AU711539B2 - Novel aryl-pyridazines - Google Patents

Novel aryl-pyridazines Download PDF

Info

Publication number: AU711539B2
Authority: AU; Australia
Prior art keywords: chlorophenyl; tetrahydro; represent; benzopyrano; alkyl
Prior art date: 1996-09-05
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.): Ceased

Application number

AU38736/97A

Other languages

English (en)

Other versions

AU3873697A (en

Inventor

John Bantick

Simon Hirst

Matthew Perry

Eifion Phillips

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Astra Pharmaceuticals Ltd

Original Assignee

Astra Pharmaceuticals Ltd

Astra Pharmaceutical Products Inc

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.)

1996-09-05

Filing date

1997-08-19

Publication date

1999-10-14

1996-09-05 Priority claimed from GBGB9618487.4A external-priority patent/GB9618487D0/en

1996-09-12 Priority claimed from GBGB9619122.6A external-priority patent/GB9619122D0/en

1996-09-20 Priority claimed from GBGB9619642.3A external-priority patent/GB9619642D0/en

1997-08-19 Application filed by Astra Pharmaceuticals Ltd, Astra Pharmaceutical Products Inc filed Critical Astra Pharmaceuticals Ltd

1998-03-26 Publication of AU3873697A publication Critical patent/AU3873697A/en

1999-10-14 Application granted granted Critical

1999-10-14 Publication of AU711539B2 publication Critical patent/AU711539B2/en

2017-08-19 Anticipated expiration legal-status Critical

Status Ceased legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 269
125000000217 alkyl group Chemical group 0.000 claims description 81
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 63
-1 nitro, cyano, phenyl Chemical group 0.000 claims description 55
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 49
229910052760 oxygen Inorganic materials 0.000 claims description 43
229910052739 hydrogen Inorganic materials 0.000 claims description 42
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
229910052799 carbon Inorganic materials 0.000 claims description 30
125000003545 alkoxy group Chemical group 0.000 claims description 28
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 27
229910052736 halogen Inorganic materials 0.000 claims description 26
150000002367 halogens Chemical class 0.000 claims description 26
229910052727 yttrium Inorganic materials 0.000 claims description 26
239000001257 hydrogen Substances 0.000 claims description 25
125000001424 substituent group Chemical group 0.000 claims description 25
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 24
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
229910052757 nitrogen Inorganic materials 0.000 claims description 22
229910052717 sulfur Inorganic materials 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 20
ZHEAXGGEDWGTDP-UHFFFAOYSA-N chromeno[4,3-c]pyrazole Chemical compound C1=CC=C2C3=NN=CC3=COC2=C1 ZHEAXGGEDWGTDP-UHFFFAOYSA-N 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 18
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
208000006673 asthma Diseases 0.000 claims description 12
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 12
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
150000002431 hydrogen Chemical group 0.000 claims description 11
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 10
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 10
238000011282 treatment Methods 0.000 claims description 10
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 9
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
LFNUPYTXYNMLTK-UHFFFAOYSA-N 2-(4-chlorophenyl)-4,4a,5,6-tetrahydro-3h-pyrido[2,3-h]cinnoline Chemical compound C1=CC(Cl)=CC=C1N1N=C2C3=CC=CN=C3CCC2CC1 LFNUPYTXYNMLTK-UHFFFAOYSA-N 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
ZNNUOTRUSLBZGJ-UHFFFAOYSA-N 2-(4-chlorophenyl)-4,4a,5,6-tetrahydro-3h-pyrido[4,3-h]cinnoline Chemical compound C1=CC(Cl)=CC=C1N1N=C2C3=CN=CC=C3CCC2CC1 ZNNUOTRUSLBZGJ-UHFFFAOYSA-N 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
230000000172 allergic effect Effects 0.000 claims description 5
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
125000005936 piperidyl group Chemical group 0.000 claims description 5
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 5
125000005493 quinolyl group Chemical group 0.000 claims description 5
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
239000012453 solvate Substances 0.000 claims description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
208000010668 atopic eczema Diseases 0.000 claims description 4
125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 4
SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 claims description 4
WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
YPXYWEFBMDYHJO-UHFFFAOYSA-N 2-(4-chlorophenyl)-3a,4-dihydro-3h-pyrazolo[4,5]thiopyrano[1,2-b]pyridine Chemical compound C1=CC(Cl)=CC=C1N1N=C2C3=CC=CN=C3SCC2C1 YPXYWEFBMDYHJO-UHFFFAOYSA-N 0.000 claims description 2
SEICHUDVTMSCNQ-UHFFFAOYSA-N 2-(4-chlorophenyl)-7-fluoro-3a,4-dihydro-3h-chromeno[4,3-c]pyrazole Chemical compound C1C2COC3=CC(F)=CC=C3C2=NN1C1=CC=C(Cl)C=C1 SEICHUDVTMSCNQ-UHFFFAOYSA-N 0.000 claims description 2
QGQBBFYXARONSN-UHFFFAOYSA-N 2-(4-chlorophenyl)-8-methoxy-3a,4-dihydro-3h-thiochromeno[4,3-c]pyrazole Chemical compound N1=C2C3=CC(OC)=CC=C3SCC2CN1C1=CC=C(Cl)C=C1 QGQBBFYXARONSN-UHFFFAOYSA-N 0.000 claims description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
JDNGNUKARFENGG-UHFFFAOYSA-N 8-chloro-2-(4-chlorophenyl)-3a,4-dihydro-3h-chromeno[4,3-c]pyrazole Chemical compound C1=CC(Cl)=CC=C1N1N=C2C3=CC(Cl)=CC=C3OCC2C1 JDNGNUKARFENGG-UHFFFAOYSA-N 0.000 claims description 2
230000004968 inflammatory condition Effects 0.000 claims description 2
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 1
SBMZPEBRNBKHMQ-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-3a,4-dihydro-3h-chromeno[4,3-c]pyrazole Chemical compound C1=CC=C2SC(N3N=C4C5=CC=CC=C5OCC4C3)=NC2=C1 SBMZPEBRNBKHMQ-UHFFFAOYSA-N 0.000 claims 1
JFAVJBLGAGZHRO-UHFFFAOYSA-N 2-(4-chlorophenyl)-3a,4-dihydro-3h-chromeno[4,3-c]pyrazole-6-carbonitrile Chemical compound C1=CC(Cl)=CC=C1N1N=C2C3=CC=CC(C#N)=C3OCC2C1 JFAVJBLGAGZHRO-UHFFFAOYSA-N 0.000 claims 1
SCPLFIUOAJIVQH-UHFFFAOYSA-N 2-(4-chlorophenyl)-3a,4-dihydro-3h-thiochromeno[4,3-c]pyrazol-8-ol Chemical compound N1=C2C3=CC(O)=CC=C3SCC2CN1C1=CC=C(Cl)C=C1 SCPLFIUOAJIVQH-UHFFFAOYSA-N 0.000 claims 1
RUNVHHQTRQZGQC-UHFFFAOYSA-N 2-(4-chlorophenyl)-4a-methyl-4,5-dihydro-3h-indeno[1,2-c]pyridazine Chemical compound C1CC2(C)CC3=CC=CC=C3C2=NN1C1=CC=C(Cl)C=C1 RUNVHHQTRQZGQC-UHFFFAOYSA-N 0.000 claims 1
LEHMHPZEAZWLCH-UHFFFAOYSA-N 2-(4-chlorophenyl)-4h-thiochromeno[4,3-c]pyrazole Chemical compound C1=CC(Cl)=CC=C1N1N=C2C3=CC=CC=C3SCC2=C1 LEHMHPZEAZWLCH-UHFFFAOYSA-N 0.000 claims 1
OSBMXEHQNXSPHF-UHFFFAOYSA-N 2-(4-chlorophenyl)-7-oxido-4,4a,5,6-tetrahydro-3h-pyrido[2,3-h]cinnolin-7-ium Chemical compound C1CC2CCC=3[N+]([O-])=CC=CC=3C2=NN1C1=CC=C(Cl)C=C1 OSBMXEHQNXSPHF-UHFFFAOYSA-N 0.000 claims 1
RNHDXYHAVHJXTH-UHFFFAOYSA-N 2-(4-chlorophenyl)-8-methoxy-3a,4-dihydro-3h-chromeno[4,3-c]pyrazole Chemical compound N1=C2C3=CC(OC)=CC=C3OCC2CN1C1=CC=C(Cl)C=C1 RNHDXYHAVHJXTH-UHFFFAOYSA-N 0.000 claims 1
OCXASIMZRIFUDL-UHFFFAOYSA-N 2-quinolin-3-yl-3a,4-dihydro-3h-thiochromeno[4,3-c]pyrazole Chemical compound C1=CC=CC2=CC(N3N=C4C5=CC=CC=C5SCC4C3)=CN=C21 OCXASIMZRIFUDL-UHFFFAOYSA-N 0.000 claims 1
IIMSFPMKSGUPPU-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1N=C2C(=C1)COC1=C2C=CC=C1.ClC1=CC=C(C=C1)N1N=C2C3=C(CCC2C1)C=CC=C3 Chemical compound ClC1=CC=C(C=C1)N1N=C2C(=C1)COC1=C2C=CC=C1.ClC1=CC=C(C=C1)N1N=C2C3=C(CCC2C1)C=CC=C3 IIMSFPMKSGUPPU-UHFFFAOYSA-N 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 228
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 171
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 114
239000000243 solution Substances 0.000 description 84
AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 76
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 65
239000007787 solid Substances 0.000 description 56
238000000034 method Methods 0.000 description 52
238000006243 chemical reaction Methods 0.000 description 51
239000003960 organic solvent Substances 0.000 description 48
238000010992 reflux Methods 0.000 description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 38
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 34
238000002360 preparation method Methods 0.000 description 34
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
239000000203 mixture Substances 0.000 description 33
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
239000011541 reaction mixture Substances 0.000 description 31
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 31
238000005481 NMR spectroscopy Methods 0.000 description 30
239000012267 brine Substances 0.000 description 30
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
239000002904 solvent Substances 0.000 description 21
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
238000001953 recrystallisation Methods 0.000 description 19
229910052938 sodium sulfate Inorganic materials 0.000 description 19
235000011152 sodium sulphate Nutrition 0.000 description 19
239000012074 organic phase Substances 0.000 description 18
239000000047 product Substances 0.000 description 18
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 17
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
239000002585 base Substances 0.000 description 17
238000004587 chromatography analysis Methods 0.000 description 16
238000001914 filtration Methods 0.000 description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
238000010438 heat treatment Methods 0.000 description 15
238000000746 purification Methods 0.000 description 15
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 14
239000000284 extract Substances 0.000 description 14
235000017557 sodium bicarbonate Nutrition 0.000 description 14
229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
238000004440 column chromatography Methods 0.000 description 13
229910052943 magnesium sulfate Inorganic materials 0.000 description 13
235000019341 magnesium sulphate Nutrition 0.000 description 13
206010039083 rhinitis Diseases 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
238000001704 evaporation Methods 0.000 description 12
230000008020 evaporation Effects 0.000 description 12
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000007858 starting material Substances 0.000 description 11
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
150000001721 carbon Chemical group 0.000 description 10
239000012954 diazonium Substances 0.000 description 10
150000001989 diazonium salts Chemical class 0.000 description 10
239000003921 oil Substances 0.000 description 10
235000019198 oils Nutrition 0.000 description 10
229910000027 potassium carbonate Inorganic materials 0.000 description 10
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
239000008096 xylene Substances 0.000 description 10
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000012299 nitrogen atmosphere Substances 0.000 description 9
125000006239 protecting group Chemical group 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 8
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
239000008346 aqueous phase Substances 0.000 description 7
239000012043 crude product Substances 0.000 description 7
239000010410 layer Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
XXNOGQJZAOXWAQ-UHFFFAOYSA-N 4-chlorophenylhydrazine Chemical compound NNC1=CC=C(Cl)C=C1 XXNOGQJZAOXWAQ-UHFFFAOYSA-N 0.000 description 6
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
230000001684 chronic effect Effects 0.000 description 6
230000003647 oxidation Effects 0.000 description 6
238000007254 oxidation reaction Methods 0.000 description 6
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 6
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
229910004298 SiO 2 Inorganic materials 0.000 description 5
UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
239000003638 chemical reducing agent Substances 0.000 description 5
239000013078 crystal Substances 0.000 description 5
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
235000010288 sodium nitrite Nutrition 0.000 description 5
YQVZREHUWCCHHX-UHFFFAOYSA-N (4-chlorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=C(Cl)C=C1 YQVZREHUWCCHHX-UHFFFAOYSA-N 0.000 description 4
CVQSWZMJOGOPAV-UHFFFAOYSA-N 2,3-dihydrothiochromen-4-one Chemical compound C1=CC=C2C(=O)CCSC2=C1 CVQSWZMJOGOPAV-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
206010020751 Hypersensitivity Diseases 0.000 description 4
206010061218 Inflammation Diseases 0.000 description 4
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NRQHPFBTLCBOTK-UHFFFAOYSA-N n-[(2-chloropyridin-3-yl)methylideneamino]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NN=CC1=CC=CN=C1Cl NRQHPFBTLCBOTK-UHFFFAOYSA-N 0.000 description 1
IJBJEQRSKOZLGD-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-3a,4-dihydro-3h-chromeno[4,3-c]pyrazol-7-yl]acetamide Chemical compound C1C2COC3=CC(NC(=O)C)=CC=C3C2=NN1C1=CC=C(Cl)C=C1 IJBJEQRSKOZLGD-UHFFFAOYSA-N 0.000 description 1
201000009240 nasopharyngitis Diseases 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
JJVNINGBHGBWJH-UHFFFAOYSA-N ortho-vanillin Chemical compound COC1=CC=CC(C=O)=C1O JJVNINGBHGBWJH-UHFFFAOYSA-N 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
239000004926 polymethyl methacrylate Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000003380 propellant Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
OYODOQNYJLSLJE-UHFFFAOYSA-N pyrazol-4-one Chemical class O=C1C=NN=C1 OYODOQNYJLSLJE-UHFFFAOYSA-N 0.000 description 1
QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
IBORBSYHSWWFAU-UHFFFAOYSA-N quinolin-3-ylhydrazine;dihydrochloride Chemical compound Cl.Cl.C1=CC=CC2=CC(NN)=CN=C21 IBORBSYHSWWFAU-UHFFFAOYSA-N 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
239000011369 resultant mixture Substances 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
229910001495 sodium tetrafluoroborate Inorganic materials 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
201000000596 systemic lupus erythematosus Diseases 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
238000003419 tautomerization reaction Methods 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 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
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
XSFFVYGQNCHUNO-UHFFFAOYSA-N thiochromeno[4,3-c]pyrazole Chemical compound C1=CC=C2C3=NN=CC3=CSC2=C1 XSFFVYGQNCHUNO-UHFFFAOYSA-N 0.000 description 1
206010043778 thyroiditis Diseases 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
208000001319 vasomotor rhinitis Diseases 0.000 description 1
201000005539 vernal conjunctivitis Diseases 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- 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
- A61P11/02—Nasal agents, e.g. decongestants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/36—Benzo-cinnolines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- 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
- C07D491/04—Ortho-condensed systems
- 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
- C07D491/12—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 three hetero rings
- C07D491/14—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Immunology (AREA)
Pulmonology (AREA)
Rheumatology (AREA)
Otolaryngology (AREA)
Pain & Pain Management (AREA)
Ophthalmology & Optometry (AREA)
Transplantation (AREA)
Dermatology (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

AU38736/97A 1996-09-05 1997-08-19 Novel aryl-pyridazines Ceased AU711539B2 (en)

Applications Claiming Priority (7)

Application Number	Priority Date	Filing Date	Title
GBGB9618487.4A GB9618487D0 (en)	1996-09-05	1996-09-05	Pharmaceutically active compounds
GB9618487		1996-09-05
GBGB9619122.6A GB9619122D0 (en)	1996-09-12	1996-09-12	Pharmaceutically active compounds
GB9619122		1996-09-12
GB9619642		1996-09-20
GBGB9619642.3A GB9619642D0 (en)	1996-09-20	1996-09-20	Compounds
PCT/SE1997/001359 WO1998009969A1 (en)	1996-09-05	1997-08-19	Novel aryl-pyridazines

Publications (2)

Publication Number	Publication Date
AU3873697A AU3873697A (en)	1998-03-26
AU711539B2 true AU711539B2 (en)	1999-10-14

Family

ID=27268459

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU38736/97A Ceased AU711539B2 (en)	1996-09-05	1997-08-19	Novel aryl-pyridazines

Country Status (6)

Country	Link
JP (1)	JP2001501180A (es)
AR (1)	AR009322A1 (es)
AU (1)	AU711539B2 (es)
CA (1)	CA2263586A1 (es)
ID (1)	ID17393A (es)
WO (1)	WO1998009969A1 (es)

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Publication number	Priority date	Publication date	Assignee	Title
AP2527A (en) *	2006-10-31	2012-12-06	Pfizer Prod Inc	Pyrazoline compounds as mineralocorticoid receptorantagonists
US7999107B2 (en)	2007-01-31	2011-08-16	Merck Sharp & Dohme Corp.	Substituted pyrano[2,3-B]pyridine derivatives as cannabinoid-1 receptor modulators
CN102372710A (zh) *	2010-08-18	2012-03-14	山东轩竹医药科技有限公司	作为盐皮质激素受体拮抗剂的并环类化合物
ES2897496T3 (es)	2012-12-22	2022-03-01	Kbp Biosciences Pte Ltd	Procedimiento para la preparación de un compuesto usado como antagonista del receptor de mineralocorticoides
WO2025082467A1 (zh) *	2023-10-19	2025-04-24	成都先导药物开发股份有限公司	一种免疫调节剂

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1989004306A1 (fr) *	1987-11-02	1989-05-18	Yoshitomi Pharmaceutical Industries, Ltd.	Composes de pyridazine fusionnes et leurs utilisations medicales
GB8818895D0 (en) *	1988-08-09	1988-09-14	Boots Co Plc	Therapeutic agents
JPH05505180A (ja) *	1990-02-02	1993-08-05	ザブーツカンパニーピーエルシー	治療薬

1997
- 1997-08-19 JP JP10512539A patent/JP2001501180A/ja active Pending
- 1997-08-19 AU AU38736/97A patent/AU711539B2/en not_active Ceased
- 1997-08-19 CA CA002263586A patent/CA2263586A1/en not_active Abandoned
- 1997-08-19 WO PCT/SE1997/001359 patent/WO1998009969A1/en not_active Ceased
- 1997-08-25 AR ARP970103852A patent/AR009322A1/es unknown
- 1997-09-04 ID IDP973081A patent/ID17393A/id unknown

Also Published As

Publication number	Publication date
AR009322A1 (es)	2000-04-12
ID17393A (id)	1997-12-24
JP2001501180A (ja)	2001-01-30
CA2263586A1 (en)	1998-03-12
WO1998009969A1 (en)	1998-03-12
AU3873697A (en)	1998-03-26

Publication	Publication Date	Title
US4690930A (en)	1987-09-01	Pyrazolo[4,3-c]quinoline-3-one and imidazo[4,3-c]cinnolin-3-one derivatives and their use as psychotropic agents
DE60219672T2 (de)	2007-12-27	Imidazopyridine, -pyrimidine und -triazine als gaba-a alpha 5 rezeptor subtyp liganden zur verbesserung kognitiver eigenschaften
JP2002533465A (ja)	2002-10-08	Ｘａ因子阻害剤としての窒素を含む複素二環類
NO178697B (no)	1996-02-05	Analogifremgangsmåte for fremstilling av terapeutisk aktive pyrazolopyridin-forbindelser
Russo et al.	1994	Synthesis of new thienopyrimidobenzothiazoles and thienopyrimidobenzoxazoles with analgesic and antiinflammatory properties
US5965730A (en)	1999-10-12	Pyridine derivatives
JP2003516989A (ja)	2003-05-20	Ｇａｂａ受容体リガンドとしてのピラゾロ−ピリジン誘導体
US6103736A (en)	2000-08-15	Fused imidazo[1,2-a]pyridines
AU711539B2 (en)	1999-10-14	Novel aryl-pyridazines
JP4693410B2 (ja)	2011-06-01	修飾ラクトン環を有するカンプトテシン
EP0239191A2 (en)	1987-09-30	Pyrazolo[4,3-b]pyridine derivatives, process for their preparation and pharmaceutical compositions containing them
US4801590A (en)	1989-01-31	Pyrido(1,8)naphthyridinones, and their use as pharmaceuticals
KR100251295B1 (ko)	2000-05-01	항앨러지성 이미다조[1,2-a](피롤로, 티에노 또는 푸라노)[2,3-d]아제핀 유도체(Antiallergic imidazo[1,2-a](pyrrolo, thieno or furano)[2,3-d]azepine derivatives)
EP0556813B1 (en)	1997-11-26	Amphoteric tricyclic compounds as antihistaminic and antiallergic agents
US4268513A (en)	1981-05-19	Pyrrolo [3,4-c]quinoline compounds and pharmaceutical compositions, methods for their use and preparation
AU708882B2 (en)	1999-08-12	Novel compounds
JP2969911B2 (ja)	1999-11-02	チオフェン化合物、その医薬用途およびその合成中間体
AU617775B2 (en)	1991-12-05	Heterocyclic substituted 5,7-dihydropyrrolo (3,2-f)- benzoxazol-6-ones, processes for the preparation thereof and pharmaceutical compositions containing them
US4440768A (en)	1984-04-03	Hexahydropyrrolo[3,4-c]quinoline compounds and pharmaceutical compositions, and methods for their use
JPH0762017B2 (ja)	1995-07-05	多環式キノリン、ナフチリジンおよびピラジノピリジン誘導体
US4350814A (en)	1982-09-21	Pyrrolo [3,4-c]quinoline compounds
AU705938B2 (en)	1999-06-03	Pyridazino quinoline compounds
JPS61227584A (ja)	1986-10-09	ポリアザ複素環誘導体
US4521419A (en)	1985-06-04	Condensed cycloaliphatic derivatives of substituted pyrido[1,2-a]pyrimidines and methods of treating allergic conditions, peptic ulcers and inhibiting gastric acid secretion with them
US6214826B1 (en)	2001-04-10	Pyridazino quinoline compounds

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2003-03-20	MK14	Patent ceased section 143(a) (annual fees not paid) or expired