CA1071195A - Les 10-imidoylacridans - Google Patents

Les 10-imidoylacridans

Info

Publication number: CA1071195A
Authority: CA; Canada
Prior art keywords: acridan; methyl; carbon atoms; pyrrolidinone; prepared
Prior art date: 1976-03-31
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

CA249,322A

Other languages

English (en)

Inventor

Yao H. Wu

Walter G. Lobeck (Jr.)

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.)

Bristol Myers Squibb Co

Original Assignee

Bristol Myers Squibb Co

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.)

1976-03-31

Filing date

1976-03-31

Publication date

1980-02-05

1976-03-31 Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co

1976-03-31 Priority to CA249,322A priority Critical patent/CA1071195A/fr

1980-02-05 Application granted granted Critical

1980-02-05 Publication of CA1071195A publication Critical patent/CA1071195A/fr

Status Expired legal-status Critical Current

Links

HJCUTNIGJHJGCF-UHFFFAOYSA-N 9,10-dihydroacridine Chemical compound C1=CC=C2CC3=CC=CC=C3NC2=C1 HJCUTNIGJHJGCF-UHFFFAOYSA-N 0.000 claims abstract description 98
125000000217 alkyl group Chemical group 0.000 claims abstract description 18
-1 dihalogen Chemical group 0.000 claims abstract description 12
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
229910052736 halogen Inorganic materials 0.000 claims abstract description 5
150000002367 halogens Chemical group 0.000 claims abstract description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
GNXVCEUMQOTOTM-UHFFFAOYSA-N 9,9-dimethyl-10-(2-methyl-3,4-dihydro-2h-pyrrol-5-yl)acridine Chemical compound CC1CCC(N2C3=CC=CC=C3C(C)(C)C3=CC=CC=C32)=N1 GNXVCEUMQOTOTM-UHFFFAOYSA-N 0.000 claims abstract 2
238000000034 method Methods 0.000 claims description 50
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 48
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 35
230000008569 process Effects 0.000 claims description 27
125000004432 carbon atom Chemical group C* 0.000 claims description 22
239000000126 substance Substances 0.000 claims description 20
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 18
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 claims description 15
YVIVRJLWYJGJTJ-UHFFFAOYSA-N gamma-Valerolactam Chemical compound CC1CCC(=O)N1 YVIVRJLWYJGJTJ-UHFFFAOYSA-N 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
150000003857 carboxamides Chemical class 0.000 claims description 12
XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 8
UUTGCNVYKLQLRV-UHFFFAOYSA-N 5,5-dimethylpyrrolidin-2-one Chemical compound CC1(C)CCC(=O)N1 UUTGCNVYKLQLRV-UHFFFAOYSA-N 0.000 claims description 4
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 4
KVTGAKFJRLBHLU-UHFFFAOYSA-N n-propan-2-ylformamide Chemical compound CC(C)NC=O KVTGAKFJRLBHLU-UHFFFAOYSA-N 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
GKOMHLQYCJIFLB-UHFFFAOYSA-N 9,9-dimethyl-10-(2-methyl-3,4-dihydro-2h-pyrrol-5-yl)acridine;hydrochloride Chemical compound Cl.CC1CCC(N2C3=CC=CC=C3C(C)(C)C3=CC=CC=C32)=N1 GKOMHLQYCJIFLB-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
229960000443 hydrochloric acid Drugs 0.000 claims 5
235000011167 hydrochloric acid Nutrition 0.000 claims 5
JSEQNGYLWKBMJI-UHFFFAOYSA-N 9,9-dimethyl-10h-acridine Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3NC2=C1 JSEQNGYLWKBMJI-UHFFFAOYSA-N 0.000 claims 2
ZMUYVKRCVIBJSM-UHFFFAOYSA-N 1-(9h-acridin-10-yl)-n-propan-2-ylmethanimine Chemical compound C1=CC=C2N(C=NC(C)C)C3=CC=CC=C3CC2=C1 ZMUYVKRCVIBJSM-UHFFFAOYSA-N 0.000 claims 1
ZWGNSBHTNDUUAO-UHFFFAOYSA-N 10-(2,3,4,5-tetrahydropyridin-6-yl)-9h-acridine Chemical compound C1CCCC(N2C3=CC=CC=C3CC3=CC=CC=C32)=N1 ZWGNSBHTNDUUAO-UHFFFAOYSA-N 0.000 claims 1
AEGLMYWBBLRNGZ-UHFFFAOYSA-N 10-(2-methyl-3,4-dihydro-2h-pyrrol-5-yl)-9h-acridine;hydrochloride Chemical compound Cl.CC1CCC(N2C3=CC=CC=C3CC3=CC=CC=C32)=N1 AEGLMYWBBLRNGZ-UHFFFAOYSA-N 0.000 claims 1
239000000050 smooth muscle relaxant Substances 0.000 abstract description 14
125000001424 substituent group Chemical group 0.000 abstract description 7
150000001408 amides Chemical class 0.000 abstract description 2
150000003951 lactams Chemical class 0.000 abstract description 2
150000002465 imidoyl halides Chemical class 0.000 abstract 1
238000011065 in-situ storage Methods 0.000 abstract 1
239000000460 chlorine Substances 0.000 description 37
TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 36
238000006243 chemical reaction Methods 0.000 description 33
239000012458 free base Substances 0.000 description 31
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
150000001875 compounds Chemical class 0.000 description 15
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
229910000041 hydrogen chloride Inorganic materials 0.000 description 14
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 12
231100000252 nontoxic Toxicity 0.000 description 11
230000003000 nontoxic effect Effects 0.000 description 11
239000000376 reactant Substances 0.000 description 11
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
230000000694 effects Effects 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
239000003921 oil Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
239000000243 solution Substances 0.000 description 7
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
150000001409 amidines Chemical class 0.000 description 6
XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000000203 mixture Substances 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
230000004044 response Effects 0.000 description 5
ZLPPJJZCOCPXDE-UHFFFAOYSA-N 2-chloro-10h-phenoxazine Chemical compound C1=CC=C2NC3=CC(Cl)=CC=C3OC2=C1 ZLPPJJZCOCPXDE-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
230000002965 anti-thrombogenic effect Effects 0.000 description 4
230000037396 body weight Effects 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
125000000623 heterocyclic group Chemical group 0.000 description 4
230000004048 modification Effects 0.000 description 4
238000012986 modification Methods 0.000 description 4
239000003506 spasmogen Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
238000001665 trituration Methods 0.000 description 4
FSIVCGKPJLLXGH-UHFFFAOYSA-N 4-chloro-10h-phenoxazine Chemical compound N1C2=CC=CC=C2OC2=C1C=CC=C2Cl FSIVCGKPJLLXGH-UHFFFAOYSA-N 0.000 description 3
YRKRGYRYEQYTOH-UHFFFAOYSA-N 4-methylpyrrolidin-2-one Chemical compound CC1CNC(=O)C1 YRKRGYRYEQYTOH-UHFFFAOYSA-N 0.000 description 3
229930008281 A03AD01 - Papaverine Natural products 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000009471 action Effects 0.000 description 3
239000007900 aqueous suspension Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
229960001789 papaverine Drugs 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
230000002040 relaxant effect Effects 0.000 description 3
210000002460 smooth muscle Anatomy 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
DHOKFNJTMOASEU-UHFFFAOYSA-N 10-(3,4-dihydro-2h-pyrrol-5-yl)phenoxazine Chemical compound C1CCN=C1N1C2=CC=CC=C2OC2=CC=CC=C21 DHOKFNJTMOASEU-UHFFFAOYSA-N 0.000 description 2
QLGPNNJCEDXCMC-UHFFFAOYSA-N 2,3-dichloro-10h-phenoxazine Chemical compound N1C2=CC=CC=C2OC2=C1C=C(Cl)C(Cl)=C2 QLGPNNJCEDXCMC-UHFFFAOYSA-N 0.000 description 2
AQKUXPJCYBZNJZ-UHFFFAOYSA-N 2-methoxy-9,10-dihydroacridine Chemical compound C1=CC=C2CC3=CC(OC)=CC=C3NC2=C1 AQKUXPJCYBZNJZ-UHFFFAOYSA-N 0.000 description 2
XTLFOIVDMKTDED-UHFFFAOYSA-N 2-methyl-10h-phenoxazine Chemical compound C1=CC=C2NC3=CC(C)=CC=C3OC2=C1 XTLFOIVDMKTDED-UHFFFAOYSA-N 0.000 description 2
DJCOPNFRRNKTKL-UHFFFAOYSA-N 2-methyl-9,10-dihydroacridine Chemical compound C1=CC=C2CC3=CC(C)=CC=C3NC2=C1 DJCOPNFRRNKTKL-UHFFFAOYSA-N 0.000 description 2
BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 2
RMQWHXDLQIILBC-UHFFFAOYSA-N 2h-oxazine;hydrochloride Chemical compound Cl.N1OC=CC=C1 RMQWHXDLQIILBC-UHFFFAOYSA-N 0.000 description 2
IODUOIUYROGXDX-UHFFFAOYSA-N 3-chloro-10h-phenoxazine Chemical compound C1=CC=C2OC3=CC(Cl)=CC=C3NC2=C1 IODUOIUYROGXDX-UHFFFAOYSA-N 0.000 description 2
APPNWOOHTWFKBN-UHFFFAOYSA-N 4-butyl-9,10-dihydroacridine Chemical compound C1C2=CC=CC=C2NC2=C1C=CC=C2CCCC APPNWOOHTWFKBN-UHFFFAOYSA-N 0.000 description 2
GZKANJTVQDDCOT-UHFFFAOYSA-N 4-methoxy-10h-phenoxazine Chemical compound N1C2=CC=CC=C2OC2=C1C=CC=C2OC GZKANJTVQDDCOT-UHFFFAOYSA-N 0.000 description 2
DKDBKUTWRXLJEX-UHFFFAOYSA-N 4-methoxy-9,10-dihydroacridine Chemical compound C1C2=CC=CC=C2NC2=C1C=CC=C2OC DKDBKUTWRXLJEX-UHFFFAOYSA-N 0.000 description 2
ZNOQJUUQBHQARO-UHFFFAOYSA-N 4-methoxy-9,9-dimethyl-10h-acridine Chemical compound N1C2=CC=CC=C2C(C)(C)C2=C1C(OC)=CC=C2 ZNOQJUUQBHQARO-UHFFFAOYSA-N 0.000 description 2
PXYRSXFVCNNBDZ-UHFFFAOYSA-N 4-methyl-10h-phenoxazine Chemical compound N1C2=CC=CC=C2OC2=C1C=CC=C2C PXYRSXFVCNNBDZ-UHFFFAOYSA-N 0.000 description 2
XEBCVPFQKUBMDF-UHFFFAOYSA-N 4-propan-2-yloxy-10h-phenoxazine Chemical compound N1C2=CC=CC=C2OC2=C1C=CC=C2OC(C)C XEBCVPFQKUBMDF-UHFFFAOYSA-N 0.000 description 2
ZCHZDOXKZQWGMC-UHFFFAOYSA-N 5,5-dibutylpyrrolidin-2-one Chemical compound CCCCC1(CCCC)CCC(=O)N1 ZCHZDOXKZQWGMC-UHFFFAOYSA-N 0.000 description 2
RXGUEHFXILQWQO-UHFFFAOYSA-N 6,6-dimethylpiperidin-2-one Chemical compound CC1(C)CCCC(=O)N1 RXGUEHFXILQWQO-UHFFFAOYSA-N 0.000 description 2
XPMMAKUHNMSONL-UHFFFAOYSA-N 6-methylpiperidin-2-one Chemical compound CC1CCCC(=O)N1 XPMMAKUHNMSONL-UHFFFAOYSA-N 0.000 description 2
ZICOGRWYQRIGEF-UHFFFAOYSA-N 9-ethyl-9-methyl-10h-acridine Chemical compound C1=CC=C2C(CC)(C)C3=CC=CC=C3NC2=C1 ZICOGRWYQRIGEF-UHFFFAOYSA-N 0.000 description 2
JKDCMAGYXLPYEQ-UHFFFAOYSA-N 9-methyl-2-(trifluoromethyl)-9,10-dihydroacridine Chemical compound C1=C(C(F)(F)F)C=C2C(C)C3=CC=CC=C3NC2=C1 JKDCMAGYXLPYEQ-UHFFFAOYSA-N 0.000 description 2
241000896072 Acrida Species 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 2
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
PECIYKGSSMCNHN-UHFFFAOYSA-N aminophylline Chemical compound NCCN.O=C1N(C)C(=O)N(C)C2=NC=N[C]21.O=C1N(C)C(=O)N(C)C2=NC=N[C]21 PECIYKGSSMCNHN-UHFFFAOYSA-N 0.000 description 2
229960003556 aminophylline Drugs 0.000 description 2
RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 2
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
WYLHQTSQMKMTGM-UHFFFAOYSA-N n-cyclopentylformamide Chemical compound O=CNC1CCCC1 WYLHQTSQMKMTGM-UHFFFAOYSA-N 0.000 description 2
DUUADMGTZDJNRI-UHFFFAOYSA-N n-cyclopropylacetamide Chemical compound CC(=O)NC1CC1 DUUADMGTZDJNRI-UHFFFAOYSA-N 0.000 description 2
AWQVKAURKXXOCG-UHFFFAOYSA-N n-cyclopropylformamide Chemical compound O=CNC1CC1 AWQVKAURKXXOCG-UHFFFAOYSA-N 0.000 description 2
XKEKKGKDCHCOSA-UHFFFAOYSA-N n-methylpentanamide Chemical compound CCCCC(=O)NC XKEKKGKDCHCOSA-UHFFFAOYSA-N 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
229940124531 pharmaceutical excipient Drugs 0.000 description 2
150000002991 phenoxazines Chemical class 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000001422 pyrrolinyl group Chemical group 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000009467 reduction Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
NLEIOFANFLPTBL-UHFFFAOYSA-N 10-(2-methyl-3,4-dihydro-2h-pyrrol-5-yl)phenoxazine Chemical compound CC1CCC(N2C3=CC=CC=C3OC3=CC=CC=C32)=N1 NLEIOFANFLPTBL-UHFFFAOYSA-N 0.000 description 1
OKIOTHRJFSLQRV-UHFFFAOYSA-N 10-(3,4-dihydro-2h-pyrrol-5-yl)-2-methoxy-9h-acridine Chemical compound C12=CC=CC=C2CC2=CC(OC)=CC=C2N1C1=NCCC1 OKIOTHRJFSLQRV-UHFFFAOYSA-N 0.000 description 1
BFTJPQSCIJSENI-UHFFFAOYSA-N 10-(3,4-dihydro-2h-pyrrol-5-yl)-2-methylphenoxazine Chemical compound C12=CC(C)=CC=C2OC2=CC=CC=C2N1C1=NCCC1 BFTJPQSCIJSENI-UHFFFAOYSA-N 0.000 description 1
YTGKTBZCZQQWQW-UHFFFAOYSA-N 10-(3,4-dihydro-2h-pyrrol-5-yl)-4-methoxyphenoxazine Chemical compound C12=CC=CC=C2OC=2C(OC)=CC=CC=2N1C1=NCCC1 YTGKTBZCZQQWQW-UHFFFAOYSA-N 0.000 description 1
AASOGGHLRLBSJM-UHFFFAOYSA-N 10-(3,4-dihydro-2h-pyrrol-5-yl)-4-methylphenoxazine Chemical compound C12=CC=CC=C2OC=2C(C)=CC=CC=2N1C1=NCCC1 AASOGGHLRLBSJM-UHFFFAOYSA-N 0.000 description 1
YWWBFNONWKPZMZ-UHFFFAOYSA-N 10-(3,4-dihydro-2h-pyrrol-5-yl)-9-ethyl-9-methylacridine Chemical compound C12=CC=CC=C2C(CC)(C)C2=CC=CC=C2N1C1=NCCC1 YWWBFNONWKPZMZ-UHFFFAOYSA-N 0.000 description 1
XRXCGEDSPPFPCN-UHFFFAOYSA-N 10-(3,4-dihydro-2h-pyrrol-5-yl)-9-methyl-2-(trifluoromethyl)-9h-acridine Chemical compound C12=CC=C(C(F)(F)F)C=C2C(C)C2=CC=CC=C2N1C1=NCCC1 XRXCGEDSPPFPCN-UHFFFAOYSA-N 0.000 description 1
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Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA249,322A 1976-03-31 1976-03-31 Les 10-imidoylacridans Expired CA1071195A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA249,322A CA1071195A (fr)	1976-03-31	1976-03-31	Les 10-imidoylacridans

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA249,322A CA1071195A (fr)	1976-03-31	1976-03-31	Les 10-imidoylacridans

Publications (1)

Publication Number	Publication Date
CA1071195A true CA1071195A (fr)	1980-02-05

Family

ID=4105605

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA249,322A Expired CA1071195A (fr)	1976-03-31	1976-03-31	Les 10-imidoylacridans

Country Status (1)

Country	Link
CA (1)	CA1071195A (fr)

1976
- 1976-03-31 CA CA249,322A patent/CA1071195A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-02-05	MKEX	Expiry

Publication	Publication Date	Title
IE47965B1 (en)	1984-08-08	Cycloalkyltriazoles and process for obtaining same
SE457081B (sv)	1988-11-28	1,2-diaminocyklobutan-3,4-dioner, foerfarande foer framstaellning av dessa, mellanprodukt och en farmaceutisk komposition
IL49205A (en)	1977-05-31	5-chloro-4-(2-imidazolin-2-ylamino)-2,1,3-benzothiadiazole its production and pharmaceutical compositions containing it
DE68925270T2 (de)	1996-06-13	Pyrrolo[3,2-e]pyrazolo[1,5-a]pyrimidinderivate und diese enthaltende Arzneimittel
HUP9903758A2 (hu)	2000-06-28	Benzoxazinon dopamin D4 receptor antagonisták és az ezeket tartalmazó gyógyszerkészítmények
US3681360A (en)	1972-08-01	Antiviral substituted acridanones
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