NO843908L - Fremgangsmaare for fremstilling av 4-alkyl-2(1h)-kinazolinon-1-alkansyrederivater - Google Patents

Fremgangsmaare for fremstilling av 4-alkyl-2(1h)-kinazolinon-1-alkansyrederivater

Info

Publication number: NO843908L
Authority: NO; Norway
Prior art keywords: quinazolinone; methyl; formula; acid; propionic acid
Prior art date: 1983-09-29

Application number

NO843908A

Other languages

English (en)

Norwegian (no)

Inventor

Ramesh M Kanojia

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 US06/537,232 external-priority patent/US4555570A/en

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

1985-04-01 Publication of NO843908L publication Critical patent/NO843908L/no

Links

239000002253 acid Substances 0.000 title claims description 27
238000000034 method Methods 0.000 title claims description 18
238000002360 preparation method Methods 0.000 title description 12
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 38
150000001875 compounds Chemical class 0.000 claims description 26
AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical compound C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 claims description 22
-1 5,8-dihydroxy-2(1H)quinazolinone Chemical compound 0.000 claims description 21
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 18
239000000460 chlorine Substances 0.000 claims description 13
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
229910000042 hydrogen bromide Inorganic materials 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
238000010992 reflux Methods 0.000 claims description 6
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 2
239000002168 alkylating agent Substances 0.000 claims description 2
229940100198 alkylating agent Drugs 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
229910052794 bromium Chemical group 0.000 claims 3
229910052801 chlorine Inorganic materials 0.000 claims 3
239000005950 Oxamyl Substances 0.000 claims 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
238000009835 boiling Methods 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical group 0.000 claims 1
229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 35
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 22
239000002904 solvent Substances 0.000 description 20
239000007787 solid Substances 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
125000004494 ethyl ester group Chemical group 0.000 description 16
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
239000003921 oil Substances 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
FQTIYMRSUOADDK-UHFFFAOYSA-N ethyl 3-bromopropanoate Chemical compound CCOC(=O)CCBr FQTIYMRSUOADDK-UHFFFAOYSA-N 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
239000011734 sodium Substances 0.000 description 6
LNBMZFHIYRDKNS-UHFFFAOYSA-N 2,2-dimethoxy-1-phenylethanone Chemical compound COC(OC)C(=O)C1=CC=CC=C1 LNBMZFHIYRDKNS-UHFFFAOYSA-N 0.000 description 5
HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical class NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
239000000203 mixture Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000000284 extract Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
238000003756 stirring Methods 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
239000003826 tablet Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002585 base Substances 0.000 description 3
239000012267 brine Substances 0.000 description 3
239000002775 capsule Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000012458 free base Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
150000004702 methyl esters Chemical class 0.000 description 3
238000000746 purification Methods 0.000 description 3
229940124550 renal vasodilator Drugs 0.000 description 3
239000001632 sodium acetate Substances 0.000 description 3
235000017281 sodium acetate Nutrition 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
230000002792 vascular Effects 0.000 description 3
IWEPVHOJXHVCJF-UHFFFAOYSA-M C(CC)(=O)[O-].[Br+] Chemical compound C(CC)(=O)[O-].[Br+] IWEPVHOJXHVCJF-UHFFFAOYSA-M 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
IQZLUWLMQNGTIW-UHFFFAOYSA-N acetoveratrone Chemical compound COC1=CC=C(C(C)=O)C=C1OC IQZLUWLMQNGTIW-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
230000004872 arterial blood pressure Effects 0.000 description 2
230000017531 blood circulation Effects 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000012043 crude product 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
239000003480 eluent Substances 0.000 description 2
238000010828 elution Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
210000002254 renal artery Anatomy 0.000 description 2
239000002002 slurry Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
235000000346 sugar Nutrition 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000010189 synthetic method Methods 0.000 description 2
MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 1
JTWHVBNYYWFXSI-UHFFFAOYSA-N 2-nitro-1-phenylethanone Chemical compound [O-][N+](=O)CC(=O)C1=CC=CC=C1 JTWHVBNYYWFXSI-UHFFFAOYSA-N 0.000 description 1
DHXNZYCXMFBMHE-UHFFFAOYSA-M 3-bromopropanoate Chemical compound [O-]C(=O)CCBr DHXNZYCXMFBMHE-UHFFFAOYSA-M 0.000 description 1
GKTGPJOMPNVMLV-UHFFFAOYSA-N 4-(2-acetyl-4,5-dimethoxyanilino)butanoic acid Chemical compound COC1=CC(NCCCC(O)=O)=C(C(C)=O)C=C1OC GKTGPJOMPNVMLV-UHFFFAOYSA-N 0.000 description 1
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 1
CZESKBVPZYBNES-UHFFFAOYSA-N 6,7-dihydroxy-4-methyl-3H-quinazolin-2-one pentanoic acid Chemical compound CCCCC(O)=O.OC1=C(O)C=C2C(C)=NC(=O)NC2=C1 CZESKBVPZYBNES-UHFFFAOYSA-N 0.000 description 1
NBDZNGSWXYEMCH-UHFFFAOYSA-N 6,7-dimethoxy-4-methyl-3h-quinazolin-2-one;ethyl butanoate Chemical compound CCCC(=O)OCC.N1C(=O)N=C(C)C2=C1C=C(OC)C(OC)=C2 NBDZNGSWXYEMCH-UHFFFAOYSA-N 0.000 description 1
241000156724 Antirhea Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
238000007126 N-alkylation reaction Methods 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000013832 Valeriana officinalis Nutrition 0.000 description 1
244000126014 Valeriana officinalis Species 0.000 description 1
206010047141 Vasodilatation Diseases 0.000 description 1
150000008062 acetophenones Chemical class 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
KXHVHNDQNVXPRD-UHFFFAOYSA-N butanoic acid 6,7-dihydroxy-4-methyl-3H-quinazolin-2-one Chemical compound CCCC(O)=O.OC1=C(O)C=C2C(C)=NC(=O)NC2=C1 KXHVHNDQNVXPRD-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 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
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000013329 compounding Methods 0.000 description 1
150000003983 crown ethers Chemical class 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
238000010908 decantation Methods 0.000 description 1
230000017858 demethylation Effects 0.000 description 1
238000010520 demethylation reaction Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
DARYXUQKCDGKJJ-UHFFFAOYSA-N ethyl 3-(2-acetyl-3,4-dimethoxyanilino)propanoate Chemical compound CCOC(=O)CCNC1=CC=C(OC)C(OC)=C1C(C)=O DARYXUQKCDGKJJ-UHFFFAOYSA-N 0.000 description 1
XBPOBCXHALHJFP-UHFFFAOYSA-N ethyl 4-bromobutanoate Chemical compound CCOC(=O)CCCBr XBPOBCXHALHJFP-UHFFFAOYSA-N 0.000 description 1
HFDPKFYPOJSVFZ-UHFFFAOYSA-N ethyl 5-(2-acetyl-4,5-dimethoxyanilino)pentanoate Chemical compound CCOC(=O)CCCCNC1=CC(OC)=C(OC)C=C1C(C)=O HFDPKFYPOJSVFZ-UHFFFAOYSA-N 0.000 description 1
AFRWBGJRWRHQOV-UHFFFAOYSA-N ethyl 5-bromopentanoate Chemical compound CCOC(=O)CCCCBr AFRWBGJRWRHQOV-UHFFFAOYSA-N 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000003979 granulating agent Substances 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
229910000043 hydrogen iodide Inorganic materials 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
239000012442 inert solvent 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
238000001990 intravenous administration Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012071 phase 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
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000008327 renal blood flow Effects 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000000375 suspending agent 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
238000012360 testing method Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
238000001665 trituration Methods 0.000 description 1
235000016788 valerian Nutrition 0.000 description 1
230000024883 vasodilation Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 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)
Steroid Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO843908A 1983-09-29 1984-09-28 Fremgangsmaare for fremstilling av 4-alkyl-2(1h)-kinazolinon-1-alkansyrederivater NO843908L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/537,232 US4555570A (en)	1983-09-29	1983-09-29	Substituted 4-alkyl-2-(1H) quinazolinone-1-alkanoic acid derivatives
US06/627,139 US4556739A (en)	1983-09-29	1984-07-02	3,4-Dialkoxy-2-alkylcarbonyl analino compounds

Publications (1)

Publication Number	Publication Date
NO843908L true NO843908L (no)	1985-04-01

Family

ID=27065422

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO843908A NO843908L (no)	1983-09-29	1984-09-28	Fremgangsmaare for fremstilling av 4-alkyl-2(1h)-kinazolinon-1-alkansyrederivater

Country Status (7)

Country	Link
US (1)	US4556739A (de)
EP (1)	EP0138492A3 (de)
KR (1)	KR900001200B1 (de)
AU (1)	AU565001B2 (de)
DK (1)	DK468184A (de)
GR (1)	GR80505B (de)
NO (1)	NO843908L (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR900003529B1 (ko) *	1985-07-29	1990-05-21	오르토 파마슈티컬 코포레이션	2-아실-3,4-디알콕시아닐린의 제조방법
US4731480A (en) *	1985-07-29	1988-03-15	Ortho Pharmaceutical Corporation	Process for preparing 2-acyl-3,4-dialkoxyanilines
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1984
- 1984-07-02 US US06/627,139 patent/US4556739A/en not_active Expired - Lifetime
- 1984-09-28 GR GR80505A patent/GR80505B/el unknown
- 1984-09-28 NO NO843908A patent/NO843908L/no unknown
- 1984-09-28 KR KR1019840006008A patent/KR900001200B1/ko not_active Expired
- 1984-09-28 EP EP84306670A patent/EP0138492A3/de not_active Withdrawn
- 1984-09-28 DK DK468184A patent/DK468184A/da not_active Application Discontinuation
- 1984-09-28 AU AU33715/84A patent/AU565001B2/en not_active Ceased

Also Published As

Publication number	Publication date
DK468184A (da)	1985-03-30
EP0138492A3 (de)	1986-01-02
AU565001B2 (en)	1987-09-03
DK468184D0 (da)	1984-09-28
KR850002260A (ko)	1985-05-10
EP0138492A2 (de)	1985-04-24
US4556739A (en)	1985-12-03
GR80505B (en)	1985-01-30
KR900001200B1 (ko)	1990-02-28
AU3371584A (en)	1985-04-18

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