CA1046519A - Derives tricycliques de l'acide acetique et de l'indole - Google Patents

Derives tricycliques de l'acide acetique et de l'indole

Info

Publication number: CA1046519A
Authority: CA; Canada
Prior art keywords: formula; hydrogen; compound; ethyl; methyl
Prior art date: 1975-08-28
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

CA234,428A

Other languages

English (en)

Other versions

CA234428S (en

Inventor

Andre A. Asselin

Leslie G. Humber

Thomas A. Dobson

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.)

Wyeth LLC

Original Assignee

American Home Products Corp

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.)

1975-08-28

Filing date

1975-08-28

Publication date

1979-01-16

1975-08-28 Application filed by American Home Products Corp filed Critical American Home Products Corp

1975-08-28 Priority to CA234,428A priority Critical patent/CA1046519A/fr

1979-01-16 Application granted granted Critical

1979-01-16 Publication of CA1046519A publication Critical patent/CA1046519A/fr

Status Expired legal-status Critical Current

Links

150000001242 acetic acid derivatives Chemical class 0.000 title abstract description 5
150000001875 compounds Chemical class 0.000 claims abstract description 144
238000000034 method Methods 0.000 claims abstract description 77
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 73
239000001257 hydrogen Substances 0.000 claims abstract description 66
125000000217 alkyl group Chemical group 0.000 claims abstract description 45
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 30
150000002431 hydrogen Chemical group 0.000 claims abstract description 20
125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 5
125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 4
125000001475 halogen functional group Chemical group 0.000 claims abstract 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 68
-1 lower alkanoloxy Chemical group 0.000 claims description 44
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 40
230000008569 process Effects 0.000 claims description 40
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 30
230000007062 hydrolysis Effects 0.000 claims description 17
238000006460 hydrolysis reaction Methods 0.000 claims description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
150000007857 hydrazones Chemical class 0.000 claims description 14
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
239000003795 chemical substances by application Substances 0.000 claims description 9
150000001350 alkyl halides Chemical class 0.000 claims description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
238000007126 N-alkylation reaction Methods 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
239000000126 substance Substances 0.000 claims 18
ZZTDHTOLLTVHQT-UHFFFAOYSA-N 2-(1,8-diethyl-2,3,4,9-tetrahydrocarbazol-1-yl)acetic acid Chemical compound C1CCC(CC)(CC(O)=O)C2=C1C(C=CC=C1CC)=C1N2 ZZTDHTOLLTVHQT-UHFFFAOYSA-N 0.000 claims 1
DZEJINUDHGEWIN-UHFFFAOYSA-N 2-(1-ethyl-8-propan-2-yl-2,3,4,9-tetrahydrocarbazol-1-yl)acetic acid Chemical compound N1C2=C(C(C)C)C=CC=C2C2=C1C(CC)(CC(O)=O)CCC2 DZEJINUDHGEWIN-UHFFFAOYSA-N 0.000 claims 1
DKTCYIDKDZDTPN-UHFFFAOYSA-N 2-(1-ethyl-8-propyl-2,3,4,9-tetrahydrocarbazol-1-yl)acetic acid Chemical compound C1CCC(CC)(CC(O)=O)C2=C1C(C=CC=C1CCC)=C1N2 DKTCYIDKDZDTPN-UHFFFAOYSA-N 0.000 claims 1
CGBBRVWMBAVALP-UHFFFAOYSA-N 2-(1-ethyl-9-methyl-3,4-dihydro-2h-carbazol-1-yl)acetic acid Chemical compound CN1C2=CC=CC=C2C2=C1C(CC)(CC(O)=O)CCC2 CGBBRVWMBAVALP-UHFFFAOYSA-N 0.000 claims 1
UITHSNZKHRVQDS-UHFFFAOYSA-N 2-(3-ethyl-2,4-dihydro-1h-cyclopenta[b]indol-3-yl)acetic acid Chemical compound N1C2=CC=CC=C2C2=C1C(CC)(CC(O)=O)CC2 UITHSNZKHRVQDS-UHFFFAOYSA-N 0.000 claims 1
IMAFBVDIUUHCMM-UHFFFAOYSA-N 2-(3-methyl-2,4-dihydro-1h-cyclopenta[b]indol-3-yl)acetic acid Chemical compound N1C2=CC=CC=C2C2=C1C(C)(CC(O)=O)CC2 IMAFBVDIUUHCMM-UHFFFAOYSA-N 0.000 claims 1
BMALOJUMBGLBAS-UHFFFAOYSA-N 2-(4,6-diethyl-7,8,9,10-tetrahydro-5h-cyclohepta[b]indol-6-yl)acetic acid Chemical compound C1CCCC(CC)(CC(O)=O)C2=C1C(C=CC=C1CC)=C1N2 BMALOJUMBGLBAS-UHFFFAOYSA-N 0.000 claims 1
ZTAXRTWETMMJLQ-UHFFFAOYSA-N 2-(5-ethyl-3-methyl-2,4-dihydro-1h-cyclopenta[b]indol-3-yl)acetic acid Chemical compound CCC1=CC=CC2=C1NC1=C2CCC1(CC(O)=O)C ZTAXRTWETMMJLQ-UHFFFAOYSA-N 0.000 claims 1
KNFUAZBGHIRXSP-UHFFFAOYSA-N 2-(6-methyl-7,8,9,10-tetrahydro-5h-cyclohepta[b]indol-6-yl)acetic acid Chemical compound OC(=O)CC1(C)CCCCC2=C1NC1=CC=CC=C21 KNFUAZBGHIRXSP-UHFFFAOYSA-N 0.000 claims 1
OPHHHVHTXIVTGW-UHFFFAOYSA-N 2-(8-butyl-1-ethyl-2,3,4,9-tetrahydrocarbazol-1-yl)acetic acid Chemical compound C1CCC(CC)(CC(O)=O)C2=C1C(C=CC=C1CCCC)=C1N2 OPHHHVHTXIVTGW-UHFFFAOYSA-N 0.000 claims 1
MVDQDXRXRUJHMG-UHFFFAOYSA-N 2-(9-ethyl-1-methyl-3,4-dihydro-2h-carbazol-1-yl)acetic acid Chemical compound C12=CC=CC=C2N(CC)C2=C1CCCC2(C)CC(O)=O MVDQDXRXRUJHMG-UHFFFAOYSA-N 0.000 claims 1
JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 claims 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 5
125000004423 acyloxy group Chemical group 0.000 abstract description 4
229910052799 carbon Inorganic materials 0.000 abstract description 4
AZZZVAUBRCDMFI-UHFFFAOYSA-N 2-(2,3,4,9-tetrahydro-1h-carbazol-1-yl)acetic acid Chemical compound N1C2=CC=CC=C2C2=C1C(CC(=O)O)CCC2 AZZZVAUBRCDMFI-UHFFFAOYSA-N 0.000 abstract description 3
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract description 3
229940121363 anti-inflammatory agent Drugs 0.000 abstract description 2
239000002260 anti-inflammatory agent Substances 0.000 abstract description 2
POZRNVCYQIMCQS-UHFFFAOYSA-N 2-(1,2,3,3a-tetrahydrocyclopenta[b]indol-3-yl)acetic acid Chemical compound C1=CC=CC2=NC3C(CC(=O)O)CCC3=C21 POZRNVCYQIMCQS-UHFFFAOYSA-N 0.000 abstract 1
UVUDAVGWAVMMSW-UHFFFAOYSA-N 2-(1,2,3,4,4a,5-hexahydrocyclohepta[b]indol-6-yl)acetic acid Chemical class C1=CC=CC(CC(=O)O)=C2NC(CCCC3)C3=C21 UVUDAVGWAVMMSW-UHFFFAOYSA-N 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 83
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 52
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
239000002253 acid Substances 0.000 description 47
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
239000000243 solution Substances 0.000 description 40
239000000203 mixture Substances 0.000 description 32
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
229910052757 nitrogen Inorganic materials 0.000 description 26
239000007858 starting material Substances 0.000 description 26
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 25
150000004702 methyl esters Chemical class 0.000 description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
238000010992 reflux Methods 0.000 description 22
239000002904 solvent Substances 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 18
238000001704 evaporation Methods 0.000 description 17
125000004494 ethyl ester group Chemical group 0.000 description 16
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
229910052943 magnesium sulfate Inorganic materials 0.000 description 15
239000003921 oil Substances 0.000 description 15
235000019198 oils Nutrition 0.000 description 15
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
239000012259 ether extract Substances 0.000 description 14
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
150000002148 esters Chemical class 0.000 description 13
230000008020 evaporation Effects 0.000 description 13
239000000047 product Substances 0.000 description 13
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
150000001412 amines Chemical class 0.000 description 12
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 11
239000012267 brine Substances 0.000 description 11
229920006395 saturated elastomer Polymers 0.000 description 11
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 10
229910052708 sodium Inorganic materials 0.000 description 10
239000011734 sodium Substances 0.000 description 10
238000012360 testing method Methods 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 9
238000001953 recrystallisation Methods 0.000 description 9
238000007363 ring formation reaction Methods 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
230000000694 effects Effects 0.000 description 7
239000010410 layer Substances 0.000 description 7
239000012312 sodium hydride Substances 0.000 description 7
229910000104 sodium hydride Inorganic materials 0.000 description 7
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 6
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000000370 acceptor Substances 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 6
125000005907 alkyl ester group Chemical group 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 6
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 6
WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 6
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Substances [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
241000700159 Rattus Species 0.000 description 5
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 5
230000003110 anti-inflammatory effect Effects 0.000 description 5
230000000144 pharmacologic effect Effects 0.000 description 5
229910052707 ruthenium Inorganic materials 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
JHPOWXCLWLEKBY-UHFFFAOYSA-N (2-ethylphenyl)hydrazine Chemical compound CCC1=CC=CC=C1NN JHPOWXCLWLEKBY-UHFFFAOYSA-N 0.000 description 4
WKYYYUWKFPFVEY-UHFFFAOYSA-N 2-ethylcyclohexan-1-one Chemical compound CCC1CCCCC1=O WKYYYUWKFPFVEY-UHFFFAOYSA-N 0.000 description 4
ZIXLDMFVRPABBX-UHFFFAOYSA-N 2-methylcyclopentan-1-one Chemical compound CC1CCCC1=O ZIXLDMFVRPABBX-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
238000001816 cooling Methods 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
238000004821 distillation Methods 0.000 description 4
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
230000009471 action Effects 0.000 description 3
230000029936 alkylation Effects 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 3
WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
230000032050 esterification Effects 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Substances Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
239000003617 indole-3-acetic acid Substances 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
230000004048 modification Effects 0.000 description 3
238000012986 modification Methods 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
229940067157 phenylhydrazine Drugs 0.000 description 3
230000009467 reduction Effects 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
MGJONKDZWRHICT-UHFFFAOYSA-N 2-(1-methyl-2,3,4,9-tetrahydrocarbazol-1-yl)acetic acid Chemical compound N1C2=CC=CC=C2C2=C1C(C)(CC(O)=O)CCC2 MGJONKDZWRHICT-UHFFFAOYSA-N 0.000 description 2
HDEDAGREICRNQD-UHFFFAOYSA-N 2-(1-methyl-2-oxocycloheptyl)acetonitrile Chemical compound N#CCC1(C)CCCCCC1=O HDEDAGREICRNQD-UHFFFAOYSA-N 0.000 description 2
UANHRLXAZYIENO-UHFFFAOYSA-N 2-(2-oxocycloheptyl)acetonitrile Chemical compound O=C1CCCCCC1CC#N UANHRLXAZYIENO-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
YKOLZVXSPGIIBJ-UHFFFAOYSA-N 2-Isopropylaniline Chemical class CC(C)C1=CC=CC=C1N YKOLZVXSPGIIBJ-UHFFFAOYSA-N 0.000 description 2
MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
LFSAPCRASZRSKS-UHFFFAOYSA-N 2-methylcyclohexan-1-one Chemical compound CC1CCCCC1=O LFSAPCRASZRSKS-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
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PSECTKHYVHZABC-UHFFFAOYSA-N methyl 2-(2,3,4,9-tetrahydro-1h-carbazol-1-yl)acetate Chemical compound N1C2=CC=CC=C2C2=C1C(CC(=O)OC)CCC2 PSECTKHYVHZABC-UHFFFAOYSA-N 0.000 description 1
QIIIHXXKWRMLGM-UHFFFAOYSA-N methyl 2-(2-methyl-9H-carbazol-1-yl)acetate Chemical compound COC(CC1=C(C=CC=2C3=CC=CC=C3NC12)C)=O QIIIHXXKWRMLGM-UHFFFAOYSA-N 0.000 description 1
KIRHAUWMZOGYFK-UHFFFAOYSA-N methyl 2-(9h-carbazol-1-yl)acetate Chemical compound N1C2=CC=CC=C2C2=C1C(CC(=O)OC)=CC=C2 KIRHAUWMZOGYFK-UHFFFAOYSA-N 0.000 description 1
DNUFEKDQCMNDGW-UHFFFAOYSA-N methyl 3-(1,4-dioxo-10-propylspiro[4.5]decan-10-yl)propanoate Chemical compound COC(=O)CCC1(CCC)CCCCC11C(=O)CCC1=O DNUFEKDQCMNDGW-UHFFFAOYSA-N 0.000 description 1
BJQGNXXBIIAVCZ-UHFFFAOYSA-N methyl 3-(2-oxo-1-propylcyclohexyl)propanoate Chemical compound COC(=O)CCC1(CCC)CCCCC1=O BJQGNXXBIIAVCZ-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000004533 oil dispersion Substances 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
229960005235 piperonyl butoxide Drugs 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000009738 saturating Methods 0.000 description 1
238000012216 screening Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 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
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
238000001665 trituration Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

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CA234,428A 1975-08-28 1975-08-28 Derives tricycliques de l'acide acetique et de l'indole Expired CA1046519A (fr)

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CA234,428A CA1046519A (fr)	1975-08-28	1975-08-28	Derives tricycliques de l'acide acetique et de l'indole

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CA234,428A CA1046519A (fr)	1975-08-28	1975-08-28	Derives tricycliques de l'acide acetique et de l'indole

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CA1046519A true CA1046519A (fr)	1979-01-16

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CA234,428A Expired CA1046519A (fr)	1975-08-28	1975-08-28	Derives tricycliques de l'acide acetique et de l'indole

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5238953A (en) *	1991-01-22	1993-08-24	Farmitalia Carlo Erba S.R.L.	N-imidazolyl derivatives of substituted tetrahydrocarbazole and cyclohept (b) indole

1975
- 1975-08-28 CA CA234,428A patent/CA1046519A/fr not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5238953A (en) *	1991-01-22	1993-08-24	Farmitalia Carlo Erba S.R.L.	N-imidazolyl derivatives of substituted tetrahydrocarbazole and cyclohept (b) indole

Publication	Publication Date	Title
US4057559A (en)	1977-11-08	Carbazole acetic acid derivatives
US3293263A (en)	1966-12-20	Diphenylbenzocycloalkenes
US4259338A (en)	1981-03-31	Benzofuranyl-tetrahydropyridines and -piperidines, their acid addition salts and antidepressant preparations thereof
Martin et al.	1979	New methods for alkaloid synthesis. Facile total syntheses of (.+-.)-O-methyljoubertiamine and (.+-.)-mesembrine
US4478750A (en)	1984-10-23	1-Phenyl-azepinoindoles
EP0033767B1 (fr)	1984-06-27	Indolobenzoxazines, procédés pour leur préparation et compositions pharmaceutiques les contenant
CA1046519A (fr)	1979-01-16	Derives tricycliques de l'acide acetique et de l'indole
Hino et al.	1988	Agents Acting on the Central Nervous System.: Synthesis of 3-Phenyl-2-piperazinyl-1-benzazocines, 3-Substituted-2-piperazinyl-1-benzazepines and Related Compounds
US3954794A (en)	1976-05-04	Heterocyclic compounds
CA1047039A (fr)	1979-01-23	Derives tricycliques d'alkylamines et leur preparation
Asselin et al.	1976	Cycloalkanoindoles. 2. 1-Alkyl-1, 2, 3, 4-tetrahydrocarbazole-1-ethanamines and related compounds. Potential antidepressants
CA1129413A (fr)	1982-08-10	Derives du tetrahydrothiopyrano ¬2,3-b\| indole
US4008277A (en)	1977-02-15	Benzo-bicyclononene derivatives
CA1132553A (fr)	1982-09-28	Derives de l'isoquinoline
GB1594450A (en)	1981-07-30	1,3-oxathiolane sulphoxides and their use in the preparation of 5,6-dihydro-2-methyl-1,4-oxathiin derivatives
EP0240176B1 (fr)	1990-11-22	Pyrimidoindoles substitués
US3965106A (en)	1976-06-22	3-Phenoxypropylamine derivatives
US3244705A (en)	1966-04-05	Triphenylhaloethylene derivatives
US3795709A (en)	1974-03-05	Benzobenzazulenes
US3442903A (en)	1969-05-06	Certain aminopropylidenebenzo(5,6)cyclohepta(1,2-d)thiazoles
US3509132A (en)	1970-04-28	Decahydro-1,6-diazecines
US3459806A (en)	1969-08-05	Benzobenzazulenes
US3956391A (en)	1976-05-11	Amino substituted tetrahydropleiadenes
US3306934A (en)	1967-02-28	5-(aminopropylidene)-and 5-hydroxy-5-(aminopropyl)-3-dialkylsulfamoyl-5h-dibenzo[a,d] cycloheptenes
US3994915A (en)	1976-11-30	Preparation of substituted oxazoles

CA1046519A - Derives tricycliques de l'acide acetique et de l'indole - Google Patents

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Priority Applications (1)

Applications Claiming Priority (1)

Publications (1)

Family

ID=4103931

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Country Status (1)

Cited By (1)

Cited By (1)

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