CZ365392A3 - Sulfonimidamide derivative, process for preparing thereof and a pharmaceutical preparation in which it is contained - Google Patents

Sulfonimidamide derivative, process for preparing thereof and a pharmaceutical preparation in which it is contained Download PDF

Info

Publication number: CZ365392A3
Authority: CZ; Czechia
Prior art keywords: group; carbonyl; methyl; hydrogen; formula
Prior art date: 1991-12-20

Application number

CS923653A

Other languages

Czech (cs)

English (en)

Inventor

James Edward Ray

John Eldon Toth

Original Assignee

Lilly Co Eli

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.)

1991-12-20

Filing date

1992-12-14

Publication date

1993-10-13

1992-12-14 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1993-10-13 Publication of CZ365392A3 publication Critical patent/CZ365392A3/cs

Links

239000000825 pharmaceutical preparation Substances 0.000 title description 5
238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 58
239000000460 chlorine Substances 0.000 claims abstract description 57
238000000034 method Methods 0.000 claims abstract description 35
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 24
229910052801 chlorine Inorganic materials 0.000 claims abstract description 18
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 17
150000003839 salts Chemical class 0.000 claims abstract description 13
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 12
229910052794 bromium Inorganic materials 0.000 claims abstract description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 10
239000002246 antineoplastic agent Substances 0.000 claims abstract description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 6
230000008569 process Effects 0.000 claims abstract description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 4
125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
229940034982 antineoplastic agent Drugs 0.000 claims abstract description 4
229910052740 iodine Inorganic materials 0.000 claims abstract description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 3
239000011630 iodine Chemical group 0.000 claims abstract description 3
206010028980 Neoplasm Diseases 0.000 claims description 43
-1 group Substances 0.000 claims description 42
229910052739 hydrogen Inorganic materials 0.000 claims description 39
239000001257 hydrogen Substances 0.000 claims description 29
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 20
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 20
239000004480 active ingredient Substances 0.000 claims description 19
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
150000002431 hydrogen Chemical class 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 14
229910052799 carbon Inorganic materials 0.000 claims description 13
INOGLHRUEYDAHX-UHFFFAOYSA-N 1-chlorobenzotriazole Chemical compound C1=CC=C2N(Cl)N=NC2=C1 INOGLHRUEYDAHX-UHFFFAOYSA-N 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
201000011510 cancer Diseases 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
239000007800 oxidant agent Substances 0.000 claims description 4
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
230000010933 acylation Effects 0.000 claims description 3
238000005917 acylation reaction Methods 0.000 claims description 3
230000003197 catalytic effect Effects 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
BTCCJSNEWMLWOE-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[(3,4,5-trimethylphenyl)sulfonimidoyl]urea Chemical compound CC1=C(C)C(C)=CC(S(=N)(=O)NC(=O)NC=2C=CC(Cl)=CC=2)=C1 BTCCJSNEWMLWOE-UHFFFAOYSA-N 0.000 claims description 2
JVUYQHDSVZWYKP-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[n-ethyl-s-(4-methylphenyl)sulfonimidoyl]urea Chemical compound C=1C=C(C)C=CC=1S(=O)(=NCC)NC(=O)NC1=CC=C(Cl)C=C1 JVUYQHDSVZWYKP-UHFFFAOYSA-N 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
YOIDHZBOHMNTNP-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1=CC=C(Cl)C=C1 YOIDHZBOHMNTNP-UHFFFAOYSA-N 0.000 claims 1
CSWDCNAHHKISFH-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[(4-chlorophenyl)sulfonimidoyl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NS(=N)(=O)C1=CC=C(Cl)C=C1 CSWDCNAHHKISFH-UHFFFAOYSA-N 0.000 claims 1
QUFVCQSBHRJKFG-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[s-(3,4-dimethylphenyl)-n-methylsulfonimidoyl]urea Chemical compound C=1C=C(C)C(C)=CC=1S(=O)(NC)=NC(=O)NC1=CC=C(Cl)C=C1 QUFVCQSBHRJKFG-UHFFFAOYSA-N 0.000 claims 1
MKZRXMVJTBPROZ-UHFFFAOYSA-N 1-(aminosulfonimidoyl)-2-methylbenzene Chemical compound CC1=CC=CC=C1S(N)(=N)=O MKZRXMVJTBPROZ-UHFFFAOYSA-N 0.000 claims 1
241001556567 Acanthamoeba polyphaga mimivirus Species 0.000 claims 1
230000000118 anti-neoplastic effect Effects 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
125000000068 chlorophenyl group Chemical group 0.000 claims 1
150000002009 diols Chemical group 0.000 claims 1
235000012459 muffins Nutrition 0.000 claims 1
238000007127 saponification reaction Methods 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 20
238000009472 formulation Methods 0.000 abstract description 5
125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 203
239000000047 product Substances 0.000 description 167
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 136
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 117
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 99
238000004458 analytical method Methods 0.000 description 99
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 86
238000005481 NMR spectroscopy Methods 0.000 description 69
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
235000019439 ethyl acetate Nutrition 0.000 description 55
238000000434 field desorption mass spectrometry Methods 0.000 description 55
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 51
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 30
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
229910052760 oxygen Inorganic materials 0.000 description 27
239000007787 solid Substances 0.000 description 27
239000000243 solution Substances 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
238000001953 recrystallisation Methods 0.000 description 17
238000003818 flash chromatography Methods 0.000 description 16
229910052757 nitrogen Inorganic materials 0.000 description 16
IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
DOQQTKLDEQSKIE-UHFFFAOYSA-N silver;isocyanate Chemical compound [Ag+].[N-]=C=O DOQQTKLDEQSKIE-UHFFFAOYSA-N 0.000 description 15
229910021529 ammonia Inorganic materials 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
239000012043 crude product Substances 0.000 description 12
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 10
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000006260 foam Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
238000001035 drying Methods 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 7
229920002472 Starch Polymers 0.000 description 7
239000012267 brine Substances 0.000 description 7
239000002775 capsule Substances 0.000 description 7
238000001914 filtration Methods 0.000 description 7
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
239000002904 solvent Substances 0.000 description 7
235000019698 starch Nutrition 0.000 description 7
239000003826 tablet Substances 0.000 description 7
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
229910004373 HOAc Inorganic materials 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
239000002585 base Substances 0.000 description 6
150000001721 carbon Chemical group 0.000 description 6
239000004615 ingredient Substances 0.000 description 6
235000019359 magnesium stearate Nutrition 0.000 description 6
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
239000008107 starch Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
241000699670 Mus sp. Species 0.000 description 5
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
230000000704 physical effect Effects 0.000 description 5
239000011734 sodium Substances 0.000 description 5
238000001291 vacuum drying Methods 0.000 description 5
229960000549 4-dimethylaminophenol Drugs 0.000 description 4
101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 4
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KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
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238000001816 cooling Methods 0.000 description 4
239000007903 gelatin capsule Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000006467 substitution reaction Methods 0.000 description 4
238000012360 testing method Methods 0.000 description 4
FCZHUROLVAKWCN-FXFZNMOHSA-N (2r,3r,5r,6r,7s)-2,3,5,6-tetrachloro-4,7-bis(dichloromethyl)-7-methylbicyclo[2.2.1]heptane Chemical compound Cl[C@H]1[C@H](Cl)C2(C(Cl)Cl)[C@@H](Cl)[C@H](Cl)C1[C@@]2(C(Cl)Cl)C FCZHUROLVAKWCN-FXFZNMOHSA-N 0.000 description 3
DYYLCPSSSFWEEA-UHFFFAOYSA-N 4-methylbenzenesulfinyl chloride Chemical compound CC1=CC=C(S(Cl)=O)C=C1 DYYLCPSSSFWEEA-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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150000001412 amines Chemical class 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
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238000002512 chemotherapy Methods 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
239000000284 extract Substances 0.000 description 3
238000002513 implantation Methods 0.000 description 3
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125000004433 nitrogen atom Chemical group N* 0.000 description 3
239000002245 particle Substances 0.000 description 3
235000011118 potassium hydroxide Nutrition 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
238000001665 trituration Methods 0.000 description 3
125000006527 (C1-C5) alkyl group Chemical group 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
BAFZLLIWBNCHAI-UHFFFAOYSA-N 3,4,5-trimethylbenzenesulfinyl chloride Chemical compound CC1=CC(S(Cl)=O)=CC(C)=C1C BAFZLLIWBNCHAI-UHFFFAOYSA-N 0.000 description 2
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RQMXKMZHKWLXMQ-UHFFFAOYSA-N 4-ethylbenzenesulfinyl chloride Chemical compound CCC1=CC=C(S(Cl)=O)C=C1 RQMXKMZHKWLXMQ-UHFFFAOYSA-N 0.000 description 2
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229910021607 Silver chloride Inorganic materials 0.000 description 2
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CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000013543 active substance Substances 0.000 description 2
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
210000004556 brain Anatomy 0.000 description 2
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125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
208000035269 cancer or benign tumor Diseases 0.000 description 2
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238000001704 evaporation Methods 0.000 description 2
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238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 2
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Classifications

- 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
- C07C381/10—Compounds containing sulfur atoms doubly-bound to nitrogen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (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)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CS923653A 1991-12-20 1992-12-14 Sulfonimidamide derivative, process for preparing thereof and a pharmaceutical preparation in which it is contained CZ365392A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US81225991A	1991-12-20	1991-12-20

Publications (1)

Publication Number	Publication Date
CZ365392A3 true CZ365392A3 (en)	1993-10-13

Family

ID=25209033

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS923653A CZ365392A3 (en)	1991-12-20	1992-12-14	Sulfonimidamide derivative, process for preparing thereof and a pharmaceutical preparation in which it is contained

Country Status (17)

Country	Link
EP (1)	EP0552553B1 (2)
JP (1)	JP3202373B2 (2)
AU (1)	AU654069B2 (2)
BR (1)	BR9205020A (2)
CA (1)	CA2085297A1 (2)
CZ (1)	CZ365392A3 (2)
DE (1)	DE69221114T2 (2)
ES (1)	ES2104857T3 (2)
FI (1)	FI925693A7 (2)
HU (1)	HUT65746A (2)
IL (1)	IL104088A0 (2)
MX (1)	MX9207264A (2)
NO (1)	NO924848L (2)
NZ (1)	NZ245458A (2)
TW (1)	TW221049B (2)
YU (1)	YU107692A (2)
ZA (1)	ZA929699B (2)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP7349981B2 (ja) *	2017-07-24	2023-09-25	ノバルティスアーゲー	Ｎｌｒｐ活性に関連する状態を治療するための化合物及び組成物
ES2988798T3 (es) *	2017-07-24	2024-11-21	Novartis Ag	Compuestos y composiciones para el tratamiento de afecciones asociadas a la actividad de NLRP
EP3692020A1 (en)	2017-10-03	2020-08-12	Inflazome Limited	Novel compounds
AU2019299444A1 (en) *	2018-07-03	2021-01-14	Novartis Ag	Methods of treating or selecting a treatment for a subject resistant to tnf inhibitor using a NLRP3 antagonist
EP3880673B1 (en)	2018-11-13	2024-01-03	Novartis AG	Compounds and compositions for treating conditions associated with nlrp activity
US12134611B2 (en)	2018-11-13	2024-11-05	Novartis Ag	Compounds and compositions for treating conditions associated with NLRP activity
WO2020102574A1 (en) *	2018-11-16	2020-05-22	Novartis Inflammasome Research, Inc.	The compounds and compositions for treating conditions associated with nlrp activity
WO2021002887A1 (en) *	2019-07-02	2021-01-07	Novartis Inflammasome Research, Inc.	Gut-targeted nlrp3 antagonists and their use in therapy

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4666506A (en)	1984-08-08	1987-05-19	E. I. Du Pont De Nemours And Company	Herbicidal pyrimidines
IL83215A (en) *	1986-07-23	1991-12-15	Lilly Co Eli	Synthesis of bicyclic heteroaromatic sulfonyl chlorides
US5187189A (en) *	1991-01-22	1993-02-16	American Home Products Corporation	S-aminoalkyl-s-arylsulfoximines as antiarrhythmic agents
US5140026A (en) *	1991-05-09	1992-08-18	A. H. Robins Company, Incorporated	N-aminoalkyl-S-aryl-S-alkyl (or substituted alkyl) sulfoximines as antiarrhythmic agents

1992
- 1992-12-14 ZA ZA929699A patent/ZA929699B/xx unknown
- 1992-12-14 IL IL104088A patent/IL104088A0/xx unknown
- 1992-12-14 CZ CS923653A patent/CZ365392A3/cs unknown
- 1992-12-14 CA CA002085297A patent/CA2085297A1/en not_active Abandoned
- 1992-12-14 NZ NZ245458A patent/NZ245458A/en unknown
- 1992-12-14 TW TW081109989A patent/TW221049B/zh active
- 1992-12-15 DE DE69221114T patent/DE69221114T2/de not_active Expired - Fee Related
- 1992-12-15 HU HU9203971A patent/HUT65746A/hu unknown
- 1992-12-15 FI FI925693A patent/FI925693A7/fi not_active Application Discontinuation
- 1992-12-15 AU AU30181/92A patent/AU654069B2/en not_active Ceased
- 1992-12-15 ES ES92311447T patent/ES2104857T3/es not_active Expired - Lifetime
- 1992-12-15 MX MX9207264A patent/MX9207264A/es unknown
- 1992-12-15 NO NO92924848A patent/NO924848L/no unknown
- 1992-12-15 BR BR9205020A patent/BR9205020A/pt not_active Application Discontinuation
- 1992-12-15 EP EP92311447A patent/EP0552553B1/en not_active Expired - Lifetime
- 1992-12-16 YU YU107692A patent/YU107692A/sh unknown
- 1992-12-16 JP JP33625392A patent/JP3202373B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
DE69221114D1 (de)	1997-08-28
FI925693A0 (fi)	1992-12-15
ZA929699B (en)	1994-06-14
YU107692A (sh)	1995-12-04
AU3018192A (en)	1993-06-24
TW221049B (2)	1994-02-11
IL104088A0 (en)	1993-05-13
NO924848L (no)	1993-06-21
EP0552553A1 (en)	1993-07-28
EP0552553B1 (en)	1997-07-23
MX9207264A (es)	1993-12-01
HU9203971D0 (en)	1993-04-28
HUT65746A (en)	1994-07-28
CA2085297A1 (en)	1993-06-21
NZ245458A (en)	1995-04-27
BR9205020A (pt)	1993-06-22
DE69221114T2 (de)	1997-12-11
NO924848D0 (no)	1992-12-15
ES2104857T3 (es)	1997-10-16
JP3202373B2 (ja)	2001-08-27
FI925693A7 (fi)	1993-06-21
AU654069B2 (en)	1994-10-20
JPH05345756A (ja)	1993-12-27

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