CA1271197A - Procede de preparation de derives du 4-phenylpropyl indole - Google Patents

Procede de preparation de derives du 4-phenylpropyl indole

Info

Publication number: CA1271197A
Authority: CA; Canada
Prior art keywords: formula; product; action; already indicated; carbon
Prior art date: 1985-06-05
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 - Fee Related

Application number

CA000510849A

Other languages

English (en)

French (fr)

Inventor

Francois Clemence

Gilles Hamon

Jacques Guillaume

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.)

Sanofi Aventis France

Original Assignee

Roussel Uclaf SA

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.)

1985-06-05

Filing date

1986-06-04

Publication date

1990-07-03

1986-06-04 Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA

1990-07-03 Application granted granted Critical

1990-07-03 Publication of CA1271197A publication Critical patent/CA1271197A/fr

2007-07-03 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title abstract 2
CMAKVGXPYNUYAE-UHFFFAOYSA-N 4-(3-phenylpropyl)-1h-indole Chemical class C=1C=CC=2NC=CC=2C=1CCCC1=CC=CC=C1 CMAKVGXPYNUYAE-UHFFFAOYSA-N 0.000 title description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 49
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 36
239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 26
239000001257 hydrogen Substances 0.000 claims abstract description 24
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
150000003839 salts Chemical class 0.000 claims abstract description 14
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 13
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
239000001301 oxygen Substances 0.000 claims abstract description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
239000011593 sulfur Substances 0.000 claims abstract description 5
150000002431 hydrogen Chemical class 0.000 claims abstract 12
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 7
125000001624 naphthyl group Chemical group 0.000 claims abstract 2
-1 alkyl radical Chemical class 0.000 claims description 121
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 98
125000004432 carbon atom Chemical group C* 0.000 claims description 63
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 claims description 50
239000011734 sodium Substances 0.000 claims description 50
229910052708 sodium Inorganic materials 0.000 claims description 50
229910021529 ammonia Inorganic materials 0.000 claims description 49
239000002904 solvent Substances 0.000 claims description 42
125000004429 atom Chemical group 0.000 claims description 39
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 36
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 34
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 32
239000002253 acid Substances 0.000 claims description 31
238000000034 method Methods 0.000 claims description 28
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 26
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 26
239000003795 chemical substances by application Substances 0.000 claims description 26
229910052801 chlorine Inorganic materials 0.000 claims description 23
239000000460 chlorine Substances 0.000 claims description 21
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 18
229910052794 bromium Inorganic materials 0.000 claims description 18
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
229910052799 carbon Inorganic materials 0.000 claims description 17
239000003054 catalyst Substances 0.000 claims description 17
229910052763 palladium Inorganic materials 0.000 claims description 17
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
239000007868 Raney catalyst Substances 0.000 claims description 16
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 16
229910000564 Raney nickel Inorganic materials 0.000 claims description 16
229910052697 platinum Inorganic materials 0.000 claims description 16
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
230000007062 hydrolysis Effects 0.000 claims description 13
238000006460 hydrolysis reaction Methods 0.000 claims description 13
238000002360 preparation method Methods 0.000 claims description 13
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
230000026030 halogenation Effects 0.000 claims description 11
238000005658 halogenation reaction Methods 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
238000003776 cleavage reaction Methods 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
230000007017 scission Effects 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
239000003513 alkali Substances 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 8
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 8
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 8
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 8
WSNDAYQNZRJGMJ-UHFFFAOYSA-N 2,2,2-trifluoroethanone Chemical compound FC(F)(F)[C]=O WSNDAYQNZRJGMJ-UHFFFAOYSA-N 0.000 claims description 7
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
229910052740 iodine Inorganic materials 0.000 claims description 6
150000003141 primary amines Chemical class 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
125000005842 heteroatom Chemical group 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
150000002829 nitrogen Chemical class 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 2
230000002140 halogenating effect Effects 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
150000003254 radicals Chemical class 0.000 claims 16
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 6
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 3
CMPXDYWLTWDIOY-UHFFFAOYSA-N 2-(3-phenylpropyl)-1h-indole Chemical compound C=1C2=CC=CC=C2NC=1CCCC1=CC=CC=C1 CMPXDYWLTWDIOY-UHFFFAOYSA-N 0.000 claims 2
HJENUMMIFDMCEN-UHFFFAOYSA-N 2-propyl-1h-indole Chemical compound C1=CC=C2NC(CCC)=CC2=C1 HJENUMMIFDMCEN-UHFFFAOYSA-N 0.000 claims 2
239000011630 iodine Substances 0.000 claims 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
210000000481 breast Anatomy 0.000 claims 1
125000004434 sulfur atom Chemical group 0.000 claims 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
239000003814 drug Substances 0.000 abstract description 4
230000003288 anthiarrhythmic effect Effects 0.000 abstract description 3
108090000312 Calcium Channels Proteins 0.000 abstract description 2
102000003922 Calcium Channels Human genes 0.000 abstract description 2
CPGKMLVTFNUAHL-UHFFFAOYSA-N [Ca].[Ca] Chemical compound [Ca].[Ca] CPGKMLVTFNUAHL-UHFFFAOYSA-N 0.000 abstract description 2
239000003416 antiarrhythmic agent Substances 0.000 abstract description 2
230000000903 blocking effect Effects 0.000 abstract description 2
125000003710 aryl alkyl group Chemical group 0.000 abstract 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000000243 solution Substances 0.000 description 12
239000002585 base Substances 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
150000002500 ions Chemical class 0.000 description 7
239000000203 mixture Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
241000700159 Rattus Species 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
238000003756 stirring Methods 0.000 description 6
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
239000000546 pharmaceutical excipient Substances 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
238000013019 agitation Methods 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000003480 eluent Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
229940072033 potash Drugs 0.000 description 4
235000015320 potassium carbonate Nutrition 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
239000003826 tablet Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
210000001367 artery Anatomy 0.000 description 3
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical class CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
239000008101 lactose Substances 0.000 description 3
239000011707 mineral Substances 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
238000002211 ultraviolet spectrum Methods 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
MUQNGPZZQDCDFT-JNQJZLCISA-N Halcinonide Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@@H]2O MUQNGPZZQDCDFT-JNQJZLCISA-N 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229910001854 alkali hydroxide Inorganic materials 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
206010003119 arrhythmia Diseases 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
239000001530 fumaric acid Substances 0.000 description 2
239000008103 glucose Substances 0.000 description 2
229940028332 halog Drugs 0.000 description 2
JFDDFGLNZWNJTK-UHFFFAOYSA-N indole-4-carbaldehyde Chemical compound O=CC1=CC=CC2=C1C=CN2 JFDDFGLNZWNJTK-UHFFFAOYSA-N 0.000 description 2
229910001629 magnesium chloride Inorganic materials 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
235000019799 monosodium phosphate Nutrition 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000012071 phase Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
235000011181 potassium carbonates Nutrition 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 2
229910000162 sodium phosphate Inorganic materials 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
GMJGVSRJFCRDSX-UHFFFAOYSA-N 1-(2-hydroxyphenyl)-3-(1h-indol-4-yl)prop-2-en-1-one Chemical compound OC1=CC=CC=C1C(=O)C=CC1=CC=CC2=C1C=CN2 GMJGVSRJFCRDSX-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-L 2,3-dihydroxybutanedioate Chemical compound [O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-L 0.000 description 1
ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical compound OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
206010019280 Heart failures Diseases 0.000 description 1
FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
241001674048 Phthiraptera Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
206010047281 Ventricular arrhythmia Diseases 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
239000011717 all-trans-retinol Substances 0.000 description 1
235000019169 all-trans-retinol Nutrition 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000006793 arrhythmia Effects 0.000 description 1
230000002763 arrhythmic effect Effects 0.000 description 1
125000005605 benzo group Chemical group 0.000 description 1
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
SRSPILBBEHNEHD-UHFFFAOYSA-N boranylformonitrile Chemical compound BC#N SRSPILBBEHNEHD-UHFFFAOYSA-N 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
UHNOAGDNODCLKN-UHFFFAOYSA-N bromine;pyridine Chemical compound [Br].C1=CC=NC=C1 UHNOAGDNODCLKN-UHFFFAOYSA-N 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
230000008602 contraction Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000009795 derivation Methods 0.000 description 1
230000001079 digestive effect Effects 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
229940048879 dl tartaric acid Drugs 0.000 description 1
229960003638 dopamine Drugs 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000000887 hydrating effect Effects 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000007943 implant Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
210000004731 jugular vein Anatomy 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
239000007788 liquid Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
CSYNQJPENMOLHR-UHFFFAOYSA-N n,n-diethylethanamine;ethyl acetate Chemical compound CCOC(C)=O.CCN(CC)CC CSYNQJPENMOLHR-UHFFFAOYSA-N 0.000 description 1
229960002748 norepinephrine Drugs 0.000 description 1
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910001414 potassium ion Inorganic materials 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000013615 primer Substances 0.000 description 1
239000002987 primer (paints) Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
230000033764 rhythmic process Effects 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
210000000329 smooth muscle myocyte Anatomy 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000000946 synaptic effect Effects 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)

CA000510849A 1985-06-05 1986-06-04 Procede de preparation de derives du 4-phenylpropyl indole Expired - Fee Related CA1271197A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR8508459A FR2583047B1 (fr)	1985-06-05	1985-06-05	Procede de preparation de derives du 4-phenylpropyl indole, et intermediaires
FR85-08459		1985-06-05

Publications (1)

Publication Number	Publication Date
CA1271197A true CA1271197A (fr)	1990-07-03

Family

ID=9319884

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000510849A Expired - Fee Related CA1271197A (fr)	1985-06-05	1986-06-04	Procede de preparation de derives du 4-phenylpropyl indole

Country Status (5)

Country	Link
AT (1)	AT386823B (de)
CA (1)	CA1271197A (de)
FI (1)	FI85465C (de)
FR (1)	FR2583047B1 (de)
HU (1)	HU196751B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2609464B1 (fr) *	1987-01-09	1990-12-07	Roussel Uclaf	Nouveaux derives du n-(1h-indol 4-yl) benzamide ainsi que leurs sels, leur application a titre de medicaments, et les compositions les renfermant
FR2608601B2 (fr) *	1985-07-11	1989-04-14	Roussel Uclaf	Nouveaux derives de l'indole carboxamide, leurs sels, procede et intermediaires de preparation, application a titre de medicaments et compositions les renfermant
DE3788207T2 (de) *	1986-12-19	1994-03-31	Roussel Uclaf	Indol-Carboxamid-Derivate und ihre Salze, Verfahren und Zwischenprodukte zur Herstellung, Anwendung als Heilmittel und Zusammenstellungen, die sie enthalten.

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1504707A (en) *	1974-08-07	1978-03-22	Bellon Labor Sa Roger	1-aryl-2-oxo-2,4,5,6,7,7a-hexahydroindoles
FR2528043A1 (fr) *	1982-06-03	1983-12-09	Roussel Uclaf	Nouveaux derives de la 1,3-dihydro 4-/1-hydroxy-2-amino-ethyl/2h-indol-2-one, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant

1985
- 1985-06-05 FR FR8508459A patent/FR2583047B1/fr not_active Expired
1986
- 1986-06-04 FI FI862376A patent/FI85465C/fi not_active IP Right Cessation
- 1986-06-04 HU HU862371A patent/HU196751B/hu not_active IP Right Cessation
- 1986-06-04 AT AT0151786A patent/AT386823B/de not_active IP Right Cessation
- 1986-06-04 CA CA000510849A patent/CA1271197A/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
FR2583047B1 (fr)	1988-01-08
FI862376A0 (fi)	1986-06-04
HU196751B (en)	1989-01-30
FR2583047A1 (fr)	1986-12-12
AT386823B (de)	1988-10-25
FI862376A7 (fi)	1986-12-06
FI85465B (fi)	1992-01-15
HUT42066A (en)	1987-06-29
FI85465C (fi)	1992-04-27
ATA151786A (de)	1988-03-15

Legal Events

Date	Code	Title	Description
1995-01-03	MKLA	Lapsed

Publication	Publication Date	Title
FR2496102A1 (fr)	1982-06-18	Benzopyranes 7-substitues, leur preparation et leur application en tant que medicaments
EP0213984B1 (de)	1991-01-09	Indolcarboxamidderivate, ihre Salze, Verfahren und Zwischenprodukte, Anwendung als Heilmittel und Zusammensetzungen die sie enthalten
CA1213892A (fr)	1986-11-12	Procede de preparation de nouveaux derives de la sulfonyluree
FR2528043A1 (fr)	1983-12-09	Nouveaux derives de la 1,3-dihydro 4-/1-hydroxy-2-amino-ethyl/2h-indol-2-one, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant
EP0566446B1 (de)	1996-02-07	Indan-1,3-Dion und Indan-1,2,3-Trionderivate, Verfahren zu ihrer Herstellung und ihrer therapeutische Verwendung
EP0021940B1 (de)	1983-01-19	Aminoderivate von Benzothiazol, Verfahren zu ihrer Herstellung und ihre Anwendung in der Heilkunde
CA1145752A (fr)	1983-05-03	Procede de preparation de nouveaux derives du n'tetrahydropyridinyl-indoles et de leurs sels
EP0150139B1 (de)	1988-05-18	Indol-Ethylphenyl-Derivate, ihre Salze, Vefahren zur Herstellung, Anwendung als Heilmittel und Zusammensetzungen die sie enthalten
CA1265805A (fr)	1990-02-13	Procede de preparation de nouveaux derives du 4- phenylpropyl indole
CA1269107A (fr)	1990-05-15	Procede de preparation de nouveaux derives de l'hydroxy alkoxy 4-phenylpropyl indole et de leurs sels
FR2512443A1 (fr)	1983-03-11	Derives de phenoxy-3 propanol-2, leur preparation et leur application en therapeutique
FR2492821A1 (fr)	1982-04-30	Derives de la pyrimidine, leur procede de preparation et les compositions pharmaceutiques les contenant
EP0275762B1 (de)	1993-11-18	Indol-Carboxamid-Derivate und ihre Salze, Verfahren und Zwischenprodukte zur Herstellung, Anwendung als Heilmittel und Zusammenstellungen, die sie enthalten
CA1266471A (fr)	1990-03-06	Derives du 4-morpholinyl 1h- indole et leurs sels, procede pour leur preparation et compositions pharmaceutiques les renfermant
FR2583047A1 (fr)	1986-12-12	Procede de preparation de derives du 4-phenylpropyl indole, et intermediaires
CH615673A5 (de)	1980-02-15
EP0022017A1 (de)	1981-01-07	Derivate von 2-Benzoyl-4-nitro-aniliden, deren Herstellung und deren Verwendung als Heilmittel
EP0275221B1 (de)	1991-04-17	N-(1H-indol-4-yl)-Benzamidderivate, ihre Salze und deren Anwendung als Heilmittel und Zusammenstellungen, die sie enthalten
CA1139754A (fr)	1983-01-18	Derives d'ortho chloro benzoyl-2 chloro-4 glycylanilide, leur preparation et leur application en tant que medicaments
FR2505824A1 (fr)	1982-11-19	Derives d'isoprenylamine et leur application a des compositions pharmaceutiques
FR2503150A1 (fr)	1982-10-08	Mercaptoacyl-carnitines, procede pour leur preparation et leurs utilisations therapeutiques dans le traitement des intoxications et des brulures et en tant qu'agents mucolytiques
CA1266050A (fr)	1990-02-20	Procede de preparation de nouveaux derives de l'indole carboxamide et de leurs sels
CA1161444A (fr)	1984-01-31	Procede de preparation de derives du cycloheptindolol et de leurs sels avec les acides
CH652386A5 (fr)	1985-11-15	Derives d'acides phenyl aliphatique carboxyliques comme medicaments.
FR2611712A1 (fr)	1988-09-09	Nouveaux derives n-substitues de l'alpha-mercaptomethyl benzene propanamide, leur procede de preparation, leur application a titre de medicaments et les compositions les renfermant