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)-α¹,α⁴-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

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

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

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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]^23.5_D 382° ± 1° (c 4, 50:50 MeOH-H₂O); D(-)-1,4- bis[2-(7-chloro-4-quinolylamino)propyl] piperazine, 250-1°, [α]²⁵_D -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]²⁴_D 28.5° ± 2° (c 1, EtOH); L(+)-4-(3-chloro-2-propylamino)-7-chloroquinoline, 146-7°, [α]²⁴_D 103 ± 1° (c 2, EtOH); L(+)-4-(3-piperazino-2-propylamino)-7-chloroquinoline, 128-30°, [α]²³_D 139 ± 1° (c 2, EtOH); D(-)-4-(3-hydroxy-2-propylamino)-7-chloroquinoline, 223-4°, [α]²⁵_D – 31 ± 2° (c 1, EtOH); D(-)-4-(3-chloro-2-propylamino)-7-chloroquinoline, 147-8°, [α]²⁴_D -101 ± 1° (c 2, EtOH); D(-)-4-(3-piperazino-2-propylamino)-7-chloroquinoline, 131-2°, [α]²³_D -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]^23.5_D + 382° ± 1° (c 4, 50/50 MeOH-H₂O); L(+)-7-chloro-4-(3-hydroxy-2-propylamino)quinoline, 223-4°, [α]²⁴_D 28.5° ± 2° (c 1, EtOH); L(+)-7-chloro-4-(3-chloro-2-propylamino)quinoline, 146-7°, [α]²⁴_D 103° + 1° (c 2, EtOH); L(+)-7-chloro-4-(3-piperazino-2-propylamino)quinoline 128-30°, [α]²³_D 139° ± 1° (c 2, EtOH); D(–)-1,4-bis[2-(7-chloro-4-quinolylamino)propyl]piperazine, 250-1°, [α]²⁵_D -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