JPH09512533A - 関節ポリシダルオキサジアジンの製造 - Google Patents
関節ポリシダルオキサジアジンの製造Info
- Publication number
- JPH09512533A JPH09512533A JP7527663A JP52766395A JPH09512533A JP H09512533 A JPH09512533 A JP H09512533A JP 7527663 A JP7527663 A JP 7527663A JP 52766395 A JP52766395 A JP 52766395A JP H09512533 A JPH09512533 A JP H09512533A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- reacting
- acid
- fluoroalkoxy
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/04—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/62—Compounds containing any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylcarbamates
- C07C271/66—Y being a hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/02—Compounds containing any of the groups, e.g. carbazates
- C07C281/04—Compounds containing any of the groups, e.g. carbazates the other nitrogen atom being further doubly-bound to a carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/68—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1. キラル中心*においてラセミ的な又は鏡像異性体的に富んでいる式I [式中、 R1は、F、Cl又はC1〜C3−フルオロアルコキシであり、そして R2は、C1〜C3−アルキルである] の化合物を製造するための方法であって、 (a)*において必要に応じて鏡像異性体的に富んでいる、式II の化合物を、酸触媒の存在下で式III H2N−NHR3 III の化合物と反応させて、式IV [式中、 R3は、保護基例えばCO2CH2(C6H5)及び類似物である] の化合物を生成させること、 (b)式IVの化合物をルイス酸の存在下でジ(C1〜C3−アルコキシ)メタ ンと反応させて式V の化合物を生成させること、 (c)式Vの化合物を水素化させて式VI の化合物を生成させること、そして (d)式VIの化合物を式VII の化合物と反応させて、式IIの化合物と実質的に同じ絶対配置を有する式Iの 化合物を生成させること を含んで成る方法。 2. 式V: の化合物を作るための方法であって、 (a)*において必要に応じて鏡像異性体的に富んでいる、式II の化合物を、酸触媒の存在下で式III H2N−NHR3 III の化合物と反応させて、式IV [これらの式中、 R1は、F、Cl又はC1〜C3−フルオロアルコキシであり、 R2は、C1〜C3−アルキルであり、そして R3は、保護基CO2CH2(C6H5)である] の化合物を生成させること、及び (b)式IVの化合物をルイス酸の存在下でジ(C1〜C3−アルコキシ)メタ ンと反応させること を含んで成る方法。 3. 式Vの化合物を水素化させることを含んで成る、式VI: の化合物を作るための請求の範囲第2項に記載の方法。 4. 式IV [式中、 R1は、F、Cl又はC1〜C3−フルオロアルコキシであり、 R2は、C1〜C3−アルキルであり、そして R3は、保護基CO2CH2(C6H5)である] の化合物を、ルイス酸の存在下でジ(C1〜C3−アルコキシ)メタンと反応させ て、式V の化合物を生成させ、そして式Vの化合物を水素化させることを含んで成る、式 VI: の化合物を作るための方法。 5. 式VIの化合物を式VII の化合物と反応させることを含んで成る、式I の化合物を作るための、請求の範囲第4項に記載の方法。 6. 式I [式中、 R1は、F、Cl又はC1〜C3−フルオロアルコキシであり、そして R2は、C1〜C3−アルキルである] の化合物を作るための方法であって、式V [式中、 R3は、保護のCO2CH2(C6H5)である] の化合物を水素化させて、式VI の化合物を生成させ、そして 式VIの化合物を式VII の化合物と反応させることを含んで成る方法。 7. [式中、 R1は、F、Cl又はC1〜C3−フルオロアルコキシであり、 R2は、C1〜C3−アルキルであり、 R3は、CO2CH2(C6H5)であり、そして R4は、H及びCO2CH2(C6H5)から選ばれる] の群から選ばれたラセミ又は鏡像異性体的に富んだ化合物。 8. 式II: [式中、 R1は、F、Cl及びC1〜C3−フルオロアルコキシの群から選ばれ、そして R2は、C1〜C3−アルキルである] の化合物の鏡像異性体的に富んだ(+)又は(−)鏡像異性体を製造するための 方法であって、 (i)ルイス酸の存在下でp−置換フェニルアセチルハロゲン化物をエチレン と反応させて式VIII の化合物を製造するステップ、 (ii)VIIIをペルオキシ酸と反応させて式IX の化合物を製造するステップ、 (iii)酸触媒の存在下でIXをC1〜C3−アルコールと反応させて式X の化合物を製造するステップ、 (iv)Xを塩基と反応させて式XI の化合物を製造するステップ、 並びに (v)キラル塩基の存在下でXIをヒドロペルオキシドと反応させて鏡像異性 体的に富んだIIを製造するステップ を含んで成る方法。 9. 式: [式中、 R1は、F、Cl及びC1〜C3−フルオロアルコキシの群から選ばれ、そして R2は、C1〜C3−アルキルである] の化合物の(+)鏡像異性体。 10. (+)メチル5−クロロ−1,3−ジヒドロ−2−ヒドロキシ−1− オキソ−2H−インデン−2−カルボキシレートである、請求の範囲第1項に記 載の化合物。 11. 式IX又はX: [式中、 R1は、F、Cl及びC1〜C3−フルオロアルコキシの群から選ばれ、そして R2は、H又はC1〜C3−アルキルである] の化合物。 12. 2−カルボキシ−5−クロロベンゼンプロパン酸である、請求の範囲 第11項に記載の化合物。 13. 5−クロロ−2−(メトキシカルボニル)ベンゼンプロパン酸メチル である、請求の範囲第11項に記載の化合物。 14. 式: の化合物。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US23056894A | 1994-04-20 | 1994-04-20 | |
US08/230,568 | 1994-04-20 | ||
US29890994A | 1994-08-31 | 1994-08-31 | |
US08/298,909 | 1994-08-31 | ||
PCT/US1995/004321 WO1995029171A1 (en) | 1994-04-20 | 1995-04-17 | Preparation of arthropodicidal oxadiazines |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006181231A Division JP4263200B2 (ja) | 1994-04-20 | 2006-06-30 | 殺節足動物性オキサジアジンの製造に用いられる化合物 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH09512533A true JPH09512533A (ja) | 1997-12-16 |
JP3882195B2 JP3882195B2 (ja) | 2007-02-14 |
Family
ID=26924355
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP52766395A Expired - Lifetime JP3882195B2 (ja) | 1994-04-20 | 1995-04-17 | 関節ポリシダルオキサジアジンの製造 |
JP2006181231A Expired - Lifetime JP4263200B2 (ja) | 1994-04-20 | 2006-06-30 | 殺節足動物性オキサジアジンの製造に用いられる化合物 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006181231A Expired - Lifetime JP4263200B2 (ja) | 1994-04-20 | 2006-06-30 | 殺節足動物性オキサジアジンの製造に用いられる化合物 |
Country Status (21)
Country | Link |
---|---|
US (1) | US5869657A (ja) |
EP (5) | EP1598332B1 (ja) |
JP (2) | JP3882195B2 (ja) |
KR (1) | KR100249448B1 (ja) |
CN (3) | CN1142922C (ja) |
AT (3) | ATE303983T1 (ja) |
AU (2) | AU687547B2 (ja) |
BR (1) | BR9507845A (ja) |
CA (3) | CA2582172C (ja) |
CZ (1) | CZ306096A3 (ja) |
DE (4) | DE69534440T2 (ja) |
ES (4) | ES2296010T3 (ja) |
HU (2) | HU214902B (ja) |
IL (3) | IL155210A (ja) |
MX (1) | MX209131B (ja) |
NZ (1) | NZ283961A (ja) |
PL (1) | PL316849A1 (ja) |
PT (3) | PT1623980E (ja) |
RU (1) | RU2138489C1 (ja) |
TW (1) | TW477790B (ja) |
WO (1) | WO1995029171A1 (ja) |
Families Citing this family (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101391953B (zh) * | 1994-04-20 | 2012-06-06 | 纳幕尔杜邦公司 | 用于制备*二嗪的中间体 |
WO1997033476A1 (en) * | 1996-03-15 | 1997-09-18 | E.I. Du Pont De Nemours And Company | Insecticidal mixtures |
USH1950H1 (en) * | 1996-08-05 | 2001-03-06 | E. I. Du Pont De Nemours And Company | Processes for preparing indeno[1,2-E][1,3,4]oxadiazine-dicarboxylates |
DE19736921A1 (de) | 1997-08-25 | 1999-03-04 | Bayer Ag | Verfahren zur Herstellung von 2-Cyanoindan-1-onen |
EP1085809A1 (en) * | 1998-06-10 | 2001-03-28 | E.I. Du Pont De Nemours And Company | Arthropodicidal carboxanilides |
DE19837069C1 (de) * | 1998-08-17 | 2000-01-05 | Bayer Ag | Substituierte Zimtsäuren und Zimtsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von substituierten Indanoncarbonsäureestern |
US6956129B2 (en) * | 2001-02-16 | 2005-10-18 | Bayer Aktiengesellschaft | Polyhalogen-substituted cinnamic acids and cinnamic acid derivatives and a process for the preparation of polyhalogen-substituted cinnamic acids and cinnamic acid derivatives |
JP4359500B2 (ja) * | 2001-06-29 | 2009-11-04 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ジルコニウム触媒によるβ−ジカルボニルのヒドロキシル化 |
WO2003040083A1 (en) * | 2001-11-07 | 2003-05-15 | E.I. Du Pont De Nemours And Company | Enantioselective hydroxylation of beta-dicarbonyls catalyzed by cinchona alkaloid derivatives |
US6916946B2 (en) | 2003-08-20 | 2005-07-12 | Daicel Chemical Industries, Ltd. | Acid halide derivatives, their production, and production of indanonecarboxylic acid esters using the same |
JP2005170803A (ja) | 2003-12-08 | 2005-06-30 | Daicel Chem Ind Ltd | 新規なマロン酸モノメチル誘導体とその製造法 |
IN241255B (ja) * | 2005-05-02 | 2010-06-25 | ||
WO2008030385A2 (en) | 2006-09-01 | 2008-03-13 | E. I. Du Pont De Nemours And Company | Local topical administration formulations containing indoxacarb |
CN101503358B (zh) * | 2009-03-10 | 2012-01-25 | 大连理工大学 | 高乌甲素作为催化剂制备手性α-羟基-β-二羰基化合物的方法 |
JP2011246436A (ja) | 2010-04-28 | 2011-12-08 | Sumitomo Chemical Co Ltd | 有害生物防除組成物 |
CN102391261A (zh) * | 2011-10-14 | 2012-03-28 | 上海交通大学 | 一种n-取代噁二嗪类化合物及其制备方法和应用 |
CN103371168B (zh) * | 2012-04-28 | 2017-02-22 | 马国丰 | 一种高效杀虫剂组合物 |
CN103033573B (zh) * | 2012-12-13 | 2014-05-21 | 黄河三角洲京博化工研究院有限公司 | 一种n-氯甲酰基-n-[4-(三氟甲氧基)苯基]氨基甲酸甲酯含量分析方法 |
CN103694193B (zh) * | 2013-10-11 | 2016-01-20 | 浙江大学 | 精茚虫威的晶型及其无定形形式 |
CN104262285B (zh) * | 2014-07-24 | 2016-08-17 | 浙江大学 | 农用杀虫剂茚虫威中间体的合成法 |
CN104193696A (zh) * | 2014-08-26 | 2014-12-10 | 常州大学 | 一种新型杀虫剂茚虫威的制备方法 |
CN104230838B (zh) * | 2014-09-11 | 2016-03-30 | 浙江大学 | 农用杀虫剂茚虫威高纯度关键中间体的制备方法 |
CN104311502B (zh) * | 2014-09-15 | 2016-08-24 | 南通施壮化工有限公司 | 从茚虫威混合体中分离提纯s体茚虫威的方法 |
CN106928062B (zh) * | 2015-12-31 | 2020-05-12 | 江苏扬农化工股份有限公司 | 一种α-羟基-β-二羰基化合物手性富集的方法 |
CN106106504A (zh) * | 2016-06-27 | 2016-11-16 | 江苏新农化工有限公司 | 含甲基毒死蜱的杀虫组合物及其制剂和应用 |
CN106397351B (zh) * | 2016-08-31 | 2018-10-30 | 京博农化科技股份有限公司 | 一种茚虫威中间体的制备方法 |
CN107043360B (zh) * | 2017-03-22 | 2019-07-12 | 京博农化科技股份有限公司 | 一种茚虫威杀虫剂的制备方法 |
CN107915692A (zh) * | 2017-10-30 | 2018-04-17 | 安徽富田农化有限公司 | 一种茚虫威的制备方法 |
CN108586292A (zh) * | 2018-01-24 | 2018-09-28 | 湖南国发精细化工科技有限公司 | N-氯甲酰基-n-[(4-三氟甲氧基)苯基]氨基甲酸甲酯的精制方法 |
CN108997254A (zh) * | 2018-08-27 | 2018-12-14 | 湖南国发精细化工科技有限公司 | 茚并噁二嗪化合物的合成方法 |
CN109704994A (zh) * | 2018-12-26 | 2019-05-03 | 山东华阳农药化工集团有限公司 | 一种合成茚虫威中间体氯甲酰基[4-(三氟甲氧基)苯基]氨基甲酸甲酯的改进方法 |
CN109651288A (zh) * | 2018-12-29 | 2019-04-19 | 京博农化科技有限公司 | 一种茚虫威中间体的制备方法 |
WO2022200364A1 (en) | 2021-03-25 | 2022-09-29 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
CN117320551A (zh) | 2021-05-14 | 2023-12-29 | 先正达农作物保护股份公司 | 种子处理组合物 |
JP2024516912A (ja) | 2021-05-14 | 2024-04-17 | シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト | 昆虫、ダニ目及び線虫有害生物の防除 |
WO2022268813A1 (en) | 2021-06-24 | 2022-12-29 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
WO2022268815A1 (en) | 2021-06-24 | 2022-12-29 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
WO2023286053A1 (en) | 2021-07-13 | 2023-01-19 | Adama Makhteshim Ltd. | Method of preparing of arthropodicidal oxadiazine intermediate |
WO2023105064A1 (en) | 2021-12-10 | 2023-06-15 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
WO2023105065A1 (en) | 2021-12-10 | 2023-06-15 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
WO2023131943A1 (en) | 2022-01-04 | 2023-07-13 | Adama Makhteshim Ltd. | Process of preparation of indoxacarb and its intermediates |
WO2023148735A1 (en) | 2022-02-02 | 2023-08-10 | Adama Makhteshim Ltd. | Novel solid state forms of indoxacarb |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3755453A (en) * | 1971-03-18 | 1973-08-28 | Atlantic Richfield Co | Process for the synthesis of adipoin (2-hydroxycylohexanone) |
DE2257344C2 (de) * | 1972-11-22 | 1982-04-22 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von N-Chlorformyl-kohlensäureamiden |
US4489074A (en) * | 1982-11-12 | 1984-12-18 | Imperial Chemical Industries, Plc | 1,3,4-Thiadiazin-2-ones |
DE3506236A1 (de) * | 1985-02-22 | 1986-08-28 | Bayer Ag, 5090 Leverkusen | 1-acyl-1-phenyl-harnstoffe |
US5462938A (en) * | 1990-12-21 | 1995-10-31 | Annus; Gary D. | Arthropodicidal oxadiazinyl, thiadiazinyl and triazinyl carboxanilides |
EP0586551A1 (en) * | 1991-05-24 | 1994-03-16 | E.I. Du Pont De Nemours And Company | Arthropodicidal anilides |
WO1993019045A1 (en) | 1992-03-26 | 1993-09-30 | E.I. Du Pont De Nemours And Company | Arthropodicidal amides |
US5510505A (en) * | 1995-04-06 | 1996-04-23 | E. I. Du Pont De Nemours And Company | Arthopodicidal oxadiazine intermediate |
-
1995
- 1995-04-17 PT PT05024812T patent/PT1623980E/pt unknown
- 1995-04-17 HU HU9602885A patent/HU214902B/hu unknown
- 1995-04-17 AT AT03007459T patent/ATE303983T1/de active
- 1995-04-17 DE DE69534440T patent/DE69534440T2/de not_active Expired - Lifetime
- 1995-04-17 MX MX9604881A patent/MX209131B/es unknown
- 1995-04-17 ES ES05014510T patent/ES2296010T3/es not_active Expired - Lifetime
- 1995-04-17 CN CNB001036327A patent/CN1142922C/zh not_active Expired - Lifetime
- 1995-04-17 AT AT95915601T patent/ATE214380T1/de active
- 1995-04-17 EP EP05014510A patent/EP1598332B1/en not_active Expired - Lifetime
- 1995-04-17 ES ES05024812T patent/ES2297591T3/es not_active Expired - Lifetime
- 1995-04-17 EP EP95915601A patent/EP0756594B1/en not_active Expired - Lifetime
- 1995-04-17 EP EP05024812A patent/EP1623980B1/en not_active Expired - Lifetime
- 1995-04-17 RU RU96122027A patent/RU2138489C1/ru active
- 1995-04-17 BR BR9507845A patent/BR9507845A/pt not_active IP Right Cessation
- 1995-04-17 NZ NZ283961A patent/NZ283961A/en not_active IP Right Cessation
- 1995-04-17 HU HU9801346A patent/HU221609B/hu unknown
- 1995-04-17 CA CA002582172A patent/CA2582172C/en not_active Expired - Lifetime
- 1995-04-17 ES ES03007459T patent/ES2248663T3/es not_active Expired - Lifetime
- 1995-04-17 PL PL95316849A patent/PL316849A1/xx unknown
- 1995-04-17 CN CN95192654A patent/CN1059901C/zh not_active Expired - Lifetime
- 1995-04-17 WO PCT/US1995/004321 patent/WO1995029171A1/en not_active Application Discontinuation
- 1995-04-17 EP EP00113734A patent/EP1048647A1/en not_active Ceased
- 1995-04-17 CN CNB031579167A patent/CN100439320C/zh not_active Expired - Lifetime
- 1995-04-17 KR KR1019960705877A patent/KR100249448B1/ko not_active IP Right Cessation
- 1995-04-17 CA CA002546165A patent/CA2546165C/en not_active Expired - Lifetime
- 1995-04-17 DE DE69525840T patent/DE69525840T2/de not_active Expired - Lifetime
- 1995-04-17 DE DE69535654T patent/DE69535654T2/de not_active Expired - Lifetime
- 1995-04-17 PT PT05014510T patent/PT1598332E/pt unknown
- 1995-04-17 AT AT05014510T patent/ATE376541T1/de active
- 1995-04-17 CA CA002188400A patent/CA2188400C/en not_active Expired - Lifetime
- 1995-04-17 CZ CZ963060A patent/CZ306096A3/cs unknown
- 1995-04-17 DE DE69535630T patent/DE69535630T2/de not_active Expired - Lifetime
- 1995-04-17 EP EP03007459A patent/EP1357107B1/en not_active Expired - Lifetime
- 1995-04-17 PT PT95915601T patent/PT756594E/pt unknown
- 1995-04-17 JP JP52766395A patent/JP3882195B2/ja not_active Expired - Lifetime
- 1995-04-17 AU AU22432/95A patent/AU687547B2/en not_active Expired
- 1995-04-17 ES ES95915601T patent/ES2171537T3/es not_active Expired - Lifetime
- 1995-04-18 IL IL155210A patent/IL155210A/en not_active IP Right Cessation
- 1995-04-18 IL IL11341295A patent/IL113412A/xx not_active IP Right Cessation
- 1995-05-08 TW TW084104553A patent/TW477790B/zh not_active IP Right Cessation
-
1996
- 1996-10-16 US US08/727,607 patent/US5869657A/en not_active Expired - Lifetime
-
1998
- 1998-01-20 AU AU52168/98A patent/AU714304B2/en not_active Expired
-
2003
- 2003-04-02 IL IL15521003A patent/IL155210A0/xx unknown
-
2006
- 2006-06-30 JP JP2006181231A patent/JP4263200B2/ja not_active Expired - Lifetime
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JPH09512533A (ja) | 関節ポリシダルオキサジアジンの製造 | |
JP2004522744A (ja) | クロピドグレルの製造方法 | |
WO1990012007A1 (fr) | Nouveaux sulfonamides derives d'acides benzocycliques ou benzoheterocycliques, leur preparation et leur application en therapeutique | |
US6232489B1 (en) | Preparation of arthropodicidal oxadiazines | |
US6479659B2 (en) | Process of making 3-phenyl-1-methylenedioxyphenyl-indane-2-carboxylic acid derivatives | |
EP0611232A1 (fr) | Procédé pour la préparatiuon de dérivés phénylbenzamides | |
JP2003171354A (ja) | 光学活性アミン化合物又はその塩の製造方法 | |
JP2833672B2 (ja) | β−ケトニトリル類の製造方法 | |
KR100359503B1 (ko) | 방향족 프로피온산 유도체의 제조방법 | |
RU2051903C1 (ru) | Способ получения (*01+)-(е)-4-этил-2-[(е)-гидроксиимино]-5-нитро-3-гексенамида | |
NZ328632A (en) | (+)1,3-dihydro-2-hydroxy-1-oxo-2h-indene-2-carboxylate and 2-carboxy-benzenepropanoic acid derivatives | |
FR2658815A1 (fr) | Dichloro-2,2'-difluoro-4',5'-acetophenone et procede pour sa preparation, son application a la preparation de l'acide chloro-2-difluoro-4,5-benzouique et nouveau procede de preparation dudit acide. | |
EP0056201A1 (fr) | Nouveau procédé de préparation du N,N-diméthyl aza-1 bicyclo 2,2,2 octyl-3 -10 10H-phénothiazinesulfonamide-2 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20060314 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20060614 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20060630 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20060731 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20061024 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20061106 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20091124 Year of fee payment: 3 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20101124 Year of fee payment: 4 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20101124 Year of fee payment: 4 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20111124 Year of fee payment: 5 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20111124 Year of fee payment: 5 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20121124 Year of fee payment: 6 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20131124 Year of fee payment: 7 |
|
EXPY | Cancellation because of completion of term |