NO800085L - Nye fenantrolinderivater, fremgangsmaate til deres fremstilling, farmasoeytiske preparater inneholdende disse og deres anvendelse - Google Patents

Nye fenantrolinderivater, fremgangsmaate til deres fremstilling, farmasoeytiske preparater inneholdende disse og deres anvendelse

Info

Publication number: NO800085L
Authority: NO; Norway
Prior art keywords: carbon atoms; formula; alkyl; lower alkyl; salt
Prior art date: 1979-01-16

Application number

NO800085A

Other languages

English (en)

Norwegian (no)

Inventor

Georges Haas

Knut A Jaeggi

Alberto Rossi

Alex Sele

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.)

1979-01-16

Filing date

1980-01-15

Publication date

1980-07-17

1980-01-15 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1980-07-17 Publication of NO800085L publication Critical patent/NO800085L/no

Links

238000000034 method Methods 0.000 title claims description 28
238000002360 preparation method Methods 0.000 title claims description 9
239000000825 pharmaceutical preparation Substances 0.000 title description 14
239000004615 ingredient Substances 0.000 title 1
-1 amino, hydroxyamino Chemical group 0.000 claims description 156
150000001875 compounds Chemical class 0.000 claims description 122
125000000217 alkyl group Chemical group 0.000 claims description 95
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 70
150000003839 salts Chemical class 0.000 claims description 70
239000002253 acid Substances 0.000 claims description 54
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 52
125000004432 carbon atom Chemical group C* 0.000 claims description 48
125000003545 alkoxy group Chemical group 0.000 claims description 40
229910052736 halogen Chemical group 0.000 claims description 29
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 25
150000002367 halogens Chemical group 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 24
125000001931 aliphatic group Chemical group 0.000 claims description 16
125000002947 alkylene group Chemical group 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
150000002431 hydrogen Chemical class 0.000 claims description 9
WZLBPZGAXJHDNS-UHFFFAOYSA-N methyl 6-methoxy-1-oxo-4h-4,7-phenanthroline-3-carboxylate Chemical compound C1=CC=C2C(C(=O)C=C(N3)C(=O)OC)=C3C=C(OC)C2=N1 WZLBPZGAXJHDNS-UHFFFAOYSA-N 0.000 claims description 9
238000012546 transfer Methods 0.000 claims description 9
125000003282 alkyl amino group Chemical group 0.000 claims description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000005237 alkyleneamino group Chemical group 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 7
125000002541 furyl group Chemical group 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
125000001544 thienyl group Chemical group 0.000 claims description 5
DXPQNYCDESOCAM-UHFFFAOYSA-N ethyl 6-methoxy-1-oxo-4h-4,7-phenanthroline-3-carboxylate Chemical compound C1=CC=C2C(C(=O)C=C(N3)C(=O)OCC)=C3C=C(OC)C2=N1 DXPQNYCDESOCAM-UHFFFAOYSA-N 0.000 claims description 4
YEVAZDOXASYOEU-UHFFFAOYSA-N propyl 6-methoxy-1-oxo-4h-4,7-phenanthroline-3-carboxylate Chemical compound C1=CC=C2C(C(=O)C=C(N3)C(=O)OCCC)=C3C=C(OC)C2=N1 YEVAZDOXASYOEU-UHFFFAOYSA-N 0.000 claims description 4
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 3
CXRAOWLRUURMEO-UHFFFAOYSA-N methyl 6-butoxy-1-oxo-4h-4,7-phenanthroline-3-carboxylate Chemical compound C12=CC=CN=C2C(OCCCC)=CC2=C1C(=O)C=C(C(=O)OC)N2 CXRAOWLRUURMEO-UHFFFAOYSA-N 0.000 claims description 3
150000005051 4,7-phenanthrolines Chemical class 0.000 claims description 2
125000005529 alkyleneoxy group Chemical group 0.000 claims 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
235000002639 sodium chloride Nutrition 0.000 description 59
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
238000006243 chemical reaction Methods 0.000 description 29
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 28
239000003795 chemical substances by application Substances 0.000 description 28
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 25
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
239000000243 solution Substances 0.000 description 22
239000002904 solvent Substances 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
150000007513 acids Chemical class 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
229910052500 inorganic mineral Inorganic materials 0.000 description 18
235000010755 mineral Nutrition 0.000 description 18
239000011707 mineral Substances 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 17
150000001732 carboxylic acid derivatives Chemical group 0.000 description 17
239000013543 active substance Substances 0.000 description 16
150000002148 esters Chemical class 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 14
229910052757 nitrogen Inorganic materials 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
238000009833 condensation Methods 0.000 description 12
230000005494 condensation Effects 0.000 description 12
238000010438 heat treatment Methods 0.000 description 12
238000002844 melting Methods 0.000 description 12
230000008018 melting Effects 0.000 description 12
125000004043 oxo group Chemical group O=* 0.000 description 12
239000007858 starting material Substances 0.000 description 12
238000011282 treatment Methods 0.000 description 12
230000007062 hydrolysis Effects 0.000 description 11
238000006460 hydrolysis reaction Methods 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
230000002378 acidificating effect Effects 0.000 description 10
239000011261 inert gas Substances 0.000 description 10
230000002829 reductive effect Effects 0.000 description 10
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
150000008044 alkali metal hydroxides Chemical class 0.000 description 9
239000002585 base Substances 0.000 description 9
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 9
125000003396 thiol group Chemical group [H]S* 0.000 description 9
150000001735 carboxylic acids Chemical class 0.000 description 8
239000003085 diluting agent Substances 0.000 description 8
238000001704 evaporation Methods 0.000 description 8
230000008020 evaporation Effects 0.000 description 8
235000011118 potassium hydroxide Nutrition 0.000 description 8
238000003756 stirring Methods 0.000 description 8
125000001424 substituent group Chemical group 0.000 description 8
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
229920002472 Starch Polymers 0.000 description 7
229910052783 alkali metal Inorganic materials 0.000 description 7
229910021529 ammonia Inorganic materials 0.000 description 7
239000002775 capsule Substances 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
229910052801 chlorine Inorganic materials 0.000 description 7
238000001816 cooling Methods 0.000 description 7
150000002430 hydrocarbons Chemical group 0.000 description 7
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
239000000126 substance Substances 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
229910000147 aluminium phosphate Inorganic materials 0.000 description 6
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 6
229930195733 hydrocarbon Natural products 0.000 description 6
239000007788 liquid Substances 0.000 description 6
ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical group O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
VBXOZQOLQYCNGW-UHFFFAOYSA-N 6-methoxy-1-oxo-4h-4,7-phenanthroline-3-carboxylic acid Chemical compound C12=CC=CN=C2C(OC)=CC2=C1C(=O)C=C(C(O)=O)N2 VBXOZQOLQYCNGW-UHFFFAOYSA-N 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
108010010803 Gelatin Proteins 0.000 description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
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 5
239000002841 Lewis acid Substances 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
235000011054 acetic acid Nutrition 0.000 description 5
125000002252 acyl group Chemical group 0.000 description 5
125000005907 alkyl ester group Chemical group 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
150000008064 anhydrides Chemical class 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
YTIVTFGABIZHHX-UHFFFAOYSA-N butynedioic acid Chemical class OC(=O)C#CC(O)=O YTIVTFGABIZHHX-UHFFFAOYSA-N 0.000 description 5
238000003776 cleavage reaction Methods 0.000 description 5
229920000159 gelatin Polymers 0.000 description 5
235000019322 gelatine Nutrition 0.000 description 5
235000011852 gelatine desserts Nutrition 0.000 description 5
238000011065 in-situ storage Methods 0.000 description 5
150000002576 ketones Chemical class 0.000 description 5
150000007517 lewis acids Chemical class 0.000 description 5
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
229920001223 polyethylene glycol Polymers 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
239000000843 powder Substances 0.000 description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
235000011121 sodium hydroxide Nutrition 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 5
239000000725 suspension Substances 0.000 description 5
239000003826 tablet Substances 0.000 description 5
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
238000005903 acid hydrolysis reaction Methods 0.000 description 4
238000006136 alcoholysis reaction Methods 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000000969 carrier Substances 0.000 description 4
230000032050 esterification Effects 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
239000000284 extract Substances 0.000 description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
239000008273 gelatin Substances 0.000 description 4
125000001841 imino group Chemical group [H]N=* 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
GVGOVPVSEBBWAT-UHFFFAOYSA-N methyl 1-ethoxy-6-methoxy-4,7-phenanthroline-3-carboxylate Chemical compound N1=CC=CC2=C3C(OCC)=CC(C(=O)OC)=NC3=CC(OC)=C21 GVGOVPVSEBBWAT-UHFFFAOYSA-N 0.000 description 4
239000007800 oxidant agent Substances 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
229940093956 potassium carbonate Drugs 0.000 description 4
235000011181 potassium carbonates Nutrition 0.000 description 4
238000010992 reflux Methods 0.000 description 4
230000007017 scission Effects 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000003381 stabilizer Substances 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
235000000346 sugar Nutrition 0.000 description 4
239000000454 talc Substances 0.000 description 4
229910052623 talc Inorganic materials 0.000 description 4
235000012222 talc Nutrition 0.000 description 4
229940100445 wheat starch Drugs 0.000 description 4
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
244000215068 Acacia senegal Species 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
229920000084 Gum arabic Polymers 0.000 description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
235000010489 acacia gum Nutrition 0.000 description 3
239000000205 acacia gum Substances 0.000 description 3
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
150000001350 alkyl halides Chemical class 0.000 description 3
125000004414 alkyl thio group Chemical group 0.000 description 3
208000026935 allergic disease Diseases 0.000 description 3
238000007098 aminolysis reaction Methods 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
150000004649 carbonic acid derivatives Chemical class 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
230000007717 exclusion Effects 0.000 description 3
BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
238000001640 fractional crystallisation Methods 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
239000008187 granular material Substances 0.000 description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
229910052742 iron Inorganic materials 0.000 description 3
239000008101 lactose Substances 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
125000001477 organic nitrogen group Chemical group 0.000 description 3
KHPXUQMNIQBQEV-UHFFFAOYSA-N oxaloacetic acid Chemical compound OC(=O)CC(=O)C(O)=O KHPXUQMNIQBQEV-UHFFFAOYSA-N 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
229910052698 phosphorus Inorganic materials 0.000 description 3
239000011574 phosphorus Substances 0.000 description 3
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
239000001267 polyvinylpyrrolidone Substances 0.000 description 3
229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
239000003380 propellant Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
239000000600 sorbitol Substances 0.000 description 3
239000008107 starch Substances 0.000 description 3
VOQAXCJAJRGRFP-UHFFFAOYSA-N 1-(6-aminoquinolin-5-yl)ethanone Chemical compound C1=CC=C2C(C(=O)C)=C(N)C=CC2=N1 VOQAXCJAJRGRFP-UHFFFAOYSA-N 0.000 description 2
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 2
SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
FOOUDKKEHNADTE-UHFFFAOYSA-N 8-methoxyquinolin-6-amine Chemical compound C1=CN=C2C(OC)=CC(N)=CC2=C1 FOOUDKKEHNADTE-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
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QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
201000008937 atopic dermatitis Diseases 0.000 description 1
239000010953 base metal Substances 0.000 description 1
229960000686 benzalkonium chloride Drugs 0.000 description 1
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
229910052797 bismuth Inorganic materials 0.000 description 1
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
229910000416 bismuth oxide Inorganic materials 0.000 description 1
239000008280 blood Substances 0.000 description 1
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
FYXIFWKTPAJKMY-UHFFFAOYSA-N butyl 6-butoxy-1-oxo-4h-4,7-phenanthroline-3-carboxylate Chemical compound C1=CC=C2C(C(=O)C=C(N3)C(=O)OCCCC)=C3C=C(OCCCC)C2=N1 FYXIFWKTPAJKMY-UHFFFAOYSA-N 0.000 description 1
125000006309 butyl amino group Chemical group 0.000 description 1
125000004744 butyloxycarbonyl group Chemical group 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
FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
229960005286 carbaryl Drugs 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
150000004653 carbonic acids Chemical class 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
ZFTFAPZRGNKQPU-UHFFFAOYSA-L carboxylato carbonate Chemical compound [O-]C(=O)OC([O-])=O ZFTFAPZRGNKQPU-UHFFFAOYSA-L 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
229940117975 chromium trioxide Drugs 0.000 description 1
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
XBWRJSSJWDOUSJ-UHFFFAOYSA-L chromium(ii) chloride Chemical compound Cl[Cr]Cl XBWRJSSJWDOUSJ-UHFFFAOYSA-L 0.000 description 1
238000000576 coating method Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000007906 compression Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([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
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([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
239000012024 dehydrating agents‎ Substances 0.000 description 1
TYIXMATWDRGMPF-UHFFFAOYSA-N dibismuth;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Bi+3].[Bi+3] TYIXMATWDRGMPF-UHFFFAOYSA-N 0.000 description 1
235000019700 dicalcium phosphate Nutrition 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
125000006371 dihalo methyl group Chemical group 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
125000004119 disulfanediyl group Chemical group *SS* 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000006196 drop Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000000975 dye Substances 0.000 description 1
238000006266 etherification reaction Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
MWDQTOGVUDXBMF-UHFFFAOYSA-N ethyl 4-(8-methoxy-6-nitro-5h-quinolin-6-yl)-2,4-dioxobutanoate Chemical compound C1=CN=C2C(OC)=CC(C(=O)CC(=O)C(=O)OCC)([N+]([O-])=O)CC2=C1 MWDQTOGVUDXBMF-UHFFFAOYSA-N 0.000 description 1
YCCUGGCJEMLMSS-UHFFFAOYSA-N ethyl 4-(8-methoxy-6-nitroquinolin-5-yl)-2,4-dioxobutanoate Chemical compound C1=CC=C2C(C(=O)CC(=O)C(=O)OCC)=C([N+]([O-])=O)C=C(OC)C2=N1 YCCUGGCJEMLMSS-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
239000002360 explosive Substances 0.000 description 1
239000003889 eye drop Substances 0.000 description 1
229940012356 eye drops Drugs 0.000 description 1
239000003885 eye ointment Substances 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
150000004674 formic acids Chemical class 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000004997 halocarbonyl group Chemical group 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
230000000887 hydrating effect Effects 0.000 description 1
125000005638 hydrazono group Chemical group 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 1
229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000010952 in-situ formation Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003951 lactams Chemical group 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
150000002730 mercury Chemical class 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
229910001092 metal group alloy Inorganic materials 0.000 description 1
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150000004706 metal oxides Chemical class 0.000 description 1
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UAYUQQVIPRWQGJ-UHFFFAOYSA-N methyl 1-chloro-6-methoxy-4,7-phenanthroline-3-carboxylate Chemical compound C1=CC=C2C3=C(Cl)C=C(C(=O)OC)N=C3C=C(OC)C2=N1 UAYUQQVIPRWQGJ-UHFFFAOYSA-N 0.000 description 1
ZXUQEPZWVQIOJE-UHFFFAOYSA-N methyl 2-chloro-2-oxoacetate Chemical compound COC(=O)C(Cl)=O ZXUQEPZWVQIOJE-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
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235000010981 methylcellulose Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 description 1
QLRIXNSGTJWNOV-UHFFFAOYSA-N n'-(5-acetyl-8-methoxyquinolin-6-yl)-n'-methyloxamide Chemical compound C1=CN=C2C(OC)=CC(N(C)C(=O)C(N)=O)=C(C(C)=O)C2=C1 QLRIXNSGTJWNOV-UHFFFAOYSA-N 0.000 description 1
BJYSOJKANJNZKN-UHFFFAOYSA-N n-(imidazole-1-carbonylcarbamoyl)imidazole-1-carboxamide Chemical compound C1=CN=CN1C(=O)NC(=O)NC(=O)N1C=CN=C1 BJYSOJKANJNZKN-UHFFFAOYSA-N 0.000 description 1
239000007923 nasal drop Substances 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
239000007764 o/w emulsion Substances 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
239000002674 ointment Substances 0.000 description 1
210000001672 ovary Anatomy 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
125000005646 oximino group Chemical group 0.000 description 1
150000002926 oxygen Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
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238000007911 parenteral administration Methods 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
235000010603 pastilles Nutrition 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
AFDMODCXODAXLC-UHFFFAOYSA-N phenylmethanimine Chemical class N=CC1=CC=CC=C1 AFDMODCXODAXLC-UHFFFAOYSA-N 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229940093932 potassium hydroxide Drugs 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
229940116317 potato starch Drugs 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
238000012545 processing Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000001012 protector Effects 0.000 description 1
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
150000004053 quinones Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
208000023504 respiratory system disease Diseases 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
229940100486 rice starch Drugs 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
229910001923 silver oxide Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
229940083608 sodium hydroxide Drugs 0.000 description 1
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
RSASPWMZKNIURZ-UHFFFAOYSA-M sodium;2-thiophen-2-ylacetate Chemical compound [Na+].[O-]C(=O)CC1=CC=CS1 RSASPWMZKNIURZ-UHFFFAOYSA-M 0.000 description 1
KSMWLICLECSXMI-UHFFFAOYSA-N sodium;benzene Chemical compound [Na+].C1=CC=[C-]C=C1 KSMWLICLECSXMI-UHFFFAOYSA-N 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
150000003899 tartaric acid esters Chemical class 0.000 description 1
PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
238000012360 testing method Methods 0.000 description 1
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
125000000464 thioxo group Chemical group S=* 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
239000002966 varnish Substances 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
239000007762 w/o emulsion Substances 0.000 description 1
150000003738 xylenes Chemical class 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
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- 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
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- 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

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Pulmonology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO800085A 1979-01-16 1980-01-15 Nye fenantrolinderivater, fremgangsmaate til deres fremstilling, farmasoeytiske preparater inneholdende disse og deres anvendelse NO800085L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH40279		1979-01-16

Publications (1)

Publication Number	Publication Date
NO800085L true NO800085L (no)	1980-07-17

Family

ID=4186203

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO800085A NO800085L (no)	1979-01-16	1980-01-15	Nye fenantrolinderivater, fremgangsmaate til deres fremstilling, farmasoeytiske preparater inneholdende disse og deres anvendelse

Country Status (15)

Country	Link
US (1)	US4297358A (es)
EP (1)	EP0013666A1 (es)
JP (1)	JPS5598182A (es)
AU (1)	AU5460980A (es)
DD (1)	DD148776A5 (es)
DK (1)	DK16480A (es)
ES (5)	ES487661A0 (es)
FI (1)	FI800100A (es)
GR (1)	GR70371B (es)
IL (1)	IL59130A0 (es)
NO (1)	NO800085L (es)
NZ (1)	NZ192622A (es)
PL (1)	PL221367A1 (es)
PT (1)	PT70695A (es)
ZA (1)	ZA80254B (es)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4652567A (en) *	1985-03-13	1987-03-24	Hoechst-Roussel Pharmaceuticals Inc.	Benzo(c)-1,5-naphthyridines useful for treating a patient having drug induced memory impairment in need of memory enhancement
JP2008507276A (ja) *	2004-07-23	2008-03-13	ポルノクスコーポレーション	抗酸化マクロモノマーおよび抗酸化ポリマー、ならびにその製造方法および使用方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3313817A (en) *	1964-01-27	1967-04-11	Sterling Drug Inc	4-alkyl (and alkenyl)-1-oxo-1, 4-dihydro-4, 7-phenanthroline-2-carboxylic acid derivatives
CA995670A (en) *	1970-10-05	1976-08-24	Wilson S. Waring	Phenanthrolines and pyrido-quinolines
US4156726A (en) *	1974-12-07	1979-05-29	Fisons Limited	4-Oxo-2-carboxyl quinoline derivatives used as antiallergic compounds

1980
- 1980-01-04 US US06/109,715 patent/US4297358A/en not_active Expired - Lifetime
- 1980-01-10 EP EP80810010A patent/EP0013666A1/de not_active Withdrawn
- 1980-01-14 GR GR60956A patent/GR70371B/el unknown
- 1980-01-14 FI FI800100A patent/FI800100A/fi not_active Application Discontinuation
- 1980-01-14 ES ES487661A patent/ES487661A0/es active Granted
- 1980-01-15 DK DK16480A patent/DK16480A/da not_active Application Discontinuation
- 1980-01-15 IL IL59130A patent/IL59130A0/xx unknown
- 1980-01-15 NZ NZ192622A patent/NZ192622A/xx unknown
- 1980-01-15 DD DD80218467A patent/DD148776A5/de unknown
- 1980-01-15 NO NO800085A patent/NO800085L/no unknown
- 1980-01-15 ZA ZA00800254A patent/ZA80254B/xx unknown
- 1980-01-15 PL PL22136780A patent/PL221367A1/xx unknown
- 1980-01-15 PT PT70695A patent/PT70695A/pt unknown
- 1980-01-15 AU AU54609/80A patent/AU5460980A/en not_active Abandoned
- 1980-01-16 JP JP269180A patent/JPS5598182A/ja active Pending
- 1980-08-29 ES ES494603A patent/ES8106519A1/es not_active Expired
- 1980-08-29 ES ES494606A patent/ES494606A0/es active Granted
- 1980-08-29 ES ES494605A patent/ES8106520A1/es not_active Expired
- 1980-08-29 ES ES494604A patent/ES494604A0/es active Granted

Also Published As

Publication number	Publication date
ES494603A0 (es)	1981-08-16
ES8106522A1 (es)	1981-08-16
ES8106519A1 (es)	1981-08-16
PL221367A1 (es)	1980-12-01
NZ192622A (en)	1982-03-16
EP0013666A1 (de)	1980-07-23
AU5460980A (en)	1980-07-24
ES494605A0 (es)	1981-08-16
ES8102127A1 (es)	1980-12-16
IL59130A0 (en)	1980-05-30
GR70371B (es)	1982-09-30
PT70695A (en)	1980-02-01
ES8106521A1 (es)	1981-08-16
ES8106520A1 (es)	1981-08-16
DD148776A5 (de)	1981-06-10
ES487661A0 (es)	1980-12-16
FI800100A (fi)	1980-07-17
DK16480A (da)	1980-07-17
ES494606A0 (es)	1981-08-16
US4297358A (en)	1981-10-27
ES494604A0 (es)	1981-08-16
JPS5598182A (en)	1980-07-25
ZA80254B (en)	1980-12-31

Publication	Publication Date	Title
KR900003496B1 (ko)	1990-05-21	티에닐 축합 피라졸 유도체의 제조방법
JP2996708B2 (ja)	2000-01-11	複素環式誘導体、その製造方法および前記誘導体を含有するロイコトリエン誘因性疾患または症状の治療に用いる薬理学的組成物
FI93358C (fi)	1995-03-27	Menetelmä terapeuttisesti käyttökelpoisten kromaanijohdannaisten valmistamiseksi
PL199783B1 (pl)	2008-10-31	Związki pochodne chinolino-3-karboksyamidu, zawierające je kompozycje farmaceutyczne, sposób ich wytwarzania i ich zastosowanie
EP0127763A1 (de)	1984-12-12	Tricyclische Ether, Verfahren zu ihrer Herstellung, ihre Anwendung und sie enthaltende Arzneimittel
CA2026890C (en)	2001-09-18	Quinoline derivatives, their production and use
US4476132A (en)	1984-10-09	Acylquinolinone derivatives, and antiallergic preparations and methods of inhibiting allergic reactions using them
EP0101330B1 (en)	1988-08-24	2-quinolone derivatives
NO800085L (no)	1980-07-17	Nye fenantrolinderivater, fremgangsmaate til deres fremstilling, farmasoeytiske preparater inneholdende disse og deres anvendelse
US4141982A (en)	1979-02-27	Benz-acylbenzimidazole-2-carboxylic acid derivatives
US3926961A (en)	1975-12-16	Sulphamoylbenzoic acid amides
JPH02145584A (ja)	1990-06-05	クロマン誘導体
JPH0551374A (ja)	1993-03-02	スルホンアミド誘導体、その製造法および該化合物を含有する、ロイコトリエン仲介疾病または医学的症状に使用するための医薬調剤
US4289777A (en)	1981-09-15	Quinolonecarboxylic acid derivatives and pharmaceutical preparations thereof for treatment of an allergic disease of the respiratory tract
CH640528A5 (de)	1984-01-13	Verfahren zur herstellung neuer benzopyranderivate.
FI67080C (fi)	1985-01-10	Foerfarande foer framstaellning av nya farmaceutiskt aktiva 5:-benso-ny-pyronderivat
EP0000488A1 (de)	1979-02-07	3-Oxaloamino-4-oxo-4H-1-benzopyranderivaten, Verfahren zu deren Herstellung und deren pharmazeutischen Verwendung
PL138474B1 (en)	1986-09-30	Method of obtaining 2-hydromethyl-6-methyl-4-p-tolilo-4,5,6,7-tetrahydro-thieno(2,3-c)-pyridine
NO780472L (no)	1978-08-14	Fremgangsmaate til fremstilling av benzoheterocycloglyoksyl-syrederivater
US4323688A (en)	1982-04-06	Benzimidazole-2-carboxylic acid and derivatives thereof
US4614745A (en)	1986-09-30	Anti-allergic 3-(carboxycarbonyl)amino benzothiopyran-4-one derivatives, compositions, and method of use therefor
US3855221A (en)	1974-12-17	Hydroxyphenyl hydroxyethylaminoalkyl theophyllines
WO1986002645A1 (en)	1986-05-09	New amino compounds, preparation process thereof, utilization thereof and drugs containing them
NO792105L (no)	1979-12-28	Fremgangsmaate ved fremstilling av n1-benzoyl-n2-fenyl-1,3-diaminopropan-2-oler
NO780473L (no)	1978-08-14	Fremgangsmaate til fremstilling av indolylglykokasyrederivater