DD253821A5 - Verfahren zur herstellung von pyrrolo-benzimidozolen, pyrrolo-benzooxazolen und pyrrolo-benzthiozole - Google Patents

Verfahren zur herstellung von pyrrolo-benzimidozolen, pyrrolo-benzooxazolen und pyrrolo-benzthiozole Download PDF

Info

Publication number: DD253821A5
Authority: DD; German Democratic Republic
Prior art keywords: group; pyrrolo; compounds; dihydro; methyl
Prior art date: 1985-09-05

Application number

DD86294089A

Other languages

German (de)

English (en)

Inventor

Wolfgang Von Der Saal

Alfred Mertens

Herbert Berger

Bernd Mueller-Beckmann

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.)

1985-09-05

Filing date

1986-09-02

Publication date

1988-02-03

1986-09-02 Application filed by ��@��@��k�� filed Critical ��@��@��k��

1988-02-03 Publication of DD253821A5 publication Critical patent/DD253821A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 14
238000002360 preparation method Methods 0.000 title abstract description 8
QINMCBGMCSLFML-UHFFFAOYSA-N 2h-pyrrolo[2,3-g][1,2]benzoxazole Chemical compound C1=CC2=CNOC2=C2C=CN=C12 QINMCBGMCSLFML-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 110
-1 amino, pyridylcarbonylamino Chemical group 0.000 claims abstract description 76
125000000217 alkyl group Chemical group 0.000 claims abstract description 24
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
239000001257 hydrogen Substances 0.000 claims abstract description 21
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
125000003342 alkenyl group Chemical group 0.000 claims abstract description 13
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
150000003839 salts Chemical class 0.000 claims abstract description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
239000001301 oxygen Substances 0.000 claims abstract description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
239000011593 sulfur Chemical group 0.000 claims abstract description 7
125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 6
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 6
150000007522 mineralic acids Chemical class 0.000 claims abstract description 6
150000007524 organic acids Chemical class 0.000 claims abstract description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 5
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 5
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 5
125000004181 carboxyalkyl group Chemical group 0.000 claims abstract description 5
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims abstract description 5
235000005985 organic acids Nutrition 0.000 claims abstract description 5
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 4
125000001118 alkylidene group Chemical group 0.000 claims abstract description 4
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 4
125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims abstract description 3
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims abstract 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
125000004430 oxygen atom Chemical group O* 0.000 claims description 11
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
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 description 5
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
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 claims description 4
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
150000001408 amides Chemical class 0.000 claims description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 3
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
238000005595 Hinsberg synthesis reaction Methods 0.000 claims description 2
238000005778 Stolle synthesis reaction Methods 0.000 claims description 2
230000015572 biosynthetic process Effects 0.000 claims description 2
125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
238000003786 synthesis reaction Methods 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 37
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 abstract description 3
125000002993 cycloalkylene group Chemical group 0.000 abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
239000002904 solvent Substances 0.000 description 25
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
238000002844 melting Methods 0.000 description 20
230000008018 melting Effects 0.000 description 20
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
239000000126 substance Substances 0.000 description 14
239000000706 filtrate Substances 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 10
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
HHDYSDWIZLXLDU-UHFFFAOYSA-N 5,6-diamino-3,3-dimethyl-1h-indol-2-one Chemical compound NC1=C(N)C=C2C(C)(C)C(=O)NC2=C1 HHDYSDWIZLXLDU-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
235000011114 ammonium hydroxide Nutrition 0.000 description 9
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 8
229920000137 polyphosphoric acid Polymers 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
HXEXZNSKKSBTJR-UHFFFAOYSA-N 5h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound C=1C2=NC=NC2=CC2=CC(=O)NC2=1 HXEXZNSKKSBTJR-UHFFFAOYSA-N 0.000 description 7
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 7
229960000583 acetic acid Drugs 0.000 description 7
238000009835 boiling Methods 0.000 description 7
239000003610 charcoal Substances 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
JYZIHLWOWKMNNX-UHFFFAOYSA-N benzimidazole Chemical compound C1=C[CH]C2=NC=NC2=C1 JYZIHLWOWKMNNX-UHFFFAOYSA-N 0.000 description 6
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
239000013078 crystal Substances 0.000 description 6
238000002425 crystallisation Methods 0.000 description 6
230000008025 crystallization Effects 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
239000012362 glacial acetic acid Substances 0.000 description 6
238000000746 purification Methods 0.000 description 6
238000007363 ring formation reaction Methods 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 5
238000001914 filtration Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
125000004434 sulfur atom Chemical group 0.000 description 5
238000011282 treatment Methods 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000012043 crude product Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000005457 ice water Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
208000024172 Cardiovascular disease Diseases 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
150000001733 carboxylic acid esters Chemical class 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000003814 drug Substances 0.000 description 3
230000032050 esterification Effects 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 3
238000011321 prophylaxis Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
RYOIZJJJQVKSQQ-UHFFFAOYSA-N 2h-pyrrolo[2,3-g][1,3]benzothiazole Chemical class C1=CC2=NCSC2=C2C=CN=C21 RYOIZJJJQVKSQQ-UHFFFAOYSA-N 0.000 description 2
PXITYTUBKOKYBD-UHFFFAOYSA-N 2h-pyrrolo[2,3-g][1,3]benzoxazole Chemical class C1=CC2=NCOC2=C2C=CN=C21 PXITYTUBKOKYBD-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
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 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
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
230000003213 activating effect Effects 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
239000000654 additive Substances 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
238000006136 alcoholysis reaction Methods 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
150000003973 alkyl amines Chemical class 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 2
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
238000006114 decarboxylation reaction Methods 0.000 description 2
239000012024 dehydrating agents‎ Substances 0.000 description 2
239000003480 eluent Substances 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
229920006158 high molecular weight polymer Polymers 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 2
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 2
239000007788 liquid 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
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
150000004682 monohydrates Chemical class 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
BKOVMXWXILSWCU-UHFFFAOYSA-N pyrrolo[3,2-e]benzimidazole Chemical class C1=CC2=NC=CC2=C2N=CN=C21 BKOVMXWXILSWCU-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
239000011877 solvent mixture Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
238000001665 trituration Methods 0.000 description 2
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
MCDFFISWJNZPNB-UHFFFAOYSA-N 1,4-diamino-3,3-dimethylindol-2-one Chemical compound NC1=C2C(C(N(C2=CC=C1)N)=O)(C)C MCDFFISWJNZPNB-UHFFFAOYSA-N 0.000 description 1
MJXGXBJFWUTCCE-UHFFFAOYSA-N 1,7,7-trimethyl-3,5-dihydropyrrolo[3,2-f]benzimidazole-2,6-dione Chemical compound C1=C2N(C)C(O)=NC2=CC2=C1C(C)(C)C(=O)N2 MJXGXBJFWUTCCE-UHFFFAOYSA-N 0.000 description 1
IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical class C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 description 1
GVTSHWPIZMVHHT-UHFFFAOYSA-N 2,7,7-trimethyl-1,5-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=C2NC(C)=NC2=CC2=C1NC(=O)C2(C)C GVTSHWPIZMVHHT-UHFFFAOYSA-N 0.000 description 1
AHRFXVFYYUAYGO-UHFFFAOYSA-N 2-(1,1,2,2,3,3,3-heptafluoropropyl)-7,7-dimethyl-1,5-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=C2C(C)(C)C(=O)NC2=CC2=C1NC(C(F)(F)C(F)(F)C(F)(F)F)=N2 AHRFXVFYYUAYGO-UHFFFAOYSA-N 0.000 description 1
CBIUVXLSJSQEHG-UHFFFAOYSA-N 2-(cyclopenten-1-yl)-7,7-dimethyl-1,5-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3C(C)(C)C(=O)NC3=CC=2NC=1C1=CCCC1 CBIUVXLSJSQEHG-UHFFFAOYSA-N 0.000 description 1
LBZOSMJCFLDNFA-UHFFFAOYSA-N 2-(methoxymethyl)-7,7-dimethyl-1,5-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=C2NC(COC)=NC2=CC2=C1NC(=O)C2(C)C LBZOSMJCFLDNFA-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
LUQBTNNXFKMUBM-UHFFFAOYSA-N 2-amino-7,7-dimethyl-1,5-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=C2C(C)(C)C(=O)NC2=CC2=C1N=C(N)N2 LUQBTNNXFKMUBM-UHFFFAOYSA-N 0.000 description 1
XTFSGCZAYGDWTC-UHFFFAOYSA-N 2-but-1-enyl-7,7-dimethyl-1,5-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=C2NC(C=CCC)=NC2=CC2=C1C(C)(C)C(=O)N2 XTFSGCZAYGDWTC-UHFFFAOYSA-N 0.000 description 1
SODVIRHQUWZJLV-UHFFFAOYSA-N 2-cyclohexyl-7-methyl-5,7-dihydro-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3C(C)C(=O)NC3=CC=2NC=1C1CCCCC1 SODVIRHQUWZJLV-UHFFFAOYSA-N 0.000 description 1
QVRZZLJIQYTGRF-UHFFFAOYSA-N 2-cyclopropyl-7,7-dimethyl-1,5-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound N1C=2C=C3C(C)(C)C(=O)NC3=CC=2N=C1C1CC1 QVRZZLJIQYTGRF-UHFFFAOYSA-N 0.000 description 1
IQQIIPCAOOITCP-UHFFFAOYSA-N 2-hexyl-7,7-dimethyl-1,5-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=C2NC(CCCCCC)=NC2=CC2=C1NC(=O)C2(C)C IQQIIPCAOOITCP-UHFFFAOYSA-N 0.000 description 1
LDUNJIVICZFTQG-UHFFFAOYSA-N 2-hydroxy-7,7-dimethyl-3,5-dihydro-2h-pyrrolo[2,3-f][1,3]benzoxazol-6-one Chemical compound C1=C2C(C)(C)C(=O)NC2=CC2=C1OC(O)N2 LDUNJIVICZFTQG-UHFFFAOYSA-N 0.000 description 1
HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
YIIULBVJZYQZDI-UHFFFAOYSA-N 2-nitro-1h-indol-3-amine Chemical class C1=CC=C2C(N)=C([N+]([O-])=O)NC2=C1 YIIULBVJZYQZDI-UHFFFAOYSA-N 0.000 description 1
UMGWGVRJXVCEBC-UHFFFAOYSA-N 2-tert-butyl-7,7-dimethyl-1,5-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=C2NC(C(C)(C)C)=NC2=CC2=C1C(C)(C)C(=O)N2 UMGWGVRJXVCEBC-UHFFFAOYSA-N 0.000 description 1
WBRPJXHHMCCDIB-UHFFFAOYSA-N 3-(7,7-dimethyl-6-oxo-1,5-dihydropyrrolo[2,3-f]benzimidazol-2-yl)propanoic acid Chemical compound C1=C2C(C)(C)C(=O)NC2=CC2=C1N=C(CCC(O)=O)N2 WBRPJXHHMCCDIB-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 1
ZOVMPRCOSCRRQQ-UHFFFAOYSA-N 5,6-diamino-3-ethyl-1,3-dihydroindol-2-one Chemical compound NC1=C(N)C=C2C(CC)C(=O)NC2=C1 ZOVMPRCOSCRRQQ-UHFFFAOYSA-N 0.000 description 1
MXMXPPXQNNGWBE-UHFFFAOYSA-N 5,6-diamino-3-methyl-1,3-dihydroindol-2-one Chemical compound NC1=C(N)C=C2C(C)C(=O)NC2=C1 MXMXPPXQNNGWBE-UHFFFAOYSA-N 0.000 description 1
PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
GLGSULOUMYONRR-UHFFFAOYSA-N 5-hydroxy-3,3-dimethyl-6-nitro-1h-indol-2-one Chemical compound [O-][N+](=O)C1=C(O)C=C2C(C)(C)C(=O)NC2=C1 GLGSULOUMYONRR-UHFFFAOYSA-N 0.000 description 1
OGMFMOAQNCBVSE-UHFFFAOYSA-N 5H-pyrrolo[2,3-f]benzimidazol-2-one Chemical compound N=1C(N=C2C=1C=C1C(=C2)NC=C1)=O OGMFMOAQNCBVSE-UHFFFAOYSA-N 0.000 description 1
ITOVEWUTBNNZNE-UHFFFAOYSA-N 6-amino-3,3-dimethyl-5-(methylamino)-1h-indol-2-one Chemical compound C1=C(N)C(NC)=CC2=C1NC(=O)C2(C)C ITOVEWUTBNNZNE-UHFFFAOYSA-N 0.000 description 1
KJIGCHMEHQYGPA-UHFFFAOYSA-N 6-amino-3,3-dimethyl-5-nitro-1h-indol-2-one Chemical compound NC1=C([N+]([O-])=O)C=C2C(C)(C)C(=O)NC2=C1 KJIGCHMEHQYGPA-UHFFFAOYSA-N 0.000 description 1
JNSPFAZNJTWRSG-UHFFFAOYSA-N 7,7-dimethyl-1,5-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=C2C(C)(C)C(=O)NC2=CC2=C1NC=N2 JNSPFAZNJTWRSG-UHFFFAOYSA-N 0.000 description 1
ZUCNVXRXIVITJH-UHFFFAOYSA-N 7,7-dimethyl-2-(trifluoromethyl)-1,5-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=C2C(C)(C)C(=O)NC2=CC2=C1N=C(C(F)(F)F)N2 ZUCNVXRXIVITJH-UHFFFAOYSA-N 0.000 description 1
AIBNJOHKUJUGAK-UHFFFAOYSA-N 7,7-dimethyl-2-methylsulfanyl-1,5-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=C2NC(SC)=NC2=CC2=C1NC(=O)C2(C)C AIBNJOHKUJUGAK-UHFFFAOYSA-N 0.000 description 1
LXWRAORBASKIQA-UHFFFAOYSA-N 7,7-dimethyl-2-prop-1-enyl-1,5-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=C2NC(C=CC)=NC2=CC2=C1NC(=O)C2(C)C LXWRAORBASKIQA-UHFFFAOYSA-N 0.000 description 1
QYCOOFYFHRHZER-UHFFFAOYSA-N 7,7-dimethyl-2-propan-2-yl-1,5-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=C2NC(C(C)C)=NC2=CC2=C1NC(=O)C2(C)C QYCOOFYFHRHZER-UHFFFAOYSA-N 0.000 description 1
JMEFBVPJQROQMS-UHFFFAOYSA-N 7,7-dimethyl-3,5-dihydro-1h-pyrrolo[2,3-f]benzimidazole-2,6-dione Chemical compound C1=C2C(C)(C)C(=O)NC2=CC2=C1N=C(O)N2 JMEFBVPJQROQMS-UHFFFAOYSA-N 0.000 description 1
YWTFUKMNASONKT-UHFFFAOYSA-N 7,7-dimethyl-3,5-dihydropyrrolo[2,3-f][1,3]benzothiazole-2,6-dione;2,7,7-trimethyl-5h-pyrrolo[2,3-f][1,3]benzothiazol-6-one Chemical compound C1=C2SC(C)=NC2=CC2=C1C(C)(C)C(=O)N2.C1=C2C(C)(C)C(=O)NC2=CC2=C1SC(=O)N2 YWTFUKMNASONKT-UHFFFAOYSA-N 0.000 description 1
QQNVHGWZCKLMAI-UHFFFAOYSA-N 7-acetyl-2,7-dimethyl-1,5-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=C2C(C(=O)C)(C)C(=O)NC2=CC2=C1N=C(C)N2 QQNVHGWZCKLMAI-UHFFFAOYSA-N 0.000 description 1
GGJPTSMKAVKSKG-UHFFFAOYSA-N 7-acetyl-2-methyl-5,7-dihydro-1h-pyrrolo[2,3-f]benzimidazol-6-one;2-methyl-5,7-dihydro-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=C2NC(C)=NC2=CC2=C1CC(=O)N2.C1=C2C(C(=O)C)C(=O)NC2=CC2=C1NC(C)=N2 GGJPTSMKAVKSKG-UHFFFAOYSA-N 0.000 description 1
KBJHOXJZQJZGSC-UHFFFAOYSA-N 7-acetyl-7-methyl-1,5-dihydropyrrolo[2,3-f]benzimidazol-6-one ethyl 7-methyl-6-oxo-1,5-dihydropyrrolo[2,3-f]benzimidazole-7-carboxylate Chemical compound C(C)OC(=O)C1(C(NC2=CC3=C(N=CN3)C=C21)=O)C.C(C)(=O)C2(C(NC1=CC3=C(N=CN3)C=C12)=O)C KBJHOXJZQJZGSC-UHFFFAOYSA-N 0.000 description 1
CVJFTJSWBTYPCO-UHFFFAOYSA-N 7-cyclohexyl-2-methyl-5,7-dihydro-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound O=C1NC=2C=C3NC(C)=NC3=CC=2C1C1CCCCC1 CVJFTJSWBTYPCO-UHFFFAOYSA-N 0.000 description 1
VYWCWIIRMCRPBN-UHFFFAOYSA-N 7-ethyl-1,3,5,7-tetrahydropyrrolo[2,3-f]benzimidazole-2,6-dione Chemical compound C1=C2C(CC)C(=O)NC2=CC2=C1NC(=O)N2 VYWCWIIRMCRPBN-UHFFFAOYSA-N 0.000 description 1
WDLKAKPOSZOFGQ-UHFFFAOYSA-N 7-ethyl-2-(trifluoromethyl)-5,7-dihydro-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=C2C(CC)C(=O)NC2=CC2=C1N=C(C(F)(F)F)N2 WDLKAKPOSZOFGQ-UHFFFAOYSA-N 0.000 description 1
NQIAKXRWXAQTCC-UHFFFAOYSA-N 7-ethyl-2-sulfanylidene-1,3,5,7-tetrahydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=C2C(CC)C(=O)NC2=CC2=C1N=C(S)N2 NQIAKXRWXAQTCC-UHFFFAOYSA-N 0.000 description 1
MJSXSOHPNJFPLU-UHFFFAOYSA-N 7-methyl-1,3,5,7-tetrahydropyrrolo[2,3-f]benzimidazole-2,6-dione Chemical compound C1=C2C(C)C(=O)NC2=CC2=C1N=C(O)N2 MJSXSOHPNJFPLU-UHFFFAOYSA-N 0.000 description 1
BUKFEHROBREHTD-UHFFFAOYSA-N 7-methyl-2-propyl-5,7-dihydro-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=C2NC(CCC)=NC2=CC2=C1NC(=O)C2C BUKFEHROBREHTD-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
241000206672 Gelidium Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
229920000388 Polyphosphate Polymers 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
238000007083 alkoxycarbonylation reaction Methods 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
229940054051 antipsychotic indole derivative Drugs 0.000 description 1
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
150000004650 carbonic acid diesters Chemical class 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000007979 citrate buffer Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000008139 complexing agent Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
PWAPCRSSMCLZHG-UHFFFAOYSA-N cyclopentylidene Chemical group [C]1CCCC1 PWAPCRSSMCLZHG-UHFFFAOYSA-N 0.000 description 1
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000469 ethanolic extract Substances 0.000 description 1
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
ZQFAFEJBCKYXPC-UHFFFAOYSA-N ethyl 3-(7,7-dimethyl-6-oxo-1,5-dihydropyrrolo[2,3-f]benzimidazol-2-yl)propanoate Chemical compound C1=C2NC(CCC(=O)OCC)=NC2=CC2=C1NC(=O)C2(C)C ZQFAFEJBCKYXPC-UHFFFAOYSA-N 0.000 description 1
WLTGMCFICZPZSG-UHFFFAOYSA-N ethyl 7-methyl-2-methylsulfanyl-6-oxo-1,5-dihydropyrrolo[2,3-f]benzimidazole-7-carboxylate Chemical compound C1=C2C(C(=O)OCC)(C)C(=O)NC2=CC2=C1N=C(SC)N2 WLTGMCFICZPZSG-UHFFFAOYSA-N 0.000 description 1
UAKVNXIRJKFKBU-UHFFFAOYSA-N ethyl 7-methyl-6-oxo-2-propan-2-yl-1,5-dihydropyrrolo[2,3-f]benzimidazole-7-carboxylate Chemical compound C1=C2C(C(=O)OCC)(C)C(=O)NC2=CC2=C1N=C(C(C)C)N2 UAKVNXIRJKFKBU-UHFFFAOYSA-N 0.000 description 1
PHROYRXVXAERSS-UHFFFAOYSA-N ethyl 7-methyl-6-oxo-2-propyl-1,5-dihydropyrrolo[2,3-f]benzimidazole-7-carboxylate Chemical compound C1=C2NC(CCC)=NC2=CC2=C1C(C)(C(=O)OCC)C(=O)N2 PHROYRXVXAERSS-UHFFFAOYSA-N 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000011790 ferrous sulphate Substances 0.000 description 1
235000003891 ferrous sulphate Nutrition 0.000 description 1
238000005187 foaming Methods 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
229910021485 fumed silica Inorganic materials 0.000 description 1
230000004927 fusion Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
125000006343 heptafluoro propyl group Chemical group 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
150000002475 indoles Chemical class 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
239000008101 lactose Substances 0.000 description 1
CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
230000004089 microcirculation Effects 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 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
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
150000007530 organic bases Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229960005489 paracetamol Drugs 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
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 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001205 polyphosphate Substances 0.000 description 1
235000011176 polyphosphates Nutrition 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000047 product Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
XVVXNXGBJNXJNU-UHFFFAOYSA-N pyridine-4-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.OC(=O)C1=CC=NC=C1 XVVXNXGBJNXJNU-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000002002 slurry Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 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
235000012222 talc Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
239000011135 tin Substances 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
238000005809 transesterification reaction Methods 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
235000019871 vegetable fat Nutrition 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/10—Spiro-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Heart & Thoracic Surgery (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Indole Compounds (AREA)
External Artificial Organs (AREA)
Lubricants (AREA)
Adhesives Or Adhesive Processes (AREA)

DD86294089A 1985-09-05 1986-09-02 Verfahren zur herstellung von pyrrolo-benzimidozolen, pyrrolo-benzooxazolen und pyrrolo-benzthiozole DD253821A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19853531678 DE3531678A1 (de)	1985-09-05	1985-09-05	Neue pyrrolo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel

Publications (1)

Publication Number	Publication Date
DD253821A5 true DD253821A5 (de)	1988-02-03

Family

ID=6280182

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86294089A DD253821A5 (de)	1985-09-05	1986-09-02	Verfahren zur herstellung von pyrrolo-benzimidozolen, pyrrolo-benzooxazolen und pyrrolo-benzthiozole

Country Status (17)

Country	Link
US (1)	US4730003A (da)
EP (1)	EP0214592B1 (da)
JP (1)	JPS6259279A (da)
KR (1)	KR870003109A (da)
AT (1)	ATE66230T1 (da)
AU (1)	AU584235B2 (da)
DD (1)	DD253821A5 (da)
DE (2)	DE3531678A1 (da)
DK (1)	DK418986A (da)
ES (1)	ES2001774A6 (da)
FI (1)	FI863565A7 (da)
GR (1)	GR862247B (da)
HU (1)	HU197010B (da)
IL (1)	IL79910A (da)
NZ (1)	NZ217418A (da)
PT (1)	PT83309B (da)
ZA (1)	ZA866704B (da)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
DE3642315A1 (de) *	1986-12-11	1988-06-23	Boehringer Mannheim Gmbh	Neue pyrrolobenzimidazole, verfahren zu ihrer herstellung sowie arzneimittel
DE3740985A1 (de) *	1987-12-03	1989-06-15	Boehringer Mannheim Gmbh	Verwendung linear anellierter tricyclen als hemmer der erythrozytenaggregation
US4963677A (en) *	1987-12-30	1990-10-16	Orion Corporation Ltd.	Heterocyclic lactam compounds
DE3855327D1 (de) *	1987-12-30	1996-07-04	Orion Yhtymae Oy	Heterocyclische Verbindungen
DE3809868A1 (de) *	1988-03-24	1989-10-05	Boehringer Mannheim Gmbh	Neue heterocyclisch substituierte 5,7-dihydro-pyrrolo(3,2-f)benzoxazol-6-one, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel
DE4027592A1 (de) *	1990-08-31	1992-03-05	Beiersdorf Ag	Neue pyrrolobenzimidazole, imidazobenzoxazinone und imidazochinolone, verfahren zu ihrer herstellung und ihre verwendung sowie die verbindungen enthaltende zubereitungen
KR20010108024A (ko)	1998-12-17	2001-12-07	프리돌린 클라우스너, 롤란드 비. 보레르	단백질 키나제 억제제로서의 4,5-피라진옥신돌
US6153634A (en) *	1998-12-17	2000-11-28	Hoffmann-La Roche Inc.	4,5-azolo-oxindoles
EP1598353A1 (en) *	2004-05-17	2005-11-23	Boehringer Ingelheim International GmbH	Pyrrolobenzimidazolones and their use as antiproliferative agents
CN102140099A (zh) *	2010-02-02	2011-08-03	山东轩竹医药科技有限公司	新的吡啶衍生物
PL3241879T3 (pl)	2014-09-25	2020-12-14	Daikin Industries, Ltd.	Kompozycja zawierająca HFC i HFO

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GR65025B (en) *	1977-07-21	1980-06-16	Thomae Gmbh Dr K	Method for the preparation of new imidazo-isokinolin-diones
DE3410168A1 (de) *	1984-03-20	1985-09-26	Boehringer Mannheim Gmbh, 6800 Mannheim	Neue isochinolin-dione, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel sowie zwischenprodukte
GR851085B (da) *	1984-05-12	1985-11-25	Boehringer Mannheim Gmbh
HU203350B (en) *	1984-08-24	1991-07-29	Pfizer	Process for producing antiinflammatory tricyclic oxindole derivatives
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
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
DE3639466A1 (de) *	1986-11-18	1988-05-19	Thomae Gmbh Dr K	Neue pyrrolo-benzimidazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung

1985
- 1985-09-05 DE DE19853531678 patent/DE3531678A1/de not_active Withdrawn
1986
- 1986-09-01 IL IL79910A patent/IL79910A/xx unknown
- 1986-09-01 NZ NZ217418A patent/NZ217418A/xx unknown
- 1986-09-02 DE DE8686112093T patent/DE3680845D1/de not_active Expired - Lifetime
- 1986-09-02 DD DD86294089A patent/DD253821A5/de not_active IP Right Cessation
- 1986-09-02 AT AT86112093T patent/ATE66230T1/de not_active IP Right Cessation
- 1986-09-02 EP EP86112093A patent/EP0214592B1/de not_active Expired - Lifetime
- 1986-09-02 DK DK418986A patent/DK418986A/da not_active Application Discontinuation
- 1986-09-02 GR GR862247A patent/GR862247B/el unknown
- 1986-09-02 AU AU62165/86A patent/AU584235B2/en not_active Ceased
- 1986-09-04 FI FI863565A patent/FI863565A7/fi not_active Application Discontinuation
- 1986-09-04 HU HU863827A patent/HU197010B/hu not_active IP Right Cessation
- 1986-09-04 US US06/904,094 patent/US4730003A/en not_active Expired - Fee Related
- 1986-09-04 ZA ZA866704A patent/ZA866704B/xx unknown
- 1986-09-04 PT PT83309A patent/PT83309B/pt unknown
- 1986-09-05 KR KR1019860007439A patent/KR870003109A/ko not_active Withdrawn
- 1986-09-05 JP JP61208117A patent/JPS6259279A/ja active Pending
- 1986-09-05 ES ES8601647A patent/ES2001774A6/es not_active Expired

Also Published As

Publication number	Publication date
PT83309A (de)	1986-10-01
FI863565A7 (fi)	1987-03-06
PT83309B (de)	1988-01-11
ZA866704B (en)	1987-05-27
AU6216586A (en)	1987-03-12
NZ217418A (en)	1988-11-29
ES2001774A6 (es)	1988-06-16
EP0214592A2 (de)	1987-03-18
DE3531678A1 (de)	1987-03-12
HUT42770A (en)	1987-08-28
HU197010B (en)	1989-02-28
KR870003109A (ko)	1987-04-15
EP0214592A3 (en)	1988-07-06
DK418986D0 (da)	1986-09-02
DE3680845D1 (de)	1991-09-19
GR862247B (en)	1986-12-31
AU584235B2 (en)	1989-05-18
ATE66230T1 (de)	1991-08-15
DK418986A (da)	1987-03-06
US4730003A (en)	1988-03-08
FI863565A0 (fi)	1986-09-04
IL79910A (en)	1990-02-09
IL79910A0 (en)	1986-12-31
EP0214592B1 (de)	1991-08-14
JPS6259279A (ja)	1987-03-14

Legal Events

Date	Code	Title	Description
1995-07-06	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0161632B1 (de)	1991-04-10	Neue Pyrrolo-Benzimidazole, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel sowie Zwischenprodukte
EP0362695B1 (de)	1991-04-03	Pyrrolocarbazol-Derivate, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel
DE3935514A1 (de)	1991-05-02	Neue bicyclo-imidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
EP0496753A1 (de)	1992-08-05	2-bicyclo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
EP0275888B1 (de)	1994-04-06	Neue tricyclische Benzimidazole, Verfahren zu ihrer Herstellung und Verwendung als Arzneimittel
EP0189103B1 (de)	1991-01-02	Neue Pyrrolo-Benzimidazole, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel sowie Zwischenprodukte
EP0327986A2 (de)	1989-08-16	Arzeneimittel enthaltend Lactame, neue substituierte Lactame und Verfahren zu ihrer Herstellung
EP0271040A2 (de)	1988-06-15	Neue Pyrrolobenzimidazole, Verfahren zu ihrer Herstellung, sowie Arzneimittel
EP0186010B1 (de)	1990-01-31	Neue Pyrrolo-Benzimidazole, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DD253821A5 (de)	1988-02-03	Verfahren zur herstellung von pyrrolo-benzimidozolen, pyrrolo-benzooxazolen und pyrrolo-benzthiozole
EP0180834B1 (de)	1989-08-30	4-Alkoxy-pyrido[2,3-d]pyrimidin-Derivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
HUT72666A (en)	1996-05-28	5,6-dihydro-4h-imidazo[2',1':2,3]imidazo[4,5,1-ij]quinoline and 4,5-dihydroimidazo[1,2-a]pyrrolo[1,2,3-cd]benzimidazol derivatives, process for producing them and pharmaceutical composition containing them
US4801590A (en)	1989-01-31	Pyrido(1,8)naphthyridinones, and their use as pharmaceuticals
US4372956A (en)	1983-02-08	5, 10-Dihydroimidazo[2,1-b]quinazolines and pharmaceutical compositions containing them
US4578397A (en)	1986-03-25	Indeno(1,2-b)pyrrole derivatives
EP0334289A1 (de)	1989-09-27	Heterocyclisch substituierte 5,7-Dihydro-pyrrolo[3,2-f]benzoxazol-6-one, Verfahren zu ihrer Herstellung sowie diese Verbindungen enthaltende Arzneimittel
EP0257334B1 (de)	1991-01-02	Tricyclische Benzotriazole, Verfahren zu ihrer Herstellung sowie Arzneimittel
US3423412A (en)	1969-01-21	Benzopyrroloquinazolinones
US4762828A (en)	1988-08-09	1,2,4-triazolo[4,3-d]-4-azatricyclo-[4.3.1.13,8 ]undecane and 3-substituted derivatives, and intermediates thereof
DE3446417A1 (de)	1986-06-26	Neue pyrrolo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel sowie zwischenprodukte
DD234867A5 (de)	1986-04-16	Neue pyrrolo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel sowie zwischenprodukte