LT3015B - 4,13-dioksabiciklo£8.2.1|tridekanono dariniai, ju gavimo budas, tarpiniai produktai jiems gauti ir juos turincios farmacines kompozicijos - Google Patents

4,13-dioksabiciklo£8.2.1|tridekanono dariniai, ju gavimo budas, tarpiniai produktai jiems gauti ir juos turincios farmacines kompozicijos Download PDF

Info

Publication number: LT3015B
Authority: LT; Lithuania
Prior art keywords: formula; methyl; compounds; content; tridec
Prior art date: 1992-01-07

Application number

LTIP187A

Other languages

English (en)

Lithuanian (lt)

Inventor

Dagmar Hoeltje

Ulf Preuschoff

Christian Eeckhout

Original Assignee

Kali Chemie Pharma Gmbh

Priority date (The priority date 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 date listed.)

1992-01-07

Filing date

1992-12-22

Publication date

1994-08-25

1992-12-22 Application filed by Kali Chemie Pharma Gmbh filed Critical Kali Chemie Pharma Gmbh

1994-03-25 Publication of LTIP187A publication Critical patent/LTIP187A/lt

1994-08-25 Publication of LT3015B publication Critical patent/LT3015B/lt

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 5
239000013067 intermediate product Substances 0.000 title 1
238000004064 recycling Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 53
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 14
QBEKGNIWIHIMOM-UHFFFAOYSA-N tridec-12-en-5-one Chemical class CCCCC(=O)CCCCCCC=C QBEKGNIWIHIMOM-UHFFFAOYSA-N 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen 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 5
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
229940124531 pharmaceutical excipient Drugs 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims 1
150000003254 radicals Chemical class 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 10
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 25
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 18
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 16
239000000047 product Substances 0.000 description 16
235000002639 sodium chloride Nutrition 0.000 description 15
239000002904 solvent Substances 0.000 description 14
230000002496 gastric effect Effects 0.000 description 13
239000000203 mixture Substances 0.000 description 13
239000000126 substance Substances 0.000 description 13
238000012360 testing method Methods 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
230000000694 effects Effects 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
229960003276 erythromycin Drugs 0.000 description 9
230000008855 peristalsis Effects 0.000 description 9
239000002585 base Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
238000000034 method Methods 0.000 description 8
-1 sodium triacetoxyborohydride Chemical compound 0.000 description 8
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 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
230000029936 alkylation Effects 0.000 description 7
238000005804 alkylation reaction Methods 0.000 description 7
239000000872 buffer Substances 0.000 description 7
230000030136 gastric emptying Effects 0.000 description 7
102000057413 Motilin receptors Human genes 0.000 description 6
108700040483 Motilin receptors Proteins 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
230000003115 biocidal effect Effects 0.000 description 6
210000001035 gastrointestinal tract Anatomy 0.000 description 6
229910052736 halogen Inorganic materials 0.000 description 6
150000002367 halogens Chemical class 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
210000002784 stomach Anatomy 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
229930006677 Erythromycin A Natural products 0.000 description 5
239000012043 crude product Substances 0.000 description 5
229910052740 iodine Inorganic materials 0.000 description 5
210000005070 sphincter Anatomy 0.000 description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
208000006687 Esophageal Fistula Diseases 0.000 description 4
102000002419 Motilin Human genes 0.000 description 4
101800002372 Motilin Proteins 0.000 description 4
206010065835 Oesophageal fistula Diseases 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
230000017858 demethylation Effects 0.000 description 4
238000010520 demethylation reaction Methods 0.000 description 4
238000009472 formulation Methods 0.000 description 4
239000011630 iodine Substances 0.000 description 4
210000000111 lower esophageal sphincter Anatomy 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000007787 solid Substances 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
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 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
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 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
150000008041 alkali metal carbonates Chemical class 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
238000003556 assay Methods 0.000 description 3
239000008120 corn starch Substances 0.000 description 3
229940099112 cornstarch Drugs 0.000 description 3
230000029087 digestion Effects 0.000 description 3
235000013305 food Nutrition 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
239000008101 lactose Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
238000005932 reductive alkylation reaction Methods 0.000 description 3
230000002829 reductive effect Effects 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
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
241001465754 Metazoa 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
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
230000009471 action Effects 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
239000000556 agonist Substances 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
230000027455 binding Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
230000008602 contraction Effects 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
230000005059 dormancy Effects 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000003480 eluent Substances 0.000 description 2
239000000284 extract Substances 0.000 description 2
230000037406 food intake Effects 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
239000011539 homogenization buffer Substances 0.000 description 2
229940088597 hormone Drugs 0.000 description 2
239000005556 hormone Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-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
210000004379 membrane Anatomy 0.000 description 2
239000012528 membrane Substances 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
239000002808 molecular sieve Substances 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 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
239000008188 pellet Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000010453 quartz Substances 0.000 description 2
102000005962 receptors Human genes 0.000 description 2
108020003175 receptors Proteins 0.000 description 2
230000001105 regulatory effect Effects 0.000 description 2
238000011160 research Methods 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-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
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
230000004936 stimulating effect Effects 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
210000001519 tissue Anatomy 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
TXOOBKBDBNRQCF-QNPWSHAKSA-N (3r,4s,5s,6r,7r,9r,11r,12r,13s,14r)-14-ethyl-7,12,13-trihydroxy-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-6-[(2s,3r,4s,6r)-3-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione 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](NC)C[C@@H](C)O2)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 TXOOBKBDBNRQCF-QNPWSHAKSA-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
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
206010012735 Diarrhoea Diseases 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
JFVYXJKGJMUGRG-KJPZRSJGSA-N Erythromycin a enol ether Chemical class O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C2=C(C)C[C@](O2)(C)[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 JFVYXJKGJMUGRG-KJPZRSJGSA-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
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
208000007101 Muscle Cramp Diseases 0.000 description 1
206010028813 Nausea Diseases 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 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
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
208000005392 Spasm Diseases 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
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
101710162629 Trypsin inhibitor Proteins 0.000 description 1
229940122618 Trypsin inhibitor Drugs 0.000 description 1
208000003443 Unconsciousness Diseases 0.000 description 1
206010047700 Vomiting Diseases 0.000 description 1
230000002159 abnormal effect Effects 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
230000002378 acidificating effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
230000001270 agonistic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 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
239000008346 aqueous phase Substances 0.000 description 1
125000002029 aromatic hydrocarbon group Chemical group 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
150000004653 carbonic acids Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000005119 centrifugation Methods 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
230000000112 colonic effect Effects 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
239000012067 demethylated product Substances 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
238000007865 diluting Methods 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
201000006549 dyspepsia Diseases 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
229940088598 enzyme Drugs 0.000 description 1
206010015037 epilepsy Diseases 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000012631 food intake Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
230000005176 gastrointestinal motility Effects 0.000 description 1
239000003626 gastrointestinal polypeptide Substances 0.000 description 1
230000001330 gastroprokinetic effect Effects 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
210000003405 ileum Anatomy 0.000 description 1
238000002513 implantation 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
238000003780 insertion Methods 0.000 description 1
230000037431 insertion Effects 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
210000000936 intestine Anatomy 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
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
229940057428 lactoperoxidase Drugs 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
KNWQLFOXPQZGPX-UHFFFAOYSA-N methanesulfonyl fluoride Chemical compound CS(F)(=O)=O KNWQLFOXPQZGPX-UHFFFAOYSA-N 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
229910052757 nitrogen Inorganic materials 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 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
239000008177 pharmaceutical agent Substances 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
239000011148 porous material Substances 0.000 description 1
230000008569 process Effects 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
230000002035 prolonged effect Effects 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-M propane-2-sulfonate Chemical compound CC(C)S([O-])(=O)=O HNDXKIMMSFCCFW-UHFFFAOYSA-M 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
230000009467 reduction Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 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
239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
230000009870 specific binding Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000007885 tablet disintegrant Substances 0.000 description 1
239000011975 tartaric acid Substances 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
230000000699 topical effect Effects 0.000 description 1
239000002753 trypsin inhibitor Substances 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)
Genetics & Genomics (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)
Biochemistry (AREA)
Biotechnology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Molecular Biology (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)
Plural Heterocyclic Compounds (AREA)
Macromonomer-Based Addition Polymer (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

LTIP187A 1992-01-07 1992-12-22 4,13-dioksabiciklo£8.2.1|tridekanono dariniai, ju gavimo budas, tarpiniai produktai jiems gauti ir juos turincios farmacines kompozicijos LT3015B (lt)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
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
LTIP187A LTIP187A (lt)	1994-03-25
LT3015B true LT3015B (lt)	1994-08-25

Family

ID=6449136

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LTIP187A LT3015B (lt)	1992-01-07	1992-12-22	4,13-dioksabiciklo£8.2.1\|tridekanono dariniai, ju gavimo budas, tarpiniai produktai jiems gauti ir juos turincios farmacines kompozicijos

Country Status (27)

Country	Link
US (1)	US5418224A (fr)
EP (1)	EP0550895B1 (fr)
JP (1)	JP3300084B2 (fr)
KR (1)	KR100273937B1 (fr)
CN (1)	CN1033646C (fr)
AT (1)	ATE155478T1 (fr)
AU (1)	AU667699B2 (fr)
CA (1)	CA2086811C (fr)
CZ (1)	CZ281773B6 (fr)
DE (2)	DE4200145A1 (fr)
DK (1)	DK0550895T3 (fr)
DZ (1)	DZ1652A1 (fr)
ES (1)	ES2104808T3 (fr)
FI (1)	FI106862B (fr)
GR (1)	GR3024859T3 (fr)
HU (2)	HU212272B (fr)
IL (1)	IL104158A (fr)
LT (1)	LT3015B (fr)
LV (1)	LV10458B (fr)
MX (1)	MX9300045A (fr)
NO (1)	NO179586C (fr)
PH (1)	PH30098A (fr)
RU (1)	RU2107070C1 (fr)
SK (1)	SK279251B6 (fr)
TW (1)	TW238308B (fr)
UA (1)	UA29393C2 (fr)
ZA (1)	ZA9339B (fr)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HUP9802433A3 (en) *	1995-10-13	2000-03-28	Neurosearch As	8-azabicyclo[3.2.1]oct-2-ene derivatives, their preparation and use
CA2247929A1 (fr) *	1996-03-01	1997-09-04	Miichiro Arita	Processus de preparation de derives d'erythromycine
US6077943A (en) *	1996-03-01	2000-06-20	Takeda Chemical Industries, Ltd.	Method of producing erythromycin derivative
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
DE19805822B4 (de) *	1998-02-13	2009-02-05	Solvay Pharmaceuticals Gmbh	11-Acetyl-12,13-dioxabicyclo[8.2.1]tridecenon-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
HRP980496B1 (en) *	1998-09-10	2007-03-31	GlaxoSmithKline istra�iva�ki centar Zagreb d.o.o.	New thilozine hydroxy derivatives and a process for the preparation thereof
WO2002014338A1 (fr) *	2000-08-17	2002-02-21	The Kitasato Institute	Nouveaux derives de pseudoerythromycine
KR100554562B1 (ko) *	2000-09-01	2006-03-03	쥬가이 세이야쿠 가부시키가이샤	에리트로마이신 유도체의 제조 방법
JP2004529184A (ja) *	2001-05-10	2004-09-24	ゾルファイ　ファーマスーティカルズ　ゲゼルシャフト　ミット　ベシュレンクテル　ハフツング	新規１−アミドメチルカルボニル−ピペリジン誘導体、該誘導体を製造するための方法及び中間体並びにこれらの化合物を含有している医薬
US20040067896A1 (en) *	2002-07-25	2004-04-08	The Kitasato Institute	Novel pseudoerythromycin derivatives
DE602004025569D1 (de)	2003-06-18	2010-04-01	Tranzyme Pharma Inc	Makrozyklische motilin rezeptorantagonisten
US7582611B2 (en) *	2005-05-24	2009-09-01	Pfizer Inc.	Motilide compounds
BRPI0619556A2 (pt) *	2005-12-08	2011-10-04	Pfizer	processo para desmetilação de grupo 3' -dimetil amino de compostos eritromicina
JP5684474B2 (ja)	2006-09-11	2015-03-11	オセラセラピューティクス，インコーポレイテッド	胃腸の運動障害疾患の治療のためのモチリン受容体の大環状アンタゴニスト
MX2009005977A (es) *	2006-12-05	2009-06-17	Pfizer	Polimorfos de motilida.
US20080287371A1 (en) *	2007-05-17	2008-11-20	Tranzyme Pharma Inc.	Macrocyclic antagonists of the motilin receptor for modulation of the migrating motor complex
WO2014156339A1 (fr) *	2013-03-25	2014-10-02	ゼリア新薬工業株式会社	Agent gastrocinétique postprandial

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2154032B2 (de)	1970-11-02	1979-05-10	Abbott Laboratories, Chicago, Ill. (V.St.A.)	Verfahren zur Demethylierung des Dimethylaminorestes in Erythromycin-AnÜbiotika
EP0349100A2 (fr)	1988-04-18	1990-01-03	Eli Lilly And Company	Compositions de macrolides dans le traitement des troubles de la motilité gastrointestinale

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5106961A (en) *	1987-05-26	1992-04-21	Eli Lilly And Company	Erythromycin ring-contracted derivatives
CA1321581C (fr) *	1987-05-26	1993-08-24	Herbert A. Kirst	Macrolides contractes en anneaux

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 PH PH45475A patent/PH30098A/en unknown
- 1992-12-18 IL IL104158A patent/IL104158A/xx not_active IP Right Cessation
- 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 AT AT92122011T patent/ATE155478T1/de not_active IP Right Cessation
- 1992-12-24 DE DE59208710T patent/DE59208710D1/de not_active Expired - Fee Related
- 1992-12-24 ES ES92122011T patent/ES2104808T3/es not_active Expired - Lifetime
- 1992-12-24 EP EP92122011A patent/EP0550895B1/fr 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 JP JP00055793A patent/JP3300084B2/ja not_active Expired - Fee Related
- 1993-01-06 LV LVP-93-01A patent/LV10458B/lv unknown
- 1993-01-06 CA CA002086811A patent/CA2086811C/fr not_active Expired - Fee Related
- 1993-01-06 AU AU31036/93A patent/AU667699B2/en not_active Ceased
- 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 MX MX9300045A patent/MX9300045A/es not_active IP Right Cessation
- 1993-01-07 FI FI930051A patent/FI106862B/fi active
- 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 (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2154032B2 (de)	1970-11-02	1979-05-10	Abbott Laboratories, Chicago, Ill. (V.St.A.)	Verfahren zur Demethylierung des Dimethylaminorestes in Erythromycin-AnÜbiotika
EP0349100A2 (fr)	1988-04-18	1990-01-03	Eli Lilly And Company	Compositions de macrolides dans le traitement des troubles de la motilité gastrointestinale

Also Published As

Publication number	Publication date
DZ1652A1 (fr)	2002-02-17
DK0550895T3 (da)	1997-08-25
ES2104808T3 (es)	1997-10-16
HU210216A9 (en)	1995-02-28
FI930051A0 (fi)	1993-01-07
MX9300045A (es)	1993-12-01
AU3103693A (en)	1993-07-08
NO930029D0 (no)	1993-01-06
KR930016436A (ko)	1993-08-26
JPH07247299A (ja)	1995-09-26
HK1014003A1 (en)	1999-09-17
SK279251B6 (sk)	1998-08-05
DE59208710D1 (de)	1997-08-21
CN1033646C (zh)	1996-12-25
CZ281773B6 (cs)	1997-01-15
EP0550895A1 (fr)	1993-07-14
NO179586C (no)	1996-11-06
LTIP187A (lt)	1994-03-25
HU9204076D0 (en)	1993-04-28
HUT66234A (en)	1994-10-28
AU667699B2 (en)	1996-04-04
JP3300084B2 (ja)	2002-07-08
US5418224A (en)	1995-05-23
SK341492A3 (en)	1995-05-10
ZA9339B (en)	1993-08-05
FI930051L (fi)	1993-07-08
ATE155478T1 (de)	1997-08-15
CN1075320A (zh)	1993-08-18
HU212272B (en)	1996-04-29
CZ341492A3 (en)	1993-07-14
FI106862B (fi)	2001-04-30
RU2107070C1 (ru)	1998-03-20
EP0550895B1 (fr)	1997-07-16
CA2086811C (fr)	2003-12-09
NO930029L (no)	1993-07-08
LV10458B (en)	1996-02-20
CA2086811A1 (fr)	1993-07-08
KR100273937B1 (ko)	2000-12-15
GR3024859T3 (en)	1998-01-30
PH30098A (en)	1996-12-27
LV10458A (lv)	1995-02-20
NO179586B (no)	1996-07-29
DE4200145A1 (de)	1993-07-08
UA29393C2 (uk)	2000-11-15
IL104158A0 (en)	1993-05-13
TW238308B (fr)	1995-01-11
IL104158A (en)	1997-07-13

Legal Events

Date	Code	Title	Description
1997-10-27	PD9A	Change of patent owner	Free format text: SOLVAY PHARMACEUTICALS GMBH,HANS-BOECKLER-ALLEE 20, D-30173 HANNOVER,DE,19970725
2009-07-27	MM9A	Lapsed patents	Effective date: 20081222

Publication	Publication Date	Title
JP3300084B2 (ja)	2002-07-08	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)	2002-04-27	Производные 10,13,15-триоксатрицикло (9.2.1.1.9.6)-пентадеканона, способ их получения и содержащие эти соединения лекарственные средства
MXPA97007974A (en)	1998-04-01	Derivatives of 10, 13, 15-trioxatriciclo [9.2.1.1 9.6] -pentadecanona, procedures for its preparation and medicines that contain these compounds
US6165985A (en)	2000-12-26	11-acetyl-12,13-dioxabicyclo[8.2.1]-tridecenone derivatives, processes for their preparation and pharmaceutical compositions comprising them
KR100584017B1 (ko)	2006-05-30	11-아세틸-12,13-디옥사바이시클로〔8.2.1〕-트리데케논 유도체,이의 제조방법 및 이 화합물을 포함하는 약제
HK1010885B (en)	2003-03-14	10,13,15-trioxatricyclo [9.2.1.1.9.6]-pentadecanone-derivates, process for their preparation and pharmaceutical containing them