HRP970684A2 - Sulfonamide substituted compounds, processes for the preparation thereof, their use as medicaments or diagnostics and pharmaceuticals containing them - Google Patents
Sulfonamide substituted compounds, processes for the preparation thereof, their use as medicaments or diagnostics and pharmaceuticals containing themInfo
- Publication number
- HRP970684A2 HRP970684A2 HR19730326.9A HRP970684A HRP970684A2 HR P970684 A2 HRP970684 A2 HR P970684A2 HR P970684 A HRP970684 A HR P970684A HR P970684 A2 HRP970684 A2 HR P970684A2
- Authority
- HR
- Croatia
- Prior art keywords
- atoms
- group
- alkyl
- methyl
- phenyl
- Prior art date
Links
- 229940124530 sulfonamide Drugs 0.000 title claims abstract description 13
- 150000001875 compounds Chemical class 0.000 title claims description 91
- 239000003814 drug Substances 0.000 title claims description 33
- 238000000034 method Methods 0.000 title claims description 17
- 125000000565 sulfonamide group Chemical group 0.000 title abstract description 9
- 238000002360 preparation method Methods 0.000 title description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 252
- -1 NEt2 Chemical group 0.000 claims abstract description 243
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 189
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 171
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 119
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 118
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 118
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims abstract description 90
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 90
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 77
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 77
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 73
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 63
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims abstract description 51
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 claims abstract description 51
- 150000003839 salts Chemical class 0.000 claims abstract description 50
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 46
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 34
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims abstract description 34
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 23
- 125000005956 isoquinolyl group Chemical group 0.000 claims abstract description 21
- 125000005493 quinolyl group Chemical group 0.000 claims abstract description 21
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims description 251
- 125000004432 carbon atom Chemical group C* 0.000 claims description 246
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 152
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 143
- 150000002431 hydrogen Chemical class 0.000 claims description 98
- 125000001424 substituent group Chemical group 0.000 claims description 85
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 82
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 71
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 229940079593 drug Drugs 0.000 claims description 21
- 238000011321 prophylaxis Methods 0.000 claims description 21
- 238000002560 therapeutic procedure Methods 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 16
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 claims description 15
- 239000013543 active substance Substances 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 11
- 206010003119 arrhythmia Diseases 0.000 claims description 10
- 150000003456 sulfonamides Chemical class 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 6
- 206010019280 Heart failures Diseases 0.000 claims description 5
- 230000006793 arrhythmia Effects 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
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- 206010012735 Diarrhoea Diseases 0.000 claims description 4
- 102000004257 Potassium Channel Human genes 0.000 claims description 4
- 208000025865 Ulcer Diseases 0.000 claims description 4
- 230000036982 action potential Effects 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 230000002496 gastric effect Effects 0.000 claims description 4
- 230000000269 nucleophilic effect Effects 0.000 claims description 4
- 108020001213 potassium channel Proteins 0.000 claims description 4
- 230000028327 secretion Effects 0.000 claims description 4
- 231100000397 ulcer Toxicity 0.000 claims description 4
- 206010003130 Arrhythmia supraventricular Diseases 0.000 claims description 3
- 206010003658 Atrial Fibrillation Diseases 0.000 claims description 3
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 3
- 206010042600 Supraventricular arrhythmias Diseases 0.000 claims description 3
- 206010047281 Ventricular arrhythmia Diseases 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 230000001746 atrial effect Effects 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 238000007336 electrophilic substitution reaction Methods 0.000 claims description 3
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000000968 intestinal effect Effects 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 208000000689 peptic esophagitis Diseases 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 230000033764 rhythmic process Effects 0.000 claims description 3
- 230000002861 ventricular Effects 0.000 claims description 3
- 208000003663 ventricular fibrillation Diseases 0.000 claims description 3
- 206010049418 Sudden Cardiac Death Diseases 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 230000001404 mediated effect Effects 0.000 claims description 2
- 150000003458 sulfonic acid derivatives Chemical class 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 206010003662 Atrial flutter Diseases 0.000 claims 1
- 206010042434 Sudden death Diseases 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 abstract description 6
- 229910052799 carbon Inorganic materials 0.000 abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 8
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract 7
- 229910006074 SO2NH2 Inorganic materials 0.000 abstract 6
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 5
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 description 58
- 239000002904 solvent Substances 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 13
- 230000009471 action Effects 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 125000004093 cyano group Chemical group *C#N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 230000000903 blocking effect Effects 0.000 description 9
- 239000000725 suspension Substances 0.000 description 8
- 108091006146 Channels Proteins 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- 239000003416 antiarrhythmic agent Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000003288 anthiarrhythmic effect Effects 0.000 description 4
- 239000012300 argon atmosphere Substances 0.000 description 4
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- 125000000623 heterocyclic group Chemical group 0.000 description 4
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 3
- 241000700199 Cavia porcellus Species 0.000 description 3
- 229910019213 POCl3 Inorganic materials 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- 125000004442 acylamino group Chemical group 0.000 description 3
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- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 3
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- 235000019439 ethyl acetate Nutrition 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
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- MGSHXMOLUWTMGP-UHFFFAOYSA-N 3'-carboxy-alpha-chromanol Chemical class C1=CC=C2C(O)CCOC2=C1 MGSHXMOLUWTMGP-UHFFFAOYSA-N 0.000 description 2
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 2
- HXEWMTXDBOQQKO-UHFFFAOYSA-N 4,7-dichloroquinoline Chemical compound ClC1=CC=NC2=CC(Cl)=CC=C21 HXEWMTXDBOQQKO-UHFFFAOYSA-N 0.000 description 2
- JOXZTUJZGKRJGL-UHFFFAOYSA-N 4-(sulfonylamino)-3,4-dihydro-2h-chromene Chemical compound C1=CC=C2C(N=S(=O)=O)CCOC2=C1 JOXZTUJZGKRJGL-UHFFFAOYSA-N 0.000 description 2
- FKSOZOHKBSIGTI-UHFFFAOYSA-N 4-chloro-2,2-dimethyl-1,3-benzoxazine Chemical compound C1=CC=C2C(Cl)=NC(C)(C)OC2=C1 FKSOZOHKBSIGTI-UHFFFAOYSA-N 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 2
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- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 230000009090 positive inotropic effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000009117 preventive therapy Methods 0.000 description 1
- 230000001536 pro-arrhythmogenic effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229960003401 ramipril Drugs 0.000 description 1
- HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 description 1
- VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 1
- 229960000620 ranitidine Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 230000002336 repolarization Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 239000000050 smooth muscle relaxant Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229960002370 sotalol Drugs 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000001975 sympathomimetic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
-
- 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
-
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
- C07D215/16—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/16—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with only hydrogen or carbon atoms directly attached in positions 2 and 4
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Quinoline Compounds (AREA)
- Pyridine Compounds (AREA)
- Pyrane Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1996152213 DE19652213A1 (de) | 1996-12-16 | 1996-12-16 | Sulfonamid-substituierte Verbindungen, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE1997130326 DE19730326A1 (de) | 1997-07-15 | 1997-07-15 | Sulfonamid-substituierte Verbindungen, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltende pharmazeutische Zubereitungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP970684A2 true HRP970684A2 (en) | 1998-10-31 |
Family
ID=26032247
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR19730326.9A HRP970684A2 (en) | 1996-12-16 | 1997-12-15 | Sulfonamide substituted compounds, processes for the preparation thereof, their use as medicaments or diagnostics and pharmaceuticals containing them |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US5856338A (hu) |
| EP (1) | EP0847996B1 (hu) |
| JP (1) | JP4317601B2 (hu) |
| KR (1) | KR19980064151A (hu) |
| CN (1) | CN1185435A (hu) |
| AT (1) | ATE234821T1 (hu) |
| AU (1) | AU725699B2 (hu) |
| BR (1) | BR9706142A (hu) |
| CA (1) | CA2224885A1 (hu) |
| CZ (1) | CZ403997A3 (hu) |
| DE (1) | DE59709560D1 (hu) |
| DK (1) | DK0847996T3 (hu) |
| ES (1) | ES2195071T3 (hu) |
| HR (1) | HRP970684A2 (hu) |
| HU (1) | HUP9702475A3 (hu) |
| ID (1) | ID19152A (hu) |
| IL (1) | IL122576A0 (hu) |
| NO (1) | NO975887L (hu) |
| NZ (1) | NZ329200A (hu) |
| PL (1) | PL323809A1 (hu) |
| PT (1) | PT847996E (hu) |
| SI (1) | SI0847996T1 (hu) |
| SK (1) | SK171797A3 (hu) |
| TR (1) | TR199701605A2 (hu) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9711220D0 (en) * | 1997-05-30 | 1997-07-23 | Isis Innovation | Antiarrhythmic agents |
| EP1276893A4 (en) | 2000-04-14 | 2005-05-04 | Univ Vanderbilt | NUCLEIC ACIDS AND PYRIFICATED POYPEPTIDES AND ISOLES COTRANSPORTORS OF POTASSIUM CHLORIDE |
| TWI349666B (en) * | 2004-03-12 | 2011-10-01 | Lundbeck & Co As H | Substituted morpholine and thiomorpholine derivatives |
| CN113402476B (zh) * | 2021-06-21 | 2022-04-19 | 广东湛江海洋医药研究院 | 一种亚胺噁嗪衍生物及其制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3737195A1 (de) * | 1987-11-03 | 1989-05-18 | Bayer Ag | Chromanderivate, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| GB8808069D0 (en) * | 1988-04-07 | 1988-05-11 | Fujisawa Pharmaceutical Co | Benzopyran derivatives & processes for preparation thereof |
| FR2639349B1 (fr) * | 1988-11-23 | 1991-02-22 | Sanofi Sa | Nouveaux derives du chromane actifs sur le systeme nerveux central, leur procede de preparation et les compositions pharmaceutiques en contenant |
| US5104890A (en) * | 1989-03-28 | 1992-04-14 | Fujisawa Pharmaceutical Company, Ltd. | Benzopyran derivatives and processes for preparation thereof |
| TW258735B (hu) * | 1992-08-17 | 1995-10-01 | Chugai Pharmaceutical Co Ltd | |
| CN1204134C (zh) * | 1996-05-15 | 2005-06-01 | 赫彻斯特股份公司 | 氨磺酰－取代的苯并二氢吡喃,其制法,作为药物或诊断剂的应用及含有它的药物 |
-
1997
- 1997-11-18 NZ NZ329200A patent/NZ329200A/xx unknown
- 1997-12-05 AT AT97121437T patent/ATE234821T1/de not_active IP Right Cessation
- 1997-12-05 SI SI9730534T patent/SI0847996T1/xx unknown
- 1997-12-05 EP EP97121437A patent/EP0847996B1/de not_active Expired - Lifetime
- 1997-12-05 ES ES97121437T patent/ES2195071T3/es not_active Expired - Lifetime
- 1997-12-05 DK DK97121437T patent/DK0847996T3/da active
- 1997-12-05 DE DE59709560T patent/DE59709560D1/de not_active Expired - Lifetime
- 1997-12-05 PT PT97121437T patent/PT847996E/pt unknown
- 1997-12-11 ID IDP973864A patent/ID19152A/id unknown
- 1997-12-12 TR TR97/01605A patent/TR199701605A2/xx unknown
- 1997-12-12 IL IL12257697A patent/IL122576A0/xx unknown
- 1997-12-12 SK SK1717-97A patent/SK171797A3/sk unknown
- 1997-12-15 US US08/990,455 patent/US5856338A/en not_active Expired - Lifetime
- 1997-12-15 HU HU9702475A patent/HUP9702475A3/hu unknown
- 1997-12-15 CN CN97125504A patent/CN1185435A/zh active Pending
- 1997-12-15 NO NO975887A patent/NO975887L/no not_active Application Discontinuation
- 1997-12-15 HR HR19730326.9A patent/HRP970684A2/hr not_active Application Discontinuation
- 1997-12-15 AU AU48373/97A patent/AU725699B2/en not_active Ceased
- 1997-12-15 JP JP34546997A patent/JP4317601B2/ja not_active Expired - Fee Related
- 1997-12-15 BR BR9706142A patent/BR9706142A/pt not_active Application Discontinuation
- 1997-12-15 CZ CZ974039A patent/CZ403997A3/cs unknown
- 1997-12-16 PL PL97323809A patent/PL323809A1/xx unknown
- 1997-12-16 KR KR1019970068995A patent/KR19980064151A/ko not_active Application Discontinuation
- 1997-12-16 CA CA002224885A patent/CA2224885A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| NZ329200A (en) | 1999-05-28 |
| JPH10182610A (ja) | 1998-07-07 |
| EP0847996B1 (de) | 2003-03-19 |
| JP4317601B2 (ja) | 2009-08-19 |
| PT847996E (pt) | 2003-07-31 |
| NO975887D0 (no) | 1997-12-15 |
| PL323809A1 (en) | 1998-06-22 |
| TR199701605A2 (xx) | 1998-07-21 |
| CN1185435A (zh) | 1998-06-24 |
| CA2224885A1 (en) | 1998-06-16 |
| DK0847996T3 (da) | 2003-06-30 |
| ATE234821T1 (de) | 2003-04-15 |
| NO975887L (no) | 1998-06-17 |
| HUP9702475A2 (hu) | 1999-06-28 |
| KR19980064151A (ko) | 1998-10-07 |
| US5856338A (en) | 1999-01-05 |
| AU725699B2 (en) | 2000-10-19 |
| SI0847996T1 (en) | 2003-08-31 |
| IL122576A0 (en) | 1998-06-15 |
| CZ403997A3 (cs) | 1998-07-15 |
| ES2195071T3 (es) | 2003-12-01 |
| BR9706142A (pt) | 1999-05-18 |
| DE59709560D1 (de) | 2003-04-24 |
| HU9702475D0 (en) | 1998-03-02 |
| SK171797A3 (en) | 1998-07-08 |
| HUP9702475A3 (en) | 2000-01-28 |
| EP0847996A1 (de) | 1998-06-17 |
| MX9710126A (es) | 1998-07-31 |
| AU4837397A (en) | 1998-06-18 |
| ID19152A (id) | 1998-06-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1OB | Publication of a patent application | ||
| AIPI | Request for the grant of a patent on the basis of a substantive examination of a patent application | ||
| ODBC | Application rejected |