CA2525325A1 - Pyrazole-amides et sulfonamides modulateurs des canaux sodiques - Google Patents

Pyrazole-amides et sulfonamides modulateurs des canaux sodiques Download PDF

Info

Publication number: CA2525325A1
Authority: CA; Canada
Prior art keywords: aryl; pyrazole; carboxamide; chlorophenyl; heterocycle
Prior art date: 2003-05-01
Legal status (The legal status 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 status listed.): Abandoned

Application number

CA002525325A

Other languages

English (en)

Inventor

Robert N. Atkinson

Irene Drizen

Robert J. Gregg

Michael F. Gross

Michael E. Kort

Lei Shi

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Abbott Laboratories

Original Assignee

Individual

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.)

2003-05-01

Filing date

2004-04-29

Publication date

2004-11-18

2003-05-01 Priority claimed from US10/427,847 external-priority patent/US20040220170A1/en

2004-04-29 Application filed by Individual filed Critical Individual

2004-11-18 Publication of CA2525325A1 publication Critical patent/CA2525325A1/fr

Status Abandoned legal-status Critical Current

Links

108010052164 Sodium Channels Proteins 0.000 title description 9
102000018674 Sodium Channels Human genes 0.000 title description 9
BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical class NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 title description 2
229940124530 sulfonamide Drugs 0.000 title description 2
150000003456 sulfonamides Chemical class 0.000 title 1
-1 heterocyclealkyl Chemical group 0.000 claims abstract description 118
150000001875 compounds Chemical class 0.000 claims abstract description 105
125000003118 aryl group Chemical group 0.000 claims abstract description 87
125000000217 alkyl group Chemical group 0.000 claims abstract description 64
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 62
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 42
150000002148 esters Chemical class 0.000 claims abstract description 34
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 31
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 31
150000003839 salts Chemical class 0.000 claims abstract description 25
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 21
239000000651 prodrug Substances 0.000 claims abstract description 21
229940002612 prodrug Drugs 0.000 claims abstract description 21
150000001408 amides Chemical class 0.000 claims abstract description 20
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 18
125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 33
239000001257 hydrogen Substances 0.000 claims description 33
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 30
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 28
125000003342 alkenyl group Chemical group 0.000 claims description 26
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
125000003545 alkoxy group Chemical group 0.000 claims description 23
125000000304 alkynyl group Chemical group 0.000 claims description 23
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 22
125000002947 alkylene group Chemical group 0.000 claims description 18
125000005843 halogen group Chemical group 0.000 claims description 18
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 17
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 17
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 17
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
125000004438 haloalkoxy group Chemical group 0.000 claims description 15
125000003396 thiol group Chemical class [H]S* 0.000 claims description 15
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 14
125000003386 piperidinyl group Chemical group 0.000 claims description 14
150000002367 halogens Chemical class 0.000 claims description 13
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 12
125000004193 piperazinyl group Chemical group 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 9
125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 8
125000004414 alkyl thio group Chemical group 0.000 claims description 8
125000003725 azepanyl group Chemical group 0.000 claims description 7
125000002393 azetidinyl group Chemical group 0.000 claims description 7
125000004069 aziridinyl group Chemical group 0.000 claims description 7
125000002757 morpholinyl group Chemical group 0.000 claims description 7
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
125000004568 thiomorpholinyl group Chemical group 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 4
ASHHDOZRIJQRJL-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-[(3,4-dichlorophenyl)methyl]-5-ethenylpyrazole-4-carboxamide Chemical compound C1=CC(Cl)=CC=C1N1C(C=C)=C(C(=O)NCC=2C=C(Cl)C(Cl)=CC=2)C=N1 ASHHDOZRIJQRJL-UHFFFAOYSA-N 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
JGYZWEZPCQPXPP-UHFFFAOYSA-N 1-(2-methoxyphenyl)-5-(trifluoromethyl)-n-[[3-(trifluoromethyl)phenyl]methyl]pyrazole-4-carboxamide Chemical compound COC1=CC=CC=C1N1C(C(F)(F)F)=C(C(=O)NCC=2C=C(C=CC=2)C(F)(F)F)C=N1 JGYZWEZPCQPXPP-UHFFFAOYSA-N 0.000 claims description 2
BFMURVKMVVFJKJ-UHFFFAOYSA-N 1-(3-chlorophenyl)-n-(3-methylsulfonylphenyl)-5-(trifluoromethyl)pyrazole-4-carboxamide Chemical group CS(=O)(=O)C1=CC=CC(NC(=O)C2=C(N(N=C2)C=2C=C(Cl)C=CC=2)C(F)(F)F)=C1 BFMURVKMVVFJKJ-UHFFFAOYSA-N 0.000 claims description 2
DRDPOYZYBHRVRE-UHFFFAOYSA-N 1-(3-methylphenyl)-n-(3-methylsulfonylphenyl)-5-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound CC1=CC=CC(N2C(=C(C(=O)NC=3C=C(C=CC=3)S(C)(=O)=O)C=N2)C(F)(F)F)=C1 DRDPOYZYBHRVRE-UHFFFAOYSA-N 0.000 claims description 2
RBSLLFOKQBUWEH-UHFFFAOYSA-N 1-(4-chlorophenyl)-5-cyano-n-(3-methylsulfonylphenyl)pyrazole-4-carboxamide Chemical compound CS(=O)(=O)C1=CC=CC(NC(=O)C2=C(N(N=C2)C=2C=CC(Cl)=CC=2)C#N)=C1 RBSLLFOKQBUWEH-UHFFFAOYSA-N 0.000 claims description 2
QKPUFGJCKMJLNB-UHFFFAOYSA-N 1-(4-chlorophenyl)-5-ethenyl-n-(3-methylsulfonylphenyl)pyrazole-4-carboxamide Chemical compound CS(=O)(=O)C1=CC=CC(NC(=O)C2=C(N(N=C2)C=2C=CC(Cl)=CC=2)C=C)=C1 QKPUFGJCKMJLNB-UHFFFAOYSA-N 0.000 claims description 2
LQTAPLCRBFRTGD-UHFFFAOYSA-N 1-(4-chlorophenyl)-5-methyl-n-(3-methylsulfonylphenyl)pyrazole-3-carboxamide Chemical compound CC1=CC(C(=O)NC=2C=C(C=CC=2)S(C)(=O)=O)=NN1C1=CC=C(Cl)C=C1 LQTAPLCRBFRTGD-UHFFFAOYSA-N 0.000 claims description 2
MCUPLZRVRSEOKE-UHFFFAOYSA-N 1-(4-chlorophenyl)-5-methyl-n-[(2-methylphenyl)methyl]pyrazole-3-carboxamide Chemical compound CC1=CC(C(=O)NCC=2C(=CC=CC=2)C)=NN1C1=CC=C(Cl)C=C1 MCUPLZRVRSEOKE-UHFFFAOYSA-N 0.000 claims description 2
SCBFDIAETJLQJO-UHFFFAOYSA-N 1-(4-chlorophenyl)-5-methyl-n-[[3-(trifluoromethyl)phenyl]methyl]pyrazole-3-carboxamide Chemical compound CC1=CC(C(=O)NCC=2C=C(C=CC=2)C(F)(F)F)=NN1C1=CC=C(Cl)C=C1 SCBFDIAETJLQJO-UHFFFAOYSA-N 0.000 claims description 2
WVGKJUNXABIEFD-UHFFFAOYSA-N 1-(4-chlorophenyl)-5-methyl-n-[[3-(trifluoromethyl)phenyl]methyl]pyrazole-4-carboxamide Chemical compound CC1=C(C(=O)NCC=2C=C(C=CC=2)C(F)(F)F)C=NN1C1=CC=C(Cl)C=C1 WVGKJUNXABIEFD-UHFFFAOYSA-N 0.000 claims description 2
JAGLKKAAKLQBKK-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-[2-(4-chlorophenyl)ethyl]-5-methylpyrazole-3-carboxamide Chemical compound CC1=CC(C(=O)NCCC=2C=CC(Cl)=CC=2)=NN1C1=CC=C(Cl)C=C1 JAGLKKAAKLQBKK-UHFFFAOYSA-N 0.000 claims description 2
FMMRLSLPZXXZMR-UHFFFAOYSA-N 1-(4-methylphenyl)-n-(3-methylsulfonylphenyl)-5-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C1=CC(C)=CC=C1N1C(C(F)(F)F)=C(C(=O)NC=2C=C(C=CC=2)S(C)(=O)=O)C=N1 FMMRLSLPZXXZMR-UHFFFAOYSA-N 0.000 claims description 2
ZWSXQCVOQXBBPM-UHFFFAOYSA-N 1-cyclohexyl-5-(trifluoromethyl)-n-[[3-(trifluoromethyl)phenyl]methyl]pyrazole-4-carboxamide Chemical compound FC(F)(F)C1=C(C(=O)NCC=2C=C(C=CC=2)C(F)(F)F)C=NN1C1CCCCC1 ZWSXQCVOQXBBPM-UHFFFAOYSA-N 0.000 claims description 2
MXFOCODSYBFVIE-UHFFFAOYSA-N 1-cyclohexyl-n-(3-methylsulfonylphenyl)-5-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound CS(=O)(=O)C1=CC=CC(NC(=O)C2=C(N(C3CCCCC3)N=C2)C(F)(F)F)=C1 MXFOCODSYBFVIE-UHFFFAOYSA-N 0.000 claims description 2
MROAQIQXZDBAPJ-UHFFFAOYSA-N 5-acetyl-1-(4-chlorophenyl)-n-(3-methylsulfonylphenyl)pyrazole-4-carboxamide Chemical compound CC(=O)C1=C(C(=O)NC=2C=C(C=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(Cl)C=C1 MROAQIQXZDBAPJ-UHFFFAOYSA-N 0.000 claims description 2
CBYCTWRBYNITAQ-UHFFFAOYSA-N 5-acetyl-1-(4-chlorophenyl)-n-[(3,4-dichlorophenyl)methyl]pyrazole-4-carboxamide Chemical compound CC(=O)C1=C(C(=O)NCC=2C=C(Cl)C(Cl)=CC=2)C=NN1C1=CC=C(Cl)C=C1 CBYCTWRBYNITAQ-UHFFFAOYSA-N 0.000 claims description 2
RKFJCKLKGHCKND-UHFFFAOYSA-N CS(=O)(=O)C1=CC=CC(NC(=O)C2=C(N(N=C2)C=2C=CC(Cl)=CC=2)O)=C1 Chemical compound CS(=O)(=O)C1=CC=CC(NC(=O)C2=C(N(N=C2)C=2C=CC(Cl)=CC=2)O)=C1 RKFJCKLKGHCKND-UHFFFAOYSA-N 0.000 claims description 2
OOXKNOOQJMJXCQ-UHFFFAOYSA-N OC1=C(C(=O)NCC=2C=CC=CC=2)C=NN1C1=CC=C(Cl)C=C1 Chemical compound OC1=C(C(=O)NCC=2C=CC=CC=2)C=NN1C1=CC=C(Cl)C=C1 OOXKNOOQJMJXCQ-UHFFFAOYSA-N 0.000 claims description 2
ALWKDWPALYVVOG-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethyl]-1-(2-methoxyphenyl)-5-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound COC1=CC=CC=C1N1C(C(F)(F)F)=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=N1 ALWKDWPALYVVOG-UHFFFAOYSA-N 0.000 claims description 2
XXMLBLWSJWIIKM-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethyl]-1-(7-chloroquinolin-4-yl)-5-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C1=NN(C=2C3=CC=C(Cl)C=C3N=CC=2)C(C(F)(F)F)=C1C(=O)NCCC1=CC=C(Cl)C=C1 XXMLBLWSJWIIKM-UHFFFAOYSA-N 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
UHUKPORCSLIULB-UHFFFAOYSA-N 1-(1-benzylpiperidin-4-yl)-n-(3-methylsulfonylphenyl)-5-(trifluoromethyl)pyrazole-4-carboxamide Chemical group CS(=O)(=O)C1=CC=CC(NC(=O)C2=C(N(C3CCN(CC=4C=CC=CC=4)CC3)N=C2)C(F)(F)F)=C1 UHUKPORCSLIULB-UHFFFAOYSA-N 0.000 claims 1
IUKPHUWSBNDUBC-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-[(2-methoxyphenyl)methyl]-5-methylpyrazole-3-carboxamide Chemical compound COC1=CC=CC=C1CNC(=O)C1=NN(C=2C=CC(Cl)=CC=2)C(C)=C1 IUKPHUWSBNDUBC-UHFFFAOYSA-N 0.000 claims 1
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 1
LMKAZJFNVXSZLM-UHFFFAOYSA-N [1-(4-chlorophenyl)-5-(trifluoromethyl)pyrazol-4-yl]-(4-cyclohexylpiperazin-1-yl)methanone Chemical group FC(F)(F)C1=C(C(=O)N2CCN(CC2)C2CCCCC2)C=NN1C1=CC=C(Cl)C=C1 LMKAZJFNVXSZLM-UHFFFAOYSA-N 0.000 claims 1
CBFDSSQYDUWBCP-UHFFFAOYSA-N [4-(3-chlorophenyl)piperazin-1-yl]-[1-(4-chlorophenyl)-5-(trifluoromethyl)pyrazol-4-yl]methanone Chemical group FC(F)(F)C1=C(C(=O)N2CCN(CC2)C=2C=C(Cl)C=CC=2)C=NN1C1=CC=C(Cl)C=C1 CBFDSSQYDUWBCP-UHFFFAOYSA-N 0.000 claims 1
FNWBWRHVMKSYAK-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-1-(4-chlorophenyl)-5-methylpyrazole-4-carboxamide Chemical group CC1=C(C(=O)NC2CCN(CC=3C=CC=CC=3)CC2)C=NN1C1=CC=C(Cl)C=C1 FNWBWRHVMKSYAK-UHFFFAOYSA-N 0.000 claims 1
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238000005160 1H NMR spectroscopy Methods 0.000 description 22
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KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
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CFMYXEVWODSLAX-QOZOJKKESA-N tetrodotoxin Chemical compound O([C@@]([C@H]1O)(O)O[C@H]2[C@@]3(O)CO)[C@H]3[C@@H](O)[C@]11[C@H]2[C@@H](O)N=C(N)N1 CFMYXEVWODSLAX-QOZOJKKESA-N 0.000 description 1
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230000004797 therapeutic response Effects 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
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125000001425 triazolyl group Chemical group 0.000 description 1
QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
210000001170 unmyelinated nerve fiber Anatomy 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA002525325A 2003-05-01 2004-04-29 Pyrazole-amides et sulfonamides modulateurs des canaux sodiques Abandoned CA2525325A1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US10/427,847		2003-05-01
US10/427,847 US20040220170A1 (en)	2003-05-01	2003-05-01	Pyrazole-amides and sulfonamides as sodium channel modulators
PCT/US2004/013530 WO2004099154A2 (fr)	2003-05-01	2004-04-29	Pyrazole-amides et sulfonamides modulateurs des canaux sodiques

Publications (1)

Publication Number	Publication Date
CA2525325A1 true CA2525325A1 (fr)	2004-11-18

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CA002525325A Abandoned CA2525325A1 (fr)	2003-05-01	2004-04-29	Pyrazole-amides et sulfonamides modulateurs des canaux sodiques

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EP (1)	EP1620405A2 (fr)
JP (1)	JP2006525355A (fr)
CA (1)	CA2525325A1 (fr)
MX (1)	MXPA05011775A (fr)

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US7638541B2 (en)	2006-12-28	2009-12-29	Metabolex Inc.	5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine
US8183381B2 (en) *	2007-07-19	2012-05-22	Metabolex Inc.	N-linked heterocyclic receptor agonists for the treatment of diabetes and metabolic disorders
WO2011041154A1 (fr)	2009-10-01	2011-04-07	Metabolex, Inc.	Sels de la tétrazol-1-yl-phénoxyméthyl-thiazol-2-yl-pipéridinyl-pyrimidine substituée
WO2012177263A1 (fr) *	2011-06-24	2012-12-27	Intra-Cellular Therapies, Inc.	Composés et procédés de prophylaxie et de traitement concernant des antagonistes de récepteur nicotinique
PE20170129A1 (es) *	2014-06-03	2017-03-30	Actelion Pharmaceuticals Ltd	Compuestos de pirazol y su uso como bloqueadores de los canales de calcio tipo t
JP2019504840A (ja) *	2016-01-28	2019-02-21	ソルヴェイ（ソシエテアノニム）	ハロゲン置換ジケトン、ピラゾール化合物およびピラゾール化合物の製造方法
CA3032432A1 (fr)	2016-08-03	2018-02-08	Charles A. Mcwherter	Composes d'aryle d'oxymethylene pour le traitement de maladies gastro-intestinales inflammatoires ou de troubles gastro-intestinaux

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WO1998028269A1 (fr) *	1996-12-23	1998-07-02	Du Pont Pharmaceuticals Company	COMPOSES HETEROAROMATIQUES CONTENANT DE L'AZOTE, UTILISES EN TANT QU'INHIBITEURS DU FACTEUR Xa
HUP0003906A2 (hu) *	1997-06-19	2001-05-28	Du Pont Pharmaceuticals Co.	Xa faktort gátló hatású heterociklusos vegyületek és ezeket tartalmazó gyógyszerkészítmények
JP2001526268A (ja) *	1997-12-22	2001-12-18	デュポンファーマシューティカルズカンパニー	Ｘａ因子阻害剤としての、オルト−置換Ｐ１を有する、窒素含有複素環式芳香族化合物
ATE306481T1 (de) *	1999-05-12	2005-10-15	Ortho Mcneil Pharm Inc	Pyrazolecarboxamide zur behandlung von fettleibigkeit und anderen erkrankungen
CN1390206A (zh) *	1999-09-17	2003-01-08	千嬉药品公司	因子Xa的抑制剂
MXPA02011400A (es) *	2000-05-22	2003-05-23	Aventis Pharm Prod Inc	Derivados de arimetilamina para uso como inhibidores de triptasa.
US6604974B2 (en) *	2000-12-22	2003-08-12	Thomson Licensing S.A.	Method and apparatus for applying crosswires to a tension focus mask
WO2004002965A1 (fr) *	2002-06-29	2004-01-08	Zentaris Gmbh	Aryl- et heteroarylcarbonylpiperazines et leur utilisation dans le traitement de maladies tumorales benignes et malignes
GB0226178D0 (en) *	2002-11-11	2002-12-18	Johnson Matthey Plc	Desulphurisation
EP1590329A1 (fr) *	2003-01-28	2005-11-02	Aventis Pharma S.A.	Produits n-aryl-heteroaromatiques, compositions les contenant et utilisation

2004
- 2004-04-29 CA CA002525325A patent/CA2525325A1/fr not_active Abandoned
- 2004-04-29 JP JP2006514200A patent/JP2006525355A/ja active Pending
- 2004-04-29 EP EP04751090A patent/EP1620405A2/fr not_active Withdrawn
- 2004-04-29 MX MXPA05011775A patent/MXPA05011775A/es not_active Application Discontinuation

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JP2006525355A (ja)	2006-11-09
EP1620405A2 (fr)	2006-02-01
MXPA05011775A (es)	2006-02-17

Legal Events

Date	Code	Title	Description
2010-04-29	FZDE	Discontinued

Publication	Publication Date	Title
US20040220170A1 (en)	2004-11-04	Pyrazole-amides and sulfonamides as sodium channel modulators
JP6238942B2 (ja)	2017-11-29	造血成長因子模倣小分子化合物およびそれらの使用
CA2362381C (fr)	2009-12-22	Composes amide et leur utilisation medicinale
US7074805B2 (en)	2006-07-11	Fused azabicyclic compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor
RU2059622C1 (ru)	1996-05-10	Производные пиразола или их фармацевтически приемлемые кислотно-аддитивные соли
JP6261340B2 (ja)	2018-01-17	造血成長因子模倣体の使用
US7595332B2 (en)	2009-09-29	Amides that inhibit vanilloid receptor subtype 1 (VR1)
ES2315704T3 (es)	2009-04-01	Compuestos azabiciclicos fusionados que inhiben el receptor vainilloide de subtipo 1 (vr1).
JP4335212B2 (ja)	2009-09-30	インダゾール誘導体
US20030158188A1 (en)	2003-08-21	Fused azabicyclic compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor
US20060189639A1 (en)	2006-08-24	Antagonists of the mGlu receptor and uses thereof
MXPA05003632A (es)	2005-06-03	Derivados de piperidina 1, 4-disustituidos y su uso como inhibidores de 11-beta-hidroesteroide deshidrogenasa humana de tipo 1 (11betahsd1).
CA2596527A1 (fr)	2006-08-03	Inhibiteur d'igf-1r
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