NL7908940A - Pyrazolo1,5-c chinazoline-derivaten. - Google Patents

Pyrazolo1,5-c chinazoline-derivaten. Download PDF

Info

Publication number: NL7908940A
Authority: NL; Netherlands
Prior art keywords: compound according; formula; compound; carboxylic acid; hydrogen
Prior art date: 1978-12-13

Application number

NL7908940A

Other languages

English (en)

Dutch (nl)

Original Assignee

Squibb & Sons Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-12-13

Filing date

1979-12-12

Publication date

1980-06-17

1979-12-12 Application filed by Squibb & Sons Inc filed Critical Squibb & Sons Inc

1980-06-17 Publication of NL7908940A publication Critical patent/NL7908940A/nl

Links

JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical class N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 54
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
150000004702 methyl esters Chemical class 0.000 claims description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 11
OKXPYKHKJCATPX-UHFFFAOYSA-N quinazoline-2-carboxylic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=NC=C21 OKXPYKHKJCATPX-UHFFFAOYSA-N 0.000 claims description 10
235000019253 formic acid Nutrition 0.000 claims description 9
238000000034 method Methods 0.000 claims description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
239000011734 sodium Substances 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 7
150000002431 hydrogen Chemical class 0.000 claims description 7
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
229910052744 lithium Inorganic materials 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
229910052708 sodium Inorganic materials 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
229910052700 potassium Inorganic materials 0.000 claims description 5
YTNBLSVLSJYVLB-UHFFFAOYSA-N quinazolin-2-ylmethanol Chemical compound C1=CC=CC2=NC(CO)=NC=C21 YTNBLSVLSJYVLB-UHFFFAOYSA-N 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
239000000203 mixture Substances 0.000 claims description 4
159000000000 sodium salts Chemical class 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
230000001225 therapeutic effect Effects 0.000 claims description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
208000026935 allergic disease Diseases 0.000 claims 2
239000002253 acid Substances 0.000 claims 1
210000000481 breast Anatomy 0.000 claims 1
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 1
239000013067 intermediate product Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
RXEQRGJSVWMYBS-UHFFFAOYSA-N methyl quinazoline-2-carboxylate Chemical compound C1=CC=CC2=NC(C(=O)OC)=NC=C21 RXEQRGJSVWMYBS-UHFFFAOYSA-N 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
-1 for example Chemical group 0.000 description 17
239000002244 precipitate Substances 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
239000000706 filtrate Substances 0.000 description 10
239000000047 product Substances 0.000 description 9
239000012043 crude product Substances 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
ZHUCCRFRDUXTFA-UHFFFAOYSA-N 3-(2-aminophenyl)-1h-pyrazole-5-carboxylic acid Chemical compound NC1=CC=CC=C1C1=CC(C(O)=O)=NN1 ZHUCCRFRDUXTFA-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000002775 capsule Substances 0.000 description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
239000000243 solution Substances 0.000 description 5
239000003826 tablet Substances 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
239000006188 syrup Substances 0.000 description 4
235000020357 syrup Nutrition 0.000 description 4
238000005406 washing Methods 0.000 description 4
ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
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 3
239000012448 Lithium borohydride Substances 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
230000003266 anti-allergic effect Effects 0.000 description 3
229960001340 histamine Drugs 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
239000006187 pill Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
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 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
230000002378 acidificating effect Effects 0.000 description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000007958 cherry flavor Substances 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
235000003599 food sweetener Nutrition 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000010410 layer Substances 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
150000003246 quinazolines Chemical class 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
239000003765 sweetening agent Substances 0.000 description 2
FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
235000006491 Acacia senegal Nutrition 0.000 description 1
208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
206010027654 Allergic conditions Diseases 0.000 description 1
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 1
206010002198 Anaphylactic reaction Diseases 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
241000167854 Bourreria succulenta Species 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
238000003716 Corey-Seebach umpolung reaction Methods 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
240000001238 Gaultheria procumbens Species 0.000 description 1
235000007297 Gaultheria procumbens Nutrition 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
208000001718 Immediate Hypersensitivity Diseases 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
206010045240 Type I hypersensitivity Diseases 0.000 description 1
OEVHZSDDUAPTGG-UHFFFAOYSA-N [3-(2-aminophenyl)-1h-pyrazol-5-yl]methanol Chemical compound NC1=CC=CC=C1C1=CC(CO)=NN1 OEVHZSDDUAPTGG-UHFFFAOYSA-N 0.000 description 1
VPHONORSHWSPFO-UHFFFAOYSA-N [3-(2-aminophenyl)-1h-pyrazol-5-yl]methanol;hydrochloride Chemical compound Cl.NC1=CC=CC=C1C1=CC(CO)=NN1 VPHONORSHWSPFO-UHFFFAOYSA-N 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
125000005037 alkyl phenyl group Chemical group 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
230000036783 anaphylactic response Effects 0.000 description 1
208000003455 anaphylaxis Diseases 0.000 description 1
239000000043 antiallergic agent Substances 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
229940125715 antihistaminic agent Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
208000010216 atopic IgE responsiveness Diseases 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
125000004799 bromophenyl group Chemical group 0.000 description 1
229940124630 bronchodilator Drugs 0.000 description 1
239000000168 bronchodilator agent Substances 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
235000019693 cherries Nutrition 0.000 description 1
229940112822 chewing gum Drugs 0.000 description 1
235000015218 chewing gum Nutrition 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
230000007012 clinical effect Effects 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000000378 dietary effect Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000010685 fatty oil Substances 0.000 description 1
239000010419 fine particle Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000001207 fluorophenyl group Chemical group 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
125000005059 halophenyl group Chemical group 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000001900 immune effect Effects 0.000 description 1
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239000012442 inert solvent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000006303 iodophenyl group Chemical group 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
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
239000001525 mentha piperita l. herb oil Substances 0.000 description 1
OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 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
125000003136 n-heptyl 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])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([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
238000006386 neutralization reaction Methods 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
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125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
235000019477 peppermint oil Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000010992 reflux Methods 0.000 description 1
206010039083 rhinitis Diseases 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
239000004208 shellac Substances 0.000 description 1
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239000002002 slurry Substances 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
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239000003381 stabilizer Substances 0.000 description 1
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150000003431 steroids Chemical class 0.000 description 1
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
235000012431 wafers Nutrition 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
- 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

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

NL7908940A 1978-12-13 1979-12-12 Pyrazolo1,5-c chinazoline-derivaten. NL7908940A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US96964278		1978-12-13
US05/969,642 US4198412A (en)	1978-12-13	1978-12-13	Pyrazolo [1,5-C] quinazoline derivatives and their use in treating allergic conditions

Publications (1)

Publication Number	Publication Date
NL7908940A true NL7908940A (nl)	1980-06-17

Family

ID=25515802

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7908940A NL7908940A (nl)	1978-12-13	1979-12-12	Pyrazolo1,5-c chinazoline-derivaten.

Country Status (15)

Country	Link
US (1)	US4198412A (fr)
JP (1)	JPS5583787A (fr)
AU (1)	AU5359379A (fr)
BE (1)	BE880607A (fr)
CA (1)	CA1122215A (fr)
DE (1)	DE2950234A1 (fr)
DK (1)	DK529179A (fr)
FR (1)	FR2444038A1 (fr)
GB (1)	GB2039896A (fr)
IT (1)	IT1164093B (fr)
LU (1)	LU81987A1 (fr)
NL (1)	NL7908940A (fr)
NO (1)	NO794064L (fr)
SE (1)	SE7910255L (fr)
ZA (1)	ZA796589B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU178523B (en) *	1979-05-18	1982-05-28	Egyt Gyogyszervegyeszeti Gyar	Process for preparing new pyrazolo-quinazoline derivatives
CN103130810B (zh) *	2013-03-11	2015-02-25	河南师范大学	一种吡唑并[1,5-c]喹唑啉类化合物的合成方法
JP6211189B2 (ja) *	2013-07-17	2017-10-11	ヒソン・マテリアル・リミテッドＨｅｅｓｕｎｇＭａｔｅｒｉａｌＬｔｄ．	窒素含有多環式化合物およびそれを用いた有機発光素子

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3313815A (en) *	1964-05-04	1967-04-11	Sterling Drug Inc	8-chloropyrazolo-[1, 5-c]quinazoline derivatives and methods of preparing same
US3899508A (en) *	1974-04-12	1975-08-12	Lilly Co Eli	5-(2-Aminophenyl)pyrazole-3-carboxylic acids and esters thereof
US3895027A (en) *	1974-04-12	1975-07-15	Lilly Co Eli	Process for preparing pyrazole-3-carboxylic acids
US4076818A (en) *	1976-07-02	1978-02-28	E. R. Squibb & Sons, Inc.	Pyrazolo [1,5-C]quinazoline derivatives and related compounds
US4129653A (en) *	1977-01-05	1978-12-12	Ortho Pharmaceutical Corporation	Substituted pyrrolo [1,2-c] quinazolines and pharmaceutical compositions and methods employing them
US4110452A (en) *	1977-10-17	1978-08-29	E. R. Squibb & Sons, Inc.	Pyrazolo (1,5-c) quinazoline derivatives and related compounds
US4112098A (en) *	1977-10-17	1978-09-05	E. R. Squibb & Sons, Inc.	Pyrazolo[1,5-c]quinazoline derivatives and related compounds
US4128644A (en) *	1977-07-29	1978-12-05	E. R. Squibb & Sons, Inc.	Pyrazolo(1,5-c)quinazoline derivatives and related compounds

1978
- 1978-12-13 US US05/969,642 patent/US4198412A/en not_active Expired - Lifetime
1979
- 1979-12-03 CA CA000341087A patent/CA1122215A/fr not_active Expired
- 1979-12-04 ZA ZA00796589A patent/ZA796589B/xx unknown
- 1979-12-07 AU AU53593/79A patent/AU5359379A/en not_active Abandoned
- 1979-12-07 GB GB7942375A patent/GB2039896A/en not_active Withdrawn
- 1979-12-12 SE SE7910255A patent/SE7910255L/xx unknown
- 1979-12-12 IT IT51070/79A patent/IT1164093B/it active
- 1979-12-12 DK DK529179A patent/DK529179A/da unknown
- 1979-12-12 NL NL7908940A patent/NL7908940A/nl not_active Application Discontinuation
- 1979-12-12 NO NO794064A patent/NO794064L/no unknown
- 1979-12-12 LU LU81987A patent/LU81987A1/fr unknown
- 1979-12-13 DE DE19792950234 patent/DE2950234A1/de not_active Withdrawn
- 1979-12-13 JP JP16264879A patent/JPS5583787A/ja active Pending
- 1979-12-13 FR FR7930624A patent/FR2444038A1/fr not_active Withdrawn
- 1979-12-13 BE BE0/198559A patent/BE880607A/fr unknown

Also Published As

Publication number	Publication date
AU5359379A (en)	1980-06-19
NO794064L (no)	1980-06-16
IT7951070A0 (it)	1979-12-12
IT1164093B (it)	1987-04-08
DE2950234A1 (de)	1980-06-26
BE880607A (fr)	1980-06-13
FR2444038A1 (fr)	1980-07-11
SE7910255L (sv)	1980-06-14
GB2039896A (en)	1980-08-20
LU81987A1 (fr)	1980-04-22
DK529179A (da)	1980-06-14
ZA796589B (en)	1980-11-26
US4198412A (en)	1980-04-15
CA1122215A (fr)	1982-04-20
JPS5583787A (en)	1980-06-24

Legal Events

Date	Code	Title	Description
1982-08-02	BV	The patent application has lapsed

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JPWO1997000258A1 (ja)	1998-08-25	三環性ベンゾアゼピン化合物
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PL128998B1 (en)	1984-03-31	Process for preparing novel 2-amino-3-benzoylphenylacetamides and their derivatives
HU181608B (en)	1983-10-28	Process for producing imidazo-thieno-pyrimidine derivatives
JPH0377191B2 (fr)	1991-12-09
US4198412A (en)	1980-04-15	Pyrazolo [1,5-C] quinazoline derivatives and their use in treating allergic conditions
GB2078736A (en)	1982-01-13	Indole and indoline derivatives
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