DE2606663A1 - Neue 9-alkylamino-erythromycine, ihre salze, verfahren zu ihrer herstellung und diese enthaltende arzneimittel - Google Patents
Neue 9-alkylamino-erythromycine, ihre salze, verfahren zu ihrer herstellung und diese enthaltende arzneimittelInfo
- Publication number
- DE2606663A1 DE2606663A1 DE19762606663 DE2606663A DE2606663A1 DE 2606663 A1 DE2606663 A1 DE 2606663A1 DE 19762606663 DE19762606663 DE 19762606663 DE 2606663 A DE2606663 A DE 2606663A DE 2606663 A1 DE2606663 A1 DE 2606663A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- erythromycylamine
- phenyl
- propyl
- carbon 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.)
- Ceased
Links
- 229940088710 antibiotic agent Drugs 0.000 title abstract 2
- 241000894006 Bacteria Species 0.000 title description 2
- 229960003276 erythromycin Drugs 0.000 title description 2
- 239000003242 anti bacterial agent Substances 0.000 title 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 29
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract 2
- -1 cyclohexylamino group Chemical group 0.000 claims description 203
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 22
- 125000003277 amino group Chemical group 0.000 claims description 16
- 150000007522 mineralic acids Chemical class 0.000 claims description 16
- 150000007524 organic acids Chemical class 0.000 claims description 16
- 235000005985 organic acids Nutrition 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 7
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 210000005053 lamin Anatomy 0.000 claims description 6
- 125000003395 phenylethylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- GAZRNXIMWKZADY-UHFFFAOYSA-N 3,5-dimethylpyrazole-1-carboximidamide Chemical compound CC=1C=C(C)N(C(N)=N)N=1 GAZRNXIMWKZADY-UHFFFAOYSA-N 0.000 claims description 4
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 239000012433 hydrogen halide Substances 0.000 claims description 4
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 4
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 3
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 3
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 3
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000003495 polar organic solvent Substances 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 4
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 3
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000005191 hydroxyalkylamino group Chemical group 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 104
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 235000019359 magnesium stearate Nutrition 0.000 description 6
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- 102000006835 Lamins Human genes 0.000 description 5
- 108010047294 Lamins Proteins 0.000 description 5
- 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 5
- 239000002904 solvent Substances 0.000 description 5
- 229920002261 Corn starch Polymers 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- 239000008120 corn starch Substances 0.000 description 4
- 239000008298 dragée Substances 0.000 description 4
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 4
- 230000007717 exclusion Effects 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution 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
- 238000004440 column chromatography Methods 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XCLJRCAJSCMIND-JCTYMORFSA-N (9S)-erythromycyclamine Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)[C@@H](N)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 XCLJRCAJSCMIND-JCTYMORFSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- PTHCMJGKKRQCBF-UHFFFAOYSA-N Cellulose, microcrystalline Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC)C(CO)O1 PTHCMJGKKRQCBF-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 235000013871 bee wax Nutrition 0.000 description 2
- 239000012166 beeswax Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 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
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
- 241000283153 Cetacea Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 238000002768 Kirby-Bauer method Methods 0.000 description 1
- 235000019687 Lamb Nutrition 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical class NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical compound OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 229940082500 cetostearyl alcohol Drugs 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- SASYSVUEVMOWPL-NXVVXOECSA-N decyl oleate Chemical compound CCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC SASYSVUEVMOWPL-NXVVXOECSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000002465 imidoyl halides Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 229960001789 papaverine Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000008389 polyethoxylated castor oil Substances 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- OHSJPLSEQNCRLW-UHFFFAOYSA-N triphenylmethyl radical Chemical compound C1=CC=CC=C1[C](C=1C=CC=CC=1)C1=CC=CC=C1 OHSJPLSEQNCRLW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)
Priority Applications (40)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762606663 DE2606663A1 (de) | 1976-02-19 | 1976-02-19 | Neue 9-alkylamino-erythromycine, ihre salze, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
| DK127676A DK139522C (da) | 1975-04-07 | 1976-03-23 | Analogifremgangsmaade til fremstilling af 9-iminoalkylamino-erythromyciner eller syreadditionssalte deraf |
| BG032726A BG27239A3 (en) | 1976-02-19 | 1976-03-29 | Production method for 9- alkylaminoerythromycines and their salts |
| US05/671,422 US4016263A (en) | 1975-04-07 | 1976-03-29 | N-Substituted erythromcylamines and salts thereof |
| ES446496A ES446496A1 (es) | 1975-04-07 | 1976-03-30 | Procedimiento para la preparacion de nuevas 9-alcohila mi- noeritromicinas. |
| CH417576A CH621559A5 (cs) | 1975-04-07 | 1976-04-02 | |
| FI760887A FI760887A7 (cs) | 1975-04-07 | 1976-04-02 | |
| DD192207A DD125720A5 (cs) | 1975-04-07 | 1976-04-05 | |
| AU12721/76A AU498502B2 (en) | 1975-04-07 | 1976-04-06 | Erythromycin derivatives |
| JP51038682A JPS51131888A (en) | 1975-04-07 | 1976-04-06 | Production of novel 99 alkylaminooerythromycine and pharmaceutical composition containing same |
| GB13943/76A GB1528343A (en) | 1975-04-07 | 1976-04-06 | Erythromycin derivatives |
| RO85431A RO70428B (ro) | 1976-02-19 | 1976-04-06 | Procedeu pentru prepararea unor 9-alchilaminoeritromicilamine |
| GR50482A GR60034B (en) | 1975-04-07 | 1976-04-06 | New 9-alkylamino-erythromycin,their salts,and process for their preparation |
| NZ180535A NZ180535A (en) | 1975-04-07 | 1976-04-06 | Erythromicin derivatives and pharmaceutical compositions |
| CS226776A CS188279B2 (en) | 1976-02-19 | 1976-04-06 | Method of producing new 9-alkylaminoerythromycines |
| CA249,641A CA1064026A (en) | 1975-04-07 | 1976-04-06 | 9-alkylamino-erythromycines, their salts and processes for their preparation |
| SU762342404A SU602119A3 (ru) | 1976-02-19 | 1976-04-06 | Способ получени 9-алкиламиноэритромициламинов или их солей |
| PL18853676A PL102374B1 (pl) | 1976-02-19 | 1976-04-06 | A method of producing new 9-alkyloaminoerythromyciloamines |
| MX000147U MX3330E (es) | 1975-04-07 | 1976-04-06 | Procedimiento para la preparacion de 9-alcohilamino-eritromicinas y sus sales |
| NO761173A NO141014C (no) | 1975-04-07 | 1976-04-06 | Analogifremgangsmaate for fremstilling av farmakologisk aktive 9-alkylamino-erytromyciner og deres salter |
| IL49360A IL49360A (en) | 1975-04-07 | 1976-04-06 | Alkylamino erythromycin derivatives,their preparation and pharmaceutical compositions containing them |
| SE7604053A SE7604053L (sv) | 1975-04-07 | 1976-04-06 | Nytt 9-alkylaminoerytromycin dess salter och forfarande for framstellning derav |
| PT64978A PT64978B (de) | 1975-04-07 | 1976-04-06 | Neue 9-alkylmino-erythromycine ihre salze und verfahren zuihrer herstellung |
| LU74718A LU74718A1 (cs) | 1975-04-07 | 1976-04-07 | |
| IE731/76A IE43575B1 (en) | 1975-04-07 | 1976-04-07 | Erythromycin derivatives |
| FR7610145A FR2306704A1 (fr) | 1975-04-07 | 1976-04-07 | Nouvelles 9-alcoylamino-erythromycines, leurs sels et procedes pour leur preparation |
| NL7603629A NL7603629A (nl) | 1975-04-07 | 1976-04-07 | Werkwijze voor de bereiding van nieuwe alkyl- amino-erythromycinen en zouten daarvan. |
| PH18348A PH14689A (en) | 1976-02-19 | 1976-04-20 | M-substituted erythromycylamines and salts thereof |
| AT282477A AT344911B (de) | 1976-02-19 | 1977-04-22 | Verfahren zur herstellung neuer 9-alkylamino-erythromycine und ihrer salze |
| AT282377A AT344910B (de) | 1976-02-19 | 1977-04-22 | Verfahren zur herstellung neuer 9-alkylamino-erythromycine und ihrer salze |
| ES459475A ES459475A1 (es) | 1976-02-19 | 1977-06-03 | Procedimiento para la preparacion de nuevas 9-alcohilamino- eritromicina. |
| ES459476A ES459476A1 (es) | 1976-02-19 | 1977-06-03 | Procedimiento para la preparacion de nuevas 9-alcohilamino- eritromicinas. |
| CH397280A CH623596A5 (cs) | 1975-04-07 | 1980-05-21 | |
| CH397580A CH624126A5 (cs) | 1975-04-07 | 1980-05-21 | |
| CH397780A CH627479A5 (de) | 1975-04-07 | 1980-05-21 | Verfahren zur herstellung neuer 9-alkylamino-erythromycine. |
| CH397080A CH622810A5 (cs) | 1975-04-07 | 1980-05-21 | |
| CH397480A CH623597A5 (cs) | 1975-04-07 | 1980-05-21 | |
| CH397180A CH623335A5 (cs) | 1975-04-07 | 1980-05-21 | |
| CH397680A CH623336A5 (cs) | 1975-04-07 | 1980-05-21 | |
| CH397380A CH622531A5 (cs) | 1975-04-07 | 1980-05-21 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762606663 DE2606663A1 (de) | 1976-02-19 | 1976-02-19 | Neue 9-alkylamino-erythromycine, ihre salze, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2606663A1 true DE2606663A1 (de) | 1977-08-25 |
Family
ID=5970306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762606663 Ceased DE2606663A1 (de) | 1975-04-07 | 1976-02-19 | Neue 9-alkylamino-erythromycine, ihre salze, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
Country Status (7)
| Country | Link |
|---|---|
| BG (1) | BG27239A3 (cs) |
| CS (1) | CS188279B2 (cs) |
| DE (1) | DE2606663A1 (cs) |
| ES (2) | ES459475A1 (cs) |
| PL (1) | PL102374B1 (cs) |
| RO (1) | RO70428B (cs) |
| SU (1) | SU602119A3 (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008139481A3 (en) * | 2007-05-16 | 2009-02-12 | Luxembourg Biotechnologies Ltd | Proton acceptor iminium/carbocation-type coupling agents |
-
1976
- 1976-02-19 DE DE19762606663 patent/DE2606663A1/de not_active Ceased
- 1976-03-29 BG BG032726A patent/BG27239A3/xx unknown
- 1976-04-06 CS CS226776A patent/CS188279B2/cs unknown
- 1976-04-06 PL PL18853676A patent/PL102374B1/pl unknown
- 1976-04-06 RO RO85431A patent/RO70428B/ro unknown
- 1976-04-06 SU SU762342404A patent/SU602119A3/ru active
-
1977
- 1977-06-03 ES ES459475A patent/ES459475A1/es not_active Expired
- 1977-06-03 ES ES459476A patent/ES459476A1/es not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008139481A3 (en) * | 2007-05-16 | 2009-02-12 | Luxembourg Biotechnologies Ltd | Proton acceptor iminium/carbocation-type coupling agents |
| US8524898B2 (en) | 2007-05-16 | 2013-09-03 | Luxembourg Bio Technologies Ltd. | Proton acceptor iminium/carbocation-type coupling agents |
Also Published As
| Publication number | Publication date |
|---|---|
| RO70428B (ro) | 1983-04-30 |
| SU602119A3 (ru) | 1978-04-05 |
| PL102374B1 (pl) | 1979-03-31 |
| RO70428A (ro) | 1983-04-29 |
| ES459475A1 (es) | 1978-04-16 |
| CS188279B2 (en) | 1979-02-28 |
| ES459476A1 (es) | 1978-04-16 |
| BG27239A3 (en) | 1979-09-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8131 | Rejection |