CH449647A - Verbindungen zur Herstellung von substituierten Hydrazinverbindungen - Google Patents
Verbindungen zur Herstellung von substituierten HydrazinverbindungenInfo
- Publication number
- CH449647A CH449647A CH1135561A CH1135561A CH449647A CH 449647 A CH449647 A CH 449647A CH 1135561 A CH1135561 A CH 1135561A CH 1135561 A CH1135561 A CH 1135561A CH 449647 A CH449647 A CH 449647A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- substituted
- compounds
- hydrazine
- bis
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 15
- 150000002429 hydrazines Chemical class 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 5
- -1 substituents halogen Chemical class 0.000 claims description 75
- 125000006239 protecting group Chemical group 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000002431 aminoalkoxy group Chemical group 0.000 claims description 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- 239000000243 solution Substances 0.000 description 37
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 235000019441 ethanol Nutrition 0.000 description 14
- 239000002253 acid Substances 0.000 description 12
- 239000000155 melt Substances 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- QPHPEPMDRYADGQ-UHFFFAOYSA-N n'-benzoyl-n'-methylbenzohydrazide Chemical compound C=1C=CC=CC=1C(=O)N(C)NC(=O)C1=CC=CC=C1 QPHPEPMDRYADGQ-UHFFFAOYSA-N 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- XKOYHHVVJGYROX-UHFFFAOYSA-N benzyl n-methyl-n-(phenylmethoxycarbonylamino)carbamate Chemical compound C=1C=CC=CC=1COC(=O)N(C)NC(=O)OCC1=CC=CC=C1 XKOYHHVVJGYROX-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 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
- 239000013078 crystal Substances 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 3
- 150000007857 hydrazones Chemical class 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- MJEDFBZXMUITPO-WHFBIAKZSA-N (1R,2R)-1,2-bis(iodomethyl)cyclopropane Chemical compound IC[C@H]1[C@@H](C1)CI MJEDFBZXMUITPO-WHFBIAKZSA-N 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- ZOGLLMFVLBBAIU-UHFFFAOYSA-N CN(N(CC(=O)OCC)C(C)=O)C(C)=O Chemical compound CN(N(CC(=O)OCC)C(C)=O)C(C)=O ZOGLLMFVLBBAIU-UHFFFAOYSA-N 0.000 description 2
- IGNAERYJVDVJBJ-BQBZGAKWSA-N CNNC[C@H]1[C@@H](C1)CNNC Chemical compound CNNC[C@H]1[C@@H](C1)CNNC IGNAERYJVDVJBJ-BQBZGAKWSA-N 0.000 description 2
- 201000009030 Carcinoma Diseases 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229910052500 inorganic mineral Chemical class 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Chemical class 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- XDILHIDHUKDARQ-UHFFFAOYSA-N n'-acetyl-n'-methylacetohydrazide Chemical compound CC(=O)N(C)NC(C)=O XDILHIDHUKDARQ-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000003578 releasing effect Effects 0.000 description 2
- GVNNGJMKAFLSHZ-NSCUHMNNSA-N (e)-1,3-dichlorobut-1-ene Chemical compound CC(Cl)\C=C\Cl GVNNGJMKAFLSHZ-NSCUHMNNSA-N 0.000 description 1
- LJVHJHLTRBXGMH-HNQUOIGGSA-N (e)-1,4-dibromobut-1-ene Chemical compound BrCC\C=C\Br LJVHJHLTRBXGMH-HNQUOIGGSA-N 0.000 description 1
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- MYALOPJJAPLQSJ-UHFFFAOYSA-N 1,4-bis(bromomethyl)cyclohexane Chemical compound BrCC1CCC(CBr)CC1 MYALOPJJAPLQSJ-UHFFFAOYSA-N 0.000 description 1
- YAHIILVEZVRPOM-UHFFFAOYSA-N 1-(cyclohexylmethyl)-2-methylhydrazine Chemical compound CNNCC1CCCCC1 YAHIILVEZVRPOM-UHFFFAOYSA-N 0.000 description 1
- FOZVXADQAHVUSV-UHFFFAOYSA-N 1-bromo-2-(2-bromoethoxy)ethane Chemical compound BrCCOCCBr FOZVXADQAHVUSV-UHFFFAOYSA-N 0.000 description 1
- HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- YUVBHAYUWNBUAP-UHFFFAOYSA-N 1-methyl-2-[3-(2-methylhydrazinyl)propyl]hydrazine Chemical compound CNNCCCNNC YUVBHAYUWNBUAP-UHFFFAOYSA-N 0.000 description 1
- NZPNOYFQRNWUDA-UHFFFAOYSA-N 1-methyl-2-[4-(2-methylhydrazinyl)butyl]hydrazine Chemical compound CNNCCCCNNC NZPNOYFQRNWUDA-UHFFFAOYSA-N 0.000 description 1
- USVQOWNGMOIJAZ-UWVGGRQHSA-N 1-methyl-2-[[(1R,2R)-2-[(2-methylhydrazinyl)methyl]cyclohexyl]methyl]hydrazine Chemical compound CNNC[C@H]1[C@@H](CCCC1)CNNC USVQOWNGMOIJAZ-UWVGGRQHSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- DCPLOIFDMMEBQZ-UHFFFAOYSA-N 2-bromo-n-phenylacetamide Chemical compound BrCC(=O)NC1=CC=CC=C1 DCPLOIFDMMEBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 206010003445 Ascites Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- IVPHNZAHUZJTAC-UHFFFAOYSA-N CNNCC(CNNC)C Chemical compound CNNCC(CNNC)C IVPHNZAHUZJTAC-UHFFFAOYSA-N 0.000 description 1
- IZZWXVZJHPHRAF-UHFFFAOYSA-N CNNCCC=CNNC Chemical compound CNNCCC=CNNC IZZWXVZJHPHRAF-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KUZIPHZNJPDQGM-UHFFFAOYSA-N Cl.CNNCC(NC1=CC=CC=C1)=O Chemical compound Cl.CNNCC(NC1=CC=CC=C1)=O KUZIPHZNJPDQGM-UHFFFAOYSA-N 0.000 description 1
- RLYCIBQNOCUQNB-UHFFFAOYSA-N Cl.Cl.CNNCCCCCCCCCCNNC Chemical compound Cl.Cl.CNNCCCCCCCCCCNNC RLYCIBQNOCUQNB-UHFFFAOYSA-N 0.000 description 1
- QTEJYNPRFSBGMT-UHFFFAOYSA-N Cl.Cl.CNNCCCCNNC Chemical compound Cl.Cl.CNNCCCCNNC QTEJYNPRFSBGMT-UHFFFAOYSA-N 0.000 description 1
- AQWKYJPDNLAKNX-UHFFFAOYSA-N Cl.Cl.CNNCCCNNC Chemical compound Cl.Cl.CNNCCCNNC AQWKYJPDNLAKNX-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- 102000053602 DNA Human genes 0.000 description 1
- 108020004414 DNA Proteins 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 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
- SWXDNKVUVKMURJ-UHFFFAOYSA-N [2-(hydroxymethyl)cyclopropyl]methanol Chemical compound OCC1CC1CO SWXDNKVUVKMURJ-UHFFFAOYSA-N 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 1
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 description 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000000320 amidine group Chemical group 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 230000003327 cancerostatic effect Effects 0.000 description 1
- 125000005242 carbamoyl alkyl group Chemical group 0.000 description 1
- 150000001727 carbonic acid monoesters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- YZGJDVPXFMTQRZ-UHFFFAOYSA-N cyclohexylmethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1CCCCC1 YZGJDVPXFMTQRZ-UHFFFAOYSA-N 0.000 description 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
- SXLDHZFJMXLFJU-UHFFFAOYSA-N diethyl cyclopropane-1,2-dicarboxylate Chemical compound CCOC(=O)C1CC1C(=O)OCC SXLDHZFJMXLFJU-UHFFFAOYSA-N 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- MEBDASBFCISMGU-UHFFFAOYSA-N hydrazine;hydron;dibromide Chemical compound Br.Br.NN MEBDASBFCISMGU-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- IVXCVROGNYFLEO-UHFFFAOYSA-N n-chloropropan-2-amine Chemical compound CC(C)NCl IVXCVROGNYFLEO-UHFFFAOYSA-N 0.000 description 1
- XDIIJQFNVMXIJQ-UHFFFAOYSA-N n-methylacetohydrazide Chemical compound CN(N)C(C)=O XDIIJQFNVMXIJQ-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/15—Oximes (>C=N—O—); Hydrazines (>N—N<); Hydrazones (>N—N=) ; Imines (C—N=C)
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL283702D NL283702A (en:Method) | 1961-09-29 | ||
| CH1135561A CH449647A (de) | 1961-09-29 | 1961-09-29 | Verbindungen zur Herstellung von substituierten Hydrazinverbindungen |
| DEH46868A DE1239315B (de) | 1961-09-29 | 1962-09-10 | Verfahren zur Herstellung von substituierten Hydrazinverbindungen |
| FR910223A FR2671M (fr) | 1961-09-29 | 1962-09-24 | Médicament a base de dérivés d'hydrazine. |
| GB36525/62A GB993036A (en) | 1961-09-29 | 1962-09-26 | Novel hydrazine derivatives and salts and a process for the manufacture thereof |
| ES281137A ES281137A1 (es) | 1961-09-29 | 1962-09-28 | Un procedimiento para la fabricación de derivados hidrazínicos sustituídos |
| US449636A US3272839A (en) | 1961-09-29 | 1965-04-20 | Substituted methylhydrazine compounds |
| MY196641A MY6600041A (en) | 1961-09-29 | 1966-12-31 | Novel hydrazine derivatives and salts and a process for the manufacture thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1135561A CH449647A (de) | 1961-09-29 | 1961-09-29 | Verbindungen zur Herstellung von substituierten Hydrazinverbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH449647A true CH449647A (de) | 1968-01-15 |
Family
ID=4372688
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1135561A CH449647A (de) | 1961-09-29 | 1961-09-29 | Verbindungen zur Herstellung von substituierten Hydrazinverbindungen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3272839A (en:Method) |
| CH (1) | CH449647A (en:Method) |
| DE (1) | DE1239315B (en:Method) |
| ES (1) | ES281137A1 (en:Method) |
| FR (1) | FR2671M (en:Method) |
| GB (1) | GB993036A (en:Method) |
| MY (1) | MY6600041A (en:Method) |
| NL (1) | NL283702A (en:Method) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH457492A (de) * | 1965-03-05 | 1968-06-15 | Hoffmann La Roche | Verfahren zur Herstellung von substituierten Hydrazinverbindungen |
| CH457401A (de) * | 1965-03-05 | 1968-06-15 | Hoffmann La Roche | Verfahren zur Herstellung von substituierten Hydrazinverbindungen |
| US4045484A (en) * | 1975-07-16 | 1977-08-30 | Uniroyal, Inc. | Process for preparing N'-methyl acethydrazide |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3110730A (en) * | 1960-06-13 | 1963-11-12 | Gever Gabriel | Process for preparing methylhydrazine |
| NL291230A (en:Method) * | 1962-04-09 |
-
0
- NL NL283702D patent/NL283702A/xx unknown
-
1961
- 1961-09-29 CH CH1135561A patent/CH449647A/de unknown
-
1962
- 1962-09-10 DE DEH46868A patent/DE1239315B/de active Granted
- 1962-09-24 FR FR910223A patent/FR2671M/fr not_active Expired
- 1962-09-26 GB GB36525/62A patent/GB993036A/en not_active Expired
- 1962-09-28 ES ES281137A patent/ES281137A1/es not_active Expired
-
1965
- 1965-04-20 US US449636A patent/US3272839A/en not_active Expired - Lifetime
-
1966
- 1966-12-31 MY MY196641A patent/MY6600041A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MY6600041A (en) | 1966-12-31 |
| GB993036A (en) | 1965-05-26 |
| NL283702A (en:Method) | 1900-01-01 |
| DE1239315C2 (en:Method) | 1967-11-09 |
| DE1239315B (de) | 1967-04-27 |
| US3272839A (en) | 1966-09-13 |
| FR2671M (fr) | 1964-07-20 |
| ES281137A1 (es) | 1963-03-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0026848B1 (de) | Tetralinderivate, ihre Herstellung und Heilmittel, welche diese Verbindungen enthalten | |
| DE2362568C2 (de) | Alkanolaminderivate und sie enthaltende pharmazeutische Zusammensetzungen | |
| DE69412109T2 (de) | Salzetersaüreester mit entzündungshemmender und/oder schmerzlindernder wirkung und verfahren zu deren herstellung | |
| DE3114239A1 (de) | "piperazinderivate" | |
| CH441366A (de) | Verfahren zur Herstellung von substituierten Hydrazinverbindungen | |
| CH449647A (de) | Verbindungen zur Herstellung von substituierten Hydrazinverbindungen | |
| DE3642105A1 (de) | Substituierte aminomethyl-5,6,7,8-tetrahydronaphtyl-oxyessigsaeuren, neue zwischenprodukte, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln | |
| DE2058532C3 (de) | Verfahren zur Herstellung von 1-Aryloxy-3-aminopropan-Derivaten und neue 1-Aryloxy-3-amino-2-propanoläther | |
| AT236931B (de) | Verfahren zur Herstellung von substituierten Hydrazinverbindungen | |
| CH616143A5 (en:Method) | ||
| CH374071A (de) | Verfahren zur Herstellung von neuen Isoindolinderivaten | |
| DE2310215A1 (de) | Neue thiophenderivate und verfahren zu ihrer herstellung | |
| DD151447A1 (de) | Verfahren zur herstellung von amidinen und deren salzen | |
| AT234663B (de) | Verfahren zur Herstellung von substituierten Hydrazinverbindungen und deren Salzen | |
| DE1215729B (de) | Verfahren zur Herstellung von neuen Bis-alkanolaminderivaten und deren Salzen | |
| AT234687B (de) | Verfahren zur Herstellung von neuen Benzodioxanderivaten, sowie von deren Säureadditionssalzen | |
| EP0102929B1 (de) | Propylamin-Derivate, Verfahren zu ihrer Herstellung, pharmazeutische Präparate enthaltend diese Verbindungen, sowie ihre therapeutische Verwendung | |
| DE3343884C2 (en:Method) | ||
| AT256863B (de) | Verfahren zur Herstellung neuer basischer Derivate des Dihydro-1, 3-benzoxazin-2, 4-dions | |
| AT225197B (de) | Verfahren zur Herstellung der neuen N-[p-3,3-disubstituierten-1-Azetidinyläthoxy)-benzyl]-3,4,5-trimethoxybenzamide | |
| DE1966174C3 (de) | Arylester der 4-Aminomethyl-benzoesäure, deren pharmazeutisch anwendbare Salze, Verfahren zur herstellung dieser Verbindungen und diese Verbindungen enthaltende pharmazeutische Präparate | |
| AT226710B (de) | Verfahren zur Herstellung von neuen Dihydrochinoxalonen-(2) und von deren Salzen | |
| CH557815A (de) | Verfahren zur herstellung von 3-indol-aliphatischen saeuren. | |
| DE2822473A1 (de) | Alkanolaminderivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zusammensetzungen | |
| AT219028B (de) | Verfahren zur Herstellung von neuen Trichlormethansulfensäurederivaten |