IL43096A - (2) -Benzofirano] Benzofirano -] g, 4 - 3 [-) 1 (- Benzofirans, their preparation and pharmaceutical preparations containing them - Google Patents
(2) -Benzofirano] Benzofirano -] g, 4 - 3 [-) 1 (- Benzofirans, their preparation and pharmaceutical preparations containing themInfo
- Publication number
- IL43096A IL43096A IL43096A IL4309673A IL43096A IL 43096 A IL43096 A IL 43096A IL 43096 A IL43096 A IL 43096A IL 4309673 A IL4309673 A IL 4309673A IL 43096 A IL43096 A IL 43096A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- compound
- compounds
- compositions
- benzopyrano
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 239000000203 mixture Substances 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 6
- 239000011707 mineral Substances 0.000 claims abstract description 6
- -1 nitro, hydroxycarbonylmethoxy Chemical group 0.000 claims abstract description 5
- 150000003901 oxalic acid esters Chemical class 0.000 claims abstract description 5
- 239000003937 drug carrier Substances 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 230000000699 topical effect Effects 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 3
- 239000000243 solution Substances 0.000 claims description 32
- 239000004480 active ingredient Substances 0.000 claims description 16
- 239000011734 sodium Substances 0.000 claims description 13
- 229910052708 sodium Inorganic materials 0.000 claims description 13
- 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 11
- 239000000725 suspension Substances 0.000 claims description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000003826 tablet Substances 0.000 claims description 8
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 claims description 5
- 239000002674 ointment Substances 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 238000007911 parenteral administration Methods 0.000 claims description 4
- 239000002775 capsule Substances 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 3
- 239000007921 spray Substances 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 239000000829 suppository Substances 0.000 claims description 2
- 239000006188 syrup Substances 0.000 claims description 2
- 235000020357 syrup Nutrition 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000006196 drop Substances 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract description 8
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract description 7
- 150000002148 esters Chemical class 0.000 abstract description 6
- 229910015900 BF3 Inorganic materials 0.000 abstract description 4
- 230000003266 anti-allergic effect Effects 0.000 abstract description 4
- 239000007858 starting material Substances 0.000 abstract description 4
- FOEUNCUWGQOUMI-UHFFFAOYSA-N C(=O)(O)OC(=O)O.CC#CC Chemical compound C(=O)(O)OC(=O)O.CC#CC FOEUNCUWGQOUMI-UHFFFAOYSA-N 0.000 abstract description 2
- 150000002596 lactones Chemical class 0.000 abstract description 2
- 150000002989 phenols Chemical class 0.000 abstract description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- 125000004423 acyloxy group Chemical group 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 150000001562 benzopyrans Chemical class 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 72
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 44
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 25
- 239000007787 solid Substances 0.000 description 24
- 238000010992 reflux Methods 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 229960000583 acetic acid Drugs 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000007859 condensation product Substances 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 8
- 239000012043 crude product Substances 0.000 description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000013058 crude material Substances 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- ATNOAWAQFYGAOY-GPTZEZBUSA-J [Na+].[Na+].[Na+].[Na+].Cc1cc(ccc1\N=N\c1ccc2c(cc(c(N)c2c1O)S([O-])(=O)=O)S([O-])(=O)=O)-c1ccc(\N=N\c2ccc3c(cc(c(N)c3c2O)S([O-])(=O)=O)S([O-])(=O)=O)c(C)c1 Chemical compound [Na+].[Na+].[Na+].[Na+].Cc1cc(ccc1\N=N\c1ccc2c(cc(c(N)c2c1O)S([O-])(=O)=O)S([O-])(=O)=O)-c1ccc(\N=N\c2ccc3c(cc(c(N)c3c2O)S([O-])(=O)=O)S([O-])(=O)=O)c(C)c1 ATNOAWAQFYGAOY-GPTZEZBUSA-J 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 229940031098 ethanolamine Drugs 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 229960003699 evans blue Drugs 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 108010058846 Ovalbumin Proteins 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 230000001766 physiological effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
- 235000010262 sodium metabisulphite Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical group [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- AGDGQHCLWQCYQU-AATRIKPKSA-N (E)-2-(2H-pyran-2-yl)but-2-enedioic acid Chemical compound O1C(C=CC=C1)/C(/C(=O)O)=C\C(=O)O AGDGQHCLWQCYQU-AATRIKPKSA-N 0.000 description 1
- UXXOGXRLAYMMCY-UHFFFAOYSA-N 1-(3-hydroxy-6,6-dimethylbenzo[c]chromen-2-yl)ethanone Chemical compound C1=CC=C2C(C=C(C(=C3)O)C(=O)C)=C3OC(C)(C)C2=C1 UXXOGXRLAYMMCY-UHFFFAOYSA-N 0.000 description 1
- ZWJMMYNLHOQMPQ-UHFFFAOYSA-N 1-(3-hydroxy-6h-benzo[c]chromen-2-yl)ethanone Chemical compound C1=CC=C2C(C=C(C(=C3)O)C(=O)C)=C3OCC2=C1 ZWJMMYNLHOQMPQ-UHFFFAOYSA-N 0.000 description 1
- FCGYRZSKKVPMHC-UHFFFAOYSA-N 1-(3-hydroxy-8,9-dimethoxy-6,6-dimethylbenzo[c]chromen-2-yl)ethanone Chemical compound C12=CC(C(C)=O)=C(O)C=C2OC(C)(C)C2=C1C=C(OC)C(OC)=C2 FCGYRZSKKVPMHC-UHFFFAOYSA-N 0.000 description 1
- DKIDEPVFCBKTRA-UHFFFAOYSA-N 1-(3-hydroxy-8-methoxy-6,6-dimethylbenzo[c]chromen-2-yl)ethanone Chemical compound CC(=O)C1=C(O)C=C2OC(C)(C)C3=CC(OC)=CC=C3C2=C1 DKIDEPVFCBKTRA-UHFFFAOYSA-N 0.000 description 1
- ASRPJUBQAYQGBZ-UHFFFAOYSA-N 1-(6,6-dibutyl-3-hydroxybenzo[c]chromen-2-yl)ethanone Chemical compound C1=CC=C2C(CCCC)(CCCC)OC3=CC(O)=C(C(C)=O)C=C3C2=C1 ASRPJUBQAYQGBZ-UHFFFAOYSA-N 0.000 description 1
- MIXRUVNIFWFXSW-UHFFFAOYSA-N 1-(9-chloro-3-hydroxy-6,6-dimethylbenzo[c]chromen-2-yl)ethanone Chemical compound C1=C(Cl)C=C2C(C=C(C(=C3)O)C(=O)C)=C3OC(C)(C)C2=C1 MIXRUVNIFWFXSW-UHFFFAOYSA-N 0.000 description 1
- PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 description 1
- XRXMNWGCKISMOH-UHFFFAOYSA-N 2-bromobenzoic acid Chemical class OC(=O)C1=CC=CC=C1Br XRXMNWGCKISMOH-UHFFFAOYSA-N 0.000 description 1
- BDDLHHRCDSJVKV-UHFFFAOYSA-N 7028-40-2 Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O BDDLHHRCDSJVKV-UHFFFAOYSA-N 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- NFHFLMVBHYUDAD-UHFFFAOYSA-N COC(=O)OC(=O)OC.C#C Chemical compound COC(=O)OC(=O)OC.C#C NFHFLMVBHYUDAD-UHFFFAOYSA-N 0.000 description 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
- 241000468081 Citrus bergamia Species 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 238000005618 Fries rearrangement reaction Methods 0.000 description 1
- 206010020751 Hypersensitivity Diseases 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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 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
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- WJGAPUXHSQQWQF-UHFFFAOYSA-N acetic acid;hydrochloride Chemical compound Cl.CC(O)=O WJGAPUXHSQQWQF-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 201000009961 allergic asthma Diseases 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 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
- 238000000354 decomposition reaction Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical class OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Cosmetics (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT742572A AT320645B (de) | 1972-08-29 | 1972-08-29 | Verfahren zur Herstellung neuer 2-Carboxy-4-oxo-4H,10H-(2)-benzopyrano-[4,3-g]-(1)-benzopyrane und ihrer Salze |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL43096A0 IL43096A0 (en) | 1973-11-28 |
| IL43096A true IL43096A (en) | 1977-06-30 |
Family
ID=3595927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL43096A IL43096A (en) | 1972-08-29 | 1973-08-28 | (2) -Benzofirano] Benzofirano -] g, 4 - 3 [-) 1 (- Benzofirans, their preparation and pharmaceutical preparations containing them |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US3901925A (en, 2012) |
| JP (1) | JPS4956999A (en, 2012) |
| AT (1) | AT320645B (en, 2012) |
| AU (1) | AU464515B2 (en, 2012) |
| BE (1) | BE804123A (en, 2012) |
| BG (2) | BG21024A3 (en, 2012) |
| CA (1) | CA1016951A (en, 2012) |
| CH (2) | CH581139A5 (en, 2012) |
| CS (1) | CS179427B2 (en, 2012) |
| DD (1) | DD109870A5 (en, 2012) |
| DE (1) | DE2343291C3 (en, 2012) |
| DK (1) | DK131569B (en, 2012) |
| ES (2) | ES418271A1 (en, 2012) |
| FR (1) | FR2197594B1 (en, 2012) |
| GB (1) | GB1439990A (en, 2012) |
| HU (1) | HU166366B (en, 2012) |
| IE (1) | IE38317B1 (en, 2012) |
| IL (1) | IL43096A (en, 2012) |
| IT (1) | IT7949487A0 (en, 2012) |
| NL (1) | NL7311799A (en, 2012) |
| NO (1) | NO138567C (en, 2012) |
| PL (1) | PL85433B1 (en, 2012) |
| RO (2) | RO63037A (en, 2012) |
| SE (1) | SE396389B (en, 2012) |
| SU (2) | SU485596A3 (en, 2012) |
| ZA (1) | ZA735838B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5498419A (en) * | 1994-06-03 | 1996-03-12 | Pars; Harry G. | Fumarate salt of 4-(diethyl-3-(1-methyloctyl)-7,8,9,10-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol, 4-(diethyl-amino) butyric |
| US5892118A (en) * | 1996-10-09 | 1999-04-06 | Daiwa Kasei Industry Co., Ltd. | Process for producing 4,6-diaminoresorcinols |
| WO2004073612A2 (en) * | 2003-02-13 | 2004-09-02 | Merck & Co. Inc. | Estrogen receptor modulators |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3741990A (en) * | 1969-07-28 | 1973-06-26 | Upjohn Co | Organic compounds and processes |
-
1972
- 1972-08-29 AT AT742572A patent/AT320645B/de not_active IP Right Cessation
-
1973
- 1973-08-21 RO RO7300078264A patent/RO63037A/ro unknown
- 1973-08-21 RO RO7300075862A patent/RO62920A/ro unknown
- 1973-08-24 CH CH796276A patent/CH581139A5/xx not_active IP Right Cessation
- 1973-08-24 CH CH1221373A patent/CH581657A5/xx not_active IP Right Cessation
- 1973-08-27 CS CS7300005972A patent/CS179427B2/cs unknown
- 1973-08-27 BG BG025537A patent/BG21024A3/xx unknown
- 1973-08-27 BG BG024398A patent/BG19797A3/xx unknown
- 1973-08-27 SU SU1962548A patent/SU485596A3/ru active
- 1973-08-27 SU SU1962550A patent/SU482042A3/ru active
- 1973-08-27 HU HUBO1459A patent/HU166366B/hu unknown
- 1973-08-27 ES ES418271A patent/ES418271A1/es not_active Expired
- 1973-08-27 ZA ZA00735838A patent/ZA735838B/xx unknown
- 1973-08-28 NL NL7311799A patent/NL7311799A/xx not_active Application Discontinuation
- 1973-08-28 US US392182A patent/US3901925A/en not_active Expired - Lifetime
- 1973-08-28 PL PL1973164886A patent/PL85433B1/pl unknown
- 1973-08-28 SE SE7311690A patent/SE396389B/xx unknown
- 1973-08-28 CA CA179,828A patent/CA1016951A/en not_active Expired
- 1973-08-28 GB GB4041773A patent/GB1439990A/en not_active Expired
- 1973-08-28 IL IL43096A patent/IL43096A/en unknown
- 1973-08-28 DE DE2343291A patent/DE2343291C3/de not_active Expired
- 1973-08-28 NO NO3383/73A patent/NO138567C/no unknown
- 1973-08-28 DK DK471873AA patent/DK131569B/da unknown
- 1973-08-28 AU AU59708/73A patent/AU464515B2/en not_active Expired
- 1973-08-28 BE BE135029A patent/BE804123A/xx unknown
- 1973-08-28 JP JP48096558A patent/JPS4956999A/ja active Pending
- 1973-08-29 FR FR7331242A patent/FR2197594B1/fr not_active Expired
- 1973-08-29 DD DD173155A patent/DD109870A5/xx unknown
- 1973-08-29 IE IE1521/73A patent/IE38317B1/xx unknown
-
1975
- 1975-04-29 ES ES437148A patent/ES437148A1/es not_active Expired
-
1979
- 1979-06-21 IT IT7949487A patent/IT7949487A0/it unknown
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