NO324792B1 - Farmasoytisk aktive sulfonamidderivater - Google Patents

Farmasoytisk aktive sulfonamidderivater Download PDF

Info

Publication number: NO324792B1
Authority: NO; Norway
Prior art keywords: sulfonyl; methyl; thien; piperidin; benzamide
Prior art date: 1999-09-28

Application number

NO20021530A

Other languages

English (en)

Norwegian (no)

Other versions

NO20021530D0 (no

NO20021530L (no

Inventor

Stephen Arkinstall

Dennis Church

Marco Biamonte

Serge Halazy

Montserrat Camps

Thomas Rueckle

Jean-Pierre Gotteland

Original Assignee

Serono Lab

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.)

1999-09-28

Filing date

2002-03-26

Publication date

2007-12-10

2002-03-26 Application filed by Serono Lab filed Critical Serono Lab

2002-03-26 Publication of NO20021530D0 publication Critical patent/NO20021530D0/no

2002-03-26 Publication of NO20021530L publication Critical patent/NO20021530L/no

2007-12-10 Publication of NO324792B1 publication Critical patent/NO324792B1/no

Links

229940124530 sulfonamide Drugs 0.000 title claims description 38
150000003456 sulfonamides Chemical class 0.000 title claims description 28
-1 cyano, hydroxyl Chemical group 0.000 claims description 118
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 89
238000000034 method Methods 0.000 claims description 54
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
238000002360 preparation method Methods 0.000 claims description 47
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
150000001412 amines Chemical class 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 24
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 22
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 20
208000035475 disorder Diseases 0.000 claims description 17
239000008194 pharmaceutical composition Substances 0.000 claims description 16
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
238000005859 coupling reaction Methods 0.000 claims description 9
125000001544 thienyl group Chemical group 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
125000001624 naphthyl group Chemical group 0.000 claims description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
150000001263 acyl chlorides Chemical class 0.000 claims description 7
239000003085 diluting agent Substances 0.000 claims description 7
RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 6
125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims description 6
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
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 claims description 6
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
150000001408 amides Chemical class 0.000 claims description 5
230000008878 coupling Effects 0.000 claims description 5
238000010168 coupling process Methods 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
230000008569 process Effects 0.000 claims description 5
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 5
125000005493 quinolyl group Chemical group 0.000 claims description 5
125000000335 thiazolyl group Chemical group 0.000 claims description 5
208000023275 Autoimmune disease Diseases 0.000 claims description 4
208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
206010040070 Septic Shock Diseases 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004188 dichlorophenyl group Chemical group 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 4
125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
208000006011 Stroke Diseases 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
RCLZUQSDCHJJLX-UHFFFAOYSA-N n-[[5-[4-(benzimidazol-1-yl)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]-4-chlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)N2C3=CC=CC=C3N=C2)S1 RCLZUQSDCHJJLX-UHFFFAOYSA-N 0.000 claims description 3
ZWTZHPSNRRFOAF-UHFFFAOYSA-N n-[[5-[4-(benzotriazol-1-yl)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]-2-hydroxybenzamide Chemical compound OC1=CC=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)N2C3=CC=CC=C3N=N2)S1 ZWTZHPSNRRFOAF-UHFFFAOYSA-N 0.000 claims description 3
QDHJPQKWODVHIM-UHFFFAOYSA-N n-[[5-[4-(benzotriazol-1-yl)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]-4-nitrobenzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)N2C3=CC=CC=C3N=N2)S1 QDHJPQKWODVHIM-UHFFFAOYSA-N 0.000 claims description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
125000003226 pyrazolyl group Chemical group 0.000 claims description 3
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
NITIZPRHXHKHKE-UHFFFAOYSA-N 2-[1-[5-[[(4-chlorobenzoyl)amino]methyl]thiophen-2-yl]sulfonylpiperidin-4-yl]benzotriazole-5-carboxylic acid Chemical compound N1=C2C=C(C(=O)O)C=CC2=NN1C(CC1)CCN1S(=O)(=O)C(S1)=CC=C1CNC(=O)C1=CC=C(Cl)C=C1 NITIZPRHXHKHKE-UHFFFAOYSA-N 0.000 claims description 2
HYJJWJZEQVCURL-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(2,6-dichlorobenzoyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCN(CC2)C(=O)C=2C(=CC=CC=2Cl)Cl)S1 HYJJWJZEQVCURL-UHFFFAOYSA-N 0.000 claims description 2
YWCKRKNLKAJANS-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(6-chlorobenzotriazol-1-yl)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)N2C3=CC(Cl)=CC=C3N=N2)S1 YWCKRKNLKAJANS-UHFFFAOYSA-N 0.000 claims description 2
KVXNWEQMXWXTRN-UHFFFAOYSA-N 4-chloro-n-[[5-[[4-(2-phenylacetyl)-1,4-diazepan-1-yl]sulfonyl]thiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCN(CCC2)C(=O)CC=2C=CC=CC=2)S1 KVXNWEQMXWXTRN-UHFFFAOYSA-N 0.000 claims description 2
OTGAXMANQKRURD-UHFFFAOYSA-N 4-nitro-n-[[5-[4-(3-nitroanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)NC=2C=C(C=CC=2)[N+]([O-])=O)S1 OTGAXMANQKRURD-UHFFFAOYSA-N 0.000 claims description 2
UUOKRQSYOPPSIK-UHFFFAOYSA-N 4-nitro-n-[[5-[4-(3-sulfamoylanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound NS(=O)(=O)C1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(=CC=3)[N+]([O-])=O)=CC=2)=C1 UUOKRQSYOPPSIK-UHFFFAOYSA-N 0.000 claims description 2
208000024827 Alzheimer disease Diseases 0.000 claims description 2
206010003210 Arteriosclerosis Diseases 0.000 claims description 2
206010006187 Breast cancer Diseases 0.000 claims description 2
208000026310 Breast neoplasm Diseases 0.000 claims description 2
208000024172 Cardiovascular disease Diseases 0.000 claims description 2
206010009944 Colon cancer Diseases 0.000 claims description 2
208000001333 Colorectal Neoplasms Diseases 0.000 claims description 2
206010019196 Head injury Diseases 0.000 claims description 2
208000023105 Huntington disease Diseases 0.000 claims description 2
208000007201 Myocardial reperfusion injury Diseases 0.000 claims description 2
206010028980 Neoplasm Diseases 0.000 claims description 2
206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
208000018737 Parkinson disease Diseases 0.000 claims description 2
208000017442 Retinal disease Diseases 0.000 claims description 2
125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
208000011775 arteriosclerosis disease Diseases 0.000 claims description 2
208000006673 asthma Diseases 0.000 claims description 2
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical group N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 claims description 2
229960003529 diazepam Drugs 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
206010015037 epilepsy Diseases 0.000 claims description 2
125000004464 hydroxyphenyl group Chemical group 0.000 claims description 2
208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
CXCWQSZCTXWQSY-UHFFFAOYSA-N methyl 3-[[1-[5-[[(3-methoxybenzoyl)amino]methyl]thiophen-2-yl]sulfonylpiperidin-4-yl]amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=C(OC)C=CC=3)=CC=2)=C1 CXCWQSZCTXWQSY-UHFFFAOYSA-N 0.000 claims description 2
201000006417 multiple sclerosis Diseases 0.000 claims description 2
208000010125 myocardial infarction Diseases 0.000 claims description 2
FONJJKKVKBISOP-UHFFFAOYSA-N n-[[5-[4-(3-benzylanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C=C(CC=3C=CC=CC=3)C=CC=2)=C1 FONJJKKVKBISOP-UHFFFAOYSA-N 0.000 claims description 2
JHFYWRCGTMMJHX-UHFFFAOYSA-N n-[[5-[4-(3-benzylanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]-4-chlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)NC=2C=C(CC=3C=CC=CC=3)C=CC=2)S1 JHFYWRCGTMMJHX-UHFFFAOYSA-N 0.000 claims description 2
XSDVWTHVEGXZQE-UHFFFAOYSA-N n-[[5-[4-(benzotriazol-1-yl)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]-3,4-dihydroxybenzamide Chemical compound C1=C(O)C(O)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)N2C3=CC=CC=C3N=N2)S1 XSDVWTHVEGXZQE-UHFFFAOYSA-N 0.000 claims description 2
125000006501 nitrophenyl group Chemical group 0.000 claims description 2
201000002528 pancreatic cancer Diseases 0.000 claims description 2
208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
230000036303 septic shock Effects 0.000 claims description 2
HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 claims 12
125000005843 halogen group Chemical group 0.000 claims 4
QQQGBUXUGKEYGK-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-(2-nitroanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C(=CC=CC=2)[N+]([O-])=O)=C1 QQQGBUXUGKEYGK-UHFFFAOYSA-N 0.000 claims 1
MHGWSCDALBVNDX-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-(3-methoxyanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=C(OC)C=CC=3)=CC=2)=C1 MHGWSCDALBVNDX-UHFFFAOYSA-N 0.000 claims 1
UHKZTGCTYZBBKT-UHFFFAOYSA-N 4-chloro-N-[[5-[4-(quinolin-5-ylamino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide 4-chloro-N-[[5-[4-(3-sulfamoylanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound ClC1=CC=C(C(=O)NCC=2SC(=CC2)S(=O)(=O)N2CCC(CC2)NC2=C3C=CC=NC3=CC=C2)C=C1.NS(=O)(=O)C=1C=C(NC2CCN(CC2)S(=O)(=O)C2=CC=C(S2)CNC(C2=CC=C(C=C2)Cl)=O)C=CC1 UHKZTGCTYZBBKT-UHFFFAOYSA-N 0.000 claims 1
CZSHQDKLMREPIH-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(2,4-difluorobenzoyl)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound FC1=CC(F)=CC=C1C(=O)C1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 CZSHQDKLMREPIH-UHFFFAOYSA-N 0.000 claims 1
MYISFLPEOBBFKR-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(3-propylanilino)piperidin-1-yl]sulfonylfuran-2-yl]methyl]benzamide Chemical compound CCCC1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2OC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)=C1 MYISFLPEOBBFKR-UHFFFAOYSA-N 0.000 claims 1
XVUHXWCAMOYWOY-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(4-chloroanilino)piperidin-1-yl]sulfonylfuran-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1NC1CCN(S(=O)(=O)C=2OC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 XVUHXWCAMOYWOY-UHFFFAOYSA-N 0.000 claims 1
YMAQMFMFCZDCBD-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(naphthalene-1-carbonyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide;4-chloro-n-[[5-[4-(3-sulfamoylanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound NS(=O)(=O)C1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)=C1.C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCN(CC2)C(=O)C=2C3=CC=CC=C3C=CC=2)S1 YMAQMFMFCZDCBD-UHFFFAOYSA-N 0.000 claims 1
UWZVGIBPCUQWRW-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(quinolin-8-ylamino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)NC=2C3=NC=CC=C3C=CC=2)S1 UWZVGIBPCUQWRW-UHFFFAOYSA-N 0.000 claims 1
ACBBNXWLABVBQR-UHFFFAOYSA-N 4-chloro-n-[[5-[4-[3-(2-hydroxyethylsulfonyl)anilino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound OCCS(=O)(=O)C1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)=C1 ACBBNXWLABVBQR-UHFFFAOYSA-N 0.000 claims 1
LGAAEFJZLLETLT-UHFFFAOYSA-N C(C)C=1C=C(NC2CCN(CC2)S(=O)(=O)C2=CC=C(S2)CNC(C2=CC(=CC=C2)OC)=O)C=CC1.C(CCC)NS(=O)(=O)C=1C=C(NC2CCN(CC2)S(=O)(=O)C2=CC=C(S2)CNC(C2=CC(=CC=C2)OC)=O)C=CC1 Chemical compound C(C)C=1C=C(NC2CCN(CC2)S(=O)(=O)C2=CC=C(S2)CNC(C2=CC(=CC=C2)OC)=O)C=CC1.C(CCC)NS(=O)(=O)C=1C=C(NC2CCN(CC2)S(=O)(=O)C2=CC=C(S2)CNC(C2=CC(=CC=C2)OC)=O)C=CC1 LGAAEFJZLLETLT-UHFFFAOYSA-N 0.000 claims 1
HVBGARUVAXPEPG-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)N1CCN(CC1)S(=O)(=O)C1=CC=C(S1)CNC(C1=CC=C(C=C1)Cl)=O.ClC1=CC=C(C(=O)NCC=2SC(=CC2)S(=O)(=O)N2CCN(CC2)C(C2=CC=C(C=C2)[N+](=O)[O-])=O)C=C1 Chemical compound C(C1=CC=CC=C1)(=O)N1CCN(CC1)S(=O)(=O)C1=CC=C(S1)CNC(C1=CC=C(C=C1)Cl)=O.ClC1=CC=C(C(=O)NCC=2SC(=CC2)S(=O)(=O)N2CCN(CC2)C(C2=CC=C(C=C2)[N+](=O)[O-])=O)C=C1 HVBGARUVAXPEPG-UHFFFAOYSA-N 0.000 claims 1
HLEZAOUYMDNPGJ-UHFFFAOYSA-N ClC1=CC=C(C(=O)NCC=2SC(=CC2)S(=O)(=O)N2CCN(CC2)C(C2=C(C=CC=C2)[N+](=O)[O-])=O)C=C1.ClC1=CC=C(C(=O)NCC=2SC(=CC2)S(=O)(=O)N2CCN(CC2)C(=O)C2=CC=CC3=CC=CC=C23)C=C1 Chemical compound ClC1=CC=C(C(=O)NCC=2SC(=CC2)S(=O)(=O)N2CCN(CC2)C(C2=C(C=CC=C2)[N+](=O)[O-])=O)C=C1.ClC1=CC=C(C(=O)NCC=2SC(=CC2)S(=O)(=O)N2CCN(CC2)C(=O)C2=CC=CC3=CC=CC=C23)C=C1 HLEZAOUYMDNPGJ-UHFFFAOYSA-N 0.000 claims 1
ZQJHRBLAJVRVJG-UHFFFAOYSA-N ClC1=CC=C(NC2CCN(CC2)S(=O)(=O)C2=CC=C(S2)CNC(C2=CC(=CC=C2)[N+](=O)[O-])=O)C=C1.[N+](=O)([O-])C=1C=C(C(=O)NCC=2SC(=CC2)S(=O)(=O)N2CCC(CC2)NC2=C(C=CC=C2)[N+](=O)[O-])C=CC1 Chemical compound ClC1=CC=C(NC2CCN(CC2)S(=O)(=O)C2=CC=C(S2)CNC(C2=CC(=CC=C2)[N+](=O)[O-])=O)C=C1.[N+](=O)([O-])C=1C=C(C(=O)NCC=2SC(=CC2)S(=O)(=O)N2CCC(CC2)NC2=C(C=CC=C2)[N+](=O)[O-])C=CC1 ZQJHRBLAJVRVJG-UHFFFAOYSA-N 0.000 claims 1
NPUSVCYOOTYAJO-UHFFFAOYSA-N OCCS(=O)(=O)C=1C=C(NC2CCN(CC2)S(=O)(=O)C2=CC=C(S2)CNC(C2=CC=C(C=C2)[N+](=O)[O-])=O)C=CC1.N(C1=CC=CC=C1)C1CCN(CC1)S(=O)(=O)C1=CC=C(S1)CNC(C1=CC(=CC=C1)[N+](=O)[O-])=O Chemical compound OCCS(=O)(=O)C=1C=C(NC2CCN(CC2)S(=O)(=O)C2=CC=C(S2)CNC(C2=CC=C(C=C2)[N+](=O)[O-])=O)C=CC1.N(C1=CC=CC=C1)C1CCN(CC1)S(=O)(=O)C1=CC=C(S1)CNC(C1=CC(=CC=C1)[N+](=O)[O-])=O NPUSVCYOOTYAJO-UHFFFAOYSA-N 0.000 claims 1
206010052779 Transplant rejections Diseases 0.000 claims 1
201000011510 cancer Diseases 0.000 claims 1
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Classifications

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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- 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
- C07D413/12—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 linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems

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Animal Behavior & Ethology (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
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General Health & Medical Sciences (AREA)
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Neurosurgery (AREA)
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Pulmonology (AREA)
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Physical Education & Sports Medicine (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO20021530A 1999-09-28 2002-03-26 Farmasoytisk aktive sulfonamidderivater NO324792B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP99810869A EP1088821A1 (en)	1999-09-28	1999-09-28	Pharmaceutically active sulfonamide derivatives
PCT/IB2000/001380 WO2001023378A1 (en)	1999-09-28	2000-09-28	Pharmaceutically active sulfonamide derivatives

Publications (3)

Publication Number	Publication Date
NO20021530D0 NO20021530D0 (no)	2002-03-26
NO20021530L NO20021530L (no)	2002-03-26
NO324792B1 true NO324792B1 (no)	2007-12-10

Family

ID=8243049

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20021530A NO324792B1 (no)	1999-09-28	2002-03-26	Farmasoytisk aktive sulfonamidderivater

Country Status (30)

Country	Link
US (1)	US8012995B1 (pl)
EP (2)	EP1088821A1 (pl)
JP (2)	JP5015397B2 (pl)
KR (1)	KR100827533B1 (pl)
CN (1)	CN1189467C (pl)
AR (1)	AR031531A1 (pl)
AT (1)	ATE309998T1 (pl)
AU (1)	AU777708B2 (pl)
BG (1)	BG65797B1 (pl)
BR (1)	BR0014641A (pl)
CA (1)	CA2379575C (pl)
CZ (1)	CZ2002880A3 (pl)
DE (1)	DE60024115T2 (pl)
DK (1)	DK1218374T3 (pl)
EA (1)	EA005368B1 (pl)
EE (1)	EE05109B1 (pl)
ES (1)	ES2248114T3 (pl)
HK (1)	HK1048306B (pl)
HU (1)	HUP0203312A3 (pl)
IL (2)	IL148876A0 (pl)
MX (1)	MXPA02003199A (pl)
NO (1)	NO324792B1 (pl)
NZ (1)	NZ517424A (pl)
PL (1)	PL212237B1 (pl)
SI (1)	SI1218374T1 (pl)
SK (1)	SK287058B6 (pl)
TR (1)	TR200200789T2 (pl)
UA (1)	UA74796C2 (pl)
WO (1)	WO2001023378A1 (pl)
ZA (1)	ZA200201509B (pl)

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WO2005118543A1 (ja) *	2004-06-03	2005-12-15	Ono Pharmaceutical Co., Ltd.	キナーゼ阻害薬およびその用途
BRPI0512781A (pt)	2004-06-29	2008-04-08	Pfizer Prod Inc	método para preparação de derivados de 5-{4-(2-hidroxi-propil)-3,5-dioxo-4,5-diidro-3h-[1,2,4]tria zin-2-il}-benzamida através da desproteção dos precursores de protetores de hidroxila
US20060094753A1 (en)	2004-10-29	2006-05-04	Alcon, Inc.	Use of inhibitors of Jun N-terminal kinases for the treatment of glaucomatous retinopathy and ocular diseases
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1999
- 1999-09-28 EP EP99810869A patent/EP1088821A1/en not_active Withdrawn
2000
- 2000-09-26 AR ARP000105044A patent/AR031531A1/es active IP Right Grant
- 2000-09-28 JP JP2001526530A patent/JP5015397B2/ja not_active Expired - Fee Related
- 2000-09-28 AT AT00960921T patent/ATE309998T1/de active
- 2000-09-28 SK SK580-2002A patent/SK287058B6/sk not_active IP Right Cessation
- 2000-09-28 IL IL14887600A patent/IL148876A0/xx unknown
- 2000-09-28 AU AU73074/00A patent/AU777708B2/en not_active Ceased
- 2000-09-28 PL PL354169A patent/PL212237B1/pl not_active IP Right Cessation
- 2000-09-28 BR BR0014641-2A patent/BR0014641A/pt not_active IP Right Cessation
- 2000-09-28 US US10/070,954 patent/US8012995B1/en not_active Expired - Fee Related
- 2000-09-28 TR TR2002/00789T patent/TR200200789T2/xx unknown
- 2000-09-28 KR KR1020027003983A patent/KR100827533B1/ko not_active Expired - Fee Related
- 2000-09-28 EE EEP200200165A patent/EE05109B1/xx not_active IP Right Cessation
- 2000-09-28 ES ES00960921T patent/ES2248114T3/es not_active Expired - Lifetime
- 2000-09-28 EP EP00960921A patent/EP1218374B1/en not_active Expired - Lifetime
- 2000-09-28 CN CNB008135681A patent/CN1189467C/zh not_active Expired - Fee Related
- 2000-09-28 EA EA200200417A patent/EA005368B1/ru not_active IP Right Cessation
- 2000-09-28 MX MXPA02003199A patent/MXPA02003199A/es active IP Right Grant
- 2000-09-28 DK DK00960921T patent/DK1218374T3/da active
- 2000-09-28 NZ NZ517424A patent/NZ517424A/en not_active IP Right Cessation
- 2000-09-28 UA UA2002032472A patent/UA74796C2/uk unknown
- 2000-09-28 CA CA2379575A patent/CA2379575C/en not_active Expired - Fee Related
- 2000-09-28 HK HK03100202.1A patent/HK1048306B/zh not_active IP Right Cessation
- 2000-09-28 WO PCT/IB2000/001380 patent/WO2001023378A1/en not_active Ceased
- 2000-09-28 HU HU0203312A patent/HUP0203312A3/hu unknown
- 2000-09-28 SI SI200030771T patent/SI1218374T1/sl unknown
- 2000-09-28 CZ CZ2002880A patent/CZ2002880A3/cs unknown
- 2000-09-28 DE DE60024115T patent/DE60024115T2/de not_active Expired - Lifetime
2002
- 2002-02-22 ZA ZA200201509A patent/ZA200201509B/xx unknown
- 2002-03-18 BG BG106527A patent/BG65797B1/bg unknown
- 2002-03-25 IL IL148876A patent/IL148876A/en not_active IP Right Cessation
- 2002-03-26 NO NO20021530A patent/NO324792B1/no not_active IP Right Cessation
2012
- 2012-02-20 JP JP2012033604A patent/JP2012121904A/ja active Pending

Also Published As

Publication number	Publication date
AU7307400A (en)	2001-04-30
US8012995B1 (en)	2011-09-06
EE05109B1 (et)	2008-12-15
BG106527A (en)	2003-02-28
HK1048306A1 (en)	2003-03-28
MXPA02003199A (es)	2002-10-31
CN1189467C (zh)	2005-02-16
TR200200789T2 (tr)	2002-08-21
DE60024115D1 (de)	2005-12-22
EA005368B1 (ru)	2005-02-24
IL148876A (en)	2010-11-30
HK1048306B (zh)	2005-06-10
ZA200201509B (en)	2003-04-30
DK1218374T3 (da)	2005-12-27
JP5015397B2 (ja)	2012-08-29
NO20021530D0 (no)	2002-03-26
SK5802002A3 (en)	2002-08-06
HUP0203312A2 (hu)	2003-01-28
ES2248114T3 (es)	2006-03-16
EA200200417A1 (ru)	2002-10-31
CA2379575A1 (en)	2001-04-05
BG65797B1 (bg)	2009-12-31
JP2003510319A (ja)	2003-03-18
AR031531A1 (es)	2003-09-24
CZ2002880A3 (cs)	2002-06-12
PL212237B1 (pl)	2012-08-31
UA74796C2 (en)	2006-02-15
AU777708B2 (en)	2004-10-28
KR100827533B1 (ko)	2008-05-06
NO20021530L (no)	2002-03-26
EP1218374A1 (en)	2002-07-03
KR20020062282A (ko)	2002-07-25
BR0014641A (pt)	2002-06-11
CA2379575C (en)	2011-03-15
ATE309998T1 (de)	2005-12-15
PL354169A1 (pl)	2003-12-29
EP1218374B1 (en)	2005-11-16
HUP0203312A3 (en)	2003-02-28
EE200200165A (et)	2003-04-15
CN1377347A (zh)	2002-10-30
JP2012121904A (ja)	2012-06-28
SI1218374T1 (sl)	2006-02-28
WO2001023378A1 (en)	2001-04-05
EP1088821A1 (en)	2001-04-04
SK287058B6 (sk)	2009-10-07
DE60024115T2 (de)	2006-07-27
NZ517424A (en)	2004-01-30
IL148876A0 (en)	2002-09-12

Legal Events

Date	Code	Title	Description
2008-01-14	CREP	Change of representative	Representative=s name: ONSAGERS AS, POSTBOKS 6963 ST OLAVS PLASS, 0130 OS
2014-04-28	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
JP5015397B2 (ja)	2012-08-29	医薬として活性なスルホンアミド誘導体
JP4927304B2 (ja)	2012-05-09	タンパク質Ｊｕｎ−キナーゼのインヒビターとしての親油性及びイオン化できる成分を担持する医薬的活性スルホンアミド誘導体
US8008341B2 (en)	2011-08-30	Pharmaceutically active benzsulfonamide derivatives as inhibitors of protein junkinases
AU2001287991A1 (en)	2002-06-20	Pharmaceutically active sulfonamide derivatives bearing both lipophilic and ionisable moieties as inhibitors of protein junkinases
AU2001287992A1 (en)	2002-06-20	Pharmaceutically active benzsulfonamide derivatives as inhibitors of protein junkinases
JP2003510320A (ja)	2003-03-18	薬剤活性のあるスルホニルアミノ酸誘導体
JP4927306B2 (ja)	2012-05-09	タンパク質Ｊｕｎ−キナーゼのインヒビターとしての医薬的活性親水性スルホンアミド誘導体
AU2001287990A1 (en)	2002-06-27	Pharmaceutically active hydrophilic sulfonamide derivatives as inhibitors of protein junkinases