CA2025939A1 - Carboxamides of isoxazole- and isothiazole-carboxylic acids - Google Patents
Carboxamides of isoxazole- and isothiazole-carboxylic acidsInfo
- Publication number
- CA2025939A1 CA2025939A1 CA002025939A CA2025939A CA2025939A1 CA 2025939 A1 CA2025939 A1 CA 2025939A1 CA 002025939 A CA002025939 A CA 002025939A CA 2025939 A CA2025939 A CA 2025939A CA 2025939 A1 CA2025939 A1 CA 2025939A1
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- cycloalkyl
- chain
- 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
- 150000003857 carboxamides Chemical class 0.000 title abstract 2
- VYRHBTFPNHLCOY-UHFFFAOYSA-N 1,2-oxazole 1,2-thiazole-3-carboxylic acid Chemical class C=1C=NOC=1.OC(=O)C=1C=CSN=1 VYRHBTFPNHLCOY-UHFFFAOYSA-N 0.000 title 1
- -1 6-membered heterocyclic radical Chemical class 0.000 abstract 8
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 6
- 125000003342 alkenyl group Chemical group 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
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000000304 alkynyl group Chemical group 0.000 abstract 3
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 3
- 125000005842 heteroatom Chemical group 0.000 abstract 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- HCXJFMDOHDNDCC-UHFFFAOYSA-N 5-$l^{1}-oxidanyl-3,4-dihydropyrrol-2-one Chemical group O=C1CCC(=O)[N]1 HCXJFMDOHDNDCC-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 abstract 1
- 239000012964 benzotriazole Substances 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical group CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000004995 haloalkylthio group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 229910052748 manganese Inorganic materials 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- 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
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
- C07D261/12—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Carboxamides Ia, Ib, Ic and Id (X = 0, S; R1 = H, halogen, substituted or unsubstituted alkyl, substi-tuted or unsubstituted benzyl, alkoxy, alkylthio, haloalkoxy, haloalkyl-thio, substituted or unsubstituted phenyl, substituted or unsubstituted phenoxy or phenylthio, a substituted or unsubstituted 5- or 6-membered heterocyclic radical containing one or two heteroatoms, cycloalkyl-substituted alkyl, substituted or unsubstituted alkenyl which may be epoxidized, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl or cycloalkenyl; R1' - cycloalkyl-substituted alkyl, substituted or unsubstituted alkenyl which may be epoxidized, substituted or unsubstituted cycloalkenyl; R2 = CHO, 4,5-dihydrooxazol-2-yl, COYR5, CONR6R7; Y = 0, S; R5 = H, substituted or unsubstituted alkyl, cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsub-stituted cycloalkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted phenyl, a 5- or 6-membered heterocyclic radical contain-ing up to 3 heteroatoms, benzotriazole, N-phthalimido, tetrahydrophthal-imido, succinimido, maleiimido, 2,2-dimethyl-1,3-dioxolan-4-ylmethyl, 1,3-dioxolan-2-on-4-ylmethyl, and when Y = 0: one equivalent of a cation from the group of the alkali or alkaline earth metals, Mn, Cu, Fe, ammonium and substituted ammonium, a radical -N=CR8R9 or -W-Z; R8, R9 = H, substituted or unsubstituted alkyl, substituted or unsubstituted halo-alkyl, cycloalkyl, alkoxy, furanyl, substituted or unsubstituted phenyl;
R8+R9 = 4-7-membered methylene chain; W = alkylene chain, ethoxyethylene chain, butylene, butynylene chain; Z = a molecular moiety bonded to W in the .omega.-position and is the same as that linked to W in the .alpha.-position of W;
R6=H, alkyl, cycloalkyl; R7=H; alkyl; -C(0-alkyl)=N-H or -C(0-alkyl)=N-alkyl; R6+R7 = 4-5-membered methylene chain; R3 = H, substituted or unsub-stituted alkyl, substituted or unsubstituted cycloalkyl; R4 = H, OH, alkoxy, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsub-stituted alkynyl, di-(C1-C4)-alkylamino, a substituted or unsubstituted 5-or 6-membered heterocyclic radical containing one or two heteroatoms, sub-stituted or unsubstituted phenyl, substituted or unsubstituted naphthyl;
R3+R4 = 4-7-membered methylene chain which may be interrupted by 0, S or N-CH3, or -(CH2) 3-CO-) and their environmentally tolerated salts.
40 The compounds Ia to Id are suitable as herbicides.
R8+R9 = 4-7-membered methylene chain; W = alkylene chain, ethoxyethylene chain, butylene, butynylene chain; Z = a molecular moiety bonded to W in the .omega.-position and is the same as that linked to W in the .alpha.-position of W;
R6=H, alkyl, cycloalkyl; R7=H; alkyl; -C(0-alkyl)=N-H or -C(0-alkyl)=N-alkyl; R6+R7 = 4-5-membered methylene chain; R3 = H, substituted or unsub-stituted alkyl, substituted or unsubstituted cycloalkyl; R4 = H, OH, alkoxy, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsub-stituted alkynyl, di-(C1-C4)-alkylamino, a substituted or unsubstituted 5-or 6-membered heterocyclic radical containing one or two heteroatoms, sub-stituted or unsubstituted phenyl, substituted or unsubstituted naphthyl;
R3+R4 = 4-7-membered methylene chain which may be interrupted by 0, S or N-CH3, or -(CH2) 3-CO-) and their environmentally tolerated salts.
40 The compounds Ia to Id are suitable as herbicides.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3931627.0 | 1989-09-22 | ||
| DE3931627A DE3931627A1 (en) | 1989-09-22 | 1989-09-22 | New amino-carbonyl-substd. iso-thiazole or isoxazole carboxylic acid d |
| DEP3933898.3 | 1989-10-11 | ||
| DE19893933898 DE3933898A1 (en) | 1989-10-11 | 1989-10-11 | New amino-carbonyl-substd. iso-thiazole or isoxazole carboxylic acid d |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2025939A1 true CA2025939A1 (en) | 1991-03-23 |
| CA2025939C CA2025939C (en) | 2002-02-19 |
Family
ID=25885411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002025939A Expired - Fee Related CA2025939C (en) | 1989-09-22 | 1990-09-21 | Carboxamides of isoxazole- and isothiazole-carboxylic acids |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0418667B1 (en) |
| JP (1) | JPH03130270A (en) |
| KR (1) | KR910006253A (en) |
| BR (1) | BR9004747A (en) |
| CA (1) | CA2025939C (en) |
| DE (1) | DE59009528D1 (en) |
| HU (1) | HU207788B (en) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4108181A1 (en) * | 1991-03-14 | 1992-09-17 | Basf Ag | ISOXAZOL AND ISOTHIAZOL 5-CARBON ACID AMIDE |
| DE4108183A1 (en) * | 1991-03-14 | 1992-09-17 | Basf Ag | ISOXAZOL AND ISOTHIAZOL 5-CARBON ACID AMIDE |
| DE4201047A1 (en) * | 1992-01-17 | 1993-07-22 | Bayer Ag | SUBSTITUTED ISOXAZOLE CARBONIC ACID AMIDES |
| DE4209848A1 (en) * | 1992-03-26 | 1993-09-30 | Basf Ag | Process for the preparation of isoxazole-3,4-dicarboxylic acid derivatives |
| DE4209849A1 (en) * | 1992-03-26 | 1993-09-30 | Basf Ag | Preparation of isoxazole-3-carboxamide-4-carboxylic acid esters by selective amidation |
| DE4214010A1 (en) * | 1992-04-29 | 1993-11-04 | Basf Ag | ISOXAZOLE CARBOXYLENEAMIDE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE |
| DE4306962A1 (en) * | 1993-03-05 | 1994-09-08 | Bayer Ag | Oxadiazolecarboxylic acid derivatives |
| CZ244394A3 (en) * | 1993-10-08 | 1995-06-14 | Shell Int Research | Herbicidal 1,2,4-oxadiazolecarboxylic acids amides, esters or halides |
| DE4406209A1 (en) | 1994-02-25 | 1995-08-31 | Basf Ag | Cyanoisoxazoles |
| ATE243204T1 (en) * | 1995-08-24 | 2003-07-15 | Basf Ag | ISOXAZOLE AND ISOTHIAZOLE-5-CARBOXAMIDE DERIVATIVES, THEIR PRODUCTION AND THEIR USE AS HERBICIDES |
| DE19614859A1 (en) * | 1996-04-16 | 1997-10-23 | Basf Ag | Herbicidal benzoylisothiazoles |
| US6297198B1 (en) | 1996-05-14 | 2001-10-02 | Syngenta Participations Ag | Isoxazole derivatives and their use as herbicides |
| EP1012150A4 (en) * | 1997-05-19 | 2002-05-29 | Sugen Inc | Heteroarylcarboxamide compounds active against protein tyrosine kinase related disorders |
| US6727272B1 (en) * | 2002-07-15 | 2004-04-27 | Unitech Pharmaceuticals, Inc. | Leflunomide analogs for treating rheumatoid arthritis |
| US7365094B2 (en) | 2002-12-23 | 2008-04-29 | 4Sc Ag | Compounds as anti-inflammatory, immunomodulatory and anti-proliferatory agents |
| WO2004056746A1 (en) | 2002-12-23 | 2004-07-08 | 4Sc Ag | Cycloalkene dicarboxylic acid compounds as anti-inflammatory, immunomodulatory and anti-proliferatory agents |
| JP2006514023A (en) * | 2002-12-23 | 2006-04-27 | ４エスシー エージー | Aromatic compounds as anti-inflammatory agents, immunomodulators and growth inhibitors |
| CN1771235B (en) * | 2003-02-11 | 2010-04-28 | 弗奈利斯(剑桥)有限公司 | Isoxazole compounds |
| TW200716576A (en) * | 2005-06-07 | 2007-05-01 | Shionogi & Co | Heterocyclic derivatives as inhibitors of 11-beta-hydroxysteroid dehydrogenase 1 |
| US8193225B2 (en) | 2006-10-13 | 2012-06-05 | The Board Of Regents Of The University Of Texas System | Isoxazole amides, derivatives and methods of chemical induction of neurogenesis |
| WO2008046072A2 (en) * | 2006-10-13 | 2008-04-17 | The Board Of Regents Of The University Of Texas System | Chemical inducers of neurogenesis |
| US9284749B2 (en) | 2012-04-17 | 2016-03-15 | Schlage Lock Company Llc | Door lock assembly |
| UA121225C2 (en) | 2014-12-16 | 2020-04-27 | Новартіс Аг | ISOXAZOLE HYDROXAMIC ACID COMPOUNDS AS LpxC INHIBITORS |
| EA036243B1 (en) | 2016-06-14 | 2020-10-16 | Новартис Аг | Crystalline form of (r)-4-(5-(cyclopropylethynyl)isoxazol-3-yl)-n-hydroxy-2-methyl-2-(methylsulfonyl)butanamide as an antibacterial agent |
| KR20220166810A (en) * | 2020-03-13 | 2022-12-19 | 더 보드 오브 리젠츠 오브 더 유니버시티 오브 텍사스 시스템 | Substituted isoxazoles as selective NAV1.7 inhibitors for pain treatment and methods for pain treatment |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3409616A (en) * | 1966-07-27 | 1968-11-05 | Pfizer & Co C | 4-oxo-10-hydroxy-1, 2, 3, 4-tetrahydroanthracene-2-(alpha-amino)acetates |
| US4890053A (en) * | 1988-04-15 | 1989-12-26 | Philip Morris Incorporated | Method and apparatus for detecting a missing object in a set of objects |
-
1990
- 1990-09-07 EP EP90117233A patent/EP0418667B1/en not_active Expired - Lifetime
- 1990-09-07 DE DE59009528T patent/DE59009528D1/en not_active Expired - Lifetime
- 1990-09-19 JP JP2247666A patent/JPH03130270A/en active Pending
- 1990-09-21 BR BR909004747A patent/BR9004747A/en not_active Application Discontinuation
- 1990-09-21 HU HU906009A patent/HU207788B/en not_active IP Right Cessation
- 1990-09-21 CA CA002025939A patent/CA2025939C/en not_active Expired - Fee Related
- 1990-09-22 KR KR1019900015118A patent/KR910006253A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| HUT55955A (en) | 1991-07-29 |
| BR9004747A (en) | 1991-09-10 |
| HU906009D0 (en) | 1991-03-28 |
| EP0418667A2 (en) | 1991-03-27 |
| JPH03130270A (en) | 1991-06-04 |
| KR910006253A (en) | 1991-04-29 |
| CA2025939C (en) | 2002-02-19 |
| HU207788B (en) | 1993-06-28 |
| DE59009528D1 (en) | 1995-09-21 |
| EP0418667B1 (en) | 1995-08-16 |
| EP0418667A3 (en) | 1992-01-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |