DE2549999A1 - Piperidin-derivate und verfahren zu ihrer herstellung - Google Patents
Piperidin-derivate und verfahren zu ihrer herstellungInfo
- Publication number
- DE2549999A1 DE2549999A1 DE19752549999 DE2549999A DE2549999A1 DE 2549999 A1 DE2549999 A1 DE 2549999A1 DE 19752549999 DE19752549999 DE 19752549999 DE 2549999 A DE2549999 A DE 2549999A DE 2549999 A1 DE2549999 A1 DE 2549999A1
- Authority
- DE
- Germany
- Prior art keywords
- piperidine
- general formula
- phenoxymethyl
- group
- benzoyl
- Prior art date
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 150000003053 piperidines Chemical class 0.000 claims description 4
- -1 aryloxy radical Chemical class 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 claims description 2
- 239000003921 oil Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 229940127557 pharmaceutical product Drugs 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000203 mixture Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- XBXHCBLBYQEYTI-UHFFFAOYSA-N piperidin-4-ylmethanol Chemical compound OCC1CCNCC1 XBXHCBLBYQEYTI-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XLHLVPVJPDGPBC-UHFFFAOYSA-N 4-(chloromethyl)piperidine;hydrochloride Chemical compound Cl.ClCC1CCNCC1 XLHLVPVJPDGPBC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ZDHKVKPZQKYREU-UHFFFAOYSA-N 4-(chloromethyl)pyridine;hydron;chloride Chemical compound Cl.ClCC1=CC=NC=C1 ZDHKVKPZQKYREU-UHFFFAOYSA-N 0.000 description 2
- VYBZUXRVMWVTEB-UHFFFAOYSA-N 4-(phenoxymethyl)pyridine Chemical compound C=1C=NC=CC=1COC1=CC=CC=C1 VYBZUXRVMWVTEB-UHFFFAOYSA-N 0.000 description 2
- SVJZXTDZALYYRB-UHFFFAOYSA-N 4-[(2-nitrophenoxy)methyl]piperidine Chemical compound [O-][N+](=O)C1=CC=CC=C1OCC1CCNCC1 SVJZXTDZALYYRB-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- CUALLDHALGTGAS-UHFFFAOYSA-N [4-(phenoxymethyl)piperidin-1-yl]-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)N(CC1)CCC1COC1=CC=CC=C1 CUALLDHALGTGAS-UHFFFAOYSA-N 0.000 description 2
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 230000003266 anti-allergic effect Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 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
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- GUOZBMRFKXWUNK-UHFFFAOYSA-N 1-(3-chloropropyl)-4-(phenoxymethyl)piperidine Chemical class C1CN(CCCCl)CCC1COC1=CC=CC=C1 GUOZBMRFKXWUNK-UHFFFAOYSA-N 0.000 description 1
- HEMZNKOBGSXYFU-UHFFFAOYSA-N 2-(phenoxymethyl)pyridine Chemical class C=1C=CC=NC=1COC1=CC=CC=C1 HEMZNKOBGSXYFU-UHFFFAOYSA-N 0.000 description 1
- YMEBBYMRVTVITA-UHFFFAOYSA-N 4-(2-phenoxyethyl)pyridine Chemical compound C=1C=CC=CC=1OCCC1=CC=NC=C1 YMEBBYMRVTVITA-UHFFFAOYSA-N 0.000 description 1
- BREBKAKBNYXIOP-UHFFFAOYSA-N 4-(phenoxymethyl)piperidine Chemical compound C1CNCCC1COC1=CC=CC=C1 BREBKAKBNYXIOP-UHFFFAOYSA-N 0.000 description 1
- FGIVWTSVLVUKOK-UHFFFAOYSA-N 4-[(2-bromophenoxy)methyl]piperidine Chemical compound BrC1=CC=CC=C1OCC1CCNCC1 FGIVWTSVLVUKOK-UHFFFAOYSA-N 0.000 description 1
- XYROETVBSCXMHN-UHFFFAOYSA-N 4-[(2-butoxyphenoxy)methyl]piperidine Chemical compound CCCCOC1=CC=CC=C1OCC1CCNCC1 XYROETVBSCXMHN-UHFFFAOYSA-N 0.000 description 1
- YEDQERJRGLCJKY-UHFFFAOYSA-N 4-[(2-chlorophenoxy)methyl]piperidine Chemical compound ClC1=CC=CC=C1OCC1CCNCC1 YEDQERJRGLCJKY-UHFFFAOYSA-N 0.000 description 1
- GTYCVCKSMFWBQA-UHFFFAOYSA-N 4-[(2-fluorophenoxy)methyl]piperidine Chemical compound FC1=CC=CC=C1OCC1CCNCC1 GTYCVCKSMFWBQA-UHFFFAOYSA-N 0.000 description 1
- PVLZQVJPOZTGMJ-UHFFFAOYSA-N 4-[(2-methylphenoxy)methyl]piperidine Chemical compound CC1=CC=CC=C1OCC1CCNCC1 PVLZQVJPOZTGMJ-UHFFFAOYSA-N 0.000 description 1
- PPHIYDGKKZEIPW-UHFFFAOYSA-N 4-[(2-propylphenoxy)methyl]piperidine Chemical compound CCCC1=CC=CC=C1OCC1CCNCC1 PPHIYDGKKZEIPW-UHFFFAOYSA-N 0.000 description 1
- JRKWHWMRJYOIEA-UHFFFAOYSA-N 4-[(3-chlorophenoxy)methyl]piperidine Chemical compound ClC1=CC=CC(OCC2CCNCC2)=C1 JRKWHWMRJYOIEA-UHFFFAOYSA-N 0.000 description 1
- BJWGYFBJEZCOEG-UHFFFAOYSA-N 4-[(3-methoxyphenoxy)methyl]piperidine Chemical compound COC1=CC=CC(OCC2CCNCC2)=C1 BJWGYFBJEZCOEG-UHFFFAOYSA-N 0.000 description 1
- IGXCLKXDHNOUIB-UHFFFAOYSA-N 4-[(3-methylphenoxy)methyl]piperidine Chemical compound CC1=CC=CC(OCC2CCNCC2)=C1 IGXCLKXDHNOUIB-UHFFFAOYSA-N 0.000 description 1
- KWLNQJLKIFFYNF-UHFFFAOYSA-N 4-[(4-chlorophenoxy)methyl]piperidine Chemical compound C1=CC(Cl)=CC=C1OCC1CCNCC1 KWLNQJLKIFFYNF-UHFFFAOYSA-N 0.000 description 1
- RERPCSOKGBHYNQ-UHFFFAOYSA-N 4-[(4-fluorophenoxy)methyl]piperidine Chemical compound C1=CC(F)=CC=C1OCC1CCNCC1 RERPCSOKGBHYNQ-UHFFFAOYSA-N 0.000 description 1
- DNIWXPWAHCHGJY-UHFFFAOYSA-N 9-[3-[4-(phenoxymethyl)piperidin-1-yl]propyl]purin-6-amine Chemical class C1=NC=2C(N)=NC=NC=2N1CCCN(CC1)CCC1COC1=CC=CC=C1 DNIWXPWAHCHGJY-UHFFFAOYSA-N 0.000 description 1
- 229930024421 Adenine Natural products 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 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
- NWOKXPKMKWWJAY-UHFFFAOYSA-N [4-(chloromethyl)piperidin-1-yl]-phenylmethanone Chemical compound C1CC(CCl)CCN1C(=O)C1=CC=CC=C1 NWOKXPKMKWWJAY-UHFFFAOYSA-N 0.000 description 1
- RLTIVBMLQJFUOB-UHFFFAOYSA-N [4-(hydroxymethyl)piperidin-1-yl]-phenylmethanone Chemical compound C1CC(CO)CCN1C(=O)C1=CC=CC=C1 RLTIVBMLQJFUOB-UHFFFAOYSA-N 0.000 description 1
- VUGZSFREUJIEKD-UHFFFAOYSA-N [4-[(2-bromophenoxy)methyl]piperidin-1-yl]-phenylmethanone Chemical compound BrC1=CC=CC=C1OCC1CCN(C(=O)C=2C=CC=CC=2)CC1 VUGZSFREUJIEKD-UHFFFAOYSA-N 0.000 description 1
- IAOBQPLNTFFTBW-UHFFFAOYSA-N [4-[(2-fluorophenoxy)methyl]piperidin-1-yl]-phenylmethanone Chemical compound FC1=CC=CC=C1OCC1CCN(C(=O)C=2C=CC=CC=2)CC1 IAOBQPLNTFFTBW-UHFFFAOYSA-N 0.000 description 1
- MAUKUXPJECWUJB-UHFFFAOYSA-N [4-[(2-methoxyphenoxy)methyl]piperidin-1-yl]-phenylmethanone Chemical compound COC1=CC=CC=C1OCC1CCN(C(=O)C=2C=CC=CC=2)CC1 MAUKUXPJECWUJB-UHFFFAOYSA-N 0.000 description 1
- ZVHXZSKGXGHGFV-UHFFFAOYSA-N [4-[(3-methylphenoxy)methyl]piperidin-1-yl]-phenylmethanone Chemical compound CC1=CC=CC(OCC2CCN(CC2)C(=O)C=2C=CC=CC=2)=C1 ZVHXZSKGXGHGFV-UHFFFAOYSA-N 0.000 description 1
- FXGPRZNHTZZKGI-UHFFFAOYSA-N [4-[(4-methylphenoxy)methyl]piperidin-1-yl]-phenylmethanone Chemical compound C1=CC(C)=CC=C1OCC1CCN(C(=O)C=2C=CC=CC=2)CC1 FXGPRZNHTZZKGI-UHFFFAOYSA-N 0.000 description 1
- 229960000643 adenine Drugs 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 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
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- PZOCACLFMYEZSG-UHFFFAOYSA-N phenyl-[4-[(2-propylphenoxy)methyl]piperidin-1-yl]methanone Chemical compound CCCC1=CC=CC=C1OCC1CCN(C(=O)C=2C=CC=CC=2)CC1 PZOCACLFMYEZSG-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- PTMBWNZJOQBTBK-UHFFFAOYSA-N pyridin-4-ylmethanol Chemical compound OCC1=CC=NC=C1 PTMBWNZJOQBTBK-UHFFFAOYSA-N 0.000 description 1
- NKBJHERHVXOEIR-UHFFFAOYSA-N pyridin-4-ylmethanol;hydrochloride Chemical compound Cl.OCC1=CC=NC=C1 NKBJHERHVXOEIR-UHFFFAOYSA-N 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Priority Applications (26)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752549999 DE2549999A1 (de) | 1975-11-07 | 1975-11-07 | Piperidin-derivate und verfahren zu ihrer herstellung |
| ZA766381A ZA766381B (en) | 1975-11-07 | 1976-10-25 | New piperidine derivatives |
| CA264,608A CA1077942A (en) | 1975-11-07 | 1976-10-28 | 4-phenoxymethylpiperidine compounds |
| IE2394/76A IE43866B1 (en) | 1975-11-07 | 1976-10-29 | Piperidine derivatives |
| US05/737,518 US4243807A (en) | 1975-11-07 | 1976-11-01 | 4-Phenoxymethyl-piperidines |
| HU76BO00001639A HU171237B (hu) | 1975-11-07 | 1976-11-01 | Sposob poluchenija proizvodnykh 4-/fenoksi-metil/-piperidina |
| DK494876A DK494876A (da) | 1975-11-07 | 1976-11-02 | Fremgangsmade til fremstilling af piperidinderivater |
| SU762415648A SU633473A3 (ru) | 1975-11-07 | 1976-11-02 | Способ получени производных пиперидина или их солей |
| FI763148A FI763148A7 (en, 2012) | 1975-11-07 | 1976-11-03 | |
| SE7612234A SE7612234L (sv) | 1975-11-07 | 1976-11-03 | Nya piperidinderivat. |
| CH1385576A CH624102A5 (en, 2012) | 1975-11-07 | 1976-11-03 | |
| GB45916/76A GB1502050A (en) | 1975-11-07 | 1976-11-04 | Piperidine derivatives |
| BE172068A BE847973A (fr) | 1975-11-07 | 1976-11-04 | Nouveaux derives de la piperidine et procedes pour leur preparation, |
| DD195610A DD126942A5 (en, 2012) | 1975-11-07 | 1976-11-04 | |
| IT29083/76A IT1063618B (it) | 1975-11-07 | 1976-11-05 | Derivati piperidinici e processo per la loro preparazione |
| FR7633389A FR2330678A1 (fr) | 1975-11-07 | 1976-11-05 | Derives de piperidine et leur procede de preparation |
| LU76141A LU76141A1 (en, 2012) | 1975-11-07 | 1976-11-05 | |
| AT823776A AT352726B (de) | 1975-11-07 | 1976-11-05 | Verfahren zur herstellung von neuen piperidin- derivaten und deren salzen |
| JP51133139A JPS6055509B2 (ja) | 1975-11-07 | 1976-11-05 | ピペリジン誘導体およびその製造法 |
| NL7612286A NL7612286A (nl) | 1975-11-07 | 1976-11-05 | Piperidinederivaten en werkwijze voor hun be- reiding. |
| SU772534003A SU662009A3 (ru) | 1975-11-07 | 1977-10-21 | Способ получени производных пиперидина или их солей |
| SU772534004A SU867298A3 (ru) | 1975-11-07 | 1977-10-21 | Способ получени производных пиперидина или их солей |
| AT712478A AT360019B (de) | 1975-11-07 | 1978-10-03 | Verfahren zur herstellung von neuen piperidin- derivaten und deren salzen |
| AT712578A AT360020B (de) | 1975-11-07 | 1978-10-03 | Verfahren zur herstellung von neuen piperidin- derivaten und deren salzen |
| CH742480A CH627166A5 (en, 2012) | 1975-11-07 | 1980-10-03 | |
| CH742380A CH625788A5 (en, 2012) | 1975-11-07 | 1980-10-03 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752549999 DE2549999A1 (de) | 1975-11-07 | 1975-11-07 | Piperidin-derivate und verfahren zu ihrer herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2549999A1 true DE2549999A1 (de) | 1977-05-12 |
| DE2549999C2 DE2549999C2 (en, 2012) | 1989-01-26 |
Family
ID=5961166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752549999 Granted DE2549999A1 (de) | 1975-11-07 | 1975-11-07 | Piperidin-derivate und verfahren zu ihrer herstellung |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4243807A (en, 2012) |
| JP (1) | JPS6055509B2 (en, 2012) |
| AT (1) | AT352726B (en, 2012) |
| BE (1) | BE847973A (en, 2012) |
| CA (1) | CA1077942A (en, 2012) |
| CH (3) | CH624102A5 (en, 2012) |
| DD (1) | DD126942A5 (en, 2012) |
| DE (1) | DE2549999A1 (en, 2012) |
| DK (1) | DK494876A (en, 2012) |
| FI (1) | FI763148A7 (en, 2012) |
| FR (1) | FR2330678A1 (en, 2012) |
| GB (1) | GB1502050A (en, 2012) |
| HU (1) | HU171237B (en, 2012) |
| IE (1) | IE43866B1 (en, 2012) |
| IT (1) | IT1063618B (en, 2012) |
| LU (1) | LU76141A1 (en, 2012) |
| NL (1) | NL7612286A (en, 2012) |
| SE (1) | SE7612234L (en, 2012) |
| SU (3) | SU633473A3 (en, 2012) |
| ZA (1) | ZA766381B (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0200826A1 (en) * | 1984-03-13 | 1986-11-12 | Aberg, Gunnar A.K. | Membrane stabilizing compounds and pharmaceutical preparations and methods employing such compounds |
| US5210086A (en) * | 1990-10-02 | 1993-05-11 | Synthelabo | 2-aminopyrimidine-4-carboxamide derivatives, their preparation and their use in therapy |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA848275B (en) * | 1983-12-28 | 1985-08-28 | Degussa | New piridine-2-ethers or pyridine-2-thioethers having a nitrogen-containing cycloaliphatic ring |
| IE66332B1 (en) * | 1986-11-03 | 1995-12-27 | Novo Nordisk As | Piperidine compounds and their preparation and use |
| US5231184A (en) * | 1987-11-23 | 1993-07-27 | Janssen Pharmaceutica N.V. | Pridazinamine derivatives |
| US4822778A (en) * | 1988-01-19 | 1989-04-18 | Gunnar Aberg | Membrane stabilizing phenoxy-piperidine compounds and pharmaceutical compositions employing such compounds |
| US5109002A (en) * | 1989-09-08 | 1992-04-28 | Du Pont Merck Pharmaceutical Company | Antipsychotic 1-cycloalkylpiperidines |
| IL99537A (en) * | 1990-09-27 | 1995-11-27 | Merck & Co Inc | Fibrinogen receptor antagonists and pharmaceutical compositions containing them |
| US5264420A (en) * | 1990-09-27 | 1993-11-23 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| NZ239846A (en) * | 1990-09-27 | 1994-11-25 | Merck & Co Inc | Sulphonamide derivatives and pharmaceutical compositions thereof |
| US5321034A (en) * | 1991-05-07 | 1994-06-14 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| FI934894A0 (fi) * | 1991-05-07 | 1993-11-05 | Merck & Co Inc | Fibrinogenreceptorantagonister |
| US5416099A (en) * | 1991-10-29 | 1995-05-16 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5272158A (en) * | 1991-10-29 | 1993-12-21 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5389631A (en) * | 1991-10-29 | 1995-02-14 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| JPH08502484A (ja) * | 1992-10-14 | 1996-03-19 | メルク エンド カンパニー インコーポレーテッド | フィブリノゲンリセプタ拮抗剤 |
| US5358956A (en) * | 1992-10-14 | 1994-10-25 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5648368A (en) * | 1992-12-01 | 1997-07-15 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5441952A (en) * | 1993-04-05 | 1995-08-15 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5334596A (en) * | 1993-05-11 | 1994-08-02 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5397791A (en) * | 1993-08-09 | 1995-03-14 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5821241A (en) * | 1994-02-22 | 1998-10-13 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5719144A (en) * | 1995-02-22 | 1998-02-17 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5750147A (en) | 1995-06-07 | 1998-05-12 | Emisphere Technologies, Inc. | Method of solubilizing and encapsulating itraconazole |
| DE69615063T2 (de) * | 1995-09-28 | 2002-04-25 | Kaken Pharmaceutical Co., Ltd. | Verfahren zur herstellung von 4-methylen piperidinen |
| US5789421A (en) * | 1995-10-26 | 1998-08-04 | Merck & Co., Inc. | Fibrinogen receptor antagonist |
| US5780480A (en) * | 1996-02-28 | 1998-07-14 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5889023A (en) * | 1996-05-10 | 1999-03-30 | Merck & Co., Inc. | Fibrinogen receptor antagonist |
| US5981584A (en) * | 1997-02-06 | 1999-11-09 | Merck & Co., Inc. | Fibrinogen receptor antagonist prodrugs |
| WO2010011811A2 (en) | 2008-07-24 | 2010-01-28 | Theravance, Inc. | 3-(phenoxyphenylmethyl)pyrrolidine compounds |
| SI2358674T1 (sl) | 2008-11-14 | 2013-04-30 | Theravance, Inc. | Postopek za pripravo 4-(2-(2-fluorofenoksimetil)fenil)piperidinskih spojin |
| US20100267743A1 (en) * | 2009-04-15 | 2010-10-21 | Stangeland Eric L | 3-(phenoxypyrrolidin-3-yl-methyl)heteroaryl, 3-(phenylpyrrolidin-3-ylmethoxy)heteroaryl, and 3-(heteroarylpyrrolidin-3-ylmethoxy)heteroaryl compounds |
| AU2010273645B2 (en) | 2009-07-13 | 2014-12-04 | Theravance Biopharma R&D Ip, Llc | 3-phenoxymethylpyrrolidine compounds |
| US8273786B2 (en) * | 2009-07-21 | 2012-09-25 | Theravance, Inc. | 3-phenoxymethylpyrrolidine compounds |
| EP2523945A1 (en) | 2010-01-11 | 2012-11-21 | Theravance, Inc. | 1 - (2 - phenoxymethylphenyl) piperazine compounds as serotonin and norepinephrine reuptake inhibitors |
| JP5769348B2 (ja) * | 2010-03-22 | 2015-08-26 | セラヴァンス バイオファーマ アール＆ディー アイピー， エルエルシー | １−（２−フェノキシメチルヘテロアリール）ピペリジン化合物および１−（２−フェノキシメチルヘテロアリール）ピペラジン化合物 |
| EP2627630B1 (en) | 2010-10-11 | 2014-12-31 | Theravance Biopharma R&D IP, LLC | Serotonin reuptake inhibitors |
| WO2012075239A1 (en) | 2010-12-03 | 2012-06-07 | Theravance, Inc. | Serotonin reuptake inhibitors |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2245061A1 (de) * | 1972-09-14 | 1974-03-28 | Boehringer Mannheim Gmbh | Derivate des adenins |
| BE824133A (fr) * | 1974-01-11 | 1975-07-07 | Nouveaux derives d'adenines n6-substituees et procedes de preparation | |
| DE2550000A1 (de) * | 1975-11-07 | 1977-05-12 | Boehringer Mannheim Gmbh | Neue purin-derivate und verfahren zu ihrer herstellung |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1268951A (en) * | 1969-06-12 | 1972-03-29 | Pfizer Ltd | Phenoxy-amines |
-
1975
- 1975-11-07 DE DE19752549999 patent/DE2549999A1/de active Granted
-
1976
- 1976-10-25 ZA ZA766381A patent/ZA766381B/xx unknown
- 1976-10-28 CA CA264,608A patent/CA1077942A/en not_active Expired
- 1976-10-29 IE IE2394/76A patent/IE43866B1/en unknown
- 1976-11-01 HU HU76BO00001639A patent/HU171237B/hu not_active IP Right Cessation
- 1976-11-01 US US05/737,518 patent/US4243807A/en not_active Expired - Lifetime
- 1976-11-02 SU SU762415648A patent/SU633473A3/ru active
- 1976-11-02 DK DK494876A patent/DK494876A/da not_active Application Discontinuation
- 1976-11-03 FI FI763148A patent/FI763148A7/fi not_active Application Discontinuation
- 1976-11-03 CH CH1385576A patent/CH624102A5/de not_active IP Right Cessation
- 1976-11-03 SE SE7612234A patent/SE7612234L/xx not_active Application Discontinuation
- 1976-11-04 DD DD195610A patent/DD126942A5/xx unknown
- 1976-11-04 BE BE172068A patent/BE847973A/xx not_active IP Right Cessation
- 1976-11-04 GB GB45916/76A patent/GB1502050A/en not_active Expired
- 1976-11-05 LU LU76141A patent/LU76141A1/xx unknown
- 1976-11-05 NL NL7612286A patent/NL7612286A/xx not_active Application Discontinuation
- 1976-11-05 IT IT29083/76A patent/IT1063618B/it active
- 1976-11-05 JP JP51133139A patent/JPS6055509B2/ja not_active Expired
- 1976-11-05 FR FR7633389A patent/FR2330678A1/fr active Granted
- 1976-11-05 AT AT823776A patent/AT352726B/de not_active IP Right Cessation
-
1977
- 1977-10-21 SU SU772534004A patent/SU867298A3/ru active
- 1977-10-21 SU SU772534003A patent/SU662009A3/ru active
-
1980
- 1980-10-03 CH CH742380A patent/CH625788A5/de not_active IP Right Cessation
- 1980-10-03 CH CH742480A patent/CH627166A5/de not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2245061A1 (de) * | 1972-09-14 | 1974-03-28 | Boehringer Mannheim Gmbh | Derivate des adenins |
| BE824133A (fr) * | 1974-01-11 | 1975-07-07 | Nouveaux derives d'adenines n6-substituees et procedes de preparation | |
| DE2550000A1 (de) * | 1975-11-07 | 1977-05-12 | Boehringer Mannheim Gmbh | Neue purin-derivate und verfahren zu ihrer herstellung |
Non-Patent Citations (1)
| Title |
|---|
| Zusätzlich sind zur Einsicht für jedermann bereitzuhalten: Versuchsprotokoll, eingegangen am 27.03.86 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0200826A1 (en) * | 1984-03-13 | 1986-11-12 | Aberg, Gunnar A.K. | Membrane stabilizing compounds and pharmaceutical preparations and methods employing such compounds |
| US5210086A (en) * | 1990-10-02 | 1993-05-11 | Synthelabo | 2-aminopyrimidine-4-carboxamide derivatives, their preparation and their use in therapy |
Also Published As
| Publication number | Publication date |
|---|---|
| CH627166A5 (en, 2012) | 1981-12-31 |
| IE43866L (en) | 1977-05-07 |
| DE2549999C2 (en, 2012) | 1989-01-26 |
| ZA766381B (en) | 1977-10-26 |
| CA1077942A (en) | 1980-05-20 |
| LU76141A1 (en, 2012) | 1977-05-18 |
| FI763148A7 (en, 2012) | 1977-05-08 |
| BE847973A (fr) | 1977-05-04 |
| SU867298A3 (ru) | 1981-09-23 |
| DK494876A (da) | 1977-05-08 |
| US4243807A (en) | 1981-01-06 |
| ATA823776A (de) | 1979-03-15 |
| AT352726B (de) | 1979-10-10 |
| JPS6055509B2 (ja) | 1985-12-05 |
| JPS5259163A (en) | 1977-05-16 |
| FR2330678A1 (fr) | 1977-06-03 |
| IT1063618B (it) | 1985-02-11 |
| CH625788A5 (en, 2012) | 1981-10-15 |
| CH624102A5 (en, 2012) | 1981-07-15 |
| FR2330678B1 (en, 2012) | 1980-11-07 |
| SU633473A3 (ru) | 1978-11-15 |
| SE7612234L (sv) | 1977-05-07 |
| NL7612286A (nl) | 1977-05-10 |
| SU662009A3 (ru) | 1979-05-05 |
| HU171237B (hu) | 1977-12-28 |
| IE43866B1 (en) | 1981-06-17 |
| GB1502050A (en) | 1978-02-22 |
| DD126942A5 (en, 2012) | 1977-08-24 |
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| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |