EA005376B1 - Новые соединения бензолсульфонамида, способ их получения и фармацевтические композиции, их содержащие - Google Patents
Новые соединения бензолсульфонамида, способ их получения и фармацевтические композиции, их содержащие Download PDFInfo
- Publication number
- EA005376B1 EA005376B1 EA200200666A EA200200666A EA005376B1 EA 005376 B1 EA005376 B1 EA 005376B1 EA 200200666 A EA200200666 A EA 200200666A EA 200200666 A EA200200666 A EA 200200666A EA 005376 B1 EA005376 B1 EA 005376B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- formula
- group
- phenyl
- ethyl
- optionally substituted
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 9
- 150000008331 benzenesulfonamides Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 103
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 38
- 125000005843 halogen group Chemical group 0.000 claims abstract description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 9
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 5
- 125000003277 amino group Chemical group 0.000 claims abstract description 3
- 125000004385 trihaloalkyl group Chemical group 0.000 claims abstract description 3
- 239000003814 drug Substances 0.000 claims abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 34
- -1 substituted Chemical class 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 24
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
- 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 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 229910052700 potassium Inorganic materials 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- 230000007062 hydrolysis Effects 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- 150000002148 esters Chemical group 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 238000010511 deprotection reaction Methods 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 238000003776 cleavage reaction Methods 0.000 claims description 4
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000005544 phthalimido group Chemical group 0.000 claims description 4
- 230000007017 scission Effects 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- OGGCYQKPNONLJU-UHFFFAOYSA-N 3-[3-[2-[(4-chlorophenyl)sulfonylamino]ethyl]-5-[2-[2-[3-(dimethylamino)propoxy]phenyl]ethyl]phenyl]propanoic acid Chemical compound CN(C)CCCOC1=CC=CC=C1CCC1=CC(CCNS(=O)(=O)C=2C=CC(Cl)=CC=2)=CC(CCC(O)=O)=C1 OGGCYQKPNONLJU-UHFFFAOYSA-N 0.000 claims description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 238000006264 debenzylation reaction Methods 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- LSGQKITYBRBEDP-UHFFFAOYSA-N 3-[3-[2-[(4-chlorophenyl)sulfonylamino]ethyl]-5-[2-[2-(2-morpholin-4-ylethoxy)phenyl]ethyl]phenyl]propanoic acid Chemical compound C=1C(CCC=2C(=CC=CC=2)OCCN2CCOCC2)=CC(CCC(=O)O)=CC=1CCNS(=O)(=O)C1=CC=C(Cl)C=C1 LSGQKITYBRBEDP-UHFFFAOYSA-N 0.000 claims description 2
- NOKGPSRNABBBRI-UHFFFAOYSA-N 3-[3-[2-[(4-chlorophenyl)sulfonylamino]ethyl]-5-[2-[2-(2-pyrrolidin-1-ylethoxy)phenyl]ethyl]phenyl]propanoic acid Chemical compound C=1C(CCC=2C(=CC=CC=2)OCCN2CCCC2)=CC(CCC(=O)O)=CC=1CCNS(=O)(=O)C1=CC=C(Cl)C=C1 NOKGPSRNABBBRI-UHFFFAOYSA-N 0.000 claims description 2
- 206010002383 Angina Pectoris Diseases 0.000 claims description 2
- 208000009079 Bronchial Spasm Diseases 0.000 claims description 2
- 208000014181 Bronchial disease Diseases 0.000 claims description 2
- 206010006482 Bronchospasm Diseases 0.000 claims description 2
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- 208000003782 Raynaud disease Diseases 0.000 claims description 2
- 208000012322 Raynaud phenomenon Diseases 0.000 claims description 2
- 208000024248 Vascular System injury Diseases 0.000 claims description 2
- 208000012339 Vascular injury Diseases 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 239000005557 antagonist Substances 0.000 claims description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 150000001733 carboxylic acid esters Chemical group 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 230000002490 cerebral effect Effects 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 208000010125 myocardial infarction Diseases 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 208000037997 venous disease Diseases 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims 2
- 150000001735 carboxylic acids Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 67
- 239000000047 product Substances 0.000 description 61
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 28
- 238000002474 experimental method Methods 0.000 description 28
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
- 239000012043 crude product Substances 0.000 description 25
- 239000011541 reaction mixture Substances 0.000 description 25
- 239000000243 solution Substances 0.000 description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 238000004587 chromatography analysis Methods 0.000 description 18
- 238000004452 microanalysis Methods 0.000 description 18
- 239000000377 silicon dioxide Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 238000000605 extraction Methods 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 10
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
- 239000000908 ammonium hydroxide Substances 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- 235000019260 propionic acid Nutrition 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- 229940076279 serotonin Drugs 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 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 4
- FEKLXZOYEQJIBC-UHFFFAOYSA-N 4-[2-(dimethylamino)ethoxy]phenol Chemical compound CN(C)CCOC1=CC=C(O)C=C1 FEKLXZOYEQJIBC-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- FKKZGQXMWVGPMH-UHFFFAOYSA-N (2-hydroxyphenyl)methyl-triphenylphosphanium;bromide Chemical compound [Br-].OC1=CC=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 FKKZGQXMWVGPMH-UHFFFAOYSA-N 0.000 description 2
- ZLDMZIXUGCGKMB-UHFFFAOYSA-N 3,5-dibromobenzaldehyde Chemical compound BrC1=CC(Br)=CC(C=O)=C1 ZLDMZIXUGCGKMB-UHFFFAOYSA-N 0.000 description 2
- DJZXRNDUFQISOD-UHFFFAOYSA-N 3-[3-[2-[(4-chlorophenyl)sulfonylamino]ethyl]-5-[2-[2-[2-[4-(6-fluoro-1,2-benzothiazol-3-yl)piperidin-1-yl]ethoxy]phenyl]ethyl]phenyl]propanoic acid Chemical compound C=1C(CCC=2C(=CC=CC=2)OCCN2CCC(CC2)C=2C3=CC=C(F)C=C3SN=2)=CC(CCC(=O)O)=CC=1CCNS(=O)(=O)C1=CC=C(Cl)C=C1 DJZXRNDUFQISOD-UHFFFAOYSA-N 0.000 description 2
- GLQPYPYHHDRTIQ-UHFFFAOYSA-N 3-[3-[2-[(4-chlorophenyl)sulfonylamino]ethyl]-5-[2-[2-[3-[4-(4-fluorophenyl)piperazin-1-yl]propoxy]phenyl]ethyl]phenyl]propanoic acid Chemical compound C=1C(CCC=2C(=CC=CC=2)OCCCN2CCN(CC2)C=2C=CC(F)=CC=2)=CC(CCC(=O)O)=CC=1CCNS(=O)(=O)C1=CC=C(Cl)C=C1 GLQPYPYHHDRTIQ-UHFFFAOYSA-N 0.000 description 2
- GOSWANBZBKTDDL-UHFFFAOYSA-N 3-[3-[2-[(4-chlorophenyl)sulfonylamino]ethyl]-5-[2-[2-[3-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]propoxy]phenyl]ethyl]phenyl]propanoic acid Chemical compound C=1C(CCC=2C(=CC=CC=2)OCCCN2CCC(CC2)C=2C3=CC=C(F)C=C3ON=2)=CC(CCC(=O)O)=CC=1CCNS(=O)(=O)C1=CC=C(Cl)C=C1 GOSWANBZBKTDDL-UHFFFAOYSA-N 0.000 description 2
- MTQLSGYXCNZOGI-UHFFFAOYSA-N 3-[3-[2-[(4-chlorophenyl)sulfonylamino]ethyl]-5-[2-[2-[4-(dimethylamino)butoxy]phenyl]ethyl]phenyl]propanoic acid Chemical compound CN(C)CCCCOC1=CC=CC=C1CCC1=CC(CCNS(=O)(=O)C=2C=CC(Cl)=CC=2)=CC(CCC(O)=O)=C1 MTQLSGYXCNZOGI-UHFFFAOYSA-N 0.000 description 2
- WGHYUJZKTJQYKW-UHFFFAOYSA-N 3-[3-[2-[(4-chlorophenyl)sulfonylamino]ethyl]-5-[2-[4-[2-(dimethylamino)ethoxy]phenyl]ethyl]phenyl]propanoic acid Chemical compound C1=CC(OCCN(C)C)=CC=C1CCC1=CC(CCNS(=O)(=O)C=2C=CC(Cl)=CC=2)=CC(CCC(O)=O)=C1 WGHYUJZKTJQYKW-UHFFFAOYSA-N 0.000 description 2
- FNMZKRIIDCVOLR-UHFFFAOYSA-N 3-[3-[2-[(4-chlorophenyl)sulfonylamino]ethyl]-5-[3-[2-[3-(dimethylamino)propoxy]phenyl]propyl]phenyl]propanoic acid Chemical compound CN(C)CCCOC1=CC=CC=C1CCCC1=CC(CCNS(=O)(=O)C=2C=CC(Cl)=CC=2)=CC(CCC(O)=O)=C1 FNMZKRIIDCVOLR-UHFFFAOYSA-N 0.000 description 2
- KCBFTYCSLACJFY-UHFFFAOYSA-N 3-[3-[2-[(4-chlorophenyl)sulfonylamino]ethyl]-5-[[2-[2-(dimethylamino)ethoxy]phenoxy]methyl]phenyl]propanoic acid Chemical compound CN(C)CCOC1=CC=CC=C1OCC1=CC(CCNS(=O)(=O)C=2C=CC(Cl)=CC=2)=CC(CCC(O)=O)=C1 KCBFTYCSLACJFY-UHFFFAOYSA-N 0.000 description 2
- MGRPGMTVUHYJGQ-UHFFFAOYSA-N 3-[3-[2-[(4-chlorophenyl)sulfonylamino]ethyl]-5-[[2-[3-(dimethylamino)propoxy]phenoxy]methyl]phenyl]propanoic acid Chemical compound CN(C)CCCOC1=CC=CC=C1OCC1=CC(CCNS(=O)(=O)C=2C=CC(Cl)=CC=2)=CC(CCC(O)=O)=C1 MGRPGMTVUHYJGQ-UHFFFAOYSA-N 0.000 description 2
- XPVKMXOCNWDIGR-UHFFFAOYSA-N 3-[3-[2-[(4-chlorophenyl)sulfonylamino]ethyl]-5-[[4-[2-(dimethylamino)ethoxy]phenoxy]methyl]phenyl]propanoic acid Chemical compound C1=CC(OCCN(C)C)=CC=C1OCC1=CC(CCNS(=O)(=O)C=2C=CC(Cl)=CC=2)=CC(CCC(O)=O)=C1 XPVKMXOCNWDIGR-UHFFFAOYSA-N 0.000 description 2
- VVEQNTFQEWMTMV-UHFFFAOYSA-N 3-[3-[2-[2-[3-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]propoxy]phenyl]ethyl]-5-[2-[(4-chlorophenyl)sulfonylamino]ethyl]phenyl]propanoic acid;hydrochloride Chemical compound Cl.C=1C(CCC=2C(=CC=CC=2)OCCCN2CCN(CC2)C=2C3=CC=CC=C3SN=2)=CC(CCC(=O)O)=CC=1CCNS(=O)(=O)C1=CC=C(Cl)C=C1 VVEQNTFQEWMTMV-UHFFFAOYSA-N 0.000 description 2
- MJMVPAGLXWQWJG-BNFZFUHLSA-N CC(C)(C)OC(=O)\C=C\C1=CC(CO)=CC(\C=C\N2C(C3=CC=CC=C3C2=O)=O)=C1 Chemical compound CC(C)(C)OC(=O)\C=C\C1=CC(CO)=CC(\C=C\N2C(C3=CC=CC=C3C2=O)=O)=C1 MJMVPAGLXWQWJG-BNFZFUHLSA-N 0.000 description 2
- FAADZNSSZLCWQU-UHFFFAOYSA-N CCCC1=CC(CCNS(C(C=C2)=CC=C2Cl)(=O)=O)=CC(CCC(C=CC=C2)=C2OCCN2CCOCC2)=C1 Chemical compound CCCC1=CC(CCNS(C(C=C2)=CC=C2Cl)(=O)=O)=CC(CCC(C=CC=C2)=C2OCCN2CCOCC2)=C1 FAADZNSSZLCWQU-UHFFFAOYSA-N 0.000 description 2
- SEIUSHQHTXLNPW-UHFFFAOYSA-N ClC1=CC=C(C=C1)S(=O)(=O)NCCC=1C=C(C=C(C1)CCC1=C(C=CC=C1)OCCN1CCCC1)CCC Chemical compound ClC1=CC=C(C=C1)S(=O)(=O)NCCC=1C=C(C=C(C1)CCC1=C(C=CC=C1)OCCN1CCCC1)CCC SEIUSHQHTXLNPW-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000035508 accumulation Effects 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
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Classifications
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
- C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
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- 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
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0109339A FR2827280B1 (fr) | 2001-07-13 | 2001-07-13 | Nouveaux derives de benzene sulfonamide, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200200666A1 EA200200666A1 (ru) | 2003-02-27 |
| EA005376B1 true EA005376B1 (ru) | 2005-02-24 |
Family
ID=8865462
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200200666A EA005376B1 (ru) | 2001-07-13 | 2002-07-12 | Новые соединения бензолсульфонамида, способ их получения и фармацевтические композиции, их содержащие |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6541471B1 (enExample) |
| EP (1) | EP1275641B1 (enExample) |
| JP (1) | JP3770858B2 (enExample) |
| KR (1) | KR100503157B1 (enExample) |
| CN (1) | CN1186318C (enExample) |
| AR (1) | AR035257A1 (enExample) |
| AT (1) | ATE286877T1 (enExample) |
| AU (1) | AU2002300092B2 (enExample) |
| BR (1) | BR0202685A (enExample) |
| CA (1) | CA2393995C (enExample) |
| DE (1) | DE60202554T2 (enExample) |
| DK (1) | DK1275641T3 (enExample) |
| EA (1) | EA005376B1 (enExample) |
| ES (1) | ES2234994T3 (enExample) |
| FR (1) | FR2827280B1 (enExample) |
| HU (1) | HUP0202284A3 (enExample) |
| MX (1) | MXPA02006853A (enExample) |
| NO (1) | NO20023390L (enExample) |
| NZ (1) | NZ520141A (enExample) |
| PL (1) | PL355009A1 (enExample) |
| PT (1) | PT1275641E (enExample) |
| SI (1) | SI1275641T1 (enExample) |
| ZA (1) | ZA200205597B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106083546A (zh) * | 2016-06-20 | 2016-11-09 | 上海引盛生物科技有限公司 | 一种3,5‑二溴苯甲醛的制备方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993013057A1 (fr) * | 1991-12-20 | 1993-07-08 | Hokuriku Pharmaceutical Co., Ltd. | Derive de benzenesulfonamide substitue |
| RU2059615C1 (ru) * | 1990-08-20 | 1996-05-10 | Эйсай Ко., Лтд. | Производные сульфонамида |
| FR2760235A1 (fr) * | 1997-02-28 | 1998-09-04 | Adir | Nouveaux derives de benzenesulfonylamine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02304022A (ja) * | 1989-05-18 | 1990-12-17 | Mitsubishi Kasei Corp | セロトニン拮抗剤 |
| US5364866A (en) * | 1989-05-19 | 1994-11-15 | Hoechst-Roussel Pharmaceuticals, Inc. | Heteroarylpiperidines, pyrrolidines and piperazines and their use as antipsychotics and analetics |
| GB9220137D0 (en) * | 1992-09-23 | 1992-11-04 | Pfizer Ltd | Therapeutic agents |
| JPH0753505A (ja) * | 1992-10-01 | 1995-02-28 | Hokuriku Seiyaku Co Ltd | ベンゼンスルホンアミド誘導体及びその用途 |
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2001
- 2001-07-13 FR FR0109339A patent/FR2827280B1/fr not_active Expired - Fee Related
-
2002
- 2002-07-11 PL PL02355009A patent/PL355009A1/xx not_active Application Discontinuation
- 2002-07-11 DE DE60202554T patent/DE60202554T2/de not_active Expired - Fee Related
- 2002-07-11 PT PT02291747T patent/PT1275641E/pt unknown
- 2002-07-11 AT AT02291747T patent/ATE286877T1/de not_active IP Right Cessation
- 2002-07-11 MX MXPA02006853A patent/MXPA02006853A/es active IP Right Grant
- 2002-07-11 ES ES02291747T patent/ES2234994T3/es not_active Expired - Lifetime
- 2002-07-11 SI SI200230073T patent/SI1275641T1/xx unknown
- 2002-07-11 EP EP02291747A patent/EP1275641B1/fr not_active Expired - Lifetime
- 2002-07-11 DK DK02291747T patent/DK1275641T3/da active
- 2002-07-12 NO NO20023390A patent/NO20023390L/no not_active Application Discontinuation
- 2002-07-12 BR BR0202685-6A patent/BR0202685A/pt not_active IP Right Cessation
- 2002-07-12 AU AU2002300092A patent/AU2002300092B2/en not_active Ceased
- 2002-07-12 JP JP2002203408A patent/JP3770858B2/ja not_active Expired - Fee Related
- 2002-07-12 NZ NZ520141A patent/NZ520141A/en unknown
- 2002-07-12 ZA ZA200205597A patent/ZA200205597B/xx unknown
- 2002-07-12 US US10/195,018 patent/US6541471B1/en not_active Expired - Fee Related
- 2002-07-12 AR ARP020102609A patent/AR035257A1/es not_active Application Discontinuation
- 2002-07-12 HU HU0202284A patent/HUP0202284A3/hu unknown
- 2002-07-12 EA EA200200666A patent/EA005376B1/ru not_active IP Right Cessation
- 2002-07-13 KR KR10-2002-0040946A patent/KR100503157B1/ko not_active Expired - Fee Related
- 2002-07-15 CN CNB021241627A patent/CN1186318C/zh not_active Expired - Fee Related
- 2002-07-15 CA CA002393995A patent/CA2393995C/fr not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2059615C1 (ru) * | 1990-08-20 | 1996-05-10 | Эйсай Ко., Лтд. | Производные сульфонамида |
| WO1993013057A1 (fr) * | 1991-12-20 | 1993-07-08 | Hokuriku Pharmaceutical Co., Ltd. | Derive de benzenesulfonamide substitue |
| FR2760235A1 (fr) * | 1997-02-28 | 1998-09-04 | Adir | Nouveaux derives de benzenesulfonylamine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
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Legal Events
| Date | Code | Title | Description |
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| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM AZ BY KZ KG MD TJ TM RU |