NO124832B - - Google Patents

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Info

Publication number: NO124832B
Authority: NO; Norway
Prior art keywords: bis; yloxy; compounds; salts; groups
Prior art date: 1965-03-25

Application number

NO3728/69A

Other languages

English (en)

Norwegian (no)

Inventor

C Fitzmaurice

Lee T Brian

R Altounyan

Original Assignee

Fisons Pharmaceuticals Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1965-03-25

Filing date

1969-09-18

Publication date

1972-06-12

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

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

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

1972-06-12 Publication of NO124832B publication Critical patent/NO124832B/no

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)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pyrane Compounds (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)

NO3728/69A 1965-03-25 1969-09-18 NO124832B (da)

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 (da)	1972-06-12

Family

ID=27544127

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
NO162258A NO124875B (da)	1965-03-25	1966-03-23
NO3728/69A NO124832B (da)	1965-03-25	1969-09-18
NO3727/69A NO137497C (no)	1965-03-25	1969-09-18	Bisfenoksyforbindelser for bruk som utgangsmaterialer ved fremstilling av biskromoner

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
NO162258A NO124875B (da)	1965-03-25	1966-03-23

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
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 (da)
JP (5)	JPS5341662B1 (da)
BE (1)	BE678175A (da)
CH (1)	CH486445A (da)
DE (1)	DE1543579C3 (da)
DK (4)	DK134646B (da)
FR (1)	FR5452M (da)
GB (2)	GB1144905A (da)
IL (1)	IL25317A (da)
IT (1)	IT1047628B (da)
MY (1)	MY7000043A (da)
NL (1)	NL147732B (da)
NO (3)	NO124875B (da)
OA (1)	OA03872A (da)
SE (3)	SE355184B (da)
YU (1)	YU32999B (da)

Families Citing this family (91)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3862175A (en) *	1965-03-25	1975-01-21	Fison House	Bis-chromone compounds
GB1144905A (en) *	1965-03-25	1969-03-12	Fisons Pharmaceuticals Ltd	Substituted bis-(2-carboxy-chromonyl-oxy) derivatives and preparation and pharmaceutical compositions thereof
GB1147976A (en) *	1965-12-21	1969-04-10	Fisons Pharmaceuticals Ltd	Chromone derivatives
GB1190193A (en) *	1966-07-05	1970-04-29	Fisons Pharmaceuticals Ltd	Bis-(2-Carboxy-Chromonyl-Oxy) Derivatives, their preparation, and Pharmaceutical Compositions thereof
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
US3933804A (en)	1970-12-14	1976-01-20	Sandoz Ltd., (Sandoz Ag)	Insecticidal 1,3-benzodioxol derivatives
US3968235A (en)	1970-12-14	1976-07-06	Sandoz Ltd.	Composition and method for combating insects with alkylenedioxyphenyl 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
GB1384530A (en) *	1971-07-29	1975-02-19	Fisons Ltd	Chromone derivatives
US4006245A (en) *	1971-07-29	1977-02-01	Fisons Limited	Chemical compounds
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
DE2634908A1 (de) *	1974-11-09	1977-04-14	Fisons Ltd	Mittel zur behandlung chronischer haut- oder augenerkrankungen
IE41922B1 (en) *	1974-11-09	1980-04-23	Fisons Ltd	Pharmaceutical compositions containing bis-chromones
US4161516A (en) *	1975-07-25	1979-07-17	Fisons Limited	Composition for treating airway disease
US4067992A (en) *	1975-09-10	1978-01-10	Fisons Limited	Method of treating a psychiatric condition
US4145438A (en) *	1975-09-10	1979-03-20	Fisons Limited	Method for treatment of eczema or psoriasis
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
DE3068213D1 (en) *	1979-09-05	1984-07-19	Glaxo Group Ltd	Phenol derivatives, processes for their preparation and pharmaceutical compositions containing them
GB2077100B (en) *	1980-04-30	1985-04-24	Fisons Ltd	Pharmaceutical compositions containing cromoglycates
DE3265715D1 (en)	1981-03-24	1985-10-03	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
US6794357B1 (en) *	1993-06-24	2004-09-21	Astrazeneca Ab	Compositions for inhalation
US6632456B1 (en)	1993-06-24	2003-10-14	Astrazeneca Ab	Compositions for inhalation
US5830853A (en)	1994-06-23	1998-11-03	Astra Aktiebolag	Systemic administration of a therapeutic preparation
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
JP4155594B2 (ja)	1994-12-22	2008-09-24	アストラゼネカ・アクチエボラーグ	エアゾール製剤
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
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
US9095621B2 (en)	2008-04-25	2015-08-04	Nektar Therapeutics	Oligome-bis-chromonyl compound conjugates
EP3567033A1 (en) *	2009-01-29	2019-11-13	The General Hospital Corporation	Cromolyn derivatives and related methods of imaging and treatment
US9925282B2 (en)	2009-01-29	2018-03-27	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.
US20140249180A1 (en) *	2011-10-03	2014-09-04	National Center For Geriatrics And Gerontology	Tau aggregation inhibitor
CN104869993B (zh)	2012-10-25	2019-01-15	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
EP2962687B1 (en)	2013-04-02	2019-06-05	The Doshisha	Tau aggregation inhibitor
US10525005B2 (en)	2013-05-23	2020-01-07	The General Hospital Corporation	Cromolyn compositions and methods thereof
AU2014340182B2 (en)	2013-10-22	2019-05-23	The General Hospital Corporation	Cromolyn derivatives and related methods of imaging and treatment
JP2017505348A (ja)	2014-02-10	2017-02-16	パタラファーマリミテッドライアビリティカンパニー	肺疾患治療のための肥満細胞安定剤
PL3104853T3 (pl)	2014-02-10	2020-05-18	Respivant Sciences Gmbh	Leczenie stabilizatorami komórek tucznych zaburzeń ogólnoustrojowych
US10265296B2 (en)	2015-08-07	2019-04-23	Respivant Sciences Gmbh	Methods for the treatment of systemic disorders treatable with mast cell stabilizers, including mast cell related 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
JP2019528320A (ja)	2016-08-31	2019-10-10	レシュピファントサイエンシスゲゼルシャフトミットベシュレンクターハフトゥングＲｅｓｐｉｖａｎｔＳｃｉｅｎｃｅｓＧｍｂｈ	特発性肺線維症による慢性咳の治療のためのクロモリン組成物
US20190240194A1 (en)	2016-08-31	2019-08-08	The General Hospital Corporation	Macrophages/microglia in neuro-inflammation associated with neurodegenerative diseases
EP3522983A4 (en)	2016-10-07	2020-06-03	Respivant Sciences GmbH	CROMOLYN COMPOSITION FOR TREATING LUNG FIBROSIS
CN111565711B (zh)	2017-07-20	2023-01-03	阿茨治疗股份有限公司	色甘酸钠和布洛芬的粉末化制剂
KR20210071943A (ko)	2018-07-02	2021-06-16	더 제너럴 하스피탈 코포레이션	크로몰린 소듐 및 α-락토스의 분말화된 제형
US12383528B2 (en)	2018-12-10	2025-08-12	The General Hospital Corporation	Cromolyn esters and uses thereof
WO2021094296A1 (en)	2019-11-12	2021-05-20	INSERM (Institut National de la Santé et de la Recherche Médicale)	Use of mast cell stabilizer for the treatment of heart failure with preserved ejection fraction
WO2021207060A1 (en)	2020-04-06	2021-10-14	The General Hospital Corporation	Methods of treatment of coronavirus-induced inflammation conditions
US12612391B2 (en)	2020-12-28	2026-04-28	The General Hospital Corporation	Cromolyn derivatives and uses thereof

Family Cites Families (3)

* Cited by examiner, † Cited by third party
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 SE03922/66A patent/SE355184B/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 SE7002534A patent/SE372941B/xx unknown
- 1966-03-25 NL NL666603997A patent/NL147732B/xx not_active IP Right Cessation
- 1966-03-25 CH CH428966A patent/CH486445A/fr 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 NO3728/69A patent/NO124832B/no unknown
- 1969-09-18 NO NO3727/69A patent/NO137497C/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 DK500371AA patent/DK128353B/da unknown
- 1971-10-14 DK DK500271AA patent/DK128318B/da unknown
- 1971-10-14 DK DK500171AA patent/DK128245B/da unknown

Also Published As

Publication number	Publication date
NL6603997A (da)	1966-09-26
YU177066A (en)	1975-08-31
JPS5343492B1 (da)	1978-11-20
SE371185B (da)	1974-11-11
US3419578A (en)	1968-12-31
DK128353B (da)	1974-04-16
SE355184B (da)	1973-04-09
GB1144906A (en)	1969-03-12
DE1543579B2 (de)	1980-01-03
JPS5341662B1 (da)	1978-11-06
NL147732B (nl)	1975-11-17
DK134646C (da)	1977-05-16
FR5452M (da)	1967-10-16
BE678175A (da)	1966-09-21
DK128245B (da)	1974-03-25
NO137497C (no)	1978-03-08
JPS5341663B1 (da)	1978-11-06
NO137497B (no)	1977-11-28
DK134646B (da)	1976-12-13
OA03872A (fr)	1971-12-24
DE1543579C3 (de)	1980-08-28
IL25317A (en)	1970-08-19
DK128318B (da)	1974-04-08
YU32999B (en)	1976-03-31
JPS5343493B1 (da)	1978-11-20
MY7000043A (en)	1970-12-31
DE1543579A1 (de)	1969-11-06
GB1144905A (en)	1969-03-12
CH486445A (fr)	1970-02-28
IT1047628B (it)	1980-10-20
US3671625A (en)	1972-06-20
NO124875B (da)	1972-06-19
JPS4843506B1 (da)	1973-12-19
SE372941B (da)	1975-01-20

Publication	Publication Date	Title
NO162258B (no)	1989-08-21	Fremgangsm te for fremstilling av nitrogengass.
US5952375A (en)	1999-09-14	Compounds and methods for synthesis and therapy
DE2362409C3 (de)	1980-05-14	N,N'-(m-Phenylen)-dioxamidsäuren und deren Derivate, Verfahren zu ihrer Herstellung und Arzneimittel, die diese Verbindungen enthalten
DE1543579B2 (de)	1980-01-03	Bis-Chromonylverbindungen und deren pharmakologisch nicht giftigen Salze oder niedrige Alkylester und Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
KR0140076B1 (ko)	1998-06-01	치환된 퀴놀린 카르복실산 및 그의 제조방법
NO160759B (no)	1989-02-20	Modulmoebel.
US3652765A (en)	1972-03-28	Pharmaceutical compositions and methods for the treatment of allergic asthma
US4950686A (en)	1990-08-21	Anti-mycoplasma agent
SU831074A3 (ru)	1981-05-15	Способ получени производных бензимида-зОлА
FI90081C (fi)	1993-12-27	Foerfarande foer framstaellning av terapeutiskt aktiva ginkgolidderivat
HUT65627A (en)	1994-07-28	Process for producing of alkynyl-derivatives of indolyl-methoxybenzoyl-benzenesulphonemide compounds and pharmaceutical compositions comprising them
SK216092A3 (en)	1995-09-13	Using of xantine derivatives for treating of secondary lesions of neurous cells and functional defects after injuring of cranium and cerebrum
EP0732329B1 (en)	2002-04-10	Chroman derivative
JPS6072843A (ja)	1985-04-24	４−フエニル−４−オキソ−２−ブテン酸の新誘導体、それらの製造法、薬剤としての使用及びそれらを含む組成物
NO166282B (no)	1991-03-18	Analogifremgangsmaate for fremstilling av terapeutisk aktivt kalsium-9-etyl-6,9-dihydro-4,6-diokso-10-propyl-4h-(3,2-g)-kinolin-2,8-di-karboksylat.
EP0455596B1 (de)	1994-11-02	Substituierte Indole
SE455420B (sv)	1988-07-11	Anvendning av 4-fenyl-4-oxo-butensyraderivat for framstellning av ett lekemedel for behandling av magakommor och gastroduodenala akommor i samband med hyperaciditet
Holland et al.	1976	Cinnoline-3-propionic acids, a new series of orally active antiallergic substances
DE2253914A1 (de)	1973-05-10	Neue chromonderivate und verfahren zu ihrer herstellung
EP0643045B1 (de)	2000-03-08	Chinolin-Verbindungen als Leukotriene Antagonisten
JPS6222993B2 (da)	1987-05-20
NO124833B (da)	1972-06-12
US4472424A (en)	1984-09-18	Esters of 2-thenoylmercaptopropionylglycine with substituted hydroxybenzenes, process for their preparation and pharmaceutical compositions containing same
NO152253B (no)	1985-05-20	Analogifremgangsmaate for fremstlling av 4-(n-(3`,4`-dihydroksybenzyliden)aminometyl)-cykloheksan-1-karboksylsyre med terapeutisk aktivitet
NO124993B (da)	1972-07-03