DE3025656A1 - Sulfonsaeurealkalimetallsalz- und sulfonamidderivate von 6,6'-methylen-bis- (2,2,4-trimethyl-1,2-dihydrochinolin) und deren dimere und trimere kondensationsprodukte, verfahren zur herstellung derselben und diese enthaltende arzneimittel - Google Patents
Sulfonsaeurealkalimetallsalz- und sulfonamidderivate von 6,6'-methylen-bis- (2,2,4-trimethyl-1,2-dihydrochinolin) und deren dimere und trimere kondensationsprodukte, verfahren zur herstellung derselben und diese enthaltende arzneimittelInfo
- Publication number
- DE3025656A1 DE3025656A1 DE19803025656 DE3025656A DE3025656A1 DE 3025656 A1 DE3025656 A1 DE 3025656A1 DE 19803025656 DE19803025656 DE 19803025656 DE 3025656 A DE3025656 A DE 3025656A DE 3025656 A1 DE3025656 A1 DE 3025656A1
- Authority
- DE
- Germany
- Prior art keywords
- dihydroquinoline
- methylene
- bis
- trimethyl
- sulfonic acid
- 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
- -1 SULPHONIC ACID ALKALIMETAL SALT Chemical class 0.000 title claims description 41
- 239000007859 condensation product Substances 0.000 title claims description 31
- 238000000034 method Methods 0.000 title claims description 18
- 229940124530 sulfonamide Drugs 0.000 title claims description 16
- 229910052783 alkali metal Inorganic materials 0.000 title claims description 15
- 239000000047 product Substances 0.000 title description 5
- 239000000539 dimer Substances 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000013638 trimer Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 38
- 150000003254 radicals Chemical class 0.000 claims description 30
- ADHZMOYUJKFKSE-UHFFFAOYSA-N 2,2,4-trimethyl-6-[(2,2,4-trimethyl-1h-quinolin-6-yl)methyl]-1h-quinoline Chemical compound N1C(C)(C)C=C(C)C2=CC(CC3=CC=C4NC(C)(C)C=C(C4=C3)C)=CC=C21 ADHZMOYUJKFKSE-UHFFFAOYSA-N 0.000 claims description 29
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical group OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 24
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 12
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 11
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 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 claims description 5
- 150000003456 sulfonamides Chemical class 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000004744 fabric Substances 0.000 claims 1
- 230000005855 radiation Effects 0.000 description 20
- 230000000694 effects Effects 0.000 description 16
- 239000000203 mixture Substances 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000003211 malignant effect Effects 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 208000025865 Ulcer Diseases 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 231100000331 toxic Toxicity 0.000 description 4
- 230000002588 toxic effect Effects 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- 231100000397 ulcer Toxicity 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003183 carcinogenic agent Substances 0.000 description 3
- LLCOIQRNSJBFSN-UHFFFAOYSA-N methane;sulfurochloridic acid Chemical compound C.OS(Cl)(=O)=O LLCOIQRNSJBFSN-UHFFFAOYSA-N 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 239000002534 radiation-sensitizing agent Substances 0.000 description 3
- 230000001235 sensitizing effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- IRFSXVIRXMYULF-UHFFFAOYSA-N 1,2-dihydroquinoline Chemical compound C1=CC=C2C=CCNC2=C1 IRFSXVIRXMYULF-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- 239000002211 L-ascorbic acid Substances 0.000 description 2
- 235000000069 L-ascorbic acid Nutrition 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- XDVMCVGTDUKDHL-UHFFFAOYSA-N [amino(2-azaniumylethylsulfanyl)methylidene]azanium;dibromide Chemical compound Br.Br.NCCSC(N)=N XDVMCVGTDUKDHL-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 230000000711 cancerogenic effect Effects 0.000 description 2
- 231100000357 carcinogen Toxicity 0.000 description 2
- 231100000315 carcinogenic Toxicity 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
- 239000012043 crude product Substances 0.000 description 2
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000036470 plasma concentration Effects 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000007348 radical reaction Methods 0.000 description 2
- 238000001959 radiotherapy Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- UQBNSDYXYHVZOD-UHFFFAOYSA-N (4-hydroxy-8-methyl-2-oxo-3,4-dihydropyrido[4,3-e][1,3]oxazin-5-yl)methyl dihydrogen phosphate Chemical compound OC1NC(=O)OC2=C1C(COP(O)(O)=O)=CN=C2C UQBNSDYXYHVZOD-UHFFFAOYSA-N 0.000 description 1
- PQNQOHDLTYFBHE-UHFFFAOYSA-N 1-ethyl-2h-quinoline Chemical compound C1=CC=C2N(CC)CC=CC2=C1 PQNQOHDLTYFBHE-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- RDDXLTPBALMBBI-UHFFFAOYSA-N 4-methyl-1,2-dihydroquinoline Chemical compound C1=CC=C2C(C)=CCNC2=C1 RDDXLTPBALMBBI-UHFFFAOYSA-N 0.000 description 1
- ARSRBNBHOADGJU-UHFFFAOYSA-N 7,12-dimethyltetraphene Chemical compound C1=CC2=CC=CC=C2C2=C1C(C)=C(C=CC=C1)C1=C2C ARSRBNBHOADGJU-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 description 1
- 206010005003 Bladder cancer Diseases 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 101000794282 Homo sapiens Putative protein C3P1 Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010021143 Hypoxia 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
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 102100030156 Putative protein C3P1 Human genes 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003217 anti-cancerogenic effect Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 208000019425 cirrhosis of liver Diseases 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 230000006326 desulfonation Effects 0.000 description 1
- 238000005869 desulfonation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000002375 environmental carcinogen Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 244000144993 groups of animals Species 0.000 description 1
- 208000007475 hemolytic anemia Diseases 0.000 description 1
- 231100000334 hepatotoxic Toxicity 0.000 description 1
- 230000003082 hepatotoxic effect Effects 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 208000018875 hypoxemia Diseases 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 230000000936 membranestabilizing effect Effects 0.000 description 1
- 229960003151 mercaptamine Drugs 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000004005 nitrosamines Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 230000004223 radioprotective effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Toxicology (AREA)
- Biochemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79MA3172A HU185208B (en) | 1979-07-06 | 1979-07-06 | Process for producing the water-soluble derivatives of 6,6-methylene-bis/2,2,4-trimetyl-1,2-dihidric quinoline/ |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3025656A1 true DE3025656A1 (de) | 1981-01-22 |
| DE3025656C2 DE3025656C2 (en, 2012) | 1989-06-22 |
Family
ID=10999106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803025656 Granted DE3025656A1 (de) | 1979-07-06 | 1980-07-07 | Sulfonsaeurealkalimetallsalz- und sulfonamidderivate von 6,6'-methylen-bis- (2,2,4-trimethyl-1,2-dihydrochinolin) und deren dimere und trimere kondensationsprodukte, verfahren zur herstellung derselben und diese enthaltende arzneimittel |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4356306A (en, 2012) |
| JP (2) | JPS5639070A (en, 2012) |
| AR (1) | AR223884A1 (en, 2012) |
| AT (1) | AT375647B (en, 2012) |
| BE (1) | BE884187A (en, 2012) |
| BR (1) | BR8004170A (en, 2012) |
| CA (1) | CA1138873A (en, 2012) |
| CH (1) | CH649536A5 (en, 2012) |
| CS (1) | CS227309B2 (en, 2012) |
| DD (1) | DD151872A5 (en, 2012) |
| DE (1) | DE3025656A1 (en, 2012) |
| DK (1) | DK156436C (en, 2012) |
| FI (1) | FI75809C (en, 2012) |
| FR (1) | FR2460933B1 (en, 2012) |
| GB (1) | GB2054582B (en, 2012) |
| HU (1) | HU185208B (en, 2012) |
| IT (1) | IT1132511B (en, 2012) |
| NL (1) | NL8003839A (en, 2012) |
| PL (2) | PL125177B1 (en, 2012) |
| SE (1) | SE447899B (en, 2012) |
| SU (2) | SU990083A3 (en, 2012) |
| YU (1) | YU41933B (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1988008420A1 (en) * | 1987-04-22 | 1988-11-03 | Materiál Vegyipari Kisszövetkezet | Condensation products of 2,2,4-trimethyl-1,2-dihydro-quinoline and oxo compounds and derivatives thereof |
| US5202338A (en) * | 1990-10-31 | 1993-04-13 | Vilmos Bar | Dihydroquinoline derivatives, pharmaceutical compositions and methods of use of dihydroquinoline derivatives as modulators of the arachidonic acid cascade |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5292497A (en) * | 1987-12-22 | 1994-03-08 | U.S. Bioscience, Inc. | Method of reducing chemotherapy toxicity using (methylaminopropylamino)propyl dihydrogen phosphorothioate |
| DE10329860A1 (de) | 2003-07-02 | 2005-01-20 | Atto-Tec Gmbh | Sulfonamidderivate polycyclischer Farbstoffe für analytische Anwendungen |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4046765A (en) * | 1971-09-07 | 1977-09-06 | Material Ksz. | Dihydroquinoline derivatives of antioxidant activity and a process for the preparation thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3047521A (en) * | 1959-08-13 | 1962-07-31 | Monsanto Chemicals | Method of making improved polymeric dihydroquinoline compositions |
| US4025631A (en) * | 1971-09-07 | 1977-05-24 | Material Ksz. | Dihydroquinoline derivatives of antioxidant activity |
| BE788509A (fr) * | 1971-09-07 | 1973-01-02 | Material Vegyi | Derives de dihydroquinoleine et procede de preparation |
-
1979
- 1979-07-06 HU HU79MA3172A patent/HU185208B/hu unknown
-
1980
- 1980-07-02 NL NL8003839A patent/NL8003839A/nl not_active Application Discontinuation
- 1980-07-02 US US06/164,526 patent/US4356306A/en not_active Expired - Lifetime
- 1980-07-03 DK DK288080A patent/DK156436C/da not_active IP Right Cessation
- 1980-07-03 YU YU1741/80A patent/YU41933B/xx unknown
- 1980-07-03 CS CS804776A patent/CS227309B2/cs unknown
- 1980-07-03 AR AR281642A patent/AR223884A1/es active
- 1980-07-04 CH CH5176/80A patent/CH649536A5/de not_active IP Right Cessation
- 1980-07-04 BR BR8004170A patent/BR8004170A/pt unknown
- 1980-07-04 PL PL1980225476A patent/PL125177B1/pl unknown
- 1980-07-04 CA CA000355543A patent/CA1138873A/en not_active Expired
- 1980-07-04 IT IT23268/80A patent/IT1132511B/it active
- 1980-07-04 FI FI802153A patent/FI75809C/fi not_active IP Right Cessation
- 1980-07-04 SE SE8004973A patent/SE447899B/sv not_active IP Right Cessation
- 1980-07-04 DD DD80222412A patent/DD151872A5/de unknown
- 1980-07-04 PL PL1980232265A patent/PL126791B1/pl unknown
- 1980-07-04 BE BE0/201307A patent/BE884187A/fr not_active IP Right Cessation
- 1980-07-04 SU SU802948199A patent/SU990083A3/ru active
- 1980-07-07 AT AT0354480A patent/AT375647B/de not_active IP Right Cessation
- 1980-07-07 FR FR8015086A patent/FR2460933B1/fr not_active Expired
- 1980-07-07 JP JP9184580A patent/JPS5639070A/ja active Granted
- 1980-07-07 GB GB8022191A patent/GB2054582B/en not_active Expired
- 1980-07-07 DE DE19803025656 patent/DE3025656A1/de active Granted
- 1980-11-17 SU SU803004799A patent/SU1108092A1/ru active
-
1986
- 1986-12-17 JP JP61299046A patent/JPS62187457A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4046765A (en) * | 1971-09-07 | 1977-09-06 | Material Ksz. | Dihydroquinoline derivatives of antioxidant activity and a process for the preparation thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1988008420A1 (en) * | 1987-04-22 | 1988-11-03 | Materiál Vegyipari Kisszövetkezet | Condensation products of 2,2,4-trimethyl-1,2-dihydro-quinoline and oxo compounds and derivatives thereof |
| US5202338A (en) * | 1990-10-31 | 1993-04-13 | Vilmos Bar | Dihydroquinoline derivatives, pharmaceutical compositions and methods of use of dihydroquinoline derivatives as modulators of the arachidonic acid cascade |
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| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |