UA75109C2 - A method for producing sulfonamide-substituted imidazotriazinones - Google Patents

A method for producing sulfonamide-substituted imidazotriazinones Download PDF

Info

Publication number: UA75109C2
Authority: UA; Ukraine
Prior art keywords: carbon atoms; necessary; unbranched; different; formula
Prior art date: 2000-12-18

Application number

UA2003076744A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Bayer Healthcare 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.)

2000-12-18

Filing date

2001-05-12

Publication date

2006-03-15

2001-05-12 Application filed by Bayer Healthcare Ag filed Critical Bayer Healthcare Ag

2006-03-15 Publication of UA75109C2 publication Critical patent/UA75109C2/uk

Links

IJYHVZICHKCLMQ-UHFFFAOYSA-N imidazo[4,5-d]triazin-4-one Chemical class O=C1N=NN=C2N=CN=C12 IJYHVZICHKCLMQ-UHFFFAOYSA-N 0.000 title abstract description 3
238000004519 manufacturing process Methods 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 55
238000000034 method Methods 0.000 claims abstract description 29
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 26
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 13
150000001412 amines Chemical class 0.000 claims abstract description 8
239000012442 inert solvent Substances 0.000 claims abstract description 6
150000004677 hydrates Chemical class 0.000 claims abstract description 3
150000003839 salts Chemical class 0.000 claims abstract description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 58
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 42
125000000217 alkyl group Chemical group 0.000 claims description 35
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
230000003993 interaction Effects 0.000 claims description 23
238000006243 chemical reaction Methods 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 22
-1 hydroxy, formyl Chemical group 0.000 claims description 22
125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
229910052757 nitrogen Inorganic materials 0.000 claims description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
125000000623 heterocyclic group Chemical group 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
150000002431 hydrogen Chemical class 0.000 claims description 10
125000003386 piperidinyl group Chemical group 0.000 claims description 10
125000002757 morpholinyl group Chemical group 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
125000002252 acyl group Chemical group 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 3
239000012346 acetyl chloride Substances 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
125000004568 thiomorpholinyl group Chemical group 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
150000001204 N-oxides Chemical class 0.000 abstract 1
238000011065 in-situ storage Methods 0.000 abstract 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 38
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
239000000047 product Substances 0.000 description 14
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
230000008569 process Effects 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000003153 chemical reaction reagent Substances 0.000 description 12
239000002904 solvent Substances 0.000 description 12
239000002585 base Substances 0.000 description 11
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
150000002430 hydrocarbons Chemical group 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 6
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 6
239000012071 phase Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
239000008096 xylene Substances 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
235000011121 sodium hydroxide Nutrition 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 4
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 4
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 4
229950005499 carbon tetrachloride Drugs 0.000 description 4
230000003197 catalytic effect Effects 0.000 description 4
229960001701 chloroform Drugs 0.000 description 4
125000004122 cyclic group Chemical group 0.000 description 4
150000002168 ethanoic acid esters Chemical class 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
229960004592 isopropanol Drugs 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
DXTLCLWOCYLDHL-UHFFFAOYSA-N 2-ethoxybenzonitrile Chemical compound CCOC1=CC=CC=C1C#N DXTLCLWOCYLDHL-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
238000004821 distillation Methods 0.000 description 3
150000008282 halocarbons Chemical class 0.000 description 3
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000008363 phosphate buffer Substances 0.000 description 3
230000009467 reduction Effects 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
238000010992 reflux Methods 0.000 description 3
238000000926 separation method Methods 0.000 description 3
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 3
DTIMTCJMOWXMGT-UHFFFAOYSA-N 2-(butanoylamino)propanoic acid Chemical compound CCCC(=O)NC(C)C(O)=O DTIMTCJMOWXMGT-UHFFFAOYSA-N 0.000 description 2
AYCUYSLVLQCKFH-UHFFFAOYSA-N 4-oxoimidazo[4,5-d]triazine-6-sulfonyl chloride Chemical compound N1=NC(=O)C2=NC(S(=O)(=O)Cl)=NC2=N1 AYCUYSLVLQCKFH-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
WBXQXRXMGCOVHA-UHFFFAOYSA-N [methyl(nitroso)amino]methyl acetate Chemical compound O=NN(C)COC(C)=O WBXQXRXMGCOVHA-UHFFFAOYSA-N 0.000 description 2
150000003973 alkyl amines Chemical class 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
238000010533 azeotropic distillation Methods 0.000 description 2
229940092714 benzenesulfonic acid Drugs 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
NGMHLSBQVIXGNZ-UHFFFAOYSA-N (2-ethoxybenzenecarboximidoyl)azanium;chloride Chemical compound Cl.CCOC1=CC=CC=C1C(N)=N NGMHLSBQVIXGNZ-UHFFFAOYSA-N 0.000 description 1
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-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
238000005160 1H NMR spectroscopy Methods 0.000 description 1
RVBUZBPJAGZHSQ-UHFFFAOYSA-N 2-chlorobutanoic acid Chemical compound CCC(Cl)C(O)=O RVBUZBPJAGZHSQ-UHFFFAOYSA-N 0.000 description 1
XCYFBAJVMNISHC-UHFFFAOYSA-N 2-ethoxybenzamide;hydrochloride Chemical compound Cl.CCOC1=CC=CC=C1C(N)=O XCYFBAJVMNISHC-UHFFFAOYSA-N 0.000 description 1
DXOHZOPKNFZZAD-UHFFFAOYSA-N 2-ethylpiperazine Chemical compound CCC1CNCCN1 DXOHZOPKNFZZAD-UHFFFAOYSA-N 0.000 description 1
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
108010044467 Isoenzymes Proteins 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
239000005844 Thymol Substances 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001409 amidines Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
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SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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230000008025 crystallization Effects 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
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SBNKFTQSBPKMBZ-UHFFFAOYSA-N ethenzamide Chemical compound CCOC1=CC=CC=C1C(N)=O SBNKFTQSBPKMBZ-UHFFFAOYSA-N 0.000 description 1
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125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
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235000011389 fruit/vegetable juice Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
201000001881 impotence Diseases 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000006328 iso-butylcarbonyl group Chemical group [H]C([H])([H])C([H])(C(*)=O)C([H])([H])[H] 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004673 propylcarbonyl group Chemical group 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
239000002994 raw material Substances 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Natural products CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 1
229960000790 thymol Drugs 0.000 description 1
125000003639 thymyl group Chemical group C1(=CC(C)=CC=C1C(C)C)* 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
CUGZEDSDRBMZMY-UHFFFAOYSA-N trihydrate;hydrochloride Chemical compound O.O.O.Cl CUGZEDSDRBMZMY-UHFFFAOYSA-N 0.000 description 1
JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
239000005051 trimethylchlorosilane Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives

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

UA2003076744A 2000-12-18 2001-05-12 A method for producing sulfonamide-substituted imidazotriazinones UA75109C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10063108A DE10063108A1 (de)	2000-12-18	2000-12-18	Verfahren zur Herstellung von Sulfonamid-substituierten Imidazotriazinonen
PCT/EP2001/014239 WO2002050076A2 (de)	2000-12-18	2001-12-05	Verfahren zur herstellung von sulfonamid-substituierten imidazotriazinonen

Publications (1)

Publication Number	Publication Date
UA75109C2 true UA75109C2 (en)	2006-03-15

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Application Number	Title	Priority Date	Filing Date
UA2003076744A UA75109C2 (en)	2000-12-18	2001-05-12	A method for producing sulfonamide-substituted imidazotriazinones

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US (3)	US6777551B2 (cs)
EP (1)	EP1345939B1 (cs)
JP (1)	JP4441175B2 (cs)
KR (1)	KR100787288B1 (cs)
CN (1)	CN1227253C (cs)
AR (1)	AR032775A1 (cs)
AT (1)	ATE328885T1 (cs)
AU (2)	AU2002217089B2 (cs)
BG (1)	BG66142B1 (cs)
BR (1)	BRPI0116227B8 (cs)
CA (1)	CA2431933C (cs)
CU (2)	CU23341B7 (cs)
CY (1)	CY1105197T1 (cs)
CZ (1)	CZ297005B6 (cs)
DE (2)	DE10063108A1 (cs)
DK (1)	DK1345939T3 (cs)
DO (1)	DOP2001000295A (cs)
EC (1)	ECSP034657A (cs)
EE (1)	EE05308B1 (cs)
ES (1)	ES2266098T3 (cs)
GT (1)	GT200100251A (cs)
HN (1)	HN2001000278A (cs)
HR (1)	HRP20030583B1 (cs)
HU (1)	HU229296B1 (cs)
IL (2)	IL156278A0 (cs)
MA (1)	MA25927A1 (cs)
MX (1)	MXPA03005429A (cs)
MY (1)	MY126689A (cs)
NO (1)	NO325398B1 (cs)
NZ (1)	NZ526477A (cs)
PE (1)	PE20020590A1 (cs)
PL (1)	PL207294B1 (cs)
PT (1)	PT1345939E (cs)
RU (1)	RU2299211C2 (cs)
SI (1)	SI1345939T1 (cs)
SK (1)	SK286894B6 (cs)
SV (1)	SV2003000766A (cs)
TW (1)	TWI289562B (cs)
UA (1)	UA75109C2 (cs)
UY (2)	UY27070A1 (cs)
WO (1)	WO2002050076A2 (cs)
ZA (1)	ZA200304705B (cs)

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DE10063108A1 (de) *	2000-12-18	2002-06-20	Bayer Ag	Verfahren zur Herstellung von Sulfonamid-substituierten Imidazotriazinonen
DE10107639A1 (de) *	2001-02-15	2002-08-22	Bayer Ag	2-Alkoxyphenyl-substituierte Imidazotriazinone
DE10232113A1 (de)	2002-07-16	2004-01-29	Bayer Ag	Vardenafil Hydrochlorid Trihydrat enthaltende Arzneimittel
DE202004006552U1 (de) *	2004-04-26	2004-07-08	Knürr AG	Kühlungssystem für Geräte- und Netzwerkschränke
DE102004023069A1 (de)	2004-05-11	2005-12-08	Bayer Healthcare Ag	Neue Darreichungsformen des PDE 5-Inhibitors Vardenafil
US7977478B2 (en) *	2006-03-13	2011-07-12	Dr. Reddy's Laboratories Limited	Polymorphic forms of vardenafil
WO2009030095A1 (fr) *	2007-09-06	2009-03-12	Topharman Shanghai Co., Ltd.	Procédé de préparation de vardénafil et de ses intermédiaires
WO2009082845A1 (fr)	2007-12-28	2009-07-09	Topharman Shanghai Co., Ltd.	N-{1-[3-(2-éthoxy-5-(4-éthylpipérazinyl)benzènesulfonyl)-4,5-dihydro-5-oxo-1,2,4-triazin-6-yl]éthyl}butyramide, son procédé de préparation et son utilisation
AU2010280358A1 (en)	2009-08-07	2012-03-08	Ranbaxy Laboratories Limited	Processes for the preparation of vardenafil
PL390079A1 (pl) *	2009-12-30	2011-07-04	Zakłady Farmaceutyczne POLPHARMA Spółka Akcyjna	Sposób otrzymywania wardenafilu i jego izolacji jako soli z kwasem cytrynowym oraz krystaliczna postać tej soli
CN102134242B (zh)	2011-01-21	2013-08-28	浙江大德药业集团有限公司	一种用于治疗阳痿的快速长效的化合物
CZ2011767A3 (cs) *	2011-11-24	2013-06-05	Zentiva, K.S.	Zpusob prípravy a izolace solí vardenafilu s kyselinami
WO2015089105A1 (en)	2013-12-09	2015-06-18	Respira Therapeutics, Inc.	Pde5 inhibitor powder formulations and methods relating thereto
PL223869B1 (pl)	2013-12-16	2016-11-30	Starogardzkie Zakłady Farm Polpharma Spółka Akcyjna	Sposób otrzymywania wardenafilu i jego soli
CN107383020A (zh) *	2017-07-29	2017-11-24	合肥创新医药技术有限公司	一种伐地那非杂质的制备方法
CN111655229A (zh)	2017-12-20	2020-09-11	卡里亚制药控股有限公司	包含伐地那非的薄膜制剂、其制备方法及其用途
CN115043757B (zh) *	2022-07-27	2023-08-08	南京桦冠生物技术有限公司	一种连续化制备苄脒盐酸盐的方法

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Publication number	Priority date	Publication date	Assignee	Title
GB9301192D0 (en) *	1993-06-09	1993-06-09	Trott Francis W	Flower shaped mechanised table
HU227841B1 (en)	1997-11-12	2012-05-02	Bayer Pharma AG	2-phenyl substituted imidazotriazinones, process for their preparation and pharmaceutical compositions thereof
DE10063108A1 (de) *	2000-12-18	2002-06-20	Bayer Ag	Verfahren zur Herstellung von Sulfonamid-substituierten Imidazotriazinonen
DE10107639A1 (de) *	2001-02-15	2002-08-22	Bayer Ag	2-Alkoxyphenyl-substituierte Imidazotriazinone

2000
- 2000-12-18 DE DE10063108A patent/DE10063108A1/de not_active Withdrawn
2001
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- 2001-11-28 AR ARP010105546A patent/AR032775A1/es active IP Right Grant
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- 2001-12-05 DE DE50110080T patent/DE50110080D1/de not_active Expired - Lifetime
- 2001-12-05 RU RU2003122192/04A patent/RU2299211C2/ru active
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- 2001-12-05 AU AU2002217089A patent/AU2002217089B2/en not_active Expired
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- 2003-06-18 ZA ZA200304705A patent/ZA200304705B/en unknown
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2004
- 2004-07-02 US US10/884,686 patent/US20050014756A1/en not_active Abandoned
2005
- 2005-05-05 US US11/124,452 patent/US6998483B2/en not_active Expired - Lifetime
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- 2006-09-05 CY CY20061101263T patent/CY1105197T1/el unknown
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- 2008-11-17 CU CUP2008000213A patent/CU23873B1/es active IP Right Grant
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Also Published As

Publication number	Publication date
US20020137930A1 (en)	2002-09-26
BG107892A (bg)	2004-08-31
EE200300294A (et)	2003-10-15
AR032775A1 (es)	2003-11-26
ATE328885T1 (de)	2006-06-15
CN1227253C (zh)	2005-11-16
EP1345939A2 (de)	2003-09-24
NO20032731D0 (no)	2003-06-16
CU20080213A7 (es)	2012-06-21
EP1345939B1 (de)	2006-06-07
HN2001000278A (es)	2002-01-30
MY126689A (en)	2006-10-31
SK286894B6 (sk)	2009-07-06
NZ526477A (en)	2004-12-24
HUP0302467A3 (en)	2004-11-29
PL365310A1 (en)	2004-12-27
CA2431933C (en)	2009-12-01
MXPA03005429A (es)	2004-05-04
CN1481386A (zh)	2004-03-10
ECSP034657A (es)	2003-07-25
IL156278A0 (en)	2004-01-04
HRP20030583B1 (hr)	2011-09-30
PT1345939E (pt)	2006-08-31
CZ20031692A3 (cs)	2003-10-15
BG66142B1 (bg)	2011-07-29
DE50110080D1 (de)	2006-07-20
JP4441175B2 (ja)	2010-03-31
NO20032731L (no)	2003-06-16
US6777551B2 (en)	2004-08-17
US20050203298A1 (en)	2005-09-15
JP2004517849A (ja)	2004-06-17
IL156278A (en)	2009-06-15
KR100787288B1 (ko)	2007-12-20
SI1345939T1 (sl)	2006-10-31
PL207294B1 (pl)	2010-11-30
SK7502003A3 (en)	2003-10-07
CY1105197T1 (el)	2010-03-03
RU2299211C2 (ru)	2007-05-20
KR20030063430A (ko)	2003-07-28
UY37172A (es)	2017-06-30
CA2431933A1 (en)	2002-06-27
CU23341B7 (es)	2009-02-20
SV2003000766A (es)	2003-01-13
DK1345939T3 (da)	2006-09-25
TWI289562B (en)	2007-11-11
AU1708902A (en)	2002-07-01
BR0116227A (pt)	2003-12-30
BRPI0116227B8 (pt)	2021-05-25
EE05308B1 (et)	2010-06-15
WO2002050076A3 (de)	2002-08-29
DE10063108A1 (de)	2002-06-20
CZ297005B6 (cs)	2006-08-16
US6998483B2 (en)	2006-02-14
US20050014756A1 (en)	2005-01-20
PE20020590A1 (es)	2002-07-13
WO2002050076A2 (de)	2002-06-27
HK1063799A1 (en)	2005-01-14
CU23873B1 (es)	2013-04-19
HU229296B1 (en)	2013-10-28
GT200100251A (es)	2002-10-01
ZA200304705B (en)	2004-08-12
NO325398B1 (no)	2008-04-21
BR0116227B1 (pt)	2014-08-26
DOP2001000295A (es)	2002-12-15
AU2002217089B2 (en)	2006-01-12
HUP0302467A2 (hu)	2003-11-28
UY27070A1 (es)	2002-07-31
ES2266098T3 (es)	2007-03-01
MA25927A1 (fr)	2003-10-01
HRP20030583A2 (en)	2005-06-30

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