NO122420B - - Google Patents
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- Publication number
- NO122420B NO122420B NO16659167A NO16659167A NO122420B NO 122420 B NO122420 B NO 122420B NO 16659167 A NO16659167 A NO 16659167A NO 16659167 A NO16659167 A NO 16659167A NO 122420 B NO122420 B NO 122420B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- general formula
- pyridyl
- mol
- reactive functional
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 27
- 150000001408 amides Chemical class 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 150000001336 alkenes Chemical class 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 150000003927 aminopyridines Chemical class 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 3
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005108 alkenylthio group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 150000007513 acids Chemical class 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 238000003756 stirring Methods 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 206010028980 Neoplasm Diseases 0.000 description 11
- 239000005457 ice water Substances 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- -1 alkenoyloxy Chemical group 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- MZFGYVZYLMNXGL-UHFFFAOYSA-N undec-10-enoyl chloride Chemical compound ClC(=O)CCCCCCCCC=C MZFGYVZYLMNXGL-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- LYAAAQLCYAWSNY-UHFFFAOYSA-N N-(5-bromopyridin-2-yl)undec-10-enamide Chemical compound BrC=1C=CC(=NC1)NC(CCCCCCCCC=C)=O LYAAAQLCYAWSNY-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 3
- GZBKVUGZEAJYHH-UHFFFAOYSA-N 2-nitropyridin-3-amine Chemical class NC1=CC=CN=C1[N+]([O-])=O GZBKVUGZEAJYHH-UHFFFAOYSA-N 0.000 description 3
- WGOLHUGPTDEKCF-UHFFFAOYSA-N 5-bromopyridin-2-amine Chemical compound NC1=CC=C(Br)C=N1 WGOLHUGPTDEKCF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- PYHRTEMNNKXNFY-UHFFFAOYSA-N CC=1C=CC(=NC1)NC(CCCCCCCCC=C)=O Chemical compound CC=1C=CC(=NC1)NC(CCCCCCCCC=C)=O PYHRTEMNNKXNFY-UHFFFAOYSA-N 0.000 description 3
- 201000009030 Carcinoma Diseases 0.000 description 3
- DGFZBFBMTVPXRT-UHFFFAOYSA-N N-(5-aminopyridin-2-yl)undec-10-enamide Chemical compound NC=1C=CC(=NC1)NC(CCCCCCCCC=C)=O DGFZBFBMTVPXRT-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IZDWAVKOOZQYPX-VNKDHWASSA-N (2E,4E)-N-(6-acetamidopyridin-3-yl)hexa-2,4-dienamide Chemical compound C(C)(=O)NC1=CC=C(C=N1)NC(\C=C\C=C\C)=O IZDWAVKOOZQYPX-VNKDHWASSA-N 0.000 description 2
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CMBSSVKZOPZBKW-UHFFFAOYSA-N 5-methylpyridin-2-amine Chemical compound CC1=CC=C(N)N=C1 CMBSSVKZOPZBKW-UHFFFAOYSA-N 0.000 description 2
- VVLPQYRZXQIATJ-UHFFFAOYSA-N 6-propoxypyridin-3-amine Chemical compound CCCOC1=CC=C(N)C=N1 VVLPQYRZXQIATJ-UHFFFAOYSA-N 0.000 description 2
- BHIZQSKWXGRDKP-UHFFFAOYSA-N C(C)OC(=O)C=1C=CC(=NC1)NC(CCCCCCCCC=C)=O Chemical compound C(C)OC(=O)C=1C=CC(=NC1)NC(CCCCCCCCC=C)=O BHIZQSKWXGRDKP-UHFFFAOYSA-N 0.000 description 2
- DLYRGPGQNMXGRT-UHFFFAOYSA-N C(CC)OC1=CC=C(C=N1)NC(CCCCCCCCC(CBr)Br)=O Chemical compound C(CC)OC1=CC=C(C=N1)NC(CCCCCCCCC(CBr)Br)=O DLYRGPGQNMXGRT-UHFFFAOYSA-N 0.000 description 2
- BPMDMVNHEHUICK-UHFFFAOYSA-N C(CCCCCCCCCCC)(=O)NC=1C=NC(=CC1)OCCC Chemical compound C(CCCCCCCCCCC)(=O)NC=1C=NC(=CC1)OCCC BPMDMVNHEHUICK-UHFFFAOYSA-N 0.000 description 2
- VWBJSIAAMRDIHB-UHFFFAOYSA-N CC=1C=CC(=NC1)NC(C=CC=CC)=O Chemical compound CC=1C=CC(=NC1)NC(C=CC=CC)=O VWBJSIAAMRDIHB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- RHRSVKYIPGQVMB-UHFFFAOYSA-N IC=1C=CC(=NC1)NC(CCCCCCCCC=C)=O Chemical compound IC=1C=CC(=NC1)NC(CCCCCCCCC=C)=O RHRSVKYIPGQVMB-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- XBUFQJJIAYRHEW-UHFFFAOYSA-N N-(6-acetamidopyridin-3-yl)undec-10-enamide Chemical compound C(C)(=O)NC1=CC=C(C=N1)NC(CCCCCCCCC=C)=O XBUFQJJIAYRHEW-UHFFFAOYSA-N 0.000 description 2
- BAHGRUMDQJFQEC-UHFFFAOYSA-N N-(6-ethylsulfanylpyridin-3-yl)undec-10-enamide Chemical compound C(C)SC1=CC=C(C=N1)NC(CCCCCCCCC=C)=O BAHGRUMDQJFQEC-UHFFFAOYSA-N 0.000 description 2
- 206010039491 Sarcoma Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 150000007530 organic bases Chemical group 0.000 description 2
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- 229960002703 undecylenic acid Drugs 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- IJENIWQCIGAZAL-MQQKCMAXSA-N (2e,4e)-n-(5-bromopyridin-2-yl)hexa-2,4-dienamide Chemical compound C\C=C\C=C\C(=O)NC1=CC=C(Br)C=N1 IJENIWQCIGAZAL-MQQKCMAXSA-N 0.000 description 1
- XWRIGYHJJSGAJZ-UHFFFAOYSA-N (4-nitrophenyl) undec-10-enoate Chemical compound [O-][N+](=O)C1=CC=C(OC(=O)CCCCCCCCC=C)C=C1 XWRIGYHJJSGAJZ-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- VVNKZWYJHLKFAD-UHFFFAOYSA-N 1-benzyl-9,10-dimethylanthracene Chemical compound CC=1C2=CC=CC=C2C(=C2C=CC=C(C=12)CC1=CC=CC=C1)C VVNKZWYJHLKFAD-UHFFFAOYSA-N 0.000 description 1
- IITCDZXAXQNBIR-UHFFFAOYSA-N 1-imidazol-1-ylundec-10-en-1-one Chemical compound C(CCCCCCCCC=C)(=O)N1C=NC=C1 IITCDZXAXQNBIR-UHFFFAOYSA-N 0.000 description 1
- CYQUTDGVVUGBRD-UHFFFAOYSA-N 10,11-dibromoundecanoyl chloride Chemical compound ClC(=O)CCCCCCCCC(Br)CBr CYQUTDGVVUGBRD-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 1
- WBEFYFVYUOCBJL-UHFFFAOYSA-N 2-ethyl-n-(5-methylpyridin-2-yl)hexanamide Chemical compound CCCCC(CC)C(=O)NC1=CC=C(C)C=N1 WBEFYFVYUOCBJL-UHFFFAOYSA-N 0.000 description 1
- VLZDKSSWOQPPMU-UHFFFAOYSA-N 3,5,5-trimethyl-N-(4-methylpyridin-2-yl)hexanamide Chemical compound CC1=CC(=NC=C1)NC(CC(CC(C)(C)C)C)=O VLZDKSSWOQPPMU-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- IVILGUFRMDBUEQ-UHFFFAOYSA-N 5-iodopyridin-2-amine Chemical compound NC1=CC=C(I)C=N1 IVILGUFRMDBUEQ-UHFFFAOYSA-N 0.000 description 1
- UGSBCCAHDVCHGI-UHFFFAOYSA-N 5-nitropyridin-2-amine Chemical compound NC1=CC=C([N+]([O-])=O)C=N1 UGSBCCAHDVCHGI-UHFFFAOYSA-N 0.000 description 1
- YFFHQSIIVNBIGD-UHFFFAOYSA-N 5-propoxypyridin-2-amine Chemical compound CCCOC1=CC=C(N)N=C1 YFFHQSIIVNBIGD-UHFFFAOYSA-N 0.000 description 1
- QPNSNROGWGPVOE-UHFFFAOYSA-N 6-ethylsulfanylpyridin-3-amine Chemical compound CCSC1=CC=C(N)C=N1 QPNSNROGWGPVOE-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- RVMNTZNXQQTMRC-UHFFFAOYSA-N C(C)(=O)NC1=CC=C(C=N1)NC(CCCCCCCCCCCC)=O Chemical compound C(C)(=O)NC1=CC=C(C=N1)NC(CCCCCCCCCCCC)=O RVMNTZNXQQTMRC-UHFFFAOYSA-N 0.000 description 1
- FRFJWLUTDLSVOX-UHFFFAOYSA-N C(C)OC(=O)C=1C=CC(=NC1)NC(C=CC=CC)=O Chemical compound C(C)OC(=O)C=1C=CC(=NC1)NC(C=CC=CC)=O FRFJWLUTDLSVOX-UHFFFAOYSA-N 0.000 description 1
- QTRSOAOLDMYDBP-UHFFFAOYSA-N C(C)OC(=O)C=1C=CC(=NC1)NC(CC(CC(C)(C)C)C)=O Chemical compound C(C)OC(=O)C=1C=CC(=NC1)NC(CC(CC(C)(C)C)C)=O QTRSOAOLDMYDBP-UHFFFAOYSA-N 0.000 description 1
- SUWGIVPVHWCQOQ-UHFFFAOYSA-N C(CC)OC1=CC=C(C=N1)NC(C=CCCCCCC)=O Chemical compound C(CC)OC1=CC=C(C=N1)NC(C=CCCCCCC)=O SUWGIVPVHWCQOQ-UHFFFAOYSA-N 0.000 description 1
- KPLUSZGTKTVGFB-UHFFFAOYSA-N C(CC)OC1=CC=C(C=N1)NC(CCCCCCCCC)=O Chemical compound C(CC)OC1=CC=C(C=N1)NC(CCCCCCCCC)=O KPLUSZGTKTVGFB-UHFFFAOYSA-N 0.000 description 1
- YELZYPKSUPRIOU-UHFFFAOYSA-N C(CC)OC1=CC=C(C=N1)NC(CCCCCCCCCC)=O Chemical compound C(CC)OC1=CC=C(C=N1)NC(CCCCCCCCCC)=O YELZYPKSUPRIOU-UHFFFAOYSA-N 0.000 description 1
- BYINANHFQQZOGZ-UHFFFAOYSA-N CC=1C=CC=C2C=3C=C4C=CC=C5CCC(C3C=CC12)=C54 Chemical compound CC=1C=CC=C2C=3C=C4C=CC=C5CCC(C3C=CC12)=C54 BYINANHFQQZOGZ-UHFFFAOYSA-N 0.000 description 1
- CCJYYRRJJTXMSF-UHFFFAOYSA-N CN(C(CCCCCCCCC=C)=O)C1=NC=C(C=C1)C Chemical compound CN(C(CCCCCCCCC=C)=O)C1=NC=C(C=C1)C CCJYYRRJJTXMSF-UHFFFAOYSA-N 0.000 description 1
- 101100401100 Caenorhabditis elegans mes-1 gene Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- FXNFFCMITPHEIT-UHFFFAOYSA-N Ethyl 10-undecenoate Chemical compound CCOC(=O)CCCCCCCCC=C FXNFFCMITPHEIT-UHFFFAOYSA-N 0.000 description 1
- 208000009889 Herpes Simplex Diseases 0.000 description 1
- 208000007514 Herpes zoster Diseases 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 241000712431 Influenza A virus Species 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 241000710769 Louping ill virus Species 0.000 description 1
- UKTQGMASWHRVRA-UHFFFAOYSA-N N-(5-chloropyridin-2-yl)-3-ethylhex-2-enamide Chemical compound ClC=1C=CC(=NC=1)NC(C=C(CCC)CC)=O UKTQGMASWHRVRA-UHFFFAOYSA-N 0.000 description 1
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- FXIMVPFWLGHJLV-UHFFFAOYSA-N N-(6-propoxypyridin-3-yl)nonanamide Chemical compound C(CC)OC1=CC=C(C=N1)NC(CCCCCCCC)=O FXIMVPFWLGHJLV-UHFFFAOYSA-N 0.000 description 1
- UAIJIOMZGPXEPN-UHFFFAOYSA-N N-(6-propoxypyridin-3-yl)octanamide Chemical compound C(CCCCCCC)(=O)NC=1C=NC(=CC1)OCCC UAIJIOMZGPXEPN-UHFFFAOYSA-N 0.000 description 1
- DSIUMCWPDASZBE-UHFFFAOYSA-N N-(6-propoxypyridin-3-yl)tridecanamide Chemical compound C(CC)OC1=CC=C(C=N1)NC(CCCCCCCCCCCC)=O DSIUMCWPDASZBE-UHFFFAOYSA-N 0.000 description 1
- NDGODNORWKJDQG-UHFFFAOYSA-N N-(6-propoxypyridin-3-yl)undec-10-enamide Chemical compound C(CC)OC1=CC=C(C=N1)NC(CCCCCCCCC=C)=O NDGODNORWKJDQG-UHFFFAOYSA-N 0.000 description 1
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- 241000700159 Rattus Species 0.000 description 1
- 241000700584 Simplexvirus Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 208000009916 Yoshida Sarcoma Diseases 0.000 description 1
- IJCVBMSXIPFVLH-UHFFFAOYSA-N [C].S=O Chemical compound [C].S=O IJCVBMSXIPFVLH-UHFFFAOYSA-N 0.000 description 1
- BVPJQGNCMRSQLF-UHFFFAOYSA-O [O-][N+]([N-]C1=CC=CC=[NH+]1)=O Chemical class [O-][N+]([N-]C1=CC=CC=[NH+]1)=O BVPJQGNCMRSQLF-UHFFFAOYSA-O 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 238000010640 amide synthesis reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 201000008275 breast carcinoma Diseases 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229940117173 croton oil Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000007256 debromination reaction Methods 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 1
- 206010014599 encephalitis Diseases 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- CWSYRJKTKIWWCR-UHFFFAOYSA-N ethyl 3-(trimethylsilylamino)pyridine-2-carboxylate Chemical compound C(C)OC(=O)C1=NC=CC=C1N[Si](C)(C)C CWSYRJKTKIWWCR-UHFFFAOYSA-N 0.000 description 1
- FIKVWPJKNMTBBD-UHFFFAOYSA-N ethyl 6-aminopyridine-3-carboxylate Chemical compound CCOC(=O)C1=CC=C(N)N=C1 FIKVWPJKNMTBBD-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229960002598 fumaric acid Drugs 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 208000037797 influenza A Diseases 0.000 description 1
- 208000037798 influenza B Diseases 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 229960000448 lactic acid Drugs 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098895 maleic acid Drugs 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 229940099690 malic acid Drugs 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- NHRFNKFLOXYNKX-UHFFFAOYSA-N n-(4-methylpyridin-2-yl)dodecanamide Chemical compound CCCCCCCCCCCC(=O)NC1=CC(C)=CC=N1 NHRFNKFLOXYNKX-UHFFFAOYSA-N 0.000 description 1
- YSYVNWFPYVHZBA-UHFFFAOYSA-N n-(4-methylpyridin-2-yl)undec-10-enamide Chemical compound CC1=CC=NC(NC(=O)CCCCCCCCC=C)=C1 YSYVNWFPYVHZBA-UHFFFAOYSA-N 0.000 description 1
- AATSEAYIALATEL-UHFFFAOYSA-N n-(5-methylpyridin-2-yl)dodecanamide Chemical compound CCCCCCCCCCCC(=O)NC1=CC=C(C)C=N1 AATSEAYIALATEL-UHFFFAOYSA-N 0.000 description 1
- ZKAYHMWYRAQKCW-UHFFFAOYSA-N n-pyridin-2-yldodecanamide Chemical compound CCCCCCCCCCCC(=O)NC1=CC=CC=N1 ZKAYHMWYRAQKCW-UHFFFAOYSA-N 0.000 description 1
- 230000009826 neoplastic cell growth Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229940116315 oxalic acid Drugs 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 201000000849 skin cancer Diseases 0.000 description 1
- 201000008261 skin carcinoma Diseases 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000005748 tumor development Effects 0.000 description 1
- UBNOUEFUWQCVFM-UHFFFAOYSA-N undec-2-enamide Chemical compound CCCCCCCCC=CC(N)=O UBNOUEFUWQCVFM-UHFFFAOYSA-N 0.000 description 1
- 230000003612 virological effect Effects 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
- C07D213/75—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
- C07D213/72—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
- C07D213/78—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH123466A CH500980A (de) | 1966-01-28 | 1966-01-28 | Verfahren zur Herstellung von neuen Amiden aliphatischer Carbonsäuren |
Publications (1)
Publication Number | Publication Date |
---|---|
NO122420B true NO122420B (es) | 1971-06-28 |
Family
ID=4205609
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO16659167A NO122420B (es) | 1966-01-28 | 1967-01-27 |
Country Status (13)
Country | Link |
---|---|
AT (2) | AT268281B (es) |
BE (1) | BE693263A (es) |
CH (1) | CH500980A (es) |
DE (1) | DE1695006A1 (es) |
DK (1) | DK115393B (es) |
ES (1) | ES336148A1 (es) |
FR (2) | FR1510319A (es) |
GB (1) | GB1179262A (es) |
GR (1) | GR35673B (es) |
IL (1) | IL27336A (es) |
NL (1) | NL6701359A (es) |
NO (1) | NO122420B (es) |
SE (1) | SE331096B (es) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1991004027A1 (en) * | 1989-09-15 | 1991-04-04 | Pfizer Inc. | New n-aryl and n-heteroarylamide and urea derivatives as inhibitors of acyl coenzyme a: cholesterol acyl transferase (acat) |
KR101612179B1 (ko) * | 2013-04-19 | 2016-04-12 | 영남대학교 산학협력단 | 아미도피리딘올 유도체 또는 이의 약제학적 허용가능한 염을 유효성분으로 함유하는 암질환 예방 또는 치료용 약학조성물 |
-
1966
- 1966-01-28 CH CH123466A patent/CH500980A/de not_active IP Right Cessation
-
1967
- 1967-01-27 GR GR670135673A patent/GR35673B/el unknown
- 1967-01-27 BE BE693263D patent/BE693263A/xx unknown
- 1967-01-27 ES ES336148A patent/ES336148A1/es not_active Expired
- 1967-01-27 AT AT80067A patent/AT268281B/de active
- 1967-01-27 FR FR92772A patent/FR1510319A/fr not_active Expired
- 1967-01-27 NL NL6701359A patent/NL6701359A/xx unknown
- 1967-01-27 GB GB411667A patent/GB1179262A/en not_active Expired
- 1967-01-27 IL IL2733667A patent/IL27336A/en unknown
- 1967-01-27 DE DE19671695006 patent/DE1695006A1/de active Pending
- 1967-01-27 SE SE121967A patent/SE331096B/xx unknown
- 1967-01-27 NO NO16659167A patent/NO122420B/no unknown
- 1967-01-27 DK DK50667A patent/DK115393B/da unknown
- 1967-01-27 AT AT125468A patent/AT268283B/de active
- 1967-04-26 FR FR104243A patent/FR6381M/fr not_active Expired
Also Published As
Publication number | Publication date |
---|---|
GB1179262A (en) | 1970-01-28 |
NL6701359A (es) | 1967-07-31 |
CH500980A (de) | 1970-12-31 |
SE331096B (es) | 1970-12-14 |
BE693263A (es) | 1967-07-27 |
GR35673B (el) | 1968-10-17 |
AT268281B (de) | 1969-02-10 |
DE1695006A1 (de) | 1971-02-25 |
FR6381M (es) | 1968-10-14 |
DK115393B (da) | 1969-10-06 |
AT268283B (de) | 1969-02-10 |
FR1510319A (fr) | 1968-01-19 |
IL27336A (en) | 1971-02-25 |
ES336148A1 (es) | 1968-04-01 |
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