CN103429573B - 顺式-烷氧基取代的螺环1h-吡咯烷-2,4-二酮衍生物 - Google Patents
顺式-烷氧基取代的螺环1h-吡咯烷-2,4-二酮衍生物 Download PDFInfo
- Publication number
- CN103429573B CN103429573B CN201280012628.2A CN201280012628A CN103429573B CN 103429573 B CN103429573 B CN 103429573B CN 201280012628 A CN201280012628 A CN 201280012628A CN 103429573 B CN103429573 B CN 103429573B
- Authority
- CN
- China
- Prior art keywords
- cis
- hydroxide
- trans
- alkyl
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- -1 alkali metal salt Chemical class 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 26
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 13
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 8
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 8
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 8
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 claims description 8
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 claims description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 2
- 239000000920 calcium hydroxide Substances 0.000 claims description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 2
- 239000000347 magnesium hydroxide Substances 0.000 claims description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 7
- 150000003839 salts Chemical class 0.000 abstract description 7
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 150000001875 compounds Chemical class 0.000 description 22
- 239000007787 solid Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 17
- 238000003756 stirring Methods 0.000 description 13
- 239000011734 sodium Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 238000000967 suction filtration Methods 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 238000001816 cooling Methods 0.000 description 7
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 6
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000002075 main ingredient Substances 0.000 description 3
- 230000002269 spontaneous effect Effects 0.000 description 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 238000004255 ion exchange chromatography Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000006150 Bucherer-Bergs reaction Methods 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 159000000009 barium salts Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
- C07D233/78—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
A | M | n |
C2H5 | Li+ | 1 |
C2H5 | Na+ | 1 |
C2H5 | K+ | 1 |
C2H5 | Rb+ | 1 |
C2H5 | Be2+ | 2 |
C2H5 | Mg2+ | 2 |
C2H5 | Ca2+ | 2 |
C2H5 | Sr2+ | 2 |
C2H5 | Ba2+ | 2 |
C3H7 | Na+ | 1 |
C3H7 | K+ | 1 |
iC3H7 | Na+ | 1 |
iC3H7 | K+ | 1 |
C4H9 | Na+ | 1 |
C4H9 | K+ | 1 |
iC4H9 | Na+ | 1 |
iC4H9 | K+ | 1 |
Claims (5)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510673003.6A CN105367501B (zh) | 2011-03-11 | 2012-03-06 | 顺式‑烷氧基取代的螺环1h‑吡咯烷‑2,4‑二酮衍生物 |
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161451783P | 2011-03-11 | 2011-03-11 | |
EP11157904 | 2011-03-11 | ||
US61/451,783 | 2011-03-11 | ||
EP11157904.1 | 2011-03-11 | ||
PCT/EP2012/053810 WO2012123287A1 (de) | 2011-03-11 | 2012-03-06 | Cis-alkoxysubstituierte spirocyclische 1-h-pyrrolidin-2,4-dion-derivate |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201510673003.6A Division CN105367501B (zh) | 2011-03-11 | 2012-03-06 | 顺式‑烷氧基取代的螺环1h‑吡咯烷‑2,4‑二酮衍生物 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN103429573A CN103429573A (zh) | 2013-12-04 |
CN103429573B true CN103429573B (zh) | 2016-01-20 |
Family
ID=43880973
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201280012628.2A Active CN103429573B (zh) | 2011-03-11 | 2012-03-06 | 顺式-烷氧基取代的螺环1h-吡咯烷-2,4-二酮衍生物 |
CN201510673003.6A Active CN105367501B (zh) | 2011-03-11 | 2012-03-06 | 顺式‑烷氧基取代的螺环1h‑吡咯烷‑2,4‑二酮衍生物 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201510673003.6A Active CN105367501B (zh) | 2011-03-11 | 2012-03-06 | 顺式‑烷氧基取代的螺环1h‑吡咯烷‑2,4‑二酮衍生物 |
Country Status (12)
Country | Link |
---|---|
US (1) | US8710238B2 (zh) |
EP (1) | EP2683695B1 (zh) |
JP (1) | JP5974021B2 (zh) |
KR (1) | KR101925162B1 (zh) |
CN (2) | CN103429573B (zh) |
BR (1) | BR112013023213A8 (zh) |
DK (1) | DK2683695T3 (zh) |
ES (1) | ES2549061T3 (zh) |
IL (1) | IL228270A (zh) |
MX (1) | MX339188B (zh) |
TW (1) | TWI519521B (zh) |
WO (1) | WO2012123287A1 (zh) |
Family Cites Families (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU666040B2 (en) | 1992-10-28 | 1996-01-25 | Bayer Aktiengesellschaft | Substituted 1-H-3-aryl-pyrrolidine-2,4-dione derivatives |
DE4425617A1 (de) | 1994-01-28 | 1995-08-03 | Bayer Ag | 1-H-3-Aryl-pyrrolidin-2,4-dion-Derivate |
DE4431730A1 (de) | 1994-02-09 | 1995-08-10 | Bayer Ag | Substituierte 1H-3-Aryl-pyrrolidin-2,4-dion-Derivate |
JP3651897B2 (ja) | 1994-04-05 | 2005-05-25 | バイエル アクチェンゲゼルシャフト | 除草剤及び有害生物防除剤として用いられるアルコキシ−アルキル−置換された1−h−3−アリール−ピロリジン−2,4−ジオン類 |
WO1996025395A1 (de) | 1995-02-13 | 1996-08-22 | Bayer Aktiengesellschaft | 2-phenylsubstituierte heterocyclische 1,3-ketoenole als herbizide und pestizide |
CN1131209C (zh) | 1995-05-09 | 2003-12-17 | 拜尔公司 | 可用作杀虫剂和除草剂的烷基-二卤代苯基取代的酮烯醇 |
CN1173947C (zh) | 1995-06-28 | 2004-11-03 | 拜尔公司 | 2,4,5-三取代的苯基酮烯醇作为农药和除草剂的应用 |
CN1229323C (zh) | 1995-06-30 | 2005-11-30 | 拜尔公司 | 二烷基-卤代苯基取代的酮-烯醇 |
WO1997036868A1 (de) | 1996-04-02 | 1997-10-09 | Bayer Aktiengesellschaft | Substituierte phenylketoenole als schädlingsbekämpfungsmittel und herbizide |
NZ334028A (en) | 1996-08-05 | 2000-11-24 | Bayer Ag | 1-heterocyclic substituted 2- and 2,5-substituted phenylketoenol derivatives |
DE19808261A1 (de) | 1998-02-27 | 1999-10-28 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
DE19813354A1 (de) | 1998-03-26 | 1999-09-30 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
DE19818732A1 (de) | 1998-04-27 | 1999-10-28 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
DE10016544A1 (de) | 2000-04-03 | 2001-10-11 | Bayer Ag | C2-phenylsubstituierte Ketoenole |
DE10029077A1 (de) | 2000-06-13 | 2001-12-20 | Bayer Ag | Thiazolylsubstituierte Heterocyclen |
DE10032587A1 (de) | 2000-07-05 | 2002-01-17 | Bayer Ag | 4-Alkoxy-cyclohexan-1-amino-carbonsäureester und Verfahren zu ihrer Herstellung |
DE10152005A1 (de) | 2001-10-22 | 2003-04-30 | Bayer Cropscience Ag | Pyrazolylsubstituierte Heterocyclen |
DE10231333A1 (de) | 2002-07-11 | 2004-01-22 | Bayer Cropscience Ag | Cis-Alkoxysubstituierte spirocyclische 1-H-Pyrrolidin-2,4-dion-Derivate |
DE10239479A1 (de) * | 2002-08-28 | 2004-03-04 | Bayer Cropscience Ag | Substituierte spirocyclische Ketoenole |
DE10301804A1 (de) | 2003-01-20 | 2004-07-29 | Bayer Cropscience Ag | 2,4-Dihalogen-6-(C2-C3-alkyl)-phenyl substituierte Tetramsäure-Derivate |
DE10326386A1 (de) | 2003-06-12 | 2004-12-30 | Bayer Cropscience Ag | N-Heterocyclyl-phenylsubstituierte cyclische Ketoenole |
DE10351646A1 (de) | 2003-11-05 | 2005-06-09 | Bayer Cropscience Ag | 2-Halogen-6-alkyl-phenyl substituierte spirocyclische Tetramsäure-Derivate |
DE10354629A1 (de) | 2003-11-22 | 2005-06-30 | Bayer Cropscience Ag | 2-Ethyl-4,6-dimethyl-phenyl substituierte spirocyclische Tetramsäure-Derivate |
DE102004001433A1 (de) | 2004-01-09 | 2005-08-18 | Bayer Cropscience Ag | cis-Alkoxyspiro-substituierte Tetramsäure-Derivate |
DE102004014620A1 (de) | 2004-03-25 | 2005-10-06 | Bayer Cropscience Ag | 2,4,6-phenylsubstituierte cyclische Ketoenole |
DE102004044827A1 (de) | 2004-09-16 | 2006-03-23 | Bayer Cropscience Ag | Jod-phenylsubstituierte cyclische Ketoenole |
DE102004053192A1 (de) | 2004-11-04 | 2006-05-11 | Bayer Cropscience Ag | 2-Alkoxy-6-alkyl-phenyl substituierte spirocyclische Tetramsäure-Derivate |
DE102004053191A1 (de) | 2004-11-04 | 2006-05-11 | Bayer Cropscience Ag | 2,6-Diethyl-4-methyl-phenyl substituierte Tetramsäure-Derivate |
JP5349960B2 (ja) * | 2005-06-23 | 2013-11-20 | エモリー ユニバーシティー | 腫瘍画像化のためのアミノ酸類似体の立体選択的合成 |
DE102006007882A1 (de) | 2006-02-21 | 2007-08-30 | Bayer Cropscience Ag | Cycloalkyl-phenylsubstituierte cyclische Ketoenole |
DE102006057037A1 (de) | 2006-12-04 | 2008-06-05 | Bayer Cropscience Ag | cis-Alkoxyspirocyclische biphenylsubstituierte Tetramsäure-Derivate |
EP1992614A1 (de) | 2007-05-16 | 2008-11-19 | Bayer CropScience Aktiengesellschaft | 3-(2-Alkoxy-phenyl)-substituierte Tetramate |
BRPI1008949B1 (pt) | 2009-03-11 | 2018-07-10 | Bayer Intellectual Property Gmbh | Cetoenóis haloalquilmetilenóxi-fenil-substituídos e seu uso, composição, seu uso e seu método de produção, métodos para combate de pestes animais e/ou crescimento de plantas indesejadas |
-
2012
- 2012-03-06 CN CN201280012628.2A patent/CN103429573B/zh active Active
- 2012-03-06 KR KR1020137026367A patent/KR101925162B1/ko active IP Right Grant
- 2012-03-06 CN CN201510673003.6A patent/CN105367501B/zh active Active
- 2012-03-06 ES ES12707584.4T patent/ES2549061T3/es active Active
- 2012-03-06 JP JP2013557071A patent/JP5974021B2/ja active Active
- 2012-03-06 BR BR112013023213A patent/BR112013023213A8/pt not_active Application Discontinuation
- 2012-03-06 MX MX2013010320A patent/MX339188B/es active IP Right Grant
- 2012-03-06 US US14/004,404 patent/US8710238B2/en active Active
- 2012-03-06 DK DK12707584.4T patent/DK2683695T3/en active
- 2012-03-06 EP EP12707584.4A patent/EP2683695B1/de active Active
- 2012-03-06 WO PCT/EP2012/053810 patent/WO2012123287A1/de active Application Filing
- 2012-03-09 TW TW101108009A patent/TWI519521B/zh active
-
2013
- 2013-09-03 IL IL228270A patent/IL228270A/en active IP Right Grant
Non-Patent Citations (1)
Title |
---|
螺虫乙酯的合成;师文娟等;《农药》;20100430;第49卷(第4期);250-251,263 * |
Also Published As
Publication number | Publication date |
---|---|
TWI519521B (zh) | 2016-02-01 |
BR112013023213A2 (pt) | 2016-07-26 |
CN103429573A (zh) | 2013-12-04 |
BR112013023213A8 (pt) | 2018-01-23 |
IL228270A (en) | 2014-11-30 |
KR20140009454A (ko) | 2014-01-22 |
DK2683695T3 (en) | 2015-11-09 |
IL228270A0 (en) | 2013-11-25 |
CN105367501B (zh) | 2017-11-28 |
MX339188B (es) | 2016-05-13 |
TW201249807A (en) | 2012-12-16 |
MX2013010320A (es) | 2013-10-28 |
ES2549061T3 (es) | 2015-10-22 |
EP2683695B1 (de) | 2015-08-05 |
CN105367501A (zh) | 2016-03-02 |
JP2014508769A (ja) | 2014-04-10 |
US20140058114A1 (en) | 2014-02-27 |
EP2683695A1 (de) | 2014-01-15 |
JP5974021B2 (ja) | 2016-08-23 |
US8710238B2 (en) | 2014-04-29 |
WO2012123287A1 (de) | 2012-09-20 |
KR101925162B1 (ko) | 2018-12-04 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN103261187A (zh) | 制备四唑取代的邻氨基苯甲酰胺衍生物的方法以及这些衍生物的新的晶体多形体 | |
MX2012013332A (es) | Preparacion de intermediarios de posaconazol. | |
WO2013148991A8 (en) | N-acyl derivatives of gamma amino - butyric acid and and beta alanine as food flavouring compounds | |
WO2011123947A8 (en) | Synthesis of chiral 2-(1h-indazol-6-yl)-spiro[cyclopropane-1,3'- indolin]-2'-ones | |
EA018227B1 (ru) | Способ получения дабигатрана и его промежуточные соединения | |
EP3444238A3 (en) | Process for preparing difluoromethylene compounds | |
IN2014CN03482A (zh) | ||
MX337804B (es) | Proceso para la preparacion de hidrazinas quirales. | |
MX2010001229A (es) | Procedimiento para la resolucion de zopiclona y compuestos intermedios. | |
CN103429573B (zh) | 顺式-烷氧基取代的螺环1h-吡咯烷-2,4-二酮衍生物 | |
MX2011008592A (es) | Preparacion libre de solventes de marco organometalico poroso basado en formiato de magnesio. | |
JP2015512381A5 (zh) | ||
JP6240346B2 (ja) | ロスバスタチンカルシウムを製造するための中間体化合物、及びそれを用いてロスバスタチンカルシウムを製造する方法 | |
EA201990236A1 (ru) | Новые способы получения стимуляторов растворимой гуанилатциклазы | |
CN104262220B (zh) | 一种二甲基-β-丙酸噻亭的制备方法 | |
CN102285997A (zh) | 一种氯代烯丙基β-内酰胺抗生素中间体的制备方法 | |
MY147894A (en) | Process for preparing intermediate compound for synthesizing an antiulcerant | |
CN1272320C (zh) | 制备4-卤烷基烟酸酯的方法 | |
RU2455287C1 (ru) | Способ получения (2s,4s)-3-(3-ацетилтиопропионил)-2-алкил(арил)-6-оксогексагидропиримидин-4-карбоновых кислот | |
CN104650143A (zh) | 制备福沙匹坦二甲葡胺中间体的方法 | |
JP2016108332A (ja) | アミノ化合物の製造方法 | |
KR20130078086A (ko) | 피타바스타틴 헤미칼슘의 제조방법 | |
JP2016534047A5 (zh) | ||
RU2425035C2 (ru) | Способ получения 4,5-дихлоримидазолов | |
RU2471792C1 (ru) | Способ получения 3-(2-хлорпропионил)амино-4-метил-2-метоксикарбонилтиофена |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CP03 | Change of name, title or address |
Address after: 50 Alfred Nobel Street, Monheim, Rhine, Germany 40789 Patentee after: BAYER INTELLECTUAL PROPERTY GmbH Address before: Germany Patentee before: BAYER INTELLECTUAL PROPERTY GmbH |
|
CP03 | Change of name, title or address | ||
TR01 | Transfer of patent right |
Effective date of registration: 20240111 Address after: 50 Alfred Nobel Street, Monheim, Rhine, Germany 40789 Patentee after: BAYER CROPSCIENCE AG Address before: 50 Alfred Nobel Street, Monheim, Rhine, Germany 40789 Patentee before: BAYER INTELLECTUAL PROPERTY GmbH |
|
TR01 | Transfer of patent right |