SK134698A3 - Aminoisoquinolines and aminothienopyridine derivatives and their use as anti-inflammatory agents - Google Patents

Aminoisoquinolines and aminothienopyridine derivatives and their use as anti-inflammatory agents Download PDF

Info

Publication number: SK134698A3
Authority: SK; Slovakia
Prior art keywords: amino; dihydroisoquinoline; phenyl; carbon atoms; pyridine
Prior art date: 1996-04-13

Application number

SK1346-98A

Other languages

English (en)

Slovak (sk)

Inventor

Peter Hamley

James Macdonald

James Matz

Alan Tinker

Original Assignee

Astra Pharma Prod

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.)

1996-04-13

Filing date

1997-04-09

Publication date

1999-06-11

1996-04-13 Priority claimed from GBGB9607717.7A external-priority patent/GB9607717D0/en

1996-04-26 Priority claimed from GBGB9608678.0A external-priority patent/GB9608678D0/en

1996-05-24 Priority claimed from GBGB9610892.3A external-priority patent/GB9610892D0/en

1997-04-09 Application filed by Astra Pharma Prod filed Critical Astra Pharma Prod

1999-06-11 Publication of SK134698A3 publication Critical patent/SK134698A3/sk

Links

229940121363 anti-inflammatory agent Drugs 0.000 title description 2
239000002260 anti-inflammatory agent Substances 0.000 title description 2
OSILBMSORKFRTB-UHFFFAOYSA-N isoquinolin-1-amine Chemical class C1=CC=C2C(N)=NC=CC2=C1 OSILBMSORKFRTB-UHFFFAOYSA-N 0.000 title 1
BLSWGDUCSOLUNT-UHFFFAOYSA-N thieno[3,2-b]pyridin-2-amine Chemical class C1=CC=C2SC(N)=CC2=N1 BLSWGDUCSOLUNT-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 164
125000000217 alkyl group Chemical group 0.000 claims abstract description 63
-1 cylcoalkyl Chemical group 0.000 claims abstract description 59
150000003839 salts Chemical class 0.000 claims abstract description 55
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 54
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 52
239000001257 hydrogen Substances 0.000 claims abstract description 46
229910052736 halogen Inorganic materials 0.000 claims abstract description 36
150000002367 halogens Chemical class 0.000 claims abstract description 36
125000003545 alkoxy group Chemical group 0.000 claims abstract description 22
150000002431 hydrogen Chemical class 0.000 claims abstract description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 20
125000005936 piperidyl group Chemical group 0.000 claims abstract description 20
125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 19
125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 18
125000000304 alkynyl group Chemical group 0.000 claims abstract description 13
238000011282 treatment Methods 0.000 claims abstract description 13
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims abstract description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
239000003814 drug Substances 0.000 claims abstract description 9
125000004001 thioalkyl group Chemical group 0.000 claims abstract description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 8
229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 8
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 6
125000005842 heteroatom Chemical group 0.000 claims abstract description 6
125000002757 morpholinyl group Chemical group 0.000 claims abstract description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 6
208000027866 inflammatory disease Diseases 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 81
238000000034 method Methods 0.000 claims description 55
238000002360 preparation method Methods 0.000 claims description 18
125000006239 protecting group Chemical group 0.000 claims description 14
125000001424 substituent group Chemical group 0.000 claims description 14
230000008569 process Effects 0.000 claims description 12
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
102000008299 Nitric Oxide Synthase Human genes 0.000 claims description 10
108010021487 Nitric Oxide Synthase Proteins 0.000 claims description 10
201000010099 disease Diseases 0.000 claims description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
238000003786 synthesis reaction Methods 0.000 claims description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
230000015572 biosynthetic process Effects 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
239000000126 substance Substances 0.000 claims description 8
UNSMGVCQMIQVKA-UHFFFAOYSA-N 3-methyl-5-trimethylsilylthiophene-2-carbonitrile Chemical compound CC=1C=C([Si](C)(C)C)SC=1C#N UNSMGVCQMIQVKA-UHFFFAOYSA-N 0.000 claims description 7
238000005804 alkylation reaction Methods 0.000 claims description 7
230000007062 hydrolysis Effects 0.000 claims description 7
238000006460 hydrolysis reaction Methods 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 7
APEWHXWIIJEJHJ-UHFFFAOYSA-N 2-methyl-5-trimethylsilylthiophene-3-carbonitrile Chemical compound CC=1SC([Si](C)(C)C)=CC=1C#N APEWHXWIIJEJHJ-UHFFFAOYSA-N 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
125000004430 oxygen atom Chemical group O* 0.000 claims description 6
238000011321 prophylaxis Methods 0.000 claims description 6
239000011593 sulfur Chemical group 0.000 claims description 6
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 5
150000001340 alkali metals Chemical class 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
150000001540 azides Chemical class 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
229930192474 thiophene Natural products 0.000 claims description 5
UCSKOUQDVWADGZ-UHFFFAOYSA-N 2-fluoro-6-methylbenzonitrile Chemical compound CC1=CC=CC(F)=C1C#N UCSKOUQDVWADGZ-UHFFFAOYSA-N 0.000 claims description 4
UDLKVLFYSBCRAD-UHFFFAOYSA-N 3-(2-azidoethyl)benzaldehyde Chemical compound [N-]=[N+]=NCCC1=CC=CC(C=O)=C1 UDLKVLFYSBCRAD-UHFFFAOYSA-N 0.000 claims description 4
SEXMQWDVEOWSGM-UHFFFAOYSA-N 3-(3-azidopropyl)benzaldehyde Chemical compound [N-]=[N+]=NCCCC1=CC=CC(C=O)=C1 SEXMQWDVEOWSGM-UHFFFAOYSA-N 0.000 claims description 4
FHKTUGAQZLCFTP-UHFFFAOYSA-N 3-[(dimethylamino)methyl]benzaldehyde Chemical compound CN(C)CC1=CC=CC(C=O)=C1 FHKTUGAQZLCFTP-UHFFFAOYSA-N 0.000 claims description 4
DMQFTNHJWVKVGE-UHFFFAOYSA-N 3-fluoro-2-methylbenzonitrile Chemical compound CC1=C(F)C=CC=C1C#N DMQFTNHJWVKVGE-UHFFFAOYSA-N 0.000 claims description 4
JPKBIODDVOUHAD-UHFFFAOYSA-N 3-methoxy-2-methylbenzonitrile Chemical group COC1=CC=CC(C#N)=C1C JPKBIODDVOUHAD-UHFFFAOYSA-N 0.000 claims description 4
RDYWNZRVHKWADW-UHFFFAOYSA-N 4,5-dihydrothieno[2,3-c]pyridin-7-amine Chemical compound NC1=NCCC2=C1SC=C2 RDYWNZRVHKWADW-UHFFFAOYSA-N 0.000 claims description 4
YMXNKRFKTKWYPG-UHFFFAOYSA-N 4-(2-azidoethyl)benzaldehyde Chemical compound [N-]=[N+]=NCCC1=CC=C(C=O)C=C1 YMXNKRFKTKWYPG-UHFFFAOYSA-N 0.000 claims description 4
VSKHIGZWONBJDV-UHFFFAOYSA-N 4-(3-azidopropoxy)benzaldehyde Chemical compound [N-]=[N+]=NCCCOC1=CC=C(C=O)C=C1 VSKHIGZWONBJDV-UHFFFAOYSA-N 0.000 claims description 4
BJBXUIUJKPOZLV-UHFFFAOYSA-N 4-fluoro-2-methylbenzonitrile Chemical compound CC1=CC(F)=CC=C1C#N BJBXUIUJKPOZLV-UHFFFAOYSA-N 0.000 claims description 4
230000029936 alkylation Effects 0.000 claims description 4
229910021529 ammonia Inorganic materials 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
125000000068 chlorophenyl group Chemical group 0.000 claims description 4
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
238000010511 deprotection reaction Methods 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000001207 fluorophenyl group Chemical group 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
125000004464 hydroxyphenyl group Chemical group 0.000 claims description 4
125000002883 imidazolyl group Chemical group 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
230000009467 reduction Effects 0.000 claims description 4
125000000335 thiazolyl group Chemical group 0.000 claims description 4
GDQBPBMIAFIRIU-UHFFFAOYSA-N thieno[2,3-c]pyridine Chemical compound C1=NC=C2SC=CC2=C1 GDQBPBMIAFIRIU-UHFFFAOYSA-N 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
125000003944 tolyl group Chemical group 0.000 claims description 4
GIRMHLSPAMODBZ-UHFFFAOYSA-N 3,6-difluoro-2-methylbenzonitrile Chemical compound CC1=C(F)C=CC(F)=C1C#N GIRMHLSPAMODBZ-UHFFFAOYSA-N 0.000 claims description 3
JQLTVUBKGSQENX-UHFFFAOYSA-N 3-(2-chlorophenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=CC=CC=C1Cl JQLTVUBKGSQENX-UHFFFAOYSA-N 0.000 claims description 3
MIUUXAKFLYGRCX-UHFFFAOYSA-N 5-trimethylsilyl-1,3-thiazole-2-carbaldehyde Chemical compound C[Si](C)(C)C1=CN=C(C=O)S1 MIUUXAKFLYGRCX-UHFFFAOYSA-N 0.000 claims description 3
PZUJYUAPVWDTTH-UHFFFAOYSA-N 6-fluoro-3-(4-fluorophenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC(F)=CC=C2C(N)=NC1C1=CC=C(F)C=C1 PZUJYUAPVWDTTH-UHFFFAOYSA-N 0.000 claims description 3
208000002193 Pain Diseases 0.000 claims description 3
108010029485 Protein Isoforms Proteins 0.000 claims description 3
102000001708 Protein Isoforms Human genes 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
WBCQLYANPBVSJJ-UHFFFAOYSA-N 3-[4-(2-aminoethyl)phenyl]-3,4-dihydroisoquinolin-1-amine Chemical compound C1=CC(CCN)=CC=C1C1N=C(N)C2=CC=CC=C2C1 WBCQLYANPBVSJJ-UHFFFAOYSA-N 0.000 claims description 2
PAMSSQOJKYZURX-UHFFFAOYSA-N 3-[4-(3-azidopropoxy)phenyl]-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=CC=C(OCCCN=[N+]=[N-])C=C1 PAMSSQOJKYZURX-UHFFFAOYSA-N 0.000 claims description 2
MGJCYGSDDRNTQF-UHFFFAOYSA-N 3-thiophen-3-yl-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C=1C=CSC=1 MGJCYGSDDRNTQF-UHFFFAOYSA-N 0.000 claims description 2
DOXSRAMHAZLQFA-UHFFFAOYSA-N 4-[tert-butyl(diphenyl)silyl]oxybenzaldehyde Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C(C)(C)C)OC1=CC=C(C=O)C=C1 DOXSRAMHAZLQFA-UHFFFAOYSA-N 0.000 claims description 2
RPRPICVFGRGLLI-UHFFFAOYSA-N 4-methylsulfanyl-6,7-dihydrothieno[3,2-c]pyridine Chemical compound CSC1=NCCC2=C1C=CS2 RPRPICVFGRGLLI-UHFFFAOYSA-N 0.000 claims description 2
208000006673 asthma Diseases 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims description 2
206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
VPKAHUMPZYVNIV-UHFFFAOYSA-N 1,4-dihydroisoquinoline Chemical compound C1=CC=C2CC=NCC2=C1 VPKAHUMPZYVNIV-UHFFFAOYSA-N 0.000 claims 2
SUMKTJDWYOSGDW-UHFFFAOYSA-N 2-(3,4-dihydro-1h-isoquinolin-2-yl)-1,3-benzothiazole Chemical compound C1=CC=C2SC(N3CC4=CC=CC=C4CC3)=NC2=C1 SUMKTJDWYOSGDW-UHFFFAOYSA-N 0.000 claims 2
RDKMXFCWQURSLL-UHFFFAOYSA-N 3-(1,3-thiazol-2-yl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=NC=CS1 RDKMXFCWQURSLL-UHFFFAOYSA-N 0.000 claims 2
PYOAJTLPLZFISJ-UHFFFAOYSA-N 3-(1h-imidazol-2-yl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=NC=CN1 PYOAJTLPLZFISJ-UHFFFAOYSA-N 0.000 claims 2
XVFZTEAZCMAZMP-UHFFFAOYSA-N 3-(2-fluorophenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=CC=CC=C1F XVFZTEAZCMAZMP-UHFFFAOYSA-N 0.000 claims 2
ILKAQXSEIAZAGJ-UHFFFAOYSA-N 3-(2-methylphenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound CC1=CC=CC=C1C1N=C(N)C2=CC=CC=C2C1 ILKAQXSEIAZAGJ-UHFFFAOYSA-N 0.000 claims 2
LCHNDJWNIUCWAD-UHFFFAOYSA-N 3-(2-phenylethynyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C#CC1=CC=CC=C1 LCHNDJWNIUCWAD-UHFFFAOYSA-N 0.000 claims 2
SIMLDIDAIWXGPT-UHFFFAOYSA-N 3-(3-chlorophenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=CC=CC(Cl)=C1 SIMLDIDAIWXGPT-UHFFFAOYSA-N 0.000 claims 2
KLWZVSPGLUAFIN-UHFFFAOYSA-N 3-(3-fluorophenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=CC=CC(F)=C1 KLWZVSPGLUAFIN-UHFFFAOYSA-N 0.000 claims 2
QLTIDNDKPCSXEY-UHFFFAOYSA-N 3-(3-methylphenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound CC1=CC=CC(C2N=C(N)C3=CC=CC=C3C2)=C1 QLTIDNDKPCSXEY-UHFFFAOYSA-N 0.000 claims 2
KWMGDJOVVNCHIR-UHFFFAOYSA-N 3-(4-fluorophenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=CC=C(F)C=C1 KWMGDJOVVNCHIR-UHFFFAOYSA-N 0.000 claims 2
YHPUTQLDLSONET-UHFFFAOYSA-N 3-(4-methoxyphenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1=CC(OC)=CC=C1C1N=C(N)C2=CC=CC=C2C1 YHPUTQLDLSONET-UHFFFAOYSA-N 0.000 claims 2
YFZZNKYZMNEJDU-UHFFFAOYSA-N 3-(4-methylphenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1=CC(C)=CC=C1C1N=C(N)C2=CC=CC=C2C1 YFZZNKYZMNEJDU-UHFFFAOYSA-N 0.000 claims 2
FHPIUNZZJDTGSZ-UHFFFAOYSA-N 3-(4-phenylmethoxyphenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C(C=C1)=CC=C1OCC1=CC=CC=C1 FHPIUNZZJDTGSZ-UHFFFAOYSA-N 0.000 claims 2
MHTRUYAUQNWPBC-UHFFFAOYSA-N 3-(furan-2-yl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=CC=CO1 MHTRUYAUQNWPBC-UHFFFAOYSA-N 0.000 claims 2
HWMWUMMILIHFLR-UHFFFAOYSA-N 3-(furan-3-yl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C=1C=COC=1 HWMWUMMILIHFLR-UHFFFAOYSA-N 0.000 claims 2
SJEMPPKPSKQEHA-UHFFFAOYSA-N 3-cyclopropyl-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1CC1 SJEMPPKPSKQEHA-UHFFFAOYSA-N 0.000 claims 2
SGASAPRGFSSJCC-UHFFFAOYSA-N 3-ethynyl-3,4-dihydroisoquinolin-1-amine Chemical compound C1=CC=C2C(N)=NC(C#C)CC2=C1 SGASAPRGFSSJCC-UHFFFAOYSA-N 0.000 claims 2
FWLROWLVILMULO-UHFFFAOYSA-N 3-methyl-3,4-dihydroisoquinolin-1-amine Chemical compound C1=CC=C2C(N)=NC(C)CC2=C1 FWLROWLVILMULO-UHFFFAOYSA-N 0.000 claims 2
NXQKWROQUYKWQS-UHFFFAOYSA-N 3-phenyl-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=CC=CC=C1 NXQKWROQUYKWQS-UHFFFAOYSA-N 0.000 claims 2
JQUYKZBUFGMQFT-UHFFFAOYSA-N 3-piperidin-4-yl-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1CCNCC1 JQUYKZBUFGMQFT-UHFFFAOYSA-N 0.000 claims 2
AQZWYRYKUGMBEY-UHFFFAOYSA-N 3-pyridin-3-yl-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=CC=CN=C1 AQZWYRYKUGMBEY-UHFFFAOYSA-N 0.000 claims 2
YVJMJORBDKLUPO-UHFFFAOYSA-N 3-pyridin-4-yl-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=CC=NC=C1 YVJMJORBDKLUPO-UHFFFAOYSA-N 0.000 claims 2
CDRBKBGYXOOEBB-UHFFFAOYSA-N 3-thiophen-2-yl-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=CC=CS1 CDRBKBGYXOOEBB-UHFFFAOYSA-N 0.000 claims 2
PYRGEFPIYBRXKZ-UHFFFAOYSA-N 4-(1-amino-3,4-dihydroisoquinolin-3-yl)phenol Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=CC=C(O)C=C1 PYRGEFPIYBRXKZ-UHFFFAOYSA-N 0.000 claims 2
JDTOGSNUBVOBFU-UHFFFAOYSA-N 5,8-difluoro-3-(4-fluorophenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=C(F)C=CC(F)=C2C(N)=NC1C1=CC=C(F)C=C1 JDTOGSNUBVOBFU-UHFFFAOYSA-N 0.000 claims 2
XRGUFKQXZAAIES-UHFFFAOYSA-N 5-(1,3-thiazol-2-yl)-4,5-dihydrothieno[2,3-c]pyridin-7-amine Chemical compound C1C=2C=CSC=2C(N)=NC1C1=NC=CS1 XRGUFKQXZAAIES-UHFFFAOYSA-N 0.000 claims 2
QVAKDIALQGODMB-UHFFFAOYSA-N 5-(1-benzylpyrrol-2-yl)-4,5-dihydrothieno[2,3-c]pyridin-7-amine Chemical compound C1C=2C=CSC=2C(N)=NC1C1=CC=CN1CC1=CC=CC=C1 QVAKDIALQGODMB-UHFFFAOYSA-N 0.000 claims 2
JQSCZZYXNHKNCQ-UHFFFAOYSA-N 5-(2-phenylethynyl)-4,5-dihydrothieno[2,3-c]pyridin-7-amine Chemical compound C1C=2C=CSC=2C(N)=NC1C#CC1=CC=CC=C1 JQSCZZYXNHKNCQ-UHFFFAOYSA-N 0.000 claims 2
WAOKDGZAIYAHLD-UHFFFAOYSA-N 5-(furan-2-yl)-4,5-dihydrothieno[2,3-c]pyridin-7-amine Chemical compound C1C=2C=CSC=2C(N)=NC1C1=CC=CO1 WAOKDGZAIYAHLD-UHFFFAOYSA-N 0.000 claims 2
OXLOREYBGOXXEV-UHFFFAOYSA-N 5-(furan-3-yl)-4,5-dihydrothieno[2,3-c]pyridin-7-amine Chemical compound C1C=2C=CSC=2C(N)=NC1C=1C=COC=1 OXLOREYBGOXXEV-UHFFFAOYSA-N 0.000 claims 2
KBBLLKUZTNRELO-UHFFFAOYSA-N 5-chloro-3-phenyl-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=C(Cl)C=CC=C2C(N)=NC1C1=CC=CC=C1 KBBLLKUZTNRELO-UHFFFAOYSA-N 0.000 claims 2
GWZRFZUSUXYFLO-UHFFFAOYSA-N 5-cyclobutyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine Chemical compound C1C=2C=CSC=2C(N)=NC1C1CCC1 GWZRFZUSUXYFLO-UHFFFAOYSA-N 0.000 claims 2
MSFKVTUZXYQWQW-UHFFFAOYSA-N 5-cyclopropyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine Chemical compound C1C=2C=CSC=2C(N)=NC1C1CC1 MSFKVTUZXYQWQW-UHFFFAOYSA-N 0.000 claims 2
NHNLFSHXMCRUSN-UHFFFAOYSA-N 5-ethyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine Chemical compound NC1=NC(CC)CC2=C1SC=C2 NHNLFSHXMCRUSN-UHFFFAOYSA-N 0.000 claims 2
YZFZKTWAMLXSPG-UHFFFAOYSA-N 5-ethynyl-2-methyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine Chemical compound C1C(C#C)N=C(N)C2=C1C=C(C)S2 YZFZKTWAMLXSPG-UHFFFAOYSA-N 0.000 claims 2
ASLZDSGYTVWLOQ-UHFFFAOYSA-N 5-ethynyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine Chemical compound NC1=NC(C#C)CC2=C1SC=C2 ASLZDSGYTVWLOQ-UHFFFAOYSA-N 0.000 claims 2
KEASVJPWDYZLCE-UHFFFAOYSA-N 5-fluoro-3-(4-fluorophenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=C(F)C=CC=C2C(N)=NC1C1=CC=C(F)C=C1 KEASVJPWDYZLCE-UHFFFAOYSA-N 0.000 claims 2
CQCMHFYGKBQABE-UHFFFAOYSA-N 5-fluoro-3-phenyl-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=C(F)C=CC=C2C(N)=NC1C1=CC=CC=C1 CQCMHFYGKBQABE-UHFFFAOYSA-N 0.000 claims 2
NVANRLMNXVPARO-UHFFFAOYSA-N 5-methoxy-3-phenyl-3,4-dihydroisoquinolin-1-amine Chemical compound C1C=2C(OC)=CC=CC=2C(N)=NC1C1=CC=CC=C1 NVANRLMNXVPARO-UHFFFAOYSA-N 0.000 claims 2
BZMKAOPCFNDOAZ-UHFFFAOYSA-N 5-methyl-3-phenyl-3,4-dihydroisoquinolin-1-amine Chemical compound C1C=2C(C)=CC=CC=2C(N)=NC1C1=CC=CC=C1 BZMKAOPCFNDOAZ-UHFFFAOYSA-N 0.000 claims 2
OJTGYEZYCLLMBZ-UHFFFAOYSA-N 5-phenyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine Chemical compound C1C=2C=CSC=2C(N)=NC1C1=CC=CC=C1 OJTGYEZYCLLMBZ-UHFFFAOYSA-N 0.000 claims 2
FPIJYFMUGDPADO-UHFFFAOYSA-N 5-prop-1-ynyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine Chemical compound NC1=NC(C#CC)CC2=C1SC=C2 FPIJYFMUGDPADO-UHFFFAOYSA-N 0.000 claims 2
WCMXTLROFWDEOH-UHFFFAOYSA-N 5-propyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine Chemical compound NC1=NC(CCC)CC2=C1SC=C2 WCMXTLROFWDEOH-UHFFFAOYSA-N 0.000 claims 2
LQTSFUGQZYFQQE-UHFFFAOYSA-N 6,7-dihydrothieno[3,2-c]pyridin-4-amine Chemical compound NC1=NCCC2=C1C=CS2 LQTSFUGQZYFQQE-UHFFFAOYSA-N 0.000 claims 2
ISNQNGVISJCDEL-UHFFFAOYSA-N 6-bromo-3-phenyl-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC(Br)=CC=C2C(N)=NC1C1=CC=CC=C1 ISNQNGVISJCDEL-UHFFFAOYSA-N 0.000 claims 2
SDSGBYHHAGJJCK-UHFFFAOYSA-N 6-cyclopropyl-6,7-dihydrothieno[3,2-c]pyridin-4-amine Chemical compound C1C=2SC=CC=2C(N)=NC1C1CC1 SDSGBYHHAGJJCK-UHFFFAOYSA-N 0.000 claims 2
NNUPDBFRVPMTCH-UHFFFAOYSA-N 6-ethynyl-6,7-dihydrothieno[3,2-c]pyridin-4-amine Chemical compound NC1=NC(C#C)CC2=C1C=CS2 NNUPDBFRVPMTCH-UHFFFAOYSA-N 0.000 claims 2
LZAUMHCTCUKFMR-UHFFFAOYSA-N 6-phenyl-6,7-dihydrothieno[3,2-c]pyridin-4-amine Chemical compound C1C=2SC=CC=2C(N)=NC1C1=CC=CC=C1 LZAUMHCTCUKFMR-UHFFFAOYSA-N 0.000 claims 2
BPKYXHOIZZBKMI-UHFFFAOYSA-N 7-fluoro-3-(4-fluorophenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=C(F)C=C2C(N)=NC1C1=CC=C(F)C=C1 BPKYXHOIZZBKMI-UHFFFAOYSA-N 0.000 claims 2
LDLSVICPILEJTP-UHFFFAOYSA-N 7-methyl-3-phenyl-3,4-dihydroisoquinolin-1-amine Chemical compound N1=C(N)C2=CC(C)=CC=C2CC1C1=CC=CC=C1 LDLSVICPILEJTP-UHFFFAOYSA-N 0.000 claims 2
MIUMJBLHBWQZPJ-UHFFFAOYSA-N 8-chloro-3-(4-fluorophenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC(Cl)=C2C(N)=NC1C1=CC=C(F)C=C1 MIUMJBLHBWQZPJ-UHFFFAOYSA-N 0.000 claims 2
UHYGAVKGLDNCFO-UHFFFAOYSA-N 8-chloro-3-(furan-2-yl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC(Cl)=C2C(N)=NC1C1=CC=CO1 UHYGAVKGLDNCFO-UHFFFAOYSA-N 0.000 claims 2
QPAHGGACAIYANQ-UHFFFAOYSA-N 8-chloro-3-phenyl-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC(Cl)=C2C(N)=NC1C1=CC=CC=C1 QPAHGGACAIYANQ-UHFFFAOYSA-N 0.000 claims 2
LCRLDHTZCMPEPS-UHFFFAOYSA-N 8-fluoro-3-(4-fluorophenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC(F)=C2C(N)=NC1C1=CC=C(F)C=C1 LCRLDHTZCMPEPS-UHFFFAOYSA-N 0.000 claims 2
OTLLMGWJZKFCGF-UHFFFAOYSA-N 8-fluoro-3-phenyl-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC(F)=C2C(N)=NC1C1=CC=CC=C1 OTLLMGWJZKFCGF-UHFFFAOYSA-N 0.000 claims 2
BKFJHQBNYUBCAU-UHFFFAOYSA-N 2-[4-(3,4-dihydroisoquinolin-1-yl)phenyl]ethanamine Chemical compound C1CN=C(C2=CC=CC=C21)C3=CC=C(C=C3)CCN BKFJHQBNYUBCAU-UHFFFAOYSA-N 0.000 claims 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
OCUUMDCHFDZDDK-UHFFFAOYSA-N 3-(4-chlorophenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=CC=C(Cl)C=C1 OCUUMDCHFDZDDK-UHFFFAOYSA-N 0.000 claims 1
RTTZUQZPBRNFLW-UHFFFAOYSA-N 3-(4-methylsulfanylphenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1=CC(SC)=CC=C1C1N=C(N)C2=CC=CC=C2C1 RTTZUQZPBRNFLW-UHFFFAOYSA-N 0.000 claims 1
NFSKGYWWFVYJLR-UHFFFAOYSA-N 3-[3-(3,4-dihydroisoquinolin-1-yl)phenyl]propan-1-amine Chemical compound NCCCC=1C=C(C=CC=1)C1=NCCC2=CC=CC=C12 NFSKGYWWFVYJLR-UHFFFAOYSA-N 0.000 claims 1
VYLJBFNFOKMCLB-UHFFFAOYSA-N 3-[3-(3-aminopropyl)phenyl]-3,4-dihydroisoquinolin-1-amine Chemical compound NCCCC1=CC=CC(C2N=C(N)C3=CC=CC=C3C2)=C1 VYLJBFNFOKMCLB-UHFFFAOYSA-N 0.000 claims 1
IUXBWVFFYMDQRD-UHFFFAOYSA-N 5-(1-methylpyrrol-2-yl)-4,5-dihydrothieno[2,3-c]pyridin-7-amine Chemical compound CN1C=CC=C1C1N=C(N)C(SC=C2)=C2C1 IUXBWVFFYMDQRD-UHFFFAOYSA-N 0.000 claims 1
DQFBGLAGAZYBJX-UHFFFAOYSA-N 5-pyridin-3-yl-4,5-dihydrothieno[2,3-c]pyridin-7-amine Chemical compound C1C=2C=CSC=2C(N)=NC1C1=CC=CN=C1 DQFBGLAGAZYBJX-UHFFFAOYSA-N 0.000 claims 1
LSTQFUCKHDHNPQ-UHFFFAOYSA-N 5-thiophen-2-yl-4,5-dihydrothieno[2,3-c]pyridin-7-amine Chemical compound C1C=2C=CSC=2C(N)=NC1C1=CC=CS1 LSTQFUCKHDHNPQ-UHFFFAOYSA-N 0.000 claims 1
SJWKMOBOBCRSTP-UHFFFAOYSA-N 8-methyl-3-phenyl-3,4-dihydroisoquinolin-1-amine Chemical compound N1=C(N)C=2C(C)=CC=CC=2CC1C1=CC=CC=C1 SJWKMOBOBCRSTP-UHFFFAOYSA-N 0.000 claims 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 claims 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract description 12
125000005605 benzo group Chemical group 0.000 abstract 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 81
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 74
239000000243 solution Substances 0.000 description 61
NWPNXBQSRGKSJB-UHFFFAOYSA-N 2-methylbenzonitrile Chemical compound CC1=CC=CC=C1C#N NWPNXBQSRGKSJB-UHFFFAOYSA-N 0.000 description 58
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 47
239000000203 mixture Substances 0.000 description 41
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 37
239000007787 solid Substances 0.000 description 32
238000006243 chemical reaction Methods 0.000 description 27
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
239000006260 foam Substances 0.000 description 21
239000003921 oil Substances 0.000 description 21
239000000543 intermediate Substances 0.000 description 20
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 17
239000011541 reaction mixture Substances 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 15
238000003818 flash chromatography Methods 0.000 description 15
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 13
229910052938 sodium sulfate Inorganic materials 0.000 description 13
235000011152 sodium sulphate Nutrition 0.000 description 13
238000003756 stirring Methods 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000002844 melting Methods 0.000 description 12
230000008018 melting Effects 0.000 description 12
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000000284 extract Substances 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 9
230000007935 neutral effect Effects 0.000 description 9
239000000047 product Substances 0.000 description 9
229920006395 saturated elastomer Polymers 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
210000004027 cell Anatomy 0.000 description 8
239000011780 sodium chloride Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 7
239000013078 crystal Substances 0.000 description 7
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 7
KFCJKQZKHMRYQF-UHFFFAOYSA-N 3,4-dihydroisoquinolin-1-amine Chemical class C1=CC=C2C(N)=NCCC2=C1 KFCJKQZKHMRYQF-UHFFFAOYSA-N 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 6
FQCCBNFLPVZWKW-UHFFFAOYSA-N 5-ethynyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.NC1=NC(C#C)CC2=C1SC=C2 FQCCBNFLPVZWKW-UHFFFAOYSA-N 0.000 description 5
150000001299 aldehydes Chemical class 0.000 description 5
238000007796 conventional method Methods 0.000 description 5
229940043279 diisopropylamine Drugs 0.000 description 5
GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
238000010992 reflux Methods 0.000 description 5
238000012360 testing method Methods 0.000 description 5
LTIWDKAKNMJETP-UHFFFAOYSA-N 3-pyridin-4-yl-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=CC=CC=C2C(N)=NC1C1=CC=NC=C1 LTIWDKAKNMJETP-UHFFFAOYSA-N 0.000 description 4
RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 4
AHEDEGJLEDMRHX-UHFFFAOYSA-N 5-prop-1-ynyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.NC1=NC(C#CC)CC2=C1SC=C2 AHEDEGJLEDMRHX-UHFFFAOYSA-N 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 4
108090000790 Enzymes Proteins 0.000 description 4
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
206010040070 Septic Shock Diseases 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
239000012230 colorless oil Substances 0.000 description 4
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 4
150000002466 imines Chemical class 0.000 description 4
229910052744 lithium Inorganic materials 0.000 description 4
239000002609 medium Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
125000004665 trialkylsilyl group Chemical group 0.000 description 4
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 3
WQWQHJNUHQEGTN-UHFFFAOYSA-N 2-chloro-6-methylbenzonitrile Chemical compound CC1=CC=CC(Cl)=C1C#N WQWQHJNUHQEGTN-UHFFFAOYSA-N 0.000 description 3
239000001431 2-methylbenzaldehyde Substances 0.000 description 3
GZLHIYBVSFUPND-UHFFFAOYSA-N 3-(3-bromophenyl)propan-1-ol Chemical compound OCCCC1=CC=CC(Br)=C1 GZLHIYBVSFUPND-UHFFFAOYSA-N 0.000 description 3
QSEOYGMXGOABPM-UHFFFAOYSA-N 3-[4-(3-azidopropoxy)phenyl]-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=CC=CC=C2C(N)=NC1C1=CC=C(OCCCN=[N+]=[N-])C=C1 QSEOYGMXGOABPM-UHFFFAOYSA-N 0.000 description 3
ZFXNHXIRRYAIRM-UHFFFAOYSA-N 3-ethynyl-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1=CC=C2C(N)=NC(C#C)CC2=C1 ZFXNHXIRRYAIRM-UHFFFAOYSA-N 0.000 description 3
LJRWLSKYGWLYIM-UHFFFAOYSA-N 3-trimethylsilylprop-2-ynal Chemical compound C[Si](C)(C)C#CC=O LJRWLSKYGWLYIM-UHFFFAOYSA-N 0.000 description 3
XQCCNZFHLCQXEP-UHFFFAOYSA-N 4-(3-bromopropoxy)benzaldehyde Chemical compound BrCCCOC1=CC=C(C=O)C=C1 XQCCNZFHLCQXEP-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
208000024827 Alzheimer disease Diseases 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
206010061218 Inflammation Diseases 0.000 description 3
239000002168 alkylating agent Substances 0.000 description 3
229940100198 alkylating agent Drugs 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
229960002173 citrulline Drugs 0.000 description 3
239000002158 endotoxin Substances 0.000 description 3
239000011521 glass Substances 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
230000004968 inflammatory condition Effects 0.000 description 3
230000004054 inflammatory process Effects 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
229920006008 lipopolysaccharide Polymers 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000003586 protic polar solvent Substances 0.000 description 3
BJDYCCHRZIFCGN-UHFFFAOYSA-N pyridin-1-ium;iodide Chemical compound I.C1=CC=NC=C1 BJDYCCHRZIFCGN-UHFFFAOYSA-N 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
MCBMVYASPQIKGE-UHFFFAOYSA-N 1-(2-azidoethyl)-3-bromobenzene Chemical compound BrC1=CC=CC(CCN=[N+]=[N-])=C1 MCBMVYASPQIKGE-UHFFFAOYSA-N 0.000 description 2
DADYIZHXQHKSII-UHFFFAOYSA-N 1-(2-azidoethyl)-4-bromobenzene Chemical compound BrC1=CC=C(CCN=[N+]=[N-])C=C1 DADYIZHXQHKSII-UHFFFAOYSA-N 0.000 description 2
IWWBWOQZBZXCBO-UHFFFAOYSA-N 1-(3-azidopropyl)-3-bromobenzene Chemical compound BrC1=CC=CC(CCCN=[N+]=[N-])=C1 IWWBWOQZBZXCBO-UHFFFAOYSA-N 0.000 description 2
ZEDPQIJYJCPIRM-UHFFFAOYSA-N 2,3-dimethylbenzonitrile Chemical compound CC1=CC=CC(C#N)=C1C ZEDPQIJYJCPIRM-UHFFFAOYSA-N 0.000 description 2
OZOQTENKIVKILK-UHFFFAOYSA-N 2,5-dimethylbenzonitrile Chemical compound CC1=CC=C(C)C(C#N)=C1 OZOQTENKIVKILK-UHFFFAOYSA-N 0.000 description 2
QSACPWSIIRFHHR-UHFFFAOYSA-N 2,6-dimethylbenzonitrile Chemical compound CC1=CC=CC(C)=C1C#N QSACPWSIIRFHHR-UHFFFAOYSA-N 0.000 description 2
ILJKKAIQFPEIBL-UHFFFAOYSA-N 2-cyclopropyl-2-hydroxyacetonitrile Chemical compound N#CC(O)C1CC1 ILJKKAIQFPEIBL-UHFFFAOYSA-N 0.000 description 2
ZWDVQMVZZYIAHO-UHFFFAOYSA-N 2-fluorobenzaldehyde Chemical compound FC1=CC=CC=C1C=O ZWDVQMVZZYIAHO-UHFFFAOYSA-N 0.000 description 2
CJMMHNSKDRDEHG-UHFFFAOYSA-N 2-methyl-5-(2-trimethylsilylethynyl)-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.C1C(C#C[Si](C)(C)C)N=C(N)C2=C1C=C(C)S2 CJMMHNSKDRDEHG-UHFFFAOYSA-N 0.000 description 2
KMMNUJOZUBVCSV-UHFFFAOYSA-N 3-(1,3-thiazol-2-yl)-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=CC=CC=C2C(N)=NC1C1=NC=CS1 KMMNUJOZUBVCSV-UHFFFAOYSA-N 0.000 description 2
ORWQOGXQRGFZSB-UHFFFAOYSA-N 3-(1h-imidazol-2-yl)-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=CC=CC=C2C(N)=NC1C1=NC=CN1 ORWQOGXQRGFZSB-UHFFFAOYSA-N 0.000 description 2
DQNXIMCPKXAXKT-UHFFFAOYSA-N 3-(2-fluorophenyl)-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=CC=CC=C2C(N)=NC1C1=CC=CC=C1F DQNXIMCPKXAXKT-UHFFFAOYSA-N 0.000 description 2
CWBMFVGIEVNOTQ-UHFFFAOYSA-N 3-[(dimethylamino)methyl]benzonitrile Chemical compound CN(C)CC1=CC=CC(C#N)=C1 CWBMFVGIEVNOTQ-UHFFFAOYSA-N 0.000 description 2
MFXUDORUNQJYPB-UHFFFAOYSA-N 3-[3-(2-aminoethyl)phenyl]-3,4-dihydroisoquinolin-1-amine;dihydrochloride Chemical compound Cl.Cl.NCCC1=CC=CC(C2N=C(N)C3=CC=CC=C3C2)=C1 MFXUDORUNQJYPB-UHFFFAOYSA-N 0.000 description 2
PKBCBXBGUNCCRD-UHFFFAOYSA-N 3-[4-(2-aminoethyl)phenyl]-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1=CC(CCN)=CC=C1C1N=C(N)C2=CC=CC=C2C1 PKBCBXBGUNCCRD-UHFFFAOYSA-N 0.000 description 2
ADGOHMSEBOVNDQ-UHFFFAOYSA-N 3-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1C1N=C(N)C2=CC=CC=C2C1 ADGOHMSEBOVNDQ-UHFFFAOYSA-N 0.000 description 2
FGTFSQNIERTOFD-UHFFFAOYSA-N 3-fluoro-6-methyl-2-trimethylsilylbenzonitrile Chemical compound CC1=CC=C(F)C([Si](C)(C)C)=C1C#N FGTFSQNIERTOFD-UHFFFAOYSA-N 0.000 description 2
RBIGKSZIQCTIJF-UHFFFAOYSA-N 3-formylthiophene Chemical compound O=CC=1C=CSC=1 RBIGKSZIQCTIJF-UHFFFAOYSA-N 0.000 description 2
AZVSIHIBYRHSLB-UHFFFAOYSA-N 3-furaldehyde Chemical compound O=CC=1C=COC=1 AZVSIHIBYRHSLB-UHFFFAOYSA-N 0.000 description 2
AZJYQNFIFMXNPH-UHFFFAOYSA-N 4-(1-amino-3,4-dihydroisoquinolin-3-yl)phenol;hydrochloride Chemical compound Cl.C1C2=CC=CC=C2C(N)=NC1C1=CC=C(O)C=C1 AZJYQNFIFMXNPH-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 2
YBKCZZYMZKMBQK-UHFFFAOYSA-N 5-(1,3-thiazol-2-yl)-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.C1C=2C=CSC=2C(N)=NC1C1=NC=CS1 YBKCZZYMZKMBQK-UHFFFAOYSA-N 0.000 description 2
RYAMPLRUXFGSSO-UHFFFAOYSA-N 5-(1-benzylpyrrol-2-yl)-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.C1C=2C=CSC=2C(N)=NC1C1=CC=CN1CC1=CC=CC=C1 RYAMPLRUXFGSSO-UHFFFAOYSA-N 0.000 description 2
JSAVSISEZJIHAG-UHFFFAOYSA-N 5-(1-methylpyrrol-2-yl)-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.CN1C=CC=C1C1N=C(N)C(SC=C2)=C2C1 JSAVSISEZJIHAG-UHFFFAOYSA-N 0.000 description 2
WHKMWLKLQWQNGR-UHFFFAOYSA-N 5-(2-phenylethynyl)-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.C1C=2C=CSC=2C(N)=NC1C#CC1=CC=CC=C1 WHKMWLKLQWQNGR-UHFFFAOYSA-N 0.000 description 2
JHSPRNFFTKFENB-UHFFFAOYSA-N 5-(furan-2-yl)-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.C1C=2C=CSC=2C(N)=NC1C1=CC=CO1 JHSPRNFFTKFENB-UHFFFAOYSA-N 0.000 description 2
PHDQLVDMDPVQSI-UHFFFAOYSA-N 5-(furan-3-yl)-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.C1C=2C=CSC=2C(N)=NC1C=1C=COC=1 PHDQLVDMDPVQSI-UHFFFAOYSA-N 0.000 description 2
FUQZRHLFJJTGOP-UHFFFAOYSA-N 5-cyclobutyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.C1C=2C=CSC=2C(N)=NC1C1CCC1 FUQZRHLFJJTGOP-UHFFFAOYSA-N 0.000 description 2
VSPUHBGAKMXFTM-UHFFFAOYSA-N 5-cyclopropyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.C1C=2C=CSC=2C(N)=NC1C1CC1 VSPUHBGAKMXFTM-UHFFFAOYSA-N 0.000 description 2
RAMQVXNALCXHPM-UHFFFAOYSA-N 5-ethynyl-2-methyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.C1C(C#C)N=C(N)C2=C1C=C(C)S2 RAMQVXNALCXHPM-UHFFFAOYSA-N 0.000 description 2
SXWLPHYNVOMCEA-UHFFFAOYSA-N 5-phenyl-2-trimethylsilyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.N1=C(N)C=2SC([Si](C)(C)C)=CC=2CC1C1=CC=CC=C1 SXWLPHYNVOMCEA-UHFFFAOYSA-N 0.000 description 2
VMKPEKWFKJPWSC-UHFFFAOYSA-N 5-phenyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.C1C=2C=CSC=2C(N)=NC1C1=CC=CC=C1 VMKPEKWFKJPWSC-UHFFFAOYSA-N 0.000 description 2
MSTZDVWVSADNMR-UHFFFAOYSA-N 5-propyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.NC1=NC(CCC)CC2=C1SC=C2 MSTZDVWVSADNMR-UHFFFAOYSA-N 0.000 description 2
FRDGRDYXWFXZLW-UHFFFAOYSA-N 5-pyridin-3-yl-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.C1C=2C=CSC=2C(N)=NC1C1=CC=CN=C1 FRDGRDYXWFXZLW-UHFFFAOYSA-N 0.000 description 2
IHIBFGIIDQMRKK-UHFFFAOYSA-N 5-thiophen-2-yl-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.C1C=2C=CSC=2C(N)=NC1C1=CC=CS1 IHIBFGIIDQMRKK-UHFFFAOYSA-N 0.000 description 2
FDQRLKJRQMPMPS-UHFFFAOYSA-N 6,7-dihydrothieno[3,2-c]pyridin-4-amine;hydroiodide Chemical compound I.NC1=NCCC2=C1C=CS2 FDQRLKJRQMPMPS-UHFFFAOYSA-N 0.000 description 2
AJXWTNRPHACFES-UHFFFAOYSA-N 6-cyclopropyl-6,7-dihydrothieno[3,2-c]pyridin-4-amine;hydrochloride Chemical compound Cl.C1C=2SC=CC=2C(N)=NC1C1CC1 AJXWTNRPHACFES-UHFFFAOYSA-N 0.000 description 2
PXFGKKZTQBIOAC-UHFFFAOYSA-N 6-ethynyl-6,7-dihydrothieno[3,2-c]pyridin-4-amine;hydrochloride Chemical compound Cl.NC1=NC(C#C)CC2=C1C=CS2 PXFGKKZTQBIOAC-UHFFFAOYSA-N 0.000 description 2
IWCFSQKYBVHJEK-UHFFFAOYSA-N 6-phenyl-6,7-dihydrothieno[3,2-c]pyridin-4-amine;hydrochloride Chemical compound Cl.C1C=2SC=CC=2C(N)=NC1C1=CC=CC=C1 IWCFSQKYBVHJEK-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
239000004475 Arginine Substances 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
208000015943 Coeliac disease Diseases 0.000 description 2
201000004624 Dermatitis Diseases 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
206010021143 Hypoxia Diseases 0.000 description 2
ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 2
229930064664 L-arginine Natural products 0.000 description 2
235000014852 L-arginine Nutrition 0.000 description 2
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
206010036618 Premenstrual syndrome Diseases 0.000 description 2
229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
206010003246 arthritis Diseases 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
125000004391 aryl sulfonyl group Chemical group 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000000969 carrier Substances 0.000 description 2
210000001072 colon Anatomy 0.000 description 2
230000006378 damage Effects 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
230000007954 hypoxia Effects 0.000 description 2
230000006698 induction Effects 0.000 description 2
230000002757 inflammatory effect Effects 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
210000002540 macrophage Anatomy 0.000 description 2
GPBINNSHRSTZQE-UHFFFAOYSA-N methyl 3-(3-bromophenyl)prop-2-enoate Chemical compound COC(=O)C=CC1=CC=CC(Br)=C1 GPBINNSHRSTZQE-UHFFFAOYSA-N 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 2
229910003446 platinum oxide Inorganic materials 0.000 description 2
229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000002243 precursor Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000004007 reversed phase HPLC Methods 0.000 description 2
230000036303 septic shock Effects 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000001119 stannous chloride Substances 0.000 description 2
235000011150 stannous chloride Nutrition 0.000 description 2
239000000725 suspension Substances 0.000 description 2
208000011580 syndromic disease Diseases 0.000 description 2
YEMUSDCFQUBPAL-SNAWJCMRSA-N (e)-3-(3-bromophenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=CC(Br)=C1 YEMUSDCFQUBPAL-SNAWJCMRSA-N 0.000 description 1
NENLYAQPNATJSU-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline Chemical compound C1NCCC2CCCCC21 NENLYAQPNATJSU-UHFFFAOYSA-N 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
RHKPJTFLRQNNGJ-UHFFFAOYSA-N 1,3-benzothiazole-2-carbaldehyde Chemical compound C1=CC=C2SC(C=O)=NC2=C1 RHKPJTFLRQNNGJ-UHFFFAOYSA-N 0.000 description 1
VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
ZPZPSZZVDFMNQS-UHFFFAOYSA-N 1-(2-bromophenyl)-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC=C1Br ZPZPSZZVDFMNQS-UHFFFAOYSA-N 0.000 description 1
LZSYGJNFCREHMD-UHFFFAOYSA-N 1-bromo-2-(bromomethyl)benzene Chemical compound BrCC1=CC=CC=C1Br LZSYGJNFCREHMD-UHFFFAOYSA-N 0.000 description 1
KQJQPCJDKBKSLV-UHFFFAOYSA-N 1-bromo-3-ethenylbenzene Chemical compound BrC1=CC=CC(C=C)=C1 KQJQPCJDKBKSLV-UHFFFAOYSA-N 0.000 description 1
RPGVLGBWYBYJBM-UHFFFAOYSA-N 1-ethylsulfanyl-3-methyl-3,4-dihydroisoquinoline Chemical compound C1=CC=C2C(SCC)=NC(C)CC2=C1 RPGVLGBWYBYJBM-UHFFFAOYSA-N 0.000 description 1
125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
VVVOJODFBWBNBI-UHFFFAOYSA-N 2,5-difluorobenzaldehyde Chemical compound FC1=CC=C(F)C(C=O)=C1 VVVOJODFBWBNBI-UHFFFAOYSA-N 0.000 description 1
WVDRPXZCCUCIAF-UHFFFAOYSA-N 2,5-dimethylthiophene-3-carbonitrile Chemical compound CC1=CC(C#N)=C(C)S1 WVDRPXZCCUCIAF-UHFFFAOYSA-N 0.000 description 1
FWEHLMFQLWSMTH-UHFFFAOYSA-N 2-(2-isothiocyanatoethyl)thiophene Chemical compound S=C=NCCC1=CC=CS1 FWEHLMFQLWSMTH-UHFFFAOYSA-N 0.000 description 1
MDAOEGJTBPQGCB-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)ethylurea Chemical compound COC1=CC=C(CCNC(N)=O)C=C1OC MDAOEGJTBPQGCB-UHFFFAOYSA-N 0.000 description 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 1
FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
QIHQWIAXCSASJY-UHFFFAOYSA-N 2-methylthiophene-3-carbonitrile Chemical compound CC=1SC=CC=1C#N QIHQWIAXCSASJY-UHFFFAOYSA-N 0.000 description 1
LMZFBIBGQYQZHC-UHFFFAOYSA-N 2-trimethylsilyl-6-(2-trimethylsilylethynyl)-6,7-dihydrothieno[3,2-c]pyridin-4-amine;hydrochloride Chemical compound Cl.NC1=NC(C#C[Si](C)(C)C)CC2=C1C=C([Si](C)(C)C)S2 LMZFBIBGQYQZHC-UHFFFAOYSA-N 0.000 description 1
YYJMVUBIHRRDQR-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1=CC=C2SC(C3N=C(C4=CC=CC=C4C3)N)=NC2=C1 YYJMVUBIHRRDQR-UHFFFAOYSA-N 0.000 description 1
MIWIDZZWESPHKW-UHFFFAOYSA-N 3-(2-methylphenyl)-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.CC1=CC=CC=C1C1N=C(N)C2=CC=CC=C2C1 MIWIDZZWESPHKW-UHFFFAOYSA-N 0.000 description 1
WAXJRURMFHHHGP-UHFFFAOYSA-N 3-(2-phenylethynyl)-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=CC=CC=C2C(N)=NC1C#CC1=CC=CC=C1 WAXJRURMFHHHGP-UHFFFAOYSA-N 0.000 description 1
KPCPQKUUEUSDGM-UHFFFAOYSA-N 3-(3-chlorophenyl)-3,4-dihydroisoquinolin-1-amine hydrochloride Chemical compound [Cl-].C1C2=CC=CC=C2C([NH3+])=NC1C1=CC=CC(Cl)=C1 KPCPQKUUEUSDGM-UHFFFAOYSA-N 0.000 description 1
VIVVCOWORHNYCU-UHFFFAOYSA-N 3-(3-fluorophenyl)-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=CC=CC=C2C(N)=NC1C1=CC=CC(F)=C1 VIVVCOWORHNYCU-UHFFFAOYSA-N 0.000 description 1
HTFUKNNDRKJGHX-UHFFFAOYSA-N 3-(3-methylphenyl)-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.CC1=CC=CC(C2N=C(N)C3=CC=CC=C3C2)=C1 HTFUKNNDRKJGHX-UHFFFAOYSA-N 0.000 description 1
SQFCVCYONNVDCX-UHFFFAOYSA-N 3-(4-chlorophenyl)-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=CC=CC=C2C(N)=NC1C1=CC=C(Cl)C=C1 SQFCVCYONNVDCX-UHFFFAOYSA-N 0.000 description 1
YTKPEPDVHUMZMJ-UHFFFAOYSA-N 3-(4-fluorophenyl)-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=CC=CC=C2C(N)=NC1C1=CC=C(F)C=C1 YTKPEPDVHUMZMJ-UHFFFAOYSA-N 0.000 description 1
MYJXGWMZZLXKNE-UHFFFAOYSA-N 3-(4-methoxyphenyl)-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1N=C(N)C2=CC=CC=C2C1 MYJXGWMZZLXKNE-UHFFFAOYSA-N 0.000 description 1
WMYYDMBUUMFNSF-UHFFFAOYSA-N 3-(4-methylphenyl)-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1=CC(C)=CC=C1C1N=C(N)C2=CC=CC=C2C1 WMYYDMBUUMFNSF-UHFFFAOYSA-N 0.000 description 1
LKOSESXQYSCXOV-UHFFFAOYSA-N 3-(4-methylsulfanylphenyl)-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1=CC(SC)=CC=C1C1N=C(N)C2=CC=CC=C2C1 LKOSESXQYSCXOV-UHFFFAOYSA-N 0.000 description 1
VRMMHQFXIGZMMX-UHFFFAOYSA-N 3-(furan-2-yl)-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=CC=CC=C2C(N)=NC1C1=CC=CO1 VRMMHQFXIGZMMX-UHFFFAOYSA-N 0.000 description 1
RASQKXNHQVLVRP-UHFFFAOYSA-N 3-(furan-3-yl)-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=CC=CC=C2C(N)=NC1C=1C=COC=1 RASQKXNHQVLVRP-UHFFFAOYSA-N 0.000 description 1
VOBLFTCBIDEBQE-UHFFFAOYSA-N 3-[3-(2-azidoethyl)phenyl]-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=CC=CC(CCN=[N+]=[N-])=C1 VOBLFTCBIDEBQE-UHFFFAOYSA-N 0.000 description 1
FWAATBISIWZKGG-UHFFFAOYSA-N 3-[3-(2-azidoethyl)phenyl]-3,4-dihydroisoquinolin-1-amine hydrochloride Chemical compound Cl.NC1=NC(Cc2ccccc12)c1cccc(CCN=[N+]=[N-])c1 FWAATBISIWZKGG-UHFFFAOYSA-N 0.000 description 1
USWZWOBSNMHDCK-UHFFFAOYSA-N 3-[3-(3-aminopropyl)phenyl]-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.NCCCC1=CC=CC(C2N=C(N)C3=CC=CC=C3C2)=C1 USWZWOBSNMHDCK-UHFFFAOYSA-N 0.000 description 1
PYFSVIGEHNHTLR-UHFFFAOYSA-N 3-[3-(3-azidopropyl)phenyl]-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=CC=CC(CCCN=[N+]=[N-])=C1 PYFSVIGEHNHTLR-UHFFFAOYSA-N 0.000 description 1
UPCPCDBVWBFPHC-UHFFFAOYSA-N 3-[3-(3-azidopropyl)phenyl]-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=CC=CC=C2C(N)=NC1C1=CC=CC(CCCN=[N+]=[N-])=C1 UPCPCDBVWBFPHC-UHFFFAOYSA-N 0.000 description 1
SWQCLSCSSYNCSQ-UHFFFAOYSA-N 3-[4-(2-azidoethyl)phenyl]-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=CC=CC=C2C(N)=NC1C1=CC=C(CCN=[N+]=[N-])C=C1 SWQCLSCSSYNCSQ-UHFFFAOYSA-N 0.000 description 1
SNNXGVXKFJWABJ-UHFFFAOYSA-N 3-[4-(3-aminopropoxy)phenyl]-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1=CC(OCCCN)=CC=C1C1N=C(N)C2=CC=CC=C2C1 SNNXGVXKFJWABJ-UHFFFAOYSA-N 0.000 description 1
FKFZTNLSUJCIMG-UHFFFAOYSA-N 3-chloro-2-methylbenzonitrile Chemical compound CC1=C(Cl)C=CC=C1C#N FKFZTNLSUJCIMG-UHFFFAOYSA-N 0.000 description 1
SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 description 1
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
PNESXZASOVBLIZ-UHFFFAOYSA-N 3-cyclopropyl-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=CC=CC=C2C(N)=NC1C1CC1 PNESXZASOVBLIZ-UHFFFAOYSA-N 0.000 description 1
PIKNVEVCWAAOMJ-UHFFFAOYSA-N 3-fluorobenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1 PIKNVEVCWAAOMJ-UHFFFAOYSA-N 0.000 description 1
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
VUVSSLDCCMJFTM-UHFFFAOYSA-N 3-methoxy-2-methylbenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1C VUVSSLDCCMJFTM-UHFFFAOYSA-N 0.000 description 1
ALZHYEITUZEZMT-UHFFFAOYSA-N 3-methylthiophene-2-carbonitrile Chemical compound CC=1C=CSC=1C#N ALZHYEITUZEZMT-UHFFFAOYSA-N 0.000 description 1
GVZWAWRNUODWHS-UHFFFAOYSA-N 3-phenyl-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=CC=CC=C2C(N)=NC1C1=CC=CC=C1 GVZWAWRNUODWHS-UHFFFAOYSA-N 0.000 description 1
XCCFOPQGIQXGNI-UHFFFAOYSA-N 3-piperidin-4-yl-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=CC=CC=C2C(N)=NC1C1CCNCC1 XCCFOPQGIQXGNI-UHFFFAOYSA-N 0.000 description 1
GHDZGHVLQVILRB-UHFFFAOYSA-N 3-pyridin-3-yl-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=CC=CC=C2C(N)=NC1C1=CC=CN=C1 GHDZGHVLQVILRB-UHFFFAOYSA-N 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
UTYOQOYXJUGBOR-UHFFFAOYSA-N 3-thiophen-2-yl-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=CC=CC=C2C(N)=NC1C1=CC=CS1 UTYOQOYXJUGBOR-UHFFFAOYSA-N 0.000 description 1
LPEBMDFRIKYFCF-UHFFFAOYSA-N 4-bromo-2-methylbenzonitrile Chemical compound CC1=CC(Br)=CC=C1C#N LPEBMDFRIKYFCF-UHFFFAOYSA-N 0.000 description 1
AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
ZVTWZSXLLMNMQC-UHFFFAOYSA-N 4-phenylmethoxybenzaldehyde Chemical compound C1=CC(C=O)=CC=C1OCC1=CC=CC=C1 ZVTWZSXLLMNMQC-UHFFFAOYSA-N 0.000 description 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
KWWKDHHGJPBYJO-UHFFFAOYSA-N 5,8-difluoro-3-(4-fluorophenyl)-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=C(F)C=CC(F)=C2C(N)=NC1C1=CC=C(F)C=C1 KWWKDHHGJPBYJO-UHFFFAOYSA-N 0.000 description 1
JKWVHJKCWTWQCG-UHFFFAOYSA-N 5-(1-benzylpyrrol-2-yl)-2-trimethylsilyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.N1=C(N)C=2SC([Si](C)(C)C)=CC=2CC1C1=CC=CN1CC1=CC=CC=C1 JKWVHJKCWTWQCG-UHFFFAOYSA-N 0.000 description 1
UKCDOSZESNLJDD-UHFFFAOYSA-N 5-(1-methylpyrrol-2-yl)-2-trimethylsilyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine hydrochloride Chemical compound Cl.CN1C=CC=C1C1N=C(N)C(SC(=C2)[Si](C)(C)C)=C2C1 UKCDOSZESNLJDD-UHFFFAOYSA-N 0.000 description 1
DTWVZORHBDWZNL-UHFFFAOYSA-N 5-(2-phenylethynyl)-2-trimethylsilyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.N1=C(N)C=2SC([Si](C)(C)C)=CC=2CC1C#CC1=CC=CC=C1 DTWVZORHBDWZNL-UHFFFAOYSA-N 0.000 description 1
LPDWSOMWJWOMAJ-UHFFFAOYSA-N 5-(3,3-dimethylbut-1-ynyl)-2-trimethylsilyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.NC1=NC(C#CC(C)(C)C)CC2=C1SC([Si](C)(C)C)=C2 LPDWSOMWJWOMAJ-UHFFFAOYSA-N 0.000 description 1
REEFYEFGXQKOBG-UHFFFAOYSA-N 5-(3,3-dimethylbut-1-ynyl)-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.NC1=NC(C#CC(C)(C)C)CC2=C1SC=C2 REEFYEFGXQKOBG-UHFFFAOYSA-N 0.000 description 1
NRVMEOQPTLRCSW-UHFFFAOYSA-N 5-(furan-2-yl)-2-trimethylsilyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.N1=C(N)C=2SC([Si](C)(C)C)=CC=2CC1C1=CC=CO1 NRVMEOQPTLRCSW-UHFFFAOYSA-N 0.000 description 1
AWYSYYVAVXKNHE-UHFFFAOYSA-N 5-(furan-3-yl)-2-trimethylsilyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.N1=C(N)C=2SC([Si](C)(C)C)=CC=2CC1C=1C=COC=1 AWYSYYVAVXKNHE-UHFFFAOYSA-N 0.000 description 1
FKJAHTIIMJZBQL-UHFFFAOYSA-N 5-chloro-3-phenyl-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=C(Cl)C=CC=C2C(N)=NC1C1=CC=CC=C1 FKJAHTIIMJZBQL-UHFFFAOYSA-N 0.000 description 1
TVIZHABTBIENPP-UHFFFAOYSA-N 5-cyclobutyl-2-trimethylsilyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.N1=C(N)C=2SC([Si](C)(C)C)=CC=2CC1C1CCC1 TVIZHABTBIENPP-UHFFFAOYSA-N 0.000 description 1
VYYCPTXGTBLACH-UHFFFAOYSA-N 5-cyclopropyl-2-trimethylsilyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.N1=C(N)C=2SC([Si](C)(C)C)=CC=2CC1C1CC1 VYYCPTXGTBLACH-UHFFFAOYSA-N 0.000 description 1
UYEPDSINGCIOGO-UHFFFAOYSA-N 5-ethyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.NC1=NC(CC)CC2=C1SC=C2 UYEPDSINGCIOGO-UHFFFAOYSA-N 0.000 description 1
CICQSHRUKAYJKH-UHFFFAOYSA-N 5-ethynyl-2-trimethylsilyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.C1C(C#C)N=C(N)C2=C1C=C([Si](C)(C)C)S2 CICQSHRUKAYJKH-UHFFFAOYSA-N 0.000 description 1
IBRODYNXELBTJC-UHFFFAOYSA-N 5-fluoro-2-methylbenzonitrile Chemical compound CC1=CC=C(F)C=C1C#N IBRODYNXELBTJC-UHFFFAOYSA-N 0.000 description 1
ZTKVQPONCQVHNR-UHFFFAOYSA-N 5-fluoro-3-(4-fluorophenyl)-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=C(F)C=CC=C2C(N)=NC1C1=CC=C(F)C=C1 ZTKVQPONCQVHNR-UHFFFAOYSA-N 0.000 description 1
YAEMVJAUQOINFD-UHFFFAOYSA-N 5-fluoro-3-phenyl-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=C(F)C=CC=C2C(N)=NC1C1=CC=CC=C1 YAEMVJAUQOINFD-UHFFFAOYSA-N 0.000 description 1
HBELDQQNSMHJKH-UHFFFAOYSA-N 5-methoxy-3-phenyl-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C=2C(OC)=CC=CC=2C(N)=NC1C1=CC=CC=C1 HBELDQQNSMHJKH-UHFFFAOYSA-N 0.000 description 1
NJFXHZBKGDJFLF-UHFFFAOYSA-N 5-methyl-3-phenyl-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C=2C(C)=CC=CC=2C(N)=NC1C1=CC=CC=C1 NJFXHZBKGDJFLF-UHFFFAOYSA-N 0.000 description 1
CELGXEISPMRLMJ-UHFFFAOYSA-N 5-prop-1-ynyl-2-trimethylsilyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.NC1=NC(C#CC)CC2=C1SC([Si](C)(C)C)=C2 CELGXEISPMRLMJ-UHFFFAOYSA-N 0.000 description 1
LSDPMVOEMMALIW-UHFFFAOYSA-N 5-pyridin-3-yl-2-trimethylsilyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.N1=C(N)C=2SC([Si](C)(C)C)=CC=2CC1C1=CC=CN=C1 LSDPMVOEMMALIW-UHFFFAOYSA-N 0.000 description 1
FOQPUOOYMVRVHE-UHFFFAOYSA-N 5-thiophen-2-yl-2-trimethylsilyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine;hydrochloride Chemical compound Cl.N1=C(N)C=2SC([Si](C)(C)C)=CC=2CC1C1=CC=CS1 FOQPUOOYMVRVHE-UHFFFAOYSA-N 0.000 description 1
JVPUZUTVEGLNSW-UHFFFAOYSA-N 6,7-dimethoxy-3,4-dihydroisoquinolin-1-amine Chemical compound C1CN=C(N)C2=C1C=C(OC)C(OC)=C2 JVPUZUTVEGLNSW-UHFFFAOYSA-N 0.000 description 1
YROUJLFYEPNXOC-UHFFFAOYSA-N 6-bromo-3-phenyl-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=CC(Br)=CC=C2C(N)=NC1C1=CC=CC=C1 YROUJLFYEPNXOC-UHFFFAOYSA-N 0.000 description 1
GMDNZVQWRAHDIW-UHFFFAOYSA-N 6-cyclopropyl-2-trimethylsilyl-6,7-dihydrothieno[3,2-c]pyridin-4-amine;hydrochloride Chemical compound Cl.S1C([Si](C)(C)C)=CC(C(=N2)N)=C1CC2C1CC1 GMDNZVQWRAHDIW-UHFFFAOYSA-N 0.000 description 1
OKQRYFFMKUXMFG-UHFFFAOYSA-N 6-methoxy-3,4-dihydroisoquinolin-1-amine Chemical compound NC1=NCCC2=CC(OC)=CC=C21 OKQRYFFMKUXMFG-UHFFFAOYSA-N 0.000 description 1
FQTYCKROTGJVNU-UHFFFAOYSA-N 6-phenyl-2-trimethylsilyl-6,7-dihydrothieno[3,2-c]pyridin-4-amine;hydrochloride Chemical compound Cl.S1C([Si](C)(C)C)=CC(C(=N2)N)=C1CC2C1=CC=CC=C1 FQTYCKROTGJVNU-UHFFFAOYSA-N 0.000 description 1
XSEUDFYWOSTTIK-UHFFFAOYSA-N 7-fluoro-3-(4-fluorophenyl)-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=CC=C(F)C=C2C(N)=NC1C1=CC=C(F)C=C1 XSEUDFYWOSTTIK-UHFFFAOYSA-N 0.000 description 1
XZPIGBPXFDPXFO-UHFFFAOYSA-N 7-methoxy-3,4-dihydroisoquinolin-1-amine Chemical compound C1CN=C(N)C2=CC(OC)=CC=C21 XZPIGBPXFDPXFO-UHFFFAOYSA-N 0.000 description 1
WGEHGGNVNTYXCY-UHFFFAOYSA-N 7-methyl-3-phenyl-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.N1=C(N)C2=CC(C)=CC=C2CC1C1=CC=CC=C1 WGEHGGNVNTYXCY-UHFFFAOYSA-N 0.000 description 1
JDWVRBPEZNFEJM-UHFFFAOYSA-N 8-chloro-3-(4-fluorophenyl)-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=CC=CC(Cl)=C2C(N)=NC1C1=CC=C(F)C=C1 JDWVRBPEZNFEJM-UHFFFAOYSA-N 0.000 description 1
XOPRZDDOSDVATP-UHFFFAOYSA-N 8-chloro-3-(furan-2-yl)-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=CC=CC(Cl)=C2C(N)=NC1C1=CC=CO1 XOPRZDDOSDVATP-UHFFFAOYSA-N 0.000 description 1
IGOYLBSKCUXCHM-UHFFFAOYSA-N 8-chloro-3-phenyl-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=CC=CC(Cl)=C2C(N)=NC1C1=CC=CC=C1 IGOYLBSKCUXCHM-UHFFFAOYSA-N 0.000 description 1
MUPFNLCISCTPFJ-UHFFFAOYSA-N 8-fluoro-3-(4-fluorophenyl)-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=CC=CC(F)=C2C(N)=NC1C1=CC=C(F)C=C1 MUPFNLCISCTPFJ-UHFFFAOYSA-N 0.000 description 1
KUAQOLFJWCQHCY-UHFFFAOYSA-N 8-fluoro-3-phenyl-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.C1C2=CC=CC(F)=C2C(N)=NC1C1=CC=CC=C1 KUAQOLFJWCQHCY-UHFFFAOYSA-N 0.000 description 1
DAJQJZVKFDANIV-UHFFFAOYSA-N 8-methyl-3-phenyl-3,4-dihydroisoquinolin-1-amine;hydrochloride Chemical compound Cl.N1=C(N)C=2C(C)=CC=CC=2CC1C1=CC=CC=C1 DAJQJZVKFDANIV-UHFFFAOYSA-N 0.000 description 1
208000030507 AIDS Diseases 0.000 description 1
206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
208000035939 Alveolitis allergic Diseases 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 description 1
206010002556 Ankylosing Spondylitis Diseases 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
108010039627 Aprotinin Proteins 0.000 description 1
208000004300 Atrophic Gastritis Diseases 0.000 description 1
206010003805 Autism Diseases 0.000 description 1
208000020706 Autistic disease Diseases 0.000 description 1
208000031729 Bacteremia Diseases 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
206010009900 Colitis ulcerative Diseases 0.000 description 1
241000272201 Columbiformes Species 0.000 description 1
206010010741 Conjunctivitis Diseases 0.000 description 1
206010010904 Convulsion Diseases 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
208000011231 Crohn disease Diseases 0.000 description 1
108090000695 Cytokines Proteins 0.000 description 1
102000004127 Cytokines Human genes 0.000 description 1
206010012289 Dementia Diseases 0.000 description 1
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
239000006144 Dulbecco’s modiﬁed Eagle's medium Substances 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
208000037487 Endotoxemia Diseases 0.000 description 1
241000400611 Eucalyptus deanei Species 0.000 description 1
208000027445 Farmer Lung Diseases 0.000 description 1
208000007882 Gastritis Diseases 0.000 description 1
208000036495 Gastritis atrophic Diseases 0.000 description 1
206010017943 Gastrointestinal conditions Diseases 0.000 description 1
208000017228 Gastrointestinal motility disease Diseases 0.000 description 1
206010017993 Gastrointestinal neoplasms Diseases 0.000 description 1
201000005569 Gout Diseases 0.000 description 1
208000010496 Heart Arrest Diseases 0.000 description 1
208000013875 Heart injury Diseases 0.000 description 1
241000590002 Helicobacter pylori Species 0.000 description 1
208000023105 Huntington disease Diseases 0.000 description 1
208000013016 Hypoglycemia Diseases 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
206010062016 Immunosuppression Diseases 0.000 description 1
102000015696 Interleukins Human genes 0.000 description 1
108010063738 Interleukins Proteins 0.000 description 1
208000006264 Korsakoff syndrome Diseases 0.000 description 1
ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
229930182816 L-glutamine Natural products 0.000 description 1
MRAUNPAHJZDYCK-BYPYZUCNSA-N L-nitroarginine Chemical compound OC(=O)[C@@H](N)CCCNC(=N)N[N+]([O-])=O MRAUNPAHJZDYCK-BYPYZUCNSA-N 0.000 description 1
GDBQQVLCIARPGH-UHFFFAOYSA-N Leupeptin Natural products CC(C)CC(NC(C)=O)C(=O)NC(CC(C)C)C(=O)NC(C=O)CCCN=C(N)N GDBQQVLCIARPGH-UHFFFAOYSA-N 0.000 description 1
208000019693 Lung disease Diseases 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
208000019695 Migraine disease Diseases 0.000 description 1
208000036831 Moderate mental retardation Diseases 0.000 description 1
208000007920 Neurogenic Inflammation Diseases 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
206010033645 Pancreatitis Diseases 0.000 description 1
208000018737 Parkinson disease Diseases 0.000 description 1
208000008469 Peptic Ulcer Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
206010036631 Presenile dementia Diseases 0.000 description 1
229940124158 Protease/peptidase inhibitor Drugs 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
206010037660 Pyrexia Diseases 0.000 description 1
208000013616 Respiratory Distress Syndrome Diseases 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical class [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
208000006011 Stroke Diseases 0.000 description 1
206010042496 Sunburn Diseases 0.000 description 1
208000000323 Tourette Syndrome Diseases 0.000 description 1
208000016620 Tourette disease Diseases 0.000 description 1
206010044248 Toxic shock syndrome Diseases 0.000 description 1
231100000650 Toxic shock syndrome Toxicity 0.000 description 1
229920004890 Triton X-100 Polymers 0.000 description 1
239000013504 Triton X-100 Substances 0.000 description 1
229940122618 Trypsin inhibitor Drugs 0.000 description 1
101710162629 Trypsin inhibitor Proteins 0.000 description 1
201000006704 Ulcerative Colitis Diseases 0.000 description 1
206010046851 Uveitis Diseases 0.000 description 1
208000001407 Vascular Headaches Diseases 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
201000000028 adult respiratory distress syndrome Diseases 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000001351 alkyl iodides Chemical class 0.000 description 1
125000006242 amine protecting group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 1
150000003927 aminopyridines Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
UKFWSNCTAHXBQN-UHFFFAOYSA-N ammonium iodide Chemical compound [NH4+].[I-] UKFWSNCTAHXBQN-UHFFFAOYSA-N 0.000 description 1
229940107816 ammonium iodide Drugs 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 description 1
229960003942 amphotericin b Drugs 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
208000002399 aphthous stomatitis Diseases 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
229960004405 aprotinin Drugs 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
235000009697 arginine Nutrition 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
239000002585 base Substances 0.000 description 1
AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 1
HQMRIBYCTLBDAK-UHFFFAOYSA-M bis(2-methylpropyl)alumanylium;chloride Chemical compound CC(C)C[Al](Cl)CC(C)C HQMRIBYCTLBDAK-UHFFFAOYSA-M 0.000 description 1
MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 1
206010006451 bronchitis Diseases 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
238000005277 cation exchange chromatography Methods 0.000 description 1
239000013592 cell lysate Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
230000003970 cerebral vascular damage Effects 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
208000016644 chronic atrophic gastritis Diseases 0.000 description 1
230000008602 contraction Effects 0.000 description 1
230000036461 convulsion Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000011262 co‐therapy Methods 0.000 description 1
239000013058 crude material Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
150000003950 cyclic amides Chemical class 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
125000002576 diazepinyl group Chemical class N1N=C(C=CC=C1)* 0.000 description 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N diisobutylaluminium hydride Substances CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
206010013663 drug dependence Diseases 0.000 description 1
230000002183 duodenal effect Effects 0.000 description 1
230000004064 dysfunction Effects 0.000 description 1
150000002084 enol ethers Chemical class 0.000 description 1
206010015037 epilepsy Diseases 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
208000022195 farmer lung disease Diseases 0.000 description 1
239000012091 fetal bovine serum Substances 0.000 description 1
FVTCRASFADXXNN-SCRDCRAPSA-N flavin mononucleotide Chemical compound OP(=O)(O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O FVTCRASFADXXNN-SCRDCRAPSA-N 0.000 description 1
229940013640 flavin mononucleotide Drugs 0.000 description 1
FVTCRASFADXXNN-UHFFFAOYSA-N flavin mononucleotide Natural products OP(=O)(O)OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O FVTCRASFADXXNN-UHFFFAOYSA-N 0.000 description 1
239000011768 flavin mononucleotide Substances 0.000 description 1
UQSQSQZYBQSBJZ-UHFFFAOYSA-M fluorosulfonate Chemical compound [O-]S(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-M 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000012737 fresh medium Substances 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
208000007565 gingivitis Diseases 0.000 description 1
239000008187 granular material Substances 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
229940037467 helicobacter pylori Drugs 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229940015607 hydro 40 Drugs 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
230000036543 hypotension Effects 0.000 description 1
208000009326 ileitis Diseases 0.000 description 1
210000003405 ileum Anatomy 0.000 description 1
210000000987 immune system Anatomy 0.000 description 1
230000001506 immunosuppresive effect Effects 0.000 description 1
238000011534 incubation Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
ZPNFWUPYTFPOJU-LPYSRVMUSA-N iniprol Chemical compound C([C@H]1C(=O)NCC(=O)NCC(=O)N[C@H]2CSSC[C@H]3C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(N[C@H](C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC=4C=CC=CC=4)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=4C=CC=CC=4)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC2=O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]2N(CCC2)C(=O)[C@@H](N)CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N2[C@@H](CCC2)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N2[C@@H](CCC2)C(=O)N3)C(=O)NCC(=O)NCC(=O)N[C@@H](C)C(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@H](C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H](C(=O)N1)C(C)C)[C@@H](C)O)[C@@H](C)CC)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 ZPNFWUPYTFPOJU-LPYSRVMUSA-N 0.000 description 1
208000014674 injury Diseases 0.000 description 1
229940047122 interleukins Drugs 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
230000007794 irritation Effects 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
150000002540 isothiocyanates Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
201000010901 lateral sclerosis Diseases 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
GDBQQVLCIARPGH-ULQDDVLXSA-N leupeptin Chemical compound CC(C)C[C@H](NC(C)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C=O)CCCN=C(N)N GDBQQVLCIARPGH-ULQDDVLXSA-N 0.000 description 1
108010052968 leupeptin Proteins 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000006166 lysate Substances 0.000 description 1
OVWYEQOVUDKZNU-UHFFFAOYSA-N m-tolualdehyde Chemical compound CC1=CC=CC(C=O)=C1 OVWYEQOVUDKZNU-UHFFFAOYSA-N 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
206010027599 migraine Diseases 0.000 description 1
208000005264 motor neuron disease Diseases 0.000 description 1
230000001537 neural effect Effects 0.000 description 1
230000004770 neurodegeneration Effects 0.000 description 1
208000015122 neurodegenerative disease Diseases 0.000 description 1
229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
SRGBVXWKCOEGJK-UHFFFAOYSA-N octane-1,2,7,8-tetramine Chemical compound NCC(N)CCCCC(N)CN SRGBVXWKCOEGJK-UHFFFAOYSA-N 0.000 description 1
229940127240 opiate Drugs 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
201000008482 osteoarthritis Diseases 0.000 description 1
GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229940056360 penicillin g Drugs 0.000 description 1
239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011148 porous material Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridine hydrochloride Substances [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000006340 racemization Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000004044 response Effects 0.000 description 1
235000019231 riboflavin-5'-phosphate Nutrition 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
FNKQXYHWGSIFBK-RPDRRWSUSA-N sapropterin Chemical compound N1=C(N)NC(=O)C2=C1NC[C@H]([C@@H](O)[C@@H](O)C)N2 FNKQXYHWGSIFBK-RPDRRWSUSA-N 0.000 description 1
229960004617 sapropterin Drugs 0.000 description 1
201000000980 schizophrenia Diseases 0.000 description 1
238000007790 scraping Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
208000019116 sleep disease Diseases 0.000 description 1
210000000813 small intestine Anatomy 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
210000000278 spinal cord Anatomy 0.000 description 1
208000020431 spinal cord injury Diseases 0.000 description 1
208000011117 substance-related disease Diseases 0.000 description 1
239000000758 substrate Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
GSXCEVHRIVLFJV-UHFFFAOYSA-N thiophene-3-carbonitrile Chemical compound N#CC=1C=CSC=1 GSXCEVHRIVLFJV-UHFFFAOYSA-N 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
BFCGWRVEKWHDGG-UHFFFAOYSA-N trimethyl(1,3-thiazol-5-yl)silane Chemical compound C[Si](C)(C)C1=CN=CS1 BFCGWRVEKWHDGG-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
239000002753 trypsin inhibitor Substances 0.000 description 1
230000002792 vascular Effects 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- 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]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Pulmonology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SK1346-98A 1996-04-13 1997-04-09 Aminoisoquinolines and aminothienopyridine derivatives and their use as anti-inflammatory agents SK134698A3 (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GBGB9607717.7A GB9607717D0 (en)	1996-04-13	1996-04-13	Pharmaceutically active comounds
GBGB9608678.0A GB9608678D0 (en)	1996-04-26	1996-04-26	Pharmaceuticlly active compounds
GBGB9610892.3A GB9610892D0 (en)	1996-05-24	1996-05-24	Pharmaceutically active compounds
PCT/SE1997/000589 WO1997038977A1 (en)	1996-04-13	1997-04-09	Aminoisoquinolines and aminothienopyridine derivatives and their use as anti-inflammatory agents

Publications (1)

Publication Number	Publication Date
SK134698A3 true SK134698A3 (en)	1999-06-11

Family

ID=27268241

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1346-98A SK134698A3 (en)	1996-04-13	1997-04-09	Aminoisoquinolines and aminothienopyridine derivatives and their use as anti-inflammatory agents

Country Status (21)

Country	Link
US (1)	US6063789A (es)
EP (1)	EP0892784A1 (es)
JP (1)	JP2000509028A (es)
KR (1)	KR20000005388A (es)
CN (1)	CN1221407A (es)
AR (1)	AR006619A1 (es)
AU (1)	AU706110B2 (es)
BR (1)	BR9708607A (es)
CA (1)	CA2251681A1 (es)
CZ (1)	CZ327698A3 (es)
EE (1)	EE9800339A (es)
HU (1)	HUP9901739A3 (es)
ID (1)	ID16575A (es)
IL (1)	IL126476A0 (es)
IS (1)	IS4862A (es)
NO (1)	NO984761L (es)
NZ (1)	NZ331932A (es)
PL (1)	PL329308A1 (es)
SK (1)	SK134698A3 (es)
TR (1)	TR199802060T2 (es)
WO (1)	WO1997038977A1 (es)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU8875398A (en)	1997-08-29	1999-03-22	Proteus Molecular Design Ltd	1-amino-7-isoquinoline derivatives as serine protease inhibitors
US6291425B1 (en)	1999-09-01	2001-09-18	Guilford Pharmaceuticals Inc.	Compounds, methods and pharmaceutical compositions for treating cellular damage, such as neural or cardiovascular tissue damage
AU9298098A (en) *	1997-09-03	1999-03-22	Guilford Pharmaceuticals Inc.	Amino-substituted compounds, methods, and compositions for inhibiting parp activity
EP1100789B1 (de)	1998-07-24	2005-02-09	Bayer CropScience AG	Substituierte benzoylcyclohexandione
IT1302677B1 (it)	1998-10-15	2000-09-29	Zambon Spa	Derivati benzazinici inibitori della fosfodiesterasi 4
TW575567B (en)	1998-10-23	2004-02-11	Akzo Nobel Nv	Serine protease inhibitor
SE9901530D0 (sv) *	1999-04-28	1999-04-28	Astra Pharma Prod	Novel compounds
DE19920791A1 (de)	1999-05-06	2000-11-09	Bayer Ag	Substituierte Benzoylisoxazole
DE19921424A1 (de)	1999-05-08	2000-11-09	Bayer Ag	Substituierte Benzoylketone
DE19946853A1 (de)	1999-09-30	2001-04-05	Bayer Ag	Substituierte Arylketone
TW591031B (en) *	2000-02-29	2004-06-11	Takeda Chemical Industries Ltd	Thienopyridine derivatives, their production and use
US7012098B2 (en) *	2001-03-23	2006-03-14	Pharmacia Corporation	Inhibitors of inducible nitric oxide synthase for chemoprevention and treatment of cancers
EP1942105B8 (en)	2005-10-25	2014-08-13	Shionogi&Co., Ltd.	Aminodihydrothiazine derivative
TW200804290A (en) *	2005-11-15	2008-01-16	Astrazeneca Ab	Compounds and uses thereof
WO2008133273A1 (ja)	2007-04-24	2008-11-06	Shionogi & Co., Ltd.	アルツハイマー症治療用医薬組成物
EP2147914B1 (en)	2007-04-24	2014-06-04	Shionogi&Co., Ltd.	Aminodihydrothiazine derivatives substituted with cyclic groups
CN102119161B (zh)	2008-06-13	2015-07-08	盐野义制药株式会社	具有β分泌酶抑制作用的含硫杂环衍生物
JPWO2010047372A1 (ja)	2008-10-22	2012-03-22	塩野義製薬株式会社	Ｂａｃｅ１阻害活性を有する２−アミノピリミジン−４−オンおよび２−アミノピリジン誘導体
MX2012006491A (es)	2009-12-11	2012-07-03	Shionogi & Co	Derivados de oxazina.
CN101863900B (zh) *	2010-06-29	2012-07-25	天津药物研究院	一氧化氮供体型噻吩并吡啶衍生物、其制备方法和用途
JP5766198B2 (ja)	2010-10-29	2015-08-19	塩野義製薬株式会社	縮合アミノジヒドロピリミジン誘導体
JP5816630B2 (ja)	2010-10-29	2015-11-18	塩野義製薬株式会社	ナフチリジン誘導体
WO2012147763A1 (ja)	2011-04-26	2012-11-01	塩野義製薬株式会社	オキサジン誘導体およびそれを含有するｂａｃｅ１阻害剤
US9540359B2 (en)	2012-10-24	2017-01-10	Shionogi & Co., Ltd.	Dihydrooxazine or oxazepine derivatives having BACE1 inhibitory activity

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3663550A (en) *	1968-12-25	1972-05-16	Shionogi & Co	2-lower alkyl-2,3-dihydrothieno(3,2-c)quinoline oxides
US3903095A (en) *	1972-02-18	1975-09-02	Merck & Co Inc	Certain substituted-thieno{8 3,2-c{9 -pyridines
GB1379111A (en) *	1972-04-13	1975-01-02	Aspro Nicholas Ltd	Preparation of fused-ring pyridine and pyrazine derivatives
US4127720A (en) *	1977-09-21	1978-11-28	Bristol-Myers Company	Pyrimido[2,1-a]isoquinoline derivatives having antiallergy activity
JPH04348326A (ja) *	1990-07-09	1992-12-03	Sumitomo Electric Ind Ltd	有機非線形光学材料
KR100342275B1 (ko) *	1993-10-21	2002-12-05	지.디. 썰 엘엘씨	산화질소신타제저해제로서유용한아미디노유도체

1997
- 1997-04-09 EP EP97918449A patent/EP0892784A1/en not_active Withdrawn
- 1997-04-09 SK SK1346-98A patent/SK134698A3/sk unknown
- 1997-04-09 EE EE9800339A patent/EE9800339A/xx unknown
- 1997-04-09 NZ NZ331932A patent/NZ331932A/en unknown
- 1997-04-09 AU AU26550/97A patent/AU706110B2/en not_active Ceased
- 1997-04-09 KR KR1019980708115A patent/KR20000005388A/ko not_active Withdrawn
- 1997-04-09 US US08/894,448 patent/US6063789A/en not_active Expired - Fee Related
- 1997-04-09 IL IL12647697A patent/IL126476A0/xx unknown
- 1997-04-09 TR TR1998/02060T patent/TR199802060T2/xx unknown
- 1997-04-09 CN CN97195337A patent/CN1221407A/zh active Pending
- 1997-04-09 BR BR9708607A patent/BR9708607A/pt unknown
- 1997-04-09 PL PL97329308A patent/PL329308A1/xx unknown
- 1997-04-09 WO PCT/SE1997/000589 patent/WO1997038977A1/en not_active Ceased
- 1997-04-09 CZ CZ983276A patent/CZ327698A3/cs unknown
- 1997-04-09 HU HU9901739A patent/HUP9901739A3/hu unknown
- 1997-04-09 CA CA002251681A patent/CA2251681A1/en not_active Abandoned
- 1997-04-09 JP JP9537011A patent/JP2000509028A/ja active Pending
- 1997-04-11 AR ARP970101464A patent/AR006619A1/es not_active Application Discontinuation
- 1997-04-14 ID IDP971239A patent/ID16575A/id unknown
1998
- 1998-10-07 IS IS4862A patent/IS4862A/is unknown
- 1998-10-12 NO NO984761A patent/NO984761L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
IS4862A (is)	1998-10-07
TR199802060T2 (xx)	1999-01-18
KR20000005388A (ko)	2000-01-25
BR9708607A (pt)	1999-08-03
NZ331932A (en)	2000-02-28
PL329308A1 (en)	1999-03-15
CN1221407A (zh)	1999-06-30
AU706110B2 (en)	1999-06-10
US6063789A (en)	2000-05-16
NO984761D0 (no)	1998-10-12
IL126476A0 (en)	1999-08-17
EP0892784A1 (en)	1999-01-27
EE9800339A (et)	1999-04-15
WO1997038977A1 (en)	1997-10-23
HUP9901739A3 (en)	2000-06-28
CA2251681A1 (en)	1997-10-23
JP2000509028A (ja)	2000-07-18
AU2655097A (en)	1997-11-07
HUP9901739A2 (hu)	1999-09-28
NO984761L (no)	1998-12-14
CZ327698A3 (cs)	1999-05-12
AR006619A1 (es)	1999-09-08
ID16575A (id)	1997-10-16

Publication	Publication Date	Title
SK134698A3 (en)	1999-06-11	Aminoisoquinolines and aminothienopyridine derivatives and their use as anti-inflammatory agents
EP1971611B1 (en)	2012-10-10	Anti-viral compounds
US6303613B1 (en)	2001-10-16	Aminopyrimidine derivatives, processes for their preparation, compositions containing them and their use as pharmaceuticals
CA2235304A1 (en)	1997-04-24	Pharmaceutically active quinazoline compounds
CS264266B2 (en)	1989-06-13	Process for preparing derivatives of purine
MX2011003968A (es)	2011-05-23	Aminas y sulfoxidos de tieno [2,3-d]pirimidina y su uso como antagonistas del receptor de adenosina a2a.
RU2441010C2 (ru)	2012-01-27	Противовирусные соединения
CA2294734A1 (en)	1999-01-14	Compounds
US6100246A (en)	2000-08-08	Spiro-piperidine derivatives as inhibitors of nitric oxide synthase
EP4514808B1 (en)	2025-12-17	Compositions useful for modulating splicing
MXPA98008153A (es)	1999-09-20	Derivados de aminoisoquinolinas y aminotienopiridinas y su uso como agentes antiinflamatorios
MX2011003961A (es)	2011-05-03	Tieno[2,3-d]pirimidinas sustituidas con fenilo y heteroarilo y su uso como antagonistas de receptores de adenosina a2a.
MX2008008161A (es)	2008-10-03	Compuestos anti-virales
HK1121765B (en)	2013-05-03	Anti-viral compounds
HK1160133A (en)	2012-08-10	Antiviral compounds
EP2345652A1 (en)	2011-07-20	Antiviral compounds
CZ367499A3 (cs)	2000-02-16	Sloučeniny
MXPA99011983A (es)	2000-09-04	Derivados de quinazolina de aminoespiropiperidina