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
Authority: JP; Japan
Prior art keywords: alkyl; carbon atoms; acid addition; formula; compound
Prior art date: 1986-01-24
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

Application number

JP62015028A

Other languages

English (en)

Japanese (ja)

Inventor

レン・ツィーグレル

ペーター・ノイマン

バルター・ヘーフリガー

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sandoz AG

Original Assignee

Sandoz AG

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.)

1986-01-24

Filing date

1987-01-23

Publication date

1987-08-20

1987-01-23 Application filed by Sandoz AG filed Critical Sandoz AG

1987-08-20 Publication of JPS62190184A publication Critical patent/JPS62190184A/ja

Status Pending legal-status Critical Current

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
239000013078 crystal Substances 0.000 description 2
229940052760 dopamine agonists Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
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239000003112 inhibitor Substances 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
150000007517 lewis acids Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
238000010561 standard procedure Methods 0.000 description 2
150000003457 sulfones Chemical class 0.000 description 2
150000003462 sulfoxides Chemical class 0.000 description 2
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
230000001629 suppression Effects 0.000 description 2
239000000725 suspension Substances 0.000 description 2
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
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
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
201000000736 Amenorrhea Diseases 0.000 description 1
206010001928 Amenorrhoea Diseases 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
208000004130 Blepharoptosis Diseases 0.000 description 1
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
229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
206010011878 Deafness Diseases 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-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
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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
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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)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Anesthesiology (AREA)
Hospice & Palliative Care (AREA)
Otolaryngology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

JP62015028A 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 Pending JPS62190184A (ja)

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)	FI870293A7 (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 (4)

* Cited by examiner, † Cited by third party
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
JP2018502889A (ja) *	2015-01-20	2018-02-01	エックスオーシーファーマシューティカルズインコーポレイテッドＸｏｃＰｈａｒｍａｃｅｕｔｉｃａｌｓ，Ｉｎｃ	イソエルゴリン化合物およびその使用
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 (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8714767D0 (en) *	1987-06-24	1987-07-29	Erba Farmitalia	Egoline derivatives
EP0160842B1 (fr) *	1984-04-09	1994-06-22	Schering Aktiengesellschaft	Dérivés d'ergoline substitués sur la position 2, procédés pour leur préparation et leur utilisation comme médicaments
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
EP2793580A4 (fr) *	2011-12-19	2015-05-20	Map Pharmaceuticals Inc	Nouveaux dérivés d'iso-ergoline

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1517971A (en) *	1974-07-19	1978-07-19	Sandoz Ltd	8alpha-substituted ergoline i derivatives
CH615929A5 (en) *	1975-06-02	1980-02-29	Sandoz Ag	Process for the preparation of novel ergoline compounds
HU197569B (en) *	1984-01-12	1989-04-28	Sandoz Ag	Process for producing 8alpha-acylaminoergoline derivatives and pharmaceuticals comprising such compounds

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 AU AU67914/87A patent/AU6791487A/en not_active Abandoned
- 1987-01-22 DK DK035787A patent/DK35787A/da not_active Application Discontinuation
- 1987-01-22 IL IL81355A patent/IL81355A0/xx unknown
- 1987-01-22 KR KR870000556A patent/KR870007175A/ko not_active Ceased
- 1987-01-22 ES ES8700163A patent/ES2003774A6/es not_active Expired
- 1987-01-22 PT PT84184A patent/PT84184A/pt unknown
- 1987-01-22 GR GR870093A patent/GR870093B/el unknown
- 1987-01-22 FR FR8700834A patent/FR2595699A1/fr active Pending
- 1987-01-22 IT IT8747551A patent/IT1216783B/it active
- 1987-01-22 SE SE8700250A patent/SE8700250L/xx not_active Application Discontinuation
- 1987-01-22 LU LU86743A patent/LU86743A1/fr unknown
- 1987-01-23 JP JP62015028A patent/JPS62190184A/ja active Pending
- 1987-01-23 ZA ZA87520A patent/ZA87520B/xx unknown
- 1987-01-23 BE BE8700046A patent/BE1000039A4/fr not_active IP Right Cessation
- 1987-01-23 FI FI870293A patent/FI870293A7/fi not_active IP Right Cessation

Cited By (4)

* Cited by examiner, † Cited by third party
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
JP2018502889A (ja) *	2015-01-20	2018-02-01	エックスオーシーファーマシューティカルズインコーポレイテッドＸｏｃＰｈａｒｍａｃｅｕｔｉｃａｌｓ，Ｉｎｃ	イソエルゴリン化合物およびその使用
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
DK35787A (da)	1987-07-25
KR870007175A (ko)	1987-08-17
GB8701274D0 (en)	1987-02-25
AU6791487A (en)	1987-07-30
SE8700250L (sv)	1987-07-25
DK35787D0 (da)	1987-01-22
HUT45248A (en)	1988-06-28
FI870293A0 (fi)	1987-01-23
PT84184A (pt)	1987-02-01
SE8700250D0 (sv)	1987-01-22
IL81355A0 (en)	1987-08-31
FI870293A7 (fi)	1987-07-25
FR2595699A1 (fr)	1987-09-18
BE1000039A4 (fr)	1987-12-15
ZA87520B (en)	1988-09-28
GR870093B (en)	1987-05-25
NL8700046A (nl)	1987-08-17
LU86743A1 (fr)	1987-09-03
IT8747551A0 (it)	1987-01-22
ES2003774A6 (es)	1988-11-16
GB2185743A (en)	1987-07-29
IT1216783B (it)	1990-03-14

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EP1399423B1 (fr)	2007-11-14	Amides d'acide anthranilique comportant une chaine laterale heteroarylsulfonyle, procede de fabrication, utilisation en tant qu'agent pharmaceutique ou diagnostique, et preparations pharmaceutiques contenant ces amides
JPS62230722A (ja)	1987-10-09	肥満および／または関連状態の治療剤
CA2107223C (fr)	2005-02-15	Chlorhydrate de tiagabine monohydrate cristallin, sa preparation et son utilisation
PT87788B (pt)	1992-10-30	Processo para a preparacao de derivados do 2,2-dimetil-3-cromanol que tem actividade anti-hipertensiva e anti-arritmica
US5426106A (en)	1995-06-20	Pyrrolo-pyridazinone derivatives
JPS5822119B2 (ja)	1983-05-06	ジチオ−ル誘導体
JPS62294674A (ja)	1987-12-22	１，４−二置換ピペラジン誘導体、これを含む薬用組成物並びにその製造方法
JPS636058B2 (fr)	1988-02-08
JPS62190184A (ja)	1987-08-20	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
JPH0625091B2 (ja)	1994-04-06	ジヒドロジベンゾシクロヘプチリデン―エチルアミン誘導体その製法ならびに医薬組成物
KR840001552B1 (ko)	1984-10-05	시클로헥센 유도체의 제조방법
JPS63290868A (ja)	1988-11-28	ジケトピペラジン誘導体およびその塩類
JPS5846089A (ja)	1983-03-17	ヘテロ環状化合物
CA2022732A1 (fr)	1991-02-08	Derives d'oxazolo pyridines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
AU2014361794A1 (en)	2016-06-16	Solid forms of an alpha, omega di-substituted dihydroxy cyclopentyl compound and methods for the preparation and use thereof
JPH06504541A (ja)	1994-05-26	４−アミノ−３−アシルキノリン誘導体の塩およびその胃酸分泌抑制剤としての使用
JP3042915B2 (ja)	2000-05-22	３−（１ｈ−インダゾール−３−イル）−４−ピリジンアミンおよびその製造法
JPS61158980A (ja)	1986-07-18	８α‐アシルアミノエルゴリン類、その製法および医薬組成物
JPH07503002A (ja)	1995-03-30	Ｎｍｄａアンタゴニストとしてのニトロキノロン誘導体
US3391136A (en)	1968-07-02	3-chloro-11-(upsilan-dimethylaminopropylidene)-5, 6-dihydromorphanthridine and derivatives
US4307091A (en)	1981-12-22	Process for treatment of allergic conditions with benzoxazinediones
JPS58188876A (ja)	1983-11-04	抗炎症剤及び抗喘息剤
EP0003286B1 (fr)	1982-03-24	Dérivés d'alcaloides ergopeptidiques, procédé pour leur préparation et compositions pharmaceutiques les contenant
JPH0352875A (ja)	1991-03-07	４，５，６，７，―四置換ベンゾオキサゾロン類
JP3182685B2 (ja)	2001-07-03	水和物結晶及びその製造方法

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

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Links

Classifications

Landscapes

Applications Claiming Priority (2)

Publications (1)

Family

ID=6292510

Family Applications (1)

Country Status (18)

Cited By (4)

Families Citing this family (5)

Family Cites Families (3)

Cited By (4)

Also Published As

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