DD283376A5 - Verfahren zur herstellung von lactamen - Google Patents

Verfahren zur herstellung von lactamen Download PDF

Info

Publication number: DD283376A5
Authority: DD; German Democratic Republic
Prior art keywords: group; alkyl; dimethyl; dihydro; alkoxy
Prior art date: 1988-02-09

Application number

DD89325587A

Other languages

German (de)

English (en)

Inventor

Harald Zilch

Alfred Mertens

Wolfgang Von Der Saal

Erwin Boehm

Klaus Strein

Original Assignee

��@��@��k��

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.)

1988-02-09

Filing date

1989-02-07

Publication date

1990-10-10

1989-02-07 Application filed by ��@��@��k�� filed Critical ��@��@��k��

1990-10-10 Publication of DD283376A5 publication Critical patent/DD283376A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 18
230000008569 process Effects 0.000 title claims abstract description 13
238000002360 preparation method Methods 0.000 title claims abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 52
150000003951 lactams Chemical class 0.000 claims abstract description 11
150000003839 salts Chemical class 0.000 claims abstract description 7
239000003814 drug Substances 0.000 claims abstract description 6
210000003743 erythrocyte Anatomy 0.000 claims abstract description 6
208000010110 spontaneous platelet aggregation Diseases 0.000 claims abstract description 6
150000001412 amines Chemical class 0.000 claims abstract description 3
238000004519 manufacturing process Methods 0.000 claims abstract 3
-1 trifluoromethanesulfonylamino Chemical group 0.000 claims description 210
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 26
JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 26
125000000217 alkyl group Chemical group 0.000 claims description 21
125000004432 carbon atom Chemical group C* 0.000 claims description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
239000004202 carbamide Substances 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 14
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
125000001424 substituent group Chemical group 0.000 claims description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 13
125000000623 heterocyclic group Chemical group 0.000 claims description 12
125000004093 cyano group Chemical group *C#N 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
125000005842 heteroatom Chemical group 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
125000003282 alkyl amino group Chemical group 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 claims description 4
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
230000002776 aggregation Effects 0.000 claims description 3
238000004220 aggregation Methods 0.000 claims description 3
125000003302 alkenyloxy group Chemical group 0.000 claims description 3
125000006598 aminocarbonylamino group Chemical group 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 3
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 3
239000012948 isocyanate Substances 0.000 claims description 3
150000002513 isocyanates Chemical class 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
229930192474 thiophene Natural products 0.000 claims description 3
125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 claims description 3
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 2
AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims description 2
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims description 2
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
125000005133 alkynyloxy group Chemical group 0.000 claims description 2
150000008064 anhydrides Chemical class 0.000 claims description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
230000002401 inhibitory effect Effects 0.000 claims description 2
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
150000003536 tetrazoles Chemical class 0.000 claims description 2
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 2
150000003852 triazoles Chemical class 0.000 claims description 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
239000000546 pharmaceutical excipient Substances 0.000 claims 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 1
JTSFIVQMXUDGAB-UHFFFAOYSA-N 4-thiomorpholin-4-ylmorpholine Chemical group C1COCCN1N1CCSCC1 JTSFIVQMXUDGAB-UHFFFAOYSA-N 0.000 claims 1
125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims 1
125000000392 cycloalkenyl group Chemical group 0.000 claims 1
125000002883 imidazolyl group Chemical group 0.000 claims 1
229940124531 pharmaceutical excipient Drugs 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 abstract description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 4
238000003786 synthesis reaction Methods 0.000 abstract description 4
201000010099 disease Diseases 0.000 abstract description 2
229940079593 drug Drugs 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
235000013877 carbamide Nutrition 0.000 description 14
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
238000006243 chemical reaction Methods 0.000 description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 9
125000004663 dialkyl amino group Chemical group 0.000 description 9
239000002904 solvent Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000000243 solution Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
JOQLZZBYKRJVBI-UHFFFAOYSA-N 1,3,4,5-tetrahydroindol-2-one Chemical compound C1=CCCC2=C1NC(=O)C2 JOQLZZBYKRJVBI-UHFFFAOYSA-N 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
239000012442 inert solvent Substances 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 4
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 4
239000013078 crystal Substances 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 3
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
RKJUIXBNRJVNHR-UHFFFAOYSA-N 3H-indole Chemical compound C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
125000005336 allyloxy group Chemical group 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
ITBHTNDFALMIRV-UHFFFAOYSA-N (3,3-dimethyl-2-oxo-1h-indol-6-yl)urea Chemical compound NC(=O)NC1=CC=C2C(C)(C)C(=O)NC2=C1 ITBHTNDFALMIRV-UHFFFAOYSA-N 0.000 description 2
125000006730 (C2-C5) alkynyl group Chemical group 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 2
BDUBTLFQHNYXPC-UHFFFAOYSA-N 3-methylbut-2-enoyl chloride Chemical compound CC(C)=CC(Cl)=O BDUBTLFQHNYXPC-UHFFFAOYSA-N 0.000 description 2
NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 description 2
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
238000007126 N-alkylation reaction Methods 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
AYVGBNGTBQLJBG-UHFFFAOYSA-N [3-(hydroxymethyl)cyclopentyl]methanol Chemical compound OCC1CCC(CO)C1 AYVGBNGTBQLJBG-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000003806 alkyl carbonyl amino group Chemical group 0.000 description 2
125000005196 alkyl carbonyloxy group Chemical group 0.000 description 2
125000004644 alkyl sulfinyl group Chemical group 0.000 description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
125000004656 alkyl sulfonylamino group Chemical group 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
230000003412 degenerative effect Effects 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
239000003480 eluent Substances 0.000 description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
150000002366 halogen compounds Chemical class 0.000 description 2
229920006158 high molecular weight polymer Polymers 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
239000005457 ice water Substances 0.000 description 2
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000463 material Substances 0.000 description 2
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 2
NNSIHVXUFLYMPU-UHFFFAOYSA-N n-(4,4-dimethyl-2-oxo-1,3-dihydroquinolin-7-yl)-3-ethoxyprop-2-enamide Chemical compound N1C(=O)CC(C)(C)C=2C1=CC(NC(=O)C=COCC)=CC=2 NNSIHVXUFLYMPU-UHFFFAOYSA-N 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
230000007017 scission Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 2
150000003672 ureas Chemical class 0.000 description 2
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MSYVMUIGTNPISO-UHFFFAOYSA-N n-(4,4-dimethyl-2-oxo-1,3-dihydroquinolin-7-yl)quinoline-4-carboxamide Chemical compound C1=CC=C2C(C(=O)NC=3C=C4NC(=O)CC(C4=CC=3)(C)C)=CC=NC2=C1 MSYVMUIGTNPISO-UHFFFAOYSA-N 0.000 description 1
230000001338 necrotic effect Effects 0.000 description 1
210000005036 nerve Anatomy 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
150000005623 oxindoles Chemical class 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
230000008506 pathogenesis Effects 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
MDHYEMXUFSJLGV-UHFFFAOYSA-N phenethyl acetate Chemical compound CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
MRPCKYWPLOEBQR-UHFFFAOYSA-N phenyl n-(3,3-dimethyl-2-oxo-1h-indol-6-yl)carbamate Chemical compound C=1C=C2C(C)(C)C(=O)NC2=CC=1NC(=O)OC1=CC=CC=C1 MRPCKYWPLOEBQR-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 description 1
125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
210000001525 retina Anatomy 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000035939 shock Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
150000004867 thiadiazoles Chemical class 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
208000019553 vascular disease Diseases 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
201000002282 venous insufficiency Diseases 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/54—Spiro-condensed
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Diabetes (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Hematology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Quinoline Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

DD89325587A 1988-02-09 1989-02-07 Verfahren zur herstellung von lactamen DD283376A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3803775A DE3803775A1 (de)	1988-02-09	1988-02-09	Neue substituierte lactame, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten

Publications (1)

Publication Number	Publication Date
DD283376A5 true DD283376A5 (de)	1990-10-10

Family

ID=6346898

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD89325587A DD283376A5 (de)	1988-02-09	1989-02-07	Verfahren zur herstellung von lactamen

Country Status (14)

Country	Link
US (2)	US4985448A (ja)
EP (1)	EP0327986A3 (ja)
JP (1)	JPH01250352A (ja)
KR (1)	KR890012966A (ja)
AU (1)	AU617760B2 (ja)
DD (1)	DD283376A5 (ja)
DE (1)	DE3803775A1 (ja)
DK (1)	DK49289A (ja)
FI (1)	FI890605A7 (ja)
HU (1)	HUT50118A (ja)
IL (1)	IL89192A0 (ja)
NZ (1)	NZ227868A (ja)
PT (1)	PT89655B (ja)
ZA (1)	ZA89958B (ja)

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DE3803775A1 (de) *	1988-02-09	1989-08-17	Boehringer Mannheim Gmbh	Neue substituierte lactame, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten
US5076835A (en) *	1990-05-31	1991-12-31	America Cyanamid Company	Aryloxyspiroalkylindolinone herbicides
DE4021063A1 (de) *	1990-07-03	1992-01-09	Boehringer Mannheim Gmbh	Neue ss-galactosidase-substrate fuer den cedia
BR9200951A (pt) *	1991-03-21	1992-11-17	Hoffmann La Roche	Compostos, processo para sua producao,preparacoes farmaceuticas e uso
DE69429584T2 (de) *	1993-11-26	2002-08-08	Tanabe Seiyaku Co., Ltd.	2-oxoindolin-derivate als cholecystokinin rezeptor antagonisten
US5565483A (en) *	1995-06-07	1996-10-15	Bristol-Myers Squibb Company	3-substituted oxindole derivatives as potassium channel modulators
DE19727117A1 (de)	1997-06-26	1999-01-07	Boehringer Ingelheim Pharma	Phenylalkylderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
AU9309898A (en) *	1997-09-09	1999-03-29	Du Pont Pharmaceuticals Company	Benzimidazolinones, benzoxazolinones, benzopiperazinones, indanones, and derivatives thereof as inhibitors of factor xa
WO2000000475A1 (en) *	1998-06-30	2000-01-06	Du Pont Pharmaceuticals Company	Substituted quinolin-2(1h)-ones useful as hiv reverse transcriptase inhibitors
CA2338804A1 (en) *	1998-07-28	2000-02-10	Smithkline Beecham Corporation	Propenamides as ccr5 modulators
JP2002523455A (ja)	1998-08-31	2002-07-30	スージェン・インコーポレーテッド	蛋白質キナーゼ活性の調節剤としての幾何学的に制限された２−インドリノン誘導体
US6566372B1 (en) *	1999-08-27	2003-05-20	Ligand Pharmaceuticals Incorporated	Bicyclic androgen and progesterone receptor modulator compounds and methods
US6586460B1 (en) *	2001-04-02	2003-07-01	The Board Of Regents For Oklahoma State University	Heteroarotinoids containing urea or thiourea linker
JP2005518371A (ja) *	2001-12-10	2005-06-23	アムジエン・インコーポレーテツド	バニロイド受容体リガンド及び治療に於けるこれらの使用
CA2553968A1 (en) *	2004-01-23	2005-08-11	Amgen Inc.	Vanilloid receptor ligands and their use in treatments of inflammatory and neuropathic pain
US20060142247A1 (en) *	2004-12-17	2006-06-29	Guy Georges	Tricyclic heterocycles
KR20070113286A (ko) *	2005-04-14	2007-11-28	에프. 호프만-라 로슈 아게	아미노피라졸 유도체, 이의 제조 및 약학 제제로서의 용도
DE602006002887D1 (de) *	2005-04-14	2008-11-06	Hoffmann La Roche	Tricyclische azolderivate, ihre herstellung und ihre verwendung als pharmazeutische mittel
JP2009530337A (ja) *	2006-03-23	2009-08-27	エフ．ホフマン−ラロシュアーゲー	置換インダゾール誘導体、その製造方法、及びその薬剤としての利用法
KR101706877B1 (ko)	2012-09-13	2017-02-15	에프. 호프만-라 로슈 아게	Cns 장애의 치료를 위한 2-옥소-2,3-다이하이드로-인돌
JP6759514B2 (ja)	2014-08-01	2020-09-23	ヌエヴォリューション・アクティーゼルスカブＮｕｅｖｏｌｕｔｉｏｎＡ／Ｓ	ブロモドメインに対して活性な化合物
CN105085492A (zh) *	2015-09-29	2015-11-25	青岛友诚高新技术有限公司	一种可用于制备治疗冠状动脉粥样硬化药物的化合物及其制备方法、用途
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DE3445669A1 (de) *	1984-12-14	1986-06-19	Boehringer Mannheim Gmbh, 6800 Mannheim	Neue pyrrolo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
JPS61145162A (ja) *	1984-12-19	1986-07-02	Otsuka Pharmaceut Co Ltd	カルボスチリル誘導体
DE3501497A1 (de) *	1985-01-18	1986-07-24	Boehringer Mannheim Gmbh, 6800 Mannheim	Neue pyrrolo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel sowie zwischenprodukte
JPS6232459A (ja) *	1985-08-05	1987-02-12	Fuji Photo Film Co Ltd	ハロゲン化銀カラ−写真感光材料
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DE3803775A1 (de) *	1988-02-09	1989-08-17	Boehringer Mannheim Gmbh	Neue substituierte lactame, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten
DE3818830A1 (de) *	1988-06-03	1989-12-14	Boehringer Mannheim Gmbh	Bicyclische carboxamide, verfahren zu ihrer herstellung, deren vorstufen, und diese verbindungen enthaltende arzneimittel

1988
- 1988-02-09 DE DE3803775A patent/DE3803775A1/de not_active Withdrawn
1989
- 1989-02-02 DK DK049289A patent/DK49289A/da not_active Application Discontinuation
- 1989-02-03 EP EP19890101868 patent/EP0327986A3/de not_active Withdrawn
- 1989-02-06 IL IL89192A patent/IL89192A0/xx unknown
- 1989-02-06 US US07/307,417 patent/US4985448A/en not_active Expired - Fee Related
- 1989-02-07 NZ NZ227868A patent/NZ227868A/en unknown
- 1989-02-07 DD DD89325587A patent/DD283376A5/de not_active IP Right Cessation
- 1989-02-07 HU HU89578A patent/HUT50118A/hu unknown
- 1989-02-08 PT PT89655A patent/PT89655B/pt active IP Right Grant
- 1989-02-08 FI FI890605A patent/FI890605A7/fi not_active Application Discontinuation
- 1989-02-08 ZA ZA89958A patent/ZA89958B/xx unknown
- 1989-02-08 AU AU29741/89A patent/AU617760B2/en not_active Expired - Fee Related
- 1989-02-09 JP JP1028819A patent/JPH01250352A/ja active Pending
- 1989-02-09 KR KR1019890001486A patent/KR890012966A/ko not_active Withdrawn
1991
- 1991-01-11 US US07/640,445 patent/US5373019A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP0327986A3 (de)	1992-01-08
HUT50118A (en)	1989-12-28
EP0327986A2 (de)	1989-08-16
DE3803775A1 (de)	1989-08-17
US5373019A (en)	1994-12-13
US4985448A (en)	1991-01-15
PT89655A (pt)	1989-10-04
DK49289D0 (da)	1989-02-02
IL89192A0 (en)	1989-09-10
FI890605A0 (fi)	1989-02-08
NZ227868A (en)	1991-03-26
KR890012966A (ko)	1989-09-20
ZA89958B (en)	1989-10-25
AU2974189A (en)	1989-08-10
AU617760B2 (en)	1991-12-05
FI890605A7 (fi)	1989-08-10
DK49289A (da)	1989-08-10
JPH01250352A (ja)	1989-10-05
PT89655B (pt)	1994-02-28

Legal Events

Date	Code	Title	Description
1995-08-17	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD283376A5 (de)	1990-10-10	Verfahren zur herstellung von lactamen
DE69433353T2 (de)	2004-09-09	Bicyclische, heterocyclische sulfonamide und sulfonsäureester
DE3935514A1 (de)	1991-05-02	Neue bicyclo-imidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE69818831T2 (de)	2004-07-29	Indolderivate als mcp-1 rezeptor antagonisten
DE69920732T2 (de)	2006-02-23	Bicyclische stickstoffheteroaryl verbindungen
EP0275888B1 (de)	1994-04-06	Neue tricyclische Benzimidazole, Verfahren zu ihrer Herstellung und Verwendung als Arzneimittel
DE3932953A1 (de)	1991-04-11	Neue 2-bicyclo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
EP0189103B1 (de)	1991-01-02	Neue Pyrrolo-Benzimidazole, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel sowie Zwischenprodukte
EP0344634B1 (de)	1994-03-30	Bicyclische Carboxamide, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
EP0647231B1 (de)	1997-08-27	N-substituierte 3-azabicyclo[3.2.0]heptan-derivate als neuroleptika usw.
DE3634066A1 (de)	1988-04-21	Neue 5-alkylbenzimidazole, verfahren zu ihrer herstellung sowie arzneimittel
EP0271040A2 (de)	1988-06-15	Neue Pyrrolobenzimidazole, Verfahren zu ihrer Herstellung, sowie Arzneimittel
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EP0216165A1 (de)	1987-04-01	Neue Benzodipyrrole, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
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