NO124832B - - Google Patents
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- Publication number
- NO124832B NO124832B NO3728/69A NO372869A NO124832B NO 124832 B NO124832 B NO 124832B NO 3728/69 A NO3728/69 A NO 3728/69A NO 372869 A NO372869 A NO 372869A NO 124832 B NO124832 B NO 124832B
- Authority
- NO
- Norway
- Prior art keywords
- bis
- yloxy
- compounds
- salts
- groups
- Prior art date
Links
- -1 chromanone compound Chemical class 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 14
- 150000001408 amides Chemical class 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 238000004519 manufacturing process Methods 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
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000007269 dehydrobromination reaction Methods 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical group [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 12
- 208000006673 asthma Diseases 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000427 antigen Substances 0.000 description 8
- 102000036639 antigens Human genes 0.000 description 8
- 108091007433 antigens Proteins 0.000 description 8
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- 229940126062 Compound A Drugs 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 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 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 4
- 229940124630 bronchodilator Drugs 0.000 description 4
- IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical group 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 4
- 239000000725 suspension Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 201000009961 allergic asthma Diseases 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical compound C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 description 2
- ZJMMCONRXYYEMQ-UHFFFAOYSA-N 5-[2-hydroxy-3-[2-(hydroxymethyl)-4-oxochromen-5-yl]oxypropoxy]-2-(hydroxymethyl)chromen-4-one Chemical compound OCC=1OC2=CC=CC(=C2C(C1)=O)OCC(COC1=C2C(C=C(OC2=CC=C1)CO)=O)O ZJMMCONRXYYEMQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 208000024711 extrinsic asthma Diseases 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 201000010659 intrinsic asthma Diseases 0.000 description 2
- 230000004199 lung function Effects 0.000 description 2
- 239000006199 nebulizer Substances 0.000 description 2
- 238000003756 stirring 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
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- HQARDVLSJLCFBA-UHFFFAOYSA-N 4-[(4-aminophenyl)carbamoyl]-1h-imidazole-5-carboxylic acid Chemical compound C1=CC(N)=CC=C1NC(=O)C1=C(C(O)=O)NC=N1 HQARDVLSJLCFBA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 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
- 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 206010036790 Productive cough Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 244000250129 Trigonella foenum graecum Species 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 208000028004 allergic respiratory disease Diseases 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 1
- 238000011340 continuous therapy Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- KRBBSLDXYDBFEC-UHFFFAOYSA-N ethyl 5-[3-(2-ethoxycarbonyl-4-oxochromen-5-yl)oxy-2-hydroxypropoxy]-4-oxochromene-2-carboxylate Chemical compound O1C(C(=O)OCC)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=C2C(=O)C=C(C(=O)OCC)OC2=CC=C1 KRBBSLDXYDBFEC-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011953 free-radical catalyst Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 231100000037 inhalation toxicity test Toxicity 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229960001317 isoprenaline Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- LMOINURANNBYCM-UHFFFAOYSA-N metaproterenol Chemical compound CC(C)NCC(O)C1=CC(O)=CC(O)=C1 LMOINURANNBYCM-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical class CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 229960002657 orciprenaline Drugs 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 239000008223 sterile water Substances 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
- 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
- 229960004418 trolamine Drugs 0.000 description 1
- 230000009385 viral infection Effects 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- 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
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Apparatuses For Bulk Treatment Of Fruits And Vegetables And Apparatuses For Preparing Feeds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (6)
| 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 | ||
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO124832B true NO124832B (ru) | 1972-06-12 |
Family
ID=27544127
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO162258A NO124875B (ru) | 1965-03-25 | 1966-03-23 | |
| NO3727/69A NO137497C (no) | 1965-03-25 | 1969-09-18 | Bisfenoksyforbindelser for bruk som utgangsmaterialer ved fremstilling av biskromoner |
| NO3728/69A NO124832B (ru) | 1965-03-25 | 1969-09-18 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO162258A NO124875B (ru) | 1965-03-25 | 1966-03-23 | |
| NO3727/69A NO137497C (no) | 1965-03-25 | 1969-09-18 | Bisfenoksyforbindelser for bruk som utgangsmaterialer ved fremstilling av biskromoner |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US3419578A (ru) |
| JP (5) | JPS5341662B1 (ru) |
| BE (1) | BE678175A (ru) |
| CH (1) | CH486445A (ru) |
| DE (1) | DE1543579C3 (ru) |
| DK (4) | DK134646B (ru) |
| FR (1) | FR5452M (ru) |
| GB (2) | GB1144905A (ru) |
| IL (1) | IL25317A (ru) |
| IT (1) | IT1047628B (ru) |
| MY (1) | MY7000043A (ru) |
| NL (1) | NL147732B (ru) |
| NO (3) | NO124875B (ru) |
| OA (1) | OA03872A (ru) |
| SE (3) | SE372941B (ru) |
| YU (1) | YU32999B (ru) |
Families Citing this family (88)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1144905A (en) * | 1965-03-25 | 1969-03-12 | Fisons Pharmaceuticals Ltd | Substituted bis-(2-carboxy-chromonyl-oxy) derivatives and preparation and pharmaceutical compositions thereof |
| US3862175A (en) * | 1965-03-25 | 1975-01-21 | Fison House | Bis-chromone 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 |
| US3957965A (en) * | 1967-08-08 | 1976-05-18 | Fisons Limited | Sodium chromoglycate inhalation medicament |
| US3860618A (en) * | 1967-08-08 | 1975-01-14 | Philip Saxton Hartley | Chromone |
| GB1292601A (en) * | 1968-10-30 | 1972-10-11 | Fisons Pharmaceuticals Ltd | Bis-(2-carboxy-chromone) compounds, their preparation and pharmaceutical compositions containing them |
| GB1340512A (en) * | 1970-01-21 | 1973-12-12 | Fisons Ltd | Production of esters of chromone-2-carboxylic acids |
| GB1326745A (en) * | 1970-04-25 | 1973-08-15 | Fisons Ltd | Chromone-2-carboxylic acid derivatives |
| US3979407A (en) * | 1970-07-31 | 1976-09-07 | Allen & Hanburys Limited | Chromone derivatives |
| US4029802A (en) * | 1970-08-27 | 1977-06-14 | Fisons Limited | The treatment of asthma, hay fever or urticaria |
| US3968235A (en) | 1970-12-14 | 1976-07-06 | Sandoz Ltd. | Composition and method for combating insects with alkylenedioxyphenyl derivatives |
| US3933804A (en) | 1970-12-14 | 1976-01-20 | Sandoz Ltd., (Sandoz Ag) | Insecticidal 1,3-benzodioxol derivatives |
| US3965122A (en) * | 1970-12-30 | 1976-06-22 | Fujisawa Pharmaceutical Co., Ltd. | Chromone compounds and preparation thereof |
| US4105781A (en) * | 1970-12-30 | 1978-08-08 | Fujisawa Pharmaceutical Co., Ltd. | Chromone compounds and preparation thereof |
| GB1399834A (en) * | 1971-05-12 | 1975-07-02 | Fisons Ltd | Pharmaceutical compositions |
| US4053628A (en) * | 1971-05-12 | 1977-10-11 | Fisons Limited | Composition |
| US3975536A (en) | 1971-05-12 | 1976-08-17 | Fisons Limited | Composition |
| US4006245A (en) * | 1971-07-29 | 1977-02-01 | Fisons Limited | Chemical compounds |
| GB1384530A (en) * | 1971-07-29 | 1975-02-19 | Fisons Ltd | Chromone derivatives |
| GB1410588A (en) * | 1971-08-10 | 1975-10-22 | Fisons Ltd | Composition |
| SU469247A3 (ru) * | 1972-01-14 | 1975-04-30 | Майлз Лабораториз Инк (Фирма) | Способ получени производных хромона |
| GB1428186A (en) * | 1972-06-21 | 1976-03-17 | Fujisawa Pharmaceutical Co | Chromone derivatives |
| FR2196795A1 (en) * | 1972-08-25 | 1974-03-22 | Aries Robert | Amine salts of bis(carboxychromones) - useful for treatment of dyspnoea and bronchoconstriction |
| GB1399647A (en) * | 1972-12-15 | 1975-07-02 | Fisons Ltd | Phenoxyalkoxy-chromone derivatives processes for their preparation and compositions containing them |
| FR2210398A1 (en) * | 1972-12-20 | 1974-07-12 | Aries Robert | Bis-(carboxy-chromone) amino ethoxy-ethyl carboxylate salts - useful as a sedative and prophylactic |
| US3948954A (en) * | 1973-01-19 | 1976-04-06 | Fisons Limited | Bis-chromone-tetrazole/hydroxamic/carboxylic acids |
| FR2217004A1 (en) * | 1973-02-15 | 1974-09-06 | Aries Robert | Sedatives and bronchodilatories - i.e. salts of 1,3-bis(2-carboxychromon-5-yloxy)propanes with 3-hydroxy-2-hydroxymethyl pyridines |
| FR2230358A2 (en) * | 1973-05-25 | 1974-12-20 | Fisons Ltd | Cromoglycate contg. solns. - contg. a second therapeutically active cpd. e.g. an antihistamine |
| US4046910A (en) * | 1974-01-28 | 1977-09-06 | The Upjohn Company | Dosage schedule |
| IL48360A (en) * | 1974-11-09 | 1978-12-17 | Fisons Ltd | Pharmaceutical compositions for the treatment of aphthous stomatitis comprising 1,3-bis-(2-carboxychromon-5-yloxy)-2-carboxychromon-5-yloxy)-2-hydroxypropane |
| DE2634908A1 (de) * | 1974-11-09 | 1977-04-14 | Fisons Ltd | Mittel zur behandlung chronischer haut- oder augenerkrankungen |
| US4161516A (en) * | 1975-07-25 | 1979-07-17 | Fisons Limited | Composition for treating airway disease |
| US4145438A (en) * | 1975-09-10 | 1979-03-20 | Fisons Limited | Method for treatment of eczema or psoriasis |
| US4067992A (en) * | 1975-09-10 | 1978-01-10 | Fisons Limited | Method of treating a psychiatric condition |
| GB1509979A (en) * | 1975-11-28 | 1978-05-10 | Fisons Ltd | Pharmaceutical compositions containing aspirin or indomethacin |
| US4097596A (en) * | 1976-11-02 | 1978-06-27 | American Home Products Corporation | Inhalation therapy for relieving bronchial spasm using quaternary salts of promethazine |
| GB1557082A (en) * | 1977-01-25 | 1979-12-05 | Fisons Ltd | Pharmaceutical mixture containing an antiinflammatory |
| DE2819859A1 (de) * | 1977-05-06 | 1978-11-09 | Fisons Ltd | Tiermedizinisches behandlungsmittel und inhalationsvorrichtung fuer tiere |
| US4192860A (en) * | 1977-05-06 | 1980-03-11 | Fisons Limited | Methods for treating disease conditions |
| AU522792B2 (en) * | 1977-07-19 | 1982-06-24 | Fisons Plc | Pressure pack formulation |
| ATE7897T1 (de) * | 1979-09-05 | 1984-06-15 | Glaxo Group Limited | Phenol-derivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zusammensetzungen. |
| CY1333A (en) * | 1980-04-30 | 1986-10-24 | Fisons Ltd | Pharmaceutical compositions containing cromoglycates |
| EP0061800B1 (en) * | 1981-03-24 | 1985-08-28 | FISONS plc | Anti srs-a carboxylic acid derivatives, processes for their production and pharmaceutical formulations containing them |
| JPS5828509U (ja) * | 1981-08-20 | 1983-02-24 | 関東電気工事株式会社 | 分岐箇所用低圧ロ−ラ |
| US4584315A (en) * | 1981-11-16 | 1986-04-22 | The Upjohn Company | Method of treating ischemic states |
| US4447449A (en) * | 1981-11-16 | 1984-05-08 | The Upjohn Company | Methods of treating ischemic states |
| US5135940A (en) * | 1982-09-23 | 1992-08-04 | Merck Frosst Canada, Inc. | Leukotriene antagonists |
| US4782176A (en) * | 1983-01-24 | 1988-11-01 | Hoffmann-La Roche Inc. | Phenoxycarboxylic acids |
| US4581225A (en) * | 1984-04-25 | 1986-04-08 | Eli Lilly And Company | Sustained release intranasal formulation and method of use thereof |
| ATE90076T1 (de) | 1986-03-27 | 1993-06-15 | Merck Frosst Canada Inc | Tetrahydrocarbazole ester. |
| US4758678A (en) * | 1986-07-18 | 1988-07-19 | Pennwalt Corporation | Preparation of 7-(2,3-epoxypropoxy)flavone |
| US5788983A (en) * | 1989-04-03 | 1998-08-04 | Rutgers, The State University Of New Jersey | Transdermal controlled delivery of pharmaceuticals at variable dosage rates and processes |
| US5428033A (en) | 1990-10-12 | 1995-06-27 | Merck Frosst Canada, Inc. | Saturated hydroxyalkylquinoline acids as leukotriene antagonists |
| US20010003739A1 (en) * | 1993-06-24 | 2001-06-14 | Astrazeneca Ab | Systemic administration of a therapeutic preparation |
| US5830853A (en) | 1994-06-23 | 1998-11-03 | Astra Aktiebolag | Systemic administration of a therapeutic preparation |
| US6632456B1 (en) | 1993-06-24 | 2003-10-14 | Astrazeneca Ab | Compositions for inhalation |
| US6794357B1 (en) | 1993-06-24 | 2004-09-21 | Astrazeneca Ab | Compositions for inhalation |
| GB9317752D0 (en) * | 1993-08-26 | 1993-10-13 | Fisons Plc | New pharmaceutical use |
| US5508451A (en) * | 1994-07-07 | 1996-04-16 | Hoechst Celanese Corporation | Process for the preparation of dialkali metal cromoglycates |
| US6524557B1 (en) * | 1994-12-22 | 2003-02-25 | Astrazeneca Ab | Aerosol formulations of peptides and proteins |
| SE9404468D0 (sv) * | 1994-12-22 | 1994-12-22 | Astra Ab | Powder formulations |
| EP1283035A3 (en) * | 1994-12-22 | 2003-03-19 | AstraZeneca AB | Therapeutic preparation for inhalation containing parathyroid hormone |
| MX9704550A (es) | 1994-12-22 | 1997-10-31 | Astra Ab | Formulaciones de medicamentos en aerosol. |
| CA2174583A1 (en) * | 1995-05-05 | 1996-11-06 | Alexander Chucholowski | Sulfuric acid esters of sugar alcohols |
| US6150400A (en) * | 1997-06-30 | 2000-11-21 | Presutti Laboratories | Method for treating vulvar vestibulitis |
| US6596284B1 (en) | 2002-04-30 | 2003-07-22 | Thomas E. Fleming | Treating eczema with a combination of isotonic saline ocean® and nasal mast cell stabilizers |
| US20050026880A1 (en) * | 2003-07-31 | 2005-02-03 | Robinson Cynthia B. | Combination of dehydroepiandrosterone or dehydroepiandrosterone-sulfate with a cromone for treatment of asthma or chronic obstructive pulmonary disease |
| WO2009131695A1 (en) | 2008-04-25 | 2009-10-29 | Nektar Therapeutics | Oligomer-bis-chromonyl compound conjugates |
| US9925282B2 (en) | 2009-01-29 | 2018-03-27 | The General Hospital Corporation | Cromolyn derivatives and related methods of imaging and treatment |
| US8617517B2 (en) | 2009-01-29 | 2013-12-31 | The General Hospital Corporation | Cromolyn derivatives and related methods of imaging and treatment |
| TR201000733A2 (tr) | 2010-02-02 | 2011-08-22 | Bi̇lgi̇ç Mahmut | Flutikazon, tiotropyum ve sodyum kromoglikat içeren farmasötik bileşimler. |
| WO2013051266A1 (ja) * | 2011-10-03 | 2013-04-11 | 独立行政法人国立長寿医療研究センター | タウ凝集阻害剤 |
| CN109846862A (zh) | 2012-10-25 | 2019-06-07 | 通用医疗公司 | 治疗阿尔茨海默病及相关疾病的组合疗法 |
| US10058530B2 (en) | 2012-10-25 | 2018-08-28 | The General Hospital Corporation | Combination therapies for the treatment of Alzheimer's disease and related disorders |
| US9907799B2 (en) | 2013-04-02 | 2018-03-06 | The Doshisha | Tau aggregation inhibitor |
| US10525005B2 (en) | 2013-05-23 | 2020-01-07 | The General Hospital Corporation | Cromolyn compositions and methods thereof |
| CN110305095A (zh) | 2013-10-22 | 2019-10-08 | 综合医院公司 | 色甘酸衍生物以及成像和治疗的相关方法 |
| PT3104854T (pt) | 2014-02-10 | 2020-06-26 | Respivant Sciences Gmbh | Estabilizadores de mastócitos para tratamento de doença pulmonar |
| WO2015120389A1 (en) | 2014-02-10 | 2015-08-13 | Patara Pharma, LLC | Mast cell stabilizers treatment for systemic disorders |
| WO2017027387A1 (en) | 2015-08-07 | 2017-02-16 | Patara Pharma, LLC | Methods for the treatment of mast cell related disorders with mast cell stabilizers |
| WO2017027402A1 (en) | 2015-08-07 | 2017-02-16 | Patara Pharma, LLC | Methods for the treatment of systemic disorders treatable with mast cell stabilizers, including mast cell related disorders |
| EP3506893A4 (en) | 2016-08-31 | 2020-01-22 | Respivant Sciences GmbH | CROMOLYNE COMPOSITIONS FOR THE TREATMENT OF CHRONIC COUGH DUE TO IDIOPATHIC PULMONARY FIBROSIS |
| US20190240194A1 (en) | 2016-08-31 | 2019-08-08 | The General Hospital Corporation | Macrophages/microglia in neuro-inflammation associated with neurodegenerative diseases |
| AU2017339366A1 (en) | 2016-10-07 | 2019-04-11 | Respivant Sciences Gmbh | Cromolyn compositions for treatment of pulmonary fibrosis |
| US10561612B2 (en) | 2017-07-20 | 2020-02-18 | The General Hospital Corporation | Powdered formulations of cromolyn sodium and ibuprofen |
| KR20210071943A (ko) | 2018-07-02 | 2021-06-16 | 더 제너럴 하스피탈 코포레이션 | 크로몰린 소듐 및 α-락토스의 분말화된 제형 |
| EP4058010A1 (en) | 2019-11-12 | 2022-09-21 | Institut National de la Santé et de la Recherche Médicale (INSERM) | Use of mast cell stabilizer for the treatment of heart failure with preserved ejection fraction |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2769015A (en) * | 1954-10-06 | 1956-10-30 | Lab Laroche Navarron | Process of preparing 3-methyl-chromone |
| US3162673A (en) * | 1960-12-28 | 1964-12-22 | Union Carbide Corp | Bis (aminoaliphatic) carbonates and process for preparation |
| GB1144905A (en) * | 1965-03-25 | 1969-03-12 | Fisons Pharmaceuticals Ltd | Substituted bis-(2-carboxy-chromonyl-oxy) derivatives and preparation and pharmaceutical compositions thereof |
-
1965
- 1965-03-25 GB GB12626/65A patent/GB1144905A/en not_active Expired
-
1966
- 1966-03-07 IL IL25317A patent/IL25317A/en unknown
- 1966-03-21 BE BE678175D patent/BE678175A/xx not_active IP Right Cessation
- 1966-03-22 IT IT6482/66A patent/IT1047628B/it active
- 1966-03-22 US US536281A patent/US3419578A/en not_active Expired - Lifetime
- 1966-03-23 DE DE1543579A patent/DE1543579C3/de not_active Expired
- 1966-03-23 NO NO162258A patent/NO124875B/no unknown
- 1966-03-24 SE SE7002534A patent/SE372941B/xx unknown
- 1966-03-24 FR FR54747A patent/FR5452M/fr not_active Expired
- 1966-03-24 SE SE7002535A patent/SE371185B/xx unknown
- 1966-03-24 SE SE03922/66A patent/SE355184B/xx unknown
- 1966-03-25 CH CH428966A patent/CH486445A/fr not_active IP Right Cessation
- 1966-03-25 NL NL666603997A patent/NL147732B/xx not_active IP Right Cessation
- 1966-03-25 DK DK156266AA patent/DK134646B/da unknown
- 1966-09-20 YU YU1770/66A patent/YU32999B/xx unknown
- 1966-09-30 OA OA52613A patent/OA03872A/xx unknown
-
1968
- 1968-08-07 GB GB37765/68A patent/GB1144906A/en not_active Expired
-
1969
- 1969-09-18 NO NO3727/69A patent/NO137497C/no unknown
- 1969-09-18 NO NO3728/69A patent/NO124832B/no unknown
-
1970
- 1970-03-12 US US19119A patent/US3671625A/en not_active Expired - Lifetime
- 1970-12-15 JP JP11131870A patent/JPS5341662B1/ja active Pending
- 1970-12-17 JP JP11255570A patent/JPS5341663B1/ja active Pending
- 1970-12-31 MY MY197043A patent/MY7000043A/xx unknown
-
1971
- 1971-01-20 JP JP711258A patent/JPS5343492B1/ja active Pending
- 1971-03-09 JP JP46012268A patent/JPS4843506B1/ja active Pending
- 1971-03-11 JP JP1282771A patent/JPS5343493B1/ja active Pending
- 1971-10-14 DK DK500271AA patent/DK128318B/da unknown
- 1971-10-14 DK DK500171AA patent/DK128245B/da unknown
- 1971-10-14 DK DK500371AA patent/DK128353B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| OA03872A (fr) | 1971-12-24 |
| DK134646B (da) | 1976-12-13 |
| IT1047628B (it) | 1980-10-20 |
| IL25317A (en) | 1970-08-19 |
| NO137497C (no) | 1978-03-08 |
| DK128318B (da) | 1974-04-08 |
| NL147732B (nl) | 1975-11-17 |
| MY7000043A (en) | 1970-12-31 |
| JPS5343493B1 (ru) | 1978-11-20 |
| YU32999B (en) | 1976-03-31 |
| CH486445A (fr) | 1970-02-28 |
| GB1144906A (en) | 1969-03-12 |
| NO124875B (ru) | 1972-06-19 |
| JPS5341662B1 (ru) | 1978-11-06 |
| DK128245B (da) | 1974-03-25 |
| DE1543579B2 (de) | 1980-01-03 |
| SE371185B (ru) | 1974-11-11 |
| SE355184B (ru) | 1973-04-09 |
| US3419578A (en) | 1968-12-31 |
| NL6603997A (ru) | 1966-09-26 |
| YU177066A (en) | 1975-08-31 |
| JPS4843506B1 (ru) | 1973-12-19 |
| JPS5343492B1 (ru) | 1978-11-20 |
| FR5452M (ru) | 1967-10-16 |
| BE678175A (ru) | 1966-09-21 |
| DK134646C (ru) | 1977-05-16 |
| GB1144905A (en) | 1969-03-12 |
| DE1543579C3 (de) | 1980-08-28 |
| JPS5341663B1 (ru) | 1978-11-06 |
| US3671625A (en) | 1972-06-20 |
| SE372941B (ru) | 1975-01-20 |
| DE1543579A1 (de) | 1969-11-06 |
| NO137497B (no) | 1977-11-28 |
| DK128353B (da) | 1974-04-16 |
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