NO124993B - - Google Patents

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Publication number: NO124993B
Authority: NO; Norway
Prior art keywords: bis; parts; yloxy; group; carboxychromon
Prior art date: 1965-03-25

Application number

NO373069A

Other languages

English (en)

Norwegian (no)

Inventor

Altounyan R Collingwood

C Fitzmaurice

Lee T Brian

Original Assignee

Fisons Pharmaceuticals Ltd

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.)

1965-03-25

Filing date

1969-09-18

Publication date

1972-07-03

1965-03-25 Priority claimed from GB12626/65A external-priority patent/GB1144905A/en

1969-04-10 Priority claimed from DE19691918142 external-priority patent/DE1918142A1/de

1969-04-22 Priority claimed from DE19691920365 external-priority patent/DE1920365A1/de

1969-09-18 Application filed by Fisons Pharmaceuticals Ltd filed Critical Fisons Pharmaceuticals Ltd

1969-09-18 Priority to NO373069A priority Critical patent/NO124993B/no

1972-07-03 Publication of NO124993B publication Critical patent/NO124993B/no

Links

RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 85
-1 2-hydroxy-trimethylene Chemical group 0.000 claims description 76
150000001875 compounds Chemical class 0.000 claims description 63
150000002148 esters Chemical class 0.000 claims description 47
238000000034 method Methods 0.000 claims description 46
238000006243 chemical reaction Methods 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 21
150000001408 amides Chemical class 0.000 claims description 16
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 6
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
230000015572 biosynthetic process Effects 0.000 claims description 5
239000007858 starting material Substances 0.000 claims description 5
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 claims description 4
125000004450 alkenylene group Chemical group 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
150000003944 halohydrins Chemical group 0.000 claims description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical group CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
230000008569 process Effects 0.000 claims description 2
125000003700 epoxy group Chemical group 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 275
238000004458 analytical method Methods 0.000 description 101
239000000243 solution Substances 0.000 description 84
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 68
239000000203 mixture Substances 0.000 description 59
238000002425 crystallisation Methods 0.000 description 57
230000008025 crystallization Effects 0.000 description 57
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
239000002253 acid Substances 0.000 description 44
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 41
239000007787 solid Substances 0.000 description 41
WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 34
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 31
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 31
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
238000010992 reflux Methods 0.000 description 23
RVMGXWBCQGAWBR-UHFFFAOYSA-N 4-oxo-1-benzopyran-2-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)=CC(=O)C2=C1 RVMGXWBCQGAWBR-UHFFFAOYSA-N 0.000 description 22
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
YPTJKHVBDCRKNF-UHFFFAOYSA-N 2',6'-Dihydroxyacetophenone Chemical compound CC(=O)C1=C(O)C=CC=C1O YPTJKHVBDCRKNF-UHFFFAOYSA-N 0.000 description 21
IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 description 21
239000002904 solvent Substances 0.000 description 21
JECYUBVRTQDVAT-UHFFFAOYSA-N 2-acetylphenol Chemical class CC(=O)C1=CC=CC=C1O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 description 20
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
238000001816 cooling Methods 0.000 description 18
230000008018 melting Effects 0.000 description 18
238000002844 melting Methods 0.000 description 18
239000003921 oil Substances 0.000 description 18
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
229910000030 sodium bicarbonate Inorganic materials 0.000 description 15
235000017557 sodium bicarbonate Nutrition 0.000 description 15
239000013078 crystal Substances 0.000 description 14
238000009835 boiling Methods 0.000 description 13
239000002244 precipitate Substances 0.000 description 13
239000000047 product Substances 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 12
239000011734 sodium Substances 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
229960000583 acetic acid Drugs 0.000 description 11
208000006673 asthma Diseases 0.000 description 11
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
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 10
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 10
125000005594 diketone group Chemical class 0.000 description 10
229910052708 sodium Inorganic materials 0.000 description 10
238000003756 stirring Methods 0.000 description 10
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 9
239000003208 petroleum Substances 0.000 description 9
238000002360 preparation method Methods 0.000 description 9
239000000725 suspension Substances 0.000 description 9
229910021529 ammonia Inorganic materials 0.000 description 8
239000000427 antigen Substances 0.000 description 8
102000036639 antigens Human genes 0.000 description 8
108091007433 antigens Proteins 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
238000009833 condensation Methods 0.000 description 8
230000005494 condensation Effects 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 8
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
MOMFXATYAINJML-UHFFFAOYSA-N 2-Acetylthiazole Chemical group CC(=O)C1=NC=CS1 MOMFXATYAINJML-UHFFFAOYSA-N 0.000 description 7
229940126062 Compound A Drugs 0.000 description 7
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
150000004682 monohydrates Chemical class 0.000 description 7
239000012286 potassium permanganate Substances 0.000 description 7
IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 6
MOWNIAOVRQFQEF-UHFFFAOYSA-N 1-[2-[5-(2-acetyl-3-hydroxyphenoxy)pentoxy]-6-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCCCCCOC2=C(C(=CC=C2)O)C(C)=O)C=CC=C1O MOWNIAOVRQFQEF-UHFFFAOYSA-N 0.000 description 6
SULYEHHGGXARJS-UHFFFAOYSA-N 2',4'-dihydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1O SULYEHHGGXARJS-UHFFFAOYSA-N 0.000 description 6
PXPNSQMWVPLERM-UHFFFAOYSA-N 2-methylchromen-4-one Chemical compound C1=CC=C2OC(C)=CC(=O)C2=C1 PXPNSQMWVPLERM-UHFFFAOYSA-N 0.000 description 6
MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical compound C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 description 6
ILAZSBMAIJXODQ-UHFFFAOYSA-N 5-[5-(2-carboxy-4-oxochromen-5-yl)oxypentoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCCCCCOC1=C2C(=O)C=C(C(=O)O)OC2=CC=C1 ILAZSBMAIJXODQ-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
238000012360 testing method Methods 0.000 description 6
NWTNHOSYXTWRQT-UHFFFAOYSA-N 6-[5-(2-carboxy-4-oxochromen-6-yl)oxypentoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=CC(OCCCCCOC=3C=C4C(=O)C=C(OC4=CC=3)C(=O)O)=CC=C21 NWTNHOSYXTWRQT-UHFFFAOYSA-N 0.000 description 5
239000001273 butane Substances 0.000 description 5
239000000284 extract Substances 0.000 description 5
238000001914 filtration Methods 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
150000002576 ketones Chemical class 0.000 description 5
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
DMVDEOWMLBKODC-UHFFFAOYSA-N 4-oxo-5-pentoxychromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCCCCC DMVDEOWMLBKODC-UHFFFAOYSA-N 0.000 description 4
STIGNTJPMPNNCK-UHFFFAOYSA-N 4-oxochromene-2-carbaldehyde Chemical compound C1=CC=C2OC(C=O)=CC(=O)C2=C1 STIGNTJPMPNNCK-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
229910000564 Raney nickel Inorganic materials 0.000 description 4
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
229940124630 bronchodilator Drugs 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
150000004683 dihydrates Chemical class 0.000 description 4
150000002118 epoxides Chemical group 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
239000002198 insoluble material Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
WLDWSGZHNBANIO-UHFFFAOYSA-N 2',5'-Dihydroxyacetophenone Chemical compound CC(=O)C1=CC(O)=CC=C1O WLDWSGZHNBANIO-UHFFFAOYSA-N 0.000 description 3
GIOKFSNYCVNEGL-UHFFFAOYSA-N O.C(=O)(O)C=1OC2=CC=CC(=C2C(C1)=O)OCCCCCOC1=C2C(C=C(OC2=CC=C1)C(=O)O)=O Chemical compound O.C(=O)(O)C=1OC2=CC=CC(=C2C(C1)=O)OCCCCCOC1=C2C(C=C(OC2=CC=C1)C(=O)O)=O GIOKFSNYCVNEGL-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
201000009961 allergic asthma Diseases 0.000 description 3
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 3
YTIVTFGABIZHHX-UHFFFAOYSA-N butynedioic acid Chemical compound OC(=O)C#CC(O)=O YTIVTFGABIZHHX-UHFFFAOYSA-N 0.000 description 3
159000000007 calcium salts Chemical class 0.000 description 3
239000002026 chloroform extract Substances 0.000 description 3
238000006356 dehydrogenation reaction Methods 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
230000006872 improvement Effects 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
229910010272 inorganic material Inorganic materials 0.000 description 3
238000011835 investigation Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
230000004048 modification Effects 0.000 description 3
238000012986 modification Methods 0.000 description 3
150000002912 oxalic acid derivatives Chemical class 0.000 description 3
UILPJVPSNHJFIK-UHFFFAOYSA-N p-methoxy-o-hydroxyacetophenone Natural products COC1=CC=C(C(C)=O)C(O)=C1 UILPJVPSNHJFIK-UHFFFAOYSA-N 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
AHQTYUNPLZYCOL-UHFFFAOYSA-N 1,4-dioxane;ethanol;hydrate Chemical compound O.CCO.C1COCCO1 AHQTYUNPLZYCOL-UHFFFAOYSA-N 0.000 description 2
RUOPAUDVYRHXDB-UHFFFAOYSA-N 1-[2-[3-(2-acetyl-3-hydroxyphenoxy)-2-hydroxypropoxy]-6-hydroxyphenyl]ethanone Chemical compound CC(=O)C1=C(O)C=CC=C1OCC(O)COC1=CC=CC(O)=C1C(C)=O RUOPAUDVYRHXDB-UHFFFAOYSA-N 0.000 description 2
BVFXPYVNONOIOL-UHFFFAOYSA-N 1-[2-[3-(2-acetyl-3-hydroxyphenoxy)propoxy]-6-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCCCOC2=C(C(=CC=C2)O)C(C)=O)C=CC=C1O BVFXPYVNONOIOL-UHFFFAOYSA-N 0.000 description 2
DHUTWEOFUONKPW-UHFFFAOYSA-N 1-[2-[4-(2-acetyl-3-hydroxyphenoxy)but-2-enoxy]-6-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCC=CCOC2=C(C(=CC=C2)O)C(C)=O)C=CC=C1O DHUTWEOFUONKPW-UHFFFAOYSA-N 0.000 description 2
KTQBMKQANYHTMS-UHFFFAOYSA-N 1-[6-[3-(2-acetyl-4-ethyl-3-hydroxyphenoxy)-2-hydroxypropoxy]-3-ethyl-2-hydroxyphenyl]ethanone Chemical compound C(C)(=O)C1=C(OCC(COC2=C(C(=C(C=C2)CC)O)C(C)=O)O)C=CC(=C1O)CC KTQBMKQANYHTMS-UHFFFAOYSA-N 0.000 description 2
CVFFLNSOIOGOFJ-UHFFFAOYSA-N 4-[5-(4-hydroxyphenoxy)pentoxy]phenol Chemical compound C1=CC(O)=CC=C1OCCCCCOC1=CC=C(O)C=C1 CVFFLNSOIOGOFJ-UHFFFAOYSA-N 0.000 description 2
CJEWQOCXIZVERD-UHFFFAOYSA-N 4-oxochromene-2-carbonitrile Chemical compound C1=CC=C2C(=O)C=C(C#N)OC2=C1 CJEWQOCXIZVERD-UHFFFAOYSA-N 0.000 description 2
YIHPBFNJUANWMM-UHFFFAOYSA-N 5-[10-(2-carboxy-4-oxochromen-5-yl)oxydecoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCCCCCCCCCCOC1=C2C(=O)C=C(C(=O)O)OC2=CC=C1 YIHPBFNJUANWMM-UHFFFAOYSA-N 0.000 description 2
MPAJUPGHFOZQQT-UHFFFAOYSA-N 5-[2-[2-(2-carboxy-4-oxochromen-5-yl)oxyethoxy]ethoxy]-4-oxochromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCCOCCOC1=C2C(=O)C=C(C(=O)O)OC2=CC=C1 MPAJUPGHFOZQQT-UHFFFAOYSA-N 0.000 description 2
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125000005504 styryl group Chemical group 0.000 description 1
239000000126 substance Substances 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
238000010998 test method Methods 0.000 description 1
UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
150000004685 tetrahydrates Chemical class 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 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
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
230000009385 viral infection Effects 0.000 description 1

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Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO373069A 1965-03-25 1969-09-18 NO124993B (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
NO373069A NO124993B (fr)	1965-03-25	1969-09-18

Applications Claiming Priority (8)

Application Number	Priority Date	Filing Date	Title
GB12626/65A GB1144905A (en)	1965-03-25	1965-03-25	Substituted bis-(2-carboxy-chromonyl-oxy) derivatives and preparation and pharmaceutical compositions thereof
GB5241465		1965-12-09
GB5374465		1965-12-17
NO162258A NO124875B (fr)	1965-03-25	1966-03-23
GB37765/68A GB1144906A (en)	1965-03-25	1968-08-07	Bis-phenoxy derivatives
DE19691918142 DE1918142A1 (de)	1969-04-10	1969-04-10	Verfahren zur Herstellung von Bischromonverbindungen
DE19691920365 DE1920365A1 (de)	1969-04-22	1969-04-22	Verfahren zur Herstellung von Bis-Chromonen
NO373069A NO124993B (fr)	1965-03-25	1969-09-18

Publications (1)

Publication Number	Publication Date
NO124993B true NO124993B (fr)	1972-07-03

Family

ID=27570482

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO373069A NO124993B (fr)	1965-03-25	1969-09-18

Country Status (1)

Country	Link
NO (1)	NO124993B (fr)

1969
- 1969-09-18 NO NO373069A patent/NO124993B/no unknown

Publication	Publication Date	Title
US3419578A (en)	1968-12-31	Bis-chromonyl compounds
NO162258B (no)	1989-08-21	Fremgangsm te for fremstilling av nitrogengass.
US3686412A (en)	1972-08-22	Compositions containing bis-chromonyl compounds for inhibiting antigen-antibody reactions
US3484445A (en)	1969-12-16	Derivatives of chromone-2-carboxylic acid
US3629290A (en)	1971-12-21	Derivatives of chromone-2-carboxylic acid
NO168643B (no)	1991-12-09	Analogifremgangsmaate for fremstilling av terapeutisk aktive dihydrobenzopyranderivater.
JPS58131936A (ja)	1983-08-06	フエニルカルボン酸誘導体、その製造法及び該化合物を含有する、緩慢にアナフイラキシ−作用する物質に対する「あ」抗剤
NO154522B (no)	1986-06-30	Analogifremgangsmaate for fremstilling av terapeutisk virksomme kinolinderivater.
US3427324A (en)	1969-02-11	Derivatives of chromone-2-carboxylic acid
US3673218A (en)	1972-06-27	Bichromonyl compounds
US3705945A (en)	1972-12-12	Pharmaceutically active compounds
US3718668A (en)	1973-02-27	Benzodipyrones
US3686320A (en)	1972-08-22	Bis-phenoxy compounds
Althuis et al.	1980	Structure-activity relationships in a series of novel 3, 4-dihydro-4-oxopyrimido [4, 5-b] quinoline-2-carboxylic acid antiallergy agents
US3777033A (en)	1973-12-04	Bis-chromonyl pharmaceutical composi-tion and methods
NO124993B (fr)	1972-07-03
US3585214A (en)	1971-06-15	Hydroxyl derivatives of coumarine and processes for the preparation thereof
NO742077L (fr)	1975-01-06
US3823165A (en)	1974-07-09	Pharmaceutically active compounds
US3862175A (en)	1975-01-21	Bis-chromone compounds
Siegel et al.	1951	The preparation of isochromans
NO144110B (no)	1981-03-16	Analogifremgangsmaate ved fremstilling av terapeutisk aktive 5:6-benzo-4-pyron-derivater
Haworth et al.	1954	Chebulinic acid. Part III. Oxidation of ellagic and flavellagic acids and the synthesis of some iso coumarin derivatives
US4335048A (en)	1982-06-15	5-(2-Hydroxypropoxy)-8-propyl-4H-1-benzopyran-4-one-2-carboxylic acid
NO124833B (fr)	1972-06-12