DE2047465A1 - Neue Oxdiazole und Verfahren zu lh rer Herstellung - Google Patents
Neue Oxdiazole und Verfahren zu lh rer HerstellungInfo
- Publication number
- DE2047465A1 DE2047465A1 DE19702047465 DE2047465A DE2047465A1 DE 2047465 A1 DE2047465 A1 DE 2047465A1 DE 19702047465 DE19702047465 DE 19702047465 DE 2047465 A DE2047465 A DE 2047465A DE 2047465 A1 DE2047465 A1 DE 2047465A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- acid
- oxdiazoles
- chain
- chloromethyl
- 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
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 3
- -1 halogenated alkyl radical Chemical class 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 150000003977 halocarboxylic acids Chemical class 0.000 claims description 6
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 14
- 229940106681 chloroacetic acid Drugs 0.000 description 14
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000010992 reflux Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 description 3
- 239000012433 hydrogen halide Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- IBQLBYSHFYJCJG-UHFFFAOYSA-N 2-(chloromethyl)-5-ethyl-1,3,4-oxadiazole Chemical compound CCC1=NN=C(CCl)O1 IBQLBYSHFYJCJG-UHFFFAOYSA-N 0.000 description 2
- DVUSDXWUQFEAQB-UHFFFAOYSA-N 2-benzyl-5-(chloromethyl)-1,3,4-oxadiazole Chemical compound O1C(CCl)=NN=C1CC1=CC=CC=C1 DVUSDXWUQFEAQB-UHFFFAOYSA-N 0.000 description 2
- SZYNGENWKNXSLU-UHFFFAOYSA-N 2-butyl-5-(chloromethyl)-1,3,4-oxadiazole Chemical compound CCCCC1=NN=C(CCl)O1 SZYNGENWKNXSLU-UHFFFAOYSA-N 0.000 description 2
- NBPLLPBYZXYAMN-UHFFFAOYSA-N 2-ethoxyacetohydrazide Chemical compound CCOCC(=O)NN NBPLLPBYZXYAMN-UHFFFAOYSA-N 0.000 description 2
- FPTCVTJCJMVIDV-UHFFFAOYSA-N 2-phenylacetohydrazide Chemical compound NNC(=O)CC1=CC=CC=C1 FPTCVTJCJMVIDV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- YTQHSQQSLTYMSL-UHFFFAOYSA-N dodecanohydrazide Chemical compound CCCCCCCCCCCC(=O)NN YTQHSQQSLTYMSL-UHFFFAOYSA-N 0.000 description 2
- FLGJKAWEVKYTSD-UHFFFAOYSA-N methyl 2-amino-5-(1-phenylethyl)thiophene-3-carboxylate Chemical compound S1C(N)=C(C(=O)OC)C=C1C(C)C1=CC=CC=C1 FLGJKAWEVKYTSD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BYTFESSQUGDMQQ-UHFFFAOYSA-N octadecanehydrazide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NN BYTFESSQUGDMQQ-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- ROFVGYAMRSGUSQ-UHFFFAOYSA-N 1-(2-bromoethyl)piperazine;hydrobromide Chemical compound Br.BrCCN1CCNCC1 ROFVGYAMRSGUSQ-UHFFFAOYSA-N 0.000 description 1
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- QNVMFLRXIRZUTR-UHFFFAOYSA-N 2-(2-methylpropyl)-1,3,4-oxadiazole Chemical compound CC(C)CC1=NN=CO1 QNVMFLRXIRZUTR-UHFFFAOYSA-N 0.000 description 1
- CPDGQEXQTVITAY-UHFFFAOYSA-N 2-(chloromethyl)-5-(2-methylpropyl)-1,3,4-oxadiazole Chemical compound CC(C)CC1=NN=C(CCl)O1 CPDGQEXQTVITAY-UHFFFAOYSA-N 0.000 description 1
- UCGJAQHFSXERIT-UHFFFAOYSA-N 2-(chloromethyl)-5-propan-2-yl-1,3,4-oxadiazole Chemical compound CC(C)C1=NN=C(CCl)O1 UCGJAQHFSXERIT-UHFFFAOYSA-N 0.000 description 1
- PXPQXVXNNQLXEG-UHFFFAOYSA-N 2-(chloromethyl)-5-undecyl-1,3,4-oxadiazole Chemical compound CCCCCCCCCCCC1=NN=C(CCl)O1 PXPQXVXNNQLXEG-UHFFFAOYSA-N 0.000 description 1
- VUZUKHXVTNNTLN-UHFFFAOYSA-N 2-ethylpentanehydrazide Chemical compound CCCC(CC)C(=O)NN VUZUKHXVTNNTLN-UHFFFAOYSA-N 0.000 description 1
- XEPXDMNZXBUSOI-UHFFFAOYSA-N 2-methoxyacetohydrazide Chemical compound COCC(=O)NN XEPXDMNZXBUSOI-UHFFFAOYSA-N 0.000 description 1
- ZMSIFDIKIXVLDF-UHFFFAOYSA-N 2-methyl-1,3,4-oxadiazole Chemical compound CC1=NN=CO1 ZMSIFDIKIXVLDF-UHFFFAOYSA-N 0.000 description 1
- XSONSBDQIFBIOY-UHFFFAOYSA-N 2-phenoxyacetohydrazide Chemical compound NNC(=O)COC1=CC=CC=C1 XSONSBDQIFBIOY-UHFFFAOYSA-N 0.000 description 1
- AJFUTCZBTOLZJK-UHFFFAOYSA-N 2-phenylpropanehydrazide Chemical compound NNC(=O)C(C)C1=CC=CC=C1 AJFUTCZBTOLZJK-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- MTWDGUWQZYXGTQ-UHFFFAOYSA-N 3-phenylprop-2-enehydrazide Chemical compound NNC(=O)C=CC1=CC=CC=C1 MTWDGUWQZYXGTQ-UHFFFAOYSA-N 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N Azide Chemical compound [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- TZYWCYJVHRLUCT-VABKMULXSA-N N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal Chemical compound CC(C)C[C@@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCC1=CC=CC=C1 TZYWCYJVHRLUCT-VABKMULXSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- BAZMYXGARXYAEQ-UHFFFAOYSA-N alpha-ethyl valeric acid Chemical compound CCCC(CC)C(O)=O BAZMYXGARXYAEQ-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- FCCCRBDJBTVFSJ-UHFFFAOYSA-N butanehydrazide Chemical compound CCCC(=O)NN FCCCRBDJBTVFSJ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- ROGBVBLYGMXQRO-UHFFFAOYSA-N decanehydrazide Chemical compound CCCCCCCCCC(=O)NN ROGBVBLYGMXQRO-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- SSVSELJXJJCANX-UHFFFAOYSA-N hexadecanehydrazide Chemical compound CCCCCCCCCCCCCCCC(=O)NN SSVSELJXJJCANX-UHFFFAOYSA-N 0.000 description 1
- QKWRNBNHSRYCOE-UHFFFAOYSA-N hexanehydrazide Chemical compound CCCCCC(=O)NN QKWRNBNHSRYCOE-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- VMUZVGRNTPFTKE-UHFFFAOYSA-N octanehydrazide Chemical compound CCCCCCCC(=O)NN VMUZVGRNTPFTKE-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 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
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
- C07F9/653—Five-membered rings
- C07F9/65306—Five-membered rings containing two nitrogen atoms
- C07F9/65312—Five-membered rings containing two nitrogen atoms having the two nitrogen atoms in positions 1 and 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702047465 DE2047465A1 (de) | 1970-09-26 | 1970-09-26 | Neue Oxdiazole und Verfahren zu lh rer Herstellung |
| GB4325571A GB1354135A (en) | 1970-09-26 | 1971-09-16 | Oxadiazoles and process for their manufacture |
| NL7112959A NL7112959A (enExample) | 1970-09-26 | 1971-09-21 | |
| FR7134483A FR2108538A5 (en) | 1970-09-26 | 1971-09-24 | 2-halomethyl-5-substd-1,3,4-oxadiazoles - as intermediates for parasiticides and drugs |
| BE773032A BE773032A (fr) | 1970-09-26 | 1971-09-24 | Oxadiazoles et leur preparation |
| IT29087/71A IT941461B (it) | 1970-09-26 | 1971-09-24 | Ossadiazoli e procedimento per la loro preparazione |
| IL37784A IL37784A0 (en) | 1970-09-26 | 1971-09-26 | Novel oxadiazoles and process for their manufacture |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702047465 DE2047465A1 (de) | 1970-09-26 | 1970-09-26 | Neue Oxdiazole und Verfahren zu lh rer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2047465A1 true DE2047465A1 (de) | 1972-03-30 |
Family
ID=5783494
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702047465 Pending DE2047465A1 (de) | 1970-09-26 | 1970-09-26 | Neue Oxdiazole und Verfahren zu lh rer Herstellung |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE773032A (enExample) |
| DE (1) | DE2047465A1 (enExample) |
| FR (1) | FR2108538A5 (enExample) |
| IL (1) | IL37784A0 (enExample) |
| IT (1) | IT941461B (enExample) |
| NL (1) | NL7112959A (enExample) |
Cited By (3)
| 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 |
| EP0156638A3 (en) * | 1984-03-23 | 1986-05-07 | Uniroyal, Inc. | Substituted oxadiazole-phosphate pesticide |
| WO2011073231A1 (en) | 2009-12-18 | 2011-06-23 | Nycomed Gmbh | 3,4,4A,10B-TETRAHYDRO-1H-THIOPYRANO-[4, 3-c] ISOQUINOLINE DERIVATIVES |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2909013A1 (de) * | 1979-03-08 | 1980-09-18 | Basf Ag | Oxadiazolylmethylthiolphosphate |
| FI4081511T6 (fi) | 2019-12-23 | 2026-06-09 | Sitryx Therapeutics Ltd | Karboksijohdannaisia, joilla on anti-inflammatorisia ominaisuuksia |
-
1970
- 1970-09-26 DE DE19702047465 patent/DE2047465A1/de active Pending
-
1971
- 1971-09-21 NL NL7112959A patent/NL7112959A/xx unknown
- 1971-09-24 IT IT29087/71A patent/IT941461B/it active
- 1971-09-24 BE BE773032A patent/BE773032A/xx unknown
- 1971-09-24 FR FR7134483A patent/FR2108538A5/fr not_active Expired
- 1971-09-26 IL IL37784A patent/IL37784A0/xx unknown
Cited By (4)
| 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 |
| EP0156638A3 (en) * | 1984-03-23 | 1986-05-07 | Uniroyal, Inc. | Substituted oxadiazole-phosphate pesticide |
| WO2011073231A1 (en) | 2009-12-18 | 2011-06-23 | Nycomed Gmbh | 3,4,4A,10B-TETRAHYDRO-1H-THIOPYRANO-[4, 3-c] ISOQUINOLINE DERIVATIVES |
| EP2813509A1 (en) | 2009-12-18 | 2014-12-17 | Takeda GmbH | 3,4,4a,10b-tetrahydro-1h-thiopyrano-[4,3-c]isoquinoline derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| IT941461B (it) | 1973-03-01 |
| IL37784A0 (en) | 1971-11-29 |
| BE773032A (fr) | 1972-03-24 |
| FR2108538A5 (en) | 1972-05-19 |
| NL7112959A (enExample) | 1972-03-28 |
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