NO310068B1 - Nye benzensulfonylaminforbindelser, fremgangsmåte ved fremstilling derav, samt farmasöytiske sammensetninger inneholdende slike - Google Patents
Nye benzensulfonylaminforbindelser, fremgangsmåte ved fremstilling derav, samt farmasöytiske sammensetninger inneholdende slike Download PDFInfo
- Publication number
- NO310068B1 NO310068B1 NO980842A NO980842A NO310068B1 NO 310068 B1 NO310068 B1 NO 310068B1 NO 980842 A NO980842 A NO 980842A NO 980842 A NO980842 A NO 980842A NO 310068 B1 NO310068 B1 NO 310068B1
- Authority
- NO
- Norway
- Prior art keywords
- group
- formula
- compound
- hydrogen atom
- same meanings
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 77
- 238000002360 preparation method Methods 0.000 title claims description 50
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 230000008569 process Effects 0.000 title claims description 7
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 title description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 157
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 51
- -1 4-chlorophenylsulfonyl Chemical group 0.000 claims description 50
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 31
- 238000004519 manufacturing process Methods 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 14
- 235000019260 propionic acid Nutrition 0.000 claims description 11
- 239000007858 starting material Substances 0.000 claims description 10
- LLNAMUJRIZIXHF-CLFYSBASSA-N (z)-2-methyl-3-phenylprop-2-en-1-ol Chemical compound OCC(/C)=C\C1=CC=CC=C1 LLNAMUJRIZIXHF-CLFYSBASSA-N 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 238000004140 cleaning Methods 0.000 claims description 7
- 229910001961 silver nitrate Inorganic materials 0.000 claims description 7
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 claims description 7
- 239000012414 tert-butyl nitrite Substances 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 230000009471 action Effects 0.000 claims description 6
- 150000001408 amides Chemical group 0.000 claims description 6
- 150000002148 esters Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
- 239000002840 nitric oxide donor Substances 0.000 claims description 4
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 4
- 238000007239 Wittig reaction Methods 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 101150100032 Tbxa2r gene Proteins 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229910052702 rhenium Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- XEYFGUPZSYKONE-UHFFFAOYSA-N 3-[6-[(4-chlorophenyl)sulfonylamino]-2-(2-nitrooxyethyl)-5,6,7,8-tetrahydronaphthalen-1-yl]propanoic acid Chemical group C1CC=2C(CCC(=O)O)=C(CCO[N+]([O-])=O)C=CC=2CC1NS(=O)(=O)C1=CC=C(Cl)C=C1 XEYFGUPZSYKONE-UHFFFAOYSA-N 0.000 claims 1
- RGZKDSPDLWGCEN-UHFFFAOYSA-N 3-[6-[(4-chlorophenyl)sulfonylamino]-3-(2-nitrooxyethyl)-5,6,7,8-tetrahydronaphthalen-1-yl]propanoic acid Chemical group C1CC=2C(CCC(=O)O)=CC(CCO[N+]([O-])=O)=CC=2CC1NS(=O)(=O)C1=CC=C(Cl)C=C1 RGZKDSPDLWGCEN-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical group OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 claims 1
- 239000002464 receptor antagonist Substances 0.000 claims 1
- 229940044551 receptor antagonist Drugs 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 5
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract description 4
- 229910004679 ONO2 Inorganic materials 0.000 abstract 3
- 125000001893 nitrooxy group Chemical group [O-][N+](=O)O* 0.000 abstract 3
- 101100042909 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) SNO2 gene Proteins 0.000 abstract 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N SnO2 Inorganic materials O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000004385 trihaloalkyl group Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 85
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
- 239000000203 mixture Substances 0.000 description 24
- 239000003480 eluent Substances 0.000 description 15
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000004587 chromatography analysis Methods 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- 238000001704 evaporation Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000005557 antagonist Substances 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 229940099508 TP receptor antagonist Drugs 0.000 description 5
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 5
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 230000008602 contraction Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 210000003752 saphenous vein Anatomy 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 210000004623 platelet-rich plasma Anatomy 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000002062 proliferating effect Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 230000002792 vascular Effects 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- IRFYUMNCLRXJBA-UHFFFAOYSA-N 2-methyl-2-trimethylsilylbutanoic acid Chemical compound CCC(C)(C(O)=O)[Si](C)(C)C IRFYUMNCLRXJBA-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 208000007536 Thrombosis Diseases 0.000 description 2
- 108090000300 Thromboxane Receptors Proteins 0.000 description 2
- 102000003938 Thromboxane Receptors Human genes 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 230000004931 aggregating effect Effects 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 230000000702 anti-platelet effect Effects 0.000 description 2
- 230000001028 anti-proliverative effect Effects 0.000 description 2
- 239000003146 anticoagulant agent Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000001010 compromised effect Effects 0.000 description 2
- 208000029078 coronary artery disease Diseases 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000002526 effect on cardiovascular system Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 230000007170 pathology Effects 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000000328 pro-aggregatory effect Effects 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000012418 sodium perborate tetrahydrate Substances 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 230000003639 vasoconstrictive effect Effects 0.000 description 2
- 229940124549 vasodilator Drugs 0.000 description 2
- 239000003071 vasodilator agent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YZCAFAKJYGDMSY-UHFFFAOYSA-N 1-amino-2-methylpropane-2-thiol;hydrochloride Chemical compound Cl.CC(C)(S)CN YZCAFAKJYGDMSY-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- TXBSZAAOZHWYSV-UHFFFAOYSA-N 2-methyl-n-(2-oxo-5,6,7,8-tetrahydrochromen-6-yl)benzenesulfonamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC1CC(C=CC(=O)O2)=C2CC1 TXBSZAAOZHWYSV-UHFFFAOYSA-N 0.000 description 1
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 1
- FTCUWYNXKXYFSD-UHFFFAOYSA-N 4-chloro-n-(2-oxo-5,6,7,8-tetrahydrochromen-6-yl)benzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC1CC(C=CC(=O)O2)=C2CC1 FTCUWYNXKXYFSD-UHFFFAOYSA-N 0.000 description 1
- RJJPBTBQAFAYQM-UHFFFAOYSA-N 4-fluoro-n-(2-oxo-5,6,7,8-tetrahydrochromen-6-yl)benzenesulfonamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NC1CC(C=CC(=O)O2)=C2CC1 RJJPBTBQAFAYQM-UHFFFAOYSA-N 0.000 description 1
- QYPHYGHRBPMFAZ-UHFFFAOYSA-N 6-[(4-chlorophenyl)sulfonylamino]-1-(3-methoxy-3-oxopropyl)-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid Chemical compound C1C2=CC=C(C(O)=O)C(CCC(=O)OC)=C2CCC1NS(=O)(=O)C1=CC=C(Cl)C=C1 QYPHYGHRBPMFAZ-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FVIGODVHAVLZOO-UHFFFAOYSA-N Dixanthogen Chemical compound CCOC(=S)SSC(=S)OCC FVIGODVHAVLZOO-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 108010078321 Guanylate Cyclase Proteins 0.000 description 1
- 102000014469 Guanylate cyclase Human genes 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 208000019693 Lung disease Diseases 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 102000008299 Nitric Oxide Synthase Human genes 0.000 description 1
- 108010021487 Nitric Oxide Synthase Proteins 0.000 description 1
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 1
- 239000000006 Nitroglycerin Substances 0.000 description 1
- RUSLEMRHCGUNMS-UHFFFAOYSA-L O[Cr](O[Cr](O)(=O)=O)(=O)=O.C(C1=CC=CC=C1)C1=CC=NC=C1.C(C1=CC=CC=C1)C1=CC=NC=C1 Chemical compound O[Cr](O[Cr](O)(=O)=O)(=O)=O.C(C1=CC=CC=C1)C1=CC=NC=C1.C(C1=CC=CC=C1)C1=CC=NC=C1 RUSLEMRHCGUNMS-UHFFFAOYSA-L 0.000 description 1
- 241000283977 Oryctolagus Species 0.000 description 1
- 208000003782 Raynaud disease Diseases 0.000 description 1
- 208000012322 Raynaud phenomenon Diseases 0.000 description 1
- 229940124639 Selective inhibitor Drugs 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- ZWZUFQPXYVYAFO-UHFFFAOYSA-N Tert-butyl (triphenylphosphoranylidene)acetate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OC(C)(C)C)C1=CC=CC=C1 ZWZUFQPXYVYAFO-UHFFFAOYSA-N 0.000 description 1
- 206010047139 Vasoconstriction Diseases 0.000 description 1
- 206010047163 Vasospasm Diseases 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000002744 anti-aggregatory effect Effects 0.000 description 1
- 230000000479 anti-thromboxane effect Effects 0.000 description 1
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical class CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- ZOOGRGPOEVQQDX-UHFFFAOYSA-N cyclic GMP Natural products O1C2COP(O)(=O)OC2C(O)C1N1C=NC2=C1NC(N)=NC2=O ZOOGRGPOEVQQDX-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 210000002889 endothelial cell Anatomy 0.000 description 1
- 210000003038 endothelium Anatomy 0.000 description 1
- 235000004626 essential fatty acids Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229960003711 glyceryl trinitrate Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000004 hemodynamic effect Effects 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
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 201000001881 impotence Diseases 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 108020004084 membrane receptors Proteins 0.000 description 1
- 102000006240 membrane receptors Human genes 0.000 description 1
- NTNUDYROPUKXNA-UHFFFAOYSA-N methyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OC)C1=CC=CC=C1 NTNUDYROPUKXNA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- RMLXHNDORNYRQE-UHFFFAOYSA-N n-(3-bromo-2-oxo-5,6,7,8-tetrahydrochromen-6-yl)-4-chlorobenzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC1CC(C=C(Br)C(=O)O2)=C2CC1 RMLXHNDORNYRQE-UHFFFAOYSA-N 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 230000036963 noncompetitive effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012285 osmium tetroxide Substances 0.000 description 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 230000003578 releasing effect Effects 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002195 synergetic effect Effects 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
- 210000001519 tissue Anatomy 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
- YLGRTLMDMVAFNI-UHFFFAOYSA-N tributyl(prop-2-enyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)CC=C YLGRTLMDMVAFNI-UHFFFAOYSA-N 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- 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
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Diabetes (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9702445A FR2760235B1 (fr) | 1997-02-28 | 1997-02-28 | Nouveaux derives de benzenesulfonylamine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (3)
Publication Number | Publication Date |
---|---|
NO980842D0 NO980842D0 (no) | 1998-02-27 |
NO980842L NO980842L (no) | 1998-08-31 |
NO310068B1 true NO310068B1 (no) | 2001-05-14 |
Family
ID=9504314
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO980842A NO310068B1 (no) | 1997-02-28 | 1998-02-27 | Nye benzensulfonylaminforbindelser, fremgangsmåte ved fremstilling derav, samt farmasöytiske sammensetninger inneholdende slike |
Country Status (20)
Country | Link |
---|---|
US (1) | US6013667A (pt) |
EP (1) | EP0864561B1 (pt) |
JP (1) | JP3917287B2 (pt) |
CN (1) | CN1160323C (pt) |
AT (1) | ATE205189T1 (pt) |
AU (1) | AU736532B2 (pt) |
BR (1) | BR9800773A (pt) |
CA (1) | CA2231026C (pt) |
DE (1) | DE69801535T2 (pt) |
DK (1) | DK0864561T3 (pt) |
ES (1) | ES2163844T3 (pt) |
FR (1) | FR2760235B1 (pt) |
GR (1) | GR3037048T3 (pt) |
HK (1) | HK1014932A1 (pt) |
HU (1) | HU224960B1 (pt) |
NO (1) | NO310068B1 (pt) |
NZ (1) | NZ329868A (pt) |
PL (1) | PL193930B1 (pt) |
PT (1) | PT864561E (pt) |
ZA (1) | ZA981681B (pt) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2803848B1 (fr) * | 2000-01-19 | 2002-02-15 | Adir | Nouveaux derives de benzenesulfonamide, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
FR2827280B1 (fr) * | 2001-07-13 | 2003-10-31 | Servier Lab | Nouveaux derives de benzene sulfonamide, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
US8152693B2 (en) | 2006-05-08 | 2012-04-10 | Nokia Corporation | Exercise data device, server, system and method |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3000377A1 (de) * | 1980-01-07 | 1981-07-09 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue sulfonamide, verfahren zu deren herstellung sowie diese verbindungen enthaltende arzneimittel |
CA2105067C (en) * | 1991-03-01 | 2002-05-14 | Kiyoshi Yoshida | Indan derivative and thromboxane antagonist containing the same |
EP0670833A1 (de) * | 1992-11-27 | 1995-09-13 | Iovis Biomedical And Pharmaceutical Consultants | Nitroxyverbindungen mit pharmazeutischen eigenschaften |
FR2711139B1 (fr) * | 1993-10-15 | 1995-12-01 | Adir | Nouveaux dérivés de 1,2,3,4-tétrahydronaphtalène, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
-
1997
- 1997-02-28 FR FR9702445A patent/FR2760235B1/fr not_active Expired - Fee Related
-
1998
- 1998-02-26 CA CA002231026A patent/CA2231026C/fr not_active Expired - Fee Related
- 1998-02-26 BR BR9800773-4A patent/BR9800773A/pt active Search and Examination
- 1998-02-26 JP JP04479498A patent/JP3917287B2/ja not_active Expired - Fee Related
- 1998-02-27 AT AT98400468T patent/ATE205189T1/de active
- 1998-02-27 DK DK98400468T patent/DK0864561T3/da active
- 1998-02-27 DE DE69801535T patent/DE69801535T2/de not_active Expired - Lifetime
- 1998-02-27 NZ NZ329868A patent/NZ329868A/xx not_active IP Right Cessation
- 1998-02-27 HU HU9800430A patent/HU224960B1/hu not_active IP Right Cessation
- 1998-02-27 EP EP98400468A patent/EP0864561B1/fr not_active Expired - Lifetime
- 1998-02-27 US US09/032,587 patent/US6013667A/en not_active Expired - Lifetime
- 1998-02-27 NO NO980842A patent/NO310068B1/no not_active IP Right Cessation
- 1998-02-27 PT PT98400468T patent/PT864561E/pt unknown
- 1998-02-27 CN CNB981080707A patent/CN1160323C/zh not_active Expired - Fee Related
- 1998-02-27 ZA ZA981681A patent/ZA981681B/xx unknown
- 1998-02-27 PL PL325082A patent/PL193930B1/pl not_active IP Right Cessation
- 1998-02-27 AU AU56360/98A patent/AU736532B2/en not_active Ceased
- 1998-02-27 ES ES98400468T patent/ES2163844T3/es not_active Expired - Lifetime
-
1999
- 1999-01-07 HK HK99100054A patent/HK1014932A1/xx not_active IP Right Cessation
-
2001
- 2001-10-30 GR GR20010401920T patent/GR3037048T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
DK0864561T3 (da) | 2001-11-19 |
EP0864561B1 (fr) | 2001-09-05 |
GR3037048T3 (en) | 2002-01-31 |
JPH10251217A (ja) | 1998-09-22 |
FR2760235B1 (fr) | 1999-04-09 |
ES2163844T3 (es) | 2002-02-01 |
PT864561E (pt) | 2001-12-28 |
NZ329868A (en) | 1999-01-28 |
NO980842D0 (no) | 1998-02-27 |
NO980842L (no) | 1998-08-31 |
ZA981681B (en) | 1998-09-04 |
DE69801535T2 (de) | 2002-05-08 |
CA2231026A1 (fr) | 1998-08-28 |
CN1195662A (zh) | 1998-10-14 |
US6013667A (en) | 2000-01-11 |
PL193930B1 (pl) | 2007-04-30 |
HU224960B1 (en) | 2006-04-28 |
HUP9800430A3 (en) | 2000-09-28 |
ATE205189T1 (de) | 2001-09-15 |
DE69801535D1 (de) | 2001-10-11 |
AU736532B2 (en) | 2001-08-02 |
JP3917287B2 (ja) | 2007-05-23 |
HK1014932A1 (en) | 1999-10-08 |
CA2231026C (fr) | 2004-02-10 |
CN1160323C (zh) | 2004-08-04 |
HU9800430D0 (en) | 1998-04-28 |
HUP9800430A2 (hu) | 1999-06-28 |
BR9800773A (pt) | 1999-12-07 |
AU5636098A (en) | 1998-09-03 |
FR2760235A1 (fr) | 1998-09-04 |
EP0864561A1 (fr) | 1998-09-16 |
PL325082A1 (en) | 1998-08-31 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN105829305B (zh) | Nrf2调节剂 | |
JP2022502385A (ja) | Shp2の活性を阻害するための化合物の製造方法 | |
BR112016008133B1 (pt) | amino-heteroaril benzamidas como inibidores de quinase, seus usos, e composição farmacêutica | |
RU2395499C2 (ru) | Ингибитор связывания сфингозин-1-фосфата | |
JP2003514762A (ja) | Srcファミリーsh2ドメインインヒビターとしてのピリドン | |
JPS6357561A (ja) | 5−アミノ−4−ヒドロキシ吉草酸誘導体の製造方法 | |
WO2016137788A1 (en) | Selective bace1 inhibitors | |
JP2000502710A (ja) | 置換n―[(アミノイミノメチル又はアミノメチル)フェニル]プロピルアミド | |
TWI793868B (zh) | 苄胺或苄醇衍生物及其用途 | |
JPH11506436A (ja) | インテグリン受容体拮抗剤としてのイソオキサゾリンおよびイソオキサゾール誘導体 | |
JPWO2008123207A1 (ja) | オルニチン誘導体 | |
KR20230040953A (ko) | 치환된 피페리딘 화합물 및 이의 적용례 | |
HUT52525A (en) | Process for producing retroviral proteaz-inhibitors and pharmaceutical compositions containing them as active components | |
JP4157158B2 (ja) | ドーパミン作動薬の新規な塩の形態 | |
KR20110117088A (ko) | 통증 및 기타 질병을 치료하기 위한 화합물 및 방법 | |
JPH06506200A (ja) | ピリジンおよびイミダゾールから誘導された心臓血管病薬 | |
KR20210097161A (ko) | 헤모글로빈 조절제로서의 피라졸 | |
JPH0544942B2 (pt) | ||
JP2011525487A (ja) | トロンビン阻害剤としての使用のための新規複素環式カルボキサミド | |
NO310068B1 (no) | Nye benzensulfonylaminforbindelser, fremgangsmåte ved fremstilling derav, samt farmasöytiske sammensetninger inneholdende slike | |
FR2758329A1 (fr) | Derives d'imidazole-4-butane boronique, leur preparation et leur utilisation en therapeutique | |
AU2019424628B2 (en) | 1,2,3,4-tetrahydroquinoxaline derivative, preparation method therefor and application thereof | |
JP2001501627A (ja) | 新規ペンタエリスリトール誘導体、その製造方法および使用ならびにその合成のための中間体 | |
WO2021110076A1 (zh) | 草酰胺类衍生物、其制备方法及其在医药上的应用 | |
WO2007012761A1 (fr) | Nouveaux composes 1,1-pyridinyl aminocyclopropanamines polysubstitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM1K | Lapsed by not paying the annual fees |