FI68827C - Analogifoerfarande foer framstaellning av nya terapeutiskt verkande 2-fenyl- eller -pyridyl-pyrazolo(4,3-c)kinolin-3(1 och5h)-oni-foereningar - Google Patents

Analogifoerfarande foer framstaellning av nya terapeutiskt verkande 2-fenyl- eller -pyridyl-pyrazolo(4,3-c)kinolin-3(1 och5h)-oni-foereningar Download PDF

Info

Publication number: FI68827C
Authority: FI; Finland
Prior art keywords: hydroxy; phenyl; alkyl; hydrogen; mixture
Prior art date: 1979-06-21

Application number

FI801964A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI801964A7 (fi

FI68827B (fi

Inventor

Naokata Yokoyama

Original Assignee

Ciba Geigy Ag

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.)

1979-06-21

Filing date

1980-06-18

Publication date

1985-11-11

1980-06-18 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1980-12-22 Publication of FI801964A7 publication Critical patent/FI801964A7/fi

1985-07-31 Application granted granted Critical

1985-07-31 Publication of FI68827B publication Critical patent/FI68827B/fi

1985-11-11 Publication of FI68827C publication Critical patent/FI68827C/fi

Links

230000001225 therapeutic effect Effects 0.000 title 2
150000001875 compounds Chemical class 0.000 claims abstract description 79
238000000034 method Methods 0.000 claims abstract description 20
238000002360 preparation method Methods 0.000 claims abstract description 11
239000000203 mixture Substances 0.000 abstract description 75
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 44
150000003839 salts Chemical class 0.000 abstract description 35
-1 nitro, amino Chemical group 0.000 abstract description 29
229910052739 hydrogen Inorganic materials 0.000 abstract description 28
239000001257 hydrogen Substances 0.000 abstract description 28
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 15
150000002431 hydrogen Chemical class 0.000 abstract description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 10
229910052783 alkali metal Inorganic materials 0.000 abstract description 9
125000004432 carbon atom Chemical group C* 0.000 abstract description 8
229910052736 halogen Inorganic materials 0.000 abstract description 8
150000002367 halogens Chemical class 0.000 abstract description 8
229910052757 nitrogen Inorganic materials 0.000 abstract description 5
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract description 5
125000004076 pyridyl group Chemical group 0.000 abstract description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract description 4
125000003277 amino group Chemical group 0.000 abstract description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 3
150000002148 esters Chemical class 0.000 abstract description 3
125000006377 halopyridyl group Chemical group 0.000 abstract description 3
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
125000004356 hydroxy functional group Chemical group O* 0.000 abstract 2
125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract 1
125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 132
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 72
239000000243 solution Substances 0.000 description 68
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
238000002844 melting Methods 0.000 description 30
230000008018 melting Effects 0.000 description 30
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
125000001309 chloro group Chemical group Cl* 0.000 description 27
239000002244 precipitate Substances 0.000 description 25
239000002253 acid Substances 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000007858 starting material Substances 0.000 description 21
238000003756 stirring Methods 0.000 description 20
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
125000000217 alkyl group Chemical group 0.000 description 13
150000007513 acids Chemical class 0.000 description 12
239000000460 chlorine Substances 0.000 description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
239000012299 nitrogen atmosphere Substances 0.000 description 10
235000019270 ammonium chloride Nutrition 0.000 description 9
230000000202 analgesic effect Effects 0.000 description 9
229910052801 chlorine Inorganic materials 0.000 description 9
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 9
229960003529 diazepam Drugs 0.000 description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
239000000047 product Substances 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
QCBUAKLOWCOUCR-UHFFFAOYSA-N cgs-9896 Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(C=NC=2C3=CC=CC=2)=C3N1 QCBUAKLOWCOUCR-UHFFFAOYSA-N 0.000 description 8
238000002329 infrared spectrum Methods 0.000 description 8
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
239000007787 solid Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
125000003545 alkoxy group Chemical group 0.000 description 7
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 7
230000002829 reductive effect Effects 0.000 description 7
MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
239000000935 antidepressant agent Substances 0.000 description 6
229940005513 antidepressants Drugs 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
239000000908 ammonium hydroxide Substances 0.000 description 5
230000001430 anti-depressive effect Effects 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
239000002585 base Substances 0.000 description 5
DWXQUAHMZWZXHP-UHFFFAOYSA-N ethyl 4-chloroquinoline-3-carboxylate Chemical compound C1=CC=CC2=C(Cl)C(C(=O)OCC)=CN=C21 DWXQUAHMZWZXHP-UHFFFAOYSA-N 0.000 description 5
230000005496 eutectics Effects 0.000 description 5
239000011737 fluorine Substances 0.000 description 5
229910052731 fluorine Inorganic materials 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000006798 ring closing metathesis reaction Methods 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
239000008096 xylene Substances 0.000 description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
XXNOGQJZAOXWAQ-UHFFFAOYSA-N 4-chlorophenylhydrazine Chemical compound NNC1=CC=C(Cl)C=C1 XXNOGQJZAOXWAQ-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
239000010410 layer Substances 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
229940067157 phenylhydrazine Drugs 0.000 description 4
238000010992 reflux Methods 0.000 description 4
ZRBQFABJKIWBNM-UHFFFAOYSA-N 2-(4-aminophenyl)-1h-pyrazolo[4,3-c]quinolin-3-one Chemical compound C1=CC(N)=CC=C1N1C(=O)C(C=NC=2C3=CC=CC=2)=C3N1 ZRBQFABJKIWBNM-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
ZLXQYMXMWMJOOP-UHFFFAOYSA-N N1=C(C2=CC=CC=C2NC=2)C=2C(=O)N1C1=CC=C(C#N)C=C1 Chemical compound N1=C(C2=CC=CC=C2NC=2)C=2C(=O)N1C1=CC=C(C#N)C=C1 ZLXQYMXMWMJOOP-UHFFFAOYSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000013543 active substance Substances 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
238000010171 animal model Methods 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 3
229910000103 lithium hydride Inorganic materials 0.000 description 3
239000012528 membrane Substances 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
235000010446 mineral oil Nutrition 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 3
230000035939 shock Effects 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
IXVPIGBFJRYAPQ-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-methylpyrazolo[4,3-c]quinolin-3-one Chemical compound O=C1C2=CN=C3C=CC=CC3=C2N(C)N1C1=CC=C(Cl)C=C1 IXVPIGBFJRYAPQ-UHFFFAOYSA-N 0.000 description 2
IHNINSVQYKIZIC-UHFFFAOYSA-N 2h-quinolin-3-one Chemical class C1=CC=CC2=CC(=O)CN=C21 IHNINSVQYKIZIC-UHFFFAOYSA-N 0.000 description 2
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
208000020401 Depressive disease Diseases 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
BLTGIWZTJSMQPE-UHFFFAOYSA-N OC=C1C(=O)N(C=2C=CC(Cl)=CC=2)N=C1C1=CC=CC=C1[N+]([O-])=O Chemical compound OC=C1C(=O)N(C=2C=CC(Cl)=CC=2)N=C1C1=CC=CC=C1[N+]([O-])=O BLTGIWZTJSMQPE-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
125000003282 alkyl amino group Chemical group 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000000872 buffer Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
239000007884 disintegrant Substances 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
239000003480 eluent Substances 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
HZHSJAYMOBNJHB-UHFFFAOYSA-N ethyl 4-[2-(2,4-dichlorophenyl)hydrazinyl]quinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2C=CC=CC2=C1NNC1=CC=C(Cl)C=C1Cl HZHSJAYMOBNJHB-UHFFFAOYSA-N 0.000 description 2
238000009472 formulation Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000002609 medium Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical compound COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
PDRXPVRLRSMGQE-UHFFFAOYSA-N n-[2-[1-(4-chlorophenyl)-5-oxo-4h-pyrazol-3-yl]phenyl]formamide Chemical compound C1=CC(Cl)=CC=C1N1C(=O)CC(C=2C(=CC=CC=2)NC=O)=N1 PDRXPVRLRSMGQE-UHFFFAOYSA-N 0.000 description 2
239000003921 oil Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229920000137 polyphosphoric acid Polymers 0.000 description 2
238000012746 preparative thin layer chromatography Methods 0.000 description 2
210000004129 prosencephalon Anatomy 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
235000015424 sodium Nutrition 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
238000010998 test method Methods 0.000 description 2
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
ZTPAUBJZUBGGEY-UHFFFAOYSA-N (2,4-dichlorophenyl)hydrazine Chemical compound NNC1=CC=C(Cl)C=C1Cl ZTPAUBJZUBGGEY-UHFFFAOYSA-N 0.000 description 1
ZXBMIRYQUFQQNX-UHFFFAOYSA-N (4-fluorophenyl)hydrazine Chemical compound NNC1=CC=C(F)C=C1 ZXBMIRYQUFQQNX-UHFFFAOYSA-N 0.000 description 1
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239000012362 glacial acetic acid Substances 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
125000004969 haloethyl group Chemical group 0.000 description 1
PUYCICVJCRLABY-UHFFFAOYSA-N heptane;oxolane Chemical compound C1CCOC1.CCCCCCC PUYCICVJCRLABY-UHFFFAOYSA-N 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
UWYVPFMHMJIBHE-OWOJBTEDSA-N hydroxymaleic acid group Chemical group O/C(/C(=O)O)=C/C(=O)O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
230000003993 interaction Effects 0.000 description 1
150000002527 isonitriles Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000155 melt Substances 0.000 description 1
201000003102 mental depression Diseases 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 1
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
239000002899 monoamine oxidase inhibitor Substances 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000004776 neurological deficiency Effects 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229960002715 nicotine Drugs 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
125000001209 o-nitrophenyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])[N+]([O-])=O 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
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000006072 paste Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
230000036515 potency Effects 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
NWELCUKYUCBVKK-UHFFFAOYSA-N pyridin-2-ylhydrazine Chemical compound NNC1=CC=CC=N1 NWELCUKYUCBVKK-UHFFFAOYSA-N 0.000 description 1
238000005932 reductive alkylation reaction Methods 0.000 description 1
238000005057 refrigeration Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000011664 signaling Effects 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
230000009870 specific binding Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000010414 supernatant solution Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000010409 thin film Substances 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
239000003029 tricyclic antidepressant agent Substances 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
238000009736 wetting Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/28—Two oxygen or sulfur atoms
- C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
- C07D231/32—Oxygen atoms

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Neurosurgery (AREA)
Life Sciences & Earth Sciences (AREA)
Biomedical Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Neurology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Anesthesiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

FI801964A 1979-06-21 1980-06-18 Analogifoerfarande foer framstaellning av nya terapeutiskt verkande 2-fenyl- eller -pyridyl-pyrazolo(4,3-c)kinolin-3(1 och5h)-oni-foereningar FI68827C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US5071679A	1979-06-21	1979-06-21
US5071679		1979-06-21

Publications (3)

Publication Number	Publication Date
FI801964A7 FI801964A7 (fi)	1980-12-22
FI68827B FI68827B (fi)	1985-07-31
FI68827C true FI68827C (fi)	1985-11-11

Family

ID=21966959

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI801964A FI68827C (fi)	1979-06-21	1980-06-18	Analogifoerfarande foer framstaellning av nya terapeutiskt verkande 2-fenyl- eller -pyridyl-pyrazolo(4,3-c)kinolin-3(1 och5h)-oni-foereningar

Country Status (22)

Country	Link
EP (1)	EP0022078B1 (2)
JP (1)	JPS5618980A (2)
KR (1)	KR840000421B1 (2)
AT (1)	ATE8629T1 (2)
AU (1)	AU538890B2 (2)
CA (1)	CA1148159A (2)
CY (1)	CY1357A (2)
DD (1)	DD151754A5 (2)
DE (1)	DE3068673D1 (2)
DK (1)	DK160762C (2)
FI (1)	FI68827C (2)
GR (1)	GR69282B (2)
HK (1)	HK47387A (2)
HU (1)	HU183156B (2)
IE (1)	IE49993B1 (2)
IL (1)	IL60357A (2)
MY (1)	MY8700556A (2)
NO (1)	NO153430C (2)
NZ (1)	NZ194102A (2)
PT (1)	PT71420A (2)
SG (1)	SG14387G (2)
ZA (1)	ZA803714B (2)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4459298A (en) *	1982-09-28	1984-07-10	Ciba-Geigy Corporation	Method of suppressing appetite
US4524146A (en) *	1982-12-08	1985-06-18	Ciba-Geigy Corporation	Certain -2-heterocycle substituted pyrazoloquinolines
US4479955A (en) *	1983-01-10	1984-10-30	Ciba-Geigy Corporation	Heterocycle-fused pyrazolo[3,4-d]pyridin-3-ones as benzodiazepine receptor modulators
EP0126970A3 (en) *	1983-04-27	1985-11-06	Beecham Group Plc	Anxiolytic and anti-depressant thienopyridine derivatives
FR2549833B1 (fr) *	1983-07-26	1985-11-08	Roussel Uclaf	Derives de la pyrazolo /4,3-c/ cinnolin-3-one, leurs sels, procede de preparation, application a titre de medicaments, compositions les renfermant et produits intermediaires
CA1263651A (en) *	1984-07-09	1989-12-05	Ciba-Geigy Ag	Certain ring-fused pyrazolo ¬3,4-d\|-pyridin-3-one derivatives
PH21213A (en) *	1984-10-26	1987-08-21	Fujisawa Pharmaceutical Co	Benzene- and pyrazole- fused heterocyclic compound and pharmaceutical composition comprising the same
JPS61112075A (ja) *	1984-11-05	1986-05-30	Shionogi & Co Ltd	チエニルピラゾロキノリン誘導体
DE3728278A1 (de) *	1986-12-17	1988-06-23	Bayer Ag	Herbizide und fungizide mittel auf basis von substituierten pyrazolin-5-on derivaten
US5243049A (en) *	1992-01-22	1993-09-07	Neurogen Corporation	Certain pyrroloquinolinones: a new class of GABA brain receptor ligands
GB9625398D0 (en) *	1996-12-06	1997-01-22	Merck Sharp & Dohme	Method of treatment,manufacture,compositions and compounds
US6835707B1 (en)	1998-10-13	2004-12-28	The Procter & Gamble Company	Laundry detergent compositions with a combination of cyclic amine based polymers and hydrophobically modified carboxy methyl cellulose
GB0305876D0 (en) *	2003-03-14	2003-04-16	Avidex Ltd	Immuno inhibitory heterocyclic compounds
US7863266B2 (en) *	2007-06-08	2011-01-04	Helicon Therapeutics, Inc.	Therapeutic pyrazoloquinoline urea derivatives
EP2483275B1 (en) *	2009-10-01	2014-10-15	Merck Sharp & Dohme Corp.	HETEROCYCLIC-FUSED PYRAZOLO[4,3-c]PYRIDIN-3-ONE M1 RECEPTOR POSITIVE ALLOSTERIC MODULATORS
EP2490692B1 (en) *	2009-10-21	2016-11-16	Merck Sharp & Dohme Corp.	Quinolinone-pyrazolone m1 receptor positive allosteric modulators
BR112013026744B1 (pt)	2011-04-21	2022-05-17	Origenis Gmbh	Compostos heterocíclicos, seus usos e seus intermediários, e composição farmacêutica
WO2014060113A1 (en)	2012-10-19	2014-04-24	Origenis Gmbh	Novel kinase inhibitors
CN114891236B (zh) *	2022-06-09	2023-04-28	安庆师范大学	一种三维Co-MOF化合物及其制备方法和应用

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3890324A (en) *	1974-04-12	1975-06-17	Lilly Co Eli	1h-pyrazolo(4,3-)quinol-4(5h)-one-3-carboxylic acids
DE2963332D1 (en) *	1978-05-26	1982-09-02	Lepetit Spa	Pyrazolo (3,4-c) and thiazolo (5,4-c) isoquinolines, methods for preparing them, these compounds for use as antiinflammatory, cns-depressant and anti-anxiety agents and pharmaceutical compositions thereof

1980
- 1980-06-16 CY CY135780A patent/CY1357A/xx unknown
- 1980-06-16 DE DE8080810200T patent/DE3068673D1/de not_active Expired
- 1980-06-16 EP EP80810200A patent/EP0022078B1/de not_active Expired
- 1980-06-16 AT AT80810200T patent/ATE8629T1/de not_active IP Right Cessation
- 1980-06-18 FI FI801964A patent/FI68827C/fi not_active IP Right Cessation
- 1980-06-19 PT PT71420A patent/PT71420A/pt unknown
- 1980-06-19 IL IL60357A patent/IL60357A/xx unknown
- 1980-06-19 CA CA000354349A patent/CA1148159A/en not_active Expired
- 1980-06-19 GR GR62257A patent/GR69282B/el unknown
- 1980-06-20 AU AU59455/80A patent/AU538890B2/en not_active Ceased
- 1980-06-20 ZA ZA00803714A patent/ZA803714B/xx unknown
- 1980-06-20 NZ NZ194102A patent/NZ194102A/xx unknown
- 1980-06-20 KR KR1019800002438A patent/KR840000421B1/ko not_active Expired
- 1980-06-20 DK DK264880A patent/DK160762C/da not_active IP Right Cessation
- 1980-06-20 IE IE1279/80A patent/IE49993B1/en not_active IP Right Cessation
- 1980-06-20 NO NO801866A patent/NO153430C/no unknown
- 1980-06-21 JP JP8449380A patent/JPS5618980A/ja active Granted
- 1980-06-23 DD DD80222091A patent/DD151754A5/de unknown
- 1980-08-21 HU HU801539A patent/HU183156B/hu unknown
1987
- 1987-02-17 SG SG143/87A patent/SG14387G/en unknown
- 1987-06-18 HK HK473/87A patent/HK47387A/xx unknown
- 1987-12-30 MY MY556/87A patent/MY8700556A/xx unknown

Also Published As

Publication number	Publication date
DD151754A5 (de)	1981-11-04
EP0022078B1 (de)	1984-07-25
IE49993B1 (en)	1986-01-22
GR69282B (2)	1982-05-13
NO801866L (no)	1980-12-22
ATE8629T1 (de)	1984-08-15
JPS5618980A (en)	1981-02-23
NO153430C (no)	1986-03-19
PT71420A (en)	1980-07-01
EP0022078A1 (de)	1981-01-07
DE3068673D1 (en)	1984-08-30
CY1357A (en)	1987-08-07
SG14387G (en)	1987-07-10
KR840000421B1 (ko)	1984-04-02
AU538890B2 (en)	1984-08-30
DK160762B (da)	1991-04-15
KR830002763A (ko)	1983-05-30
IL60357A (en)	1984-05-31
DK264880A (da)	1980-12-22
ZA803714B (en)	1981-06-24
CA1148159A (en)	1983-06-14
NO153430B (no)	1985-12-09
IL60357A0 (en)	1980-09-16
AU5945580A (en)	1981-01-08
MY8700556A (en)	1987-12-31
DK160762C (da)	1991-09-23
JPH039114B2 (2)	1991-02-07
FI801964A7 (fi)	1980-12-22
NZ194102A (en)	1983-04-12
FI68827B (fi)	1985-07-31
HK47387A (en)	1987-06-26
HU183156B (en)	1984-04-28
IE801279L (en)	1980-12-21

Legal Events

Date	Code	Title	Description
1995-01-11	MM	Patent lapsed
2004-08-31	MM	Patent lapsed	Owner name: CIBA-GEIGY AG

Publication	Publication Date	Title
FI68827B (fi)	1985-07-31	Analogifoerfarande foer framstaellning av nya terapeutiskt verkande 2-fenyl- eller -pyridyl-pyrazolo(4,3-c)kinolin-3(1 och5h)-oni-foereningar
US4312870A (en)	1982-01-26	Pyrazoloquinolines
US5112820A (en)	1992-05-12	Anti-glaucoma compositions containing 2- and 3-aminomethyl-6-arylcarbonyl- or 6-phenylthio-2,3-dihydropyrrolo-(1,2,3-de)-1,4-benzoxazines and method of use thereof
AU8713998A (en)	1999-04-29	Amide derivative
US6451809B2 (en)	2002-09-17	Oxo-pyridoimidazole-carboxamides: GABA brain receptor ligands
CH674368A5 (2)	1990-05-31
FI77865C (fi)	1989-05-10	Foerfarande foer framstaellning av terapeutiskt anvaendbara benso/b/pyrrolo/3,2,1-j,k//1,4/bensodiazepinderivat.
US5512590A (en)	1996-04-30	5,6-dihydro-4h-imidazo 2',1':2,3!imidazo- 4,5,1-ij!quinoline and 4,5-dihydroimidazo- 1,2-a!pyrolo 1,2,3-cd!benzimidazole derivatives, their preparation and application in therapeutics
HUP0002650A2 (hu)	2001-01-29	4-Oxo-3,5-dihidro-4H-piridazino[4,5-b]-indol-1-acetamid-származékok, eljárás a vegyületek előállítására és a vegyületeket tartalmazó gyógyszerkészítmények
NO873108L (no)	1988-01-26	Fremgangsmaate for fremstilling av terapeutisk aktive 1,4-benzodiazepiner.
JPH0225486A (ja)	1990-01-26	新規イミダゾキノキサリン化合物、その製造方法並びにその使用
Hall et al.	1977	Quinoline derivatives as antiallergy agents. 2. Fused-ring quinaldic acids
FI83775C (fi)	1991-08-26	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara bensazepinderivat.
US4268513A (en)	1981-05-19	Pyrrolo [3,4-c]quinoline compounds and pharmaceutical compositions, methods for their use and preparation
US4440768A (en)	1984-04-03	Hexahydropyrrolo[3,4-c]quinoline compounds and pharmaceutical compositions, and methods for their use
NO823132L (no)	1983-03-17	Framgangsmaate til fremstilling av nye polycykliske polyazaheterocykler.
US4771052A (en)	1988-09-13	Tetrahydropyrido[3',4':4,5]pyrrolo[2,3-c]quinolines and their use as hypotensive agents
US4806560A (en)	1989-02-21	Imidazo[4,5-b]pyridin-2-one derivatives
US5278158A (en)	1994-01-11	Oxazinobenzazole compounds
FI74470C (fi)	1988-02-08	Foerfarande foer framstaellning av 5-pyridyletenylderivat av 1h-pyrazolo/1,5-a/pyrimidiner.
US4350814A (en)	1982-09-21	Pyrrolo [3,4-c]quinoline compounds
JPS59141580A (ja)	1984-08-14	インド−ル誘導体
US4324786A (en)	1982-04-13	Pyrido[2,3-e]-as-triazine derivatives and pharmaceutical compositions
JPWO1998031679A1 (ja)	2000-02-29	チオフェン化合物およびその医薬用途
US4880818A (en)	1989-11-14	1-Acyl-4-[1-(4-quinolinyl)-hydrazin-2-ylidene]piperidines and their use as hypotensive agents