CH617920A5 - - Google Patents

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Publication number: CH617920A5
Authority: CH; Switzerland
Prior art keywords: carbon atoms; dihydro; radical; methanoanthracene; reduction
Prior art date: 1974-12-13

Application number

CH1615775A

Other languages

German (de)

English (en)

Inventor

Makoto Sunagawa

Hiromi Sato

Junki Katsube

Hisao Yamamoto

Original Assignee

Sumitomo Chemical Co

Priority date (The priority date 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 date listed.)

1974-12-13

Filing date

1975-12-12

Publication date

1980-06-30

1974-12-13 Priority claimed from JP14373474A external-priority patent/JPS5170760A/ja

1974-12-27 Priority claimed from JP752909A external-priority patent/JPS585182B2/ja

1975-04-04 Priority claimed from JP4145275A external-priority patent/JPS5821904B2/ja

1975-07-07 Priority claimed from JP8387175A external-priority patent/JPS5911576B2/ja

1975-12-12 Application filed by Sumitomo Chemical Co filed Critical Sumitomo Chemical Co

1980-01-08 Priority to CH10780A priority Critical patent/CH623298A5/de

1980-01-08 Priority to CH10980A priority patent/CH622763A5/de

1980-01-08 Priority to CH10880A priority patent/CH623299A5/de

1980-06-30 Publication of CH617920A5 publication Critical patent/CH617920A5/de

Links

-1 aralkyl radical Chemical class 0.000 claims description 82
125000004432 carbon atom Chemical group C* 0.000 claims description 72
150000001875 compounds Chemical class 0.000 claims description 36
230000009467 reduction Effects 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 17
238000000034 method Methods 0.000 claims description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
238000010992 reflux Methods 0.000 claims description 13
239000012442 inert solvent Substances 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
239000003638 chemical reducing agent Substances 0.000 claims description 10
238000001816 cooling Methods 0.000 claims description 7
231100000252 nontoxic Toxicity 0.000 claims description 7
230000003000 nontoxic effect Effects 0.000 claims description 7
229910052987 metal hydride Inorganic materials 0.000 claims description 6
150000004681 metal hydrides Chemical class 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000006684 polyhaloalkyl group Polymers 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
150000005840 aryl radicals Chemical class 0.000 claims description 4
150000003254 radicals Chemical class 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
230000001476 alcoholic effect Effects 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000002560 nitrile group Chemical group 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
239000003513 alkali Substances 0.000 claims 1
125000004450 alkenylene group Chemical group 0.000 claims 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 66
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
239000000243 solution Substances 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
ZAELYRWEXINIKF-UHFFFAOYSA-N ctk2f1535 Chemical compound C12=CC=CC=C2C2(C=O)C3=CC=CC=C3C1C2 ZAELYRWEXINIKF-UHFFFAOYSA-N 0.000 description 19
238000002844 melting Methods 0.000 description 16
230000008018 melting Effects 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 16
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
239000000203 mixture Substances 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 12
239000012280 lithium aluminium hydride Substances 0.000 description 10
238000009835 boiling Methods 0.000 description 9
239000013078 crystal Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
230000000694 effects Effects 0.000 description 8
230000008707 rearrangement Effects 0.000 description 8
KMQFIAHMFOCATJ-UHFFFAOYSA-N 1-aminotetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaen-15-ol Chemical compound C12=CC=CC=C2C2(N)C3=CC=CC=C3C1CC2O KMQFIAHMFOCATJ-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
239000000739 antihistaminic agent Substances 0.000 description 6
235000019260 propionic acid Nutrition 0.000 description 6
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
239000002024 ethyl acetate extract Substances 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
125000000896 monocarboxylic acid group Chemical group 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
YEMCWAQXCZYBBW-UHFFFAOYSA-N tetracyclo[6.6.1.02,7.09,14]pentadeca-2,4,6,9,11,13-hexaene Chemical compound C12=CC=CC=C2C2CC1C1=CC=CC=C12 YEMCWAQXCZYBBW-UHFFFAOYSA-N 0.000 description 5
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000000825 pharmaceutical preparation Substances 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
RLAWQNBRBDSSQS-UHFFFAOYSA-N 1h-cyclopropa[a]anthracene Chemical class C1=CC=CC2=CC3=C4CC4=CC=C3C=C21 RLAWQNBRBDSSQS-UHFFFAOYSA-N 0.000 description 3
UJYLVBYLUYEPNY-UHFFFAOYSA-N 9-tosyloxymethyl-9,10-dihydro-9,10-methanoanthracene Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1(C2=CC=CC=C22)C3=CC=CC=C3C2C1 UJYLVBYLUYEPNY-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 3
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 3
238000007239 Wittig reaction Methods 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000000794 anti-serotonin Effects 0.000 description 3
239000000935 antidepressant agent Substances 0.000 description 3
229940125715 antihistaminic agent Drugs 0.000 description 3
239000003420 antiserotonin agent Substances 0.000 description 3
239000002249 anxiolytic agent Substances 0.000 description 3
230000037396 body weight Effects 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000000284 extract Substances 0.000 description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
235000010288 sodium nitrite Nutrition 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000007858 starting material Substances 0.000 description 3
NAJSLFHKTAUDPL-UHFFFAOYSA-N (9,10-dihydro-9,10-methano-9-anthryl)acetonitrile Chemical compound C12=CC=CC=C2C2(CC#N)C3=CC=CC=C3C1C2 NAJSLFHKTAUDPL-UHFFFAOYSA-N 0.000 description 2
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
NMSCHAVZGNIZJT-UHFFFAOYSA-N 9,10-dihydro-9,10-methano-9-anthracenecarboxylic acid Chemical compound C12=CC=CC=C2C2(C(=O)O)C3=CC=CC=C3C1C2 NMSCHAVZGNIZJT-UHFFFAOYSA-N 0.000 description 2
JNEZKOQYZFBAEE-UHFFFAOYSA-N 9,10-dihydro-9,10-methanoanthracene-9-carbonitrile Chemical compound C12=CC=CC=C2C2(C#N)C3=CC=CC=C3C1C2 JNEZKOQYZFBAEE-UHFFFAOYSA-N 0.000 description 2
IYUARCMLAXIYFP-UHFFFAOYSA-N 9,10-dihydro-9,10-methanoanthracene-9-carboxamide Chemical compound C12=CC=CC=C2C2(C(=O)N)C3=CC=CC=C3C1C2 IYUARCMLAXIYFP-UHFFFAOYSA-N 0.000 description 2
IZUFWQBEJCIXMX-UHFFFAOYSA-N 9-aminomethyl-9,10-dihydro-9,10-methanoanthracene Chemical class C12=CC=CC=C2C2(CN)C3=CC=CC=C3C1C2 IZUFWQBEJCIXMX-UHFFFAOYSA-N 0.000 description 2
ONHIINJTLUFUOA-UHFFFAOYSA-N 9-γ-hydroxypropyl-9,10-dihydro-9,10-methanoanthracene Chemical compound C12=CC=CC=C2C2(CCCO)C3=CC=CC=C3C1C2 ONHIINJTLUFUOA-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
238000006969 Curtius rearrangement reaction Methods 0.000 description 2
238000006238 Demjanov rearrangement reaction Methods 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
231100000403 acute toxicity Toxicity 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
125000000304 alkynyl group Chemical group 0.000 description 2
YCNZFPXXIWEFCF-UHFFFAOYSA-N alumane;sodium Chemical compound [Na].[AlH3] YCNZFPXXIWEFCF-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
CMBLOUYWEHGGES-UHFFFAOYSA-N anthracene;hydrochloride Chemical compound Cl.C1=CC=CC2=CC3=CC=CC=C3C=C21 CMBLOUYWEHGGES-UHFFFAOYSA-N 0.000 description 2
230000001004 anti-acetylcholinic effect Effects 0.000 description 2
230000003266 anti-allergic effect Effects 0.000 description 2
230000001387 anti-histamine Effects 0.000 description 2
239000000043 antiallergic agent Substances 0.000 description 2
230000000949 anxiolytic effect Effects 0.000 description 2
150000001540 azides Chemical class 0.000 description 2
KXTIBXNAPDIXQE-UHFFFAOYSA-N ctk1j0466 Chemical compound C12=CC=CC=C2C2(CC(=O)OCC)C3=CC=CC=C3C1C2 KXTIBXNAPDIXQE-UHFFFAOYSA-N 0.000 description 2
WXBZAVSJTILQFW-UHFFFAOYSA-N ctk2f1533 Chemical compound C12=CC=CC=C2C2(C=CC(=O)O)C3=CC=CC=C3C1C2 WXBZAVSJTILQFW-UHFFFAOYSA-N 0.000 description 2
VPPCQVCZKDIGGG-UHFFFAOYSA-N dibenzobicyclo[2.2.2]octadiene Chemical compound C12=CC=CC=C2C2CCC1C1=CC=CC=C12 VPPCQVCZKDIGGG-UHFFFAOYSA-N 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
239000012948 isocyanate Chemical class 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
QJQAMHYHNCADNR-UHFFFAOYSA-N n-methylpropanamide Chemical compound CCC(=O)NC QJQAMHYHNCADNR-UHFFFAOYSA-N 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
238000006053 organic reaction Methods 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 2
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
MRXQGJKCSBGHHW-UHFFFAOYSA-N (1-isocyanato-15-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaenyl) acetate Chemical compound C12=CC=CC=C2C2CC(OC(=O)C)C1(N=C=O)C1=CC=CC=C12 MRXQGJKCSBGHHW-UHFFFAOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
KGMDODIDEQTIRA-UHFFFAOYSA-N 1,2-dihydrocyclobuta[a]anthracene Chemical class C1=CC2=CC3=CC=CC=C3C=C2C2=C1CC2 KGMDODIDEQTIRA-UHFFFAOYSA-N 0.000 description 1
VNEJVZBVWJYDCF-UHFFFAOYSA-N 1-(1-tetracyclo[6.6.1.02,7.09,14]pentadeca-2,4,6,9,11,13-hexaenylmethyl)piperidine Chemical compound C1C(C=2C3=CC=CC=2)C2=CC=CC=C2C13CN1CCCCC1 VNEJVZBVWJYDCF-UHFFFAOYSA-N 0.000 description 1
ZKFWGWXNKDTHQE-UHFFFAOYSA-N 15-acetyloxytetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-1-carboxylic acid Chemical compound C12=CC=CC=C2C2CC(OC(=O)C)C1(C(O)=O)C1=CC=CC=C12 ZKFWGWXNKDTHQE-UHFFFAOYSA-N 0.000 description 1
MLCJTYCLPSUUSU-UHFFFAOYSA-N 2-(1-tetracyclo[6.6.1.02,7.09,14]pentadeca-2,4,6,9,11,13-hexaenyl)acetic acid Chemical compound C12=CC=CC=C2C2(CC(=O)O)C3=CC=CC=C3C1C2 MLCJTYCLPSUUSU-UHFFFAOYSA-N 0.000 description 1
CQCAYWAIRTVXIY-UHFFFAOYSA-N 2-(triphenyl-$l^{5}-phosphanylidene)acetaldehyde Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC=O)C1=CC=CC=C1 CQCAYWAIRTVXIY-UHFFFAOYSA-N 0.000 description 1
125000004810 2-methylpropylene group Chemical group [H]C([H])([H])C([H])(C([H])([H])[*:2])C([H])([H])[*:1] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
AMUXWPADJWGRLY-UHFFFAOYSA-N 4-(1-tetracyclo[6.6.1.02,7.09,14]pentadeca-2,4,6,9,11,13-hexaenylmethyl)morpholine Chemical compound C1C(C=2C3=CC=CC=2)C2=CC=CC=C2C13CN1CCOCC1 AMUXWPADJWGRLY-UHFFFAOYSA-N 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
QSCXNFMVBPYYDL-UHFFFAOYSA-N 9-hydroxymethyl-9,10-dihydro-9,10-methanoanthracene Chemical compound C12=CC=CC=C2C2(CO)C3=CC=CC=C3C1C2 QSCXNFMVBPYYDL-UHFFFAOYSA-N 0.000 description 1
OTNXLGJQLUFCPB-UHFFFAOYSA-N 9-γ-aminopropyl-9,10-dihydro-9,10-methanoanthracene Chemical compound C12=CC=CC=C2C2(CCCN)C3=CC=CC=C3C1C2 OTNXLGJQLUFCPB-UHFFFAOYSA-N 0.000 description 1
XESRGWMRJRMUKW-UHFFFAOYSA-N 9-γ-morpholinopropyl-9,10-dihydro-9,10-methanoanthracene Chemical compound C1C(C=2C3=CC=CC=2)C2=CC=CC=C2C13CCCN1CCOCC1 XESRGWMRJRMUKW-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
238000006218 Arndt-Eistert homologation reaction Methods 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
RORZPMFTONYUBB-UHFFFAOYSA-N C12=CC=CC=C2C2CC(OC(=O)C)C1(C(Cl)=O)C1=CC=CC=C12 Chemical compound C12=CC=CC=C2C2CC(OC(=O)C)C1(C(Cl)=O)C1=CC=CC=C12 RORZPMFTONYUBB-UHFFFAOYSA-N 0.000 description 1
101100328518 Caenorhabditis elegans cnt-1 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
MWHHSFZFAZNDOF-UHFFFAOYSA-N Cl.C1=CC=CC2=C3C4=CC=CC=C4C(=C12)C3 Chemical compound Cl.C1=CC=CC2=C3C4=CC=CC=C4C(=C12)C3 MWHHSFZFAZNDOF-UHFFFAOYSA-N 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical class CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
206010015995 Eyelid ptosis Diseases 0.000 description 1
HILUWRPVFKJTAD-ZGHMGGRHSA-N GA21 Chemical compound O=C(O)[C@H]1[C@@H]2[C@]3(C(=O)O)C(=O)O[C@@]2([C@H]2[C@]41CC(=C)[C@@](O)(C4)CC2)CCC3 HILUWRPVFKJTAD-ZGHMGGRHSA-N 0.000 description 1
238000003747 Grignard reaction Methods 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
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 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
BMXFTPUKGWSDKG-UHFFFAOYSA-N N,N-diethyl-2-(4-tetracyclo[6.6.1.02,7.09,14]pentadeca-2(7),3,5,9,11,13-hexaenyl)ethanamine Chemical compound C(C)N(CC)CCC=1C=CC=2C3C4=CC=CC=C4C(C=2C=1)C3 BMXFTPUKGWSDKG-UHFFFAOYSA-N 0.000 description 1
OLRAMQCHLASJNJ-UHFFFAOYSA-N N-(1-tetracyclo[6.6.1.02,7.09,14]pentadeca-2,4,6,9,11,13-hexaenylmethyl)ethanamine Chemical compound C12=CC=CC=C2C2(CNCC)C3=CC=CC=C3C1C2 OLRAMQCHLASJNJ-UHFFFAOYSA-N 0.000 description 1
MBUQSIOIHBMFGX-UHFFFAOYSA-N N-methyl-1-(1-tetracyclo[6.6.1.02,7.09,14]pentadeca-2,4,6,9,11,13-hexaenyl)methanamine Chemical compound C12=CC=CC=C2C2(CNC)C3=CC=CC=C3C1C2 MBUQSIOIHBMFGX-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
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238000006680 Reformatsky reaction Methods 0.000 description 1
PQQTZWYTYDIGPP-UHFFFAOYSA-N S(=O)(=O)(C1=CC=C(C)C=C1)OCCC=1C=CC=2C3C4=CC=CC=C4C(C2C1)C3 Chemical compound S(=O)(=O)(C1=CC=C(C)C=C1)OCCC=1C=CC=2C3C4=CC=CC=C4C(C2C1)C3 PQQTZWYTYDIGPP-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 description 1
JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
231100001259 acute cardiotoxicity Toxicity 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000004103 aminoalkyl group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
230000001078 anti-cholinergic effect Effects 0.000 description 1
230000003326 anti-histaminergic effect Effects 0.000 description 1
230000000891 anti-reserpine Effects 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
229940005530 anxiolytics Drugs 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
229940117975 chromium trioxide Drugs 0.000 description 1
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
YKOCVSGATTYCSG-UHFFFAOYSA-N ctk1j0467 Chemical compound C12=CC=CC=C2C2(CNC(=O)C)C3=CC=CC=C3C1C2 YKOCVSGATTYCSG-UHFFFAOYSA-N 0.000 description 1
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical group 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000012458 free base Substances 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000008187 granular material Substances 0.000 description 1
UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
229960002456 hexobarbital Drugs 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
230000002631 hypothermal effect Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
SJFNDMHZXCUXSA-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 SJFNDMHZXCUXSA-UHFFFAOYSA-M 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000003158 myorelaxant agent Substances 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
210000000653 nervous system Anatomy 0.000 description 1
239000003176 neuroleptic agent Substances 0.000 description 1
229960002748 norepinephrine Drugs 0.000 description 1
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
239000004304 potassium nitrite Substances 0.000 description 1
235000010289 potassium nitrite Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000004089 psychotropic agent Substances 0.000 description 1
201000003004 ptosis Diseases 0.000 description 1
238000000746 purification Methods 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
238000006462 rearrangement reaction Methods 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
230000002040 relaxant effect Effects 0.000 description 1
238000006049 ring expansion reaction Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
229910001923 silver oxide Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
229960005333 tetrabenazine Drugs 0.000 description 1
XVWGGWYDDICSQC-UHFFFAOYSA-N tetracyclo[6.6.1.02,7.09,14]pentadeca-1,3,5,7,9,11,13-heptaene Chemical compound C1=CC=CC2=C3C4=CC=CC=C4C(=C12)C3 XVWGGWYDDICSQC-UHFFFAOYSA-N 0.000 description 1
VNVBAPKOJGLIDO-UHFFFAOYSA-N tetracyclo[6.6.2.02,7.09,14]hexadeca-1,3,5,7,9,11,13-heptaene Chemical class C12=CC=CC=C2C2=C(C=CC=C3)C3=C1CC2 VNVBAPKOJGLIDO-UHFFFAOYSA-N 0.000 description 1
125000005505 thiomorpholino group Chemical group 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
125000006000 trichloroethyl group Chemical group 0.000 description 1
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/235—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/235—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings
- C07C47/238—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings having unsaturation outside the aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
- C07C47/453—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
- C07C57/50—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid containing condensed ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/39—Unsaturated compounds containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH1615775A 1974-12-13 1975-12-12 CH617920A5 (pt)

Priority Applications (3)

Application Number	Priority Date	Filing Date	Title
CH10780A CH623298A5 (en)	1974-12-13	1980-01-08	Process for the preparation of methanoanthracene derivatives
CH10980A CH622763A5 (en)	1974-12-13	1980-01-08	Process for the preparation of 9-formyl-9,10-dihydro-9,10-methanoanthracene
CH10880A CH623299A5 (en)	1974-12-13	1980-01-08	Process for the preparation of novel tricyclic compounds

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP14373474A JPS5170760A (ja)	1974-12-13	1974-12-13	Metanooantorasenjudotaino shinkiseizoho
JP752909A JPS585182B2 (ja)	1974-12-27	1974-12-27	シンキナメタノ−アントラセンユウドウタイノセイゾウホウ
JP4145275A JPS5821904B2 (ja)	1975-04-04	1975-04-04	シンキナメタノ−アントラセンユウドウタイノセイゾウホウホウ
JP8387175A JPS5911576B2 (ja)	1975-07-07	1975-07-07	新規なメタノ−アントラセン誘導体の製造法

Publications (1)

Publication Number	Publication Date
CH617920A5 true CH617920A5 (pt)	1980-06-30

Family

ID=27453741

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1615775A CH617920A5 (pt)	1974-12-13	1975-12-12

Country Status (13)

Country	Link
US (1)	US4224344A (pt)
AR (2)	AR212586A1 (pt)
BE (1)	BE836599A (pt)
CA (2)	CA1061787A (pt)
CH (1)	CH617920A5 (pt)
DE (1)	DE2556143A1 (pt)
ES (3)	ES443487A1 (pt)
FR (2)	FR2293940A1 (pt)
GB (1)	GB1508669A (pt)
NL (1)	NL7514601A (pt)
NO (1)	NO792908L (pt)
NZ (1)	NZ179530A (pt)
SE (2)	SE429040B (pt)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5512575A (en) *	1991-08-15	1996-04-30	Zeneca Limited	Methanoanthraceneyl methyl piperidinyl compounds
GB9216298D0 (en) *	1991-08-15	1992-09-16	Ici Plc	Piperidine derivatives
GB9117639D0 (en) *	1991-08-15	1991-10-02	Ici Plc	Therapeutic compounds
GB9216297D0 (en) *	1991-08-15	1992-09-16	Ici Plc	Therapeutic agents
KR20080065704A (ko)	2005-11-09	2008-07-14	콤비네이토릭스, 인코포레이티드	의학적 이상의 치료 방법들, 조성물들, 및 키트들

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL127069C (pt) *	1961-10-10
US3622630A (en) *	1968-07-03	1971-11-23	Smith Kline French Lab	10-aminoalkyl-9,10-dihydroanthracenes
US3708525A (en) *	1969-11-20	1973-01-02	Merck & Co Inc	Chemical compounds and processes for preparing same
IL38772A (en) *	1971-02-23	1975-06-25	Ciba Geigy Ag	Aminopropenyl-anthracene derivatives,their manufacture and pharmaceutical compositions containing them

1975
- 1975-12-11 GB GB42689/77A patent/GB1508669A/en not_active Expired
- 1975-12-11 US US05/639,974 patent/US4224344A/en not_active Expired - Lifetime
- 1975-12-12 SE SE7514077A patent/SE429040B/xx unknown
- 1975-12-12 NZ NZ179530A patent/NZ179530A/xx unknown
- 1975-12-12 AR AR261582A patent/AR212586A1/es active
- 1975-12-12 DE DE19752556143 patent/DE2556143A1/de not_active Withdrawn
- 1975-12-12 BE BE162715A patent/BE836599A/xx not_active IP Right Cessation
- 1975-12-12 CA CA241,665A patent/CA1061787A/en not_active Expired
- 1975-12-12 FR FR7538185A patent/FR2293940A1/fr active Granted
- 1975-12-12 CH CH1615775A patent/CH617920A5/de not_active IP Right Cessation
- 1975-12-13 ES ES75443487A patent/ES443487A1/es not_active Expired
- 1975-12-15 NL NL7514601A patent/NL7514601A/xx not_active Application Discontinuation
1976
- 1976-06-04 FR FR7617140A patent/FR2308610A1/fr active Granted
- 1976-09-27 AR AR264868A patent/AR213412A1/es active
1977
- 1977-05-02 ES ES77458426A patent/ES458426A1/es not_active Expired
- 1977-05-02 ES ES77458428A patent/ES458428A1/es not_active Expired
1978
- 1978-04-18 CA CA301,335A patent/CA1052393A/en not_active Expired
1979
- 1979-08-23 SE SE7907050A patent/SE7907050L/sv not_active Application Discontinuation
- 1979-09-07 NO NO79792908A patent/NO792908L/no unknown

Also Published As

Publication number	Publication date
NL7514601A (nl)	1976-06-15
SE7907050L (sv)	1979-08-23
AR212586A1 (es)	1978-08-15
CA1061787A (en)	1979-09-04
SE7514077L (sv)	1976-06-14
NZ179530A (en)	1978-04-28
ES443487A1 (es)	1977-11-01
US4224344A (en)	1980-09-23
NO792908L (no)	1976-06-15
FR2293940B1 (pt)	1981-12-04
FR2293940A1 (fr)	1976-07-09
GB1508669A (en)	1978-04-26
FR2308610A1 (fr)	1976-11-19
BE836599A (fr)	1976-06-14
ES458426A1 (es)	1978-04-01
DE2556143A1 (de)	1976-06-16
SE429040B (sv)	1983-08-08
CA1052393A (en)	1979-04-10
ES458428A1 (es)	1978-12-16
AR213412A1 (es)	1979-01-31
FR2308610B1 (pt)	1979-06-29
AU8741075A (en)	1977-06-16

Publication	Publication Date	Title
DE1695556C3 (de)	1981-06-25	3-Alkyl-1,2,3,4,4a,9-hexahydropyrazino[1,2-f]morphanthridinderivate
DE2820938A1 (de)	1978-11-23	Neue imidazoazine und imidazodiazine
DE69914594T2 (de)	2004-12-09	Aryl-annellierte azapolycyclische verbindungen
DE69530988T2 (de)	2003-12-04	Benzimidazolderivate mit dopaminerger wirkung
CH646426A5 (en)	1984-11-30	Process for the preparation of hydantoin derivatives
DE2314636A1 (de)	1973-10-04	Pharmakodynamisch aktive, basisch substituierte indanderivate
DE3103372A1 (de)	1982-09-02	Neue indanyl-derivate, ihre herstellung und verwendung
DD272648A5 (de)	1989-10-18	Chromon-derivate
CH617920A5 (pt)	1980-06-30
DE68906340T2 (de)	1993-08-12	Tetrahydronaphthalin und indan-derivate.
DD151408A5 (de)	1981-10-21	Verfahren zur herstellung neuer pharmazeutisch aktiver phenylpiperazinderivate
DE3151201A1 (de)	1983-07-28	Substituierte phenoxyalkanolamine und phenoxyalkanol-cycloalkylamine, verfahren zu ihrer herstellung, diese verbindungen enthaltende pharmazeutische zubereitungen und zwischenprodukte
DE2619617C2 (pt)	1987-10-01
DE2526966A1 (de)	1976-01-08	Tricyclische alkylaminverbindungen, verfahren zu ihrer herstellung und sie enthaltende mittel
DE2609437C2 (pt)	1987-10-01
DE2609862C2 (pt)	1987-09-24
EP0472166A1 (de)	1992-02-26	Tricyclische Pyridonderivate
CH623811A5 (pt)	1981-06-30
CH623298A5 (en)	1981-05-29	Process for the preparation of methanoanthracene derivatives
CH622792A5 (pt)	1981-04-30
DE1151509B (de)	1963-07-18	Verfahren zur Herstellung von Phenthiazinderivaten
EP0259871A1 (de)	1988-03-16	Heterocyclisch substituierte Indolinone, Verfahren zu ihrer Herstellung, Arzneimittel sowie Zwischenprodukte
AT363094B (de)	1981-07-10	Verfahren zur herstellung von neuen piperazinderivaten und deren salzen
AT371113B (de)	1983-06-10	Verfahren zur herstellung von neuen imidazolen und deren salzen
AT376423B (de)	1984-11-26	Verfahren zur herstellung von neuen 1,2,4triazolderivaten

Legal Events

Date	Code	Title	Description
1985-08-30	PL	Patent ceased
2024-10-31	PL	Patent ceased