NO743655L - - Google Patents

Info

Publication number: NO743655L
Authority: NO; Norway
Prior art keywords: carboxylic acid; formula; compound; pharmaceutically acceptable; acceptable salt
Prior art date: 1973-10-11

Application number

NO743655A

Other languages

English (en)

Norwegian (no)

Inventor

D R Buckle

B C C Cantello

H Smith

Original Assignee

Beecham Group 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.)

1973-10-11

Filing date

1974-10-10

Publication date

1975-05-05

1974-10-10 Application filed by Beecham Group Ltd filed Critical Beecham Group Ltd

1975-05-05 Publication of NO743655L publication Critical patent/NO743655L/no

Links

150000001875 compounds Chemical class 0.000 claims description 70
238000000034 method Methods 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 25
-1 Isocoumarin-3-carboxylic acid 4-methylisocoumarin-3-carboxylic acid 6,7-Dimethoxyisocoumarin-3-carboxylic acid Chemical compound 0.000 claims description 21
238000002360 preparation method Methods 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 10
125000000623 heterocyclic group Chemical group 0.000 claims description 8
238000005903 acid hydrolysis reaction Methods 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 6
NKQDTSMNXMTHOU-UHFFFAOYSA-N 8-methyl-1-oxoisochromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)OC(=O)C2=C1C=CC=C2C NKQDTSMNXMTHOU-UHFFFAOYSA-N 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
229910021529 ammonia Inorganic materials 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 5
239000000126 substance Substances 0.000 claims description 5
KYWCUACNBIYDNL-UHFFFAOYSA-N 1-Hydroxy-isochinolin-3-carbonsaeure Natural products C1=CC=C2C(=O)NC(C(=O)O)=CC2=C1 KYWCUACNBIYDNL-UHFFFAOYSA-N 0.000 claims description 4
125000004423 acyloxy group Chemical group 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
125000002837 carbocyclic group Chemical group 0.000 claims description 4
125000002843 carboxylic acid group Chemical group 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 4
238000011282 treatment Methods 0.000 claims description 4
239000003513 alkali Substances 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
RIZUCYSQUWMQLX-UHFFFAOYSA-N 2,3-dimethylbenzoic acid Chemical compound CC1=CC=CC(C(O)=O)=C1C RIZUCYSQUWMQLX-UHFFFAOYSA-N 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
239000000203 mixture Substances 0.000 description 10
238000012360 testing method Methods 0.000 description 10
241001465754 Metazoa Species 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000010992 reflux Methods 0.000 description 6
230000004044 response Effects 0.000 description 6
239000007787 solid Substances 0.000 description 6
CRPAMTZHVXHTKH-UHFFFAOYSA-N 1-oxo-1H-isochromene-3-carboxylic acid Chemical compound C1=CC=C2C(=O)OC(C(=O)O)=CC2=C1 CRPAMTZHVXHTKH-UHFFFAOYSA-N 0.000 description 5
CAGOEILZMOBELD-UHFFFAOYSA-N 6,7-dimethoxy-1-oxoisochromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)OC(=O)C2=C1C=C(OC)C(OC)=C2 CAGOEILZMOBELD-UHFFFAOYSA-N 0.000 description 5
208000010201 Exanthema Diseases 0.000 description 5
241000700159 Rattus Species 0.000 description 5
201000005884 exanthem Diseases 0.000 description 5
206010037844 rash Diseases 0.000 description 5
210000002966 serum Anatomy 0.000 description 5
PDPBEHRWSYREIE-UHFFFAOYSA-N 4-methyl-1-oxoisochromene-3-carboxylic acid Chemical compound C1=CC=C2C(C)=C(C(O)=O)OC(=O)C2=C1 PDPBEHRWSYREIE-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
238000010790 dilution Methods 0.000 description 4
239000012895 dilution Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
WGTKWKSCUZJIBY-UHFFFAOYSA-N 7-methoxy-1-oxoisochromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)OC(=O)C2=CC(OC)=CC=C21 WGTKWKSCUZJIBY-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
239000000427 antigen Substances 0.000 description 3
102000036639 antigens Human genes 0.000 description 3
108091007433 antigens Proteins 0.000 description 3
FNJVDWXUKLTFFL-UHFFFAOYSA-N diethyl 2-bromopropanedioate Chemical compound CCOC(=O)C(Br)C(=O)OCC FNJVDWXUKLTFFL-UHFFFAOYSA-N 0.000 description 3
239000000243 solution Substances 0.000 description 3
MFYRORXZDLTDBJ-UHFFFAOYSA-N 1-oxoisothiochromene-3-carboxylic acid Chemical compound C1=CC=C2C(=O)SC(C(=O)O)=CC2=C1 MFYRORXZDLTDBJ-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
POWKKYPZXIUSLQ-UHFFFAOYSA-N 4,6,7-trimethyl-1-oxoisochromene-3-carboxylic acid;hydrate Chemical compound O.CC1=C(C(O)=O)OC(=O)C2=C1C=C(C)C(C)=C2 POWKKYPZXIUSLQ-UHFFFAOYSA-N 0.000 description 2
VVQDKSRVNCYJNC-UHFFFAOYSA-N 7-bromo-2-oxochromene-3-carboxylic acid Chemical compound C1=C(Br)C=C2OC(=O)C(C(=O)O)=CC2=C1 VVQDKSRVNCYJNC-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
229910004373 HOAc Inorganic materials 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
108010058846 Ovalbumin Proteins 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
230000003266 anti-allergic effect Effects 0.000 description 2
208000006673 asthma Diseases 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
239000000872 buffer Substances 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229940092253 ovalbumin Drugs 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 2
238000013207 serial dilution Methods 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
SGVBAFTXLZKMIP-UHFFFAOYSA-N 2-[(4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=C1C(=O)NC(=S)S1 SGVBAFTXLZKMIP-UHFFFAOYSA-N 0.000 description 1
PIWLKMHKNURVRN-UHFFFAOYSA-N 2-acetyl-6-methylbenzoic acid Chemical compound CC(=O)C1=CC=CC(C)=C1C(O)=O PIWLKMHKNURVRN-UHFFFAOYSA-N 0.000 description 1
QDAWXRKTSATEOP-UHFFFAOYSA-N 2-acetylbenzoic acid Chemical compound CC(=O)C1=CC=CC=C1C(O)=O QDAWXRKTSATEOP-UHFFFAOYSA-N 0.000 description 1
CXANNUKKXKKTKG-UHFFFAOYSA-N 2-formyl-4,5-dimethoxybenzoic acid Chemical compound COC1=CC(C=O)=C(C(O)=O)C=C1OC CXANNUKKXKKTKG-UHFFFAOYSA-N 0.000 description 1
LMWSIQGMRIVDCJ-UHFFFAOYSA-N 2-formyl-5-methoxybenzoic acid Chemical compound COC1=CC=C(C=O)C(C(O)=O)=C1 LMWSIQGMRIVDCJ-UHFFFAOYSA-N 0.000 description 1
QCEQRNBCDJKUMU-UHFFFAOYSA-N 2-formyl-6-methylbenzoic acid Chemical compound CC1=CC=CC(C=O)=C1C(O)=O QCEQRNBCDJKUMU-UHFFFAOYSA-N 0.000 description 1
DYNFCHNNOHNJFG-UHFFFAOYSA-N 2-formylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=O DYNFCHNNOHNJFG-UHFFFAOYSA-N 0.000 description 1
UXOFKBQEKNWDJR-UHFFFAOYSA-N 4,8-dimethyl-1-oxoisochromene-3-carboxylic acid Chemical compound CC1=C(C(O)=O)OC(=O)C2=C1C=CC=C2C UXOFKBQEKNWDJR-UHFFFAOYSA-N 0.000 description 1
IIVRZNNHCNKESQ-UHFFFAOYSA-N 4-methyl-1-oxoisothiochromene-3-carboxylic acid Chemical compound C1=CC=C2C(C)=C(C(O)=O)SC(=O)C2=C1 IIVRZNNHCNKESQ-UHFFFAOYSA-N 0.000 description 1
WAMUJTFUQTUCJQ-UHFFFAOYSA-N 5-bromo-2-formylbenzoic acid Chemical compound OC(=O)C1=CC(Br)=CC=C1C=O WAMUJTFUQTUCJQ-UHFFFAOYSA-N 0.000 description 1
HVXXOIGTXJOVON-UHFFFAOYSA-N 6-formyl-2,3-dimethoxybenzoic acid Chemical compound COC1=CC=C(C=O)C(C(O)=O)=C1OC HVXXOIGTXJOVON-UHFFFAOYSA-N 0.000 description 1
IGDXBFZUBGQGMM-UHFFFAOYSA-N 7,8-dimethoxy-2-oxochromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)OC2=C(OC)C(OC)=CC=C21 IGDXBFZUBGQGMM-UHFFFAOYSA-N 0.000 description 1
YAPSJYCJCTVIQZ-UHFFFAOYSA-N 7-bromo-1-oxoisochromene-3-carboxylic acid Chemical compound C1=C(Br)C=C2C(=O)OC(C(=O)O)=CC2=C1 YAPSJYCJCTVIQZ-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
206010002198 Anaphylactic reaction Diseases 0.000 description 1
241000272814 Anser sp. Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
241001239379 Calophysus macropterus Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
206010011224 Cough Diseases 0.000 description 1
206010013142 Disinhibition Diseases 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
241000124008 Mammalia Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000700157 Rattus norvegicus Species 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000036783 anaphylactic response Effects 0.000 description 1
208000003455 anaphylaxis Diseases 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
229940124630 bronchodilator Drugs 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000002775 capsule Substances 0.000 description 1
238000012754 cardiac puncture Methods 0.000 description 1
BPHHNXJPFPEJOF-UHFFFAOYSA-J chembl296966 Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC(S([O-])(=O)=O)=C(N)C2=C(O)C(N=NC3=CC=C(C=C3OC)C=3C=C(C(=CC=3)N=NC=3C(=C4C(N)=C(C=C(C4=CC=3)S([O-])(=O)=O)S([O-])(=O)=O)O)OC)=CC=C21 BPHHNXJPFPEJOF-UHFFFAOYSA-J 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000008105 immune reaction Effects 0.000 description 1
230000002401 inhibitory effect Effects 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
229910052740 iodine Inorganic materials 0.000 description 1
229960001317 isoprenaline Drugs 0.000 description 1
239000007788 liquid Substances 0.000 description 1
SKBDLRWFSRLIPP-UHFFFAOYSA-N meta-hemipinic acid Natural products COC1=CC(C(O)=O)=C(C(O)=O)C=C1OC SKBDLRWFSRLIPP-UHFFFAOYSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal 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
150000007530 organic bases Chemical class 0.000 description 1
210000001672 ovary Anatomy 0.000 description 1
229940066827 pertussis vaccine Drugs 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
206010039083 rhinitis Diseases 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- 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
- C07D311/76—Benzo[c]pyrans

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Pyrane Compounds (AREA)

NO743655A 1973-10-11 1974-10-10 NO743655L (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB47485/73A GB1480737A (en)	1973-10-11	1973-10-11	Isocoumarins thiaisocoumarins and isocarbostyrils and pharmaceutical compositions containing them

Publications (1)

Publication Number	Publication Date
NO743655L true NO743655L (fr)	1975-05-05

Family

ID=10445157

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO743655A NO743655L (fr)	1973-10-11	1974-10-10

Country Status (13)

Country	Link
US (1)	US3975535A (fr)
JP (1)	JPS5064274A (fr)
BE (1)	BE820791A (fr)
DE (1)	DE2448387A1 (fr)
DK (1)	DK530174A (fr)
ES (2)	ES430949A1 (fr)
FI (1)	FI295274A (fr)
FR (1)	FR2247223B1 (fr)
GB (1)	GB1480737A (fr)
NL (1)	NL7413376A (fr)
NO (1)	NO743655L (fr)
SE (2)	SE7412714L (fr)
ZA (1)	ZA746271B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4187309A (en) *	1977-06-20	1980-02-05	Sandoz, Inc.	4-Hydroxy-2-quinolinone-3-carboxylic acids and salts thereof
US4360527A (en) *	1977-10-13	1982-11-23	Warner-Lambert Company	9-(Hydroxy, lower alkoxy or lower alkanoyloxy)-2-(1H-tetrazol-5-yl)naphtho-(2,1-b)-pyran-1-ones and anti-allergic use thereof
US4210667A (en) *	1979-04-19	1980-07-01	Pfizer Inc.	Pharmaceutical preparations containing coumarin carboxylic acid derivatives
JPS5910570A (ja) *	1982-07-08	1984-01-20	Wakamoto Pharmaceut Co Ltd	新規イソカルボスチリル誘導体及びその製法
ZA916646B (en) *	1990-08-23	1992-07-29	Synphar Lab Inc	Novel isocarbostiryl compounds and anti-tumor use thereof
WO2013030358A1 (fr)	2011-08-31	2013-03-07	Merz Pharma Gmbh & Co. Kgaa	Antagonistes de glycine b

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1049289A (en) *	1962-08-18	1966-11-23	Benger Lab Ltd	Chromone derivatives and pharmaceutical compositions containing them
GB1147976A (en) *	1965-12-21	1969-04-10	Fisons Pharmaceuticals Ltd	Chromone derivatives
US3578705A (en) *	1967-07-26	1971-05-11	Merck & Co Inc	Process for the preparation of homophthalic acid
US3864493A (en) *	1967-08-17	1975-02-04	Fisons Ltd Felixstowe	Compositions and methods for the prevention of asthmatic symptoms
US3733338A (en) *	1971-07-29	1973-05-15	Ikeda Pharmaceutical Industry	1-oxo-isochromenes
US3885038A (en) *	1971-08-23	1975-05-20	Syntex Inc	Method of using substituted xanthone carboxylic acid
US3883653A (en) *	1972-10-24	1975-05-13	Pfizer	Method of preventing asthmatic symptoms
US3879544A (en) *	1973-05-09	1975-04-22	Carter Wallace	Method for suppressing histamine release

1973
- 1973-10-11 GB GB47485/73A patent/GB1480737A/en not_active Expired
1974
- 1974-09-30 US US05/510,803 patent/US3975535A/en not_active Expired - Lifetime
- 1974-10-02 ZA ZA00746271A patent/ZA746271B/xx unknown
- 1974-10-07 FR FR7433636A patent/FR2247223B1/fr not_active Expired
- 1974-10-07 BE BE149292A patent/BE820791A/fr unknown
- 1974-10-09 SE SE7412714A patent/SE7412714L/xx unknown
- 1974-10-10 NO NO743655A patent/NO743655L/no unknown
- 1974-10-10 DE DE19742448387 patent/DE2448387A1/de not_active Withdrawn
- 1974-10-10 DK DK530174A patent/DK530174A/da unknown
- 1974-10-10 FI FI2952/74A patent/FI295274A/fi unknown
- 1974-10-10 NL NL7413376A patent/NL7413376A/xx not_active Application Discontinuation
- 1974-10-11 ES ES430949A patent/ES430949A1/es not_active Expired
- 1974-10-11 JP JP49117000A patent/JPS5064274A/ja active Pending
1976
- 1976-07-08 ES ES449699A patent/ES449699A1/es not_active Expired
1977
- 1977-10-19 SE SE7711779A patent/SE7711779L/xx unknown

Also Published As

Publication number	Publication date
AU7409174A (en)	1976-04-15
DK530174A (fr)	1975-06-09
FR2247223A1 (fr)	1975-05-09
DE2448387A1 (de)	1975-04-17
ES449699A1 (es)	1977-07-01
US3975535A (en)	1976-08-17
FI295274A (fr)	1975-04-12
NL7413376A (nl)	1975-04-15
SE7412714L (fr)	1975-04-14
JPS5064274A (fr)	1975-05-31
FR2247223B1 (fr)	1978-07-21
BE820791A (fr)	1975-04-07
GB1480737A (en)	1977-07-20
ES430949A1 (es)	1977-01-01
ZA746271B (en)	1975-10-29
SE7711779L (sv)	1977-10-19

Publication	Publication Date	Title
US4006237A (en)	1977-02-01	Tetrahydrocarbostyril derivatives for the prophylaxis of asthma, hayfever and rhinitis
SU1072803A3 (ru)	1984-02-07	Способ получени производных фталазин-4-илуксусной кислоты или их солей
US4110337A (en)	1978-08-29	Triazolobenzodiazepines
US4036964A (en)	1977-07-19	Isocarbostyril-3-carboxylic acid derivatives for the prophylaxis of asthma, hayfever and rhinitis
US3974289A (en)	1976-08-10	Coumarin derivatives for the treatment of allergies
EP0237028A1 (fr)	1987-09-16	Dérivés de N-(phényl) ou N-(phénylcyclopropyl)-2,5-dihydro-2-oxo-4[(phényl substitué)amino]-3-furannecarboxamide
NO743655L (fr)	1975-05-05
US4012407A (en)	1977-03-15	2-Cyano indan-1,3-diones
US4760078A (en)	1988-07-26	Immunomodulator 1,2-dithiol-3-thione derivative composition, use method and process of producing the same
US4406908A (en)	1983-09-27	Tetrazolylcoumarin derivatives and antiallergic compositions containing the same
US4031099A (en)	1977-06-21	4-Hydroxy-3-nitro-5,6,7,8 tetrahydro-carbostyrils
US4192944A (en)	1980-03-11	Optionally substituted 4-oxo-4H-pyrido[1,2-a]pyrimidine-3-N-(1H-tetrazol-4-yl)carboxamides and their use as antiallergy agents
US4032544A (en)	1977-06-28	3-cyano-4-hydroxy coumarin derivatives
US4065457A (en)	1977-12-27	4-Hydroxy-3-nitro-carbostyril compounds
US4798832A (en)	1989-01-17	Pyrido[1,2-a]pyrimidine compounds, corresponding intermediates and use as SRS-A antagonists
NO150280B (no)	1984-06-12	Analogifremgangsmaate ved fremstilling av terapeutisk aktive 9-aminopyrido(1,2-a)pyrimidinderivater
NO743654L (fr)	1975-05-05
JPS6222993B2 (fr)	1987-05-20
EP0002562B1 (fr)	1981-05-20	Dérivés de la triazolo-quinoléine, procédés pour leur préparation et leur utilisation pharmaceutique
SU1512482A3 (ru)	1989-09-30	Способ получени производных пиримидоизохинолина или их фармацевтически приемлемых солей
US3983156A (en)	1976-09-28	Substituted ω-nitroacetophenones
JP2003520768A (ja)	2003-07-08	ＴＮＦα阻害剤として有用なチアゾロピリミジン
US4845122A (en)	1989-07-04	Anti-allergy treatment using 2-(substituted amino)-4,5-dihydro-4-oxo-3-furancarboxylic acids and derivatives thereof
US4059704A (en)	1977-11-22	Tetrazole coumarin derivatives
US4005219A (en)	1977-01-25	Pharmaceutical compositions and their administration for the prophylaxis of asthma, hayfever and rhinitis