UA73789C2 - 1,3-dioxolans with antitussive activity - Google Patents

1,3-dioxolans with antitussive activity Download PDF

Info

Publication number: UA73789C2
Authority: UA; Ukraine
Prior art keywords: phenylpiperazin; diol; propane; cyclohexylidene; formula
Prior art date: 2000-07-28

Application number

UA2003021767A

Other languages

English (en)

Ukrainian (uk)

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.)

2000-07-28

Filing date

2001-07-18

Publication date

2005-09-15

2001-07-18 Application filed filed Critical

2005-09-15 Publication of UA73789C2 publication Critical patent/UA73789C2/uk

Links

230000000954 anitussive effect Effects 0.000 title claims description 6
238000000034 method Methods 0.000 claims abstract description 15
150000001875 compounds Chemical class 0.000 claims description 30
YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 8
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
230000003993 interaction Effects 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
229940095064 tartrate Drugs 0.000 claims description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
239000008096 xylene Substances 0.000 claims description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
125000002837 carbocyclic group Chemical group 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
229940126601 medicinal product Drugs 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
150000003839 salts Chemical class 0.000 abstract description 15
238000002360 preparation method Methods 0.000 abstract description 9
PTVWPYVOOKLBCG-ZDUSSCGKSA-N levodropropizine Chemical compound C1CN(C[C@H](O)CO)CCN1C1=CC=CC=C1 PTVWPYVOOKLBCG-ZDUSSCGKSA-N 0.000 abstract description 6
229960002265 levodropropizine Drugs 0.000 abstract description 6
150000001241 acetals Chemical class 0.000 abstract description 3
239000003434 antitussive agent Substances 0.000 abstract description 3
229940124584 antitussives Drugs 0.000 abstract description 3
239000000543 intermediate Substances 0.000 abstract description 3
239000000243 solution Substances 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 8
239000000443 aerosol Substances 0.000 description 7
206010011224 Cough Diseases 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
239000000594 mannitol Substances 0.000 description 4
239000012071 phase Substances 0.000 description 4
229960004063 propylene glycol Drugs 0.000 description 4
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
239000004146 Propane-1,2-diol Substances 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
229960002504 capsaicin Drugs 0.000 description 3
238000001816 cooling Methods 0.000 description 3
150000004862 dioxolanes Chemical class 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000003814 drug Substances 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
235000013772 propylene glycol Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000010561 standard procedure Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
241000700198 Cavia Species 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
125000004036 acetal group Chemical group 0.000 description 2
239000003513 alkali Substances 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
235000017663 capsaicin Nutrition 0.000 description 2
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
230000002255 enzymatic effect Effects 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
238000000926 separation method Methods 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
MLIWQXBKMZNZNF-KUHOPJCQSA-N (2e)-2,6-bis[(4-azidophenyl)methylidene]-4-methylcyclohexan-1-one Chemical compound O=C1\C(=C\C=2C=CC(=CC=2)N=[N+]=[N-])CC(C)CC1=CC1=CC=C(N=[N+]=[N-])C=C1 MLIWQXBKMZNZNF-KUHOPJCQSA-N 0.000 description 1
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
BOHGAOWOIJMTPZ-UHFFFAOYSA-N 1,3-dioxolan-4-ylmethanol Chemical class OCC1COCO1 BOHGAOWOIJMTPZ-UHFFFAOYSA-N 0.000 description 1
125000006091 1,3-dioxolane group Chemical class 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
YOWQWFMSQCOSBA-UHFFFAOYSA-N 2-methoxypropene Chemical compound COC(C)=C YOWQWFMSQCOSBA-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
PTVWPYVOOKLBCG-UHFFFAOYSA-N 3-(4-phenyl-1-piperazinyl)propane-1,2-diol Chemical compound C1CN(CC(O)CO)CCN1C1=CC=CC=C1 PTVWPYVOOKLBCG-UHFFFAOYSA-N 0.000 description 1
TZBLDNXQFGCZRB-UHFFFAOYSA-N 3-(4-phenylpiperazin-1-yl)propane-1,1-diol;hydrochloride Chemical compound Cl.C1CN(CCC(O)O)CCN1C1=CC=CC=C1 TZBLDNXQFGCZRB-UHFFFAOYSA-N 0.000 description 1
ZZKDGABMFBCSRP-UHFFFAOYSA-N 3-ethyl-2-methylpyridine Chemical compound CCC1=CC=CN=C1C ZZKDGABMFBCSRP-UHFFFAOYSA-N 0.000 description 1
XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 1
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
206010013911 Dysgeusia Diseases 0.000 description 1
CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical group CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
-1 anhydride chloride Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
239000012965 benzophenone Substances 0.000 description 1
239000012455 biphasic mixture Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229960000846 camphor Drugs 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
238000005119 centrifugation Methods 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical class C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N malonic acid group Chemical group C(CC(=O)O)(=O)O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
LLCOIQRNSJBFSN-UHFFFAOYSA-N methane;sulfurochloridic acid Chemical compound C.OS(Cl)(=O)=O LLCOIQRNSJBFSN-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000006864 oxidative decomposition reaction Methods 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 description 1
239000001230 potassium iodate Substances 0.000 description 1
235000006666 potassium iodate Nutrition 0.000 description 1
229940093930 potassium iodate Drugs 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
230000007017 scission Effects 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003459 sulfonic acid esters Chemical class 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000009967 tasteless effect Effects 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Pulmonology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Glass Compositions (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Hydrogenated Pyridines (AREA)

UA2003021767A 2000-07-28 2001-07-18 1,3-dioxolans with antitussive activity UA73789C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT2000MI001734A IT1318650B1 (it)	2000-07-28	2000-07-28	1,3-diossolani ad attivita' antitosse.
PCT/EP2001/008304 WO2002010149A1 (en)	2000-07-28	2001-07-18	1,3-dioxolanes with antitussive activity

Publications (1)

Publication Number	Publication Date
UA73789C2 true UA73789C2 (en)	2005-09-15

Family

ID=11445591

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2003021767A UA73789C2 (en)	2000-07-28	2001-07-18	1,3-dioxolans with antitussive activity

Country Status (26)

Country	Link
US (1)	US6835734B2 (de)
EP (1)	EP1307441B1 (de)
JP (1)	JP5107497B2 (de)
KR (1)	KR100781403B1 (de)
CN (1)	CN1204135C (de)
AT (1)	ATE266018T1 (de)
AU (1)	AU2001287638A1 (de)
BR (1)	BR0112765A (de)
CZ (1)	CZ301087B6 (de)
DE (1)	DE60103164T2 (de)
DK (1)	DK1307441T3 (de)
EE (1)	EE05178B1 (de)
ES (1)	ES2219562T3 (de)
HU (1)	HUP0301497A3 (de)
IL (2)	IL153515A0 (de)
IT (1)	IT1318650B1 (de)
MX (1)	MXPA02012920A (de)
PL (1)	PL206307B1 (de)
PT (1)	PT1307441E (de)
RS (1)	RS50861B (de)
RU (1)	RU2276149C2 (de)
SI (1)	SI21040A (de)
SK (1)	SK286794B6 (de)
TR (1)	TR200401315T4 (de)
UA (1)	UA73789C2 (de)
WO (1)	WO2002010149A1 (de)

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IT1318651B1 (it) *	2000-07-28	2003-08-27	Dompe Spa	Sintesi di (+-)1,3-diossolani e loro risoluzione ottica.
TWI496776B (zh) *	2007-11-15	2015-08-21	Astrazeneca Ab	製備(3aR,4S,6R,6aS)-6-胺基-2,2-二甲基四氫-3aH-環戊并[d][1,3]二氧雜環戊烯-4-醇之純非對映異構性之二苯甲醯-L-酒石酸鹽之方法
EP2070915A1 (de) *	2007-12-03	2009-06-17	A.M.S.A. ANONIMA MATERIE SINTETICHE E AFFINI S.p.A.	Neues Verfahren zur Synthese von Moguistein

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US4049660A (en) *	1971-06-18	1977-09-20	Delalande S.A.	N-substituted derivatives of 4 (N-piperazinylmethyl) spiro dibenzocycloheptadi- (or tri-) ene-5, 2-dioxolane (1,3) their method of preparation and their application in therapeutics
IT1203721B (it) *	1983-12-29	1989-02-23	Dompe Farmaceutici Spa	Composti otticamente attivi ad attivita' antitosse e sedativa centrale,procedimento per la preparazione e composizioni che li contengono
NL8801622A (nl) *	1988-06-25	1990-01-16	Stamicarbon	Bereiding van enantiomeren van dropropizine.
IT1226570B (it) *	1988-08-01	1991-01-24	Bidachem Spa	Procedimento di preparazione della levo- e destro-dropropizina
DE4041482A1 (de) *	1990-12-22	1992-06-25	Boehringer Ingelheim Kg	Neue pharmazeutische verwendung carbocyclisch und heterocyclisch annelierter dihydropyridine
IT1254452B (it) *	1992-02-14	1995-09-25	Dompe Farmaceutici Spa	N-ossidi ed n,n'-diossidi di 3-(piperazin-1-il)-propan-1,2-dioli
IT1254993B (it) *	1992-06-24	1995-10-11		Procedimento per la preparazione degli enantiomeri della dropropizina
IL111730A (en) *	1993-11-29	1998-12-06	Fujisawa Pharmaceutical Co	Piperazine derivatives processes for the preparation thereof and pharmaceutical compositions containing the same
IT1318651B1 (it) *	2000-07-28	2003-08-27	Dompe Spa	Sintesi di (+-)1,3-diossolani e loro risoluzione ottica.

2000
- 2000-07-28 IT IT2000MI001734A patent/IT1318650B1/it active
2001
- 2001-07-18 JP JP2002515880A patent/JP5107497B2/ja not_active Expired - Fee Related
- 2001-07-18 SI SI200120036A patent/SI21040A/sl not_active IP Right Cessation
- 2001-07-18 KR KR1020037000945A patent/KR100781403B1/ko not_active Expired - Fee Related
- 2001-07-18 RS YUP-30/03A patent/RS50861B/sr unknown
- 2001-07-18 HU HU0301497A patent/HUP0301497A3/hu unknown
- 2001-07-18 BR BR0112765-9A patent/BR0112765A/pt not_active Application Discontinuation
- 2001-07-18 PL PL361172A patent/PL206307B1/pl not_active IP Right Cessation
- 2001-07-18 CZ CZ20030268A patent/CZ301087B6/cs not_active IP Right Cessation
- 2001-07-18 MX MXPA02012920A patent/MXPA02012920A/es active IP Right Grant
- 2001-07-18 AT AT01967203T patent/ATE266018T1/de active
- 2001-07-18 ES ES01967203T patent/ES2219562T3/es not_active Expired - Lifetime
- 2001-07-18 TR TR2004/01315T patent/TR200401315T4/xx unknown
- 2001-07-18 RU RU2003105691/04A patent/RU2276149C2/ru not_active IP Right Cessation
- 2001-07-18 PT PT01967203T patent/PT1307441E/pt unknown
- 2001-07-18 UA UA2003021767A patent/UA73789C2/uk unknown
- 2001-07-18 AU AU2001287638A patent/AU2001287638A1/en not_active Abandoned
- 2001-07-18 WO PCT/EP2001/008304 patent/WO2002010149A1/en not_active Ceased
- 2001-07-18 SK SK89-2003A patent/SK286794B6/sk not_active IP Right Cessation
- 2001-07-18 DK DK01967203T patent/DK1307441T3/da active
- 2001-07-18 IL IL15351501A patent/IL153515A0/xx active IP Right Grant
- 2001-07-18 EP EP01967203A patent/EP1307441B1/de not_active Expired - Lifetime
- 2001-07-18 CN CNB018134564A patent/CN1204135C/zh not_active Expired - Fee Related
- 2001-07-18 DE DE60103164T patent/DE60103164T2/de not_active Expired - Lifetime
- 2001-07-18 EE EEP200300036A patent/EE05178B1/xx not_active IP Right Cessation
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2002
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Also Published As

Publication number	Publication date
HK1058797A1 (en)	2004-06-04
BR0112765A (pt)	2004-01-13
IT1318650B1 (it)	2003-08-27
JP2004505073A (ja)	2004-02-19
ATE266018T1 (de)	2004-05-15
EE05178B1 (et)	2009-06-15
JP5107497B2 (ja)	2012-12-26
PT1307441E (pt)	2004-09-30
PL361172A1 (en)	2004-09-20
CN1204135C (zh)	2005-06-01
KR20030016425A (ko)	2003-02-26
DE60103164D1 (de)	2004-06-09
SI21040A (sl)	2003-04-30
KR100781403B1 (ko)	2007-12-03
AU2001287638A1 (en)	2002-02-13
EP1307441A1 (de)	2003-05-07
TR200401315T4 (tr)	2004-07-21
US6835734B2 (en)	2004-12-28
DE60103164T2 (de)	2005-05-04
ITMI20001734A1 (it)	2002-01-28
YU3003A (sh)	2006-05-25
HUP0301497A2 (hu)	2003-09-29
ES2219562T3 (es)	2004-12-01
SK892003A3 (en)	2003-09-11
US20040038989A1 (en)	2004-02-26
RU2276149C2 (ru)	2006-05-10
MXPA02012920A (es)	2004-04-20
CN1444578A (zh)	2003-09-24
DK1307441T3 (da)	2004-08-09
ITMI20001734A0 (it)	2000-07-28
HUP0301497A3 (en)	2005-08-29
PL206307B1 (pl)	2010-07-30
IL153515A0 (en)	2003-07-06
SK286794B6 (sk)	2009-05-07
CZ2003268A3 (cs)	2003-06-18
CZ301087B6 (cs)	2009-11-04
WO2002010149A1 (en)	2002-02-07
EE200300036A (et)	2004-10-15
RS50861B (sr)	2010-08-31
IL153515A (en)	2006-12-10
EP1307441B1 (de)	2004-05-06

Publication	Publication Date	Title
US3268582A (en)	1966-08-23	Phenylalkyl-carboxylic acid amides
RU2276149C2 (ru)	2006-05-10	1,3-диоксоланы, способ их получения и фармацевтическая композиция
EP1307440B1 (de)	2005-03-09	2,2-disubstituierte 1,3-dioxolane als hustenmittel
EP0069962B1 (de)	1985-01-02	1,1-Dioxopenicillansäure-Ester, Verfahren zu seiner Herstellung und seine Verwendung als Beta-lactamase Hemmstoff
HK1058797B (en)	2005-09-16	1,3-dioxolanes with antitussive activity
JPH054949A (ja)	1993-01-14	光学活性シクロブチルアミン類の製造方法