SE426825B - Cykloalkenokromoner med antiallergisk verkan - Google Patents

Cykloalkenokromoner med antiallergisk verkan

Info

Publication number: SE426825B
Authority: SE; Sweden
Prior art keywords: chromone; tetrazolyl; carboxy; solution; calculated
Prior art date: 1977-12-23

Application number

SE7813282A

Other languages

English (en)

Swedish (sv)

Other versions

SE7813282L (sv

Inventor

B T Warren

J W Spicer

T Miller

Original Assignee

Miles Lab

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.)

1977-12-23

Filing date

1978-12-22

Publication date

1983-02-14

1978-12-22 Application filed by Miles Lab filed Critical Miles Lab

1979-06-24 Publication of SE7813282L publication Critical patent/SE7813282L/xx

1983-02-14 Publication of SE426825B publication Critical patent/SE426825B/sv

Links

230000003266 anti-allergic effect Effects 0.000 title description 7
OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 claims description 90
-1 methylthio, methylsulfonyl Chemical group 0.000 claims description 44
150000001875 compounds Chemical class 0.000 claims description 43
FLGZHHJNRZUPIL-UHFFFAOYSA-N chromene-4-thione Chemical compound C1=CC=C2C(=S)C=COC2=C1 FLGZHHJNRZUPIL-UHFFFAOYSA-N 0.000 claims description 18
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
239000011734 sodium Substances 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 9
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 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052708 sodium Inorganic materials 0.000 claims description 8
125000003831 tetrazolyl group Chemical group 0.000 claims description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
159000000000 sodium salts Chemical class 0.000 claims description 7
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
150000002431 hydrogen Chemical group 0.000 claims description 6
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
239000000243 solution Substances 0.000 description 89
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 68
238000000034 method Methods 0.000 description 60
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 57
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 53
239000000203 mixture Substances 0.000 description 53
238000002844 melting Methods 0.000 description 51
230000008018 melting Effects 0.000 description 51
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 49
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 30
238000001816 cooling Methods 0.000 description 28
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 26
239000000543 intermediate Substances 0.000 description 22
229960000583 acetic acid Drugs 0.000 description 21
239000007787 solid Substances 0.000 description 21
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 20
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 19
238000003756 stirring Methods 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 17
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 16
239000002244 precipitate Substances 0.000 description 16
239000000706 filtrate Substances 0.000 description 15
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
239000012362 glacial acetic acid Substances 0.000 description 14
229910052943 magnesium sulfate Inorganic materials 0.000 description 13
235000019341 magnesium sulphate Nutrition 0.000 description 13
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 12
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 12
WZHXVERXLFPQCU-UHFFFAOYSA-N 2-acetyloxy-5-iodobenzoic acid Chemical compound CC(=O)OC1=CC=C(I)C=C1C(O)=O WZHXVERXLFPQCU-UHFFFAOYSA-N 0.000 description 11
239000000047 product Substances 0.000 description 11
239000000725 suspension Substances 0.000 description 11
235000019441 ethanol Nutrition 0.000 description 10
239000002253 acid Substances 0.000 description 9
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 9
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 8
229910052804 chromium Inorganic materials 0.000 description 8
239000011651 chromium Substances 0.000 description 8
239000010410 layer Substances 0.000 description 8
230000003647 oxidation Effects 0.000 description 8
238000007254 oxidation reaction Methods 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
235000017557 sodium bicarbonate Nutrition 0.000 description 8
229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
229910000029 sodium carbonate Inorganic materials 0.000 description 8
235000019270 ammonium chloride Nutrition 0.000 description 7
239000003610 charcoal Substances 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000013078 crystal Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 6
239000000284 extract Substances 0.000 description 6
210000003630 histaminocyte Anatomy 0.000 description 6
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
238000001914 filtration Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 4
206010020751 Hypersensitivity Diseases 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
230000000172 allergic effect Effects 0.000 description 4
208000006673 asthma Diseases 0.000 description 4
208000010668 atopic eczema Diseases 0.000 description 4
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 4
239000012153 distilled water Substances 0.000 description 4
150000002081 enamines Chemical class 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
238000010992 reflux Methods 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
239000002904 solvent Substances 0.000 description 4
PFIRJCHMLXRCTM-UHFFFAOYSA-N 2-hydroxy-4-(2-iodoacetyl)benzoic acid Chemical compound OC(=O)C1=CC=C(C(=O)CI)C=C1O PFIRJCHMLXRCTM-UHFFFAOYSA-N 0.000 description 3
DUPNZSZWNYYFPS-UHFFFAOYSA-N 5-(2-iodoacetyl)-2-sulfanylbenzoic acid Chemical compound OC(=O)C1=CC(C(=O)CI)=CC=C1S DUPNZSZWNYYFPS-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical class CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 3
229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
229960001138 acetylsalicylic acid Drugs 0.000 description 3
208000026935 allergic disease Diseases 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
239000010949 copper Substances 0.000 description 3
239000012259 ether extract Substances 0.000 description 3
229940032296 ferric chloride Drugs 0.000 description 3
229940044631 ferric chloride hexahydrate Drugs 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
NQXWGWZJXJUMQB-UHFFFAOYSA-K iron trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].Cl[Fe+]Cl NQXWGWZJXJUMQB-UHFFFAOYSA-K 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000003506 spasmogen Substances 0.000 description 3
CAOBRCYYSGFZIY-UHFFFAOYSA-N 2-acetylsulfanyl-4-iodobenzoic acid Chemical compound CC(=O)SC1=CC(I)=CC=C1C(O)=O CAOBRCYYSGFZIY-UHFFFAOYSA-N 0.000 description 2
DHZXSVFKTDBCGT-UHFFFAOYSA-N 4-iodo-2-sulfanylbenzoic acid Chemical compound OC(=O)C1=CC=C(I)C=C1S DHZXSVFKTDBCGT-UHFFFAOYSA-N 0.000 description 2
DSEOHZFMNDXZGY-UHFFFAOYSA-N 5-iodo-2-sulfanylbenzoic acid Chemical compound OC(=O)C1=CC(I)=CC=C1S DSEOHZFMNDXZGY-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
125000004442 acylamino group Chemical group 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 2
230000007815 allergy Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
229960000265 cromoglicic acid Drugs 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
239000004913 cyclooctene Substances 0.000 description 2
239000012954 diazonium Substances 0.000 description 2
VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
150000002366 halogen compounds Chemical class 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
230000020477 pH reduction Effects 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
229960002052 salbutamol Drugs 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
125000004434 sulfur atom Chemical group 0.000 description 2
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 description 1
HIHUAMSKWMGUNW-UHFFFAOYSA-N 2-acetylsulfanylbenzoic acid Chemical class CC(=O)SC1=CC=CC=C1C(O)=O HIHUAMSKWMGUNW-UHFFFAOYSA-N 0.000 description 1
GOLGILSVWFKZRQ-UHFFFAOYSA-N 2-amino-5-iodobenzoic acid Chemical compound NC1=CC=C(I)C=C1C(O)=O GOLGILSVWFKZRQ-UHFFFAOYSA-N 0.000 description 1
SWDNKOFGNPGRPI-UHFFFAOYSA-N 2-hydroxy-5-iodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC=C1O SWDNKOFGNPGRPI-UHFFFAOYSA-N 0.000 description 1
JTJHGUDPCUXMHJ-UHFFFAOYSA-N 2-hydroxy-5-propanethioylbenzoic acid Chemical compound CCC(=S)C1=CC=C(C(C(=O)O)=C1)O JTJHGUDPCUXMHJ-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
206010006482 Bronchospasm Diseases 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
102000015439 Phospholipases Human genes 0.000 description 1
108010064785 Phospholipases Proteins 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
239000013566 allergen Substances 0.000 description 1
208000030961 allergic reaction Diseases 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
210000003567 ascitic fluid Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000007885 bronchoconstriction Effects 0.000 description 1
229940124630 bronchodilator Drugs 0.000 description 1
239000000168 bronchodilator agent Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229940068911 chloride hexahydrate Drugs 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000006071 cream Substances 0.000 description 1
IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound 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 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
230000003112 degranulating effect Effects 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
VOAPTKOANCCNFV-UHFFFAOYSA-N hexahydrate;hydrochloride Chemical compound O.O.O.O.O.O.Cl VOAPTKOANCCNFV-UHFFFAOYSA-N 0.000 description 1
238000001802 infusion Methods 0.000 description 1
208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
229910003480 inorganic solid Inorganic materials 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
150000002497 iodine compounds Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000002372 labelling Methods 0.000 description 1
229940099596 manganese sulfate Drugs 0.000 description 1
239000011702 manganese sulphate Substances 0.000 description 1
235000007079 manganese sulphate Nutrition 0.000 description 1
SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
NCBIJQMSMHJMLP-UHFFFAOYSA-N n,n-diethylethanamine;2-hydroxy-5-(2-iodoacetyl)benzoic acid Chemical compound CCN(CC)CC.OC(=O)C1=CC(C(=O)CI)=CC=C1O NCBIJQMSMHJMLP-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000007935 oral tablet Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000006190 sub-lingual tablet Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000829 suppository Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
229950003937 tolonium Drugs 0.000 description 1
HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 1
238000001665 trituration Methods 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
- C07D311/94—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 condensed with rings other than six-membered or with ring systems containing such rings
- 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
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D311/86—Oxygen atoms, e.g. xanthones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
- C07D335/14—Thioxanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D335/16—Oxygen atoms, e.g. thioxanthones

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)

SE7813282A 1977-12-23 1978-12-22 Cykloalkenokromoner med antiallergisk verkan SE426825B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/863,688 US4221800A (en)	1977-12-23	1977-12-23	Cycloalkenochromone

Publications (2)

Publication Number	Publication Date
SE7813282L SE7813282L (sv)	1979-06-24
SE426825B true SE426825B (sv)	1983-02-14

Family

ID=25341580

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE7813282A SE426825B (sv)	1977-12-23	1978-12-22	Cykloalkenokromoner med antiallergisk verkan

Country Status (9)

Country	Link
US (1)	US4221800A (fr)
BE (1)	BE873043A (fr)
CA (1)	CA1129866A (fr)
DK (1)	DK580678A (fr)
ES (1)	ES476219A1 (fr)
FI (1)	FI76796C (fr)
NL (1)	NL176561C (fr)
NO (1)	NO152652C (fr)
SE (1)	SE426825B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5562082A (en) *	1978-11-01	1980-05-10	Kowa Co	Tetrahydroxanthone derivative
US4571405A (en) *	1984-05-29	1986-02-18	Miles Laboratories, Inc.	Anti-allergic chromone- or thiochromone-5-oxamic acid derivatives, compositions, and method of use therefor

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3232945A (en) *	1962-08-13	1966-02-01	S E Massengill Company	7,8,9,10-tetrahalo-6h-cyclohepta-(b)-quinolines
US3244720A (en) *	1965-01-21	1966-04-05	Mcneilab Inc	Octahydro-9-acridanones
BE759292A (fr) *	1969-11-27	1971-05-24	Allen & Hanburys Ltd	Derives de xanthone, leur preparation et leur emploi
GB1447031A (en) *	1972-05-19	1976-08-25	Wellcome Found	Tricyclic sulphones and pharmaceutical compositions containing them
US3886162A (en) *	1972-07-19	1975-05-27	Syntex Inc	Acridone carboxylic acids and derivatives
DE2337474C2 (de) *	1973-07-24	1982-01-21	Hoechst Ag, 6000 Frankfurt	Chemotherapeutisch wirksame Tetrahydroacridone, Verfahren zu ihrer Herstellung und sie enthaltende Mittel

1977
- 1977-12-23 US US05/863,688 patent/US4221800A/en not_active Expired - Lifetime
1978
- 1978-12-12 CA CA317,749A patent/CA1129866A/fr not_active Expired
- 1978-12-14 FI FI783839A patent/FI76796C/fi not_active IP Right Cessation
- 1978-12-21 ES ES476219A patent/ES476219A1/es not_active Expired
- 1978-12-22 NL NLAANVRAGE7812509,A patent/NL176561C/xx not_active IP Right Cessation
- 1978-12-22 BE BE192540A patent/BE873043A/fr not_active IP Right Cessation
- 1978-12-22 SE SE7813282A patent/SE426825B/sv not_active IP Right Cessation
- 1978-12-22 NO NO784347A patent/NO152652C/no unknown
- 1978-12-22 DK DK580678A patent/DK580678A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
DK580678A (da)	1979-06-24
ES476219A1 (es)	1979-11-16
US4221800A (en)	1980-09-09
SE7813282L (sv)	1979-06-24
NO152652B (no)	1985-07-22
NO152652C (no)	1985-10-30
NL176561C (nl)	1985-05-01
BE873043A (fr)	1979-06-22
NL7812509A (nl)	1979-06-26
NL176561B (nl)	1984-12-03
FI76796C (fi)	1988-12-12
FI783839A7 (fi)	1979-06-24
FI76796B (fi)	1988-08-31
CA1129866A (fr)	1982-08-17
NO784347L (no)	1979-06-26

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Title

Description

1995-01-31

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SE451071B (sv)	1987-08-31	Kveveheterocykliska foreningar innehallande pyrano- eller tiopyranoring, kompositioner innehallande dessa och forfarande for framstellning av dessa
JPS61176591A (ja)	1986-08-08	新規チエノ‐トリアゾロ‐１，４‐ジアゼピノ‐２‐カルボン酸アミド
EP0024290B1 (fr)	1982-12-22	Phényl-8 purines, leur préparation et médicaments les contenant
CH644116A5 (de)	1984-07-13	Imidazolderivate.
EP0047323B1 (fr)	1984-10-10	Derives de 1,4-naphthoquinone et leur utilisation
SE426825B (sv)	1983-02-14	Cykloalkenokromoner med antiallergisk verkan
DE2740836A1 (de)	1979-03-22	Anellierte indolderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
US3355459A (en)	1967-11-28	Derivatives of thiachromanes and process for preparation
Abdel-Hafez et al.	2016	An Efficient Route for Synthesis and Reactions of Seleno-[2, 3-c] Coumarin
NO742077L (fr)	1975-01-06
JPS5967292A (ja)	1984-04-16	チアジン誘導体
EP0251039B1 (fr)	1991-09-18	Esters de salsalate avec gaiacol pour le traitement des bronchopneumopathies phlogistiques
FI84482B (fi)	1991-08-30	Foerfarande foer framstaellning av farmakologiskt vaerdefulla bensodipyran.
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
CA1110249A (fr)	1981-10-06	Indolopyrones ayant des proprietes antiallergiques
EP0211157A1 (fr)	1987-02-25	Derivés d'isoxazole, procédé de préparation et préparations pharmaceutiques les contenant
JPS58188876A (ja)	1983-11-04	抗炎症剤及び抗喘息剤
DE2265052A1 (de)	1976-01-08	Neue substituierte xanthoncarbonsaeureamide
US3954981A (en)	1976-05-04	Triazolocycloalkylhydrothiadiazine derivatives
US4221797A (en)	1980-09-09	Dihydroquinoline-one derivatives
JPH09502704A (ja)	1997-03-18	新規な１，２−ジチイン抗感染症剤
US2990407A (en)	1961-06-27	Co cha
Khan et al.	1978	Synthesis of 3-substituted 1, 4-benzodiazepine-2-ones
JPS5850225B2 (ja)	1983-11-09	新規なキサントン類、それらの塩及びエステル並びにこれらの化合物よりなる医薬
CH510008A (de)	1971-07-15	Verfahren zur Herstellung von neuen heterocyclischen Carbonsäuren