CH629774A5 - Verfahren zur herstellung von 3-(3-carboxy-4-hydroxyphenyl)-4,5-dihydro-2-phenylbenz(e)indol. - Google Patents
Verfahren zur herstellung von 3-(3-carboxy-4-hydroxyphenyl)-4,5-dihydro-2-phenylbenz(e)indol. Download PDFInfo
- Publication number
- CH629774A5 CH629774A5 CH664677A CH664677A CH629774A5 CH 629774 A5 CH629774 A5 CH 629774A5 CH 664677 A CH664677 A CH 664677A CH 664677 A CH664677 A CH 664677A CH 629774 A5 CH629774 A5 CH 629774A5
- Authority
- CH
- Switzerland
- Prior art keywords
- phenacyl
- dihydro
- carboxy
- phenylbenz
- enammonium
- Prior art date
Links
- 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 claims description 9
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims description 18
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 15
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 claims description 8
- 229960004963 mesalazine Drugs 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 7
- -1 naphthalene compound Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 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 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 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
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- KCKZIWSINLBROE-UHFFFAOYSA-N 3,4-dihydro-1h-naphthalen-2-one Chemical compound C1=CC=C2CC(=O)CCC2=C1 KCKZIWSINLBROE-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000002244 precipitate Substances 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
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 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
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000002081 enamines Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 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 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
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 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
- 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 description 1
- ZFOQAJYJFVWBKU-UHFFFAOYSA-N n,n-dipentyl-3,4-dihydronaphthalen-2-amine Chemical compound C1=CC=C2CCC(N(CCCCC)CCCCC)=CC2=C1 ZFOQAJYJFVWBKU-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 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
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/112—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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]
-
- 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/60—Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH629774A5 true CH629774A5 (de) | 1982-05-14 |
Family
ID=24780138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH664677A CH629774A5 (de) | 1976-06-03 | 1977-05-31 | Verfahren zur herstellung von 3-(3-carboxy-4-hydroxyphenyl)-4,5-dihydro-2-phenylbenz(e)indol. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4066659A (en, 2012) |
| JP (1) | JPS5325556A (en, 2012) |
| AT (1) | AT353786B (en, 2012) |
| BE (1) | BE855406A (en, 2012) |
| CA (1) | CA1105936A (en, 2012) |
| CH (1) | CH629774A5 (en, 2012) |
| DE (1) | DE2724601A1 (en, 2012) |
| DK (1) | DK145296C (en, 2012) |
| ES (1) | ES459256A1 (en, 2012) |
| FI (1) | FI65059C (en, 2012) |
| HU (1) | HU176801B (en, 2012) |
| IT (1) | IT1076781B (en, 2012) |
| NL (1) | NL7705807A (en, 2012) |
| SE (1) | SE425391B (en, 2012) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1356431A (en) * | 1971-06-03 | 1974-06-12 | Wyeth John & Brother Ltd | Substituted benz-g-indoles |
| US3931407A (en) * | 1973-03-01 | 1976-01-06 | American Hoechst Corporation | Method of treatment with and compositions containing condensed pyrroles bearing an N-phenyl substituent |
-
1976
- 1976-06-03 US US05/692,331 patent/US4066659A/en not_active Expired - Lifetime
-
1977
- 1977-05-26 NL NL7705807A patent/NL7705807A/xx not_active Application Discontinuation
- 1977-05-28 ES ES459256A patent/ES459256A1/es not_active Expired
- 1977-05-31 CH CH664677A patent/CH629774A5/de not_active IP Right Cessation
- 1977-06-01 IT IT24269/77A patent/IT1076781B/it active
- 1977-06-01 FI FI771747A patent/FI65059C/fi not_active IP Right Cessation
- 1977-06-01 DE DE19772724601 patent/DE2724601A1/de active Granted
- 1977-06-02 DK DK243677A patent/DK145296C/da active
- 1977-06-02 HU HU77HO1992A patent/HU176801B/hu not_active IP Right Cessation
- 1977-06-02 AT AT392877A patent/AT353786B/de not_active IP Right Cessation
- 1977-06-02 CA CA279,689A patent/CA1105936A/en not_active Expired
- 1977-06-03 SE SE7706526A patent/SE425391B/xx not_active IP Right Cessation
- 1977-06-03 BE BE178212A patent/BE855406A/xx not_active IP Right Cessation
- 1977-06-03 JP JP6568277A patent/JPS5325556A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| AT353786B (de) | 1979-12-10 |
| DE2724601C2 (en, 2012) | 1988-03-03 |
| DK243677A (da) | 1977-12-04 |
| HU176801B (en) | 1981-05-28 |
| FI771747A7 (en, 2012) | 1977-12-04 |
| DK145296B (da) | 1982-10-25 |
| BE855406A (fr) | 1977-12-05 |
| ATA392877A (de) | 1979-05-15 |
| FI65059B (fi) | 1983-11-30 |
| ES459256A1 (es) | 1978-03-01 |
| FI65059C (fi) | 1984-03-12 |
| DK145296C (da) | 1983-03-14 |
| DE2724601A1 (de) | 1977-12-22 |
| SE425391B (sv) | 1982-09-27 |
| US4066659A (en) | 1978-01-03 |
| CA1105936A (en) | 1981-07-28 |
| NL7705807A (nl) | 1977-12-06 |
| SE7706526L (sv) | 1977-12-04 |
| IT1076781B (it) | 1985-04-27 |
| JPS5325556A (en) | 1978-03-09 |
| JPS6120546B2 (en, 2012) | 1986-05-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |