IL100603A - ביפירידילים מותמרים תהליך להכנתם ותכשירי רוקחות המכילים אותם - Google Patents

ביפירידילים מותמרים תהליך להכנתם ותכשירי רוקחות המכילים אותם

Info

Publication number: IL100603A
Authority: IL; Israel
Prior art keywords: formula; radicals; lower alkyl; compound; salt
Prior art date: 1991-01-14

Application number

IL10060392A

Other languages

English (en)

Other versions

IL100603A0 (en

Original Assignee

Ciba Geigy Ag

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.)

1991-01-14

Filing date

1992-01-07

Publication date

1996-05-14

1992-01-07 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1992-09-06 Publication of IL100603A0 publication Critical patent/IL100603A0/xx

1996-05-14 Publication of IL100603A publication Critical patent/IL100603A/he

Links

238000002360 preparation method Methods 0.000 title claims description 14
239000008194 pharmaceutical composition Substances 0.000 title claims description 13
238000000034 method Methods 0.000 title claims description 12
230000008569 process Effects 0.000 title claims description 10
150000001875 compounds Chemical class 0.000 claims abstract description 123
229910052717 sulfur Inorganic materials 0.000 claims abstract description 50
150000003839 salts Chemical class 0.000 claims description 57
125000000217 alkyl group Chemical group 0.000 claims description 55
-1 carboxy, hydroxy Chemical class 0.000 claims description 45
229910052739 hydrogen Inorganic materials 0.000 claims description 29
239000001257 hydrogen Substances 0.000 claims description 28
125000003545 alkoxy group Chemical group 0.000 claims description 21
229910052736 halogen Inorganic materials 0.000 claims description 19
150000002367 halogens Chemical class 0.000 claims description 19
150000002431 hydrogen Chemical group 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
229910052760 oxygen Inorganic materials 0.000 claims description 14
125000002947 alkylene group Chemical group 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
JITDTXIWFDRQKH-UHFFFAOYSA-N 6-(6-carbamimidoyl-4-methoxypyridin-2-yl)-4-methoxypyridine-2-carboximidamide Chemical compound COC1=CC(C(N)=N)=NC(C=2N=C(C=C(OC)C=2)C(N)=N)=C1 JITDTXIWFDRQKH-UHFFFAOYSA-N 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
230000000842 anti-protozoal effect Effects 0.000 claims 2
239000003904 antiprotozoal agent Substances 0.000 claims 2
208000028172 protozoa infectious disease Diseases 0.000 claims 2
REQZIUVDPDRBQT-UHFFFAOYSA-N 6-(6-carbamimidoyl-4-methylpyridin-2-yl)-4-methylpyridine-2-carboximidamide Chemical compound CC1=CC(C(N)=N)=NC(C=2N=C(C=C(C)C=2)C(N)=N)=C1 REQZIUVDPDRBQT-UHFFFAOYSA-N 0.000 claims 1
VWWWRCNHKBNGLT-UHFFFAOYSA-N 6-(6-carbamimidoyl-5-methylpyridin-2-yl)-3-methylpyridine-2-carboximidamide Chemical compound N1=C(C(N)=N)C(C)=CC=C1C1=CC=C(C)C(C(N)=N)=N1 VWWWRCNHKBNGLT-UHFFFAOYSA-N 0.000 claims 1
208000015181 infectious disease Diseases 0.000 abstract 1
239000000203 mixture Substances 0.000 description 25
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
125000004093 cyano group Chemical group *C#N 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 19
238000012360 testing method Methods 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
239000004480 active ingredient Substances 0.000 description 18
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 18
239000000243 solution Substances 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
125000004356 hydroxy functional group Chemical group O* 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
125000005115 alkyl carbamoyl group Chemical group 0.000 description 11
239000000543 intermediate Substances 0.000 description 11
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
102000005758 Adenosylmethionine decarboxylase Human genes 0.000 description 9
108010070753 Adenosylmethionine decarboxylase Proteins 0.000 description 9
125000005907 alkyl ester group Chemical group 0.000 description 9
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
239000007858 starting material Substances 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
125000003282 alkyl amino group Chemical group 0.000 description 6
150000001409 amidines Chemical group 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
210000004027 cell Anatomy 0.000 description 6
238000010348 incorporation Methods 0.000 description 6
238000011534 incubation Methods 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
239000002775 capsule Substances 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
238000001816 cooling Methods 0.000 description 5
125000004997 halocarbonyl group Chemical group 0.000 description 5
FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 5
230000002401 inhibitory effect Effects 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
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
229920000768 polyamine Polymers 0.000 description 5
238000010992 reflux Methods 0.000 description 5
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 4
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
229910000037 hydrogen sulfide Inorganic materials 0.000 description 4
125000001841 imino group Chemical group [H]N=* 0.000 description 4
239000003112 inhibitor Substances 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
238000007911 parenteral administration Methods 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
230000009467 reduction Effects 0.000 description 4
150000003335 secondary amines Chemical class 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
239000004215 Carbon black (E152) Substances 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 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
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 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
230000002378 acidificating effect Effects 0.000 description 3
125000004423 acyloxy group Chemical group 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
125000003302 alkenyloxy group Chemical group 0.000 description 3
125000005530 alkylenedioxy group Chemical group 0.000 description 3
239000002585 base Substances 0.000 description 3
125000001589 carboacyl group Chemical group 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
235000010980 cellulose Nutrition 0.000 description 3
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
230000012010 growth Effects 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229910052744 lithium Inorganic materials 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
239000000463 material Substances 0.000 description 3
239000002609 medium Substances 0.000 description 3
230000002503 metabolic effect Effects 0.000 description 3
238000001465 metallisation Methods 0.000 description 3
239000007758 minimum essential medium Substances 0.000 description 3
150000002825 nitriles Chemical class 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
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000000600 sorbitol Substances 0.000 description 3
235000010356 sorbitol Nutrition 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
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-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
NBPGPQJFYXNFKN-UHFFFAOYSA-N 4-methyl-2-(4-methylpyridin-2-yl)pyridine Chemical compound CC1=CC=NC(C=2N=CC=C(C)C=2)=C1 NBPGPQJFYXNFKN-UHFFFAOYSA-N 0.000 description 2
HGFUQVOYHMXNQK-UHFFFAOYSA-N 6-(6-cyano-5-methylpyridin-2-yl)-3-methylpyridine-2-carbonitrile Chemical compound N1=C(C#N)C(C)=CC=C1C1=CC=C(C)C(C#N)=N1 HGFUQVOYHMXNQK-UHFFFAOYSA-N 0.000 description 2
102000016893 Amine Oxidase (Copper-Containing) Human genes 0.000 description 2
108010028700 Amine Oxidase (Copper-Containing) Proteins 0.000 description 2
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 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 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
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-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
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
241000124008 Mammalia Species 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
206010028980 Neoplasm Diseases 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
206010037075 Protozoal infections Diseases 0.000 description 2
238000006434 Ritter amidation reaction Methods 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
241001442397 Trypanosoma brucei rhodesiense Species 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
125000005153 alkyl sulfamoyl group Chemical group 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
125000005237 alkyleneamino group Chemical group 0.000 description 2
125000005133 alkynyloxy group Chemical group 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
235000019270 ammonium chloride Nutrition 0.000 description 2
150000003863 ammonium salts Chemical class 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
244000309464 bull Species 0.000 description 2
239000001506 calcium phosphate Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 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
ZWWWLCMDTZFSOO-UHFFFAOYSA-N diethoxyphosphorylformonitrile Chemical compound CCOP(=O)(C#N)OCC ZWWWLCMDTZFSOO-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
239000002702 enteric coating Substances 0.000 description 2
238000009505 enteric coating Methods 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
239000008101 lactose Substances 0.000 description 2
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 2
239000011777 magnesium Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
229920000137 polyphosphoric acid Polymers 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
150000003141 primary amines Chemical class 0.000 description 2
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 2
235000000346 sugar Nutrition 0.000 description 2
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
239000002511 suppository base Substances 0.000 description 2
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 2
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 2
201000002311 trypanosomiasis Diseases 0.000 description 2
229940100445 wheat starch Drugs 0.000 description 2
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
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
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NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
229940116317 potato starch Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000011533 pre-incubation Methods 0.000 description 1
238000012545 processing Methods 0.000 description 1
210000001236 prokaryotic cell Anatomy 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])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
125000006239 protecting group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant 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
229920006395 saturated elastomer Polymers 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
230000035945 sensitivity Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
210000002966 serum Anatomy 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
201000002612 sleeping sickness Diseases 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
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 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
229940054269 sodium pyruvate Drugs 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000007787 solid 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
229960004793 sucrose Drugs 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup 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
125000003396 thiol group Chemical class [H]S* 0.000 description 1
125000005505 thiomorpholino group Chemical group 0.000 description 1
229940104230 thymidine Drugs 0.000 description 1
239000004408 titanium dioxide Substances 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
210000004881 tumor cell Anatomy 0.000 description 1
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 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
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- 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

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Tropical Medicine & Parasitology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)

IL10060392A 1991-01-14 1992-01-07 ביפירידילים מותמרים תהליך להכנתם ותכשירי רוקחות המכילים אותם IL100603A (he)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH8591		1991-01-14

Publications (2)

Publication Number	Publication Date
IL100603A0 IL100603A0 (en)	1992-09-06
IL100603A true IL100603A (he)	1996-05-14

Family

ID=4178927

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10060392A IL100603A (he)	1991-01-14	1992-01-07	ביפירידילים מותמרים תהליך להכנתם ותכשירי רוקחות המכילים אותם

Country Status (13)

Country	Link
US (1)	US5354761A (he)
EP (1)	EP0495749A1 (he)
JP (1)	JPH04312576A (he)
KR (1)	KR920014796A (he)
AU (1)	AU648377B2 (he)
CA (1)	CA2059051A1 (he)
HU (1)	HU214339B (he)
IE (1)	IE920094A1 (he)
IL (1)	IL100603A (he)
MA (1)	MA22385A1 (he)
MX (1)	MX9200120A (he)
ZA (1)	ZA92224B (he)
ZW (1)	ZW692A1 (he)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2212118C (en) *	1995-03-15	2007-07-31	Novartis Ag	Piperidinyl-2-alkyl subst. linear polyamines for the reduction of intracellular, endogenic polyamine levels such as putrescine, spermidine and spermine, and their impact on cell proliferation
NZ524980A (en) *	2000-09-01	2005-10-28	Biogen Idec Inc	Novel CD40:CD154 binding interruptor compounds and use thereof to treat immunological complications

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4086244A (en) *	1976-12-10	1978-04-25	E. R. Squibb & Sons, Inc.	Amidines
US4495934A (en) *	1978-07-25	1985-01-29	Shaw Jr Seth T	IUD Arrangement
US4284074A (en) *	1978-07-26	1981-08-18	Shaw Jr Seth T	IUD Arrangement
AU538963B2 (en) *	1979-07-09	1984-09-06	Seth Thomas Shaw Jr.	Drug for use with an iud
DOP1981004033A (es) *	1980-12-23	1990-12-29	Ciba Geigy Ag	Procedimiento para proteger plantas de cultivo de la accion fitotoxica de herbicidas.
US4598073A (en) *	1982-12-06	1986-07-01	Research Corporation	Certain polycyclo-palladium-bipyridine complexes having anti-tumor activity
MX16687A (es) *	1988-07-07	1994-01-31	Ciba Geigy Ag	Compuestos de biarilo y procedimiento para su preparacion.

1992
- 1992-01-06 EP EP92810003A patent/EP0495749A1/de not_active Ceased
- 1992-01-07 IL IL10060392A patent/IL100603A/he not_active IP Right Cessation
- 1992-01-10 CA CA002059051A patent/CA2059051A1/en not_active Abandoned
- 1992-01-10 JP JP4002578A patent/JPH04312576A/ja active Pending
- 1992-01-13 KR KR1019920000331A patent/KR920014796A/ko not_active Abandoned
- 1992-01-13 ZA ZA92224A patent/ZA92224B/xx unknown
- 1992-01-13 HU HU9200105A patent/HU214339B/hu not_active IP Right Cessation
- 1992-01-13 MX MX9200120A patent/MX9200120A/es unknown
- 1992-01-13 IE IE009492A patent/IE920094A1/en unknown
- 1992-01-13 ZW ZW6/92A patent/ZW692A1/xx unknown
- 1992-01-13 MA MA22669A patent/MA22385A1/fr unknown
- 1992-01-13 AU AU10176/92A patent/AU648377B2/en not_active Ceased
1993
- 1993-06-01 US US08/069,660 patent/US5354761A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
MA22385A1 (fr)	1992-10-01
HU214339B (hu)	1998-03-02
ZA92224B (en)	1992-08-26
KR920014796A (ko)	1992-08-25
IL100603A0 (en)	1992-09-06
CA2059051A1 (en)	1992-07-15
AU1017692A (en)	1992-07-16
US5354761A (en)	1994-10-11
IE920094A1 (en)	1992-07-15
ZW692A1 (en)	1992-08-08
JPH04312576A (ja)	1992-11-04
AU648377B2 (en)	1994-04-21
MX9200120A (es)	1992-12-01
HUT63832A (en)	1993-10-28
EP0495749A1 (de)	1992-07-22
HU9200105D0 (en)	1992-04-28

Legal Events

Date	Code	Title
1996-10-16	FF	Patent granted
1996-12-05	KB	Patent renewed
1998-12-27	RH	Patent void

Publication	Publication Date	Title
US5064832A (en)	1991-11-12	Biaryl compounds
US4971986A (en)	1990-11-20	Arylhydrazones useful as SAMDC inhibitors
US3632645A (en)	1972-01-04	Substituted phenylacetyl derivatives of guanidine o-alkylisoureas s-alkylisothioureas and p-nitrobenzylisothiourea
BG62023B2 (bg)	1998-12-30	Тетрахидробензтиазоли,метод за получаването и приложението им като междинни продукти или като лекарствени средства
US9309203B2 (en)	2016-04-12	Malignant and non-malignant disease treatment with Ras antagonists
US3862152A (en)	1975-01-21	3-carbamoylamino-4-phenyl quinoline compounds
CA2041832C (en)	2002-09-17	Hydrazones
HK1000919B (en)	1998-05-08	Hydrazones
US5354761A (en)	1994-10-11	Bipyridyls
US5376685A (en)	1994-12-27	Arylhydrazones using as SAMDC inhibitors
EP0290558B1 (en)	1993-06-16	Antifolate agents
NZ241272A (en)	1994-10-26	6,6'-(di)amidine, (di)carboxamido and (di)thiocarboxamido-2,2'-bipyridine derivatives; preparatory processes and pharmaceutical compositions
HU226954B1 (en)	2010-03-29	Process for producing hydrazonic acids and pharmaceutical composition containing them
US4713390A (en)	1987-12-15	Sulfurated hydantoin derivatives and pharmaceutical compositions containing same
US4576948A (en)	1986-03-18	Composition and method for inhibiting terminal deoxyribonucleotidyl transferase activity
US4745118A (en)	1988-05-17	Substituted quinazoline-3-oxides providing pharmacological activity
TW299322B (he)	1997-03-01
JPWO1996026208A1 (ja)	1998-03-31	プリン化合物及びキサンチンオキシダーゼ阻害剤