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 fremstillingInfo
- Publication number
- NO843909L NO843909L NO843909A NO843909A NO843909L NO 843909 L NO843909 L NO 843909L NO 843909 A NO843909 A NO 843909A NO 843909 A NO843909 A NO 843909A NO 843909 L NO843909 L NO 843909L
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- quinazolinone
- formula
- hydrogen
- propionic acid
- Prior art date
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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 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
- 230000002792 vascular Effects 0.000 description 3
- 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
- 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
- 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
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 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
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000003937 drug carrier Substances 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
- 239000000706 filtrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 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
- 239000000843 powder Substances 0.000 description 2
- 229940124550 renal vasodilator Drugs 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 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
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical group CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 1
- 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
- NLXKAIBKKDTOAS-UHFFFAOYSA-N 4-methyl-6-methylsulfanyl-3h-quinazolin-2-one Chemical compound N1C(=O)N=C(C)C2=CC(SC)=CC=C21 NLXKAIBKKDTOAS-UHFFFAOYSA-N 0.000 description 1
- SWGPIDCNYAYXMJ-UHFFFAOYSA-N 5-chloro-2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1C=O SWGPIDCNYAYXMJ-UHFFFAOYSA-N 0.000 description 1
- OAGAVRRTCDOVFL-UHFFFAOYSA-N 5-chloro-7,8-dimethoxy-4-methyl-3h-quinazolin-2-one Chemical compound CC1=NC(=O)NC2=C(OC)C(OC)=CC(Cl)=C21 OAGAVRRTCDOVFL-UHFFFAOYSA-N 0.000 description 1
- MJJXWPHZDBIHIM-UHFFFAOYSA-N 5-isocyanato-1,2,3-trimethoxybenzene Chemical compound COC1=CC(N=C=O)=CC(OC)=C1OC MJJXWPHZDBIHIM-UHFFFAOYSA-N 0.000 description 1
- FUFPVXFYMUAEEG-UHFFFAOYSA-N 6-chloro-3,4-dimethoxy-2-nitrobenzoic acid Chemical compound COC1=CC(Cl)=C(C(O)=O)C([N+]([O-])=O)=C1OC FUFPVXFYMUAEEG-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 206010047141 Vasodilatation Diseases 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000008321 arterial blood flow Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 239000002327 cardiovascular agent Substances 0.000 description 1
- 229940125692 cardiovascular agent Drugs 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 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
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000796 flavoring agent 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
- GGQOPZKTDHXXON-UHFFFAOYSA-N hexane;methanol Chemical compound OC.CCCCCC GGQOPZKTDHXXON-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 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)
- 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)
- Steroid Compounds (AREA)
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 (de) |
EP (1) | EP0138491A3 (de) |
DK (1) | DK468084A (de) |
GR (1) | GR80506B (de) |
NO (1) | NO843909L (de) |
Families Citing this family (10)
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 |
DE60234057D1 (de) | 2001-07-25 | 2009-11-26 | Raptor Pharmaceutical Inc | Zusammensetzungen und verfahren zur modulation des transports durch die blut-hirn-schranke |
CA2789262C (en) | 2005-04-28 | 2016-10-04 | Proteus Digital Health, Inc. | Pharma-informatics system |
AU2007275696B2 (en) * | 2006-07-17 | 2011-11-10 | Amgen Inc. | Quinazoline and pyridopyrimidine derivatives as p38 kinase inhibitors |
EP2063905B1 (de) | 2006-09-18 | 2014-07-30 | Raptor Pharmaceutical Inc | Behandlungen von lebererkrankungen durch verabreichung von konjugaten aus rezeptor-assoziierten proteinen |
PL2398500T3 (pl) | 2009-02-20 | 2019-09-30 | 2-Bbb Medicines B.V. | System dostarczania leków na bazie glutationu |
KR101741629B1 (ko) | 2009-05-06 | 2017-05-31 | 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 (7)
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 |
JPS5795966A (en) * | 1980-12-04 | 1982-06-15 | Sumitomo Chem Co Ltd | Novel 2(1h)-quinazolinone derivative |
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 GR GR80506A patent/GR80506B/el unknown
- 1984-09-28 NO NO843909A patent/NO843909L/no unknown
- 1984-09-28 EP EP84306669A patent/EP0138491A3/de not_active Withdrawn
- 1984-09-28 DK DK468084A patent/DK468084A/da not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
EP0138491A3 (de) | 1986-01-15 |
GR80506B (en) | 1985-01-30 |
DK468084A (da) | 1985-03-30 |
DK468084D0 (da) | 1984-09-28 |
US4656267A (en) | 1987-04-07 |
EP0138491A2 (de) | 1985-04-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3594480A (en) | Nitrogen heterocycles for therapeutic administration | |
US4098786A (en) | Benzodiazepin derivatives | |
US3920636A (en) | Quinazoline compounds | |
US4029792A (en) | (2-Imidazolin-2-ylamino) substituted -quinoxalines and -quinazolines as antihypertensive agents | |
CS201040B2 (en) | Method of producing etherified hydroxy-benzo-diheterocyclic compounds | |
IE41539B1 (en) | Chroman derivatives | |
RU2001910C1 (ru) | Способ получени хинолинового производного | |
NZ202471A (en) | Heterocyclic derivatives and pharmaceutical compositions having cardiotonic and/or antihypertensive properties | |
NO843909L (no) | Substituerte 2(1h)-kinazolinon-1-alkansyrer og -estere samt fremgangsmaate for deres fremstilling | |
EP1484301B1 (de) | Verfahren zur herstellung eines trans-4-amino-1-cyclohexancarbonsäurederivats | |
EP0227450A2 (de) | Substituierte 5,6-Dialkoxychinazolin-Derivate | |
JPH0692371B2 (ja) | 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) | ベンズアゼピン誘導体 | |
US4555571A (en) | Substituted 2(1H)-quinazolinone-1-alkanoic acids and esters | |
NZ206823A (en) | N-piperazinylalkanoylanilides and pharmaceutical compositions | |
US5084456A (en) | Oxazolopyridine compounds | |
US4639518A (en) | Substituted quinazolinediones | |
NO773300L (no) | Fremgangsmaate for fremstilling av nye eddiksyrederivater | |
NO843908L (no) | Fremgangsmaare for fremstilling av 4-alkyl-2(1h)-kinazolinon-1-alkansyrederivater | |
HU179391B (en) | Process for producing thiasolo-square bracket-2,3-b-square bracket closed-quinasoline derivatives | |
US3949081A (en) | 4-Carbamoyl-1-benzazepines as antiinflammatory agents | |
NL8002071A (nl) | 2-hydroxy-5-(1-hydroxy-2-piperazinylethyl)- benzoee- zuurderivaten, werkwijze voor de bereiding daarvan, alsmede farmaceutische preparaten die deze bevatten. | |
US3793322A (en) | 1,4-disubstituted piperazines | |
EP0243982A1 (de) | 1-Acyl-2,3-dihydro-4(1H)-chinolinon-4-oxim-Derivate, Verfahren zur Herstellung davon, pharmazeutische Zusammensetzungen und Zwischenprodukte | |
US5071849A (en) | Dihydropyrimidothiazine derivatives |