GB1316424A - Alpha-hydroxy-substituted-phenyl-alpha-2-piperidyl-methanols and process for the preparation thereof - Google Patents
Alpha-hydroxy-substituted-phenyl-alpha-2-piperidyl-methanols and process for the preparation thereofInfo
- Publication number
- GB1316424A GB1316424A GB2563469A GB1316424DA GB1316424A GB 1316424 A GB1316424 A GB 1316424A GB 2563469 A GB2563469 A GB 2563469A GB 1316424D A GB1316424D A GB 1316424DA GB 1316424 A GB1316424 A GB 1316424A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyridyl
- alkoxy
- phenyl
- alkyl
- poly
- 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
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- -1 diphenyl-alkyl Chemical group 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000005036 alkoxyphenyl group Chemical group 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- QPOWUYJWCJRLEE-UHFFFAOYSA-N dipyridin-2-ylmethanone Chemical class C=1C=CC=NC=1C(=O)C1=CC=CC=N1 QPOWUYJWCJRLEE-UHFFFAOYSA-N 0.000 abstract 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 abstract 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 abstract 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 abstract 1
- 229940035437 1,3-propanediol Drugs 0.000 abstract 1
- 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 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- 230000003182 bronchodilatating effect Effects 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- JDOZOOBCADNBIJ-UHFFFAOYSA-N lithium;2h-pyridin-2-ide Chemical compound [Li+].C1=CC=N[C-]=C1 JDOZOOBCADNBIJ-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000008024 pharmaceutical diluent Substances 0.000 abstract 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 abstract 1
- 229940081066 picolinic acid Drugs 0.000 abstract 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/02—Preparation by ring-closure or hydrogenation
-
- 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2563469 | 1969-05-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1316424A true GB1316424A (en) | 1973-05-09 |
Family
ID=10230843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2563469A Expired GB1316424A (en) | 1969-05-20 | 1969-05-20 | Alpha-hydroxy-substituted-phenyl-alpha-2-piperidyl-methanols and process for the preparation thereof |
Country Status (12)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991018602A1 (en) * | 1990-06-01 | 1991-12-12 | Merrell Dow Pharmaceuticals Inc. | (+)-α-(2,3-DIMETHOXYPHENYL)-1-[2-(4-FLUOROPHENYL)ETHYL]-4-PIPERIDINEMETHANOL |
| US6004980A (en) * | 1990-06-01 | 1999-12-21 | Merrell Pharmaceuticals, Inc. | (+)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol |
| US6028083A (en) * | 1997-07-25 | 2000-02-22 | Hoechst Marion Roussel, Inc. | Esters of (+)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl) ethyl]-4-piperidinemethanol |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA960676A (en) * | 1970-05-21 | 1975-01-07 | Smith Kline And French Canada Ltd. | 3-sulfonamido-4-hydroxyphenyl-2-piperidinylcarbinols |
| US5169096A (en) * | 1985-07-02 | 1992-12-08 | Merrell Dow Pharmaceuticals Inc. | N-aralkyl-piperidine-methanol derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE569836A (enrdf_load_stackoverflow) * |
-
1969
- 1969-05-20 GB GB2563469A patent/GB1316424A/en not_active Expired
-
1970
- 1970-05-12 ZA ZA703208A patent/ZA703208B/xx unknown
- 1970-05-16 DE DE2024049A patent/DE2024049C3/de not_active Expired
- 1970-05-17 IL IL34537A patent/IL34537A/en unknown
- 1970-05-19 NO NO1909/70A patent/NO133448C/no unknown
- 1970-05-19 CH CH740570A patent/CH541557A/de not_active IP Right Cessation
- 1970-05-19 FR FR7018131A patent/FR2051549B1/fr not_active Expired
- 1970-05-19 BE BE750590D patent/BE750590A/xx not_active IP Right Cessation
- 1970-05-19 DK DK253670AA patent/DK124027B/da not_active IP Right Cessation
- 1970-05-19 SE SE7006827A patent/SE374366B/xx unknown
- 1970-05-20 JP JP45042819A patent/JPS4920787B1/ja active Pending
- 1970-05-20 NL NLAANVRAGE7007303,A patent/NL169314C/xx not_active IP Right Cessation
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991018602A1 (en) * | 1990-06-01 | 1991-12-12 | Merrell Dow Pharmaceuticals Inc. | (+)-α-(2,3-DIMETHOXYPHENYL)-1-[2-(4-FLUOROPHENYL)ETHYL]-4-PIPERIDINEMETHANOL |
| US5134149A (en) * | 1990-06-01 | 1992-07-28 | Merrell Dow Pharmaceuticals Inc. | (+)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol |
| US5700813A (en) * | 1990-06-01 | 1997-12-23 | Merrell Pharmaceuticals Inc. | (+)-α-(2,3-dimethoxyphenyl)-1- 2-(4-fluorophenyl)ethyl!-4-piperidinemethanol |
| US5700812A (en) * | 1990-06-01 | 1997-12-23 | Merrell Pharmaceuticals Inc. | (+)-α-(2,3-dimethoxyphenyl)-1- 2-(4-fluorophenyl)ethyl!-4-piperidinemethanol |
| US5874445A (en) * | 1990-06-01 | 1999-02-23 | Merrell Pharmaceutical, Inc. | (+) -α- (2,3-dimethoxyphenyl)-1-(2-(4-fluorephenyl) ethyl)-4-piepridinemethanol |
| US6004980A (en) * | 1990-06-01 | 1999-12-21 | Merrell Pharmaceuticals, Inc. | (+)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol |
| US6028083A (en) * | 1997-07-25 | 2000-02-22 | Hoechst Marion Roussel, Inc. | Esters of (+)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl) ethyl]-4-piperidinemethanol |
| US6063793A (en) * | 1997-07-25 | 2000-05-16 | Hoechst Marion Roussel, Inc. | Esters of (+)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidi nemethanol |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2051549B1 (enrdf_load_stackoverflow) | 1974-08-30 |
| CH541557A (de) | 1973-09-15 |
| NL7007303A (enrdf_load_stackoverflow) | 1970-11-24 |
| IL34537A0 (en) | 1970-07-19 |
| IL34537A (en) | 1973-03-30 |
| DE2024049A1 (enrdf_load_stackoverflow) | 1970-12-17 |
| DE2024049B2 (de) | 1977-11-24 |
| NO133448B (enrdf_load_stackoverflow) | 1976-01-26 |
| SE374366B (enrdf_load_stackoverflow) | 1975-03-03 |
| NO133448C (enrdf_load_stackoverflow) | 1976-05-05 |
| DE2024049C3 (de) | 1978-07-20 |
| NL169314B (nl) | 1982-02-01 |
| ZA703208B (en) | 1971-01-27 |
| NL169314C (nl) | 1982-07-01 |
| DK124027B (da) | 1972-09-04 |
| BE750590A (fr) | 1970-11-19 |
| JPS4920787B1 (enrdf_load_stackoverflow) | 1974-05-27 |
| FR2051549A1 (enrdf_load_stackoverflow) | 1971-04-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 429A | Application made for amendment of specification (sect. 29/1949) | ||
| 429N | Application abandoned (sect. 29/1949) | ||
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |