CA1248097A - Intermediaires d'anthra ¬1-9-cd|-pyrazol-6(2h)- ones substitues - Google Patents

Intermediaires d'anthra ¬1-9-cd|-pyrazol-6(2h)- ones substitues

Info

Publication number: CA1248097A
Authority: CA; Canada
Prior art keywords: amino; ethyl; pyrazol; anthra; chloro
Prior art date: 1982-07-23
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

Application number

CA000550173A

Other languages

English (en)

Inventor

Howard D.H. Showalter

Leslie M. Werbel

Judith L. Johnson

Edward F. Elslager

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Warner Lambert Co LLC

Original Assignee

Warner Lambert Co LLC

Priority date (The priority date 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 date listed.)

1982-07-23

Filing date

1987-10-23

Publication date

1989-01-03

1983-06-28 Priority claimed from US06/507,961 external-priority patent/US4556654A/en

1983-07-18 Priority claimed from CA000432584A external-priority patent/CA1230115A/fr

1987-10-23 Application filed by Warner Lambert Co LLC filed Critical Warner Lambert Co LLC

1987-10-23 Priority to CA000550173A priority Critical patent/CA1248097A/fr

1989-01-03 Application granted granted Critical

1989-01-03 Publication of CA1248097A publication Critical patent/CA1248097A/fr

Status Expired legal-status Critical Current

Links

239000000543 intermediate Substances 0.000 title abstract description 10
150000001875 compounds Chemical class 0.000 claims abstract description 148
-1 benzyloxy, p-chlorobenzyloxy Chemical group 0.000 claims abstract description 57
238000000034 method Methods 0.000 claims abstract description 46
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 41
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 3
150000003839 salts Chemical class 0.000 claims description 202
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims description 10
230000008569 process Effects 0.000 claims description 9
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 4
GUTZZPZKDICQHB-UHFFFAOYSA-N 10-chloro-14-[2-(2-hydroxyethylamino)ethyl]-14,15-diazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2,4,6,9,11,13(16)-heptaen-8-one Chemical compound C12=CC=CC=C2C(=O)C2=C(Cl)C=CC3=C2C1=NN3CCNCCO GUTZZPZKDICQHB-UHFFFAOYSA-N 0.000 claims 1
GWVFGAPBSANAIA-UHFFFAOYSA-N 10-chloro-14-[2-(diethylamino)ethyl]-3,6-dihydroxy-14,15-diazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2,4,6,9,11,13(16)-heptaen-8-one Chemical compound ClC=1C=CC=2N(N=C3C2C1C(C1=C(C=CC(=C13)O)O)=O)CCN(CC)CC GWVFGAPBSANAIA-UHFFFAOYSA-N 0.000 claims 1
NYBUYAFAURNUGG-UHFFFAOYSA-N 10-chloro-14-[2-(dimethylamino)ethyl]-3,6-dihydroxy-14,15-diazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2,4,6,9,11,13(16)-heptaen-8-one Chemical compound ClC=1C=CC=2N(N=C3C2C1C(C1=C(C=CC(=C13)O)O)=O)CCN(C)C NYBUYAFAURNUGG-UHFFFAOYSA-N 0.000 claims 1
FYYPSFNNIRJVKP-UHFFFAOYSA-N 10-chloro-14-[2-[2-(dimethylamino)ethylamino]ethyl]-3,6-dihydroxy-14,15-diazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2,4,6,9,11,13(16)-heptaen-8-one Chemical compound ClC=1C=CC=2N(N=C3C2C1C(C1=C(C=CC(=C13)O)O)=O)CCNCCN(C)C FYYPSFNNIRJVKP-UHFFFAOYSA-N 0.000 claims 1
JPTMXTMOSRKAFG-UHFFFAOYSA-N 10-chloro-14-[3-(dimethylamino)propyl]-3,6-dihydroxy-14,15-diazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2,4,6,9,11,13(16)-heptaen-8-one Chemical compound ClC=1C=CC=2N(N=C3C2C1C(C1=C(C=CC(=C13)O)O)=O)CCCN(C)C JPTMXTMOSRKAFG-UHFFFAOYSA-N 0.000 claims 1
PFACCKONAYISNP-UHFFFAOYSA-N 10-chloro-3,6-dihydroxy-14-(2-hydroxyethyl)-14,15-diazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2,4,6,9,11,13(16)-heptaen-8-one Chemical compound ClC=1C=CC=2N(N=C3C2C1C(C1=C(C=CC(=C13)O)O)=O)CCO PFACCKONAYISNP-UHFFFAOYSA-N 0.000 claims 1
VHUNHRLYZREDQS-UHFFFAOYSA-N 10-chloro-3,6-dihydroxy-14-[2-(2-hydroxyethylamino)ethyl]-14,15-diazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2,4,6,9,11,13(16)-heptaen-8-one Chemical compound ClC=1C=CC=2N(N=C3C2C1C(C1=C(C=CC(=C13)O)O)=O)CCNCCO VHUNHRLYZREDQS-UHFFFAOYSA-N 0.000 claims 1
FXCRZHQYPSBZQN-UHFFFAOYSA-N 14-(2-aminoethyl)-10-chloro-3,6-dihydroxy-14,15-diazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2,4,6,9,11,13(16)-heptaen-8-one Chemical compound NCCN1N=C2C3=C1C=CC(=C3C(C3=C(C=CC(=C32)O)O)=O)Cl FXCRZHQYPSBZQN-UHFFFAOYSA-N 0.000 claims 1
229910015845 BBr3 Inorganic materials 0.000 claims 1
229910015844 BCl3 Inorganic materials 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 16
ACPOUJIDANTYHO-UHFFFAOYSA-N anthra[1,9-cd]pyrazol-6(2H)-one Chemical class C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=NNC2=C1 ACPOUJIDANTYHO-UHFFFAOYSA-N 0.000 abstract description 9
230000000845 anti-microbial effect Effects 0.000 abstract 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 281
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 235
239000000047 product Substances 0.000 description 166
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 150
238000006243 chemical reaction Methods 0.000 description 139
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 136
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 129
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 122
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 112
239000000203 mixture Substances 0.000 description 106
125000004432 carbon atom Chemical group C* 0.000 description 98
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 97
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 90
229910000041 hydrogen chloride Inorganic materials 0.000 description 90
238000000354 decomposition reaction Methods 0.000 description 87
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
125000000217 alkyl group Chemical group 0.000 description 71
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 69
239000007787 solid Substances 0.000 description 56
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 48
229960004592 isopropanol Drugs 0.000 description 46
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 45
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
238000010992 reflux Methods 0.000 description 36
239000000243 solution Substances 0.000 description 35
230000015572 biosynthetic process Effects 0.000 description 28
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
239000000460 chlorine Substances 0.000 description 27
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 22
239000002904 solvent Substances 0.000 description 20
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
150000002500 ions Chemical class 0.000 description 19
238000010626 work up procedure Methods 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
229960000583 acetic acid Drugs 0.000 description 18
LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 18
239000001257 hydrogen Substances 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 17
241000124008 Mammalia Species 0.000 description 16
125000002947 alkylene group Chemical group 0.000 description 16
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 16
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 15
239000005977 Ethylene Substances 0.000 description 15
150000001412 amines Chemical class 0.000 description 15
239000003937 drug carrier Substances 0.000 description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
239000008194 pharmaceutical composition Substances 0.000 description 14
229910000027 potassium carbonate Inorganic materials 0.000 description 14
235000011181 potassium carbonates Nutrition 0.000 description 14
229920001817 Agar Polymers 0.000 description 13
239000007983 Tris buffer Substances 0.000 description 13
239000008272 agar Substances 0.000 description 13
230000000875 corresponding effect Effects 0.000 description 13
239000000741 silica gel Substances 0.000 description 13
229910002027 silica gel Inorganic materials 0.000 description 13
125000001424 substituent group Chemical group 0.000 description 13
239000000725 suspension Substances 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
125000003386 piperidinyl group Chemical group 0.000 description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
239000002253 acid Substances 0.000 description 11
239000012362 glacial acetic acid Substances 0.000 description 11
239000000843 powder Substances 0.000 description 11
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 10
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 10
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
206010028980 Neoplasm Diseases 0.000 description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 10
229910052760 oxygen Inorganic materials 0.000 description 10
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 10
229910052717 sulfur Inorganic materials 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
229910052786 argon Inorganic materials 0.000 description 9
210000004027 cell Anatomy 0.000 description 9
238000004587 chromatography analysis Methods 0.000 description 9
229940012017 ethylenediamine Drugs 0.000 description 9
239000010410 layer Substances 0.000 description 9
MEHLXACDLXEVBE-UHFFFAOYSA-N 1,4-dichloro-5,8-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC(Cl)=C2C(=O)C2=C1C(O)=CC=C2O MEHLXACDLXEVBE-UHFFFAOYSA-N 0.000 description 8
239000004480 active ingredient Substances 0.000 description 8
238000004090 dissolution Methods 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 8
239000011698 potassium fluoride Substances 0.000 description 8
235000003270 potassium fluoride Nutrition 0.000 description 8
238000012545 processing Methods 0.000 description 8
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 8
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 8
238000001665 trituration Methods 0.000 description 8
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 7
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 7
238000001311 chemical methods and process Methods 0.000 description 7
238000002425 crystallisation Methods 0.000 description 7
230000008025 crystallization Effects 0.000 description 7
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 7
239000012458 free base Substances 0.000 description 7
239000000463 material Substances 0.000 description 7
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 7
239000003826 tablet Substances 0.000 description 7
229940086542 triethylamine Drugs 0.000 description 7
GIFIYDUDNBESHK-UHFFFAOYSA-N 2-(2-hydrazinylethylamino)ethanol Chemical compound NNCCNCCO GIFIYDUDNBESHK-UHFFFAOYSA-N 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
150000002431 hydrogen Chemical class 0.000 description 6
239000007788 liquid Substances 0.000 description 6
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 6
229910000028 potassium bicarbonate Inorganic materials 0.000 description 6
235000015497 potassium bicarbonate Nutrition 0.000 description 6
239000011736 potassium bicarbonate Substances 0.000 description 6
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 6
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
238000010561 standard procedure Methods 0.000 description 6
239000000126 substance Substances 0.000 description 6
238000012360 testing method Methods 0.000 description 6
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 5
239000006185 dispersion Substances 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
CAHGWVAXFJXDNI-UHFFFAOYSA-N 1,4-dichloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Cl)=CC=C2Cl CAHGWVAXFJXDNI-UHFFFAOYSA-N 0.000 description 4
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
229910021591 Copper(I) chloride Inorganic materials 0.000 description 4
101100152865 Danio rerio thraa gene Proteins 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
239000003429 antifungal agent Substances 0.000 description 4
229940121375 antifungal agent Drugs 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
230000001580 bacterial effect Effects 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 4
229940045803 cuprous chloride Drugs 0.000 description 4
230000000694 effects Effects 0.000 description 4
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 4
229960000443 hydrochloric acid Drugs 0.000 description 4
235000011167 hydrochloric acid Nutrition 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 4
230000000813 microbial effect Effects 0.000 description 4
DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
239000011734 sodium Substances 0.000 description 4
241000894007 species Species 0.000 description 4
101150014006 thrA gene Proteins 0.000 description 4
MQIUMARJCOGCIM-UHFFFAOYSA-N 1,5-dichloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C=CC=C2Cl MQIUMARJCOGCIM-UHFFFAOYSA-N 0.000 description 3
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
USCXAEBVEUSNSG-UHFFFAOYSA-N 4-(2-aminoethyl)piperazine-1-carboxylic acid Chemical compound NCCN1CCN(C(O)=O)CC1 USCXAEBVEUSNSG-UHFFFAOYSA-N 0.000 description 3
SCTWWYJJYPRROF-UHFFFAOYSA-N 5,8-dichloroanthracene-1,4,9,10-tetrone Chemical compound ClC1=CC=C(Cl)C(C2=O)=C1C(=O)C1=C2C(=O)C=CC1=O SCTWWYJJYPRROF-UHFFFAOYSA-N 0.000 description 3
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LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
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DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
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125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
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TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
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239000011345 viscous material Substances 0.000 description 1
239000012138 yeast extract Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA000550173A 1982-07-23 1987-10-23 Intermediaires d'anthra ¬1-9-cd|-pyrazol-6(2h)- ones substitues Expired CA1248097A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000550173A CA1248097A (fr)	1982-07-23	1987-10-23	Intermediaires d'anthra ¬1-9-cd\|-pyrazol-6(2h)- ones substitues

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US40115782A	1982-07-23	1982-07-23
US401,157		1982-07-23
US06/507,961 US4556654A (en)	1983-06-28	1983-06-28	Antimicrobial substituted anthra[1,9-cd]pyrazol-6(2H)-ones
US507,961		1983-06-28
CA000432584A CA1230115A (fr)	1982-07-23	1983-07-18	Anthra[1,9-cd]pyrazol-6(2h)-ones substitues
CA000550173A CA1248097A (fr)	1982-07-23	1987-10-23	Intermediaires d'anthra ¬1-9-cd\|-pyrazol-6(2h)- ones substitues

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000432584A Division CA1230115A (fr)	1982-07-23	1983-07-18	Anthra[1,9-cd]pyrazol-6(2h)-ones substitues

Publications (1)

Publication Number	Publication Date
CA1248097A true CA1248097A (fr)	1989-01-03

Family

ID=27167359

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CA000550175A Expired CA1251442A (fr)	1982-07-23	1987-10-23	Produits intermediaires pour derives de substitution d'anthra ¬1,9-cd\|-pyrazol-6(2h)-ones
CA000550174A Expired CA1256431A (fr)	1982-07-23	1987-10-23	Derives de substitution d'anthra¬1,9-cd\|pyrasol- 6-(2h)-ones
CA000550173A Expired CA1248097A (fr)	1982-07-23	1987-10-23	Intermediaires d'anthra ¬1-9-cd\|-pyrazol-6(2h)- ones substitues

Family Applications Before (2)

Application Number	Title	Priority Date	Filing Date
CA000550175A Expired CA1251442A (fr)	1982-07-23	1987-10-23	Produits intermediaires pour derives de substitution d'anthra ¬1,9-cd\|-pyrazol-6(2h)-ones
CA000550174A Expired CA1256431A (fr)	1982-07-23	1987-10-23	Derives de substitution d'anthra¬1,9-cd\|pyrasol- 6-(2h)-ones

Country Status (1)

Country	Link
CA (3)	CA1251442A (fr)

1987
- 1987-10-23 CA CA000550175A patent/CA1251442A/fr not_active Expired
- 1987-10-23 CA CA000550174A patent/CA1256431A/fr not_active Expired
- 1987-10-23 CA CA000550173A patent/CA1248097A/fr not_active Expired

Also Published As

Publication number	Publication date
CA1251442A (fr)	1989-03-21
CA1256431A (fr)	1989-06-27

Legal Events

Date	Code	Title	Description
2006-01-03	MKEX	Expiry

Publication	Publication Date	Title
EP1509521B1 (fr)	2008-08-20	Derives de 1h-imidazo[4,5-c]quinoline servant au traitement de maladies dependant de proteines kinases
EP0145226B1 (fr)	1988-10-05	1-Amino-4-nitro-acridinones, compositions pharmaceutiques les contenant et procédés pour les obtenir
US4556654A (en)	1985-12-03	Antimicrobial substituted anthra[1,9-cd]pyrazol-6(2H)-ones
SE438675B (sv)	1985-04-29	9-hydrazono-pyrido(1,2-a)pyrimidinderivat
EP0988302B1 (fr)	2003-02-19	Benzonaphthyridine
EP0103381B1 (fr)	1987-09-23	Anthra(1,9-cd)pyrazol-6(2H)-ones
US4555572A (en)	1985-11-26	Pyrazolo[3,4,5-kl]acridine compositions and methods for their production and use
EP0064317B1 (fr)	1986-02-26	Dérivés du pyrrolo (2,3-d) carbazole, procédé pour leur préparation et leur application thérapeutique
CA1206153A (fr)	1986-06-17	Compositions a base de benzothiopyrano¬4,3,2-cd\| indazole; preparation et applications
CA1248097A (fr)	1989-01-03	Intermediaires d'anthra ¬1-9-cd\|-pyrazol-6(2h)- ones substitues
AU2001270783B2 (en)	2006-06-15	Variolin derivatives as anti-cancer agents
DE60111553T2 (de)	2006-04-06	Hexahydropyrazino[1'2':1,6]-pyrido[3,4-b]indole-1,4-dion-derivate zur behandlung von cardiovaskulären erkrankungen und erektionsstörungen
DK160991B (da)	1991-05-13	5,14-dihydrobenzoe5,6aaisoindolooe2,1-baaisoquinolin-8,13-dionderivater, fremgangsmaade til fremstilling deraf og farmaceutisk praeparat indeholdende en saadan forbindelse
US4621086A (en)	1986-11-04	Method of treating leukemia with pyrazolo[3,4,5-kl]acridines
US4588730A (en)	1986-05-13	Pyrazolo[3,4,5-k1]acridine compositions and methods for their use as antimicrobials
CA1134363A (fr)	1982-10-26	Composes pyrano-heterocycliques, procede de preparation et medicament les contenant
ES2835061T3 (es)	2021-06-21	Forma de sal y forma cristalina de 1,2,5-tiadiazolidina 1,1-dióxido, método de preparación de las mismas e intermedios
Walls	1947	13. Researches in the phenanthridine series. Part VIII. Further investigation of trypanocidal types
US4720496A (en)	1988-01-19	Pyridotriazoloquinazolines and triazolopyridoquinazolines useful as antiallergics
JPS60136567A (ja)	1985-07-20	置換１−アミノ−４−ニトロ−アクリジノン類
EP0230016B1 (fr)	1991-09-11	6H-Isoxazolo[3,4-d]pyrazolo[3,4-b]pyridines, procédé pour leur préparation et leur application comme médicaments
US3558632A (en)	1971-01-26	2-(benzonaphthyridin-2-yl acyl) benzonaphthyridines
JPS6144868A (ja)	1986-03-04	新規なフレデリカマイシンａ誘導体
JPH01165577A (ja)	1989-06-29	置換されたベンズイミダゾール類およびベンゾチアジアゾール類
DD299649A5 (de)	1992-04-30	Dipyrido (3,2-b:2',3'-e)(1,4)oxazepin(und thiazepin)-6-(5h)-one und -thione und ihre verwendung zur verhuetung oder behandlung von aids