HRP20040032A2 - Method for preparing 4-methylamino-4-phenylpiperidine - Google Patents
Method for preparing 4-methylamino-4-phenylpiperidine Download PDFInfo
- Publication number
- HRP20040032A2 HRP20040032A2 HR20040032A HRP20040032A HRP20040032A2 HR P20040032 A2 HRP20040032 A2 HR P20040032A2 HR 20040032 A HR20040032 A HR 20040032A HR P20040032 A HRP20040032 A HR P20040032A HR P20040032 A2 HRP20040032 A2 HR P20040032A2
- Authority
- HR
- Croatia
- Prior art keywords
- phenylpiperidine
- benzyl
- methylamino
- toluene
- formula
- Prior art date
Links
- UORMPYQLQRCWRN-UHFFFAOYSA-N n-methyl-4-phenylpiperidin-4-amine Chemical compound C=1C=CC=CC=1C1(NC)CCNCC1 UORMPYQLQRCWRN-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims description 17
- -1 alkali metal alkoxide Chemical class 0.000 claims abstract description 14
- AUBONLVMDCVPQE-UHFFFAOYSA-N 1-benzyl-4-phenylpiperidine-4-carbonitrile Chemical compound C1CC(C#N)(C=2C=CC=CC=2)CCN1CC1=CC=CC=C1 AUBONLVMDCVPQE-UHFFFAOYSA-N 0.000 claims abstract description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 11
- LTUVVZKXVNALKM-UHFFFAOYSA-N 1-benzyl-4-phenylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N)(C=2C=CC=CC=2)CCN1CC1=CC=CC=C1 LTUVVZKXVNALKM-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 9
- 230000002378 acidificating effect Effects 0.000 claims abstract description 5
- 230000007062 hydrolysis Effects 0.000 claims abstract description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 108
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 19
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
- 239000012458 free base Substances 0.000 claims description 9
- GKCPMLGASLOVJJ-UHFFFAOYSA-N methyl n-(1-benzyl-4-phenylpiperidin-4-yl)carbamate Chemical compound C1CC(NC(=O)OC)(C=2C=CC=CC=2)CCN1CC1=CC=CC=C1 GKCPMLGASLOVJJ-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 8
- 235000019253 formic acid Nutrition 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 6
- 238000006722 reduction reaction Methods 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 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 claims description 5
- 238000006264 debenzylation reaction Methods 0.000 claims description 5
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 5
- NRBVGONDKPGVKH-UHFFFAOYSA-N 1-benzyl-n-methyl-4-phenylpiperidin-4-amine Chemical compound C1CC(NC)(C=2C=CC=CC=2)CCN1CC1=CC=CC=C1 NRBVGONDKPGVKH-UHFFFAOYSA-N 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 2
- SCKHFKLKDRRXQG-UHFFFAOYSA-N 4-benzyl-4-piperidin-1-ylcyclohexa-1,5-diene-1-carbonitrile Chemical compound C1CCN(CC1)C2(CC=C(C=C2)C#N)CC3=CC=CC=C3 SCKHFKLKDRRXQG-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 239000000203 mixture Substances 0.000 description 30
- 239000000243 solution Substances 0.000 description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000012071 phase Substances 0.000 description 10
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 7
- 238000001556 precipitation Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- ONIXPLWOBQXCKH-UHFFFAOYSA-N n-methyl-4-phenylpiperidin-4-amine;oxalic acid Chemical compound OC(=O)C(O)=O.OC(=O)C(O)=O.C=1C=CC=CC=1C1(NC)CCNCC1 ONIXPLWOBQXCKH-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000010533 azeotropic distillation Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- SPXFNRMZPRHYRH-UHFFFAOYSA-N 1-benzyl-4-phenylpiperidin-1-ium-4-carbonitrile;chloride Chemical compound Cl.C1CC(C#N)(C=2C=CC=CC=2)CCN1CC1=CC=CC=C1 SPXFNRMZPRHYRH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- OUVZXDBUVYNERG-UHFFFAOYSA-N 1-benzyl-4-phenylpiperidin-4-amine Chemical compound C1CC(N)(C=2C=CC=CC=2)CCN1CC1=CC=CC=C1 OUVZXDBUVYNERG-UHFFFAOYSA-N 0.000 description 1
- FCLMXEAPEVBCKQ-UHFFFAOYSA-N 1-benzyl-4-phenylpiperidin-4-ol Chemical compound C1CC(O)(C=2C=CC=CC=2)CCN1CC1=CC=CC=C1 FCLMXEAPEVBCKQ-UHFFFAOYSA-N 0.000 description 1
- VOGNORUMSNKNHW-UHFFFAOYSA-N 1-benzyl-n-methyl-4-phenylpiperidin-4-amine;formic acid Chemical compound OC=O.C1CC(NC)(C=2C=CC=CC=2)CCN1CC1=CC=CC=C1 VOGNORUMSNKNHW-UHFFFAOYSA-N 0.000 description 1
- SJZKULRDWHPHGG-UHFFFAOYSA-N 1-benzylpiperidin-4-one Chemical compound C1CC(=O)CCN1CC1=CC=CC=C1 SJZKULRDWHPHGG-UHFFFAOYSA-N 0.000 description 1
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 102000003141 Tachykinin Human genes 0.000 description 1
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- JZIHXLNGPVLLDT-UHFFFAOYSA-N n-(1-benzyl-4-phenylpiperidin-4-yl)acetamide Chemical compound C1CC(NC(=O)C)(C=2C=CC=CC=2)CCN1CC1=CC=CC=C1 JZIHXLNGPVLLDT-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 108060008037 tachykinin Proteins 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0109575A FR2827281B1 (fr) | 2001-07-16 | 2001-07-16 | Procede pour la preparation de la 4-methylamino-4-phenylpiperidine |
| PCT/FR2002/002498 WO2003008381A1 (fr) | 2001-07-16 | 2002-07-15 | Procede pour la preparation de la 4-methylamino-4-phenylpiperidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20040032A2 true HRP20040032A2 (en) | 2004-06-30 |
Family
ID=8865643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20040032A HRP20040032A2 (en) | 2001-07-16 | 2004-01-14 | Method for preparing 4-methylamino-4-phenylpiperidine |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6916929B2 (de) |
| EP (1) | EP1409457B1 (de) |
| JP (1) | JP4307996B2 (de) |
| CN (1) | CN1254467C (de) |
| AT (1) | ATE334963T1 (de) |
| BR (1) | BR0211135A (de) |
| CA (1) | CA2450362A1 (de) |
| DE (1) | DE60213603T2 (de) |
| ES (1) | ES2269766T3 (de) |
| FR (1) | FR2827281B1 (de) |
| HR (1) | HRP20040032A2 (de) |
| HU (1) | HUP0401458A2 (de) |
| MX (1) | MXPA04000513A (de) |
| PL (1) | PL368938A1 (de) |
| WO (1) | WO2003008381A1 (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7576216B2 (en) | 2004-07-30 | 2009-08-18 | Abbott Laboratories | Preparation of pyridonecarboxylic acid antibacterials |
| ES2506143T3 (es) * | 2004-07-30 | 2014-10-13 | Abbvie Inc. | Preparación de sustancias antibacterianas de ácido piridonacarboxílico |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6262066B1 (en) * | 1998-07-27 | 2001-07-17 | Schering Corporation | High affinity ligands for nociceptin receptor ORL-1 |
-
2001
- 2001-07-16 FR FR0109575A patent/FR2827281B1/fr not_active Expired - Fee Related
-
2002
- 2002-07-15 EP EP02770025A patent/EP1409457B1/de not_active Expired - Lifetime
- 2002-07-15 DE DE60213603T patent/DE60213603T2/de not_active Expired - Lifetime
- 2002-07-15 JP JP2003513941A patent/JP4307996B2/ja not_active Expired - Fee Related
- 2002-07-15 US US10/483,475 patent/US6916929B2/en not_active Expired - Fee Related
- 2002-07-15 WO PCT/FR2002/002498 patent/WO2003008381A1/fr active IP Right Grant
- 2002-07-15 CN CNB028140966A patent/CN1254467C/zh not_active Expired - Fee Related
- 2002-07-15 PL PL02368938A patent/PL368938A1/xx unknown
- 2002-07-15 AT AT02770025T patent/ATE334963T1/de not_active IP Right Cessation
- 2002-07-15 HU HU0401458A patent/HUP0401458A2/hu unknown
- 2002-07-15 CA CA002450362A patent/CA2450362A1/en not_active Abandoned
- 2002-07-15 BR BR0211135-7A patent/BR0211135A/pt not_active IP Right Cessation
- 2002-07-15 MX MXPA04000513A patent/MXPA04000513A/es not_active Application Discontinuation
- 2002-07-15 ES ES02770025T patent/ES2269766T3/es not_active Expired - Lifetime
-
2004
- 2004-01-14 HR HR20040032A patent/HRP20040032A2/hr not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0401458A2 (hu) | 2004-12-28 |
| DE60213603T2 (de) | 2007-10-11 |
| EP1409457A1 (de) | 2004-04-21 |
| JP4307996B2 (ja) | 2009-08-05 |
| DE60213603D1 (de) | 2006-09-14 |
| US6916929B2 (en) | 2005-07-12 |
| CA2450362A1 (en) | 2003-01-30 |
| BR0211135A (pt) | 2004-06-29 |
| EP1409457B1 (de) | 2006-08-02 |
| CN1527817A (zh) | 2004-09-08 |
| MXPA04000513A (es) | 2004-07-23 |
| CN1254467C (zh) | 2006-05-03 |
| ATE334963T1 (de) | 2006-08-15 |
| US20040181071A1 (en) | 2004-09-16 |
| ES2269766T3 (es) | 2007-04-01 |
| PL368938A1 (en) | 2005-04-04 |
| FR2827281A1 (fr) | 2003-01-17 |
| WO2003008381A1 (fr) | 2003-01-30 |
| JP2004536130A (ja) | 2004-12-02 |
| FR2827281B1 (fr) | 2003-12-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20060148866A1 (en) | Novel process for preparing pramipexole and its optical isomeric mixture by reduction with sodium triacetoxyborohydride | |
| US9725420B2 (en) | Processes | |
| US6495700B1 (en) | Process for producing phenserine and its analog | |
| JP2815614B2 (ja) | ４―アミノ―３―カルボキシ―ナフチリジン誘導体、その製法および医薬組成物 | |
| WO2000062782A1 (en) | Novel synthesis and crystallization of piperazine ring-containing compounds | |
| HRP20040032A2 (en) | Method for preparing 4-methylamino-4-phenylpiperidine | |
| US20220204514A1 (en) | Polymorphs of 7-cyclopentyl-n,n-dimethyl-2-{[5-(piperazin-1-yl) pyridin-2-yl]-amino}-7h-pyrrolo[2,3-d]pyrimidine-6-carboxamide and its pharmaceutically acceptable salts and process for the preparation thereof | |
| CA2038908A1 (en) | Indole derivatives | |
| US20010051718A1 (en) | Novel synthesis and crystallization of piperazine ring-containing compounds | |
| NZ503062A (en) | Preparing dihydrate form of L-tartaric acid without isolating (3aR)-2,3a,4,5,6,7-hexahydro-2-methyl-3a-(phenylmethyl)-3H-pyrazolo[4,3-c]pyridin-3-one whereupon the appropriate form is crystallised upon cooling | |
| SK3952004A3 (sk) | Spôsob izolácie 14-hydroxykodeinonu | |
| WO2006070379A1 (en) | A process for preparation of 4-amino-1-isobutyl-1h-imidazo[4,5-c]-quinoline (imiquimod) | |
| EP1048667B1 (de) | Verfahren zur Herstellung von 8-cyclopentyl-6-ethyl-3 (substituierten)-5,8-dihydro-4H-1,2,3A,7,8-penta aza-as-Indacenen und dafür geeigneter Zwischenprodukte | |
| US20100228032A1 (en) | Process for Making Apomorphine and Apocodeine | |
| CA2936192A1 (en) | Processes for the synthesis of substituted urea compounds | |
| US3430258A (en) | Barbituric acid derivatives and a process for preparation thereof | |
| US20120259116A1 (en) | Novel Process for the Preparation of Paliperidone | |
| US6603003B2 (en) | Method for the preparation of piperazine and its derivatives | |
| JP2003514908A (ja) | テトラヒドロ−［１，８］−ナフチリジンに向けた方法および中間体 | |
| US20040176591A1 (en) | Novel synthesis and crystallization of peperazine ring-containing compounds | |
| US20220127236A1 (en) | Process for the preparation of substituted pyrazole derivatives | |
| US4351944A (en) | Improved process for preparing 3-(4-pyridinyl)aniline | |
| Mueller et al. | Some Derivatives of 7-Methoxy-and 10-Methoxybenzo (f) quinoline | |
| HRP20040031A2 (en) | Method for preparing 4-amino-4-phenylpiperidines | |
| JPH11255745A (ja) | ナフチリドンの製造方法及び中間体 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1OB | Publication of a patent application | ||
| ARAI | Request for the grant of a patent on the basis of the submitted results of a substantive examination of a patent application | ||
| PNAN | Change of the applicant name, address/residence |
Owner name: SANOFI-AVENTIS, FR |
|
| ODRP | Renewal fee for the maintenance of a patent |
Payment date: 20060607 Year of fee payment: 5 |
|
| OBST | Application withdrawn |