HU192242B - Process for production of derivatives of substituated dihydroxi-2/1/1/-quinoline and medical preparatives containing them - Google Patents

Process for production of derivatives of substituated dihydroxi-2/1/1/-quinoline and medical preparatives containing them Download PDF

Info

Publication number: HU192242B
Authority: HU; Hungary
Prior art keywords: formula; methyl; quinazolinone; compound; dimethoxy
Prior art date: 1982-09-30

Application number

HU833392A

Other languages

English (en)

Hungarian (hu)

Inventor

Victor T Banduro

Seymour D Levine

Dennis M Mulvey

Alfonso J Tobia

Original Assignee

Ortho Pharma Corp

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.)

1982-09-30

Filing date

1983-09-29

Publication date

1988-10-28

1982-09-30 Priority claimed from US06/430,552 external-priority patent/US4490374A/en

1983-09-29 Application filed by Ortho Pharma Corp filed Critical Ortho Pharma Corp

1988-10-28 Publication of HU192242B publication Critical patent/HU192242B/hu

Links

238000000034 method Methods 0.000 title claims description 11
238000004519 manufacturing process Methods 0.000 title description 2
-1 amine salt Chemical class 0.000 claims abstract description 27
150000003839 salts Chemical class 0.000 claims abstract description 13
125000000217 alkyl group Chemical group 0.000 claims abstract description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
150000001414 amino alcohols Chemical class 0.000 claims abstract description 3
125000003545 alkoxy group Chemical group 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 40
238000002360 preparation method Methods 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 13
AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
150000001336 alkenes Chemical class 0.000 claims description 5
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 5
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 3
MCVVUJPXSBQTRZ-ONEGZZNKSA-N methyl (e)-but-2-enoate Chemical compound COC(=O)\C=C\C MCVVUJPXSBQTRZ-ONEGZZNKSA-N 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
208000024172 Cardiovascular disease Diseases 0.000 claims 1
206010020772 Hypertension Diseases 0.000 claims 1
150000001342 alkaline earth metals Chemical class 0.000 claims 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
229910000039 hydrogen halide Inorganic materials 0.000 claims 1
239000012433 hydrogen halide Substances 0.000 claims 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims 1
239000004575 stone Substances 0.000 claims 1
125000004385 trihaloalkyl group Chemical group 0.000 claims 1
229940124550 renal vasodilator Drugs 0.000 abstract description 3
125000003118 aryl group Chemical group 0.000 abstract description 2
239000002327 cardiovascular agent Substances 0.000 abstract description 2
229940125692 cardiovascular agent Drugs 0.000 abstract description 2
IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 abstract description 2
PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 abstract 2
239000000543 intermediate Substances 0.000 abstract 2
239000003513 alkali Substances 0.000 abstract 1
125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
150000001350 alkyl halides Chemical class 0.000 abstract 1
235000001014 amino acid Nutrition 0.000 abstract 1
125000003435 aroyl group Chemical group 0.000 abstract 1
150000001602 bicycloalkyls Chemical group 0.000 abstract 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
125000001589 carboacyl group Chemical group 0.000 abstract 1
239000000496 cardiotonic agent Substances 0.000 abstract 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
125000001188 haloalkyl group Chemical group 0.000 abstract 1
125000001072 heteroaryl group Chemical group 0.000 abstract 1
239000002184 metal Substances 0.000 abstract 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 111
239000000243 solution Substances 0.000 description 59
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
239000000203 mixture Substances 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 32
239000007787 solid Substances 0.000 description 27
239000011541 reaction mixture Substances 0.000 description 24
239000002904 solvent Substances 0.000 description 24
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
239000002244 precipitate Substances 0.000 description 21
239000000047 product Substances 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
238000003756 stirring Methods 0.000 description 15
239000000725 suspension Substances 0.000 description 14
239000000463 material Substances 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
235000019441 ethanol Nutrition 0.000 description 10
238000001914 filtration Methods 0.000 description 10
239000005457 ice water Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 9
239000012043 crude product Substances 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
239000007858 starting material Substances 0.000 description 9
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 8
238000010992 reflux Methods 0.000 description 8
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
239000000284 extract Substances 0.000 description 7
239000003921 oil Substances 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
229920000137 polyphosphoric acid Polymers 0.000 description 4
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
SXUFERDRAFUQGD-UHFFFAOYSA-N 6,7-dimethoxy-4-methyl-3h-quinazolin-2-one Chemical compound N1C(=O)N=C(C)C2=C1C=C(OC)C(OC)=C2 SXUFERDRAFUQGD-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
239000002775 capsule Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
229910000042 hydrogen bromide Inorganic materials 0.000 description 3
229910000043 hydrogen iodide Inorganic materials 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
239000007788 liquid Substances 0.000 description 3
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
229910017604 nitric acid Inorganic materials 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000002002 slurry Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
KWXFQMHMUVDCGC-UHFFFAOYSA-N 2,3-dimethoxy-6-nitrobenzaldehyde Chemical compound COC1=CC=C([N+]([O-])=O)C(C=O)=C1OC KWXFQMHMUVDCGC-UHFFFAOYSA-N 0.000 description 2
KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical class NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 2
XRZJCCJKHICMRD-UHFFFAOYSA-N 5,6-dimethoxy-4-methyl-3,4-dihydro-1h-quinazolin-2-one Chemical compound N1C(=O)NC(C)C2=C(OC)C(OC)=CC=C21 XRZJCCJKHICMRD-UHFFFAOYSA-N 0.000 description 2
IUOLSQXLCXVPMZ-UHFFFAOYSA-N 7-methoxy-4-methyl-3h-quinazolin-2-one Chemical compound CC1=NC(=O)NC2=CC(OC)=CC=C21 IUOLSQXLCXVPMZ-UHFFFAOYSA-N 0.000 description 2
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
239000005695 Ammonium acetate Substances 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
238000006418 Brown reaction Methods 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
NTURVSFTOYPGON-UHFFFAOYSA-N Dihydroquinazoline Chemical class C1=CC=C2C=NCNC2=C1 NTURVSFTOYPGON-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-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
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
229940043376 ammonium acetate Drugs 0.000 description 2
235000019257 ammonium acetate Nutrition 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000002026 chloroform extract Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
238000001802 infusion Methods 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
239000012948 isocyanate Substances 0.000 description 2
150000002513 isocyanates Chemical class 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 2
238000002156 mixing Methods 0.000 description 2
150000004682 monohydrates Chemical class 0.000 description 2
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
JJVNINGBHGBWJH-UHFFFAOYSA-N ortho-vanillin Chemical compound COC1=CC=CC(C=O)=C1O JJVNINGBHGBWJH-UHFFFAOYSA-N 0.000 description 2
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
239000012071 phase Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
150000003246 quinazolines Chemical group 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 2
150000003673 urethanes Chemical class 0.000 description 2
230000002792 vascular Effects 0.000 description 2
239000008096 xylene Substances 0.000 description 2
GKABHORTMXJPSN-UHFFFAOYSA-N (1,3-dihydroxy-2-methylpropan-2-yl)azanium;hydroxide Chemical compound [OH-].OCC([NH3+])(C)CO GKABHORTMXJPSN-UHFFFAOYSA-N 0.000 description 1
SYSZENVIJHPFNL-UHFFFAOYSA-N (alpha-D-mannosyl)7-beta-D-mannosyl-diacetylchitobiosyl-L-asparagine, isoform B (protein) Chemical compound COC1=CC=C(I)C=C1 SYSZENVIJHPFNL-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
SUGXZLKUDLDTKX-UHFFFAOYSA-N 1-(2-nitrophenyl)ethanone Chemical class CC(=O)C1=CC=CC=C1[N+]([O-])=O SUGXZLKUDLDTKX-UHFFFAOYSA-N 0.000 description 1
VSKSBSORLCDRHS-UHFFFAOYSA-N 1-fluoro-3-iodobenzene Chemical compound FC1=CC=CC(I)=C1 VSKSBSORLCDRHS-UHFFFAOYSA-N 0.000 description 1
KGNQDBQYEBMPFZ-UHFFFAOYSA-N 1-fluoro-4-iodobenzene Chemical compound FC1=CC=C(I)C=C1 KGNQDBQYEBMPFZ-UHFFFAOYSA-N 0.000 description 1
FTAHQVWNRWZINV-UHFFFAOYSA-N 1-hydroxyquinazolin-2-one Chemical class C1=CC=C2C=NC(=O)N(O)C2=C1 FTAHQVWNRWZINV-UHFFFAOYSA-N 0.000 description 1
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KUIZKZHDMPERHR-UHFFFAOYSA-N 1-phenylprop-2-en-1-one Chemical compound C=CC(=O)C1=CC=CC=C1 KUIZKZHDMPERHR-UHFFFAOYSA-N 0.000 description 1
FHBBETAOBPMWTJ-UHFFFAOYSA-N 1h-quinazolin-5-one Chemical compound N1C=NC=C2C(=O)C=CC=C21 FHBBETAOBPMWTJ-UHFFFAOYSA-N 0.000 description 1
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KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 1
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YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 1
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VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
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239000007864 aqueous solution Substances 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
235000009697 arginine Nutrition 0.000 description 1
230000008321 arterial blood flow Effects 0.000 description 1
230000004872 arterial blood pressure Effects 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
239000012455 biphasic mixture Substances 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000017531 blood circulation Effects 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
229910000085 borane Inorganic materials 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
230000003177 cardiotonic effect Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
CCRCUPLGCSFEDV-UHFFFAOYSA-N cinnamic acid methyl ester Natural products COC(=O)C=CC1=CC=CC=C1 CCRCUPLGCSFEDV-UHFFFAOYSA-N 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
230000001186 cumulative effect Effects 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
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229960003638 dopamine Drugs 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
HSGQCWJKQPAHHO-UHFFFAOYSA-N ethyl n-(2-formyl-3,4-dimethoxyphenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C(OC)C(OC)=C1C=O HSGQCWJKQPAHHO-UHFFFAOYSA-N 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
239000011888 foil Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000003979 granulating agent Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
GVLGAFRNYJVHBC-UHFFFAOYSA-N hydrate;hydrobromide Chemical compound O.Br GVLGAFRNYJVHBC-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
235000015243 ice cream Nutrition 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
YWDQMQUSUGZXMK-UHFFFAOYSA-N methyl 3-(4-chlorophenyl)propanoate Chemical compound COC(=O)CCC1=CC=C(Cl)C=C1 YWDQMQUSUGZXMK-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
CCRCUPLGCSFEDV-BQYQJAHWSA-N methyl trans-cinnamate Chemical compound COC(=O)\C=C\C1=CC=CC=C1 CCRCUPLGCSFEDV-BQYQJAHWSA-N 0.000 description 1
150000002780 morpholines Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
ZYZMFAILUWTEQK-UHFFFAOYSA-N n-[(3,4-dimethoxyphenyl)carbamoyl]propanamide Chemical compound CCC(=O)NC(=O)NC1=CC=C(OC)C(OC)=C1 ZYZMFAILUWTEQK-UHFFFAOYSA-N 0.000 description 1
KAQGUAVUISEXHF-UHFFFAOYSA-N n-[(3-methoxyphenyl)carbamoyl]acetamide Chemical compound COC1=CC=CC(NC(=O)NC(C)=O)=C1 KAQGUAVUISEXHF-UHFFFAOYSA-N 0.000 description 1
GASFVSRUEBGMDI-UHFFFAOYSA-N n-aminohydroxylamine Chemical group NNO GASFVSRUEBGMDI-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229960003104 ornithine Drugs 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
229940117803 phenethylamine Drugs 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
RIBFXMJCUYXJDZ-UHFFFAOYSA-N propanoyl bromide Chemical class CCC(Br)=O RIBFXMJCUYXJDZ-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
229910052705 radium Inorganic materials 0.000 description 1
HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 1
210000002254 renal artery Anatomy 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000011775 sodium fluoride Substances 0.000 description 1
235000013024 sodium fluoride Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 0.000 description 1
UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/80—Oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicinal Preparation (AREA)
Cosmetics (AREA)
Manufacture Of Tobacco Products (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

HU833392A 1982-09-30 1983-09-29 Process for production of derivatives of substituated dihydroxi-2/1/1/-quinoline and medical preparatives containing them HU192242B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/430,552 US4490374A (en)	1982-09-30	1982-09-30	5,6-Dialkoxy-3,4-optionally substituted-2(1H)quinazolinones, composition and method of use

Publications (1)

Publication Number	Publication Date
HU192242B true HU192242B (en)	1988-10-28

Family

ID=23708017

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU833392A HU192242B (en)	1982-09-30	1983-09-29	Process for production of derivatives of substituated dihydroxi-2/1/1/-quinoline and medical preparatives containing them

Country Status (13)

Country	Link
KR (1)	KR840006218A (fr)
AT (2)	ATE34979T1 (fr)
DE (2)	DE3382013D1 (fr)
ES (4)	ES8503671A1 (fr)
HU (1)	HU192242B (fr)
IL (1)	IL69849A (fr)
NO (1)	NO833541L (fr)
NZ (1)	NZ205685A (fr)
PH (2)	PH19508A (fr)
RO (2)	RO87466B (fr)
SG (1)	SG31887G (fr)
YU (2)	YU196983A (fr)
ZW (1)	ZW20883A1 (fr)

1983
- 1983-09-21 NZ NZ205685A patent/NZ205685A/en unknown
- 1983-09-28 PH PH29609A patent/PH19508A/en unknown
- 1983-09-28 IL IL69849A patent/IL69849A/xx unknown
- 1983-09-29 HU HU833392A patent/HU192242B/hu unknown
- 1983-09-29 NO NO833541A patent/NO833541L/no unknown
- 1983-09-29 AT AT83305895T patent/ATE34979T1/de active
- 1983-09-29 AT AT86201912T patent/ATE58531T1/de not_active IP Right Cessation
- 1983-09-29 ES ES526133A patent/ES8503671A1/es not_active Expired
- 1983-09-29 ZW ZW208/83A patent/ZW20883A1/xx unknown
- 1983-09-29 RO RO112200A patent/RO87466B/ro unknown
- 1983-09-29 DE DE8686201912T patent/DE3382013D1/de not_active Expired - Lifetime
- 1983-09-29 RO RO83116473A patent/RO89787A/fr unknown
- 1983-09-29 DE DE8383305895T patent/DE3376978D1/de not_active Expired
- 1983-09-30 YU YU01969/83A patent/YU196983A/xx unknown
- 1983-09-30 KR KR1019830004638A patent/KR840006218A/ko not_active Ceased
1984
- 1984-05-29 ES ES532918A patent/ES532918A0/es active Granted
- 1984-05-29 ES ES532919A patent/ES8507511A1/es not_active Expired
- 1984-05-29 ES ES532920A patent/ES532920A0/es active Granted
1985
- 1985-05-24 PH PH32313A patent/PH21757A/en unknown
- 1985-12-11 YU YU01922/85A patent/YU192285A/xx unknown
1987
- 1987-03-31 SG SG318/87A patent/SG31887G/en unknown

Also Published As

Publication number	Publication date
ES8507510A1 (es)	1985-09-01
RO87466A (fr)	1985-08-31
ES8507512A1 (es)	1985-09-01
ES526133A0 (es)	1985-03-16
KR840006218A (ko)	1984-11-22
DE3382013D1 (de)	1991-01-03
DE3376978D1 (en)	1988-07-14
ATE58531T1 (de)	1990-12-15
NZ205685A (en)	1987-03-31
IL69849A0 (en)	1983-12-30
ZW20883A1 (en)	1985-05-01
PH19508A (en)	1986-05-14
ES8503671A1 (es)	1985-03-16
ES532920A0 (es)	1985-09-01
RO87466B (ro)	1985-08-31
YU196983A (en)	1987-02-28
IL69849A (en)	1987-11-30
ATE34979T1 (de)	1988-06-15
SG31887G (en)	1987-07-17
YU192285A (en)	1987-12-31
ES532919A0 (es)	1985-09-01
NO833541L (no)	1984-04-02
RO89787A (fr)	1986-07-30
PH21757A (en)	1988-02-18
ES532918A0 (es)	1985-09-01
ES8507511A1 (es)	1985-09-01

Legal Events

Date	Code	Title	Description
1990-06-28	HU90	Patent valid on 900628

Publication	Publication Date	Title
CA2012628C (fr)	2000-08-29	Nouveaux derives fluoro-4 benzoiques, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent
US4490374A (en)	1984-12-25	5,6-Dialkoxy-3,4-optionally substituted-2(1H)quinazolinones, composition and method of use
JPH07502272A (ja)	1995-03-09	新規な化合物
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CA2444024A1 (fr)	2002-10-17	Hiohydantoines et leur utilisation dans le traitement du diabete
AU653245B2 (en)	1994-09-22	Novel benzopyran derivatives
US4925850A (en)	1990-05-15	Derivatives of 2-((4-piperidinyl)methyl)-1,2,3,4-tetrahydroisoquinoline, their preparation and their application in therapeutics
WO2014020101A1 (fr)	2014-02-06	Derives de griseofulvine
US4061769A (en)	1977-12-06	Method and composition for treating hypertension
US4678791A (en)	1987-07-07	6-phenyl-1,2-3,4,4a,5-6,10b-octahydrobenz(h)isoquinolines useful for treating depression
US5096900A (en)	1992-03-17	(4-piperidyl)methyl-2,3-dihydro-1h-isoindole and -2,3,4,5-tetrahydro-1h-benzazepine derivatives, their preparation and their application in therapy
PL191091B1 (pl)	2006-03-31	Nowe związki indanolowe, zawierające je kompozycje farmaceutyczne oraz ich zastosowanie
FR2558835A1 (fr)	1985-08-02	Derives d'hydantoine, leur procede de production et medicament les contenant
HU192242B (en)	1988-10-28	Process for production of derivatives of substituated dihydroxi-2/1/1/-quinoline and medical preparatives containing them
US4631283A (en)	1986-12-23	Ortho substituted dihydroxy-2(1H)quinazolinone-1-alkanoic acids
US4672064A (en)	1987-06-09	1,5-benzoxathiepin derivatives, their production and use
NZ229899A (en)	1990-11-27	Benzazepine and isoindole derivatives and pharmaceutical compositions
US5578596A (en)	1996-11-26	2-alkoxy-5,6,7,8-tetrahydroquinoxaline derivatives, and production method and use thereof
EP0302787B1 (fr)	1991-10-30	Dérivés de (pipéridinyl-4)méthyl-2 benzofuro[2,3-c]pyridines, leur préparation et leur application en thérapeutique
IE49469B1 (en)	1985-10-16	Substituted quinazolines
CA1271754A (fr)	1990-07-17	Derives de 1,5-benzoxathiepine; preparation et utilisation
FR2639944A1 (fr)	1990-06-08	Nouveaux derives de l'indole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
CZ2002342A3 (cs)	2002-06-12	Isochinolinové deriváty, farmaceutické přípravky s jejich obsahem a způsob přípravy účinné látky
CA1125170A (fr)	1982-06-08	Quinazolin-2-ones
CA1224468A (fr)	1987-07-21	Derives de substitution en ortho d'acides dihydroxy-2(1h)quinazolinone-1-alcanoiques