CH616158A5 - - Google Patents
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- Publication number
- CH616158A5 CH616158A5 CH517575A CH517575A CH616158A5 CH 616158 A5 CH616158 A5 CH 616158A5 CH 517575 A CH517575 A CH 517575A CH 517575 A CH517575 A CH 517575A CH 616158 A5 CH616158 A5 CH 616158A5
- Authority
- CH
- Switzerland
- Prior art keywords
- oxide
- diaminopyrimidine
- mol
- added
- amino
- Prior art date
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- -1 alkyl radical Chemical class 0.000 description 86
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 56
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 125000004432 carbon atom Chemical group C* 0.000 description 35
- 239000000203 mixture Substances 0.000 description 34
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 28
- 229910000027 potassium carbonate Inorganic materials 0.000 description 28
- 235000011181 potassium carbonates Nutrition 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 150000001875 compounds Chemical class 0.000 description 26
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 20
- 125000000217 alkyl group Chemical group 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 150000002084 enol ethers Chemical class 0.000 description 15
- QJPPQCHGWZNHKY-UHFFFAOYSA-N NC=1C(=[N+](C(=NC=1)N)[O-])N Chemical compound NC=1C(=[N+](C(=NC=1)N)[O-])N QJPPQCHGWZNHKY-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- FIMAYKDZLLQUDW-UHFFFAOYSA-N fluoro(dioxido)borane;trimethyloxidanium Chemical compound C[O+](C)C.C[O+](C)C.[O-]B([O-])F FIMAYKDZLLQUDW-UHFFFAOYSA-N 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 239000002253 acid Substances 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 5
- OQZGLXOADHKTDN-UHFFFAOYSA-N 1-oxidopyrimidin-1-ium Chemical class [O-][N+]1=CC=CN=C1 OQZGLXOADHKTDN-UHFFFAOYSA-N 0.000 description 4
- ANLQHFYDQPMDJY-UHFFFAOYSA-N 3-oxo-3-piperidin-1-ylpropanenitrile Chemical compound N#CCC(=O)N1CCCCC1 ANLQHFYDQPMDJY-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002168 alkylating agent Substances 0.000 description 4
- 229940100198 alkylating agent Drugs 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 150000002431 hydrogen Chemical group 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical class CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 150000002443 hydroxylamines Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- DGJMPUGMZIKDRO-NJFSPNSNSA-N 2-cyanoacetamide Chemical class NC(=O)[14CH2]C#N DGJMPUGMZIKDRO-NJFSPNSNSA-N 0.000 description 2
- QJIUMVUZDYPQRT-UHFFFAOYSA-N 6-chloro-2,4-pyrimidinediamine Chemical compound NC1=CC(Cl)=NC(N)=N1 QJIUMVUZDYPQRT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- BEZFCIXYQOVZCV-UHFFFAOYSA-N CNC1=CC(=[N+](C(=N1)N)[O-])N Chemical compound CNC1=CC(=[N+](C(=N1)N)[O-])N BEZFCIXYQOVZCV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- ZFMITUMMTDLWHR-UHFFFAOYSA-N Minoxidil Chemical compound NC1=[N+]([O-])C(N)=CC(N2CCCCC2)=N1 ZFMITUMMTDLWHR-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- JZZUKPAAFVSBJA-UHFFFAOYSA-N NC1=CC(N)=[N+]([O-])C(N)=N1 Chemical class NC1=CC(N)=[N+]([O-])C(N)=N1 JZZUKPAAFVSBJA-UHFFFAOYSA-N 0.000 description 2
- FMVJDYVWXJHAFZ-UHFFFAOYSA-N NC1=[N+]([O-])C(N)=CC(N2CCCC2)=N1 Chemical compound NC1=[N+]([O-])C(N)=CC(N2CCCC2)=N1 FMVJDYVWXJHAFZ-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical class NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 2
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- ZHGASCUQXLPSDT-UHFFFAOYSA-N cyclohexanesulfonic acid Chemical compound OS(=O)(=O)C1CCCCC1 ZHGASCUQXLPSDT-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-M fluorosulfonate Chemical compound [O-]S(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-M 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
- MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- CXAPGRNCBJXCEF-UHFFFAOYSA-N (2-cyano-1-piperidin-1-ylethylidene)cyanamide Chemical compound N#CCC(=NC#N)N1CCCCC1 CXAPGRNCBJXCEF-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- DPVIABCMTHHTGB-UHFFFAOYSA-N 2,4,6-trichloropyrimidine Chemical compound ClC1=CC(Cl)=NC(Cl)=N1 DPVIABCMTHHTGB-UHFFFAOYSA-N 0.000 description 1
- SWELIMKTDYHAOY-UHFFFAOYSA-N 2,4-diamino-6-hydroxypyrimidine Chemical compound NC1=CC(=O)N=C(N)N1 SWELIMKTDYHAOY-UHFFFAOYSA-N 0.000 description 1
- GGVUMZLSLQWRJJ-UHFFFAOYSA-N 2-cyano-N-cyclopentylhex-3-enamide Chemical compound C1(CCCC1)NC(C(C=CCC)C#N)=O GGVUMZLSLQWRJJ-UHFFFAOYSA-N 0.000 description 1
- LCDCJBPLBRPXBH-UHFFFAOYSA-N 2-cyano-n,n-dicyclohexylacetamide Chemical compound C1CCCCC1N(C(CC#N)=O)C1CCCCC1 LCDCJBPLBRPXBH-UHFFFAOYSA-N 0.000 description 1
- RURWLUVLDBYUEN-UHFFFAOYSA-N 2-cyano-n-cyclohexylacetamide Chemical compound N#CCC(=O)NC1CCCCC1 RURWLUVLDBYUEN-UHFFFAOYSA-N 0.000 description 1
- HKHWGARMGIPQRV-UHFFFAOYSA-N 2-cyano-n-decylacetamide Chemical compound CCCCCCCCCCNC(=O)CC#N HKHWGARMGIPQRV-UHFFFAOYSA-N 0.000 description 1
- BGYYGENARUYSSN-UHFFFAOYSA-N 2-cyano-n-ethyl-n-methylpropanamide Chemical compound CCN(C)C(=O)C(C)C#N BGYYGENARUYSSN-UHFFFAOYSA-N 0.000 description 1
- VARXTXAOJGBDDV-UHFFFAOYSA-N 2-cyano-n-ethylacetamide Chemical compound CCNC(=O)CC#N VARXTXAOJGBDDV-UHFFFAOYSA-N 0.000 description 1
- LIHUTSFYFGCWQP-UHFFFAOYSA-N 2-cyano-n-methylacetamide Chemical compound CNC(=O)CC#N LIHUTSFYFGCWQP-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical class C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical class NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000006041 3-hexenyl group Chemical group 0.000 description 1
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 description 1
- DBPKMSBWOKAKLA-UHFFFAOYSA-N 4-chloropyrimidine Chemical compound ClC1=CC=NC=N1 DBPKMSBWOKAKLA-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Chemical class 0.000 description 1
- JRBHRVWUMSLUTQ-UHFFFAOYSA-N C(C)NC1=CC(=[N+](C(=N1)N)[O-])N Chemical compound C(C)NC1=CC(=[N+](C(=N1)N)[O-])N JRBHRVWUMSLUTQ-UHFFFAOYSA-N 0.000 description 1
- IUSLIFJNUYVIGS-UHFFFAOYSA-N C(CCC)NC1=CC(=[N+](C(=N1)N)[O-])N Chemical compound C(CCC)NC1=CC(=[N+](C(=N1)N)[O-])N IUSLIFJNUYVIGS-UHFFFAOYSA-N 0.000 description 1
- QQMCNEYSSDZRKF-UHFFFAOYSA-N C(CCCCCCCCC)NC1=CC(=[N+](C(=N1)N)[O-])N Chemical compound C(CCCCCCCCC)NC1=CC(=[N+](C(=N1)N)[O-])N QQMCNEYSSDZRKF-UHFFFAOYSA-N 0.000 description 1
- FPVVIGKEAJFAET-UHFFFAOYSA-N C1(CCCCC1)NC1=CC(=[N+](C(=N1)N)[O-])N Chemical compound C1(CCCCC1)NC1=CC(=[N+](C(=N1)N)[O-])N FPVVIGKEAJFAET-UHFFFAOYSA-N 0.000 description 1
- QVVVMSAXGCGZPH-UHFFFAOYSA-N CC(C)=CC1=C(N2CCCCC2)N=C(N)[N+]([O-])=C1N Chemical compound CC(C)=CC1=C(N2CCCCC2)N=C(N)[N+]([O-])=C1N QVVVMSAXGCGZPH-UHFFFAOYSA-N 0.000 description 1
- CFUOXRRUWHUOET-UHFFFAOYSA-N CC=1C(=[N+](C(=NC1N1CCCCC1)N)[O-])N Chemical compound CC=1C(=[N+](C(=NC1N1CCCCC1)N)[O-])N CFUOXRRUWHUOET-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- SGMBAEQDJRWLIU-UHFFFAOYSA-N N1(CCCCC1)C1=C(C(=[N+](C(=N1)N)[O-])N)C(C)C Chemical compound N1(CCCCC1)C1=C(C(=[N+](C(=N1)N)[O-])N)C(C)C SGMBAEQDJRWLIU-UHFFFAOYSA-N 0.000 description 1
- WDCBTBGKHUPUGH-UHFFFAOYSA-N N1(CCCCC1)C1=C(C(=[N+](C(=N1)N)[O-])N)C(CCCC)C1=CC=CC=C1 Chemical compound N1(CCCCC1)C1=C(C(=[N+](C(=N1)N)[O-])N)C(CCCC)C1=CC=CC=C1 WDCBTBGKHUPUGH-UHFFFAOYSA-N 0.000 description 1
- SUEZVWTVFDZRJN-UHFFFAOYSA-N N1(CCCCC1)C1=C(C(=[N+](C(=N1)N)[O-])N)C1CCCCC1 Chemical compound N1(CCCCC1)C1=C(C(=[N+](C(=N1)N)[O-])N)C1CCCCC1 SUEZVWTVFDZRJN-UHFFFAOYSA-N 0.000 description 1
- DZKCZSVBDBBGHC-UHFFFAOYSA-N N1(CCCCC1)C1=C(C(=[N+](C(=N1)N)[O-])N)CCC Chemical compound N1(CCCCC1)C1=C(C(=[N+](C(=N1)N)[O-])N)CCC DZKCZSVBDBBGHC-UHFFFAOYSA-N 0.000 description 1
- WFCACTSNVJNSPA-UHFFFAOYSA-N N1(CCCCC1)C1=C(C(=[N+](C(=N1)N)[O-])N)CCC(C)C Chemical compound N1(CCCCC1)C1=C(C(=[N+](C(=N1)N)[O-])N)CCC(C)C WFCACTSNVJNSPA-UHFFFAOYSA-N 0.000 description 1
- WJPOQIIJYXHWSP-UHFFFAOYSA-N N1(CCCCC1)C1=C(C(=[N+](C(=N1)N)[O-])N)CCCC Chemical compound N1(CCCCC1)C1=C(C(=[N+](C(=N1)N)[O-])N)CCCC WJPOQIIJYXHWSP-UHFFFAOYSA-N 0.000 description 1
- NHJHJELKINPALA-UHFFFAOYSA-N NC1=C(C(=[N+](C(=N1)N)[O-])N)C Chemical compound NC1=C(C(=[N+](C(=N1)N)[O-])N)C NHJHJELKINPALA-UHFFFAOYSA-N 0.000 description 1
- BTDIGQWLFAKJPU-UHFFFAOYSA-N NC1=C[N+]([O-])=C(N)N=C1N Chemical class NC1=C[N+]([O-])=C(N)N=C1N BTDIGQWLFAKJPU-UHFFFAOYSA-N 0.000 description 1
- SZKKQCPJLIXWIH-UHFFFAOYSA-N NC1=NC(=CC(=[N+]1[O-])N)N1CCNCC1 Chemical compound NC1=NC(=CC(=[N+]1[O-])N)N1CCNCC1 SZKKQCPJLIXWIH-UHFFFAOYSA-N 0.000 description 1
- BAEWURLBOZSGIA-UHFFFAOYSA-N NC1=NC=CC=[N+]1[O-] Chemical compound NC1=NC=CC=[N+]1[O-] BAEWURLBOZSGIA-UHFFFAOYSA-N 0.000 description 1
- KTNALBSPIHZDLZ-UHFFFAOYSA-N NC1=[N+](C(=CC(=N1)N1CCOCC1)N)[O-] Chemical compound NC1=[N+](C(=CC(=N1)N1CCOCC1)N)[O-] KTNALBSPIHZDLZ-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 238000010934 O-alkylation reaction Methods 0.000 description 1
- DROZDPKLUFOVRQ-UHFFFAOYSA-N O1CCN(CC1)C1=C(C(=[N+](C(=N1)N)[O-])N)CCC(CC)C1=CC=CC=C1 Chemical compound O1CCN(CC1)C1=C(C(=[N+](C(=N1)N)[O-])N)CCC(CC)C1=CC=CC=C1 DROZDPKLUFOVRQ-UHFFFAOYSA-N 0.000 description 1
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002156 adsorbate Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical class O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- NQOJWOIPQBVKKX-UHFFFAOYSA-N cyclooctane Chemical compound [CH]1CCCCCCC1 NQOJWOIPQBVKKX-UHFFFAOYSA-N 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- AQGDCTOQZUOEOK-UHFFFAOYSA-N ethyl 2-cyano-3-(1-methylcyclohexa-2,4-dien-1-yl)propanoate Chemical compound C(C)OC(C(C#N)CC1(CC=CC=C1)C)=O AQGDCTOQZUOEOK-UHFFFAOYSA-N 0.000 description 1
- SYKQOFCBFHMCJV-UHFFFAOYSA-N ethyl 2-cyano-3-phenylpropanoate Chemical compound CCOC(=O)C(C#N)CC1=CC=CC=C1 SYKQOFCBFHMCJV-UHFFFAOYSA-N 0.000 description 1
- IQOSOHJXPUJHSV-UHFFFAOYSA-N ethyl 2-cyano-4-phenylpentanoate Chemical compound CCOC(=O)C(C#N)CC(C)C1=CC=CC=C1 IQOSOHJXPUJHSV-UHFFFAOYSA-N 0.000 description 1
- YMUSKLAPOQSFAH-UHFFFAOYSA-N ethyl 2-cyanohexanoate Chemical compound CCCCC(C#N)C(=O)OCC YMUSKLAPOQSFAH-UHFFFAOYSA-N 0.000 description 1
- MIHRVXYXORIINI-UHFFFAOYSA-N ethyl 2-cyanopropionate Chemical compound CCOC(=O)C(C)C#N MIHRVXYXORIINI-UHFFFAOYSA-N 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000004634 hexahydroazepinyl group Chemical group N1(CCCCCC1)* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- CQPQBICYNIUIIF-UHFFFAOYSA-N n,n-dibutyl-2-cyanoacetamide Chemical compound CCCCN(CCCC)C(=O)CC#N CQPQBICYNIUIIF-UHFFFAOYSA-N 0.000 description 1
- MGZNARROBKPUST-UHFFFAOYSA-N n-butyl-2-cyanoacetamide Chemical compound CCCCNC(=O)CC#N MGZNARROBKPUST-UHFFFAOYSA-N 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Chemical class OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000004346 phenylpentyl group Chemical group C1(=CC=CC=C1)CCCCC* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 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 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-OUBTZVSYSA-N potassium-40 Chemical compound [40K] ZLMJMSJWJFRBEC-OUBTZVSYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- XCXLEIPEAAEYTF-UHFFFAOYSA-M sodium fluorosulfate Chemical compound [Na+].[O-]S(F)(=O)=O XCXLEIPEAAEYTF-UHFFFAOYSA-M 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/195—Radicals derived from nitrogen analogues of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/50—Three nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US464476A US3910928A (en) | 1974-04-26 | 1974-04-26 | 3-(Cyanimino)-propionitriles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH616158A5 true CH616158A5 (cs) | 1980-03-14 |
Family
ID=23844086
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1166378A CH612924A5 (cs) | 1974-04-26 | 1975-04-23 | |
| CH517575A CH616158A5 (cs) | 1974-04-26 | 1975-04-23 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1166378A CH612924A5 (cs) | 1974-04-26 | 1975-04-23 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3910928A (cs) |
| JP (2) | JPS6039670B2 (cs) |
| BE (1) | BE828440A (cs) |
| CA (1) | CA1038388A (cs) |
| CH (2) | CH612924A5 (cs) |
| DE (1) | DE2516868C2 (cs) |
| DK (1) | DK157293C (cs) |
| ES (1) | ES436654A1 (cs) |
| FR (1) | FR2270250B1 (cs) |
| GB (1) | GB1450010A (cs) |
| HU (2) | HU172103B (cs) |
| IL (1) | IL46897A (cs) |
| NL (1) | NL182562C (cs) |
| SE (1) | SE458766B (cs) |
| SU (2) | SU645570A3 (cs) |
| ZA (1) | ZA752076B (cs) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4032559A (en) * | 1975-07-28 | 1977-06-28 | The Upjohn Company | N,2-dicyanoacetimidates |
| CH638216A5 (de) * | 1977-02-04 | 1983-09-15 | Hoffmann La Roche | Oxadiazolopyrimidin-deriate. |
| US4098791A (en) * | 1977-07-29 | 1978-07-04 | The Upjohn Company | Process for preparing 3-(cyanimino)-3-amino-propionitriles |
| CA1103245A (en) * | 1978-07-21 | 1981-06-16 | Jean-Claude Muller | Process for the manufacture of novel oxadiazolopyrimidine derivatives |
| US4308271A (en) * | 1980-06-23 | 1981-12-29 | The Upjohn Company | Animal feed and process |
| EP0042669A3 (en) * | 1980-06-23 | 1982-03-24 | The Upjohn Company | Compounds and compositions for use in animal feeds |
| JPS5973573A (ja) * | 1982-09-09 | 1984-04-25 | ワ−ナ−−ランバ−ト・コンパニ− | ジアミノピリミジン化合物 |
| LU86695A1 (fr) * | 1986-12-01 | 1988-07-14 | Oreal | Nouveaux derives de piperazinyl-1 pyrimidine,leur preparation et leur application en therapeutique et cosmetique |
| LU86960A1 (fr) * | 1987-07-31 | 1989-03-08 | Oreal | Procede de preparation de piperidino-6 diamino-2,4 pyrimidine oxyde-3 et composes nouveaux |
| JPH0662567B2 (ja) * | 1988-12-27 | 1994-08-17 | 麒麟麦酒株式会社 | ピリジンカルボキシイミダミド誘導体、その製造中間体、製造法および用途 |
| US5272164A (en) * | 1988-12-27 | 1993-12-21 | Kirin Beer Kabushiki Kaisha | Carboximidamide derivatives |
| US4959475A (en) * | 1989-01-04 | 1990-09-25 | Lonza Ltd. | Process for the production of 2,4-diamino-6-piperidinyl-pyrimidine-3-N-oxide |
| FR2671082B1 (fr) * | 1990-12-28 | 1993-04-16 | Oreal | Agent a plusieurs composants ou kit de preparation de la forme sulfo-conjuguee de composes pyrimidino- ou triazino-n-oxyde et procede de mise en óoeuvre. |
| WO2002100821A1 (en) * | 2001-06-12 | 2002-12-19 | Ube Industries, Ltd. | 3,3-dialkoxy-2-hydroxyiminopropionitriles, process for preparation thereof and process of preparing 5-amino -4-nitrosopyrazoles or salts thereof by the use of the same |
| CN111018838B (zh) * | 2019-11-25 | 2022-12-27 | 重庆东寰科技开发有限公司 | 吡咯烷基二氨基嘧啶氮氧化物的合成方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3382247A (en) * | 1965-11-01 | 1968-05-07 | Upjohn Co | 6-amino-1, 2-dihydro-1-hydroxy-2-imino-4-phenoxypyrimidines |
-
1974
- 1974-04-26 US US464476A patent/US3910928A/en not_active Expired - Lifetime
-
1975
- 1975-03-17 CA CA222,286A patent/CA1038388A/en not_active Expired
- 1975-03-21 IL IL46897A patent/IL46897A/xx unknown
- 1975-03-24 GB GB1211275A patent/GB1450010A/en not_active Expired
- 1975-04-02 ZA ZA00752076A patent/ZA752076B/xx unknown
- 1975-04-16 ES ES436654A patent/ES436654A1/es not_active Expired
- 1975-04-17 DE DE2516868A patent/DE2516868C2/de not_active Expired
- 1975-04-21 JP JP50047619A patent/JPS6039670B2/ja not_active Expired
- 1975-04-22 HU HU75UO00000125A patent/HU172103B/hu not_active IP Right Cessation
- 1975-04-22 HU HUUO110A patent/HU170090B/hu not_active IP Right Cessation
- 1975-04-23 CH CH1166378A patent/CH612924A5/xx not_active IP Right Cessation
- 1975-04-23 CH CH517575A patent/CH616158A5/de not_active IP Right Cessation
- 1975-04-24 DK DK179675A patent/DK157293C/da not_active IP Right Cessation
- 1975-04-24 NL NLAANVRAGE7504846,A patent/NL182562C/xx not_active IP Right Cessation
- 1975-04-24 SE SE7504762A patent/SE458766B/xx not_active IP Right Cessation
- 1975-04-25 FR FR7513011A patent/FR2270250B1/fr not_active Expired
- 1975-04-25 BE BE155822A patent/BE828440A/xx not_active IP Right Cessation
- 1975-04-25 SU SU752129052A patent/SU645570A3/ru active
- 1975-10-01 SU SU7502176209A patent/SU584770A3/ru active
-
1985
- 1985-02-13 JP JP60024576A patent/JPS60190753A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60190753A (ja) | 1985-09-28 |
| JPH0219829B2 (cs) | 1990-05-07 |
| ES436654A1 (es) | 1977-01-01 |
| DK157293B (da) | 1989-12-04 |
| JPS50148367A (cs) | 1975-11-27 |
| BE828440A (fr) | 1975-10-27 |
| JPS6039670B2 (ja) | 1985-09-06 |
| GB1450010A (en) | 1976-09-22 |
| SE458766B (sv) | 1989-05-08 |
| HU170090B (cs) | 1977-03-28 |
| DK179675A (da) | 1975-10-27 |
| NL182562B (nl) | 1987-11-02 |
| ZA752076B (en) | 1976-03-31 |
| CA1038388A (en) | 1978-09-12 |
| DE2516868C2 (de) | 1986-10-23 |
| FR2270250B1 (cs) | 1979-10-05 |
| DE2516868A1 (de) | 1975-11-13 |
| DK157293C (da) | 1990-05-07 |
| SE7504762L (sv) | 1975-10-27 |
| HU172103B (hu) | 1978-05-28 |
| IL46897A0 (en) | 1975-05-22 |
| IL46897A (en) | 1979-10-31 |
| FR2270250A1 (cs) | 1975-12-05 |
| AU7981875A (en) | 1976-10-07 |
| SU584770A3 (ru) | 1977-12-15 |
| NL7504846A (nl) | 1975-10-28 |
| NL182562C (nl) | 1988-04-05 |
| SU645570A3 (ru) | 1979-01-30 |
| CH612924A5 (cs) | 1979-08-31 |
| US3910928A (en) | 1975-10-07 |
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