WO1999032463A1 - INHIBITION OF p38 KINASE USING SYMMETRICAL AND UNSYMMETRICAL DIPHENYL UREAS - Google Patents
INHIBITION OF p38 KINASE USING SYMMETRICAL AND UNSYMMETRICAL DIPHENYL UREAS Download PDFInfo
- Publication number
- WO1999032463A1 WO1999032463A1 PCT/US1998/027265 US9827265W WO9932463A1 WO 1999032463 A1 WO1999032463 A1 WO 1999032463A1 US 9827265 W US9827265 W US 9827265W WO 9932463 A1 WO9932463 A1 WO 9932463A1
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- WO
- WIPO (PCT)
- Prior art keywords
- urea
- halogen
- alkyl
- methoxyphenyl
- phenyl
- Prior art date
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- 0 Cc(cc1)ccc1NC(Nc(cc(cc1)S(*)(=O)=O)c1OC)=O Chemical compound Cc(cc1)ccc1NC(Nc(cc(cc1)S(*)(=O)=O)c1OC)=O 0.000 description 8
- JTPZTKBRUCILQD-UHFFFAOYSA-N CN(CCN1)C1=O Chemical compound CN(CCN1)C1=O JTPZTKBRUCILQD-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N CN(CCC1)C1=O Chemical compound CN(CCC1)C1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- BVQMUAAELWHQSF-UHFFFAOYSA-N CC(C)(C)OC(Nc1ccc(Cc(cc2)ccc2N)cc1)=O Chemical compound CC(C)(C)OC(Nc1ccc(Cc(cc2)ccc2N)cc1)=O BVQMUAAELWHQSF-UHFFFAOYSA-N 0.000 description 1
- PPLCOMGNLPEPRO-UHFFFAOYSA-N CC(C)(C)OC(Nc1ccc(Cc(cc2)ccc2[N+]([O-])=O)cc1)=O Chemical compound CC(C)(C)OC(Nc1ccc(Cc(cc2)ccc2[N+]([O-])=O)cc1)=O PPLCOMGNLPEPRO-UHFFFAOYSA-N 0.000 description 1
- BSCQIKFZFGQIFQ-UHFFFAOYSA-N CC(C)(C)c(cc1N)ccc1OCC(N1CC=[O]CC1)=O Chemical compound CC(C)(C)c(cc1N)ccc1OCC(N1CC=[O]CC1)=O BSCQIKFZFGQIFQ-UHFFFAOYSA-N 0.000 description 1
- KYEACNNYFNZCST-UHFFFAOYSA-N CN(C(CC1)=O)C1=O Chemical compound CN(C(CC1)=O)C1=O KYEACNNYFNZCST-UHFFFAOYSA-N 0.000 description 1
- WFCGUFNWWIAHAK-UHFFFAOYSA-N Cc(cc1)ncc1Oc1cccc(N)c1 Chemical compound Cc(cc1)ncc1Oc1cccc(N)c1 WFCGUFNWWIAHAK-UHFFFAOYSA-N 0.000 description 1
- XYZKXQHSXCNURY-UHFFFAOYSA-N Nc1ccc(Cc2cnccc2)cc1 Chemical compound Nc1ccc(Cc2cnccc2)cc1 XYZKXQHSXCNURY-UHFFFAOYSA-N 0.000 description 1
- GPIUUMROPXDNRH-UHFFFAOYSA-N O=C(C1C2C3C=CC1C3)NC2=O Chemical compound O=C(C1C2C3C=CC1C3)NC2=O GPIUUMROPXDNRH-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N O=C1NCCC1 Chemical compound O=C1NCCC1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- DGFKBUUOLHCUBO-UHFFFAOYSA-M [O-][N+](C1=CC=CC(S[AlH2])=CC=C1)=O Chemical compound [O-][N+](C1=CC=CC(S[AlH2])=CC=C1)=O DGFKBUUOLHCUBO-UHFFFAOYSA-M 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
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- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
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- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
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- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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- C07C205/20—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C07C205/21—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings having nitro groups and hydroxy groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C205/22—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings having nitro groups and hydroxy groups bound to carbon atoms of the same non-condensed six-membered aromatic ring having one nitro groups bound to the ring
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- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
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- C07C205/38—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. nitrodiphenyl ethers
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Definitions
- the mitogen-activated protein (MAP) kinase family is made up of a series of structurally related proline-directed serine/threonine kinases which are activated either by growth factors (such as EGF) and phorbol esters (ERK), or by IL-1, TNF ⁇ or stress ( ⁇ 38, JNK).
- the MAP kinases are responsible for the activation of a wide variety of transcription factors and proteins involved in transcriptional control of cytokine production.
- a pair of novel protein kinases involved in the regulation of cytokine synthesis was recently described by a group from SmithKline Beecham (Lee et al. Nature 1994, 372, 739).
- CSAJDSs cytokine suppressive anti-inflammatory drugs
- HIN human immunodeficiency virus
- the compounds of formula I are of formula la
- R 3 , R 4 , R 5 and R 6 are each independently H, halogen, C 0 - alkyl optionally substituted by halogen, up to perhalo, C,. 10 -alkoxy, optionally substituted by at least one hydroxy group or by halogen, up to perhalo; C ⁇ ,- aryl, optionally substituted by C,. 10 alkoxy or halogen, C 5 -, 2 hetaryl, optionally substitued by C,- 10 alkyl, C,. 10 alkoxy or halogen; NO 2 , SO 2 F or -SO 2 CH p X 3 .
- Y is phenyl, pyridyl, naphthyl, pyridone, pyrazine, benzodixane, benzopyridine ⁇ pyrimidine or benzothiazole, each optionally substituted by C ⁇ _ 10 -alkyl,
- Suitable alkyl groups and alkyl portions of groups, e.g., alkoxy, etc. throughout include methyl, ethyl, propyl, butyl, etc., including all straight-chain and branched isomers such as isopropyl, isobutyl, sec-butyl, tert-butyl, etc.
- Suitable aryl groups include, for example, phenyl and 1- and 2-naphthyl.
- R 3 is Cl, F, C ⁇ -branched alkyl, -SO 2 F or -SO 2 CF 3 ; and R 6 is hydroxy; C ⁇ o -alkoxy optionally substituted by at least one hydroxy group; -COOR 1 ; - OR'CONHR 1 ; -NHCOR 1 ; -SR 1 ; phenyl optionally substituted by halo or C,. I0 -alkoxy; NH 2 ; furyloxy,
- Preferred 2-naphthyl ureas are:
- pharmaceutically acceptable salts include acid salts of inorganic bases, such as salts containing alkaline cations (e.g., Li + Na + or K + ), alkaline earth cations (e.g., Mg +2 , Ca +2 or Ba +2 ), the ammonium cation, as well as acid salts of organic bases, including aliphatic and aromatic substituted ammonium, and quaternary ammonium cations, such as those arising from protonation or peralkylation of triethylamine, N,N-diethylamine, NN-dicyclohexylamine, pyridine, N,N- dimethylaminopyridine (DMAP), l,4-diazabiclo[2.2.2]octane (DABCO), 1,5- diazabicyclo[4.3.0]non-5-ene (DB ⁇ ) and l,8-diazabicyclo[5.4.0]undec-7-ene (DBU).
- H 2 / catalyst eg. Ni, Pd, Pt
- the optimal course of treatment i.e., the mode of treatment and the daily number of doses of a compound of Formula I or a pharmaceutically acceptable salt thereof given for a defined number of days, can be ascertained by those skilled in the art using conventional course of treatnce tests.
- Step 3 4-tert-Butyl-2-methoxyaniline: A solution of 2-nitro-5-tert-butylanisole (3.95 g, 18.9 mmol) in MeOH (65 mL) and added to a flask containing 10% Pd/C in MeOH (0.400 g), then placed under a H 2 atmosphere (balloon).
- Step 4.2-Amino-3-methoxynaphthalene A slurry of 2-(N-(carbobenzyloxy)amino-3- methoxynaphthalene (5.0 g, 16.3 mmol) and 10% Pd/C (0.5 g) in EtOAc (70mL) was maintained under a H 2 atmospheric (balloon) at room temp, overnight.
- Step 1.5-te/*-Buryl-2-(trifluoromethanesulfonyI)oxy-l-nitrobenzene To an ice cold solution of 4-tert-butyl-2-nitrophenol (6.14 g, 31.5 mmol) and pyridine (10 mL, 125 mmol) in CH 2 C1 2 (50 mL) was slowly added trifluoromethanesulfonic anhydride (10 g, 35.5 mmol) via syringe. The reaction mixture was stirred for 15 min, then allowed to warm up to room temp, and diluted with CH 2 C1 2 (100 mL).
- Step 1 4-(6-Methyl-3-pyridinyloxy)-l-nitrobenzene: To a solution of 5-hydroxy-2- methylpyridine (5.0 g, 45.8 mmol) and l-fluoro-4-nitrobenzene (6.5 g, 45.8 mmol) in anh DMF (50 mL) was added K 2 CO 3 (13.0 g, 91.6 mmol) in one portion. The mixture was heated at the reflux temp, with stirring for 18 h and then allowed to cool to room temp. The resulting mixture was poured into water (200 mL) and extracted with EtOAc (3 x 150 mL).
- Step 2 5-Hydroxy-2-methoxypyridine: To a stirred solution of 5-bromo-2- methoxypyridine (8.9 g, 47.9 mmol) in THF (175 mL) at -78 °C was added an n- butyllithium solution (2.5 M in hexane; 28.7 mL, 71.8 mmol) dropwise and the resulting mixture was allowed to stir at -78 °C for 45 min. Trimethyl borate (7.06 mL, 62.2 mmol) was added via syringe and the resulting mixture was stirred for an additional 2 h. The bright orange reaction mixture was warmed to 0 °C and was treated with a mixture of a 3 N NaOH solution (25 mL, 71.77 mmol) and a hydrogen peroxide solution (30%; approx.
- Step 2 3-(4-Pyridinyl)methyIaniline: 3-(4-Nitrobenzyl)pyridine was reduced to the aniline in a manner analogous to that described in Method Bl .
- N-(2-Methoxy-5-(trifluoromethyl)phenyl)-N , -(4-(4-pyridinyIthio)phenyl)urea To a solution of pyridine (0.61 mL, 7.5 mmol, 3.0 equiv) and phosgene (20% in toluene; 2.65 mL, 5.0 mmol, 2.0 equiv) in CH 2 C1 2 (20 mL) was added 4-(4-pyridinylthio)aniline (0.506 g, 2.5 mmol) at 0 °C. After stirring for 3 h at room temp., the mixture was treated with anh. toluene (100 mL) then concentrated under reduced pressure.
- N-(3-Methoxy-2-naphthyl)-N'-(4-methylphenyl)urea To a solution of 3-methoxy-2- naphthoic acid (Method A6, Step 2; 0.762 g, 3.80 mmol) and Et 3 N (0.588 mL, 4.2 mmol) in anh toluene (20 mL) at room temp, was added a solution of diphenylphosphoryl azide (1.16 g, 4.2 mmol) in toluene (5 mL). The resulting mixture was heated to 80 °C for 2 h, cooled to room temp., and p -toluidine (0.455 g, 4.1 mmol) was added.
- the residue was purified by column chromatography (gradient form 100% CH 2 C1 2 to 5% MeOH/95% CH 2 C1 2 ) to give bis(4-chloro-3- (trifluoromethyl)phenyl)urea followed by N-(3-tert-butyl-5-isoxazolyl)-N'-(4-chloro-3- (trifluoromethyl)phenyl)urea.
- the residue from the symmetrical urea fractions was triturated (Et,O/hexane) to give the urea as a white solid (0.110 g): TLC (3% MeOH/97% CH 2 C1 2 ) R O.55; FAB-MS m/z 417 ((M+H) + ).
- N-(5-tert-Butyl-2-methoxyphenyl)-N'-(2-amino-4-methylphenyI)urea A solution of N-(5-tert-butyl-2-methoxyphenyl)-N'-(2-nitro-4-methylphenyl)urea (prepared in a manner analogous to Method Bla; 4.0 g, 11.2 mmol) in EtOH (100 mL) was added to a slurry of 10% Pd/C (0.40 g) in EtOH (10 mL), and the resulting mixture was stirred under an atmosphere of H 2 (balloon) at room temp, for 18 h.
Abstract
Description
Claims
Priority Applications (13)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK98964221T DK1042305T3 (en) | 1997-12-22 | 1998-12-22 | Inhibition of p38 kinase using symmetric and asymmetric diphenylureas |
IL13673798A IL136737A0 (en) | 1997-12-22 | 1998-12-22 | Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas |
DE1042305T DE1042305T1 (en) | 1997-12-22 | 1998-12-22 | INHIBITION OF p38 KINASE USING SYMMETRIC AND ASYMMETRIC DIPHENYL UREAS |
SI9830784T SI1042305T1 (en) | 1997-12-22 | 1998-12-22 | INHIBITION OF p38 KINASE USING SYMMETRICAL AND UNSYMMETRICAL DIPHENYL UREAS |
CA2315715A CA2315715C (en) | 1997-12-22 | 1998-12-22 | Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas |
EP98964221A EP1042305B1 (en) | 1997-12-22 | 1998-12-22 | INHIBITION OF p38 KINASE USING SYMMETRICAL AND UNSYMMETRICAL DIPHENYL UREAS |
AU19399/99A AU1939999A (en) | 1997-12-22 | 1998-12-22 | Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas |
DE69830513T DE69830513T2 (en) | 1997-12-22 | 1998-12-22 | INHIBITION OF THE p38 KINASE USING SYMMETRICAL AND ASYMMETRIC DIPHENYL HYDROGEN |
JP2000525400A JP3887769B2 (en) | 1997-12-22 | 1998-12-22 | Inhibition of p38 kinase using symmetric and asymmetric diphenylureas |
AT98964221T ATE297383T1 (en) | 1997-12-22 | 1998-12-22 | INHIBITION OF P38 KINASE USING SYMMETRIC AND ASYMMETRIC DIPHENYL UREASES |
IL136737A IL136737A (en) | 1997-12-22 | 2000-06-13 | Symmetrical and unsymmetrical diphenyl ureas and pharmaceutical compositions comprising them |
HK01102468A HK1032050A1 (en) | 1997-12-22 | 2001-04-07 | Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas. |
IL170235A IL170235A (en) | 1997-12-22 | 2005-08-11 | Diphenyl ureas and their use for the preparation of medicaments for treating diseases, other than cancer, mediated by p38 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US99574997A | 1997-12-22 | 1997-12-22 | |
US08/995,749 | 1997-12-22 |
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WO1999032463A1 true WO1999032463A1 (en) | 1999-07-01 |
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PCT/US1998/027265 WO1999032463A1 (en) | 1997-12-22 | 1998-12-22 | INHIBITION OF p38 KINASE USING SYMMETRICAL AND UNSYMMETRICAL DIPHENYL UREAS |
Country Status (12)
Country | Link |
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EP (2) | EP1042305B1 (en) |
JP (1) | JP3887769B2 (en) |
AT (1) | ATE297383T1 (en) |
AU (1) | AU1939999A (en) |
CA (1) | CA2315715C (en) |
DE (2) | DE1042305T1 (en) |
DK (1) | DK1042305T3 (en) |
ES (1) | ES2154252T3 (en) |
HK (1) | HK1032050A1 (en) |
IL (3) | IL136737A0 (en) |
PT (1) | PT1042305E (en) |
WO (1) | WO1999032463A1 (en) |
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IL136737A (en) | 2006-12-10 |
DE69830513T2 (en) | 2006-03-16 |
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IL170235A (en) | 2010-04-15 |
ES2154252T1 (en) | 2001-04-01 |
DE69830513D1 (en) | 2005-07-14 |
DE1042305T1 (en) | 2001-04-19 |
EP1042305A1 (en) | 2000-10-11 |
ATE297383T1 (en) | 2005-06-15 |
DK1042305T3 (en) | 2005-09-19 |
HK1032050A1 (en) | 2001-07-06 |
JP3887769B2 (en) | 2007-02-28 |
PT1042305E (en) | 2005-10-31 |
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