CA1103250A - Process for the preparation of novel piperidine derivatives - Google Patents

Process for the preparation of novel piperidine derivatives

Info

Publication number: CA1103250A
Authority: CA; Canada
Prior art keywords: formula; compound; hydrogen atom; radical; group
Prior art date: 1977-07-27
Legal status (The legal status 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 status listed.): Expired

Application number

CA308,039A

Other languages

English (en)

French (fr)

Inventor

Herbert Schroter

Kurt Eichenberger

Hans Kuhnis

Christian Egli

Oswald Schier

Franz Ostermayer

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Original Assignee

Ciba Geigy Investments Ltd

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.)

1977-07-27

Filing date

1978-07-25

Publication date

1981-06-16

1978-07-25 Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd

1981-06-16 Application granted granted Critical

1981-06-16 Publication of CA1103250A publication Critical patent/CA1103250A/en

Status Expired legal-status Critical Current

Links

150000003053 piperidines Chemical class 0.000 title claims abstract description 6
238000000034 method Methods 0.000 title claims description 34
238000002360 preparation method Methods 0.000 title claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 48
150000003839 salts Chemical group 0.000 claims abstract description 41
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 34
125000004043 oxo group Chemical group O=* 0.000 claims abstract description 21
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims abstract description 3
101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims abstract 8
150000001875 compounds Chemical class 0.000 claims description 104
-1 o-phenylene radical Chemical class 0.000 claims description 48
239000002253 acid Substances 0.000 claims description 29
239000001257 hydrogen Substances 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 24
125000001424 substituent group Chemical group 0.000 claims description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
239000000126 substance Substances 0.000 claims description 16
125000003545 alkoxy group Chemical group 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 13
150000003254 radicals Chemical class 0.000 claims description 13
125000004414 alkyl thio group Chemical group 0.000 claims description 11
239000007858 starting material Substances 0.000 claims description 11
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 8
125000004076 pyridyl group Chemical group 0.000 claims description 8
125000003373 pyrazinyl group Chemical group 0.000 claims description 7
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 6
239000002184 metal Substances 0.000 claims description 6
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 5
231100000252 nontoxic Toxicity 0.000 claims description 5
230000003000 nontoxic effect Effects 0.000 claims description 5
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 5
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims description 4
125000001589 carboacyl group Chemical group 0.000 claims description 4
125000003700 epoxy group Chemical group 0.000 claims description 4
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 claims description 4
230000003287 optical effect Effects 0.000 claims description 4
125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
238000006482 condensation reaction Methods 0.000 claims description 3
125000002950 monocyclic group Chemical group 0.000 claims description 3
229910019020 PtO2 Inorganic materials 0.000 claims description 2
FMFSVZQZWVMVKB-UHFFFAOYSA-N [C]1=CN=CC=N1 Chemical class [C]1=CN=CC=N1 FMFSVZQZWVMVKB-UHFFFAOYSA-N 0.000 claims description 2
YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 claims description 2
150000001450 anions Chemical class 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 5
AYIIEIDYKLEGMA-UHFFFAOYSA-N 2-[1-[2-hydroxy-3-(3-methoxypyrazin-2-yl)oxypropyl]piperidin-4-yl]-3,4-dihydroisoquinolin-1-one Chemical compound COC1=NC=CN=C1OCC(O)CN1CCC(N2C(C3=CC=CC=C3CC2)=O)CC1 AYIIEIDYKLEGMA-UHFFFAOYSA-N 0.000 claims 3
ZRLLOUJXRKQVIG-UHFFFAOYSA-N 2-[1-[3-(3-chloropyrazin-2-yl)oxy-2-hydroxypropyl]piperidin-4-yl]-3,4-dihydroisoquinolin-1-one Chemical compound C1CC(N2C(C3=CC=CC=C3CC2)=O)CCN1CC(O)COC1=NC=CN=C1Cl ZRLLOUJXRKQVIG-UHFFFAOYSA-N 0.000 claims 2
DVLJOTZCAIWGLV-UHFFFAOYSA-N 2-[1-[3-(3-ethylsulfanylpyrazin-2-yl)oxy-2-hydroxypropyl]piperidin-4-yl]-3,4-dihydroisoquinolin-1-one Chemical compound CCSC1=NC=CN=C1OCC(O)CN1CCC(N2C(C3=CC=CC=C3CC2)=O)CC1 DVLJOTZCAIWGLV-UHFFFAOYSA-N 0.000 claims 2
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 2
FYEKJXSXDASODO-UHFFFAOYSA-N 2-chloro-3-(oxiran-2-ylmethoxy)pyrazine Chemical compound ClC1=NC=CN=C1OCC1OC1 FYEKJXSXDASODO-UHFFFAOYSA-N 0.000 claims 1
150000004707 phenolate Chemical class 0.000 claims 1
239000002220 antihypertensive agent Substances 0.000 abstract description 3
230000003276 anti-hypertensive effect Effects 0.000 abstract description 2
239000003416 antiarrhythmic agent Substances 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 28
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 15
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 14
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 14
239000003054 catalyst Substances 0.000 description 14
239000003795 chemical substances by application Substances 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
238000006722 reduction reaction Methods 0.000 description 12
150000008064 anhydrides Chemical class 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
150000002148 esters Chemical class 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
150000007513 acids Chemical class 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
239000002904 solvent Substances 0.000 description 8
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 7
229910052783 alkali metal Inorganic materials 0.000 description 7
125000003277 amino group Chemical group 0.000 description 7
239000002585 base Substances 0.000 description 7
239000000284 extract Substances 0.000 description 7
238000005984 hydrogenation reaction Methods 0.000 description 7
229910052763 palladium Inorganic materials 0.000 description 7
229910052697 platinum Inorganic materials 0.000 description 7
239000011734 sodium Substances 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000009903 catalytic hydrogenation reaction Methods 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
229910052801 chlorine Inorganic materials 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
239000007868 Raney catalyst Substances 0.000 description 5
229910000564 Raney nickel Inorganic materials 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229940074995 bromine Drugs 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
150000004820 halides Chemical class 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 4
YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 4
150000008065 acid anhydrides Chemical class 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
229910001385 heavy metal Inorganic materials 0.000 description 4
238000007327 hydrogenolysis reaction Methods 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
229910052759 nickel Inorganic materials 0.000 description 4
239000000825 pharmaceutical preparation Substances 0.000 description 4
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-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
239000004215 Carbon black (E152) Substances 0.000 description 3
241000700199 Cavia porcellus Species 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
229960004592 isopropanol Drugs 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
229940031826 phenolate Drugs 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
235000011149 sulphuric acid Nutrition 0.000 description 3
125000003396 thiol group Chemical class [H]S* 0.000 description 3
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 2
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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 2
235000011054 acetic acid Nutrition 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
229940030600 antihypertensive agent Drugs 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
150000001540 azides Chemical class 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
239000000470 constituent Substances 0.000 description 2
JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
LTYRAPJYLUPLCI-UHFFFAOYSA-N glycolonitrile Chemical compound OCC#N LTYRAPJYLUPLCI-UHFFFAOYSA-N 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
- 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
- C07D401/14—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 three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA308,039A 1977-07-27 1978-07-25 Process for the preparation of novel piperidine derivatives Expired CA1103250A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
LU77856		1977-07-27
LU77856A LU77856A1 (de)	1977-07-27	1977-07-27	Verfahren zur herstellung von neuen piperidin-derivaten

Publications (1)

Publication Number	Publication Date
CA1103250A true CA1103250A (en)	1981-06-16

Family

ID=19728649

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA308,039A Expired CA1103250A (en)	1977-07-27	1978-07-25	Process for the preparation of novel piperidine derivatives

Country Status (7)

Country	Link
EP (1)	EP0000869A1 (de)
JP (1)	JPS5424880A (de)
AU (1)	AU3836078A (de)
CA (1)	CA1103250A (de)
DK (1)	DK334078A (de)
IT (1)	IT7850455A0 (de)
LU (1)	LU77856A1 (de)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK141752B (da) *	1974-07-31	1980-06-09	Ciba Geigy Ag	Aalogifremgangsmåde til fremstilling af piperidiner eller salte deraf.
DE2701794A1 (de) *	1976-01-21	1977-07-28	Ciba Geigy Ag	Oxigenierte n-aryl-diazacyclen

1977
- 1977-07-27 LU LU77856A patent/LU77856A1/de unknown
1978
- 1978-07-19 EP EP78100431A patent/EP0000869A1/de not_active Withdrawn
- 1978-07-25 CA CA308,039A patent/CA1103250A/en not_active Expired
- 1978-07-25 IT IT7850455A patent/IT7850455A0/it unknown
- 1978-07-26 AU AU38360/78A patent/AU3836078A/en active Pending
- 1978-07-26 DK DK334078A patent/DK334078A/da unknown
- 1978-07-27 JP JP9102278A patent/JPS5424880A/ja active Pending

Also Published As

Publication number	Publication date
EP0000869A1 (de)	1979-03-07
AU3836078A (en)	1980-01-31
IT7850455A0 (it)	1978-07-25
JPS5424880A (en)	1979-02-24
LU77856A1 (de)	1979-03-26
DK334078A (da)	1979-01-28

Legal Events

Date	Code	Title	Description
1998-06-16	MKEX	Expiry

Publication	Publication Date	Title
EP0193256B1 (de)	1989-04-05	Thiazolidindion-Derivate, deren Herstellung und Anwendung
CA1244418A (en)	1988-11-08	Glutarimide antianxiety and antihypertensive agents
US4171370A (en)	1979-10-16	Phenoxy-amino-propanols
CA1049511A (en)	1979-02-27	2-tetrahydrofurfuryl-6,7-benzomorphanes, their acid addition salts, their use as pharmaceuticals and processes for their production
CS201040B2 (en)	1980-10-31	Method of producing etherified hydroxy-benzo-diheterocyclic compounds
HU193161B (en)	1987-08-28	Process for preparing new n-alkyl-norscopines
CA1288102C (en)	1991-08-27	Pyridine derivatives, their preparation and their use
US4210653A (en)	1980-07-01	Pyridyloxypropanolamines
EP0144991B1 (de)	1989-03-29	Polymethoxybenzyl-Piperazin-Derivate, Verfahren zu ihrer Herstellung und diese Derivate enthaltende pharmazeutische Zusammensetzungen
KR880002704B1 (ko)	1988-12-26	1,4-디하이드로피리딘 화합물의 제조방법
IE44276B1 (en)	1981-09-23	Oxygenated n-aryl-diazacyclic compounds
JPS6123790B2 (de)	1986-06-07
US4882316A (en)	1989-11-21	Pyrimidine derivatives
GB2068373A (en)	1981-08-12	Cyclohexene derivatives
US2355659A (en)	1944-08-15	Piperidine derivatives and process for the manufacture of the same
EP0009075A1 (de)	1980-04-02	Pyridyloxypropanolamine und ihre Ester, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
KR840001919B1 (ko)	1984-10-25	치환된 펜옥시-아미노프로판올 유도체의 제조방법
US4304912A (en)	1981-12-08	Piperidine derivatives
CA1105021A (en)	1981-07-14	Process for the manufacture of new 1-amino-2-hydroxy- 3-heterocyclyloxy-propanes
US3332949A (en)	1967-07-25	1-phenyl-4-[2-(2-pyridyl)-ethyl] piperazines
EP0394484A1 (de)	1990-10-31	Benzothiadiazepin-derivate
US4029795A (en)	1977-06-14	4(2' Isoquinolin-1-one)piperidines
GB1565055A (en)	1980-04-16	Tetrahydropyridine and piperidine derivatives and processes for the preparation thereof
CA1131636A (en)	1982-09-14	Quinazoline antihypertensives
JPS5988467A (ja)	1984-05-22	フエノキシアミノプロパノ−ル誘導体