DD284004A5 - Verfahren zur herstellung von biarylverbindungen - Google Patents

Verfahren zur herstellung von biarylverbindungen Download PDF

Info

Publication number: DD284004A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; radicals; compounds; independently; lower alkyl
Prior art date: 1988-07-07

Application number

DD89330468A

Other languages

German (de)

English (en)

Inventor

Jaroslav Stanek

Giorgio Caravatti

Joerg Frei

Hans-Georg Capraro

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.)

1988-07-07

Filing date

1989-07-05

Publication date

1990-10-31

1989-07-05 Application filed by ��`��@��k�� filed Critical ��`��@��k��

1990-10-31 Publication of DD284004A5 publication Critical patent/DD284004A5/de

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-1 BIARYL COMPOUNDS Chemical class 0.000 title claims abstract description 35
238000000034 method Methods 0.000 title claims description 20
230000008569 process Effects 0.000 title claims description 7
238000004519 manufacturing process Methods 0.000 title abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 114
238000002360 preparation method Methods 0.000 claims abstract description 12
150000003839 salts Chemical class 0.000 claims description 37
125000000217 alkyl group Chemical group 0.000 claims description 25
229910052739 hydrogen Inorganic materials 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 24
150000002431 hydrogen Chemical class 0.000 claims description 14
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
125000002947 alkylene group Chemical group 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
239000000463 material Substances 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
YYMQJGIRGGDLAL-UHFFFAOYSA-N 4-(2-carbamimidoylpyridin-4-yl)pyridine-2-carboximidamide Chemical group C1=NC(C(=N)N)=CC(C=2C=C(N=CC=2)C(N)=N)=C1 YYMQJGIRGGDLAL-UHFFFAOYSA-N 0.000 claims 1
UUSJIECFMYLBBU-UHFFFAOYSA-N 6-(6-carbamimidoylpyridin-2-yl)pyridine-2-carboximidamide Chemical compound NC(=N)C1=CC=CC(C=2N=C(C=CC=2)C(N)=N)=N1 UUSJIECFMYLBBU-UHFFFAOYSA-N 0.000 claims 1
238000009938 salting Methods 0.000 claims 1
206010028980 Neoplasm Diseases 0.000 abstract description 3
125000001424 substituent group Chemical group 0.000 abstract 2
125000005841 biaryl group Chemical group 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 20
125000004093 cyano group Chemical group *C#N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
239000000203 mixture Substances 0.000 description 13
239000004480 active ingredient Substances 0.000 description 12
239000000543 intermediate Substances 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000007858 starting material Substances 0.000 description 8
125000005115 alkyl carbamoyl group Chemical group 0.000 description 7
229910021529 ammonia Inorganic materials 0.000 description 7
239000002775 capsule Substances 0.000 description 7
239000000825 pharmaceutical preparation Substances 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
150000001409 amidines Chemical group 0.000 description 6
239000000047 product Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
102000004190 Enzymes Human genes 0.000 description 5
108090000790 Enzymes Proteins 0.000 description 5
239000013543 active substance Substances 0.000 description 5
125000005907 alkyl ester group Chemical group 0.000 description 5
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
125000004997 halocarbonyl group Chemical group 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
150000002367 halogens Chemical class 0.000 description 5
125000004356 hydroxy functional group Chemical group O* 0.000 description 5
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
229920000768 polyamine Polymers 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
125000003282 alkyl amino group Chemical group 0.000 description 4
238000009835 boiling Methods 0.000 description 4
238000000576 coating method Methods 0.000 description 4
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 4
239000008298 dragée Substances 0.000 description 4
229910000037 hydrogen sulfide Inorganic materials 0.000 description 4
239000003112 inhibitor Substances 0.000 description 4
230000002401 inhibitory effect Effects 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000000454 talc Substances 0.000 description 4
229910052623 talc Inorganic materials 0.000 description 4
235000012222 talc Nutrition 0.000 description 4
229910052720 vanadium Inorganic materials 0.000 description 4
IUMFOUVCDJGKNS-UHFFFAOYSA-N 2-(4-cyanopyridin-2-yl)pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC(C=2N=CC=C(C=2)C#N)=C1 IUMFOUVCDJGKNS-UHFFFAOYSA-N 0.000 description 3
QLDRPYNMCLPAAE-UHFFFAOYSA-N 3-(2-methylsulfanyl-4-oxo-1h-pyrimidin-6-yl)benzonitrile Chemical compound CSC1=NC(O)=CC(C=2C=C(C=CC=2)C#N)=N1 QLDRPYNMCLPAAE-UHFFFAOYSA-N 0.000 description 3
UHIWNRVLVWFQMZ-UHFFFAOYSA-N 6-(3-cyanophenyl)pyrimidine-4-carbonitrile Chemical compound N#CC1=CC=CC(C=2N=CN=C(C=2)C#N)=C1 UHIWNRVLVWFQMZ-UHFFFAOYSA-N 0.000 description 3
KTYGOEZHIBSNMW-UHFFFAOYSA-N 6-(6-cyanopyridin-2-yl)pyridine-2-carbonitrile Chemical compound N#CC1=CC=CC(C=2N=C(C=CC=2)C#N)=N1 KTYGOEZHIBSNMW-UHFFFAOYSA-N 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
241000251730 Chondrichthyes Species 0.000 description 3
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
150000001356 alkyl thiols Chemical class 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000007789 gas Substances 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
150000002825 nitriles Chemical class 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
238000007911 parenteral administration Methods 0.000 description 3
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
239000001267 polyvinylpyrrolidone Substances 0.000 description 3
229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
239000000600 sorbitol Substances 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
239000000126 substance Substances 0.000 description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
BYSLPIMHIFXRBB-UHFFFAOYSA-N 2-(3-bromophenyl)-4-chloropyridine Chemical compound ClC1=CC=NC(C=2C=C(Br)C=CC=2)=C1 BYSLPIMHIFXRBB-UHFFFAOYSA-N 0.000 description 2
QCMOAPGNXYERMF-UHFFFAOYSA-N 2-(3-cyanophenyl)pyridine-4-carbonitrile Chemical compound N#CC1=CC=CC(C=2N=CC=C(C=2)C#N)=C1 QCMOAPGNXYERMF-UHFFFAOYSA-N 0.000 description 2
LNSBMMBJCHVIEW-UHFFFAOYSA-N 3-(1-oxidopyridin-1-ium-2-yl)benzonitrile Chemical compound [O-][N+]1=CC=CC=C1C1=CC=CC(C#N)=C1 LNSBMMBJCHVIEW-UHFFFAOYSA-N 0.000 description 2
KTNBKNQUBNZOIO-UHFFFAOYSA-N 3-(1-oxidopyridin-1-ium-4-yl)benzonitrile Chemical compound C1=C[N+]([O-])=CC=C1C1=CC=CC(C#N)=C1 KTNBKNQUBNZOIO-UHFFFAOYSA-N 0.000 description 2
MWOOKDULMBMMPN-UHFFFAOYSA-N 3-(2-ethyl-1,2-oxazol-2-ium-5-yl)benzenesulfonate Chemical compound O1[N+](CC)=CC=C1C1=CC=CC(S([O-])(=O)=O)=C1 MWOOKDULMBMMPN-UHFFFAOYSA-N 0.000 description 2
SQCDIDNIDAVFPS-UHFFFAOYSA-N 3-(2-methylsulfanylpyrimidin-4-yl)benzonitrile Chemical compound CSC1=NC=CC(C=2C=C(C=CC=2)C#N)=N1 SQCDIDNIDAVFPS-UHFFFAOYSA-N 0.000 description 2
SGHDMBJSLYGKPL-UHFFFAOYSA-N 3-(2-methylsulfonylpyrimidin-4-yl)benzonitrile Chemical compound CS(=O)(=O)C1=NC=CC(C=2C=C(C=CC=2)C#N)=N1 SGHDMBJSLYGKPL-UHFFFAOYSA-N 0.000 description 2
MGLBVUCXWVFGDA-UHFFFAOYSA-N 3-(3-carbamothioylphenyl)benzenecarbothioamide Chemical group NC(=S)C1=CC=CC(C=2C=C(C=CC=2)C(N)=S)=C1 MGLBVUCXWVFGDA-UHFFFAOYSA-N 0.000 description 2
OCYRECWBTXIHJO-UHFFFAOYSA-N 3-(4-oxo-1h-pyrimidin-6-yl)benzonitrile Chemical compound C1=NC(O)=CC(C=2C=C(C=CC=2)C#N)=N1 OCYRECWBTXIHJO-UHFFFAOYSA-N 0.000 description 2
QIUXOFGANUKCKY-UHFFFAOYSA-N 3-(6-chloro-2-methylsulfanylpyrimidin-4-yl)benzonitrile Chemical compound CSC1=NC(Cl)=CC(C=2C=C(C=CC=2)C#N)=N1 QIUXOFGANUKCKY-UHFFFAOYSA-N 0.000 description 2
XDMJJWRNNDGWRQ-UHFFFAOYSA-N 3-(6-chloropyrimidin-4-yl)benzonitrile Chemical compound C1=NC(Cl)=CC(C=2C=C(C=CC=2)C#N)=N1 XDMJJWRNNDGWRQ-UHFFFAOYSA-N 0.000 description 2
JUBACFMBYWFAJC-UHFFFAOYSA-N 4-(2-cyanopyridin-4-yl)pyridine-2-carbonitrile Chemical compound C1=NC(C#N)=CC(C=2C=C(N=CC=2)C#N)=C1 JUBACFMBYWFAJC-UHFFFAOYSA-N 0.000 description 2
TXNQLYXOAFGPDH-UHFFFAOYSA-N 4-(3-cyanophenyl)pyridine-2-carbonitrile Chemical compound N#CC1=CC=CC(C=2C=C(N=CC=2)C#N)=C1 TXNQLYXOAFGPDH-UHFFFAOYSA-N 0.000 description 2
YHWHFPFTPKWUDK-UHFFFAOYSA-N 4-(3-cyanophenyl)pyrimidine-2-carbonitrile Chemical compound N#CC1=CC=CC(C=2N=C(N=CC=2)C#N)=C1 YHWHFPFTPKWUDK-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
RVJSRIMBOYMNCV-UHFFFAOYSA-N 6-(3-cyanophenyl)pyridine-2-carbonitrile Chemical compound N#CC1=CC=CC(C=2N=C(C=CC=2)C#N)=C1 RVJSRIMBOYMNCV-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
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 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
229910019213 POCl3 Inorganic materials 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
238000006434 Ritter amidation reaction Methods 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
230000008901 benefit Effects 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
239000001506 calcium phosphate Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
229920001429 chelating resin Polymers 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
239000000945 filler Substances 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
210000004051 gastric juice Anatomy 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
239000008187 granular material Substances 0.000 description 2
230000012010 growth Effects 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
238000006263 metalation reaction Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
150000002905 orthoesters Chemical class 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
150000003141 primary amines Chemical class 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
230000009467 reduction Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
150000003335 secondary amines Chemical class 0.000 description 2
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
235000000346 sugar Nutrition 0.000 description 2
239000002511 suppository base Substances 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
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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
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201000004792 malaria Diseases 0.000 description 1
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239000000594 mannitol Substances 0.000 description 1
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239000002609 medium Substances 0.000 description 1
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VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
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229920000609 methyl cellulose Polymers 0.000 description 1
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125000001624 naphthyl group Chemical group 0.000 description 1
230000017095 negative regulation of cell growth Effects 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
150000002826 nitrites Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003791 organic solvent mixture Substances 0.000 description 1
239000002818 ornithine decarboxylase inhibitor Substances 0.000 description 1
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239000012188 paraffin wax Substances 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
238000003408 phase transfer catalysis Methods 0.000 description 1
AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 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
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
239000000049 pigment Substances 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
102000007739 porin activity proteins Human genes 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
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230000003389 potentiating effect Effects 0.000 description 1
210000001236 prokaryotic cell Anatomy 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
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000746 purification Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
238000012552 review Methods 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
229940100486 rice starch Drugs 0.000 description 1
230000007017 scission Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000003248 secreting effect Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
235000002639 sodium chloride Nutrition 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
125000005505 thiomorpholino group Chemical group 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
125000005490 tosylate group Chemical group 0.000 description 1
238000006257 total synthesis reaction Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
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210000004881 tumor cell Anatomy 0.000 description 1
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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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/83—Thioacids; Thioesters; Thioamides; Thioimides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)

DD89330468A 1988-07-07 1989-07-05 Verfahren zur herstellung von biarylverbindungen DD284004A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH258888		1988-07-07

Publications (1)

Publication Number	Publication Date
DD284004A5 true DD284004A5 (de)	1990-10-31

Family

ID=4237163

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD89330468A DD284004A5 (de)	1988-07-07	1989-07-05	Verfahren zur herstellung von biarylverbindungen

Country Status (15)

Country	Link
US (2)	US4968804A (pt)
EP (1)	EP0350448A1 (pt)
JP (1)	JPH0276843A (pt)
KR (1)	KR900001677A (pt)
AU (1)	AU622188B2 (pt)
DD (1)	DD284004A5 (pt)
DK (1)	DK336089A (pt)
FI (1)	FI893266A7 (pt)
HU (1)	HU208811B (pt)
IL (1)	IL90793A0 (pt)
MX (1)	MX16687A (pt)
NO (1)	NO892810L (pt)
NZ (1)	NZ229841A (pt)
PT (1)	PT91068B (pt)
ZA (1)	ZA895141B (pt)

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EP0495749A1 (de) *	1991-01-14	1992-07-22	Ciba-Geigy Ag	Bipyridyle
JPH07508537A (ja) *	1993-04-21	1995-09-21	イーストマンコダックカンパニー	イオン感受性化合物
DK1231910T3 (da) *	1999-11-16	2009-08-31	Oncozyme Pharma Inc	Pentamidin til behandling af cancer
DE10035908A1 (de)	2000-07-21	2002-03-07	Asta Medica Ag	Neue Heteroaryl-Derivate und deren Verwendung als Arzneimittel
GB0124933D0 (en) *	2001-10-17	2001-12-05	Glaxo Group Ltd	Chemical compounds
GB0124941D0 (en) *	2001-10-17	2001-12-05	Glaxo Group Ltd	Chemical compounds
GB0124936D0 (en) *	2001-10-17	2001-12-05	Glaxo Group Ltd	Chemical compounds
GB0124934D0 (en) *	2001-10-17	2001-12-05	Glaxo Group Ltd	Chemical compounds
GB0124931D0 (en) *	2001-10-17	2001-12-05	Glaxo Group Ltd	Chemical compounds
GB0124939D0 (en) *	2001-10-17	2001-12-05	Glaxo Group Ltd	Chemical compounds
GB0124938D0 (en) *	2001-10-17	2001-12-05	Glaxo Group Ltd	Chemical compounds
ATE375980T1 (de)	2002-02-12	2007-11-15	Smithkline Beecham Corp	Nicotinamide und deren verwendung als p38 inhibitoren
GB0217757D0 (en)	2002-07-31	2002-09-11	Glaxo Group Ltd	Novel compounds
GB0308185D0 (en) *	2003-04-09	2003-05-14	Smithkline Beecham Corp	Novel compounds
GB0402143D0 (en) *	2004-01-30	2004-03-03	Smithkline Beecham Corp	Novel compounds
US20080051416A1 (en) *	2004-10-05	2008-02-28	Smithkline Beecham Corporation	Novel Compounds
GB0512429D0 (en) *	2005-06-17	2005-07-27	Smithkline Beecham Corp	Novel compound
WO2009045385A1 (en) *	2007-10-04	2009-04-09	Merck & Co., Inc.	N-hydroxy-naphthalene dicarboxamide and n-hydroxy-biphenyl-dicarboxamide compounds as histone deacetylase inhibitors
JP5693452B2 (ja) *	2008-08-04	2015-04-01	シーエイチディーアイファウンデーション，インコーポレーテッド	特定のキヌレニン−３−モノオキシゲナーゼインヒビター、医薬組成物およびそれらの使用方法
CA2787365A1 (en)	2010-01-25	2011-07-28	Chdi Foundation, Inc.	Certain kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof
KR20140072037A (ko)	2011-08-30	2014-06-12	씨에이치디아이 파운데이션, 인코포레이티드	키뉴레닌-3-모노옥시게나제 억제제, 약학적 조성물 및 이의 사용 방법
SI2750677T1 (sl)	2011-08-30	2017-10-30	Chdi Foundation, Inc.	Inhibitorji kinurenin-3-monooksigenaze, farmacevtski sestavki in postopki njihove uporabe
AU2015289492B2 (en)	2014-07-17	2020-02-20	Chdi Foundation, Inc.	Methods and compositions for treating HIV-related disorders
CN106389415B (zh) *	2016-04-22	2019-02-19	三峡大学	小分子共价抑制剂在制备抑制s-腺苷甲硫氨酸脱羧酶的药物上的应用及其筛选方法
CN106407739B (zh) *	2016-04-22	2019-02-22	三峡大学	小分子共价抑制剂计算机筛选方法及其在筛选s-腺苷甲硫氨酸脱羧酶共价抑制剂的应用
CN106389399B (zh) *	2016-04-22	2019-02-19	三峡大学	一种小分子共价抑制剂在制备抑制s-腺苷甲硫氨酸脱羧酶的药物上的应用及其筛选方法
CN106389403B (zh) *	2016-04-22	2019-02-19	三峡大学	小分子共价抑制剂在制备抑制s-腺苷甲硫氨酸脱羧酶的药物上的应用及筛选方法

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1989
- 1989-06-05 MX MX1668789A patent/MX16687A/es unknown
- 1989-06-28 AU AU37174/89A patent/AU622188B2/en not_active Ceased
- 1989-06-28 EP EP89810491A patent/EP0350448A1/de not_active Ceased
- 1989-06-29 IL IL90793A patent/IL90793A0/xx not_active IP Right Cessation
- 1989-07-05 US US07/375,760 patent/US4968804A/en not_active Expired - Fee Related
- 1989-07-05 DD DD89330468A patent/DD284004A5/de not_active IP Right Cessation
- 1989-07-05 FI FI893266A patent/FI893266A7/fi not_active IP Right Cessation
- 1989-07-05 PT PT91068A patent/PT91068B/pt active IP Right Grant
- 1989-07-05 NZ NZ229841A patent/NZ229841A/en unknown
- 1989-07-06 JP JP1173144A patent/JPH0276843A/ja active Pending
- 1989-07-06 DK DK336089A patent/DK336089A/da not_active Application Discontinuation
- 1989-07-06 HU HU893434A patent/HU208811B/hu not_active IP Right Cessation
- 1989-07-06 ZA ZA895141A patent/ZA895141B/xx unknown
- 1989-07-06 NO NO89892810A patent/NO892810L/no unknown
- 1989-07-06 KR KR1019890009573A patent/KR900001677A/ko not_active Withdrawn
1990
- 1990-08-16 US US07/568,371 patent/US5064832A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
PT91068A (pt)	1990-02-08
AU622188B2 (en)	1992-04-02
HUT50778A (en)	1990-03-28
IL90793A0 (en)	1990-01-18
DK336089D0 (da)	1989-07-06
JPH0276843A (ja)	1990-03-16
EP0350448A1 (de)	1990-01-10
HU208811B (en)	1994-01-28
FI893266A7 (fi)	1990-01-08
DK336089A (da)	1990-01-08
MX16687A (es)	1994-01-31
NZ229841A (en)	1990-11-27
FI893266A0 (fi)	1989-07-05
US4968804A (en)	1990-11-06
PT91068B (pt)	1994-12-30
NO892810L (no)	1990-01-08
NO892810D0 (no)	1989-07-06
US5064832A (en)	1991-11-12
KR900001677A (ko)	1990-02-27
ZA895141B (en)	1990-02-28
AU3717489A (en)	1990-01-11

Legal Events

Date	Code	Title	Description
2000-06-08	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD284004A5 (de)	1990-10-31	Verfahren zur herstellung von biarylverbindungen
EP0335832B1 (de)	1993-02-10	Arylhydrazone
AT363096B (de)	1981-07-10	Verfahren zur herstellung von neuen phthalazinderivaten und deren salzen
DE69132961T2 (de)	2002-09-19	Styrylsubstituierte heteroarylverbindungen, welche egf-rezeptor-tyrosinkinase inhibieren
DE69207017T2 (de)	1996-09-05	Benzamide
DE69120100T2 (de)	1996-11-14	Annelierte Thiophen-Derivate, ihre Herstellung und Verwendung
DE4129603A1 (de)	1993-03-11	Kondensierte 5-gliedrige heterocyclen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
EP0516588B1 (de)	1994-07-13	Substituierte Diaminophthalimide und Analoga
DE69523298T2 (de)	2002-06-27	Aminostilbazolderivate und medikament
EP0547517B1 (de)	1995-05-17	Neue Pyridylderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
DE19851421A1 (de)	2000-05-11	Neue Pyrimidine, deren Herstellung und Verwendung
EP0124476B1 (de)	1988-06-22	Carboxamide, Verfahren zur Herstellung und pharmazeutische Präparate, die diese enthalten
DE2149249B2 (de)	1974-11-07	4-Amino-6-arylpyrimidine
DE1965264A1 (de)	1970-07-16	Pyrazinoylsulfamide und Verfahren zu ihrer Herstellung
EP0408509B1 (de)	1996-03-06	Substituierte Benzonitrile
EP0456133B1 (de)	1995-03-15	Hydrazone
DE2112349A1 (de)	1971-10-14	Di- und tri-substituierte Imidazole
DE3923675A1 (de)	1991-01-24	Amonoalkylsubstituierte 2-aminothiazole und diese enthaltende therapeutische mittel
EP0477141B1 (de)	1997-02-26	Heteroarylmethylbenzole-Aromatasehemmer
DE3427985A1 (de)	1986-01-30	Neue 2h-l-benzopyran-2-on-derivate, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten
DE3216843A1 (de)	1983-11-17	Thiomethylpyridin-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
US4318915A (en)	1982-03-09	Substituted guandines and methods of preparation thereof
CH634074A5 (de)	1983-01-14	Verfahren zur herstellung von neuen cephemcarbonsaeurederivaten.
EP0331093A1 (de)	1989-09-06	Neue Benzimidazo[1,2-c] chinazoline, ihre Herstellung und Verwendung
DD154487A5 (de)	1982-03-24	Verfahren zur herstellung von 1-benzoxepin-5(2h)-on-derivaten