GB1187393A - Improvements in or relating to Piperidine Compounds - Google Patents
Improvements in or relating to Piperidine CompoundsInfo
- Publication number
- GB1187393A GB1187393A GB31393/66A GB3139366A GB1187393A GB 1187393 A GB1187393 A GB 1187393A GB 31393/66 A GB31393/66 A GB 31393/66A GB 3139366 A GB3139366 A GB 3139366A GB 1187393 A GB1187393 A GB 1187393A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- substituents
- carry
- halogen
- group
- 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
- 150000003053 piperidines Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 150000002367 halogens Chemical group 0.000 abstract 5
- -1 hydrocarbon radical Chemical class 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 229910052736 halogen Chemical group 0.000 abstract 3
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 abstract 2
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical group C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 2
- DIXBSCZRIZDQGC-UHFFFAOYSA-N diaziridine Chemical group C1NN1 DIXBSCZRIZDQGC-UHFFFAOYSA-N 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- HUUPVABNAQUEJW-UHFFFAOYSA-N 1-methylpiperidin-4-one Chemical compound CN1CCC(=O)CC1 HUUPVABNAQUEJW-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 150000001602 bicycloalkyls Chemical group 0.000 abstract 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- MRRXGLNCXPJBJU-UHFFFAOYSA-N piperidin-4-imine Chemical compound N=C1CCNCC1 MRRXGLNCXPJBJU-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 150000003413 spiro compounds Chemical class 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
1,187,393. Spiro compounds. NOVO TERAPEUTISK LABORATORIUM A/S. 28 June, 1967 [13 July, 1966], No. 31393/66. Heading C2C. Novel, therapeutic compounds I (including salts thereof) in which Y represents a group of the Formula II or III wherein R 1 and R 2 signify hydrogen; nalkyl, iso-alkyl, alkenyl or alkynyl, which may carry halogen substituents; hydroxyalkyl, which may carry halogen substituents, or esters or ethers thereof; dialkylamino-alkyl; cycloalkyl, bicycloalkyl or aza-cycloalkyl which may all carry alkyl substituents; acyl ; carbamyl or substituted carbamyl where the substituents may be alkyl, cycloalkyl, aryl or arylsulphonyl, which substituents may be substituted by alkyl, alkoxy or halogen; or R 3 -X-, wherein -X- is a bivalent aliphatic and/or cycloaliphatic hydrocarbon radical with 1 to 8 carbons and which may carry halogen and hydroxy substituents, and R 3 means cycloalkyl, aryl or a heterocyclic radical with nitrogen or oxygen as hetero atoms, all of which may carry alkyl or alkoxy substituents, R 4 is hydrogen, alkyl, acyl, or aralkyl and R 6 , R 7 , R 8 , R 9 , R 10 and R 11 mean hydrogen, alkyl or aryl, with the addition that R 8 (or R 9 ) may together with R, or R 6 form an ethylene bridge (Z = -CH 2 -CH 2 -) are prepared: (i) by reacting an appropriate 4-piperidone (may contain the Z-bridge) with ammonia or an amine and a compound of formula R<SP>1</SP>NHR, wherein R is -OSO 2 OH or halogen and R<SP>1</SP> is hydrogen or alkyl; or (ii) by reacting an appropriate 4-imino-piperidine (may contain the Z-bridge) with the compound R<SP>1</SP>NHR; and thereafter, if desired, oxidizing a resulting unsubstituted diaziridine group to form a diazirine group and converting a resulting diazirine, an unsubstituted diaziridine or monosubstituted diaziridine group into a mono- or di-substituted diaziridine group. 1 - Methylpiperidine - 4 - benzylimme is obtained by the interaction of 1-methyl-4-piperidone and benzylamine.
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB31393/66A GB1187393A (en) | 1966-07-13 | 1966-07-13 | Improvements in or relating to Piperidine Compounds |
| GR670133975A GR33975B (en) | 1966-07-13 | 1967-07-05 | METHOD FOR THE PRODUCTION OF PIPERIDINE PRODUCERS. |
| DE19671695565 DE1695565A1 (en) | 1966-07-13 | 1967-07-12 | Novel piperidine derivatives and processes for their preparation |
| BE701293D BE701293A (en) | 1966-07-13 | 1967-07-12 | |
| ES342940A ES342940A1 (en) | 1966-07-13 | 1967-07-12 | Improvements in or relating to Piperidine Compounds |
| NL6709754A NL6709754A (en) | 1966-07-13 | 1967-07-13 | |
| FR1562790D FR1562790A (en) | 1966-07-13 | 1967-07-13 | |
| AT657867A AT268324B (en) | 1966-07-13 | 1967-07-13 | Process for the preparation of new diazirine or diaziridine derivatives and their salts |
| FR124432A FR7176M (en) | 1966-07-13 | 1967-10-13 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB31393/66A GB1187393A (en) | 1966-07-13 | 1966-07-13 | Improvements in or relating to Piperidine Compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1187393A true GB1187393A (en) | 1970-04-08 |
Family
ID=10322434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB31393/66A Expired GB1187393A (en) | 1966-07-13 | 1966-07-13 | Improvements in or relating to Piperidine Compounds |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT268324B (en) |
| BE (1) | BE701293A (en) |
| DE (1) | DE1695565A1 (en) |
| ES (1) | ES342940A1 (en) |
| FR (2) | FR1562790A (en) |
| GB (1) | GB1187393A (en) |
| GR (1) | GR33975B (en) |
| NL (1) | NL6709754A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49118419A (en) * | 1973-03-12 | 1974-11-12 | ||
| WO2013121334A3 (en) * | 2012-02-17 | 2013-10-31 | Cro Consulting Limited | Agents for treating neurodegenerative disorders |
-
1966
- 1966-07-13 GB GB31393/66A patent/GB1187393A/en not_active Expired
-
1967
- 1967-07-05 GR GR670133975A patent/GR33975B/en unknown
- 1967-07-12 ES ES342940A patent/ES342940A1/en not_active Expired
- 1967-07-12 DE DE19671695565 patent/DE1695565A1/en active Pending
- 1967-07-12 BE BE701293D patent/BE701293A/xx unknown
- 1967-07-13 AT AT657867A patent/AT268324B/en active
- 1967-07-13 FR FR1562790D patent/FR1562790A/fr not_active Expired
- 1967-07-13 NL NL6709754A patent/NL6709754A/xx unknown
- 1967-10-13 FR FR124432A patent/FR7176M/fr not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49118419A (en) * | 1973-03-12 | 1974-11-12 | ||
| JPS549888B2 (en) * | 1973-03-12 | 1979-04-28 | ||
| WO2013121334A3 (en) * | 2012-02-17 | 2013-10-31 | Cro Consulting Limited | Agents for treating neurodegenerative disorders |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6709754A (en) | 1968-01-15 |
| AT268324B (en) | 1969-02-10 |
| BE701293A (en) | 1968-01-12 |
| DE1695565A1 (en) | 1970-07-16 |
| FR7176M (en) | 1969-08-11 |
| GR33975B (en) | 1968-02-29 |
| ES342940A1 (en) | 1968-08-01 |
| FR1562790A (en) | 1969-04-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 416 | Proceeding under section 16 patents act 1949 | ||
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |