OA12727A - Indole-2-carboxamides as factor XA inhibitors. - Google Patents

Indole-2-carboxamides as factor XA inhibitors. Download PDF

Info

Publication number: OA12727A
Authority: OA; OAPI
Prior art keywords: chloro; indole; piperidin; thiophen; amide
Prior art date: 2001-11-22

Application number

OA1200400142A

Other languages

English (en)

Inventor

Marc Nazare

Melanie Essrich

David William Will

Hans Matt-Ter

Krut Ritter

Wolkmar Wehner

Original Assignee

Aventis Pharma Gmbh

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.)

2001-11-22

Filing date

2002-11-08

Publication date

2006-06-27

2002-11-08 Application filed by Aventis Pharma Gmbh filed Critical Aventis Pharma Gmbh

2006-06-27 Publication of OA12727A publication Critical patent/OA12727A/en

Links

VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical class C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-UHFFFAOYSA-N 0.000 title 1
229940123583 Factor Xa inhibitor Drugs 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 302
238000000034 method Methods 0.000 claims abstract description 72
230000005764 inhibitory process Effects 0.000 claims abstract description 20
230000023555 blood coagulation Effects 0.000 claims abstract description 12
238000002560 therapeutic procedure Methods 0.000 claims abstract description 12
239000003814 drug Substances 0.000 claims abstract description 9
230000008569 process Effects 0.000 claims abstract description 6
208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 5
208000001435 Thromboembolism Diseases 0.000 claims abstract description 3
-1 phenylpyridyl Chemical group 0.000 claims description 262
239000002253 acid Substances 0.000 claims description 140
ZRQQXFMGYSOKDF-UHFFFAOYSA-N 1-propan-2-ylpiperidin-4-amine Chemical compound CC(C)N1CCC(N)CC1 ZRQQXFMGYSOKDF-UHFFFAOYSA-N 0.000 claims description 118
239000000203 mixture Substances 0.000 claims description 92
239000000460 chlorine Substances 0.000 claims description 70
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 69
125000000217 alkyl group Chemical group 0.000 claims description 69
125000001072 heteroaryl group Chemical group 0.000 claims description 62
229910052736 halogen Inorganic materials 0.000 claims description 55
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 54
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 49
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 45
150000002367 halogens Chemical class 0.000 claims description 45
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
RJCRRLMFYIXJAH-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]indole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=CC=CC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 RJCRRLMFYIXJAH-UHFFFAOYSA-N 0.000 claims description 41
125000003118 aryl group Chemical group 0.000 claims description 41
229960000583 acetic acid Drugs 0.000 claims description 40
150000003839 salts Chemical class 0.000 claims description 38
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 36
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 36
229910052757 nitrogen Inorganic materials 0.000 claims description 36
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 31
230000015572 biosynthetic process Effects 0.000 claims description 30
150000002148 esters Chemical class 0.000 claims description 28
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 27
125000004122 cyclic group Chemical group 0.000 claims description 22
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 21
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 21
229910052760 oxygen Inorganic materials 0.000 claims description 21
239000001301 oxygen Substances 0.000 claims description 21
229910052717 sulfur Inorganic materials 0.000 claims description 21
239000011593 sulfur Substances 0.000 claims description 21
125000001041 indolyl group Chemical group 0.000 claims description 20
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 19
125000005842 heteroatom Chemical group 0.000 claims description 18
229920006395 saturated elastomer Polymers 0.000 claims description 18
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 17
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 17
125000002950 monocyclic group Chemical group 0.000 claims description 17
150000003536 tetrazoles Chemical class 0.000 claims description 17
125000002883 imidazolyl group Chemical group 0.000 claims description 16
BTDZSVPICJLNIN-UHFFFAOYSA-N 1-pyridin-4-ylpiperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=NC=C1 BTDZSVPICJLNIN-UHFFFAOYSA-N 0.000 claims description 15
125000002619 bicyclic group Chemical group 0.000 claims description 15
229910052801 chlorine Inorganic materials 0.000 claims description 15
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 15
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 14
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 14
125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
125000004076 pyridyl group Chemical group 0.000 claims description 14
125000001544 thienyl group Chemical group 0.000 claims description 14
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 12
FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 12
CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims description 12
JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 12
QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 12
POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 claims description 12
MSRJJSCOWHWGGX-UHFFFAOYSA-N 2h-1,3-diazepine Chemical compound C1N=CC=CC=N1 MSRJJSCOWHWGGX-UHFFFAOYSA-N 0.000 claims description 12
WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims description 12
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 12
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 12
DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims description 12
XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 12
229910052794 bromium Inorganic materials 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
125000000524 functional group Chemical group 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 12
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 12
125000003373 pyrazinyl group Chemical group 0.000 claims description 12
125000003226 pyrazolyl group Chemical group 0.000 claims description 12
125000002098 pyridazinyl group Chemical group 0.000 claims description 12
125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 12
125000000335 thiazolyl group Chemical group 0.000 claims description 12
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 12
LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims description 11
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
229910052731 fluorine Inorganic materials 0.000 claims description 11
125000000842 isoxazolyl group Chemical group 0.000 claims description 11
125000000168 pyrrolyl group Chemical group 0.000 claims description 11
125000001113 thiadiazolyl group Chemical group 0.000 claims description 11
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
125000004429 atom Chemical group 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000002541 furyl group Chemical group 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
125000001786 isothiazolyl group Chemical group 0.000 claims description 10
125000003831 tetrazolyl group Chemical group 0.000 claims description 10
NBNWLLXCAIOATK-UHFFFAOYSA-N 1-[(3-methoxyphenyl)methyl]indole-2-carboxylic acid Chemical compound COC1=CC=CC(CN2C3=CC=CC=C3C=C2C(O)=O)=C1 NBNWLLXCAIOATK-UHFFFAOYSA-N 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 9
125000002971 oxazolyl group Chemical group 0.000 claims description 9
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 9
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
208000007536 Thrombosis Diseases 0.000 claims description 8
239000003146 anticoagulant agent Substances 0.000 claims description 8
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
SJGALSBBFTYSBA-UHFFFAOYSA-N oxaziridine Chemical compound C1NO1 SJGALSBBFTYSBA-UHFFFAOYSA-N 0.000 claims description 8
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 8
IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 claims description 8
OEACEEHJARIXJW-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]indole-5-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC(C(O)=O)=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 OEACEEHJARIXJW-UHFFFAOYSA-N 0.000 claims description 7
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 7
150000001408 amides Chemical class 0.000 claims description 7
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 7
239000002243 precursor Substances 0.000 claims description 7
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 7
ZFCKJGACJXTSOI-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-7-methylindole-2-carboxylic acid Chemical compound C1=2C(C)=CC=CC=2C=C(C(O)=O)N1CC(=NO1)C=C1C1=CC=C(Cl)S1 ZFCKJGACJXTSOI-UHFFFAOYSA-N 0.000 claims description 6
208000005189 Embolism Diseases 0.000 claims description 6
230000001154 acute effect Effects 0.000 claims description 6
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 6
201000010099 disease Diseases 0.000 claims description 6
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
150000004702 methyl esters Chemical class 0.000 claims description 6
125000003386 piperidinyl group Chemical group 0.000 claims description 6
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 6
125000005494 pyridonyl group Chemical group 0.000 claims description 6
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
125000005493 quinolyl group Chemical group 0.000 claims description 6
238000001356 surgical procedure Methods 0.000 claims description 6
125000001425 triazolyl group Chemical group 0.000 claims description 6
DQJGJGNWFRPEHZ-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]indole-4-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=C(C(O)=O)C=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 DQJGJGNWFRPEHZ-UHFFFAOYSA-N 0.000 claims description 5
ZUEKSECYPXHXAQ-UHFFFAOYSA-N 1-pyrimidin-4-ylpiperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=NC=N1 ZUEKSECYPXHXAQ-UHFFFAOYSA-N 0.000 claims description 5
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 5
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 5
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
208000037803 restenosis Diseases 0.000 claims description 5
230000002792 vascular Effects 0.000 claims description 5
IYCMYOWBZQNVBV-UHFFFAOYSA-N (1-propan-2-ylpiperidin-4-yl)methanamine Chemical compound CC(C)N1CCC(CN)CC1 IYCMYOWBZQNVBV-UHFFFAOYSA-N 0.000 claims description 4
CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 claims description 4
125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 4
ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical compound C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 claims description 4
ZDEGYYDOWMXDCH-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-5-methylsulfonyl-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC(S(C)(=O)=O)=CC=C2N1CC(=O)NC1=CC=C(Cl)C=N1 ZDEGYYDOWMXDCH-UHFFFAOYSA-N 0.000 claims description 4
JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 claims description 4
MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 4
KGWNRZLPXLBMPS-UHFFFAOYSA-N 2h-1,3-oxazine Chemical compound C1OC=CC=N1 KGWNRZLPXLBMPS-UHFFFAOYSA-N 0.000 claims description 4
NTYABNDBNKVWOO-UHFFFAOYSA-N 2h-1,3-thiazine Chemical compound C1SC=CC=N1 NTYABNDBNKVWOO-UHFFFAOYSA-N 0.000 claims description 4
YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims description 4
ZAISDHPZTZIFQF-UHFFFAOYSA-N 2h-1,4-thiazine Chemical compound C1SC=CN=C1 ZAISDHPZTZIFQF-UHFFFAOYSA-N 0.000 claims description 4
BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 4
XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 claims description 4
GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical compound C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 claims description 4
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 4
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 4
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 4
230000020764 fibrinolysis Effects 0.000 claims description 4
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
125000005956 isoquinolyl group Chemical group 0.000 claims description 4
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
MIJCTFQIMWKOJZ-UHFFFAOYSA-N n-(4-chlorophenyl)-2-[2-[4-(pyridin-4-ylamino)piperidine-1-carbonyl]indol-1-yl]acetamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)CN1C2=CC=CC=C2C=C1C(=O)N1CCC(NC=2C=CN=CC=2)CC1 MIJCTFQIMWKOJZ-UHFFFAOYSA-N 0.000 claims description 4
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 4
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
229930192474 thiophene Natural products 0.000 claims description 4
230000002537 thrombolytic effect Effects 0.000 claims description 4
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
UOCPLRLVNRLSHU-UHFFFAOYSA-N (3-pyridin-4-yl-4,5-dihydro-1,2-oxazol-5-yl)methanamine Chemical compound O1C(CN)CC(C=2C=CN=CC=2)=N1 UOCPLRLVNRLSHU-UHFFFAOYSA-N 0.000 claims description 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
125000006565 (C4-C7) cyclic group Chemical group 0.000 claims description 3
ZXVWFOMYPHVUGO-UHFFFAOYSA-N 1-(2-methylpropyl)piperidin-4-amine Chemical compound CC(C)CN1CCC(N)CC1 ZXVWFOMYPHVUGO-UHFFFAOYSA-N 0.000 claims description 3
XUKZYTNPGQPSGF-UHFFFAOYSA-N 1-(3-chlorophenyl)indole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=CC=CC=C2N1C1=CC=CC(Cl)=C1 XUKZYTNPGQPSGF-UHFFFAOYSA-N 0.000 claims description 3
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WGAOEHZSJWVLBY-UHFFFAOYSA-N methyl 5-chloro-1h-indole-2-carboxylate Chemical compound ClC1=CC=C2NC(C(=O)OC)=CC2=C1 WGAOEHZSJWVLBY-UHFFFAOYSA-N 0.000 description 1
QUZGGDBUGGJROM-UHFFFAOYSA-N methyl 5-fluoro-1h-indole-2-carboxylate Chemical compound FC1=CC=C2NC(C(=O)OC)=CC2=C1 QUZGGDBUGGJROM-UHFFFAOYSA-N 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
YGZYVBHJLLVOKE-UHFFFAOYSA-N n-(1-propan-2-ylpiperidin-4-yl)-1h-indole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC=CC=C2N1 YGZYVBHJLLVOKE-UHFFFAOYSA-N 0.000 description 1
ABRZLNLFABKMCJ-UHFFFAOYSA-N n-(1-pyridin-4-ylpiperidin-4-yl)pyridin-4-amine Chemical compound C1CN(C=2C=CN=CC=2)CCC1NC1=CC=NC=C1 ABRZLNLFABKMCJ-UHFFFAOYSA-N 0.000 description 1
WHVRIEBTPHOXEE-UHFFFAOYSA-N n-(4-chlorophenyl)-2-[2-(4-pyrrolidin-1-ylpiperidine-1-carbonyl)indol-1-yl]acetamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)CN1C2=CC=CC=C2C=C1C(=O)N1CCC(N2CCCC2)CC1 WHVRIEBTPHOXEE-UHFFFAOYSA-N 0.000 description 1
CJWRWSIZDGWSLT-UHFFFAOYSA-N n-(4-iodophenyl)-1-[(3-methoxyphenyl)methyl]indole-2-carboxamide Chemical compound COC1=CC=CC(CN2C3=CC=CC=C3C=C2C(=O)NC=2C=CC(I)=CC=2)=C1 CJWRWSIZDGWSLT-UHFFFAOYSA-N 0.000 description 1
YSCLDBIQLDEDMZ-UHFFFAOYSA-N n-[1-(2-chloropyrimidin-4-yl)piperidin-4-yl]-1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]indole-2-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3C=C2C(=O)NC2CCN(CC2)C=2N=C(Cl)N=CC=2)=NO1 YSCLDBIQLDEDMZ-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical compound CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 1
KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical class ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
NNKPHNTWNILINE-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-4-methyl-5-[3-[[1-[2-[2-(methylamino)ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]benzamide Chemical compound CNCCOC1=CC=CC=C1C1(NC=2C(N(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)C=CN=2)=O)CC1 NNKPHNTWNILINE-UHFFFAOYSA-N 0.000 description 1
TVWJOMGXJWDIQA-UHFFFAOYSA-N n-methyl-1-pyridin-4-ylpiperidin-4-amine Chemical compound C1CC(NC)CCN1C1=CC=NC=C1 TVWJOMGXJWDIQA-UHFFFAOYSA-N 0.000 description 1
SESXBIFUTWZZOU-UHFFFAOYSA-N n-piperidin-4-ylpyridin-4-amine Chemical compound C1CNCCC1NC1=CC=NC=C1 SESXBIFUTWZZOU-UHFFFAOYSA-N 0.000 description 1
GINABUAPACIWCA-UHFFFAOYSA-N n-propan-2-ylpiperidin-4-amine Chemical compound CC(C)NC1CCNCC1 GINABUAPACIWCA-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
150000003901 oxalic acid esters Chemical class 0.000 description 1
JMJRYTGVHCAYCT-UHFFFAOYSA-N oxan-4-one Chemical compound O=C1CCOCC1 JMJRYTGVHCAYCT-UHFFFAOYSA-N 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
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239000000546 pharmaceutical excipient Substances 0.000 description 1
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125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
125000005954 phenoxathiinyl group Chemical group 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl chloride Substances ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
230000004962 physiological condition Effects 0.000 description 1
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IYPZRUYMFDWKSS-UHFFFAOYSA-N piperazin-1-amine Chemical compound NN1CCNCC1 IYPZRUYMFDWKSS-UHFFFAOYSA-N 0.000 description 1
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 description 1
JLPGSSHHLKZYMJ-UHFFFAOYSA-N piperidin-4-amine;hydrochloride Chemical compound Cl.NC1CCNCC1 JLPGSSHHLKZYMJ-UHFFFAOYSA-N 0.000 description 1
KBOGICFUPOMDKS-UHFFFAOYSA-N piperidin-4-ylcarbamic acid Chemical compound OC(=O)NC1CCNCC1 KBOGICFUPOMDKS-UHFFFAOYSA-N 0.000 description 1
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229920005990 polystyrene resin Polymers 0.000 description 1
LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
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238000011533 pre-incubation Methods 0.000 description 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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150000003141 primary amines Chemical class 0.000 description 1
JGDTVBLOYMDZNS-UHFFFAOYSA-N propan-2-yl 1h-indole-5-carboxylate Chemical compound CC(C)OC(=O)C1=CC=C2NC=CC2=C1 JGDTVBLOYMDZNS-UHFFFAOYSA-N 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
108010014806 prothrombinase complex Proteins 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
IWRRRCZSVINKHU-UHFFFAOYSA-N pyrazol-3-ylidenemethanone Chemical class O=C=C1C=CN=N1 IWRRRCZSVINKHU-UHFFFAOYSA-N 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
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229940107700 pyruvic acid Drugs 0.000 description 1
125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 1
125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 description 1
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125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
238000011160 research Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
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208000013223 septicemia Diseases 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
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150000003462 sulfoxides Chemical class 0.000 description 1
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238000006557 surface reaction Methods 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
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235000002906 tartaric acid Nutrition 0.000 description 1
BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
OMRJWYAXNHIRDD-UHFFFAOYSA-N tert-butyl 4-[[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]indole-2-carbonyl]amino]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1NC(=O)C1=CC2=CC=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 OMRJWYAXNHIRDD-UHFFFAOYSA-N 0.000 description 1
QMZFIRHRGPLKEV-UHFFFAOYSA-N tert-butyl 4-aminopiperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(N)CC1 QMZFIRHRGPLKEV-UHFFFAOYSA-N 0.000 description 1
LZRDHSFPLUWYAX-UHFFFAOYSA-N tert-butyl 4-aminopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(N)CC1 LZRDHSFPLUWYAX-UHFFFAOYSA-N 0.000 description 1
ORDWBNAADSSUPV-UHFFFAOYSA-N tert-butyl 4-bromo-1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OC(C)(C)C)=CC2=C1Br ORDWBNAADSSUPV-UHFFFAOYSA-N 0.000 description 1
QHPWESLNMUXZMX-UHFFFAOYSA-N tert-butyl n-(1-cyclopropylpiperidin-4-yl)carbamate Chemical compound C1CC(NC(=O)OC(C)(C)C)CCN1C1CC1 QHPWESLNMUXZMX-UHFFFAOYSA-N 0.000 description 1
AUFRDMQSECOCAZ-UHFFFAOYSA-N tert-butyl n-(1-pyridin-4-ylpiperidin-4-yl)carbamate Chemical compound C1CC(NC(=O)OC(C)(C)C)CCN1C1=CC=NC=C1 AUFRDMQSECOCAZ-UHFFFAOYSA-N 0.000 description 1
VHYXAWLOJGIJPC-UHFFFAOYSA-N tert-butyl n-(piperidin-4-ylmethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC1CCNCC1 VHYXAWLOJGIJPC-UHFFFAOYSA-N 0.000 description 1
238000012360 testing method Methods 0.000 description 1
UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
239000003868 thrombin inhibitor Substances 0.000 description 1
230000001732 thrombotic effect Effects 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
239000012588 trypsin Substances 0.000 description 1
229960001322 trypsin Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
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Classifications

- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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
- 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
- A61P9/08—Vasodilators for multiple indications
- 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
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
- C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
- C04B35/632—Organic additives
- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/22—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an aralkyl radical attached to the ring nitrogen atom
- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
- 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
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- 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
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- 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
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- 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
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- C07—ORGANIC CHEMISTRY
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- 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
- 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
- C07D417/14—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 three or more hetero rings

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OA1200400142A 2001-11-22 2002-11-08 Indole-2-carboxamides as factor XA inhibitors. OA12727A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP01127809A EP1314733A1 (de)	2001-11-22	2001-11-22	Indol-2-carbonsäureamide als Faktor-Xa-Hemmer

Publications (1)

Publication Number	Publication Date
OA12727A true OA12727A (en)	2006-06-27

Family

ID=8179313

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200400142A OA12727A (en)	2001-11-22	2002-11-08	Indole-2-carboxamides as factor XA inhibitors.

Country Status (30)

Country	Link
US (3)	US6906084B2 (de)
EP (2)	EP1314733A1 (de)
JP (1)	JP4664592B2 (de)
KR (2)	KR100954508B1 (de)
CN (1)	CN1283638C (de)
AR (1)	AR037656A1 (de)
AU (1)	AU2002351918B2 (de)
BR (1)	BR0214396A (de)
CA (1)	CA2467374C (de)
CO (1)	CO5580764A2 (de)
EC (1)	ECSP045115A (de)
HR (1)	HRP20040453A2 (de)
HU (1)	HUP0402063A3 (de)
IL (2)	IL162105A0 (de)
MA (1)	MA27350A1 (de)
ME (1)	MEP43008A (de)
MX (1)	MXPA04004797A (de)
MY (1)	MY131516A (de)
NO (1)	NO327466B1 (de)
NZ (1)	NZ533044A (de)
OA (1)	OA12727A (de)
PE (1)	PE20030593A1 (de)
PL (1)	PL210986B1 (de)
RS (1)	RS40404A (de)
RU (1)	RU2299881C2 (de)
TN (1)	TNSN04091A1 (de)
TW (1)	TWI291950B (de)
UA (1)	UA78731C2 (de)
WO (1)	WO2003044014A1 (de)
ZA (1)	ZA200402945B (de)

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2001
- 2001-11-22 EP EP01127809A patent/EP1314733A1/de not_active Withdrawn
2002
- 2002-08-11 UA UA20040604882A patent/UA78731C2/uk unknown
- 2002-11-08 EP EP02787604.4A patent/EP1451185B1/de not_active Expired - Lifetime
- 2002-11-08 ME MEP-430/08A patent/MEP43008A/xx unknown
- 2002-11-08 HU HU0402063A patent/HUP0402063A3/hu unknown
- 2002-11-08 RU RU2004118710/04A patent/RU2299881C2/ru not_active IP Right Cessation
- 2002-11-08 BR BR0214396-8A patent/BR0214396A/pt active Search and Examination
- 2002-11-08 AU AU2002351918A patent/AU2002351918B2/en not_active Ceased
- 2002-11-08 CA CA2467374A patent/CA2467374C/en not_active Expired - Fee Related
- 2002-11-08 CN CNB028232488A patent/CN1283638C/zh not_active Expired - Fee Related
- 2002-11-08 KR KR1020047007838A patent/KR100954508B1/ko not_active Expired - Fee Related
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- 2002-11-08 MX MXPA04004797A patent/MXPA04004797A/es active IP Right Grant
- 2002-11-08 KR KR1020107003845A patent/KR101033798B1/ko not_active Expired - Fee Related
- 2002-11-08 JP JP2003545651A patent/JP4664592B2/ja not_active Expired - Fee Related
- 2002-11-08 NZ NZ533044A patent/NZ533044A/en not_active IP Right Cessation
- 2002-11-08 RS YUP-404/04A patent/RS40404A/sr unknown
- 2002-11-08 IL IL16210502A patent/IL162105A0/xx unknown
- 2002-11-08 WO PCT/EP2002/012500 patent/WO2003044014A1/en not_active Ceased
- 2002-11-08 PL PL368949A patent/PL210986B1/pl unknown
- 2002-11-08 HR HR20040453A patent/HRP20040453A2/xx not_active Application Discontinuation
- 2002-11-19 PE PE2002001105A patent/PE20030593A1/es not_active Application Discontinuation
- 2002-11-20 TW TW091133782A patent/TWI291950B/zh not_active IP Right Cessation
- 2002-11-20 AR ARP020104452A patent/AR037656A1/es active IP Right Grant
- 2002-11-21 US US10/301,397 patent/US6906084B2/en not_active Expired - Lifetime
- 2002-11-22 MY MYPI20024375A patent/MY131516A/en unknown
2004
- 2004-04-19 ZA ZA2004/02945A patent/ZA200402945B/en unknown
- 2004-04-22 MA MA27647A patent/MA27350A1/fr unknown
- 2004-05-20 CO CO04046947A patent/CO5580764A2/es active IP Right Grant
- 2004-05-20 EC EC2004005115A patent/ECSP045115A/es unknown
- 2004-05-20 IL IL162105A patent/IL162105A/en not_active IP Right Cessation
- 2004-05-21 TN TNP2004000091A patent/TNSN04091A1/en unknown
- 2004-06-21 NO NO20042592A patent/NO327466B1/no not_active IP Right Cessation
- 2004-08-26 US US10/926,909 patent/US20050043302A1/en not_active Abandoned
2008
- 2008-05-12 US US12/119,013 patent/US20090069565A1/en not_active Abandoned

Also Published As

Publication number	Publication date
JP2005514365A (ja)	2005-05-19
UA78731C2 (en)	2007-04-25
TW200408625A (en)	2004-06-01
AU2002351918A1 (en)	2003-06-10
CA2467374A1 (en)	2003-05-30
US20090069565A1 (en)	2009-03-12
EP1451185A1 (de)	2004-09-01
IL162105A (en)	2012-05-31
IL162105A0 (en)	2005-11-20
HK1070352A1 (en)	2005-06-17
JP4664592B2 (ja)	2011-04-06
HUP0402063A3 (en)	2008-03-28
KR20100027248A (ko)	2010-03-10
WO2003044014A8 (en)	2004-07-22
TWI291950B (en)	2008-01-01
MXPA04004797A (es)	2004-08-11
CN1283638C (zh)	2006-11-08
PL210986B1 (pl)	2012-03-30
RS40404A (sr)	2007-11-15
CA2467374C (en)	2012-11-27
MA27350A1 (fr)	2005-06-01
NO20042592L (no)	2004-06-21
US20030199689A1 (en)	2003-10-23
EP1451185B1 (de)	2014-08-06
HUP0402063A2 (hu)	2005-02-28
HRP20040453A2 (en)	2005-08-31
RU2299881C2 (ru)	2007-05-27
KR20040073441A (ko)	2004-08-19
RU2004118710A (ru)	2005-03-27
CO5580764A2 (es)	2005-11-30
MY131516A (en)	2007-08-30
NO327466B1 (no)	2009-07-06
ECSP045115A (es)	2004-07-23
US20050043302A1 (en)	2005-02-24
CN1589270A (zh)	2005-03-02
TNSN04091A1 (en)	2006-06-01
PL368949A1 (en)	2005-04-04
US6906084B2 (en)	2005-06-14
EP1314733A1 (de)	2003-05-28
AR037656A1 (es)	2004-12-01
WO2003044014A1 (en)	2003-05-30
ZA200402945B (en)	2005-02-23
KR100954508B1 (ko)	2010-04-27
MEP43008A (en)	2011-02-10
PE20030593A1 (es)	2003-08-21
KR101033798B1 (ko)	2011-05-13
NZ533044A (en)	2005-11-25
BR0214396A (pt)	2004-09-14
AU2002351918B2 (en)	2008-04-03

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US20080280946A1 (en)	2008-11-13	Azaindole-Derivatives As Factor Xa Inhibitors
AU2004238500B2 (en)	2010-07-22	Azaindole-derivatives as factor Xa inhibitors
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