NO314498B1 - Substituerte 3-aryl-3-karboksylalkyl-glutarimider, fremgangsmåte ved fremstilling av disse ved 4-arylo-4-cyanoheptan-dikarboksylsyrecyklisering, og anvendelse derav for fremstilling av 3-aryl-3-hydroksyalkylpiperidiner - Google Patents

Substituerte 3-aryl-3-karboksylalkyl-glutarimider, fremgangsmåte ved fremstilling av disse ved 4-arylo-4-cyanoheptan-dikarboksylsyrecyklisering, og anvendelse derav for fremstilling av 3-aryl-3-hydroksyalkylpiperidiner Download PDF

Info

Publication number: NO314498B1
Authority: NO; Norway
Prior art keywords: formula; salts; compound; dichlorophenyl; acid
Prior art date: 1996-03-07

Application number

NO19984083A

Other languages

English (en)

Norwegian (no)

Other versions

NO984083L (no

NO984083D0 (no

Inventor

Philippe Camus

Marcel Descamps

Joel Radisson

Original Assignee

Sanofi Synthelabo

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.)

1996-03-07

Filing date

1998-09-04

Publication date

2003-03-31

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=9489959&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NO314498(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1998-09-04 Application filed by Sanofi Synthelabo filed Critical Sanofi Synthelabo

1998-09-04 Publication of NO984083L publication Critical patent/NO984083L/no

1998-09-04 Publication of NO984083D0 publication Critical patent/NO984083D0/no

2003-03-31 Publication of NO314498B1 publication Critical patent/NO314498B1/no

Links

238000000034 method Methods 0.000 title claims description 32
238000002360 preparation method Methods 0.000 title claims description 22
230000008569 process Effects 0.000 title claims description 9
238000007363 ring formation reaction Methods 0.000 title description 11
150000001875 compounds Chemical class 0.000 claims description 58
150000003839 salts Chemical class 0.000 claims description 51
-1 (C-j-C-4 alkoxy Chemical group 0.000 claims description 44
KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 claims description 40
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 29
239000005977 Ethylene Chemical group 0.000 claims description 29
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 24
125000001424 substituent group Chemical group 0.000 claims description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 15
125000004093 cyano group Chemical group *C#N 0.000 claims description 14
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 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
125000004076 pyridyl group Chemical group 0.000 claims description 11
125000001544 thienyl group Chemical group 0.000 claims description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
ACZANAQHXOREOK-UHFFFAOYSA-N 3,5-dicyano-3-(3,4-dichlorophenyl)pentanoic acid Chemical compound N#CCCC(CC(=O)O)(C#N)C1=CC=C(Cl)C(Cl)=C1 ACZANAQHXOREOK-UHFFFAOYSA-N 0.000 claims description 10
229910000085 borane Inorganic materials 0.000 claims description 10
239000007858 starting material Substances 0.000 claims description 9
150000001412 amines Chemical class 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
239000002585 base Substances 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
125000004185 ester group Chemical group 0.000 claims description 4
239000012458 free base Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
MZGHAKHDLACYAT-UHFFFAOYSA-N 4-cyano-4-(3,4-dichlorophenyl)-7-methoxy-7-oxoheptanoic acid Chemical compound COC(=O)CCC(CCC(O)=O)(C#N)C1=CC=C(Cl)C(Cl)=C1 MZGHAKHDLACYAT-UHFFFAOYSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
RWSLGEHCZNXJBR-UHFFFAOYSA-N 3-[3-(3,4-dichlorophenyl)piperidin-3-yl]propan-1-ol Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(CCCO)CCCNC1 RWSLGEHCZNXJBR-UHFFFAOYSA-N 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims description 2
235000005985 organic acids Nutrition 0.000 claims description 2
VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 claims description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 7
238000006722 reduction reaction Methods 0.000 claims 2
NFEQUCGNNCYRCD-UHFFFAOYSA-N 2-[3-(3,4-dichlorophenyl)piperidin-3-yl]ethanol Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(CCO)CCCNC1 NFEQUCGNNCYRCD-UHFFFAOYSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 49
239000000543 intermediate Substances 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
239000000047 product Substances 0.000 description 26
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
239000011541 reaction mixture Substances 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 18
150000002148 esters Chemical class 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 14
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 13
238000010992 reflux Methods 0.000 description 13
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 10
230000009467 reduction Effects 0.000 description 10
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
238000007127 saponification reaction Methods 0.000 description 9
239000002244 precipitate Substances 0.000 description 8
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
QWZNCAFWRZZJMA-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)acetonitrile Chemical compound ClC1=CC=C(CC#N)C=C1Cl QWZNCAFWRZZJMA-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
238000001914 filtration Methods 0.000 description 6
150000002825 nitriles Chemical class 0.000 description 6
IZYOPMWZZTXWKZ-UHFFFAOYSA-N 2-[3-(3,4-dichlorophenyl)-2,6-dioxopiperidin-3-yl]acetic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(CC(=O)O)CCC(=O)NC1=O IZYOPMWZZTXWKZ-UHFFFAOYSA-N 0.000 description 5
HXMKDQGJBDSOIM-UHFFFAOYSA-N 3-[3-(3,4-dichlorophenyl)-2,6-dioxopiperidin-3-yl]propanoic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(CCC(=O)O)CCC(=O)NC1=O HXMKDQGJBDSOIM-UHFFFAOYSA-N 0.000 description 5
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical class C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 5
238000001035 drying Methods 0.000 description 5
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
230000003287 optical effect Effects 0.000 description 4
238000000926 separation method Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 3
KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
150000005690 diesters Chemical class 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 3
CNAVWAPJMJUJHS-UHFFFAOYSA-N methyl 3-cyano-3-(3,4-difluorophenyl)propanoate Chemical compound COC(=O)CC(C#N)C1=CC=C(F)C(F)=C1 CNAVWAPJMJUJHS-UHFFFAOYSA-N 0.000 description 3
125000000896 monocarboxylic acid group Chemical group 0.000 description 3
230000006340 racemization Effects 0.000 description 3
239000000725 suspension Substances 0.000 description 3
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
GNPYERUNJMDEFQ-UHFFFAOYSA-N 2-(3,4-difluorophenyl)acetonitrile Chemical compound FC1=CC=C(CC#N)C=C1F GNPYERUNJMDEFQ-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
UZSGNCYEUGJVLO-UHFFFAOYSA-N 3-cyano-3-(3,4-dichlorophenyl)propanoic acid Chemical compound OC(=O)CC(C#N)C1=CC=C(Cl)C(Cl)=C1 UZSGNCYEUGJVLO-UHFFFAOYSA-N 0.000 description 2
BEHSQNGGFJOVRQ-UHFFFAOYSA-N 4-cyano-4-(3,4-difluorophenyl)-6-methoxy-6-oxohexanoic acid Chemical compound COC(=O)CC(CCC(O)=O)(C#N)C1=CC=C(F)C(F)=C1 BEHSQNGGFJOVRQ-UHFFFAOYSA-N 0.000 description 2
TWJDEKLKGSORCG-UHFFFAOYSA-N 4-cyano-4-(3,4-difluorophenyl)-7-methoxy-7-oxoheptanoic acid Chemical compound COC(=O)CCC(CCC(O)=O)(C#N)C1=CC=C(F)C(F)=C1 TWJDEKLKGSORCG-UHFFFAOYSA-N 0.000 description 2
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 2
MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
238000010907 mechanical stirring Methods 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
150000003053 piperidines Chemical class 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 2
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
NQHFSECYQAQZBN-LSYPWIJNSA-M 1-[(3s)-3-(3,4-dichlorophenyl)-3-[2-(4-phenyl-1-azoniabicyclo[2.2.2]octan-1-yl)ethyl]piperidin-1-yl]-2-(3-propan-2-yloxyphenyl)ethanone;chloride Chemical compound [Cl-].CC(C)OC1=CC=CC(CC(=O)N2C[C@](CC[N+]34CCC(CC3)(CC4)C=3C=CC=CC=3)(CCC2)C=2C=C(Cl)C(Cl)=CC=2)=C1 NQHFSECYQAQZBN-LSYPWIJNSA-M 0.000 description 1
OIPHWUPMXHQWLR-UHFFFAOYSA-N 2-pyridin-3-ylacetonitrile Chemical compound N#CCC1=CC=CN=C1 OIPHWUPMXHQWLR-UHFFFAOYSA-N 0.000 description 1
CLSHQIDDCJTHAJ-UHFFFAOYSA-N 2-thienylacetonitrile Chemical compound N#CCC1=CC=CS1 CLSHQIDDCJTHAJ-UHFFFAOYSA-N 0.000 description 1
GWZCLMWEJWPFFA-UHFFFAOYSA-N 2-thiophen-3-ylacetonitrile Chemical compound N#CCC=1C=CSC=1 GWZCLMWEJWPFFA-UHFFFAOYSA-N 0.000 description 1
BXMIPJQCDPLZQD-UHFFFAOYSA-N 3,4,5-tricyano-4-(3,4-dichlorophenyl)pentanoic acid Chemical group OC(=O)CC(C#N)C(CC#N)(C#N)C1=CC=C(Cl)C(Cl)=C1 BXMIPJQCDPLZQD-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
QTNMWKIEGLSCSV-UHFFFAOYSA-N 4-cyano-4-(3,4-dichlorophenyl)-6-methoxy-6-oxohexanoic acid Chemical compound COC(=O)CC(CCC(O)=O)(C#N)C1=CC=C(Cl)C(Cl)=C1 QTNMWKIEGLSCSV-UHFFFAOYSA-N 0.000 description 1
PBDHNEFKJULMGJ-UHFFFAOYSA-N 4-cyano-7-methoxy-7-oxo-4-pyridin-3-ylheptanoic acid Chemical compound COC(=O)CCC(CCC(O)=O)(C#N)C1=CC=CN=C1 PBDHNEFKJULMGJ-UHFFFAOYSA-N 0.000 description 1
GXSQEBPMPIUOGW-UHFFFAOYSA-N 4-cyano-7-methoxy-7-oxo-4-thiophen-2-ylheptanoic acid Chemical compound COC(=O)CCC(CCC(O)=O)(C#N)C1=CC=CS1 GXSQEBPMPIUOGW-UHFFFAOYSA-N 0.000 description 1
BMWGJHQEYJQWQW-UHFFFAOYSA-N 4-cyano-7-methoxy-7-oxo-4-thiophen-3-ylheptanoic acid Chemical compound COC(=O)CCC(CCC(O)=O)(C#N)C=1C=CSC=1 BMWGJHQEYJQWQW-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
235000001258 Cinchona calisaya Nutrition 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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000009471 action Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000005250 alkyl acrylate group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
239000001166 ammonium sulphate Substances 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
230000008901 benefit Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 1
UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 1
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
150000001916 cyano esters Chemical class 0.000 description 1
238000001212 derivatisation Methods 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000007429 general method Methods 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
PBPZECKNZBQALL-UHFFFAOYSA-N methyl 3-cyano-3-(3,4-dichlorophenyl)propanoate Chemical compound COC(=O)CC(C#N)C1=CC=C(Cl)C(Cl)=C1 PBPZECKNZBQALL-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
DZOJBGLFWINFBF-UUWRZZSWSA-N n-[1-[3-[(3s)-1-benzoyl-3-(3,4-dichlorophenyl)piperidin-3-yl]propyl]-4-phenylpiperidin-4-yl]-n-methylacetamide Chemical compound C([C@@](C1)(CCCN2CCC(CC2)(N(C(C)=O)C)C=2C=CC=CC=2)C=2C=C(Cl)C(Cl)=CC=2)CCN1C(=O)C1=CC=CC=C1 DZOJBGLFWINFBF-UUWRZZSWSA-N 0.000 description 1
239000002740 neurokinin 3 receptor antagonist Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
DZOJBGLFWINFBF-UMSFTDKQSA-N osanetant Chemical compound C([C@](C1)(CCCN2CCC(CC2)(N(C(C)=O)C)C=2C=CC=CC=2)C=2C=C(Cl)C(Cl)=CC=2)CCN1C(=O)C1=CC=CC=C1 DZOJBGLFWINFBF-UMSFTDKQSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
150000005458 piperidinediones Chemical class 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
229960000948 quinine Drugs 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000011144 upstream manufacturing Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- C07D211/80—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 two double bonds between ring members or between ring members and non-ring members
- C07D211/84—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 two 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 directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
- C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO19984083A 1996-03-07 1998-09-04 Substituerte 3-aryl-3-karboksylalkyl-glutarimider, fremgangsmåte ved fremstilling av disse ved 4-arylo-4-cyanoheptan-dikarboksylsyrecyklisering, og anvendelse derav for fremstilling av 3-aryl-3-hydroksyalkylpiperidiner NO314498B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9602880A FR2745811B1 (fr)	1996-03-07	1996-03-07	Glutarimide disubstitue procede pour sa preparation, et son utilisation
PCT/FR1997/000388 WO1997032852A1 (fr)	1996-03-07	1997-03-05	Glutarimides 3-aryl-3-carboxyalkyl substitues, leur preparation par cyclisation d'acides dicarboxyliques de la 4-aryl-4-cyanoheptane et leur utilisation pour la preparation de 3-aryl-3-hydroxyalkylpiperidines

Publications (3)

Publication Number	Publication Date
NO984083L NO984083L (no)	1998-09-04
NO984083D0 NO984083D0 (no)	1998-09-04
NO314498B1 true NO314498B1 (no)	2003-03-31

Family

ID=9489959

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19984083A NO314498B1 (no)	1996-03-07	1998-09-04	Substituerte 3-aryl-3-karboksylalkyl-glutarimider, fremgangsmåte ved fremstilling av disse ved 4-arylo-4-cyanoheptan-dikarboksylsyrecyklisering, og anvendelse derav for fremstilling av 3-aryl-3-hydroksyalkylpiperidiner

Country Status (19)

Country	Link
US (2)	US6008360A (es)
EP (1)	EP0888304B1 (es)
JP (1)	JP3116051B2 (es)
AR (1)	AR006139A1 (es)
AT (1)	ATE206399T1 (es)
AU (1)	AU2163497A (es)
BR (1)	BR9707943C8 (es)
CA (1)	CA2244771C (es)
CY (1)	CY2276B1 (es)
DE (1)	DE69707114T2 (es)
DK (1)	DK0888304T3 (es)
ES (1)	ES2165594T3 (es)
FR (1)	FR2745811B1 (es)
MY (1)	MY128754A (es)
NO (1)	NO314498B1 (es)
PT (1)	PT888304E (es)
TW (1)	TW381080B (es)
WO (1)	WO1997032852A1 (es)
ZA (1)	ZA971999B (es)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2787449B3 (fr)	1998-12-15	2001-01-12	Sanofi Sa	Derives de 3-phenyl-2,6-dioxopiperidin-3-yl propionamide et leur procede de preparation
FR2787448B3 (fr) *	1998-12-18	2001-01-12	Sanofi Sa	Ester d'alkyle inferieur de l'acide 3-(3,4-dihalogenophenyl) -2,6-dioxopiperidine3-propionique et son mode de preparation
RU2152386C1 (ru) *	1999-05-27	2000-07-10	Российский Университет Дружбы Народов	Способ получения 2,3,5,6-тетраоксо-4-нитропиридата аммония
DE10002509A1 (de) *	2000-01-21	2001-07-26	Gruenenthal Gmbh	Substituierte Glutarimide
WO2002046156A2 (en)	2000-12-06	2002-06-13	Sepracor, Inc.	4,4-disubstituted piperidines for use as dopamine, serotonin and norepinephrine ligands

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3379731A (en) *	1967-06-15	1968-04-23	Ciba Geigy Corp	1, 4-dihydro-1, 4-ethano-isoquinolines
US3647797A (en)	1969-07-24	1972-03-07	Richardson Merrell Inc	6-chloro - 2 3-dihydrospiro(naphthalene-(7h) 3'-piperidine)-2' 4 6'-triones
US3985888A (en) *	1969-07-24	1976-10-12	Richardson-Merrell Inc.	Methods of inducing sedation using certain spiroalkanone-imides
BE787767A (fr) *	1971-08-21	1973-02-19	Merck Patent Gmbh	Procede de preparation d'amides d'acides oxocarboxyliques et d'acides oxocarboxyliques
US5001125A (en) *	1984-03-26	1991-03-19	Janssen Pharmaceutica N.V.	Anti-virally active pyridazinamines
FR2676055B1 (fr) *	1991-05-03	1993-09-03	Sanofi Elf	Composes polycycliques amines et leurs enantiomeres, procede pour leur preparation et compositions pharmaceutiques les contenant.
US5625060A (en) *	1991-05-03	1997-04-29	Elf Sanofi	Polycyclic amine compounds and their enantiomers, their method of preparation and pharmaceutical compositions on which they are present
US5583134A (en) *	1992-09-30	1996-12-10	Sanofi	1-azoniabicyclo[2.2.2] octanes and pharmaceutical compositions in which they are present
FR2696178B1 (fr) *	1992-09-30	1994-12-30	Sanofi Elf	Amides basiques quaternaires, procédé pour leur préparation et compositions pharmaceutiques en contenant.
FR2719311B1 (fr) *	1994-03-18	1998-06-26	Sanofi Sa	Composés antagonistes sélectifs du récepteur NK3 humain et leur utilisation comme médicaments et outils de diagnostic.

1996
- 1996-03-07 FR FR9602880A patent/FR2745811B1/fr not_active Expired - Fee Related
1997
- 1997-03-05 JP JP09531525A patent/JP3116051B2/ja not_active Expired - Fee Related
- 1997-03-05 DK DK97914357T patent/DK0888304T3/da active
- 1997-03-05 AU AU21634/97A patent/AU2163497A/en not_active Abandoned
- 1997-03-05 AT AT97914357T patent/ATE206399T1/de not_active IP Right Cessation
- 1997-03-05 US US09/142,306 patent/US6008360A/en not_active Expired - Fee Related
- 1997-03-05 PT PT97914357T patent/PT888304E/pt unknown
- 1997-03-05 CA CA002244771A patent/CA2244771C/en not_active Expired - Fee Related
- 1997-03-05 BR BRPI9707943-0C8A patent/BR9707943C8/pt not_active IP Right Cessation
- 1997-03-05 EP EP97914357A patent/EP0888304B1/fr not_active Expired - Lifetime
- 1997-03-05 DE DE69707114T patent/DE69707114T2/de not_active Expired - Fee Related
- 1997-03-05 WO PCT/FR1997/000388 patent/WO1997032852A1/fr not_active Ceased
- 1997-03-05 ES ES97914357T patent/ES2165594T3/es not_active Expired - Lifetime
- 1997-03-06 MY MYPI97000946A patent/MY128754A/en unknown
- 1997-03-06 TW TW086102748A patent/TW381080B/zh not_active IP Right Cessation
- 1997-03-07 AR ARP970100909A patent/AR006139A1/es active IP Right Grant
- 1997-03-07 ZA ZA9701999A patent/ZA971999B/xx unknown
1998
- 1998-09-04 NO NO19984083A patent/NO314498B1/no unknown
1999
- 1999-11-10 US US09/437,362 patent/US6242607B1/en not_active Expired - Fee Related
2002
- 2002-05-15 CY CY0200029A patent/CY2276B1/xx unknown

Also Published As

Publication number	Publication date
ZA971999B (en)	1997-09-09
DE69707114D1 (de)	2001-11-08
US6008360A (en)	1999-12-28
NO984083L (no)	1998-09-04
AU2163497A (en)	1997-09-22
NO984083D0 (no)	1998-09-04
EP0888304B1 (fr)	2001-10-04
BR9707943A (pt)	1999-07-27
JPH11506124A (ja)	1999-06-02
BR9707943B (pt)	2008-05-20
ATE206399T1 (de)	2001-10-15
DE69707114T2 (de)	2002-06-06
FR2745811A1 (fr)	1997-09-12
ES2165594T3 (es)	2002-03-16
FR2745811B1 (fr)	1998-05-22
US6242607B1 (en)	2001-06-05
BR9707943C8 (pt)	2014-11-18
CA2244771C (en)	2004-07-13
EP0888304A1 (fr)	1999-01-07
AR006139A1 (es)	1999-08-11
PT888304E (pt)	2002-02-28
CY2276B1 (en)	2003-07-04
WO1997032852A1 (fr)	1997-09-12
TW381080B (en)	2000-02-01
DK0888304T3 (da)	2002-03-04
MY128754A (en)	2007-02-28
JP3116051B2 (ja)	2000-12-11
CA2244771A1 (en)	1997-09-12

Publication	Publication Date	Title
US4572909A (en)	1986-02-25	2-(Secondary aminoalkoxymethyl) dihydropyridine derivatives as anti-ischaemic and antihypertensive agents
RU1831476C (ru)	1993-07-30	Способ получени производных дигидропиридина
RU2056420C1 (ru)	1996-03-20	Производные 1,4-бензодиоксана или их соли и способ их получения
WO2004013100A2 (fr)	2004-02-12	Derives de n-[phenyl(piperidin-2-yl)methyl]benzamide, leur preparation et leur application en therapeutique
NO323613B1 (no)	2007-06-18	Fremgangsmate for fremstilling av 2-tienyletylamin-derivater
HU201003B (en)	1990-09-28	Process for producing indan derivatives and pharmaceutical compositions compirising same
DK165950B (da)	1993-02-15	Fremgangsmaade til fremstilling af herbicide 2-(4,4-disubstitueret-5-oxo-2-imidazolin-2-yl)benzoesyrer, -nicotinsyrer og -quinolin-3-carboxylsyrer, estere og salte deraf
NO314498B1 (no)	2003-03-31	Substituerte 3-aryl-3-karboksylalkyl-glutarimider, fremgangsmåte ved fremstilling av disse ved 4-arylo-4-cyanoheptan-dikarboksylsyrecyklisering, og anvendelse derav for fremstilling av 3-aryl-3-hydroksyalkylpiperidiner
US7943660B2 (en)	2011-05-17	Inhibitors of the LFA-1/ICAM-1 interaction and uses thereof
JP2003522122A (ja)	2003-07-22	置換ピペリジン−４−オンの製造
HU203338B (en)	1991-07-29	Process for producing thiofene derivatives
KR20080020613A (ko)	2008-03-05	(치환된) (ｒ)- 또는 (ｓ)-만델산의 동적 분할 방법
JPH07113016B2 (ja)	1995-12-06	１，４−ジヒドロピリジン誘導体、その製造方法及びその誘導体を含有する高血圧治療用組成物
US7112604B2 (en)	2006-09-26	Process for the preparation of Atorvastatin and intermediates
JP2021526142A (ja)	2021-09-30	２−（１−（ｔｅｒｔ−ブトキシカルボニル）ピペリジン−４−イル）安息香酸を調製するためのプロセス
US5780666A (en)	1998-07-14	Process for the preparation of an optically pure aminoalcohol
US5310899A (en)	1994-05-10	Process for the preparation of chiral 4-aryloxyazetidinones
JPS6125708B2 (es)	1986-06-17
JPH0534351B2 (es)	1993-05-21
JP4260911B2 (ja)	2009-04-30	ピロリジノン誘導体のラセミ化方法
JPH04342579A (ja)	1992-11-30	１−アリールスルホニルピペラジン類及び薬剤として許容され得るその酸付加塩
JPH09227557A (ja)	1997-09-02	チエニルオキサゾール誘導体及びチエニルピラゾール誘導体
JPH0667943B2 (ja)	1994-08-31	新規な環状アミド化合物
JPH0278661A (ja)	1990-03-19	心臓血管系に作用する化合物
JPS59101464A (ja)	1984-06-12	置換ジヒドロピリジンの製造方法及びその中間体