AR108184A1 - Proceso para preparar compuestos de isoxazolina - Google Patents
Proceso para preparar compuestos de isoxazolinaInfo
- Publication number
- AR108184A1 AR108184A1 ARP170100879A ARP170100879A AR108184A1 AR 108184 A1 AR108184 A1 AR 108184A1 AR P170100879 A ARP170100879 A AR P170100879A AR P170100879 A ARP170100879 A AR P170100879A AR 108184 A1 AR108184 A1 AR 108184A1
- Authority
- AR
- Argentina
- Prior art keywords
- ring
- alkyl
- cycloalkyl
- alkoxy
- halogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- 150000002547 isoxazolines Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 12
- 125000003545 alkoxy group Chemical group 0.000 abstract 8
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 8
- 125000001424 substituent group Chemical group 0.000 abstract 8
- 125000003282 alkyl amino group Chemical group 0.000 abstract 7
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 7
- 229910052736 halogen Inorganic materials 0.000 abstract 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 6
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 6
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 abstract 6
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 abstract 6
- 125000003342 alkenyl group Chemical group 0.000 abstract 5
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 abstract 5
- 125000004414 alkyl thio group Chemical group 0.000 abstract 5
- 125000000304 alkynyl group Chemical group 0.000 abstract 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 5
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 5
- 125000004995 haloalkylthio group Chemical group 0.000 abstract 5
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 abstract 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 125000001188 haloalkyl group Chemical group 0.000 abstract 4
- 125000005843 halogen group Chemical group 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- -1 isoxazoline compound Chemical class 0.000 abstract 3
- 235000001258 Cinchona calisaya Nutrition 0.000 abstract 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 abstract 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 abstract 2
- 125000004992 haloalkylamino group Chemical group 0.000 abstract 2
- 125000005347 halocycloalkyl group Chemical group 0.000 abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000003444 phase transfer catalyst Substances 0.000 abstract 2
- 229960000948 quinine Drugs 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 abstract 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 1
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 230000002141 anti-parasite Effects 0.000 abstract 1
- 239000003096 antiparasitic agent Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000004452 carbocyclyl group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000000262 haloalkenyl group Chemical group 0.000 abstract 1
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000006809 haloalkylaminocarbonyl group Chemical group 0.000 abstract 1
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 abstract 1
- 125000000232 haloalkynyl group Chemical group 0.000 abstract 1
- 125000005549 heteroarylene group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000005835 indanylene group Chemical group 0.000 abstract 1
- 125000004957 naphthylene group Chemical group 0.000 abstract 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
- 125000003396 thiol group Chemical class [H]S* 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 229920002554 vinyl polymer Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
-
- 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
- A01N43/72—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
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
- A01N55/08—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing boron
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- 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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
- C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine
-
- 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
- C07D491/02—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 two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- 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
- C07B2200/07—Optical isomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Procesos para la preparación de compuestos antiparasitarios de isoxazolina enriquecidos en un enantiómero usando un catalizador de transferencia de fase quiral a base de quinina. También, catalizadores de transferencia de fase a base de quinina y una forma de solvato con tolueno del compuesto de isoxazolina de la solicitud. Reivindicación 1: Un proceso para la preparación del compuesto de isoxazolina de fórmula (1), que está enriquecido en un enantiómero, donde: B¹, B², B³, son cada uno independientemente C-R o N; cada R es independientemente H, halógeno, ciano, -NO₂, alquilo, haloalquilo, alcoxi, haloalcoxi, alquiltio, haloalquiltio, alquilsulfinilo, haloalquilsulfinilo, alquilsulfonilo, haloalquilsulfonilo, alquilamino, dialquilamino o alcoxicarbonilo; R¹ es C₁₋₃alquilo o C₁₋₃haloalquilo; Y es un fenileno, naftileno, indanileno opcionalmente sustituido, un heteroarileno de 5 ó 6 miembros o un heterobiciclileno fusionado de entre 8 y 10 miembros, donde los sustituyentes opcionales se seleccionan entre el grupo que consiste en halógeno, alquilo, haloalquilo, cicloalquilo, halocicloalquilo, alcoxi, haloalcoxi, alquiltio, haloalquiltio, alquilsulfinilo, haloalquilsulfinilo, alquilsulfonilo, haloalquilsulfonilo, alquilamino, dialquilamino, -CN o -NO₂ y NH₂-C(=S)-; Q es T-NR²R³, el grupo (-CH₂-)(-CH₂-)N-R³, OH, NH₂, alcoxi, haloalcoxi, alquilamino, haloalquilamino, dialquilamino, halodialquilamino, tiol, alquiltio, haloalquiltio, alquilsulfinilo, haloalquilsulfinilo, alquilsulfonilo, haloalquilsulfonilo, o un anillo carbociclilo, heterociclilo o heteroarilo de 5 ó 6 miembros opcionalmente sustituido; T es (CH₂)ₙ, CH(CH₃), CH(CN), C(=O) o C(=S); R² es H, alquilo, alquenilo, alquinilo, cicloalquilo, alquilcicloalquilo, cicloalquilalquilo, alquilcarbonilo o alcoxicarbonilo; R³ es H, OR⁷, NR⁸R⁹ o Q¹; o alquilo, haloalquilo, alquenilo, haloalquenilo, alquinilo, haloalquinilo, cicloalquilo, alquilcicloalquilo, cicloalquilalquilo, alquilcarbonilo, alcoxicarbonilo, aminocarbonilo, alquilaminocarbonilo o dialquilaminocarbonilo, cada uno de los cuales opcionalmente puede estar sustituido con uno o más sustituyentes que se seleccionan independientemente entre los R⁴; o R² y R³ se toman junto con el nitrógeno al que están unidos para formar un anillo que contiene entre 2 y 6 átomos de carbono y opcionalmente un átomo adicional que se selecciona entre el grupo que consiste en N, S y O, donde dicho anillo opcionalmente sustituido con entre 1 y 4 sustituyentes se selecciona independientemente entre el grupo que consiste en alquilo, halógeno, -CN, -NO₂ y alcoxi; cada R⁴ es independientemente halógeno; alquilo, cicloalquilo, alcoxi, alquiltio, haloalquiltio, alquilsulfinilo, haloalquilsulfinilo, alquilsulfonilo, haloalquilsulfonilo, alquilamino, haloalquilamino, dialquilamino, dihaloalquilamino, cicloalquilamino, alquilcarbonilo, alcoxicarbonilo, alquilaminocarbonilo, dialquilaminocarbonilo, haloalquilcarbonilo, haloalcoxicarbonilo, haloalquilaminocarbonilo, dihaloalquilaminocarbonilo, hidroxi, -NH₂, -CN o -NO₂; o Q²; cada R⁵ es independientemente halógeno, alcoxi, haloalcoxi, alquiltio haloalquiltio, alquilsulfinilo, haloalquilsulfinilo, alquilsulfonilo, haloalquilsulfonilo, alquilamino, dialquilamino, alcoxicarbonilo, -CN o -NO₂; cada R⁶ es independientemente halógeno, alquilo, haloalquilo, cicloalquilo, halocicloalquilo, alcoxi, haloalcoxi, alquiltio, haloalquiltio, alquilsulfinilo, haloalquilsulfinilo, alquilsulfonilo, haloalquilsulfonilo, alquilamino, dialquilamino, -CN, -NO₂, fenilo o piridinilo; R⁷ es H; o alquilo, alquenilo, alquinilo, cicloalquilo, alquilcicloalquilo o cicloalquilalquilo, cada uno de los cuales opcionalmente puede estar sustituido con uno o más átomos de halógeno; R⁸ es H, alquilo, alquenilo, alquinilo, cicloalquilo, alquilcicloalquilo, cicloalquilalquilo, alquilcarbonilo o alcoxicarbonilo; R⁹ es H; Q³; o alquilo, alquenilo, alquinilo, cicloalquilo, alquilcicloalquilo o cicloalquilalquilo, cada uno de los cuales opcionalmente puede estar sustituido con uno o más sustituyentes que se seleccionan independientemente entre los R⁴; o R⁸ y R⁹ se toman junto con el nitrógeno al que están unidos para formar un anillo que contiene entre 2 y 6 átomos de carbono y opcionalmente un átomo adicional que se selecciona entre el grupo que consiste en N, S y O, donde dicho anillo opcionalmente sustituido con entre 1 y 4 sustituyentes se selecciona independientemente entre el grupo que consiste en alquilo, halógeno, -CN, -NO₂ y alcoxi; Q¹ es un anillo fenilo, un anillo heterocíclico de 5 ó 6 miembros, o un sistema de anillos bicíclicos fusionados de 8, 9 ó 10 miembros que opcionalmente contiene entre uno y tres heteroátomos que se seleccionan entre hasta 1 O, hasta 1 S y hasta 3 N, donde cada anillo o sistema de anillos opcionalmente está sustituido con uno o más sustituyentes que se seleccionan independientemente entre los R⁵; Q² es independientemente un anillo fenilo o un anillo heterocíclico de 5 ó 6 miembros, donde cada anillo opcionalmente está sustituido con uno o más sustituyentes que se seleccionan independientemente entre los R⁶; Q³ es un anillo fenilo o un anillo heterocíclico de 5 ó 6 miembros, donde cada anillo opcionalmente está sustituido con uno o más sustituyentes que se seleccionan independientemente entre los R⁶; y n es 0, 1 ó 2; donde el asterisco representa que el átomo de carbono es un átomo de carbono cuaternario quiral; caracterizado porque comprende hacer reaccionar un compuesto de fórmula (2), donde B¹, B², B³, R¹, Y y Q son como se los definió para la fórmula (1), con hidroxilamina en presencia de agua, una base y un catalizador de transferencia de fase quiral de fórmula (3a) ó (3b), donde R es arilo o heteroarilo sustituido con uno o más grupos aralcoxi, amino, alquilamino o dialquilamino; R es hidrógeno o C₁₋₃alcoxi; W es etilo o vinilo; y X⁻ es un anión; y aislar el compuesto.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662319207P | 2016-04-06 | 2016-04-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR108184A1 true AR108184A1 (es) | 2018-07-25 |
Family
ID=58549312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP170100879A AR108184A1 (es) | 2016-04-06 | 2017-04-05 | Proceso para preparar compuestos de isoxazolina |
Country Status (31)
| Country | Link |
|---|---|
| US (3) | US10433552B2 (es) |
| EP (2) | EP3440062B1 (es) |
| KR (2) | KR102403531B1 (es) |
| CN (2) | CN114805234A (es) |
| AR (1) | AR108184A1 (es) |
| AU (2) | AU2017246305B2 (es) |
| CA (2) | CA3214922A1 (es) |
| CL (2) | CL2018002838A1 (es) |
| CO (3) | CO2018010719A2 (es) |
| CY (1) | CY1124797T1 (es) |
| DK (1) | DK3440062T3 (es) |
| EA (1) | EA201892245A1 (es) |
| ES (1) | ES2903286T3 (es) |
| HR (1) | HRP20211979T1 (es) |
| HU (1) | HUE056909T2 (es) |
| IL (2) | IL262093B (es) |
| LT (1) | LT3440062T (es) |
| MD (2) | MD4846C1 (es) |
| MX (2) | MX2018012184A (es) |
| MY (1) | MY189534A (es) |
| NZ (2) | NZ786434A (es) |
| PL (1) | PL3440062T3 (es) |
| PT (1) | PT3440062T (es) |
| RS (1) | RS62755B1 (es) |
| SG (1) | SG11201808756XA (es) |
| SI (1) | SI3440062T1 (es) |
| TW (1) | TWI753897B (es) |
| UA (1) | UA127309C2 (es) |
| UY (1) | UY37196A (es) |
| WO (1) | WO2017176948A1 (es) |
| ZA (1) | ZA201806675B (es) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UY37137A (es) | 2016-02-24 | 2017-09-29 | Merial Inc | Compuestos antiparasitarios de isoxazolina, formulaciones inyectables de acción prolongada que los comprenden, métodos y usos de los mismos |
| AR111412A1 (es) * | 2017-04-05 | 2019-07-10 | Merial Inc | Formas cristalinas de (s)-afoxolaner |
| JP2021503465A (ja) | 2017-11-16 | 2021-02-12 | アビスタ ファーマ ソリューションズ，インコーポレーテッド | 単一エナンチオマーの抗寄生生物化合物 |
| US10835517B2 (en) | 2017-12-15 | 2020-11-17 | Tarsus Pharmaceuticals, Inc. | Methods for treating ocular demodex using isoxazoline parasiticide formulations |
| TWI812673B (zh) * | 2018-02-12 | 2023-08-21 | 美商富曼西公司 | 用於防治無脊椎害蟲之萘異噁唑啉化合物 |
| AU2019369659A1 (en) | 2018-10-29 | 2021-04-29 | Basf Se | Process for preparation of optically enriched aldol compounds |
| CN115768753B (zh) * | 2020-06-19 | 2024-04-26 | 东莞市东阳光动物保健药品有限公司 | 一种gaba抑制剂的晶型及其制备方法 |
| WO2022020585A1 (en) | 2020-07-24 | 2022-01-27 | Elanco Us Inc. | Process for making an isoxazoline compound and intermediate thereof |
| CN112724095A (zh) * | 2020-09-25 | 2021-04-30 | 安徽省公众检验研究院有限公司 | 氟雷拉钠晶型及其制备方法 |
| CN117915782A (zh) * | 2021-06-25 | 2024-04-19 | 碗中动物健康公司 | 猫科动物口服饲料和在猫科动物中控制蚤侵袭的方法 |
| EP4384514A1 (en) | 2021-08-11 | 2024-06-19 | Elanco Us Inc. | Process for making diaryl isoxazoline derivative |
| CN115710185B (zh) * | 2021-08-23 | 2024-05-03 | 中国石油化工股份有限公司 | 利用金属碳化物催化剂生产甲胺的方法 |
| CN114113388B (zh) * | 2021-11-24 | 2023-05-23 | 丽珠集团新北江制药股份有限公司 | 一种4-肟甲基-1-萘甲酸中有关物质的检测方法 |
| CN116903488B (zh) * | 2022-11-25 | 2023-12-15 | 济南久隆医药科技有限公司 | 一种阿福拉纳的合成方法 |
| CN115959979A (zh) * | 2022-12-29 | 2023-04-14 | 南京正荣医药化学有限公司 | 一种3-氯-4-氟-5-三氟甲基三氟苯乙酮的制备方法 |
| CN116143652B (zh) * | 2023-01-13 | 2024-06-28 | 四川青木制药有限公司 | 一种阿福拉纳中间体及其制备方法和应用 |
Family Cites Families (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3060084A (en) | 1961-06-09 | 1962-10-23 | Du Pont | Improved homogeneous, readily dispersed, pesticidal concentrate |
| US3299566A (en) | 1964-06-01 | 1967-01-24 | Olin Mathieson | Water soluble film containing agricultural chemicals |
| US4144050A (en) | 1969-02-05 | 1979-03-13 | Hoechst Aktiengesellschaft | Micro granules for pesticides and process for their manufacture |
| US3920442A (en) | 1972-09-18 | 1975-11-18 | Du Pont | Water-dispersible pesticide aggregates |
| US4172714A (en) | 1976-12-20 | 1979-10-30 | E. I. Du Pont De Nemours And Company | Dry compactible, swellable herbicidal compositions and pellets produced therefrom |
| GB2095558B (en) | 1981-03-30 | 1984-10-24 | Avon Packers Ltd | Formulation of agricultural chemicals |
| US5180587A (en) | 1988-06-28 | 1993-01-19 | E. I. Du Pont De Nemours And Company | Tablet formulations of pesticides |
| ES2126553T3 (es) | 1989-08-30 | 1999-04-01 | Aeci Ltd | Dispositivo dosificador y su uso. |
| CA2083185A1 (en) | 1990-03-12 | 1991-09-13 | William Lawrence Geigle | Water-dispersible or water-soluble pesticide granules from heat-activated binders |
| DE69122201T2 (de) | 1990-10-11 | 1997-02-06 | Sumitomo Chemical Co | Pestizide Zusammensetzung |
| DE4322211A1 (de) | 1993-07-03 | 1995-01-12 | Basf Ag | Wäßrige, mehrphasige, stabile Fertigformulierung für Pflanzenschutz-Wirkstoffe und Verfahren zu ihrer Herstellung |
| CN1930136B (zh) | 2004-03-05 | 2012-02-08 | 日产化学工业株式会社 | 异*唑啉取代苯甲酰胺化合物及有害生物防除剂 |
| ES2443690T3 (es) | 2005-09-02 | 2014-02-20 | Nissan Chemical Industries, Ltd. | Compuesto de benzamida sustituido con isoxazolina y agente controlador de organismos dañinos |
| EP1965645A2 (en) | 2005-12-14 | 2008-09-10 | E.I. Du Pont De Nemours And Company | Isoxazolines for controlling invertebrate pests |
| TW200803740A (en) | 2005-12-16 | 2008-01-16 | Du Pont | 5-aryl isoxazolines for controlling invertebrate pests |
| TWI412322B (zh) | 2005-12-30 | 2013-10-21 | Du Pont | 控制無脊椎害蟲之異唑啉 |
| AU2007240954A1 (en) | 2006-04-20 | 2007-11-01 | E. I. Du Pont De Nemours And Company | Pyrazolines for controlling invertebrate pests |
| JP2008044880A (ja) | 2006-08-15 | 2008-02-28 | Bayer Cropscience Ag | 殺虫性イソオキサゾリン類 |
| US8466150B2 (en) | 2006-12-28 | 2013-06-18 | Abbott Laboratories | Inhibitors of poly(ADP-ribose)polymerase |
| JP5256753B2 (ja) | 2007-03-29 | 2013-08-07 | 住友化学株式会社 | イソオキサゾリン化合物とその有害生物防除用途 |
| NZ580241A (en) | 2007-04-10 | 2011-02-25 | Bayer Cropscience Ag | Insecticidal aryl isoxazoline derivatives |
| AU2008261793A1 (en) * | 2007-06-13 | 2008-12-18 | E. I. Du Pont De Nemours And Company | Isoxazoline insecticides |
| TWI430995B (zh) * | 2007-06-26 | 2014-03-21 | Du Pont | 萘異唑啉無脊椎有害動物控制劑 |
| US8952175B2 (en) | 2007-06-27 | 2015-02-10 | Nissan Chemical Industries, Ltd. | Method for production of 3-hydroxypropan-1-one compound, method for production of 2-propen-1-one compound and method for production of isoxazoline compound |
| TWI556741B (zh) | 2007-08-17 | 2016-11-11 | 英特威特國際股份有限公司 | 異唑啉組成物及其作為抗寄生蟲藥上的應用 |
| TWI649303B (zh) | 2007-08-17 | 2019-02-01 | 杜邦股份有限公司 | 製備４-乙醯基-ｎ-〔２-側氧基-２-〔（２，２，２-三氟乙基）胺基〕乙基〕-１-萘甲醯胺之化合物及方法 |
| US8367584B2 (en) | 2007-10-03 | 2013-02-05 | E.I. Du Pont De Nemours And Company | Naphthalene isoxazoline compounds for control of invertebrate pests |
| WO2009063910A1 (ja) | 2007-11-12 | 2009-05-22 | Nissan Chemical Industries, Ltd. | 光学活性イソキサゾリン化合物の触媒的不斉合成方法 |
| JP2011527307A (ja) | 2008-07-09 | 2011-10-27 | ビーエーエスエフ ソシエタス・ヨーロピア | イソオキサゾリン化合物ｉを含む殺有害生物活性混合物 |
| CA2747354C (en) | 2008-12-19 | 2016-12-06 | Novartis Ag | Isoxazoline derivatives and their use as pesticide |
| TWI487486B (zh) | 2009-12-01 | 2015-06-11 | Syngenta Participations Ag | 以異唑啉衍生物為主之殺蟲化合物 |
| WO2011104089A1 (en) * | 2010-02-25 | 2011-09-01 | Syngenta Participations Ag | Process for the preparation of isoxazoline derivatives |
| US20130203591A1 (en) | 2010-06-09 | 2013-08-08 | Syngenta Crop Protection Llc | Pesticidal mixtures including isoxazoline derivatives |
| SI2683723T1 (sl) * | 2011-03-10 | 2016-07-29 | Zoetis Services Llc | Spirociklični izoksazolinski derivati kot antiparazitiki |
| WO2013069731A1 (ja) | 2011-11-08 | 2013-05-16 | 日産化学工業株式会社 | 光学活性イソキサゾリン化合物の触媒的不斉合成方法及び光学活性イソキサゾリン化合物 |
| EP2809667A1 (en) | 2012-02-03 | 2014-12-10 | Zoetis LLC | Process for the preparation of chiral isoxazoline azetidine derivatives as antiparasitic agents |
| CN104918944B (zh) | 2012-11-21 | 2017-05-10 | 硕腾服务有限责任公司 | 螺环异噁唑啉衍生物的合成 |
| WO2014090918A1 (en) * | 2012-12-13 | 2014-06-19 | Novartis Ag | Process for the enantiomeric enrichment of diaryloxazoline derivatives |
| MX367952B (es) * | 2013-01-31 | 2019-09-12 | Boehringer Ingelheim Animal Health Usa Inc | Método para tratar y curar leishmaniosis usando fexinidazol. |
| AR096022A1 (es) * | 2013-04-11 | 2015-12-02 | Basf Se | Compuestos de pirimidinio sustituido, útiles para combatir plagas de animales |
-
2017
- 2017-04-05 EP EP17718286.2A patent/EP3440062B1/en active Active
- 2017-04-05 ES ES17718286T patent/ES2903286T3/es active Active
- 2017-04-05 RS RS20211583A patent/RS62755B1/sr unknown
- 2017-04-05 HR HRP20211979TT patent/HRP20211979T1/hr unknown
- 2017-04-05 MX MX2018012184A patent/MX2018012184A/es unknown
- 2017-04-05 MX MX2020013754A patent/MX2020013754A/es unknown
- 2017-04-05 SG SG11201808756XA patent/SG11201808756XA/en unknown
- 2017-04-05 KR KR1020187032223A patent/KR102403531B1/ko active IP Right Grant
- 2017-04-05 LT LTEPPCT/US2017/026245T patent/LT3440062T/lt unknown
- 2017-04-05 MY MYPI2018001696A patent/MY189534A/en unknown
- 2017-04-05 KR KR1020217042747A patent/KR102438541B1/ko active IP Right Grant
- 2017-04-05 CN CN202210256802.3A patent/CN114805234A/zh active Pending
- 2017-04-05 EA EA201892245A patent/EA201892245A1/ru unknown
- 2017-04-05 UA UAA201810929A patent/UA127309C2/uk unknown
- 2017-04-05 SI SI201730954T patent/SI3440062T1/sl unknown
- 2017-04-05 CN CN201780033192.8A patent/CN109195955B/zh active Active
- 2017-04-05 AR ARP170100879A patent/AR108184A1/es active IP Right Grant
- 2017-04-05 AU AU2017246305A patent/AU2017246305B2/en active Active
- 2017-04-05 EP EP21190677.1A patent/EP3978483B1/en active Active
- 2017-04-05 PT PT177182862T patent/PT3440062T/pt unknown
- 2017-04-05 MD MDA20180090A patent/MD4846C1/ro active IP Right Grant
- 2017-04-05 US US15/480,316 patent/US10433552B2/en active Active
- 2017-04-05 NZ NZ786434A patent/NZ786434A/en unknown
- 2017-04-05 PL PL17718286T patent/PL3440062T3/pl unknown
- 2017-04-05 CA CA3214922A patent/CA3214922A1/en active Pending
- 2017-04-05 HU HUE17718286A patent/HUE056909T2/hu unknown
- 2017-04-05 DK DK17718286.2T patent/DK3440062T3/da active
- 2017-04-05 WO PCT/US2017/026245 patent/WO2017176948A1/en active Application Filing
- 2017-04-05 MD MDA20220052A patent/MD20220052A2/ro unknown
- 2017-04-05 CA CA3019947A patent/CA3019947A1/en active Pending
- 2017-04-05 NZ NZ747676A patent/NZ747676A/en unknown
- 2017-04-06 UY UY0001037196A patent/UY37196A/es active IP Right Grant
- 2017-04-06 TW TW106111606A patent/TWI753897B/zh active
-
2018
- 2018-10-03 IL IL262093A patent/IL262093B/en active IP Right Grant
- 2018-10-04 CO CONC2018/0010719A patent/CO2018010719A2/es unknown
- 2018-10-04 CO CONC2019/0013500A patent/CO2019013500A2/es unknown
- 2018-10-04 CO CONC2019/0013841A patent/CO2019013841A2/es unknown
- 2018-10-05 CL CL2018002838A patent/CL2018002838A1/es unknown
- 2018-10-08 ZA ZA2018/06675A patent/ZA201806675B/en unknown
- 2018-11-07 US US16/182,838 patent/US10750744B2/en active Active
-
2019
- 2019-11-12 CL CL2019003235A patent/CL2019003235A1/es unknown
-
2020
- 2020-07-14 US US16/928,493 patent/US11324220B2/en active Active
-
2021
- 2021-02-07 IL IL280679A patent/IL280679B/en unknown
- 2021-05-17 AU AU2021203129A patent/AU2021203129B2/en active Active
- 2021-12-02 CY CY20211101056T patent/CY1124797T1/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AR108184A1 (es) | Proceso para preparar compuestos de isoxazolina | |
| AR104202A1 (es) | Derivados heterocíclicos bicíclicos condensados como pesticidas | |
| ES2618703T3 (es) | Nuevos compuestos diazaspirocicloalcano y azaspirocicloalcano | |
| AR095312A1 (es) | Compuestos de biarilamida como inhibidores de cinasa | |
| AR090488A1 (es) | Derivados de n-ciclobutilbenzamida, un proceso para su obtencion, intermediarios para su sintesis, composiciones pesticidas y farmaceuticas que los comprenden y metodos para controlar daños debidos a una plaga y/u hongos | |
| AR099823A1 (es) | Compuestos bicíclicos de 7 eslabones | |
| PE20181024A1 (es) | Derivados de ciclohexano sustituido con amido | |
| AR108388A2 (es) | Compuestos de oxazol sustituidos con indazol como inhibidores de pi3-quinasas | |
| AR061369A1 (es) | Derivados de pirimidina y composiciones farmaceuticas que los comprenden | |
| RU2017123114A (ru) | 3-оксо-3-(ариламино)пропионаты, способ их получения и их применение в получении пирролидинонов | |
| AR061372A1 (es) | Amino-imidazoles y sus usos como medicamentos para el tratamiento de mal de alzheimer, demencia y neurodegeneracion | |
| AR096979A1 (es) | Derivados de pirrol, su procedimiento de preparación y las composiciones farmacéuticas que los contienen | |
| PE20171177A1 (es) | Compuestos aminopirimidinilo inhibidores de jak | |
| AR090203A1 (es) | Compuestos heterobiciclicos como inhibidores de pde10 | |
| AR081139A1 (es) | Uracilos herbicidas | |
| AR092645A1 (es) | Derivados biciclicos inhibidores de autotaxina (atx) | |
| AR078168A1 (es) | Derivados de piperidinas y piperazinas, procesos para prepararlos y sus usos como moduladores de gpr119 | |
| AR093504A1 (es) | 4-(orto)-fluorofenil-5-fluoropirimidin-2-ilaminas que contienen un grupo sulfoximina como inhibidores de cdk9, un intermediario para su sintesis y metodos de obtencion de ambos compuestos | |
| AR052898A1 (es) | Derivados de la n-[(4,5-difenil -2-tienil) metil] amina, su preparacion, composiciones farmaceuticas que los contienen y su uso en la fabricacion de un medicamento para enfermedades mediadas por los receptores canabinoides cb1 | |
| AR108076A1 (es) | Derivados heterocíclicos con sustituyentes que contienen azufre activos como plaguicidas | |
| AR110282A1 (es) | Compuestos de amida bicíclica y uso de éstos en el tratamiento de enfermedades mediadas por rip1 | |
| AR054725A1 (es) | Pirazolopiridinas y sales de las mismas, una composicion farmaceutica que comprende dichos compuestos, un metodo para prepararlos y su uso | |
| AR084515A1 (es) | Derivados heterociclicos nitrogenados, composiciones farmaceuticas que los contienen y uso de los mismos en el tratamiento de enfermedades asociadas al sistema nervioso central tales como parkinson y alzheimer, entre otras | |
| AR093047A1 (es) | Compuestos heterociclicos nitrogenados | |
| BR112017019439A2 (pt) | inibidores kv1.3 e sua aplicação médica |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant, registration |