CA2540021A1

CA2540021A1 - Hcv inhibitors and methods of using them

Hcv inhibitors and methods of using them Download PDF

Info

Publication number: CA2540021A1
Authority: CA; Canada
Prior art keywords: quinoline; alkyl; carboxamide; chloro; tetrazolo
Prior art date: 2003-09-26
Legal status : Abandoned

Application number

CA002540021A

Other languages

English (en)

French (fr)

Inventor

Sambaiah Thota

Ankush Argade

Rajinder Singh

Henry H. Lu

Peiyong Huang

Current Assignee

Rigel Pharmaceuticals Inc

Original Assignee

Individual

Priority date

2003-09-26

Filing date

2004-09-27

Publication date

2005-04-07

2004-09-27 Application filed by Individual filed Critical Individual

2005-04-07 Publication of CA2540021A1 publication Critical patent/CA2540021A1/en

Status Abandoned legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 38
239000003112 inhibitor Substances 0.000 title abstract description 9
150000001875 compounds Chemical class 0.000 claims abstract description 117
239000000203 mixture Substances 0.000 claims abstract description 21
208000015181 infectious disease Diseases 0.000 claims abstract description 8
241000124008 Mammalia Species 0.000 claims abstract description 6
239000003937 drug carrier Substances 0.000 claims abstract description 6
-1 C1-C6-alkyl-OH Chemical group 0.000 claims description 88
239000001257 hydrogen Substances 0.000 claims description 63
229910052739 hydrogen Inorganic materials 0.000 claims description 63
125000003118 aryl group Chemical group 0.000 claims description 52
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 51
125000001072 heteroaryl group Chemical group 0.000 claims description 45
125000005843 halogen group Chemical group 0.000 claims description 41
229910052736 halogen Inorganic materials 0.000 claims description 35
125000000623 heterocyclic group Chemical group 0.000 claims description 34
125000004093 cyano group Chemical group *C#N 0.000 claims description 33
150000002431 hydrogen Chemical class 0.000 claims description 32
150000002367 halogens Chemical class 0.000 claims description 31
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
125000001309 chloro group Chemical group Cl* 0.000 claims description 23
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 21
LEWDKQKVAFOMPI-UHFFFAOYSA-N quinoline-4-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CC=NC2=C1 LEWDKQKVAFOMPI-UHFFFAOYSA-N 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 21
125000001475 halogen functional group Chemical group 0.000 claims description 20
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
229910052757 nitrogen Inorganic materials 0.000 claims description 15
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
229910052799 carbon Inorganic materials 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 9
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
230000002401 inhibitory effect Effects 0.000 claims description 8
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
125000001246 bromo group Chemical group Br* 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 6
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
DDTGYDHKNWYLBW-UHFFFAOYSA-N 8-chloro-N-hydroxytetrazolo[1,5-a]quinoline-4-carboxamide Chemical compound ONC(=O)C1=CC2=CC=C(Cl)C=C2N2C1=NN=N2 DDTGYDHKNWYLBW-UHFFFAOYSA-N 0.000 claims description 4
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
150000001768 cations Chemical group 0.000 claims description 4
125000002346 iodo group Chemical group I* 0.000 claims description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
125000002950 monocyclic group Chemical group 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
229920002554 vinyl polymer Polymers 0.000 claims description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
HHFCAUSIBNOUOP-UHFFFAOYSA-N tetrazolo[1,5-a]quinoline Chemical compound C1=CC2=NN=NN2C2=CC=CC=C21 HHFCAUSIBNOUOP-UHFFFAOYSA-N 0.000 claims description 3
BGBWNDUMVSMUIY-UHFFFAOYSA-N 8-methoxytetrazolo[1,5-a]quinoline-4-carbaldehyde Chemical compound C1=C(C=O)C2=NN=NN2C2=CC(OC)=CC=C21 BGBWNDUMVSMUIY-UHFFFAOYSA-N 0.000 claims description 2
AKDKWURLXQDXAL-UHFFFAOYSA-N 9-methyltetrazolo[1,5-a]quinoline-4-carboxylic acid Chemical compound C1=C(C(O)=O)C2=NN=NN2C2=C1C=CC=C2C AKDKWURLXQDXAL-UHFFFAOYSA-N 0.000 claims description 2
VRQNZQJZNWPUPD-UHFFFAOYSA-N N'-hydroxytetrazolo[1,5-a]quinoline-4-carboximidamide Chemical compound ONC(=N)C1=CC2=CC=CC=C2N2C1=NN=N2 VRQNZQJZNWPUPD-UHFFFAOYSA-N 0.000 claims description 2
150000001721 carbon Chemical group 0.000 claims description 2
XDNHKLHSBNCBBV-UHFFFAOYSA-N ethyl 6-azidotetrazolo[1,5-a]quinoline-4-carboxylate Chemical compound CCOC(=O)C1=CC2=C(N=[N+]=[N-])C=CC=C2N2C1=NN=N2 XDNHKLHSBNCBBV-UHFFFAOYSA-N 0.000 claims description 2
230000035755 proliferation Effects 0.000 claims description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
229910006074 SO2NH2 Inorganic materials 0.000 claims 3
RCXYSMWMBZENQN-UHFFFAOYSA-N 9-chloro-n-(2-methylpropoxy)tetrazolo[1,5-a]quinoline-4-carboxamide Chemical compound CC(C)CONC(=O)C1=CC2=CC=CC(Cl)=C2N2C1=NN=N2 RCXYSMWMBZENQN-UHFFFAOYSA-N 0.000 claims 2
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 2
HGPBQTVIAUITCB-UHFFFAOYSA-N 1-(8-chlorotetrazolo[1,5-a]quinolin-4-yl)-3-methylurea Chemical compound CNC(=O)NC1=CC2=CC=C(Cl)C=C2N2C1=NN=N2 HGPBQTVIAUITCB-UHFFFAOYSA-N 0.000 claims 1
CWVQAOTUAFYFIQ-UHFFFAOYSA-N 1-(8-ethyltetrazolo[1,5-a]quinolin-4-yl)-n-methoxymethanimine Chemical compound C1=C(C=NOC)C2=NN=NN2C2=CC(CC)=CC=C21 CWVQAOTUAFYFIQ-UHFFFAOYSA-N 0.000 claims 1
VZMHVLAVYYNZRZ-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-(8-chlorotetrazolo[1,5-a]quinolin-4-yl)urea Chemical compound C12=NN=NN2C2=CC(Cl)=CC=C2C=C1NC(=O)NS(=O)(=O)C1=CC=CC=C1 VZMHVLAVYYNZRZ-UHFFFAOYSA-N 0.000 claims 1
UBISGVGWIURTMF-UHFFFAOYSA-N 1-chloro-8-fluoro-n-(oxan-2-yloxy)-[1,2,4]triazolo[4,3-a]quinoline-4-carboxamide Chemical compound C12=NN=C(Cl)N2C2=CC(F)=CC=C2C=C1C(=O)NOC1CCCCO1 UBISGVGWIURTMF-UHFFFAOYSA-N 0.000 claims 1
VFLGJOLLSLRBFU-UHFFFAOYSA-N 1-chloro-8-fluoro-n-hydroxy-[1,2,4]triazolo[4,3-a]quinoline-4-carboxamide Chemical compound ONC(=O)C1=CC2=CC=C(F)C=C2N2C1=NN=C2Cl VFLGJOLLSLRBFU-UHFFFAOYSA-N 0.000 claims 1
USWKATACKGFEJT-UHFFFAOYSA-N 2-(8-chlorotetrazolo[1,5-a]quinolin-4-yl)benzonitrile Chemical compound C12=NN=NN2C2=CC(Cl)=CC=C2C=C1C1=CC=CC=C1C#N USWKATACKGFEJT-UHFFFAOYSA-N 0.000 claims 1
DHNMJRIZBXIEOU-UHFFFAOYSA-N 2-(dichloromethyl)-5-(tetrazolo[1,5-a]quinolin-5-yl)-1,3,4-oxadiazole Chemical compound O1C(C(Cl)Cl)=NN=C1C1=CC2=NN=NN2C2=CC=CC=C12 DHNMJRIZBXIEOU-UHFFFAOYSA-N 0.000 claims 1
JVFUGOQEGOULRF-UHFFFAOYSA-N 3,4,5,6,14-pentazapentacyclo[11.7.0.02,6.07,12.015,20]icosa-1(13),2,4,7,9,11,15,17,19-nonaene Chemical compound C12=NN=NN2C2=CC=CC=C2C2=C1C1=CC=CC=C1N2 JVFUGOQEGOULRF-UHFFFAOYSA-N 0.000 claims 1
125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
LIRHINFDFZWXPL-UHFFFAOYSA-N 4-(2h-tetrazol-5-yl)tetrazolo[1,5-a]quinoline Chemical compound C=1C=CC=C(N2N=NN=C22)C=1C=C2C=1N=NNN=1 LIRHINFDFZWXPL-UHFFFAOYSA-N 0.000 claims 1
IYNNWROSEXQPTA-UHFFFAOYSA-N 4-[3,5-bis(trifluoromethyl)phenyl]-8-chlorotetrazolo[1,5-a]quinoline Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C=2C3=NN=NN3C3=CC(Cl)=CC=C3C=2)=C1 IYNNWROSEXQPTA-UHFFFAOYSA-N 0.000 claims 1
XPINKUJGISQSEO-UHFFFAOYSA-N 5-methyltetrazolo[1,5-a]quinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C)=C(C(O)=O)C3=NN=NN3C2=C1 XPINKUJGISQSEO-UHFFFAOYSA-N 0.000 claims 1
UDCVFAWOMCICDM-UHFFFAOYSA-N 5-phenyltetrazolo[1,5-a]quinoline-4-carboxylic acid Chemical compound C12=CC=CC=C2N2N=NN=C2C(C(=O)O)=C1C1=CC=CC=C1 UDCVFAWOMCICDM-UHFFFAOYSA-N 0.000 claims 1
COSTWHPVXQXHAE-UHFFFAOYSA-N 6-chloro-N-hydroxytetrazolo[1,5-a]quinoline-4-carboxamide Chemical compound ONC(=O)C1=CC2=C(Cl)C=CC=C2N2C1=NN=N2 COSTWHPVXQXHAE-UHFFFAOYSA-N 0.000 claims 1
CPYBYSOALMGUHF-UHFFFAOYSA-N 6-chloro-n-(oxan-2-yloxy)tetrazolo[1,5-a]quinoline-4-carboxamide Chemical compound ClC1=CC=CC(N2N=NN=C22)=C1C=C2C(=O)NOC1CCCCO1 CPYBYSOALMGUHF-UHFFFAOYSA-N 0.000 claims 1
SAMJJAMISAFPFF-UHFFFAOYSA-N 6-methyltetrazolo[1,5-a]quinoline-4-carboxylic acid Chemical compound C1=C(C(O)=O)C2=NN=NN2C2=C1C(C)=CC=C2 SAMJJAMISAFPFF-UHFFFAOYSA-N 0.000 claims 1
QCQYTJGDNNHZDX-UHFFFAOYSA-N 7,8-dimethoxy-n-(oxan-2-yloxy)tetrazolo[1,5-a]quinoline-4-carboxamide Chemical compound C12=NN=NN2C=2C=C(OC)C(OC)=CC=2C=C1C(=O)NOC1CCCCO1 QCQYTJGDNNHZDX-UHFFFAOYSA-N 0.000 claims 1
UMXNWJUCQCKDLA-UHFFFAOYSA-N 7,8-dimethoxytetrazolo[1,5-a]quinoline-4-carbaldehyde Chemical compound C1=C(C=O)C2=NN=NN2C2=C1C=C(OC)C(OC)=C2 UMXNWJUCQCKDLA-UHFFFAOYSA-N 0.000 claims 1
RNXRPXAHGZQSEZ-UHFFFAOYSA-N 7,8-dimethoxytetrazolo[1,5-a]quinoline-4-carboxylic acid Chemical compound C1=C(C(O)=O)C2=NN=NN2C2=C1C=C(OC)C(OC)=C2 RNXRPXAHGZQSEZ-UHFFFAOYSA-N 0.000 claims 1
DUHCPEDSCGDXDJ-UHFFFAOYSA-N 7,8-dimethyltetrazolo[1,5-a]quinoline-4-carboxylic acid Chemical compound C1=C(C(O)=O)C2=NN=NN2C2=C1C=C(C)C(C)=C2 DUHCPEDSCGDXDJ-UHFFFAOYSA-N 0.000 claims 1
LWFMXTCGXIXNGB-UHFFFAOYSA-N 7,9-dichloro-[1,2,4]triazolo[4,3-a]quinoline-4-carboxylic acid Chemical compound OC(=O)C1=CC2=CC(Cl)=CC(Cl)=C2N2C1=NN=C2 LWFMXTCGXIXNGB-UHFFFAOYSA-N 0.000 claims 1
PGELZFSUDCOYPM-UHFFFAOYSA-N 7,9-dichloro-n-(oxan-2-yloxy)tetrazolo[1,5-a]quinoline-4-carboxamide Chemical compound C=1C(Cl)=CC(Cl)=C(N2N=NN=C22)C=1C=C2C(=O)NOC1CCCCO1 PGELZFSUDCOYPM-UHFFFAOYSA-N 0.000 claims 1
WKLAMSXASRKVMT-UHFFFAOYSA-N 7,9-dichloro-n-hydroxy-[1,2,4]triazolo[4,3-a]quinoline-4-carboxamide Chemical compound ONC(=O)C1=CC2=CC(Cl)=CC(Cl)=C2N2C1=NN=C2 WKLAMSXASRKVMT-UHFFFAOYSA-N 0.000 claims 1
LHVNENYXACKXOM-UHFFFAOYSA-N 7,9-dimethyl-n-(oxan-2-yloxy)tetrazolo[1,5-a]quinoline-4-carboxamide Chemical compound C=1C(C)=CC(C)=C(N2N=NN=C22)C=1C=C2C(=O)NOC1CCCCO1 LHVNENYXACKXOM-UHFFFAOYSA-N 0.000 claims 1
INYZBCOIFKSUBO-UHFFFAOYSA-N 7-bromotetrazolo[1,5-a]quinoline-4-carboxylic acid Chemical compound OC(=O)C1=CC2=CC(Br)=CC=C2N2C1=NN=N2 INYZBCOIFKSUBO-UHFFFAOYSA-N 0.000 claims 1
JAZKRDMIFAWNBQ-UHFFFAOYSA-N 7-chloro-N-hydroxytetrazolo[1,5-a]quinoline-4-carboxamide Chemical compound ONC(=O)C1=CC2=CC(Cl)=CC=C2N2C1=NN=N2 JAZKRDMIFAWNBQ-UHFFFAOYSA-N 0.000 claims 1
SZPVXTFMYQECNS-UHFFFAOYSA-N 7-chloro-n-(oxan-2-yloxy)-[1,2,4]triazolo[4,3-a]quinoline-4-carboxamide Chemical compound C=1C(Cl)=CC=C(N2C=NN=C22)C=1C=C2C(=O)NOC1CCCCO1 SZPVXTFMYQECNS-UHFFFAOYSA-N 0.000 claims 1
BZTXSQMDBCODLF-UHFFFAOYSA-N 7-chloro-n-(oxan-2-yloxy)tetrazolo[1,5-a]quinoline-4-carboxamide Chemical compound C=1C(Cl)=CC=C(N2N=NN=C22)C=1C=C2C(=O)NOC1CCCCO1 BZTXSQMDBCODLF-UHFFFAOYSA-N 0.000 claims 1
FCCDDQUZXWXHQK-UHFFFAOYSA-N 7-chloro-n-hydroxy-1-methyl-[1,2,4]triazolo[4,3-a]quinoline-4-carboxamide Chemical compound ClC1=CC=C2N3C(C)=NN=C3C(C(=O)NO)=CC2=C1 FCCDDQUZXWXHQK-UHFFFAOYSA-N 0.000 claims 1
UTCROWSGSPDXBH-UHFFFAOYSA-N 7-chloro-n-hydroxy-[1,2,4]triazolo[4,3-a]quinoline-4-carboxamide Chemical compound ONC(=O)C1=CC2=CC(Cl)=CC=C2N2C1=NN=C2 UTCROWSGSPDXBH-UHFFFAOYSA-N 0.000 claims 1
PQXHXUSZQIYQIO-UHFFFAOYSA-N 7-chlorotetrazolo[1,5-a]quinoline-4-carboxylic acid Chemical compound OC(=O)C1=CC2=CC(Cl)=CC=C2N2C1=NN=N2 PQXHXUSZQIYQIO-UHFFFAOYSA-N 0.000 claims 1
YJRANNFIFFMKEY-UHFFFAOYSA-N 7-fluoro-N-hydroxytetrazolo[1,5-a]quinoline-4-carboxamide Chemical compound ONC(=O)C1=CC2=CC(F)=CC=C2N2C1=NN=N2 YJRANNFIFFMKEY-UHFFFAOYSA-N 0.000 claims 1
ICVNUJBAFJWFQH-UHFFFAOYSA-N 8-(trifluoromethoxy)tetrazolo[1,5-a]quinoline-4-carboxylic acid Chemical compound OC(=O)C1=CC2=CC=C(OC(F)(F)F)C=C2N2C1=NN=N2 ICVNUJBAFJWFQH-UHFFFAOYSA-N 0.000 claims 1
KDDGJCDUHXXMLH-UHFFFAOYSA-N 8-chloro-4-(3,4-difluorophenyl)tetrazolo[1,5-a]quinoline Chemical compound C1=C(F)C(F)=CC=C1C1=CC2=CC=C(Cl)C=C2N2C1=NN=N2 KDDGJCDUHXXMLH-UHFFFAOYSA-N 0.000 claims 1
LTZVUBITQQJLAI-UHFFFAOYSA-N 8-chloro-4-(3-fluorophenyl)tetrazolo[1,5-a]quinoline Chemical compound FC1=CC=CC(C=2C3=NN=NN3C3=CC(Cl)=CC=C3C=2)=C1 LTZVUBITQQJLAI-UHFFFAOYSA-N 0.000 claims 1
WOQOOPOVMWZXNS-UHFFFAOYSA-N 8-chloro-4-[3-(trifluoromethoxy)phenyl]tetrazolo[1,5-a]quinoline Chemical compound FC(F)(F)OC1=CC=CC(C=2C3=NN=NN3C3=CC(Cl)=CC=C3C=2)=C1 WOQOOPOVMWZXNS-UHFFFAOYSA-N 0.000 claims 1
DLVPUTGSCDEBRW-UHFFFAOYSA-N 8-chloro-4-[4-(trifluoromethoxy)phenyl]tetrazolo[1,5-a]quinoline Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC2=CC=C(Cl)C=C2N2C1=NN=N2 DLVPUTGSCDEBRW-UHFFFAOYSA-N 0.000 claims 1
PHTMAUOFIUJJMR-UHFFFAOYSA-N 8-chloro-4-imidazol-1-yltetrazolo[1,5-a]quinoline Chemical compound C12=NN=NN2C2=CC(Cl)=CC=C2C=C1N1C=CN=C1 PHTMAUOFIUJJMR-UHFFFAOYSA-N 0.000 claims 1
OTWRRFGQUTZVBJ-UHFFFAOYSA-N 8-chloro-4-pyridin-2-ylsulfonyltetrazolo[1,5-a]quinoline Chemical compound C12=NN=NN2C2=CC(Cl)=CC=C2C=C1S(=O)(=O)C1=CC=CC=N1 OTWRRFGQUTZVBJ-UHFFFAOYSA-N 0.000 claims 1
HINZTMACMJVGHO-UHFFFAOYSA-N 8-chloro-7-methoxy-n-(oxan-2-yloxy)tetrazolo[1,5-a]quinoline-4-carboxamide Chemical compound C12=NN=NN2C=2C=C(Cl)C(OC)=CC=2C=C1C(=O)NOC1CCCCO1 HINZTMACMJVGHO-UHFFFAOYSA-N 0.000 claims 1
MAQHFKAGUKUSSR-UHFFFAOYSA-N 8-chloro-7-methoxytetrazolo[1,5-a]quinoline-4-carbaldehyde Chemical compound C1=C(C=O)C2=NN=NN2C2=C1C=C(OC)C(Cl)=C2 MAQHFKAGUKUSSR-UHFFFAOYSA-N 0.000 claims 1
YJXHIVRBMRDLCW-UHFFFAOYSA-N 8-chloro-7-methoxytetrazolo[1,5-a]quinoline-4-carboxylic acid Chemical compound C1=C(C(O)=O)C2=NN=NN2C2=C1C=C(OC)C(Cl)=C2 YJXHIVRBMRDLCW-UHFFFAOYSA-N 0.000 claims 1
SOCJUVBQFYOIEW-UHFFFAOYSA-N 8-chloro-N-hydroxy-7-methoxytetrazolo[1,5-a]quinoline-4-carboxamide Chemical compound C1=C(C(=O)NO)C2=NN=NN2C2=C1C=C(OC)C(Cl)=C2 SOCJUVBQFYOIEW-UHFFFAOYSA-N 0.000 claims 1
RYOLJLMJDXZSGA-UHFFFAOYSA-N 8-chloro-n-(oxan-2-yloxy)tetrazolo[1,5-a]quinoline-4-carboxamide Chemical compound C12=NN=NN2C2=CC(Cl)=CC=C2C=C1C(=O)NOC1CCCCO1 RYOLJLMJDXZSGA-UHFFFAOYSA-N 0.000 claims 1
XFNUMICOXOOYPH-UHFFFAOYSA-N 8-chloro-n-hydroxy-n-methyltetrazolo[1,5-a]quinoline-4-carboxamide Chemical compound CN(O)C(=O)C1=CC2=CC=C(Cl)C=C2N2C1=NN=N2 XFNUMICOXOOYPH-UHFFFAOYSA-N 0.000 claims 1
DEUIAEXOWPWFDU-UHFFFAOYSA-N 8-chlorotetrazolo[1,5-a]quinoline-4-carboxamide Chemical compound NC(=O)C1=CC2=CC=C(Cl)C=C2N2C1=NN=N2 DEUIAEXOWPWFDU-UHFFFAOYSA-N 0.000 claims 1
MBPXGTGMOLMQMS-UHFFFAOYSA-N 8-cyclopentyloxytetrazolo[1,5-a]quinoline-4-carbaldehyde Chemical compound C1=C2N3N=NN=C3C(C=O)=CC2=CC=C1OC1CCCC1 MBPXGTGMOLMQMS-UHFFFAOYSA-N 0.000 claims 1
RRIJFEZOBOHYFS-UHFFFAOYSA-N 8-ethyltetrazolo[1,5-a]quinoline-4-carboxylic acid Chemical compound C1=C(C(O)=O)C2=NN=NN2C2=CC(CC)=CC=C21 RRIJFEZOBOHYFS-UHFFFAOYSA-N 0.000 claims 1
CVFKXMFUMWRFGN-UHFFFAOYSA-N 8-fluoro-[1,2,4]triazolo[4,3-a]quinoline-4-carboxylic acid Chemical compound OC(=O)C1=CC2=CC=C(F)C=C2N2C1=NN=C2 CVFKXMFUMWRFGN-UHFFFAOYSA-N 0.000 claims 1
ZPCPXFIMJQIQMO-UHFFFAOYSA-N 8-fluoro-n-(2h-tetrazol-5-yl)tetrazolo[1,5-a]quinoline-4-carboxamide Chemical compound C12=NN=NN2C2=CC(F)=CC=C2C=C1C(=O)NC1=NN=NN1 ZPCPXFIMJQIQMO-UHFFFAOYSA-N 0.000 claims 1
CCXMUTGFPIKURB-UHFFFAOYSA-N 8-methoxy-n-(oxan-2-yloxy)tetrazolo[1,5-a]quinoline-4-carboxamide Chemical compound C12=NN=NN2C2=CC(OC)=CC=C2C=C1C(=O)NOC1CCCCO1 CCXMUTGFPIKURB-UHFFFAOYSA-N 0.000 claims 1
HQVANFACLZYYAW-UHFFFAOYSA-N 8-methylsulfanyltetrazolo[1,5-a]quinoline-4-carbaldehyde Chemical compound C1=C(C=O)C2=NN=NN2C2=CC(SC)=CC=C21 HQVANFACLZYYAW-UHFFFAOYSA-N 0.000 claims 1
DZPAWGYBIQHQCG-UHFFFAOYSA-N 8-methylsulfonyltetrazolo[1,5-a]quinoline-4-carboxylic acid Chemical compound C1=C(C(O)=O)C2=NN=NN2C2=CC(S(=O)(=O)C)=CC=C21 DZPAWGYBIQHQCG-UHFFFAOYSA-N 0.000 claims 1
NWEKWRGATCIRGC-UHFFFAOYSA-N 8-propan-2-yltetrazolo[1,5-a]quinoline-4-carboxylic acid Chemical compound C1=C(C(O)=O)C2=NN=NN2C2=CC(C(C)C)=CC=C21 NWEKWRGATCIRGC-UHFFFAOYSA-N 0.000 claims 1
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