CZ20012528A3 - 1-Heterocyklicky substituované diarylaminy, farmaceutické kompozice na jejich bázi a způsoby léčení - Google Patents
1-Heterocyklicky substituované diarylaminy, farmaceutické kompozice na jejich bázi a způsoby léčení Download PDFInfo
- Publication number
- CZ20012528A3 CZ20012528A3 CZ20012528A CZ20012528A CZ20012528A3 CZ 20012528 A3 CZ20012528 A3 CZ 20012528A3 CZ 20012528 A CZ20012528 A CZ 20012528A CZ 20012528 A CZ20012528 A CZ 20012528A CZ 20012528 A3 CZ20012528 A3 CZ 20012528A3
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- CZ
- Czechia
- Prior art keywords
- methyl
- iodo
- fluoro
- phenyl
- benzenesulfonamide
- Prior art date
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- 238000000034 method Methods 0.000 title abstract description 18
- 125000005266 diarylamine group Chemical group 0.000 title abstract description 5
- 238000011282 treatment Methods 0.000 title description 8
- 239000008194 pharmaceutical composition Substances 0.000 title description 5
- 239000000203 mixture Substances 0.000 abstract description 27
- -1 hydrocarbon radicals Chemical class 0.000 description 384
- 150000001875 compounds Chemical class 0.000 description 49
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 102000004232 Mitogen-Activated Protein Kinase Kinases Human genes 0.000 description 23
- 108090000744 Mitogen-Activated Protein Kinase Kinases Proteins 0.000 description 23
- 125000000217 alkyl group Chemical group 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 150000001408 amides Chemical class 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- DBAMGXGOUQVLEV-UHFFFAOYSA-N 5-[6-(2-chloro-4-iodoanilino)-7-fluoro-1,3-dihydro-2-benzothiophen-5-yl]-3h-1,3,4-oxadiazol-2-one Chemical compound O1C(O)=NN=C1C(C(=C1F)NC=2C(=CC(I)=CC=2)Cl)=CC2=C1CSC2 DBAMGXGOUQVLEV-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
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- 108091000080 Phosphotransferase Proteins 0.000 description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
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- AOSLGLAFPKSSNJ-UHFFFAOYSA-N 5-(3-amino-1,2-oxazol-5-yl)-2,3-difluoro-4-(4-iodo-2-methylanilino)benzenesulfonamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(S(N)(=O)=O)C=C1C1=CC(N)=NO1 AOSLGLAFPKSSNJ-UHFFFAOYSA-N 0.000 description 8
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- KISWVXRQTGLFGD-UHFFFAOYSA-N 2-[[2-[[6-amino-2-[[2-[[2-[[5-amino-2-[[2-[[1-[2-[[6-amino-2-[(2,5-diamino-5-oxopentanoyl)amino]hexanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-(diaminomethylideneamino)p Chemical compound C1CCN(C(=O)C(CCCN=C(N)N)NC(=O)C(CCCCN)NC(=O)C(N)CCC(N)=O)C1C(=O)NC(CO)C(=O)NC(CCC(N)=O)C(=O)NC(CCCN=C(N)N)C(=O)NC(CO)C(=O)NC(CCCCN)C(=O)NC(C(=O)NC(CC(C)C)C(O)=O)CC1=CC=C(O)C=C1 KISWVXRQTGLFGD-UHFFFAOYSA-N 0.000 description 7
- CKQFDRMKSBKNTR-UHFFFAOYSA-N 5-(3-amino-1,2-oxazol-4-yl)-4-(2-chloro-4-iodoanilino)-2,3-difluorobenzenesulfonamide Chemical compound NC1=NOC=C1C1=CC(S(N)(=O)=O)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl CKQFDRMKSBKNTR-UHFFFAOYSA-N 0.000 description 7
- YALWEHBJSHKOGV-UHFFFAOYSA-N 5-(5-amino-1,3,4-oxadiazol-2-yl)-4-(2-chloro-4-iodoanilino)-2-fluorobenzenesulfonamide Chemical compound O1C(N)=NN=C1C1=CC(S(N)(=O)=O)=C(F)C=C1NC1=CC=C(I)C=C1Cl YALWEHBJSHKOGV-UHFFFAOYSA-N 0.000 description 7
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- 230000004913 activation Effects 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 6
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- 238000012360 testing method Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
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- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
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Classifications
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- C07D291/00—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms
- C07D291/02—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms not condensed with other rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
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- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
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- Immunology (AREA)
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- Oncology (AREA)
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- Urology & Nephrology (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11587599P | 1999-01-13 | 1999-01-13 | |
| US12242099P | 1999-03-02 | 1999-03-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CZ20012528A3 true CZ20012528A3 (cs) | 2002-06-12 |
Family
ID=26813666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ20012528A CZ20012528A3 (cs) | 1999-01-13 | 1999-12-21 | 1-Heterocyklicky substituované diarylaminy, farmaceutické kompozice na jejich bázi a způsoby léčení |
Country Status (29)
| Country | Link |
|---|---|
| US (2) | US6545030B1 (enExample) |
| EP (1) | EP1144394B1 (enExample) |
| JP (1) | JP2002534515A (enExample) |
| KR (1) | KR20010108093A (enExample) |
| CN (1) | CN1149204C (enExample) |
| AP (1) | AP2001002225A0 (enExample) |
| AT (1) | ATE302761T1 (enExample) |
| AU (1) | AU2482700A (enExample) |
| BG (1) | BG105801A (enExample) |
| BR (1) | BR9916896A (enExample) |
| CA (1) | CA2355374A1 (enExample) |
| CZ (1) | CZ20012528A3 (enExample) |
| DE (1) | DE69926914T2 (enExample) |
| EA (1) | EA200100773A1 (enExample) |
| EE (1) | EE200100374A (enExample) |
| ES (1) | ES2249060T3 (enExample) |
| GE (1) | GEP20032999B (enExample) |
| HR (1) | HRP20010525A2 (enExample) |
| HU (1) | HUP0105092A3 (enExample) |
| IL (1) | IL144215A0 (enExample) |
| IS (1) | IS5975A (enExample) |
| MA (1) | MA26770A1 (enExample) |
| NO (1) | NO20013451L (enExample) |
| NZ (1) | NZ513432A (enExample) |
| OA (1) | OA11819A (enExample) |
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| SK (1) | SK9822001A3 (enExample) |
| TR (1) | TR200102029T2 (enExample) |
| WO (1) | WO2000042029A1 (enExample) |
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-
1999
- 1999-12-21 EP EP99968150A patent/EP1144394B1/en not_active Expired - Lifetime
- 1999-12-21 HR HR20010525A patent/HRP20010525A2/hr not_active Application Discontinuation
- 1999-12-21 WO PCT/US1999/030416 patent/WO2000042029A1/en not_active Ceased
- 1999-12-21 OA OA1200100185A patent/OA11819A/en unknown
- 1999-12-21 JP JP2000593597A patent/JP2002534515A/ja not_active Abandoned
- 1999-12-21 AU AU24827/00A patent/AU2482700A/en not_active Abandoned
- 1999-12-21 HU HU0105092A patent/HUP0105092A3/hu unknown
- 1999-12-21 KR KR1020017008828A patent/KR20010108093A/ko not_active Withdrawn
- 1999-12-21 IL IL14421599A patent/IL144215A0/xx unknown
- 1999-12-21 CZ CZ20012528A patent/CZ20012528A3/cs unknown
- 1999-12-21 TR TR2001/02029T patent/TR200102029T2/xx unknown
- 1999-12-21 CA CA002355374A patent/CA2355374A1/en not_active Abandoned
- 1999-12-21 ES ES99968150T patent/ES2249060T3/es not_active Expired - Lifetime
- 1999-12-21 EA EA200100773A patent/EA200100773A1/ru unknown
- 1999-12-21 PL PL99348870A patent/PL348870A1/xx not_active Application Discontinuation
- 1999-12-21 BR BR9916896-0A patent/BR9916896A/pt not_active Application Discontinuation
- 1999-12-21 NZ NZ513432A patent/NZ513432A/xx unknown
- 1999-12-21 DE DE69926914T patent/DE69926914T2/de not_active Expired - Fee Related
- 1999-12-21 SK SK982-2001A patent/SK9822001A3/sk unknown
- 1999-12-21 AT AT99968150T patent/ATE302761T1/de not_active IP Right Cessation
- 1999-12-21 US US09/889,104 patent/US6545030B1/en not_active Expired - Fee Related
- 1999-12-21 CN CNB998156191A patent/CN1149204C/zh not_active Expired - Fee Related
- 1999-12-21 AP APAP/P/2001/002225A patent/AP2001002225A0/en unknown
- 1999-12-21 GE GEAP19996049A patent/GEP20032999B/en unknown
- 1999-12-21 EE EEP200100374A patent/EE200100374A/xx unknown
-
2001
- 2001-06-22 IS IS5975A patent/IS5975A/is unknown
- 2001-07-12 NO NO20013451A patent/NO20013451L/no not_active Application Discontinuation
- 2001-08-09 BG BG105801A patent/BG105801A/bg unknown
- 2001-08-10 MA MA26292A patent/MA26770A1/fr unknown
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2002
- 2002-07-23 US US10/201,146 patent/US20030004193A1/en not_active Abandoned
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