NO843909L - Substituerte 2(1h)-kinazolinon-1-alkansyrer og -estere samt fremgangsmaate for deres fremstilling - Google Patents

Substituerte 2(1h)-kinazolinon-1-alkansyrer og -estere samt fremgangsmaate for deres fremstilling

Info

Publication number: NO843909L
Authority: NO; Norway
Prior art keywords: methyl; quinazolinone; formula; hydrogen; propionic acid
Prior art date: 1983-09-29

Application number

NO843909A

Other languages

English (en)

Norwegian (no)

Inventor

Victor T Bandurco

Seymour D Levine

Alfonso J Tobia

Dennis M Mulvey

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.)

1983-09-29

Filing date

1984-09-28

Publication date

1985-04-01

1983-09-29 Priority claimed from US06/537,233 external-priority patent/US4555571A/en

1984-09-28 Application filed by Ortho Pharma Corp filed Critical Ortho Pharma Corp

1985-04-01 Publication of NO843909L publication Critical patent/NO843909L/no

Links

238000000034 method Methods 0.000 title claims description 31
239000002253 acid Substances 0.000 title claims description 18
238000002360 preparation method Methods 0.000 title description 7
150000007513 acids Chemical class 0.000 title description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 48
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
150000001875 compounds Chemical class 0.000 claims description 33
AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical compound C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 claims description 31
229910052739 hydrogen Inorganic materials 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 23
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
125000003545 alkoxy group Chemical group 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 16
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 15
150000002431 hydrogen Chemical group 0.000 claims description 15
-1 morpholino, methylpiperazino, hydroxy Chemical group 0.000 claims description 12
125000004423 acyloxy group Chemical group 0.000 claims description 11
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 11
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical group [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 claims description 11
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
150000002148 esters Chemical class 0.000 claims description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
150000008065 acid anhydrides Chemical class 0.000 claims description 2
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
150000001336 alkenes Chemical class 0.000 claims 4
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims 4
125000004663 dialkyl amino group Chemical group 0.000 claims 4
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 4
150000007530 organic bases Chemical class 0.000 claims 4
230000003301 hydrolyzing effect Effects 0.000 claims 3
238000004519 manufacturing process Methods 0.000 claims 3
ADYZJRIEZVZJKL-UHFFFAOYSA-N 5-hydroxy-1h-quinazoline-2,4-dione Chemical compound N1C(=O)N=C(O)C2=C1C=CC=C2O ADYZJRIEZVZJKL-UHFFFAOYSA-N 0.000 claims 2
150000008064 anhydrides Chemical class 0.000 claims 1
125000001589 carboacyl group Chemical group 0.000 claims 1
238000002844 melting Methods 0.000 description 41
230000008018 melting Effects 0.000 description 41
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 22
239000000047 product Substances 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
125000004432 carbon atom Chemical group C* 0.000 description 14
239000000243 solution Substances 0.000 description 14
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 12
235000019260 propionic acid Nutrition 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 11
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238000006243 chemical reaction Methods 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 9
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
238000001914 filtration Methods 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
229910052742 iron Inorganic materials 0.000 description 5
239000003921 oil Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000002002 slurry Substances 0.000 description 4
HVXQVXNQKCPSLH-UHFFFAOYSA-N 1-(5-chloro-2-nitrophenyl)ethanone Chemical compound CC(=O)C1=CC(Cl)=CC=C1[N+]([O-])=O HVXQVXNQKCPSLH-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
239000002775 capsule Substances 0.000 description 3
229910000042 hydrogen bromide Inorganic materials 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
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RCIIBQQGPHJINW-UHFFFAOYSA-N (7-chloro-4-methyl-2-oxo-3h-quinazolin-6-yl)urea Chemical compound ClC1=C(NC(N)=O)C=C2C(C)=NC(=O)NC2=C1 RCIIBQQGPHJINW-UHFFFAOYSA-N 0.000 description 2
JCBLTXXNEXJVFT-UHFFFAOYSA-N 1-(2-amino-5-fluorophenyl)ethanone Chemical compound CC(=O)C1=CC(F)=CC=C1N JCBLTXXNEXJVFT-UHFFFAOYSA-N 0.000 description 2
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical compound NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
PZLQQSIMSBQNIN-UHFFFAOYSA-N 4-butyl-6,7-dimethoxy-5-methyl-3h-quinazolin-2-one Chemical compound COC1=C(OC)C(C)=C2C(CCCC)=NC(=O)NC2=C1 PZLQQSIMSBQNIN-UHFFFAOYSA-N 0.000 description 2
BLJBXLZLEHTKAM-UHFFFAOYSA-N 4-morpholin-4-yl-1h-quinazolin-2-one Chemical compound C12=CC=CC=C2NC(=O)N=C1N1CCOCC1 BLJBXLZLEHTKAM-UHFFFAOYSA-N 0.000 description 2
GIAZCPDENZXJFW-UHFFFAOYSA-N 5,6,7-trimethoxy-4-methyl-3h-quinazolin-2-one Chemical compound N1C(=O)N=C(C)C2=C1C=C(OC)C(OC)=C2OC GIAZCPDENZXJFW-UHFFFAOYSA-N 0.000 description 2
CKYSMEWLRZZFCC-UHFFFAOYSA-N 6,7-dimethoxy-4,5-dimethyl-3h-quinazolin-2-one Chemical compound N1C(=O)N=C(C)C2=C1C=C(OC)C(OC)=C2C CKYSMEWLRZZFCC-UHFFFAOYSA-N 0.000 description 2
LWCHLJXPFSHDCU-UHFFFAOYSA-N 6-(dimethylamino)-1h-quinazolin-2-one Chemical compound N1C(=O)N=CC2=CC(N(C)C)=CC=C21 LWCHLJXPFSHDCU-UHFFFAOYSA-N 0.000 description 2
NFEMTTPIPXXATI-UHFFFAOYSA-N 6-(dimethylamino)-4-methyl-3h-quinazolin-2-one Chemical compound N1C(=O)N=C(C)C2=CC(N(C)C)=CC=C21 NFEMTTPIPXXATI-UHFFFAOYSA-N 0.000 description 2
QAGKRQBHOYXDIU-UHFFFAOYSA-N 6-chloro-4-methyl-3h-quinazolin-2-one Chemical compound C1=C(Cl)C=C2C(C)=NC(=O)NC2=C1 QAGKRQBHOYXDIU-UHFFFAOYSA-N 0.000 description 2
IGRXCBOIENURHF-UHFFFAOYSA-N 6-fluoro-4-methyl-3h-quinazolin-2-one Chemical compound C1=C(F)C=C2C(C)=NC(=O)NC2=C1 IGRXCBOIENURHF-UHFFFAOYSA-N 0.000 description 2
JDPJGOLIUFPZRP-UHFFFAOYSA-N 7-(dimethylamino)-4-methyl-3h-quinazolin-2-one Chemical compound CC1=NC(=O)NC2=CC(N(C)C)=CC=C21 JDPJGOLIUFPZRP-UHFFFAOYSA-N 0.000 description 2
MTDINIIHAHDWTR-UHFFFAOYSA-N 7-chloro-4-methyl-6-methylsulfanyl-3h-quinazolin-2-one Chemical compound CC1=NC(=O)NC2=C1C=C(SC)C(Cl)=C2 MTDINIIHAHDWTR-UHFFFAOYSA-N 0.000 description 2
RZJUZOSRWCQGNA-UHFFFAOYSA-N 7-chloro-6-(dimethylamino)-4-methyl-3h-quinazolin-2-one Chemical compound CC1=NC(=O)NC2=C1C=C(N(C)C)C(Cl)=C2 RZJUZOSRWCQGNA-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
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239000005695 Ammonium acetate Substances 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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229910052783 alkali metal Inorganic materials 0.000 description 2
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230000004872 arterial blood pressure Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
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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
239000000706 filtrate Substances 0.000 description 2
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238000010438 heat treatment Methods 0.000 description 2
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238000006460 hydrolysis reaction Methods 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
IJGTWJBHBMDMKF-UHFFFAOYSA-N n-carbamoyl-n-(3,4,5-trimethoxyphenyl)acetamide Chemical compound COC1=CC(N(C(C)=O)C(N)=O)=CC(OC)=C1OC IJGTWJBHBMDMKF-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
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229940124550 renal vasodilator Drugs 0.000 description 2
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
WBPAOUHWPONFEQ-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C(Cl)=C1 WBPAOUHWPONFEQ-UHFFFAOYSA-N 0.000 description 1
PUUYGMZERWRIDS-UHFFFAOYSA-N 1-(4-chloro-2-nitrophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1[N+]([O-])=O PUUYGMZERWRIDS-UHFFFAOYSA-N 0.000 description 1
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
SDQJTWBNWQABLE-UHFFFAOYSA-N 1h-quinazoline-2,4-dione Chemical class C1=CC=C2C(=O)NC(=O)NC2=C1 SDQJTWBNWQABLE-UHFFFAOYSA-N 0.000 description 1
MZBOFQKASKNTRJ-UHFFFAOYSA-N 2,2-diamino-1-phenylethanone Chemical compound NC(N)C(=O)C1=CC=CC=C1 MZBOFQKASKNTRJ-UHFFFAOYSA-N 0.000 description 1
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
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CQFWLSBTSYUMBI-UHFFFAOYSA-N 3,4-dimethoxy-2-methyl-1-phenylpentan-1-one Chemical compound COC(C)C(OC)C(C)C(=O)C1=CC=CC=C1 CQFWLSBTSYUMBI-UHFFFAOYSA-N 0.000 description 1
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230000020335 dealkylation Effects 0.000 description 1
238000006900 dealkylation reaction Methods 0.000 description 1
NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
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GGQOPZKTDHXXON-UHFFFAOYSA-N hexane;methanol Chemical compound OC.CCCCCC GGQOPZKTDHXXON-UHFFFAOYSA-N 0.000 description 1
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238000001990 intravenous administration Methods 0.000 description 1
SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 description 1
LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
238000004321 preservation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
210000002254 renal artery Anatomy 0.000 description 1
230000008327 renal blood flow Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
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 description 1
230000024883 vasodilation Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/112—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

NO843909A 1983-09-29 1984-09-28 Substituerte 2(1h)-kinazolinon-1-alkansyrer og -estere samt fremgangsmaate for deres fremstilling NO843909L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/537,233 US4555571A (en)	1983-09-29	1983-09-29	Substituted 2(1H)-quinazolinone-1-alkanoic acids and esters
US06/627,138 US4656267A (en)	1983-09-29	1984-07-02	Substituted 2(1H)-quinazolinone-1-alkanoic acids and esters

Publications (1)

Publication Number	Publication Date
NO843909L true NO843909L (no)	1985-04-01

Family

ID=27065423

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO843909A NO843909L (no)	1983-09-29	1984-09-28	Substituerte 2(1h)-kinazolinon-1-alkansyrer og -estere samt fremgangsmaate for deres fremstilling

Country Status (5)

Country	Link
US (1)	US4656267A (da)
EP (1)	EP0138491A3 (da)
DK (1)	DK468084A (da)
GR (1)	GR80506B (da)
NO (1)	NO843909L (da)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4751304A (en) *	1984-09-26	1988-06-14	Ortho Pharmaceutical Corporation	Process for preparing 5,6-dialkoxy-4-alkyl-2(1H)-quinazolinones
DE19506739A1 (de) *	1995-02-27	1996-08-29	Bayer Ag	[3-Amino]-tetrahydrocarbazol-propansäureester
CA2450073C (en)	2001-07-25	2017-08-29	Biomarin Pharmaceutical Inc.	Compositions and methods for modulating blood-brain barrier transport
EP2671508B1 (en)	2005-04-28	2020-09-16	Proteus Digital Health, Inc.	Pharma-informatics system
CA2656507C (en) *	2006-07-17	2012-03-20	Amgen Inc.	Quinazoline and pyridopyrimidine derivatives as p38 kinase inhibitors
JP2010503710A (ja)	2006-09-18	2010-02-04	ラプトールファーマシューティカルインコーポレイテッド	受容体関連タンパク質（ｒａｐ）結合体の投与による肝障害の処置
ES2919563T3 (es)	2009-02-20	2022-07-27	Enhanx Biopharm Inc	Sistema de administración de medicamentos a base de glutatión
KR20180114970A (ko)	2009-05-06	2018-10-19	라보라토리 스킨 케어, 인크.	활성제-칼슘 포스페이트 입자 복합체를 포함하는 피부 전달 조성물 및 이들을 이용하는 방법
US20120077778A1 (en)	2010-09-29	2012-03-29	Andrea Bourdelais	Ladder-Frame Polyether Conjugates
US10111873B1 (en)	2018-01-17	2018-10-30	King Saud University	Dihydropyrimidinone derivatives

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2118315C3 (de) *	1970-04-20	1975-04-03	Sumitomo Chemical Co., Ltd., Osaka (Japan)	2-(1H)-Chinazolinonderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
US4001238A (en) *	1976-02-18	1977-01-04	Bristol-Myers Company	1,3,4-oxadiazole amides
US4146712A (en) *	1976-03-11	1979-03-27	Ciba-Geigy Corporation	Process for the manufacture of coumarin dyes
US4490374A (en) *	1982-09-30	1984-12-25	Ortho Pharmaceutical Corporation	5,6-Dialkoxy-3,4-optionally substituted-2(1H)quinazolinones, composition and method of use
US4555571A (en) *	1983-09-29	1985-11-26	Ortho Pharmaceutical Corporation	Substituted 2(1H)-quinazolinone-1-alkanoic acids and esters
US4555570A (en) *	1983-09-29	1985-11-26	Ortho Pharmaceutical Corporation	Substituted 4-alkyl-2-(1H) quinazolinone-1-alkanoic acid derivatives

1984
- 1984-07-02 US US06/627,138 patent/US4656267A/en not_active Expired - Lifetime
- 1984-09-28 DK DK468084A patent/DK468084A/da not_active Application Discontinuation
- 1984-09-28 GR GR80506A patent/GR80506B/el unknown
- 1984-09-28 NO NO843909A patent/NO843909L/no unknown
- 1984-09-28 EP EP84306669A patent/EP0138491A3/en not_active Withdrawn

Also Published As

Publication number	Publication date
GR80506B (en)	1985-01-30
EP0138491A3 (en)	1986-01-15
EP0138491A2 (en)	1985-04-24
DK468084D0 (da)	1984-09-28
US4656267A (en)	1987-04-07
DK468084A (da)	1985-03-30

Publication	Publication Date	Title
US3594480A (en)	1971-07-20	Nitrogen heterocycles for therapeutic administration
US4098786A (en)	1978-07-04	Benzodiazepin derivatives
US3920636A (en)	1975-11-18	Quinazoline compounds
US4029792A (en)	1977-06-14	(2-Imidazolin-2-ylamino) substituted -quinoxalines and -quinazolines as antihypertensive agents
CS201040B2 (en)	1980-10-31	Method of producing etherified hydroxy-benzo-diheterocyclic compounds
NO171785B (no)	1993-01-25	Analogifremgangsmaate for fremstilling av terapeutisk virksomme kinazolinderivater
IE41539B1 (en)	1980-01-30	Chroman derivatives
NZ202471A (en)	1985-09-13	Heterocyclic derivatives and pharmaceutical compositions having cardiotonic and/or antihypertensive properties
EP1484301B1 (en)	2010-08-11	PROCESS FOR PRODUCING trans-4-AMINO-1-CYCLOHEXANECARBOXYLIC ACID DERIVATIVE
US4656267A (en)	1987-04-07	Substituted 2(1H)-quinazolinone-1-alkanoic acids and esters
JPH0692371B2 (ja)	1994-11-16	新規複素環誘導体、その製法およびこれらを含有し、アルド−ス還元酵素抑制剤として特に有用な医薬の製法
JPS61286367A (ja)	1986-12-16	ベンズアゼピン誘導体
US4555571A (en)	1985-11-26	Substituted 2(1H)-quinazolinone-1-alkanoic acids and esters
NZ206823A (en)	1987-07-31	N-piperazinylalkanoylanilides and pharmaceutical compositions
NO773300L (no)	1978-03-29	Fremgangsmaate for fremstilling av nye eddiksyrederivater
US5084456A (en)	1992-01-28	Oxazolopyridine compounds
US4639518A (en)	1987-01-27	Substituted quinazolinediones
US4649198A (en)	1987-03-10	Imidazo(1,5-a)pyrimidine derivatives and their use as antimycotic agents
NO843908L (no)	1985-04-01	Fremgangsmaare for fremstilling av 4-alkyl-2(1h)-kinazolinon-1-alkansyrederivater
HU179391B (en)	1982-10-28	Process for producing thiasolo-square bracket-2,3-b-square bracket closed-quinasoline derivatives
US3949081A (en)	1976-04-06	4-Carbamoyl-1-benzazepines as antiinflammatory agents
NL8002071A (nl)	1980-11-06	2-hydroxy-5-(1-hydroxy-2-piperazinylethyl)- benzoee- zuurderivaten, werkwijze voor de bereiding daarvan, alsmede farmaceutische preparaten die deze bevatten.
US3793322A (en)	1974-02-19	1,4-disubstituted piperazines
US5071849A (en)	1991-12-10	Dihydropyrimidothiazine derivatives
EP0243982A1 (en)	1987-11-04	1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime derivative, process for the production thereof, pharmaceutical composition and intermediates