CN1193320A - 1,3-噁(噻)嗪衍生物 - Google Patents
1,3-噁(噻)嗪衍生物 Download PDFInfo
- Publication number
- CN1193320A CN1193320A CN96196351A CN96196351A CN1193320A CN 1193320 A CN1193320 A CN 1193320A CN 96196351 A CN96196351 A CN 96196351A CN 96196351 A CN96196351 A CN 96196351A CN 1193320 A CN1193320 A CN 1193320A
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- CN
- China
- Prior art keywords
- alkyl
- monobasic
- different mode
- phenyl
- essentially
- 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.)
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- 125000000446 sulfanediyl group Chemical group *S* 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 70
- 238000000034 method Methods 0.000 claims abstract description 65
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 39
- 239000001301 oxygen Substances 0.000 claims abstract description 38
- 239000001257 hydrogen Substances 0.000 claims abstract description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 23
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 11
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 9
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract description 3
- 239000000460 chlorine Substances 0.000 claims description 119
- 150000001875 compounds Chemical class 0.000 claims description 115
- -1 ethylidene dioxy Chemical group 0.000 claims description 114
- 229910052801 chlorine Inorganic materials 0.000 claims description 91
- 229910052731 fluorine Inorganic materials 0.000 claims description 83
- 239000000203 mixture Substances 0.000 claims description 46
- 239000002585 base Substances 0.000 claims description 45
- 239000003795 chemical substances by application Substances 0.000 claims description 34
- 238000002360 preparation method Methods 0.000 claims description 30
- 239000011737 fluorine Substances 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 27
- 229910052794 bromium Inorganic materials 0.000 claims description 25
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 241000238631 Hexapoda Species 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 241000790917 Dioxys <bee> Species 0.000 claims description 14
- 239000005864 Sulphur Chemical group 0.000 claims description 14
- 150000001408 amides Chemical class 0.000 claims description 13
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 12
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 10
- 150000001336 alkenes Chemical class 0.000 claims description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 8
- UFTHEDBYLPFRDP-UHFFFAOYSA-N 5,6-dihydro-2h-oxazine Chemical class C1CC=CNO1 UFTHEDBYLPFRDP-UHFFFAOYSA-N 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 125000005504 styryl group Chemical group 0.000 claims description 8
- SMDGVPQREIZILS-UHFFFAOYSA-N $l^{1}-oxidanylmethylbenzene Chemical compound [O]CC1=CC=CC=C1 SMDGVPQREIZILS-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- DWDAZFJBSZTCCM-UHFFFAOYSA-N [O]C1CCCCC1 Chemical compound [O]C1CCCCC1 DWDAZFJBSZTCCM-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 125000005605 benzo group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- VBXAEFHLULAXHG-UHFFFAOYSA-N nitrosomethylbenzene Chemical compound O=NCC1=CC=CC=C1 VBXAEFHLULAXHG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 12
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 9
- 229910052717 sulfur Chemical group 0.000 abstract description 2
- 241000534944 Thia Species 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 abstract 1
- 125000002619 bicyclic group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- 239000011593 sulfur Chemical group 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 239000003921 oil Substances 0.000 description 21
- 235000019198 oils Nutrition 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 230000000694 effects Effects 0.000 description 18
- 239000000463 material Substances 0.000 description 18
- 239000003995 emulsifying agent Substances 0.000 description 17
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- 150000003851 azoles Chemical class 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- RNHSZHATICHNOX-UHFFFAOYSA-N O1NC=CC=C1.S1C=CC=C1 Chemical class O1NC=CC=C1.S1C=CC=C1 RNHSZHATICHNOX-UHFFFAOYSA-N 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- 239000003999 initiator Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 240000007594 Oryza sativa Species 0.000 description 9
- 235000007164 Oryza sativa Nutrition 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 9
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- 125000001424 substituent group Chemical group 0.000 description 8
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- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
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- 125000002877 alkyl aryl group Chemical group 0.000 description 6
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- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
-
- 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
- A01N43/86—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/16—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with only hydrogen or carbon atoms directly attached in positions 2 and 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
- C07D279/08—1,3-Thiazines; Hydrogenated 1,3-thiazines condensed with carbocyclic rings or ring systems
-
- 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
- C07D413/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19523087.6 | 1995-06-26 | ||
DE19523087A DE19523087A1 (de) | 1995-06-26 | 1995-06-26 | 1,3-Oxa(thia)zin-Derivate |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1193320A true CN1193320A (zh) | 1998-09-16 |
Family
ID=7765227
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN96196351A Pending CN1193320A (zh) | 1995-06-26 | 1996-06-13 | 1,3-噁(噻)嗪衍生物 |
Country Status (9)
Country | Link |
---|---|
EP (1) | EP0842162A1 (ko) |
JP (1) | JP2000502319A (ko) |
KR (1) | KR19990028393A (ko) |
CN (1) | CN1193320A (ko) |
AU (1) | AU6302896A (ko) |
BR (1) | BR9609310A (ko) |
DE (1) | DE19523087A1 (ko) |
TW (1) | TW336229B (ko) |
WO (1) | WO1997001546A1 (ko) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112789278A (zh) * | 2018-10-06 | 2021-05-11 | 先正达参股股份有限公司 | 杀微生物的喹啉二氢-(噻嗪)噁嗪衍生物 |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2839699A1 (en) | 2011-06-24 | 2012-12-27 | Amgen Inc. | Trpm8 antagonists and their use in treatments |
MX2013015058A (es) | 2011-06-24 | 2014-01-20 | Amgen Inc | Antagonistas de melastatina 8 de potencial receptor transitorio y su uso en tratamientos. |
US8952009B2 (en) | 2012-08-06 | 2015-02-10 | Amgen Inc. | Chroman derivatives as TRPM8 inhibitors |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1545671A1 (de) * | 1965-05-05 | 1969-08-07 | Huels Chemische Werke Ag | Verfahren zur Herstellung von 4H-5,6-Dihydro-1,3-oxazinen |
NZ259033A (en) * | 1992-12-25 | 1997-01-29 | Nippon Soda Co | 1,3-(thio)morpholine derivatives and biocidal compositions thereof |
AU681882B2 (en) * | 1993-07-21 | 1997-09-11 | Bayer Aktiengesellschaft | Azine derivatives |
-
1995
- 1995-06-26 DE DE19523087A patent/DE19523087A1/de not_active Withdrawn
-
1996
- 1996-06-12 TW TW085107036A patent/TW336229B/zh active
- 1996-06-13 KR KR1019970709709A patent/KR19990028393A/ko not_active Application Discontinuation
- 1996-06-13 CN CN96196351A patent/CN1193320A/zh active Pending
- 1996-06-13 BR BR9609310A patent/BR9609310A/pt not_active Application Discontinuation
- 1996-06-13 EP EP96921979A patent/EP0842162A1/de not_active Withdrawn
- 1996-06-13 JP JP9504127A patent/JP2000502319A/ja active Pending
- 1996-06-13 WO PCT/EP1996/002552 patent/WO1997001546A1/de not_active Application Discontinuation
- 1996-06-13 AU AU63028/96A patent/AU6302896A/en not_active Abandoned
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112789278A (zh) * | 2018-10-06 | 2021-05-11 | 先正达参股股份有限公司 | 杀微生物的喹啉二氢-(噻嗪)噁嗪衍生物 |
Also Published As
Publication number | Publication date |
---|---|
MX9710358A (es) | 1998-07-31 |
TW336229B (en) | 1998-07-11 |
DE19523087A1 (de) | 1997-01-02 |
KR19990028393A (ko) | 1999-04-15 |
WO1997001546A1 (de) | 1997-01-16 |
BR9609310A (pt) | 1999-07-06 |
AU6302896A (en) | 1997-01-30 |
JP2000502319A (ja) | 2000-02-29 |
EP0842162A1 (de) | 1998-05-20 |
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