SK9162001A3 - Substituted (aminoiminomethyl or aminomethyl)benzoheteroaryl compounds as factor xa inhibitors - Google Patents

Substituted (aminoiminomethyl or aminomethyl)benzoheteroaryl compounds as factor xa inhibitors Download PDF

Info

Publication number: SK9162001A3
Authority: SK; Slovakia
Prior art keywords: ethyl; carbamimidoyl; indol; benzamide; pyrimidin
Prior art date: 1998-12-24

Application number

SK916-2001A

Other languages

English (en)

Slovak (sk)

Inventor

William P Dankulich

Daniel G Mcgarry

Christopher Burns

Timothy F Gallagher

Francis A Volz

Original Assignee

Aventis Pharm Prod Inc

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.)

1998-12-24

Filing date

1999-12-22

Publication date

2002-01-07

1999-12-22 Application filed by Aventis Pharm Prod Inc filed Critical Aventis Pharm Prod Inc

2002-01-07 Publication of SK9162001A3 publication Critical patent/SK9162001A3/sk

Links

-1 aminoiminomethyl Chemical group 0.000 title claims abstract description 643
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 title abstract description 3
229940123583 Factor Xa inhibitor Drugs 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 167
238000000034 method Methods 0.000 claims abstract description 109
239000000203 mixture Substances 0.000 claims abstract description 97
108010074860 Factor Xa Proteins 0.000 claims abstract description 31
230000015572 biosynthetic process Effects 0.000 claims abstract description 30
238000002360 preparation method Methods 0.000 claims abstract description 22
230000000694 effects Effects 0.000 claims abstract description 9
230000002401 inhibitory effect Effects 0.000 claims abstract description 9
108090000190 Thrombin Proteins 0.000 claims abstract description 6
229960004072 thrombin Drugs 0.000 claims abstract description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 362
KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 103
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 87
125000001072 heteroaryl group Chemical group 0.000 claims description 84
125000000623 heterocyclic group Chemical group 0.000 claims description 66
150000001408 amides Chemical class 0.000 claims description 61
125000000217 alkyl group Chemical group 0.000 claims description 51
125000003118 aryl group Chemical group 0.000 claims description 45
150000003839 salts Chemical class 0.000 claims description 44
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 41
125000000753 cycloalkyl group Chemical group 0.000 claims description 36
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 34
125000000392 cycloalkenyl group Chemical group 0.000 claims description 28
229910052739 hydrogen Inorganic materials 0.000 claims description 25
239000001257 hydrogen Substances 0.000 claims description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
125000003710 aryl alkyl group Chemical group 0.000 claims description 16
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
WKSIHEZXQNJQCB-UHFFFAOYSA-N 2-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1C(O)=O WKSIHEZXQNJQCB-UHFFFAOYSA-N 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
125000002947 alkylene group Chemical group 0.000 claims description 14
239000000126 substance Substances 0.000 claims description 14
GSYIVQLTSZFJRV-UHFFFAOYSA-N 3-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC(C(O)=O)=C1 GSYIVQLTSZFJRV-UHFFFAOYSA-N 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
125000004350 aryl cycloalkyl group Chemical group 0.000 claims description 9
230000002792 vascular Effects 0.000 claims description 9
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 8
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 8
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 8
125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims description 8
230000004962 physiological condition Effects 0.000 claims description 8
239000012453 solvate Substances 0.000 claims description 8
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 7
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 7
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
RJAORKRYFLHWDP-UHFFFAOYSA-N 2-[[4-[4-[2-(3-carbamimidoyl-1H-indol-5-yl)ethylcarbamoyl]phenyl]pyrimidin-2-yl]methylamino]ethanesulfonic acid Chemical compound C(N)(=N)C1=CNC2=CC=C(C=C12)CCNC(=O)C1=CC=C(C=C1)C1=NC(=NC=C1)CNCCS(=O)(=O)O RJAORKRYFLHWDP-UHFFFAOYSA-N 0.000 claims description 6
ABPJAFATKIUAOP-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-[2-(2,3-dihydroxypropylamino)pyrimidin-4-yl]benzamide Chemical compound C1=C2C(C(=N)N)=CNC2=CC=C1CCNC(=O)C(C=C1)=CC=C1C1=CC=NC(NCC(O)CO)=N1 ABPJAFATKIUAOP-UHFFFAOYSA-N 0.000 claims description 6
208000007536 Thrombosis Diseases 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
229940002612 prodrug Drugs 0.000 claims description 6
239000000651 prodrug Substances 0.000 claims description 6
125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
RHSDKKXEPUBAAS-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-(6-methoxypyridazin-3-yl)benzamide Chemical compound N1=NC(OC)=CC=C1C1=CC=C(C(=O)NCCC=2C=C3C(C(N)=N)=CNC3=CC=2)C=C1 RHSDKKXEPUBAAS-UHFFFAOYSA-N 0.000 claims description 5
KXVGBKDPNYLUJA-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-[2-(3-hydroxypropylamino)pyrimidin-4-yl]benzamide Chemical compound C1=C2C(C(=N)N)=CNC2=CC=C1CCNC(=O)C(C=C1)=CC=C1C1=CC=NC(NCCCO)=N1 KXVGBKDPNYLUJA-UHFFFAOYSA-N 0.000 claims description 5
ROIXWIYSXXTORR-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-[2-(3-imidazol-1-ylpropylamino)pyrimidin-4-yl]benzamide Chemical compound C1=C2C(C(=N)N)=CNC2=CC=C1CCNC(=O)C(C=C1)=CC=C1C(N=1)=CC=NC=1NCCCN1C=CN=C1 ROIXWIYSXXTORR-UHFFFAOYSA-N 0.000 claims description 5
MQQZETXGPBVQBE-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-[2-(3-methoxypropylamino)pyrimidin-4-yl]benzamide Chemical compound COCCCNC1=NC=CC(C=2C=CC(=CC=2)C(=O)NCCC=2C=C3C(C(N)=N)=CNC3=CC=2)=N1 MQQZETXGPBVQBE-UHFFFAOYSA-N 0.000 claims description 5
RUTLFMUUQDKHAW-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-[2-(4-hydroxypiperidin-1-yl)pyrimidin-4-yl]benzamide Chemical compound C1=C2C(C(=N)N)=CNC2=CC=C1CCNC(=O)C(C=C1)=CC=C1C(N=1)=CC=NC=1N1CCC(O)CC1 RUTLFMUUQDKHAW-UHFFFAOYSA-N 0.000 claims description 5
PLXIXULXKLHIEZ-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-[2-(6-morpholin-4-ylhexylamino)pyrimidin-4-yl]benzamide Chemical compound C1=C2C(C(=N)N)=CNC2=CC=C1CCNC(=O)C(C=C1)=CC=C1C(N=1)=CC=NC=1NCCCCCCN1CCOCC1 PLXIXULXKLHIEZ-UHFFFAOYSA-N 0.000 claims description 5
ADMLORQGBBTBHH-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-[2-(6-piperidin-1-ylhexylamino)pyrimidin-4-yl]benzamide Chemical compound C1=C2C(C(=N)N)=CNC2=CC=C1CCNC(=O)C(C=C1)=CC=C1C(N=1)=CC=NC=1NCCCCCCN1CCCCC1 ADMLORQGBBTBHH-UHFFFAOYSA-N 0.000 claims description 5
VEFFMJSAQHSYEO-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-[2-(6-pyrrolidin-1-ylhexylamino)pyrimidin-4-yl]benzamide Chemical compound C1=C2C(C(=N)N)=CNC2=CC=C1CCNC(=O)C(C=C1)=CC=C1C(N=1)=CC=NC=1NCCCCCCN1CCCC1 VEFFMJSAQHSYEO-UHFFFAOYSA-N 0.000 claims description 5
KJZJJBVXRDAEQI-UHFFFAOYSA-N N-[[4-[4-[2-(3-carbamimidoyl-1H-indol-5-yl)ethylcarbamoyl]phenyl]pyridin-2-yl]methyl]piperidine-4-carboxamide Chemical compound NC(=N)c1c[nH]c2ccc(CCNC(=O)c3ccc(cc3)-c3ccnc(CNC(=O)C4CCNCC4)c3)cc12 KJZJJBVXRDAEQI-UHFFFAOYSA-N 0.000 claims description 5
239000003146 anticoagulant agent Substances 0.000 claims description 5
125000005215 cycloalkylheteroaryl group Chemical group 0.000 claims description 5
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 5
125000006308 propyl amino group Chemical group 0.000 claims description 5
238000002560 therapeutic procedure Methods 0.000 claims description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
UQDONLZZHSEBEA-UHFFFAOYSA-N 4-[2-(aminomethyl)pyridin-4-yl]-N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]benzamide Chemical compound C1=NC(CN)=CC(C=2C=CC(=CC=2)C(=O)NCCC=2C=C3C(C(N)=N)=CNC3=CC=2)=C1 UQDONLZZHSEBEA-UHFFFAOYSA-N 0.000 claims description 4
AKFFQHGSBAMFJH-UHFFFAOYSA-N 4-[2-[(2-amino-2-oxoethyl)-methylamino]pyrimidin-4-yl]-N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]benzamide Chemical compound NC(=O)CN(C)C1=NC=CC(C=2C=CC(=CC=2)C(=O)NCCC=2C=C3C(C(N)=N)=CNC3=CC=2)=N1 AKFFQHGSBAMFJH-UHFFFAOYSA-N 0.000 claims description 4
STEMQBXSHCLCCI-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-2-(4-chlorophenyl)acetamide Chemical compound C1=C2C(C(=N)N)=CNC2=CC=C1CCNC(=O)CC1=CC=C(Cl)C=C1 STEMQBXSHCLCCI-UHFFFAOYSA-N 0.000 claims description 4
QSUZAKHEXNCQKH-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-(1,2,3,6-tetrahydropyridin-4-yl)benzamide Chemical compound C1=C2C(C(=N)N)=CNC2=CC=C1CCNC(=O)C(C=C1)=CC=C1C1=CCNCC1 QSUZAKHEXNCQKH-UHFFFAOYSA-N 0.000 claims description 4
IAJFROLKDRQSJF-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-(2-morpholin-4-ylpyrimidin-4-yl)benzamide Chemical compound C1=C2C(C(=N)N)=CNC2=CC=C1CCNC(=O)C(C=C1)=CC=C1C(N=1)=CC=NC=1N1CCOCC1 IAJFROLKDRQSJF-UHFFFAOYSA-N 0.000 claims description 4
ZAIIZEGKFXYLOO-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-(2-piperidin-1-ylpyrimidin-4-yl)benzamide Chemical compound C1=C2C(C(=N)N)=CNC2=CC=C1CCNC(=O)C(C=C1)=CC=C1C(N=1)=CC=NC=1N1CCCCC1 ZAIIZEGKFXYLOO-UHFFFAOYSA-N 0.000 claims description 4
UMTXZESFKJLYBE-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-(7H-pyrrolo[2,3-d]pyrimidin-6-yl)benzamide Chemical compound N1=CN=C2NC(C3=CC=C(C=C3)C(=O)NCCC3=CC=C4NC=C(C4=C3)C(=N)N)=CC2=C1 UMTXZESFKJLYBE-UHFFFAOYSA-N 0.000 claims description 4
BKESRDZZGNNQIL-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-[2-(3-morpholin-4-ylpropylamino)pyrimidin-4-yl]benzamide Chemical compound C1=C2C(C(=N)N)=CNC2=CC=C1CCNC(=O)C(C=C1)=CC=C1C(N=1)=CC=NC=1NCCCN1CCOCC1 BKESRDZZGNNQIL-UHFFFAOYSA-N 0.000 claims description 4
UAXJFXFVBMARIS-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-[2-(3-piperidin-1-ylpropylamino)pyrimidin-4-yl]benzamide Chemical compound C1=C2C(C(=N)N)=CNC2=CC=C1CCNC(=O)C(C=C1)=CC=C1C(N=1)=CC=NC=1NCCCN1CCCCC1 UAXJFXFVBMARIS-UHFFFAOYSA-N 0.000 claims description 4
UVJPAFBBJVNEMD-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-[2-(4-methylpiperazin-1-yl)pyrimidin-4-yl]benzamide Chemical compound C1CN(C)CCN1C1=NC=CC(C=2C=CC(=CC=2)C(=O)NCCC=2C=C3C(C(N)=N)=CNC3=CC=2)=N1 UVJPAFBBJVNEMD-UHFFFAOYSA-N 0.000 claims description 4
SJIKADMDMOMMFT-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-[2-(4-piperidin-1-ylbutylamino)pyrimidin-4-yl]benzamide Chemical compound C1=C2C(C(=N)N)=CNC2=CC=C1CCNC(=O)C(C=C1)=CC=C1C(N=1)=CC=NC=1NCCCCN1CCCCC1 SJIKADMDMOMMFT-UHFFFAOYSA-N 0.000 claims description 4
DGKVIYZJGDRJIO-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-[2-(5-piperidin-1-ylpentylamino)pyrimidin-4-yl]benzamide Chemical compound C1=C2C(C(=N)N)=CNC2=CC=C1CCNC(=O)C(C=C1)=CC=C1C(N=1)=CC=NC=1NCCCCCN1CCCCC1 DGKVIYZJGDRJIO-UHFFFAOYSA-N 0.000 claims description 4
UYWSEIOOPBTNBS-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-[2-(5-pyrrolidin-1-ylpentylamino)pyrimidin-4-yl]benzamide Chemical compound C1=C2C(C(=N)N)=CNC2=CC=C1CCNC(=O)C(C=C1)=CC=C1C(N=1)=CC=NC=1NCCCCCN1CCCC1 UYWSEIOOPBTNBS-UHFFFAOYSA-N 0.000 claims description 4
230000002159 abnormal effect Effects 0.000 claims description 4
206010000891 acute myocardial infarction Diseases 0.000 claims description 4
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
125000004367 cycloalkylaryl group Chemical group 0.000 claims description 4
230000002093 peripheral effect Effects 0.000 claims description 4
125000004964 sulfoalkyl group Chemical group 0.000 claims description 4
FKBYDGHOPOEEEP-UHFFFAOYSA-N 2-pyridin-2-ylbenzamide Chemical compound NC(=O)C1=CC=CC=C1C1=CC=CC=N1 FKBYDGHOPOEEEP-UHFFFAOYSA-N 0.000 claims description 3
YBVBYISUXSWSPQ-UHFFFAOYSA-N 4-(3-aminoprop-1-ynyl)-N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]benzamide Chemical compound C1=CC(C#CCN)=CC=C1C(=O)NCCC1=CC=C(NC=C2C(N)=N)C2=C1 YBVBYISUXSWSPQ-UHFFFAOYSA-N 0.000 claims description 3
DLJQUHVSBIXDOP-UHFFFAOYSA-N 4-(4-aminopiperidin-1-yl)-N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]benzamide Chemical compound C1CC(N)CCN1C1=CC=C(C(=O)NCCC=2C=C3C(C(N)=N)=CNC3=CC=2)C=C1 DLJQUHVSBIXDOP-UHFFFAOYSA-N 0.000 claims description 3
PYWKNXLVIMZLBM-UHFFFAOYSA-N 4-[2-(1-amino-1-oxopropan-2-yl)oxypyrimidin-4-yl]-N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]benzamide Chemical compound NC(=O)C(C)OC1=NC=CC(C=2C=CC(=CC=2)C(=O)NCCC=2C=C3C(C(N)=N)=CNC3=CC=2)=N1 PYWKNXLVIMZLBM-UHFFFAOYSA-N 0.000 claims description 3
OJHRHRDVHNEARP-UHFFFAOYSA-N 4-[4-[2-(3-carbamimidoyl-1H-indol-5-yl)ethylcarbamoyl]phenyl]piperidine-1-carboxamide Chemical compound C1CN(C(=O)N)CCC1C1=CC=C(C(=O)NCCC=2C=C3C(C(N)=N)=CNC3=CC=2)C=C1 OJHRHRDVHNEARP-UHFFFAOYSA-N 0.000 claims description 3
AAPAWXJPSXFAQU-UHFFFAOYSA-N 5-(2-aminoethyl)-1H-indole-3-carboximidamide Chemical compound C1=CC2=C(C=C1CCN)C(=CN2)C(=N)N AAPAWXJPSXFAQU-UHFFFAOYSA-N 0.000 claims description 3
TZOUWMUZXDSWAN-UHFFFAOYSA-N CC(=O)NN1C=C(C=CC1=O)C2=CC=C(C=C2)C(=O)NCCC3=CC4=C(C=C3)NC=C4C(=N)N Chemical compound CC(=O)NN1C=C(C=CC1=O)C2=CC=C(C=C2)C(=O)NCCC3=CC4=C(C=C3)NC=C4C(=N)N TZOUWMUZXDSWAN-UHFFFAOYSA-N 0.000 claims description 3
206010053567 Coagulopathies Diseases 0.000 claims description 3
HQECSLXGFWOJAX-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-3-chlorobenzamide Chemical compound C1=C2C(C(=N)N)=CNC2=CC=C1CCNC(=O)C1=CC=CC(Cl)=C1 HQECSLXGFWOJAX-UHFFFAOYSA-N 0.000 claims description 3
FAWTUOUHTZMPFU-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-(1,2,4-thiadiazol-5-yl)benzamide Chemical compound C1=C2C(C(=N)N)=CNC2=CC=C1CCNC(=O)C(C=C1)=CC=C1C1=NC=NS1 FAWTUOUHTZMPFU-UHFFFAOYSA-N 0.000 claims description 3
SDZGYCFQWLWLNC-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-(1-methylpiperidin-4-yl)benzamide Chemical compound C1CN(C)CCC1C1=CC=C(C(=O)NCCC=2C=C3C(C(N)=N)=CNC3=CC=2)C=C1 SDZGYCFQWLWLNC-UHFFFAOYSA-N 0.000 claims description 3
YJFFVBQHLGZUDV-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-(2-methoxypyrimidin-4-yl)benzamide Chemical compound COC1=NC=CC(C=2C=CC(=CC=2)C(=O)NCCC=2C=C3C(C(N)=N)=CNC3=CC=2)=N1 YJFFVBQHLGZUDV-UHFFFAOYSA-N 0.000 claims description 3
VUABHZSREJTHTK-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-(2-piperazin-1-ylpyrimidin-4-yl)benzamide Chemical compound C1=C2C(C(=N)N)=CNC2=CC=C1CCNC(=O)C(C=C1)=CC=C1C(N=1)=CC=NC=1N1CCNCC1 VUABHZSREJTHTK-UHFFFAOYSA-N 0.000 claims description 3
YNNUOFWPUPXYTD-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-(2-pyrrolidin-1-ylpyrimidin-4-yl)benzamide Chemical compound C1=C2C(C(=N)N)=CNC2=CC=C1CCNC(=O)C(C=C1)=CC=C1C(N=1)=CC=NC=1N1CCCC1 YNNUOFWPUPXYTD-UHFFFAOYSA-N 0.000 claims description 3
COGFRJXDZBYKGA-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-(6-oxo-1H-pyridazin-3-yl)benzamide Chemical compound C1=C2C(C(=N)N)=CNC2=CC=C1CCNC(=O)C(C=C1)=CC=C1C=1C=CC(=O)NN=1 COGFRJXDZBYKGA-UHFFFAOYSA-N 0.000 claims description 3
UTGGHUXMBXGHGA-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-(6-oxopiperidin-3-yl)benzamide Chemical compound C1=C2C(C(=N)N)=CNC2=CC=C1CCNC(=O)C(C=C1)=CC=C1C1CCC(=O)NC1 UTGGHUXMBXGHGA-UHFFFAOYSA-N 0.000 claims description 3
VZDWMMLHJHXJKO-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-[2-(2,2,2-trifluoroethoxy)pyrimidin-4-yl]benzamide Chemical compound C1=C2C(C(=N)N)=CNC2=CC=C1CCNC(=O)C(C=C1)=CC=C1C1=CC=NC(OCC(F)(F)F)=N1 VZDWMMLHJHXJKO-UHFFFAOYSA-N 0.000 claims description 3
HZOUGSSHRXFIDY-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-[2-(2-methoxyethoxy)pyrimidin-4-yl]benzamide Chemical compound COCCOC1=NC=CC(C=2C=CC(=CC=2)C(=O)NCCC=2C=C3C(C(N)=N)=CNC3=CC=2)=N1 HZOUGSSHRXFIDY-UHFFFAOYSA-N 0.000 claims description 3
SGDIZNXOVUCKEN-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-[2-(2-pyrrolidin-1-ylethoxy)pyrimidin-4-yl]benzamide Chemical compound C1=C2C(C(=N)N)=CNC2=CC=C1CCNC(=O)C(C=C1)=CC=C1C(N=1)=CC=NC=1OCCN1CCCC1 SGDIZNXOVUCKEN-UHFFFAOYSA-N 0.000 claims description 3
OAWHZKAZIYSAAU-UHFFFAOYSA-N N-[2-(3-carbamimidoyl-1H-indol-5-yl)ethyl]-4-[2-(cyclopropylmethylamino)pyrimidin-4-yl]benzamide Chemical compound C1=C2C(C(=N)N)=CNC2=CC=C1CCNC(=O)C(C=C1)=CC=C1C(N=1)=CC=NC=1NCC1CC1 OAWHZKAZIYSAAU-UHFFFAOYSA-N 0.000 claims description 3
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125000004181 carboxyalkyl group Chemical group 0.000 description 2
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238000006555 catalytic reaction Methods 0.000 description 2
ZDQWVKDDJDIVAL-UHFFFAOYSA-N catecholborane Chemical compound C1=CC=C2O[B]OC2=C1 ZDQWVKDDJDIVAL-UHFFFAOYSA-N 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
230000004663 cell proliferation Effects 0.000 description 2
BJDCWCLMFKKGEE-CMDXXVQNSA-N chembl252518 Chemical compound C([C@@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2O[C@H](O)[C@@H]4C BJDCWCLMFKKGEE-CMDXXVQNSA-N 0.000 description 2
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LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
230000008878 coupling Effects 0.000 description 2
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
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HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 2
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150000002009 diols Chemical class 0.000 description 2
MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
229940088598 enzyme Drugs 0.000 description 2
BMHLYVICYWOZQO-UHFFFAOYSA-N ethyl 4-(3,4-dimethoxyphenyl)benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C1=CC=C(OC)C(OC)=C1 BMHLYVICYWOZQO-UHFFFAOYSA-N 0.000 description 2
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125000004494 ethyl ester group Chemical group 0.000 description 2
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238000001704 evaporation Methods 0.000 description 2
IAWCIZWLKMTPLL-UHFFFAOYSA-N fluoroethyne Chemical compound FC#C IAWCIZWLKMTPLL-UHFFFAOYSA-N 0.000 description 2
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125000000524 functional group Chemical group 0.000 description 2
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150000004820 halides Chemical class 0.000 description 2
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230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
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239000012535 impurity Substances 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
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239000010410 layer Substances 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
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229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
QHJOWSXZDCTNQX-UHFFFAOYSA-N methyl 2-(4-bromophenyl)acetate Chemical compound COC(=O)CC1=CC=C(Br)C=C1 QHJOWSXZDCTNQX-UHFFFAOYSA-N 0.000 description 2
KBVKTEXEJFBWDW-UHFFFAOYSA-N methyl 2-[4-(furan-2-yl)phenyl]-2-methylpropanoate Chemical compound C1=CC(C(C)(C)C(=O)OC)=CC=C1C1=CC=CO1 KBVKTEXEJFBWDW-UHFFFAOYSA-N 0.000 description 2
QGWZUSJDKNEEFZ-UHFFFAOYSA-N methyl 4-(6-methoxypyridin-3-yl)-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC=C1C1=CC=C(OC)N=C1 QGWZUSJDKNEEFZ-UHFFFAOYSA-N 0.000 description 2
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ZGKLUEUQVJRLTO-UHFFFAOYSA-N methyl 4-(7h-pyrrolo[2,3-d]pyrimidin-6-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC2=CN=CN=C2N1 ZGKLUEUQVJRLTO-UHFFFAOYSA-N 0.000 description 2
ILQHMKDRKUWPGR-UHFFFAOYSA-N methyl 4-[1-[2-(dimethylamino)ethyl]-6-oxopyridazin-3-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NN(CCN(C)C)C(=O)C=C1 ILQHMKDRKUWPGR-UHFFFAOYSA-N 0.000 description 2
JPGRSTBIEYGVNO-UHFFFAOYSA-N methyl 4-ethynylbenzoate Chemical compound COC(=O)C1=CC=C(C#C)C=C1 JPGRSTBIEYGVNO-UHFFFAOYSA-N 0.000 description 2
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KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
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238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
230000007794 irritation Effects 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
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125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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125000001786 isothiazolyl group Chemical group 0.000 description 1
238000004750 isotope dilution mass spectroscopy Methods 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
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235000014655 lactic acid Nutrition 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
125000005647 linker group Chemical group 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 1
229960003646 lysine Drugs 0.000 description 1
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
239000000347 magnesium hydroxide Substances 0.000 description 1
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VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
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125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
XYIMTNQZOCLBNT-UHFFFAOYSA-N methyl 3-chloro-4-(6-methoxypyridin-3-yl)benzoate Chemical compound ClC1=CC(C(=O)OC)=CC=C1C1=CC=C(OC)N=C1 XYIMTNQZOCLBNT-UHFFFAOYSA-N 0.000 description 1
JJEJBUNCUNIKPV-UHFFFAOYSA-N methyl 3-chloro-4-(trifluoromethylsulfonyloxy)benzoate Chemical compound COC(=O)C1=CC=C(OS(=O)(=O)C(F)(F)F)C(Cl)=C1 JJEJBUNCUNIKPV-UHFFFAOYSA-N 0.000 description 1
ZSBIMTDWIGWJPW-UHFFFAOYSA-N methyl 3-chloro-4-hydroxybenzoate Chemical compound COC(=O)C1=CC=C(O)C(Cl)=C1 ZSBIMTDWIGWJPW-UHFFFAOYSA-N 0.000 description 1
NTMOENLZDSKKRW-UHFFFAOYSA-N methyl 4-(1,3-dimethyl-2-oxo-1,3-diazinan-5-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1CN(C)C(=O)N(C)C1 NTMOENLZDSKKRW-UHFFFAOYSA-N 0.000 description 1
GVYILCIXRUNVAT-UHFFFAOYSA-N methyl 4-(1-methylpiperidin-4-yl)oxybenzoate Chemical compound C1=CC(C(=O)OC)=CC=C1OC1CCN(C)CC1 GVYILCIXRUNVAT-UHFFFAOYSA-N 0.000 description 1
YTSOKYCHDGMLDH-UHFFFAOYSA-N methyl 4-(1h-pyrrolo[3,2-c]pyridin-2-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC2=CN=CC=C2N1 YTSOKYCHDGMLDH-UHFFFAOYSA-N 0.000 description 1
YXJOGPHQFGNWMK-UHFFFAOYSA-N methyl 4-(2-carbamoylpyridin-4-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=NC(C(N)=O)=C1 YXJOGPHQFGNWMK-UHFFFAOYSA-N 0.000 description 1
GAJCPTDIYHFRDB-UHFFFAOYSA-N methyl 4-(2-methoxypyrimidin-4-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=NC(OC)=N1 GAJCPTDIYHFRDB-UHFFFAOYSA-N 0.000 description 1
KUDBGJKVFHQIRF-UHFFFAOYSA-N methyl 4-(2-oxo-1,3-diazinan-5-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1CNC(=O)NC1 KUDBGJKVFHQIRF-UHFFFAOYSA-N 0.000 description 1
ATQBKAKXTSJGQT-UHFFFAOYSA-N methyl 4-(2-oxo-1h-pyrimidin-5-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CNC(=O)N=C1 ATQBKAKXTSJGQT-UHFFFAOYSA-N 0.000 description 1
OMKQKBOYVRHLRP-UHFFFAOYSA-N methyl 4-(2-trimethylsilylethynyl)benzoate Chemical compound COC(=O)C1=CC=C(C#C[Si](C)(C)C)C=C1 OMKQKBOYVRHLRP-UHFFFAOYSA-N 0.000 description 1
DCRAOUFTJQRVGW-UHFFFAOYSA-N methyl 4-(6-methoxypyridazin-3-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(OC)N=N1 DCRAOUFTJQRVGW-UHFFFAOYSA-N 0.000 description 1
SZXUBUCWZIVCCK-UHFFFAOYSA-N methyl 4-[2-[(dimethylamino)methyl]pyridin-4-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=NC(CN(C)C)=C1 SZXUBUCWZIVCCK-UHFFFAOYSA-N 0.000 description 1
CYEXEOXALMJXDI-UHFFFAOYSA-N methyl 4-bromo-2-methylbenzoate Chemical compound COC(=O)C1=CC=C(Br)C=C1C CYEXEOXALMJXDI-UHFFFAOYSA-N 0.000 description 1
UFZCEGCJKXHARR-UHFFFAOYSA-N methyl 4-furo[3,2-c]pyridin-2-ylbenzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC2=CN=CC=C2O1 UFZCEGCJKXHARR-UHFFFAOYSA-N 0.000 description 1
QQQMCQRQWVXBOY-UHFFFAOYSA-N methyl 4-pyridin-4-ylbenzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=NC=C1 QQQMCQRQWVXBOY-UHFFFAOYSA-N 0.000 description 1
LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
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125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
VZTFAKOSXBSKCA-UHFFFAOYSA-N n-[1-(3-cyano-1h-indol-5-yl)propan-2-yl]-4-(6-oxo-1h-pyridin-3-yl)benzamide Chemical compound C=1C=C2NC=C(C#N)C2=CC=1CC(C)NC(=O)C(C=C1)=CC=C1C=1C=CC(=O)NC=1 VZTFAKOSXBSKCA-UHFFFAOYSA-N 0.000 description 1
VSRTWIQSFDDWNS-UHFFFAOYSA-N n-[2-(3-cyano-1-methylindol-5-yl)ethyl]-4-(6-methoxypyridin-3-yl)benzamide Chemical compound C1=NC(OC)=CC=C1C1=CC=C(C(=O)NCCC=2C=C3C(C#N)=CN(C)C3=CC=2)C=C1 VSRTWIQSFDDWNS-UHFFFAOYSA-N 0.000 description 1
GQHIHFMWSQANJJ-UHFFFAOYSA-N n-[2-(3-cyano-1h-indol-5-yl)ethyl]-4-(1,2,3,6-tetrahydropyridin-4-yl)benzamide Chemical compound C=1C=C2NC=C(C#N)C2=CC=1CCNC(=O)C(C=C1)=CC=C1C1=CCNCC1 GQHIHFMWSQANJJ-UHFFFAOYSA-N 0.000 description 1
CXYDJUBMKMXNOC-UHFFFAOYSA-N n-[2-(3-cyano-1h-indol-5-yl)ethyl]-4-(1-methylpiperidin-4-yl)benzamide Chemical compound C1CN(C)CCC1C1=CC=C(C(=O)NCCC=2C=C3C(C#N)=CNC3=CC=2)C=C1 CXYDJUBMKMXNOC-UHFFFAOYSA-N 0.000 description 1
QPBHAYHTAVNNKE-UHFFFAOYSA-N n-[2-(3-cyano-1h-indol-5-yl)ethyl]-4-(1h-imidazol-5-yl)benzamide Chemical compound C=1C=C2NC=C(C#N)C2=CC=1CCNC(=O)C(C=C1)=CC=C1C1=CN=CN1 QPBHAYHTAVNNKE-UHFFFAOYSA-N 0.000 description 1
YKZFZMQXUBEGKU-UHFFFAOYSA-N n-[2-(3-cyano-1h-indol-5-yl)ethyl]-4-(6-methoxypyridazin-3-yl)benzamide Chemical compound N1=NC(OC)=CC=C1C1=CC=C(C(=O)NCCC=2C=C3C(C#N)=CNC3=CC=2)C=C1 YKZFZMQXUBEGKU-UHFFFAOYSA-N 0.000 description 1
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BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
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125000001544 thienyl group Chemical group 0.000 description 1
125000004149 thio group Chemical group *S* 0.000 description 1
MHRLWUPLSHYLOK-UHFFFAOYSA-N thiomorpholine-3,5-dicarboxylic acid Chemical compound OC(=O)C1CSCC(C(O)=O)N1 MHRLWUPLSHYLOK-UHFFFAOYSA-N 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
WRTMQOHKMFDUKX-UHFFFAOYSA-N triiodide Chemical compound I[I-]I WRTMQOHKMFDUKX-UHFFFAOYSA-N 0.000 description 1
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
238000000825 ultraviolet detection Methods 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
239000002966 varnish Substances 0.000 description 1
230000009723 vascular congestion Effects 0.000 description 1
210000004509 vascular smooth muscle cell Anatomy 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
229940007718 zinc hydroxide Drugs 0.000 description 1
229910021511 zinc hydroxide Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- 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
- C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
- 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur 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
- 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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 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
- 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
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Diabetes (AREA)
Vascular Medicine (AREA)
Surgery (AREA)
Cardiology (AREA)
Virology (AREA)
Urology & Nephrology (AREA)
Hematology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Indole Compounds (AREA)

SK916-2001A 1998-12-24 1999-12-22 Substituted (aminoiminomethyl or aminomethyl)benzoheteroaryl compounds as factor xa inhibitors SK9162001A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US11371098P	1998-12-24	1998-12-24
PCT/US1999/030623 WO2000039087A2 (en)	1998-12-24	1999-12-22	Substituted (aminoiminomethyl or aminomethyl)benzoheteroaryl compounds as factor xa inhibitors

Publications (1)

Publication Number	Publication Date
SK9162001A3 true SK9162001A3 (en)	2002-01-07

Family

ID=22351040

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK916-2001A SK9162001A3 (en)	1998-12-24	1999-12-22	Substituted (aminoiminomethyl or aminomethyl)benzoheteroaryl compounds as factor xa inhibitors

Country Status (19)

Country	Link
US (2)	US6541505B1 (de)
EP (1)	EP1140901A2 (de)
JP (1)	JP2002533438A (de)
KR (1)	KR20010086461A (de)
CN (1)	CN1333766A (de)
AU (1)	AU760983B2 (de)
BR (1)	BR9916845A (de)
CA (1)	CA2358047A1 (de)
CZ (1)	CZ20012350A3 (de)
EE (1)	EE200100341A (de)
HK (1)	HK1041696A1 (de)
HU (1)	HUP0104994A3 (de)
ID (1)	ID30516A (de)
IL (1)	IL143906A0 (de)
NO (1)	NO20013142L (de)
NZ (1)	NZ512548A (de)
PL (1)	PL349267A1 (de)
SK (1)	SK9162001A3 (de)
WO (1)	WO2000039087A2 (de)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AR036873A1 (es)	2001-09-07	2004-10-13	Euro Celtique Sa	Piridinas aril sustituidas a, composiciones farmaceuticas y el uso de las mismas para la preparacion de un medicamento
AR037233A1 (es)	2001-09-07	2004-11-03	Euro Celtique Sa	Piridinas aril sustituidas, composiciones farmaceuticas y el uso de dichos compuestos para la elaboracion de un medicamento
EP1569912B1 (de)	2002-12-03	2015-04-29	Pharmacyclics, Inc.	2-(2-hydroxybiphenyl-3-yl)-1h-benzoimidazole-5-carboxamidinderivate als faktor vii-a hemmer
TW200533357A (en) *	2004-01-08	2005-10-16	Millennium Pharm Inc	2-(amino-substituted)-4-aryl pyrimidines and related compounds useful for treating inflammatory diseases
US7429604B2 (en) *	2004-06-15	2008-09-30	Bristol Myers Squibb Company	Six-membered heterocycles useful as serine protease inhibitors
BRPI0418939A (pt) *	2004-07-06	2008-04-08	Xenon Pharmaceuticals Inc	derivados de nicotinamida e sua utilização como agentes terapêuticos
AR055271A1 (es) *	2004-10-05	2007-08-15	Smithkline Beecham Corp	Compuesto del acido bifenil carboxilico, composicion farmaceutica que lo comprende, su uso para preparar esta ultima y proceso para prepararlo
JP4932735B2 (ja)	2004-12-17	2012-05-16	アムジエン・インコーポレーテツド	アミノピリミジン化合物および使用方法
SI2094702T1 (sl) *	2006-12-14	2016-03-31	Gilead Sciences, Inc.	Virusni inhibitorji
CA2707492A1 (en) *	2007-12-13	2009-06-18	Amgen Inc.	Gamma secretase modulators
JP2013508350A (ja) *	2009-10-20	2013-03-07	ファイザー・インク	ガンマ−セクレターゼモジュレーターとしての新規なヘテロアリールイミダゾールおよびヘテロアリールトリアゾール
EP2316820A1 (de) *	2009-10-28	2011-05-04	Dompe S.p.A.	Als Bradykinin-Rezeptorantagonisten nützliche 2-Arylpropionamid-Derivate und pharmazeutische Zusammensetzungen damit
US8354410B2 (en) *	2010-03-11	2013-01-15	Bristol-Meyers Squibb Company	Compounds for the treatment of hepatitis C
CN103242239B (zh) *	2013-05-20	2015-09-23	洛阳师范学院	多取代嘧啶基苯甲醇及其制备方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2400518A1 (fr)	1977-08-18	1979-03-16	Parcor	Benzo(b)thieno(3,2-c) et (2,3-c)pyridines, leur procede de preparation et leur application en therapeutique
NZ227841A (en)	1988-02-12	1991-08-27	Merck Sharp & Dohme	Heterocyclic compounds with at least two non-condensed five membered rings and pharmaceutical compositions
US5340833A (en)	1992-05-01	1994-08-23	Eisai Co., Ltd.	Urokinase inhibitors
US5597823A (en) *	1995-01-27	1997-01-28	Abbott Laboratories	Tricyclic substituted hexahydrobenz [e]isoindole alpha-1 adrenergic antagonists
CA2241904C (en) *	1996-01-02	2004-12-21	Rhone-Poulenc Rorer Pharmaceuticals Inc.	Substituted n-[(aminoiminomethyl or aminomethyl)phenyl]propyl amides
JP2002514162A (ja) *	1996-07-08	2002-05-14	デュポンファーマシューティカルズカンパニー	Ｘａ因子阻害薬およびトロンビン阻害薬としてのアミジノインドール類、アミジノアゾール類、およびそれらの類似体

1999
- 1999-12-22 CZ CZ20012350A patent/CZ20012350A3/cs unknown
- 1999-12-22 NZ NZ512548A patent/NZ512548A/en unknown
- 1999-12-22 BR BR9916845-6A patent/BR9916845A/pt not_active IP Right Cessation
- 1999-12-22 KR KR1020017008037A patent/KR20010086461A/ko not_active Withdrawn
- 1999-12-22 IL IL14390699A patent/IL143906A0/xx unknown
- 1999-12-22 EP EP99966560A patent/EP1140901A2/de not_active Withdrawn
- 1999-12-22 HK HK02103389.1A patent/HK1041696A1/zh unknown
- 1999-12-22 JP JP2000590999A patent/JP2002533438A/ja active Pending
- 1999-12-22 CA CA002358047A patent/CA2358047A1/en not_active Abandoned
- 1999-12-22 HU HU0104994A patent/HUP0104994A3/hu unknown
- 1999-12-22 WO PCT/US1999/030623 patent/WO2000039087A2/en not_active Ceased
- 1999-12-22 EE EEP200100341A patent/EE200100341A/xx unknown
- 1999-12-22 CN CN99815691A patent/CN1333766A/zh active Pending
- 1999-12-22 AU AU22071/00A patent/AU760983B2/en not_active Ceased
- 1999-12-22 PL PL99349267A patent/PL349267A1/xx unknown
- 1999-12-22 SK SK916-2001A patent/SK9162001A3/sk unknown
- 1999-12-22 ID IDW00200101374A patent/ID30516A/id unknown
2000
- 2000-06-30 US US09/609,103 patent/US6541505B1/en not_active Expired - Fee Related
2001
- 2001-06-22 NO NO20013142A patent/NO20013142L/no not_active Application Discontinuation
2003
- 2003-02-24 US US10/372,499 patent/US20030153604A1/en not_active Abandoned

Also Published As

Publication number	Publication date
HUP0104994A2 (hu)	2002-04-29
CZ20012350A3 (cs)	2001-09-12
US20030153604A1 (en)	2003-08-14
PL349267A1 (en)	2002-07-01
HUP0104994A3 (en)	2002-06-28
AU2207100A (en)	2000-07-31
AU760983B2 (en)	2003-05-29
KR20010086461A (ko)	2001-09-12
ID30516A (id)	2001-12-13
JP2002533438A (ja)	2002-10-08
NO20013142L (no)	2001-08-21
WO2000039087A2 (en)	2000-07-06
WO2000039087A3 (en)	2000-11-09
BR9916845A (pt)	2001-10-30
EE200100341A (et)	2002-12-16
CA2358047A1 (en)	2000-07-06
EP1140901A2 (de)	2001-10-10
IL143906A0 (en)	2002-04-21
HK1041696A1 (zh)	2002-07-19
US6541505B1 (en)	2003-04-01
NZ512548A (en)	2003-08-29
CN1333766A (zh)	2002-01-30
NO20013142D0 (no)	2001-06-22

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