IL125286A - Phenanthridine compounds and medicaments containing the same - Google Patents

Phenanthridine compounds and medicaments containing the same

Info

Publication number: IL125286A
Authority: IL; Israel
Prior art keywords: hydrogen; alkyl; alkoxy; compounds; formula
Prior art date: 1996-01-31

Application number

IL12528697A

Other languages

English (en)

Other versions

IL125286A0 (en

Original Assignee

Byk Gulden Lomberg Chem Fab

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.)

1996-01-31

Filing date

1997-01-30

Publication date

2002-08-14

1997-01-30 Application filed by Byk Gulden Lomberg Chem Fab filed Critical Byk Gulden Lomberg Chem Fab

1997-01-30 Priority claimed from PCT/EP1997/000402 external-priority patent/WO1997028131A1/de

1999-03-12 Publication of IL125286A0 publication Critical patent/IL125286A0/xx

2002-08-14 Publication of IL125286A publication Critical patent/IL125286A/en

Links

239000003814 drug Substances 0.000 title claims description 15
150000005053 phenanthridines Chemical class 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 107
239000001257 hydrogen Substances 0.000 claims abstract description 67
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 67
150000002431 hydrogen Chemical class 0.000 claims abstract description 38
150000003839 salts Chemical class 0.000 claims abstract description 34
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
229910052731 fluorine Inorganic materials 0.000 claims abstract description 15
239000011737 fluorine Substances 0.000 claims abstract description 15
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
-1 methoxy, ethoxy Chemical group 0.000 claims description 44
238000011282 treatment Methods 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 6
208000023504 respiratory system disease Diseases 0.000 claims description 2
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 2
150000001768 cations Chemical class 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 abstract description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 83
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
235000019441 ethanol Nutrition 0.000 description 29
239000003921 oil Substances 0.000 description 24
238000000034 method Methods 0.000 description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
238000000921 elemental analysis Methods 0.000 description 20
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
239000007858 starting material Substances 0.000 description 14
239000000203 mixture Substances 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 12
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
230000003287 optical effect Effects 0.000 description 12
230000002829 reductive effect Effects 0.000 description 12
239000002904 solvent Substances 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
239000002253 acid Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
239000002585 base Substances 0.000 description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
208000035475 disorder Diseases 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
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 description 5
208000006673 asthma Diseases 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000003112 inhibitor Substances 0.000 description 5
239000002571 phosphodiesterase inhibitor Substances 0.000 description 5
238000011321 prophylaxis Methods 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
239000007868 Raney catalyst Substances 0.000 description 4
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
229910000564 Raney nickel Inorganic materials 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
108060008682 Tumor Necrosis Factor Proteins 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
208000010668 atopic eczema Diseases 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
230000002757 inflammatory effect Effects 0.000 description 4
JVTZFYYHCGSXJV-UHFFFAOYSA-N isovanillin Chemical compound COC1=CC=C(C=O)C=C1O JVTZFYYHCGSXJV-UHFFFAOYSA-N 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
230000008569 process Effects 0.000 description 4
208000017520 skin disease Diseases 0.000 description 4
239000000725 suspension Substances 0.000 description 4
102000003390 tumor necrosis factor Human genes 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
RKEFGUYRAHCSMV-UHFFFAOYSA-N 2-(3,4-diethoxyphenyl)cyclohexan-1-one Chemical compound C1=C(OCC)C(OCC)=CC=C1C1C(=O)CCCC1 RKEFGUYRAHCSMV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
206010040070 Septic Shock Diseases 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
230000000172 allergic effect Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 3
239000002674 ointment Substances 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
230000009467 reduction Effects 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
239000000126 substance Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 description 2
BIVMWDQSMDXTCT-RYUDHWBXSA-N (1s,2s)-2-(3,4-dimethoxyphenyl)cyclohexan-1-amine Chemical compound C1=C(OC)C(OC)=CC=C1[C@H]1[C@@H](N)CCCC1 BIVMWDQSMDXTCT-RYUDHWBXSA-N 0.000 description 2
HFGWXWJFQQCBEY-NWDGAFQWSA-N 1,2-dimethoxy-4-[(1s,6r)-6-nitrocyclohex-3-en-1-yl]benzene Chemical compound C1=C(OC)C(OC)=CC=C1[C@H]1[C@H]([N+]([O-])=O)CC=CC1 HFGWXWJFQQCBEY-NWDGAFQWSA-N 0.000 description 2
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
ZIOBKYXYQVFUJT-UHFFFAOYSA-N 3-(difluoromethoxy)-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1OC(F)F ZIOBKYXYQVFUJT-UHFFFAOYSA-N 0.000 description 2
XXWONCALJGBUFK-UHFFFAOYSA-N 6-phenylphenanthridine Chemical class C1=CC=CC=C1C1=NC2=CC=CC=C2C2=CC=CC=C12 XXWONCALJGBUFK-UHFFFAOYSA-N 0.000 description 2
206010001052 Acute respiratory distress syndrome Diseases 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 2
102000004127 Cytokines Human genes 0.000 description 2
108090000695 Cytokines Proteins 0.000 description 2
208000010228 Erectile Dysfunction Diseases 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
108010044467 Isoenzymes Proteins 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
208000013616 Respiratory Distress Syndrome Diseases 0.000 description 2
IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
230000009471 action Effects 0.000 description 2
230000004913 activation Effects 0.000 description 2
208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 2
201000000028 adult respiratory distress syndrome Diseases 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
230000002917 arthritic effect Effects 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000011575 calcium Substances 0.000 description 2
230000001413 cellular effect Effects 0.000 description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
230000001684 chronic effect Effects 0.000 description 2
229940095074 cyclic amp Drugs 0.000 description 2
238000006352 cycloaddition reaction Methods 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000000499 gel Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
210000003714 granulocyte Anatomy 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
239000005457 ice water Substances 0.000 description 2
201000001881 impotence Diseases 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
210000004969 inflammatory cell Anatomy 0.000 description 2
230000004054 inflammatory process Effects 0.000 description 2
208000030603 inherited susceptibility to asthma Diseases 0.000 description 2
238000011835 investigation Methods 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
150000002617 leukotrienes Chemical class 0.000 description 2
210000002540 macrophage Anatomy 0.000 description 2
239000000463 material Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
210000000440 neutrophil Anatomy 0.000 description 2
230000003448 neutrophilic effect Effects 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
239000002777 nucleoside Substances 0.000 description 2
150000003833 nucleoside derivatives Chemical class 0.000 description 2
239000000843 powder Substances 0.000 description 2
230000002062 proliferating effect Effects 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
230000019254 respiratory burst Effects 0.000 description 2
230000000241 respiratory effect Effects 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
230000028327 secretion Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000007921 spray Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
239000003826 tablet Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 description 2
HJMQDJPMQIHLPB-UHFFFAOYSA-N zardaverine Chemical compound C1=C(OC(F)F)C(OC)=CC(C2=NNC(=O)C=C2)=C1 HJMQDJPMQIHLPB-UHFFFAOYSA-N 0.000 description 2
229950001080 zardaverine Drugs 0.000 description 2
AFWKDPKNOPLGEL-VRJTXETASA-N (1s,2s)-2-(3,4-diethoxyphenyl)-n-(1-phenylethyl)cyclohexan-1-amine Chemical compound C1=C(OCC)C(OCC)=CC=C1[C@H]1[C@@H](NC(C)C=2C=CC=CC=2)CCCC1 AFWKDPKNOPLGEL-VRJTXETASA-N 0.000 description 1
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-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
CKUUWZSXSMTFIO-RYUDHWBXSA-N 1,2-dimethoxy-4-[(1s,2s)-2-nitrocyclohexyl]benzene Chemical compound C1=C(OC)C(OC)=CC=C1[C@H]1[C@@H]([N+]([O-])=O)CCCC1 CKUUWZSXSMTFIO-RYUDHWBXSA-N 0.000 description 1
HFGWXWJFQQCBEY-RYUDHWBXSA-N 1,2-dimethoxy-4-[(1s,6s)-6-nitrocyclohex-3-en-1-yl]benzene Chemical compound C1=C(OC)C(OC)=CC=C1[C@H]1[C@@H]([N+]([O-])=O)CC=CC1 HFGWXWJFQQCBEY-RYUDHWBXSA-N 0.000 description 1
125000004815 1,2-dimethylethylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([*:2])C([H])([H])[H] 0.000 description 1
GEUOBOMZZQKTHL-UHFFFAOYSA-N 1-ethenyl-4,5-dimethoxy-5-nitrocyclohexa-1,3-diene Chemical compound COC1=CC=C(C=C)CC1(OC)[N+]([O-])=O GEUOBOMZZQKTHL-UHFFFAOYSA-N 0.000 description 1
125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
YGTUPRIZNBMOFV-UHFFFAOYSA-N 2-(4-hydroxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(O)C=C1 YGTUPRIZNBMOFV-UHFFFAOYSA-N 0.000 description 1
HVAUUPRFYPCOCA-AREMUKBSSA-N 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](OC(C)=O)COP([O-])(=O)OCC[N+](C)(C)C HVAUUPRFYPCOCA-AREMUKBSSA-N 0.000 description 1
IUVCFHHAEHNCFT-INIZCTEOSA-N 2-[(1s)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1[C@@H](C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 IUVCFHHAEHNCFT-INIZCTEOSA-N 0.000 description 1
WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 1
ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
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230000002588 toxic effect Effects 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
210000000626 ureter Anatomy 0.000 description 1
230000000304 vasodilatating effect Effects 0.000 description 1
239000008096 xylene 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
- C07D221/10—Aza-phenanthrenes
- C07D221/12—Phenanthridines
- 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
- A61P11/08—Bronchodilators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pulmonology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Saccharide Compounds (AREA)

IL12528697A 1996-01-31 1997-01-30 Phenanthridine compounds and medicaments containing the same IL125286A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19603321A DE19603321A1 (de)	1996-01-31	1996-01-31	Neue Phenanthridine
PCT/EP1997/000402 WO1997028131A1 (de)	1996-01-31	1997-01-30	Neue phenanthridine

Publications (2)

Publication Number	Publication Date
IL125286A0 IL125286A0 (en)	1999-03-12
IL125286A true IL125286A (en)	2002-08-14

Family

ID=7784067

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL12528697A IL125286A (en)	1996-01-31	1997-01-30	Phenanthridine compounds and medicaments containing the same

Country Status (8)

Country	Link
CN (1)	CN1142914C (pl)
AU (1)	AU707058B2 (pl)
DE (1)	DE19603321A1 (pl)
IL (1)	IL125286A (pl)
NO (1)	NO311214B1 (pl)
NZ (1)	NZ331374A (pl)
PL (1)	PL187127B1 (pl)
SK (1)	SK282084B6 (pl)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6548490B1 (en) *	1997-10-28	2003-04-15	Vivus, Inc.	Transmucosal administration of phosphodiesterase inhibitors for the treatment of erectile dysfunction
US6403597B1 (en)	1997-10-28	2002-06-11	Vivus, Inc.	Administration of phosphodiesterase inhibitors for the treatment of premature ejaculation

1996
- 1996-01-31 DE DE19603321A patent/DE19603321A1/de not_active Withdrawn
1997
- 1997-01-30 NZ NZ331374A patent/NZ331374A/xx unknown
- 1997-01-30 AU AU17199/97A patent/AU707058B2/en not_active Ceased
- 1997-01-30 SK SK1024-98A patent/SK282084B6/sk unknown
- 1997-01-30 IL IL12528697A patent/IL125286A/en not_active IP Right Cessation
- 1997-01-30 PL PL97328019A patent/PL187127B1/pl not_active IP Right Cessation
- 1997-01-30 CN CNB971934584A patent/CN1142914C/zh not_active Expired - Fee Related
1998
- 1998-07-30 NO NO19983505A patent/NO311214B1/no unknown

Also Published As

Publication number	Publication date
NO983505D0 (no)	1998-07-30
PL187127B1 (pl)	2004-05-31
DE19603321A1 (de)	1997-08-07
AU707058B2 (en)	1999-07-01
NZ331374A (en)	2000-01-28
CN1214681A (zh)	1999-04-21
SK102498A3 (en)	1999-03-12
NO983505L (no)	1998-09-11
IL125286A0 (en)	1999-03-12
AU1719997A (en)	1997-08-22
SK282084B6 (sk)	2001-10-08
CN1142914C (zh)	2004-03-24
PL328019A1 (en)	1999-01-04
NO311214B1 (no)	2001-10-29

Legal Events

Date	Code	Title
2003-02-12	FF	Patent granted
2003-04-10	KB	Patent renewed
2007-05-21	KB	Patent renewed
2011-09-27	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
CA2245142C (en)	2004-11-30	New phenanthridines
US6127378A (en)	2000-10-03	Phenanthridines substituted in the 6 position
AU718752B2 (en)	2000-04-20	Novel phenanthridines substituted in the 6 position
AU753615B2 (en)	2002-10-24	Novel tetrazole derivatives
IL133825A (en)	2005-12-18	Substituted 6-phenylphenanthridines, medicaments containing same and use thereof in the production of medicaments
US6534518B1 (en)	2003-03-18	Polysubstituted 6-phenylphenanthridines with PDE-IV inhibiting activity
EP1000034B1 (en)	2002-09-18	Substituted 6-alkylphenanthridines
EP1147088B1 (en)	2006-01-04	6-arylphenanthridines with pde-iv inhibiting activity
US6538005B2 (en)	2003-03-25	Phenanthridine-N-oxides with PDE-IV inhibiting activity
US6630483B2 (en)	2003-10-07	Phenanthridine-N-oxides
AU707058B2 (en)	1999-07-01	Novel phenanthridines
WO2002006239A1 (en)	2002-01-24	Phenanthridine n-oxides