GB2044260A - New piperidine derivatives process for their preparation and their therapeutic applications - Google Patents
New piperidine derivatives process for their preparation and their therapeutic applications Download PDFInfo
- Publication number
- GB2044260A GB2044260A GB8005923A GB8005923A GB2044260A GB 2044260 A GB2044260 A GB 2044260A GB 8005923 A GB8005923 A GB 8005923A GB 8005923 A GB8005923 A GB 8005923A GB 2044260 A GB2044260 A GB 2044260A
- Authority
- GB
- United Kingdom
- Prior art keywords
- piperidine
- compound
- composition
- preparation
- benzyloxy
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 5
- 230000001225 therapeutic effect Effects 0.000 title claims description 4
- 150000003053 piperidines Chemical class 0.000 title description 3
- 150000003839 salts Chemical class 0.000 claims description 11
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- ILJHWVWEYBJDDM-UHFFFAOYSA-N 4-phenylmethoxypiperidine Chemical compound C=1C=CC=CC=1COC1CCNCC1 ILJHWVWEYBJDDM-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 4
- 229940073608 benzyl chloride Drugs 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 230000002921 anti-spasmodic effect Effects 0.000 claims description 3
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 claims description 3
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000007911 parenteral administration Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- GKGCPWOZAGTHMX-UHFFFAOYSA-N (4-hydroxypiperidin-1-yl)-(4-nitrophenyl)methanone Chemical compound C1CC(O)CCN1C(=O)C1=CC=C([N+]([O-])=O)C=C1 GKGCPWOZAGTHMX-UHFFFAOYSA-N 0.000 description 2
- LAOQIHVQAMCKLS-UHFFFAOYSA-N 4-phenylmethoxypiperidine hydrobromide Chemical compound Br.C(C1=CC=CC=C1)OC1CCNCC1 LAOQIHVQAMCKLS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 2
- 229910001626 barium chloride Inorganic materials 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 229960001789 papaverine Drugs 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 208000002881 Colic Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 238000011785 NMRI mouse Methods 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010046823 Uterine spasm Diseases 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 206010003230 arteritis Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000003170 musculotropic effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- -1 p - nitrobenzoyl -4- benzyloxy - piperidine Chemical compound 0.000 description 1
- KGCNHWXDPDPSBV-UHFFFAOYSA-N p-nitrobenzyl chloride Chemical compound [O-][N+](=O)C1=CC=C(CCl)C=C1 KGCNHWXDPDPSBV-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- UFLMJULGUPSTCY-UHFFFAOYSA-M sodium;4-nitrobenzoate Chemical compound [Na+].[O-]C(=O)C1=CC=C([N+]([O-])=O)C=C1 UFLMJULGUPSTCY-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 230000009278 visceral effect Effects 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
- C07D211/36—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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7906070A FR2450816A1 (fr) | 1979-03-09 | 1979-03-09 | Nouveaux derives de la piperidine, leur procede de preparation et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2044260A true GB2044260A (en) | 1980-10-15 |
Family
ID=9222953
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8005923A Withdrawn GB2044260A (en) | 1979-03-09 | 1980-02-21 | New piperidine derivatives process for their preparation and their therapeutic applications |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0015817A1 (enExample) |
| JP (1) | JPS55122761A (enExample) |
| AU (1) | AU5594080A (enExample) |
| BE (1) | BE882122A (enExample) |
| ES (1) | ES489042A1 (enExample) |
| FR (1) | FR2450816A1 (enExample) |
| GB (1) | GB2044260A (enExample) |
| IT (1) | IT8067364A0 (enExample) |
| NO (1) | NO800660L (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE13425T1 (de) | 1981-10-15 | 1985-06-15 | Synthelabo | Piperidin-derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel. |
| US4529730A (en) * | 1981-10-21 | 1985-07-16 | Synthelabo | Piperidine derivatives, their preparation and pharmaceutical compositions containing them |
| GB8321157D0 (en) * | 1983-08-05 | 1983-09-07 | Fordonal Sa | Piperidine derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3260723A (en) * | 1963-08-27 | 1966-07-12 | Parke Davis & Co | 4-phenoxy piperidines; alpha4-phenoxy piperideines |
-
1979
- 1979-03-09 FR FR7906070A patent/FR2450816A1/fr active Granted
-
1980
- 1980-02-21 GB GB8005923A patent/GB2044260A/en not_active Withdrawn
- 1980-02-25 EP EP80400258A patent/EP0015817A1/fr not_active Withdrawn
- 1980-02-27 AU AU55940/80A patent/AU5594080A/en not_active Abandoned
- 1980-02-28 ES ES489042A patent/ES489042A1/es not_active Expired
- 1980-03-07 BE BE0/199707A patent/BE882122A/fr unknown
- 1980-03-07 JP JP2906880A patent/JPS55122761A/ja active Pending
- 1980-03-07 IT IT8067364A patent/IT8067364A0/it unknown
- 1980-03-07 NO NO800660A patent/NO800660L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2450816A1 (fr) | 1980-10-03 |
| NO800660L (no) | 1980-09-10 |
| IT8067364A0 (it) | 1980-03-07 |
| BE882122A (fr) | 1980-09-08 |
| FR2450816B1 (enExample) | 1981-05-22 |
| EP0015817A1 (fr) | 1980-09-17 |
| ES489042A1 (es) | 1980-09-16 |
| AU5594080A (en) | 1980-09-11 |
| JPS55122761A (en) | 1980-09-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |