DE2406200A1 - Verfahren zur herstellung von neuen 3,6-diamino-3,4-dihydropyridonen-2 und ihre verwendung als arzneimittel - Google Patents
Verfahren zur herstellung von neuen 3,6-diamino-3,4-dihydropyridonen-2 und ihre verwendung als arzneimittelInfo
- Publication number
- DE2406200A1 DE2406200A1 DE19742406200 DE2406200A DE2406200A1 DE 2406200 A1 DE2406200 A1 DE 2406200A1 DE 19742406200 DE19742406200 DE 19742406200 DE 2406200 A DE2406200 A DE 2406200A DE 2406200 A1 DE2406200 A1 DE 2406200A1
- Authority
- DE
- Germany
- Prior art keywords
- dihydropyridone
- radical
- alkyl
- diamino
- formula
- 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- Withdrawn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 10
- 230000008569 process Effects 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 229940126601 medicinal product Drugs 0.000 title description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- -1 Alkenyl radical Chemical class 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- QHJJSLUZWHFHTK-UHFFFAOYSA-N 3-amino-3-azaniumylidenepropanoate Chemical class NC(=N)CC(O)=O QHJJSLUZWHFHTK-UHFFFAOYSA-N 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- IYFFBKXNBQQSAA-UHFFFAOYSA-N 3,6-diamino-3,4-dihydro-1h-pyridin-2-one Chemical compound NC1CC=C(N)NC1=O IYFFBKXNBQQSAA-UHFFFAOYSA-N 0.000 claims 1
- 235000019441 ethanol Nutrition 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000009835 boiling Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- HSDKTLKBDJXJQU-UHFFFAOYSA-N ethyl 3-amino-3-iminopropanoate Chemical compound CCOC(=O)CC(N)=N HSDKTLKBDJXJQU-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 150000001409 amidines Chemical group 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 230000002792 vascular Effects 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000002220 antihypertensive agent Substances 0.000 description 2
- 229940030600 antihypertensive agent Drugs 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 210000003748 coronary sinus Anatomy 0.000 description 2
- 210000004351 coronary vessel Anatomy 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011435 rock Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 210000002460 smooth muscle Anatomy 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KCOPAESEGCGTKM-UHFFFAOYSA-N 1,3-oxazol-4-one Chemical compound O=C1COC=N1 KCOPAESEGCGTKM-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZPOODPZCZLCUAN-UHFFFAOYSA-N 3,4-dihydro-1h-pyridin-2-one Chemical compound O=C1CCC=CN1 ZPOODPZCZLCUAN-UHFFFAOYSA-N 0.000 description 1
- 206010001497 Agitation Diseases 0.000 description 1
- 240000002470 Amphicarpaea bracteata Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 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 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- NTDQSSGUDPPZRP-UHFFFAOYSA-N butyl 3-amino-3-iminopropanoate Chemical compound CCCCOC(=O)CC(N)=N NTDQSSGUDPPZRP-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- VUWPIBNKJSEYIN-UHFFFAOYSA-N diethyl 2-benzylidenepropanedioate Chemical compound CCOC(=O)C(C(=O)OCC)=CC1=CC=CC=C1 VUWPIBNKJSEYIN-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- YPMPTULBFPFSEQ-PLNGDYQASA-N ethyl (z)-3-aminobut-2-enoate Chemical compound CCOC(=O)\C=C(\C)N YPMPTULBFPFSEQ-PLNGDYQASA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- ZPIBCEJYARVVQI-UHFFFAOYSA-N methyl 3-amino-3-iminopropanoate Chemical compound COC(=O)CC(N)=N ZPIBCEJYARVVQI-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- HZYFTIHNZZQVFR-UHFFFAOYSA-N prop-2-ynyl 3-amino-3-iminopropanoate Chemical compound NC(=N)CC(=O)OCC#C HZYFTIHNZZQVFR-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- ZVWPDJQEKLAOHT-UHFFFAOYSA-N propan-2-yl 3-amino-3-iminopropanoate Chemical compound CC(C)OC(=O)CC(N)=N ZVWPDJQEKLAOHT-UHFFFAOYSA-N 0.000 description 1
- LDCBBNBRKMDBSZ-UHFFFAOYSA-N propyl 3-amino-3-iminopropanoate Chemical compound CCCOC(=O)CC(N)=N LDCBBNBRKMDBSZ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Stabilization Of Oscillater, Synchronisation, Frequency Synthesizers (AREA)
Priority Applications (22)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742406200 DE2406200A1 (de) | 1974-02-09 | 1974-02-09 | Verfahren zur herstellung von neuen 3,6-diamino-3,4-dihydropyridonen-2 und ihre verwendung als arzneimittel |
| US05/545,299 US4001259A (en) | 1974-02-09 | 1975-01-30 | 3,6-diamino-3,4-dihydro-2-pyridones |
| CA219,243A CA1049525A (en) | 1974-02-09 | 1975-02-03 | 3,6-diamino-3,4-dihydro-2-pyridones and their production |
| AU77865/75A AU484385B2 (en) | 1974-02-09 | 1975-02-04 | 3, 6-diamino-3, 4-dihydro-2-pyridones and their use as medicaments |
| FI750325A FI750325A7 (en:Method) | 1974-02-09 | 1975-02-06 | |
| BE153109A BE825246A (fr) | 1974-02-09 | 1975-02-06 | Nouvelles 3,6-diamino-3,4-dihydropyridones-2, leur procede de preparation et medicament les contenant |
| IL46578A IL46578A (en) | 1974-02-09 | 1975-02-06 | 3,6-diamino-3,4-dihydro-2-pyridones their preparation and pharmaceutical compositions containing them |
| LU71812A LU71812A1 (en:Method) | 1974-02-09 | 1975-02-07 | |
| SE7501389A SE402588B (sv) | 1974-02-09 | 1975-02-07 | Sett att framstella nya 3,6-diamino-3,4-dihydropyridoner-2 |
| AT94875A AT339904B (de) | 1974-02-09 | 1975-02-07 | Verfahren zur herstellung von neuen 3,6-diamino- 3,4 -dihydropyridonen-2 |
| CH150375A CH605753A5 (en:Method) | 1974-02-09 | 1975-02-07 | |
| ES434547A ES434547A1 (es) | 1974-02-09 | 1975-02-07 | Procedimiento para la obtencion de 3, 6-diamino-3, 4-dihi- dropiridonas-2. |
| NL7501499A NL7501499A (nl) | 1974-02-09 | 1975-02-07 | Werkwijze voor het bereiden van dihydropyridonen, ijze voor het bereiden van geneesmiddelen de gevormde geneesmiddelen. |
| ZA00750789A ZA75789B (en) | 1974-02-09 | 1975-02-07 | 3,6-diamino-3,4-dihydro-2-pyridones and their use as medicaments |
| HUBA3202A HU168593B (en:Method) | 1974-02-09 | 1975-02-07 | |
| JP50015501A JPS50108269A (en:Method) | 1974-02-09 | 1975-02-07 | |
| DD184074A DD118426A5 (en:Method) | 1974-02-09 | 1975-02-07 | |
| FR7503896A FR2260346B1 (en:Method) | 1974-02-09 | 1975-02-07 | |
| GB531375A GB1444879A (en) | 1974-02-09 | 1975-02-07 | 3-acylamino-6-amino-3,4-dihydro-2-pyridones and their use as medicaments |
| IE246/75A IE40588B1 (en) | 1974-02-09 | 1975-02-07 | 3-acylamino-6-amino-3,4-dihydro-2-pyridones and their use as medicaments |
| DK44375*#A DK44375A (en:Method) | 1974-02-09 | 1975-02-07 | |
| PL1975177899A PL92432B1 (en:Method) | 1974-02-09 | 1975-02-08 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742406200 DE2406200A1 (de) | 1974-02-09 | 1974-02-09 | Verfahren zur herstellung von neuen 3,6-diamino-3,4-dihydropyridonen-2 und ihre verwendung als arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2406200A1 true DE2406200A1 (de) | 1975-08-14 |
Family
ID=5906985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742406200 Withdrawn DE2406200A1 (de) | 1974-02-09 | 1974-02-09 | Verfahren zur herstellung von neuen 3,6-diamino-3,4-dihydropyridonen-2 und ihre verwendung als arzneimittel |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4001259A (en:Method) |
| JP (1) | JPS50108269A (en:Method) |
| AT (1) | AT339904B (en:Method) |
| BE (1) | BE825246A (en:Method) |
| CA (1) | CA1049525A (en:Method) |
| CH (1) | CH605753A5 (en:Method) |
| DD (1) | DD118426A5 (en:Method) |
| DE (1) | DE2406200A1 (en:Method) |
| DK (1) | DK44375A (en:Method) |
| ES (1) | ES434547A1 (en:Method) |
| FI (1) | FI750325A7 (en:Method) |
| FR (1) | FR2260346B1 (en:Method) |
| GB (1) | GB1444879A (en:Method) |
| HU (1) | HU168593B (en:Method) |
| IE (1) | IE40588B1 (en:Method) |
| IL (1) | IL46578A (en:Method) |
| LU (1) | LU71812A1 (en:Method) |
| NL (1) | NL7501499A (en:Method) |
| PL (1) | PL92432B1 (en:Method) |
| SE (1) | SE402588B (en:Method) |
| ZA (1) | ZA75789B (en:Method) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5232216A (en) * | 1975-09-05 | 1977-03-11 | Matsushita Electric Ind Co Ltd | Ghost eliminating equipment |
| DE2706977A1 (de) * | 1977-02-18 | 1978-08-24 | Hoechst Ag | Benzoesaeuren und deren derivate sowie verfahren zu ihrer herstellung |
| US5725789A (en) * | 1995-03-31 | 1998-03-10 | Minnesota Mining And Manufacturing Company | Aqueous oil and water repellent compositions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3862161A (en) * | 1970-01-24 | 1975-01-21 | Bayer Ag | 4-pyridyl substituted 1,4-dihydropyridines |
| US3887558A (en) * | 1972-03-06 | 1975-06-03 | Bayer Ag | Process for producing 2,6-diamino -1,4- dihydro-3,5-pyridine-dicarboxylates and derivatives thereof |
-
1974
- 1974-02-09 DE DE19742406200 patent/DE2406200A1/de not_active Withdrawn
-
1975
- 1975-01-30 US US05/545,299 patent/US4001259A/en not_active Expired - Lifetime
- 1975-02-03 CA CA219,243A patent/CA1049525A/en not_active Expired
- 1975-02-06 FI FI750325A patent/FI750325A7/fi not_active Application Discontinuation
- 1975-02-06 IL IL46578A patent/IL46578A/en unknown
- 1975-02-06 BE BE153109A patent/BE825246A/xx unknown
- 1975-02-07 DK DK44375*#A patent/DK44375A/da unknown
- 1975-02-07 SE SE7501389A patent/SE402588B/xx unknown
- 1975-02-07 GB GB531375A patent/GB1444879A/en not_active Expired
- 1975-02-07 FR FR7503896A patent/FR2260346B1/fr not_active Expired
- 1975-02-07 NL NL7501499A patent/NL7501499A/xx not_active Application Discontinuation
- 1975-02-07 ZA ZA00750789A patent/ZA75789B/xx unknown
- 1975-02-07 CH CH150375A patent/CH605753A5/xx not_active IP Right Cessation
- 1975-02-07 IE IE246/75A patent/IE40588B1/xx unknown
- 1975-02-07 ES ES434547A patent/ES434547A1/es not_active Expired
- 1975-02-07 AT AT94875A patent/AT339904B/de not_active IP Right Cessation
- 1975-02-07 LU LU71812A patent/LU71812A1/xx unknown
- 1975-02-07 HU HUBA3202A patent/HU168593B/hu unknown
- 1975-02-07 JP JP50015501A patent/JPS50108269A/ja active Pending
- 1975-02-07 DD DD184074A patent/DD118426A5/xx unknown
- 1975-02-08 PL PL1975177899A patent/PL92432B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH605753A5 (en:Method) | 1978-10-13 |
| IL46578A (en) | 1977-11-30 |
| DK44375A (en:Method) | 1975-10-06 |
| IL46578A0 (en) | 1975-04-25 |
| SE7501389L (en:Method) | 1975-08-11 |
| IE40588B1 (en) | 1979-07-04 |
| US4001259A (en) | 1977-01-04 |
| BE825246A (fr) | 1975-08-06 |
| FI750325A7 (en:Method) | 1975-08-10 |
| PL92432B1 (en:Method) | 1977-04-30 |
| SE402588B (sv) | 1978-07-10 |
| ES434547A1 (es) | 1976-12-16 |
| USB545299I5 (en:Method) | 1976-02-24 |
| CA1049525A (en) | 1979-02-27 |
| NL7501499A (nl) | 1975-08-12 |
| JPS50108269A (en:Method) | 1975-08-26 |
| ZA75789B (en) | 1976-03-31 |
| IE40588L (en) | 1975-08-09 |
| HU168593B (en:Method) | 1976-06-28 |
| AU7786575A (en) | 1976-08-05 |
| FR2260346B1 (en:Method) | 1980-01-11 |
| AT339904B (de) | 1977-11-10 |
| ATA94875A (de) | 1977-03-15 |
| DD118426A5 (en:Method) | 1976-03-05 |
| FR2260346A1 (en:Method) | 1975-09-05 |
| GB1444879A (en) | 1976-08-04 |
| LU71812A1 (en:Method) | 1975-12-09 |
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