CA2352045A1 - Substituted benzo[de]isoquinoline-1,3-diones - Google Patents
Substituted benzo[de]isoquinoline-1,3-diones Download PDFInfo
- Publication number
- CA2352045A1 CA2352045A1 CA002352045A CA2352045A CA2352045A1 CA 2352045 A1 CA2352045 A1 CA 2352045A1 CA 002352045 A CA002352045 A CA 002352045A CA 2352045 A CA2352045 A CA 2352045A CA 2352045 A1 CA2352045 A1 CA 2352045A1
- Authority
- CA
- Canada
- Prior art keywords
- chz
- conh
- nhz
- phenyl
- benzo
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical class C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 148
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 239000012453 solvate Substances 0.000 claims abstract description 17
- 239000005557 antagonist Substances 0.000 claims abstract description 8
- 102000003886 Glycoproteins Human genes 0.000 claims abstract description 6
- 108090000288 Glycoproteins Proteins 0.000 claims abstract description 6
- -1 pyrazol-4-yl Chemical group 0.000 claims description 309
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 152
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
- 229910052717 sulfur Inorganic materials 0.000 claims description 29
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 25
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 208000007536 Thrombosis Diseases 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 9
- 229940080818 propionamide Drugs 0.000 claims description 9
- 150000003254 radicals Chemical class 0.000 claims description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 125000004957 naphthylene group Chemical group 0.000 claims description 5
- VKHWCSUSDNUMGL-UHFFFAOYSA-N 6-(3-aminopropylamino)-2-(4-carbazol-9-ylphenyl)benzo[de]isoquinoline-1,3-dione Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C(C=C1)=CC=C1N(C1=O)C(=O)C2=CC=C(NCCCN)C3=C2C1=CC=C3 VKHWCSUSDNUMGL-UHFFFAOYSA-N 0.000 claims description 4
- ZEXVKHBNFJZYRP-UHFFFAOYSA-N 6-(3-aminopropylamino)-2-[4-(4-methoxyphenyl)phenyl]benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N2C(C=3C=CC(NCCCN)=C4C=CC=C(C=34)C2=O)=O)C=C1 ZEXVKHBNFJZYRP-UHFFFAOYSA-N 0.000 claims description 4
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 4
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 4
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims description 3
- 206010002383 Angina Pectoris Diseases 0.000 claims description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- 206010038563 Reocclusion Diseases 0.000 claims description 3
- 208000006011 Stroke Diseases 0.000 claims description 3
- 208000032109 Transient ischaemic attack Diseases 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 238000002399 angioplasty Methods 0.000 claims description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 230000000181 anti-adherent effect Effects 0.000 claims description 3
- 150000001499 aryl bromides Chemical class 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 3
- 239000007943 implant Substances 0.000 claims description 3
- 238000002513 implantation Methods 0.000 claims description 3
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 208000010125 myocardial infarction Diseases 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 230000002093 peripheral effect Effects 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 238000011321 prophylaxis Methods 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 208000037803 restenosis Diseases 0.000 claims description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 3
- CHWFVJRKVULOKZ-UHFFFAOYSA-N 2-[[3-[[[2-[4-(4-methoxyphenyl)phenyl]-1,3-dioxobenzo[de]isoquinolin-6-yl]amino]methyl]phenyl]methyl]guanidine Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N2C(C=3C=CC(NCC=4C=C(CN=C(N)N)C=CC=4)=C4C=CC=C(C=34)C2=O)=O)C=C1 CHWFVJRKVULOKZ-UHFFFAOYSA-N 0.000 claims description 2
- JZLUZCGYTSGWFH-UHFFFAOYSA-N 3-[3-[6-[2-(diaminomethylideneamino)ethylamino]-1,3-dioxobenzo[de]isoquinolin-2-yl]phenyl]-n-(4-phenylbutyl)propanamide Chemical compound O=C1C(C2=3)=CC=CC=3C(NCCN=C(N)N)=CC=C2C(=O)N1C(C=1)=CC=CC=1CCC(=O)NCCCCC1=CC=CC=C1 JZLUZCGYTSGWFH-UHFFFAOYSA-N 0.000 claims description 2
- IIJYGVDBNLSICR-UHFFFAOYSA-N 3-[3-[6-[[4-[(diaminomethylideneamino)methyl]phenyl]methylamino]-1,3-dioxobenzo[de]isoquinolin-2-yl]phenyl]-n-[2-(4-sulfamoylphenyl)ethyl]propanamide Chemical compound C1=CC(CN=C(N)N)=CC=C1CNC1=CC=C2C3=C1C=CC=C3C(=O)N(C=1C=C(CCC(=O)NCCC=3C=CC(=CC=3)S(N)(=O)=O)C=CC=1)C2=O IIJYGVDBNLSICR-UHFFFAOYSA-N 0.000 claims description 2
- QNOKUJOULCMTPE-UHFFFAOYSA-N 6-(3-aminopropylamino)-2-(2,3-dimethoxyphenyl)benzo[de]isoquinoline-1,3-dione Chemical compound COC1=CC=CC(N2C(C=3C=CC(NCCCN)=C4C=CC=C(C=34)C2=O)=O)=C1OC QNOKUJOULCMTPE-UHFFFAOYSA-N 0.000 claims description 2
- VQXVNJFSQKAWNS-UHFFFAOYSA-N 6-(3-aminopropylamino)-2-(3,4,5-trimethoxyphenyl)benzo[de]isoquinoline-1,3-dione Chemical compound COC1=C(OC)C(OC)=CC(N2C(C=3C=CC(NCCCN)=C4C=CC=C(C=34)C2=O)=O)=C1 VQXVNJFSQKAWNS-UHFFFAOYSA-N 0.000 claims description 2
- LCJLRTACSNAUGF-UHFFFAOYSA-N 6-(3-aminopropylamino)-2-(7-hydroxynaphthalen-1-yl)benzo[de]isoquinoline-1,3-dione Chemical compound C1=C(O)C=C2C(N3C(=O)C4=CC=C(C=5C=CC=C(C4=5)C3=O)NCCCN)=CC=CC2=C1 LCJLRTACSNAUGF-UHFFFAOYSA-N 0.000 claims description 2
- RZUMCJLNXRHEMC-UHFFFAOYSA-N NCCCNC1=CC=C2C3=C1C(N(C(C3=CC=C2)=O)C2=C(C(=CC=C2C#N)OC)OC)=O Chemical compound NCCCNC1=CC=C2C3=C1C(N(C(C3=CC=C2)=O)C2=C(C(=CC=C2C#N)OC)OC)=O RZUMCJLNXRHEMC-UHFFFAOYSA-N 0.000 claims description 2
- LFSSPMJJZJBEHV-UHFFFAOYSA-N NCCCNC=1C=CC=2C(N(C(C3=CC=CC=1C=23)=O)C1=CC(=C(C=C1)C1=CC=C(C=C1)O)C)=O Chemical compound NCCCNC=1C=CC=2C(N(C(C3=CC=CC=1C=23)=O)C1=CC(=C(C=C1)C1=CC=C(C=C1)O)C)=O LFSSPMJJZJBEHV-UHFFFAOYSA-N 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 125000005620 boronic acid group Chemical class 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 238000005661 deetherification reaction Methods 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- MTJKHMLLZIZOFC-UHFFFAOYSA-N n-[2-(3-chlorophenyl)ethyl]-3-[3-[6-[[4-[(diaminomethylideneamino)methyl]cyclohexyl]methylamino]-1,3-dioxobenzo[de]isoquinolin-2-yl]phenyl]propanamide Chemical compound C1CC(CN=C(N)N)CCC1CNC1=CC=C2C3=C1C=CC=C3C(=O)N(C=1C=C(CCC(=O)NCCC=3C=C(Cl)C=CC=3)C=CC=1)C2=O MTJKHMLLZIZOFC-UHFFFAOYSA-N 0.000 claims description 2
- JXMVOTAZKZTZLL-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethyl]-3-[3-[6-[[4-[(diaminomethylideneamino)methyl]cyclohexyl]methylamino]-1,3-dioxobenzo[de]isoquinolin-2-yl]phenyl]propanamide Chemical compound C1CC(CN=C(N)N)CCC1CNC1=CC=C2C3=C1C=CC=C3C(=O)N(C=1C=C(CCC(=O)NCCC=3C=CC(Cl)=CC=3)C=CC=1)C2=O JXMVOTAZKZTZLL-UHFFFAOYSA-N 0.000 claims description 2
- BLQQCHMXQDLWCV-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethyl]-3-[3-[6-[[4-[(diaminomethylideneamino)methyl]phenyl]methylamino]-1,3-dioxobenzo[de]isoquinolin-2-yl]phenyl]propanamide Chemical compound C1=CC(CN=C(N)N)=CC=C1CNC1=CC=C2C3=C1C=CC=C3C(=O)N(C=1C=C(CCC(=O)NCCC=3C=CC(Cl)=CC=3)C=CC=1)C2=O BLQQCHMXQDLWCV-UHFFFAOYSA-N 0.000 claims description 2
- 230000000269 nucleophilic effect Effects 0.000 claims description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000004962 sulfoxyl group Chemical group 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 229910006074 SO2NH2 Inorganic materials 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 2
- CBSLBDYWSHOIER-UHFFFAOYSA-N C(C1=CC=CC=C1)NC=1C=CC2C(N(C(C3=CC=CC=1C23)=O)C1=C(C=CC(=C1)Cl)Cl)=O Chemical compound C(C1=CC=CC=C1)NC=1C=CC2C(N(C(C3=CC=CC=1C23)=O)C1=C(C=CC(=C1)Cl)Cl)=O CBSLBDYWSHOIER-UHFFFAOYSA-N 0.000 claims 1
- ALDVNYGMHFYXSI-UHFFFAOYSA-N N(C(=N)N)C(CNC=1C=CC2C(N(C(C3=CC=CC=1C23)=O)C=1C=C(C=CC=1)CCC(=O)NCCC1=CC=C(C=C1)C)=O)C Chemical compound N(C(=N)N)C(CNC=1C=CC2C(N(C(C3=CC=CC=1C23)=O)C=1C=C(C=CC=1)CCC(=O)NCCC1=CC=C(C=C1)C)=O)C ALDVNYGMHFYXSI-UHFFFAOYSA-N 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical group Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 claims 1
- 238000007336 electrophilic substitution reaction Methods 0.000 claims 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
- 238000011282 treatment Methods 0.000 claims 1
- 238000004949 mass spectrometry Methods 0.000 description 74
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 54
- LKOZHLXUWUBRDK-UHFFFAOYSA-N 4-nitro-1,8-naphthalic anhydride Chemical compound O=C1OC(=O)C2=CC=CC3=C2C1=CC=C3[N+](=O)[O-] LKOZHLXUWUBRDK-UHFFFAOYSA-N 0.000 description 50
- 229910052739 hydrogen Inorganic materials 0.000 description 42
- 125000006239 protecting group Chemical group 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- QFNFDHNZVTWZED-UHFFFAOYSA-N tert-butyl n-[[(2-methylpropan-2-yl)oxycarbonylamino]-pyrazol-1-ylmethylidene]carbamate Chemical compound CC(C)(C)OC(=O)NC(=NC(=O)OC(C)(C)C)N1C=CC=N1 QFNFDHNZVTWZED-UHFFFAOYSA-N 0.000 description 34
- UJEUBSWHCGDJQU-UHFFFAOYSA-N 4-chloro-1,8-naphthalic anhydride Chemical compound O=C1OC(=O)C2=CC=CC3=C2C1=CC=C3Cl UJEUBSWHCGDJQU-UHFFFAOYSA-N 0.000 description 24
- 150000004985 diamines Chemical class 0.000 description 24
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 10
- 125000003282 alkyl amino group Chemical group 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- 239000012442 inert solvent Substances 0.000 description 9
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 9
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000005916 2-methylpentyl group Chemical group 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- VLVCDUSVTXIWGW-UHFFFAOYSA-N 4-iodoaniline Chemical compound NC1=CC=C(I)C=C1 VLVCDUSVTXIWGW-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000004663 dialkyl amino group Chemical group 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 125000000565 sulfonamide group Chemical group 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
- 230000002792 vascular Effects 0.000 description 5
- 229910052727 yttrium Inorganic materials 0.000 description 5
- JGYSBUTWKGTFRU-UHFFFAOYSA-N 2-(4-iodophenyl)-6-nitrobenzo[de]isoquinoline-1,3-dione Chemical compound O=C1C(C2=3)=CC=CC=3C([N+](=O)[O-])=CC=C2C(=O)N1C1=CC=C(I)C=C1 JGYSBUTWKGTFRU-UHFFFAOYSA-N 0.000 description 4
- FFCSRWGYGMRBGD-UHFFFAOYSA-N 3-iodoaniline Chemical compound NC1=CC=CC(I)=C1 FFCSRWGYGMRBGD-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 102000019997 adhesion receptor Human genes 0.000 description 4
- 108010013985 adhesion receptor Proteins 0.000 description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19941398A | 1998-11-25 | 1998-11-25 | |
| US09/199,413 | 1998-11-25 | ||
| US39878399A | 1999-09-20 | 1999-09-20 | |
| US09/398,783 | 1999-09-20 | ||
| PCT/EP1999/008561 WO2000032577A2 (en) | 1998-11-25 | 1999-11-09 | Substituted benzo[de]isoquinoline-1,3-diones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2352045A1 true CA2352045A1 (en) | 2000-06-08 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002352045A Abandoned CA2352045A1 (en) | 1998-11-25 | 1999-11-09 | Substituted benzo[de]isoquinoline-1,3-diones |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP1144381A2 (xx) |
| JP (1) | JP2002537225A (xx) |
| KR (1) | KR20010080569A (xx) |
| CN (1) | CN1330638A (xx) |
| AU (1) | AU760136B2 (xx) |
| BR (1) | BR9915648A (xx) |
| CA (1) | CA2352045A1 (xx) |
| CZ (1) | CZ20011782A3 (xx) |
| HU (1) | HUP0104520A3 (xx) |
| ID (1) | ID28982A (xx) |
| NO (1) | NO20012544L (xx) |
| PL (1) | PL348204A1 (xx) |
| SK (1) | SK7022001A3 (xx) |
| TW (1) | TW473474B (xx) |
| WO (1) | WO2000032577A2 (xx) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998007421A1 (fr) * | 1996-08-16 | 1998-02-26 | Ishihara Sangyo Kaisha, Ltd. | Composition medicinale |
| EP1088821A1 (en) * | 1999-09-28 | 2001-04-04 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active sulfonamide derivatives |
| US7547716B2 (en) | 2001-06-08 | 2009-06-16 | Institute Of Medicinal Molecular Design, Inc. | Sulfonamide derivatives |
| US6693198B2 (en) * | 2002-04-22 | 2004-02-17 | Xanthus Life Sciences, Inc. | Amonafide salts |
| US8097725B2 (en) * | 2004-12-03 | 2012-01-17 | Roche Diagnostics Operations, Inc. | Luminescent indicator dye and optical sensor |
| FR2915685A1 (fr) * | 2007-05-02 | 2008-11-07 | Thales Sa | Compose fluorescent a l'etat solide dans l'eau,procede de synthese et utilisation dans des capteurs |
| WO2014149198A1 (en) * | 2013-03-15 | 2014-09-25 | Alumend, Llc | Compositions and methods of using the compositions for plaque softening |
| CN107417616A (zh) * | 2013-05-01 | 2017-12-01 | 中央研究院 | 治疗β‑地中海贫血和镰状细胞病的方法和组合物 |
| CN103450176B (zh) * | 2013-08-15 | 2016-07-06 | 大连理工大学 | 一类含2-（4-氨基苯基）苯并噻唑萘酰亚胺化合物及其应用 |
| CN107087409B (zh) * | 2014-09-19 | 2020-07-31 | 吕衍达 | 苯并杂环化合物及其应用 |
| CN106905237B (zh) * | 2017-02-08 | 2019-05-14 | 上海师范大学 | 一种pH和乏氧双响应定位肿瘤细胞的萘酰亚胺类比率荧光探针及其合成方法 |
| CN110283123B (zh) * | 2019-07-08 | 2022-06-17 | 桂林医学院 | 4-对甲苯磺酰基哌嗪-3-硝基-1,8-萘酰亚胺衍生物及其合成方法和应用 |
| CN110272388B (zh) * | 2019-07-08 | 2022-06-17 | 桂林医学院 | 4-二硫代甲酸哌嗪-3-硝基-1,8-萘酰亚胺衍生物及其合成方法和应用 |
| CN110407865B (zh) * | 2019-08-02 | 2022-04-15 | 山东师范大学 | 基于苯磺酰胺结构的式（i）化合物及其制备方法与应用 |
| CN111518075B (zh) * | 2020-04-17 | 2023-03-28 | 西南大学 | 萘酰亚胺哌嗪三唑类化合物及其制备方法和应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2423546C2 (de) * | 1974-05-15 | 1983-01-27 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von 4-Amino-1,8- naphthalsäure-N-arylimid-Verbindungen |
| ES459497A1 (es) * | 1977-06-04 | 1978-04-16 | Made Labor Sa | Un metodo para la preparacion industrial de naftalimidas y sus derivados. |
| DE3635711A1 (de) * | 1986-10-21 | 1988-04-28 | Knoll Ag | 5-nitrobenzo(de)isochinolin-1,3-dione, ihre herstellung und verwendung |
| KR20000052691A (ko) * | 1996-10-21 | 2000-08-25 | 스트라칸 그라함 | 뉴로트로핀 길항제 조성물 |
| WO1998018764A1 (de) * | 1996-10-28 | 1998-05-07 | Merck Patent Gmbh | Dihydrobenzoanthracenone, -pyrimidinone oder dihydronaphthochinolinone |
-
1999
- 1999-11-09 AU AU26603/00A patent/AU760136B2/en not_active Ceased
- 1999-11-09 BR BR9915648-2A patent/BR9915648A/pt not_active IP Right Cessation
- 1999-11-09 KR KR1020017006547A patent/KR20010080569A/ko not_active Application Discontinuation
- 1999-11-09 CN CN99813687A patent/CN1330638A/zh active Pending
- 1999-11-09 CZ CZ20011782A patent/CZ20011782A3/cs unknown
- 1999-11-09 ID IDW00200101392A patent/ID28982A/id unknown
- 1999-11-09 WO PCT/EP1999/008561 patent/WO2000032577A2/en not_active Application Discontinuation
- 1999-11-09 JP JP2000585219A patent/JP2002537225A/ja active Pending
- 1999-11-09 CA CA002352045A patent/CA2352045A1/en not_active Abandoned
- 1999-11-09 EP EP99968783A patent/EP1144381A2/en not_active Withdrawn
- 1999-11-09 SK SK702-2001A patent/SK7022001A3/sk unknown
- 1999-11-09 PL PL99348204A patent/PL348204A1/xx unknown
- 1999-11-09 HU HU0104520A patent/HUP0104520A3/hu unknown
- 1999-11-24 TW TW088120540A patent/TW473474B/zh not_active IP Right Cessation
-
2001
- 2001-05-23 NO NO20012544A patent/NO20012544L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20010080569A (ko) | 2001-08-22 |
| NO20012544D0 (no) | 2001-05-23 |
| ID28982A (id) | 2001-07-19 |
| TW473474B (en) | 2002-01-21 |
| PL348204A1 (en) | 2002-05-06 |
| WO2000032577A2 (en) | 2000-06-08 |
| HUP0104520A3 (en) | 2002-10-28 |
| AU760136B2 (en) | 2003-05-08 |
| HUP0104520A2 (hu) | 2002-04-29 |
| AU2660300A (en) | 2000-06-19 |
| JP2002537225A (ja) | 2002-11-05 |
| CZ20011782A3 (cs) | 2001-09-12 |
| CN1330638A (zh) | 2002-01-09 |
| BR9915648A (pt) | 2001-08-14 |
| SK7022001A3 (en) | 2002-09-10 |
| NO20012544L (no) | 2001-05-23 |
| WO2000032577A3 (en) | 2000-09-21 |
| EP1144381A2 (en) | 2001-10-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |