
- alkyl
- spp
- haloalkyl
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- 125000004961 1-arylpyrazolyl group Chemical group 0.000 title abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 184
- 239000000203 mixture Substances 0.000 claims abstract description 183
- -1 for example Substances 0.000 claims abstract description 153
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- 125000000217 alkyl group Chemical group 0.000 claims description 210
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 156
- 125000001188 haloalkyl group Chemical group 0.000 claims description 145
- 229910052736 halogen Inorganic materials 0.000 claims description 130
- 150000002367 halogens Chemical class 0.000 claims description 130
- 125000003118 aryl group Chemical group 0.000 claims description 122
- 125000001072 heteroaryl group Chemical group 0.000 claims description 117
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 105
- 229910052739 hydrogen Inorganic materials 0.000 claims description 97
- 125000003342 alkenyl group Chemical group 0.000 claims description 96
- 125000000304 alkynyl group Chemical group 0.000 claims description 94
- 239000001257 hydrogen Substances 0.000 claims description 68
- 125000003545 alkoxy group Chemical group 0.000 claims description 67
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- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
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- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- KVJXBPDAXMEYOA-CXANFOAXSA-N trilostane Chemical compound OC1=C(C#N)C[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@@]32O[C@@H]31 KVJXBPDAXMEYOA-CXANFOAXSA-N 0.000 description 1
- 229960001670 trilostane Drugs 0.000 description 1
- 229960003223 tripelennamine Drugs 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 229960004059 tylosin Drugs 0.000 description 1
- WBPYTXDJUQJLPQ-VMXQISHHSA-N tylosin Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 WBPYTXDJUQJLPQ-VMXQISHHSA-N 0.000 description 1
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- QTFFGPOXNNGTGZ-RCSCTSIBSA-N u3c8e5bwkr Chemical compound O.CS(O)(=O)=O.C1=CC=C2C(C(OC3C[C@@H]4CC5C[C@@H](N4CC5=O)C3)=O)=CNC2=C1 QTFFGPOXNNGTGZ-RCSCTSIBSA-N 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 1
- 229960000604 valproic acid Drugs 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229940045605 vanadium Drugs 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
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- 229960004298 vecuronium bromide Drugs 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 239000000273 veterinary drug Substances 0.000 description 1
- KDQAABAKXDWYSZ-PNYVAJAMSA-N vinblastine sulfate Chemical compound OS(O)(=O)=O.C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 KDQAABAKXDWYSZ-PNYVAJAMSA-N 0.000 description 1
- 229960004982 vinblastine sulfate Drugs 0.000 description 1
- AQTQHPDCURKLKT-JKDPCDLQSA-N vincristine sulfate Chemical compound OS(O)(=O)=O.C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C=O)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 AQTQHPDCURKLKT-JKDPCDLQSA-N 0.000 description 1
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- 229960001600 xylazine Drugs 0.000 description 1
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- 239000008096 xylene Substances 0.000 description 1
- BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
-
- 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pest Control & Pesticides (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Public Health (AREA)
- Agronomy & Crop Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11602108P | 2008-11-19 | 2008-11-19 | |
| US61/116,021 | 2008-11-19 | ||
| CA2743553A CA2743553C (en) | 2008-11-19 | 2009-11-18 | Dimeric 1-arylpyrazole derivatives |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2743553A Division CA2743553C (en) | 2008-11-19 | 2009-11-18 | Dimeric 1-arylpyrazole derivatives |
Publications (2)
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|---|---|
| CA2952443A1 CA2952443A1 (en) | 2010-05-27 |
| CA2952443C true CA2952443C (en) | 2019-04-02 |
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| CA2952443A Active CA2952443C (en) | 2008-11-19 | 2009-11-18 | Dimeric 1-arylpyrazole derivatives |
| CA2743553A Active CA2743553C (en) | 2008-11-19 | 2009-11-18 | Dimeric 1-arylpyrazole derivatives |
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| Application Number | Title | Priority Date | Filing Date |
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| CA2743553A Active CA2743553C (en) | 2008-11-19 | 2009-11-18 | Dimeric 1-arylpyrazole derivatives |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8642636B2 (enExample) |
| EP (1) | EP2364300B1 (enExample) |
| JP (1) | JP2012509338A (enExample) |
| CN (1) | CN102264706A (enExample) |
| AU (1) | AU2009316710B2 (enExample) |
| BR (1) | BRPI0922042B1 (enExample) |
| CA (2) | CA2952443C (enExample) |
| EA (1) | EA020923B1 (enExample) |
| ES (1) | ES2605811T3 (enExample) |
| MX (1) | MX2011005214A (enExample) |
| NZ (1) | NZ592985A (enExample) |
| WO (1) | WO2010059719A2 (enExample) |
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| MY173181A (en) | 2011-05-13 | 2020-01-02 | Array Biopharma Inc | Pyrrolidinyl urea, pyrrolidinyl thiourea and pyrrolidinyl guanidine compounds as trka kinase inhibitors |
| WO2014078378A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | Pyrrolidinyl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| US9822118B2 (en) | 2012-11-13 | 2017-11-21 | Array Biopharma Inc. | Bicyclic heteroaryl urea, thiourea, guanidine and cyanoguanidine compounds as TrkA kinase inhibitors |
| US9790178B2 (en) | 2012-11-13 | 2017-10-17 | Array Biopharma Inc. | Pyrrolidinyl urea, thiourea, guanidine and cyanoguanidine compounds as TrkA kinase inhibitors |
| EP2920166B1 (en) | 2012-11-13 | 2016-11-02 | Array Biopharma, Inc. | Bicyclic urea, thiourea, guanidine and cyanoguanidine compounds useful for the treatment of pain |
| WO2014078325A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | N-(monocyclic aryl),n'-pyrazolyl-urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| WO2014078331A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | N-(arylalkyl)-n'-pyrazolyl-urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| WO2014078328A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | N-bicyclic aryl,n'-pyrazolyl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| EP2922844B1 (en) | 2012-11-13 | 2018-01-10 | Array Biopharma, Inc. | N-pyrrolidinyl, n'-pyrazolyl- urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| US9981959B2 (en) | 2012-11-13 | 2018-05-29 | Array Biopharma Inc. | Thiazolyl and oxazolyl urea, thiourea, guanidine and cyanoguanidine compounds as TrkA kinase inhibitors |
| US9809578B2 (en) | 2012-11-13 | 2017-11-07 | Array Biopharma Inc. | Pyrazolyl urea, thiourea, guanidine and cyanoguanidine compounds as trkA kinase inhibitors |
| JP2016164125A (ja) * | 2013-07-02 | 2016-09-08 | 国立大学法人帯広畜産大学 | バベシア症の治療剤及び予防剤 |
| LT3154959T (lt) | 2014-05-15 | 2019-09-25 | Array Biopharma, Inc. | 1-((3s,4r)-4-(3-fluorfenil)-1-(2-metoksietil)pirolidin-3-il)-3-(4-metil-3-(2-metilpirimidin-5-il)-1-fenil-1h-pirazol-5-il)karbamidas kaip trka kinazės inhibitorius |
| US11384032B2 (en) | 2016-05-12 | 2022-07-12 | Verdesian Life Sciences, U.S., Llc | Compositions for controlling enzyme-induced urea decomposition |
| WO2018183562A1 (en) | 2017-03-28 | 2018-10-04 | Verdesian Life Sciences, U.S., Llc | Triarylmethane compounds for controlling enzyme-induced urea decomposition |
| WO2020096831A1 (en) | 2018-11-06 | 2020-05-14 | Dow Agrosciences Llc | Safened compositions comprising pyridine carboxylate herbicides and cloquintocet |
| WO2020096832A1 (en) * | 2018-11-06 | 2020-05-14 | Dow Agrosciences Llc | Compositions comprising pyridine carboxylate herbicides and azole carboxylate safeners |
| US12285012B2 (en) | 2018-11-07 | 2025-04-29 | Corteva Agriscience Llc | Compositions comprising pyridine carboxylate herbicides with acetolactate synthase (ALS) inhibitor herbicides |
| EA202191265A1 (ru) | 2018-11-07 | 2021-07-27 | КОРТЕВА АГРИСАЙЕНС ЭлЭлСи | Композиции, содержащие гербицид на основе пиридинкарбоксилата и гербициды, представляющие собой ингибиторы протопорфириногеноксидазы (protox) |
| BR112021008843A2 (pt) | 2018-11-07 | 2021-08-17 | Corteva Agriscience Llc | composições que compreendem herbicidas de carboxilato de piridina com fotossistema ii e herbicidas inibidores da hppd opcionais |
| CN112996393B (zh) | 2018-11-07 | 2023-05-12 | 科迪华农业科技有限责任公司 | 包含羧酸吡啶除草剂与合成生长素除草剂或生长素转运抑制剂的组合物 |
| WO2020096936A1 (en) | 2018-11-07 | 2020-05-14 | Dow Agrosciences Llc | Compositions comprising pyridine carboxylate herbicides and 4-hydroxyphenyl-pyruvate dioxygenase (hppd) inhibitor herbicides |
| EP3886854A4 (en) | 2018-11-30 | 2022-07-06 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| KR20230043904A (ko) | 2020-07-24 | 2023-03-31 | 엘랑코 유에스 인코포레이티드 | 이속사졸린 화합물 및 이의 중간체의 제조 공정 |
| EP4208157A1 (en) | 2020-09-04 | 2023-07-12 | Elanco Us Inc. | Palatable formulations |
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| US3966900A (en) * | 1969-03-12 | 1976-06-29 | Airwick Industries, Inc. | Evaporator system comprising a stabilized pesticidal phosphoric acid ester and method for stabilizing such ester enclosed in an evaporator |
| AU784798B2 (en) * | 1999-12-02 | 2006-06-22 | Boehringer Ingelheim Animal Health USA Inc. | Control of arthropods in animals |
| US7262214B2 (en) * | 2003-02-26 | 2007-08-28 | Merial Limited | 1-N-arylpyrazole derivatives in prevention of arthropod-borne and mosquito-borne diseases |
| WO2006000313A1 (en) * | 2004-06-26 | 2006-01-05 | Merial Ltd. | N-phenylpyrazole derivatives as pesticides |
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2009
- 2009-11-18 EP EP09756226.8A patent/EP2364300B1/en active Active
- 2009-11-18 CN CN2009801525502A patent/CN102264706A/zh active Pending
- 2009-11-18 ES ES09756226.8T patent/ES2605811T3/es active Active
- 2009-11-18 NZ NZ592985A patent/NZ592985A/xx unknown
- 2009-11-18 MX MX2011005214A patent/MX2011005214A/es active IP Right Grant
- 2009-11-18 AU AU2009316710A patent/AU2009316710B2/en active Active
- 2009-11-18 JP JP2011537582A patent/JP2012509338A/ja active Pending
- 2009-11-18 EA EA201100800A patent/EA020923B1/ru not_active IP Right Cessation
- 2009-11-18 WO PCT/US2009/064981 patent/WO2010059719A2/en not_active Ceased
- 2009-11-18 US US13/129,031 patent/US8642636B2/en active Active
- 2009-11-18 BR BRPI0922042A patent/BRPI0922042B1/pt active IP Right Grant
- 2009-11-18 CA CA2952443A patent/CA2952443C/en active Active
- 2009-11-18 CA CA2743553A patent/CA2743553C/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EA201100800A1 (ru) | 2011-12-30 |
| JP2012509338A (ja) | 2012-04-19 |
| AU2009316710A1 (en) | 2010-05-27 |
| BRPI0922042B1 (pt) | 2020-01-28 |
| CA2743553C (en) | 2017-03-14 |
| MX2011005214A (es) | 2011-06-01 |
| CN102264706A (zh) | 2011-11-30 |
| CA2952443A1 (en) | 2010-05-27 |
| EP2364300B1 (en) | 2016-10-19 |
| HK1160852A1 (en) | 2012-08-17 |
| EP2364300A2 (en) | 2011-09-14 |
| BRPI0922042A2 (pt) | 2016-11-01 |
| US8642636B2 (en) | 2014-02-04 |
| CA2743553A1 (en) | 2010-05-27 |
| ES2605811T3 (es) | 2017-03-16 |
| US20110245157A1 (en) | 2011-10-06 |
| EA020923B1 (ru) | 2015-02-27 |
| WO2010059719A3 (en) | 2010-11-18 |
| AU2009316710B2 (en) | 2015-08-06 |
| WO2010059719A2 (en) | 2010-05-27 |
| NZ592985A (en) | 2013-04-26 |
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| EEER | Examination request |
Effective date: 20161221 |