DE1770092A1 - Oxadiazolderivate - Google Patents
OxadiazolderivateInfo
- Publication number
- DE1770092A1 DE1770092A1 DE19681770092 DE1770092A DE1770092A1 DE 1770092 A1 DE1770092 A1 DE 1770092A1 DE 19681770092 DE19681770092 DE 19681770092 DE 1770092 A DE1770092 A DE 1770092A DE 1770092 A1 DE1770092 A1 DE 1770092A1
- Authority
- DE
- Germany
- Prior art keywords
- oxadiazole
- compound
- formula
- formaldehyde
- alkyl
- 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.)
- Pending
Links
- 150000004866 oxadiazoles Chemical class 0.000 title 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 9
- -1 azidophenyl Chemical group 0.000 claims 8
- 238000000034 method Methods 0.000 claims 6
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000005882 oxadiazolinyl group Chemical group 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 2
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 claims 1
- PQPRLUWLXNSHBH-VOTSOKGWSA-N 3-[(e)-2-phenylethenyl]-1,2,4-oxadiazole Chemical compound N1=CON=C1/C=C/C1=CC=CC=C1 PQPRLUWLXNSHBH-VOTSOKGWSA-N 0.000 claims 1
- QEXMQHPBSDSREQ-UHFFFAOYSA-N 3-[2-(4-chlorophenyl)ethenyl]-2,5-dihydro-1,2,4-oxadiazole Chemical compound C1=CC(Cl)=CC=C1C=CC1=NOCN1 QEXMQHPBSDSREQ-UHFFFAOYSA-N 0.000 claims 1
- ZAMQOEGKTJELQU-UHFFFAOYSA-N 3-[2-(4-fluorophenyl)ethenyl]-1,2,4-oxadiazole Chemical compound C1=CC(F)=CC=C1C=CC1=NOC=N1 ZAMQOEGKTJELQU-UHFFFAOYSA-N 0.000 claims 1
- MVOQHIAGXHPXDY-UHFFFAOYSA-N 3-[2-(4-fluorophenyl)ethenyl]-2,5-dihydro-1,2,4-oxadiazole Chemical compound C1=CC(F)=CC=C1C=CC1=NOCN1 MVOQHIAGXHPXDY-UHFFFAOYSA-N 0.000 claims 1
- IETFLZBLFOMDBM-UHFFFAOYSA-N 3-[2-[4-(trifluoromethyl)phenyl]ethenyl]-1,2,4-oxadiazole Chemical compound C1=CC(C(F)(F)F)=CC=C1C=CC1=NOC=N1 IETFLZBLFOMDBM-UHFFFAOYSA-N 0.000 claims 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 230000002141 anti-parasite Effects 0.000 claims 1
- 239000003096 antiparasitic agent Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229910021386 carbon form Inorganic materials 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 125000004802 cyanophenyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 230000022244 formylation Effects 0.000 claims 1
- 238000006170 formylation reaction Methods 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims 1
- 239000011968 lewis acid catalyst Substances 0.000 claims 1
- 125000006501 nitrophenyl group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000007699 photoisomerization reaction Methods 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- ZMRUPTIKESYGQW-UHFFFAOYSA-N propranolol hydrochloride Chemical compound [H+].[Cl-].C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 ZMRUPTIKESYGQW-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
- C07C259/14—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/24—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/28—Halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Claims (23)
1. Verbindungen der Formel
G-B-R7 A
in der A eine der "beiden folgenden Gruppen ist
HN HC . j
\ ' H2C X
und B eine der beiden nachfolgenden Gruppen ist
R^l Ro
(in welcher R. und Rp Wasserstoff, Halogen oder niedrig-Alkyl
sind) und R5, entweder Aryl, substituiertes Aryl, Oxadiazolyl,
öxadiazolinyl oder Thienyl ist.
2. Verbindungen nach Anspruch 1, in denen die Gruppe R-, entweder
Phenyl, Halophenyl, Azidophenyl, Cyanophenyl, Nitrophenyl,
Aminophenyl, niedrig-Alkylphenyl, Hydroxyphenyl, niedrig-Al
te j xyphenyl, Trif lourmethylphenyl, niedrig-Alkyl fchxophenyl,
109882/1788
SiNAL INSPECTED
niedrig-Alkylsulfinylphenyl, niedrig-Alkylsulfonylphenyl,
Formamidophenyl oder Thiocyanotophenyl ist.
3. 3-Styryl-1,2,4-oxadiazol.
4-· 3-(p-Chlorstyryl)-i,2,4-oxadiazol.
5. 4,5-Dihydro-3-(p-chlorstyryl)-1,2,4-oxadiazol.
6. 1,2-bis(1,2-Oxadia2,ol-3-yl)äthylen.
7· 3-p-(Cyanostyryl)-1,2,4-oxadiazol.
8. 3-(p-Bromsfcyryl)-1,2,4-oxadiazol.
9· 4,5-Dihydro-3-(p-bromstyryl)-1,2,4-oxadiazol.
10. 3-(p-Fluorstyryl)-1,2,4-oxadiazol.
11. 4,5-Dihydro-3-(p-fluorstyryl)-1,2,4-oxadiazol.
12. 3-(p-Azidostyryl)-1,2,4-oxadiazol.
13· 3-(p-Methylsulfinylstyryl)-1,2,4-oxadiazol.
14. 3-(p-Trifluormethylstyryl)-1,2,4-oxadiazol.
15. 3-Phenyläthinyl-1,2,4-oxadiazol.
16. 3-(p-Chlorphenyläthinyl)-1,2,4-oxadiazol.
17. Verwendung von Verbindungen nach Anspruch 1, zusammen mit einem Träger- oder Verdünnungsmittel, als antiparasitische Zusammensetzungen.
18. Verfahren zur Herstellung von Verbindungen der Formel I:
XN C— CR
Her ν
109882/17
in der R,- und Rp, die gleich oder verschieden sein können,
jeder ein Wasserstoffatom, ein Halogenatom oder eine Alkylgruppe
mit 1 bis 5 Kohlenstoffatomen bedeuten oder R^ und R2
zusammen mit den Kohlenstoffatomen, an die sie gebunden sind, eine Kohlenstoff-Kohlenstoff-Bindung bilden; R7 einen Aryl-,
Oxadiazolyl-, Oxadiazolinyl- oder Thienylrest bedeutet, wobei
jede der Gruppen substituiert sein kann; und X und X beide Wasserstoffatome bedeuten oder zusammen eine Stickstoff-Kohlenstoff-Bindung
bilden, dadurch gekennzeichnet, daß eine Verbindung der Formel II
Ηρα.
C-
mit einem Formylierungsmittel oder Formaldehyd oder polymerem
Formaldehyd umgesetzt wird und die Gruppe R, im Produkt gewünschtenfalls
in bekannter Weise in eine andere Gruppe R? umgewandelt wird.
19. Verfahren nach Anspruch 18, dadurch gekennzeichnet, daß das Formylierungsmittel ein Alkylorthoformiat, Ameisen—
säure, Formamid, ein gemischtes Anhydrid mit Ameisensäure, ein Formylhalogenid oder ein Komplex aus Formamid und Fhosphoroxychlorid
ist.
20. Verfahren nach einem der Ansprüche 18 oder 19S dadurch
gekcnnzeichnet,laß die Formylierung in Gegenwart eines Säure-
109882/1788
oder Lewis-Säurekatalysators durchgeführt wird·
21. Verfahren nach einem der Ansprüche 18 bis 20, dadurch gekennzeichnet, daß die Formulierung in Gegenwart eines Lösungsmittels
durchgeführt wird.
22. Verfahren nach einem der Ansprüche 18 bis 21, dadurch gekennzeichnet, daß die Verbindung der Formel I mit Formaldehyd
oder einem polymeren Formaldehyd umgesetzt wird und die entstandene Verbindung oxydiert wird.
23. Verfahren nach einem der Ansprüche 18 bis 22, dadurch gekennzeichnet, daß wenn das Reaktionsprodukt eine trans_-Verbindung
ist, diese Verbindung durch Photoisomerisierung in die entsprechende
eis-Verbindung umgewandelt wird.
θΓ,-iccha-
Q nicht
sind.
sind.
109882/1788
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1496167 | 1967-03-31 | ||
| US47306474A | 1974-05-24 | 1974-05-24 | |
| US05/556,324 US4012377A (en) | 1967-03-31 | 1975-03-07 | Oxadiazole and oxadiazoline derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1770092A1 true DE1770092A1 (de) | 1972-01-05 |
Family
ID=27257195
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681770092 Pending DE1770092A1 (de) | 1967-03-31 | 1968-03-29 | Oxadiazolderivate |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4012377A (de) |
| CH (1) | CH502364A (de) |
| DE (1) | DE1770092A1 (de) |
| DK (1) | DK124826B (de) |
| FR (2) | FR1579544A (de) |
| GB (1) | GB1228142A (de) |
| NL (1) | NL6804496A (de) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4212970A (en) * | 1977-11-28 | 1980-07-15 | Fuji Photo Film Co., Ltd. | 2-Halomethyl-5-vinyl-1,3,4-oxadiazole compounds |
| DE3622296A1 (de) * | 1986-07-03 | 1988-01-07 | Basf Ag | Verfahren zur herstellung von (beta)-halogenvinyl- und (beta),(beta)-dihalogenethylarylketonen |
| DE4041474A1 (de) * | 1990-12-22 | 1992-06-25 | Bayer Ag | Verwendung von substituierten 1,2,4-oxadiazolderivaten zur bekaempfung von endoparasiten, neue substituierte 1,2,4-oxadiazolderivate und verfahren zu ihrer herstellung |
| DE4124151A1 (de) * | 1991-07-20 | 1993-01-21 | Bayer Ag | Insektizide und akarizide pflanzenschutzmittel enthaltend substituierte 1,2,4-oxadiazolderivate |
| DE4232418A1 (de) * | 1992-09-28 | 1994-03-31 | Bayer Ag | Verwendung von substituierten 1,2,4-Oxadiazolderivaten zur Bekämpfung von Endoparasiten, neue substituierte 1,2,4-Oxadiazolderivate und Verfahren zu ihrer Herstellung |
| FR2735473A1 (fr) * | 1995-06-13 | 1996-12-20 | Hoechst Schering Agrevo Sa | Nouveaux derives de l'acide beta-methoxy acrylique, leur procede de preparation et leur application comme pesticides |
| US6043259A (en) * | 1998-07-09 | 2000-03-28 | Medicure Inc. | Treatment of cardiovascular and related pathologies |
| ATE306489T1 (de) | 1999-03-08 | 2005-10-15 | Medicure Inc | Pyridoxal-analoge zur behandlung von störungen ausgelöst durch einen vitamin b6 mangel |
| CA2376029A1 (en) | 1999-07-13 | 2001-01-18 | Medicure Inc. | Use of pyridoxin derivatives for the treatment of diabetes and related complications |
| JP2003507418A (ja) | 1999-08-24 | 2003-02-25 | メディキュア インターナショナル インコーポレイテッド | 心血管疾患とその関連疾患の治療 |
| WO2001064692A1 (en) | 2000-02-29 | 2001-09-07 | Medicure International Inc. | Cardioprotective phosphonates and malonates |
| US6586414B2 (en) | 2000-03-28 | 2003-07-01 | Medicure International Inc. | Treatment of cerebrovascular disease |
| US6897228B2 (en) | 2000-07-07 | 2005-05-24 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: new uses |
| US6548519B1 (en) | 2001-07-06 | 2003-04-15 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: novel uses |
| AU2001272263B2 (en) | 2000-07-07 | 2005-12-15 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: cardiovascular therapeutics |
| US20060019929A1 (en) * | 2004-07-07 | 2006-01-26 | Albert Friesen | Combination therapies employing platelet aggregation drugs |
| US7459468B2 (en) * | 2004-10-28 | 2008-12-02 | Medicure International, Inc. | Aryl sulfonic pyridoxines as antiplatelet agents |
| CA2585165A1 (en) * | 2004-10-28 | 2006-05-18 | Medicure International Inc. | Dual antiplatelet/anticoagulant pyridoxine analogs |
| US20060094749A1 (en) * | 2004-10-28 | 2006-05-04 | Medicure International Inc. | Substituted pyridoxines as anti-platelet agents |
| WO2007059631A1 (en) * | 2005-11-28 | 2007-05-31 | Medicure International Inc. | Selected dosage for the treatment of cardiovascular and related pathologies |
| WO2008097538A1 (en) * | 2007-02-08 | 2008-08-14 | Merck & Co., Inc. | Therapeutic agents |
| RU2009144998A (ru) * | 2007-05-07 | 2011-06-20 | Шеринг Корпорейшн (US) | Модуляторы гамма-секретазы |
| WO2010054064A1 (en) * | 2008-11-06 | 2010-05-14 | Schering Corporation | Gamma secretase modulators |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL291628A (de) * | 1962-04-17 | |||
| NL302339A (de) * | 1963-03-22 | |||
| US3574222A (en) * | 1965-12-29 | 1971-04-06 | Mallinckrodt Chemical Works | Preparation of 5-amino-1,2,4-oxadiazoles |
| DE1670338A1 (de) * | 1966-03-14 | 1972-08-10 | Heyden Chem Fab | Verfahren zur Herstellung von antimikrobiell wirksamen Nitrofuranderivaten |
| US3471621A (en) * | 1966-05-02 | 1969-10-07 | Gulf Research Development Co | Method of combating nematodes with 3-cyclopropyl - 5 - dichloromethyl-1,2,4-oxadiazole |
| US3356684A (en) * | 1966-07-28 | 1967-12-05 | Lilly Co Eli | Novel compositions for the treatment of helminthiasis |
| US3637707A (en) * | 1970-11-24 | 1972-01-25 | Pfizer | 2-(substituted) 2-thiazolines for the control of rice blast |
-
1967
- 1967-03-31 GB GB1496167A patent/GB1228142A/en not_active Expired
-
1968
- 1968-03-29 DE DE19681770092 patent/DE1770092A1/de active Pending
- 1968-03-29 NL NL6804496A patent/NL6804496A/xx unknown
- 1968-03-29 FR FR1579544D patent/FR1579544A/fr not_active Expired
- 1968-03-29 CH CH466768A patent/CH502364A/de not_active IP Right Cessation
- 1968-03-29 DK DK139168AA patent/DK124826B/da unknown
- 1968-06-25 FR FR156899A patent/FR8333M/fr not_active Expired
-
1975
- 1975-03-07 US US05/556,324 patent/US4012377A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US4012377A (en) | 1977-03-15 |
| DK124826B (da) | 1972-11-27 |
| NL6804496A (de) | 1968-10-01 |
| GB1228142A (de) | 1971-04-15 |
| CH502364A (de) | 1971-01-31 |
| FR1579544A (de) | 1969-08-29 |
| FR8333M (de) | 1970-12-14 |
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