CA1092126A - Methode de preparation du 3-(3-carboxy-4- hydroxyphenyl)4,5-dihydro-2-phenylbenz[e]indole et intermediaires - Google Patents

Methode de preparation du 3-(3-carboxy-4- hydroxyphenyl)4,5-dihydro-2-phenylbenz[e]indole et intermediaires

Info

Publication number: CA1092126A
Authority: CA; Canada
Prior art keywords: phenacyl; dihydronaphthalene; preparation; hydrobromide; pyrrolidino
Prior art date: 1976-06-03
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

CA344,310A

Other languages

English (en)

Inventor

Richard C. Effland

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.)

Hoechst AG

Original Assignee

Hoechst AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-06-03

Filing date

1980-01-24

Publication date

1980-12-23

1976-06-03 Priority claimed from US05/692,331 external-priority patent/US4066659A/en

1980-01-24 Application filed by Hoechst AG filed Critical Hoechst AG

1980-01-24 Priority to CA344,310A priority Critical patent/CA1092126A/fr

1980-12-23 Application granted granted Critical

1980-12-23 Publication of CA1092126A publication Critical patent/CA1092126A/fr

Status Expired legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims abstract description 8
238000000034 method Methods 0.000 title claims description 24
239000000543 intermediate Substances 0.000 title abstract description 6
HAWWPSYXSLJRBO-UHFFFAOYSA-N fendosal Chemical compound C1=C(O)C(C(=O)O)=CC(N2C(=CC=3C4=CC=CC=C4CCC=32)C=2C=CC=CC=2)=C1 HAWWPSYXSLJRBO-UHFFFAOYSA-N 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 9
-1 napthalene compound Chemical class 0.000 claims abstract description 5
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims abstract description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052794 bromium Inorganic materials 0.000 claims abstract description 3
125000001246 bromo group Chemical group Br* 0.000 claims abstract description 3
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
229910052801 chlorine Chemical group 0.000 claims abstract description 3
239000000460 chlorine Chemical group 0.000 claims abstract description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 3
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 13
239000002904 solvent Substances 0.000 claims description 8
LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 claims description 6
WYJDRDMLKVLOFR-UHFFFAOYSA-N 2-[2-(dimethylamino)-3,4-dihydronaphthalen-1-yl]-1-phenylethanone;hydrobromide Chemical compound Br.C12=CC=CC=C2CCC(N(C)C)=C1CC(=O)C1=CC=CC=C1 WYJDRDMLKVLOFR-UHFFFAOYSA-N 0.000 claims description 3
239000000126 substance Substances 0.000 claims 4
QUSLRVPVUZMBTO-UHFFFAOYSA-N n,n-dimethyl-3,4-dihydronaphthalen-2-amine Chemical compound C1=CC=C2CCC(N(C)C)=CC2=C1 QUSLRVPVUZMBTO-UHFFFAOYSA-N 0.000 claims 1
UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 1
230000000202 analgesic effect Effects 0.000 abstract description 2
230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
239000000825 pharmaceutical preparation Substances 0.000 abstract 1
229940127557 pharmaceutical product Drugs 0.000 abstract 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 4
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 4
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 4
KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 4
229960004963 mesalazine Drugs 0.000 description 4
239000000203 mixture Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
150000002081 enamines Chemical class 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
238000000967 suction filtration Methods 0.000 description 2
BSRHTXNBIWIZPC-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-3h-benzo[e]indole Chemical compound N1C=2CCC3=CC=CC=C3C=2C=C1C1=CC=CC=C1 BSRHTXNBIWIZPC-UHFFFAOYSA-N 0.000 description 1
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229960004909 aminosalicylic acid Drugs 0.000 description 1
238000009835 boiling Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
ZUMAGUBZZXWNRS-UHFFFAOYSA-N n,n-dibutyl-3,4-dihydronaphthalen-2-amine Chemical compound C1=CC=C2CCC(N(CCCC)CCCC)=CC2=C1 ZUMAGUBZZXWNRS-UHFFFAOYSA-N 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
150000003233 pyrroles Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 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
239000012258 stirred mixture Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1

Landscapes

Indole Compounds (AREA)

CA344,310A 1976-06-03 1980-01-24 Methode de preparation du 3-(3-carboxy-4- hydroxyphenyl)4,5-dihydro-2-phenylbenz[e]indole et intermediaires Expired CA1092126A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA344,310A CA1092126A (fr)	1976-06-03	1980-01-24	Methode de preparation du 3-(3-carboxy-4- hydroxyphenyl)4,5-dihydro-2-phenylbenz[e]indole et intermediaires

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US692,331		1976-06-03
US05/692,331 US4066659A (en)	1976-06-03	1976-06-03	Method of preparation of 3-(3-carboxy-4-hydroxyphenyl)-4,5-dihydro-2-phenylbenz (e) indole and valuable intermediates related thereto
CA279,689A CA1105936A (fr)	1976-06-03	1977-06-02	Obtention de 3-(3-carboxy-4-hydroxyphenyl)-4,5- dihydro-2-phenylbenz[e]indole et de ses intermediaires interessants
CA344,310A CA1092126A (fr)	1976-06-03	1980-01-24	Methode de preparation du 3-(3-carboxy-4- hydroxyphenyl)4,5-dihydro-2-phenylbenz[e]indole et intermediaires

Publications (1)

Publication Number	Publication Date
CA1092126A true CA1092126A (fr)	1980-12-23

Family

ID=27165102

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA344,310A Expired CA1092126A (fr)	1976-06-03	1980-01-24	Methode de preparation du 3-(3-carboxy-4- hydroxyphenyl)4,5-dihydro-2-phenylbenz[e]indole et intermediaires

Country Status (1)

Country	Link
CA (1)	CA1092126A (fr)

1980
- 1980-01-24 CA CA344,310A patent/CA1092126A/fr not_active Expired

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Legal Events

Date	Code	Title	Description
1997-12-23	MKEX	Expiry