JPS62190184A - ８α−アクリルアミノエルゴリン、その製造方法および該化合物を含有する医薬組成物 - Google Patents
８α−アクリルアミノエルゴリン、その製造方法および該化合物を含有する医薬組成物Info
- Publication number
- JPS62190184A JPS62190184A JP62015028A JP1502887A JPS62190184A JP S62190184 A JPS62190184 A JP S62190184A JP 62015028 A JP62015028 A JP 62015028A JP 1502887 A JP1502887 A JP 1502887A JP S62190184 A JPS62190184 A JP S62190184A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- carbon atoms
- acid addition
- formula
- compound
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title description 30
- 238000004519 manufacturing process Methods 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims description 94
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 125000004432 carbon atom Chemical group C* 0.000 claims description 49
- 150000003839 salts Chemical class 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 16
- -1 R_2 is CN Chemical group 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 239000000935 antidepressant agent Substances 0.000 claims description 4
- 229940005513 antidepressants Drugs 0.000 claims description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
- 230000001430 anti-depressive effect Effects 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- ZIIMQMYFQHBXEN-ZBQZNYHESA-N N-[(6aR,9S,10aR)-5-ethynyl-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]-2,2-dimethylpropanamide Chemical compound CN1C[C@H](C[C@@H]2C=3C=CC=C4NC(=C(C[C@@H]12)C=34)C#C)NC(C(C)(C)C)=O ZIIMQMYFQHBXEN-ZBQZNYHESA-N 0.000 claims description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 230000003340 mental effect Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 26
- 238000002844 melting Methods 0.000 description 26
- 230000008018 melting Effects 0.000 description 26
- 239000000243 solution Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 102000003946 Prolactin Human genes 0.000 description 10
- 108010057464 Prolactin Proteins 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 229940097325 prolactin Drugs 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 230000028327 secretion Effects 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- JHWDWUPYEQIICX-HRBVQNPCSA-N (6ar,10ar)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-amine Chemical compound C1=CC([C@@H]2[C@H](NCC(C2)N)C2)=C3C2=CNC3=C1 JHWDWUPYEQIICX-HRBVQNPCSA-N 0.000 description 7
- 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 7
- 229960004046 apomorphine Drugs 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 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 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 229960005333 tetrabenazine Drugs 0.000 description 6
- 208000009132 Catalepsy Diseases 0.000 description 5
- 206010015995 Eyelid ptosis Diseases 0.000 description 5
- 206010047853 Waxy flexibility Diseases 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- 239000003136 dopamine receptor stimulating agent Substances 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- 230000006651 lactation Effects 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 201000003004 ptosis Diseases 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- NUVLGIVUSHTJSS-YSVLISHTSA-N CN1C[C@H](C[C@@H]2C=3C=CC=C4NC=C(C[C@@H]12)C34)NC(C(C)(C)C)=O Chemical compound CN1C[C@H](C[C@@H]2C=3C=CC=C4NC=C(C[C@@H]12)C34)NC(C(C)(C)C)=O NUVLGIVUSHTJSS-YSVLISHTSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- 239000005557 antagonist Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- 238000010998 test method Methods 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000012730 sustained-release form Substances 0.000 description 3
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 206010022998 Irritability Diseases 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- IQSAXIAAXHYOPY-ZBQZNYHESA-N N-[(6aR,9S,10aR)-5-ethyl-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]-2,2-dimethylpropanamide Chemical compound CN1C[C@H](C[C@@H]2C=3C=CC=C4NC(=C(C[C@@H]12)C34)CC)NC(C(C)(C)C)=O IQSAXIAAXHYOPY-ZBQZNYHESA-N 0.000 description 2
- QQOBKRMCHVRFBU-NORZTCDRSA-N N-[(6aR,9S,10aR)-5-iodo-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]-2,2-dimethylpropanamide Chemical compound IC1=C2C[C@H]3N(C[C@H](C[C@@H]3C=3C=CC=C(N1)C32)NC(C(C)(C)C)=O)C QQOBKRMCHVRFBU-NORZTCDRSA-N 0.000 description 2
- 208000018737 Parkinson disease Diseases 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 150000002688 maleic acid derivatives Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- 239000012279 sodium borohydride Substances 0.000 description 2
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- 150000003457 sulfones Chemical class 0.000 description 2
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- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
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- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
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- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 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
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 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 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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- CWMLSLXOWMDNMN-JCKWVBRZSA-N N-[(6aR,9S,10aR)-5-acetamido-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]-2,2-dimethylpropanamide Chemical compound CN1C[C@H](C[C@@H]2C=3C=CC=C4NC(=C(C[C@@H]12)C34)NC(C)=O)NC(C(C)(C)C)=O CWMLSLXOWMDNMN-JCKWVBRZSA-N 0.000 description 1
- GGMZAKZOWXSHQG-JCKWVBRZSA-N N-[(6aR,9S,10aR)-5-acetyl-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]-2,2-dimethylpropanamide Chemical compound C(C)(=O)C1=C2C[C@H]3N(C[C@H](C[C@@H]3C=3C=CC=C(N1)C32)NC(C(C)(C)C)=O)C GGMZAKZOWXSHQG-JCKWVBRZSA-N 0.000 description 1
- WNDMNAVMWRQBBQ-WPKBUWHJSA-N N-[(6aR,9S,10aR)-5-formyl-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]-2,2-dimethylpropanamide Chemical compound C(=O)C1=C2C[C@H]3N(C[C@H](C[C@@H]3C=3C=CC=C(N1)C32)NC(C(C)(C)C)=O)C WNDMNAVMWRQBBQ-WPKBUWHJSA-N 0.000 description 1
- ZYVJMYQOGXTAOV-WPKBUWHJSA-N N-[(6aR,9S,10aR)-7-methyl-5-(2,2,2-trifluoroethyl)-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]-2,2-dimethylpropanamide Chemical compound FC(CC1=C2C[C@H]3N(C[C@H](C[C@@H]3C=3C=CC=C(N1)C32)NC(C(C)(C)C)=O)C)(F)F ZYVJMYQOGXTAOV-WPKBUWHJSA-N 0.000 description 1
- LAYCLWZDGNOUEU-JCKWVBRZSA-N N-[(6aR,9S,10aR)-7-methyl-5-[2-(trifluoromethyl)-1,3-dithiolan-2-yl]-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]-2,2-dimethylpropanamide Chemical compound FC(C1(SCCS1)C1=C2C[C@H]3N(C[C@H](C[C@@H]3C=3C=CC=C(N1)C32)NC(C(C)(C)C)=O)C)(F)F LAYCLWZDGNOUEU-JCKWVBRZSA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 231100000540 amenorrhea Toxicity 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- OKTJSMMVPCPJKN-BJUDXGSMSA-N carbon-11 Chemical group [11C] OKTJSMMVPCPJKN-BJUDXGSMSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 231100000895 deafness Toxicity 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 230000023556 desulfurization Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 239000003210 dopamine receptor blocking agent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 208000016354 hearing loss disease Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000012336 iodinating agent Substances 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- RSEAASAWECJNTP-DXCKQFNASA-N methyl (6aR,9S,10aR)-9-(2,2-dimethylpropanoylamino)-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-5-carboxylate Chemical compound C(=O)(OC)C1=C2C[C@H]3N(C[C@H](C[C@@H]3C=3C=CC=C(N1)C32)NC(C(C)(C)C)=O)C RSEAASAWECJNTP-DXCKQFNASA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- PYVXLMQALOZKES-UHFFFAOYSA-M tetrabutylazanium;periodate Chemical compound [O-]I(=O)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC PYVXLMQALOZKES-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/10—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hetero atoms directly attached in position 8
- C07D457/12—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- 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
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3602058.3 | 1986-01-24 | ||
| DE3602058 | 1986-01-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62190184A true JPS62190184A (ja) | 1987-08-20 |
Family
ID=6292510
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62015028A Pending JPS62190184A (ja) | 1986-01-24 | 1987-01-23 | ８α−アクリルアミノエルゴリン、その製造方法および該化合物を含有する医薬組成物 |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS62190184A (fr) |
| KR (1) | KR870007175A (fr) |
| AU (1) | AU6791487A (fr) |
| BE (1) | BE1000039A4 (fr) |
| DK (1) | DK35787A (fr) |
| ES (1) | ES2003774A6 (fr) |
| FI (1) | FI870293A (fr) |
| FR (1) | FR2595699A1 (fr) |
| GB (1) | GB2185743A (fr) |
| GR (1) | GR870093B (fr) |
| HU (1) | HUT45248A (fr) |
| IL (1) | IL81355A0 (fr) |
| IT (1) | IT1216783B (fr) |
| LU (1) | LU86743A1 (fr) |
| NL (1) | NL8700046A (fr) |
| PT (1) | PT84184A (fr) |
| SE (1) | SE8700250L (fr) |
| ZA (1) | ZA87520B (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014517076A (ja) * | 2011-06-23 | 2014-07-17 | マップ・ファーマシューティカルズ・インコーポレイテッド | 新規のフルオロエルゴリン類似体 |
| US10703753B2 (en) | 2015-01-20 | 2020-07-07 | Xoc Pharmaceuticals, Inc. | Ergoline compounds and uses thereof |
| US10815235B2 (en) | 2017-06-01 | 2020-10-27 | Xoc Pharmaceuticals | Polycyclic compounds and uses thereof |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8714767D0 (en) * | 1987-06-24 | 1987-07-29 | Erba Farmitalia | Egoline derivatives |
| ATE107647T1 (de) * | 1984-04-09 | 1994-07-15 | Schering Ag | 2-substituierte ergolin-derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel. |
| DK338789A (da) * | 1988-07-15 | 1990-01-16 | Schering Ag | 2-substituerede ergolinylurinstofderivater og fremgangsmaade til fremstilling deraf, deres anvendelse som laegemidler samt mellemprodukter til fremstilling deraf |
| DE3915950A1 (de) * | 1989-05-12 | 1990-11-15 | Schering Ag | 8(alpha)-acylamino-ergoline, ihre herstellung und verwendung als arzneimittel |
| WO2013095707A1 (fr) * | 2011-12-19 | 2013-06-27 | Map Pharmaceuticals, Inc. | Nouveaux dérivés d'iso-ergoline |
| CA2974113A1 (fr) * | 2015-01-20 | 2016-07-28 | Xoc Pharmaceuticals, Inc. | Composes d'isoergoline et leurs utilisations |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1517973A (en) * | 1974-07-19 | 1978-07-19 | Sandoz Ltd | 6-methyl-8alpha-n,n-dimethylsulphamoylaminoergoline i |
| CH615929A5 (en) * | 1975-06-02 | 1980-02-29 | Sandoz Ag | Process for the preparation of novel ergoline compounds |
| CH664568A5 (de) * | 1984-01-12 | 1988-03-15 | Sandoz Ag | 8-alpha-acylaminoergoline. |
-
1987
- 1987-01-12 HU HU8792A patent/HUT45248A/hu unknown
- 1987-01-12 NL NL8700046A patent/NL8700046A/nl not_active Application Discontinuation
- 1987-01-21 GB GB08701274A patent/GB2185743A/en not_active Withdrawn
- 1987-01-22 ES ES8700163A patent/ES2003774A6/es not_active Expired
- 1987-01-22 DK DK035787A patent/DK35787A/da not_active Application Discontinuation
- 1987-01-22 IL IL81355A patent/IL81355A0/xx unknown
- 1987-01-22 FR FR8700834A patent/FR2595699A1/fr active Pending
- 1987-01-22 KR KR870000556A patent/KR870007175A/ko not_active Application Discontinuation
- 1987-01-22 SE SE8700250A patent/SE8700250L/xx not_active Application Discontinuation
- 1987-01-22 AU AU67914/87A patent/AU6791487A/en not_active Abandoned
- 1987-01-22 IT IT8747551A patent/IT1216783B/it active
- 1987-01-22 PT PT84184A patent/PT84184A/pt unknown
- 1987-01-22 GR GR870093A patent/GR870093B/el unknown
- 1987-01-22 LU LU86743A patent/LU86743A1/fr unknown
- 1987-01-23 FI FI870293A patent/FI870293A/fi not_active IP Right Cessation
- 1987-01-23 BE BE8700046A patent/BE1000039A4/fr not_active IP Right Cessation
- 1987-01-23 JP JP62015028A patent/JPS62190184A/ja active Pending
- 1987-01-23 ZA ZA87520A patent/ZA87520B/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014517076A (ja) * | 2011-06-23 | 2014-07-17 | マップ・ファーマシューティカルズ・インコーポレイテッド | 新規のフルオロエルゴリン類似体 |
| US10703753B2 (en) | 2015-01-20 | 2020-07-07 | Xoc Pharmaceuticals, Inc. | Ergoline compounds and uses thereof |
| US10815235B2 (en) | 2017-06-01 | 2020-10-27 | Xoc Pharmaceuticals | Polycyclic compounds and uses thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA87520B (en) | 1988-09-28 |
| FI870293A0 (fi) | 1987-01-23 |
| IT1216783B (it) | 1990-03-14 |
| FI870293A (fi) | 1987-07-25 |
| ES2003774A6 (es) | 1988-11-16 |
| GB8701274D0 (en) | 1987-02-25 |
| IT8747551A0 (it) | 1987-01-22 |
| DK35787A (da) | 1987-07-25 |
| NL8700046A (nl) | 1987-08-17 |
| LU86743A1 (fr) | 1987-09-03 |
| IL81355A0 (en) | 1987-08-31 |
| BE1000039A4 (fr) | 1987-12-15 |
| DK35787D0 (da) | 1987-01-22 |
| HUT45248A (en) | 1988-06-28 |
| FR2595699A1 (fr) | 1987-09-18 |
| SE8700250D0 (sv) | 1987-01-22 |
| PT84184A (pt) | 1987-02-01 |
| SE8700250L (sv) | 1987-07-25 |
| GB2185743A (en) | 1987-07-29 |
| AU6791487A (en) | 1987-07-30 |
| KR870007175A (ko) | 1987-08-17 |
| GR870093B (en) | 1987-05-25 |
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