IE37697L - Piperazine derivatives - Google Patents
Piperazine derivativesInfo
- Publication number
- IE37697L IE37697L IE117372A IE117372A IE37697L IE 37697 L IE37697 L IE 37697L IE 117372 A IE117372 A IE 117372A IE 117372 A IE117372 A IE 117372A IE 37697 L IE37697 L IE 37697L
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- formula
- reacting
- hal
- product
- Prior art date
Links
- 150000004885 piperazines Chemical class 0.000 title 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 8
- 150000001412 amines Chemical class 0.000 abstract 5
- -1 1-Trifluoromethylphenyl Chemical group 0.000 abstract 3
- 238000000297 Sandmeyer reaction Methods 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 231100000252 nontoxic Toxicity 0.000 abstract 2
- 230000003000 nontoxic effect Effects 0.000 abstract 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 abstract 1
- HXTMLBZHJLMPCW-UHFFFAOYSA-N 2-[4-[4-bromo-3-(trifluoromethyl)phenyl]piperazin-1-yl]ethanamine Chemical compound NCCN1CCN(CC1)C1=CC(=C(C=C1)Br)C(F)(F)F HXTMLBZHJLMPCW-UHFFFAOYSA-N 0.000 abstract 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 abstract 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 150000001448 anilines Chemical class 0.000 abstract 1
- 230000036528 appetite Effects 0.000 abstract 1
- 235000019789 appetite Nutrition 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 abstract 1
- 238000006193 diazotization reaction Methods 0.000 abstract 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 229940014800 succinic anhydride Drugs 0.000 abstract 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
1368256 1-Trifluoromethylphenyl 4-(cyclic amido-alkyl)-piperazines PFIZER Ltd 4 Sept 1972 [4 Sept 1971 3 May 1972] 41322/71 and 20536/72 Heading C2C Novel compounds of the Formula (I) where R denotes a succinimido, glutarimido, 2,4 - dioxo - 1 (or 3) - imidazolidinyl or 2,4- dioxo - 1 (or 3) - hexahydropyrimidinyl group, the last two groups being optionally substituted on the imino N atom with a CH 3 or C 2 H 5 group; X denotes H, F, Cl or Br; and n is 2 or 3, and their non-toxic acid addition salts, are obtained (1) by reacting a 1-aryl piperazine (II) with an alkyl halide hal-(CH 2 ) n R, where hal is a halogen atom, e.g. Cl or Br, or a tosylalate tosyl(OH 2 ) n -R by heating in a dry inert organic solvent in the presence of a base; (2) by reacting a compound of the Formula (III) with a lower alkyl isocyanate or #-isocyanatopropionate to form a compound (IV) where R<SP>1</SP> is lower alkyl and m is 1 or 2, and then heating this product to effect ring closure, e.g. using an oil bath at 200‹ C. for several hours, (3) by reacting an amine of Formula (III) with a hal-CH 2 COOR<SP>2</SP> or hal-CH 2 CH 2 COOR<SP>2</SP>, in which the lower alkyl group R<SP>2</SP> is preferably methyl or ethyl, to yield a product of Formula (V) which is then reacted with methyl or ethyl isocyanate to yield (VI) (4) by reacting an amine (III) with succinic anhydride or glutaric anhydride at elevated temperature with or without solvent to form a product (VII) in which p is 2 or 3; (5) by appropriate nuclear aromatic halogenation of compounds (I) in which X is H; (6) by nitrosating a compound (I) in which X is H, reducing the nitroso group to amino, diazotizing followed by Sandmeyer reaction with CuCl or CuBr to form the Cl- or Br-substituted product; (7) by reducing a compound of Formula (I) in which X is NO 2 to an -NH 2 followed by diazotization and Sandmeyer reaction as a (6); (8) by reacting an aniline derivative (XII) with a compound [Y(CH 2 ) 3 ] 2 N-(CH 2 ) n R in which Y is OH or halogen. An intermediate, 1-(2-aminoethyl)-4-(4-bromo- 3 - trifluoromethylphenyl)piperazine is obtained by brominating 1 - (2 - aminomethyl) - 4 - (3- trifluoromethylphenyl)piperazine. A pharmaceutical composition for reducing appetite comprises a compound of Formula (I) above with a non-toxic carrier or diluent in forms suitable for oral or parenteral administration.
[GB1368256A]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4132271 | 1971-09-04 | ||
| GB2053672A GB1368256A (en) | 1971-09-04 | 1972-05-03 | 1- trifluoromethyl-phenyl- 4-cyclic-amidoalkyl- piperazines useful as amorectic agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE37697L true IE37697L (en) | 1973-03-04 |
| IE37697B1 IE37697B1 (en) | 1977-09-28 |
Family
ID=26254732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE117372A IE37697B1 (en) | 1971-09-04 | 1972-08-29 | 1-(trifluoromethyl-phenyl)-4-(cyclic-amido-alkyl)piperazines useful as anorectic agents |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS4885584A (en) |
| AR (1) | AR200387A1 (en) |
| AT (2) | AT320655B (en) |
| AU (1) | AU4594072A (en) |
| BE (1) | BE788280A (en) |
| CH (2) | CH554899A (en) |
| DE (1) | DE2242382A1 (en) |
| ES (1) | ES406374A1 (en) |
| FR (1) | FR2154449A1 (en) |
| GB (1) | GB1368256A (en) |
| IE (1) | IE37697B1 (en) |
| NL (1) | NL7211694A (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2263211A1 (en) * | 1972-12-23 | 1974-07-04 | Boehringer Sohn Ingelheim | NEW ARYLPIPERAZINE AND PROCESS FOR THEIR PRODUCTION |
| DE2727469A1 (en) * | 1977-06-18 | 1978-12-21 | Hoechst Ag | NEW HEXAHYDROPYRIMIDINE, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS |
| AU532411B2 (en) * | 1979-03-01 | 1983-09-29 | Duphar International Research B.V. | Phenyl piperazine derivatives |
| NL8005133A (en) * | 1980-09-12 | 1982-04-01 | Duphar Int Res | PHENYLPIPERAZINE DERIVATIVES WITH ANTIAGRESSIVE ACTION. |
| NL8005131A (en) * | 1980-09-12 | 1982-04-01 | Duphar Int Res | PHENYLPIPERAZINE DERIVATIVES WITH ANALGETIC ACTION. |
| US4452798A (en) * | 1982-06-22 | 1984-06-05 | Warner-Lambert Company | 1-Substituted phenyl-4-alkyl hydantoin piperazine compounds as antihypertensive agents |
| JPS5976059A (en) * | 1982-10-21 | 1984-04-28 | Sumitomo Chem Co Ltd | Cyclic imide derivative and its acid addition salt |
| US6083950A (en) * | 1997-11-13 | 2000-07-04 | Ranbaxy Laboratories Limited | 1-(4-arylpiperazin-1-yl)-ω-[n-(α,ω-dicarboximido)]-alka nes useful as uro-selective α1-adrenoceptor blockers |
| AU1979799A (en) * | 1998-07-21 | 2000-02-14 | Ranbaxy Laboratories Limited | Arylpiperazine derivatives useful as uro-selective alpha-1-adrenoceptor blockers |
| NZ509388A (en) * | 1998-07-21 | 2003-12-19 | Ranbaxy Lab Ltd | Arylpiperazine derivatives useful as uroselective alpha1-adrenoceptor blockers |
| EP1495000A4 (en) * | 2002-04-08 | 2005-10-05 | Ranbaxy Lab Ltd | Alpha, omega-dicarboximide derivatives as useful uro-selective a1a adrenoceptor blockers |
-
0
- BE BE788280D patent/BE788280A/en unknown
-
1972
- 1972-05-03 GB GB2053672A patent/GB1368256A/en not_active Expired
- 1972-08-24 AU AU45940/72A patent/AU4594072A/en not_active Expired
- 1972-08-28 NL NL7211694A patent/NL7211694A/xx unknown
- 1972-08-29 DE DE19722242382 patent/DE2242382A1/en active Pending
- 1972-08-29 IE IE117372A patent/IE37697B1/en unknown
- 1972-09-01 CH CH1293572A patent/CH554899A/en not_active IP Right Cessation
- 1972-09-01 AR AR24388272A patent/AR200387A1/en active
- 1972-09-01 AT AT1089573A patent/AT320655B/en not_active IP Right Cessation
- 1972-09-01 FR FR7231080A patent/FR2154449A1/fr not_active Withdrawn
- 1972-09-01 AT AT752072A patent/AT321307B/en not_active IP Right Cessation
- 1972-09-01 CH CH356874A patent/CH551430A/en not_active IP Right Cessation
- 1972-09-04 JP JP8802072A patent/JPS4885584A/ja active Pending
- 1972-09-04 ES ES406374A patent/ES406374A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES406374A1 (en) | 1975-07-16 |
| DE2242382A1 (en) | 1973-03-15 |
| AR200387A1 (en) | 1974-11-08 |
| FR2154449A1 (en) | 1973-05-11 |
| GB1368256A (en) | 1974-09-25 |
| JPS4885584A (en) | 1973-11-13 |
| AU4594072A (en) | 1974-02-28 |
| AT320655B (en) | 1975-02-25 |
| AT321307B (en) | 1975-03-25 |
| IE37697B1 (en) | 1977-09-28 |
| CH554899A (en) | 1974-10-15 |
| BE788280A (en) | 1973-02-28 |
| NL7211694A (en) | 1973-03-06 |
| CH551430A (en) | 1974-07-15 |
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