CA1100136A - 4a-aryl octahydro-1h-2-pyrindines - Google Patents

4a-aryl octahydro-1h-2-pyrindines

Info

Publication number: CA1100136A
Authority: CA; Canada
Prior art keywords: octahydro; pyrindine; hydroxyphenyl; phenyl; compound
Prior art date: 1976-11-02
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA289,687A

Other languages

English (en)

French (fr)

Inventor

Dennis M. Zimmerman

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.)

Eli Lilly and Co

Original Assignee

Eli Lilly and 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.)

1976-11-02

Filing date

1977-10-27

Publication date

1981-04-28

1977-10-27 Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co

1980-11-17 Priority to CA000364856A priority Critical patent/CA1119175A/en

1981-04-28 Application granted granted Critical

1981-04-28 Publication of CA1100136A publication Critical patent/CA1100136A/en

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims abstract description 68
239000003795 chemical substances by application Substances 0.000 claims abstract description 13
239000002168 alkylating agent Substances 0.000 claims abstract description 12
229940100198 alkylating agent Drugs 0.000 claims abstract description 12
238000004519 manufacturing process Methods 0.000 claims abstract description 8
-1 lithium aluminum hydride Chemical compound 0.000 claims description 65
238000000034 method Methods 0.000 claims description 49
239000002253 acid Substances 0.000 claims description 29
150000003839 salts Chemical class 0.000 claims description 26
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 25
229910052739 hydrogen Inorganic materials 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
239000012280 lithium aluminium hydride Substances 0.000 claims description 13
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 11
125000003342 alkenyl group Chemical group 0.000 claims description 11
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
229960000583 acetic acid Drugs 0.000 claims description 10
150000002431 hydrogen Chemical class 0.000 claims description 10
231100000252 nontoxic Toxicity 0.000 claims description 6
230000003000 nontoxic effect Effects 0.000 claims description 6
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
NNTYFRJCGLTEMW-UHFFFAOYSA-N 4a-(3-methoxyphenyl)-1,2,3,4,5,6,7,7a-octahydrocyclopenta[c]pyridine Chemical compound COC1=CC=CC(C23C(CCC2)CNCC3)=C1 NNTYFRJCGLTEMW-UHFFFAOYSA-N 0.000 claims description 5
125000002541 furyl group Chemical group 0.000 claims description 5
239000012362 glacial acetic acid Substances 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
UHMCIKFAUSFZLW-UHFFFAOYSA-N 3-(1,2,3,4,5,6,7,7a-octahydrocyclopenta[c]pyridin-4a-yl)phenol Chemical compound OC1=CC=CC(C23C(CCC2)CNCC3)=C1 UHMCIKFAUSFZLW-UHFFFAOYSA-N 0.000 claims description 4
HTEVNWBCKRJEST-UHFFFAOYSA-N 4a-(3-methoxyphenyl)-2-pentyl-3,4,5,6,7,7a-hexahydro-1h-cyclopenta[c]pyridine Chemical compound C1CCC2CN(CCCCC)CCC21C1=CC=CC(OC)=C1 HTEVNWBCKRJEST-UHFFFAOYSA-N 0.000 claims description 4
HFEHLDPGIKPNKL-UHFFFAOYSA-N allyl iodide Chemical compound ICC=C HFEHLDPGIKPNKL-UHFFFAOYSA-N 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 claims description 3
WHHZDVZHTFWSRD-UHFFFAOYSA-N 3-[2-(cyclopropylmethyl)-3,4,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyridin-4a-yl]phenol Chemical compound OC=1C=C(C=CC1)C12CCN(CC2CCC1)CC1CC1 WHHZDVZHTFWSRD-UHFFFAOYSA-N 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
VOHILFSOWRNVJJ-UHFFFAOYSA-N 2-(bromomethyl)oxolane Chemical compound BrCC1CCCO1 VOHILFSOWRNVJJ-UHFFFAOYSA-N 0.000 claims description 2
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 claims description 2
239000000126 substance Substances 0.000 claims 13
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 6
230000002152 alkylating effect Effects 0.000 claims 4
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 3
VUKNOJLWFRGGOF-UHFFFAOYSA-N 4a-(3-methoxyphenyl)-2-propyl-3,4,5,6,7,7a-hexahydro-1h-cyclopenta[c]pyridine Chemical compound C1CCC2CN(CCC)CCC21C1=CC=CC(OC)=C1 VUKNOJLWFRGGOF-UHFFFAOYSA-N 0.000 claims 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
XNFIZOUXSFKBHL-UHFFFAOYSA-N 3-(2-pentyl-3,4,5,6,7,7a-hexahydro-1h-cyclopenta[c]pyridin-4a-yl)phenol Chemical compound C1CCC2CN(CCCCC)CCC21C1=CC=CC(O)=C1 XNFIZOUXSFKBHL-UHFFFAOYSA-N 0.000 claims 2
QOZKQIRLIRKQIE-UHFFFAOYSA-N 3-(2-prop-2-enyl-3,4,5,6,7,7a-hexahydro-1h-cyclopenta[c]pyridin-4a-yl)phenol Chemical compound OC1=CC=CC(C23C(CCC2)CN(CC=C)CC3)=C1 QOZKQIRLIRKQIE-UHFFFAOYSA-N 0.000 claims 2
UTOZTQIBZHHHNJ-UHFFFAOYSA-N 3-(2-propyl-3,4,5,6,7,7a-hexahydro-1h-cyclopenta[c]pyridin-4a-yl)phenol Chemical compound C1CCC2CN(CCC)CCC21C1=CC=CC(O)=C1 UTOZTQIBZHHHNJ-UHFFFAOYSA-N 0.000 claims 2
YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 claims 1
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims 1
239000000730 antalgic agent Substances 0.000 abstract description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 95
239000000243 solution Substances 0.000 description 58
239000011541 reaction mixture Substances 0.000 description 47
FGFBEHFJSQBISW-UHFFFAOYSA-N 1h-cyclopenta[b]pyridine Chemical class C1=CNC2=CC=CC2=C1 FGFBEHFJSQBISW-UHFFFAOYSA-N 0.000 description 46
238000006243 chemical reaction Methods 0.000 description 44
239000002904 solvent Substances 0.000 description 35
239000003921 oil Substances 0.000 description 34
235000019198 oils Nutrition 0.000 description 34
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
239000000047 product Substances 0.000 description 31
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
238000004458 analytical method Methods 0.000 description 24
238000001704 evaporation Methods 0.000 description 23
230000008020 evaporation Effects 0.000 description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
238000010992 reflux Methods 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
230000000694 effects Effects 0.000 description 12
239000000284 extract Substances 0.000 description 12
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 11
239000002585 base Substances 0.000 description 11
229910000042 hydrogen bromide Inorganic materials 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
230000000202 analgesic effect Effects 0.000 description 10
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
239000007787 solid Substances 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
235000011121 sodium hydroxide Nutrition 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
125000000217 alkyl group Chemical group 0.000 description 8
238000003556 assay Methods 0.000 description 8
239000003638 chemical reducing agent Substances 0.000 description 8
230000005764 inhibitory process Effects 0.000 description 8
150000004880 oxines Chemical class 0.000 description 8
150000001412 amines Chemical class 0.000 description 7
239000000543 intermediate Substances 0.000 description 7
239000010410 layer Substances 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
150000003141 primary amines Chemical class 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
IVAATAQAFOAALG-UHFFFAOYSA-N 2h-cyclopenta[c]pyridine Chemical class C1=CNC=C2C=CC=C21 IVAATAQAFOAALG-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
229940035676 analgesics Drugs 0.000 description 6
238000001816 cooling Methods 0.000 description 6
MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 5
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
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 5
241000124008 Mammalia Species 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
125000003545 alkoxy group Chemical group 0.000 description 5
238000005804 alkylation reaction Methods 0.000 description 5
230000036592 analgesia Effects 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000007789 gas Substances 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
150000002500 ions Chemical class 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
229940093956 potassium carbonate Drugs 0.000 description 5
235000011181 potassium carbonates Nutrition 0.000 description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
229960001407 sodium bicarbonate Drugs 0.000 description 5
239000007858 starting material Substances 0.000 description 5
238000007920 subcutaneous administration Methods 0.000 description 5
PGJZFAPVZDXDNA-UHFFFAOYSA-N 4a-phenyl-1,2,3,4,5,6,7,7a-octahydrocyclopenta[c]pyridine Chemical compound C1CCC2CNCCC21C1=CC=CC=C1 PGJZFAPVZDXDNA-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
230000010933 acylation Effects 0.000 description 4
238000005917 acylation reaction Methods 0.000 description 4
239000005557 antagonist Substances 0.000 description 4
230000036461 convulsion Effects 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
238000004821 distillation Methods 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000003814 drug Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
238000012360 testing method Methods 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
KPXSPHQLZBMRLW-UHFFFAOYSA-N 2,3,4,4a,5,6,7,7a-octahydro-1h-cyclopenta[c]pyridine Chemical class C1CNCC2CCCC21 KPXSPHQLZBMRLW-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
241000699666 Mus <mouse, genus> Species 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
239000012346 acetyl chloride Substances 0.000 description 3
230000029936 alkylation Effects 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
239000007810 chemical reaction solvent Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000010779 crude oil Substances 0.000 description 3
238000006264 debenzylation reaction Methods 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 3
239000012458 free base Substances 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
UZHSEJADLWPNLE-GRGSLBFTSA-N naloxone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4CC=C UZHSEJADLWPNLE-GRGSLBFTSA-N 0.000 description 3
229960004127 naloxone Drugs 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000000725 suspension Substances 0.000 description 3
FRVZWIGAQXKWER-UHFFFAOYSA-N 2-benzyl-4a-(3-methoxyphenyl)-5,6,7,7a-tetrahydro-4h-cyclopenta[c]pyridine-1,3-dione Chemical compound COC1=CC=CC(C23C(CCC2)C(=O)N(CC=2C=CC=CC=2)C(=O)C3)=C1 FRVZWIGAQXKWER-UHFFFAOYSA-N 0.000 description 2
DTGIQJKGEJIAAL-UHFFFAOYSA-N 2-ethyl-4a-phenyl-3,4,5,6,7,7a-hexahydro-1h-cyclopenta[c]pyridine Chemical compound C1CCC2CN(CC)CCC21C1=CC=CC=C1 DTGIQJKGEJIAAL-UHFFFAOYSA-N 0.000 description 2
BPPPUFSZQDCMEE-UHFFFAOYSA-N 2-oxocyclohexane-1-carbaldehyde Chemical class O=CC1CCCCC1=O BPPPUFSZQDCMEE-UHFFFAOYSA-N 0.000 description 2
DRLVMOAWNVOSPE-UHFFFAOYSA-N 2-phenylcyclohexan-1-one Chemical compound O=C1CCCCC1C1=CC=CC=C1 DRLVMOAWNVOSPE-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
LPMQLTPCZIWTLF-UHFFFAOYSA-N 3-[2-(2-phenylethyl)-3,4,5,6,7,7a-hexahydro-1h-cyclopenta[c]pyridin-4a-yl]phenol Chemical compound OC1=CC=CC(C23C(CCC2)CN(CCC=2C=CC=CC=2)CC3)=C1 LPMQLTPCZIWTLF-UHFFFAOYSA-N 0.000 description 2
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 2
DAUWHPNJBHKVJK-UHFFFAOYSA-N 4a-(3-methoxyphenyl)-2-methyl-3,4,5,6,7,7a-hexahydro-1h-cyclopenta[c]pyridine Chemical compound COC1=CC=CC(C23C(CCC2)CN(C)CC3)=C1 DAUWHPNJBHKVJK-UHFFFAOYSA-N 0.000 description 2
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
206010012335 Dependence Diseases 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
239000000556 agonist Substances 0.000 description 2
239000012670 alkaline solution Substances 0.000 description 2
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
NGPGDYLVALNKEG-UHFFFAOYSA-N azanium;azane;2,3,4-trihydroxy-4-oxobutanoate Chemical compound [NH4+].[NH4+].[O-]C(=O)C(O)C(O)C([O-])=O NGPGDYLVALNKEG-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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235000010724 Wisteria floribunda Nutrition 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
230000007815 allergy Effects 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
AQIHMSVIAGNIDM-UHFFFAOYSA-N benzoyl bromide Chemical compound BrC(=O)C1=CC=CC=C1 AQIHMSVIAGNIDM-UHFFFAOYSA-N 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
CHIWXYAWZYPFJS-UHFFFAOYSA-N bromomethoxybenzene Chemical compound BrCOC1=CC=CC=C1 CHIWXYAWZYPFJS-UHFFFAOYSA-N 0.000 description 1
125000003865 brosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)S(*)(=O)=O 0.000 description 1
KKBWAGPOKIAPAW-UHFFFAOYSA-N butoxyalumane Chemical compound CCCCO[AlH2] KKBWAGPOKIAPAW-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229960001948 caffeine Drugs 0.000 description 1
VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
ZVTQWXCKQTUVPY-UHFFFAOYSA-N chloromethylcyclopropane Chemical compound ClCC1CC1 ZVTQWXCKQTUVPY-UHFFFAOYSA-N 0.000 description 1
WTEVQBCEXWBHNA-JXMROGBWSA-N citral A Natural products CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
239000000470 constituent Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
AVLJDNPAYGPMMJ-UHFFFAOYSA-N cyclobutanecarbonyl bromide Chemical compound BrC(=O)C1CCC1 AVLJDNPAYGPMMJ-UHFFFAOYSA-N 0.000 description 1
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
IABZFPLSDXDLRS-UHFFFAOYSA-N cyclohexylmethyl methanesulfonate Chemical compound CS(=O)(=O)OCC1CCCCC1 IABZFPLSDXDLRS-UHFFFAOYSA-N 0.000 description 1
CGFCQGODEOUVFT-UHFFFAOYSA-N cyclopenta[b]pyran-2,3-dione Chemical class O=C1C(=O)OC2=CC=CC2=C1 CGFCQGODEOUVFT-UHFFFAOYSA-N 0.000 description 1
QFWIZBDAWJSJOT-UHFFFAOYSA-N cyclopenta[c]pyridine-1,3-dione Chemical compound O=C1NC(C=C2C=CC=C12)=O QFWIZBDAWJSJOT-UHFFFAOYSA-N 0.000 description 1
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)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
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 description 1
229960004193 dextropropoxyphene Drugs 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
ZEUNFSXJLTXSBS-UHFFFAOYSA-N ethyl 2-[1-(3-hydroxyphenyl)-2-oxocyclohexyl]acetate Chemical compound C=1C=CC(O)=CC=1C1(CC(=O)OCC)CCCCC1=O ZEUNFSXJLTXSBS-UHFFFAOYSA-N 0.000 description 1
XIAYIHJKGNBZON-UHFFFAOYSA-N ethyl 2-[1-(3-methoxyphenyl)-2-oxocyclohexyl]acetate Chemical compound C=1C=CC(OC)=CC=1C1(CC(=O)OCC)CCCCC1=O XIAYIHJKGNBZON-UHFFFAOYSA-N 0.000 description 1
NBGQWTYYPGXUBM-UHFFFAOYSA-N ethyl 2-[3-formyl-1-(3-methoxyphenyl)-2-oxocyclohexyl]acetate Chemical compound C=1C=CC(OC)=CC=1C1(CC(=O)OCC)CCCC(C=O)C1=O NBGQWTYYPGXUBM-UHFFFAOYSA-N 0.000 description 1
IMMGIMKNXZXXLY-UHFFFAOYSA-N ethyl 3-diazo-6-methyl-2-oxo-1-phenylcyclohexane-1-carboxylate Chemical compound C1(=CC=CC=C1)C1(C(C(CCC1C)=[N+]=[N-])=O)C(=O)OCC IMMGIMKNXZXXLY-UHFFFAOYSA-N 0.000 description 1
VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
GFAUNYMRSKVDJL-UHFFFAOYSA-N formyl chloride Chemical compound ClC=O GFAUNYMRSKVDJL-UHFFFAOYSA-N 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
PIXBVQFCTGBRHV-UHFFFAOYSA-N hex-4-enoyl chloride Chemical compound CC=CCCC(Cl)=O PIXBVQFCTGBRHV-UHFFFAOYSA-N 0.000 description 1
PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000043 hydrogen iodide Inorganic materials 0.000 description 1
ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
125000004464 hydroxyphenyl group Chemical group 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002537 isoquinolines Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
ANAFTYVSHCSQPP-UHFFFAOYSA-N lithium;trimethoxyalumane Chemical compound [Li].CO[Al](OC)OC ANAFTYVSHCSQPP-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
BWLHABBEJLLEBV-UHFFFAOYSA-N methyl 2-(2-ethoxy-2-oxoethyl)-2-(3-methoxyphenyl)cyclopentane-1-carboxylate Chemical compound C=1C=CC(OC)=CC=1C1(CC(=O)OCC)CCCC1C(=O)OC BWLHABBEJLLEBV-UHFFFAOYSA-N 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
239000002687 nonaqueous vehicle Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
229940127240 opiate Drugs 0.000 description 1
230000000945 opiatelike Effects 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
230000008058 pain sensation Effects 0.000 description 1
229960005489 paracetamol Drugs 0.000 description 1
XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000002831 pharmacologic agent Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229960003975 potassium Drugs 0.000 description 1
235000007686 potassium Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000007157 ring contraction reaction Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
229940083608 sodium hydroxide Drugs 0.000 description 1
239000012265 solid product Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
NDLIRBZKZSDGSO-UHFFFAOYSA-N tosyl azide Chemical compound CC1=CC=C(S(=O)(=O)[N-][N+]#N)C=C1 NDLIRBZKZSDGSO-UHFFFAOYSA-N 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
229940086542 triethylamine Drugs 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/757—Unsaturated compounds containing a keto groups being part of a ring containing —CHO groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pain & Pain Management (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Rheumatology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Indole Compounds (AREA)

CA289,687A 1976-11-02 1977-10-27 4a-aryl octahydro-1h-2-pyrindines Expired CA1100136A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000364856A CA1119175A (en)	1976-11-02	1980-11-17	4a-aryl octahydro-1h-2-pyrindines

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US73795876A	1976-11-02	1976-11-02
US737,958		1976-11-02

Publications (1)

Publication Number	Publication Date
CA1100136A true CA1100136A (en)	1981-04-28

Family

ID=24965981

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA289,687A Expired CA1100136A (en)	1976-11-02	1977-10-27	4a-aryl octahydro-1h-2-pyrindines

Country Status (26)

Country	Link
JP (1)	JPS5356669A (cs)
AR (1)	AR223454A1 (cs)
AT (1)	ATA782177A (cs)
AU (1)	AU513679B2 (cs)
BE (1)	BE860314A (cs)
CA (1)	CA1100136A (cs)
CS (1)	CS211380B2 (cs)
DD (1)	DD133795A5 (cs)
DE (1)	DE2748466A1 (cs)
DK (1)	DK485277A (cs)
ES (3)	ES463783A1 (cs)
FR (1)	FR2369267A1 (cs)
GB (1)	GB1590155A (cs)
GR (1)	GR70053B (cs)
HU (1)	HU176231B (cs)
IE (1)	IE45901B1 (cs)
IL (1)	IL53236A0 (cs)
NL (1)	NL7712053A (cs)
NZ (1)	NZ185539A (cs)
PH (1)	PH12590A (cs)
PL (3)	PL108466B1 (cs)
PT (1)	PT67194B (cs)
RO (3)	RO72900A (cs)
SE (3)	SE7712218L (cs)
SU (3)	SU812174A3 (cs)
ZA (1)	ZA776497B (cs)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PT68934A (en) *	1977-12-27	1979-01-01	Lilly Co Eli	Process for preparing 4a-aryl-octahydro-1h-2-pyrindines
US4277608A (en) *	1979-06-21	1981-07-07	Eli Lilly And Company	Method of preparing 4a-arylhexahydro-1H-2-pyrindines and 4a-aryloctahydroisoquinolines
US4236009A (en) *	1979-06-21	1980-11-25	Eli Lilly And Company	Method of preparing 4A-arylhexahydro-1H-2-pyrindines and 4A-aryloctahydroisoquinolines
ZA9510829B (en) *	1994-12-23	1996-07-03	Smithkline Beecham Corp	3,3-(disubstituted)cyclohexan-1-one monomers and related compounds
US8598164B2 (en)	2010-05-06	2013-12-03	Vertex Pharmaceuticals Incorporated	Heterocyclic chromene-spirocyclic piperidine amides as modulators of ion channels
KR101923367B1 (ko)	2011-02-02	2018-12-04	버텍스 파마슈티칼스 인코포레이티드	이온 채널의 조절제로서의 피롤로피라진―스피로사이클릭 피페리딘 아미드
WO2012112743A1 (en)	2011-02-18	2012-08-23	Vertex Pharmaceuticals Incorporated	Chroman - spirocyclic piperidine amides as modulators of ion channels
US8828996B2 (en)	2011-03-14	2014-09-09	Vertex Pharmaceuticals Incorporated	Morpholine-spirocyclic piperidine amides as modulators of ion channels

1977
- 1977-10-26 PT PT67194A patent/PT67194B/pt unknown
- 1977-10-27 GB GB44729/77A patent/GB1590155A/en not_active Expired
- 1977-10-27 NZ NZ185539A patent/NZ185539A/xx unknown
- 1977-10-27 CA CA289,687A patent/CA1100136A/en not_active Expired
- 1977-10-27 IL IL53236A patent/IL53236A0/xx unknown
- 1977-10-28 IE IE2206/77A patent/IE45901B1/en unknown
- 1977-10-28 BE BE1008483A patent/BE860314A/xx unknown
- 1977-10-28 SE SE7712218A patent/SE7712218L/xx unknown
- 1977-10-28 PH PH20380A patent/PH12590A/en unknown
- 1977-10-28 DE DE19772748466 patent/DE2748466A1/de not_active Withdrawn
- 1977-10-28 FR FR7732776A patent/FR2369267A1/fr active Granted
- 1977-10-29 GR GR54664A patent/GR70053B/el unknown
- 1977-10-31 AR AR269797A patent/AR223454A1/es active
- 1977-11-01 ZA ZA00776497A patent/ZA776497B/xx unknown
- 1977-11-01 NL NL7712053A patent/NL7712053A/xx not_active Application Discontinuation
- 1977-11-01 HU HU77EI768A patent/HU176231B/hu unknown
- 1977-11-01 AU AU30235/77A patent/AU513679B2/en not_active Expired
- 1977-11-01 DK DK485277A patent/DK485277A/da unknown
- 1977-11-02 RO RO7792007A patent/RO72900A/ro unknown
- 1977-11-02 ES ES463783A patent/ES463783A1/es not_active Expired
- 1977-11-02 PL PL1977212226A patent/PL108466B1/pl unknown
- 1977-11-02 PL PL1977212225A patent/PL108610B1/pl unknown
- 1977-11-02 DD DD7700201831A patent/DD133795A5/xx unknown
- 1977-11-02 AT AT0782177A patent/ATA782177A/de not_active Application Discontinuation
- 1977-11-02 SU SU772539649A patent/SU812174A3/ru active
- 1977-11-02 ES ES463784A patent/ES463784A1/es not_active Expired
- 1977-11-02 RO RO7799434A patent/RO78300A/ro unknown
- 1977-11-02 JP JP13211177A patent/JPS5356669A/ja active Pending
- 1977-11-02 CS CS777150A patent/CS211380B2/cs unknown
- 1977-11-02 RO RO7799435A patent/RO77935A/ro unknown
- 1977-11-02 PL PL1977201885A patent/PL109690B1/pl unknown
1978
- 1978-08-01 ES ES472276A patent/ES472276A1/es not_active Expired
- 1978-10-03 SU SU782669355A patent/SU913941A3/ru active
- 1978-10-03 SU SU782669395A patent/SU845777A3/ru active
1981
- 1981-05-18 SE SE8103106A patent/SE8103106L/sv unknown
- 1981-05-18 SE SE8103107A patent/SE8103107L/sv unknown

Also Published As

Publication number	Publication date
ZA776497B (en)	1979-06-27
PL109690B1 (en)	1980-06-30
RO72900A (ro)	1981-11-04
SE7712218L (sv)	1978-05-03
AR223454A1 (es)	1981-08-31
DD133795A5 (de)	1979-01-24
PT67194B (en)	1979-03-23
PH12590A (en)	1979-06-27
SE8103107L (sv)	1981-05-18
GR70053B (cs)	1982-07-26
GB1590155A (en)	1981-05-28
PL108466B1 (en)	1980-04-30
JPS5356669A (en)	1978-05-23
FR2369267B1 (cs)	1980-05-16
IE45901B1 (en)	1982-12-29
SU913941A3 (en)	1982-03-15
ES463784A1 (es)	1978-06-16
NL7712053A (nl)	1978-05-05
ES472276A1 (es)	1979-10-01
SE8103106L (sv)	1981-05-18
ES463783A1 (es)	1979-07-16
PL201885A1 (pl)	1978-12-04
SU845777A3 (ru)	1981-07-07
SU812174A3 (ru)	1981-03-07
PT67194A (en)	1977-11-01
AU513679B2 (en)	1980-12-18
HU176231B (en)	1981-01-28
RO78300A (ro)	1982-04-12
IE45901L (en)	1978-05-02
CS211380B2 (en)	1982-02-26
DK485277A (da)	1978-05-03
IL53236A0 (en)	1977-12-30
PL108610B1 (en)	1980-04-30
ATA782177A (de)	1981-10-15
DE2748466A1 (de)	1978-05-03
FR2369267A1 (fr)	1978-05-26
AU3023577A (en)	1979-05-10
BE860314A (fr)	1978-04-28
NZ185539A (en)	1979-12-11
RO77935A (ro)	1981-12-25

Legal Events

Date	Code	Title	Description
1998-04-28	MKEX	Expiry

Publication	Publication Date	Title
US4337341A (en)	1982-06-29	4a-Aryl-octahydro-1H-2-pyrindines
JPS6350354B2 (cs)	1988-10-07
US4374139A (en)	1983-02-15	Levorotatory N-substituted acylmorphinans useful as analgesic agents
CA1161047A (en)	1984-01-24	Process for preparing 2(3h)-indolones
JPS5989625A (ja)	1984-05-23	芳香族置換環状アミジン止瀉剤
JPS6012350B2 (ja)	1985-04-01	新規アリ−ルピペリジン誘導体の製造方法
US4001248A (en)	1977-01-04	N-cycloalkylmethyl decahydroisoquinolines
US2820817A (en)	1958-01-21	Oxygenated indan compounds and method of making the same
US4001247A (en)	1977-01-04	1-ethyl 3a-(substituted-phenyl) decahydroisoquinoline
CA1105026A (en)	1981-07-14	4a-aryl-octahydro-1h-2-pyrindines
GB1590155A (en)	1981-05-28	Cis-4a-phenyl-2,3,4,4a,5,6,7,7a-octahydro-1h-2-pyrindines and pharmaceutical compositions containing them
GB1594687A (en)	1981-08-05	2-aminotetralin derivatives and processes for producing the same
CA1148150A (en)	1983-06-14	Phenylmorphans, intermediates and method of preparation
US3914232A (en)	1975-10-21	2-And 4-acryloxy-N-substituted-morphinan derivatives
US4194044A (en)	1980-03-18	Process for preparing 3-phenoxy morphinans
US4247697A (en)	1981-01-27	3-Phenoxy morphinans and their derivatives
US4029796A (en)	1977-06-14	Novel N-cycloalkylmethyl decahydroisoquinolines for producing opiate-like analgesia
Elslager et al.	1964	Synthetic Schistosomicides. VI. 4-Substituted 1-(Dialkylaminoalkylamino) naphthalenes1
US4906640A (en)	1990-03-06	3-sulfonyl-3,7-diazabicyclo[3,3,1]nonane compounds and medicaments containing said compounds
US4278797A (en)	1981-07-14	Intermediates to phenylmorphans and method of preparation thereof
CA1119175A (en)	1982-03-02	4a-aryl octahydro-1h-2-pyrindines
US3965104A (en)	1976-06-22	1-(Substituted-aminoalkyl)-3-benzoyl-4-hydroxy-4-phenylpiperidines and related compounds
US4219652A (en)	1980-08-26	N-Methyl and N-phenethyl-cis-decahydroisoquinolines
CA1094554A (en)	1981-01-27	Decahydrocyclopent(c)azepines
US4996223A (en)	1991-02-26	New organic compounds having opioid properties