GB973903A - Substituted bis-[(quinolylamino)alkyl]piperazines - Google Patents
Substituted bis-[(quinolylamino)alkyl]piperazinesInfo
- Publication number
- GB973903A GB973903A GB148/62A GB14862A GB973903A GB 973903 A GB973903 A GB 973903A GB 148/62 A GB148/62 A GB 148/62A GB 14862 A GB14862 A GB 14862A GB 973903 A GB973903 A GB 973903A
- Authority
- GB
- United Kingdom
- Prior art keywords
- piperazine
- compound
- reacting
- formula
- 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
- 125000000217 alkyl group Chemical group 0.000 title abstract 3
- 150000004885 piperazines Chemical class 0.000 title abstract 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 10
- 150000001875 compounds Chemical class 0.000 abstract 8
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 125000006239 protecting group Chemical group 0.000 abstract 4
- 238000000034 method Methods 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 239000000839 emulsion Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 239000000725 suspension Substances 0.000 abstract 2
- OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 abstract 1
- QNGUPQRODVPRDC-UHFFFAOYSA-N 7-chloroquinoline Chemical group C1=CC=NC2=CC(Cl)=CC=C21 QNGUPQRODVPRDC-UHFFFAOYSA-N 0.000 abstract 1
- -1 7-chloroquinolyl radical Chemical class 0.000 abstract 1
- 229940123907 Disease modifying antirheumatic drug Drugs 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 238000006683 Mannich reaction Methods 0.000 abstract 1
- LGEBFLRLRIUXPZ-UHFFFAOYSA-N N-(1-piperazin-1-ylpropan-2-ylidene)hydroxylamine Chemical compound N(O)=C(CN1CCNCC1)C LGEBFLRLRIUXPZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 229940124323 amoebicide Drugs 0.000 abstract 1
- 230000000507 anthelmentic effect Effects 0.000 abstract 1
- 229940124339 anthelmintic agent Drugs 0.000 abstract 1
- 239000000921 anthelmintic agent Substances 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 230000003356 anti-rheumatic effect Effects 0.000 abstract 1
- 239000003435 antirheumatic agent Substances 0.000 abstract 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000000950 dibromo group Chemical group Br* 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- ADYDCWWHQBOFHC-UHFFFAOYSA-N n-(1-chloropropan-2-ylidene)hydroxylamine Chemical compound ClCC(C)=NO ADYDCWWHQBOFHC-UHFFFAOYSA-N 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 150000002923 oximes Chemical class 0.000 abstract 1
- 239000008016 pharmaceutical coating Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000006187 pill Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 150000003248 quinolines Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000000829 suppository Substances 0.000 abstract 1
- 239000006188 syrup Substances 0.000 abstract 1
- 235000020357 syrup Nutrition 0.000 abstract 1
- 239000003826 tablet Substances 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/46—Nitrogen atoms attached in position 4 with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention comprises compounds of general formula <FORM:0973903/C1/1> wherein A represents a divalent straight or branched chain alkylen group containing 2 to 6 carbon atoms, and one or more carbon atoms of the piperazine nucleus may carry an alkyl group containing up to 4 carbon atoms; and sterioisomers; and their acid addition salts; and their preparation by (1) reacting a corresponding compound of formula <FORM:0973903/C1/2> with two moles of a 7-chloroquinoline substituted in the 4-positio by an atom or group capable of reacting with the amino group of the piperazine starting material to introduce the 7-chloroquinolyl radical, (2) reacting a piperazine with two moles of a compound of formula <FORM:0973903/C1/3> where X represents the acid residue of a reactive ester and R represents a hydrogen atom or a group which is readily removable protecting the amino group during the reaction and when R is a protecting group subsequently removing it from the intermediate product in known manner; (3) reacting a compound of formula <FORM:0973903/C1/4> with a compound of Formula III and when R is a protecting group subsequently removing it in known manner. Piperazines may be prepared by the following methods: (1) <FORM:0973903/C1/5> where A1 is hydrogen or alkyl and A2 alkylene so that A1-CH(NH2)-A2- contains 2-6 carbon atoms, (2) <FORM:0973903/C1/6> and the variation wherein a dibromo or a chlorobromo-alkane is condensed with a piperazine, and the product aminated, (3) <FORM:0973903/C1/7> where Hal represents halogen, (4) <FORM:0973903/C1/8> <FORM:0973903/C1/9> where -CH2-A3- corresponds to -A-, (6) <FORM:0973903/C1/100> (7) performing than Mannich reaction and then proceeding via the oxime, for example (another example uses acetone) <FORM:0973903/C1/111> (8) chloroacetone oxime is reacted with piperazine and the 1, 4-bi (2-oximinopropyl)-piperazine produced is reduced. Quinolines III may be prepared by the methods (1) <FORM:0973903/C1/122> <FORM:0973903/C1/133> Dihetero cyclyl compounds IV may be prepared by the methods (1) <FORM:0973903/C1/144> where R1 is a protecting group, and if a Compound IV having protecting group R is required this is introduced before the selective hydrolysis of R1, (2) reacting excess of a piperazine with a Compound (III). Pharmaceutical compositions comprise Compounds I and non-toxic aci addition salts thereof with pharmaceutical carriers or coatings. Oral (tablets, pills, powders, granules, capsules, emulsions, solutions, suspensions, syrups, elixirs), rectal (suppositories) and parenteral (solutions suspensions, emulsions) administration is described. The compounds include anti-inflammatories, anti-rheumatics, anthelmintics and amoebicides.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR848669 | 1961-01-03 | ||
| FR863189 | 1961-05-29 | ||
| FR879154 | 1961-11-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB973903A true GB973903A (en) | 1964-11-04 |
Family
ID=27245808
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB148/62A Expired GB973903A (en) | 1961-01-03 | 1962-01-02 | Substituted bis-[(quinolylamino)alkyl]piperazines |
Country Status (6)
| Country | Link |
|---|---|
| AT (3) | AT241468B (en) |
| CH (1) | CH414636A (en) |
| ES (1) | ES273400A1 (en) |
| GB (1) | GB973903A (en) |
| LU (1) | LU40911A1 (en) |
| SE (1) | SE304005B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100326276A1 (en) * | 2009-06-30 | 2010-12-30 | Blair Alan M | Acid gas scrubbing composition |
| EP2640507A1 (en) * | 2010-11-19 | 2013-09-25 | Nalco Company | Acid gas absorbent composition |
| US20130327983A1 (en) * | 2009-06-30 | 2013-12-12 | Nalco Company | Acid gas scrubbing composition |
-
1961
- 1961-12-06 LU LU40911D patent/LU40911A1/xx unknown
- 1961-12-27 CH CH1501461A patent/CH414636A/en unknown
-
1962
- 1962-01-02 GB GB148/62A patent/GB973903A/en not_active Expired
- 1962-01-02 SE SE18/62A patent/SE304005B/xx unknown
- 1962-01-03 ES ES273400A patent/ES273400A1/en not_active Expired
- 1962-01-03 AT AT410463A patent/AT241468B/en active
- 1962-01-03 AT AT3362A patent/AT241467B/en active
- 1962-01-03 AT AT410563A patent/AT241469B/en active
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100326276A1 (en) * | 2009-06-30 | 2010-12-30 | Blair Alan M | Acid gas scrubbing composition |
| EP2448654A2 (en) * | 2009-06-30 | 2012-05-09 | Nalco Company | Acid gas scrubbing composition |
| US20120145001A1 (en) * | 2009-06-30 | 2012-06-14 | Blair Alan M | Process For Reducing Contaminants In An Industrial Fluid Stream |
| EP2448654A4 (en) * | 2009-06-30 | 2012-12-05 | Nalco Co | Acid gas scrubbing composition |
| US8461335B2 (en) * | 2009-06-30 | 2013-06-11 | Nalco Company | Acid gas scrubbing composition |
| US8551435B2 (en) * | 2009-06-30 | 2013-10-08 | Nalco Company | Process for reducing contaminants in an industrial fluid stream |
| US20130327983A1 (en) * | 2009-06-30 | 2013-12-12 | Nalco Company | Acid gas scrubbing composition |
| US9555364B2 (en) | 2009-06-30 | 2017-01-31 | Nalco Company | Acid gas scrubbing composition |
| EP2640507A1 (en) * | 2010-11-19 | 2013-09-25 | Nalco Company | Acid gas absorbent composition |
| US8765083B2 (en) | 2010-11-19 | 2014-07-01 | Nalco Company | Acid gas absorbent composition |
| EP2640507A4 (en) * | 2010-11-19 | 2014-10-01 | Nalco Co | Acid gas absorbent composition |
| AU2011329882B2 (en) * | 2010-11-19 | 2016-06-23 | Championx Llc | Acid gas absorbent composition |
Also Published As
| Publication number | Publication date |
|---|---|
| CH414636A (en) | 1966-06-15 |
| AT241468B (en) | 1965-07-26 |
| AT241467B (en) | 1965-07-26 |
| AT241469B (en) | 1965-07-26 |
| ES273400A1 (en) | 1962-10-01 |
| LU40911A1 (en) | 1962-02-06 |
| SE304005B (en) | 1968-09-16 |
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