NO792703L - Nye nitroforbindelser av pyrano-heterocykler samt fremgangsmaate til deres fremstilling. - Google Patents

Nye nitroforbindelser av pyrano-heterocykler samt fremgangsmaate til deres fremstilling.

Info

Publication number: NO792703L
Authority: NO; Norway
Prior art keywords: formula; atoms; hydrogen; alkyl; compounds
Prior art date: 1978-08-21

Application number

NO792703A

Other languages

English (en)

Norwegian (no)

Inventor

Friedrich-Johannes Kaemmerer

Ulrich Gebert

Hans Georg Alpermann

Original Assignee

Hoechst 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.)

1978-08-21

Filing date

1979-08-20

Publication date

1980-02-22

1979-08-20 Application filed by Hoechst Ag filed Critical Hoechst Ag

1980-02-22 Publication of NO792703L publication Critical patent/NO792703L/no

Links

238000000034 method Methods 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 13
NLLHXVBITYTYHA-UHFFFAOYSA-N Nitrofor Chemical class CCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O NLLHXVBITYTYHA-UHFFFAOYSA-N 0.000 title 1
229910052739 hydrogen Inorganic materials 0.000 claims description 47
239000001257 hydrogen Substances 0.000 claims description 47
150000001875 compounds Chemical class 0.000 claims description 35
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
125000000217 alkyl group Chemical group 0.000 claims description 28
125000004432 carbon atom Chemical group C* 0.000 claims description 28
150000003839 salts Chemical class 0.000 claims description 21
150000002431 hydrogen Chemical class 0.000 claims description 19
238000006243 chemical reaction Methods 0.000 claims description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 13
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 12
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
229910017604 nitric acid Inorganic materials 0.000 claims description 8
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 7
239000005977 Ethylene Substances 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
229960000583 acetic acid Drugs 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
125000001188 haloalkyl group Chemical group 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
239000003513 alkali Substances 0.000 claims description 4
150000003863 ammonium salts Chemical class 0.000 claims description 4
238000009835 boiling Methods 0.000 claims description 4
239000012362 glacial acetic acid Substances 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
150000002690 malonic acid derivatives Chemical class 0.000 claims description 4
238000006396 nitration reaction Methods 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 4
239000002270 dispersing agent Substances 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
150000002828 nitro derivatives Chemical class 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
208000026935 allergic disease Diseases 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims description 2
239000002585 base Substances 0.000 claims description 2
229940079593 drug Drugs 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
238000011321 prophylaxis Methods 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
238000011282 treatment Methods 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 1
229940126601 medicinal product Drugs 0.000 claims 1
239000013078 crystal Substances 0.000 description 14
238000001953 recrystallisation Methods 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
159000000000 sodium salts Chemical class 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000003756 stirring Methods 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
-1 methoxy, ethoxy, propoxy Chemical group 0.000 description 8
238000000354 decomposition reaction Methods 0.000 description 7
239000000243 solution Substances 0.000 description 7
LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 6
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
229910052731 fluorine Inorganic materials 0.000 description 6
239000011737 fluorine Substances 0.000 description 6
239000000843 powder Substances 0.000 description 6
PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical compound C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical group CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 4
108010058846 Ovalbumin Proteins 0.000 description 4
208000003455 anaphylaxis Diseases 0.000 description 4
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
229960000265 cromoglicic acid Drugs 0.000 description 4
VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 description 4
229940092253 ovalbumin Drugs 0.000 description 4
238000010992 reflux Methods 0.000 description 4
206010002198 Anaphylactic reaction Diseases 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000013543 active substance Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000000969 carrier Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 2
PASUADIMFGAUDB-UHFFFAOYSA-N 6-chloro-1,2,3,4-tetrahydroquinoline Chemical compound N1CCCC2=CC(Cl)=CC=C21 PASUADIMFGAUDB-UHFFFAOYSA-N 0.000 description 2
SDZHFVGCGGXEQJ-UHFFFAOYSA-N 8-chloro-6-ethyl-4-hydroxy-3-nitropyrano[3,2-c]quinoline-2,5-dione Chemical compound O1C(=O)C([N+]([O-])=O)=C(O)C2=C1C1=CC=C(Cl)C=C1N(CC)C2=O SDZHFVGCGGXEQJ-UHFFFAOYSA-N 0.000 description 2
ADIHELYWPVIKMT-UHFFFAOYSA-N 8-chloro-6-ethyl-4-hydroxypyrano[3,2-c]quinoline-2,5-dione Chemical compound O1C(=O)C=C(O)C2=C1C1=CC=C(Cl)C=C1N(CC)C2=O ADIHELYWPVIKMT-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
230000036783 anaphylactic response Effects 0.000 description 2
230000003266 anti-allergic effect Effects 0.000 description 2
125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 2
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 2
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
150000002169 ethanolamines Chemical class 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
LUNFYXBUYWMPBY-UHFFFAOYSA-N 3-chloro-n-ethylaniline Chemical compound CCNC1=CC=CC(Cl)=C1 LUNFYXBUYWMPBY-UHFFFAOYSA-N 0.000 description 1
RQOVHZWFOBHZSX-UHFFFAOYSA-N 4h-quinolizin-4-ol Chemical compound C1=CC=CN2C(O)C=CC=C21 RQOVHZWFOBHZSX-UHFFFAOYSA-N 0.000 description 1
GCXSLNNRXHFLAW-UHFFFAOYSA-N 6-ethyl-4-hydroxy-9-(trifluoromethyl)pyrano[3,2-c]quinoline-2,5-dione Chemical compound O1C(=O)C=C(O)C2=C1C1=CC(C(F)(F)F)=CC=C1N(CC)C2=O GCXSLNNRXHFLAW-UHFFFAOYSA-N 0.000 description 1
GRWQCZPNWFTDHU-UHFFFAOYSA-N 6-ethyl-9-fluoro-4-hydroxy-3-nitropyrano[3,2-c]quinoline-2,5-dione Chemical compound O1C(=O)C([N+]([O-])=O)=C(O)C2=C1C1=CC(F)=CC=C1N(CC)C2=O GRWQCZPNWFTDHU-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
RGVXJXDEDKPFLP-UHFFFAOYSA-N 8,9-dichloro-6-ethyl-4-hydroxy-3-nitropyrano[3,2-c]quinoline-2,5-dione Chemical compound O1C(=O)C([N+]([O-])=O)=C(O)C2=C1C1=CC(Cl)=C(Cl)C=C1N(CC)C2=O RGVXJXDEDKPFLP-UHFFFAOYSA-N 0.000 description 1
KFPPOZRZVIKQCK-UHFFFAOYSA-N 9-chloro-4-hydroxy-6-methyl-3-nitropyrano[3,2-c]quinoline-2,5-dione Chemical compound O1C(=O)C([N+]([O-])=O)=C(O)C2=C1C1=CC(Cl)=CC=C1N(C)C2=O KFPPOZRZVIKQCK-UHFFFAOYSA-N 0.000 description 1
GZRXGIBLXJPTEG-UHFFFAOYSA-N 9-chloro-4-hydroxy-6-methylpyrano[3,2-c]quinoline-2,5-dione Chemical compound O1C(=O)C=C(O)C2=C1C1=CC(Cl)=CC=C1N(C)C2=O GZRXGIBLXJPTEG-UHFFFAOYSA-N 0.000 description 1
OPDMFZYQBUGABU-UHFFFAOYSA-N 9-chloro-6-ethyl-4-hydroxypyrano[3,2-c]quinoline-2,5-dione Chemical compound O1C(=O)C=C(O)C2=C1C1=CC(Cl)=CC=C1N(CC)C2=O OPDMFZYQBUGABU-UHFFFAOYSA-N 0.000 description 1
241000588832 Bordetella pertussis Species 0.000 description 1
COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
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 1
KRVYUCMYYZAARV-UHFFFAOYSA-N N,N-dimethylformamide 2-methylpropan-1-ol Chemical compound CC(C)CO.CN(C)C=O KRVYUCMYYZAARV-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
241001126260 Nippostrongylus Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
ZYNLTPVBLIFSBC-UHFFFAOYSA-N [Na].C(C)N1C(C2=C(C=3C=CC(=CC13)Cl)OC(C(=C2O)[N+](=O)[O-])=O)=O Chemical compound [Na].C(C)N1C(C2=C(C=3C=CC(=CC13)Cl)OC(C(=C2O)[N+](=O)[O-])=O)=O ZYNLTPVBLIFSBC-UHFFFAOYSA-N 0.000 description 1
IKWTVSLWAPBBKU-UHFFFAOYSA-N a1010_sial Chemical compound O=[As]O[As]=O IKWTVSLWAPBBKU-UHFFFAOYSA-N 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
239000010775 animal oil Substances 0.000 description 1
230000002804 anti-anaphylactic effect Effects 0.000 description 1
239000000427 antigen Substances 0.000 description 1
102000036639 antigens Human genes 0.000 description 1
108091007433 antigens Proteins 0.000 description 1
229940125715 antihistaminic agent Drugs 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
229910000413 arsenic oxide Inorganic materials 0.000 description 1
229960002594 arsenic trioxide Drugs 0.000 description 1
UVZGOOXAARJPHD-UHFFFAOYSA-N butan-2-one;methanol Chemical compound OC.CCC(C)=O UVZGOOXAARJPHD-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
150000001923 cyclic compounds Chemical class 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000950 dibromo group Chemical group Br* 0.000 description 1
125000003963 dichloro group Chemical group Cl* 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000006196 drop Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
YQOFHFBILFQCLU-UHFFFAOYSA-N ethyl 6-ethyl-4-hydroxy-3-nitro-2,5-dioxopyrano[3,2-c]quinoline-9-carboxylate Chemical compound OC1=C([N+]([O-])=O)C(=O)OC2=C1C(=O)N(CC)C1=CC=C(C(=O)OCC)C=C12 YQOFHFBILFQCLU-UHFFFAOYSA-N 0.000 description 1
229960003699 evans blue Drugs 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000004438 haloalkoxy group Chemical group 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
230000008105 immune reaction Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid 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
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000003094 microcapsule Substances 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000000802 nitrating effect Effects 0.000 description 1
GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
239000012053 oil suspension Substances 0.000 description 1
206010033675 panniculitis Diseases 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
FVHNEDLBZCSUSN-UHFFFAOYSA-N pyrano[2,3-c]pyrazole Chemical compound O1C=CC=C2C=NN=C21 FVHNEDLBZCSUSN-UHFFFAOYSA-N 0.000 description 1
LYYKXLNKDJVDPU-UHFFFAOYSA-N pyrano[2,3-h]quinolin-2-one Chemical class O1C=CC=C2C3=NC(=O)C=CC3=CC=C21 LYYKXLNKDJVDPU-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
210000004304 subcutaneous tissue Anatomy 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- 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

Landscapes

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

NO792703A 1978-08-21 1979-08-20 Nye nitroforbindelser av pyrano-heterocykler samt fremgangsmaate til deres fremstilling. NO792703L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19782836470 DE2836470A1 (de)	1978-08-21	1978-08-21	Neue nitroverbindungen von pyrano- heterocyclen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel

Publications (1)

Publication Number	Publication Date
NO792703L true NO792703L (no)	1980-02-22

Family

ID=6047524

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO792703A NO792703L (no)	1978-08-21	1979-08-20	Nye nitroforbindelser av pyrano-heterocykler samt fremgangsmaate til deres fremstilling.

Country Status (12)

Country	Link
US (1)	US4258046A (da)
EP (1)	EP0008439B1 (da)
JP (1)	JPS5528997A (da)
AT (1)	ATE854T1 (da)
AU (1)	AU5006679A (da)
CA (1)	CA1134363A (da)
DE (2)	DE2836470A1 (da)
DK (1)	DK347379A (da)
ES (1)	ES483391A1 (da)
IL (1)	IL58070A0 (da)
NO (1)	NO792703L (da)
ZA (1)	ZA794380B (da)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6169687A (ja) *	1984-09-14	1986-04-10	三菱重工業株式会社	伸縮スプレツダの位置決め装置
GB8704089D0 (en) *	1987-02-21	1987-03-25	Fisons Plc	Method of treatment
US8349864B2 (en) *	2008-03-25	2013-01-08	New Mexico Technical Research Foundation	Pyrano [3,2-C] pyridones and related heterocyclic compounds as pharmaceutical agents for treating disorders responsive to apoptosis, antiproliferation or vascular disruption, and the use thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS609513B2 (ja) *	1976-03-05	1985-03-11	三菱油化薬品株式会社	キノロピラン―４―オン―２―カルボン酸誘導体およびアレルギー性喘息治療薬

1978
- 1978-08-21 DE DE19782836470 patent/DE2836470A1/de not_active Withdrawn
1979
- 1979-08-14 ES ES483391A patent/ES483391A1/es not_active Expired
- 1979-08-16 DE DE7979102981T patent/DE2962515D1/de not_active Expired
- 1979-08-16 AT AT79102981T patent/ATE854T1/de not_active IP Right Cessation
- 1979-08-16 EP EP79102981A patent/EP0008439B1/de not_active Expired
- 1979-08-19 IL IL58070A patent/IL58070A0/xx unknown
- 1979-08-20 CA CA000334066A patent/CA1134363A/en not_active Expired
- 1979-08-20 ZA ZA00794380A patent/ZA794380B/xx unknown
- 1979-08-20 NO NO792703A patent/NO792703L/no unknown
- 1979-08-20 DK DK347379A patent/DK347379A/da unknown
- 1979-08-20 AU AU50066/79A patent/AU5006679A/en not_active Abandoned
- 1979-08-21 JP JP10559379A patent/JPS5528997A/ja active Pending
- 1979-08-22 US US06/068,679 patent/US4258046A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CA1134363A (en)	1982-10-26
EP0008439B1 (de)	1982-04-14
ZA794380B (en)	1980-08-27
DK347379A (da)	1980-02-22
ES483391A1 (es)	1980-04-16
US4258046A (en)	1981-03-24
DE2962515D1 (en)	1982-05-27
ATE854T1 (de)	1982-04-15
JPS5528997A (en)	1980-02-29
DE2836470A1 (de)	1980-02-28
AU5006679A (en)	1980-03-20
EP0008439A1 (de)	1980-03-05
IL58070A0 (en)	1979-12-30

Publication	Publication Date	Title
US5281620A (en)	1994-01-25	Compounds having antitumor and antibacterial properties
CN102329325B (zh)	2013-11-27	吡咯并嘧啶酮类dpp-iv抑制剂
Baker et al.	1952	An antimalarial alkaloid from Hydrangea. XIV. Synthesis of 5-, 6-, 7-, and 8-monosubstituted derivatives
US4013665A (en)	1977-03-22	Antiviral, substituted 1,3-dimethyl-1h-pyrazolo(3,4b)quinolines
JPH0146514B2 (da)	1989-10-09
US2650229A (en)	1953-08-25	Derivatives of 2:3-dihydro-4-methyltfuro(3:2-c) quinoline and preparation thereof
NO792703L (no)	1980-02-22	Nye nitroforbindelser av pyrano-heterocykler samt fremgangsmaate til deres fremstilling.
Wuest et al.	1951	Some Derivatives of 3-Pyridol with Parasympathomimetic Properties1
NO873108L (no)	1988-01-26	Fremgangsmaate for fremstilling av terapeutisk aktive 1,4-benzodiazepiner.
FI73673C (fi)	1987-11-09	Foerfarande foer framstaellning av farmakologiskt vaerdefulla 1,5-difenylpyrazolin-3-on-foereningar.
LEONARD et al.	1946	Cinnolines. Ii. Synthesis of 4-hydroxycinnolines1
SU858570A3 (ru)	1981-08-23	Способ получени производных 3-/тетразол-5-ил/-1-азаксантона или их солей
JPH10505333A (ja)	1998-05-26	イミダゾピリジン−アゾリジノン
KR880001719B1 (ko)	1988-09-08	1,4,9,10-테트라하이드로-피라졸로[4,3-e]-피리도[3,2-b][1,4]디아제핀-10-온의 제조 방법
Tamura et al.	1982	A synthesis of 5‐amino‐and 5‐hydroxy‐l‐ethyl‐1, 4‐dihydrio‐4‐oxo‐3‐quinolinecarboxylic acids and their derivatives
US4254118A (en)	1981-03-03	1-Oxo-5H-pyrimido[2,1-c][1,4]benzthiazine-2-carboxylic acid esters
NO830758L (no)	1983-09-06	Analogifremgangsmaate for fremstilling av terapeutisk aktive 4-fenyl-4,5,6,7-tetrahydro tieno (2,3-c) pyridin-derivater
IE46258B1 (en)	1983-04-20	11-oxo-ii-(ih)-pyrido(2,1-b)quinazolines
US3567716A (en)	1971-03-02	1,8-naphthyridine derivatives and intermediates thereof
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US4298610A (en)	1981-11-03	Ester derivatives of quinolopyran-4-one-2-carboxylic acids and antiallergic antasthmatics
US3988476A (en)	1976-10-26	Pharmaceutical compositions and methods of treating allergic conditions utilizing 2-nitroindane-1,3-dione derivatives as the active agent
US3925557A (en)	1975-12-09	Anti-allergic pharmaceutical compositions
SU952848A1 (ru)	1982-08-23	Способ получени 9-замещенных 2,3-дигидроимидазо [1,2-а] бензимидазола или их солей
US3637724A (en)	1972-01-25	Benzothiadiazole salicylamides