NO882085L - Cyklobutenmellomprodukt. - Google Patents

Cyklobutenmellomprodukt.

Info

Publication number: NO882085L
Authority: NO; Norway
Prior art keywords: formula; compound; cyclobutene; dione; mol
Prior art date: 1987-05-14

Application number

NO88882085A

Other languages

English (en)

Norwegian (no)

Other versions

NO882085D0 (no

Inventor

James L Douglas

Guy Fabre

Claude Demonsthene

Original Assignee

Bristol Myers Co

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.)

1987-05-14

Filing date

1988-05-13

Publication date

1988-11-15

1988-05-13 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1988-05-13 Publication of NO882085D0 publication Critical patent/NO882085D0/no

1988-11-15 Publication of NO882085L publication Critical patent/NO882085L/no

Links

125000000217 alkyl group Chemical group 0.000 claims abstract description 20
-1 pyrrolidino, methylpyrrolidino, piperidino, methylpiperidino Chemical group 0.000 claims abstract description 13
239000003054 catalyst Substances 0.000 claims abstract description 8
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 6
239000003960 organic solvent Substances 0.000 claims abstract description 5
150000001412 amines Chemical class 0.000 claims abstract description 4
231100000252 nontoxic Toxicity 0.000 claims abstract description 3
230000003000 nontoxic effect Effects 0.000 claims abstract description 3
150000003839 salts Chemical class 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 73
238000000034 method Methods 0.000 claims description 12
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
239000007983 Tris buffer Substances 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
UDYGXWPMSJPFDG-UHFFFAOYSA-M benzyl(tributyl)azanium;bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 UDYGXWPMSJPFDG-UHFFFAOYSA-M 0.000 claims description 3
229910052736 halogen Chemical group 0.000 claims description 3
150000002367 halogens Chemical group 0.000 claims description 3
QWCGXANSAOXRFE-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanamine Chemical compound COCCOCCN QWCGXANSAOXRFE-UHFFFAOYSA-N 0.000 claims description 2
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
IULJSGIJJZZUMF-UHFFFAOYSA-N 2-hydroxybenzenesulfonic acid Chemical group OC1=CC=CC=C1S(O)(=O)=O IULJSGIJJZZUMF-UHFFFAOYSA-N 0.000 claims 1
KSBYXRUNSLGUNE-UHFFFAOYSA-N 3-amino-4-[3-[3-(piperidin-1-ylmethyl)phenoxy]propylamino]cyclobut-3-ene-1,2-dione Chemical compound O=C1C(=O)C(N)=C1NCCCOC1=CC=CC(CN2CCCCC2)=C1 KSBYXRUNSLGUNE-UHFFFAOYSA-N 0.000 claims 1
239000000376 reactant Substances 0.000 claims 1
CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 0.000 abstract 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
239000012442 inert solvent Substances 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
239000000243 solution Substances 0.000 description 48
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 42
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
239000000203 mixture Substances 0.000 description 36
238000003756 stirring Methods 0.000 description 29
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 23
239000007787 solid Substances 0.000 description 23
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 22
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
238000001914 filtration Methods 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
238000010992 reflux Methods 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
229910000027 potassium carbonate Inorganic materials 0.000 description 9
235000011181 potassium carbonates Nutrition 0.000 description 9
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
238000001816 cooling Methods 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
239000010410 layer Substances 0.000 description 7
239000000843 powder Substances 0.000 description 7
PQIYSSSTRHVOBW-UHFFFAOYSA-N 3-bromopropan-1-amine;hydron;bromide Chemical compound Br.NCCCBr PQIYSSSTRHVOBW-UHFFFAOYSA-N 0.000 description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
235000011114 ammonium hydroxide Nutrition 0.000 description 6
239000012141 concentrate Substances 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
239000005909 Kieselgur Substances 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
239000002002 slurry Substances 0.000 description 5
PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 description 5
239000000725 suspension Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
RLSQIOZFIPIWAP-UHFFFAOYSA-N 3-(3-bromopropylamino)-4-butoxycyclobut-3-ene-1,2-dione Chemical compound CCCCOC1=C(NCCCBr)C(=O)C1=O RLSQIOZFIPIWAP-UHFFFAOYSA-N 0.000 description 4
ZTGQZSKPSJUEBU-UHFFFAOYSA-N 3-bromopropan-1-amine Chemical compound NCCCBr ZTGQZSKPSJUEBU-UHFFFAOYSA-N 0.000 description 4
IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000000908 ammonium hydroxide Substances 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
229960001340 histamine Drugs 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
239000003921 oil Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
XBRWELTXMQSEIN-UHFFFAOYSA-N squaric acid dibutyl ester Chemical compound CCCCOC1=C(OCCCC)C(=O)C1=O XBRWELTXMQSEIN-UHFFFAOYSA-N 0.000 description 4
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000005557 antagonist Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000003485 histamine H2 receptor antagonist Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000013067 intermediate product Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
WFDUPHCVSSKDFW-UHFFFAOYSA-N 3-(3-bromopropylamino)-4-(2,2-dimethylpropoxy)cyclobut-3-ene-1,2-dione Chemical compound CC(C)(C)COC1=C(NCCCBr)C(=O)C1=O WFDUPHCVSSKDFW-UHFFFAOYSA-N 0.000 description 2
UVZLPEXKMCUKDY-UHFFFAOYSA-N 3-butoxy-4-(3-hydroxypropylamino)cyclobut-3-ene-1,2-dione Chemical compound CCCCOC1=C(NCCCO)C(=O)C1=O UVZLPEXKMCUKDY-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-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
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
229940122957 Histamine H2 receptor antagonist Drugs 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
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
208000008469 Peptic Ulcer Diseases 0.000 description 2
WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000012267 brine Substances 0.000 description 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000000284 extract Substances 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 2
239000011698 potassium fluoride Substances 0.000 description 2
235000003270 potassium fluoride Nutrition 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
235000017550 sodium carbonate Nutrition 0.000 description 2
235000009518 sodium iodide Nutrition 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
230000003595 spectral effect Effects 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
BCRQVSRWRCLQRV-UHFFFAOYSA-N 1,2-dichloroethane;hydrate Chemical compound O.ClCCCl BCRQVSRWRCLQRV-UHFFFAOYSA-N 0.000 description 1
125000002817 1-piperidinomethyl group Chemical group [H]C([H])([*])N1C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
BHKFGQPSAJDECE-UHFFFAOYSA-N 3-(3-bromopropylamino)-4-(2-methylpropoxy)cyclobut-3-ene-1,2-dione Chemical compound CC(C)COC1=C(NCCCBr)C(=O)C1=O BHKFGQPSAJDECE-UHFFFAOYSA-N 0.000 description 1
ORGBERFQYFWYGX-UHFFFAOYSA-N 3-(piperidin-1-ylmethyl)phenol Chemical compound OC1=CC=CC(CN2CCCCC2)=C1 ORGBERFQYFWYGX-UHFFFAOYSA-N 0.000 description 1
YWJNJCYEGUSUCK-UHFFFAOYSA-N 3-[3-(benzenesulfonyl)propylamino]-4-butoxycyclobut-3-ene-1,2-dione Chemical compound O=C1C(=O)C(OCCCC)=C1NCCCS(=O)(=O)C1=CC=CC=C1 YWJNJCYEGUSUCK-UHFFFAOYSA-N 0.000 description 1
BCFLXSGCJYZLCU-UHFFFAOYSA-N 3-amino-4-[3-[3-(piperidin-1-ylmethyl)phenoxy]propylamino]cyclobut-3-ene-1,2-dione;hydrochloride Chemical compound Cl.O=C1C(=O)C(N)=C1NCCCOC1=CC=CC(CN2CCCCC2)=C1 BCFLXSGCJYZLCU-UHFFFAOYSA-N 0.000 description 1
KMMHZIBWCXYAAH-UHFFFAOYSA-N 4-bromobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(Br)C=C1 KMMHZIBWCXYAAH-UHFFFAOYSA-N 0.000 description 1
JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
241000400611 Eucalyptus deanei Species 0.000 description 1
244000166102 Eucalyptus leucoxylon Species 0.000 description 1
235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical group [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
239000002876 beta blocker Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000013078 crystal Substances 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000000295 fuel oil Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical group BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
ZMNRQTFKKWTKRA-UHFFFAOYSA-N n,3-dibromopropan-1-amine Chemical compound BrCCCNBr ZMNRQTFKKWTKRA-UHFFFAOYSA-N 0.000 description 1
125000006606 n-butoxy group Chemical group 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
230000037361 pathway Effects 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
208000011906 peptic ulcer disease Diseases 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
229940093956 potassium carbonate Drugs 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/20—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the carbon skeleton
- 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
- C07D295/08—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 bound oxygen or sulfur atoms
- C07D295/096—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Steroid Compounds (AREA)
Physical Or Chemical Processes And Apparatus (AREA)
Fats And Perfumes (AREA)
Compositions Of Macromolecular Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Plural Heterocyclic Compounds (AREA)
Macromonomer-Based Addition Polymer (AREA)
Inks, Pencil-Leads, Or Crayons (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO88882085A 1987-05-14 1988-05-13 Cyklobutenmellomprodukt. NO882085L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US5067087A	1987-05-14	1987-05-14
US07/174,443 US4927970A (en)	1987-05-14	1988-04-11	Substituted 3-cyclobutene-1,2-dione intermediates

Publications (2)

Publication Number	Publication Date
NO882085D0 NO882085D0 (no)	1988-05-13
NO882085L true NO882085L (no)	1988-11-15

Family

ID=26728514

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO88882085A NO882085L (no)	1987-05-14	1988-05-13	Cyklobutenmellomprodukt.

Country Status (23)

Country	Link
US (1)	US4927970A (de)
EP (1)	EP0294615B1 (de)
JP (1)	JPS6470448A (de)
KR (1)	KR960008663B1 (de)
CN (1)	CN1025187C (de)
AT (1)	ATE74904T1 (de)
AU (1)	AU612146B2 (de)
CA (1)	CA1301753C (de)
DE (1)	DE3870038D1 (de)
DK (1)	DK263988A (de)
EG (1)	EG18604A (de)
ES (1)	ES2031551T3 (de)
FI (1)	FI882255A (de)
GR (1)	GR3004388T3 (de)
HU (2)	HU207835B (de)
IE (1)	IE61576B1 (de)
IL (1)	IL86342A (de)
MY (1)	MY103523A (de)
NO (1)	NO882085L (de)
NZ (1)	NZ224609A (de)
PT (1)	PT87480B (de)
ZA (1)	ZA883163B (de)
ZW (1)	ZW5388A1 (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5168103A (en) *	1991-01-22	1992-12-01	American Home Products Corporation	[[2-(amino-3,4-dioxo-1-cyclobuten-1-yl) amino]alkyl]-acid derivatives
US5231190A (en)	1991-05-06	1993-07-27	Polaroid Corporation	Squarylium compounds, and processes and intermediates for the synthesis of these compounds
KR100742086B1 (ko) *	2001-07-27	2007-07-23	주식회사유한양행	4-페닐-3-사이클로부텐-1,2-다이온 유도체 및 그의 제조방법
CN112321534A (zh) *	2020-11-13	2021-02-05	哈药集团技术中心	一种高纯度药用盐酸罗沙替丁醋酸酯的制备方法

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1518660A1 (de) *	1965-07-09	1969-08-14	Huels Chemische Werke Ag	Verfahren zur Herstellung aminosubstituierter Dioxocyclobutene
NL7603598A (nl) *	1975-04-18	1976-10-20	Ciba Geigy	Werkwijze voor het bereiden van preparaten voor het beinvloeden van de plantegroei alsmede de toepassing daarvan.
US4522943A (en) *	1981-05-18	1985-06-11	Bristol-Myers Company	Chemical compounds
US4390701A (en) *	1981-05-18	1983-06-28	Bristol-Myers Company	1-Amino-2-[3-(3-piperidinomethylphenoxy)propylamino]cyclobutene-3,4-dione
US4395553A (en) *	1981-05-18	1983-07-26	Bristol-Myers Company	Chemical compounds
US4788184A (en) *	1981-05-18	1988-11-29	Bristol-Myers Company	Substituted 3-cyclobutene-1,2-diones as anti-ulcer agents
US4526973A (en) *	1981-05-18	1985-07-02	Bristol-Myers Company	Chemical compounds
AU1956283A (en) *	1982-10-02	1984-04-05	Smith Kline & French Laboratories Limited	1-(3-(4-(substited aminomethyl)pyrid-2-yl-oxy)-prop-1-yl- amino) - 2-aminocyclobut-i-ene-3,4-diones
DE3408327A1 (de) *	1984-03-07	1985-09-12	Ludwig Heumann & Co GmbH, 8500 Nürnberg	Diaminderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel

1988
- 1988-04-11 US US07/174,443 patent/US4927970A/en not_active Expired - Fee Related
- 1988-05-04 ZW ZW53/88A patent/ZW5388A1/xx unknown
- 1988-05-04 ZA ZA883163A patent/ZA883163B/xx unknown
- 1988-05-11 IL IL86342A patent/IL86342A/xx unknown
- 1988-05-12 EG EG261/88A patent/EG18604A/xx active
- 1988-05-13 EP EP88107741A patent/EP0294615B1/de not_active Expired - Lifetime
- 1988-05-13 NZ NZ224609A patent/NZ224609A/en unknown
- 1988-05-13 CA CA000566730A patent/CA1301753C/en not_active Expired - Lifetime
- 1988-05-13 PT PT87480A patent/PT87480B/pt not_active IP Right Cessation
- 1988-05-13 HU HU882405A patent/HU207835B/hu unknown
- 1988-05-13 DE DE8888107741T patent/DE3870038D1/de not_active Expired - Fee Related
- 1988-05-13 DK DK263988A patent/DK263988A/da not_active Application Discontinuation
- 1988-05-13 IE IE145888A patent/IE61576B1/en not_active IP Right Cessation
- 1988-05-13 ES ES198888107741T patent/ES2031551T3/es not_active Expired - Lifetime
- 1988-05-13 HU HU92584A patent/HUT62258A/hu unknown
- 1988-05-13 AT AT88107741T patent/ATE74904T1/de not_active IP Right Cessation
- 1988-05-13 MY MYPI88000504A patent/MY103523A/en unknown
- 1988-05-13 FI FI882255A patent/FI882255A/fi not_active Application Discontinuation
- 1988-05-13 NO NO88882085A patent/NO882085L/no unknown
- 1988-05-13 AU AU16153/88A patent/AU612146B2/en not_active Ceased
- 1988-05-14 JP JP63118048A patent/JPS6470448A/ja active Pending
- 1988-05-14 KR KR1019880005691A patent/KR960008663B1/ko active IP Right Grant
- 1988-05-14 CN CN88102844A patent/CN1025187C/zh not_active Expired - Fee Related
1992
- 1992-04-16 GR GR920400557T patent/GR3004388T3/el unknown

Also Published As

Publication number	Publication date
KR960008663B1 (ko)	1996-06-28
ES2031551T3 (es)	1992-12-16
NO882085D0 (no)	1988-05-13
DE3870038D1 (de)	1992-05-21
EP0294615B1 (de)	1992-04-15
IL86342A0 (en)	1988-11-15
HUT50087A (en)	1989-12-28
IE881458L (en)	1988-11-14
DK263988D0 (da)	1988-05-13
GR3004388T3 (de)	1993-03-31
US4927970A (en)	1990-05-22
ZW5388A1 (en)	1989-05-31
PT87480B (pt)	1992-09-30
HUT62258A (en)	1993-04-28
HU207835B (en)	1993-06-28
FI882255A0 (fi)	1988-05-13
DK263988A (da)	1988-11-15
KR880013876A (ko)	1988-12-22
FI882255A (fi)	1988-11-15
IL86342A (en)	1992-03-29
MY103523A (en)	1993-07-31
ATE74904T1 (de)	1992-05-15
ZA883163B (en)	1990-03-28
NZ224609A (en)	1991-06-25
CN1025187C (zh)	1994-06-29
EP0294615A1 (de)	1988-12-14
AU612146B2 (en)	1991-07-04
PT87480A (pt)	1989-05-31
EG18604A (en)	1993-08-30
AU1615388A (en)	1988-11-17
HU9200584D0 (en)	1992-05-28
CA1301753C (en)	1992-05-26
CN1031076A (zh)	1989-02-15
JPS6470448A (en)	1989-03-15
IE61576B1 (en)	1994-11-16

Publication	Publication Date	Title
DK1797037T3 (en)	2015-03-30	PROCESS FOR THE PREPARATION OF 4- {4 - [({[4-chloro-3- (trifluoromethyl) phenyl] AMINO} CARBONYL) AMINO] PHENYOXY} N-methylpyridine-2-carboxamide
US4254031A (en)	1981-03-03	Synthesis for the preparation of tetracyclic compounds
NO882085L (no)	1988-11-15	Cyklobutenmellomprodukt.
JPS634544B2 (de)	1988-01-29
NO166712B (no)	1991-05-21	Fremgangsmaate ved fremstilling av pyrrolidonderivater.
NO151387B (no)	1984-12-17	Innstillingsinnretning for en elektronisk digitalindikator
US4217452A (en)	1980-08-12	Synthesis for the preparation of tetracyclic compounds
US4108894A (en)	1978-08-22	Amidines
NO147838B (no)	1983-03-14	Mellomprodukt til bruk ved fremstilling av det hypotensive middel 2-(4-(2-furoyl)piperazin-1-yl)-4-amino-6,7-dimetoksykinazolin
CZ294957B6 (cs)	2005-04-13	Způsob přípravy substituované imidazopyridinové sloučeniny
KR20020052213A (ko)	2002-07-02	6-메틸-2-(4-메틸-페닐)-이미다조[1,2-ａ]피리미딘-3-(Ｎ,Ｎ-디메틸-아세트아미드) 및 중간체의 제조 방법
KR100377782B1 (ko)	2003-03-29	발기부전 치료에 효과를 갖는 피라졸로피리미디논화합물의 제조방법
EP0090275B1 (de)	1987-10-28	Isoxazole (5,4-b) Pyridine
JP2001521498A (ja)	2001-11-06	Ｏ−（３−アミノ−２−ヒドロキシ−プロピル）−ヒドロキシミック酸ハロゲン化物の製造方法
EP3915984A1 (de)	2021-12-01	Synthese von 3-brom-5-(2-ethylimidazo[1,2-alpha]pyridin-3-carbonyl)-2-hydroxybenzonitril
JPH02289563A (ja)	1990-11-29	ｏ―カルボキシピリジル―およびｏ―カルボキシキノリルイミダゾリノンの改良製造法
JPH07285920A (ja)	1995-10-31	新規なアミノカルボン酸エステル及びその製法
US4118501A (en)	1978-10-03	Thiazolidine derivatives
HU217445B (hu)	2000-01-28	Eljárás 2-{4-[4-(4-klór-1-pirazolil)-butil]-1-piperazinil}-pirimidin előállítására
CN109988172B (zh)	2020-09-29	一种吡唑并[1,5-a]嘧啶类杂环化合物及衍生物的合成方法
US4156735A (en)	1979-05-29	Thiazolidine derivatives
US5952494A (en)	1999-09-14	Method for the preparation of pyrido benzoxazine derivatives
HU195485B (en)	1988-05-30	Process for producing aromatic carboxylic acid derivatives and -carboxamide derivatives
SU1056904A3 (ru)	1983-11-23	Способ получени производных 1,4-диазепина
KR850000742B1 (ko)	1985-05-24	티아졸린 유도체의 제조방법