GB1076531A - 4-substituted-n-(substituted-allyl)-piperidines - Google Patents
4-substituted-n-(substituted-allyl)-piperidinesInfo
- Publication number
- GB1076531A GB1076531A GB195965A GB195965A GB1076531A GB 1076531 A GB1076531 A GB 1076531A GB 195965 A GB195965 A GB 195965A GB 195965 A GB195965 A GB 195965A GB 1076531 A GB1076531 A GB 1076531A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- substituted
- hydroxyphenyl
- piperidines
- hydrogen
- 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 13
- 229910052739 hydrogen Inorganic materials 0.000 abstract 10
- 239000001257 hydrogen Substances 0.000 abstract 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 10
- 150000001875 compounds Chemical class 0.000 abstract 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 6
- 229910052801 chlorine Inorganic materials 0.000 abstract 6
- 239000000460 chlorine Substances 0.000 abstract 6
- -1 hydroxy, methoxy Chemical group 0.000 abstract 6
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 abstract 4
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 abstract 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 4
- 229910052794 bromium Inorganic materials 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 abstract 4
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 abstract 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- LXKNAUOWEJWGTE-UHFFFAOYSA-N 2-(3-methoxyphenyl)acetonitrile Chemical compound COC1=CC=CC(CC#N)=C1 LXKNAUOWEJWGTE-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 abstract 2
- 230000000202 analgesic effect Effects 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 239000011737 fluorine Chemical group 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 229960005181 morphine Drugs 0.000 abstract 2
- 231100000252 nontoxic Toxicity 0.000 abstract 2
- 230000003000 nontoxic effect Effects 0.000 abstract 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 2
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 abstract 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- UOORRWUZONOOLO-OWOJBTEDSA-N (E)-1,3-dichloropropene Chemical compound ClC\C=C\Cl UOORRWUZONOOLO-OWOJBTEDSA-N 0.000 abstract 1
- AHDWGYQKJRIOKW-UHFFFAOYSA-N 1-(3-hydroxyphenyl)piperidine-4-carboxylic acid Chemical compound OC=1C=C(C=CC1)N1CCC(CC1)C(=O)O AHDWGYQKJRIOKW-UHFFFAOYSA-N 0.000 abstract 1
- XQOHGUZOLKLXLU-UHFFFAOYSA-N 1-but-2-enylpiperidine Chemical class CC=CCN1CCCCC1 XQOHGUZOLKLXLU-UHFFFAOYSA-N 0.000 abstract 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 abstract 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- ALFGKMXHOUSVAD-UHFFFAOYSA-N Ketobemidone Chemical compound C=1C=CC(O)=CC=1C1(C(=O)CC)CCN(C)CC1 ALFGKMXHOUSVAD-UHFFFAOYSA-N 0.000 abstract 1
- XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 230000003042 antagnostic effect Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 abstract 1
- 238000001640 fractional crystallisation Methods 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 150000004658 ketimines Chemical class 0.000 abstract 1
- 229960003029 ketobemidone Drugs 0.000 abstract 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 229960000482 pethidine Drugs 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 abstract 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 abstract 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 abstract 1
- 235000017557 sodium bicarbonate Nutrition 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- UOORRWUZONOOLO-UHFFFAOYSA-N telone II Natural products ClCC=CCl UOORRWUZONOOLO-UHFFFAOYSA-N 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 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
- C07D211/30—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 doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—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 doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom 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
- C07D211/36—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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
- C07D211/64—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having an aryl radical as the second substituent in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0075148 | 1964-01-24 | ||
| DEB0075540 | 1964-02-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1076531A true GB1076531A (en) | 1967-07-19 |
Family
ID=25966942
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB195965A Expired GB1076531A (en) | 1964-01-24 | 1965-01-15 | 4-substituted-n-(substituted-allyl)-piperidines |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE658583A (enrdf_load_stackoverflow) |
| CH (3) | CH512469A (enrdf_load_stackoverflow) |
| DE (2) | DE1445518A1 (enrdf_load_stackoverflow) |
| DK (3) | DK118283B (enrdf_load_stackoverflow) |
| FR (2) | FR4317M (enrdf_load_stackoverflow) |
| GB (1) | GB1076531A (enrdf_load_stackoverflow) |
| NL (1) | NL6500808A (enrdf_load_stackoverflow) |
| SE (1) | SE323370B (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH492710A (de) * | 1968-01-11 | 1970-06-30 | Geigy Ag J R | Verfahren zur Herstellung von neuen Piperidinderivaten |
| CH491918A (de) * | 1968-01-11 | 1970-06-15 | Geigy Ag J R | Verfahren zur Herstellung von neuen Piperidinderivaten |
| GB9924797D0 (en) * | 1999-10-20 | 1999-12-22 | West Pharm Serv Drug Res Ltd | Compound |
-
1964
- 1964-01-24 DE DE19641445518 patent/DE1445518A1/de active Pending
- 1964-02-21 DE DE19641445520 patent/DE1445520A1/de active Pending
-
1965
- 1965-01-15 GB GB195965A patent/GB1076531A/en not_active Expired
- 1965-01-20 BE BE658583D patent/BE658583A/xx unknown
- 1965-01-20 FR FR2645A patent/FR4317M/fr not_active Expired
- 1965-01-20 FR FR2646A patent/FR1455818A/fr not_active Expired
- 1965-01-21 CH CH1748267A patent/CH512469A/de not_active IP Right Cessation
- 1965-01-21 CH CH1147671A patent/CH512470A/de not_active IP Right Cessation
- 1965-01-21 CH CH86565A patent/CH453358A/de unknown
- 1965-01-22 NL NL6500808A patent/NL6500808A/xx unknown
- 1965-01-22 SE SE85665A patent/SE323370B/xx unknown
- 1965-01-23 DK DK38565A patent/DK118283B/da unknown
- 1965-12-30 DK DK670065A patent/DK121373B/da unknown
-
1966
- 1966-11-04 DK DK575566A patent/DK115392B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH512470A (de) | 1971-09-15 |
| FR1455818A (fr) | 1966-10-21 |
| DK118283B (da) | 1970-08-03 |
| DK121373B (da) | 1971-10-11 |
| SE323370B (enrdf_load_stackoverflow) | 1970-05-04 |
| NL6500808A (enrdf_load_stackoverflow) | 1965-07-26 |
| DE1445520A1 (de) | 1968-12-12 |
| FR4317M (enrdf_load_stackoverflow) | 1966-09-05 |
| BE658583A (enrdf_load_stackoverflow) | 1965-07-20 |
| DK115392B (da) | 1969-10-06 |
| CH512469A (de) | 1971-09-15 |
| DE1445518A1 (de) | 1968-12-05 |
| CH453358A (de) | 1968-06-14 |
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