NO743654L - - Google Patents
Info
- Publication number
- NO743654L NO743654L NO743654A NO743654A NO743654L NO 743654 L NO743654 L NO 743654L NO 743654 A NO743654 A NO 743654A NO 743654 A NO743654 A NO 743654A NO 743654 L NO743654 L NO 743654L
- Authority
- NO
- Norway
- Prior art keywords
- tetrazol
- coumarin
- methyl
- compound
- stated
- Prior art date
Links
- -1 6-bromo-4-methyl-3-(tetrazol-5-yl)coumarin Chemical compound 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 37
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 10
- 235000001671 coumarin Nutrition 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- UAZDIGCOBKKMPU-UHFFFAOYSA-O azanium;azide Chemical compound [NH4+].[N-]=[N+]=[N-] UAZDIGCOBKKMPU-UHFFFAOYSA-O 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229960000956 coumarin Drugs 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- KZUGEWLMVUIEQL-UHFFFAOYSA-N 4,6-dimethyl-3-(2h-tetrazol-5-yl)chromen-2-one Chemical compound CC=1C2=CC(C)=CC=C2OC(=O)C=1C=1N=NNN=1 KZUGEWLMVUIEQL-UHFFFAOYSA-N 0.000 claims description 2
- QUAWYAXCXRJKHT-UHFFFAOYSA-N 8-chloro-4-methyl-3-(2h-tetrazol-5-yl)chromen-2-one Chemical compound O=C1OC=2C(Cl)=CC=CC=2C(C)=C1C=1N=NNN=1 QUAWYAXCXRJKHT-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 238000012360 testing method Methods 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 7
- 125000003831 tetrazolyl group Chemical group 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- 208000010201 Exanthema Diseases 0.000 description 5
- 201000005884 exanthem Diseases 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 206010037844 rash Diseases 0.000 description 5
- 210000002966 serum Anatomy 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 241000700159 Rattus Species 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- QQCGYZHQVZKLFD-UHFFFAOYSA-N 4-methyl-3-(2h-tetrazol-5-yl)chromen-2-one Chemical compound O=C1OC=2C=CC=CC=2C(C)=C1C=1N=NNN=1 QQCGYZHQVZKLFD-UHFFFAOYSA-N 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 238000011282 treatment Methods 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 2
- 108010058846 Ovalbumin Proteins 0.000 description 2
- 241000700157 Rattus norvegicus Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000003266 anti-allergic effect Effects 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 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 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229940092253 ovalbumin Drugs 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000013207 serial dilution Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 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
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
- HFRXUQUNIYAAKH-UHFFFAOYSA-N 2-oxo-4-phenylchromene-3-carbonitrile Chemical compound N#CC=1C(=O)OC=2C=CC=CC=2C=1C1=CC=CC=C1 HFRXUQUNIYAAKH-UHFFFAOYSA-N 0.000 description 1
- QYFMBGJKYQCXIQ-UHFFFAOYSA-N 2-oxo-4-propylchromene-3-carbonitrile Chemical compound C1=CC=CC2=C1OC(=O)C(C#N)=C2CCC QYFMBGJKYQCXIQ-UHFFFAOYSA-N 0.000 description 1
- QKJALQPLNMEDAV-UHFFFAOYSA-N 2-oxochromene-3-carbonitrile Chemical compound C1=CC=CC2=C1OC(=O)C(C#N)=C2 QKJALQPLNMEDAV-UHFFFAOYSA-N 0.000 description 1
- GGHGOYSZPZVHJJ-UHFFFAOYSA-N 4,6,7-trimethyl-2-oxochromene-3-carbonitrile Chemical compound O1C(=O)C(C#N)=C(C)C2=C1C=C(C)C(C)=C2 GGHGOYSZPZVHJJ-UHFFFAOYSA-N 0.000 description 1
- UXGFULJYXBXUDP-UHFFFAOYSA-N 4,6-dimethyl-2-oxochromene-3-carbonitrile Chemical compound O1C(=O)C(C#N)=C(C)C2=CC(C)=CC=C21 UXGFULJYXBXUDP-UHFFFAOYSA-N 0.000 description 1
- FZGHMDGFNLQOOG-UHFFFAOYSA-N 4,7-dimethyl-2-oxochromene-3-carbonitrile Chemical compound CC1=C(C#N)C(=O)OC2=CC(C)=CC=C21 FZGHMDGFNLQOOG-UHFFFAOYSA-N 0.000 description 1
- MEXDLKPPFQVZQB-UHFFFAOYSA-N 4-ethyl-2-oxochromene-3-carbonitrile Chemical compound C1=CC=CC2=C1OC(=O)C(C#N)=C2CC MEXDLKPPFQVZQB-UHFFFAOYSA-N 0.000 description 1
- FFBLBFMTKGSSPY-UHFFFAOYSA-N 4-methyl-2-oxochromene-3-carbonitrile Chemical compound C1=CC=CC2=C1OC(=O)C(C#N)=C2C FFBLBFMTKGSSPY-UHFFFAOYSA-N 0.000 description 1
- NPCFOYALAZMRDI-UHFFFAOYSA-N 6-bromo-4-methyl-2-oxochromene-3-carbonitrile Chemical compound C1=CC(Br)=CC2=C1OC(=O)C(C#N)=C2C NPCFOYALAZMRDI-UHFFFAOYSA-N 0.000 description 1
- JYTVXFGXASPMRG-UHFFFAOYSA-N 6-chloro-4-methyl-2-oxochromene-3-carbonitrile Chemical compound C1=CC(Cl)=CC2=C1OC(=O)C(C#N)=C2C JYTVXFGXASPMRG-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
- 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
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- 241000272814 Anser sp. Species 0.000 description 1
- 241001239379 Calophysus macropterus Species 0.000 description 1
- 241000282472 Canis lupus familiaris 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
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 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 1
- 229930195725 Mannitol Natural products 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 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
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 208000010668 atopic eczema Diseases 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
- 230000004071 biological effect Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000012754 cardiac puncture Methods 0.000 description 1
- 239000000969 carrier Substances 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
- 150000004775 coumarins Chemical class 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([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
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 244000144993 groups of animals Species 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000008105 immune reaction Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229960001317 isoprenaline Drugs 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 229940066827 pertussis vaccine Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 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
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 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
- 238000010992 reflux Methods 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012258 stirred mixture 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
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4748473A GB1434645A (en) | 1973-10-11 | 1973-10-11 | Tetrazole coumarin derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO743654L true NO743654L (it) | 1975-05-05 |
Family
ID=10445154
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO743654A NO743654L (it) | 1973-10-11 | 1974-10-10 |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5064273A (it) |
| AT (1) | AT336606B (it) |
| AU (1) | AU7365674A (it) |
| BE (1) | BE820792A (it) |
| DE (1) | DE2448450A1 (it) |
| DK (1) | DK530074A (it) |
| ES (1) | ES430905A1 (it) |
| FI (1) | FI295174A (it) |
| FR (1) | FR2247231B1 (it) |
| GB (1) | GB1434645A (it) |
| NL (1) | NL7413210A (it) |
| NO (1) | NO743654L (it) |
| SE (1) | SE7412712L (it) |
| ZA (1) | ZA745980B (it) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5576873A (en) * | 1978-11-30 | 1980-06-10 | Kaken Pharmaceut Co Ltd | Coumarin derivative, its preparation, and antiallergic drugs containing it as active constituent |
| JPS56158781A (en) | 1980-05-10 | 1981-12-07 | Kaken Pharmaceut Co Ltd | Tetrazolecoumarin derivative, its preparation and antiallergic agent containing the same as active constitutent |
-
1973
- 1973-10-11 GB GB4748473A patent/GB1434645A/en not_active Expired
-
1974
- 1974-09-20 ZA ZA00745980A patent/ZA745980B/xx unknown
- 1974-09-24 AU AU73656/74A patent/AU7365674A/en not_active Expired
- 1974-10-07 BE BE149293A patent/BE820792A/xx unknown
- 1974-10-07 FR FR7433635A patent/FR2247231B1/fr not_active Expired
- 1974-10-08 NL NL7413210A patent/NL7413210A/xx unknown
- 1974-10-08 AT AT806874A patent/AT336606B/de not_active IP Right Cessation
- 1974-10-09 SE SE7412712A patent/SE7412712L/xx unknown
- 1974-10-09 JP JP49116779A patent/JPS5064273A/ja active Pending
- 1974-10-10 DK DK530074A patent/DK530074A/da unknown
- 1974-10-10 FI FI2951/74A patent/FI295174A/fi unknown
- 1974-10-10 NO NO743654A patent/NO743654L/no unknown
- 1974-10-10 ES ES430905A patent/ES430905A1/es not_active Expired
- 1974-10-10 DE DE19742448450 patent/DE2448450A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5064273A (it) | 1975-05-31 |
| ATA806874A (de) | 1976-09-15 |
| NL7413210A (nl) | 1975-04-15 |
| DE2448450A1 (de) | 1975-04-24 |
| AU7365674A (en) | 1976-04-01 |
| FI295174A (it) | 1975-04-12 |
| ES430905A1 (es) | 1976-10-16 |
| AT336606B (de) | 1977-05-10 |
| FR2247231A1 (it) | 1975-05-09 |
| DK530074A (it) | 1975-06-09 |
| ZA745980B (en) | 1975-10-29 |
| GB1434645A (en) | 1976-05-05 |
| SE7412712L (it) | 1975-04-14 |
| FR2247231B1 (it) | 1978-07-21 |
| BE820792A (fr) | 1975-04-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4006237A (en) | Tetrahydrocarbostyril derivatives for the prophylaxis of asthma, hayfever and rhinitis | |
| CA1098520A (en) | Optionally substituted 3-(1h-tetrazol-5-yl)-4h- pyrido¬1,2-a| pyrimidin-4-ones | |
| KR100267802B1 (ko) | 치환된티에닐-또는피롤일카르복시산유도체,그의제조방법및그를함유하는약제학적조성물 | |
| WO1989005297A1 (en) | Compounds | |
| US4569938A (en) | Diuretic, antihypertensive and antihistaminic 7-carboxymethoxy-furo-(3,4-c)-pyridine derivatives | |
| DE2740588A1 (de) | Imidazo- eckige klammer auf 1,2-a eckige klammer zu -chinolin-2-carbon- saeuren und deren derivate sowie pharmazeutische zubereitungen, die diese verbindungen enthalten | |
| NZ207552A (en) | 1,3-dihydro-6-methyl-7-hydroxy-furo-(3,4-c)-pyridine derivatives and pharmaceutical compositions | |
| US4119720A (en) | Unsaturated esters of 4-hydroxy-2-quinolinone-3-carboxylic acids and salts thereof | |
| US4036964A (en) | Isocarbostyril-3-carboxylic acid derivatives for the prophylaxis of asthma, hayfever and rhinitis | |
| US3974289A (en) | Coumarin derivatives for the treatment of allergies | |
| JPS6388185A (ja) | 新規な９−デアザグアニン類 | |
| JPH0225906B2 (it) | ||
| US4031099A (en) | 4-Hydroxy-3-nitro-5,6,7,8 tetrahydro-carbostyrils | |
| NO743654L (it) | ||
| US4082751A (en) | Therapeutic agents | |
| NO743655L (it) | ||
| US4267332A (en) | 3-(Tetrazol-5-yl)-1-azaxanthones | |
| EP0000153A1 (en) | 4-Hydroxy-2-quinolinone-3-carboxylic acids, their preparation and pharmaceutical compositions containing them. | |
| US4031093A (en) | 1,6-Dihydro-6-oxo-2-(ortho-substituted phenyl)pyrimidine-5-carboxylic acid derivatives | |
| US4059704A (en) | Tetrazole coumarin derivatives | |
| US4798832A (en) | Pyrido[1,2-a]pyrimidine compounds, corresponding intermediates and use as SRS-A antagonists | |
| US3979468A (en) | 4'-Chloro-4-ethynylbiphenyl and method of preparing same | |
| NO150280B (no) | Analogifremgangsmaate ved fremstilling av terapeutisk aktive 9-aminopyrido(1,2-a)pyrimidinderivater | |
| CA1300150C (en) | 1,3-dihydro-6-aminomethyl-7-hydroxy-furo-(3,4-c)-pyridine derivatives | |
| US4845122A (en) | Anti-allergy treatment using 2-(substituted amino)-4,5-dihydro-4-oxo-3-furancarboxylic acids and derivatives thereof |