EA019031B1 - Способ получения 6-{4-[3-((r)-2-метилпирролидин-1-ил)пропокси]фенил}-2н-пиридазин-3-она и его фармацевтически приемлемой соли - Google Patents
Способ получения 6-{4-[3-((r)-2-метилпирролидин-1-ил)пропокси]фенил}-2н-пиридазин-3-она и его фармацевтически приемлемой соли Download PDFInfo
- Publication number
- EA019031B1 EA019031B1 EA200971019A EA200971019A EA019031B1 EA 019031 B1 EA019031 B1 EA 019031B1 EA 200971019 A EA200971019 A EA 200971019A EA 200971019 A EA200971019 A EA 200971019A EA 019031 B1 EA019031 B1 EA 019031B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- methylpyrrolidine
- tartrate
- phenyl
- mixture
- propoxy
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 17
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 4
- 238000000034 method Methods 0.000 claims abstract description 60
- 239000000203 mixture Substances 0.000 claims abstract description 56
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 54
- 239000002904 solvent Substances 0.000 claims abstract description 47
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 41
- 239000003054 catalyst Substances 0.000 claims abstract description 39
- 239000012458 free base Substances 0.000 claims abstract description 19
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims abstract description 13
- MUUWQYQRBFVTIB-UHFFFAOYSA-N 5-methyl-2,3-dihydro-1h-pyrrole Chemical compound CC1=CCCN1 MUUWQYQRBFVTIB-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002585 base Substances 0.000 claims abstract description 11
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 claims description 52
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 22
- 230000003287 optical effect Effects 0.000 claims description 20
- 229940095064 tartrate Drugs 0.000 claims description 14
- 229910052697 platinum Inorganic materials 0.000 claims description 11
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 claims description 6
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 4
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 4
- 230000008520 organization Effects 0.000 claims 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical group [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims 1
- 229910003446 platinum oxide Inorganic materials 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 abstract description 18
- 239000000543 intermediate Substances 0.000 abstract description 12
- AVAOHVDRAKDFRF-KLPPUMKISA-N (2r,3r)-2,3-dihydroxybutanedioic acid;(2r)-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1.OC(=O)[C@H](O)[C@@H](O)C(O)=O AVAOHVDRAKDFRF-KLPPUMKISA-N 0.000 abstract 5
- RGHPCLZJAFCTIK-RXMQYKEDSA-N (R)-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1 RGHPCLZJAFCTIK-RXMQYKEDSA-N 0.000 abstract 2
- XUKROCVZGZNGSI-CQSZACIVSA-N irdabisant Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C2=NNC(=O)C=C2)C=C1 XUKROCVZGZNGSI-CQSZACIVSA-N 0.000 abstract 2
- RGHPCLZJAFCTIK-YFKPBYRVSA-N (2s)-2-methylpyrrolidine Chemical compound C[C@H]1CCCN1 RGHPCLZJAFCTIK-YFKPBYRVSA-N 0.000 abstract 1
- 238000010963 scalable process Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
- 238000001953 recrystallisation Methods 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- RGHPCLZJAFCTIK-UHFFFAOYSA-N 2-methylpyrrolidine Chemical compound CC1CCCN1 RGHPCLZJAFCTIK-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000004817 gas chromatography Methods 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 230000001476 alcoholic effect Effects 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 230000003993 interaction Effects 0.000 description 6
- 150000003892 tartrate salts Chemical class 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 125000003158 alcohol group Chemical group 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000011975 tartaric acid Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical group O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000002638 heterogeneous catalyst Substances 0.000 description 3
- 239000002815 homogeneous catalyst Substances 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 230000009972 noncorrosive effect Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 229940127557 pharmaceutical product Drugs 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- TVCXVUHHCUYLGX-UHFFFAOYSA-N 2-Methylpyrrole Chemical compound CC1=CC=CN1 TVCXVUHHCUYLGX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- -1 methylpyrrolidin-1-yl Chemical group 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- MOOYVEVEDVVKGD-UHFFFAOYSA-N oxaldehydic acid;hydrate Chemical compound O.OC(=O)C=O MOOYVEVEDVVKGD-UHFFFAOYSA-N 0.000 description 1
- 239000004031 partial agonist Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000011995 wilkinson's catalyst Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US92735607P | 2007-05-03 | 2007-05-03 | |
| PCT/US2008/005702 WO2008137087A1 (en) | 2007-05-03 | 2008-05-02 | Processes for preparing (r)-2-methylpyrrolidine and (s)-2-methylpyrrolidine and tartrate salts thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200971019A1 EA200971019A1 (ru) | 2010-04-30 |
| EA019031B1 true EA019031B1 (ru) | 2013-12-30 |
Family
ID=39688886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200971019A EA019031B1 (ru) | 2007-05-03 | 2008-05-02 | Способ получения 6-{4-[3-((r)-2-метилпирролидин-1-ил)пропокси]фенил}-2н-пиридазин-3-она и его фармацевтически приемлемой соли |
Country Status (14)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ574873A (en) | 2006-07-25 | 2012-03-30 | Cephalon Inc | Pyridazinone derivatives as h3 inhibitors |
| US8383657B2 (en) | 2007-12-21 | 2013-02-26 | Abbott Laboratories | Thiazolylidine urea and amide derivatives and methods of use thereof |
| EP2752406A1 (en) * | 2008-01-30 | 2014-07-09 | Cephalon, Inc. | Substituted pyridazine derivatives which have histamine H3 antagonist activity |
| US10259794B2 (en) * | 2014-12-23 | 2019-04-16 | Cephalon, Inc. | Methods for preparing fused bicyclic 2, 4-diaminopyrimidine derivatives |
| EP3847157B1 (en) * | 2018-09-07 | 2022-05-18 | Sanofi | Process for the preparation of methyl 6-(2,4-dichlorophenyl)-5-[4-[(3s)-1-(3-fluoropropyl)pyrrolidin-3-yl]oxyphenyl]-8,9-dihydro-7h-benzo[7]annulene-2-carboxylate and a salt thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004024707A2 (en) * | 2002-09-16 | 2004-03-25 | Abbott Laboratories | Process for preparing amine type substituted benzofurans |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3329974A1 (de) | 1983-08-19 | 1985-02-28 | Bayer Ag, 5090 Leverkusen | Herstellung von hydrierten nitrilkautschuken |
| DE3433392A1 (de) | 1984-09-12 | 1986-03-20 | Bayer Ag, 5090 Leverkusen | Hydrierung nitrilgruppenhaltiger ungesaettigter polymerer |
| FR2714849B1 (fr) | 1994-01-13 | 1996-04-05 | Inst Francais Du Petrole | Procédé de préparation d'un catalyseur d'hydrogénation soluble en phase liquide organique. |
| DE4403479A1 (de) | 1994-02-04 | 1995-08-10 | Basf Ag | Verfahren zur Herstellung von Hydroxylammoniumsalzen |
| US7153889B2 (en) | 2002-11-12 | 2006-12-26 | Abbott Laboratories | Bicyclic-substituted amines as histamine-3 receptor ligands |
| WO2005085307A1 (ja) | 2004-03-08 | 2005-09-15 | Japan Science And Technology Agency | 高分子担持金属クラスター組成物 |
| US7145005B2 (en) | 2004-05-12 | 2006-12-05 | Abbott Laboratories | 2-(6-{2-[(2R)-2-Methyl-1-pyrrolidin-1-yl]-ethyl}-2-naphthalen-2-yl)-2H-pyridazin-3-one salts and their preparation |
| DE602005004404T2 (de) | 2004-06-02 | 2009-01-15 | F. Hoffmann-La Roche Ag | Als histamin-3-rezeptorliganden einsetzbare naphthalene-derivate |
| WO2006059778A1 (ja) | 2004-12-01 | 2006-06-08 | Banyu Pharmaceutical Co., Ltd. | 置換ピリドン誘導体 |
| JP2008524252A (ja) | 2004-12-17 | 2008-07-10 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | Ｃｎｓ障害の処置のためのテトラヒドロイソキノリン化合物 |
| JP2008526895A (ja) | 2005-01-21 | 2008-07-24 | シェーリング コーポレイション | ヒスタミンｈ３アンタゴニストとして有用なイミダゾールおよびベンゾイミダゾール誘導体 |
| US7790720B2 (en) | 2005-03-31 | 2010-09-07 | Ucb Pharma, S.A. | Compounds comprising an oxazole or thiazole moiety, processes for making them, and their uses |
| GB0514812D0 (en) | 2005-07-19 | 2005-08-24 | Glaxo Group Ltd | Compounds |
| US7943605B2 (en) | 2005-10-27 | 2011-05-17 | Ucb Pharma S.A. | Compounds comprising a lactam or a lactam derivative moiety, processes for making them, and their uses |
| WO2007094962A2 (en) | 2006-02-09 | 2007-08-23 | Athersys, Inc. | Pyrazoles for the treatment of obesity and other cns disorders |
| WO2007099423A1 (en) | 2006-03-02 | 2007-09-07 | Pfizer Products Inc. | 1-pyrrolidine indane derivatives as histamine-3 receptor antagonists |
| WO2007105053A2 (en) | 2006-03-13 | 2007-09-20 | Pfizer Products Inc. | Tetralines antagonists of the h-3 receptor |
| WO2008005338A1 (en) | 2006-06-29 | 2008-01-10 | Arena Pharmaceuticals, Inc. | Modulators of the histamine h3-receptor useful for the treatment of disorders related thereto |
| NZ574873A (en) * | 2006-07-25 | 2012-03-30 | Cephalon Inc | Pyridazinone derivatives as h3 inhibitors |
-
2008
- 2008-05-02 CA CA002686033A patent/CA2686033A1/en not_active Abandoned
- 2008-05-02 CN CN200880021225A patent/CN101679237A/zh active Pending
- 2008-05-02 EP EP08754205A patent/EP2152669A1/en not_active Withdrawn
- 2008-05-02 NZ NZ580948A patent/NZ580948A/en not_active IP Right Cessation
- 2008-05-02 KR KR1020097025141A patent/KR20100017565A/ko not_active Ceased
- 2008-05-02 BR BRPI0810330-5A2A patent/BRPI0810330A2/pt not_active IP Right Cessation
- 2008-05-02 WO PCT/US2008/005702 patent/WO2008137087A1/en active Application Filing
- 2008-05-02 MX MX2009011787A patent/MX2009011787A/es active IP Right Grant
- 2008-05-02 UA UAA200912476A patent/UA99913C2/ru unknown
- 2008-05-02 EA EA200971019A patent/EA019031B1/ru not_active IP Right Cessation
- 2008-05-02 JP JP2010507416A patent/JP5698887B2/ja not_active Expired - Fee Related
- 2008-05-02 AU AU2008248168A patent/AU2008248168B2/en not_active Ceased
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2009
- 2009-10-19 IL IL201627A patent/IL201627A/en not_active IP Right Cessation
- 2009-10-30 ZA ZA2009/07643A patent/ZA200907643B/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004024707A2 (en) * | 2002-09-16 | 2004-03-25 | Abbott Laboratories | Process for preparing amine type substituted benzofurans |
Non-Patent Citations (3)
| Title |
|---|
| ETIENNE, ANDRE ET AL.: "Derivatives of 2-pyrrolidone", BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, (10), 3704-12 CODEN: BSCFAS; ISSN: 0037-8968, 1969, XP002493270, compound 13B * |
| SAKURAI, RUMIKO ET AL.: "Dielectricallу Controlled Enantiomeric Resolution (DCR) of (R)- and (S)-2-Methylpyrrolidine by (R,R)-Tartaric Acid", CRYSTAL GROWTH & DESIGN, 6(7), 1606-1610 CODEN: CGDEFU; ISSN: 1528-7483, 2006, XP002493271, page 1606, left-hand column - page 1606, right-hand column; table 1 * |
| VAN DE KUIL, LUCIA A. ET AL.: "Organonickel(II) complexes containing aryl ligands with chiral pyrrolidinyl ring systems; syntheses and use as homogeneous catalysts for the Kharasch addition reaction", RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS, 113(5), 267-77 CODEN: RTCPA3; ISSN: 0165-0513, 1994, XP000611664, page 274, right-hand column; compounds 1A, B * |
Also Published As
| Publication number | Publication date |
|---|---|
| EA200971019A1 (ru) | 2010-04-30 |
| CN101679237A (zh) | 2010-03-24 |
| IL201627A0 (en) | 2010-05-31 |
| KR20100017565A (ko) | 2010-02-16 |
| CA2686033A1 (en) | 2008-11-13 |
| AU2008248168A1 (en) | 2008-11-13 |
| MX2009011787A (es) | 2009-11-13 |
| NZ580948A (en) | 2011-04-29 |
| BRPI0810330A2 (pt) | 2014-10-14 |
| EP2152669A1 (en) | 2010-02-17 |
| IL201627A (en) | 2014-06-30 |
| WO2008137087A1 (en) | 2008-11-13 |
| AU2008248168B2 (en) | 2013-03-21 |
| JP5698887B2 (ja) | 2015-04-08 |
| JP2010526142A (ja) | 2010-07-29 |
| UA99913C2 (ru) | 2012-10-25 |
| ZA200907643B (en) | 2014-03-26 |
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