RU2107070C1 - Производные [2r,3r (2'r,3'r,), 6r,7s,8s,9r,10r] -3-(2',3'-дигидроксипент-2'-ил)-2,6,8,10,12-пентаметил -4,13-диоксабицикло [8,2,1]-тридец-12-ен-5-она, способ их получения, фармацевтическое средство - Google Patents
Производные [2r,3r (2'r,3'r,), 6r,7s,8s,9r,10r] -3-(2',3'-дигидроксипент-2'-ил)-2,6,8,10,12-пентаметил -4,13-диоксабицикло [8,2,1]-тридец-12-ен-5-она, способ их получения, фармацевтическое средство Download PDFInfo
- Publication number
- RU2107070C1 RU2107070C1 RU92016224A RU92016224A RU2107070C1 RU 2107070 C1 RU2107070 C1 RU 2107070C1 RU 92016224 A RU92016224 A RU 92016224A RU 92016224 A RU92016224 A RU 92016224A RU 2107070 C1 RU2107070 C1 RU 2107070C1
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- formula
- dihydroxypent
- pentamethyl
- derivatives
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- 239000008177 pharmaceutical agent Substances 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 239000002253 acid Substances 0.000 claims description 17
- -1 2,3-dihydroxypent-2-yl Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000013543 active substance Substances 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 239000012059 conventional drug carrier Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 17
- 230000000694 effects Effects 0.000 abstract description 14
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- LVRVABPNVHYXRT-BQWXUCBYSA-N 52906-92-0 Chemical compound C([C@H](N)C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCC(N)=O)C(O)=O)C(C)C)C1=CC=CC=C1 LVRVABPNVHYXRT-BQWXUCBYSA-N 0.000 description 11
- 210000002784 stomach Anatomy 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 239000002585 base Substances 0.000 description 9
- 229960003276 erythromycin Drugs 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 102000002419 Motilin Human genes 0.000 description 8
- 101800002372 Motilin Proteins 0.000 description 8
- 229930006677 Erythromycin A Natural products 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 230000030136 gastric emptying Effects 0.000 description 7
- 230000004899 motility Effects 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 6
- 102000057413 Motilin receptors Human genes 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 210000005070 sphincter Anatomy 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 108700040483 Motilin receptors Proteins 0.000 description 5
- 230000029936 alkylation Effects 0.000 description 5
- 238000005804 alkylation reaction Methods 0.000 description 5
- 230000003115 biocidal effect Effects 0.000 description 5
- 239000007853 buffer solution Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 230000002496 gastric effect Effects 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- 230000004936 stimulating effect Effects 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 206010016717 Fistula Diseases 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 230000017858 demethylation Effects 0.000 description 4
- 238000010520 demethylation reaction Methods 0.000 description 4
- 210000003238 esophagus Anatomy 0.000 description 4
- 230000003890 fistula Effects 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 230000002183 duodenal effect Effects 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 210000000111 lower esophageal sphincter Anatomy 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000005932 reductive alkylation reaction Methods 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 235000019759 Maize starch Nutrition 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 210000000936 intestine Anatomy 0.000 description 2
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 210000004379 membrane Anatomy 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 108010023244 Lactoperoxidase Proteins 0.000 description 1
- 102000045576 Lactoperoxidases Human genes 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 208000007542 Paresis Diseases 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 230000001270 agonistic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 210000003403 autonomic nervous system Anatomy 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 230000001713 cholinergic effect Effects 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940099112 cornstarch Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- IQDXNHZDRQHKEF-UHFFFAOYSA-N dialuminum;dicalcium;dioxido(oxo)silane Chemical compound [Al+3].[Al+3].[Ca+2].[Ca+2].[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O IQDXNHZDRQHKEF-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
- 210000003736 gastrointestinal content Anatomy 0.000 description 1
- 230000001330 gastroprokinetic effect Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 208000008384 ileus Diseases 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 208000003243 intestinal obstruction Diseases 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- PGLTVOMIXTUURA-UHFFFAOYSA-N iodoacetamide Chemical compound NC(=O)CI PGLTVOMIXTUURA-UHFFFAOYSA-N 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940057428 lactoperoxidase Drugs 0.000 description 1
- 210000002429 large intestine Anatomy 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 210000001595 mastoid Anatomy 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 229950000964 pepstatin Drugs 0.000 description 1
- 108010091212 pepstatin Proteins 0.000 description 1
- FAXGPCHRFPCXOO-LXTPJMTPSA-N pepstatin A Chemical compound OC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)CC(C)C FAXGPCHRFPCXOO-LXTPJMTPSA-N 0.000 description 1
- 239000000813 peptide hormone Substances 0.000 description 1
- 230000008855 peristalsis Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- IVNFTPCOZIGNAE-UHFFFAOYSA-N propan-2-yl hydrogen sulfate Chemical compound CC(C)OS(O)(=O)=O IVNFTPCOZIGNAE-UHFFFAOYSA-N 0.000 description 1
- HNDXKIMMSFCCFW-UHFFFAOYSA-N propane-2-sulphonic acid Chemical compound CC(C)S(O)(=O)=O HNDXKIMMSFCCFW-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Biotechnology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Genetics & Genomics (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4200145.5 | 1992-01-07 | ||
| DEP4200145,5 | 1992-01-07 | ||
| DE4200145A DE4200145A1 (de) | 1992-01-07 | 1992-01-07 | 7,10-epoxy-oxacyclododecan-derivate, verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU92016224A RU92016224A (ru) | 1995-11-27 |
| RU2107070C1 true RU2107070C1 (ru) | 1998-03-20 |
Family
ID=6449136
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU92016224A RU2107070C1 (ru) | 1992-01-07 | 1992-12-30 | Производные [2r,3r (2'r,3'r,), 6r,7s,8s,9r,10r] -3-(2',3'-дигидроксипент-2'-ил)-2,6,8,10,12-пентаметил -4,13-диоксабицикло [8,2,1]-тридец-12-ен-5-она, способ их получения, фармацевтическое средство |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US5418224A (OSRAM) |
| EP (1) | EP0550895B1 (OSRAM) |
| JP (1) | JP3300084B2 (OSRAM) |
| KR (1) | KR100273937B1 (OSRAM) |
| CN (1) | CN1033646C (OSRAM) |
| AT (1) | ATE155478T1 (OSRAM) |
| AU (1) | AU667699B2 (OSRAM) |
| CA (1) | CA2086811C (OSRAM) |
| CZ (1) | CZ281773B6 (OSRAM) |
| DE (2) | DE4200145A1 (OSRAM) |
| DK (1) | DK0550895T3 (OSRAM) |
| DZ (1) | DZ1652A1 (OSRAM) |
| ES (1) | ES2104808T3 (OSRAM) |
| FI (1) | FI106862B (OSRAM) |
| GR (1) | GR3024859T3 (OSRAM) |
| HU (2) | HU212272B (OSRAM) |
| IL (1) | IL104158A (OSRAM) |
| LT (1) | LT3015B (OSRAM) |
| LV (1) | LV10458B (OSRAM) |
| MX (1) | MX9300045A (OSRAM) |
| NO (1) | NO179586C (OSRAM) |
| PH (1) | PH30098A (OSRAM) |
| RU (1) | RU2107070C1 (OSRAM) |
| SK (1) | SK279251B6 (OSRAM) |
| TW (1) | TW238308B (OSRAM) |
| UA (1) | UA29393C2 (OSRAM) |
| ZA (1) | ZA9339B (OSRAM) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2218346C2 (ru) * | 1998-02-13 | 2003-12-10 | Солвей Фармасьютикалс Гмбх | Производные 11-ацетил-12,13-диоксабицикло [8.2.1] тридеценона, способ их получения и содержащие эти соединения лекарственные средства |
| RU2220149C2 (ru) * | 1998-09-10 | 2003-12-27 | Плива Фармацойтска Индустрия, Дионичко Друштво | 12,13-дигидроксипроизводные тилозина, способ их получения |
| RU2248981C2 (ru) * | 2000-09-01 | 2005-03-27 | Чугаи Сейяку Кабусики Кайся | Способ получения и очистки производных эритромицина |
| EA014711B1 (ru) * | 2005-05-24 | 2011-02-28 | Пфайзер Инк. | Мотилидные соединения, содержащая их фармацевтическая композиция, их применение, способ лечения заболевания со сниженной моторикой желудочно-кишечного тракта и способ индукции сокращения ткани |
| RU2422453C2 (ru) * | 2006-12-05 | 2011-06-27 | Пфайзер Инк. | Полиморфы мотилида |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69637097T2 (de) * | 1995-10-13 | 2007-09-20 | Neurosearch A/S | 8-Azabicyclo(3.2.1)Oct-2-en-Derivate, deren Herstellung und Anwendung |
| US6077943A (en) * | 1996-03-01 | 2000-06-20 | Takeda Chemical Industries, Ltd. | Method of producing erythromycin derivative |
| EP0884322A4 (en) * | 1996-03-01 | 2002-04-24 | Takeda Chemical Industries Ltd | METHOD FOR PRODUCING ERYTHROMYCIN DERIVATIVES |
| DE19644195A1 (de) * | 1996-10-24 | 1998-04-30 | Solvay Pharm Gmbh | 10,13,15-Trioxatricyclo[9.2.1.1.·9·.·6·]-pentadecanon-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US6165985A (en) * | 1998-02-13 | 2000-12-26 | Solvay Pharmaceuticals Gmbh | 11-acetyl-12,13-dioxabicyclo[8.2.1]-tridecenone derivatives, processes for their preparation and pharmaceutical compositions comprising them |
| CA2386828C (en) | 2000-08-17 | 2006-01-24 | The Kitasato Institute | Novel pseudoerythromycin derivatives |
| DE50204789D1 (de) * | 2001-05-10 | 2005-12-08 | Solvay Pharm Gmbh | Neue 1-amidomethylcarbonyl-piperidinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US20040067896A1 (en) * | 2002-07-25 | 2004-04-08 | The Kitasato Institute | Novel pseudoerythromycin derivatives |
| CA2528375C (en) | 2003-06-18 | 2013-11-19 | Tranzyme Pharma, Inc. | Macrocyclic antagonists of the motilin receptor |
| NZ568763A (en) * | 2005-12-08 | 2010-04-30 | Pfizer | Method for demethylating the 3'-dimethylamino group of erythromycin compounds |
| EP2431380A3 (en) | 2006-09-11 | 2013-07-03 | Tranzyme Pharma, Inc. | Macrocyclic antagonist of the motilin receptor for treatment of gastrointestinal dysmotility disorders |
| US20080287371A1 (en) * | 2007-05-17 | 2008-11-20 | Tranzyme Pharma Inc. | Macrocyclic antagonists of the motilin receptor for modulation of the migrating motor complex |
| TWI662967B (zh) * | 2013-03-25 | 2019-06-21 | 日商志瑞亞新藥工業股份有限公司 | 食後期之胃運動亢進劑 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0349100B1 (en) * | 1988-04-18 | 1996-06-26 | Eli Lilly And Company | Macrolide compositions for treating gastro-intestinal motility disorders |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3725385A (en) | 1970-11-02 | 1973-04-03 | Abbott Lab | Process for the demethylation of 3-amino macrolides |
| US5106961A (en) * | 1987-05-26 | 1992-04-21 | Eli Lilly And Company | Erythromycin ring-contracted derivatives |
| CA1321581C (en) * | 1987-05-26 | 1993-08-24 | Herbert A. Kirst | Ring-contracted macrolides |
-
1992
- 1992-01-07 DE DE4200145A patent/DE4200145A1/de not_active Withdrawn
- 1992-11-18 CZ CS923414A patent/CZ281773B6/cs not_active IP Right Cessation
- 1992-11-18 SK SK3414-92A patent/SK279251B6/sk unknown
- 1992-12-13 DZ DZ920162A patent/DZ1652A1/fr active
- 1992-12-18 IL IL104158A patent/IL104158A/xx not_active IP Right Cessation
- 1992-12-18 PH PH45475A patent/PH30098A/en unknown
- 1992-12-21 HU HU9204076A patent/HU212272B/hu not_active IP Right Cessation
- 1992-12-22 LT LTIP187A patent/LT3015B/lt not_active IP Right Cessation
- 1992-12-23 US US07/996,083 patent/US5418224A/en not_active Expired - Lifetime
- 1992-12-24 DK DK92122011.7T patent/DK0550895T3/da active
- 1992-12-24 ES ES92122011T patent/ES2104808T3/es not_active Expired - Lifetime
- 1992-12-24 DE DE59208710T patent/DE59208710D1/de not_active Expired - Fee Related
- 1992-12-24 AT AT92122011T patent/ATE155478T1/de not_active IP Right Cessation
- 1992-12-24 EP EP92122011A patent/EP0550895B1/de not_active Expired - Lifetime
- 1992-12-28 KR KR1019920026335A patent/KR100273937B1/ko not_active Expired - Fee Related
- 1992-12-30 RU RU92016224A patent/RU2107070C1/ru not_active IP Right Cessation
-
1993
- 1993-01-05 ZA ZA9339A patent/ZA9339B/xx unknown
- 1993-01-06 AU AU31036/93A patent/AU667699B2/en not_active Ceased
- 1993-01-06 CA CA002086811A patent/CA2086811C/en not_active Expired - Fee Related
- 1993-01-06 JP JP00055793A patent/JP3300084B2/ja not_active Expired - Fee Related
- 1993-01-06 LV LVP-93-01A patent/LV10458B/lv unknown
- 1993-01-06 NO NO930029A patent/NO179586C/no unknown
- 1993-01-06 CN CN93100166A patent/CN1033646C/zh not_active Expired - Fee Related
- 1993-01-07 FI FI930051A patent/FI106862B/fi active
- 1993-01-07 MX MX9300045A patent/MX9300045A/es not_active IP Right Cessation
- 1993-03-25 TW TW082102267A patent/TW238308B/zh active
- 1993-04-22 UA UA93002699A patent/UA29393C2/uk unknown
-
1994
- 1994-09-30 HU HU94P/P00031P patent/HU210216A9/hu unknown
-
1997
- 1997-09-24 GR GR970402503T patent/GR3024859T3/el unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0349100B1 (en) * | 1988-04-18 | 1996-06-26 | Eli Lilly And Company | Macrolide compositions for treating gastro-intestinal motility disorders |
Non-Patent Citations (1)
| Title |
|---|
| J. of Org. Chem 52, N 19, 1987, p.4359 - 4362. * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2218346C2 (ru) * | 1998-02-13 | 2003-12-10 | Солвей Фармасьютикалс Гмбх | Производные 11-ацетил-12,13-диоксабицикло [8.2.1] тридеценона, способ их получения и содержащие эти соединения лекарственные средства |
| RU2220149C2 (ru) * | 1998-09-10 | 2003-12-27 | Плива Фармацойтска Индустрия, Дионичко Друштво | 12,13-дигидроксипроизводные тилозина, способ их получения |
| RU2248981C2 (ru) * | 2000-09-01 | 2005-03-27 | Чугаи Сейяку Кабусики Кайся | Способ получения и очистки производных эритромицина |
| EA014711B1 (ru) * | 2005-05-24 | 2011-02-28 | Пфайзер Инк. | Мотилидные соединения, содержащая их фармацевтическая композиция, их применение, способ лечения заболевания со сниженной моторикой желудочно-кишечного тракта и способ индукции сокращения ткани |
| RU2422453C2 (ru) * | 2006-12-05 | 2011-06-27 | Пфайзер Инк. | Полиморфы мотилида |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3300084B2 (ja) | ４，１３−ジオキサビシクロ［８．２．１］トリデセノン誘導体、その製造のための方法および中間製品ならびに該化合物を含有する医薬品 | |
| RU2181727C2 (ru) | Производные 10,13,15-триоксатрицикло (9.2.1.1.9.6)-пентадеканона, способ их получения и содержащие эти соединения лекарственные средства | |
| MXPA97007974A (en) | Derivatives of 10, 13, 15-trioxatriciclo [9.2.1.1 9.6] -pentadecanona, procedures for its preparation and medicines that contain these compounds | |
| KR100584017B1 (ko) | 11-아세틸-12,13-디옥사바이시클로〔8.2.1〕-트리데케논 유도체,이의 제조방법 및 이 화합물을 포함하는 약제 | |
| HK1010885B (en) | 10,13,15-trioxatricyclo [9.2.1.1.9.6]-pentadecanone-derivates, process for their preparation and pharmaceutical containing them | |
| HK1023575B (en) | 11-acetyl-12, 13-dioxabicyclo (8.2.1)-tridecenone derivates, processes for the preparation thereof and medicaments containing these compounds | |
| MXPA99001491A (en) | Derivatives of 11-acetyl-12,13 dioxabiciclo [8.2.1] tridecenone, procedure for its preparation, and medications containing these compounds | |
| HK1014003B (en) | 4, 13-dioxabicyclo [8.2.1] tridecenone-derivatives, method and intermediates for their preparation, and medicaments containing the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20081231 |