CA1051427A - 6-h-pyrimido- (1,2-c) (1,3,5) benzoxadiazepines - Google Patents

6-h-pyrimido- (1,2-c) (1,3,5) benzoxadiazepines

Info

Publication number: CA1051427A
Authority: CA; Canada
Prior art keywords: compound; carbons; hydrogen; alkyl; pyrimido
Prior art date: 1973-07-26
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

CA203,723A

Other languages

English (en)

Other versions

CA203723S (en

Inventor

Harry L. Yale

Ramesh B. Petigara

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.)

ER Squibb and Sons LLC

Original Assignee

ER Squibb and Sons 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.)

1973-07-26

Filing date

1974-06-28

Publication date

1979-03-27

1974-06-28 Application filed by ER Squibb and Sons LLC filed Critical ER Squibb and Sons LLC

1979-03-27 Application granted granted Critical

1979-03-27 Publication of CA1051427A publication Critical patent/CA1051427A/fr

Status Expired legal-status Critical Current

Links

KRQOTYZAJQIMGY-UHFFFAOYSA-N 1,3,5-benzoxadiazepine Chemical class O1C=NC=NC2=CC=CC=C12 KRQOTYZAJQIMGY-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 49
-1 mono-substituted phenyl Chemical group 0.000 claims abstract description 23
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 13
125000000217 alkyl group Chemical group 0.000 claims abstract description 10
229910052794 bromium Inorganic materials 0.000 claims abstract description 10
229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
150000003839 salts Chemical class 0.000 claims abstract description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
238000004519 manufacturing process Methods 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 18
239000000460 chlorine Substances 0.000 claims description 9
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 8
229910052783 alkali metal Inorganic materials 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 5
NWGOCMQTBAMTNM-UHFFFAOYSA-N 6h-pyrimido[1,2-c][1,3,5]benzoxadiazepine Chemical compound C1OC2=CC=CC=C2N=C2N=CC=CN12 NWGOCMQTBAMTNM-UHFFFAOYSA-N 0.000 claims description 4
239000010949 copper Substances 0.000 claims description 4
229910052802 copper Inorganic materials 0.000 claims description 4
229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 3
150000008041 alkali metal carbonates Chemical class 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
229910000318 alkali metal phosphate Inorganic materials 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
239000007858 starting material Substances 0.000 claims 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
QAKXCYJYBKJJCG-UHFFFAOYSA-N 11-methyl-8-phenyl-11,12-dihydropyrimido[2,1-b][6,1,3]benzoxadiazocine Chemical compound C1=C2OC(C)CN3C=CC=NC3=NC2=CC=C1C1=CC=CC=C1 QAKXCYJYBKJJCG-UHFFFAOYSA-N 0.000 claims 1
XELVJSSFQBXFMY-UHFFFAOYSA-N 2-chloro-6h-pyrimido[1,2-c][1,3,5]benzoxadiazepine Chemical compound O1CN2C=CC(Cl)=NC2=NC2=CC=CC=C21 XELVJSSFQBXFMY-UHFFFAOYSA-N 0.000 claims 1
150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
150000001340 alkali metals Chemical class 0.000 claims 1
239000003054 catalyst Substances 0.000 claims 1
LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 abstract description 9
229910052731 fluorine Inorganic materials 0.000 abstract description 7
239000000543 intermediate Substances 0.000 abstract description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 6
239000003158 myorelaxant agent Substances 0.000 abstract description 5
229910052736 halogen Inorganic materials 0.000 abstract description 4
150000002367 halogens Chemical group 0.000 abstract description 4
150000002431 hydrogen Chemical class 0.000 abstract description 4
229910052740 iodine Inorganic materials 0.000 abstract description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 abstract description 3
229940035363 muscle relaxants Drugs 0.000 abstract description 3
125000003545 alkoxy group Chemical group 0.000 abstract description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 2
210000003169 central nervous system Anatomy 0.000 abstract description 2
230000004936 stimulating effect Effects 0.000 abstract description 2
125000001424 substituent group Chemical group 0.000 abstract description 2
239000000203 mixture Substances 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
239000000047 product Substances 0.000 description 17
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 12
239000007787 solid Substances 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
238000010992 reflux Methods 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
229920002261 Corn starch Polymers 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000008120 corn starch Substances 0.000 description 7
230000000694 effects Effects 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000002775 capsule Substances 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
239000008096 xylene Substances 0.000 description 5
DMTVEFFTCXZRHY-UHFFFAOYSA-N 1,2,3-benzoxadiazepine Chemical compound O1N=NC=CC2=CC=CC=C12 DMTVEFFTCXZRHY-UHFFFAOYSA-N 0.000 description 4
VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
WINXNKPZLFISPD-UHFFFAOYSA-M Saccharin sodium Chemical group [Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 WINXNKPZLFISPD-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
239000000975 dye Substances 0.000 description 3
239000000796 flavoring agent Substances 0.000 description 3
239000008187 granular material Substances 0.000 description 3
239000008101 lactose Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
DNAKJQYSYLJGCB-UHFFFAOYSA-N (2-bromo-4-chlorophenoxy)methanesulfonic acid Chemical compound OS(=O)(=O)COC1=CC=C(Cl)C=C1Br DNAKJQYSYLJGCB-UHFFFAOYSA-N 0.000 description 2
RTDNESHWBNWLKO-UHFFFAOYSA-N (2-bromophenoxy)methanesulfonic acid Chemical class OS(=O)(=O)COC1=CC=CC=C1Br RTDNESHWBNWLKO-UHFFFAOYSA-N 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
ZIYRDJLAJYTELF-UHFFFAOYSA-N 2-bromo-4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1Br ZIYRDJLAJYTELF-UHFFFAOYSA-N 0.000 description 2
NEBQYYGAMOFILW-UHFFFAOYSA-N 2-chloro-6h-pyrimido[1,2-c][1,3,5]benzoxadiazepine;hydrochloride Chemical compound Cl.O1CN2C=CC(Cl)=NC2=NC2=CC=CC=C21 NEBQYYGAMOFILW-UHFFFAOYSA-N 0.000 description 2
229920001817 Agar Polymers 0.000 description 2
241000167854 Bourreria succulenta Species 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
229910020656 PBr5 Inorganic materials 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000008272 agar Substances 0.000 description 2
239000003513 alkali Substances 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 2
235000019693 cherries Nutrition 0.000 description 2
239000007958 cherry flavor Substances 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
235000019634 flavors Nutrition 0.000 description 2
235000003599 food sweetener Nutrition 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
230000000813 microbial effect Effects 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
239000006187 pill Substances 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
IDXKTTNFXPPXJY-UHFFFAOYSA-N pyrimidin-1-ium;chloride Chemical compound Cl.C1=CN=CN=C1 IDXKTTNFXPPXJY-UHFFFAOYSA-N 0.000 description 2
150000003230 pyrimidines Chemical class 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 2
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
229940081974 saccharin Drugs 0.000 description 2
235000019204 saccharin Nutrition 0.000 description 2
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 2
235000010234 sodium benzoate Nutrition 0.000 description 2
239000004299 sodium benzoate Substances 0.000 description 2
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
235000010265 sodium sulphite Nutrition 0.000 description 2
ABYVLIWKJMBHJO-UHFFFAOYSA-M sodium;bromomethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CBr ABYVLIWKJMBHJO-UHFFFAOYSA-M 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
239000003765 sweetening agent Substances 0.000 description 2
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
ZRSKKRWCHNPOPE-UHFFFAOYSA-N 1,1-dibromobutane Chemical compound CCCC(Br)Br ZRSKKRWCHNPOPE-UHFFFAOYSA-N 0.000 description 1
APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
QBLPUSMNBSNAHZ-UHFFFAOYSA-N 1,1-dibromopentane Chemical compound CCCCC(Br)Br QBLPUSMNBSNAHZ-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
KSHFHYGYMMKDMR-UHFFFAOYSA-N 1-[(2-bromophenoxy)methyl]pyrimidin-1-ium-2-amine;chloride Chemical compound [Cl-].NC1=NC=CC=[N+]1COC1=CC=CC=C1Br KSHFHYGYMMKDMR-UHFFFAOYSA-N 0.000 description 1
DEEYDHPEYYABHU-UHFFFAOYSA-N 1-bromo-2-(2-chloropropoxy)benzene Chemical compound CC(Cl)COC1=CC=CC=C1Br DEEYDHPEYYABHU-UHFFFAOYSA-N 0.000 description 1
YMHXXJJTAGKFBA-UHFFFAOYSA-N 1-bromo-2-chloropropane Chemical compound CC(Cl)CBr YMHXXJJTAGKFBA-UHFFFAOYSA-N 0.000 description 1
KYRHNMRVOXNROG-UHFFFAOYSA-N 16-oxa-4,6,14,15-tetrazatricyclo[8.6.0.02,7]hexadeca-1(10),2,4,6,8,11,13-heptaene Chemical class O1NN=CC=CC2=C1C1=C(C=C2)N=CN=C1 KYRHNMRVOXNROG-UHFFFAOYSA-N 0.000 description 1
GUXWVUVLXIJHQF-UHFFFAOYSA-N 2,5-dibromophenol Chemical compound OC1=CC(Br)=CC=C1Br GUXWVUVLXIJHQF-UHFFFAOYSA-N 0.000 description 1
125000005273 2-acetoxybenzoic acid group Chemical group 0.000 description 1
BGXIEVDGWFEPEE-UHFFFAOYSA-N 2-bromo-4-chloro-1-(chloromethoxy)benzene Chemical compound ClCOC1=CC=C(Cl)C=C1Br BGXIEVDGWFEPEE-UHFFFAOYSA-N 0.000 description 1
SKEPGKNNHNMXEH-UHFFFAOYSA-N 2-bromo-5-(2-methylpropyl)phenol Chemical compound CC(C)CC1=CC=C(Br)C(O)=C1 SKEPGKNNHNMXEH-UHFFFAOYSA-N 0.000 description 1
SDWRSCDDUQXWKD-UHFFFAOYSA-N 2-bromo-5-butylphenol Chemical compound CCCCC1=CC=C(Br)C(O)=C1 SDWRSCDDUQXWKD-UHFFFAOYSA-N 0.000 description 1
FMRKYXVZQWHGDA-UHFFFAOYSA-N 2-bromo-5-chlorophenol Chemical compound OC1=CC(Cl)=CC=C1Br FMRKYXVZQWHGDA-UHFFFAOYSA-N 0.000 description 1
SWIGUEDLPKNRMQ-UHFFFAOYSA-N 2-bromo-5-ethylsulfonylphenol Chemical compound CCS(=O)(=O)C1=CC=C(Br)C(O)=C1 SWIGUEDLPKNRMQ-UHFFFAOYSA-N 0.000 description 1
HUVAOAVBKOVPBZ-UHFFFAOYSA-N 2-bromo-5-fluorophenol Chemical compound OC1=CC(F)=CC=C1Br HUVAOAVBKOVPBZ-UHFFFAOYSA-N 0.000 description 1
VRITXTVQJJMQIT-UHFFFAOYSA-N 2-bromo-5-iodophenol Chemical compound OC1=CC(I)=CC=C1Br VRITXTVQJJMQIT-UHFFFAOYSA-N 0.000 description 1
LTJNJOSNHALAPB-UHFFFAOYSA-N 2-chloro-1-(2-chloropropoxy)propane Chemical compound CC(Cl)COCC(C)Cl LTJNJOSNHALAPB-UHFFFAOYSA-N 0.000 description 1
MWLXUTKFPIRZJK-UHFFFAOYSA-N 2h-1,2,3-benzoxadiazocine Chemical compound O1NN=CC=CC2=CC=CC=C21 MWLXUTKFPIRZJK-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
UKZIGIIGSCRZEX-UHFFFAOYSA-N 4-bromo-3-hydroxybenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(Br)C(O)=C1 UKZIGIIGSCRZEX-UHFFFAOYSA-N 0.000 description 1
JYGOFGJNWGAPAN-UHFFFAOYSA-N 5-phenylpyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=CC=CC=C1 JYGOFGJNWGAPAN-UHFFFAOYSA-N 0.000 description 1
YIUIVFFUEVPRIU-UHFFFAOYSA-N 8-chlorotheophylline Chemical compound O=C1N(C)C(=O)N(C)C2=NC(Cl)=N[C]21 YIUIVFFUEVPRIU-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
244000246386 Mentha pulegium Species 0.000 description 1
235000016257 Mentha pulegium Nutrition 0.000 description 1
235000004357 Mentha x piperita Nutrition 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
229910004835 Na2B4O7 Inorganic materials 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
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241000607132 Salmonella enterica subsp. enterica serovar Gallinarum Species 0.000 description 1
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KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
241000193996 Streptococcus pyogenes Species 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
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239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
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230000001580 bacterial effect Effects 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
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238000004166 bioassay Methods 0.000 description 1
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239000000872 buffer Substances 0.000 description 1
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239000001506 calcium phosphate Substances 0.000 description 1
239000007963 capsule composition Substances 0.000 description 1
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239000001768 carboxy methyl cellulose Substances 0.000 description 1
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235000015218 chewing gum Nutrition 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
150000002085 enols Chemical class 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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125000001153 fluoro group Chemical group F* 0.000 description 1
235000013305 food Nutrition 0.000 description 1
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238000009472 formulation Methods 0.000 description 1
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229920000159 gelatin Polymers 0.000 description 1
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239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
239000007887 hard shell capsule Substances 0.000 description 1
235000001050 hortel pimenta Nutrition 0.000 description 1
ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-O hydron;pyrimidine Chemical compound C1=CN=C[NH+]=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-O 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000000155 melt Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000011812 mixed powder Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000004570 mortar (masonry) Substances 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000007968 orange flavor Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012071 phase Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
229940007042 proteus vulgaris Drugs 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
WPFGFHJALYCVMO-UHFFFAOYSA-L rubidium carbonate Chemical compound [Rb+].[Rb+].[O-]C([O-])=O WPFGFHJALYCVMO-UHFFFAOYSA-L 0.000 description 1
229910000026 rubidium carbonate Inorganic materials 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000004208 shellac Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
241000894007 species Species 0.000 description 1
229940076156 streptococcus pyogenes Drugs 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
201000008827 tuberculosis Diseases 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
239000009637 wintergreen oil Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA203,723A 1973-07-26 1974-06-28 6-h-pyrimido- (1,2-c) (1,3,5) benzoxadiazepines Expired CA1051427A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US382803A US3886158A (en)	1973-07-26	1973-07-26	6H-pyrimido{8 1,2-c{9 {8 1,3,5{9 {0 benzoxadiazepines

Publications (1)

Publication Number	Publication Date
CA1051427A true CA1051427A (fr)	1979-03-27

Family

ID=23510470

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA203,723A Expired CA1051427A (fr)	1973-07-26	1974-06-28	6-h-pyrimido- (1,2-c) (1,3,5) benzoxadiazepines

Country Status (6)

Country	Link
US (1)	US3886158A (fr)
JP (1)	JPS5041893A (fr)
CA (1)	CA1051427A (fr)
DE (1)	DE2435383A1 (fr)
FR (1)	FR2238492B1 (fr)
GB (1)	GB1476124A (fr)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3833588A (en) *	1972-04-25	1974-09-03	Sandoz Ag	Unsaturated-substituted tricyclic quinazolinones

1973
- 1973-07-26 US US382803A patent/US3886158A/en not_active Expired - Lifetime
1974
- 1974-06-28 CA CA203,723A patent/CA1051427A/fr not_active Expired
- 1974-07-03 GB GB2953374A patent/GB1476124A/en not_active Expired
- 1974-07-23 DE DE2435383A patent/DE2435383A1/de not_active Withdrawn
- 1974-07-26 FR FR7426131A patent/FR2238492B1/fr not_active Expired
- 1974-07-26 JP JP49086508A patent/JPS5041893A/ja active Pending

Also Published As

Publication number	Publication date
FR2238492A1 (fr)	1975-02-21
US3886158A (en)	1975-05-27
GB1476124A (en)	1977-06-10
DE2435383A1 (de)	1975-02-13
FR2238492B1 (fr)	1978-07-28
JPS5041893A (fr)	1975-04-16

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US7005432B2 (en)	2006-02-28	Substituted imidazol-pyridazine derivatives
US5824698A (en)	1998-10-20	Antibacterial dibenzimidazole derivatives
NO155884B (no)	1987-03-09	Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazol-derivater.
JPS6033114B2 (ja)	1985-08-01	１，２−ベンズイソキサゾ−ル誘導体
CA1051429A (fr)	1979-03-27	Composes de 6h-pyrimido (1,2-c) (1,3,5) benzothiadiazoiques
CA1051427A (fr)	1979-03-27	6-h-pyrimido- (1,2-c) (1,3,5) benzoxadiazepines
US3965101A (en)	1976-06-22	1-(O-Bromo-phenoxyalkyl)-1,2-dihydro-2-iminopyrimidines
US4652584A (en)	1987-03-24	Acetylenic phenoxypropanol derivatives and pharmaceutical compositions for the treatment of hypertension
US4612312A (en)	1986-09-16	Glutarimide antianxiety and antihypertensive agents
US4737516A (en)	1988-04-12	Benzothienylallylamines processes for their production and their use as pharmaceuticals
US4340595A (en)	1982-07-20	Aminopropanol derivatives of 6-hydroxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one and pharmaceutical formulations containing the said compounds
EP0585116B1 (fr)	1996-02-28	Dérivés de 1-alkoxy-naphtalène-2-carboxamide avec grande affinité pour le récepteur de sérotonine 5-HT1A
CA1051885A (fr)	1979-04-03	Composes therapeutiques et leurs intermediaires
US4517311A (en)	1985-05-14	2'-Substituted-spiro[benzofuran-2(3H),1'-cycloalkanes] and their analgesic and anti-depressant compositions
US3957785A (en)	1976-05-18	Bβ-Pyrimidino-aminomethyl-10α-ergoline and 10α-methoxyergoline derivatives
US3995042A (en)	1976-11-30	Pyridine containing compounds
US3957787A (en)	1976-05-18	1,2-dihydro-2-imino-1-(bromophenylalkyl)pyrimidines
US3966733A (en)	1976-06-29	Intermediates for certain benzothiadiazepine and benzothiadiazocine compounds
US4062846A (en)	1977-12-13	Hydroxy pyrimido compounds
US4134975A (en)	1979-01-16	Stimulating the central nervous system
US3957806A (en)	1976-05-18	Intermediates for use in preparing therapeutic compounds
US4511566A (en)	1985-04-16	2-N-Cycloalkylmethyl 3-oxo 5,6-diaryl-as-triazines
NO792275L (no)	1980-01-11	Fremgangsmaate for fremstilling av farmakologisk aktive pyrazolo-pyridinderivater