DE3107583A1 - Innere salze von sulfooxytriazinium-, sulfooxypyrimidinium- und sulfooxypyridinium-hydroxid - Google Patents
Innere salze von sulfooxytriazinium-, sulfooxypyrimidinium- und sulfooxypyridinium-hydroxidInfo
- Publication number
- DE3107583A1 DE3107583A1 DE19813107583 DE3107583A DE3107583A1 DE 3107583 A1 DE3107583 A1 DE 3107583A1 DE 19813107583 DE19813107583 DE 19813107583 DE 3107583 A DE3107583 A DE 3107583A DE 3107583 A1 DE3107583 A1 DE 3107583A1
- Authority
- DE
- Germany
- Prior art keywords
- sulfooxy
- hydroxide
- inner salt
- diamino
- amino
- 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.)
- Granted
Links
- XKUGNOSPEPNWNB-UHFFFAOYSA-N [O-]S(O[N+]1=CC=CN=N1)(=O)=O Chemical class [O-]S(O[N+]1=CC=CN=N1)(=O)=O XKUGNOSPEPNWNB-UHFFFAOYSA-N 0.000 title description 4
- FKWJWULESKQADD-UHFFFAOYSA-N pyridin-1-ium-1-yl hydrogen sulfate;hydroxide Chemical class [OH-].OS(=O)(=O)O[N+]1=CC=CC=C1 FKWJWULESKQADD-UHFFFAOYSA-N 0.000 title description 4
- MLATXMYELRPHEP-UHFFFAOYSA-N [O-]S(O[N+]1=CC=CN=C1)(=O)=O Chemical class [O-]S(O[N+]1=CC=CN=C1)(=O)=O MLATXMYELRPHEP-UHFFFAOYSA-N 0.000 title description 3
- 150000003839 salts Chemical class 0.000 claims description 146
- -1 and vice versa Chemical group 0.000 claims description 121
- 150000001875 compounds Chemical class 0.000 claims description 55
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 5
- WGQIDCOHKCCLLX-UHFFFAOYSA-N (2-amino-6-methyl-4-pyrrolidin-1-ylpyrimidin-1-ium-1-yl) hydrogen sulfate;hydroxide Chemical compound [OH-].NC1=[N+](OS(O)(=O)=O)C(C)=CC(N2CCCC2)=N1 WGQIDCOHKCCLLX-UHFFFAOYSA-N 0.000 claims description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- OLCAPZGCVMBTID-UHFFFAOYSA-N [2,6-diamino-4-[bis(prop-2-enyl)amino]-1,3,5-triazin-1-ium-1-yl] hydrogen sulfate;hydroxide Chemical compound [OH-].NC1=NC(N(CC=C)CC=C)=NC(N)=[N+]1OS(O)(=O)=O OLCAPZGCVMBTID-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- 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 claims description 3
- HJFHFZKOWGESRO-UHFFFAOYSA-N (2-amino-6-methyl-4-morpholin-4-ylpyrimidin-1-ium-1-yl) hydrogen sulfate;hydroxide Chemical compound [OH-].NC1=[N+](OS(O)(=O)=O)C(C)=CC(N2CCOCC2)=N1 HJFHFZKOWGESRO-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 126
- 239000000203 mixture Substances 0.000 description 56
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 13
- FBPINGSGHKXIQA-UHFFFAOYSA-N 2-amino-3-(2-carboxyethylsulfanyl)propanoic acid Chemical compound OC(=O)C(N)CSCCC(O)=O FBPINGSGHKXIQA-UHFFFAOYSA-N 0.000 description 11
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical compound CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 10
- 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 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 150000003230 pyrimidines Chemical class 0.000 description 6
- 206010020802 Hypertensive crisis Diseases 0.000 description 5
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 206010019280 Heart failures Diseases 0.000 description 4
- 206010020772 Hypertension Diseases 0.000 description 4
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 4
- 150000003222 pyridines Chemical class 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 150000003918 triazines Chemical class 0.000 description 4
- 206010007559 Cardiac failure congestive Diseases 0.000 description 3
- 206010017711 Gangrene Diseases 0.000 description 3
- ZFMITUMMTDLWHR-UHFFFAOYSA-N Minoxidil Chemical compound NC1=[N+]([O-])C(N)=CC(N2CCCCC2)=N1 ZFMITUMMTDLWHR-UHFFFAOYSA-N 0.000 description 3
- 208000018262 Peripheral vascular disease Diseases 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- YJERJOFXWLQPRV-UHFFFAOYSA-N (2,6-diamino-4-piperidin-1-yl-1,3,5-triazin-1-ium-1-yl) hydrogen sulfate;hydroxide Chemical compound [OH-].NC1=[N+](OS(O)(=O)=O)C(N)=NC(N2CCCCC2)=N1 YJERJOFXWLQPRV-UHFFFAOYSA-N 0.000 description 2
- XBKYXKRWSHMDMZ-UHFFFAOYSA-N (2,6-diamino-4-piperidin-1-ylpyridin-1-ium-1-yl) hydrogen sulfate;hydroxide Chemical compound [OH-].NC1=[N+](OS(O)(=O)=O)C(N)=CC(N2CCCCC2)=C1 XBKYXKRWSHMDMZ-UHFFFAOYSA-N 0.000 description 2
- GVOBHHNCKRTUTC-UHFFFAOYSA-N (2,6-diamino-4-piperidin-1-ylpyrimidin-1-ium-1-yl) hydrogen sulfate;hydroxide Chemical compound [OH-].NC1=[N+](OS(O)(=O)=O)C(N)=CC(N2CCCCC2)=N1 GVOBHHNCKRTUTC-UHFFFAOYSA-N 0.000 description 2
- KAPMNIPMIYWLJH-UHFFFAOYSA-N (2,6-diamino-4-thiomorpholin-4-ylpyrimidin-1-ium-1-yl) hydrogen sulfate;hydroxide Chemical compound [OH-].NC1=[N+](OS(O)(=O)=O)C(N)=CC(N2CCSCC2)=N1 KAPMNIPMIYWLJH-UHFFFAOYSA-N 0.000 description 2
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SZWGIPTXMNCPAM-UHFFFAOYSA-N [2,6-diamino-4-(2,5-dihydropyrrol-1-yl)pyrimidin-1-ium-1-yl] hydrogen sulfate;hydroxide Chemical compound [OH-].NC1=[N+](OS(O)(=O)=O)C(N)=CC(N2CC=CC2)=N1 SZWGIPTXMNCPAM-UHFFFAOYSA-N 0.000 description 2
- UMPSHBQRDOOIPL-UHFFFAOYSA-N [2,6-diamino-4-(2-phenylethylamino)pyrimidin-1-ium-1-yl] hydrogen sulfate;hydroxide Chemical compound [OH-].NC1=[N+](OS(O)(=O)=O)C(N)=CC(NCCC=2C=CC=CC=2)=N1 UMPSHBQRDOOIPL-UHFFFAOYSA-N 0.000 description 2
- YFHNIPMFAYXLCR-UHFFFAOYSA-N [2,6-diamino-4-(hex-3-enylamino)pyridin-1-ium-1-yl] hydrogen sulfate;hydroxide Chemical compound [OH-].CCC=CCCNC1=CC(N)=[N+](OS(O)(=O)=O)C(N)=C1 YFHNIPMFAYXLCR-UHFFFAOYSA-N 0.000 description 2
- DDYNJMAECXIKBJ-UHFFFAOYSA-N [2,6-diamino-4-(oct-2-enylamino)-1,3,5-triazin-1-ium-1-yl] hydrogen sulfate;hydroxide Chemical compound [OH-].CCCCCC=CCNC1=NC(N)=[N+](OS(O)(=O)=O)C(N)=N1 DDYNJMAECXIKBJ-UHFFFAOYSA-N 0.000 description 2
- OHNONQQRMJKGIV-UHFFFAOYSA-N [2,6-diamino-4-[bis(prop-2-enyl)amino]pyrimidin-1-ium-1-yl] hydrogen sulfate;hydroxide Chemical compound [OH-].NC1=CC(N(CC=C)CC=C)=NC(N)=[N+]1OS(O)(=O)=O OHNONQQRMJKGIV-UHFFFAOYSA-N 0.000 description 2
- RNGRRUTUCVKNAK-UHFFFAOYSA-N [2-amino-4-(4-ethylpiperazin-1-yl)-6-methylpyridin-1-ium-1-yl] hydrogen sulfate;hydroxide Chemical compound [OH-].C1CN(CC)CCN1C1=CC(C)=[N+](OS(O)(=O)=O)C(N)=C1 RNGRRUTUCVKNAK-UHFFFAOYSA-N 0.000 description 2
- WXZCSJTWZMYIGE-UHFFFAOYSA-N [2-amino-4-(6-methyl-2,3,4,7-tetrahydroazepin-1-yl)-6-(propan-2-ylamino)pyridin-1-ium-1-yl] hydrogen sulfate;hydroxide Chemical compound [OH-].NC1=[N+](OS(O)(=O)=O)C(NC(C)C)=CC(N2CC(C)=CCCC2)=C1 WXZCSJTWZMYIGE-UHFFFAOYSA-N 0.000 description 2
- QCXSUEBDJNZHRD-UHFFFAOYSA-N [2-amino-4-[ethyl(methyl)amino]-6-(propylamino)-1,3,5-triazin-1-ium-1-yl] hydrogen sulfate;hydroxide Chemical compound [OH-].CCCNC1=NC(N(C)CC)=NC(N)=[N+]1OS(O)(=O)=O QCXSUEBDJNZHRD-UHFFFAOYSA-N 0.000 description 2
- LSJCVLWEOVLJRL-UHFFFAOYSA-N [2-amino-6-(methylamino)-4-thiomorpholin-4-ylpyridin-1-ium-1-yl] hydrogen sulfate;hydroxide Chemical compound [OH-].NC1=[N+](OS(O)(=O)=O)C(NC)=CC(N2CCSCC2)=C1 LSJCVLWEOVLJRL-UHFFFAOYSA-N 0.000 description 2
- 229940030600 antihypertensive agent Drugs 0.000 description 2
- 239000002220 antihypertensive agent Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000005394 methallyl group Chemical group 0.000 description 2
- YYHPEVZFVMVUNJ-UHFFFAOYSA-N n,n-diethylethanamine;sulfur trioxide Chemical compound O=S(=O)=O.CCN(CC)CC YYHPEVZFVMVUNJ-UHFFFAOYSA-N 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 2
- LSYJHRREPKXURZ-UHFFFAOYSA-N pyrimidine;hydrate Chemical compound O.C1=CN=CN=C1 LSYJHRREPKXURZ-UHFFFAOYSA-N 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 229940124549 vasodilator Drugs 0.000 description 2
- 239000003071 vasodilator agent Substances 0.000 description 2
- KLOBOMDGMQHPJD-UHFFFAOYSA-N (2,6-diamino-4-morpholin-4-yl-1,3,5-triazin-1-ium-1-yl) hydrogen sulfate;hydroxide Chemical compound [OH-].NC1=[N+](OS(O)(=O)=O)C(N)=NC(N2CCOCC2)=N1 KLOBOMDGMQHPJD-UHFFFAOYSA-N 0.000 description 1
- PHZXDFWGWNASNT-UHFFFAOYSA-N (2,6-diamino-4-morpholin-4-ylpyridin-1-ium-1-yl) hydrogen sulfate;hydroxide Chemical compound [OH-].NC1=[N+](OS(O)(=O)=O)C(N)=CC(N2CCOCC2)=C1 PHZXDFWGWNASNT-UHFFFAOYSA-N 0.000 description 1
- HGZFPSRKFXRKCR-UHFFFAOYSA-N (2,6-diamino-4-pyrrolidin-1-ylpyridin-1-ium-1-yl) hydrogen sulfate;hydroxide Chemical compound [OH-].NC1=[N+](OS(O)(=O)=O)C(N)=CC(N2CCCC2)=C1 HGZFPSRKFXRKCR-UHFFFAOYSA-N 0.000 description 1
- WBFHOJUQLZHKDZ-UHFFFAOYSA-N (2,6-diamino-4-thiomorpholin-4-yl-1,3,5-triazin-1-ium-1-yl) hydrogen sulfate;hydroxide Chemical compound [OH-].NC1=[N+](OS(O)(=O)=O)C(N)=NC(N2CCSCC2)=N1 WBFHOJUQLZHKDZ-UHFFFAOYSA-N 0.000 description 1
- WAXSLIMHPATHNP-UHFFFAOYSA-N (2,6-diamino-4-thiomorpholin-4-ylpyridin-1-ium-1-yl) hydrogen sulfate;hydroxide Chemical compound [OH-].NC1=[N+](OS(O)(=O)=O)C(N)=CC(N2CCSCC2)=C1 WAXSLIMHPATHNP-UHFFFAOYSA-N 0.000 description 1
- VDLPGVTZWOHXHL-UHFFFAOYSA-N (2-amino-4-morpholin-4-yl-6-propan-2-ylpyridin-1-ium-1-yl) hydrogen sulfate;hydroxide Chemical compound [OH-].NC1=[N+](OS(O)(=O)=O)C(C(C)C)=CC(N2CCOCC2)=C1 VDLPGVTZWOHXHL-UHFFFAOYSA-N 0.000 description 1
- YWSBZHYFKKCSLZ-UHFFFAOYSA-N (2-amino-6-ethyl-4-piperidin-1-ylpyridin-1-ium-1-yl) hydrogen sulfate;hydroxide Chemical compound [OH-].NC1=[N+](OS(O)(=O)=O)C(CC)=CC(N2CCCCC2)=C1 YWSBZHYFKKCSLZ-UHFFFAOYSA-N 0.000 description 1
- JFUZJXIIZNHAKU-UHFFFAOYSA-N (2-amino-6-ethyl-4-piperidin-1-ylpyrimidin-1-ium-1-yl) hydrogen sulfate;hydroxide Chemical compound [OH-].NC1=[N+](OS(O)(=O)=O)C(CC)=CC(N2CCCCC2)=N1 JFUZJXIIZNHAKU-UHFFFAOYSA-N 0.000 description 1
- ITQQVWCXPUNTFG-UHFFFAOYSA-N (2-amino-6-methyl-4-piperidin-1-yl-1,3,5-triazin-1-ium-1-yl) hydrogen sulfate;hydroxide Chemical compound [OH-].NC1=[N+](OS(O)(=O)=O)C(C)=NC(N2CCCCC2)=N1 ITQQVWCXPUNTFG-UHFFFAOYSA-N 0.000 description 1
- QTPVEIPRUJMMLF-UHFFFAOYSA-N (2-amino-6-methyl-4-piperidin-1-ylpyridin-1-ium-1-yl) hydrogen sulfate;hydroxide Chemical compound [OH-].NC1=[N+](OS(O)(=O)=O)C(C)=CC(N2CCCCC2)=C1 QTPVEIPRUJMMLF-UHFFFAOYSA-N 0.000 description 1
- IAOXRRMNSZIOEH-UHFFFAOYSA-N (2-amino-6-methyl-4-piperidin-1-ylpyrimidin-1-ium-1-yl) hydrogen sulfate;hydroxide Chemical compound [OH-].NC1=[N+](OS(O)(=O)=O)C(C)=CC(N2CCCCC2)=N1 IAOXRRMNSZIOEH-UHFFFAOYSA-N 0.000 description 1
- QGSCSUKRZKFYEV-UHFFFAOYSA-N (2-amino-6-methyl-4-pyrrolidin-1-ylpyridin-1-ium-1-yl) hydrogen sulfate;hydroxide Chemical compound [OH-].NC1=[N+](OS(O)(=O)=O)C(C)=CC(N2CCCC2)=C1 QGSCSUKRZKFYEV-UHFFFAOYSA-N 0.000 description 1
- RGWMGFZQDZLLQE-UHFFFAOYSA-N (2-amino-6-octyl-4-pyrrolidin-1-ylpyrimidin-1-ium-1-yl) hydrogen sulfate;hydroxide Chemical compound [OH-].NC1=[N+](OS(O)(=O)=O)C(CCCCCCCC)=CC(N2CCCC2)=N1 RGWMGFZQDZLLQE-UHFFFAOYSA-N 0.000 description 1
- AMFXGIRPBVMGFA-UHFFFAOYSA-N 1,3,5-triazin-1-ium-1-yl hydrogen sulfate hydroxide Chemical compound [OH-].S(=O)(=O)(O)O[N+]1=CN=CN=C1 AMFXGIRPBVMGFA-UHFFFAOYSA-N 0.000 description 1
- 150000000182 1,3,5-triazines Chemical class 0.000 description 1
- 125000006065 1,3-dimethyl-2-butenyl group Chemical group 0.000 description 1
- ZPEGLCWNMPVGQE-UHFFFAOYSA-N 1-hydroxy-6-imino-4-piperidin-1-ylpyridin-2-amine Chemical compound N=C1N(O)C(N)=CC(N2CCCCC2)=C1 ZPEGLCWNMPVGQE-UHFFFAOYSA-N 0.000 description 1
- 125000006028 1-methyl-2-butenyl group Chemical group 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000006069 2,3-dimethyl-2-butenyl group Chemical group 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006029 2-methyl-2-butenyl group Chemical group 0.000 description 1
- 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 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- AJVXORIUPJGFTR-UHFFFAOYSA-N 3-hydroxy-2-imino-6-(4-methylpiperazin-1-yl)pyrimidin-4-amine Chemical compound C1CN(C)CCN1C1=NC(=N)N(O)C(N)=C1 AJVXORIUPJGFTR-UHFFFAOYSA-N 0.000 description 1
- 125000006051 4-methyl-2-pentenyl group Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
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- XEYBHCRIKKKOSS-UHFFFAOYSA-N disodium;azanylidyneoxidanium;iron(2+);pentacyanide Chemical compound [Na+].[Na+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].[O+]#N XEYBHCRIKKKOSS-UHFFFAOYSA-N 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000002445 nipple Anatomy 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012521 purified sample Substances 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- OENLEHTYJXMVBG-UHFFFAOYSA-N pyridine;hydrate Chemical compound [OH-].C1=CC=[NH+]C=C1 OENLEHTYJXMVBG-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229940083618 sodium nitroprusside Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 238000002424 x-ray crystallography Methods 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- 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
- C07D239/48—Two nitrogen atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/70—Other substituted melamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/128,995 US4287338A (en) | 1980-03-10 | 1980-03-10 | Sulfooxy-pyrimidinium, -pyridinium, and -triazinium hydroxide inner salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3107583A1 true DE3107583A1 (de) | 1982-01-07 |
| DE3107583C2 DE3107583C2 (enExample) | 1989-11-02 |
Family
ID=22437996
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813107583 Granted DE3107583A1 (de) | 1980-03-10 | 1981-02-27 | Innere salze von sulfooxytriazinium-, sulfooxypyrimidinium- und sulfooxypyridinium-hydroxid |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4287338A (enExample) |
| JP (1) | JPS56150066A (enExample) |
| AU (1) | AU536166B2 (enExample) |
| BE (1) | BE887850A (enExample) |
| CA (1) | CA1154761A (enExample) |
| CH (1) | CH645626A5 (enExample) |
| DE (1) | DE3107583A1 (enExample) |
| FI (1) | FI70410C (enExample) |
| FR (1) | FR2477541A1 (enExample) |
| GB (1) | GB2071092B (enExample) |
| HK (1) | HK98088A (enExample) |
| IT (1) | IT1142667B (enExample) |
| NL (1) | NL8101114A (enExample) |
| SE (1) | SE448876B (enExample) |
| ZA (1) | ZA811057B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5183817A (en) * | 1981-02-17 | 1993-02-02 | Bazzano Gail S | Combinations of retinoids and minoxidil-type compounds for hair growth |
| US5514672A (en) * | 1981-02-17 | 1996-05-07 | Bazzano; Gail S. | Use of retinoids and compositions containing same for hair growth |
| US4532240A (en) * | 1982-09-09 | 1985-07-30 | Warner-Lambert Company | Diaminopyrimidines |
| EP0210227B1 (en) * | 1985-01-25 | 1990-05-02 | The Upjohn Company | Pyrimidine sulfates for hair growth |
| FR2590897B1 (fr) * | 1985-12-06 | 1988-02-19 | Kemyos Bio Medical Research Sr | Nouveaux derives de 6 amino 1,2-dihydro-1-hydroxy-2-imino-pyrimidine, leur procede de preparation et compositions cosmetiques les renfermant |
| US4927626A (en) * | 1988-10-28 | 1990-05-22 | Devillez Richard L | Method for enhancement of unguis growth |
| FR2651122B1 (fr) * | 1989-08-29 | 1994-10-28 | Oreal | Compositions destinees a etre utilisees pour freiner la chute des cheveux et pour induire et stimuler leur croissance, contenant des derives de l'amino-2 pyrimidine oxyde-3 et nouveaux composes derives de l'amino-2 pyrimidine oxyde-3. |
| GB8929022D0 (en) * | 1989-12-22 | 1990-02-28 | Ici Plc | Diazine derivatives |
| GB9008818D0 (en) * | 1990-04-19 | 1990-06-13 | Ici Plc | Amine derivatives |
| EP0557301B1 (en) * | 1990-11-14 | 1995-03-22 | The Upjohn Company | 5-fluoro-2,4,6-pyrimidinetriamine compounds for preventing hair loss |
| 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. |
| FR2677884B1 (fr) * | 1991-06-20 | 1993-07-09 | Oreal | Composition pour freiner la chute des cheveux a base de pyrimidines n-oxyde trisubstitues ou leurs derives sulfoconjugues, nouveaux composes pyrimidines n-oxyde ou leurs derives sulfoconjugues. |
| AU8681498A (en) * | 1997-08-01 | 1999-02-22 | Reilly Industries, Inc. | Supernucleophilic 4-substituted-pyridine catalysts, and processes useful for preparing same |
| US7705010B2 (en) * | 2005-02-22 | 2010-04-27 | Cedars-Sinai Medical Center | Use of minoxidil sulfate as an anti-tumor drug |
| CL2008000467A1 (es) * | 2007-02-14 | 2008-08-22 | Janssen Pharmaceutica Nv | Compuestos derivados de 2-aminopirimidina, moduladores del receptor histamina h4; su procedimiento de preparacion; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar un trastorno inflamatorio seleccionado de alegia, asma |
| WO2008122378A1 (en) * | 2007-04-04 | 2008-10-16 | Ucb Pharma, S.A. | Novel pyridine derivatives, processes for preparing them, pharmaceutical compositions thereof |
| US8470833B2 (en) | 2009-12-15 | 2013-06-25 | Mcneil-Ppc, Inc. | Hair growth and/or regrowth compositions |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3270014A (en) * | 1965-07-01 | 1966-08-30 | Upjohn Co | 1, 2-dihydro-1-hydroxy-1, 3, 5-triazines |
| NL6615385A (enExample) * | 1965-11-01 | 1967-05-02 | ||
| FR1513739A (fr) * | 1966-02-21 | 1968-02-16 | Upjohn Co | Dérivés pyrimidiniques |
| US3973016A (en) * | 1974-08-05 | 1976-08-03 | Warner-Lambert Company | Blood pressure reducing hydroxypyrimidines |
| US4021562A (en) * | 1975-12-08 | 1977-05-03 | Mead Johnson & Company | 4-Tertiary-amino-2,6-diaminopyridine 1-oxides |
-
1980
- 1980-03-10 US US06/128,995 patent/US4287338A/en not_active Expired - Lifetime
-
1981
- 1981-02-11 CA CA000370601A patent/CA1154761A/en not_active Expired
- 1981-02-17 AU AU67371/81A patent/AU536166B2/en not_active Ceased
- 1981-02-17 ZA ZA00811057A patent/ZA811057B/xx unknown
- 1981-02-26 CH CH130681A patent/CH645626A5/de not_active IP Right Cessation
- 1981-02-27 DE DE19813107583 patent/DE3107583A1/de active Granted
- 1981-03-04 FI FI810681A patent/FI70410C/fi not_active IP Right Cessation
- 1981-03-05 GB GB8106936A patent/GB2071092B/en not_active Expired
- 1981-03-05 SE SE8101421A patent/SE448876B/sv not_active IP Right Cessation
- 1981-03-09 BE BE0/204051A patent/BE887850A/fr not_active IP Right Cessation
- 1981-03-09 FR FR8104662A patent/FR2477541A1/fr active Granted
- 1981-03-09 NL NL8101114A patent/NL8101114A/nl not_active Application Discontinuation
- 1981-03-09 IT IT47976/81A patent/IT1142667B/it active
- 1981-03-10 JP JP3448481A patent/JPS56150066A/ja active Granted
-
1988
- 1988-12-01 HK HK980/88A patent/HK98088A/xx unknown
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3270014A (en) * | 1965-07-01 | 1966-08-30 | Upjohn Co | 1, 2-dihydro-1-hydroxy-1, 3, 5-triazines |
| NL6615385A (enExample) * | 1965-11-01 | 1967-05-02 | ||
| FR1513739A (fr) * | 1966-02-21 | 1968-02-16 | Upjohn Co | Dérivés pyrimidiniques |
| US3973016A (en) * | 1974-08-05 | 1976-08-03 | Warner-Lambert Company | Blood pressure reducing hydroxypyrimidines |
| US4021562A (en) * | 1975-12-08 | 1977-05-03 | Mead Johnson & Company | 4-Tertiary-amino-2,6-diaminopyridine 1-oxides |
| US4080500A (en) * | 1975-12-08 | 1978-03-21 | Mead Johnson & Company | 4-Tertiary-amino-2,6-diaminopyridine 1-oxides |
Non-Patent Citations (1)
| Title |
|---|
| Chem. of Heterocycl.Compds., Pyridine and its Derivatives, Suppl. II, Wiley and Sons, 1974, S. 103 * |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA811057B (en) | 1982-03-31 |
| BE887850A (fr) | 1981-09-09 |
| SE448876B (sv) | 1987-03-23 |
| NL8101114A (nl) | 1981-10-01 |
| JPH0145467B2 (enExample) | 1989-10-03 |
| FI70410B (fi) | 1986-03-27 |
| SE8101421L (sv) | 1981-09-11 |
| FR2477541B1 (enExample) | 1984-06-01 |
| FI70410C (fi) | 1986-09-19 |
| JPS56150066A (en) | 1981-11-20 |
| IT1142667B (it) | 1986-10-15 |
| US4287338A (en) | 1981-09-01 |
| AU536166B2 (en) | 1984-04-19 |
| AU6737181A (en) | 1981-09-17 |
| IT8147976A0 (it) | 1981-03-09 |
| DE3107583C2 (enExample) | 1989-11-02 |
| CA1154761A (en) | 1983-10-04 |
| GB2071092B (en) | 1983-09-07 |
| HK98088A (en) | 1988-12-09 |
| FR2477541A1 (fr) | 1981-09-11 |
| CH645626A5 (de) | 1984-10-15 |
| GB2071092A (en) | 1981-09-16 |
| FI810681L (fi) | 1981-09-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: HENKEL, G., DR.PHIL. FEILER, L., DR.RER.NAT. HAENZ |
|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |