NO329384B1 - Aminoindazolderivater, fremstilling derav samt farmasoytiske preparater og medisinske produkter inneholdende forbindelsene - Google Patents

Aminoindazolderivater, fremstilling derav samt farmasoytiske preparater og medisinske produkter inneholdende forbindelsene Download PDF

Info

Publication number: NO329384B1
Authority: NO; Norway
Prior art keywords: indazol; chloro; butanamide; indazole; amino
Prior art date: 2002-03-11

Application number

NO20044137A

Other languages

English (en)

Norwegian (no)

Other versions

NO20044137L (no

Inventor

Gilles Dutruc-Rosset

Dominique Le Suisse

Thomas Rooney

Franck Halley

Original Assignee

Aventis Pharma Sa

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.)

2002-03-11

Filing date

2004-09-29

Publication date

2010-10-11

2004-09-29 Application filed by Aventis Pharma Sa filed Critical Aventis Pharma Sa

2004-11-25 Publication of NO20044137L publication Critical patent/NO20044137L/no

2010-10-11 Publication of NO329384B1 publication Critical patent/NO329384B1/no

Links

150000001875 compounds Chemical class 0.000 title claims description 30
229940127554 medical product Drugs 0.000 title claims description 7
239000000825 pharmaceutical preparation Substances 0.000 title claims description 6
238000002360 preparation method Methods 0.000 title claims description 5
YDTDKKULPWTHRV-UHFFFAOYSA-N 1H-indazol-3-amine Chemical class C1=CC=C2C(N)=NNC2=C1 YDTDKKULPWTHRV-UHFFFAOYSA-N 0.000 title description 10
-1 trifluoromethylsulfanyl Chemical group 0.000 claims description 187
239000000203 mixture Substances 0.000 claims description 155
DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 67
125000000217 alkyl group Chemical group 0.000 claims description 47
125000003118 aryl group Chemical group 0.000 claims description 40
125000001072 heteroaryl group Chemical group 0.000 claims description 39
229910052736 halogen Inorganic materials 0.000 claims description 32
150000002367 halogens Chemical class 0.000 claims description 32
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 30
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 29
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 21
125000001424 substituent group Chemical group 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
UEXIIADMDJKGQI-UHFFFAOYSA-N n-(6-chloro-1h-indazol-3-yl)-2,2,2-trifluoroacetamide Chemical compound ClC1=CC=C2C(NC(=O)C(F)(F)F)=NNC2=C1 UEXIIADMDJKGQI-UHFFFAOYSA-N 0.000 claims description 18
238000000034 method Methods 0.000 claims description 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
125000000623 heterocyclic group Chemical group 0.000 claims description 15
150000002431 hydrogen Chemical class 0.000 claims description 15
125000003342 alkenyl group Chemical group 0.000 claims description 14
SCRIVIIUSSVXFD-UHFFFAOYSA-N 2-amino-n-(1h-indazol-3-yl)benzamide Chemical compound NC1=CC=CC=C1C(=O)NC1=NNC2=CC=CC=C12 SCRIVIIUSSVXFD-UHFFFAOYSA-N 0.000 claims description 12
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 12
LGOIHNJTDXKOSR-UHFFFAOYSA-N n-(1h-indazol-3-yl)-2-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)NC1=NNC2=CC=CC=C12 LGOIHNJTDXKOSR-UHFFFAOYSA-N 0.000 claims description 12
VCFLLXDSOODEGV-UHFFFAOYSA-N n-(1h-indazol-3-yl)acetamide Chemical compound C1=CC=C2C(NC(=O)C)=NNC2=C1 VCFLLXDSOODEGV-UHFFFAOYSA-N 0.000 claims description 12
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 11
125000000304 alkynyl group Chemical group 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 10
125000005592 polycycloalkyl group Polymers 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
QRUMCIZXFCVYTO-UHFFFAOYSA-N n-(6-chloro-1h-indazol-3-yl)thiophene-2-carboxamide Chemical compound N=1NC2=CC(Cl)=CC=C2C=1NC(=O)C1=CC=CS1 QRUMCIZXFCVYTO-UHFFFAOYSA-N 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 7
125000005842 heteroatom Chemical group 0.000 claims description 7
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 6
OWTWZUTUKNTZIO-UHFFFAOYSA-N 2-amino-4-chloro-n-(1h-indazol-3-yl)benzamide Chemical compound NC1=CC(Cl)=CC=C1C(=O)NC1=NNC2=CC=CC=C12 OWTWZUTUKNTZIO-UHFFFAOYSA-N 0.000 claims description 6
LIXCJYSXXFTWLM-UHFFFAOYSA-N 2-amino-5-chloro-n-(1h-indazol-3-yl)benzamide Chemical compound NC1=CC=C(Cl)C=C1C(=O)NC1=NNC2=CC=CC=C12 LIXCJYSXXFTWLM-UHFFFAOYSA-N 0.000 claims description 6
CXLVEGLVHJLQKM-UHFFFAOYSA-N 2-hydroxy-n-(1h-indazol-3-yl)benzamide Chemical compound OC1=CC=CC=C1C(=O)NC1=NNC2=CC=CC=C12 CXLVEGLVHJLQKM-UHFFFAOYSA-N 0.000 claims description 6
DYMSJANEHGEKSI-UHFFFAOYSA-N 3,3-diphenylpropanamide Chemical compound C=1C=CC=CC=1C(CC(=O)N)C1=CC=CC=C1 DYMSJANEHGEKSI-UHFFFAOYSA-N 0.000 claims description 6
JICLIKCVSDSJAI-UHFFFAOYSA-N 3-chloro-n-(6-chloro-1h-indazol-3-yl)benzamide Chemical compound ClC1=CC=CC(C(=O)NC=2C3=CC=C(Cl)C=C3NN=2)=C1 JICLIKCVSDSJAI-UHFFFAOYSA-N 0.000 claims description 6
CNNQMHOWGDBJEB-UHFFFAOYSA-N 4-chloro-n-(1h-indazol-3-yl)-2-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1C(=O)NC1=NNC2=CC=CC=C12 CNNQMHOWGDBJEB-UHFFFAOYSA-N 0.000 claims description 6
XAGHPNMJJUUUSB-UHFFFAOYSA-N 4-chloro-n-(1h-indazol-3-yl)benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NC1=NNC2=CC=CC=C12 XAGHPNMJJUUUSB-UHFFFAOYSA-N 0.000 claims description 6
QACYZJSZIJWGME-UHFFFAOYSA-N 4-chloro-n-(6-chloro-1h-indazol-3-yl)benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NC1=NNC2=CC(Cl)=CC=C12 QACYZJSZIJWGME-UHFFFAOYSA-N 0.000 claims description 6
UCRMWGBHOQEQFF-UHFFFAOYSA-N 5-chloro-n-(1h-indazol-3-yl)-2-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1C(=O)NC1=NNC2=CC=CC=C12 UCRMWGBHOQEQFF-UHFFFAOYSA-N 0.000 claims description 6
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
YSPJSIDLBHTWLD-UHFFFAOYSA-N n-(1h-indazol-3-yl)-2-phenylacetamide Chemical compound N=1NC2=CC=CC=C2C=1NC(=O)CC1=CC=CC=C1 YSPJSIDLBHTWLD-UHFFFAOYSA-N 0.000 claims description 6
RUBJJMGJJGCPIS-UHFFFAOYSA-N n-(1h-indazol-3-yl)-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC1=NNC2=CC=CC=C12 RUBJJMGJJGCPIS-UHFFFAOYSA-N 0.000 claims description 6
IANRATJJDNGXNL-UHFFFAOYSA-N n-(1h-indazol-3-yl)-4-nitrobenzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)NC1=NNC2=CC=CC=C12 IANRATJJDNGXNL-UHFFFAOYSA-N 0.000 claims description 6
NUFIKDKHBWSZOM-UHFFFAOYSA-N n-(1h-indazol-3-yl)benzamide Chemical compound N=1NC2=CC=CC=C2C=1NC(=O)C1=CC=CC=C1 NUFIKDKHBWSZOM-UHFFFAOYSA-N 0.000 claims description 6
RVWAZXOEPGFVQF-UHFFFAOYSA-N n-(1h-indazol-3-yl)butanamide Chemical compound C1=CC=C2C(NC(=O)CCC)=NNC2=C1 RVWAZXOEPGFVQF-UHFFFAOYSA-N 0.000 claims description 6
IMFPOAQRILJQSH-UHFFFAOYSA-N n-(5-amino-1h-indazol-3-yl)acetamide Chemical compound C1=C(N)C=C2C(NC(=O)C)=NNC2=C1 IMFPOAQRILJQSH-UHFFFAOYSA-N 0.000 claims description 6
VIUDBQFHKZLPEN-UHFFFAOYSA-N n-(6-chloro-1h-indazol-3-yl)-4-hexoxybenzamide Chemical compound C1=CC(OCCCCCC)=CC=C1C(=O)NC1=NNC2=CC(Cl)=CC=C12 VIUDBQFHKZLPEN-UHFFFAOYSA-N 0.000 claims description 6
FIDGEFATSZSPPC-UHFFFAOYSA-N n-(6-chloro-1h-indazol-3-yl)furan-2-carboxamide Chemical compound N=1NC2=CC(Cl)=CC=C2C=1NC(=O)C1=CC=CO1 FIDGEFATSZSPPC-UHFFFAOYSA-N 0.000 claims description 6
230000008569 process Effects 0.000 claims description 6
239000011593 sulfur Chemical group 0.000 claims description 6
QUQLDSFMMZCQHF-UHFFFAOYSA-N n-(6-chloro-1h-indazol-3-yl)acetamide Chemical compound ClC1=CC=C2C(NC(=O)C)=NNC2=C1 QUQLDSFMMZCQHF-UHFFFAOYSA-N 0.000 claims description 5
VHQZZDZWVQELLJ-UHFFFAOYSA-N n-(6-chloro-1h-indazol-3-yl)butanamide Chemical compound ClC1=CC=C2C(NC(=O)CCC)=NNC2=C1 VHQZZDZWVQELLJ-UHFFFAOYSA-N 0.000 claims description 5
230000004770 neurodegeneration Effects 0.000 claims description 5
208000015122 neurodegenerative disease Diseases 0.000 claims description 5
108090000623 proteins and genes Proteins 0.000 claims description 5
102000004169 proteins and genes Human genes 0.000 claims description 5
208000007530 Essential hypertension Diseases 0.000 claims description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
206010061598 Immunodeficiency Diseases 0.000 claims description 4
208000029462 Immunodeficiency disease Diseases 0.000 claims description 4
206010028980 Neoplasm Diseases 0.000 claims description 4
208000008589 Obesity Diseases 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
201000011510 cancer Diseases 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
230000007813 immunodeficiency Effects 0.000 claims description 4
125000004245 indazol-3-yl group Chemical group [H]N1N=C(*)C2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 4
208000014674 injury Diseases 0.000 claims description 4
QQVNXRROZHWJNS-UHFFFAOYSA-N n-(6-bromo-1h-indazol-3-yl)butanamide Chemical compound BrC1=CC=C2C(NC(=O)CCC)=NNC2=C1 QQVNXRROZHWJNS-UHFFFAOYSA-N 0.000 claims description 4
LBEIKJLOCIYZFH-UHFFFAOYSA-N n-[6-(4-nitrophenyl)-1h-indazol-3-yl]butanamide Chemical compound C=1C=C2C(NC(=O)CCC)=NNC2=CC=1C1=CC=C([N+]([O-])=O)C=C1 LBEIKJLOCIYZFH-UHFFFAOYSA-N 0.000 claims description 4
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208000027232 peripheral nervous system disease Diseases 0.000 claims description 4
208000033808 peripheral neuropathy Diseases 0.000 claims description 4
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125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
208000011580 syndromic disease Diseases 0.000 claims description 4
230000001225 therapeutic effect Effects 0.000 claims description 4
230000008733 trauma Effects 0.000 claims description 4
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 3
208000024827 Alzheimer disease Diseases 0.000 claims description 3
206010012289 Dementia Diseases 0.000 claims description 3
201000011240 Frontotemporal dementia Diseases 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
208000018737 Parkinson disease Diseases 0.000 claims description 3
208000000609 Pick Disease of the Brain Diseases 0.000 claims description 3
KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 3
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208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
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FKLRXXUPAZZVPP-UHFFFAOYSA-N n-(5-nitro-1h-indazol-3-yl)acetamide Chemical compound C1=C([N+]([O-])=O)C=C2C(NC(=O)C)=NNC2=C1 FKLRXXUPAZZVPP-UHFFFAOYSA-N 0.000 claims description 3
GEDASJHDXVAVLN-UHFFFAOYSA-N n-(5-nitro-1h-indazol-3-yl)butanamide Chemical compound C1=C([N+]([O-])=O)C=C2C(NC(=O)CCC)=NNC2=C1 GEDASJHDXVAVLN-UHFFFAOYSA-N 0.000 claims description 3
JTDQNZOUNKWCNO-UHFFFAOYSA-N n-(6-bromo-7-nitro-1h-indazol-3-yl)butanamide Chemical compound BrC1=CC=C2C(NC(=O)CCC)=NNC2=C1[N+]([O-])=O JTDQNZOUNKWCNO-UHFFFAOYSA-N 0.000 claims description 3
BVIWKIBBSPTOPO-UHFFFAOYSA-N n-(6-phenyl-1h-indazol-3-yl)butanamide Chemical compound C=1C=C2C(NC(=O)CCC)=NNC2=CC=1C1=CC=CC=C1 BVIWKIBBSPTOPO-UHFFFAOYSA-N 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
125000005593 norbornanyl group Chemical group 0.000 claims description 3
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230000026731 phosphorylation Effects 0.000 claims description 3
238000006366 phosphorylation reaction Methods 0.000 claims description 3
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 3
UMIPSPNTPGXRBY-UHFFFAOYSA-N 2-chloro-n-(6,7-difluoro-1h-indazol-3-yl)acetamide Chemical compound FC1=CC=C2C(NC(=O)CCl)=NNC2=C1F UMIPSPNTPGXRBY-UHFFFAOYSA-N 0.000 claims description 2
LXIGXAWGTPTFCO-UHFFFAOYSA-N 4-amino-N-(6-chloro-1H-indazol-3-yl)piperidine-1-carboxamide N-(6-chloro-1H-indazol-3-yl)morpholine-4-carboxamide Chemical compound Clc1ccc2c(NC(=O)N3CCOCC3)n[nH]c2c1.NC1CCN(CC1)C(=O)Nc1n[nH]c2cc(Cl)ccc12 LXIGXAWGTPTFCO-UHFFFAOYSA-N 0.000 claims description 2
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FRQHANAVLTVQOL-UHFFFAOYSA-N ClC1=C(C=CC(=C1)O)C1=CC=C2C(=NNC2=C1)NC(CCC)=O.ClC1=C(C=CC(=C1)OCC1=CC=CC=C1)C1=CC=C2C(=NNC2=C1)NC(CCC)=O.ClC1=C(C=C2C(=NNC2=C1)NC(CCC)=O)C1=COC=C1 Chemical compound ClC1=C(C=CC(=C1)O)C1=CC=C2C(=NNC2=C1)NC(CCC)=O.ClC1=C(C=CC(=C1)OCC1=CC=CC=C1)C1=CC=C2C(=NNC2=C1)NC(CCC)=O.ClC1=C(C=C2C(=NNC2=C1)NC(CCC)=O)C1=COC=C1 FRQHANAVLTVQOL-UHFFFAOYSA-N 0.000 claims description 2
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QIPZNZHCZXZALV-MYDAVQQHSA-N ClC1=CC=C2C(=NNC2=C1)NC(/C=C/C(=O)OCC)=O.ClC1=CC=C2C(=NNC2=C1)NC(/C=C/C(=O)O)=O.ClC1=CC=C2C(=NNC2=C1)NC(\C=C/C(=O)O)=O Chemical group ClC1=CC=C2C(=NNC2=C1)NC(/C=C/C(=O)OCC)=O.ClC1=CC=C2C(=NNC2=C1)NC(/C=C/C(=O)O)=O.ClC1=CC=C2C(=NNC2=C1)NC(\C=C/C(=O)O)=O QIPZNZHCZXZALV-MYDAVQQHSA-N 0.000 claims 1
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BFGNZTADCJNFAK-VHMCZHJXSA-N FC(C1=CC=C2C(=NNC2=C1)NC(CCC(=O)OCC)=O)(F)F.FC(C1=CC=C2C(=NNC2=C1)NC(\C=C/C)=O)(F)F.FC(C1=CC=C2C(=NNC2=C1)NC(\C=C\C)=O)(F)F Chemical compound FC(C1=CC=C2C(=NNC2=C1)NC(CCC(=O)OCC)=O)(F)F.FC(C1=CC=C2C(=NNC2=C1)NC(\C=C/C)=O)(F)F.FC(C1=CC=C2C(=NNC2=C1)NC(\C=C\C)=O)(F)F BFGNZTADCJNFAK-VHMCZHJXSA-N 0.000 claims 1
QCCNEAXLQVZWPI-UHFFFAOYSA-N FC(C=1C=C2C(=NNC2=CC1)NC(C=C/C)=O)(F)F.FC(C=1C=C2C(=NNC2=CC1)NC(C=CC)=O)(F)F Chemical compound FC(C=1C=C2C(=NNC2=CC1)NC(C=C/C)=O)(F)F.FC(C=1C=C2C(=NNC2=CC1)NC(C=CC)=O)(F)F QCCNEAXLQVZWPI-UHFFFAOYSA-N 0.000 claims 1
UMQJHYTWQGKARS-UHFFFAOYSA-N N-[5,6-bis(4-hydroxyphenyl)-1H-indazol-3-yl]butanamide N-[5,6-bis(4-phenylmethoxyphenyl)-1H-indazol-3-yl]butanamide Chemical compound CCCC(=O)Nc1n[nH]c2cc(-c3ccc(O)cc3)c(cc12)-c1ccc(O)cc1.CCCC(=O)Nc1n[nH]c2cc(-c3ccc(OCc4ccccc4)cc3)c(cc12)-c1ccc(OCc2ccccc2)cc1 UMQJHYTWQGKARS-UHFFFAOYSA-N 0.000 claims 1
BAGQYOIGQSAIBC-UHFFFAOYSA-N N-[5-benzoyl-6-(4-hydroxyphenyl)-1H-indazol-3-yl]butanamide Chemical compound C=1C=CC=CC=1C(=O)C=1C=C2C(NC(=O)CCC)=NNC2=CC=1C1=CC=C(O)C=C1 BAGQYOIGQSAIBC-UHFFFAOYSA-N 0.000 claims 1
239000005864 Sulphur Substances 0.000 claims 1
208000013044 corticobasal degeneration disease Diseases 0.000 claims 1
SDRUEXONAYGMDS-WAYWQWQTSA-N ethyl (z)-4-[(6-chloro-1h-indazol-3-yl)amino]-4-oxobut-2-enoate Chemical compound ClC1=CC=C2C(NC(=O)\C=C/C(=O)OCC)=NNC2=C1 SDRUEXONAYGMDS-WAYWQWQTSA-N 0.000 claims 1
GVMSSASBWGBNMJ-UHFFFAOYSA-N n-(4-iodo-1h-indazol-3-yl)butanamide Chemical compound C1=CC(I)=C2C(NC(=O)CCC)=NNC2=C1 GVMSSASBWGBNMJ-UHFFFAOYSA-N 0.000 claims 1
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FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 92
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239000002609 medium Substances 0.000 description 38
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125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 description 26
CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 26
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RZCPLOMUUCFPQA-UHFFFAOYSA-N (4-ethylphenyl)boronic acid Chemical compound CCC1=CC=C(B(O)O)C=C1 RZCPLOMUUCFPQA-UHFFFAOYSA-N 0.000 description 3
DMJHEIDWSIAXCS-UHFFFAOYSA-N (4-phenylmethoxyphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1OCC1=CC=CC=C1 DMJHEIDWSIAXCS-UHFFFAOYSA-N 0.000 description 3
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 3
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BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
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CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
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Classifications

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NO20044137A 2002-03-11 2004-09-29 Aminoindazolderivater, fremstilling derav samt farmasoytiske preparater og medisinske produkter inneholdende forbindelsene NO329384B1 (no)

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FR0202997A FR2836915B1 (fr)	2002-03-11	2002-03-11	Derives d'aminoindazoles, procede de preparation et intermediaires de ce procede a titre de medicaments et compositions pharmaceutiques les renfermant
PCT/FR2003/000752 WO2003078403A2 (fr)	2002-03-11	2003-03-07	Derives d’aminoindazoles comme inhibiteurs de proteine-kinase

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FR (1)	FR2836915B1 (pl)
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KR100423899B1 (ko) *	2000-05-10	2004-03-24	주식회사 엘지생명과학	세포 증식 억제제로 유용한 1,1-디옥소이소티아졸리딘을갖는 인다졸

2002
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2003
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2004
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Also Published As

Publication number	Publication date
KR101068770B1 (ko)	2011-09-30
FR2836915B1 (fr)	2008-01-11
BR0308373A (pt)	2005-01-11
RS52396B (sr)	2013-02-28
MEP16108A (en)	2010-06-10
US6949579B2 (en)	2005-09-27
UY27713A1 (es)	2003-09-30
HRP20040824A2 (en)	2005-06-30
NZ535147A (en)	2007-08-31
JP2010222357A (ja)	2010-10-07
US20040014802A1 (en)	2004-01-22
JP2005530711A (ja)	2005-10-13
MY138269A (en)	2009-05-29
PA8568301A1 (es)	2005-02-04
EP1487804A2 (fr)	2004-12-22
JO2326B1 (en)	2006-06-28
KR20040091121A (ko)	2004-10-27
CA2478542A1 (fr)	2003-09-25
AR038915A1 (es)	2005-02-02
MXPA04007478A (es)	2004-11-10
ME00058B (me)	2010-10-10
MA27230A1 (fr)	2005-02-01
RU2345070C2 (ru)	2009-01-27
EP1487804B1 (fr)	2014-02-26
CN1656078A (zh)	2005-08-17
SV2003001494A (es)	2003-07-10
NO20044137L (no)	2004-11-25
HRP20040824B1 (hr)	2013-05-31
JP5315287B2 (ja)	2013-10-16
WO2003078403A2 (fr)	2003-09-25
AU2003242809B8 (en)	2010-04-15
PE20040155A1 (es)	2004-04-18
TWI329103B (en)	2010-08-21
RU2004129780A (ru)	2005-04-10
CA2478542C (fr)	2012-02-21
PL370478A1 (pl)	2005-05-30
IL163831A (en)	2010-12-30
IL163831A0 (en)	2005-12-18
CN101962365A (zh)	2011-02-02
WO2003078403A3 (fr)	2004-04-22
FR2836915A1 (fr)	2003-09-12
GT200300057A (es)	2006-10-19
JP4648630B2 (ja)	2011-03-09
AU2003242809A1 (en)	2003-09-29
ZA200406687B (en)	2005-10-26
AU2003242809B2 (en)	2010-03-18
RS79504A (sr)	2006-12-15
TW200403226A (en)	2004-03-01

Legal Events

Date	Code	Title	Description
2014-11-03	MM1K	Lapsed by not paying the annual fees

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