CH502339A - Verfahren zur Herstellung neuer substituierter Aminopyridine - Google Patents
Verfahren zur Herstellung neuer substituierter AminopyridineInfo
- Publication number
- CH502339A CH502339A CH666467A CH666467A CH502339A CH 502339 A CH502339 A CH 502339A CH 666467 A CH666467 A CH 666467A CH 666467 A CH666467 A CH 666467A CH 502339 A CH502339 A CH 502339A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- radicals
- groups
- amino
- group
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- RGJOEKWQDUBAIZ-IBOSZNHHSA-N CoASH Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCS)O[C@H]1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-IBOSZNHHSA-N 0.000 title abstract 4
- 229940093530 coenzyme a Drugs 0.000 title abstract 4
- 238000000034 method Methods 0.000 claims abstract description 16
- -1 carbalkoxy Chemical group 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 235000010233 benzoic acid Nutrition 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000005035 acylthio group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 150000001727 carbonic acid monoesters Chemical class 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000001559 benzoic acids Chemical class 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims 1
- STUHQDIOZQUPGP-UHFFFAOYSA-N morpholin-4-ium-4-carboxylate Chemical compound OC(=O)N1CCOCC1 STUHQDIOZQUPGP-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 3
- 241000186146 Brevibacterium Species 0.000 abstract 3
- RGJOEKWQDUBAIZ-UHFFFAOYSA-N coenzime A Natural products OC1C(OP(O)(O)=O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-UHFFFAOYSA-N 0.000 abstract 3
- 239000005516 coenzyme A Substances 0.000 abstract 3
- KDTSHFARGAKYJN-UHFFFAOYSA-N dephosphocoenzyme A Natural products OC1C(O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 KDTSHFARGAKYJN-UHFFFAOYSA-N 0.000 abstract 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- 241000186216 Corynebacterium Species 0.000 abstract 2
- 241000589516 Pseudomonas Species 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 244000005700 microbiome Species 0.000 abstract 2
- 241000186063 Arthrobacter Species 0.000 abstract 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 abstract 1
- 241000187694 Rhodococcus fascians Species 0.000 abstract 1
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 150000001720 carbohydrates Chemical class 0.000 abstract 1
- 235000014633 carbohydrates Nutrition 0.000 abstract 1
- 235000021466 carotenoid Nutrition 0.000 abstract 1
- 150000001747 carotenoids Chemical class 0.000 abstract 1
- 239000001963 growth medium Substances 0.000 abstract 1
- 150000003431 steroids Chemical class 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 230000010933 acylation Effects 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WERABQRUGJIMKQ-UHFFFAOYSA-N 6-chloro-3-nitropyridin-2-amine Chemical compound NC1=NC(Cl)=CC=C1[N+]([O-])=O WERABQRUGJIMKQ-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 230000001376 precipitating effect Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- BAZVFQBTJPBRTJ-UHFFFAOYSA-N 2-chloro-5-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C(Cl)N=C1 BAZVFQBTJPBRTJ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 description 1
- NJYFRQQXXXRJHK-UHFFFAOYSA-N (4-aminophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1 NJYFRQQXXXRJHK-UHFFFAOYSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- DTGGNTMERRTPLR-UHFFFAOYSA-N 1,2-diphenylethanamine Chemical compound C=1C=CC=CC=1C(N)CC1=CC=CC=C1 DTGGNTMERRTPLR-UHFFFAOYSA-N 0.000 description 1
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 1
- NCJKSYXFAADORS-UHFFFAOYSA-N 2-n-(pyridin-2-ylmethyl)pyridine-2,5-diamine Chemical compound N1=CC(N)=CC=C1NCC1=CC=CC=N1 NCJKSYXFAADORS-UHFFFAOYSA-N 0.000 description 1
- RXIMIBAZIQKSFF-UHFFFAOYSA-N 2-n-benzylpyridine-2,5-diamine Chemical compound N1=CC(N)=CC=C1NCC1=CC=CC=C1 RXIMIBAZIQKSFF-UHFFFAOYSA-N 0.000 description 1
- DKULSTMKCYRQCP-UHFFFAOYSA-N 2-phenylethyl carbonochloridate Chemical compound ClC(=O)OCCC1=CC=CC=C1 DKULSTMKCYRQCP-UHFFFAOYSA-N 0.000 description 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- SZVXACKCKQCFMT-UHFFFAOYSA-N 5-nitro-n-(pyridin-2-ylmethyl)pyridin-2-amine Chemical compound N1=CC([N+](=O)[O-])=CC=C1NCC1=CC=CC=N1 SZVXACKCKQCFMT-UHFFFAOYSA-N 0.000 description 1
- ZVCIIRBNNSUNCH-UHFFFAOYSA-N 6-n-[(4-fluorophenyl)methyl]-3-nitropyridine-2,6-diamine Chemical compound C1=C([N+]([O-])=O)C(N)=NC(NCC=2C=CC(F)=CC=2)=C1 ZVCIIRBNNSUNCH-UHFFFAOYSA-N 0.000 description 1
- LAZNAMZDZMZYPR-UHFFFAOYSA-N 6-n-benzylpyridine-2,3,6-triamine Chemical compound N1=C(N)C(N)=CC=C1NCC1=CC=CC=C1 LAZNAMZDZMZYPR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- SHTIFNOCYQHYLC-UHFFFAOYSA-N Cl.NC1=NC(=CC=C1NC(C=C)=O)NCC1=CC=CC=C1 Chemical compound Cl.NC1=NC(=CC=C1NC(C=C)=O)NCC1=CC=CC=C1 SHTIFNOCYQHYLC-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- OLPRNYAGDJRKRD-UHFFFAOYSA-N N-[6-(pyridin-2-ylmethylamino)pyridin-3-yl]propanamide Chemical compound CCC(=O)NC1=CN=C(NCC2=NC=CC=C2)C=C1 OLPRNYAGDJRKRD-UHFFFAOYSA-N 0.000 description 1
- KPHXFXIJXGYUJU-UHFFFAOYSA-N NC1=NC(=CC=C1N)CC1=CC(=CC=C1)C(F)(F)F Chemical compound NC1=NC(=CC=C1N)CC1=CC(=CC=C1)C(F)(F)F KPHXFXIJXGYUJU-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- SBXJERWDNDIHAR-UHFFFAOYSA-N [6-amino-5-(propoxycarbonylamino)pyridin-2-yl]-benzylazanium chloride Chemical compound Cl.NC1=NC(=CC=C1NC(=O)OCCC)NCC1=CC=CC=C1 SBXJERWDNDIHAR-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- GIUICJKMNNJFFZ-UHFFFAOYSA-N benzyl-[5-(ethoxycarbonylamino)pyridin-2-yl]azanium chloride Chemical compound [Cl-].CCOC(=O)Nc1ccc([NH2+]Cc2ccccc2)nc1 GIUICJKMNNJFFZ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- QQKDTTWZXHEGAQ-UHFFFAOYSA-N propyl carbonochloridate Chemical compound CCCOC(Cl)=O QQKDTTWZXHEGAQ-UHFFFAOYSA-N 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridine hydrochloride Substances [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- 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
- C07D213/79—Acids; Esters
-
- 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
- C07D213/84—Nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED0050093 | 1966-05-12 | ||
| DE1670522A DE1670522C3 (de) | 1966-05-12 | 1966-05-12 | Neue Benzylaminopyridine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH502339A true CH502339A (de) | 1971-01-31 |
Family
ID=25972357
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH666467A CH502339A (de) | 1966-05-12 | 1967-05-11 | Verfahren zur Herstellung neuer substituierter Aminopyridine |
| CH666367A CH555828A (de) | 1966-05-12 | 1967-05-11 | Verfahren zur herstellung neuer substituierter aminopyridine. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH666367A CH555828A (de) | 1966-05-12 | 1967-05-11 | Verfahren zur herstellung neuer substituierter aminopyridine. |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US3481943A (2) |
| BE (1) | BE698384A (2) |
| CH (2) | CH502339A (2) |
| DE (2) | DE1670522C3 (2) |
| DK (1) | DK119978B (2) |
| ES (1) | ES340336A2 (2) |
| FI (1) | FI49301C (2) |
| FR (1) | FR6877M (2) |
| GB (1) | GB1191302A (2) |
| NL (1) | NL139972B (2) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0000816A1 (en) * | 1977-08-06 | 1979-02-21 | Beecham Group Plc | Substituted amino-pyridine derivatives, processes for their preparation and pharmaceutical compositions containing them |
| DE3369315D1 (en) * | 1982-10-27 | 1987-02-26 | Degussa | Derivatives of 2-amino-3-acylamino-6-benzylamino pyridine with an anti-epileptic activity |
| CA1224788A (en) * | 1984-02-21 | 1987-07-28 | Edward R. Lavagnino | Diaminopyridines via hydrogenation of nitrobenzylaminopyridines |
| NO860825L (no) * | 1985-03-23 | 1986-09-24 | Degussa | Fremgangsmaate til fremstilling av 2-amino-3-nitro-6-(4-fluor-benzylamino)-pyridin samt 2-amino-3-karbetoksyamino-6-(4-fluor-benzylamino)-pyridin. |
| MC2029A1 (fr) * | 1988-05-16 | 1990-04-25 | Asta Pharma Ag | (n-heterocyclyl)-3 diamino-2,6 pyridines substituees et leurs n-oxydes,preparation de ces composes et leur application comme medicaments |
| US6022884A (en) | 1997-11-07 | 2000-02-08 | Amgen Inc. | Substituted pyridine compounds and methods of use |
| EP1688141A1 (en) * | 2005-01-31 | 2006-08-09 | elbion AG | The use of flupirtine for the treatment of overactive bladder and associated diseases, and for the treatment of irritable bowel syndrome |
| US20080279930A1 (en) * | 2007-05-07 | 2008-11-13 | Bernd Terhaag | Controlled-Release Flupirtine Compositions, Compacts, Kits and Methods of Making and Use Thereof |
| CN102241626B (zh) * | 2011-05-03 | 2013-07-03 | 北京华睿鼎信科技有限公司 | 一种马来酸氟吡汀的合成工艺 |
| CN102850265B (zh) * | 2011-06-29 | 2015-11-25 | 陈小花 | 一种氟吡汀偶联物及其制备方法和用途 |
| CN102351786A (zh) * | 2011-11-01 | 2012-02-15 | 东南大学 | 一种氟吡汀丙二酸盐及其制备方法 |
| WO2013080215A1 (en) | 2011-11-30 | 2013-06-06 | Arch Pharmalabs Limited | An improved process for the preparation of flupirtine and pharmaceutically acceptable salts thereof |
| CN103910674B (zh) * | 2013-12-19 | 2015-12-02 | 天津红日药业股份有限公司 | 用于马来酸氟吡汀分析中的参比化合物 |
| WO2019014547A1 (en) * | 2017-07-14 | 2019-01-17 | Texas Tech University System | FUNCTIONALIZED PYRIDINE CARBAMATES HAVING ENHANCED NEUROPROTECTOR ACTIVITY |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL132603C (2) * | 1964-08-29 | |||
| FR1462263A (fr) * | 1964-08-29 | 1966-04-15 | Degussa | Procédé de préparation de nouvelles diaminopyridines substituées |
-
1966
- 1966-05-12 DE DE1670522A patent/DE1670522C3/de not_active Expired
- 1966-05-12 DE DE19661670523 patent/DE1670523A1/de active Pending
-
1967
- 1967-04-27 NL NL676705973A patent/NL139972B/xx not_active IP Right Cessation
- 1967-05-10 ES ES340336A patent/ES340336A2/es not_active Expired
- 1967-05-10 US US637322A patent/US3481943A/en not_active Expired - Lifetime
- 1967-05-11 DK DK248867AA patent/DK119978B/da unknown
- 1967-05-11 CH CH666467A patent/CH502339A/de not_active IP Right Cessation
- 1967-05-11 CH CH666367A patent/CH555828A/xx not_active IP Right Cessation
- 1967-05-11 BE BE698384D patent/BE698384A/xx unknown
- 1967-05-12 FI FI671370A patent/FI49301C/fi active
- 1967-05-12 GB GB22222/67A patent/GB1191302A/en not_active Expired
- 1967-07-11 FR FR105743A patent/FR6877M/fr not_active Expired
-
1969
- 1969-07-25 US US845058A patent/US3513171A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| BE698384A (2) | 1967-10-16 |
| NL6705973A (2) | 1967-11-13 |
| FI49301C (fi) | 1975-05-12 |
| US3513171A (en) | 1970-05-19 |
| FI49301B (2) | 1975-01-31 |
| NL139972B (nl) | 1973-10-15 |
| FR6877M (2) | 1969-04-14 |
| CH555828A (de) | 1974-11-15 |
| GB1191302A (en) | 1970-05-13 |
| DE1670522A1 (de) | 1970-11-12 |
| ES340336A2 (es) | 1968-06-01 |
| DE1670522C3 (de) | 1978-08-31 |
| DE1670522B2 (de) | 1977-12-15 |
| DK119978B (da) | 1971-03-22 |
| DE1670523A1 (de) | 1970-12-03 |
| US3481943A (en) | 1969-12-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH502339A (de) | Verfahren zur Herstellung neuer substituierter Aminopyridine | |
| CH493528A (de) | Verfahren zur Herstellung neuer substituierter Aminopyrimidine | |
| DE2366625C2 (2) | ||
| CH620899A5 (2) | ||
| CH522603A (de) | Verfahren zur Herstellung von substituierten Pyridylharnstoffen | |
| DE834102C (de) | Verfahren zur Herstellung neuer Tropasaeureabkoemmlinge | |
| US2540946A (en) | Pyridoxal-histamine and processes for preparing the same | |
| DE812316C (de) | Verfahren zur Herstellung von 2-(p-Aminobenzolsulfonamido)-4-methylpyrimidin | |
| DE2008692A1 (de) | Verfahren zur Herstellung von Indol-3carbonsäurederivaten und nach dem Verfahren erhältliche, neue Verbindungen | |
| US3671535A (en) | 4-imino-oxazolidin-2-ones and process of preparation | |
| EP0004611A1 (de) | Verfahren zur Herstellung von Acetoacetylarylamiden | |
| DE2649855C2 (de) | Substituierte 5-Acetyl-4-hydroxy-3-phenylamino-2H-pyran-2,6(3H)-dione, Verfahren zu deren Herstellung und deren Verwendung | |
| AT270647B (de) | Verfahren zur Herstellung neuer substituierter Aminopyridine, von deren Salzen und optisch aktiven Isomeren | |
| DE2151487A1 (de) | Pharmazeutische Massen | |
| EP0039835B1 (de) | Verfahren zur Herstellung von 2-Amino-6-nitrobenzthiazol | |
| US2476464A (en) | Intermediates for the production of vitamin b6 and processes of preparing the same | |
| DE2142792A1 (de) | Heterocyclische Verbindungen | |
| AT258904B (de) | Verfahren zur Herstellung neuer substituierter Aminopyridine | |
| AT284126B (de) | Verfahren zur Herstellung neuer substituierter Aminopyrimidine und deren Salze und optisch aktiven Isomere | |
| AT267527B (de) | Verfahren zur Herstellung neuer substituierter Aminopyridine, von deren Salzen und optisch aktiven Isomeren | |
| AT266075B (de) | Verfahren zur Herstellung von neuen Sulfonaniliden und deren Säureadditions- und Metallsalzen | |
| AT255418B (de) | Verfahren zur Herstellung von neuen Sulfonamiden und ihren Salzen | |
| DE974506C (de) | Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen | |
| AT238193B (de) | Verfahren zur Herstellung von neuen Triazolidinen | |
| CH655930A5 (de) | Verfahren zur herstellung von 3-hydroxybenzdiazepinonen. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |