DE2547590A1 - Neue 1-sulfonyl-4-amino-pyridiniumsalze und verfahren zu ihrer herstellung - Google Patents
Neue 1-sulfonyl-4-amino-pyridiniumsalze und verfahren zu ihrer herstellungInfo
- Publication number
- DE2547590A1 DE2547590A1 DE19752547590 DE2547590A DE2547590A1 DE 2547590 A1 DE2547590 A1 DE 2547590A1 DE 19752547590 DE19752547590 DE 19752547590 DE 2547590 A DE2547590 A DE 2547590A DE 2547590 A1 DE2547590 A1 DE 2547590A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- anion
- alkyl
- hydrogen
- atoms
- 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- Withdrawn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
- 238000000034 method Methods 0.000 title claims description 14
- 230000008569 process Effects 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 7
- WSLOUIWEJZHGNJ-UHFFFAOYSA-N 1-sulfonyl-2h-pyridin-1-ium-4-amine Chemical class NC1=CC[N+](=S(=O)=O)C=C1 WSLOUIWEJZHGNJ-UHFFFAOYSA-N 0.000 title description 6
- -1 F " Chemical class 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 24
- 239000003795 chemical substances by application Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000001450 anions Chemical class 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 150000003928 4-aminopyridines Chemical class 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 7
- 150000008064 anhydrides Chemical class 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 5
- 239000003586 protic polar solvent Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- BPSUJSDZHLTNJR-UHFFFAOYSA-N sulfamide;hydrochloride Chemical class Cl.NS(N)(=O)=O BPSUJSDZHLTNJR-UHFFFAOYSA-N 0.000 claims description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
- 125000004964 sulfoalkyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 150000005619 secondary aliphatic amines Chemical class 0.000 claims description 2
- 239000011877 solvent mixture Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000003139 primary aliphatic amines Chemical class 0.000 claims 1
- 102000004196 processed proteins & peptides Human genes 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 claims 1
- 102000004169 proteins and genes Human genes 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 15
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 13
- 229960004979 fampridine Drugs 0.000 description 13
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910001916 chloryl Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 229940124530 sulfonamide Drugs 0.000 description 4
- 150000003456 sulfonamides Chemical class 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
- ZJXMKPARTVOUAM-UHFFFAOYSA-N 2,6-dimethylpyridin-4-amine Chemical class CC1=CC(N)=CC(C)=N1 ZJXMKPARTVOUAM-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- AVPYLKIIPLFMHQ-UHFFFAOYSA-N 1,2,6-oxadithiane 2,2,6,6-tetraoxide Chemical compound O=S1(=O)CCCS(=O)(=O)O1 AVPYLKIIPLFMHQ-UHFFFAOYSA-N 0.000 description 2
- KDTUHGXEVKEQDB-UHFFFAOYSA-N 1-sulfonyl-2h-pyridin-1-ium Chemical class O=S(=O)=[N+]1CC=CC=C1 KDTUHGXEVKEQDB-UHFFFAOYSA-N 0.000 description 2
- 150000003930 2-aminopyridines Chemical class 0.000 description 2
- GNCLPNMQEGMNTG-UHFFFAOYSA-N 2-methylpyridin-4-amine Chemical class CC1=CC(N)=CC=N1 GNCLPNMQEGMNTG-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-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
- FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000003927 aminopyridines Chemical class 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-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
- 229940125904 compound 1 Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 230000006103 sulfonylation Effects 0.000 description 2
- 238000005694 sulfonylation reaction Methods 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- PSBDWGZCVUAZQS-UHFFFAOYSA-N (dimethylsulfonio)acetate Chemical compound C[S+](C)CC([O-])=O PSBDWGZCVUAZQS-UHFFFAOYSA-N 0.000 description 1
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QTLDNGFPYAWPLR-UHFFFAOYSA-N 2,1$l^{6},3$l^{6}-benzoxadithiole 1,1,3,3-tetraoxide Chemical compound C1=CC=C2S(=O)(=O)OS(=O)(=O)C2=C1 QTLDNGFPYAWPLR-UHFFFAOYSA-N 0.000 description 1
- UFNXQFILCHKKPD-UHFFFAOYSA-N 2,3,5,6-tetramethylpyridin-4-amine Chemical compound CC1=NC(C)=C(C)C(N)=C1C UFNXQFILCHKKPD-UHFFFAOYSA-N 0.000 description 1
- LIDGFHXPUOJZMK-UHFFFAOYSA-N 2,6-dimethyl-1-oxidopyridin-1-ium Chemical compound CC1=CC=CC(C)=[N+]1[O-] LIDGFHXPUOJZMK-UHFFFAOYSA-N 0.000 description 1
- WTSZSAHZIMPSDM-UHFFFAOYSA-N 2-(benzenesulfonamido)acetic acid Chemical compound OC(=O)CNS(=O)(=O)C1=CC=CC=C1 WTSZSAHZIMPSDM-UHFFFAOYSA-N 0.000 description 1
- LTZMAQOKPJMBRZ-UHFFFAOYSA-N 2-(methanesulfonamido)acetic acid Chemical compound CS(=O)(=O)NCC(O)=O LTZMAQOKPJMBRZ-UHFFFAOYSA-N 0.000 description 1
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 1
- VHCSBTPOPKFYIU-UHFFFAOYSA-N 2-chloroethanesulfonyl chloride Chemical compound ClCCS(Cl)(=O)=O VHCSBTPOPKFYIU-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- HSPMUFVIWJXJHX-UHFFFAOYSA-N 2-ethoxypyridin-4-amine Chemical compound CCOC1=CC(N)=CC=N1 HSPMUFVIWJXJHX-UHFFFAOYSA-N 0.000 description 1
- QFLLABOTLITCPP-UHFFFAOYSA-N 3,5-dimethylpyridin-4-amine Chemical compound CC1=CN=CC(C)=C1N QFLLABOTLITCPP-UHFFFAOYSA-N 0.000 description 1
- 150000003929 3-aminopyridines Chemical class 0.000 description 1
- QNDMDMFWRZOZEB-UHFFFAOYSA-N 3-ethoxypyridin-4-amine Chemical compound CCOC1=CN=CC=C1N QNDMDMFWRZOZEB-UHFFFAOYSA-N 0.000 description 1
- ROUXTDYIQSLWBU-UHFFFAOYSA-N 3-ethyl-n-methylpyridin-4-amine Chemical compound CCC1=CN=CC=C1NC ROUXTDYIQSLWBU-UHFFFAOYSA-N 0.000 description 1
- ODKNKXQVRUFTPT-UHFFFAOYSA-N 3-ethylpyridin-4-amine Chemical compound CCC1=CN=CC=C1N ODKNKXQVRUFTPT-UHFFFAOYSA-N 0.000 description 1
- VGJLGPCXUGIXRQ-UHFFFAOYSA-N 3-methylpyridin-4-amine Chemical compound CC1=CN=CC=C1N VGJLGPCXUGIXRQ-UHFFFAOYSA-N 0.000 description 1
- QCXAZPBETOAZBK-UHFFFAOYSA-N 3-propan-2-ylpyridin-4-amine Chemical compound CC(C)C1=CN=CC=C1N QCXAZPBETOAZBK-UHFFFAOYSA-N 0.000 description 1
- JBPWDSBIMSBCMB-UHFFFAOYSA-N 4-(2,6-dimethylpyridin-4-yl)morpholine Chemical compound CC1=NC(C)=CC(N2CCOCC2)=C1 JBPWDSBIMSBCMB-UHFFFAOYSA-N 0.000 description 1
- OFDXXPVRNNRMHI-UHFFFAOYSA-N 4-aminopyridine-3-carboxamide Chemical compound NC(=O)C1=CN=CC=C1N OFDXXPVRNNRMHI-UHFFFAOYSA-N 0.000 description 1
- DPJVRASYWYOFSJ-UHFFFAOYSA-N 4-chloro-1-oxidopyridin-1-ium Chemical group [O-][N+]1=CC=C(Cl)C=C1 DPJVRASYWYOFSJ-UHFFFAOYSA-N 0.000 description 1
- SXCXPXVEOPFPOH-UHFFFAOYSA-N 4-chloro-2,6-dimethylpyridine Chemical compound CC1=CC(Cl)=CC(C)=N1 SXCXPXVEOPFPOH-UHFFFAOYSA-N 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- JBAVNFBLQOGCRB-UHFFFAOYSA-N 4-methyl-3h-1,2,6-oxadithiine 2,2,6,6-tetraoxide Chemical compound CC1=CS(=O)(=O)OS(=O)(=O)C1 JBAVNFBLQOGCRB-UHFFFAOYSA-N 0.000 description 1
- RXKNNAKAVAHBNK-UHFFFAOYSA-N 4-nitropyridine-n-oxide Chemical class [O-][N+](=O)C1=CC=[N+]([O-])C=C1 RXKNNAKAVAHBNK-UHFFFAOYSA-N 0.000 description 1
- MTPBUCCXRGSDCR-UHFFFAOYSA-N 4-piperidin-1-ylpyridine Chemical compound C1CCCCN1C1=CC=NC=C1 MTPBUCCXRGSDCR-UHFFFAOYSA-N 0.000 description 1
- QJWQYVJVCXMTJP-UHFFFAOYSA-N 4-pyridin-4-ylmorpholine Chemical compound C1COCCN1C1=CC=NC=C1 QJWQYVJVCXMTJP-UHFFFAOYSA-N 0.000 description 1
- WIJOOIFTTQXTBL-UHFFFAOYSA-N 5-ethyl-2-methylpyridin-4-amine Chemical compound CCC1=CN=C(C)C=C1N WIJOOIFTTQXTBL-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical class ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- 238000006681 Combes synthesis reaction Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- PRRAMVWLJGCSOS-UHFFFAOYSA-N N-(methylsulfamoyl)methanamine hydrochloride Chemical compound Cl.CNS(NC)(=O)=O PRRAMVWLJGCSOS-UHFFFAOYSA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- MLWPJXZKQOPTKZ-UHFFFAOYSA-N benzenesulfonyl benzenesulfonate Chemical compound C=1C=CC=CC=1S(=O)(=O)OS(=O)(=O)C1=CC=CC=C1 MLWPJXZKQOPTKZ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- JESCPVSKEGXYSC-UHFFFAOYSA-N chlorobenzene;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.ClC1=CC=CC=C1 JESCPVSKEGXYSC-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 229940126540 compound 41 Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 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 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical class OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- LLCOIQRNSJBFSN-UHFFFAOYSA-N methane;sulfurochloridic acid Chemical compound C.OS(Cl)(=O)=O LLCOIQRNSJBFSN-UHFFFAOYSA-N 0.000 description 1
- GAWQMBKSZUJMML-UHFFFAOYSA-N n,n,3-trimethylpyridin-4-amine Chemical compound CN(C)C1=CC=NC=C1C GAWQMBKSZUJMML-UHFFFAOYSA-N 0.000 description 1
- ZKROIIKNWZGVTE-UHFFFAOYSA-N n-butylpyridin-4-amine Chemical compound CCCCNC1=CC=NC=C1 ZKROIIKNWZGVTE-UHFFFAOYSA-N 0.000 description 1
- WDRQQCOWXCWKGZ-UHFFFAOYSA-N n-cyclohexylpyridin-4-amine Chemical compound C1CCCCC1NC1=CC=NC=C1 WDRQQCOWXCWKGZ-UHFFFAOYSA-N 0.000 description 1
- OTIDWUALRXXVIM-UHFFFAOYSA-N n-ethylpyridin-4-amine Chemical compound CCNC1=CC=NC=C1 OTIDWUALRXXVIM-UHFFFAOYSA-N 0.000 description 1
- LSCYTCMNCWMCQE-UHFFFAOYSA-N n-methylpyridin-4-amine Chemical compound CNC1=CC=NC=C1 LSCYTCMNCWMCQE-UHFFFAOYSA-N 0.000 description 1
- DKQSRQLSDPYGCJ-UHFFFAOYSA-N n-phenylpyridin-4-amine Chemical compound C=1C=NC=CC=1NC1=CC=CC=C1 DKQSRQLSDPYGCJ-UHFFFAOYSA-N 0.000 description 1
- BIPRNRDNBVGHNV-UHFFFAOYSA-N n-propan-2-ylpyridin-4-amine Chemical compound CC(C)NC1=CC=NC=C1 BIPRNRDNBVGHNV-UHFFFAOYSA-N 0.000 description 1
- HBBSAGHMADHTBB-UHFFFAOYSA-N n-pyridin-4-ylmethanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=NC=C1 HBBSAGHMADHTBB-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 description 1
- 229910001488 sodium perchlorate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- GECHUMIMRBOMGK-UHFFFAOYSA-N sulfapyridine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=CC=N1 GECHUMIMRBOMGK-UHFFFAOYSA-N 0.000 description 1
- 229960002211 sulfapyridine Drugs 0.000 description 1
- 229940117986 sulfobetaine Drugs 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- FVIRGMIYFJWRGC-UHFFFAOYSA-N sulfurobromidic acid Chemical class OS(Br)(=O)=O FVIRGMIYFJWRGC-UHFFFAOYSA-N 0.000 description 1
- QSHRCSUARRBOEL-UHFFFAOYSA-N sulfurochloridic acid;1,3,5-trimethylbenzene Chemical compound OS(Cl)(=O)=O.CC1=CC(C)=CC(C)=C1 QSHRCSUARRBOEL-UHFFFAOYSA-N 0.000 description 1
- BBDNZMUIQBRBJH-UHFFFAOYSA-N sulfurochloridic acid;toluene Chemical compound OS(Cl)(=O)=O.CC1=CC=CC=C1 BBDNZMUIQBRBJH-UHFFFAOYSA-N 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Quinoline Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752547590 DE2547590A1 (de) | 1975-10-24 | 1975-10-24 | Neue 1-sulfonyl-4-amino-pyridiniumsalze und verfahren zu ihrer herstellung |
| BE1007681A BE847061A (nl) | 1975-10-24 | 1976-10-08 | Nieuwe 1-sulfonyl-4-amino-pyridinium-zouteen en werkwijzen voor de vervaardiging ervan, |
| GB4315976A GB1537461A (en) | 1975-10-24 | 1976-10-18 | 1-sulphonyl-4-amino-pyridinium salts and a process for their preparation |
| JP12637476A JPS5251372A (en) | 1975-10-24 | 1976-10-22 | New 11sulphonyll44aminoo pyridinium salt and preparation method thereof |
| FR7631930A FR2328699A1 (fr) | 1975-10-24 | 1976-10-22 | Nouveaux sels de sulfonyl-1 amino-4 pyridinium et procede de leur preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752547590 DE2547590A1 (de) | 1975-10-24 | 1975-10-24 | Neue 1-sulfonyl-4-amino-pyridiniumsalze und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2547590A1 true DE2547590A1 (de) | 1977-04-28 |
Family
ID=5959961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752547590 Withdrawn DE2547590A1 (de) | 1975-10-24 | 1975-10-24 | Neue 1-sulfonyl-4-amino-pyridiniumsalze und verfahren zu ihrer herstellung |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5251372A (enExample) |
| BE (1) | BE847061A (enExample) |
| DE (1) | DE2547590A1 (enExample) |
| FR (1) | FR2328699A1 (enExample) |
| GB (1) | GB1537461A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4787493B2 (ja) * | 2004-12-24 | 2011-10-05 | 健治 石川 | 精密熱かしめ装置 |
| US9051248B2 (en) * | 2009-08-10 | 2015-06-09 | Bhi Limited Partnership | Methods, compounds, and compositions for delivering 1,3-propanedisulfonic acid |
-
1975
- 1975-10-24 DE DE19752547590 patent/DE2547590A1/de not_active Withdrawn
-
1976
- 1976-10-08 BE BE1007681A patent/BE847061A/xx unknown
- 1976-10-18 GB GB4315976A patent/GB1537461A/en not_active Expired
- 1976-10-22 FR FR7631930A patent/FR2328699A1/fr active Granted
- 1976-10-22 JP JP12637476A patent/JPS5251372A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1537461A (en) | 1978-12-29 |
| JPS5251372A (en) | 1977-04-25 |
| BE847061A (nl) | 1977-04-08 |
| FR2328699A1 (fr) | 1977-05-20 |
| FR2328699B1 (enExample) | 1982-03-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |