DE2858177C2 - Arzneimittel enthaltend N-substituierte 2-Cyanaziridine - Google Patents
Arzneimittel enthaltend N-substituierte 2-CyanaziridineInfo
- Publication number
- DE2858177C2 DE2858177C2 DE19782858177 DE2858177A DE2858177C2 DE 2858177 C2 DE2858177 C2 DE 2858177C2 DE 19782858177 DE19782858177 DE 19782858177 DE 2858177 A DE2858177 A DE 2858177A DE 2858177 C2 DE2858177 C2 DE 2858177C2
- Authority
- DE
- Germany
- Prior art keywords
- mono
- aziridine
- polysubstituted
- udf54
- udf53
- 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.)
- Expired
Links
- 229940126601 medicinal product Drugs 0.000 title claims 2
- -1 tetrahydrofurfuryl Chemical group 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000002246 antineoplastic agent Substances 0.000 claims description 10
- 229940127089 cytotoxic agent Drugs 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 8
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 claims description 7
- 229960005091 chloramphenicol Drugs 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 239000000969 carrier Substances 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 13
- 239000000126 substance Substances 0.000 description 11
- 230000003308 immunostimulating effect Effects 0.000 description 8
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 6
- 210000000265 leukocyte Anatomy 0.000 description 5
- 101100311330 Schizosaccharomyces pombe (strain 972 / ATCC 24843) uap56 gene Proteins 0.000 description 4
- 210000004698 lymphocyte Anatomy 0.000 description 4
- 101150018444 sub2 gene Proteins 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PGZUFTROELAOMP-UHFFFAOYSA-N aziridine-2-carbonitrile Chemical class N#CC1CN1 PGZUFTROELAOMP-UHFFFAOYSA-N 0.000 description 3
- 230000003385 bacteriostatic effect Effects 0.000 description 3
- 229960001438 immunostimulant agent Drugs 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 231100000299 mutagenicity Toxicity 0.000 description 3
- 230000007886 mutagenicity Effects 0.000 description 3
- BLBSHRFZHWOWNW-UHFFFAOYSA-N 1-benzylaziridine-2-carbonitrile Chemical compound N#CC1CN1CC1=CC=CC=C1 BLBSHRFZHWOWNW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000890 drug combination Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- 239000003022 immunostimulating agent Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection 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
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- ZDSLWQTWYUJOJR-UHFFFAOYSA-N 1-(1-adamantyl)aziridine-2-carbonitrile Chemical compound N#CC1CN1C1(C2)CC(C3)CC2CC3C1 ZDSLWQTWYUJOJR-UHFFFAOYSA-N 0.000 description 1
- PXRQJBFQKFGYPW-UHFFFAOYSA-N 1-(2-cyano-1-phenylethenyl)aziridine-2-carbonitrile Chemical group C=1C=CC=CC=1C(=CC#N)N1CC1C#N PXRQJBFQKFGYPW-UHFFFAOYSA-N 0.000 description 1
- KUFHSAOGAVKLAB-UHFFFAOYSA-N 1-(furan-2-ylmethyl)aziridine-2-carbonitrile Chemical compound N#CC1CN1CC1=CC=CO1 KUFHSAOGAVKLAB-UHFFFAOYSA-N 0.000 description 1
- QVGUJBCKGUQJIK-UHFFFAOYSA-N 1-[(4-hydroxyphenyl)methyl]aziridine-2-carbonitrile Chemical compound C1=CC(O)=CC=C1CN1C(C#N)C1 QVGUJBCKGUQJIK-UHFFFAOYSA-N 0.000 description 1
- OFGUDXIHTSHDIV-UHFFFAOYSA-N 1-methylaziridine-2-carbonitrile Chemical compound CN1CC1C#N OFGUDXIHTSHDIV-UHFFFAOYSA-N 0.000 description 1
- LWWMXPUFGZOIFI-UHFFFAOYSA-N 1-propan-2-ylaziridine-2-carbonitrile Chemical compound CC(C)N1CC1C#N LWWMXPUFGZOIFI-UHFFFAOYSA-N 0.000 description 1
- BSBUUBUYBRAQMM-UHFFFAOYSA-N 1-tert-butylaziridine-2-carbonitrile Chemical compound CC(C)(C)N1CC1C#N BSBUUBUYBRAQMM-UHFFFAOYSA-N 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- RMSRKYVNQYEPHO-UHFFFAOYSA-N 2-cyanoaziridine-1-carboxamide Chemical compound NC(=O)N1CC1C#N RMSRKYVNQYEPHO-UHFFFAOYSA-N 0.000 description 1
- FUBFWTUFPGFHOJ-UHFFFAOYSA-N 2-nitrofuran Chemical class [O-][N+](=O)C1=CC=CO1 FUBFWTUFPGFHOJ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 238000010953 Ames test Methods 0.000 description 1
- 231100000039 Ames test Toxicity 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- 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 1
- 229930195725 Mannitol Natural products 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 238000011785 NMRI mouse Methods 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- XIPUIGPNIDKXJU-UHFFFAOYSA-N [CH]1CC1 Chemical compound [CH]1CC1 XIPUIGPNIDKXJU-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- LZRVAAYXGFWSDY-UHFFFAOYSA-N aziridine-2-carboxamide Chemical compound NC(=O)C1CN1 LZRVAAYXGFWSDY-UHFFFAOYSA-N 0.000 description 1
- 150000001541 aziridines Chemical class 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 244000052616 bacterial pathogen Species 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
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 229960004397 cyclophosphamide Drugs 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- FHGDKPLGGUQPPO-UHFFFAOYSA-N ethyl 2-(2-cyanoaziridin-1-yl)cyclohexene-1-carboxylate Chemical compound C1CCCC(C(=O)OCC)=C1N1C(C#N)C1 FHGDKPLGGUQPPO-UHFFFAOYSA-N 0.000 description 1
- RMGXMQYFBYUDTL-UHFFFAOYSA-N ethyl 3-(2-cyanoaziridin-1-yl)propanoate Chemical compound CCOC(=O)CCN1CC1C#N RMGXMQYFBYUDTL-UHFFFAOYSA-N 0.000 description 1
- NQSNFGHURVSURB-UHFFFAOYSA-N ethyl 3-[(2-cyanoaziridin-1-yl)methyl]-2-methylbenzoate Chemical compound CCOC(=O)C1=CC=CC(CN2C(C2)C#N)=C1C NQSNFGHURVSURB-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000000499 gel Substances 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
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 206010024378 leukocytosis Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- QZIQJVCYUQZDIR-UHFFFAOYSA-N mechlorethamine hydrochloride Chemical class Cl.ClCCN(C)CCCl QZIQJVCYUQZDIR-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 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
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 210000004989 spleen cell Anatomy 0.000 description 1
- 238000013223 sprague-dawley female rat Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782858177 DE2858177C2 (de) | 1978-08-03 | 1978-08-03 | Arzneimittel enthaltend N-substituierte 2-Cyanaziridine |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782833986 DE2833986A1 (de) | 1978-08-03 | 1978-08-03 | Immunstimulierende n-substituierte aziridin-2-carbonsaeurederivate, verfahren zu ihrer herstellung sowie arzneimittel, die diese substanzen enthalten |
| DE19782858177 DE2858177C2 (de) | 1978-08-03 | 1978-08-03 | Arzneimittel enthaltend N-substituierte 2-Cyanaziridine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2858177C2 true DE2858177C2 (de) | 1987-05-07 |
Family
ID=25775267
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782858177 Expired DE2858177C2 (de) | 1978-08-03 | 1978-08-03 | Arzneimittel enthaltend N-substituierte 2-Cyanaziridine |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2858177C2 (US07368563-20080506-C00056.png) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2528460A1 (de) * | 1975-06-26 | 1977-01-13 | Boehringer Mannheim Gmbh | Verwendung von l-carboxamido-2- cyan-aziridin als immunstimulans |
-
1978
- 1978-08-03 DE DE19782858177 patent/DE2858177C2/de not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2528460A1 (de) * | 1975-06-26 | 1977-01-13 | Boehringer Mannheim Gmbh | Verwendung von l-carboxamido-2- cyan-aziridin als immunstimulans |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0559238B1 (de) | Cyancrotonsäureamidverbindung als Arzneimittel mit immunmodulierenden Eigenschaften | |
| DE69432644T2 (de) | Kombination eines Angiotensin-II antagonistisch wirkendes Benzimidazols mit ein Diuretikum | |
| DE69114117T2 (de) | Neue Verwendung von Peptidderivat. | |
| EP0014976B1 (de) | N-substituierte 2-Cyanaziridine, Verfahren zu deren Herstellung sowie diese Substanzen enthaltende Arzneimittel, entsprechend substituierte Aziridin-2-carbonsäureamide und deren Herstellung | |
| EP0977570A1 (de) | Chinoxaline in dreier-kombination mit proteaseinhibitoren und reverse transkriptaseinhibitoren als arzneimittel zur behandlung von aids | |
| DE10043282A1 (de) | Verwendung von Inhibitoren der Amyloid-beta-Protein-Bildung | |
| DE19506742A1 (de) | Verwendung von Chinoxalinen in Kombination mit Protease-Inhibitoren als Arzneimittel zur Behandlung von AIDS und/oder HIV-Infektionen | |
| EP0038438A2 (de) | Substituierte 1,2,5-Oxadiazol-2-oxide zur Anwendung als Arzneimittel und sie enthaltende Arzneimittel | |
| DE68915269T2 (de) | Polyvalentes entzündungshemmendes mittel. | |
| EP0269899A2 (de) | Verwendung von aromatischen Carbonsäureamiden | |
| EP0003602A1 (de) | Pyrrolidin-Derivate zur Anwendung als therapeutische Wirkstoffe und diese enthaltende Arzneimittel | |
| DE2833986C2 (US07368563-20080506-C00056.png) | ||
| DE3035688C2 (US07368563-20080506-C00056.png) | ||
| DE2951671C2 (de) | Arzneimittelzubereitung mit Antithrombosewirkung und Hemmwirkung auf die Agglomeration der Blutplättchen | |
| DE2858177C2 (de) | Arzneimittel enthaltend N-substituierte 2-Cyanaziridine | |
| DE69201066T2 (de) | Colominsäure und Produkte einer teilweisen Hydrolyse von Colominsäure zur Herstellung von Arzneimitteln zur Behandlung von Hepatitis, Nephritis und Arthritis. | |
| DE60211938T2 (de) | Pharmazeutische zusammensetzung enthaltend eine kombination aus metformin und einer 4-oxobutansäure und ihre verwendung zur behandlung von diabetes | |
| DE4014672A1 (de) | Verwendung von adamantan-derivaten zur zytoprotektion von nicht-infizierten und virus-infizierten lymphozyten als auch anderen zelltypen | |
| EP1137438A1 (de) | Zubereitung mit verbesserter therapeutischer breite, enthaltend nukleotidsyntheseinhibitoren | |
| DE3780343T2 (de) | Antivirale 8-phenylxanthine. | |
| DE3608726A1 (de) | Verwendung aminosubstituierter benzoesaeuren als heilmittel gegen diarrhoe und arzneimittel auf basis dieser verbindungen | |
| DE2528460A1 (de) | Verwendung von l-carboxamido-2- cyan-aziridin als immunstimulans | |
| DE4202184A1 (de) | Substituierte salicylaldehyde zur behandlung von krankheiten | |
| DE2708327A1 (de) | Entzuendungshemmendes mittel | |
| DE1792447C3 (de) | Oral anwendbares, cytostatisches Mittel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| Q172 | Divided out of (supplement): |
Ref country code: DE Ref document number: 2833986 |
|
| 8125 | Change of the main classification |
Ipc: A61K 31/395 |
|
| 8110 | Request for examination paragraph 44 | ||
| AC | Divided out of |
Ref country code: DE Ref document number: 2833986 Format of ref document f/p: P |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| AC | Divided out of |
Ref country code: DE Ref document number: 2833986 Format of ref document f/p: P |
|
| 8339 | Ceased/non-payment of the annual fee |