DE2737542A1 - Cyclische alkylidenyl-n-(pyridazinyl)- aminomethylenmalonate und deren herstellung - Google Patents
Cyclische alkylidenyl-n-(pyridazinyl)- aminomethylenmalonate und deren herstellungInfo
- Publication number
- DE2737542A1 DE2737542A1 DE19772737542 DE2737542A DE2737542A1 DE 2737542 A1 DE2737542 A1 DE 2737542A1 DE 19772737542 DE19772737542 DE 19772737542 DE 2737542 A DE2737542 A DE 2737542A DE 2737542 A1 DE2737542 A1 DE 2737542A1
- Authority
- DE
- Germany
- Prior art keywords
- cyclic
- amino
- pyridazine
- malonate
- morpholinyl
- 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.)
- Withdrawn
Links
- -1 (PYRIDAZINYL) AMINOMETHYLENE MALONATES Chemical class 0.000 title claims description 38
- 238000004519 manufacturing process Methods 0.000 title description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 82
- 239000000203 mixture Substances 0.000 claims description 59
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 29
- DJDDYWYYTKNZPM-UHFFFAOYSA-N 2-amino-1,3-dioxane-4,6-dione Chemical compound NC1OC(=O)CC(=O)O1 DJDDYWYYTKNZPM-UHFFFAOYSA-N 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 18
- 230000001843 schistosomicidal effect Effects 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 241000242678 Schistosoma Species 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 150000007514 bases Chemical class 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 201000004409 schistosomiasis Diseases 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 97
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 79
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 33
- 239000007787 solid Substances 0.000 description 28
- 239000000047 product Substances 0.000 description 25
- 239000000243 solution Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 13
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 238000000354 decomposition reaction Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- DTXVKPOKPFWSFF-UHFFFAOYSA-N 3(S)-hydroxy-13-cis-eicosenoyl-CoA Chemical compound NC1=CC=C(Cl)N=N1 DTXVKPOKPFWSFF-UHFFFAOYSA-N 0.000 description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- DCKQFOVEXFIKND-UHFFFAOYSA-N 6-pyrrolidin-1-ylpyridazin-3-amine Chemical compound N1=NC(N)=CC=C1N1CCCC1 DCKQFOVEXFIKND-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000012458 free base Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical compound CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- HCJUYHLHJLPMFT-UHFFFAOYSA-N 6-piperidin-1-ylpyridazin-3-amine Chemical compound N1=NC(N)=CC=C1N1CCCCC1 HCJUYHLHJLPMFT-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- AXIZUTHGDYPRAS-UHFFFAOYSA-N 3-n,3-n-dimethylpyridazine-3,6-diamine;hydrochloride Chemical compound Cl.CN(C)C1=CC=C(N)N=N1 AXIZUTHGDYPRAS-UHFFFAOYSA-N 0.000 description 4
- ZBHPDTSJLMYIQI-UHFFFAOYSA-N 3-n,3-n-dipropylpyridazine-3,6-diamine Chemical compound CCCN(CCC)C1=CC=C(N)N=N1 ZBHPDTSJLMYIQI-UHFFFAOYSA-N 0.000 description 4
- BFTNCHQTLUQFEX-UHFFFAOYSA-N 6-(2,6-dimethylmorpholin-4-yl)pyridazin-3-amine Chemical compound C1C(C)OC(C)CN1C1=CC=C(N)N=N1 BFTNCHQTLUQFEX-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- LTJFPCBECZHXNS-UHFFFAOYSA-N 2,3-dimethylmorpholine Chemical compound CC1NCCOC1C LTJFPCBECZHXNS-UHFFFAOYSA-N 0.000 description 3
- RPSYMAMREDJAES-UHFFFAOYSA-N 2,5-dimethylmorpholine Chemical compound CC1COC(C)CN1 RPSYMAMREDJAES-UHFFFAOYSA-N 0.000 description 3
- GUSWJGOYDXFJSI-UHFFFAOYSA-N 3,6-dichloropyridazine Chemical compound ClC1=CC=C(Cl)N=N1 GUSWJGOYDXFJSI-UHFFFAOYSA-N 0.000 description 3
- NYOJAXJOBBCOEF-UHFFFAOYSA-N 3-chloro-6-pyrrolidin-1-ylpyridazine Chemical compound N1=NC(Cl)=CC=C1N1CCCC1 NYOJAXJOBBCOEF-UHFFFAOYSA-N 0.000 description 3
- XZGRUEIFRPTITR-UHFFFAOYSA-N 6-(4-methylpiperazin-1-yl)pyridazin-3-amine Chemical compound C1CN(C)CCN1C1=CC=C(N)N=N1 XZGRUEIFRPTITR-UHFFFAOYSA-N 0.000 description 3
- KCEJDUWJJNSRKB-UHFFFAOYSA-N 6-chloro-n,n-dipropylpyridazin-3-amine Chemical compound CCCN(CCC)C1=CC=C(Cl)N=N1 KCEJDUWJJNSRKB-UHFFFAOYSA-N 0.000 description 3
- IEUHTZVAUDMKQJ-UHFFFAOYSA-N 6-morpholin-4-ylpyridazin-3-amine Chemical compound N1=NC(N)=CC=C1N1CCOCC1 IEUHTZVAUDMKQJ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 230000000973 chemotherapeutic effect Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000002178 crystalline material Substances 0.000 description 3
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000003701 inert diluent Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- VBBRLWRHGXSWKX-UHFFFAOYSA-N n-(6-chloro-5-methylpyridazin-3-yl)acetamide Chemical compound CC(=O)NC1=CC(C)=C(Cl)N=N1 VBBRLWRHGXSWKX-UHFFFAOYSA-N 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- QUMRLXXCRQWODL-UHFFFAOYSA-N 1-methylpiperazin-1-ium;chloride Chemical compound [Cl-].C[NH+]1CCNCC1 QUMRLXXCRQWODL-UHFFFAOYSA-N 0.000 description 2
- GVGCGIPIDFQMFA-UHFFFAOYSA-N 2,2,6,6-tetramethylmorpholine Chemical compound CC1(C)CNCC(C)(C)O1 GVGCGIPIDFQMFA-UHFFFAOYSA-N 0.000 description 2
- XDAMZGXFTHZDFD-UHFFFAOYSA-N 2,3,5-trimethylmorpholine Chemical compound CC1COC(C)C(C)N1 XDAMZGXFTHZDFD-UHFFFAOYSA-N 0.000 description 2
- LPNZFNBNRWCBKA-UHFFFAOYSA-N 2,6-diethylmorpholine Chemical compound CCC1CNCC(CC)O1 LPNZFNBNRWCBKA-UHFFFAOYSA-N 0.000 description 2
- RGNFMQJLAOONTP-UHFFFAOYSA-N 2-ethylmorpholine Chemical compound CCC1CNCCO1 RGNFMQJLAOONTP-UHFFFAOYSA-N 0.000 description 2
- LQMMFVPUIVBYII-UHFFFAOYSA-N 2-methylmorpholine Chemical compound CC1CNCCO1 LQMMFVPUIVBYII-UHFFFAOYSA-N 0.000 description 2
- DNBOOEPFXFVICE-UHFFFAOYSA-N 2-propan-2-ylmorpholine Chemical compound CC(C)C1CNCCO1 DNBOOEPFXFVICE-UHFFFAOYSA-N 0.000 description 2
- QGJFIIKVYPIQAZ-UHFFFAOYSA-N 2-propylmorpholine Chemical compound CCCC1CNCCO1 QGJFIIKVYPIQAZ-UHFFFAOYSA-N 0.000 description 2
- YCSHCQUVDDBCFR-UHFFFAOYSA-N 3,3,5,5-tetramethylmorpholine Chemical compound CC1(C)COCC(C)(C)N1 YCSHCQUVDDBCFR-UHFFFAOYSA-N 0.000 description 2
- HEYGLTRAXBZNAD-UHFFFAOYSA-N 3,3-dimethylmorpholine Chemical compound CC1(C)COCCN1 HEYGLTRAXBZNAD-UHFFFAOYSA-N 0.000 description 2
- JBQWQBSRIAGTJT-UHFFFAOYSA-N 3-ethylmorpholine Chemical compound CCC1COCCN1 JBQWQBSRIAGTJT-UHFFFAOYSA-N 0.000 description 2
- SFWWGMKXCYLZEG-UHFFFAOYSA-N 3-methylmorpholine Chemical compound CC1COCCN1 SFWWGMKXCYLZEG-UHFFFAOYSA-N 0.000 description 2
- ZGDBMBXBBFEGIB-UHFFFAOYSA-N 3-n,3-n-diethylpyridazine-3,6-diamine Chemical compound CCN(CC)C1=CC=C(N)N=N1 ZGDBMBXBBFEGIB-UHFFFAOYSA-N 0.000 description 2
- NOPSPOQXLFJTRR-UHFFFAOYSA-N 3-n,3-n-dimethylpyridazine-3,6-diamine Chemical compound CN(C)C1=CC=C(N)N=N1 NOPSPOQXLFJTRR-UHFFFAOYSA-N 0.000 description 2
- IRIGZVVCFHIWNG-UHFFFAOYSA-N 3-n-methylpyridazine-3,6-diamine;hydrochloride Chemical compound Cl.CNC1=CC=C(N)N=N1 IRIGZVVCFHIWNG-UHFFFAOYSA-N 0.000 description 2
- ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 2
- MNGOCGNQLBTUAX-UHFFFAOYSA-N 5-ethyl-2-methylmorpholine Chemical compound CCC1COC(C)CN1 MNGOCGNQLBTUAX-UHFFFAOYSA-N 0.000 description 2
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- OHECYHCEVNYHAS-UHFFFAOYSA-N 6-(2,6-dimethylmorpholin-4-yl)pyridazine-3-carboxamide Chemical compound C1C(C)OC(C)CN1C1=CC=C(C(N)=O)N=N1 OHECYHCEVNYHAS-UHFFFAOYSA-N 0.000 description 2
- OKLWNDHAJHJTSA-UHFFFAOYSA-N 6-(2-ethylmorpholin-4-yl)pyridazin-3-amine Chemical compound C1COC(CC)CN1C1=CC=C(N)N=N1 OKLWNDHAJHJTSA-UHFFFAOYSA-N 0.000 description 2
- JFHVFRZGOGXGRO-UHFFFAOYSA-N 6-(2-methylmorpholin-4-yl)pyridazin-3-amine Chemical compound C1COC(C)CN1C1=CC=C(N)N=N1 JFHVFRZGOGXGRO-UHFFFAOYSA-N 0.000 description 2
- ZECPTQUKQDHLLX-UHFFFAOYSA-N 6-(2-propan-2-ylmorpholin-4-yl)pyridazin-3-amine Chemical compound C1COC(C(C)C)CN1C1=CC=C(N)N=N1 ZECPTQUKQDHLLX-UHFFFAOYSA-N 0.000 description 2
- HCODNXMBWUMGJS-UHFFFAOYSA-N 6-(2-propylmorpholin-4-yl)pyridazin-3-amine Chemical compound C1COC(CCC)CN1C1=CC=C(N)N=N1 HCODNXMBWUMGJS-UHFFFAOYSA-N 0.000 description 2
- RAKFHUONVOXSID-UHFFFAOYSA-N 6-(3-ethylmorpholin-4-yl)pyridazin-3-amine Chemical compound CCC1COCCN1C1=CC=C(N)N=N1 RAKFHUONVOXSID-UHFFFAOYSA-N 0.000 description 2
- JGMOGOOFMYZLTP-UHFFFAOYSA-N 6-(3-methylmorpholin-4-yl)pyridazin-3-amine Chemical compound CC1COCCN1C1=CC=C(N)N=N1 JGMOGOOFMYZLTP-UHFFFAOYSA-N 0.000 description 2
- UCFZEMUQWSGGCL-UHFFFAOYSA-N 6-(dimethylamino)pyridazine-3-carboxamide Chemical compound CN(C)C1=CC=C(C(N)=O)N=N1 UCFZEMUQWSGGCL-UHFFFAOYSA-N 0.000 description 2
- IDHMPIIGGVNFMC-UHFFFAOYSA-N 6-piperidin-1-ylpyridazine-3-carboxamide Chemical compound N1=NC(C(=O)N)=CC=C1N1CCCCC1 IDHMPIIGGVNFMC-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
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- 241000242683 Schistosoma haematobium Species 0.000 description 2
- 241000242680 Schistosoma mansoni Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
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- 239000003085 diluting agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
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- 239000011521 glass Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 150000002780 morpholines Chemical class 0.000 description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 150000004892 pyridazines Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three 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
- C07D237/20—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71569976A | 1976-08-19 | 1976-08-19 | |
| US05/805,419 US4104385A (en) | 1976-08-19 | 1977-06-10 | Cyclic alkylidenyl N-[6-(amino)-3-pyridazinyl]aminomethylenemalonates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2737542A1 true DE2737542A1 (de) | 1978-02-23 |
Family
ID=27109402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772737542 Withdrawn DE2737542A1 (de) | 1976-08-19 | 1977-08-19 | Cyclische alkylidenyl-n-(pyridazinyl)- aminomethylenmalonate und deren herstellung |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5334782A (ja) |
| AR (1) | AR221687A1 (ja) |
| AU (1) | AU515629B2 (ja) |
| DE (1) | DE2737542A1 (ja) |
| DK (1) | DK368177A (ja) |
| EG (1) | EG12733A (ja) |
| FR (1) | FR2362141A1 (ja) |
| GB (1) | GB1542030A (ja) |
| IL (1) | IL52681A (ja) |
| LU (1) | LU77976A1 (ja) |
| NL (1) | NL7709162A (ja) |
| NZ (1) | NZ184875A (ja) |
| PH (1) | PH12796A (ja) |
| PT (1) | PT66928B (ja) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001521025A (ja) * | 1997-10-27 | 2001-11-06 | ニューロサーチ、アクティーゼルスカブ | ニコチン性アセチルコリンレセプターに於けるコリン作動性リガンドとしてのヘテロアリールジアザシクロアルカン |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03133573A (ja) * | 1989-07-26 | 1991-06-06 | Sanso Aaku Kogyo Kk | 溶断棒 |
-
1977
- 1977-08-04 GB GB7732801A patent/GB1542030A/en not_active Expired
- 1977-08-08 AU AU27704/77A patent/AU515629B2/en not_active Expired
- 1977-08-08 IL IL52681A patent/IL52681A/xx unknown
- 1977-08-09 NZ NZ184875A patent/NZ184875A/xx unknown
- 1977-08-10 PH PH20107A patent/PH12796A/en unknown
- 1977-08-16 AR AR268813A patent/AR221687A1/es active
- 1977-08-16 EG EG484/77A patent/EG12733A/xx active
- 1977-08-16 PT PT66928A patent/PT66928B/pt unknown
- 1977-08-17 LU LU77976A patent/LU77976A1/xx unknown
- 1977-08-18 DK DK368177A patent/DK368177A/da not_active Application Discontinuation
- 1977-08-18 NL NL7709162A patent/NL7709162A/xx not_active Application Discontinuation
- 1977-08-19 FR FR7725414A patent/FR2362141A1/fr active Granted
- 1977-08-19 DE DE19772737542 patent/DE2737542A1/de not_active Withdrawn
- 1977-08-19 JP JP9942077A patent/JPS5334782A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001521025A (ja) * | 1997-10-27 | 2001-11-06 | ニューロサーチ、アクティーゼルスカブ | ニコチン性アセチルコリンレセプターに於けるコリン作動性リガンドとしてのヘテロアリールジアザシクロアルカン |
Also Published As
| Publication number | Publication date |
|---|---|
| AU515629B2 (en) | 1981-04-16 |
| EG12733A (en) | 1979-09-30 |
| IL52681A (en) | 1981-06-29 |
| AU2770477A (en) | 1979-02-15 |
| FR2362141B1 (ja) | 1981-07-17 |
| AR221687A1 (es) | 1981-03-13 |
| IL52681A0 (en) | 1977-10-31 |
| PT66928B (en) | 1979-02-05 |
| DK368177A (da) | 1978-02-20 |
| GB1542030A (en) | 1979-03-14 |
| NZ184875A (en) | 1979-03-28 |
| PH12796A (en) | 1979-08-17 |
| NL7709162A (nl) | 1978-02-21 |
| PT66928A (en) | 1977-09-01 |
| LU77976A1 (ja) | 1978-04-27 |
| FR2362141A1 (fr) | 1978-03-17 |
| JPS5334782A (en) | 1978-03-31 |
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| 8139 | Disposal/non-payment of the annual fee |