DE2316881A1 - Biologisch aktive verbindungen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate - Google Patents
Biologisch aktive verbindungen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparateInfo
- Publication number
- DE2316881A1 DE2316881A1 DE2316881A DE2316881A DE2316881A1 DE 2316881 A1 DE2316881 A1 DE 2316881A1 DE 2316881 A DE2316881 A DE 2316881A DE 2316881 A DE2316881 A DE 2316881A DE 2316881 A1 DE2316881 A1 DE 2316881A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- formula
- alk
- radical
- pyridyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims description 55
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 15
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- -1 4-carbamylphenoxy Chemical group 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
- 101100371682 Caenorhabditis elegans cyk-3 gene Proteins 0.000 claims 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 20
- 235000002639 sodium chloride Nutrition 0.000 description 17
- 235000019441 ethanol Nutrition 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 230000002218 hypoglycaemic effect Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- HIMXGTXNXJYFGB-UHFFFAOYSA-N alloxan Chemical compound O=C1NC(=O)C(=O)C(=O)N1 HIMXGTXNXJYFGB-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000004283 biguanides Chemical class 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 206010012601 diabetes mellitus Diseases 0.000 description 3
- 229940126601 medicinal product Drugs 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241000700198 Cavia Species 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 102000004877 Insulin Human genes 0.000 description 2
- 108090001061 Insulin Proteins 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229940100389 Sulfonylurea Drugs 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229940125396 insulin Drugs 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 210000000813 small intestine Anatomy 0.000 description 2
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 1
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 1
- NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 description 1
- BXGYBSJAZFGIPX-UHFFFAOYSA-N 2-pyridin-2-ylethanol Chemical compound OCCC1=CC=CC=N1 BXGYBSJAZFGIPX-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 235000021537 Beetroot Nutrition 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 240000007839 Kleinhovia hospita Species 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000282695 Saimiri Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- FWZUNOYOVVKUNF-UHFFFAOYSA-N allyl acetate Chemical compound CC(=O)OCC=C FWZUNOYOVVKUNF-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- NWPWRAWAUYIELB-UHFFFAOYSA-N ethyl 4-methylbenzoate Chemical compound CCOC(=O)C1=CC=C(C)C=C1 NWPWRAWAUYIELB-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000004190 glucose uptake Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000055 hyoplipidemic effect Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 208000006443 lactic acidosis Diseases 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 235000021395 porridge Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical compound OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 210000003625 skull Anatomy 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
- 239000008096 xylene Substances 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1528072A GB1437781A (en) | 1972-04-04 | 1972-04-04 | Pyridine derivatives having hypoglycaemic activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2316881A1 true DE2316881A1 (de) | 1973-10-11 |
Family
ID=10056262
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2316881A Pending DE2316881A1 (de) | 1972-04-04 | 1973-04-04 | Biologisch aktive verbindungen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate |
Country Status (20)
Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0759755A4 (en) * | 1994-05-13 | 1997-05-07 | Sanofi Winthrop Inc | THIADIAZOLES AND THEIR USE AS ANTIPICORNAVIRAL AGENTS |
| WO1997039748A1 (en) * | 1996-04-19 | 1997-10-30 | Novo Nordisk A/S | Modulators of molecules with phosphotyrosine recognition units |
| WO2000001690A1 (en) * | 1998-07-03 | 2000-01-13 | Celltech Therapeutics Limited | Cinnamic acid derivatives as cell adhesion molecules |
| US6043247A (en) * | 1996-04-19 | 2000-03-28 | Novo Nordisk A/S | Modulators of molecules with phosphotyrosine recognition units |
| US6110945A (en) * | 1998-06-03 | 2000-08-29 | Celltech Therapeutics Limited | Aromatic amine derivatives |
| US6274577B1 (en) | 1998-09-30 | 2001-08-14 | Celltech Therapeutics Limited | Benzodiazepines |
| US6319922B1 (en) | 1998-11-23 | 2001-11-20 | Celltech Therapeutics Limited | Propanoic acid derivatives |
| US6329362B1 (en) | 1998-03-16 | 2001-12-11 | Celltech Therapeutics Limited | Cinnamic acid derivatives |
| US6329372B1 (en) | 1998-01-27 | 2001-12-11 | Celltech Therapeutics Limited | Phenylalanine derivatives |
| US6348463B1 (en) | 1998-09-28 | 2002-02-19 | Celltech Therapeutics Limited | Phenylalanine derivatives |
| US6362204B1 (en) | 1998-05-22 | 2002-03-26 | Celltech Therapeutics, Ltd | Phenylalanine derivatives |
| US6403608B1 (en) | 2000-05-30 | 2002-06-11 | Celltech R&D, Ltd. | 3-Substituted isoquinolin-1-yl derivatives |
| US6455539B2 (en) | 1999-12-23 | 2002-09-24 | Celltech R&D Limited | Squaric acid derivates |
| US6469025B1 (en) | 2000-08-02 | 2002-10-22 | Celltech R&D Ltd. | 3-substituted isoquinolin-1-yl derivatives |
| US6518283B1 (en) | 1999-05-28 | 2003-02-11 | Celltech R&D Limited | Squaric acid derivatives |
| US6521626B1 (en) | 1998-03-24 | 2003-02-18 | Celltech R&D Limited | Thiocarboxamide derivatives |
| US6534513B1 (en) | 1999-09-29 | 2003-03-18 | Celltech R&D Limited | Phenylalkanoic acid derivatives |
| US6545013B2 (en) | 2000-05-30 | 2003-04-08 | Celltech R&D Limited | 2,7-naphthyridine derivatives |
| US6555562B1 (en) | 1998-02-26 | 2003-04-29 | Celltech R&D Limited | Phenylalanine derivatives |
| US6610700B2 (en) | 2000-04-17 | 2003-08-26 | Celltech R & D Limited | Enamine derivatives |
| US6740654B2 (en) | 2000-07-07 | 2004-05-25 | Celltech R & D Limited | Squaric acid derivatives |
| US6911451B1 (en) | 1998-06-05 | 2005-06-28 | Celltech R&D Limited | Phenylalanine derivatives |
| US6953798B1 (en) | 1998-11-30 | 2005-10-11 | Celltech R&D Limited | β-alanine derivates |
| WO2015000900A3 (en) * | 2013-07-01 | 2015-04-30 | Givaudan Sa | Organic compounds |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4409227A (en) | 1979-08-09 | 1983-10-11 | The Dow Chemical Co. | 4-(((Heterocyclo)thio)methyl)benzoic acids, esters and amides and their pharmaceutical use |
| DE69202126T2 (de) * | 1991-07-03 | 1995-08-24 | Unilever Nv | Verbesserte Schokolade-Zusammensetzung. |
| ATE126673T1 (de) * | 1991-07-03 | 1995-09-15 | Unilever Nv | Pralinenfüllung enthaltend ein zusatzmittel gegen fettbelag. |
| CN100344616C (zh) * | 2001-06-12 | 2007-10-24 | 维尔斯达医疗公司 | 用于治疗代谢失调的化合物 |
| GB0405033D0 (en) * | 2004-03-05 | 2004-04-07 | Karobio Ab | Novel pharmaceutical compositions |
| TWI490214B (zh) * | 2008-05-30 | 2015-07-01 | 艾德克 上野股份有限公司 | 苯或噻吩衍生物及該等作為ｖａｐ－１抑制劑之用途 |
| AR074760A1 (es) * | 2008-12-18 | 2011-02-09 | Metabolex Inc | Agonistas del receptor gpr120 y usos de los mismos en medicamentos para el tratamiento de diabetes y el sindrome metabolico. |
| WO2016167153A1 (ja) * | 2015-04-15 | 2016-10-20 | 長谷川香料株式会社 | ピリジン誘導体またはその塩を有効成分とする香味変調剤 |
| EP3440052B1 (en) * | 2016-04-06 | 2023-10-25 | University Of Oulu | Compounds for use in the treatment of cancer |
-
1972
- 1972-04-04 GB GB1528072A patent/GB1437781A/en not_active Expired
-
1973
- 1973-01-01 AR AR247376A patent/AR208269A1/es active
- 1973-03-15 IE IE426/73A patent/IE37412B1/xx unknown
- 1973-03-16 ZA ZA731853A patent/ZA731853B/xx unknown
- 1973-03-19 IL IL41825A patent/IL41825A/en unknown
- 1973-03-30 HU HURO717A patent/HU165731B/hu unknown
- 1973-04-02 AT AT286773A patent/AT339301B/de not_active IP Right Cessation
- 1973-04-03 NL NL7304610A patent/NL7304610A/xx not_active Application Discontinuation
- 1973-04-03 CA CA167,818A patent/CA999868A/en not_active Expired
- 1973-04-03 RO RO7300083382A patent/RO63069A/ro unknown
- 1973-04-03 JP JP48038610A patent/JPS49100091A/ja active Pending
- 1973-04-03 RO RO7300074369A patent/RO62274A/ro unknown
- 1973-04-03 BE BE129595A patent/BE797715A/xx unknown
- 1973-04-03 ES ES413279A patent/ES413279A1/es not_active Expired
- 1973-04-03 CS CS7300002387A patent/CS183689B2/cs unknown
- 1973-04-04 PL PL1973161704A patent/PL96043B1/pl unknown
- 1973-04-04 DE DE2316881A patent/DE2316881A1/de active Pending
- 1973-04-04 FR FR7312133A patent/FR2182933B1/fr not_active Expired
- 1973-04-04 CH CH482673A patent/CH576961A5/xx not_active IP Right Cessation
- 1973-04-04 BG BG023170A patent/BG20352A3/xx unknown
- 1973-04-04 DD DD169942A patent/DD106834A5/xx unknown
Cited By (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0759755A4 (en) * | 1994-05-13 | 1997-05-07 | Sanofi Winthrop Inc | THIADIAZOLES AND THEIR USE AS ANTIPICORNAVIRAL AGENTS |
| WO1997039748A1 (en) * | 1996-04-19 | 1997-10-30 | Novo Nordisk A/S | Modulators of molecules with phosphotyrosine recognition units |
| US6043247A (en) * | 1996-04-19 | 2000-03-28 | Novo Nordisk A/S | Modulators of molecules with phosphotyrosine recognition units |
| US6329372B1 (en) | 1998-01-27 | 2001-12-11 | Celltech Therapeutics Limited | Phenylalanine derivatives |
| US6555562B1 (en) | 1998-02-26 | 2003-04-29 | Celltech R&D Limited | Phenylalanine derivatives |
| US6329362B1 (en) | 1998-03-16 | 2001-12-11 | Celltech Therapeutics Limited | Cinnamic acid derivatives |
| US6521626B1 (en) | 1998-03-24 | 2003-02-18 | Celltech R&D Limited | Thiocarboxamide derivatives |
| US6362204B1 (en) | 1998-05-22 | 2002-03-26 | Celltech Therapeutics, Ltd | Phenylalanine derivatives |
| US6369229B1 (en) | 1998-06-03 | 2002-04-09 | Celltech Therapeutics, Limited | Pyridylalanine derivatives |
| US6110945A (en) * | 1998-06-03 | 2000-08-29 | Celltech Therapeutics Limited | Aromatic amine derivatives |
| US6911451B1 (en) | 1998-06-05 | 2005-06-28 | Celltech R&D Limited | Phenylalanine derivatives |
| US6465471B1 (en) | 1998-07-03 | 2002-10-15 | Celltech Therapeutics Limited | Cinnamic acid derivatives |
| WO2000001690A1 (en) * | 1998-07-03 | 2000-01-13 | Celltech Therapeutics Limited | Cinnamic acid derivatives as cell adhesion molecules |
| US6348463B1 (en) | 1998-09-28 | 2002-02-19 | Celltech Therapeutics Limited | Phenylalanine derivatives |
| US6677339B2 (en) | 1998-09-28 | 2004-01-13 | Celltech R & D Limited | Phenylalanine derivatives |
| US6274577B1 (en) | 1998-09-30 | 2001-08-14 | Celltech Therapeutics Limited | Benzodiazepines |
| US6319922B1 (en) | 1998-11-23 | 2001-11-20 | Celltech Therapeutics Limited | Propanoic acid derivatives |
| US6953798B1 (en) | 1998-11-30 | 2005-10-11 | Celltech R&D Limited | β-alanine derivates |
| US6518283B1 (en) | 1999-05-28 | 2003-02-11 | Celltech R&D Limited | Squaric acid derivatives |
| US6534513B1 (en) | 1999-09-29 | 2003-03-18 | Celltech R&D Limited | Phenylalkanoic acid derivatives |
| US6455539B2 (en) | 1999-12-23 | 2002-09-24 | Celltech R&D Limited | Squaric acid derivates |
| US6610700B2 (en) | 2000-04-17 | 2003-08-26 | Celltech R & D Limited | Enamine derivatives |
| US6780874B2 (en) | 2000-04-17 | 2004-08-24 | Celltech R & D Limited | Enamine derivatives |
| US6545013B2 (en) | 2000-05-30 | 2003-04-08 | Celltech R&D Limited | 2,7-naphthyridine derivatives |
| US6403608B1 (en) | 2000-05-30 | 2002-06-11 | Celltech R&D, Ltd. | 3-Substituted isoquinolin-1-yl derivatives |
| US6740654B2 (en) | 2000-07-07 | 2004-05-25 | Celltech R & D Limited | Squaric acid derivatives |
| US6469025B1 (en) | 2000-08-02 | 2002-10-22 | Celltech R&D Ltd. | 3-substituted isoquinolin-1-yl derivatives |
| WO2015000900A3 (en) * | 2013-07-01 | 2015-04-30 | Givaudan Sa | Organic compounds |
| US10178875B2 (en) | 2013-07-01 | 2019-01-15 | Givaudan S.A. | Methods of modifying or imparting taste using organic compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| PL96043B1 (pl) | 1977-11-30 |
| IL41825A0 (en) | 1973-05-31 |
| AT339301B (de) | 1977-10-10 |
| ATA286773A (de) | 1977-02-15 |
| ES413279A1 (es) | 1976-01-01 |
| CH576961A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-06-30 |
| AR208269A1 (es) | 1976-12-20 |
| HU165731B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-10-28 |
| RO63069A (fr) | 1978-08-15 |
| FR2182933B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-05-14 |
| IL41825A (en) | 1977-03-31 |
| BE797715A (fr) | 1973-10-03 |
| IE37412L (en) | 1973-10-04 |
| JPS49100091A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-09-20 |
| CS183689B2 (en) | 1978-07-31 |
| GB1437781A (en) | 1976-06-03 |
| NL7304610A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-10-08 |
| BG20352A3 (bg) | 1975-11-05 |
| ZA731853B (en) | 1974-01-30 |
| IE37412B1 (en) | 1977-07-20 |
| CA999868A (en) | 1976-11-16 |
| FR2182933A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-12-14 |
| DD106834A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-07-05 |
| RO62274A (fr) | 1977-12-15 |
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Legal Events
| Date | Code | Title | Description |
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| OHJ | Non-payment of the annual fee |