CH650774A5 - Derivati della piridossina ad attivita farmacologica. - Google Patents
Derivati della piridossina ad attivita farmacologica. Download PDFInfo
- Publication number
- CH650774A5 CH650774A5 CH6972/79A CH697279A CH650774A5 CH 650774 A5 CH650774 A5 CH 650774A5 CH 6972/79 A CH6972/79 A CH 6972/79A CH 697279 A CH697279 A CH 697279A CH 650774 A5 CH650774 A5 CH 650774A5
- Authority
- CH
- Switzerland
- Prior art keywords
- propionic
- phenyl
- acid
- formula
- compounds
- Prior art date
Links
- -1 PYRIDOXY Chemical class 0.000 title claims description 54
- 230000000144 pharmacologic effect Effects 0.000 title description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 41
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 32
- 235000008160 pyridoxine Nutrition 0.000 claims description 28
- 239000011677 pyridoxine Substances 0.000 claims description 28
- 229940011671 vitamin b6 Drugs 0.000 claims description 28
- SUULQCVVCFHEIU-UHFFFAOYSA-N 4,5-bis(hydroxymethyl)-2-(2-methylprop-1-enyl)pyridin-3-ol Chemical compound CC(C)=CC1=NC=C(CO)C(CO)=C1O SUULQCVVCFHEIU-UHFFFAOYSA-N 0.000 claims description 23
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 150000007513 acids Chemical class 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 10
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 9
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 5
- 235000001968 nicotinic acid Nutrition 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 230000032050 esterification Effects 0.000 claims description 4
- 238000005886 esterification reaction Methods 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 229960004889 salicylic acid Drugs 0.000 claims description 4
- 230000000699 topical effect Effects 0.000 claims description 4
- 150000005166 2-hydroxybenzoic acids Chemical class 0.000 claims description 3
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 150000003840 hydrochlorides Chemical class 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 150000003227 pyridoxines Chemical class 0.000 claims description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 2
- ARHWPKZXBHOEEE-UHFFFAOYSA-N alclofenac Chemical compound OC(=O)CC1=CC=C(OCC=C)C(Cl)=C1 ARHWPKZXBHOEEE-UHFFFAOYSA-N 0.000 claims description 2
- 229960005142 alclofenac Drugs 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000002814 niacins Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 150000003873 salicylate salts Chemical class 0.000 claims description 2
- 150000003890 succinate salts Chemical class 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
- 150000003892 tartrate salts Chemical class 0.000 claims description 2
- LODHFNUFVRVKTH-ZHACJKMWSA-N 2-hydroxy-n'-[(e)-3-phenylprop-2-enoyl]benzohydrazide Chemical compound OC1=CC=CC=C1C(=O)NNC(=O)\C=C\C1=CC=CC=C1 LODHFNUFVRVKTH-ZHACJKMWSA-N 0.000 claims 2
- 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 claims 1
- 239000000654 additive Substances 0.000 claims 1
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000003981 vehicle Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 235000019441 ethanol Nutrition 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 230000003110 anti-inflammatory effect Effects 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 230000001562 ulcerogenic effect Effects 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 5
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 229940022682 acetone Drugs 0.000 description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000011664 nicotinic acid Substances 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 244000144725 Amygdalus communis Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000020224 almond Nutrition 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 239000000679 carrageenan Substances 0.000 description 2
- 229940113118 carrageenan Drugs 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- QXVRLFIKHYCFJS-UHFFFAOYSA-N 2-[4-(2-methylpropyl)phenyl]propanoyl chloride Chemical compound CC(C)CC1=CC=C(C(C)C(Cl)=O)C=C1 QXVRLFIKHYCFJS-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- JZFPYUNJRRFVQU-UHFFFAOYSA-N Niflumic acid Chemical compound OC(=O)C1=CC=CN=C1NC1=CC=CC(C(F)(F)F)=C1 JZFPYUNJRRFVQU-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XGEJPZWLVJMNCR-UHFFFAOYSA-N OC(O)=O.Cl.Cl.Cl.Cl Chemical compound OC(O)=O.Cl.Cl.Cl.Cl XGEJPZWLVJMNCR-UHFFFAOYSA-N 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000001618 algogenic effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical class OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- LPEPZBJOKDYZAD-UHFFFAOYSA-N flufenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 LPEPZBJOKDYZAD-UHFFFAOYSA-N 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 description 1
- CACWGKXXWFHZRW-UHFFFAOYSA-N methyl 2-[3-(trifluoromethyl)anilino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 CACWGKXXWFHZRW-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000004537 pulping Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000008247 solid mixture Substances 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
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000005406 washing Methods 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
- C07D213/60—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
- C07D213/80—Acids; Esters in position 3
-
- 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
- C07D213/65—One oxygen atom attached in position 3 or 5
- C07D213/66—One oxygen atom attached in position 3 or 5 having in position 3 an oxygen atom and in each of the positions 4 and 5 a carbon atom bound to an oxygen, sulphur, or nitrogen atom, e.g. pyridoxal
- C07D213/67—2-Methyl-3-hydroxy-4,5-bis(hydroxy-methyl)pyridine, i.e. pyridoxine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT26327/78A IT1097601B (it) | 1978-07-31 | 1978-07-31 | Derivati della piridosina ad attivita' farmacologica |
| IT2293279A IT1165076B (it) | 1979-05-23 | 1979-05-23 | Derivati della piridossina ad attivita' farmacologica |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH650774A5 true CH650774A5 (it) | 1985-08-15 |
Family
ID=26328291
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH6972/79A CH650774A5 (it) | 1978-07-31 | 1979-07-27 | Derivati della piridossina ad attivita farmacologica. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4233304A (en, 2012) |
| AT (1) | AT373582B (en, 2012) |
| AU (1) | AU514304B2 (en, 2012) |
| CA (1) | CA1123829A (en, 2012) |
| CH (1) | CH650774A5 (en, 2012) |
| DE (1) | DE2931105A1 (en, 2012) |
| DK (1) | DK156651C (en, 2012) |
| ES (1) | ES482949A1 (en, 2012) |
| FR (1) | FR2433516A1 (en, 2012) |
| GB (1) | GB2027022B (en, 2012) |
| MX (1) | MX5955E (en, 2012) |
| NL (1) | NL185454C (en, 2012) |
| NO (1) | NO151933C (en, 2012) |
| PT (1) | PT70002A (en, 2012) |
| SE (1) | SE431645B (en, 2012) |
| YU (2) | YU42488B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1133963B (it) * | 1980-10-21 | 1986-07-24 | D & D Srl | Derivati piridossinici ad attivita' terapeutica,procedimento per la loro preparazione e relative composizioni farmaceutiche |
| US4376767A (en) * | 1981-01-02 | 1983-03-15 | Merck & Co., Inc. | Pyridylmethyl esters of selected bio-affecting carboxylic acids |
| US4666929A (en) * | 1985-04-10 | 1987-05-19 | Shiseido Company Ltd. | Anthranilic acid ester derivatives and antiinflammatory and analgetic external preparations containing the same |
| US20060147508A1 (en) * | 2002-10-04 | 2006-07-06 | Bioderm Research | Concurrent Enhancement of Skin Penetration of Organic Base Active Agents and Organic Hydroxy Acid Active Agents as Their Ion-Pair Complexes |
| WO2022076597A1 (en) * | 2020-10-06 | 2022-04-14 | Percheron Power, LLC | Bi-directional fish pass helix |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1022934A (en) * | 1963-07-12 | 1966-03-16 | Takeda Chemical Industries Ltd | A process for producing pyridoxine |
| US3557131A (en) * | 1965-06-15 | 1971-01-19 | Dainippon Pharmaceutical Co | Nicotinate derivatives of vitamin b6 |
| US3644385A (en) * | 1967-11-27 | 1972-02-22 | Tanabe Seiyaku Co | Alpha**5-o-acyl-pyridoxal derivatives |
| ES431712A1 (es) * | 1974-11-06 | 1976-11-16 | Zambeletti Espana | Procedimiento para la preparacion de derivados de la piri- doxina. |
| US4125616A (en) * | 1975-11-04 | 1978-11-14 | Zambeletti Espana, S.A. | Pyridoxylidine amino benzoate compounds |
-
1979
- 1979-07-03 US US06/054,613 patent/US4233304A/en not_active Expired - Lifetime
- 1979-07-04 AU AU48643/79A patent/AU514304B2/en not_active Ceased
- 1979-07-18 YU YU1753/79A patent/YU42488B/xx unknown
- 1979-07-25 NL NLAANVRAGE7905774,A patent/NL185454C/xx not_active IP Right Cessation
- 1979-07-26 AT AT0517679A patent/AT373582B/de active
- 1979-07-27 CH CH6972/79A patent/CH650774A5/it not_active IP Right Cessation
- 1979-07-27 GB GB7926223A patent/GB2027022B/en not_active Expired
- 1979-07-30 ES ES482949A patent/ES482949A1/es not_active Expired
- 1979-07-30 DK DK320479A patent/DK156651C/da not_active IP Right Cessation
- 1979-07-30 PT PT70002A patent/PT70002A/pt unknown
- 1979-07-30 NO NO792511A patent/NO151933C/no unknown
- 1979-07-30 SE SE7906440A patent/SE431645B/sv not_active IP Right Cessation
- 1979-07-30 MX MX798273U patent/MX5955E/es unknown
- 1979-07-31 FR FR7919714A patent/FR2433516A1/fr active Granted
- 1979-07-31 CA CA332,909A patent/CA1123829A/en not_active Expired
- 1979-07-31 DE DE19792931105 patent/DE2931105A1/de active Granted
-
1983
- 1983-02-11 YU YU322/83A patent/YU42070B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU42488B (en) | 1988-10-31 |
| GB2027022A (en) | 1980-02-13 |
| FR2433516B1 (en, 2012) | 1983-07-18 |
| FR2433516A1 (fr) | 1980-03-14 |
| DE2931105A1 (de) | 1980-02-14 |
| NO792511L (no) | 1980-02-01 |
| NL185454C (nl) | 1990-04-17 |
| ES482949A1 (es) | 1980-07-01 |
| DK156651B (da) | 1989-09-18 |
| GB2027022B (en) | 1982-12-22 |
| AT373582B (de) | 1984-02-10 |
| YU32283A (en) | 1984-02-29 |
| NL185454B (nl) | 1989-11-16 |
| ATA517679A (de) | 1983-06-15 |
| NL7905774A (nl) | 1980-02-04 |
| AU514304B2 (en) | 1981-02-05 |
| DK156651C (da) | 1990-02-05 |
| DE2931105C2 (en, 2012) | 1988-10-13 |
| PT70002A (en) | 1979-08-01 |
| MX5955E (es) | 1984-09-06 |
| SE7906440L (sv) | 1980-02-01 |
| DK320479A (da) | 1980-02-01 |
| CA1123829A (en) | 1982-05-18 |
| YU42070B (en) | 1988-04-30 |
| YU175379A (en) | 1984-02-29 |
| US4233304A (en) | 1980-11-11 |
| AU4864379A (en) | 1980-02-07 |
| SE431645B (sv) | 1984-02-20 |
| NO151933B (no) | 1985-03-25 |
| NO151933C (no) | 1985-07-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4032534A (en) | Certain 2-(2-thioethyl)thiazolidine-4-carboxylic acids | |
| JPH0662562B2 (ja) | ピロール酢酸アミド | |
| NZ260350A (en) | Phenoxyisobutyric acid derivatives, preparation and pharmaceutical compositions thereof | |
| PL84190B1 (en) | 3-aroyl-alkenyleneimines[us3835149a] | |
| CH650774A5 (it) | Derivati della piridossina ad attivita farmacologica. | |
| CA2030732C (fr) | Nouveaux derives du thiophene, leur procede de preparation et les compositions pharmaceutiques les renfermant | |
| JPH0278675A (ja) | ベンゾフラニル酢酸誘導体、その製法、粘液調節剤および抗ヒスタミン剤 | |
| KR910008183B1 (ko) | 머캅토-아세트산 및 머캅토프로피온산 아미드 유도체의 제조방법 | |
| JPS61218571A (ja) | 新規ラクタム誘導体及び新規チオラクタム誘導体並びに抗炎症剤 | |
| US4521538A (en) | Ester of the 1-methyl-5-p-toluoylpyrrole-2-acetic acid having antiinflammatory, mucolytic and antitussive properties, process for its preparation and pharmaceutical compositions containing them | |
| US4816472A (en) | Derivatives of 19,20-Bis-nor-prostanoic acid with antiulcer and anorectic activity, process for their preparation and pharmaceutical compositions thereof | |
| JPS584699B2 (ja) | 置換フエニル酢酸誘導体及びその製法 | |
| USRE37078E1 (en) | Thiophene compounds | |
| JPH0710863B2 (ja) | エーテル化若しくはエステル化しうるジヒドロキシ基により位置２で置換された４―ｏｈキノリンカルボン酸の新規の誘導体、その製造方法、及び医薬としてのその使用 | |
| US4260613A (en) | Pyridoxine derivatives | |
| PL81176B1 (en, 2012) | ||
| JPS62123180A (ja) | ｐ−アミノフエノ−ル誘導体 | |
| CA1054630A (en) | Substituted indanylpropionic acids | |
| JPS6324498B2 (en, 2012) | ||
| AU706163B2 (en) | New thiophene compounds, a process for their preparation and pharmaceutical compositions containing them | |
| JPS60222455A (ja) | １’ω―メルカプトプロパンアミド及びその塩、その製造方法並びにそれを含有する薬剤 | |
| LU86706A1 (fr) | Nouveaux derives du benzo(4,5)cyclohepta(1,2-b)thiophene,leur preparation et leur utilisation comme medicaments | |
| JPS6130669B2 (en, 2012) | ||
| JPS6011903B2 (ja) | ピリドキシン誘導体 | |
| Pau et al. | Synthesis of N-[4-(propyl) cyclohexyl]-amides with anti-inflammatory and analgesic activities |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |