NO800868L - Fremgangsmaate til fremstilling av 2,6-diaminonbularin-forbindelser - Google Patents

Fremgangsmaate til fremstilling av 2,6-diaminonbularin-forbindelser

Info

Publication number: NO800868L
Authority: NO; Norway
Prior art keywords: compound; amino; substituted; reaction; formula
Prior art date: 1979-04-02

Application number

NO800868A

Other languages

English (en)

Norwegian (no)

Inventor

Yoichi Sawa

Yoshiyuki Kawakami

Ryuji Marumoto

Original Assignee

Takeda Chemical Industries Ltd

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.)

1979-04-02

Filing date

1980-03-25

Publication date

1980-10-03

1980-03-25 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

1980-10-03 Publication of NO800868L publication Critical patent/NO800868L/no

Links

150000001875 compounds Chemical class 0.000 title claims description 57
238000000034 method Methods 0.000 title claims description 42
238000002360 preparation method Methods 0.000 title claims description 3
238000006243 chemical reaction Methods 0.000 claims description 33
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 30
RTRQQBHATOEIAF-UUOKFMHZSA-N acadesine Chemical compound NC1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 RTRQQBHATOEIAF-UUOKFMHZSA-N 0.000 claims description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
125000006239 protecting group Chemical group 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
ZBNZAJFNDPPMDT-UHFFFAOYSA-N 1h-imidazole-5-carboxamide Chemical compound NC(=O)C1=CNC=N1 ZBNZAJFNDPPMDT-UHFFFAOYSA-N 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 8
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
125000004414 alkyl thio group Chemical group 0.000 claims description 6
238000006297 dehydration reaction Methods 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
238000010511 deprotection reaction Methods 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
QRJZGVVKGFIGLI-UHFFFAOYSA-N 2-phenylguanidine Chemical compound NC(=N)NC1=CC=CC=C1 QRJZGVVKGFIGLI-UHFFFAOYSA-N 0.000 claims description 4
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000001589 carboacyl group Chemical group 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical class 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 2
125000005843 halogen group Chemical group 0.000 claims 2
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 2
150000002460 imidazoles Chemical class 0.000 claims 1
239000000203 mixture Substances 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
239000002904 solvent Substances 0.000 description 16
-1 2-substituted amino-inosine Chemical class 0.000 description 15
239000013078 crystal Substances 0.000 description 14
238000002844 melting Methods 0.000 description 14
230000008018 melting Effects 0.000 description 14
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
238000000921 elemental analysis Methods 0.000 description 12
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
238000001816 cooling Methods 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
238000001914 filtration Methods 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical class C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
NWVGXXPWOYZODV-UHFFFAOYSA-N 1h-imidazole-5-carbonitrile Chemical compound N#CC1=CN=CN1 NWVGXXPWOYZODV-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
210000005097 arteria cerebelosa anteroinferior Anatomy 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
239000012258 stirred mixture Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
XDSYAIICRRZSJX-UHFFFAOYSA-N carbamimidoyl(phenyl)azanium;hydrogen carbonate Chemical compound OC(O)=O.NC(N)=NC1=CC=CC=C1 XDSYAIICRRZSJX-UHFFFAOYSA-N 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
150000002905 orthoesters Chemical class 0.000 description 3
239000000047 product Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
ZDTFMPXQUSBYRL-UUOKFMHZSA-N 2-Aminoadenosine Chemical class C12=NC(N)=NC(N)=C2N=CN1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O ZDTFMPXQUSBYRL-UUOKFMHZSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000009825 accumulation Methods 0.000 description 2
125000001931 aliphatic 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
150000001412 amines Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
210000004351 coronary vessel Anatomy 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 1
HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
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 1
IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
HRVBGZYMNGAXAT-NFBAFIMDSA-N [(2r,3r,4r,5r)-5-(5-amino-4-cyanoimidazol-1-yl)-3,4-di(propanoyloxy)oxolan-2-yl]methyl propanoate Chemical compound CCC(=O)O[C@@H]1[C@H](OC(=O)CC)[C@@H](COC(=O)CC)O[C@H]1N1C(N)=C(C#N)N=C1 HRVBGZYMNGAXAT-NFBAFIMDSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
238000005915 ammonolysis reaction Methods 0.000 description 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 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
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
VAPIAHQTQHBYRF-UHFFFAOYSA-N carbonic acid;2-(4-ethoxyphenyl)guanidine Chemical compound OC(O)=O.CCOC1=CC=C(N=C(N)N)C=C1 VAPIAHQTQHBYRF-UHFFFAOYSA-N 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
230000000916 dilatatory effect Effects 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 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
230000002401 inhibitory effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
NROPRCUPBJFONT-UHFFFAOYSA-N methyl n'-phenylcarbamimidothioate Chemical compound CSC(N)=NC1=CC=CC=C1 NROPRCUPBJFONT-UHFFFAOYSA-N 0.000 description 1
125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-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
238000001953 recrystallisation Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/052—Imidazole radicals
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Life Sciences & Earth Sciences (AREA)
Saccharide Compounds (AREA)
Silver Salt Photography Or Processing Solution Therefor (AREA)
Luminescent Compositions (AREA)
Plural Heterocyclic Compounds (AREA)

NO800868A 1979-04-02 1980-03-25 Fremgangsmaate til fremstilling av 2,6-diaminonbularin-forbindelser NO800868L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP3956279A JPS55130998A (en)	1979-04-02	1979-04-02	N2-substituted 2,6-diaminonebularin

Publications (1)

Publication Number	Publication Date
NO800868L true NO800868L (no)	1980-10-03

Family

ID=12556512

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO800868A NO800868L (no)	1979-04-02	1980-03-25	Fremgangsmaate til fremstilling av 2,6-diaminonbularin-forbindelser

Country Status (12)

Country	Link
US (1)	US4293690A (da)
EP (1)	EP0017465A1 (da)
JP (1)	JPS55130998A (da)
AU (1)	AU5698280A (da)
DK (1)	DK134580A (da)
ES (1)	ES490101A0 (da)
FI (1)	FI801033A7 (da)
GR (1)	GR67615B (da)
IL (1)	IL59602A0 (da)
NO (1)	NO800868L (da)
NZ (1)	NZ193324A (da)
PH (1)	PH15849A (da)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS56152437U (da) *	1980-04-14	1981-11-14
JPS60193997A (ja) *	1984-03-14	1985-10-02	Sumitomo Chem Co Ltd	新規シアノイミダゾ−ルリボヌクレオシド誘導体およびその製造法
US4954504A (en) *	1986-11-14	1990-09-04	Ciba-Geigy Corporation	N9 -cyclopentyl-substituted adenine derivatives having adenosine-2 receptor stimulating activity
US5063233A (en) *	1986-11-14	1991-11-05	Ciba-Geigy Corporation	N9 -cyclopentyl-substituted adenine derivatives useful as adenosine receptor agonists
US4968697A (en) *	1987-02-04	1990-11-06	Ciba-Geigy Corporation	2-substituted adenosine 5'-carboxamides as antihypertensive agents
KR927003044A (ko) *	1990-01-11	1992-12-17	크리스토퍼 케이. 미라벨리	Rna 활성과 유전자 발현을 검출하고 조절하는 조성물 및 그 방법
US6262241B1 (en)	1990-08-13	2001-07-17	Isis Pharmaceuticals, Inc.	Compound for detecting and modulating RNA activity and gene expression
DE19718065A1 (de) *	1997-04-29	1998-11-05	Henkel Kgaa	Reinigungsmittel für nachvernetzende Polyurethan-Hotmelts
ES2192495B1 (es) *	2002-03-21	2005-02-16	Universidad De Barcelona	Nuevo uso terapeutico del ribosido de 5-aminoimidazol-4-carboxamida (acadesina).
AU2003221636B2 (en) *	2002-05-09	2009-11-12	Baker Idi Heart And Diabetes Institute Holdings Limited	Amino acid analogues
AU2005231440B9 (en) *	2004-04-02	2012-02-23	Dogwood Pharmaceuticals, Inc.	Selective antagonists of A2A adenosine receptors
CN119792485B (zh) *	2025-03-17	2025-06-24	温州医科大学附属口腔医院	一种抑菌促修复水凝胶敷料及制备方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3134778A (en) *	1963-08-20	1964-05-26	Smith Kline French Lab	2,5,7-triamino-4-phenyl (or thienyl)-pyrimido[4,5-d]pyrimidines
FR1535561A (fr) *	1966-06-18	1968-08-09	Ajinomoto Kk	Méthode de préparation de l'adénine, de ses dérivés et intermédiaires
US3857842A (en) *	1970-05-06	1974-12-31	Sagami Chem Res	Process for preparing purine compounds by reaction of a carbonitrile with formic acid
US3826803A (en) *	1972-02-17	1974-07-30	Icn Pharmaceuticals	Arabinofuranosyl-8-azaadenines
DE2359536C2 (de) *	1972-12-08	1984-08-02	Takeda Chemical Industries, Ltd., Osaka	2,6-Diaminonebularinderivate
US4056674A (en) *	1973-07-06	1977-11-01	Icn Pharmaceuticals, Inc.	Derivatives of 3-deazaguanine
JPS5461194A (en) *	1977-10-21	1979-05-17	Takeda Chem Ind Ltd	Preparation of n22substituted 2*66diaminonebularin

1979
- 1979-04-02 JP JP3956279A patent/JPS55130998A/ja active Pending
1980
- 1980-03-12 IL IL59602A patent/IL59602A0/xx unknown
- 1980-03-25 NO NO800868A patent/NO800868L/no unknown
- 1980-03-28 DK DK134580A patent/DK134580A/da unknown
- 1980-03-28 US US06/136,072 patent/US4293690A/en not_active Expired - Lifetime
- 1980-03-31 GR GR61579A patent/GR67615B/el unknown
- 1980-03-31 AU AU56982/80A patent/AU5698280A/en not_active Abandoned
- 1980-03-31 ES ES490101A patent/ES490101A0/es active Granted
- 1980-04-01 NZ NZ193324A patent/NZ193324A/xx unknown
- 1980-04-01 FI FI801033A patent/FI801033A7/fi not_active Application Discontinuation
- 1980-04-01 PH PH23848A patent/PH15849A/en unknown
- 1980-04-01 EP EP80301024A patent/EP0017465A1/en not_active Withdrawn

Also Published As

Publication number	Publication date
AU5698280A (en)	1980-10-09
US4293690A (en)	1981-10-06
IL59602A0 (en)	1980-06-30
DK134580A (da)	1980-10-03
FI801033A7 (fi)	1981-01-01
EP0017465A1 (en)	1980-10-15
NZ193324A (en)	1982-09-07
PH15849A (en)	1983-04-13
ES8104323A1 (es)	1981-04-01
JPS55130998A (en)	1980-10-11
GR67615B (da)	1981-08-31
ES490101A0 (es)	1981-04-01

Publication	Publication Date	Title
DK1797037T3 (da)	2015-03-30	Fremgangsmåde til fremstilling af 4-{4-[({[4-chlor-3-(trifluormethyl)phenyl]amino}carbonyl)amino]phenyoxy}n-methylpyridin-2-carboxamid
SU691089A3 (ru)	1979-10-05	Способ получени карбонилзамещенных 1-сульфонилбензимидазолов
NO800868L (no)	1980-10-03	Fremgangsmaate til fremstilling av 2,6-diaminonbularin-forbindelser
DK149623B (da)	1986-08-18	Fremgangsmaade til fremstilling af alfa-hydroxycarboxylsyreamider
FI59991B (fi)	1981-07-31	Foerfarande foer framstaellning av 2-arylamino-2-imidazolin-derivat och deras salter
US4255565A (en)	1981-03-10	Production of 2,6-diaminonebularines
CN113072436A (zh)	2021-07-06	一种苄基芳基醚的制备方法
US5116993A (en)	1992-05-26	Process for the preparation of 2-chloro-5-chloromethylpyridine, and new intermediates
US5391733A (en)	1995-02-21	Synthesis intermediates for 2-amino-6-halogenopurines
JPH0597840A (ja)	1993-04-20	３−アシルアミノ−６−フエニルオキシ−７−アルキルスルホニルアミノ−４ｈ−１−ベンゾピラン−４−オンまたはその塩の製造法
JPH0570437A (ja)	1993-03-23	１−カルバモイルピラゾールの製造方法
GB1597428A (en)	1981-09-09	Manufacture of pyridoxin
JPH05125072A (ja)	1993-05-21	３−アシルアミノ−６−フエニルオキシ−７−アルキルスルホニルアミノ−４ｈ−１−ベンゾピラン−４−オン誘導体またはその塩の製造法
US5663434A (en)	1997-09-02	Process for preparing N-(3-amino-4-chlorophenyl) acylamides
US4423219A (en)	1983-12-27	Production of purine derivatives and intermediates therefor
US4236017A (en)	1980-11-25	Process for synthesizing 2-substituted semicarbazones and carbalkoxy hydrazones
US3247224A (en)	1966-04-19	6h-[b, f] [1, 4, 5] dibenzo-oxathiazepins
US5162529A (en)	1992-11-10	Process for the preparation of 5-hydroxy-3,4,5,6-tetrahydro-pyrimidine derivatives
KR810001172B1 (ko)	1981-09-25	N²-치환-2,6-디아미노네불라린의 제조방법
CN113956209B (zh)	2022-11-29	Nh-1,2,3-三氮唑类化合物的制备方法
CZ150893A3 (en)	1994-03-16	Process for preparing imidazopyridines
HU198179B (en)	1989-08-28	Process for producing n-methyl-1-alkylthio-2-nitroethenamine derivatives
PL164340B1 (pl)	1994-07-29	Sposób wytwarzania nowych pochodnych benzotiazyny PL PL
JP4126944B2 (ja)	2008-07-30	５−アミノ−４−ニトロソピラゾール化合物の製法
KR950009482B1 (ko)	1995-08-23	2,5-디메톡시-4-할로아닐린의 제조방법