• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    The invention provides certain dibenzo[a,d]cycloocten-5,12-(and 6,12)- imines and their substituted derivatives and pharmaceutically acceptable salts of such compounds, methods of preparing such compounds and pharmaceutically acceptable compositions containing them. The compounds, the free-base forms of which have the formula: <IMAGE> where R, R<1> and R<2> are hydrogen or certain hydrocarbon residues, and R<3> and R<4> are hydrogen, halogen, alkoxy, CF3S-, -CN, -COOH or -OH, are useful as antianxiety agents, as muscle relaxants and in the treatment of extrapyramidal disorders such as in Parkinson's disease.
    公开号:SU908248A3
    申请号:SU2664652
    申请日:1978-09-19
    公开日:1982-02-23
    发明作者:С.Андерсон Пол；Е.Кристи Марсиа；Е.Эванс Бен；С.Реми Дэвид
    申请人:Мерк Энд Ко., Инк (Фирма)；
    IPC主号:
    专利说明:

    and the reaction is carried out, for example, in ethylene glycol or butyllithium 8 tetrahydrofuran or 1,2-dimethoxyethane is used.
    The desired products are isolated in the form of pharmaceutically acceptable salts with acids such as hydrochloric, fumaric, maleic, succinic, acetic, citric, tartaric, carbonic, phosphoric, and others.
     EXAMPLE D 1, 12 -1 -Dimethyl 5, 6,7,12-tetrahydrodibenzo a, cycloooctene-6, 12-iminohydrochloride. Stage A.
    Preparation of 6, 6-spiro (ethylenedioxy-12-OXO-5, 6,7,12-tetrahydrodibenso a, dj cycloctene.
    A mixture of kQ g 6, 12-DIOXO-5, 6,7,12-tetrahydro-dibenzo a, d-cyclooctene, 35 ml of ethylene glycol, 250 mg of C-toluene sulfonic acid and 600 ml of benzene is heated to reflux in a Dean-Stark apparatus for 22 h The cooled mixture is filtered and the solid is washed with water (substance A). The organic filtrate is dried over, filtered and the solvent is distilled to dryness. The residue is washed with a small amount of cold benzene and hexane with the obtained &amp; n solid substances B. Substances A and B are combined. The yield is 3 g of 6,6-spiro (ethylenedioxy) -12-oxo-5, 6, 6, 12-tetrahydrodibenzo a, octene, m.p. . Stage B.
    Preparation of 12-methylene-5, 6, 7, 12-tetrahydro-dibenzo (a, d) cyclocten-6-one.
    A solution (125 ml) of 2.0 molar methyl lithium in diethyl ether was added dropwise with stirring to a suspension, 3 g of ethylenedioxy compound of stage A in 1 l of ether. After stirring overnight, the mixture was poured into ice water. The ether is washed with 2 x 200 ml of water, dried over, filtered and distilled to dryness. The residue is treated with 00 ml of chloroform and 200 ml of 4 n. hydrochloric acid and heated to reflux for 18 hours. The organic phase is washed with water (2 X 150 ml) and the water is extracted again with 150 ml of chloroform. United chloroform
    the layers are dried over (), filtered from the drying agent and concentrated to a dry residue. The crystalline residue is washed with hexane and get 3 +, 5 g of 5 (9 on diketone) 12-methylene-5,6, 7, 12-tetrahydrodibeiso a, dJ cyclo-6-one with so pl. 68-7 ° C. Step B. Preparation of 6-methylamino-12-methy-len-5,6,7,12-tetrahydrodibenzoGa, dj cyclooctene or its hydrochloride salt.
    The product of step B (2.0 g) is added to a solution of 6.5 g of methylamine in
    5 20Q ml of tetrahydrofuran (THF). Some molecular sieves are added as a drying agent and the mixture is stirred for 1 hour. After cooling, 3 g are added.
    0 acetic acid, then after 15 minutes 3 g of sodium cyanoborohydride are added and the mixture is stirred for about 72 hours. The reaction mixture is filtered and the filtrate is evaporated to dryness.
    5 residues. The residue is treated with 150 ml of water and concentrated hydrochloric acid to pH 1-2. After
    The mixture is washed with 100 ml of ether for 1 hour and the ether is distilled off. The mixture is alkalinized
     aqueous ammonia and extracted with diethyl ether (3x100 ml). The combined extracts are dried over (), filtered and concentrated to dryness. The residue is washed with hexane and 1.9 g of product are obtained in the form of a free base. It is dissolved in 20 ml of 4N. methanol hydrogen chloride and concentrated to a dry residue. OstaQ TOK is triturated with ether and recrystallized from acetonitrile to obtain 1.9 g of 6-methylamino-12-methylene-5, 6,7,12-tetrahydrodibenzo | a, dj cycloctene hydrochloride,
    j with so pl. 238-2 2 C Eng.). Stage G.
    Preparation of 12,13-dimethyl-5,6,7,12-tetrahydrodibenzo a, d cyclocten-6, 12-imine hydrochloride.
    权利要求:
    Claims (1)
    [1]
     A mixture of 7.1 g of the secondary amine of stage B, 6 g of solid potassium hydroxide and 150 ml of ethylene glycol is heated to reflux with a NIC in nitrogen atmosphere for 18 hours. Ethylene glycol flOO ml) is distilled from the mixture at 62 ° C / 0.3. mm Hg, the reaction mixture is poured into 600 ml of water and extracted with diethyl ether (3 X 250 ml). The extracts are combined, washed with 200 ml of water, dried over, filtered and evaporated to dryness. The residue is suspended in 350 ml of water containing 15 ml of concentrated hydrochloric acid, washed with 100 ml of ether, basified with concentrated aqueous ammonia and extracted with diethyl ether (3 X 150 ml. The ether extracts are combined, dried over Na2SQi, filtered and evaporated to dryness. 5.8 crude products are obtained, which are diluted in 75 ml of acetone and treated with 2.0 g of oxalic acid in 20 ml of hot acetone.Cooling gives a precipitation of 6.0 g of oxalate, which is recrystallized from methanol to give 5.2 g of oxalic acid salt. It is dissolved in 200 ml of aqueous ammonia and 250 ml of ether. The ether is separated, washed with water, dried over Na2-0, filtered and evaporated to a dry residue. The residue is dissolved in 50 ml of methanol and treated with 3.5 ml 11N ethanolic hydrogen chloride. The mixture is concentrated to a dry residue, which is suspended with 200 ml of ether and collected on a filter C, 6 g of a solid. The latter is heated with 100 ml of acetone to reflux, cooled in a freezer, filtered with obtaining 3.7 g of product, so pl. 2 + 9-245 ° C. Recrystallization from 350 ml of acetone after concentrated to 150 ml gives 3.1 g of 12.13-Dimethyl-5, 6, 7, 12-tetrahydrodibenzo a, octene-6, 12-imine hydrochloride, m.p. 252-25 ° C. Stage G (alternative). Preparation of 12.1Z-Dimethyl-5,6,7,12 -tetrahydrin-dibenzo a, dJ cyclocten-6, 12-imine acid oxalate. To 2.1 g (7.3 mol) of 6-methylamino-12-methylene-5, 6,7,12-tetrahydrobenz Ha, d cycloctane hydrochloride, stirred at room temperature in dry tetrahydrofuran (75 m Outyllithium in hexane is added (6.5 ml, 1, 6 M). The mixture is stirred for 2 hours, treated with ice-cold water (2 ml) and concentrated under reduced pressure. The residue is treated with water (50 ml) and extracted with diethyl ether (3 X 25 ml ). The volume of eight ether solutions is washed with water, dried over, filtered and evaporated to a dry residue under reduced pressure to obtain 12,1З-Dimethyl-5,6,7,12-t trahydrodioHsoj a, d cyclooctyl-6, 12-imine as a yellow oil. The oil, dissolved in acetone (2 ml), is treated with oxalic acid (0.96 g, 0.01 mol) in acetone and subjected to deep cooling to give 12, 3-Dimethyl-5,6,7,12-tetrahydrodibenzo a, d cyclocten-6, 12-imine acid oxalate as a white powder (2.4 g, 9b). Recrystallization from methanol gives 1, 2 g (k8% ) of the target product with a melting point of 181.5-183.5C (decomp.). EXAMPLE 2: 12-ETHYL-13-methyl-5, 6,7,12-tetrahydrodibenzo a, dJ cyclooctene-6, 12-imine hydrochloride. Stage A. Preparation of 6, 6-thio (ethylenedioxy) -12-ethylidene-5, 6,6,12-tetrahydro-dibenzo a, d of cyclooctene. To a stirred suspension of methyltriphenylphosphonium bromide (40.9 g, 0.11 mol) in diethyl ether (400 ml) was added butyl lithium in hexane 50.3 ml, 2.17M). To the resulting solution is added a solution of 6, 6-spiro (ethylenedioxy) -12-OXO-5,6,7,12-tetrahydrodibenzo | a, d cyclooctene (29 g, 0.10 mol) in dry THF (300 ml). After being heated to reflux for 10 hours, the solution was distilled off and the solvent was distilled off and the residue was partitioned between (300 ml) and HCCl, (500 ml). The solution in HCC1; i, dried over filtered and evaporated. The residue is chromatographed on silica gel, eluting with HCCI, to give 20.3 g of 6,6-spiro (ethylenedioxy) -12-ethylidene-5, 6,7,12-tetrahydrodibenzo a, dZcyclooctene, m.p. C. Stage B. Preparation of 12-ethylidene-5,6,7,12-tetrahydrodibenzo a, d cyclocten-6-one. A solution of 6,6-spipo (ethylenedioxy) 7 12-ethylidene-5,6, 7,12-tetrahydropy. Benzo a, d cyclooctene (15, g 0.053 mol) in НСС1з (00 ml) is suspended and heated to reflux together with 4 n. aqueous HC1 (200 ml) for 3 hours. The organic layer is separated, washed with H2O and. dried over. The drying agent was filtered off and the filtrate was evaporated. The residue is recrystallized from acetonitrile to give 11.8 g of 12-ethylidene-5,6,7,12-tetrabane; a, d is cycooctane-6-one with m.p. . Using the technique identical to that described in Example 1 (Stages C and D), but replacing the 12-metipen-5,6 with 7,12-tetrahydrodibide-isoGa, d cyclocton-6-one, used in stage B, the following compounds are obtained successively. Step B. 12-Ethylidene-6-methylamino-5,6,7,1 -tetrahydrodibenzo a, d cycloocten and its hydrochloride salt. Stage G. 12-ETHYL-13-methyl-5, 6,7,12-tetrahydrodibenzo {a, З3cyclooctene-6, 12-imine hydrochloride or acid oxalate. PRI me R 3. 6,12,13 Trimethyl 5, 6, 7 .12-tetrahydrodibenzo a, looctene-6,12-im. Stage A. Preparation of 6-hydroxy-6-methyl-12-methylene-5, 6, 7.12-tetrahydro-dibenzoGa, d cyclooctene. . Magnesium shavings (3.03 T), 0.125 mol) spay 18 ml of ether. Then a solution of 7.8 ml (17.9 0.126 mol) of methyl iodide in 37 ml of ether is prepared and about ml of it is added to the magnesium suspension. The mixture is carefully heated prior to the initiation of the Grignard reagent, and the remaining iodide solution is added so that the reaction mass boils slightly. The mixture was kept under nitrogen at reflux under reflux for one hour, then cooled to room temperature. A solution of 15 L g (0.0 6 mol) 12-methylene-6-oxo-5, 6, 7,12-tetrahydro-dibenzo a, dZ cyclooctene in 100 ml of diethyl ether is added to the stirred Grignard reagent solution for 5 minutes. The resulting mixture is stirred for one hour at room temperature and quickly poured into 1 liter of ice water containing 5 g of ammonium chloride. The resulting mixture is extracted three times with ether (200 ml) and the combined ether layers are washed once with dilute aqueous sodium bisulfite, then dilute sodium bicarbonate, and twice with water. The washed ether solution is dried with sodium bicarbonate and twice with water. The washed ethereal solution is dried over potassium carbonate, filtered and evaporated in vacuo to give 6-hydroxy-b-methyl-12-methylene 5, 6,7,12-tetrahydrodibenzo-a, dJ cyclooctene as a colorless, 17.7 g Step B. Preparation of 6, 12-dimethyl-6-hydroxy-5, 6, 7-12-tetrahydrodibenzo a, cyclooctene. The crude methylene compound of stage A (17.7 g) in 100 ml of absolute ethanol is treated with 1 g of decolorizing carbon and filtered. An additional 80 ml of ethanol is then added, followed by the addition of 0.5 g of catalyst (101 Pd / coal and the mixture is hydrogenated at 3.52 ac.) The hydrogenation is continued until one mole equivalent of hydrogen is absorbed. The mixture is filtered and evaporated vacuum to give 15.8 g of crude 6,12-dimethyl-6-hydroxy-5, 6,7,12-tetrahydro-dibenzo | a, d} cycloctene with mp 100135 ° C, which is a mixture of two isomers. B. Preparation of 6-acetylamino-6,12-dimethyl-5, 6, 7,12-tetrahydrodibenzo a, dj cyclooctene. Dimethyl carbinol stage B (11.5 g 0 mol molA 120 ml of acetonitrile and added dropwise to 50 ml of 95% sulfuric acid with stirring and cooling in ice so that the temperature of the mixture is kept approximately equal. After the addition of sulfuric acid is complete, the mixture is stirred for 3 hours at room temperature and then quickly poured into 700 ml of ice-water. The suspension obtained is stirred for 15 minutes, then filtered. The filtrate is extracted twice with chloroform and the filtered solid is dissolved in the same Gocolo solvent (00 ml full volume), Combined The chloroform fractions are washed twice with water, once with sodium bicarbonate solution and once again with water, dried over potassium carbonate, filtered and evaporated in vacuo. The solid obtained is dried, in vacuo overnight at iiO ° C, to give 6-acetylamino-6, 12-dimethyl-5,6,7,12-tetrahyd rhodbenzo a, g cyclooctene with m.p. 8S-22 C (mixture of isomers). After recrystallization from ethanol so pl. 232-233.5 ° C. Step G. Preparation of 6- (M-acetyl-K-methylamino) -6,12-dimethyl-5,6,7,12-tetrahydro dibenzoGa, dJ cycloctene. Diisopropylamine (7.6 g, 0.075 mol in 75 ml of tetrahydrofuran, previously dried over molecular sieves, is stirred in an ice bath and maintained under a nitrogen atmosphere while adding dropwise methyl lithium in ether (k2 ml of a 1.8 M solution, 0.076 mol ). The mixture is stirred under cooling with an ice bath for 1/2 h, then transferred with a sprig into a separating funnel of the reaction apparatus, where 12.7 g (0.033 mol) of the amide compound of stage B and 50 g of triphenylmethane, solution rented in 150 ml of THF. The amide solution is stirred under ice-cooling in nitrogen atmosphere and lithium solution-diisopropylamide are added dropwise so that the reaction temperature is below 10 ° C. The addition is continued until the orange color due to the presence of triphenyl methyl anion of the metal anion is maintained. The mixture is stirred for 15 minutes and processed 17 ml of methyl iodide in 20 ml of THF, added at a rate such that the internal temperature of the system is kept below 10 ° C. The mixture is stirred for one hour while cooling with an ice bath and another hour at room temperature. The solution is quickly poured into 1.5 L of ice water and extracted three times with chloroform. The combined chloroform fractions are washed twice with water, twice with 1N. HCl, twice diluted with sodium bisulfite solution and twice with water, dried over potassium carbonate, filtered and evaporated in vacuo to give 11.2 g (0.03b mol) 6- (N-acetyl-N-methyl but) -6, 12-dimethyl -5-6,7,12 -tragonable a, d cycloctane, with so pl. 118-1 ° 7 ° C (mixture of isomers). Chromatography on silica gel, elution of CHCIi and recrystallization from acetone / hexane gave a mp. 150151,. Stage D. Preparation of 6- (N-acethyl-N-methyl amino) -6-methyl-12-methylene-5,6,7,12-tetrahydrobenzo a, dZ cycloctene. A mixture of the N-methylamide compound of stage D (11.9 g 0.039 mol), 11 g (mol) of 2,3-dichloro-5, 6-dicyano-1,4-benzoquinone and 1.1 l of benzene are heated to reflux. for 40 h under nitrogen, then cooled, 3 times 1 n. a solution of sodium hydroxide and twice with water, dried over potassium carbonate, filtered and evaporated in vacuo to give 11.4. g 6- (N-acetyl- -methylamino) -6-methyl-12-methylene-5, 6,7, 12-tetrahydrodibenzo a / 1 cyclooctene as a brown oil. Step E. Preparation of 6,12,13-trimethyl-5,6,7,12 tetrahydrodibenzo a, d cycloocten-6, 12-imine. 1 M-Methylamide of stage D (8.6 g, 0.033 mol) in 86 ml of ethylene glycol is treated with 2.9 g (0.052 mol) of potassium hydroxide. The mixture is heated to reflux under nitrogen atmosphere for 2 hours. The solution is cooled, quickly poured into 1 liter of ice water and the resulting suspension was extracted three times with chloroform. The chloroform extracts are combined, washed with water, dried over potassium carbonate (boil off and evaporated in vacuo. 6.5 g of orange-brown oil are obtained. The oil is treated with an ethanolic solution of HC1 (excess) and evaporated in vacuo. The residue is triturated twice with ether and again evaporated to give U, g of a crude gray solid. Recrystallization from ethanol gives 6, 12,13-trimethyl-5,6,7,12-tetrahydrodibenzo a, d cycloctene-6, 12-imine hydrochloride, with T. PL. .287283 C. Dibenzo a, d cyclooctene-6,12-imini or their pharmaceutically acceptable salts could can be used as ankmolytic sedatives, muscle relaxants and for the treatment of extrapyramidal disorders, e.g. Parkinson's disease. 1 Claim of the invention Method of producing dibenzo a, loocten-6, 12-imines obi (her Lormulas 1 ft, DXfb where R - methyl "5 R is a hydrogen atom and methyl; R is a lower alkyl or their pharmaceutically acceptable salts, characterized in that the compound of the total formula of 11 p 8 is the value of R and R with which Y is a hydrogen atom or acene is higher; I) - lower alkylene, thyl; is reacted with a strong base at a temperature of 150 or, if Y is a hydrogen atom with alkyl lithium in an ether medium, and the obtained target product is isolated in free form or in the form of a pharmaceutically acceptable salt. Sources of information, taken into account during the examination 1. Zeigand-Hilgetag. Experimental methods in organic chemistry. M., 1966, p. 372.
    类似技术:
    公开号 | 公开日 | 专利标题
    JP3108483B2|2000-11-13|Indole derivatives and anti-ulcer drugs containing the same as active ingredients
    EP0204285B1|1992-01-15|Imidazoheterocyclic compounds processes for preparation thereof and pharmaceutical compositions comprising them
    JP4863591B2|2012-01-25|Substituted heterocyclic fused gamma-carboline
    SU588916A3|1978-01-15|Method of preparing 2-tetrahydrofuril-6,7-benzomorphanes or salts thereof
    SU511005A3|1976-04-15|The method of obtaining | 6,7-benzomorfan or morphinan
    EP0140070A1|1985-05-08|Pyridoindole derivatives, process for their preparation and their use
    EP0167901B1|1990-04-04|Active compounds
    DE3002367A1|1980-07-24|2-SUBSTITUTED TRANS-5-ARYL-2,3,4,4A, 5, 9B-HEXAHYDRO-1H-PYRIDO SQUARE CLAMP ON 4.3-SQUARE CLAMP TO INDOLE
    SU908248A3|1982-02-23|Process for preparing dibenzo-/a,d/-cyclooctene-6-12-imines or their pharmaceutically acceptable salts
    KR870001159B1|1987-06-13|Process for preparing pyrazole-ring alkylated pyrazoloquinolines
    US4087532A|1978-05-02|Analgesically useful 2-tetrahydrofurfuryl-5-lower alkyl-2-oxy-6,7-benzomorphans and salts thereof
    CA1250582A|1989-02-28|Tetrahydrocorynantheine derivatives and process fortheir preparation
    US4624954A|1986-11-25|6,7,8,9-tetrahydro-10-methylpyrido[1,2-a]indol-9-amines and derivatives thereof, useful for the treatment of cognitive impairments
    EA005491B1|2005-02-24|Method for the preparation of citalopram
    US4925867A|1990-05-15|Hydrocarbon substituted pyrrolidinones, intermediates therefor, and anti-convulsant use thereof
    EP0050387B1|1984-08-15|Benzo | pyrano | pyrroles, processes for their preparation and pharmaceutical preparations containing same
    US4665183A|1987-05-12|Process for preparing 6,7,8,9-tetrahydro-10-methylpyrido[1,2-a]indol-9-amines and derivatives thereof useful for the treatment of cognitive impairments
    US4353911A|1982-10-12|Indolo|quinolizidines, useful in increasing femoral and vertebral blood flow
    US3408396A|1968-10-29|alpha-cyclohexyl-3, 4-disubstituted-phenyl acetamides
    JPH07291974A|1995-11-07|Epi-epibatidine derivative and its preparation
    Kapples et al.1997|Synthesis of 1‐alkyl‐2, 3‐dihydro‐2‐|‐1H‐isoindoles as potential selective serotonin reuptake inhibitors
    EP0399159A2|1990-11-28|Quinoline derivatives
    CA1336514C|1995-08-01|Cyclo-octane neuroprotective agents
    FI78091B|1989-02-28|ANALOGIFICATE FARING FOR THE PREPARATION OF SAUSOM DOPAMINOAGONISTER ANVAENDBARA PYRIMIDO / 4,5-G / KINOLINDERIVAT.
    US4235903A|1980-11-25|1-Hydroxyalkanamine tetrahydrocarbazoles and cyclopent[b]indoles, compositions and method of use
    同族专利:
    公开号 | 公开日
    JPS5452099A|1979-04-24|
    GB2004550B|1982-03-10|
    US4329465A|1982-05-11|
    AR222978A1|1981-07-15|
    DE2840770A1|1979-03-22|
    FI782681A|1979-03-20|
    AT367422B|1982-07-12|
    GR64987B|1980-06-11|
    FR2403341B1|1982-12-31|
    CA1097633A|1981-03-17|
    FR2403341A1|1979-04-13|
    PT68545A|1978-10-01|
    ATA669678A|1981-11-15|
    JPS5636195B2|1981-08-22|
    SE7809186L|1979-03-20|
    DE2840770C2|1987-07-16|
    NL7808848A|1979-03-21|
    CH641180A5|1984-02-15|
    IE47358B1|1984-02-22|
    ZA785290B|1980-04-30|
    PL209599A1|1979-06-04|
    LU80198A1|1979-06-01|
    AU3966978A|1980-03-13|
    BE870563A|1979-03-19|
    IT1113287B|1986-01-20|
    IT7851125D0|1978-09-18|
    IE781877L|1979-03-19|
    IL55537D0|1978-12-17|
    NO783016L|1979-03-20|
    GB2004550A|1979-04-04|
    DK385478A|1979-03-20|
    ES473461A1|1979-11-01|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US3361767A|1966-04-04|1968-01-02|American Home Prod|10, 5-10, 11-dihydro-5h-dibenzo[a, d]cyclohepten-13-one and derivatives|
    NL7007464A|1969-05-30|1970-12-02|
    BE794904A|1972-02-04|1973-08-02|Roussel Uclaf|NEW DIBENZOCYCLOHEPTENE DERIVATIVES AND THEIR PREPARATION|
    US4052508A|1974-08-19|1977-10-04|Merck & Co., Inc.|Heterocyclic dihydroanthracen imines|
    US4064139A|1975-04-07|1977-12-20|Merck & Co., Inc.|Substituted 9,10-dihydroanthracen-9,10-imines|
    US4123596A|1977-03-02|1978-10-31|Chloride Silent Power Limited|Cathode structure for sodium sulphur cells|GB8600783D0|1986-01-14|1986-02-19|Merck Sharp & Dohme|N-methyl-d-aspartate receptor antagonists|
    NZ225634A|1987-08-10|1991-03-26|Merck & Co Inc|10,11-dihydro-5h-dibenzocyclohepten-5,10-imine derivatives and pharmaceutical compositions|
    GB8727989D0|1987-11-30|1988-01-06|Merck Sharp & Dohme|Therapeutic agents|
    EP0332246A1|1988-03-11|1989-09-13|Akzo N.V.|Tricyclic amine derivatives|
    US5260309A|1989-06-01|1993-11-09|Pfizer Inc.|4,5,6,11-tetrahydrobenzo [6,7] cycloocta [1,2-b]thiophen-6,11-imines and 6,11-dihydrobenzo [6,7] cycloocta [1,2-b] thiophen-6,11-imines|
    WO1990015060A1|1989-06-01|1990-12-13|Pfizer Inc.|4,5,6,11-TETRAHYDROBENZO[6,7]CYCLOOCTA[1,2-b]THIOPHEN-6,11-IMINES AND 6,11-DIHYDROBENZO[6,7]CYCLOOCTA[1,2-b]THIOPHEN-6,11-IMINES|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    US83434377A| true| 1977-09-19|1977-09-19|
    [返回顶部]