DD283394A5 - Verfahren zur herstellung von indilocarbazol-derivaten - Google Patents

Verfahren zur herstellung von indilocarbazol-derivaten Download PDF

Info

Publication number: DD283394A5
Authority: DD; German Democratic Republic
Prior art keywords: atoms; propyl; group; hydrogen; radicals
Prior art date: 1988-02-06

Application number

DD89325511A

Other languages

German (de)

English (en)

Inventor

Juergen Kleinschroth

Johannes Hartenstein

Hubert Barth

Christoph Schaechtele

Claus Rudolph

Guenter Weinheimer

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.)

1988-02-06

Filing date

1989-02-03

Publication date

1990-10-10

1989-02-03 Application filed by ��@��k�� filed Critical ��@��k��

1990-10-10 Publication of DD283394A5 publication Critical patent/DD283394A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 22
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 44
150000001875 compounds Chemical class 0.000 claims abstract description 42
239000001257 hydrogen Substances 0.000 claims abstract description 35
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 35
150000002431 hydrogen Chemical class 0.000 claims abstract description 24
VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 claims abstract description 16
125000000217 alkyl group Chemical group 0.000 claims abstract description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
238000002360 preparation method Methods 0.000 claims abstract description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 7
239000003814 drug Substances 0.000 claims abstract description 6
150000003839 salts Chemical class 0.000 claims abstract description 6
125000002252 acyl group Chemical group 0.000 claims abstract description 5
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 5
125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
125000002947 alkylene group Chemical group 0.000 claims abstract description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 3
-1 1,1-disubstituted 3-hydroxyazetidinium halide Chemical class 0.000 claims description 81
150000003254 radicals Chemical class 0.000 claims description 28
229960005544 indolocarbazole Drugs 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 8
208000024172 Cardiovascular disease Diseases 0.000 claims description 4
206010020751 Hypersensitivity Diseases 0.000 claims description 4
206010028980 Neoplasm Diseases 0.000 claims description 4
230000007815 allergy Effects 0.000 claims description 4
201000011510 cancer Diseases 0.000 claims description 4
210000003169 central nervous system Anatomy 0.000 claims description 4
230000003412 degenerative effect Effects 0.000 claims description 4
230000004054 inflammatory process Effects 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
DXGTUUQHTDOFFQ-UHFFFAOYSA-N [N].C1=CC=C2NC=CC2=C1 Chemical group [N].C1=CC=C2NC=CC2=C1 DXGTUUQHTDOFFQ-UHFFFAOYSA-N 0.000 claims description 3
238000005661 deetherification reaction Methods 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
150000003949 imides Chemical class 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
206010003210 Arteriosclerosis Diseases 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
206010020772 Hypertension Diseases 0.000 claims description 2
208000007536 Thrombosis Diseases 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
238000010640 amide synthesis reaction Methods 0.000 claims description 2
208000011775 arteriosclerosis disease Diseases 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical group 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 2
238000006722 reduction reaction Methods 0.000 claims description 2
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 19
229940079593 drug Drugs 0.000 abstract description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 33
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 24
239000013078 crystal Substances 0.000 description 20
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
239000012312 sodium hydride Substances 0.000 description 11
229910000104 sodium hydride Inorganic materials 0.000 description 11
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
239000002480 mineral oil Substances 0.000 description 8
235000010446 mineral oil Nutrition 0.000 description 8
102000003923 Protein Kinase C Human genes 0.000 description 7
108090000315 Protein Kinase C Proteins 0.000 description 7
GAAWKLUURLVNGE-UHFFFAOYSA-N pyrrolo[3,4-c]carbazole Chemical compound C1=CC=C2C3=C4C=NC=C4C=CC3=NC2=C1 GAAWKLUURLVNGE-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
239000012043 crude product Substances 0.000 description 6
239000011701 zinc Substances 0.000 description 6
229910052725 zinc Inorganic materials 0.000 description 6
229910000497 Amalgam Inorganic materials 0.000 description 5
239000007789 gas Substances 0.000 description 5
239000003112 inhibitor Substances 0.000 description 5
MEXUTNIFSHFQRG-UHFFFAOYSA-N 6,7,12,13-tetrahydro-5h-indolo[2,3-a]pyrrolo[3,4-c]carbazol-5-one Chemical compound C12=C3C=CC=C[C]3NC2=C2NC3=CC=C[CH]C3=C2C2=C1C(=O)NC2 MEXUTNIFSHFQRG-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
102000001253 Protein Kinase Human genes 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
108060006633 protein kinase Proteins 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
229930182474 N-glycoside Natural products 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
230000002152 alkylating effect Effects 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
230000000813 microbial effect Effects 0.000 description 2
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 1
ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
YKNYWLSBLXFZLP-UHFFFAOYSA-N 23-ethyl-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4,6,8,10,15,17,19,21-nonaen-12-one Chemical compound C1=CC=C2NC3=C4N(CC)C5=CC=CC=C5C4=C(CNC4=O)C4=C3C2=C1 YKNYWLSBLXFZLP-UHFFFAOYSA-N 0.000 description 1
NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 1
GZSUIHUAFPHZSU-UHFFFAOYSA-N 9-ethyl-2,3-dihydro-1h-carbazol-4-one Chemical compound C12=CC=CC=C2N(CC)C2=C1C(=O)CCC2 GZSUIHUAFPHZSU-UHFFFAOYSA-N 0.000 description 1
CHDFPGBOLATSAW-UHFFFAOYSA-N C1=CC=C2NC3=C4N(CC(O)CN(CC)CC)C5=CC=CC=C5C4=C(CNC4=O)C4=C3C2=C1 Chemical compound C1=CC=C2NC3=C4N(CC(O)CN(CC)CC)C5=CC=CC=C5C4=C(CNC4=O)C4=C3C2=C1 CHDFPGBOLATSAW-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 1
150000000996 L-ascorbic acids Chemical class 0.000 description 1
KAJXOWFGKYKMMZ-UHFFFAOYSA-N LSM-3627 Chemical compound C12=C3C=CC=C[C]3NC2=C2NC3=CC=C[CH]C3=C2C2=C1C(=O)NC2=O KAJXOWFGKYKMMZ-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
238000003556 assay Methods 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
150000001982 diacylglycerols Chemical class 0.000 description 1
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
229940008406 diethyl sulfate Drugs 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
230000031146 intracellular signal transduction Effects 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
150000003951 lactams Chemical group 0.000 description 1
150000002691 malonic acids Chemical class 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002900 organolithium compounds Chemical class 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003870 salicylic acids Chemical class 0.000 description 1
230000003248 secreting effect Effects 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
235000011044 succinic acid Nutrition 0.000 description 1
150000003444 succinic acids Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- 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
- C07D487/12—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 three hetero rings
- C07D487/14—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- 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
- 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
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- 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
- A61P9/12—Antihypertensives

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Immunology (AREA)
Diabetes (AREA)
Urology & Nephrology (AREA)
Hematology (AREA)
Pulmonology (AREA)
Vascular Medicine (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pain & Pain Management (AREA)
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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Indole Compounds (AREA)

DD89325511A 1988-02-06 1989-02-03 Verfahren zur herstellung von indilocarbazol-derivaten DD283394A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3803620A DE3803620A1 (de)	1988-02-06	1988-02-06	Indolocarbazol-derivate, verfahren zu deren herstellung und diese enthaltende arzneimittel

Publications (1)

Publication Number	Publication Date
DD283394A5 true DD283394A5 (de)	1990-10-10

Family

ID=6346797

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD89325511A DD283394A5 (de)	1988-02-06	1989-02-03	Verfahren zur herstellung von indilocarbazol-derivaten

Country Status (16)

Country	Link
EP (1)	EP0328000B1 (da)
JP (1)	JP2866096B2 (da)
KR (1)	KR890013035A (da)
CN (1)	CN1035667A (da)
AT (1)	ATE117304T1 (da)
AU (1)	AU616468B2 (da)
CA (1)	CA1337767C (da)
DD (1)	DD283394A5 (da)
DE (2)	DE3803620A1 (da)
DK (1)	DK51489A (da)
ES (1)	ES2066798T3 (da)
GR (1)	GR3015194T3 (da)
HU (1)	HU203758B (da)
IE (1)	IE65256B1 (da)
PT (1)	PT89623B (da)
ZA (1)	ZA89861B (da)

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JP3010675B2 (ja) *	1989-03-23	2000-02-21	萬有製薬株式会社	抗腫瘍性物質ｂｅ―１３７９３ｃ
US5618809A (en) *	1989-12-14	1997-04-08	Schering Corporation	Indolocarbazoles from saccharothrix aerocolonigenes copiosa subsp. nov SCC 1951 ATCC 53856
AU7035991A (en) *	1989-12-14	1991-07-18	Schering Corporation	Indolocarbazoles from saccharothrix aerocolonigenes subsp. copiosa subsp. nov. scc 1951 atcc 53856
DE3942296A1 (de) *	1989-12-21	1991-06-27	Goedecke Ag	Indolocarbazol-derivate, verfahren zu deren herstellung und deren verwendung
US5668271A (en) *	1991-11-29	1997-09-16	Banyu Pharmaceutical Co., Ltd.	Indolopyrrolocarbazole derivatives
US5591842A (en) *	1991-11-29	1997-01-07	Banyu Pharmaceutical Co., Ltd.	Indolopyrrolocarbazole derivatives
WO1993018766A1 (en) *	1992-03-20	1993-09-30	The Wellcome Foundation Limited	Further indole derivatives with antiviral activity
DE4243321A1 (de) *	1992-12-21	1994-06-23	Goedecke Ag	Aminosäurederivate von Heterocyclen als PKC-Inhibitoren
AU678435B2 (en) *	1993-05-10	1997-05-29	F. Hoffmann-La Roche Ag	Substituted pyrroles
US5721230A (en) *	1993-05-10	1998-02-24	Hoffmann-La Roche Inc.	Substituted pyrroles
EP0839814A3 (en) *	1993-05-28	1998-09-16	Cephalon, Inc.	Indolocarbazole derivatives and their use for the treatment of prostate gland disorders
US5468872A (en) *	1993-09-16	1995-11-21	Cephalon, Inc.	K-252a functional derivatives potentiate neurotrophin-3 for the treatment of neurological disorders
US5624949A (en) *	1993-12-07	1997-04-29	Eli Lilly And Company	Protein kinase C inhibitors
CA2137203C (en) *	1993-12-07	2006-11-28	William Francis Heath Jr.	Protein kinase c inhibitors
US5843935A (en) *	1993-12-07	1998-12-01	Eli Lilly And Company	Protein kinase C inhibitors
US5541347A (en) *	1993-12-07	1996-07-30	Eli Lilly And Company	Synthesis of bisindolylmaleimides
US5723456A (en) *	1993-12-07	1998-03-03	Eli Lilly & Company	Therapeutic treatment for cardiovascular diseases
DE69418978T2 (de) *	1993-12-07	1999-10-28	Eli Lilly And Co., Indianapolis	Synthese von Bisindolylmaleimiden
ATE456367T1 (de) *	1993-12-23	2010-02-15	Lilly Co Eli	Proteinkinase c inhibitoren
US5922860A (en) *	1994-05-09	1999-07-13	Banyu Pharmaceutical Co., Ltd.	Antitumor indolopyrrolocarbazole derivatives
US5804564A (en) *	1994-05-09	1998-09-08	Banyu Pharmaceutical Co., Ltd.	Antitumor indolopyrrolocarbazole derivatives
US5481003A (en) *	1994-06-22	1996-01-02	Eli Lilly And Company	Protein kinase C inhibitors
US5491242A (en) *	1994-06-22	1996-02-13	Eli Lilly And Company	Protein kinase C inhibitors
US5616724A (en) *	1996-02-21	1997-04-01	Cephalon, Inc.	Fused pyrrolo[2,3-c]carbazole-6-ones
AU758241B2 (en) *	1998-03-13	2003-03-20	University Of British Columbia, The	Granulatimide derivatives for use in cancer treatment
CA2245029A1 (en)	1998-03-13	1999-09-13	University Of British Columbia	Granulatimide compounds as g2 checkpoint inhibitors
US6653290B2 (en)	2000-10-06	2003-11-25	Bristol-Myers Squibb Company	Tumor proliferation inhibitors
EE200300456A (et)	2001-03-22	2004-02-16	Bristol-Myers Squibb Company	Indolopürrolokarbasoolide topoisomeraas I selektiivsed tsütotoksilised suhkruderivaadid ning nende kasutamine
CA2393720C (en)	2002-07-12	2010-09-14	Eli Lilly And Company	Crystalline 2,5-dione-3-(1-methyl-1h-indol-3-yl)-4-[1-(pyridin-2-ylmethyl)piperidin-4-yl]-1h-indol-3-yl]-1h-pyrrole mono-hydrochloride
CN117486782A (zh) *	2023-12-29	2024-02-02	中国医学科学院药用植物研究所	一种n-取代咔唑衍生物及其制备方法和应用

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US4737496A (en) *	1986-10-01	1988-04-12	Ciba-Geigy Corporation	1,3,4,16b-tetrahydro-2H,10H-indolo[2,1-c]pyrazino-[1,2-a][1,4]benzodiazepines useful as serotonin-2 receptor antagonists

1988
- 1988-02-06 DE DE3803620A patent/DE3803620A1/de not_active Withdrawn
1989
- 1989-02-03 EP EP89101940A patent/EP0328000B1/de not_active Expired - Lifetime
- 1989-02-03 AU AU29607/89A patent/AU616468B2/en not_active Ceased
- 1989-02-03 PT PT89623A patent/PT89623B/pt not_active IP Right Cessation
- 1989-02-03 ZA ZA89861A patent/ZA89861B/xx unknown
- 1989-02-03 IE IE35989A patent/IE65256B1/en not_active IP Right Cessation
- 1989-02-03 AT AT89101940T patent/ATE117304T1/de not_active IP Right Cessation
- 1989-02-03 HU HU89548A patent/HU203758B/hu not_active IP Right Cessation
- 1989-02-03 ES ES89101940T patent/ES2066798T3/es not_active Expired - Lifetime
- 1989-02-03 DD DD89325511A patent/DD283394A5/de not_active IP Right Cessation
- 1989-02-03 DE DE58908892T patent/DE58908892D1/de not_active Expired - Fee Related
- 1989-02-03 DK DK051489A patent/DK51489A/da not_active Application Discontinuation
- 1989-02-03 CA CA000590001A patent/CA1337767C/en not_active Expired - Fee Related
- 1989-02-04 KR KR1019890001349A patent/KR890013035A/ko not_active Withdrawn
- 1989-02-04 CN CN89100641A patent/CN1035667A/zh active Pending
- 1989-02-06 JP JP1027350A patent/JP2866096B2/ja not_active Expired - Fee Related
1995
- 1995-02-27 GR GR950400404T patent/GR3015194T3/el unknown

Also Published As

Publication number	Publication date
GR3015194T3 (en)	1995-05-31
JPH02149520A (ja)	1990-06-08
AU2960789A (en)	1989-08-10
PT89623A (pt)	1989-10-04
DE3803620A1 (de)	1989-08-17
EP0328000A2 (de)	1989-08-16
ATE117304T1 (de)	1995-02-15
ES2066798T3 (es)	1995-03-16
ZA89861B (en)	1989-11-29
IE890359L (en)	1989-08-06
DK51489D0 (da)	1989-02-03
HU203758B (en)	1991-09-30
CA1337767C (en)	1995-12-19
KR890013035A (ko)	1989-09-21
EP0328000B1 (de)	1995-01-18
PT89623B (pt)	1994-02-28
IE65256B1 (en)	1995-10-18
JP2866096B2 (ja)	1999-03-08
AU616468B2 (en)	1991-10-31
CN1035667A (zh)	1989-09-20
DE58908892D1 (de)	1995-03-02
DK51489A (da)	1989-08-07
EP0328000A3 (de)	1991-04-03

Legal Events

Date	Code	Title	Description
1996-06-20	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD283394A5 (de)	1990-10-10	Verfahren zur herstellung von indilocarbazol-derivaten
AT405283B (de)	1999-06-25	Neues kristallines 7-(z)-(2-(2-aminothiazol-4-yl) -2-hydroxyiminoacetamido)-3-vinyl-3-cephem-4- carbonsäure dicyclohexylammoniumsalz und verfahren zu dessen herstellung
DE2760372C2 (da)	1991-05-29
DE69533277T2 (de)	2005-07-21	Dc-89 derivat
DE2129675C3 (de)	1981-07-09	7-Methoxycephalosporinderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
EP0362695B1 (de)	1991-04-03	Pyrrolocarbazol-Derivate, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel
NZ241110A (en)	1994-04-27	7,8-methylenedioxy-n-acyl-2,3-benzodiazepine derivatives, preparation and pharmaceutical compositions thereof
EP0434057B1 (de)	1996-07-31	Indolocarbazol-Derivate, Verfahren zu deren Herstellung und deren Verwendung
DE3018590A1 (de)	1980-11-20	Bisester von methandiol mit penicillinen und penicillansaeure-1,1-dioxid
DE2609486C2 (da)	1988-11-03
EP0370236B1 (de)	1991-12-27	Indolocarbazol-Derivate, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel
AT394853B (de)	1992-07-10	Verfahren zur herstellung von neuen mitosanderivaten
DE69113284T2 (de)	1996-02-22	Chinolinderivat.
DE69322673T2 (de)	1999-05-06	Imidazopyridazine als Antiasthmatika
DE112005003752T5 (de)	2008-11-13	Neues Pyrrolo[2,1-c][1,4]benzodiapezinhybrid und ein Verfahren zu dessen Herstellung
DE3705934A1 (de)	1988-09-08	Indolyl-derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
EP0253171A1 (de)	1988-01-20	Pyrido [1,8] naphthyridinone, Verfahren zu ihrer Herstellung und ihre Verwendung sowie diese Verbindungen enthaltende Zubereitungen
DE69111640T2 (de)	1996-01-25	7-(Diphenylmethyl)oxy-9a-methoxymitosan, seine Herstellung und Verwendung.
DE2601473A1 (de)	1976-07-22	2,3-dihydroergoline und verfahren zu ihrer herstellung
WO1988008843A2 (en)	1988-11-17	New imidazols
NZ205669A (en)	1987-02-20	Anthracycline glycosides,intermediates,and pharmaceutical compositions
DE4217963A1 (de)	1993-12-02	Verwendung von Indolocarbazolen zur Behandlung von AIDS
DE60002891T2 (de)	2004-03-11	Streptograminderivate, ihre herstellung und sie enthaltende zubereitungen
DE2408666A1 (de)	1974-09-12	Antibiotische derivate und verfahren zu deren herstellung
DE69009765T2 (de)	1994-11-24	Kynurensäurederivate, deren herstellung und diese enthaltende pharmazeutische zusammensetzungen.