WO2001016089A1 - A process for the preparation of cis-(1s,4s)-n-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine hydrochloride - Google Patents
A process for the preparation of cis-(1s,4s)-n-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine hydrochloride Download PDFInfo
- Publication number
- WO2001016089A1 WO2001016089A1 PCT/IB2000/001182 IB0001182W WO0116089A1 WO 2001016089 A1 WO2001016089 A1 WO 2001016089A1 IB 0001182 W IB0001182 W IB 0001182W WO 0116089 A1 WO0116089 A1 WO 0116089A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- cis
- hydrochloride
- dichlorophenyl
- compound
- Prior art date
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 31
- 230000008569 process Effects 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims abstract description 26
- GLQPTZAAUROJMO-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)benzaldehyde Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(C=O)C=C1 GLQPTZAAUROJMO-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229960003660 sertraline hydrochloride Drugs 0.000 claims abstract description 14
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000007868 Raney catalyst Substances 0.000 claims abstract description 7
- 229910000564 Raney nickel Inorganic materials 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 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 claims abstract description 5
- 229910052751 metal Inorganic materials 0.000 claims abstract description 4
- 239000002184 metal Substances 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 8
- 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 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- RZPFVRFSYMUDJO-UHFFFAOYSA-N 2h-naphthalen-1-one Chemical compound C1=CC=C2C(=O)CC=CC2=C1 RZPFVRFSYMUDJO-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 3
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 229960002510 mandelic acid Drugs 0.000 claims description 2
- 239000003586 protic polar solvent Substances 0.000 claims description 2
- 239000003772 serotonin uptake inhibitor Substances 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 abstract description 10
- AELCINSCMGFISI-DTWKUNHWSA-N (1R,2S)-tranylcypromine Chemical compound N[C@@H]1C[C@H]1C1=CC=CC=C1 AELCINSCMGFISI-DTWKUNHWSA-N 0.000 abstract 1
- VGKDLMBJGBXTGI-SJKOYZFVSA-N (1r,4r)-4-(3,4-dichlorophenyl)-n-methyl-1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C1([C@H]2CC[C@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJKOYZFVSA-N 0.000 abstract 1
- -1 amine hydrochloride Chemical class 0.000 abstract 1
- LKLWVKCEYSPQHL-KKSFZXQISA-O cyclanoline Chemical compound C12=CC(O)=C(OC)C=C2CC[N@+]2(C)[C@H]1CC1=CC=C(OC)C(O)=C1C2 LKLWVKCEYSPQHL-KKSFZXQISA-O 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 150000002576 ketones Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DETWFIUAXSWCIK-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-ylazanium;chloride Chemical compound [Cl-].C1=CC=C2C([NH3+])CCCC2=C1 DETWFIUAXSWCIK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000011946 reduction process Methods 0.000 description 2
- 238000006268 reductive amination reaction Methods 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 229960002073 sertraline Drugs 0.000 description 2
- 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 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 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 description 1
- 229940123445 Tricyclic antidepressant Drugs 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 230000000697 serotonin reuptake Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
- C07C209/26—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with hydrogen
Definitions
- This invention relates to a process for the preparation of N-methyl-4-
- sertraline hydrochloride which is cis-(l S,4S)-N-methyl-4-(3 ,4-
- serotonin resides in the cis-1 S,4S isomer i.e. cis-(l S, 4S)-N-methyl-4-
- hydrochloride (I) commonly known as sertraline hydrochloride.
- hydrochloride (II) are known in the literature.
- the inline was hydrogenated using 10% Pd/C as catalyst to give the
- a metal hydride reagent e.g. sodium
- titanium tetrachloride is crucial, as the reagent is moisture sensitive and
- the first object of the invention is to produce sertraline hydrochloride
- Another object of the present invention is to produce cis-N-methyl-4-
- Yet another object of the present invention is to produce the said
- the present invention provides a process for preparation
- naphthalenearnine hydrochloride i.e. sertraline hydrochloride of the
- metal catalyst such as Raney Nickel
- the invention also provides for preparation of intermediate cis-N-
- hydrochloride of formula - VI which comprises the process steps (a), (b)
- Solvent for the reaction is protic polar in the nature.
- Protic polar solvent is protic polar solvent
- lower alcohol such as C 1 -C 3 alcohols may be used.
- C 1 -C 3 alcohols may be used.
- the temperature as one of the preferred
- parameters may be varied over the range of room temperature to 100°C.
- Preferred solvent is methanol.
- Preferred hydrogen pressure is 450-500 psi
- isomer is carried out by separating all cis-isomers from the said isomeric
- naphthalenone (15.0 gm) is taken, followed by addition of 250 ml.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU65875/00A AU6587500A (en) | 1999-09-01 | 2000-08-28 | A process for the preparation of cis-(1s,4s)-n-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahyd ro-1-naphthaleneamine hydrochloride |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN748/CAL/99 | 1999-09-01 | ||
| IN748CA1999 IN185109B (enrdf_load_stackoverflow) | 1999-09-01 | 1999-09-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2001016089A1 true WO2001016089A1 (en) | 2001-03-08 |
Family
ID=11084493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IB2000/001182 WO2001016089A1 (en) | 1999-09-01 | 2000-08-28 | A process for the preparation of cis-(1s,4s)-n-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine hydrochloride |
Country Status (4)
| Country | Link |
|---|---|
| AR (1) | AR025461A1 (enrdf_load_stackoverflow) |
| AU (1) | AU6587500A (enrdf_load_stackoverflow) |
| IN (1) | IN185109B (enrdf_load_stackoverflow) |
| WO (1) | WO2001016089A1 (enrdf_load_stackoverflow) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002096860A1 (en) * | 2001-05-31 | 2002-12-05 | Orion Corporation Fermion | Process for preparing sertraline intermediates |
| US6723878B2 (en) | 2001-06-15 | 2004-04-20 | Orion Corporation Fermion | Method for preparing sertraline |
| US6809221B2 (en) | 2000-03-14 | 2004-10-26 | Teva Pharmaceutical Industries Ltd. | Process for preparing (+)-cis-sertraline |
| US6897340B2 (en) | 2002-04-29 | 2005-05-24 | Teva Pharmaceutical Industries Ltd. | Processes for preparation of polymorphic form II of sertraline hydrochloride |
| WO2006091732A1 (en) * | 2005-02-23 | 2006-08-31 | Teva Pharmaceutical Industries Ltd. | Processes for preparing sertraline |
| WO2006129324A2 (en) | 2005-06-03 | 2006-12-07 | Hetero Drugs Limited | A highly stereoselective synthesis of sertraline |
| US7262327B2 (en) | 2003-09-05 | 2007-08-28 | Teva Pharmaceutical Industries Ltd. | Recycling process for preparing sertraline |
| US7276629B2 (en) | 2003-04-14 | 2007-10-02 | Teva Pharmaceutical Industries Ltd. | Hydrogenation of imine intermediates of sertraline with catalysts |
| US7345201B2 (en) | 2005-02-23 | 2008-03-18 | Teva Pharmaceutical Industries, Ltd. | Processes for preparing sertraline |
| WO2007119247A3 (en) * | 2006-04-17 | 2009-05-14 | Unichem Lab Ltd | Improved manufacturing procedure for the preparation of polymorphic form ii of cis-(1s)-n-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthleneamine hydrochloride (sertraline hydrochloride) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0030081A1 (en) * | 1979-11-01 | 1981-06-10 | Pfizer Inc. | Antidepressant derivatives of cis-4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine and pharmaceutical compositions thereof |
| WO1999036394A1 (en) * | 1998-01-16 | 1999-07-22 | Pfizer Products Inc. | Novel process for preparing a ketimine |
-
1999
- 1999-09-01 IN IN748CA1999 patent/IN185109B/en unknown
-
2000
- 2000-08-28 WO PCT/IB2000/001182 patent/WO2001016089A1/en active Application Filing
- 2000-08-28 AU AU65875/00A patent/AU6587500A/en not_active Abandoned
- 2000-08-31 AR ARP000104545A patent/AR025461A1/es unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0030081A1 (en) * | 1979-11-01 | 1981-06-10 | Pfizer Inc. | Antidepressant derivatives of cis-4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine and pharmaceutical compositions thereof |
| WO1999036394A1 (en) * | 1998-01-16 | 1999-07-22 | Pfizer Products Inc. | Novel process for preparing a ketimine |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6809221B2 (en) | 2000-03-14 | 2004-10-26 | Teva Pharmaceutical Industries Ltd. | Process for preparing (+)-cis-sertraline |
| WO2002096860A1 (en) * | 2001-05-31 | 2002-12-05 | Orion Corporation Fermion | Process for preparing sertraline intermediates |
| US6723878B2 (en) | 2001-06-15 | 2004-04-20 | Orion Corporation Fermion | Method for preparing sertraline |
| US6897340B2 (en) | 2002-04-29 | 2005-05-24 | Teva Pharmaceutical Industries Ltd. | Processes for preparation of polymorphic form II of sertraline hydrochloride |
| US7276629B2 (en) | 2003-04-14 | 2007-10-02 | Teva Pharmaceutical Industries Ltd. | Hydrogenation of imine intermediates of sertraline with catalysts |
| US7262327B2 (en) | 2003-09-05 | 2007-08-28 | Teva Pharmaceutical Industries Ltd. | Recycling process for preparing sertraline |
| WO2006091732A1 (en) * | 2005-02-23 | 2006-08-31 | Teva Pharmaceutical Industries Ltd. | Processes for preparing sertraline |
| US7345201B2 (en) | 2005-02-23 | 2008-03-18 | Teva Pharmaceutical Industries, Ltd. | Processes for preparing sertraline |
| US7518018B2 (en) | 2005-02-23 | 2009-04-14 | Teva Pharmaceutical Industries Ltd. | Processes for preparing sertraline |
| WO2006129324A2 (en) | 2005-06-03 | 2006-12-07 | Hetero Drugs Limited | A highly stereoselective synthesis of sertraline |
| WO2007119247A3 (en) * | 2006-04-17 | 2009-05-14 | Unichem Lab Ltd | Improved manufacturing procedure for the preparation of polymorphic form ii of cis-(1s)-n-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthleneamine hydrochloride (sertraline hydrochloride) |
Also Published As
| Publication number | Publication date |
|---|---|
| AU6587500A (en) | 2001-03-26 |
| AR025461A1 (es) | 2002-11-27 |
| IN185109B (enrdf_load_stackoverflow) | 2000-11-18 |
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