SK282208B6 - Spôsob výroby 2,5-diamino-4,6-dichlórpyrimidínu a jeho formamidu, n-(2-amino-4,6-dichlórpyrimidin-5-yl)formamid a 4,6-dichlórpyrimidíny - Google Patents

Spôsob výroby 2,5-diamino-4,6-dichlórpyrimidínu a jeho formamidu, n-(2-amino-4,6-dichlórpyrimidin-5-yl)formamid a 4,6-dichlórpyrimidíny Download PDF

Info

Publication number: SK282208B6
Authority: SK; Slovakia
Prior art keywords: formula; amino; formamide; dichloropyrimidin; preparation
Prior art date: 1994-04-27

Application number

SK541-95A

Other languages

English (en)

Slovak (sk)

Other versions

SK54195A3 (en

Inventor

Gerhard Stucky

Ren� Imwinkelried

Original Assignee

Lonza 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.)

1994-04-27

Filing date

1995-04-26

Publication date

2001-12-03

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=4207186&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=SK282208(B6) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1995-04-26 Application filed by Lonza Ag filed Critical Lonza Ag

1995-11-08 Publication of SK54195A3 publication Critical patent/SK54195A3/sk

2001-12-03 Publication of SK282208B6 publication Critical patent/SK282208B6/sk

Links

238000000034 method Methods 0.000 title claims abstract description 20
XYWHZUCZNRMJGO-UHFFFAOYSA-N n-(2-amino-4,6-dichloropyrimidin-5-yl)formamide Chemical compound NC1=NC(Cl)=C(NC=O)C(Cl)=N1 XYWHZUCZNRMJGO-UHFFFAOYSA-N 0.000 title claims abstract description 16
ZXWGHENZKVQKPX-UHFFFAOYSA-N 4,6-dichloropyrimidine-2,5-diamine Chemical compound NC1=NC(Cl)=C(N)C(Cl)=N1 ZXWGHENZKVQKPX-UHFFFAOYSA-N 0.000 title claims abstract description 12
XJPZKYIHCLDXST-UHFFFAOYSA-N 4,6-dichloropyrimidine Chemical compound ClC1=CC(Cl)=NC=N1 XJPZKYIHCLDXST-UHFFFAOYSA-N 0.000 title claims abstract description 10
238000004519 manufacturing process Methods 0.000 title description 7
ZHNUHDYFZUAESO-NJFSPNSNSA-N aminoformaldehyde Chemical compound N[14CH]=O ZHNUHDYFZUAESO-NJFSPNSNSA-N 0.000 title 1
238000002360 preparation method Methods 0.000 claims abstract description 25
-1 aminomalonic acid ester Chemical class 0.000 claims abstract description 17
150000003839 salts Chemical class 0.000 claims abstract description 12
150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 11
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims abstract description 8
150000001408 amides Chemical class 0.000 claims abstract description 6
239000012320 chlorinating reagent Substances 0.000 claims abstract description 6
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims abstract description 4
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims abstract description 4
239000012467 final product Substances 0.000 claims abstract description 4
HWSJQFCTYLBBOF-UHFFFAOYSA-N 2,5-diamino-4-hydroxy-1h-pyrimidin-6-one Chemical compound NC1=NC(O)=C(N)C(O)=N1 HWSJQFCTYLBBOF-UHFFFAOYSA-N 0.000 claims abstract 2
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 14
239000000543 intermediate Substances 0.000 claims description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 8
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 6
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 6
238000010992 reflux Methods 0.000 claims description 6
238000005660 chlorination reaction Methods 0.000 claims description 5
239000002585 base Substances 0.000 claims description 4
235000019260 propionic acid Nutrition 0.000 claims description 4
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 3
OTHBCWKTCXJYAW-UHFFFAOYSA-N n,n-dibenzylformamide Chemical compound C=1C=CC=CC=1CN(C=O)CC1=CC=CC=C1 OTHBCWKTCXJYAW-UHFFFAOYSA-N 0.000 claims description 3
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
238000002955 isolation Methods 0.000 claims description 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
150000001340 alkali metals Chemical class 0.000 claims 1
125000003729 nucleotide group Chemical group 0.000 abstract description 7
150000003230 pyrimidines Chemical class 0.000 abstract description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
239000000047 product Substances 0.000 description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 21
238000005160 1H NMR spectroscopy Methods 0.000 description 12
239000007787 solid Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000000725 suspension Substances 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
239000000203 mixture Substances 0.000 description 8
238000001035 drying Methods 0.000 description 7
150000002168 ethanoic acid esters Chemical class 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
UDVOODLCOPGSIL-UHFFFAOYSA-N 9-butyl-6-chloropurin-2-amine Chemical compound N1=C(N)N=C2N(CCCC)C=NC2=C1Cl UDVOODLCOPGSIL-UHFFFAOYSA-N 0.000 description 5
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
FLSVUQSDOOPGNL-UHFFFAOYSA-N n'-(2-amino-4,6-dichloropyrimidin-5-yl)-n,n-dimethylmethanimidamide Chemical compound CN(C)C=NC1=C(Cl)N=C(N)N=C1Cl FLSVUQSDOOPGNL-UHFFFAOYSA-N 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
IIVYOQGIZSPVFZ-UHFFFAOYSA-N 2,5-diamino-4-hydroxy-1h-pyrimidin-6-one;hydrochloride Chemical compound Cl.NC1=NC(O)=C(N)C(=O)N1 IIVYOQGIZSPVFZ-UHFFFAOYSA-N 0.000 description 3
HUQVKUVITLUPKC-UHFFFAOYSA-N 4,6-dichloro-5-(piperidin-1-ylmethylideneamino)pyrimidin-2-amine Chemical compound ClC1=NC(N)=NC(Cl)=C1N=CN1CCCCC1 HUQVKUVITLUPKC-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000002243 precursor Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000004611 spectroscopical analysis Methods 0.000 description 3
238000005406 washing Methods 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
JBRCFKQCSJRVPK-UHFFFAOYSA-N 2-amino-9-butyl-6-chloro-7h-purin-8-one Chemical compound NC1=NC(Cl)=C2NC(=O)N(CCCC)C2=N1 JBRCFKQCSJRVPK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
230000000840 anti-viral effect Effects 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
229960004198 guanidine Drugs 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 2
DZSWTTZDZJHMIN-UHFFFAOYSA-N n-[4,6-dichloro-2-(piperidin-1-ylmethylideneamino)pyrimidin-5-yl]-1-piperidin-1-ylmethanimine Chemical compound N=1C(Cl)=C(N=CN2CCCCC2)C(Cl)=NC=1N=CN1CCCCC1 DZSWTTZDZJHMIN-UHFFFAOYSA-N 0.000 description 2
XHRJBLIFOPBAIK-UHFFFAOYSA-N n-[4,6-dichloro-5-(dimethylaminomethylideneamino)pyrimidin-2-yl]formamide Chemical compound CN(C)C=NC1=C(Cl)N=C(NC=O)N=C1Cl XHRJBLIFOPBAIK-UHFFFAOYSA-N 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
FVRFYPFFMLTSJG-UHFFFAOYSA-N 3,6-diamino-4-hydroxy-1h-pyridin-2-one Chemical compound NC1=CC(O)=C(N)C(=O)N1 FVRFYPFFMLTSJG-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
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 1
GIXWSQWZEZRRMS-UHFFFAOYSA-N N'-(5-amino-4,6-dichloropyrimidin-2-yl)-N,N-dimethylmethanimidamide Chemical compound ClC1=NC(=NC(=C1N)Cl)N=CN(C)C GIXWSQWZEZRRMS-UHFFFAOYSA-N 0.000 description 1
UKAHNBNVGOXJAV-UHFFFAOYSA-N N'-(5-aminopyrimidin-2-yl)-N,N-dimethylmethanimidamide Chemical compound CN(C)C=NC1=NC=C(C=N1)N UKAHNBNVGOXJAV-UHFFFAOYSA-N 0.000 description 1
SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000009435 amidation Effects 0.000 description 1
238000007112 amidation reaction Methods 0.000 description 1
JINBYESILADKFW-UHFFFAOYSA-N aminomalonic acid Chemical class OC(=O)C(N)C(O)=O JINBYESILADKFW-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000015572 biosynthetic process Effects 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
229910052801 chlorine Inorganic materials 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
150000005378 cyclohexanecarboxylic acids Chemical class 0.000 description 1
JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 1
HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229960000789 guanidine hydrochloride Drugs 0.000 description 1
PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 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
238000011065 in-situ storage Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
KTKOGYHDCBXJIS-UHFFFAOYSA-N n'-[4,6-dichloro-2-(dimethylaminomethylideneamino)pyrimidin-5-yl]-n,n-dimethylmethanimidamide Chemical compound CN(C)C=NC1=NC(Cl)=C(N=CN(C)C)C(Cl)=N1 KTKOGYHDCBXJIS-UHFFFAOYSA-N 0.000 description 1
UNBDDZDKBWPHAX-UHFFFAOYSA-N n,n-di(propan-2-yl)formamide Chemical compound CC(C)N(C=O)C(C)C UNBDDZDKBWPHAX-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
238000003672 processing method Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
JYMQQKIMCZOSMX-UHFFFAOYSA-N thiomorpholine-4-carbaldehyde Chemical compound O=CN1CCSCC1 JYMQQKIMCZOSMX-UHFFFAOYSA-N 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Virology (AREA)
Communicable Diseases (AREA)
General Chemical & Material Sciences (AREA)
Oncology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Saccharide Compounds (AREA)
Pyridine Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SK541-95A 1994-04-27 1995-04-26 Spôsob výroby 2,5-diamino-4,6-dichlórpyrimidínu a jeho formamidu, n-(2-amino-4,6-dichlórpyrimidin-5-yl)formamid a 4,6-dichlórpyrimidíny SK282208B6 (sk)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH129994		1994-04-27

Publications (2)

Publication Number	Publication Date
SK54195A3 SK54195A3 (en)	1995-11-08
SK282208B6 true SK282208B6 (sk)	2001-12-03

Family

ID=4207186

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK541-95A SK282208B6 (sk)	1994-04-27	1995-04-26	Spôsob výroby 2,5-diamino-4,6-dichlórpyrimidínu a jeho formamidu, n-(2-amino-4,6-dichlórpyrimidin-5-yl)formamid a 4,6-dichlórpyrimidíny

Country Status (18)

Country	Link
US (4)	US5583226A (fr)
EP (2)	EP0684236B2 (fr)
JP (2)	JP3811966B2 (fr)
KR (1)	KR100327996B1 (fr)
CN (2)	CN1193991C (fr)
AT (2)	ATE167672T1 (fr)
CA (1)	CA2145928C (fr)
CZ (1)	CZ287261B6 (fr)
DE (2)	DE59502637D1 (fr)
DK (2)	DK0684236T4 (fr)
ES (2)	ES2120099T5 (fr)
FI (2)	FI109119B (fr)
HU (3)	HU219986B (fr)
NO (2)	NO306461B1 (fr)
PL (1)	PL190855B1 (fr)
PT (1)	PT816344E (fr)
SK (1)	SK282208B6 (fr)
TW (1)	TW442474B (fr)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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1995
- 1995-03-30 CA CA002145928A patent/CA2145928C/fr not_active Expired - Fee Related
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Also Published As

Publication number	Publication date
CA2145928C (fr)	2007-10-09
JP3811966B2 (ja)	2006-08-23
EP0816344B1 (fr)	2003-06-18
SK54195A3 (en)	1995-11-08
US5693800A (en)	1997-12-02
DK0684236T4 (da)	2008-05-05
JPH07300466A (ja)	1995-11-14
FI109119B (fi)	2002-05-31
ATE243200T1 (de)	2003-07-15
CA2145928A1 (fr)	1995-10-28
HU219716B (hu)	2001-06-28
JP2006199707A (ja)	2006-08-03
CN1193991C (zh)	2005-03-23
CZ287261B6 (en)	2000-10-11
ES2201229T3 (es)	2004-03-16
EP0816344A1 (fr)	1998-01-07
HU0003725D0 (fr)	1995-04-26
PT816344E (pt)	2003-10-31
EP0684236B2 (fr)	2007-12-26
CZ106795A3 (en)	1995-11-15
FI20011433L (fi)	2001-07-02
NO984588D0 (no)	1998-10-01
NO984588L (no)	1995-10-30
EP0684236A3 (fr)	1996-07-17
CN1113237A (zh)	1995-12-13
ES2120099T3 (es)	1998-10-16
EP0684236A2 (fr)	1995-11-29
TW442474B (en)	2001-06-23
DK0684236T3 (da)	1998-11-02
KR100327996B1 (ko)	2002-07-27
ATE167672T1 (de)	1998-07-15
HU219986B (hu)	2001-10-28
DK0816344T3 (da)	2003-10-06
FI952009A0 (fi)	1995-04-27
HUT70700A (en)	1995-10-30
PL190855B1 (pl)	2006-02-28
JP4525625B2 (ja)	2010-08-18
US5663340A (en)	1997-09-02
NO951594D0 (no)	1995-04-26
HU0003724D0 (fr)	2000-11-28
CN1065862C (zh)	2001-05-16
FI109693B (fi)	2002-09-30
HU219712B (hu)	2001-06-28
NO951594L (no)	1995-10-30
US5583226A (en)	1996-12-10
NO306461B1 (no)	1999-11-08
NO306859B1 (no)	2000-01-03
CN1259517A (zh)	2000-07-12
FI952009L (fi)	1995-10-28
EP0684236B1 (fr)	1998-06-24
ES2120099T5 (es)	2008-05-16
PL308394A1 (en)	1995-10-30
US5744601A (en)	1998-04-28
KR950032143A (ko)	1995-12-20
DE59510726D1 (de)	2003-07-24
HU9501194D0 (en)	1995-06-28
DE59502637D1 (de)	1998-07-30

Legal Events

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2013-01-02	MM4A	Patent lapsed due to non-payment of maintenance fees	Effective date: 20120426

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SK282208B6 (sk)	2001-12-03	Spôsob výroby 2,5-diamino-4,6-dichlórpyrimidínu a jeho formamidu, n-(2-amino-4,6-dichlórpyrimidin-5-yl)formamid a 4,6-dichlórpyrimidíny
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CA2230894A1 (fr)	1997-03-13	Carboxamides de pyrimidine et composes associes, et methodes de traitement d'etats inflammatoires
AU2009242076B2 (en)	2013-10-10	Process for the preparation of 5-(2-amino-pyrimidin-4-yl)-2-aryl-1H-pyrrole-3-carboxamides
SK279618B6 (sk)	1999-01-11	N-5-chránené 2,5-diamino-4,6-dichlórpyrimidíny a s
CA2512305C (fr)	2010-06-01	Un procede de production de 2,5-diamino-4,6-dichloropyrimidine
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CN102438994A (zh)	2012-05-02	制备嘧啶衍生物的方法
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US7619084B2 (en)	2009-11-17	Process for preparing 4-aminopyrimidine compound
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JPH0625157B2 (ja)	1994-04-06	４―ヒドロキシピリミジン類の製造方法