JPS6129950B2 - - Google Patents
Info
- Publication number
- JPS6129950B2 JPS6129950B2 JP57148452A JP14845282A JPS6129950B2 JP S6129950 B2 JPS6129950 B2 JP S6129950B2 JP 57148452 A JP57148452 A JP 57148452A JP 14845282 A JP14845282 A JP 14845282A JP S6129950 B2 JPS6129950 B2 JP S6129950B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- compound
- hydrogen atom
- lower alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 72
- -1 pyrrolidino, piperidino Chemical group 0.000 claims abstract description 37
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
- 125000005843 halogen group Chemical group 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 9
- 239000011707 mineral Substances 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 150000007524 organic acids Chemical class 0.000 claims abstract description 8
- 125000002252 acyl group Chemical group 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
- 230000003287 optical effect Effects 0.000 claims abstract description 7
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 5
- 239000000935 antidepressant agent Substances 0.000 claims abstract description 4
- 229940005513 antidepressants Drugs 0.000 claims abstract description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 11
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 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 claims description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 230000000949 anxiolytic effect Effects 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- ATYBXHSAIOKLMG-UHFFFAOYSA-N oxepin Chemical compound O1C=CC=CC=C1 ATYBXHSAIOKLMG-UHFFFAOYSA-N 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 230000001430 anti-depressive effect Effects 0.000 claims description 2
- 239000002249 anxiolytic agent Substances 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical class CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims 2
- 150000003335 secondary amines Chemical class 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 238000006969 Curtius rearrangement reaction Methods 0.000 claims 1
- 208000020401 Depressive disease Diseases 0.000 claims 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 239000003849 aromatic solvent Substances 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 150000003956 methylamines Chemical class 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 3
- 239000001257 hydrogen Substances 0.000 abstract description 3
- 125000004193 piperazinyl group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- 230000008018 melting Effects 0.000 description 27
- 238000002844 melting Methods 0.000 description 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 241000700159 Rattus Species 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 150000002596 lactones Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- WXLCDTBTIVJDCE-UHFFFAOYSA-N 1,4-oxazepine Chemical compound O1C=CC=NC=C1 WXLCDTBTIVJDCE-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 230000016571 aggressive behavior Effects 0.000 description 5
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
- 150000001540 azides Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- NTNUDYROPUKXNA-UHFFFAOYSA-N methyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OC)C1=CC=CC=C1 NTNUDYROPUKXNA-UHFFFAOYSA-N 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 241000282414 Homo sapiens Species 0.000 description 2
- 206010020843 Hyperthermia Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 150000003947 ethylamines Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000036031 hyperthermia Effects 0.000 description 2
- 230000002631 hypothermal effect Effects 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000000926 neurological effect Effects 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000010254 subcutaneous injection Methods 0.000 description 2
- 239000007929 subcutaneous injection Substances 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229960005333 tetrabenazine Drugs 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000005406 washing Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 1
- WEZRXVVNYSKFHY-UHFFFAOYSA-N 2-benzo[c][1]benzoxepin-6-ylethanol Chemical compound O1C(CCO)=C2C=CC=CC2=CC2=CC=CC=C21 WEZRXVVNYSKFHY-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- SLGIBJWUMUWIFH-UHFFFAOYSA-N 6,11-dihydrobenzo[c][1,5]benzoxazepine Chemical compound C1OC2=CC=CC=C2NC2=CC=CC=C12 SLGIBJWUMUWIFH-UHFFFAOYSA-N 0.000 description 1
- FPIWJQQRYHEICX-UHFFFAOYSA-N 6,11-dihydrobenzo[c][1]benzoxepine Chemical compound C1OC2=CC=CC=C2CC2=CC=CC=C12 FPIWJQQRYHEICX-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- BEUDCHGZCTUAOG-UHFFFAOYSA-N 6h-benzo[c]chromene Chemical compound C1=CC=C2COC3=CC=CC=C3C2=C1 BEUDCHGZCTUAOG-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 241000699660 Mus musculus Species 0.000 description 1
- 244000089486 Phragmites australis subsp australis Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- 206010039660 School refusal Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940005530 anxiolytics Drugs 0.000 description 1
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
- 229960004046 apomorphine Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940090047 auto-injector Drugs 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 210000000744 eyelid Anatomy 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- ZIGNSNGGNVSKET-UHFFFAOYSA-N methyl 1-methylidene-2H-benzo[c][1]benzoxepine-6-carboxylate Chemical compound O1C(C(=O)OC)=C2C=CC=CC2=CC2=C1C=CCC2=C ZIGNSNGGNVSKET-UHFFFAOYSA-N 0.000 description 1
- VDPZRDUBGJDMSK-UHFFFAOYSA-N methyl 2-(11-acetylbenzo[c][1,5]benzoxazepin-6-ylidene)acetate Chemical compound COC(=O)C=C1OC2=CC=CC=C2N(C(C)=O)C2=CC=CC=C12 VDPZRDUBGJDMSK-UHFFFAOYSA-N 0.000 description 1
- QUZHETYGXCOZJV-UHFFFAOYSA-N methyl 2-benzo[c][1]benzoxepin-6-ylacetate Chemical compound O1C(CC(=O)OC)=C2C=CC=CC2=CC2=CC=CC=C21 QUZHETYGXCOZJV-UHFFFAOYSA-N 0.000 description 1
- KQACHGKROWTUPZ-UHFFFAOYSA-N methyl 2-benzo[c]chromen-6-ylideneacetate Chemical compound COC(=O)C=C1C2=C(C3=C(O1)C=CC=C3)C=CC=C2 KQACHGKROWTUPZ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 210000000196 olfactory nerve Anatomy 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D313/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D313/12—[b,e]-condensed
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D267/16—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D267/18—[b, e]-condensed
-
- 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)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Anesthesiology (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Luminescent Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8116347A FR2512024A1 (fr) | 1981-08-27 | 1981-08-27 | Ethers tricycliques, leur preparation et les compositions pharmaceutiques les contenant |
| FR8116347 | 1981-08-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5874673A JPS5874673A (ja) | 1983-05-06 |
| JPS6129950B2 true JPS6129950B2 ( ) | 1986-07-10 |
Family
ID=9261704
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57148452A Granted JPS5874673A (ja) | 1981-08-27 | 1982-08-26 | 三環式エ−テル化合物及びその製法並びに該化合物を有効成分とする製剤 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4496557A ( ) |
| EP (1) | EP0074304B1 ( ) |
| JP (1) | JPS5874673A ( ) |
| AT (1) | ATE12497T1 ( ) |
| AU (1) | AU8773082A ( ) |
| CA (1) | CA1227481A ( ) |
| DE (1) | DE3262880D1 ( ) |
| ES (1) | ES8400422A1 ( ) |
| FR (1) | FR2512024A1 ( ) |
| GR (1) | GR77595B ( ) |
| IL (1) | IL66650A ( ) |
| NZ (1) | NZ201740A ( ) |
| PT (1) | PT75471B ( ) |
| ZA (1) | ZA826252B ( ) |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8500273D0 (sv) * | 1985-01-22 | 1985-01-22 | Leo Ab | Nya tricykliska foreningar, kompositioner innehallande sadana foreningar, framstellningsforfaranden och behandlingsmetoder |
| EP0332246A1 (en) * | 1988-03-11 | 1989-09-13 | Akzo N.V. | Tricyclic amine derivatives |
| US5180736A (en) * | 1989-03-23 | 1993-01-19 | Warner-Lambert Company | Polycyclic amines useful as cerebrovascular agents |
| US5006536A (en) * | 1989-12-26 | 1991-04-09 | Hoechst-Roussel Pharmaceuticals Inc. | Thienobenzoxepins and analgesic compositions thereof |
| US5260319A (en) * | 1989-12-26 | 1993-11-09 | Hoechst-Roussel Pharmaceuticals Incorporated | Thienobenzoxepins and naphthothiophenes |
| US5574173A (en) * | 1993-12-06 | 1996-11-12 | Schering Corporation | Tricyclic derivatives, compositions and methods of use |
| US5698551A (en) * | 1995-04-07 | 1997-12-16 | Novo Nordisk A/S | Heterocyclic compounds |
| WO2006058160A2 (en) | 2004-11-26 | 2006-06-01 | Hologic, Inc. | Integrated multi-mode mammography/tomosynthesis x-ray system and method |
| US7616801B2 (en) | 2002-11-27 | 2009-11-10 | Hologic, Inc. | Image handling and display in x-ray mammography and tomosynthesis |
| US7577282B2 (en) | 2002-11-27 | 2009-08-18 | Hologic, Inc. | Image handling and display in X-ray mammography and tomosynthesis |
| US8565372B2 (en) | 2003-11-26 | 2013-10-22 | Hologic, Inc | System and method for low dose tomosynthesis |
| US8571289B2 (en) | 2002-11-27 | 2013-10-29 | Hologic, Inc. | System and method for generating a 2D image from a tomosynthesis data set |
| US7123684B2 (en) * | 2002-11-27 | 2006-10-17 | Hologic, Inc. | Full field mammography with tissue exposure control, tomosynthesis, and dynamic field of view processing |
| US10638994B2 (en) | 2002-11-27 | 2020-05-05 | Hologic, Inc. | X-ray mammography with tomosynthesis |
| US8768026B2 (en) | 2003-11-26 | 2014-07-01 | Hologic, Inc. | X-ray imaging with x-ray markers that provide adjunct information but preserve image quality |
| US7662082B2 (en) | 2004-11-05 | 2010-02-16 | Theragenics Corporation | Expandable brachytherapy device |
| US7702142B2 (en) | 2004-11-15 | 2010-04-20 | Hologic, Inc. | Matching geometry generation and display of mammograms and tomosynthesis images |
| US7245694B2 (en) | 2005-08-15 | 2007-07-17 | Hologic, Inc. | X-ray mammography/tomosynthesis of patient's breast |
| US7465268B2 (en) | 2005-11-18 | 2008-12-16 | Senorx, Inc. | Methods for asymmetrical irradiation of a body cavity |
| US8532745B2 (en) | 2006-02-15 | 2013-09-10 | Hologic, Inc. | Breast biopsy and needle localization using tomosynthesis systems |
| US7630533B2 (en) | 2007-09-20 | 2009-12-08 | Hologic, Inc. | Breast tomosynthesis with display of highlighted suspected calcifications |
| US7991106B2 (en) * | 2008-08-29 | 2011-08-02 | Hologic, Inc. | Multi-mode tomosynthesis/mammography gain calibration and image correction using gain map information from selected projection angles |
| EP3311748A3 (en) | 2008-09-04 | 2018-05-09 | Hologic Inc. | Integrated multi-mode mammography/tomosynthesis x-ray system |
| US9248311B2 (en) | 2009-02-11 | 2016-02-02 | Hologic, Inc. | System and method for modifying a flexibility of a brachythereapy catheter |
| US9579524B2 (en) | 2009-02-11 | 2017-02-28 | Hologic, Inc. | Flexible multi-lumen brachytherapy device |
| US8170320B2 (en) | 2009-03-03 | 2012-05-01 | Hologic, Inc. | Mammography/tomosynthesis systems and methods automatically deriving breast characteristics from breast x-ray images and automatically adjusting image processing parameters accordingly |
| US10207126B2 (en) | 2009-05-11 | 2019-02-19 | Cytyc Corporation | Lumen visualization and identification system for multi-lumen balloon catheter |
| ES2862525T3 (es) | 2009-10-08 | 2021-10-07 | Hologic Inc | Sistema de biopsia de mama con aguja y método de uso |
| US9352172B2 (en) | 2010-09-30 | 2016-05-31 | Hologic, Inc. | Using a guide member to facilitate brachytherapy device swap |
| AU2011312086B2 (en) | 2010-10-05 | 2015-09-17 | Hologic, Inc. | Upright x-ray breast imaging with a CT mode, multiple tomosynthesis modes, and a mammography mode |
| WO2012071429A1 (en) | 2010-11-26 | 2012-05-31 | Hologic, Inc. | User interface for medical image review workstation |
| US10342992B2 (en) | 2011-01-06 | 2019-07-09 | Hologic, Inc. | Orienting a brachytherapy applicator |
| AU2012225398B2 (en) | 2011-03-08 | 2017-02-02 | Hologic, Inc. | System and method for dual energy and/or contrast enhanced breast imaging for screening, diagnosis and biopsy |
| EP2782505B1 (en) | 2011-11-27 | 2020-04-22 | Hologic, Inc. | System and method for generating a 2d image using mammography and/or tomosynthesis image data |
| JP6240097B2 (ja) | 2012-02-13 | 2017-11-29 | ホロジック インコーポレイティッド | 合成画像データを使用してトモシンセシススタックをナビゲートする方法 |
| US10092358B2 (en) | 2013-03-15 | 2018-10-09 | Hologic, Inc. | Tomosynthesis-guided biopsy apparatus and method |
| EP3055837B1 (en) | 2013-10-09 | 2021-08-04 | Hologic, Inc. | X-ray breast tomosynthesis enhancing spatial resolution including in the thickness direction of a flattened breast |
| EP3110332B1 (en) | 2014-02-28 | 2018-04-11 | Hologic Inc. | System and method for generating and displaying tomosynthesis image slabs |
| AU2015343319B2 (en) | 2014-11-07 | 2020-07-23 | Hologic, Inc. | Pivoting paddle apparatus for mammography/tomosynthesis x-ray system |
| JP7085492B2 (ja) | 2016-04-22 | 2022-06-16 | ホロジック，インコーポレイテッド | アドレス指定可能なアレイを使用する偏移焦点ｘ線システムを用いるトモシンセシス |
| JP2019533510A (ja) | 2016-11-08 | 2019-11-21 | ホロジック, インコーポレイテッドHologic, Inc. | 湾曲した圧迫要素を用いた撮像 |
| WO2018183550A1 (en) | 2017-03-30 | 2018-10-04 | Hologic, Inc. | System and method for targeted object enhancement to generate synthetic breast tissue images |
| JP7277053B2 (ja) | 2017-03-30 | 2023-05-18 | ホロジック， インコーポレイテッド | 階層式マルチレベル特徴画像合成および提示のためのシステムおよび方法 |
| EP3600051B1 (en) | 2017-03-30 | 2024-05-01 | Hologic, Inc. | Method for synthesizing low-dimensional image data from high-dimensional image data using an object grid enhancement |
| US11403483B2 (en) | 2017-06-20 | 2022-08-02 | Hologic, Inc. | Dynamic self-learning medical image method and system |
| WO2019033022A1 (en) | 2017-08-11 | 2019-02-14 | Hologic, Inc. | BREAST COMPRESSION PLATE COMPRISING AN INFLATABLE ENVELOPE |
| US11672493B2 (en) | 2017-08-11 | 2023-06-13 | Hologic, Inc. | Breast compression paddle with access corners |
| US11707244B2 (en) | 2017-08-16 | 2023-07-25 | Hologic, Inc. | Techniques for breast imaging patient motion artifact compensation |
| EP3449835B1 (en) | 2017-08-22 | 2023-01-11 | Hologic, Inc. | Computed tomography system and method for imaging multiple anatomical targets |
| US11090017B2 (en) | 2018-09-13 | 2021-08-17 | Hologic, Inc. | Generating synthesized projection images for 3D breast tomosynthesis or multi-mode x-ray breast imaging |
| EP3832689A3 (en) | 2019-12-05 | 2021-08-11 | Hologic, Inc. | Systems and methods for improved x-ray tube life |
| US11622736B2 (en) | 2020-01-24 | 2023-04-11 | Hologic, Inc. | Horizontally-displaceable foam breast compression paddle |
| US11471118B2 (en) | 2020-03-27 | 2022-10-18 | Hologic, Inc. | System and method for tracking x-ray tube focal spot position |
| US11786191B2 (en) | 2021-05-17 | 2023-10-17 | Hologic, Inc. | Contrast-enhanced tomosynthesis with a copper filter |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3609167A (en) * | 1962-04-02 | 1971-09-28 | Smith Kline French Lab | IBENZO{8 b,e{9 {0 THIEPINES |
| NL125253C ( ) * | 1963-12-05 | |||
| NL152845B (nl) * | 1966-03-11 | 1977-04-15 | Boehringer Mannheim Gmbh | Werkwijze voor het bereiden van een geneesmiddel met een psychotrope en bloedsomloopstimulerende werking, alsmede het aldus verkregen gevormde geneesmiddel, en werkwijze voor het bereiden van een geneeskrachtig omega,omega-difenylalkylaminederivaat. |
| FR1518226A (fr) * | 1966-04-09 | 1968-03-22 | Boehringer & Soehne Gmbh | Procédé pour la préparation de dérivés tricy cliques n-alcoylés de l'acétamide |
| US4463001A (en) * | 1980-10-20 | 1984-07-31 | Farmitalia Carlo Erba S.P.A. | 6-Substituted 6H-dibenzo[b,d]pyran derivatives and process for their preparation |
-
1981
- 1981-08-27 FR FR8116347A patent/FR2512024A1/fr active Granted
-
1982
- 1982-08-16 US US06/408,451 patent/US4496557A/en not_active Expired - Fee Related
- 1982-08-20 CA CA000409886A patent/CA1227481A/fr not_active Expired
- 1982-08-24 AT AT82401567T patent/ATE12497T1/de active
- 1982-08-24 EP EP82401567A patent/EP0074304B1/fr not_active Expired
- 1982-08-24 DE DE8282401567T patent/DE3262880D1/de not_active Expired
- 1982-08-25 GR GR69103A patent/GR77595B/el unknown
- 1982-08-25 ES ES515232A patent/ES8400422A1/es not_active Expired
- 1982-08-26 ZA ZA826252A patent/ZA826252B/xx unknown
- 1982-08-26 JP JP57148452A patent/JPS5874673A/ja active Granted
- 1982-08-26 AU AU87730/82A patent/AU8773082A/en not_active Abandoned
- 1982-08-26 PT PT75471A patent/PT75471B/pt unknown
- 1982-08-26 IL IL66650A patent/IL66650A/xx unknown
- 1982-08-27 NZ NZ201740A patent/NZ201740A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL66650A (en) | 1985-08-30 |
| DE3262880D1 (en) | 1985-05-09 |
| US4496557A (en) | 1985-01-29 |
| FR2512024A1 (fr) | 1983-03-04 |
| EP0074304B1 (fr) | 1985-04-03 |
| JPS5874673A (ja) | 1983-05-06 |
| ZA826252B (en) | 1983-07-27 |
| FR2512024B1 ( ) | 1984-01-06 |
| PT75471A (fr) | 1982-09-01 |
| AU8773082A (en) | 1983-03-03 |
| ES515232A0 (es) | 1983-11-01 |
| IL66650A0 (en) | 1982-12-31 |
| PT75471B (fr) | 1984-11-19 |
| EP0074304A1 (fr) | 1983-03-16 |
| ES8400422A1 (es) | 1983-11-01 |
| ATE12497T1 (de) | 1985-04-15 |
| GR77595B ( ) | 1984-09-25 |
| NZ201740A (en) | 1985-05-31 |
| CA1227481A (fr) | 1987-09-29 |
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