PL192111B1 - Sposób otrzymywania wysokiej czystości 4-(3,4-dwuchloro-fenylo)-3,4-dwuwodoro-1(2H)-naftalen-1-onu - Google Patents
Sposób otrzymywania wysokiej czystości 4-(3,4-dwuchloro-fenylo)-3,4-dwuwodoro-1(2H)-naftalen-1-onuInfo
- Publication number
- PL192111B1 PL192111B1 PL332779A PL33277997A PL192111B1 PL 192111 B1 PL192111 B1 PL 192111B1 PL 332779 A PL332779 A PL 332779A PL 33277997 A PL33277997 A PL 33277997A PL 192111 B1 PL192111 B1 PL 192111B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- dichloro
- mixture
- phenyl
- dihydro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 41
- 150000001875 compounds Chemical class 0.000 title abstract description 16
- 230000001052 transient effect Effects 0.000 title 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims abstract description 23
- 238000002425 crystallisation Methods 0.000 claims abstract description 16
- 230000008025 crystallization Effects 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims abstract description 6
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 6
- 239000002798 polar solvent Substances 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 48
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 24
- RZPFVRFSYMUDJO-UHFFFAOYSA-N 2h-naphthalen-1-one Chemical compound C1=CC=C2C(=O)CC=CC2=C1 RZPFVRFSYMUDJO-UHFFFAOYSA-N 0.000 claims description 21
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 12
- 239000012454 non-polar solvent Substances 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 239000006227 byproduct Substances 0.000 abstract description 7
- 238000002360 preparation method Methods 0.000 abstract description 7
- JGMBHJNMQVKDMW-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1C2=CC=CC=C2C(=O)CC1 JGMBHJNMQVKDMW-UHFFFAOYSA-N 0.000 abstract 1
- 230000003247 decreasing effect Effects 0.000 abstract 1
- 229940117389 dichlorobenzene Drugs 0.000 abstract 1
- 239000012450 pharmaceutical intermediate Substances 0.000 abstract 1
- 239000013078 crystal Substances 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 238000003756 stirring Methods 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 11
- 239000000047 product Substances 0.000 description 9
- -1 2,3-dichloro-phenyl Chemical group 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000003610 charcoal Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000012456 homogeneous solution Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 3
- 229960002073 sertraline Drugs 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- CADNHVPYLGFYJI-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-3,4-dihydro-2h-naphthalen-1-one Chemical compound ClC1=CC(Cl)=CC=C1C1C2=CC=CC=C2C(=O)CC1 CADNHVPYLGFYJI-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- NSXYYYUKWBLFQH-MHECFPHRSA-N methyl (2r)-4-hydroxy-2-[[(3s)-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-6-yl]methyl]-3-(4-hydroxyphenyl)-5-oxofuran-2-carboxylate Chemical compound O([C@@]1(CC=2C=C3C[C@H](O)C(C)(C)OC3=CC=2)C(=O)OC)C(=O)C(O)=C1C1=CC=C(O)C=C1 NSXYYYUKWBLFQH-MHECFPHRSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- AVBGNFCMKJOFIN-UHFFFAOYSA-N triethylammonium acetate Chemical compound CC(O)=O.CCN(CC)CC AVBGNFCMKJOFIN-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- FLSBZXWDASEHJU-UHFFFAOYSA-N 4,4-diphenylbutanoic acid Chemical class C=1C=CC=CC=1C(CCC(=O)O)C1=CC=CC=C1 FLSBZXWDASEHJU-UHFFFAOYSA-N 0.000 description 1
- DPCXOOJTAKKWIC-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=C(Cl)C(Cl)=C1 DPCXOOJTAKKWIC-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000006600 Stobbe condensation reaction Methods 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical compound FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 201000003102 mental depression Diseases 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/512—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being a free hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9602762A HUP9602762A2 (en) | 1996-10-09 | 1996-10-09 | Process for producing naphtalene derivatives |
| HU9701137A HU218599B (hu) | 1996-10-09 | 1997-07-02 | Eljárás 4-(3,4-diklór-fenil)-3,4-dihidro-1-(2H)-naftalin-1-on előállítására |
| PCT/HU1997/000058 WO1998015516A1 (en) | 1996-10-09 | 1997-10-08 | Process for the preparation of a pharmaceutical intermediate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL332779A1 PL332779A1 (en) | 1999-10-11 |
| PL192111B1 true PL192111B1 (pl) | 2006-08-31 |
Family
ID=89995311
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL332779A PL192111B1 (pl) | 1996-10-09 | 1997-10-08 | Sposób otrzymywania wysokiej czystości 4-(3,4-dwuchloro-fenylo)-3,4-dwuwodoro-1(2H)-naftalen-1-onu |
Country Status (7)
| Country | Link |
|---|---|
| AU (1) | AU4878897A (hu) |
| CZ (1) | CZ295766B6 (hu) |
| HU (1) | HU218599B (hu) |
| PL (1) | PL192111B1 (hu) |
| RO (1) | RO120194B1 (hu) |
| SK (1) | SK284671B6 (hu) |
| WO (1) | WO1998015516A1 (hu) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60020153T2 (de) * | 1999-11-16 | 2006-01-26 | Ciba Speciality Chemicals Holding Inc. | Verfahren zur herstellung von ketiminen |
| IN187170B (hu) | 2000-01-04 | 2002-02-23 | Sun Pharmaceutical Ind Ltd | |
| CN116041160A (zh) * | 2021-10-28 | 2023-05-02 | 上虞京新药业有限公司 | 一种将异舍曲酮转化为舍曲酮的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2632633B1 (fr) * | 1988-06-08 | 1991-04-05 | Delalande Sa | Procede de preparation de 4-aryl-1-tetralones |
-
1997
- 1997-07-02 HU HU9701137A patent/HU218599B/hu not_active IP Right Cessation
- 1997-10-08 WO PCT/HU1997/000058 patent/WO1998015516A1/en active IP Right Grant
- 1997-10-08 SK SK341-99A patent/SK284671B6/sk unknown
- 1997-10-08 PL PL332779A patent/PL192111B1/pl not_active IP Right Cessation
- 1997-10-08 RO RO99-00294A patent/RO120194B1/ro unknown
- 1997-10-08 CZ CZ19991207A patent/CZ295766B6/cs not_active IP Right Cessation
- 1997-10-08 AU AU48788/97A patent/AU4878897A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CZ295766B6 (cs) | 2005-10-12 |
| CZ120799A3 (cs) | 1999-09-15 |
| HUP9701137A2 (hu) | 1999-04-28 |
| RO120194B1 (ro) | 2005-10-28 |
| HUP9701137A3 (en) | 1999-05-28 |
| SK284671B6 (sk) | 2005-08-04 |
| WO1998015516A1 (en) | 1998-04-16 |
| HU9701137D0 (en) | 1997-08-28 |
| SK34199A3 (en) | 2000-03-13 |
| HU218599B (hu) | 2000-10-28 |
| AU4878897A (en) | 1998-05-05 |
| PL332779A1 (en) | 1999-10-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5021575A (en) | Method for introducing a 1,2 double bond into azasteroids | |
| CZ283215B6 (cs) | Způsob výroby 3-(alfa-methyxy)methylenbenzofuranonů | |
| US5322954A (en) | Synthesis of 4-substituted phthalic anhydrides | |
| US4417065A (en) | Process for the preparation of isosorbide 2-nitrate | |
| US4350813A (en) | Process for producing 7-alkoxycarbonyl-6,8-dimethyl-4-hydroxymethyl-1-phthalazone and its intermediates | |
| PL192111B1 (pl) | Sposób otrzymywania wysokiej czystości 4-(3,4-dwuchloro-fenylo)-3,4-dwuwodoro-1(2H)-naftalen-1-onu | |
| US4894457A (en) | 7-bromo-beta-carboline compound and method for producing same | |
| US4424361A (en) | Process for preparing polycyclic triazoles used to inhibit allergic responses | |
| US4314939A (en) | Process for the preparation of 15-hydroxyimino-E-homoeburnane and intermediates therefor | |
| JPH051071A (ja) | 抗アテローム性動脈硬化症フロクロモン | |
| EP0238411A1 (fr) | Dihydro-1,2 méthyl-4 oxo-1 5-H pyrido (4,3-b) indoles et leur procédé de synthèse | |
| NO149353B (no) | Fremgangsmaate ved fremstilling av 6-klor-alfa-metylkarbazol-2-eddiksyre | |
| US4464532A (en) | Intermediates of 7-alkoxycarbonyl-6,8-dimethyl-4-hydroxymethyl-1-phthalazone | |
| US4343738A (en) | Halogenated 15-hydroxy-E-homoeburane derivatives | |
| SU1017167A3 (ru) | Способ получени @ -5-ацетамидо-4,5,6,7-тетрагидро-2н-бензо/с/пиррола | |
| JPS61152673A (ja) | ジベンズ〔ｂ，ｅ〕オキセピン誘導体の製造法 | |
| US4677228A (en) | Chemical process | |
| US4642384A (en) | Process for the preparation of derivatives of pyrrolidine and piperidine | |
| Takakis et al. | Preparation of benzofuroxans and benzofurazans of 2, 3, 4, 5‐tetrahydrobenzo [b][1, 4] dioxocin and related compounds | |
| US4650873A (en) | Process for the preparation of a derivative of piperidine | |
| US5053533A (en) | Process for preparing naproxen | |
| JPH06247918A (ja) | フェニルベンズアミド誘導体の製造方法 | |
| JP2000506889A (ja) | ヒドロキシ芳香族化合物のアルキル化及びスマイルス転位の方法 | |
| JPH02300148A (ja) | ナフタレン誘導体の製法及びその合成中間体 | |
| DE69409101T2 (de) | Verfahren zur herstellung von 6-fluoro-2-halogeno-chinolin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Decisions on the lapse of the protection rights |
Effective date: 20071008 |