HU176801B - Process for preparing 3-/3-carboxy-4-hydroxyphenyl/-4,5-dihydro-2-phenyl-benz/e/indole - Google Patents
Process for preparing 3-/3-carboxy-4-hydroxyphenyl/-4,5-dihydro-2-phenyl-benz/e/indole Download PDFInfo
- Publication number
- HU176801B HU176801B HU77HO1992A HUHO001992A HU176801B HU 176801 B HU176801 B HU 176801B HU 77HO1992 A HU77HO1992 A HU 77HO1992A HU HO001992 A HUHO001992 A HU HO001992A HU 176801 B HU176801 B HU 176801B
- Authority
- HU
- Hungary
- Prior art keywords
- indole
- hydroxyphenyl
- dihydro
- carboxy
- phenacyl
- Prior art date
Links
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title description 6
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims description 7
- -1 3- (3-carboxy-4-hydroxyphenyl) -4,5-dihydro-2-phenylbenzene indole Chemical compound 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- WYJDRDMLKVLOFR-UHFFFAOYSA-N 2-[2-(dimethylamino)-3,4-dihydronaphthalen-1-yl]-1-phenylethanone;hydrobromide Chemical group Br.C12=CC=CC=C2CCC(N(C)C)=C1CC(=O)C1=CC=CC=C1 WYJDRDMLKVLOFR-UHFFFAOYSA-N 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 4
- 108090000623 proteins and genes Proteins 0.000 abstract 3
- 206010028980 Neoplasm Diseases 0.000 abstract 2
- 230000001613 neoplastic effect Effects 0.000 abstract 2
- 210000004881 tumor cell Anatomy 0.000 abstract 2
- 206010025323 Lymphomas Diseases 0.000 abstract 1
- 206010061309 Neoplasm progression Diseases 0.000 abstract 1
- 210000000481 breast Anatomy 0.000 abstract 1
- 201000011510 cancer Diseases 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 abstract 1
- 238000003745 diagnosis Methods 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 230000002496 gastric effect Effects 0.000 abstract 1
- 208000032839 leukemia Diseases 0.000 abstract 1
- 208000037841 lung tumor Diseases 0.000 abstract 1
- 230000003211 malignant effect Effects 0.000 abstract 1
- 201000001441 melanoma Diseases 0.000 abstract 1
- 230000001394 metastastic effect Effects 0.000 abstract 1
- 206010061289 metastatic neoplasm Diseases 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- 230000005751 tumor progression Effects 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 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 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
- 229960000583 acetic acid Drugs 0.000 description 8
- 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 description 7
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 6
- 229960004963 mesalazine Drugs 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 150000001875 compounds Chemical class 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
- 239000000543 intermediate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 150000002081 enamines Chemical class 0.000 description 2
- 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 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 description 1
- UCGVRRXOEFAKFW-UHFFFAOYSA-N 2-[2-(dibutylamino)-3,4-dihydronaphthalen-1-yl]-1-phenylethanone;hydrobromide Chemical compound Br.C12=CC=CC=C2CCC(N(CCCC)CCCC)=C1CC(=O)C1=CC=CC=C1 UCGVRRXOEFAKFW-UHFFFAOYSA-N 0.000 description 1
- ZHNDHRRQWDSRCE-UHFFFAOYSA-N 2-[2-(dipentylamino)-3,4-dihydronaphthalen-1-yl]-1-phenylethanone;hydrobromide Chemical compound Br.C12=CC=CC=C2CCC(N(CCCCC)CCCCC)=C1CC(=O)C1=CC=CC=C1 ZHNDHRRQWDSRCE-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 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
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- 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
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 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
- 238000010189 synthetic method Methods 0.000 description 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 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)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analysing Biological Materials (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 |
|---|---|
| HU176801B true HU176801B (en) | 1981-05-28 |
Family
ID=24780138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU77HO1992A HU176801B (en) | 1976-06-03 | 1977-06-02 | Process for preparing 3-/3-carboxy-4-hydroxyphenyl/-4,5-dihydro-2-phenyl-benz/e/indole |
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 |
| 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 |
| CH629774A5 (de) | 1982-05-14 |
| 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 |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |