FI67556C - Foerfarande foer framstaellning av nya saosom antivirala medelanvaendbara substituerade acetofenonderivat - Google Patents
Foerfarande foer framstaellning av nya saosom antivirala medelanvaendbara substituerade acetofenonderivat Download PDFInfo
- Publication number
- FI67556C FI67556C FI801661A FI801661A FI67556C FI 67556 C FI67556 C FI 67556C FI 801661 A FI801661 A FI 801661A FI 801661 A FI801661 A FI 801661A FI 67556 C FI67556 C FI 67556C
- Authority
- FI
- Finland
- Prior art keywords
- phosphonooxy
- dimethoxy
- ethoxy
- formula
- antivirala
- Prior art date
Links
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000003443 antiviral agent Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 150000008062 acetophenones Chemical class 0.000 claims 1
- -1 methoxy, ethoxy, propoxy Chemical group 0.000 description 20
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 8
- 230000000840 anti-viral effect Effects 0.000 description 8
- 235000005513 chalcones Nutrition 0.000 description 8
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 7
- 239000000825 pharmaceutical preparation Substances 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241000700605 Viruses Species 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 230000000120 cytopathologic effect Effects 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 230000003612 virological effect Effects 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 241000709677 Coxsackievirus B1 Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000709661 Enterovirus Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- RNVAZNMRYDRPNT-UHFFFAOYSA-N [3,5-dimethoxy-2-(3-thiophen-2-ylprop-2-enoyl)phenyl] dihydrogen phosphate Chemical compound OP(=O)(O)OC1=CC(OC)=CC(OC)=C1C(=O)C=CC1=CC=CS1 RNVAZNMRYDRPNT-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 125000002541 furyl group Chemical class 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
- 239000000843 powder Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- PWVBSDQARMAGHJ-CMDGGOBGSA-N (e)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methylphenyl)prop-2-en-1-one Chemical compound COC1=CC(OC)=CC(O)=C1C(=O)\C=C\C1=CC=C(C)C=C1 PWVBSDQARMAGHJ-CMDGGOBGSA-N 0.000 description 1
- KJMORCJTWYATST-UHFFFAOYSA-N 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-thiophen-2-ylprop-2-en-1-one Chemical compound COC1=CC(OC)=CC(O)=C1C(=O)C=CC1=CC=CS1 KJMORCJTWYATST-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- BCBTTXMSVCLDKM-UHFFFAOYSA-N 3-(4-ethoxyphenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one Chemical compound C1=CC(OCC)=CC=C1C=CC(=O)C1=C(O)C=C(OC)C=C1OC BCBTTXMSVCLDKM-UHFFFAOYSA-N 0.000 description 1
- NDZUMKRLIPIEQP-UHFFFAOYSA-N 4,10-dihydroxyperylene-3,9-dione Chemical compound C1=CC2=C(C=CC3=O)C4C3=C(O)C=CC4C(C=CC3=O)=C2C3=C1O NDZUMKRLIPIEQP-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 241000220479 Acacia Species 0.000 description 1
- HVXKHWAYGBRHJT-UHFFFAOYSA-N COC1=CC(=C(C(=C1)OP(=O)(O)O)C(=O)C(=C)C2=CC=CS2)OC Chemical compound COC1=CC(=C(C(=C1)OP(=O)(O)O)C(=O)C(=C)C2=CC=CS2)OC HVXKHWAYGBRHJT-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000430519 Human rhinovirus sp. Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 206010061494 Rhinovirus infection Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 229940125716 antipyretic agent Drugs 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 230000001332 colony forming effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical compound CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000008011 inorganic excipient Substances 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 210000005265 lung cell Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000008012 organic excipient Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- 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
- C07C45/72—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 of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—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 of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Saccharide Compounds (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7917973 | 1979-05-23 | ||
| GB7917973 | 1979-05-23 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI801661A FI801661A (fi) | 1980-11-21 |
| FI67556B FI67556B (fi) | 1984-12-31 |
| FI67556C true FI67556C (fi) | 1985-04-10 |
Family
ID=10505387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI801661A FI67556C (fi) | 1979-05-23 | 1980-05-22 | Foerfarande foer framstaellning av nya saosom antivirala medelanvaendbara substituerade acetofenonderivat |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4327088A (pt) |
| EP (1) | EP0021000B1 (pt) |
| JP (1) | JPS55157534A (pt) |
| AR (1) | AR230064A1 (pt) |
| AT (1) | ATE6357T1 (pt) |
| AU (1) | AU538581B2 (pt) |
| BR (1) | BR8003235A (pt) |
| CA (1) | CA1137082A (pt) |
| CS (1) | CS212716B2 (pt) |
| CU (1) | CU35266A (pt) |
| DE (1) | DE3066676D1 (pt) |
| DK (1) | DK224980A (pt) |
| ES (1) | ES491728A0 (pt) |
| FI (1) | FI67556C (pt) |
| GR (1) | GR67305B (pt) |
| HU (1) | HU184288B (pt) |
| IE (1) | IE49816B1 (pt) |
| IL (1) | IL60115A (pt) |
| MC (1) | MC1330A1 (pt) |
| NO (1) | NO152898C (pt) |
| NZ (1) | NZ193750A (pt) |
| PH (1) | PH16056A (pt) |
| PT (1) | PT71289B (pt) |
| YU (1) | YU140280A (pt) |
| ZA (1) | ZA802927B (pt) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6385526A (ja) * | 1986-09-30 | 1988-04-16 | Nippon Oil & Fats Co Ltd | 非線形光学材料 |
| CA2051501C (en) * | 1990-09-20 | 2004-02-17 | Robert J. Dinerstein | 1-phenyl-3-phenyl-2-propyne-1-ones as calcium uptake inhibitors |
| IL118657A0 (en) * | 1996-06-14 | 1996-10-16 | Arad Dorit | Inhibitors for picornavirus proteases |
| IL122591A0 (en) | 1997-12-14 | 1998-06-15 | Arad Dorit | Pharmaceutical compositions comprising cystein protease inhibitors |
| CA2371910A1 (en) | 1999-01-21 | 2000-07-27 | Brian E. Peerce | Inhibitors of intestinal apical membrane na/phosphate co-transportation |
| US20030162753A1 (en) * | 1999-01-21 | 2003-08-28 | Peerce Brian E. | Inhibition of intestinal apical membrane Na/phosphate co-transportation in humans |
| WO2005042467A1 (en) * | 2003-10-31 | 2005-05-12 | Lica Pharmaceuticals A/S | Quaternary amino-functional chalcones |
| US20060270614A1 (en) * | 2005-05-24 | 2006-11-30 | Sekhar Boddupalli | Use of chalcones for the treatment of viral disorders |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL76438C (pt) * | 1949-11-30 | |||
| GB1007332A (en) * | 1960-12-09 | 1965-10-13 | Cooper Mcdougall & Robertson | New halogen-containing phosphoric and thiophosphoric acid esters and formulations containing them |
| FR1476531A (fr) | 1965-04-26 | 1967-04-14 | Chimetron Sarl | Nouvelles cétones halogénées dérivées du benzimidazole |
| US3583894A (en) * | 1968-03-29 | 1971-06-08 | Us Agriculture | Enzyme preparation of hesperetin dihydrochalcone glucoside |
| US3629322A (en) * | 1969-02-17 | 1971-12-21 | Buckman Labor Inc | Organic esters and their use as ultraviolet light absorbers and as heat stabilizers |
| GB1283981A (en) * | 1969-03-05 | 1972-08-02 | Orsymonde | 2,4,6-trihydroxy chalcone derivatives |
| GB1398528A (en) * | 1971-08-17 | 1975-06-25 | Leo Ab | Pharmaceutically active secondary phosphoric acid esters |
| JPS598250B2 (ja) * | 1974-02-09 | 1984-02-23 | 大正製薬株式会社 | カルコンエ−テルの合成法 |
| JPS5912094B2 (ja) * | 1974-01-19 | 1984-03-21 | 大正製薬株式会社 | カルコン体の合成法 |
| JPS598249B2 (ja) * | 1974-01-19 | 1984-02-23 | 大正製薬株式会社 | カルコン類の合成法 |
| JPS593460B2 (ja) * | 1974-04-19 | 1984-01-24 | 大正製薬株式会社 | カルコンルイ ノ ゴウセイホウ |
| JPS598251B2 (ja) * | 1974-04-19 | 1984-02-23 | 大正製薬株式会社 | イソプレニルカルコン類の合成法 |
| JPS50140430A (pt) * | 1974-04-23 | 1975-11-11 | ||
| FR2307820A1 (fr) * | 1975-04-17 | 1976-11-12 | Hayashibara Seibutsu Chem Inst | Glycosides d'echinatine et leur preparation |
| DD123466A1 (pt) | 1975-12-01 | 1976-12-20 | ||
| US4122191A (en) * | 1976-12-20 | 1978-10-24 | Richardson-Merrell Inc. | Antirhinovirus agents |
| US4154756A (en) * | 1977-12-15 | 1979-05-15 | American Cyanamid Company | 2-Substituted-4'-(monoalkylamino)-acetophenones |
| NZ192641A (en) * | 1979-01-26 | 1984-10-19 | Hoffmann La Roche | Substituted acetophenones and pharmaceutical compositions |
-
1980
- 1980-05-02 CA CA000351137A patent/CA1137082A/en not_active Expired
- 1980-05-12 US US06/148,616 patent/US4327088A/en not_active Expired - Lifetime
- 1980-05-13 EP EP80102661A patent/EP0021000B1/de not_active Expired
- 1980-05-13 AT AT80102661T patent/ATE6357T1/de not_active IP Right Cessation
- 1980-05-13 DE DE8080102661T patent/DE3066676D1/de not_active Expired
- 1980-05-15 CU CU8035266A patent/CU35266A/es unknown
- 1980-05-16 AU AU58465/80A patent/AU538581B2/en not_active Ceased
- 1980-05-16 NZ NZ193750A patent/NZ193750A/en unknown
- 1980-05-16 ZA ZA00802927A patent/ZA802927B/xx unknown
- 1980-05-19 HU HU801236A patent/HU184288B/hu unknown
- 1980-05-19 CS CS803494A patent/CS212716B2/cs unknown
- 1980-05-19 IL IL60115A patent/IL60115A/xx unknown
- 1980-05-21 GR GR62006A patent/GR67305B/el unknown
- 1980-05-22 AR AR281160A patent/AR230064A1/es active
- 1980-05-22 IE IE1068/80A patent/IE49816B1/en unknown
- 1980-05-22 DK DK224980A patent/DK224980A/da not_active Application Discontinuation
- 1980-05-22 ES ES491728A patent/ES491728A0/es active Granted
- 1980-05-22 PT PT71289A patent/PT71289B/pt unknown
- 1980-05-22 NO NO801542A patent/NO152898C/no unknown
- 1980-05-22 FI FI801661A patent/FI67556C/fi not_active IP Right Cessation
- 1980-05-22 JP JP6721880A patent/JPS55157534A/ja active Pending
- 1980-05-23 PH PH24063A patent/PH16056A/en unknown
- 1980-05-23 BR BR8003235A patent/BR8003235A/pt unknown
- 1980-05-23 YU YU01402/80A patent/YU140280A/xx unknown
- 1980-05-23 MC MC801451A patent/MC1330A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE3066676D1 (en) | 1984-03-29 |
| NZ193750A (en) | 1984-12-14 |
| GR67305B (pt) | 1981-06-29 |
| PT71289A (en) | 1980-06-01 |
| NO801542L (no) | 1980-11-24 |
| CU35266A (en) | 1982-03-28 |
| AR230064A1 (es) | 1984-02-29 |
| US4327088A (en) | 1982-04-27 |
| NO152898B (no) | 1985-09-02 |
| DK224980A (da) | 1980-11-24 |
| MC1330A1 (fr) | 1981-04-21 |
| ES8104812A1 (es) | 1981-04-01 |
| PH16056A (en) | 1983-06-09 |
| HU184288B (en) | 1984-07-30 |
| IE801068L (en) | 1980-11-23 |
| ATE6357T1 (de) | 1984-03-15 |
| EP0021000A3 (en) | 1981-12-02 |
| CA1137082A (en) | 1982-12-07 |
| FI67556B (fi) | 1984-12-31 |
| YU140280A (en) | 1983-12-31 |
| NO152898C (no) | 1985-12-11 |
| EP0021000B1 (de) | 1984-02-22 |
| AU538581B2 (en) | 1984-08-23 |
| AU5846580A (en) | 1980-11-27 |
| IL60115A0 (en) | 1980-07-31 |
| ZA802927B (en) | 1982-01-27 |
| ES491728A0 (es) | 1981-04-01 |
| EP0021000A2 (de) | 1981-01-07 |
| CS212716B2 (en) | 1982-03-26 |
| PT71289B (en) | 1981-09-21 |
| FI801661A (fi) | 1980-11-21 |
| JPS55157534A (en) | 1980-12-08 |
| IE49816B1 (en) | 1985-12-25 |
| IL60115A (en) | 1986-02-28 |
| BR8003235A (pt) | 1980-12-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1950376B (zh) | 莪术醇衍生物、含该衍生物的组合物及所述衍生物的制药用途 | |
| SU1424732A3 (ru) | Способ получени 2,4-диамино-5-(замещенных)пиримидинов или их солей | |
| US5229378A (en) | Glycyrrhetic acid derivatives | |
| DK149022B (da) | Analogifremgangsmaade til fremstilling af aminderivater af di-o-(n-alkyl- eller alkenyl)-glyceroler eller farmaceutisk acceptable syreadditionssalte deraf | |
| FI70699B (fi) | Foerfarande foer framstaellning av antivirala substituerade actofenoner | |
| FI67556C (fi) | Foerfarande foer framstaellning av nya saosom antivirala medelanvaendbara substituerade acetofenonderivat | |
| Antoszczak et al. | Anti-trypanosomal activity of doubly modified salinomycin derivatives | |
| US4394389A (en) | Hydroxybenzohydroxamic acids, benzamides and esters as ribonucleotide reductase inhibitors | |
| HU189991B (en) | Process for producing benzene derivatives with four substituents | |
| US4448730A (en) | Hydroxybenzohydroxamic acids, benzamides and esters and related compounds as ribonucleotide reductase inhibitors | |
| US4139531A (en) | 1-Nitro-9-alkylaminoalkylaminoacridines and salts thereof | |
| SU1470198A3 (ru) | Способ получени производных стероидов | |
| JPS63101369A (ja) | インデノキノリン系化合物、その製造法及びその化合物を有効成分とする抗癌剤 | |
| EP0102175A1 (en) | 5-Oxo-5H-(1)benzopyrano(2,3-b)pyridine derivatives, their production and use | |
| FI90081C (fi) | Foerfarande foer framstaellning av terapeutiskt aktiva ginkgolidderivat | |
| ZA200502226B (en) | Sorbicillactone-A derivatives for the treatment oftumour and viral diseases. | |
| EP0272810A2 (en) | Antitumor and antiviral alkaloids | |
| CN101050179B (zh) | 2,3,4,5-四取代的苯丙烯类衍生物及其制备方法和用途 | |
| US7148253B2 (en) | 4-thio coumarins | |
| JP2632121B2 (ja) | シアタン誘導体及びこれを有効成分とする神経成長因子産生誘導剤並びに抗菌剤 | |
| KR850000428B1 (ko) | 치환된 아세토페논의 제조방법 | |
| CA1174978A (en) | Xanthates | |
| US5753695A (en) | Flavilium compounds and method of using | |
| PT87605B (pt) | Processo para a preparacao do isomero s de um derivado de purina | |
| US3309270A (en) | Organic phosphorus anthelmintics and method of using the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: F HOFFMANN-LA ROCHE & CO |