BG108272A - Арилсулфонамиди като противовирусни средства - Google Patents

Арилсулфонамиди като противовирусни средства Download PDF

Info

Publication number: BG108272A
Authority: BG; Bulgaria
Prior art keywords: hydroxy; amino; alkyl; halogen; general formula
Prior art date: 2001-04-19

Application number

BG108272A

Other languages

Bulgarian (bg)

English (en)

Inventor

Tobias Wunberg

Wolfgang Bender

Peter Eckenberg

Sabine Hallenberger

Kerstin Henninger

Joerg Keldenich

Armin Kern

Siegfried Raddatz

Juergen Reefschlaeger

Gunter Schmidt

Holger Zimmermann

Franz Zumpe

Martin Radtke

Original Assignee

Bayer Aktiengesellschaft

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2001-04-19

Filing date

2003-10-14

Publication date

2004-10-29

2001-10-02 Priority claimed from DE10148598A external-priority patent/DE10148598A1/de

2003-10-14 Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft

2004-10-29 Publication of BG108272A publication Critical patent/BG108272A/bg

Links

239000003443 antiviral agent Substances 0.000 title abstract description 3
125000004421 aryl sulphonamide group Chemical group 0.000 title abstract 2
238000000034 method Methods 0.000 claims abstract description 75
125000001424 substituent group Chemical group 0.000 claims abstract description 22
-1 hydroxy, amino Chemical group 0.000 claims description 108
150000001875 compounds Chemical class 0.000 claims description 101
229910052736 halogen Inorganic materials 0.000 claims description 63
150000002367 halogens Chemical class 0.000 claims description 63
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 39
239000000203 mixture Substances 0.000 claims description 39
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 37
239000001257 hydrogen Substances 0.000 claims description 35
229910052739 hydrogen Inorganic materials 0.000 claims description 35
125000004432 carbon atom Chemical group C* 0.000 claims description 32
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 30
239000000460 chlorine Substances 0.000 claims description 29
229910052760 oxygen Inorganic materials 0.000 claims description 28
239000001301 oxygen Substances 0.000 claims description 28
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 27
229910052801 chlorine Inorganic materials 0.000 claims description 27
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 26
125000005842 heteroatom Chemical group 0.000 claims description 26
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
125000004093 cyano group Chemical group *C#N 0.000 claims description 21
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
229910052717 sulfur Inorganic materials 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 19
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 18
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
239000011593 sulfur Substances 0.000 claims description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
125000000623 heterocyclic group Chemical group 0.000 claims description 16
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 15
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 14
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 13
150000002431 hydrogen Chemical class 0.000 claims description 13
238000011282 treatment Methods 0.000 claims description 13
125000004043 oxo group Chemical group O=* 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 12
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 11
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 10
150000001204 N-oxides Chemical class 0.000 claims description 10
YMIXWSVDZOGUBN-UHFFFAOYSA-N amino hypofluorite Chemical compound NOF YMIXWSVDZOGUBN-UHFFFAOYSA-N 0.000 claims description 10
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 10
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
125000001072 heteroaryl group Chemical group 0.000 claims description 8
AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
230000003612 virological effect Effects 0.000 claims description 8
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
230000008569 process Effects 0.000 claims description 6
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 5
BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 5
206010011831 Cytomegalovirus infection Diseases 0.000 claims description 5
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
201000010099 disease Diseases 0.000 claims description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
125000002883 imidazolyl group Chemical group 0.000 claims description 5
125000001041 indolyl group Chemical group 0.000 claims description 5
125000003373 pyrazinyl group Chemical group 0.000 claims description 5
125000003226 pyrazolyl group Chemical group 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
125000000168 pyrrolyl group Chemical group 0.000 claims description 5
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims description 4
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
125000002971 oxazolyl group Chemical group 0.000 claims description 4
230000002265 prevention Effects 0.000 claims description 4
238000000926 separation method Methods 0.000 claims description 4
229940124530 sulfonamide Drugs 0.000 claims description 4
150000003456 sulfonamides Chemical class 0.000 claims description 4
125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
125000000335 thiazolyl group Chemical group 0.000 claims description 4
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 claims description 3
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000003282 alkyl amino group Chemical group 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 claims description 2
ZYZFSGQIHMVWMA-UHFFFAOYSA-N OCl(F)N Chemical compound OCl(F)N ZYZFSGQIHMVWMA-UHFFFAOYSA-N 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 claims 1
125000006239 protecting group Chemical group 0.000 claims 1
241000701022 Cytomegalovirus Species 0.000 abstract description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 90
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 65
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 44
238000004128 high performance liquid chromatography Methods 0.000 description 43
239000000243 solution Substances 0.000 description 36
229920005989 resin Polymers 0.000 description 35
239000011347 resin Substances 0.000 description 35
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
210000004027 cell Anatomy 0.000 description 25
239000002904 solvent Substances 0.000 description 25
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 22
239000000126 substance Substances 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
238000003786 synthesis reaction Methods 0.000 description 16
238000005160 1H NMR spectroscopy Methods 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
229910004373 HOAc Inorganic materials 0.000 description 15
241000701024 Human betaherpesvirus 5 Species 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
230000015572 biosynthetic process Effects 0.000 description 14
239000000725 suspension Substances 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
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239000003480 eluent Substances 0.000 description 12
208000015181 infectious disease Diseases 0.000 description 11
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238000006243 chemical reaction Methods 0.000 description 10
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 10
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DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
241000699670 Mus sp. Species 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
239000002609 medium Substances 0.000 description 8
239000011734 sodium Substances 0.000 description 8
241001465754 Metazoa Species 0.000 description 7
239000002253 acid Substances 0.000 description 7
239000013543 active substance Substances 0.000 description 7
239000002585 base Substances 0.000 description 7
230000037396 body weight Effects 0.000 description 7
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 7
241000701029 Murid betaherpesvirus 1 Species 0.000 description 6
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238000005917 acylation reaction Methods 0.000 description 6
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239000001294 propane Substances 0.000 description 6
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OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
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WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
229960002695 phenobarbital Drugs 0.000 description 1
239000002953 phosphate buffered saline Substances 0.000 description 1
230000004962 physiological condition Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920005990 polystyrene resin Polymers 0.000 description 1
239000011148 porous material Substances 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229960001225 rifampicin Drugs 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
239000010902 straw Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 1
229960003604 testosterone Drugs 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
239000003106 tissue adhesive Substances 0.000 description 1
238000004448 titration Methods 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
YFDSDPIBEUFTMI-UHFFFAOYSA-N tribromoethanol Chemical compound OCC(Br)(Br)Br YFDSDPIBEUFTMI-UHFFFAOYSA-N 0.000 description 1
229950004616 tribromoethanol Drugs 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Virology (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Oncology (AREA)
Pharmacology & Pharmacy (AREA)
Communicable Diseases (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Biotechnology (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

BG108272A 2001-04-19 2003-10-14 Арилсулфонамиди като противовирусни средства BG108272A (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10119137		2001-04-19
DE10148598A DE10148598A1 (de)	2001-04-19	2001-10-02	Neue Arylsulfonamide als antivirale Mittel

Publications (1)

Publication Number	Publication Date
BG108272A true BG108272A (bg)	2004-10-29

Family

ID=26009118

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG108272A BG108272A (bg)	2001-04-19	2003-10-14	Арилсулфонамиди като противовирусни средства

Country Status (20)

Country	Link
US (1)	US7115612B2 (ja)
EP (1)	EP1383749B1 (ja)
JP (1)	JP4480941B2 (ja)
CN (1)	CN1516695A (ja)
AT (1)	ATE308529T1 (ja)
BG (1)	BG108272A (ja)
BR (1)	BR0209054A (ja)
CA (1)	CA2444123C (ja)
DE (1)	DE50204780D1 (ja)
EE (1)	EE200300515A (ja)
ES (1)	ES2252455T3 (ja)
HU (1)	HUP0303813A3 (ja)
IL (1)	IL158324A0 (ja)
MX (1)	MXPA03009548A (ja)
NO (1)	NO20034667L (ja)
PL (1)	PL363990A1 (ja)
RU (1)	RU2003133750A (ja)
SK (1)	SK12662003A3 (ja)
UY (1)	UY27263A1 (ja)
WO (1)	WO2002085869A1 (ja)

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NZ537980A (en) *	2002-08-23	2007-08-31	Rigel Pharmaceuticals Inc	Pyridyl substituted heterocycles useful for treating or preventing HCV infection
DE10319612A1 (de)	2003-05-02	2004-11-18	Bayer Healthcare Ag	Substituierte Dihydrochinazoline
SI3549936T1 (sl)	2003-04-11	2021-09-30	Ptc Therapeutics, Inc.	Spojina 1,2,4-oksadiazol benzojske kisline in njena uporaba za supresijo nesmiselne mutacije in zdravljenje bolezni
DE102006009928A1 (de) *	2006-03-03	2007-09-06	Aicuris Gmbh & Co. Kg	Substituierte Arylsulfonamide
RU2462246C2 (ru)	2006-03-30	2012-09-27	ПиТиСи ТЕРАПЬЮТИКС, ИНК.	Способы получения функционального белка из днк, имеющей нонсенс-мутацию, и лечения нарушений, ассоциированных с ней
US20080255203A1 (en) *	2007-04-12	2008-10-16	Abbott Laboratories	Heterocyclic compounds and their methods of use
JP2010531850A (ja) *	2007-07-02	2010-09-30	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	新規化合物
EP2177521A1 (en) *	2008-10-14	2010-04-21	Almirall, S.A.	New 2-Amidothiadiazole Derivatives
EP2202232A1 (en) *	2008-12-26	2010-06-30	Laboratorios Almirall, S.A.	1,2,4-oxadiazole derivatives and their therapeutic use
ES2626601T3 (es) *	2010-06-28	2017-07-25	Bayer Intellectual Property Gmbh	Compuestos heterocíclicos como pesticidas
EP2593434A1 (en)	2010-07-16	2013-05-22	Purdue Pharma LP	Pyridine compounds as sodium channel blockers
WO2013136170A1 (en)	2012-03-16	2013-09-19	Purdue Pharma L.P.	Substituted pyridines as sodium channel blockers
JP6482466B2 (ja)	2012-11-03	2019-03-13	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	サイトメガロウイルスの阻害剤
US9334249B2 (en)	2012-11-03	2016-05-10	Boehringer Ingelheim International Gmbh	Inhibitors of cytomegalovirus
WO2014096941A1 (en)	2012-12-20	2014-06-26	Purdue Pharma L.P.	Cyclic sulfonamides as sodium channel blockers
TWI636978B (zh)	2014-03-06	2018-10-01	美商Ｐｔｃ治療公司	１，２，４－二唑苯甲酸之鹽及醫藥組合物
US10730866B2 (en)	2014-04-07	2020-08-04	Purdue Pharma L.P.	Indole derivatives and use thereof
JP6749344B2 (ja) *	2015-02-13	2020-09-02	アジエンダ・オスペダリエラ・ウニベルシタリア・セネーゼ	治療剤としてのヒトヘリカーゼｄｄｘ３阻害剤
US10517853B2 (en)	2015-10-30	2019-12-31	Ptc Therapeutics, Inc.	Methods for treating epilepsy

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DE19802437A1 (de)	1998-01-23	1999-07-29	Bayer Ag	Verwendung von substituierten Sulfonamiden als anitvirale Mittel und neue Stoffe
EP1172361A4 (en)	1999-04-19	2002-05-08	Shionogi & Co	SULFONAMIDE DERIVATIVES HAVING OXADIAZOLE CORES

2002
- 2002-04-08 JP JP2002583396A patent/JP4480941B2/ja not_active Expired - Lifetime
- 2002-04-08 IL IL15832402A patent/IL158324A0/xx unknown
- 2002-04-08 WO PCT/EP2002/003858 patent/WO2002085869A1/de active IP Right Grant
- 2002-04-08 US US10/474,916 patent/US7115612B2/en not_active Expired - Lifetime
- 2002-04-08 RU RU2003133750/04A patent/RU2003133750A/ru not_active Application Discontinuation
- 2002-04-08 MX MXPA03009548A patent/MXPA03009548A/es unknown
- 2002-04-08 HU HU0303813A patent/HUP0303813A3/hu unknown
- 2002-04-08 BR BR0209054-6A patent/BR0209054A/pt not_active IP Right Cessation
- 2002-04-08 ES ES02730119T patent/ES2252455T3/es not_active Expired - Lifetime
- 2002-04-08 AT AT02730119T patent/ATE308529T1/de not_active IP Right Cessation
- 2002-04-08 EE EEP200300515A patent/EE200300515A/xx unknown
- 2002-04-08 SK SK1266-2003A patent/SK12662003A3/sk unknown
- 2002-04-08 CN CNA028121589A patent/CN1516695A/zh active Pending
- 2002-04-08 CA CA2444123A patent/CA2444123C/en not_active Expired - Lifetime
- 2002-04-08 DE DE50204780T patent/DE50204780D1/de not_active Expired - Lifetime
- 2002-04-08 PL PL02363990A patent/PL363990A1/xx not_active Application Discontinuation
- 2002-04-08 EP EP02730119A patent/EP1383749B1/de not_active Expired - Lifetime
- 2002-04-17 UY UY27263A patent/UY27263A1/es not_active Application Discontinuation
2003
- 2003-10-14 BG BG108272A patent/BG108272A/bg unknown
- 2003-10-17 NO NO20034667A patent/NO20034667L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
HUP0303813A2 (hu)	2004-03-29
ATE308529T1 (de)	2005-11-15
CA2444123C (en)	2010-09-21
NO20034667D0 (no)	2003-10-17
JP2004531536A (ja)	2004-10-14
DE50204780D1 (de)	2005-12-08
WO2002085869A1 (de)	2002-10-31
SK12662003A3 (sk)	2004-04-06
JP4480941B2 (ja)	2010-06-16
EP1383749A1 (de)	2004-01-28
UY27263A1 (es)	2002-11-29
EP1383749B1 (de)	2005-11-02
US7115612B2 (en)	2006-10-03
MXPA03009548A (es)	2004-05-24
US20040176374A1 (en)	2004-09-09
NO20034667L (no)	2003-12-12
EE200300515A (et)	2004-02-16
CN1516695A (zh)	2004-07-28
CA2444123A1 (en)	2002-10-31
BR0209054A (pt)	2004-04-20
PL363990A1 (en)	2004-11-29
ES2252455T3 (es)	2006-05-16
HUP0303813A3 (en)	2005-05-30
RU2003133750A (ru)	2005-05-10
IL158324A0 (en)	2004-05-12

Publication	Publication Date	Title
BG108272A (bg)	2004-10-29	Арилсулфонамиди като противовирусни средства
AU2010307006B2 (en)	2016-08-11	Hematopoietic growth factor mimetic small molecule compounds and their uses
JP5379132B2 (ja)	2013-12-25	イミダゾ−、ピラゾロピラジン類およびイミダゾトリアジン類およびそれらの使用
KR20040070348A (ko)	2004-08-07	Ｈｃｖ 감염 치료용으로 유용한 치환된 디페닐헤테로사이클
CZ20012297A3 (cs)	2002-09-11	Piperidiny jako modulátory CCR5
CA2608718A1 (en)	2006-11-23	1, 2, 4-triazole derivatives as vasopressin antagonists
KR20030088509A (ko)	2003-11-19	항바이러스제로서의 신규한 아릴술폰아미드
KR20050100615A (ko)	2005-10-19	화합물, 조성물 및 방법
MXPA05005406A (es)	2005-08-03	Compuestos quimicos novedosos.
AU2007344509A1 (en)	2008-07-24	5-([1,3,4] oxadiazol-2-yl)-1H-indazol and 5-([1,3,4] thiadiazol-2-yl)-1H-indazol derivatives as SGK inhibitors for the treatment of diabetes
AU2007216543A1 (en)	2007-08-23	Hetero-bycyclic antiviral compounds
JP2006526656A (ja)	2006-11-24	５員ヘテロ環ベースのｐ−３８阻害剤
JP2010522186A (ja)	2010-07-01	化合物
US20100222363A1 (en)	2010-09-02	Bicyclic Derivatives as P38 Inhibitors
EA016300B1 (ru)	2012-04-30	НОВЫЕ ГЕТЕРОЦИКЛИЧЕСКИЕ ИНГИБИТОРЫ NF-κB
JP2010527999A (ja)	2010-08-19	ＰＫＣ−θ阻害剤としてのプリノン類および１Ｈ−イミダゾピリジノン類
AU2022296371A1 (en)	2024-01-25	Sulfoximide substituted indazole irak4 kinase inhibitor, preparation method therefor, and use thereof
KR20090014223A (ko)	2009-02-06	니코틴성 아세틸콜린 수용체 리간드로서의 2-페닐-5-아미노-1,3,4-옥사디아졸 및 그의 용도
AU2007214602A1 (en)	2007-08-23	Heterocyclic antiviral compounds
JPWO2004111024A1 (ja)	2006-07-20	チアジアゾリン誘導体
JP4481003B2 (ja)	2010-06-16	ヘテロシクリルアリールスルホンアミド類
CZ279559B6 (cs)	1995-05-17	Deriváty amidů kyseliny thiazolidinkarboxylové mající antialergickou aktivitu,jejich příprava a použití
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