SE430983B - Farmaceutiskt aktiva derivat av 1-hydroxi-oktahydrofenantren-9-on, 1,9-dihydroxi-oktahydrofenantren och 1-hydroxi-hexa-hydrofenantren-9-on - Google Patents
Farmaceutiskt aktiva derivat av 1-hydroxi-oktahydrofenantren-9-on, 1,9-dihydroxi-oktahydrofenantren och 1-hydroxi-hexa-hydrofenantren-9-onInfo
- Publication number
- SE430983B SE430983B SE7811653A SE7811653A SE430983B SE 430983 B SE430983 B SE 430983B SE 7811653 A SE7811653 A SE 7811653A SE 7811653 A SE7811653 A SE 7811653A SE 430983 B SE430983 B SE 430983B
- Authority
- SE
- Sweden
- Prior art keywords
- hydrogen
- phenyl
- compounds
- hydroxy
- methyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 126
- -1 pyrollo Chemical group 0.000 claims abstract description 61
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 35
- 239000001257 hydrogen Substances 0.000 claims abstract description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
- 239000000543 intermediate Substances 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 12
- 229940035676 analgesics Drugs 0.000 claims abstract description 11
- 239000000730 antalgic agent Substances 0.000 claims abstract description 11
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 5
- 125000001589 carboacyl group Chemical group 0.000 claims abstract 5
- 150000002431 hydrogen Chemical group 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 15
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical class C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 208000010412 Glaucoma Diseases 0.000 claims description 3
- 230000002936 tranquilizing effect Effects 0.000 claims description 3
- 206010012335 Dependence Diseases 0.000 claims description 2
- 230000003276 anti-hypertensive effect Effects 0.000 claims description 2
- 239000002249 anxiolytic agent Substances 0.000 claims description 2
- 239000002934 diuretic Substances 0.000 claims description 2
- 239000003018 immunosuppressive agent Substances 0.000 claims description 2
- 230000003533 narcotic effect Effects 0.000 claims description 2
- 239000003204 tranquilizing agent Substances 0.000 claims description 2
- GHEWQAQCRFNDDG-UHFFFAOYSA-N 1-hydroxy-2,3,4,4a,4b,5,6,7-octahydro-1h-phenanthren-9-one Chemical class C1CCC=C2C(=O)C=C3C(O)CCCC3C21 GHEWQAQCRFNDDG-UHFFFAOYSA-N 0.000 claims 1
- NTRQACIKHXYOAI-UHFFFAOYSA-N 2-(hydroxymethylidene)-3,4-dihydronaphthalen-1-one Chemical class C1=CC=C2C(=O)C(=CO)CCC2=C1 NTRQACIKHXYOAI-UHFFFAOYSA-N 0.000 claims 1
- 230000000949 anxiolytic effect Effects 0.000 claims 1
- 229940005530 anxiolytics Drugs 0.000 claims 1
- 229940030606 diuretics Drugs 0.000 claims 1
- 229940125721 immunosuppressive agent Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 20
- 125000000217 alkyl group Chemical group 0.000 abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 abstract description 3
- 230000008569 process Effects 0.000 abstract description 2
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 abstract 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 230000036592 analgesia Effects 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000005936 piperidyl group Chemical group 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 137
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 39
- 239000000243 solution Substances 0.000 description 38
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 32
- 238000012360 testing method Methods 0.000 description 29
- 239000003921 oil Substances 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 27
- 125000003118 aryl group Chemical group 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- 238000010171 animal model Methods 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 20
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 19
- 239000012267 brine Substances 0.000 description 19
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 18
- 235000019341 magnesium sulphate Nutrition 0.000 description 18
- 230000000694 effects Effects 0.000 description 17
- 239000012071 phase Substances 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 13
- 238000001704 evaporation Methods 0.000 description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 12
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 12
- 229910000104 sodium hydride Inorganic materials 0.000 description 12
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
- 239000012312 sodium hydride Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 10
- 230000000202 analgesic effect Effects 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 230000009467 reduction Effects 0.000 description 10
- 238000006722 reduction reaction Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000012280 lithium aluminium hydride Substances 0.000 description 9
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical class BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- 238000001819 mass spectrum Methods 0.000 description 8
- 241000282472 Canis lupus familiaris Species 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 7
- 125000002252 acyl group Chemical group 0.000 description 7
- 235000019445 benzyl alcohol Nutrition 0.000 description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- 230000036461 convulsion Effects 0.000 description 7
- 238000010828 elution Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- 125000004309 pyranyl group Chemical class O1C(C=CC=C1)* 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- OODQYWKHHBWACC-UHFFFAOYSA-N 1-methoxycyclohexa-3,5-diene-1,3-dicarbaldehyde Chemical compound COC1(CC(C=O)=CC=C1)C=O OODQYWKHHBWACC-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 6
- 239000012259 ether extract Substances 0.000 description 6
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 229960005181 morphine Drugs 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- 230000003040 nociceptive effect Effects 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 238000005292 vacuum distillation Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 4
- 229940073608 benzyl chloride Drugs 0.000 description 4
- 238000010531 catalytic reduction reaction Methods 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- MVQFDTAUXDFOPA-UHFFFAOYSA-N methyl 3-acetyl-5-methoxybenzoate Chemical compound COC(=O)C1=CC(OC)=CC(C(C)=O)=C1 MVQFDTAUXDFOPA-UHFFFAOYSA-N 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- GEJXUAMLSHIAKE-UHFFFAOYSA-N 6,8-dihydroxy-3,3-dimethyl-2,4-dihydronaphthalen-1-one Chemical compound C1=C(O)C=C2CC(C)(C)CC(=O)C2=C1O GEJXUAMLSHIAKE-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- 206010010904 Convulsion Diseases 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 108010079943 Pentagastrin Proteins 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 125000001743 benzylic group Chemical group 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- PRMBJTVISCMRNW-UHFFFAOYSA-N dimethyl 1-methoxycyclohexa-3,5-diene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)(OC)C1 PRMBJTVISCMRNW-UHFFFAOYSA-N 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 229960001340 histamine Drugs 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 210000004698 lymphocyte Anatomy 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- OFXSXYCSPVKZPF-UHFFFAOYSA-N methoxyperoxymethane Chemical compound COOOC OFXSXYCSPVKZPF-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 3
- 229960000444 pentagastrin Drugs 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 230000035939 shock Effects 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
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- HECULCWTVRHVGP-FNORWQNLSA-N ethyl (e)-2-cyanopent-2-enoate Chemical compound CCOC(=O)C(\C#N)=C\CC HECULCWTVRHVGP-FNORWQNLSA-N 0.000 description 1
- PZMDAADKKAXROL-UHFFFAOYSA-N ethyl 2-cyano-3-methylbut-2-enoate Chemical compound CCOC(=O)C(C#N)=C(C)C PZMDAADKKAXROL-UHFFFAOYSA-N 0.000 description 1
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- HNDJOYYPCHPVBY-UHFFFAOYSA-N ethyl 3-(7-benzyl-7-ethyl-4-hydroxy-5-oxo-6,8-dihydronaphthalen-2-yl)propanoate Chemical compound C1C2=CC(CCC(=O)OCC)=CC(O)=C2C(=O)CC1(CC)CC1=CC=CC=C1 HNDJOYYPCHPVBY-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
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- 239000000796 flavoring agent Substances 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
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- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
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- TYDWBLYJIGSBPU-UHFFFAOYSA-M magnesium;1-methanidyl-3,5-dimethoxybenzene;chloride Chemical compound [Mg+2].[Cl-].COC1=CC([CH2-])=CC(OC)=C1 TYDWBLYJIGSBPU-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
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- 230000037040 pain threshold Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
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- 230000028327 secretion Effects 0.000 description 1
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- 239000000932 sedative agent Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000012679 serum free medium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000011421 subcutaneous treatment Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
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- 239000003826 tablet Substances 0.000 description 1
- 229960002494 tetracaine hydrochloride Drugs 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
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- 239000003981 vehicle Substances 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 125000002348 vinylic group Chemical group 0.000 description 1
Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
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- 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
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- 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
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- 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
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- 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
- C07C45/73—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 hydrogenation
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- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
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- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
- C07C49/755—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups a keto group being part of a condensed ring system with two or three rings, at least one ring being a six-membered aromatic ring
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- C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Anesthesiology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/851,503 US4188495A (en) | 1977-11-14 | 1977-11-14 | 1,9-Dihydroxyoctahydrophenanthrenes and intermediates therefor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7811653L SE7811653L (sv) | 1979-05-15 |
| SE430983B true SE430983B (sv) | 1983-12-27 |
Family
ID=25310929
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7811653A SE430983B (sv) | 1977-11-14 | 1978-11-10 | Farmaceutiskt aktiva derivat av 1-hydroxi-oktahydrofenantren-9-on, 1,9-dihydroxi-oktahydrofenantren och 1-hydroxi-hexa-hydrofenantren-9-on |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4188495A (da) |
| JP (1) | JPS5484562A (da) |
| AR (1) | AR220158A1 (da) |
| AT (1) | AT358024B (da) |
| AU (1) | AU509680B2 (da) |
| BE (1) | BE871907A (da) |
| CA (1) | CA1097668A (da) |
| CH (1) | CH635813A5 (da) |
| DE (1) | DE2849224C2 (da) |
| DK (3) | DK414778A (da) |
| ES (1) | ES475040A1 (da) |
| FI (1) | FI71120C (da) |
| FR (2) | FR2411821A1 (da) |
| GB (4) | GB2078721B (da) |
| IE (1) | IE47505B1 (da) |
| IL (1) | IL55930A (da) |
| IT (1) | IT1100945B (da) |
| LU (1) | LU80509A1 (da) |
| NL (1) | NL180206C (da) |
| PH (2) | PH14713A (da) |
| PT (1) | PT68775A (da) |
| SE (1) | SE430983B (da) |
| YU (2) | YU40834B (da) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4285867A (en) * | 1980-09-19 | 1981-08-25 | Pfizer Inc. | Pharmacologically active 4-[2-hydroxy-4-(substituted)phenyl]naphthalen-2(1H)-ones and 2-ols, derivatives thereof and intermediates therefor |
| US4870084A (en) * | 1982-03-16 | 1989-09-26 | Pfizer Inc. | Bicyclic benzo fused pyran compounds used for nausea treatment and prevention |
| US4486428A (en) * | 1982-03-16 | 1984-12-04 | Pfizer Inc. | Bicyclic benzo fused compounds |
| US4476131A (en) * | 1982-03-16 | 1984-10-09 | Pfizer Inc. | Substituted hexahydropyrrolo[1,2-a]-quinolines, hexahydro-1H-pyrido[1,2-a]-q |
| US4841078A (en) * | 1982-03-16 | 1989-06-20 | Pfizer Inc. | Benzopyrans |
| US4920221A (en) * | 1982-03-16 | 1990-04-24 | Pfizer Inc. | Substituted decahydro-1H-pyrido[1,2-f]phenanthridines and decahydropyrrolo[1,2-f]phenanthridines |
| US4473704A (en) * | 1982-03-16 | 1984-09-25 | Pfizer Inc. | Substituted dodecahydrotriphenylenes, decahydro-1H-cyclopenta[1]phenanthrenes, decahydro-1H-pyrido[1,2-f]phenanthridines and decahydropyrrolo[1,2-f]phenanthridines as CNS agents |
| US4863934A (en) * | 1982-03-16 | 1989-09-05 | Pfizer Inc. | Bicyclic benzo fused pyran compounds used for producing analgesia |
| US4576964A (en) * | 1982-03-16 | 1986-03-18 | Pfizer Inc. | Substituted hexahydrobenzo[e]indene and octahydrophenanthrene CNS agents and pharmaceutical compositions thereof |
| US4680404A (en) * | 1983-01-13 | 1987-07-14 | Pfizer Inc. | Benzopyrans |
| DK196688A (da) * | 1987-04-28 | 1988-10-29 | Fujisawa Pharmaceutical Co | Bicykliske forbindelser og fremgangsmaade til fremstilling deraf |
| CA2340445A1 (en) * | 1998-05-04 | 1999-11-11 | The University Of Connecticut | Novel analgesic and immunomodulatory cannabinoids |
| US7897598B2 (en) * | 1998-06-09 | 2011-03-01 | Alexandros Makriyannis | Inhibitors of the anandamide transporter |
| US7589220B2 (en) * | 1998-06-09 | 2009-09-15 | University Of Connecticut | Inhibitors of the anandamide transporter |
| US7161016B1 (en) | 1998-11-24 | 2007-01-09 | University Of Connecticut | Cannabimimetic lipid amides as useful medications |
| US7276613B1 (en) | 1998-11-24 | 2007-10-02 | University Of Connecticut | Retro-anandamides, high affinity and stability cannabinoid receptor ligands |
| US6943266B1 (en) * | 1999-10-18 | 2005-09-13 | University Of Connecticut | Bicyclic cannabinoid agonists for the cannabinoid receptor |
| US7741365B2 (en) * | 1999-10-18 | 2010-06-22 | University Of Connecticut | Peripheral cannabinoid receptor (CB2) selective ligands |
| US6900236B1 (en) | 1999-10-18 | 2005-05-31 | University Of Connecticut | Cannabimimetic indole derivatives |
| US7393842B2 (en) * | 2001-08-31 | 2008-07-01 | University Of Connecticut | Pyrazole analogs acting on cannabinoid receptors |
| CA2387764A1 (en) | 1999-10-18 | 2001-04-26 | University Of Connecticut | Peripheral cannabinoid receptor (cb2) selective ligands |
| US7119108B1 (en) | 1999-10-18 | 2006-10-10 | University Of Connecticut | Pyrazole derivatives as cannabinoid receptor antagonists |
| US8084467B2 (en) * | 1999-10-18 | 2011-12-27 | University Of Connecticut | Pyrazole derivatives as cannabinoid receptor antagonists |
| US6340774B1 (en) * | 2000-01-31 | 2002-01-22 | The Board Of Trustees Of The Leland Stanford Junior University | Non-steroidal estrogen-receptor antagonists |
| EP1361876A4 (en) * | 2001-01-26 | 2004-03-31 | Univ Connecticut | NEW CANNABIMIMETIC LIGANDS |
| DE60237431D1 (de) | 2001-01-29 | 2010-10-07 | Univ Connecticut | Rezeptor-selektive cannabimimetische aminoalkylindole |
| JP4312594B2 (ja) * | 2001-07-13 | 2009-08-12 | ユニバーシティ オブ コネチカット | 新規な二環式及び三環式カンナビノイド |
| US7666867B2 (en) * | 2001-10-26 | 2010-02-23 | University Of Connecticut | Heteroindanes: a new class of potent cannabimimetic ligands |
| AU2003265663A1 (en) | 2002-08-23 | 2004-03-11 | University Of Connecticut | Keto cannabinoids with therapeutic indications |
| MXPA05004966A (es) * | 2002-11-12 | 2005-08-02 | Mallinckrodt Inc | Derivados cristalinos de canabinoide y procesos de purificacion de canabinoide. |
| CN1884265A (zh) * | 2005-06-20 | 2006-12-27 | 美时化学制药股份有限公司 | 治疗糖尿病的阿朴芬及次阿朴芬化合物 |
| RU2408367C1 (ru) * | 2009-07-14 | 2011-01-10 | Государственное образовательное учреждение высшего профессионального образования "Алтайский государственный медицинский университет Росздрава" (ГОУ ВПО АГМУ Росздрава) | Диуретическое средство |
| US20220317097A1 (en) * | 2021-04-05 | 2022-10-06 | Grant Kraus | Atmospheric Triphasic Chromatography (ATC) method |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3775471A (en) * | 1967-05-15 | 1973-11-27 | Syntex Corp | Novel phenanthrene-2-carboxylic acids and derivatives thereof |
| US3833726A (en) * | 1971-12-13 | 1974-09-03 | Warner Lambert Co | 1-oxo-substituted-tetrahydronaphthalenes (substituted-tetralones) |
-
1977
- 1977-11-14 US US05/851,503 patent/US4188495A/en not_active Expired - Lifetime
-
1978
- 1978-09-19 DK DK414778A patent/DK414778A/da not_active Application Discontinuation
- 1978-10-24 CA CA314,035A patent/CA1097668A/en not_active Expired
- 1978-11-07 GB GB8114314A patent/GB2078721B/en not_active Expired
- 1978-11-07 GB GB8114315A patent/GB2079269B/en not_active Expired
- 1978-11-07 GB GB7843558A patent/GB2007665B/en not_active Expired
- 1978-11-07 GB GB8114313A patent/GB2078720B/en not_active Expired
- 1978-11-09 YU YU2615/78A patent/YU40834B/xx unknown
- 1978-11-10 SE SE7811653A patent/SE430983B/sv not_active IP Right Cessation
- 1978-11-10 PT PT68775A patent/PT68775A/pt unknown
- 1978-11-10 BE BE191647A patent/BE871907A/xx not_active IP Right Cessation
- 1978-11-13 CH CH1166478A patent/CH635813A5/fr not_active IP Right Cessation
- 1978-11-13 AT AT812078A patent/AT358024B/de not_active IP Right Cessation
- 1978-11-13 ES ES475040A patent/ES475040A1/es not_active Expired
- 1978-11-13 IT IT29727/78A patent/IT1100945B/it active
- 1978-11-13 JP JP13975878A patent/JPS5484562A/ja active Granted
- 1978-11-13 PH PH21801A patent/PH14713A/en unknown
- 1978-11-13 LU LU80509A patent/LU80509A1/fr unknown
- 1978-11-13 DE DE2849224A patent/DE2849224C2/de not_active Expired
- 1978-11-13 IE IE2238/78A patent/IE47505B1/en not_active IP Right Cessation
- 1978-11-13 FI FI783456A patent/FI71120C/fi not_active IP Right Cessation
- 1978-11-13 AU AU41521/78A patent/AU509680B2/en not_active Expired
- 1978-11-13 FR FR7831980A patent/FR2411821A1/fr active Granted
- 1978-11-13 IL IL55930A patent/IL55930A/xx unknown
- 1978-11-14 AR AR274426A patent/AR220158A1/es active
- 1978-11-14 NL NLAANVRAGE7811235,A patent/NL180206C/xx not_active IP Right Cessation
-
1979
- 1979-04-06 FR FR7908769A patent/FR2414035A1/fr active Granted
-
1980
- 1980-05-15 PH PH24033A patent/PH15429A/en unknown
-
1982
- 1982-12-15 YU YU02772/82A patent/YU277282A/xx unknown
-
1988
- 1988-08-18 DK DK463288A patent/DK463288D0/da not_active Application Discontinuation
- 1988-08-18 DK DK463388A patent/DK463388D0/da not_active Application Discontinuation
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