NO782450L - Fremgangsmaate for fremstilling av nye benzopyranderivater - Google Patents

Fremgangsmaate for fremstilling av nye benzopyranderivater

Info

Publication number: NO782450L
Authority: NO; Norway
Prior art keywords: oxo; benzopyran; salt; produced; group
Prior art date: 1977-07-15

Application number

NO782450A

Other languages

English (en)

Norwegian (no)

Inventor

Georges Haas

Alberto Rossi

Knut A Jaeggi

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.)

1977-07-15

Filing date

1978-07-14

Publication date

1979-01-16

1978-07-14 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1979-01-16 Publication of NO782450L publication Critical patent/NO782450L/no

Links

238000000034 method Methods 0.000 title claims description 61
150000001562 benzopyrans Chemical class 0.000 title 1
-1 ester halide Chemical class 0.000 claims description 120
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 100
150000001875 compounds Chemical class 0.000 claims description 88
150000003839 salts Chemical group 0.000 claims description 76
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 70
239000002253 acid Substances 0.000 claims description 47
125000000217 alkyl group Chemical group 0.000 claims description 44
125000004432 carbon atom Chemical group C* 0.000 claims description 39
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 33
125000003431 oxalo group Chemical group 0.000 claims description 27
229910052736 halogen Inorganic materials 0.000 claims description 25
150000002367 halogens Chemical class 0.000 claims description 24
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
125000002252 acyl group Chemical group 0.000 claims description 21
125000003545 alkoxy group Chemical group 0.000 claims description 21
125000001931 aliphatic group Chemical group 0.000 claims description 20
125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
125000002947 alkylene group Chemical group 0.000 claims description 17
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
238000002360 preparation method Methods 0.000 claims description 12
125000005530 alkylenedioxy group Chemical group 0.000 claims description 10
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
229910052740 iodine Inorganic materials 0.000 claims description 8
CLNIGTPSRSZTRV-UHFFFAOYSA-N 2-oxo-2-[(4-oxochromen-3-yl)amino]acetic acid Chemical class C1=CC=C2C(=O)C(NC(=O)C(=O)O)=COC2=C1 CLNIGTPSRSZTRV-UHFFFAOYSA-N 0.000 claims description 7
ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
150000002431 hydrogen Chemical class 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
JJWBENQSMVHYRS-UHFFFAOYSA-N 2-[(5,8-dimethyl-4-oxochromen-3-yl)amino]-2-oxoacetic acid Chemical compound O1C=C(NC(=O)C(O)=O)C(=O)C2=C1C(C)=CC=C2C JJWBENQSMVHYRS-UHFFFAOYSA-N 0.000 claims description 5
YHEUQJLUSPFCOM-UHFFFAOYSA-N 2-[(6-chloro-4-oxochromen-3-yl)amino]-2-oxoacetic acid Chemical compound C1=C(Cl)C=C2C(=O)C(NC(=O)C(=O)O)=COC2=C1 YHEUQJLUSPFCOM-UHFFFAOYSA-N 0.000 claims description 5
UWFGUKKEHDTUHR-UHFFFAOYSA-N 2-[(6-hydroxy-4-oxochromen-3-yl)amino]-2-oxoacetic acid Chemical compound C1=C(O)C=C2C(=O)C(NC(=O)C(=O)O)=COC2=C1 UWFGUKKEHDTUHR-UHFFFAOYSA-N 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 4
LVYQKDNCCZSEJF-UHFFFAOYSA-N 2-[(5,7-dimethyl-4-oxochromen-3-yl)amino]-2-oxoacetic acid Chemical compound O1C=C(NC(=O)C(O)=O)C(=O)C=2C1=CC(C)=CC=2C LVYQKDNCCZSEJF-UHFFFAOYSA-N 0.000 claims description 3
PJWOQHLOBZKJRB-UHFFFAOYSA-N 2-[(6,7-dimethyl-4-oxochromen-3-yl)amino]-2-oxoacetic acid Chemical compound O1C=C(NC(=O)C(O)=O)C(=O)C2=C1C=C(C)C(C)=C2 PJWOQHLOBZKJRB-UHFFFAOYSA-N 0.000 claims description 3
JZXDICVANPVUJR-UHFFFAOYSA-N 2-[(6-methoxy-4-oxochromen-3-yl)amino]-2-oxoacetic acid Chemical compound O1C=C(NC(=O)C(O)=O)C(=O)C2=CC(OC)=CC=C21 JZXDICVANPVUJR-UHFFFAOYSA-N 0.000 claims description 3
NMELSRLESRVEMA-UHFFFAOYSA-N 2-[(6-methyl-4-oxochromen-3-yl)amino]-2-oxoacetic acid Chemical compound O1C=C(NC(=O)C(O)=O)C(=O)C2=CC(C)=CC=C21 NMELSRLESRVEMA-UHFFFAOYSA-N 0.000 claims description 3
150000003949 imides Chemical class 0.000 claims description 2
150000002905 orthoesters Chemical class 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 7
125000001589 carboacyl group Chemical group 0.000 claims 5
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 2
AIKDEQPSBFKXTI-UHFFFAOYSA-N 2-[(6-chloro-7-methyl-4-oxochromen-3-yl)amino]-2-oxoacetic acid Chemical compound O1C=C(NC(=O)C(O)=O)C(=O)C2=C1C=C(C)C(Cl)=C2 AIKDEQPSBFKXTI-UHFFFAOYSA-N 0.000 claims 1
SHQPVTGHIOTYGN-UHFFFAOYSA-N 2-[(6-chloro-8-methyl-4-oxochromen-3-yl)amino]-2-oxoacetic acid Chemical compound ClC=1C=C(C2=C(C(C(=CO2)NC(=O)C(=O)O)=O)C=1)C SHQPVTGHIOTYGN-UHFFFAOYSA-N 0.000 claims 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
238000003797 solvolysis reaction Methods 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
238000006243 chemical reaction Methods 0.000 description 40
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 28
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
239000000243 solution Substances 0.000 description 22
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
239000013543 active substance Substances 0.000 description 20
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
239000002585 base Substances 0.000 description 17
239000003795 chemical substances by application Substances 0.000 description 17
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
239000000825 pharmaceutical preparation Substances 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
238000011282 treatment Methods 0.000 description 14
150000002430 hydrocarbons Chemical group 0.000 description 13
239000007858 starting material Substances 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
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 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
229910052500 inorganic mineral Inorganic materials 0.000 description 12
239000011707 mineral Substances 0.000 description 12
235000010755 mineral Nutrition 0.000 description 12
239000000203 mixture Substances 0.000 description 12
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 11
238000000354 decomposition reaction Methods 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
230000002378 acidificating effect Effects 0.000 description 10
150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
239000012442 inert solvent Substances 0.000 description 10
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
235000006408 oxalic acid Nutrition 0.000 description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
239000000460 chlorine Substances 0.000 description 9
229910052801 chlorine Inorganic materials 0.000 description 9
150000002148 esters Chemical class 0.000 description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
238000010438 heat treatment Methods 0.000 description 8
238000003756 stirring Methods 0.000 description 8
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 7
229920002472 Starch Polymers 0.000 description 7
235000011054 acetic acid Nutrition 0.000 description 7
150000007513 acids Chemical class 0.000 description 7
239000011230 binding agent Substances 0.000 description 7
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
235000011121 sodium hydroxide Nutrition 0.000 description 7
239000000725 suspension Substances 0.000 description 7
239000003826 tablet Substances 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
150000008064 anhydrides Chemical class 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000003381 stabilizer Substances 0.000 description 6
125000005907 alkyl ester group Chemical group 0.000 description 5
229910000147 aluminium phosphate Inorganic materials 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
150000004945 aromatic hydrocarbons Chemical group 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000002775 capsule Substances 0.000 description 5
239000007788 liquid Substances 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
125000001477 organic nitrogen group Chemical group 0.000 description 5
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 5
229920001223 polyethylene glycol Polymers 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
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 4
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
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 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
208000026935 allergic disease Diseases 0.000 description 4
239000000969 carrier Substances 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
238000001816 cooling Methods 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
239000008101 lactose Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 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
HUFVYEZNQDSHPS-UHFFFAOYSA-N 3-amino-5,7-dimethylchromen-4-one Chemical compound O1C=C(N)C(=O)C=2C1=CC(C)=CC=2C HUFVYEZNQDSHPS-UHFFFAOYSA-N 0.000 description 3
KHHXAUPSBBQGKY-UHFFFAOYSA-N 3-aminochromen-4-one Chemical compound C1=CC=C2C(=O)C(N)=COC2=C1 KHHXAUPSBBQGKY-UHFFFAOYSA-N 0.000 description 3
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
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
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
229920000084 Gum arabic Polymers 0.000 description 3
206010020751 Hypersensitivity Diseases 0.000 description 3
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
235000010489 acacia gum Nutrition 0.000 description 3
239000000205 acacia gum Substances 0.000 description 3
150000008065 acid anhydrides Chemical class 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
238000006136 alcoholysis reaction Methods 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000008044 alkali metal hydroxides Chemical class 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
125000005115 alkyl carbamoyl group Chemical group 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
150000003863 ammonium salts Chemical class 0.000 description 3
208000006673 asthma Diseases 0.000 description 3
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 3
238000000576 coating method Methods 0.000 description 3
239000008298 dragée Substances 0.000 description 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
239000008273 gelatin Substances 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
239000007903 gelatin capsule Substances 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
239000008187 granular material Substances 0.000 description 3
125000004997 halocarbonyl group Chemical group 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
230000003647 oxidation Effects 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
239000012286 potassium permanganate Substances 0.000 description 3
239000003380 propellant Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000000600 sorbitol Substances 0.000 description 3
239000007921 spray Substances 0.000 description 3
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
239000011975 tartaric acid Substances 0.000 description 3
235000002906 tartaric acid Nutrition 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
150000003626 triacylglycerols Chemical class 0.000 description 3
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
TYPCQHXFVXIHBK-UHFFFAOYSA-N 2-[(7-methoxy-4-oxochromen-3-yl)amino]-2-oxoacetic acid Chemical compound O1C=C(NC(=O)C(O)=O)C(=O)C=2C1=CC(OC)=CC=2 TYPCQHXFVXIHBK-UHFFFAOYSA-N 0.000 description 2
LJMSAUILRDVXCA-UHFFFAOYSA-N 2-methoxy-2-oxoacetic acid;hydrochloride Chemical compound Cl.COC(=O)C(O)=O LJMSAUILRDVXCA-UHFFFAOYSA-N 0.000 description 2
NGQCCVZGZZDMNE-UHFFFAOYSA-N 3-amino-2-methylchromen-4-one Chemical compound C1=CC=C2C(=O)C(N)=C(C)OC2=C1 NGQCCVZGZZDMNE-UHFFFAOYSA-N 0.000 description 2
OGHLYDLAKNGYQK-UHFFFAOYSA-N 3-amino-7-methoxychromen-4-one Chemical compound O1C=C(N)C(=O)C=2C1=CC(OC)=CC=2 OGHLYDLAKNGYQK-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
NQNLVRGWKBTARN-UHFFFAOYSA-N 3-nitrochromen-4-one Chemical class C1=CC=C2C(=O)C([N+](=O)[O-])=COC2=C1 NQNLVRGWKBTARN-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
JHHWFHNZMMUDKY-UHFFFAOYSA-N 7-methoxy-3-nitrochromen-4-one Chemical compound O1C=C([N+]([O-])=O)C(=O)C=2C1=CC(OC)=CC=2 JHHWFHNZMMUDKY-UHFFFAOYSA-N 0.000 description 2
206010002198 Anaphylactic reaction Diseases 0.000 description 2
241000416162 Astragalus gummifer Species 0.000 description 2
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235000015281 sodium iodate Nutrition 0.000 description 1
229940032753 sodium iodate Drugs 0.000 description 1
NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical group [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
125000005300 thiocarboxy group Chemical group C(=S)(O)* 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000005809 transesterification reaction Methods 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
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
125000004953 trihalomethyl group Chemical group 0.000 description 1
230000007306 turnover Effects 0.000 description 1
239000002966 varnish Substances 0.000 description 1
239000007762 w/o emulsion Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrane Compounds (AREA)
Cephalosporin Compounds (AREA)

NO782450A 1977-07-15 1978-07-14 Fremgangsmaate for fremstilling av nye benzopyranderivater NO782450L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
LU77786A LU77786A1 (de)	1977-07-15	1977-07-15	Verfahren zur herstellung neuer benzopyranderivate

Publications (1)

Publication Number	Publication Date
NO782450L true NO782450L (no)	1979-01-16

Family

ID=19728641

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO782450A NO782450L (no)	1977-07-15	1978-07-14	Fremgangsmaate for fremstilling av nye benzopyranderivater

Country Status (19)

Country	Link
US (3)	US4216155A (de)
EP (1)	EP0000488A1 (de)
JP (1)	JPS5419982A (de)
AT (1)	AT363086B (de)
AU (1)	AU3800678A (de)
CS (1)	CS207633B2 (de)
DD (1)	DD139578A5 (de)
DK (1)	DK316178A (de)
ES (1)	ES471696A1 (de)
FI (1)	FI782228A (de)
GR (1)	GR72857B (de)
IL (1)	IL55134A0 (de)
LU (1)	LU77786A1 (de)
NO (1)	NO782450L (de)
NZ (1)	NZ187851A (de)
PL (1)	PL208434A1 (de)
PT (1)	PT68289A (de)
SU (1)	SU904521A3 (de)
ZA (1)	ZA784016B (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3065568D1 (en) *	1977-07-18	1983-12-22	Ciba Geigy Ag	Intermediates in the preparation of cephalosporin derivatives, process for their preparation and use
DE3270785D1 (en) *	1981-10-29	1986-05-28	Bayer Ag	Process for preparing solid fast-releasing drug formulations of dihydropyridines
USRE33963E (en) *	1981-10-29	1992-06-16	Bayer Aktiengesellschaft	Solid rapidly released medicament preparations containing dihydropyridines, and processes for their preparation
JPS5994369A (ja) *	1982-11-22	1984-05-31	Furukawa Battery Co Ltd:The	アルカリ蓄電池用極板の製造方法
US4614745A (en) *	1984-04-24	1986-09-30	Ciba-Geigy Corporation	Anti-allergic 3-(carboxycarbonyl)amino benzothiopyran-4-one derivatives, compositions, and method of use therefor
US5135754A (en) *	1988-01-06	1992-08-04	Delalande S.A.	Method of preparing a copolymer of two α-amino acids and a copolymer thus obtained
US5579789A (en) *	1995-01-04	1996-12-03	Whirlpool Corporation	Food soil handling system for a dishwasher
KR20170110998A (ko)	2016-03-24	2017-10-12	다우 코닝 코포레이션	낮은 스토리지 모듈러스 실리콘 기재층을 포함하는 광학용 실리콘 양면 테이프

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3952013A (en) *	1969-02-12	1976-04-20	Fisons Limited	1-Thiachromone-2-carboxylic acids and derivatives
US3862143A (en) *	1972-12-04	1975-01-21	Warner Lambert Co	Substituted chromone-3-carbonitriles, carboxamides and carboxylic acids
US4007173A (en) *	1973-05-07	1977-02-08	Smithkline Corporation	α-amino-α-(ureidophenyl)acetamidocephalosporins
US3937719A (en) *	1975-01-06	1976-02-10	American Home Products Corporation	(4-oxo-4h-1-benzopyran-2-yl)-oxamic acid, salts and esters anti-allergic agents
US4076729A (en) *	1976-08-02	1978-02-28	Warner-Lambert Company	(4-Oxo-4H-1-benzopyran-3-yl)aminooxoacetic acids and their derivatives
US4313945A (en) *	1978-11-23	1982-02-02	Ciba-Geigy Corporation	7-Thiazolyl-acetamido-cephem derivatives with terminal aminocarboxylic acid grouping
US4242509A (en) *	1979-04-13	1980-12-30	Eli Lilly And Company	Process for producing 7-amino-7-alkoxycephalosporins

1977
- 1977-07-15 LU LU77786A patent/LU77786A1/de unknown
1978
- 1978-07-07 EP EP78100327A patent/EP0000488A1/de not_active Ceased
- 1978-07-11 US US05/923,522 patent/US4216155A/en not_active Expired - Lifetime
- 1978-07-12 CS CS784665A patent/CS207633B2/cs unknown
- 1978-07-12 FI FI782228A patent/FI782228A/fi not_active Application Discontinuation
- 1978-07-13 PT PT68289A patent/PT68289A/de unknown
- 1978-07-13 NZ NZ187851A patent/NZ187851A/xx unknown
- 1978-07-13 ES ES471696A patent/ES471696A1/es not_active Expired
- 1978-07-13 AU AU38006/78A patent/AU3800678A/en active Pending
- 1978-07-13 IL IL55134A patent/IL55134A0/xx unknown
- 1978-07-13 DD DD78206709A patent/DD139578A5/de unknown
- 1978-07-14 GR GR56778A patent/GR72857B/el unknown
- 1978-07-14 DK DK783161A patent/DK316178A/da unknown
- 1978-07-14 AT AT0509978A patent/AT363086B/de not_active IP Right Cessation
- 1978-07-14 NO NO782450A patent/NO782450L/no unknown
- 1978-07-14 ZA ZA00784016A patent/ZA784016B/xx unknown
- 1978-07-15 PL PL20843478A patent/PL208434A1/xx unknown
- 1978-07-15 JP JP8666878A patent/JPS5419982A/ja active Pending
1979
- 1979-06-15 SU SU792774403A patent/SU904521A3/ru active
1980
- 1980-01-07 US US06/110,077 patent/US4288450A/en not_active Expired - Lifetime
- 1980-02-11 US US06/120,591 patent/US4374134A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
US4216155A (en)	1980-08-05
CS207633B2 (en)	1981-08-31
PT68289A (de)	1978-08-01
DK316178A (da)	1979-01-16
PL208434A1 (pl)	1979-06-04
DD139578A5 (de)	1980-01-09
IL55134A0 (en)	1978-09-29
NZ187851A (en)	1980-05-27
EP0000488A1 (de)	1979-02-07
FI782228A (fi)	1979-01-16
GR72857B (de)	1983-12-09
LU77786A1 (de)	1979-03-26
US4288450A (en)	1981-09-08
JPS5419982A (en)	1979-02-15
ES471696A1 (es)	1979-10-01
SU904521A3 (ru)	1982-02-07
US4374134A (en)	1983-02-15
AU3800678A (en)	1980-01-17
AT363086B (de)	1981-07-10
ZA784016B (en)	1979-07-25
ATA509978A (de)	1980-12-15

Publication	Publication Date	Title
US4140789A (en)	1979-02-20	Etherified hydroxy-benzodiheterocyclic compounds
EP0148725B1 (de)	1987-05-06	Sulfonamido-Benzamid-Derivate
US3586694A (en)	1971-06-22	1-benzoylbenzimidazol-2-ylacetic acids
PT95655B (pt)	1996-09-30	Processo para a preparacao de derivados de benzimidazol
NO782450L (no)	1979-01-16	Fremgangsmaate for fremstilling av nye benzopyranderivater
IE58751B1 (en)	1993-11-03	New benzamides
NO150279B (no)	1984-06-12	Analogifremgangsmaate til fremstilling av nye terapeutisk virksomme benzopyranderivater
US4505913A (en)	1985-03-19	Substituted anthranilamides and pharmaceutical preparations containing these compounds
GB2078715A (en)	1982-01-13	N-(diethylaminoethyl)-2-alkoxybenzamide derivatives
US3590047A (en)	1971-06-29	2-benzoylbenzimidazol-1-ylacetic acids
GB1573186A (en)	1980-08-20	4-aminoquinoline derivatives
US4267332A (en)	1981-05-12	3-(Tetrazol-5-yl)-1-azaxanthones
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
CS268189B2 (en)	1990-03-14	Method of quinazolinediones and pyridopyrimidinodiones production
US4323688A (en)	1982-04-06	Benzimidazole-2-carboxylic acid and derivatives thereof
EP0184801B1 (de)	1990-09-26	Chromenderivate, Verfahren zu ihrer Herstellung und diese enthaltendes anti-allergisches Mittel
PL112249B1 (en)	1980-10-31	Process for preparing novel derivatives of 1-/3-/3,4,5-trimethoxyphenoxy/-2-hydroxypropyl/-4-arylpiperazine
NO851617L (no)	1985-10-25	3-substituerte tiopyroner.
US3828073A (en)	1974-08-06	4-hydroxy-2h-1-benzothiopyran-3-carboxamides and their corresponding s-oxides
US3814772A (en)	1974-06-04	Ortho-amino benzoyl hydrazine derivatives and process for preparing the same
US4221806A (en)	1980-09-09	Novel benzothiopyran derivatives
NO881899L (no)	1988-11-03	Nye 2-aminoalkyl-4-benzyl-1-(2h)-ftalazino-derivater.
NO852062L (no)	1985-11-25	Fremgangsmaate til fremstilling av ny resorcineter.
GB2127809A (en)	1984-04-18	Certain beta -oxo- alpha -carbamoyl- pyrrolepropionitriles
NO800085L (no)	1980-07-17	Nye fenantrolinderivater, fremgangsmaate til deres fremstilling, farmasoeytiske preparater inneholdende disse og deres anvendelse