NO300970B1 - Fremstilling av substituerte piperidiner samt mellomprodukter deri - Google Patents

Fremstilling av substituerte piperidiner samt mellomprodukter deri Download PDF

Info

Publication number: NO300970B1
Authority: NO; Norway
Prior art keywords: formula; compound; phenyl; alkoxy; alkyl
Prior art date: 1991-11-27

Application number

NO941958A

Other languages

English (en)

Norwegian (no)

Other versions

NO941958L (no

NO941958D0 (no

Inventor

Dennis Michael Godek

Sally Gut-Ruggeri

Terry Jay Rosen

Lewin T Wint

Original Assignee

Pfizer

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1991-11-27

Filing date

1994-05-26

Publication date

1997-08-25

1994-05-26 Application filed by Pfizer filed Critical Pfizer

1994-05-26 Publication of NO941958L publication Critical patent/NO941958L/no

1994-05-26 Publication of NO941958D0 publication Critical patent/NO941958D0/no

1997-08-25 Publication of NO300970B1 publication Critical patent/NO300970B1/no

Links

238000002360 preparation method Methods 0.000 title abstract description 7
150000003053 piperidines Chemical class 0.000 title abstract description 4
239000000543 intermediate Chemical class 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 66
238000000034 method Methods 0.000 claims abstract description 17
238000006243 chemical reaction Methods 0.000 claims description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 19
-1 cyano, hydroxyl Chemical group 0.000 claims description 19
239000003638 chemical reducing agent Substances 0.000 claims description 17
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
229910052794 bromium Inorganic materials 0.000 claims description 16
229910052801 chlorine Inorganic materials 0.000 claims description 16
239000000460 chlorine Substances 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
229910052736 halogen Inorganic materials 0.000 claims description 13
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
229910052731 fluorine Inorganic materials 0.000 claims description 10
239000011737 fluorine Substances 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 8
125000003282 alkyl amino group Chemical group 0.000 claims description 8
239000012321 sodium triacetoxyborohydride Substances 0.000 claims description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
229910052740 iodine Chemical group 0.000 claims description 6
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 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
239000011630 iodine Chemical group 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 4
125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 3
125000004663 dialkyl amino group Chemical group 0.000 claims description 3
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 3
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 8
125000004433 nitrogen atom Chemical group N* 0.000 claims 3
238000004519 manufacturing process Methods 0.000 claims 2
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000003054 catalyst Substances 0.000 description 12
239000000203 mixture Substances 0.000 description 12
239000002904 solvent Substances 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
239000012442 inert solvent Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
239000012458 free base Substances 0.000 description 5
150000002466 imines Chemical class 0.000 description 5
150000002902 organometallic compounds Chemical class 0.000 description 5
238000010992 reflux Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
102100024304 Protachykinin-1 Human genes 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
101800003906 Substance P Proteins 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
229910052744 lithium Inorganic materials 0.000 description 4
239000000463 material Substances 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
229910052723 transition metal Inorganic materials 0.000 description 4
150000003624 transition metals Chemical class 0.000 description 4
IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 description 3
IWYDHOAUDWTVEP-ZETCQYMHSA-N (S)-mandelic acid Chemical compound OC(=O)[C@@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-ZETCQYMHSA-N 0.000 description 3
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
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 3
239000002585 base Substances 0.000 description 3
239000002274 desiccant Substances 0.000 description 3
239000010410 layer Substances 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
229910001623 magnesium bromide Inorganic materials 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 3
239000007787 solid Substances 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical class O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 2
RHWHWJGHOFRMMN-QQTWVUFVSA-N (2s,3s)-n-[[2-methoxy-5-(trifluoromethoxy)phenyl]methyl]-2-phenylpiperidin-3-amine;hydrochloride Chemical compound Cl.COC1=CC=C(OC(F)(F)F)C=C1CN[C@@H]1[C@H](C=2C=CC=CC=2)NCCC1 RHWHWJGHOFRMMN-QQTWVUFVSA-N 0.000 description 2
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 2
RFJZMFAQTFZUIV-UHFFFAOYSA-N 2-chloro-n-[[2-methoxy-5-(trifluoromethoxy)phenyl]methyl]pyridin-3-amine Chemical compound COC1=CC=C(OC(F)(F)F)C=C1CNC1=CC=CN=C1Cl RFJZMFAQTFZUIV-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
208000018522 Gastrointestinal disease Diseases 0.000 description 2
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 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
102000003141 Tachykinin Human genes 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
239000003456 ion exchange resin Substances 0.000 description 2
229920003303 ion-exchange polymer Polymers 0.000 description 2
238000002955 isolation Methods 0.000 description 2
238000002156 mixing Methods 0.000 description 2
WDWWWRCSIXNNKK-UHFFFAOYSA-N n-[[2-methoxy-5-(trifluoromethoxy)phenyl]methyl]-2-phenylpyridin-3-amine Chemical compound COC1=CC=C(OC(F)(F)F)C=C1CNC1=CC=CN=C1C1=CC=CC=C1 WDWWWRCSIXNNKK-UHFFFAOYSA-N 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
238000006053 organic reaction Methods 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
239000011736 potassium bicarbonate Substances 0.000 description 2
235000015497 potassium bicarbonate Nutrition 0.000 description 2
229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
229940086066 potassium hydrogencarbonate Drugs 0.000 description 2
239000000047 product Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
238000000638 solvent extraction Methods 0.000 description 2
108060008037 tachykinin Proteins 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
239000011701 zinc Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
ZIWFCOIGUNPHPM-HKUYNNGSSA-N (2s,3s)-n-[[2-methoxy-5-(trifluoromethoxy)phenyl]methyl]-2-phenylpiperidin-3-amine Chemical compound COC1=CC=C(OC(F)(F)F)C=C1CN[C@@H]1[C@H](C=2C=CC=CC=2)NCCC1 ZIWFCOIGUNPHPM-HKUYNNGSSA-N 0.000 description 1
MEQBJJUWDCYIAB-UHFFFAOYSA-N 2-chloropyridin-3-amine Chemical compound NC1=CC=CN=C1Cl MEQBJJUWDCYIAB-UHFFFAOYSA-N 0.000 description 1
ATRDCTRZAJKDPL-UHFFFAOYSA-N 2-methoxy-5-(trifluoromethoxy)benzaldehyde Chemical compound COC1=CC=C(OC(F)(F)F)C=C1C=O ATRDCTRZAJKDPL-UHFFFAOYSA-N 0.000 description 1
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
XQDSIGDVDWFZPP-UHFFFAOYSA-N 2-phenylpiperidin-1-amine Chemical compound NN1CCCCC1C1=CC=CC=C1 XQDSIGDVDWFZPP-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
208000019901 Anxiety disease Diseases 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
208000006561 Cluster Headache Diseases 0.000 description 1
206010009900 Colitis ulcerative Diseases 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
208000011231 Crohn disease Diseases 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
208000001640 Fibromyalgia Diseases 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
208000019695 Migraine disease Diseases 0.000 description 1
102000002002 Neurokinin-1 Receptors Human genes 0.000 description 1
108010040718 Neurokinin-1 Receptors Proteins 0.000 description 1
102000003797 Neuropeptides Human genes 0.000 description 1
108090000189 Neuropeptides Proteins 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
208000002193 Pain Diseases 0.000 description 1
208000025747 Rheumatic disease Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
201000006704 Ulcerative Colitis Diseases 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000003275 alpha amino acid group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
208000015114 central nervous system disease Diseases 0.000 description 1
208000018912 cluster headache syndrome Diseases 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
XXECWTBMGGXMKP-UHFFFAOYSA-L dichloronickel;2-diphenylphosphanylethyl(diphenyl)phosphane Chemical group Cl[Ni]Cl.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 XXECWTBMGGXMKP-UHFFFAOYSA-L 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
RDFJFVXMRYVOAC-UHFFFAOYSA-N methiodal Chemical compound OS(=O)(=O)CI RDFJFVXMRYVOAC-UHFFFAOYSA-N 0.000 description 1
206010027599 migraine Diseases 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
230000007310 pathophysiology Effects 0.000 description 1
ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
208000023504 respiratory system disease Diseases 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
201000000980 schizophrenia Diseases 0.000 description 1
239000002002 slurry Substances 0.000 description 1
210000002460 smooth muscle Anatomy 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
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
230000007306 turnover Effects 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
229910052720 vanadium Inorganic materials 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- 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
- 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]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Rheumatology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pain & Pain Management (AREA)
Biomedical Technology (AREA)
Pulmonology (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pyridine Compounds (AREA)

NO941958A 1991-11-27 1994-05-26 Fremstilling av substituerte piperidiner samt mellomprodukter deri NO300970B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US07/800,667 US5364943A (en)	1991-11-27	1991-11-27	Preparation of substituted piperidines
PCT/US1992/009929 WO1993011110A1 (en)	1991-11-27	1992-11-24	Preparation of substituted piperidines

Publications (3)

Publication Number	Publication Date
NO941958L NO941958L (no)	1994-05-26
NO941958D0 NO941958D0 (no)	1994-05-26
NO300970B1 true NO300970B1 (no)	1997-08-25

Family

ID=25179032

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO941958A NO300970B1 (no)	1991-11-27	1994-05-26	Fremstilling av substituerte piperidiner samt mellomprodukter deri

Country Status (19)

Country	Link
US (2)	US5364943A (fi)
EP (1)	EP0619806B1 (fi)
JP (1)	JP2587903B2 (fi)
KR (1)	KR0150254B1 (fi)
AT (1)	ATE132487T1 (fi)
AU (1)	AU670765B2 (fi)
BR (1)	BR9206823A (fi)
CA (1)	CA2124083C (fi)
CZ (1)	CZ292947B6 (fi)
DE (1)	DE69207429T2 (fi)
DK (1)	DK0619806T3 (fi)
ES (1)	ES2081636T3 (fi)
FI (1)	FI107049B (fi)
GR (1)	GR3018679T3 (fi)
HU (1)	HUT70514A (fi)
NO (1)	NO300970B1 (fi)
PL (1)	PL173659B1 (fi)
RU (1)	RU2081112C1 (fi)
WO (1)	WO1993011110A1 (fi)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1994003445A1 (en) *	1992-08-04	1994-02-17	Pfizer Inc.	3-benzylamino-2-phenyl-piperidine derivatives as substance p receptor antagonists
CA2162400A1 (en) *	1993-05-28	1994-12-08	William M. Snyder	Process for preparing and resolving 2-phenyl-3-aminopiperidine
GB9317987D0 (en) *	1993-08-26	1993-10-13	Glaxo Group Ltd	Chemical compounds
TW340842B (en) *	1995-08-24	1998-09-21	Pfizer	Substituted benzylaminopiperidine compounds
PT780375E (pt)	1995-12-21	2002-12-31	Pfizer	3-¬(benzilo substituido em 5)amino\|-2-phenilpiperidinas como antagonistas da substancia p
US5922898A (en) *	1997-04-08	1999-07-13	Catalytica Pharmaceuticals, Inc.	Process for preparing biaryl compounds
US6194599B1 (en)	1997-04-08	2001-02-27	Catalytica, Inc.	Process for preparing biaryl compounds
NZ329807A (en) *	1997-04-23	2000-07-28	Pfizer	NK-1 receptor antagonists and P receptor antagonists 2-Diarylmethyl-3-amino-1-azabicyclo[2.2.2]octane derivatives and amino substituted N-containing rings as agents for treating irritable bowel syndrome
CA2291734A1 (en)	1997-06-27	1999-01-07	Merck Sharp & Dohme Limited	Substituted 3-(benzylamino)piperidine derivatives and their use as therapeutic agents
DE19824470A1 (de) *	1998-05-30	1999-12-02	Boehringer Ingelheim Pharma	Neue Neurokininantagonisten, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen
DE60014216T2 (de)	1999-02-24	2006-03-02	F. Hoffmann-La Roche Ag	4-Phenylpyridinderivate und deren Verwendung als NK-1 Rezeptorantagonisten
RS49964B (sr) *	1999-05-17	2008-09-29	Pfizer Products Inc.,	Postupak za dobijanje 2-fenil-3-aminopiridina,njegovih supstituisanih fenil derivata, i njegovih soli
US6962999B2 (en) *	2001-07-25	2005-11-08	Pharmacore, Inc.	Process for preparing unsymmetrical biaryls and alkylated aromatic compounds from arylnitriles
US6911544B2 (en) *	2002-10-23	2005-06-28	Pfizer Inc.	Process for the preparation of (S,S)-cis-2-phenyl-3-aminopiperidine
US7105467B2 (en) *	2003-07-08	2006-09-12	Pharmacore, Inc.	Nickel catalyzed cross-coupling reactions between organomagnesium compounds and anisole derivatives
TWI280239B (en)	2003-07-15	2007-05-01	Hoffmann La Roche	Process for preparation of pyridine derivatives
US7105707B2 (en) *	2003-12-17	2006-09-12	Pharmacore, Inc.	Process for preparing alkynyl-substituted aromatic and heterocyclic compounds
JP5523706B2 (ja)	2005-09-23	2014-06-18	エフ．ホフマン−ラロシュアーゲー	新規投薬配合物

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3560510A (en) *	1969-03-05	1971-02-02	Aldrich Chem Co Inc	2-benzhydrylquinuclidines
CA1160229A (en) *	1979-03-13	1984-01-10	Pieter T. Haken	Pyridyliminomethylbenzene derivatives
GB2056974B (en) *	1979-07-19	1984-02-29	Shell Int Research	Heterocyclic acylamino compounds having fungicidal herbicidal and plant-growth regulating properties
CA1231710A (en) *	1979-07-19	1988-01-19	Haken Pieter Ten	Heterocyclic compounds having fungicidal, herbicidal and plant-growth regulating properties
GB2067187B (en) *	1979-12-07	1983-11-30	Cosmos Enterprise	Process for the preparation of 1-(4-hydroxyphenyl)-2-(4-benzylpiperidino)-1-propanol and acid addition salts thereof
EP0100158A3 (en) *	1982-07-28	1985-03-27	The Upjohn Company	(3-pyridinyl)heteroalkarylalkanols, alkanoic acids and esters
US4552960A (en) *	1983-06-20	1985-11-12	Eli Lilly And Company	Fungicidal amines
US4680283A (en) *	1984-09-26	1987-07-14	Merck & Co., Inc.	Analogs of substance P and eledoisin
MX18467A (es) *	1988-11-23	1993-07-01	Pfizer	Agentes terapeuticos de quinuclidinas
WO1991009844A1 (en) *	1990-01-04	1991-07-11	Pfizer Inc.	Substance p antagonists
EP0532515B1 (en) *	1990-05-31	1996-10-23	Pfizer Inc.	Preparation of substituted piperidines
US5138060A (en) *	1991-01-03	1992-08-11	Pfizer Inc.	Process and intermediates for preparing azabicyclo(2.2.2)octan-3-imines
CA2100163A1 (en) *	1991-01-10	1992-07-11	John A. Lowe, Iii	N-alkyl quinuclidinium salts
CA2106200C (en) *	1991-03-26	1996-11-19	Terry J. Rosen	Stereoselective preparation of substituted piperidines
ES2092113T3 (es) *	1991-06-20	1996-11-16	Pfizer	Derivados fluoroalcoxibencilamino de heterociclos que contienen nitrogeno.
TW202432B (fi) *	1991-06-21	1993-03-21	Pfizer

1991
- 1991-11-27 US US07/800,667 patent/US5364943A/en not_active Expired - Lifetime
1992
- 1992-11-24 JP JP5510148A patent/JP2587903B2/ja not_active Expired - Fee Related
- 1992-11-24 AT AT92925298T patent/ATE132487T1/de not_active IP Right Cessation
- 1992-11-24 EP EP92925298A patent/EP0619806B1/en not_active Expired - Lifetime
- 1992-11-24 HU HU9401584A patent/HUT70514A/hu unknown
- 1992-11-24 PL PL92303982A patent/PL173659B1/pl not_active IP Right Cessation
- 1992-11-24 BR BR9206823A patent/BR9206823A/pt not_active Application Discontinuation
- 1992-11-24 ES ES92925298T patent/ES2081636T3/es not_active Expired - Lifetime
- 1992-11-24 DE DE69207429T patent/DE69207429T2/de not_active Expired - Fee Related
- 1992-11-24 WO PCT/US1992/009929 patent/WO1993011110A1/en not_active Application Discontinuation
- 1992-11-24 KR KR1019940701782A patent/KR0150254B1/ko not_active IP Right Cessation
- 1992-11-24 CZ CZ19941300A patent/CZ292947B6/cs not_active IP Right Cessation
- 1992-11-24 AU AU31408/93A patent/AU670765B2/en not_active Ceased
- 1992-11-24 DK DK92925298.9T patent/DK0619806T3/da active
- 1992-11-24 RU RU9294027570A patent/RU2081112C1/ru not_active IP Right Cessation
- 1992-11-24 CA CA002124083A patent/CA2124083C/en not_active Expired - Fee Related
1994
- 1994-05-26 NO NO941958A patent/NO300970B1/no unknown
- 1994-05-26 FI FI942457A patent/FI107049B/fi not_active IP Right Cessation
- 1994-07-12 US US08/273,662 patent/US5663349A/en not_active Expired - Fee Related
1996
- 1996-01-17 GR GR960400080T patent/GR3018679T3/el unknown

Also Published As

Publication number	Publication date
US5663349A (en)	1997-09-02
EP0619806A1 (en)	1994-10-19
DE69207429T2 (de)	1996-05-15
FI942457A0 (fi)	1994-05-26
HU9401584D0 (en)	1994-08-29
CZ130094A3 (en)	1995-11-15
JPH06510795A (ja)	1994-12-01
HUT70514A (en)	1995-10-30
KR0150254B1 (ko)	1998-10-15
ES2081636T3 (es)	1996-03-16
BR9206823A (pt)	1995-04-25
NO941958L (no)	1994-05-26
DK0619806T3 (da)	1996-02-05
NO941958D0 (no)	1994-05-26
CZ292947B6 (cs)	2004-01-14
WO1993011110A1 (en)	1993-06-10
DE69207429D1 (de)	1996-02-15
AU670765B2 (en)	1996-08-01
RU2081112C1 (ru)	1997-06-10
FI107049B (fi)	2001-05-31
US5364943A (en)	1994-11-15
FI942457A (fi)	1994-05-26
AU3140893A (en)	1993-06-28
PL173659B1 (pl)	1998-04-30
CA2124083C (en)	2001-08-14
JP2587903B2 (ja)	1997-03-05
ATE132487T1 (de)	1996-01-15
EP0619806B1 (en)	1996-01-03
GR3018679T3 (en)	1996-04-30
CA2124083A1 (en)	1993-06-10

Publication	Publication Date	Title
NO300970B1 (no)	1997-08-25	Fremstilling av substituerte piperidiner samt mellomprodukter deri
KR20210068472A (ko)	2021-06-09	Shp2 활성의 억제를 위한 화합물 및 조성물의 제조
AU648558B2 (en)	1994-04-28	Preparation of substituted piperidines
US5965734A (en)	1999-10-12	Processes and intermediates for preparing 2-substituted piperidine stereoisomers
JP2965675B2 (ja)	1999-10-18	（―）―１―ベンジル―４―〔（５，６―ジメトキシ―１―インダノン）―２―イル〕メチルピペリジンの製造方法
US6066737A (en)	2000-05-23	Process for the preparation of optically enriched 4-aryl-3-hydromethyl substituted piperidines to be used as intermediates in the synthesis of paroxetine
JPH04266875A (ja)	1992-09-22	新規なイミダゾール化合物、その製造方法およびこれらの化合物を含有する医薬組成物
EP1257527B1 (en)	2003-10-29	(2s)-aminoindan derivatives, a process for their preparation and their use as selective dopamine d3 ligands
TW202216723A (zh)	2022-05-01	用於抑制shp2活性的化合物及組成物之製造
EP1442017A1 (en)	2004-08-04	Preparation of benzosuberonylpiperidine compounds
RU2797951C2 (ru)	2023-06-13	Производство соединений и композиций для подавления активности shp2
EP0251547A2 (en)	1988-01-07	Chiral synthesis of (+)-trans-la-2,3,4A, 5,6-hexahydro-9-hydroxy-4-propyl-4H-naphth-(1,2-B)-1,4-oxazine
JPH07206861A (ja)	1995-08-08	２−フエニル−７−アザビシクロヘプタン類及び６−フエニル−８−アザビシクロオクタン類