CH615673A5 - - Google Patents
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- Publication number
- CH615673A5 CH615673A5 CH362279A CH362279A CH615673A5 CH 615673 A5 CH615673 A5 CH 615673A5 CH 362279 A CH362279 A CH 362279A CH 362279 A CH362279 A CH 362279A CH 615673 A5 CH615673 A5 CH 615673A5
- Authority
- CH
- Switzerland
- Prior art keywords
- compound
- formula
- parts
- radical
- hydroxy
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- -1 alkali metal salts Chemical class 0.000 description 12
- 239000000243 solution Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000000427 antigen Substances 0.000 description 5
- 102000036639 antigens Human genes 0.000 description 5
- 108091007433 antigens Proteins 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- YQCGBHBRCNCNLL-UHFFFAOYSA-N 5-(2-hydroxypropoxy)-4-oxo-8-propylchromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C(CCC)=CC=C2OCC(C)O YQCGBHBRCNCNLL-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 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 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 208000006673 asthma Diseases 0.000 description 3
- 210000003238 esophagus Anatomy 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
- 239000008101 lactose Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 210000005095 gastrointestinal system Anatomy 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000000750 progressive effect Effects 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- LULUSKLIVDXHON-UHFFFAOYSA-N 5-(2-hydroxypropoxy)-4-oxo-8-propylchromene-2-carbonitrile Chemical compound O1C(C#N)=CC(=O)C2=C1C(CCC)=CC=C2OCC(C)O LULUSKLIVDXHON-UHFFFAOYSA-N 0.000 description 1
- JLCUCYZXSXFTPB-UHFFFAOYSA-N 5-(2-hydroxypropoxy)-4-oxo-8-propylchromene-2-carboxamide Chemical compound O1C(C(N)=O)=CC(=O)C2=C1C(CCC)=CC=C2OCC(C)O JLCUCYZXSXFTPB-UHFFFAOYSA-N 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 208000009793 Milk Hypersensitivity Diseases 0.000 description 1
- 201000010859 Milk allergy Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 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 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 201000009961 allergic asthma Diseases 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003153 chemical reaction reagent Chemical class 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- LOAKCJHVAZDMKD-UHFFFAOYSA-N ethyl 5-(2-hydroxypropoxy)-4-oxo-8-propylchromene-2-carboxylate Chemical compound O1C(C(=O)OCC)=CC(=O)C2=C1C(CCC)=CC=C2OCC(C)O LOAKCJHVAZDMKD-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 208000030533 eye disease Diseases 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 201000005298 gastrointestinal allergy Diseases 0.000 description 1
- 238000001033 granulometry Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 201000001371 inclusion conjunctivitis Diseases 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 201000010659 intrinsic asthma Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000003901 oxalic acid esters Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 206010044325 trachoma Diseases 0.000 description 1
- 239000000080 wetting agent 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
- C07D311/24—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 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 in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB30647/74A GB1488707A (en) | 1974-07-10 | 1974-07-10 | 5-(2-hydroxy-propoxy)-4-oxo-8-propyl-4h-1-benzopyran-2-carboxylic acid and derivatives thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH615673A5 true CH615673A5 (fi) | 1980-02-15 |
Family
ID=10310913
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH117082A CH637650A5 (fr) | 1974-07-10 | 1975-07-09 | Procede de preparation d'un acide chromone carboxylique. |
| CH897275A CH613201A5 (fi) | 1974-07-10 | 1975-07-09 | |
| CH362279A CH615673A5 (fi) | 1974-07-10 | 1979-04-17 | |
| CH691680A CH625799A5 (fi) | 1974-07-10 | 1980-09-16 | |
| CH442682A CH639083A5 (fr) | 1974-07-10 | 1982-07-20 | Procede de preparation d'un acide chromone carboxylique. |
| CH53983A CH640529A5 (fr) | 1974-07-10 | 1983-01-31 | Procede de preparation d'un acide chromone carboxylique. |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH117082A CH637650A5 (fr) | 1974-07-10 | 1975-07-09 | Procede de preparation d'un acide chromone carboxylique. |
| CH897275A CH613201A5 (fi) | 1974-07-10 | 1975-07-09 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH691680A CH625799A5 (fi) | 1974-07-10 | 1980-09-16 | |
| CH442682A CH639083A5 (fr) | 1974-07-10 | 1982-07-20 | Procede de preparation d'un acide chromone carboxylique. |
| CH53983A CH640529A5 (fr) | 1974-07-10 | 1983-01-31 | Procede de preparation d'un acide chromone carboxylique. |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4335048A (fi) |
| JP (1) | JPS5134164A (fi) |
| AR (1) | AR207470A1 (fi) |
| BE (1) | BE831178A (fi) |
| BR (1) | BR7504313A (fi) |
| CA (1) | CA1065330A (fi) |
| CH (6) | CH637650A5 (fi) |
| DD (1) | DD118627A5 (fi) |
| DE (1) | DE2530289A1 (fi) |
| DK (1) | DK146127C (fi) |
| ES (1) | ES439261A1 (fi) |
| FI (1) | FI751997A (fi) |
| FR (1) | FR2277578A1 (fi) |
| GB (1) | GB1488707A (fi) |
| IE (1) | IE41577B1 (fi) |
| IL (1) | IL47606A (fi) |
| LU (1) | LU72945A1 (fi) |
| NL (1) | NL7508162A (fi) |
| NO (1) | NO143501C (fi) |
| SE (1) | SE419337B (fi) |
| YU (2) | YU174175A (fi) |
| ZA (1) | ZA754128B (fi) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2819859A1 (de) * | 1977-05-06 | 1978-11-09 | Fisons Ltd | Tiermedizinisches behandlungsmittel und inhalationsvorrichtung fuer tiere |
| US4317833A (en) * | 1978-12-27 | 1982-03-02 | Fisons Limited | Method for the reduction of excess gastric acid secretion |
| JPS597933Y2 (ja) * | 1979-06-14 | 1984-03-12 | 積水ハウス株式会社 | 壁体の隙間閉塞構造 |
| EP0040489A1 (en) * | 1980-05-17 | 1981-11-25 | FISONS plc | Mixtures, salts, packages and pharmaceutical compositions containing 5-(2-hydroxypropoxy)-4-oxo-8-propyl-4H-1-benzopyran-2-carboxylic acid or a derivative thereof and an H2 receptor antagonist antihistamine |
| EP0104018A3 (en) * | 1982-09-21 | 1985-06-26 | FISONS plc | Benzopyran, benzothiapyran and quinoline compounds and pharmaceutical compositions containing them |
| US5659051A (en) * | 1993-07-13 | 1997-08-19 | Sumitomo Chemical Company, Limited | Process of producing 2-cyano-4-oxo-4H-benzopyran compounds |
Family Cites Families (8)
| 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 |
| NL140730B (nl) * | 1963-09-27 | 1974-01-15 | Fisons Pharmaceuticals Ltd | Werkwijze voor de bereiding van gesubstitueerde chromoncabonzuur-2-derivaten met remmende werking op anafylactische reacties. |
| US3686320A (en) * | 1965-03-25 | 1972-08-22 | Fisons Pharmaceuticals Ltd | Bis-phenoxy compounds |
| GB1147976A (en) * | 1965-12-21 | 1969-04-10 | Fisons Pharmaceuticals Ltd | Chromone derivatives |
| GB1190194A (en) * | 1966-07-05 | 1970-04-29 | Fisons Pharmaceuticals Ltd | Bis-Phenoxy Compounds and Chromanone and Chromone Derivatives |
| US3629920A (en) * | 1967-06-12 | 1971-12-28 | Hurth Masch Zahnrad Carl | Gear cutter |
| YU35250B (en) * | 1970-08-25 | 1980-10-31 | Fisons Ltd | Process for obtaining 4-oxo-4h-1-benzopyran derivatives |
| GB1389227A (en) * | 1971-09-16 | 1975-04-03 | Fisons Ltd | Chromone-2-carboxylic acid derivatives methods for their preparation and compositions containing them |
-
1974
- 1974-07-10 GB GB30647/74A patent/GB1488707A/en not_active Expired
-
1975
- 1975-01-01 AR AR259483A patent/AR207470A1/es active
- 1975-06-27 ZA ZA00754128A patent/ZA754128B/xx unknown
- 1975-06-30 IL IL47606A patent/IL47606A/xx unknown
- 1975-07-07 IE IE1505/75A patent/IE41577B1/en unknown
- 1975-07-07 DE DE19752530289 patent/DE2530289A1/de not_active Withdrawn
- 1975-07-08 BR BR5527/75D patent/BR7504313A/pt unknown
- 1975-07-08 YU YU01741/75A patent/YU174175A/xx unknown
- 1975-07-08 DK DK309075A patent/DK146127C/da not_active IP Right Cessation
- 1975-07-09 CH CH117082A patent/CH637650A5/fr not_active IP Right Cessation
- 1975-07-09 BE BE158136A patent/BE831178A/xx not_active IP Right Cessation
- 1975-07-09 SE SE7507887A patent/SE419337B/xx unknown
- 1975-07-09 CH CH897275A patent/CH613201A5/xx not_active IP Right Cessation
- 1975-07-09 ES ES74439261A patent/ES439261A1/es not_active Expired
- 1975-07-09 FI FI751997A patent/FI751997A/fi not_active Application Discontinuation
- 1975-07-09 NL NL7508162A patent/NL7508162A/xx not_active Application Discontinuation
- 1975-07-09 FR FR7521558A patent/FR2277578A1/fr active Granted
- 1975-07-09 NO NO752461A patent/NO143501C/no unknown
- 1975-07-10 CA CA231,228A patent/CA1065330A/en not_active Expired
- 1975-07-10 LU LU72945A patent/LU72945A1/xx unknown
- 1975-07-10 DD DD187239A patent/DD118627A5/xx unknown
- 1975-07-10 JP JP50084036A patent/JPS5134164A/ja active Pending
-
1979
- 1979-04-17 CH CH362279A patent/CH615673A5/fr not_active IP Right Cessation
-
1980
- 1980-02-19 US US06/122,284 patent/US4335048A/en not_active Expired - Lifetime
- 1980-09-16 CH CH691680A patent/CH625799A5/fr not_active IP Right Cessation
-
1981
- 1981-07-03 YU YU01657/81A patent/YU165781A/xx unknown
-
1982
- 1982-07-20 CH CH442682A patent/CH639083A5/fr not_active IP Right Cessation
-
1983
- 1983-01-31 CH CH53983A patent/CH640529A5/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK309075A (da) | 1976-01-11 |
| NO143501C (no) | 1981-02-25 |
| IE41577L (en) | 1976-01-10 |
| NL7508162A (nl) | 1976-01-13 |
| ES439261A1 (es) | 1977-06-01 |
| DD118627A5 (fi) | 1976-03-12 |
| FI751997A (fi) | 1976-01-11 |
| NO752461L (fi) | 1976-01-13 |
| CH639083A5 (fr) | 1983-10-31 |
| BR7504313A (pt) | 1976-07-06 |
| CH640529A5 (fr) | 1984-01-13 |
| CA1065330A (en) | 1979-10-30 |
| DE2530289A1 (de) | 1976-01-29 |
| YU165781A (en) | 1982-02-28 |
| DK146127C (da) | 1983-11-28 |
| JPS5134164A (en) | 1976-03-23 |
| NO143501B (no) | 1980-11-17 |
| IE41577B1 (en) | 1980-01-30 |
| BE831178A (fr) | 1976-01-09 |
| IL47606A0 (en) | 1975-08-31 |
| AU8289275A (en) | 1977-01-13 |
| IL47606A (en) | 1979-09-30 |
| FR2277578B1 (fi) | 1979-02-23 |
| US4335048A (en) | 1982-06-15 |
| ZA754128B (en) | 1976-06-30 |
| SE7507887L (sv) | 1976-01-12 |
| CH613201A5 (fi) | 1979-09-14 |
| AR207470A1 (es) | 1976-10-08 |
| GB1488707A (en) | 1977-10-12 |
| FR2277578A1 (fr) | 1976-02-06 |
| DK146127B (da) | 1983-07-04 |
| CH637650A5 (fr) | 1983-08-15 |
| YU174175A (en) | 1982-02-28 |
| LU72945A1 (fi) | 1976-05-31 |
| SE419337B (sv) | 1981-07-27 |
| CH625799A5 (fi) | 1981-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PFA | Name/firm changed |
Owner name: FISONS PLC |
|
| PL | Patent ceased | ||
| PL | Patent ceased |