NL8801063A - Chinoline thioethers. - Google Patents

Chinoline thioethers. Download PDF

Info

Publication number: NL8801063A
Authority: NL; Netherlands
Prior art keywords: general formula; compound; formula; formula sheet; sheet
Prior art date: 1987-04-24

Application number

NL8801063A

Other languages

English (en)

Dutch (nl)

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

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.)

1987-04-24

Filing date

1988-04-22

Publication date

1988-11-16

1988-04-22 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

1988-11-16 Publication of NL8801063A publication Critical patent/NL8801063A/nl

Links

-1 QUINOLINE THIOETHERS Chemical class 0.000 title claims description 19
SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title description 10
150000001875 compounds Chemical class 0.000 claims description 86
150000003839 salts Chemical class 0.000 claims description 33
238000000034 method Methods 0.000 claims description 32
239000002253 acid Substances 0.000 claims description 31
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
230000000949 anxiolytic effect Effects 0.000 claims description 11
125000001589 carboacyl group Chemical group 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
239000002249 anxiolytic agent Substances 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
230000010933 acylation Effects 0.000 claims description 7
238000005917 acylation reaction Methods 0.000 claims description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
150000008065 acid anhydrides Chemical class 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
AHCXKCZNNMWWQM-UHFFFAOYSA-N 7-chloro-4-ethylsulfanylquinolin-3-amine Chemical compound ClC1=CC=C2C(SCC)=C(N)C=NC2=C1 AHCXKCZNNMWWQM-UHFFFAOYSA-N 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
239000000825 pharmaceutical preparation Substances 0.000 claims description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000006193 alkinyl group Chemical group 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
239000002609 medium Substances 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
239000002798 polar solvent Substances 0.000 claims description 4
229910052979 sodium sulfide Inorganic materials 0.000 claims description 4
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims description 4
IMCGVHYQOMAJAX-UHFFFAOYSA-N 3-nitro-1h-quinoline-4-thione Chemical compound C1=CC=CC2=C(S)C([N+](=O)[O-])=CN=C21 IMCGVHYQOMAJAX-UHFFFAOYSA-N 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
239000000203 mixture Substances 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
239000012736 aqueous medium Substances 0.000 claims description 2
125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
239000011230 binding agent Substances 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
JTWBDVCXSDAHKT-UHFFFAOYSA-N ClC1=CC=C2C=CC=NC2=C1.NC=1C=NC2=CC=CC=C2C1SCC Chemical compound ClC1=CC=C2C=CC=NC2=C1.NC=1C=NC2=CC=CC=C2C1SCC JTWBDVCXSDAHKT-UHFFFAOYSA-N 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
241000700159 Rattus Species 0.000 description 23
241001465754 Metazoa Species 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
238000002474 experimental method Methods 0.000 description 10
239000000047 product Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
208000007101 Muscle Cramp Diseases 0.000 description 9
229940079593 drug Drugs 0.000 description 9
239000003814 drug Substances 0.000 description 9
ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 8
229960004782 chlordiazepoxide Drugs 0.000 description 8
229960003529 diazepam Drugs 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
239000008188 pellet Substances 0.000 description 8
230000001624 sedative effect Effects 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
230000000049 anti-anxiety effect Effects 0.000 description 7
230000000694 effects Effects 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
229910000041 hydrogen chloride Inorganic materials 0.000 description 6
239000000872 buffer Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000007983 Tris buffer Substances 0.000 description 4
239000002585 base Substances 0.000 description 4
239000007979 citrate buffer Substances 0.000 description 4
230000035622 drinking Effects 0.000 description 4
239000006187 pill Substances 0.000 description 4
229920005862 polyol Polymers 0.000 description 4
150000003077 polyols Chemical class 0.000 description 4
239000000932 sedative agent Substances 0.000 description 4
QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 4
238000012360 testing method Methods 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
229940126062 Compound A Drugs 0.000 description 3
102000004300 GABA-A Receptors Human genes 0.000 description 3
108090000839 GABA-A Receptors Proteins 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000037396 body weight Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
238000005119 centrifugation Methods 0.000 description 3
235000013305 food Nutrition 0.000 description 3
239000007903 gelatin capsule Substances 0.000 description 3
238000011534 incubation Methods 0.000 description 3
231100000518 lethal Toxicity 0.000 description 3
230000001665 lethal effect Effects 0.000 description 3
238000005259 measurement Methods 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
YJBLTYRYUXKJLE-UHFFFAOYSA-N 3-amino-1h-quinoline-4-thione Chemical compound C1=CC=C2C(=S)C(N)=CNC2=C1 YJBLTYRYUXKJLE-UHFFFAOYSA-N 0.000 description 2
HPCLSFSEORFCOS-UHFFFAOYSA-N 3-amino-7-chloro-1h-quinoline-4-thione Chemical compound C1=C(Cl)C=CC2=C(S)C(N)=CN=C21 HPCLSFSEORFCOS-UHFFFAOYSA-N 0.000 description 2
ZWCPOYJWZMOJOR-UHFFFAOYSA-N 4-ethylsulfanylquinolin-3-amine Chemical compound C1=CC=C2C(SCC)=C(N)C=NC2=C1 ZWCPOYJWZMOJOR-UHFFFAOYSA-N 0.000 description 2
RCTCFMHYEPJDRG-UHFFFAOYSA-N 7-chloro-4-ethylsulfanylquinolin-3-amine;hydrochloride Chemical compound Cl.ClC1=CC=C2C(SCC)=C(N)C=NC2=C1 RCTCFMHYEPJDRG-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 2
LHNKBXRFNPMIBR-UHFFFAOYSA-N Picrotoxin Natural products CC(C)(O)C1(O)C2OC(=O)C1C3(O)C4OC4C5C(=O)OC2C35C LHNKBXRFNPMIBR-UHFFFAOYSA-N 0.000 description 2
241001279009 Strychnos toxifera Species 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
239000003513 alkali Substances 0.000 description 2
239000002168 alkylating agent Substances 0.000 description 2
229940100198 alkylating agent Drugs 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
239000008298 dragée Substances 0.000 description 2
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
239000003925 fat Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000011630 iodine Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000007788 liquid Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000463 material Substances 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
229960002695 phenobarbital Drugs 0.000 description 2
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 2
VJKUPQSHOVKBCO-AHMKVGDJSA-N picrotoxin Chemical compound O=C([C@@]12O[C@@H]1C[C@]1(O)[C@@]32C)O[C@@H]3[C@H]2[C@@H](C(=C)C)[C@@H]1C(=O)O2.O=C([C@@]12O[C@@H]1C[C@]1(O)[C@@]32C)O[C@@H]3[C@H]2[C@@H](C(C)(O)C)[C@@H]1C(=O)O2 VJKUPQSHOVKBCO-AHMKVGDJSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
229960005453 strychnine Drugs 0.000 description 2
238000007920 subcutaneous administration Methods 0.000 description 2
229960004793 sucrose Drugs 0.000 description 2
239000000829 suppository Substances 0.000 description 2
239000008399 tap water Substances 0.000 description 2
235000020679 tap water Nutrition 0.000 description 2
150000003573 thiols Chemical class 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
239000001993 wax Substances 0.000 description 2
DESYRYQLEHXUSU-UHFFFAOYSA-N 2-methylsulfanylquinoline;hydrochloride Chemical compound Cl.C1=CC=CC2=NC(SC)=CC=C21 DESYRYQLEHXUSU-UHFFFAOYSA-N 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
CFIHQMVJDWKMMI-UHFFFAOYSA-N 3-azidoquinoline Chemical compound C1=CC=CC2=CC(N=[N+]=[N-])=CN=C21 CFIHQMVJDWKMMI-UHFFFAOYSA-N 0.000 description 1
PHIWEHKXLBPYCK-UHFFFAOYSA-N 4-benzylsulfanyl-7-chloroquinolin-3-amine Chemical compound NC=1C=NC2=CC(=CC=C2C=1SCC1=CC=CC=C1)Cl PHIWEHKXLBPYCK-UHFFFAOYSA-N 0.000 description 1
BFAZSOLHSFOAOH-UHFFFAOYSA-N 4-methylsulfanylquinolin-3-amine;hydrochloride Chemical compound Cl.C1=CC=C2C(SC)=C(N)C=NC2=C1 BFAZSOLHSFOAOH-UHFFFAOYSA-N 0.000 description 1
MCIDOSPSVXOABU-UHFFFAOYSA-N 4-propylsulfanylquinolin-3-amine Chemical compound NC=1C=NC2=CC=CC=C2C=1SCCC MCIDOSPSVXOABU-UHFFFAOYSA-N 0.000 description 1
QLKOWRXUQGIAQU-UHFFFAOYSA-N 7-chloro-4-methylsulfanylquinolin-3-amine;hydrochloride Chemical compound Cl.ClC1=CC=C2C(SC)=C(N)C=NC2=C1 QLKOWRXUQGIAQU-UHFFFAOYSA-N 0.000 description 1
MYGXWPFHDQMCJB-UHFFFAOYSA-N 7-chloro-4-prop-2-ynylsulfanylquinolin-3-amine Chemical compound NC=1C=NC2=CC(=CC=C2C=1SCC#C)Cl MYGXWPFHDQMCJB-UHFFFAOYSA-N 0.000 description 1
RARFGWYBVLISQA-UHFFFAOYSA-N 7-chloro-4-propan-2-ylsulfanylquinolin-3-amine Chemical compound NC=1C=NC2=CC(=CC=C2C=1SC(C)C)Cl RARFGWYBVLISQA-UHFFFAOYSA-N 0.000 description 1
VWUFXLMFBSNWFU-UHFFFAOYSA-N 7-chloro-4-propylsulfanylquinolin-3-amine Chemical compound NC=1C=NC2=CC(=CC=C2C=1SCCC)Cl VWUFXLMFBSNWFU-UHFFFAOYSA-N 0.000 description 1
229940110385 Benzodiazepine receptor antagonist Drugs 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
NGMNYETXSRMEMS-UHFFFAOYSA-N Cl.NC=1C=NC2=CC(=C(C=C2C1SCC)OC)OC Chemical compound Cl.NC=1C=NC2=CC(=C(C=C2C1SCC)OC)OC NGMNYETXSRMEMS-UHFFFAOYSA-N 0.000 description 1
RHNNJBMMYQHDOH-UHFFFAOYSA-N Cl.NC=1C=NC2=CC=C(C=C2C1SCC)Cl Chemical compound Cl.NC=1C=NC2=CC=C(C=C2C1SCC)Cl RHNNJBMMYQHDOH-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
229920005372 Plexiglas® Polymers 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
238000000692 Student's t-test Methods 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000000556 agonist Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
230000002921 anti-spasmodic effect Effects 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
229960003965 antiepileptics Drugs 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
229940049706 benzodiazepine Drugs 0.000 description 1
239000000749 benzodiazepine receptor blocking agent Substances 0.000 description 1
150000001557 benzodiazepines Chemical class 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000012490 blank solution Substances 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013256 coordination polymer Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
230000009089 cytolysis Effects 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
235000013681 dietary sucrose Nutrition 0.000 description 1
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
229940008406 diethyl sulfate Drugs 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
XDRMBCMMABGNMM-UHFFFAOYSA-N ethyl benzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=CC=C1 XDRMBCMMABGNMM-UHFFFAOYSA-N 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
235000003642 hunger Nutrition 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
239000003446 ligand Substances 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000014380 magnesium carbonate Nutrition 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000012528 membrane Substances 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
LCBWVXLDBWYMRH-UHFFFAOYSA-N n-(4-ethylsulfanylquinolin-3-yl)acetamide Chemical compound C1=CC=C2C(SCC)=C(NC(C)=O)C=NC2=C1 LCBWVXLDBWYMRH-UHFFFAOYSA-N 0.000 description 1
PNZDXYQNQSEQQW-UHFFFAOYSA-N n-(4-methylsulfanylquinolin-3-yl)acetamide Chemical compound C1=CC=C2C(SC)=C(NC(C)=O)C=NC2=C1 PNZDXYQNQSEQQW-UHFFFAOYSA-N 0.000 description 1
NOPJILNRRAFNTI-UHFFFAOYSA-N n-(4-propylsulfanylquinolin-3-yl)acetamide Chemical compound C1=CC=C2C(SCCC)=C(NC(C)=O)C=NC2=C1 NOPJILNRRAFNTI-UHFFFAOYSA-N 0.000 description 1
PRBRYOIPARHJCU-UHFFFAOYSA-N n-(7-chloro-4-methylsulfanylquinolin-3-yl)acetamide Chemical compound ClC1=CC=C2C(SC)=C(NC(C)=O)C=NC2=C1 PRBRYOIPARHJCU-UHFFFAOYSA-N 0.000 description 1
IRXXCJTVINCDOE-UHFFFAOYSA-N n-(7-chloro-4-propan-2-ylsulfanylquinolin-3-yl)acetamide Chemical compound ClC1=CC=C2C(SC(C)C)=C(NC(C)=O)C=NC2=C1 IRXXCJTVINCDOE-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000001537 neural effect Effects 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
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
WRLGYAWRGXKSKG-UHFFFAOYSA-M phenobarbital sodium Chemical compound [Na+].C=1C=CC=CC=1C1(CC)C(=O)NC([O-])=NC1=O WRLGYAWRGXKSKG-UHFFFAOYSA-M 0.000 description 1
238000006303 photolysis reaction Methods 0.000 description 1
230000015843 photosynthesis, light reaction Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000004926 polymethyl methacrylate Substances 0.000 description 1
229920001592 potato starch Polymers 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
230000001681 protective effect Effects 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
239000002994 raw material Substances 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
235000002639 sodium chloride Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 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
238000010257 thawing Methods 0.000 description 1
238000001149 thermolysis Methods 0.000 description 1
230000001256 tonic effect Effects 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- 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
- C07D215/36—Sulfur atoms
- 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
- C07D215/38—Nitrogen atoms
- 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
- A61P25/22—Anxiolytics

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Biomedical Technology (AREA)
Public Health (AREA)
Anesthesiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Quinoline Compounds (AREA)

NL8801063A 1987-04-24 1988-04-22 Chinoline thioethers. NL8801063A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU871778A HU199424B (en)	1987-04-24	1987-04-24	Process for producing quinoline thioethers and pharmaceutical compositions comprising such compounds
HU177887		1987-04-24

Publications (1)

Publication Number	Publication Date
NL8801063A true NL8801063A (nl)	1988-11-16

Family

ID=10956151

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8801063A NL8801063A (nl)	1987-04-24	1988-04-22	Chinoline thioethers.

Country Status (26)

Country	Link
US (1)	US4921960A (it)
JP (1)	JPS63280067A (it)
KR (1)	KR880012557A (it)
CN (1)	CN88102436A (it)
AT (1)	AT394553B (it)
AU (1)	AU602209B2 (it)
CH (1)	CH675876A5 (it)
DD (1)	DD284676A5 (it)
DE (1)	DE3813675A1 (it)
DK (1)	DK220388A (it)
ES (1)	ES2009601A6 (it)
FI (1)	FI881921A7 (it)
FR (1)	FR2618431B1 (it)
GB (1)	GB2204583B (it)
GR (1)	GR1000471B (it)
HU (1)	HU199424B (it)
IL (1)	IL86148A (it)
IT (1)	IT1217192B (it)
NL (1)	NL8801063A (it)
PH (1)	PH24864A (it)
PL (1)	PL272026A1 (it)
PT (1)	PT87311B (it)
SE (1)	SE8801505L (it)
SU (1)	SU1609446A3 (it)
YU (1)	YU81688A (it)
ZA (1)	ZA882862B (it)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU199423B (en) *	1987-04-24	1990-02-28	Egyt Gyogyszervegyeszeti Gyar	Process for producing 3-amino-4-/ethylthio/-quinoline and pharmaceutical compositions comprising such compounds
RU2136679C1 (ru) *	1998-07-06	1999-09-10	Пермская государственная фармацевтическая академия	5-нитрофурфурилиденгидразид 2-амино-5,6,7,8-тетрагидрохинолин-3-карбоновой кислоты

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2918591A1 (de) *	1979-05-09	1980-11-20	Hoechst Ag	Neue 4-substituierte 5,6,7,8-tetrahydrochinoline, ihre herstellung und verwendung
FR2582514B1 (fr) *	1985-05-30	1988-02-19	Rhone Poulenc Sante	Medicaments a base d'amides, nouveaux amides et leur preparation
HU199423B (en) *	1987-04-24	1990-02-28	Egyt Gyogyszervegyeszeti Gyar	Process for producing 3-amino-4-/ethylthio/-quinoline and pharmaceutical compositions comprising such compounds

1987
- 1987-04-24 HU HU871778A patent/HU199424B/hu not_active IP Right Cessation
1988
- 1988-04-18 PH PH36809A patent/PH24864A/en unknown
- 1988-04-20 CH CH1477/88A patent/CH675876A5/de not_active IP Right Cessation
- 1988-04-22 FR FR888805337A patent/FR2618431B1/fr not_active Expired - Lifetime
- 1988-04-22 ES ES8801244A patent/ES2009601A6/es not_active Expired
- 1988-04-22 ZA ZA882862A patent/ZA882862B/xx unknown
- 1988-04-22 KR KR1019880004593A patent/KR880012557A/ko not_active Withdrawn
- 1988-04-22 PL PL27202688A patent/PL272026A1/xx unknown
- 1988-04-22 GR GR880100265A patent/GR1000471B/el unknown
- 1988-04-22 CN CN198888102436A patent/CN88102436A/zh active Pending
- 1988-04-22 IT IT20306/88A patent/IT1217192B/it active
- 1988-04-22 DD DD88315011A patent/DD284676A5/de not_active IP Right Cessation
- 1988-04-22 DE DE3813675A patent/DE3813675A1/de not_active Withdrawn
- 1988-04-22 DK DK220388A patent/DK220388A/da not_active Application Discontinuation
- 1988-04-22 IL IL86148A patent/IL86148A/xx unknown
- 1988-04-22 SE SE8801505A patent/SE8801505L/xx not_active Application Discontinuation
- 1988-04-22 JP JP63098434A patent/JPS63280067A/ja active Pending
- 1988-04-22 AT AT0103088A patent/AT394553B/de not_active IP Right Cessation
- 1988-04-22 US US07/184,796 patent/US4921960A/en not_active Expired - Fee Related
- 1988-04-22 NL NL8801063A patent/NL8801063A/nl not_active Application Discontinuation
- 1988-04-22 AU AU15105/88A patent/AU602209B2/en not_active Ceased
- 1988-04-22 PT PT87311A patent/PT87311B/pt not_active IP Right Cessation
- 1988-04-22 YU YU00816/88A patent/YU81688A/xx unknown
- 1988-04-22 FI FI881921A patent/FI881921A7/fi not_active IP Right Cessation
- 1988-04-22 SU SU884355577A patent/SU1609446A3/ru active
- 1988-04-22 GB GB8809520A patent/GB2204583B/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
DK220388A (da)	1988-10-25
GR880100265A (en)	1989-01-31
SU1609446A3 (ru)	1990-11-23
DK220388D0 (da)	1988-04-22
ZA882862B (en)	1989-01-25
IL86148A0 (en)	1988-11-15
GB2204583A (en)	1988-11-16
IL86148A (en)	1991-09-16
JPS63280067A (ja)	1988-11-17
DE3813675A1 (de)	1988-11-17
HUT49579A (en)	1989-10-30
GR1000471B (el)	1992-07-30
SE8801505L (sv)	1988-10-25
US4921960A (en)	1990-05-01
DD284676A5 (de)	1990-11-21
PH24864A (en)	1990-12-26
IT8820306A0 (it)	1988-04-22
PT87311B (pt)	1992-08-31
HU199424B (en)	1990-02-28
FR2618431A1 (fr)	1989-01-27
FR2618431B1 (fr)	1992-04-03
CN88102436A (zh)	1988-11-09
FI881921A7 (fi)	1988-10-25
FI881921A0 (fi)	1988-04-22
SE8801505D0 (sv)	1988-04-22
ATA103088A (de)	1991-10-15
AU1510588A (en)	1988-10-27
YU81688A (en)	1989-10-31
CH675876A5 (it)	1990-11-15
ES2009601A6 (es)	1989-10-01
IT1217192B (it)	1990-03-14
PL272026A1 (en)	1989-01-23
GB8809520D0 (en)	1988-05-25
AT394553B (de)	1992-05-11
GB2204583B (en)	1991-03-27
KR880012557A (ko)	1988-11-28
AU602209B2 (en)	1990-10-04
PT87311A (pt)	1988-05-01

Legal Events

Date	Code	Title	Description
1992-12-01	BV	The patent application has lapsed

Publication	Publication Date	Title
JP2003529591A (ja)	2003-10-07	ベンゾイルピラゾールおよび除草剤としてのその使用
EP0201735B1 (de)	1990-09-12	N-Indolylethyl-sulfonsäureamide, Verfahren zu ihrer Herstellung und ihre Verwendung
DE1493955A1 (de)	1971-08-19	Verfahren zur Herstellung substituierter Sulfonanilide
EP0778271A2 (de)	1997-06-11	Aminoalkyl-substituierte benzo-heterocyclische Verbindungen
CH644597A5 (de)	1984-08-15	Imidazolderivate, verfahren zu ihrer herstellung und diese enthaltende arzneimittel.
EA016883B1 (ru)	2012-08-30	4-(4-трифторметил-3-тиобензоил)пиразолы и их применение в качестве гербицидов
JPS63500310A (ja)	1988-02-04	新規カルボン酸誘導体、その製法、その使用並びにこの化合物を含有する医薬品
EP0021973A2 (fr)	1981-01-07	Aminopipéridines anorexigènes, procédé pour leur préparation et médicaments les contenant
DE3872620T2 (de)	1992-12-03	(arylsulphonyl)-nitromethane, verfahren zu deren herstellung und deren verwendung in pharmazeutischen zusammensetzungen.
CH632495A5 (de)	1982-10-15	Verfahren zur herstellung neuer substituierter pyridine.
FR2567519A1 (fr)	1986-01-17	Nouvelles isoindolinyl-alcoyl-piperazines, compositions pharmaceutiques les contenant, et leur procede de preparation
CH635481A5 (de)	1983-04-15	Fungizides mittel.
NL8801063A (nl)	1988-11-16	Chinoline thioethers.
HU203726B (en)	1991-09-30	Fungicide compositions containing 2-anilino-cyanopyridines as active components and process for producing the active components
EP0177907B1 (de)	1988-06-01	Neue 2-Pyridin-thiol-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
JPS6348266A (ja)	1988-02-29	ヘテロアリ−ルエチルアミン、その製造法及びその家畜生産促進剤としての使用
US3453365A (en)	1969-07-01	Substituted quinoxalines as fungicides
CN86101080A (zh)	1986-10-22	咪唑衍生物的制备方法和作为杀菌剂的应用
DE3138121A1 (de)	1982-04-15	Chinolone, verfahren zur ihrer herstellung und ihre verwendung in therapeutischen zubereitungen
CH631965A5 (en)	1982-09-15	2-Trifluoromethylalkanesulphonanilides substituted in the p position, and agents and methods for modifying plant growth
FR2753450A1 (fr)	1998-03-20	Heteroaryloxypyridines herbicides
US4289765A (en)	1981-09-15	4-Aminopyridines and medicaments containing the same
DE3804346A1 (de)	1989-08-24	Tert.-butylphenyl-pyridyl-amide - verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel
DE3003933A1 (de)	1981-08-13	(beta) -imidazolylalkohole, verfahren zu ihrer herstellung, diese enthaltende fungizide und verfahren zur bekaempfung von pilzen mit ihnen
EP0007067A1 (de)	1980-01-23	Neue Phenylpiperidinderivate, Verfahren zu ihrer Herstellung, diese enthaltende pharmazeutische Präparate und ihre Verwendung