Dichlorquinazine

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str1

Unii-ccx4U97PF3.png

CORRECT STR OF Dichlorquinazine

7-chloro-N-[1-[4-[2-[(7-chloroquinolin-4-yl)amino]propyl]piperazin-1-yl]propan-2-yl]quinolin-4-amine;methanesulfonic acid

  • 1,4-Piperazinediethanamine, N,N’-bis(7-chloro-4-quinolinyl)-α,α’-dimethyl- (9CI)
  • Quinoline, 4,4-[1,4-piperazinediylbis[(1-methylethylene)imino]]bis[7-chloro- (7CI)
  • Quinoline, 4,4′-[1,4-piperazinediylbis[(1-methylethylene)imino]]bis[7-chloro- (8CI)
  • N1,N4-Bis(7-chloro-4-quinolinyl)-α14-dimethyl-1,4-piperazinediethanamine
  • 1,4-Bis[2-(7-chloro-4-quinolylamino)propyl]piperazine
  • Bis[(chloro-7”-quinolyl-4”)amino-2′-propyl]-1,4-piperazine
  • Dichlorquinazine
  • N,N’-Bis(7-chloro-4-quinolyl)-α,α’-dimethylpiperazine-1,4-diethylamine
  • NSC 129790
  • RP 12278
  • WR 3863

WRONG STRUCTURE

4,4'-(1,4-Piperazinediylbis((1-methylethylene)imino))bis(7-chloroquinoline).png

WRONG STRUCTURE

Dichlorquinazine

 

  • BRN 0867697
  • Dichlorquinazine
  • EINECS 234-130-6
  • NSC 129790
  • RP 12278
  • UNII-HT3GAD2SCM
  • WR 3863

 

cas 10547-40-7

C28H32Cl2N6, mw

523.5

7-chloro-N-[2-[4-[2-[(7-chloroquinolin-4-yl)amino]propan-2-yl]piperazin-1-yl]propan-2-yl]quinolin-4-amine

 

VARIANT

 

2D chemical structure of 23256-65-7

RN: 23256-65-7

Molecular Formula, C28-H32-Cl2-N6.C-H4-O3-S, Molecular Weight, 619.6144

  • RP-12278 mesylate
  • WR-3863 mesylate
  • Quinoline, 4,4′-(1,4-piperazinediylbis((1-methylethylene)imino))bis(7-chloro-, tetramethanesulfonate bis((7-chloro-4”-quinolyl)-2′-aminopropyl)-1,4-piperazine methanesulfonate
wdt-16

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RESEARCHGATE

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PATENTS

BE 626239

4-(Chloro or alkoxy)quinolines are treated with a 1,4-bis(aminoalkyl)piperazine to give the title compds. which can be used as antiinflammatory agents and as amebicides.  Thus, a mixt. of 16.3 g. 4-chloroquinoline, 10 g. 1,4-bis(3-aminopropyl)piperazine, 55 g. PhOH, and 0.2 g. NH4Cl is heated 5 hrs. at 175°, poured into a mixt. of 500 ml. H2O and 100 ml. NaOH (d. 1.33), filtered, the ppt. is treated with a mixt. of 80 ml. H2O and 20 ml. NaOH, the mixt. filtered, and the ppt. washed with 500 ml. H2O and dried to give 15.9 g. 1,4-bis[3-(4-quinolyl)aminopropyl]piperazine, m. 210°(MeOH-H2O).  Similarly prepd. are the following I:  n, R, R1, R2, X, Y, m.p.; 2, H, H, H, MeO, H, 245° (HCONMe2); 2, H, H, H, H, SO2NMe2, 271° (HCONMe2); 2, H, H, H, H, CF3, 293° (HCONMe2); 3, Me, H, H, H, H, ∼100°; 3, Me, Ac, H, H, H, -(1); 3, Me, H, H, MeOH, 180° and 190°; 3, Me, Ac, H, MeO, H, -(2); 1, Me, H, Me, H, Cl, 264°; 2, H, H, H, Cl, H, 264° (BuOH); 1, Me, H, H, H, CF3, 240° (MeCOEt); 2, H, H, H, H, MeO, 200° (EtOH); 2, H, H, Me, H, MeO, 216° (EtOH); 3, Me, H, H, H, MeO, 218° (CH2Cl2); (1) bis(acid maleate) m. 155° (iso-PrOH), (2) bis(acid maleate) m. 155°  The following II were also prepd.:  n, R, R1, R2, m.p.; 1, Me, A(R = R1 = X = Y = H,Z =Cl), A(R = R1 = X = Z = H,Y = Cl), 208-10° (HCONMe2); 1, Me, A(R = R1 = X = Y= H, Z = Cl), A(R = R1 = X = Y = H,Z = MeO), 206-8° (HCONMe2); 1, Me, A(R1 = X = Y = H, R = 4-ClC6H4, Z = Cl), A(R = R1 = X = Y = H,Z = Cl, 230-2° (HCONMe2)  The following III were prepd.:  n, R, m, R1, R2, m.p.; 3, Me, 1, H, A(R = R1 = X = Y = H, Z= Cl), 190-1° and 213-15°; 2, H, 2, H, A(R = X = Y = H, R1 = Me, Z =Cl), 198° (PrOH); 3, Me, 2, H, A(R = R1 = X = Y = H,Z = Cl), 160-2°; 1, Me, 1, H, A(R = R1 = X = Y = H,Z = Cl), 178°; 1, Me, 1, Me, A(R1 = X = Z = H,R = Me, Y =AcNH), 330° (decompn.) (EtOH); 2, H, 2, H, A(R1 = X = Y = H,R = 4-ClC6H4,Z = Cl), 320-1° (HCONMe2); 2, H, 2, H, A(R = Y = Z = H, R1 = Me, X = Cl) 96° (iso-PrOH); 1, Me, 1, Me, A(R = R1 = X = Z = H, Y = Cl), 220° and 246-8°; 1, Me, 1, Me, A(R1 = X = Z = H, R = Me, Y = NH2), 305° (EtOH-H2O); 1, Me, 1, Me, A(R1 = X = Z = H, R = Me, Y = MeO, 244° (EtOH)  Also prepd. were (m.p. given): 1,4-bis[2-(7-chloro-4-quinolylamino)propyl]hexahydro-1,4-diazepine, 169°; 1-[5-(7-chloro-4-quinolylamino)-2-pentyl]-4-[2-(7-chloro-4-quinolylamino)propyl] piperazine, 210-12°(HCONMe2); 1,4-bis[3-(7-chloro- 4-quinolylamino)propyl] hexahydro-1,4-diazepine, 186° (HCONMe2).  The following were prepd. (m.p. and optical rotation given):L(+)-1,4-bis[2-(7-chloro-4-quinolylamino)propyl]piperazine, 250-1°, [α]23.5D 382° ± 1° (c 4, 50:50 MeOH-H2O); D(-)-1,4- bis[2-(7-chloro-4-quinolylamino)propyl] piperazine, 250-1°, [α]25D -382.5° ± 1° (c 4, 50:50 MeOH-H2O); DL-1,4-bis[2-(7-chloro-4-quinolylamino)propyl]piperazine (IV), 266-8°, -; meso-1,4-bis [2-(7-chloro-4-quinolylamino)propyl] piperazine (V), 270-1° (HCONMe2), -; equimol. mixt. of IV and V, 250-2°, -; 1,4-bis[2-(6-chloro-4-quinolylamino)propyl]piperazine-form A (VI-form A), 227° -; VI-form B, 110° and 245°, -.  Also prepd. are the following intermediates of the general formula VII (R = H) (X, Y, Z, and m.p. given): OH, H, SO2NMe2, ∼288°; Cl, H,SO2NMe2, 170°; HO(CH2)3CHMeNH, H, H, 158° (EtOH); AcO(CH2)3CHMeNAc, H, H, -; HO(CH2)3CHMeNAc, H, H, -; MeSO3(CH2)3CHMeNAc, H, H, -; N-(5-piperazino-2-pentyl)acetamido, H, H, -; HO(CH2)3CHMeNH, MeO, H, -; AcO(CH2)3CHMeNAc, MeO, H, -; HO(CH2)3CHMeNAc, MeO, H, -; MeSO3(CH2)3CHMeNAc, MeO, H, -; N-(5-piperazino-2-pentyl)acetamido, MeO, H, -; Me(HOCH2)CH, H, Cl, 210°; Me(ClCH2)CH, H, Cl, 148-50°; Me(HOCH2)CH, Cl, H, 192°; Me(ClCH2)CH, Cl, H, 142°; Me(HOCH2)CH, H, MeO, 170°; Me(ClCH2)CH, H, MeO, 160°.  Also prepd. were (m.p. given): VII (R = CO2Et, X = OH, Y = H, Z = SO2NMe2), ∼335°; VII (R = CO2H, X = OH, Y = H, Z = SO2HMe2), 310° (decompn.); 1,4-bis(2-oxopropyl)hexahydro-1,4-diazepine, -; 1,4-bis(2-oximinopropyl)hexahydro-1,4-diazepine, 180-1°; 1,4-bis(2-aminopropyl)hexahydro-1,4-diazepine, -; 1,4-bis(2-cyanoethyl)-hexahydro-1,4-diazepine, -.  The following were prepd. (m.p. and optical rotation given): L(+)-4-(3-hydroxy-2-propylamino)-7-chloroquinoline, 223-4°, [α]24D 28.5° ± 2° (c 1, EtOH); L(+)-4-(3-chloro-2-propylamino)-7-chloroquinoline, 146-7°, [α]24D 103 ± 1° (c 2, EtOH); L(+)-4-(3-piperazino-2-propylamino)-7-chloroquinoline, 128-30°, [α]23D 139 ± 1° (c 2, EtOH); D(-)-4-(3-hydroxy-2-propylamino)-7-chloroquinoline, 223-4°, [α]25D – 31 ± 2° (c 1, EtOH); D(-)-4-(3-chloro-2-propylamino)-7-chloroquinoline, 147-8°, [α]24D -101 ± 1° (c 2, EtOH); D(-)-4-(3-piperazino-2-propylamino)-7-chloroquinoline, 131-2°, [α]23D -137 ± 1° (c 2, EtOH)

PATENT

FR CAM42 19631007.

Piperazines (I) are antiinflammatory and anthelmintic agents.  A mixt. of 8.25 g. MeCH(NH2)CH2OH, 19.8 g. 4,6-dichloroquinoline, and 55 g. PhOH is heated to give 16.0 g. 6-chloro-4-[(3-hydroxy-2-propyl)-amino]quinoline (II), m. 192°.  II (14.0 g.) is treated with a soln. of 10.6 g. SOCl2 in 40 ml. CHCl3 to give 12.5 g. 6-chloro-4-[(3-chloro-2-propyl)amino]quinoline (III), m. 142°.  A mixt. of 13.2 g. 1-[2-(7-chloro-4-quinolylamino)propyl]piperazine, 11.0 g. III, 6.4 g. NaI, 2.3 g. anhyd. Et3N, and 200 ml. AcEt is refluxed 18 hrs., the solvent is distd. in vacuo, and the residue is taken up in 100 ml. MeOH.  The mixt. is made alk. with 110 ml. NaOH (d. 1.33), poured into 1000 ml. H2O, and the ppt. that forms is filtered off, washed with H2O, and recrystd. in HCONMe2 to give 11.0 g. 1-[2-(7-chloro-4-quinolylamino)propyl]-4-[2-(6-chloro-4-quinolylamino)propyl]piperazine, m. 208-10°.  Similarly prepd. are the following I (R, m, R1, n, R2, R3, R4, and m.p. given): H, 2, H, 2, H, MeO, H, 245°; H, 2, H, 2, H, H, SO2NMe2, 271°; H, 2, H, 2, H, H, CF3, 293°; Me, 3, Me, 3, H, MeO, H, 180° and 190°; Me, 3, H, 1, H, H, Cl, 190-1° and 213-15°; H, 2, H, 2, H, Cl, H, 264°; Me, 1, Me, 1, H, H, CF3, 240°; H, 2, H, 2, H, H, MeO, 200°; Me, 3, H, 2, H, H, Cl, 160-2°; Me, 1, H, 1, H, H, Cl, 178°; Me, 1, Me, 1, Me, AcNH, H, 330°; H, 2, H, 2, p-ClC6H4, H, Cl, 320-1°; Me, 1, Me, 1, H, Cl, H, 227° (form A); Me, 1, Me, 1, H, Cl, H, 110° and 245° (form B); H, 3, H, 3, H, H, Cl, 239-41°; Me, 1, Me, 1, Me, NH2, H, 305°; Me, 1, Me, 1, Me, MeO, H, 244°; Me, 3, Me, 3, Me, 3, H, H, MeO, 218°; H, 3, H, 3, H, H, Cl, 240-2°.  Also prepd. are (m.p. given): 1,4-bis[2-(7-chloro-4-quinolylamino)propyl]hexahydrodiazepine, 169°; 2,5-dimethyl-1,4-bis[2-(7-chloro-4-quinolylamino)propyl)piperazine, 264°; 1-[5-(7-chloro-4-quinolylamino [-2-pentyl]-4-[2-(7-chloro -4-quinolylamino)propyl]piperazine, 210-12°; 2,5-dimethyl-1,4-bis[3-(7-methoxy-4-quinolylamino)propyl]piperazine, 216°; 1,4-bis[3-(3-methyl-7-chloro-4-quinolylamino)propyl] piperazine, 198°; 1,4-bis[3-(7-chloro-4-quinolylamino)propyl]hexahydrodiazepine, 186°;  1-[2(7-chloro-4-quinolylamino)propyl]-4-[2-(7-methoxy-4-quinolylamino)propyl]piperazine, 206-8°; 1,4-bis[3-(3-methyl-5-chloro-4- quinolylamino)propyl]piperazine, 96°; 1 – [2 -[2 -(p – chlorophenyl)- 7- chloro- 4- quinolylamino]propyl] -4 – [2 – (7 – chloro – 4-quinolylamino)propyl]piperazine, 230-2°; L(+) 1,4-bis[2-(7-chloro-4-quinolylamino)propyl]piperazine, 250-1°, [α]23.5D + 382° ± 1° (c 4, 50/50 MeOH-H2O); L(+)-7-chloro-4-(3-hydroxy-2-propylamino)quinoline, 223-4°, [α]24D 28.5° ± 2° (c 1, EtOH); L(+)-7-chloro-4-(3-chloro-2-propylamino)quinoline, 146-7°, [α]24D 103° + 1° (c 2, EtOH); L(+)-7-chloro-4-(3-piperazino-2-propylamino)quinoline 128-30°, [α]23D 139° ± 1° (c 2, EtOH); D(–)-1,4-bis[2-(7-chloro-4-quinolylamino)propyl]piperazine, 250-1°, [α]25D -382° ± 1° (c 4, 50:50 MeOH-H2O); meso- 1,4 – bis [2 – (7 – chloro – 4 – quinolylamino)propyl] piperazine, 270-1°.

Patent Information

BE 612207

 

 

Publication Number
Title
Priority Date
Grant Date
US-2016045487-A1 Compositions and methods for treating neuropathy 2013-03-27
WO-2014160811-A1 Compositions and methods for treating neuropathy 2013-03-27
AU-2014234258-A1 Piperaquine microcapsules and compositions containing them 2013-03-22
AU-2014234258-B2 Piperaquine microcapsules and compositions containing them 2013-03-22 2019-02-14
CA-2907628-A1 Piperaquine microcapsules and compositions containing them 2013-03-22
Publication Number
Title
Priority Date
Grant Date
EP-2976069-A1 Piperaquine microcapsules and compositions containing them 2013-03-22
EP-2976069-B1 Piperaquine microcapsules and compositions containing them 2013-03-22 2020-05-06
US-2014322296-A1 Piperaquine microcapsules and compositions containing them 2013-03-22
US-2016045447-A1 Piperaquine microcapsules and compositions containing them 2013-03-22
US-9668979-B2 Piperaquine microcapsules and compositions containing them 2013-03-22 2017-06-06
Publication Number
Title
Priority Date
Grant Date
WO-2014147242-A1 Piperaquine microcapsules and compositions containing them 2013-03-22
AU-2009215107-A1 Treatments for neuropathy 2008-02-12
AU-2009215107-B2 Treatments for neuropathy 2008-02-12 2013-05-09
AU-2013203934-A1 Treatments for neuropathy 2008-02-12
CA-2714676-A1 Treatments for neuropathy 2008-02-12
Publication Number
Title
Priority Date
Grant Date
CA-2714676-C Treatments for neuropathy 2008-02-12 2015-04-14
EP-2240177-A2 Treatments for neuropathy 2008-02-12
US-2009203735-A1 Treatments for neuropathy 2008-02-12
US-2011086878-A1 Treatments for Neuropathy 2008-02-12
US-2016058749-A1 Treatments for neuropathy 2008-02-12

////////////////Dichlorquinazine, BRN 0867697, Dichlorquinazine, EINECS 234-130-6, NSC 129790, RP 12278, UNII-HT3GAD2SCM, WR 3863

CC(C)(NC1=C2C=CC(=CC2=NC=C1)Cl)N3CCN(CC3)C(C)(C)NC4=C5C=CC(=CC5=NC=C4)Cl

WRONG

CC(CN1CCN(CC(C)Nc2ccnc3cc(Cl)ccc23)CC1)Nc4ccnc5cc(Cl)ccc45.CS(=O)(=O)O

AND

Clc1ccc2c(c1)nccc2NC(C)CN1CCN(CC(C)Nc2ccnc3cc(Cl)ccc32)CC1

CORRECT

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