DE1470123C3 - 4-(2,6-Dioxo-3-phenyl-3-piperidyl>piperidine, deren pharmakologisch verträgliche Säureadditionssalze und Verfahren zu ihrer Herstellung - Google Patents
4-(2,6-Dioxo-3-phenyl-3-piperidyl>piperidine, deren pharmakologisch verträgliche Säureadditionssalze und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE1470123C3 DE1470123C3 DE1470123A DE1470123A DE1470123C3 DE 1470123 C3 DE1470123 C3 DE 1470123C3 DE 1470123 A DE1470123 A DE 1470123A DE 1470123 A DE1470123 A DE 1470123A DE 1470123 C3 DE1470123 C3 DE 1470123C3
- Authority
- DE
- Germany
- Prior art keywords
- parts
- piperidyl
- phenyl
- dioxo
- piperidine
- 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.)
- Expired
Links
- -1 2,6-Dioxo-3-phenyl-3-piperidyl Chemical group 0.000 title description 17
- 239000002253 acid Substances 0.000 title description 12
- 150000003839 salts Chemical class 0.000 title description 11
- 238000002360 preparation method Methods 0.000 title description 4
- 238000000034 method Methods 0.000 title description 3
- 150000003053 piperidines Chemical class 0.000 title description 2
- WCKABEIXAFZEIO-UHFFFAOYSA-N 3-phenyl-3-piperidin-4-ylpiperidine-2,6-dione Chemical class O=C1NC(=O)CCC1(C=1C=CC=CC=1)C1CCNCC1 WCKABEIXAFZEIO-UHFFFAOYSA-N 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 238000002844 melting Methods 0.000 description 22
- 230000008018 melting Effects 0.000 description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 19
- 238000001816 cooling Methods 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000000843 powder Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
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- 238000006243 chemical reaction Methods 0.000 description 8
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 6
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
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- 239000002244 precipitate Substances 0.000 description 6
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- RUCTVLMLGCMCSB-UHFFFAOYSA-N 2-phenyl-2-piperidin-4-ylpentanedinitrile Chemical class C(#N)C(CCC#N)(C1=CC=CC=C1)C1CCNCC1 RUCTVLMLGCMCSB-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- XSOOSXRNMDUWEM-UHFFFAOYSA-N 3-(1-benzylpiperidin-1-ium-4-yl)-3-phenylpiperidine-2,6-dione;chloride Chemical compound Cl.O=C1NC(=O)CCC1(C=1C=CC=CC=1)C1CCN(CC=2C=CC=CC=2)CC1 XSOOSXRNMDUWEM-UHFFFAOYSA-N 0.000 description 2
- LQQIVYSCPWCSSD-UHFFFAOYSA-N Benzetimide Chemical compound O=C1NC(=O)CCC1(C=1C=CC=CC=1)C1CCN(CC=2C=CC=CC=2)CC1 LQQIVYSCPWCSSD-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
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- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- GIJXKZJWITVLHI-PMOLBWCYSA-N benzatropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(C=1C=CC=CC=1)C1=CC=CC=C1 GIJXKZJWITVLHI-PMOLBWCYSA-N 0.000 description 2
- 229960001081 benzatropine Drugs 0.000 description 2
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- 239000003054 catalyst Substances 0.000 description 2
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- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
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- 230000003389 potentiating effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
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- CIVCELMLGDGMKZ-UHFFFAOYSA-N 2,4-dichloro-6-methylpyridine-3-carboxylic acid Chemical compound CC1=CC(Cl)=C(C(O)=O)C(Cl)=N1 CIVCELMLGDGMKZ-UHFFFAOYSA-N 0.000 description 1
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- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
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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
- C07D211/80—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
- 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
- C07D211/34—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19540462A | 1962-05-17 | 1962-05-17 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1470123A1 DE1470123A1 (de) | 1969-05-08 |
| DE1470123B2 DE1470123B2 (de) | 1974-02-21 |
| DE1470123C3 true DE1470123C3 (de) | 1974-10-03 |
Family
ID=22721293
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1470123A Expired DE1470123C3 (de) | 1962-05-17 | 1963-05-09 | 4-(2,6-Dioxo-3-phenyl-3-piperidyl>piperidine, deren pharmakologisch verträgliche Säureadditionssalze und Verfahren zu ihrer Herstellung |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3125578A (https=) |
| BE (1) | BE632403A (https=) |
| BR (1) | BR6349213D0 (https=) |
| CH (2) | CH460770A (https=) |
| DE (1) | DE1470123C3 (https=) |
| FR (2) | FR1364179A (https=) |
| GB (1) | GB1024521A (https=) |
| SE (2) | SE325570B (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT393122B (de) * | 1987-09-25 | 1991-08-26 | Madaus Ag | Verfahren zur herstellung von neuen 3-aryl-3-cycloalkyl-piperidin-2,6-dion-derivaten und ihren salzen |
| US5281601A (en) * | 1989-12-12 | 1994-01-25 | Pfizer Inc. | Muscarinic receptor antagonists |
| GB8928043D0 (en) * | 1989-12-12 | 1990-02-14 | Pfizer Ltd | Muscarinic receptor antagonists |
| WO1995011234A1 (en) * | 1993-10-22 | 1995-04-27 | Australian Nuclear Science & Technology Organisation | Radiolabelled ligands for muscarinic receptors |
| BRPI0707623A2 (pt) * | 2006-02-10 | 2011-05-10 | Janssen Pharmaceutica Nv | derivados de piperidina como antagonistas de receptores de cxcr3 |
| BRPI0707629A2 (pt) * | 2006-02-10 | 2011-05-10 | Janssen Pharmaceutica Nv | derivados de piperidina como antagonistas do receptor de cxcr3 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2749346A (en) * | 1956-06-05 | Tetrahydropyridine compounds |
-
0
- US US3125578D patent/US3125578A/en not_active Expired - Lifetime
- BE BE632403D patent/BE632403A/xx unknown
-
1963
- 1963-05-06 CH CH566663A patent/CH460770A/de unknown
- 1963-05-06 CH CH279067A patent/CH493517A/de not_active IP Right Cessation
- 1963-05-09 GB GB18450/63A patent/GB1024521A/en not_active Expired
- 1963-05-09 DE DE1470123A patent/DE1470123C3/de not_active Expired
- 1963-05-16 FR FR935118A patent/FR1364179A/fr not_active Expired
- 1963-05-16 SE SE05464/63A patent/SE325570B/xx unknown
- 1963-05-17 BR BR149213/63A patent/BR6349213D0/pt unknown
- 1963-08-14 FR FR944811A patent/FR2983M/fr not_active Expired
-
1967
- 1967-03-13 SE SE03448/67A patent/SE333929B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR1364179A (fr) | 1964-06-19 |
| FR2983M (https=) | 1964-12-07 |
| SE325570B (https=) | 1970-07-06 |
| CH460770A (de) | 1968-08-15 |
| GB1024521A (en) | 1966-03-30 |
| DE1470123A1 (de) | 1969-05-08 |
| BE632403A (https=) | 1900-01-01 |
| CH493517A (de) | 1970-07-15 |
| BR6349213D0 (pt) | 1973-08-02 |
| US3125578A (en) | 1964-03-17 |
| SE333929B (https=) | 1971-04-05 |
| DE1470123B2 (de) | 1974-02-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |