NO314304B1 - Isokinoloner og fremgangsmåte for fremstilling derav - Google Patents

Isokinoloner og fremgangsmåte for fremstilling derav Download PDF

Info

Publication number: NO314304B1
Authority: NO; Norway
Prior art keywords: dione; benzo; isoquinoline; hydroxy; mmol
Prior art date: 1996-11-01

Application number

NO19992104A

Other languages

English (en)

Norwegian (no)

Other versions

NO992104D0 (no

NO992104L (no

Inventor

Albert Kudzoi Amegadzie

Maureen Elizabeth Carey

John Michael Domagala

Liren Huang

Ronald George Micetich

Rajeshwar Singh

Michael Andrew Stier

Arkadii Vaisburg

Joseph Peter Sanchez

Original Assignee

Warner Lambert Co

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.)

1996-11-01

Filing date

1999-04-30

Publication date

2003-03-03

1999-04-30 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

1999-04-30 Publication of NO992104D0 publication Critical patent/NO992104D0/no

1999-04-30 Publication of NO992104L publication Critical patent/NO992104L/no

2003-03-03 Publication of NO314304B1 publication Critical patent/NO314304B1/no

Links

238000000034 method Methods 0.000 title description 92
238000002360 preparation method Methods 0.000 title description 15
VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical class C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 title description 2
230000008569 process Effects 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 289
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 48
238000006243 chemical reaction Methods 0.000 claims description 48
-1 4-aminopiperidin-1-yl Chemical group 0.000 claims description 40
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 36
229910052739 hydrogen Inorganic materials 0.000 claims description 30
125000000623 heterocyclic group Chemical group 0.000 claims description 28
229910052794 bromium Inorganic materials 0.000 claims description 25
239000001257 hydrogen Substances 0.000 claims description 22
239000000460 chlorine Substances 0.000 claims description 20
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 17
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 16
229910052801 chlorine Inorganic materials 0.000 claims description 16
229910052757 nitrogen Inorganic materials 0.000 claims description 16
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
229910052731 fluorine Inorganic materials 0.000 claims description 15
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
125000006239 protecting group Chemical group 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
125000005842 heteroatom Chemical group 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000002757 morpholinyl group Chemical group 0.000 claims description 8
125000004193 piperazinyl group Chemical group 0.000 claims description 8
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
125000003386 piperidinyl group Chemical group 0.000 claims description 6
125000004568 thiomorpholinyl group Chemical group 0.000 claims description 6
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
VCNMFLKYEGUCKM-UHFFFAOYSA-N 2-hydroxy-5-methoxy-6-(4-methylpiperazin-1-yl)benzo[de]isoquinoline-1,3-dione Chemical compound COC1=CC(=C23)C(=O)N(O)C(=O)C3=CC=CC2=C1N1CCN(C)CC1 VCNMFLKYEGUCKM-UHFFFAOYSA-N 0.000 claims description 4
DWUBPAASNUUBCU-UHFFFAOYSA-N 2-hydroxy-6-piperidin-1-ylbenzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(=C23)C(=O)N(O)C(=O)C2=CC=CC3=C1N1CCCCC1 DWUBPAASNUUBCU-UHFFFAOYSA-N 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
IDZVLKHXQYTTOG-UHFFFAOYSA-N 2,5-dihydroxy-4-methyl-6-piperidin-1-ylbenzo[de]isoquinoline-1,3-dione Chemical compound C=12C=3C=CC=C2C(=O)N(O)C(=O)C=1C(C)=C(O)C=3N1CCCCC1 IDZVLKHXQYTTOG-UHFFFAOYSA-N 0.000 claims description 3
LAKUFAAPCUJNPX-UHFFFAOYSA-N 2-hydroxy-1,3-dioxo-6-pyrrolidin-1-ylbenzo[de]isoquinoline-5-carbonitrile Chemical compound N#CC1=CC(=C23)C(=O)N(O)C(=O)C2=CC=CC3=C1N1CCCC1 LAKUFAAPCUJNPX-UHFFFAOYSA-N 0.000 claims description 3
UGJDLNPCBHXMOA-UHFFFAOYSA-N 2-hydroxy-5-nitro-7-pyrrolidin-1-ylbenzo[de]isoquinoline-1,3-dione Chemical compound C=12C3=CC([N+]([O-])=O)=CC=1C(=O)N(O)C(=O)C2=CC=C3N1CCCC1 UGJDLNPCBHXMOA-UHFFFAOYSA-N 0.000 claims description 3
DQEDYLYGNXBYEL-UHFFFAOYSA-N 2-hydroxy-6-pyrrolidin-1-ylbenzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(=C23)C(=O)N(O)C(=O)C2=CC=CC3=C1N1CCCC1 DQEDYLYGNXBYEL-UHFFFAOYSA-N 0.000 claims description 3
KFLBGPGBDPQKHA-UHFFFAOYSA-N 5,6-dichloro-2-hydroxy-7-pyrrolidin-1-ylbenzo[de]isoquinoline-1,3-dione Chemical compound C=12C3=C(Cl)C(Cl)=CC=1C(=O)N(O)C(=O)C2=CC=C3N1CCCC1 KFLBGPGBDPQKHA-UHFFFAOYSA-N 0.000 claims description 3
PXAQYRGXLYOJMD-UHFFFAOYSA-N 5-amino-2-hydroxy-6-pyrrolidin-1-ylbenzo[de]isoquinoline-1,3-dione Chemical compound NC1=CC(=C23)C(=O)N(O)C(=O)C3=CC=CC2=C1N1CCCC1 PXAQYRGXLYOJMD-UHFFFAOYSA-N 0.000 claims description 3
NNTARCMWJIHGAU-UHFFFAOYSA-N 5-bromo-2-hydroxy-6-(3-methylpiperidin-1-yl)benzo[de]isoquinoline-1,3-dione Chemical compound C1C(C)CCCN1C1=C(Br)C=C2C3=C1C=CC=C3C(=O)N(O)C2=O NNTARCMWJIHGAU-UHFFFAOYSA-N 0.000 claims description 3
GWXFJYZUOJYIKL-UHFFFAOYSA-N 5-bromo-2-hydroxy-6-(4-methylpiperazin-1-yl)benzo[de]isoquinoline-1,3-dione Chemical compound C1CN(C)CCN1C1=C(Br)C=C2C3=C1C=CC=C3C(=O)N(O)C2=O GWXFJYZUOJYIKL-UHFFFAOYSA-N 0.000 claims description 3
PKACYCVWDJAOII-UHFFFAOYSA-N 5-bromo-2-hydroxy-6-piperidin-1-ylbenzo[de]isoquinoline-1,3-dione Chemical compound BrC1=CC(=C23)C(=O)N(O)C(=O)C2=CC=CC3=C1N1CCCCC1 PKACYCVWDJAOII-UHFFFAOYSA-N 0.000 claims description 3
150000001298 alcohols Chemical class 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 3
SURCGQGDUADKBL-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-5-nitrobenzo[de]isoquinoline-1,3-dione Chemical compound [O-][N+](=O)C1=CC(C(N(NCCO)C2=O)=O)=C3C2=CC=CC3=C1 SURCGQGDUADKBL-UHFFFAOYSA-N 0.000 claims description 2
FWFSQTLRNHWDCI-UHFFFAOYSA-N 2-hydroxy-1,3-dioxo-6-piperidin-1-ylbenzo[de]isoquinoline-5-carbonitrile Chemical compound N#CC1=CC(=C23)C(=O)N(O)C(=O)C2=CC=CC3=C1N1CCCCC1 FWFSQTLRNHWDCI-UHFFFAOYSA-N 0.000 claims description 2
CPMFJQQUQBZYRL-UHFFFAOYSA-N 2-hydroxy-5,8-dinitro-6-pyrrolidin-1-ylbenzo[de]isoquinoline-1,3-dione Chemical compound [O-][N+](=O)C1=CC(=C23)C(=O)N(O)C(=O)C2=CC([N+]([O-])=O)=CC3=C1N1CCCC1 CPMFJQQUQBZYRL-UHFFFAOYSA-N 0.000 claims description 2
CFGXDQWLLZACHI-UHFFFAOYSA-N 2-hydroxy-5-methoxy-6-morpholin-4-ylbenzo[de]isoquinoline-1,3-dione Chemical compound COC1=CC(=C23)C(=O)N(O)C(=O)C3=CC=CC2=C1N1CCOCC1 CFGXDQWLLZACHI-UHFFFAOYSA-N 0.000 claims description 2
IMHJUABQUNHEMK-UHFFFAOYSA-N 2-hydroxy-5-methoxy-7-pyrrolidin-1-ylbenzo[de]isoquinoline-1,3-dione Chemical compound C1=2C3=CC(OC)=CC=2C(=O)N(O)C(=O)C1=CC=C3N1CCCC1 IMHJUABQUNHEMK-UHFFFAOYSA-N 0.000 claims description 2
JPUIXQUVMINRFJ-UHFFFAOYSA-N 2-hydroxy-5-nitro-6-pyrrolidin-1-ylbenzo[de]isoquinoline-1,3-dione Chemical compound [O-][N+](=O)C1=CC(=C23)C(=O)N(O)C(=O)C2=CC=CC3=C1N1CCCC1 JPUIXQUVMINRFJ-UHFFFAOYSA-N 0.000 claims description 2
OUDNMYOPYPGBOD-UHFFFAOYSA-N 2-hydroxy-6-(4-methylpiperazin-1-yl)benzo[de]isoquinoline-1,3-dione Chemical compound C1CN(C)CCN1C1=CC=C2C3=C1C=CC=C3C(=O)N(O)C2=O OUDNMYOPYPGBOD-UHFFFAOYSA-N 0.000 claims description 2
HXRJLYQLUFXROP-UHFFFAOYSA-N 2-hydroxy-6-morpholin-4-ylbenzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(=C23)C(=O)N(O)C(=O)C2=CC=CC3=C1N1CCOCC1 HXRJLYQLUFXROP-UHFFFAOYSA-N 0.000 claims description 2
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
KUFPJTLNHJRYJE-UHFFFAOYSA-N 5-bromo-2-hydroxy-6-pyrrolidin-1-ylbenzo[de]isoquinoline-1,3-dione Chemical compound BrC1=CC(=C23)C(=O)N(O)C(=O)C2=CC=CC3=C1N1CCCC1 KUFPJTLNHJRYJE-UHFFFAOYSA-N 0.000 claims description 2
LKSHJTJDRCAWEU-UHFFFAOYSA-N 5-chloro-2-hydroxy-6-(3-methoxypyrrolidin-1-yl)benzo[de]isoquinoline-1,3-dione Chemical compound C1C(OC)CCN1C1=C(Cl)C=C2C3=C1C=CC=C3C(=O)N(O)C2=O LKSHJTJDRCAWEU-UHFFFAOYSA-N 0.000 claims description 2
HVCIKRLEWIFUPO-UHFFFAOYSA-N 5-chloro-2-hydroxy-8-nitro-6-pyrrolidin-1-ylbenzo[de]isoquinoline-1,3-dione Chemical compound C=12C3=CC([N+]([O-])=O)=CC=1C(=O)N(O)C(=O)C2=CC(Cl)=C3N1CCCC1 HVCIKRLEWIFUPO-UHFFFAOYSA-N 0.000 claims description 2
HRCMUWXKQHOULX-UHFFFAOYSA-N 5-fluoro-2-hydroxy-6-pyrrolidin-1-ylbenzo[de]isoquinoline-1,3-dione Chemical compound FC1=CC(=C23)C(=O)N(O)C(=O)C2=CC=CC3=C1N1CCCC1 HRCMUWXKQHOULX-UHFFFAOYSA-N 0.000 claims description 2
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
PISMCGHINLJCAB-UHFFFAOYSA-N 8-bromo-5-chloro-2-hydroxy-6-pyrrolidin-1-ylbenzo[de]isoquinoline-1,3-dione Chemical compound ClC1=CC(=C23)C(=O)N(O)C(=O)C2=CC(Br)=CC3=C1N1CCCC1 PISMCGHINLJCAB-UHFFFAOYSA-N 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
238000010511 deprotection reaction Methods 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
SKBHZSLCDPEXBF-UHFFFAOYSA-N 11-hydroxy-4-(pyridin-2-ylmethyl)-6-oxa-4,11-diazatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),8,13,15-pentaene-10,12-dione Chemical compound C1OC2=CC(=C34)C(=O)N(O)C(=O)C3=CC=CC4=C2CN1CC1=CC=CC=N1 SKBHZSLCDPEXBF-UHFFFAOYSA-N 0.000 claims 1
OUOPXQSYZJBTMB-UHFFFAOYSA-N 2-hydroxy-5-methoxy-6-piperidin-1-ylbenzo[de]isoquinoline-1,3-dione Chemical compound COC1=CC(=C23)C(=O)N(O)C(=O)C3=CC=CC2=C1N1CCCCC1 OUOPXQSYZJBTMB-UHFFFAOYSA-N 0.000 claims 1
FCIHRNHSIWJAJP-UHFFFAOYSA-N 6-(3-aminopyrrolidin-1-yl)-2-hydroxy-5-methoxybenzo[de]isoquinoline-1,3-dione Chemical compound COC1=CC(=C23)C(=O)N(O)C(=O)C3=CC=CC2=C1N1CCC(N)C1 FCIHRNHSIWJAJP-UHFFFAOYSA-N 0.000 claims 1
125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 1
NOKUPYDPWYMPCL-QRPNPIFTSA-N C1CN(C[C@H]1N)C2=C(C=C3C4=C2C=CC=C4C(=O)N(C3=O)O)Br.Cl Chemical compound C1CN(C[C@H]1N)C2=C(C=C3C4=C2C=CC=C4C(=O)N(C3=O)O)Br.Cl NOKUPYDPWYMPCL-QRPNPIFTSA-N 0.000 claims 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 157
229910001868 water Inorganic materials 0.000 description 139
239000000243 solution Substances 0.000 description 125
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 124
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 116
239000000203 mixture Substances 0.000 description 112
239000007787 solid Substances 0.000 description 91
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 89
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 84
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 80
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 77
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 75
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 69
239000002244 precipitate Substances 0.000 description 62
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 58
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
238000005481 NMR spectroscopy Methods 0.000 description 52
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 50
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 41
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 41
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 39
239000000725 suspension Substances 0.000 description 37
239000011541 reaction mixture Substances 0.000 description 35
239000002904 solvent Substances 0.000 description 32
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 31
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 25
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 25
229960000583 acetic acid Drugs 0.000 description 25
229910017604 nitric acid Inorganic materials 0.000 description 25
239000005457 ice water Substances 0.000 description 23
238000001914 filtration Methods 0.000 description 22
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
239000000047 product Substances 0.000 description 20
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 19
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
239000002585 base Substances 0.000 description 18
238000005984 hydrogenation reaction Methods 0.000 description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
238000003756 stirring Methods 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
238000010992 reflux Methods 0.000 description 16
229940086542 triethylamine Drugs 0.000 description 16
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 15
150000008064 anhydrides Chemical class 0.000 description 15
238000004440 column chromatography Methods 0.000 description 15
150000001412 amines Chemical class 0.000 description 14
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 12
239000003054 catalyst Substances 0.000 description 10
239000003795 chemical substances by application Substances 0.000 description 10
239000012044 organic layer Substances 0.000 description 10
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FHIMETDUFUEOOJ-UHFFFAOYSA-N (5-acetamido-1,3-dioxobenzo[de]isoquinolin-2-yl) acetate Chemical compound C1=CC2=CC(NC(=O)C)=CC(C(=O)N(OC(C)=O)C3=O)=C2C3=C1 FHIMETDUFUEOOJ-UHFFFAOYSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
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CCQJLRYBHHEKMZ-UHFFFAOYSA-N 11-hydroxy-3-methoxy-4,6-dioxa-11-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),8,13,15-pentaene-10,12-dione Chemical compound C1=CC2=C3C(OC)OCOC3=CC(C(=O)N(O)C3=O)=C2C3=C1 CCQJLRYBHHEKMZ-UHFFFAOYSA-N 0.000 description 1
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HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
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KHAMRMOSVBRUGE-UHFFFAOYSA-N n-[6-chloro-2-[(2-methylpropan-2-yl)oxy]-1,3-dioxobenzo[de]isoquinolin-5-yl]acetamide Chemical compound C1=CC2=C(Cl)C(NC(=O)C)=CC(C(=O)N(OC(C)(C)C)C3=O)=C2C3=C1 KHAMRMOSVBRUGE-UHFFFAOYSA-N 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
108020004707 nucleic acids Proteins 0.000 description 1
150000007523 nucleic acids Chemical class 0.000 description 1
102000039446 nucleic acids Human genes 0.000 description 1
ORAQFQGEIBFOCW-UHFFFAOYSA-N o-(1,3-dioxo-2-phenylmethoxybenzo[de]isoquinolin-5-yl) n,n-dimethylcarbamothioate Chemical compound O=C1C(C=23)=CC=CC3=CC(OC(=S)N(C)C)=CC=2C(=O)N1OCC1=CC=CC=C1 ORAQFQGEIBFOCW-UHFFFAOYSA-N 0.000 description 1
SSUCKKNRCOFUPT-UHFFFAOYSA-N o-[tert-butyl(dimethyl)silyl]hydroxylamine Chemical compound CC(C)(C)[Si](C)(C)ON SSUCKKNRCOFUPT-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
ZMLDXWLZKKZVSS-UHFFFAOYSA-N palladium tin Chemical compound [Pd].[Sn] ZMLDXWLZKKZVSS-UHFFFAOYSA-N 0.000 description 1
UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
239000006201 parenteral dosage form Substances 0.000 description 1
230000037361 pathway Effects 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
SDFVUQINJAUPSH-UHFFFAOYSA-M potassium;2-hydroxy-1,3-dioxobenzo[de]isoquinoline-6-sulfonate Chemical compound [K+].C1=CC(C(N(O)C2=O)=O)=C3C2=CC=CC3=C1S([O-])(=O)=O SDFVUQINJAUPSH-UHFFFAOYSA-M 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
NGXSWUFDCSEIOO-UHFFFAOYSA-N pyrrolidin-3-amine Chemical compound NC1CCNC1 NGXSWUFDCSEIOO-UHFFFAOYSA-N 0.000 description 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
230000001105 regulatory effect Effects 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
229960004889 salicylic acid Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 description 1
229910000367 silver sulfate Inorganic materials 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
229940063673 spermidine Drugs 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000010959 steel Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003760 tallow Substances 0.000 description 1
IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
239000012414 tert-butyl nitrite Substances 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
210000001541 thymus gland Anatomy 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
238000006257 total synthesis reaction Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
239000011345 viscous material Substances 0.000 description 1

Classifications

- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- 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
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/06—Peri-condensed systems
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Other In-Based Heterocyclic Compounds (AREA)

NO19992104A 1996-11-01 1999-04-30 Isokinoloner og fremgangsmåte for fremstilling derav NO314304B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US2990996P	1996-11-01	1996-11-01
PCT/US1997/019872 WO1998019648A2 (en)	1996-11-01	1997-10-31	N-oxy-naphthalimides as antibacterial agents

Publications (3)

Publication Number	Publication Date
NO992104D0 NO992104D0 (no)	1999-04-30
NO992104L NO992104L (no)	1999-04-30
NO314304B1 true NO314304B1 (no)	2003-03-03

Family

ID=21851529

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19992104A NO314304B1 (no)	1996-11-01	1999-04-30	Isokinoloner og fremgangsmåte for fremstilling derav

Country Status (12)

Country	Link
US (2)	US6177423B1 (de)
EP (1)	EP0939754A2 (de)
JP (1)	JP2001505554A (de)
KR (1)	KR20000052949A (de)
AU (1)	AU748749B2 (de)
BR (1)	BR9712715A (de)
CA (1)	CA2263301A1 (de)
IL (1)	IL128516A0 (de)
NO (1)	NO314304B1 (de)
NZ (1)	NZ334896A (de)
PL (1)	PL333238A1 (de)
WO (1)	WO1998019648A2 (de)

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AU2005209845A1 (en) *	2004-01-30	2005-08-18	Chemgenex Pharmaceuticals, Inc.	Naphthalimide dosing by N-acetyl transferase genotyping
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WO2011087011A1 (ja) *	2010-01-13	2011-07-21	株式会社Adeka	新規スルホン酸誘導体化合物及び新規ナフタル酸誘導体化合物
CN103012185A (zh) *	2012-12-24	2013-04-03	辽宁本源制药有限公司	一种治疗抑郁症的药物阿戈美拉汀的制备方法
CN105492428A (zh) *	2013-05-01	2016-04-13	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
CN106083850B (zh) *	2016-07-13	2018-01-02	河南大学	一类嘧啶并萘酰亚胺衍生物及其制备方法和应用
CN109384720B (zh) *	2018-11-01	2022-06-28	上海博栋化学科技有限公司	合成6-(2-甲氧基乙氧基)-n-羟基萘酰亚胺三氟甲磺酸的方法
CN109932349B (zh) *	2019-04-04	2021-04-20	济南大学	一种检测次氯酸的有机硅小分子荧光探针
CN110078666B (zh) *	2019-06-15	2023-01-24	山东省医学科学院药物研究所(山东省抗衰老研究中心山东省新技术制药研究所)	一种基于萘酰亚胺的镍离子荧光探针、制备方法及其应用
CN110194741B (zh) *	2019-07-08	2022-09-09	桂林医学院	4-苯甲酰哌嗪-3-硝基-1,8-萘酰亚胺衍生物及其制备方法和应用
CN110317171B (zh) *	2019-07-08	2022-06-17	桂林医学院	4-二硫代甲酸哌嗪-1,8-萘酰亚胺衍生物及其制备方法和应用
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
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
CN110283163B (zh) *	2019-07-08	2023-03-14	桂林医学院	4-叔丁氧羰基哌嗪-3-硝基-1,8-萘酰亚胺衍生物及其合成方法和应用
CN110194740B (zh) *	2019-07-08	2022-06-17	桂林医学院	4-叔丁氧羰基哌嗪-1,8-萘酰亚胺衍生物及其合成方法和应用

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1997
- 1997-10-31 US US09/254,645 patent/US6177423B1/en not_active Expired - Fee Related
- 1997-10-31 WO PCT/US1997/019872 patent/WO1998019648A2/en not_active Ceased
- 1997-10-31 JP JP52161898A patent/JP2001505554A/ja not_active Abandoned
- 1997-10-31 KR KR1019990703822A patent/KR20000052949A/ko not_active Ceased
- 1997-10-31 IL IL12851697A patent/IL128516A0/xx unknown
- 1997-10-31 PL PL97333238A patent/PL333238A1/xx unknown
- 1997-10-31 AU AU51604/98A patent/AU748749B2/en not_active Ceased
- 1997-10-31 BR BR9712715-9A patent/BR9712715A/pt not_active Application Discontinuation
- 1997-10-31 CA CA002263301A patent/CA2263301A1/en not_active Abandoned
- 1997-10-31 EP EP97946438A patent/EP0939754A2/de not_active Withdrawn
- 1997-10-31 NZ NZ334896A patent/NZ334896A/xx unknown
1999
- 1999-04-30 NO NO19992104A patent/NO314304B1/no not_active IP Right Cessation
2000
- 2000-08-11 US US09/637,949 patent/US6362181B1/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
IL128516A0 (en)	2000-01-31
WO1998019648A3 (en)	1999-03-04
AU748749B2 (en)	2002-06-13
CA2263301A1 (en)	1998-05-14
WO1998019648A2 (en)	1998-05-14
US6362181B1 (en)	2002-03-26
NO992104D0 (no)	1999-04-30
NO992104L (no)	1999-04-30
NZ334896A (en)	2001-01-26
BR9712715A (pt)	2000-05-16
AU5160498A (en)	1998-05-29
JP2001505554A (ja)	2001-04-24
KR20000052949A (ko)	2000-08-25
PL333238A1 (en)	1999-11-22
EP0939754A2 (de)	1999-09-08
US6177423B1 (en)	2001-01-23

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Date	Code	Title	Description
2004-10-18	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
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