LU87150A1 - Nouveau carbamate de phenyle,sa preparation et son utilisation comme medicament - Google Patents

Nouveau carbamate de phenyle,sa preparation et son utilisation comme medicament Download PDF

Info

Publication number: LU87150A1
Authority: LU; Luxembourg
Prior art keywords: ethyl; compound; pharmaceutically acceptable; formula; free base
Prior art date: 1987-03-04

Application number

LU87150A

Other languages

English (en)

French (fr)

Original Assignee

Sandoz Sa

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.)

1987-03-04

Filing date

1988-03-02

Publication date

1988-11-17

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=6322236&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=LU87150(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1988-03-02 Application filed by Sandoz Sa filed Critical Sandoz Sa

1988-11-17 Publication of LU87150A1 publication Critical patent/LU87150A1/fr

Links

238000002360 preparation method Methods 0.000 title claims description 9
BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 49
150000003839 salts Chemical class 0.000 claims description 20
239000012458 free base Substances 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 18
239000013543 active substance Substances 0.000 claims description 17
238000000034 method Methods 0.000 claims description 17
239000003814 drug Substances 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 14
239000008194 pharmaceutical composition Substances 0.000 claims description 13
-1 3- [1- (dimethylamino) -ethyl] -phenyl Chemical group 0.000 claims description 7
230000009885 systemic effect Effects 0.000 claims description 7
208000024827 Alzheimer disease Diseases 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
FEWJPZIEWOKRBE-JCYAYHJZSA-M L-tartrate(1-) Chemical compound OC(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-M 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
239000003085 diluting agent Substances 0.000 claims description 4
206010003591 Ataxia Diseases 0.000 claims description 3
201000010374 Down Syndrome Diseases 0.000 claims description 3
208000023105 Huntington disease Diseases 0.000 claims description 3
206010020651 Hyperkinesia Diseases 0.000 claims description 3
208000000269 Hyperkinesis Diseases 0.000 claims description 3
206010026749 Mania Diseases 0.000 claims description 3
206010039966 Senile dementia Diseases 0.000 claims description 3
230000001154 acute effect Effects 0.000 claims description 3
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
208000035475 disorder Diseases 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
238000002560 therapeutic procedure Methods 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
KMJTTWREVXZPTK-UHFFFAOYSA-M n-ethyl-n-methylcarbamate Chemical compound CCN(C)C([O-])=O KMJTTWREVXZPTK-UHFFFAOYSA-M 0.000 claims 4
XSVMFMHYUFZWBK-UHFFFAOYSA-N [3-[1-(dimethylamino)ethyl]phenyl] n-ethyl-n-methylcarbamate Chemical compound CCN(C)C(=O)OC1=CC=CC(C(C)N(C)C)=C1 XSVMFMHYUFZWBK-UHFFFAOYSA-N 0.000 claims 1
125000004433 nitrogen atom Chemical group N* 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 claims 1
229940127557 pharmaceutical product Drugs 0.000 claims 1
230000001225 therapeutic effect Effects 0.000 claims 1
102100033639 Acetylcholinesterase Human genes 0.000 description 22
108010022752 Acetylcholinesterase Proteins 0.000 description 22
229940022698 acetylcholinesterase Drugs 0.000 description 22
230000000694 effects Effects 0.000 description 22
241000700159 Rattus Species 0.000 description 20
210000004556 brain Anatomy 0.000 description 17
229940126062 Compound A Drugs 0.000 description 16
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 16
238000012360 testing method Methods 0.000 description 15
230000005764 inhibitory process Effects 0.000 description 13
229960004373 acetylcholine Drugs 0.000 description 12
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 9
229940079593 drug Drugs 0.000 description 9
210000001577 neostriatum Anatomy 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 8
229910052722 tritium Inorganic materials 0.000 description 8
210000001320 hippocampus Anatomy 0.000 description 7
241001465754 Metazoa Species 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
230000009471 action Effects 0.000 description 6
239000000126 substance Substances 0.000 description 6
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 5
238000000338 in vitro Methods 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
CFFZDZCDUFSOFZ-UHFFFAOYSA-N 3,4-Dihydroxy-phenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C(O)=C1 CFFZDZCDUFSOFZ-UHFFFAOYSA-N 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 4
108090000790 Enzymes Proteins 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
229940088598 enzyme Drugs 0.000 description 4
QRMZSPFSDQBLIX-UHFFFAOYSA-N homovanillic acid Chemical compound COC1=CC(CC(O)=O)=CC=C1O QRMZSPFSDQBLIX-UHFFFAOYSA-N 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
239000003112 inhibitor Substances 0.000 description 4
239000011159 matrix material Substances 0.000 description 4
230000035515 penetration Effects 0.000 description 4
VRYALKFFQXWPIH-PBXRRBTRSA-N (3r,4s,5r)-3,4,5,6-tetrahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)CC=O VRYALKFFQXWPIH-PBXRRBTRSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000009825 accumulation Methods 0.000 description 3
210000005013 brain tissue Anatomy 0.000 description 3
210000003169 central nervous system Anatomy 0.000 description 3
238000005119 centrifugation Methods 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
230000004907 flux Effects 0.000 description 3
230000000971 hippocampal effect Effects 0.000 description 3
229920001477 hydrophilic polymer Polymers 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
230000004060 metabolic process Effects 0.000 description 3
239000002207 metabolite Substances 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
239000011505 plaster Substances 0.000 description 3
230000000638 stimulation Effects 0.000 description 3
238000007920 subcutaneous administration Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
206010008674 Cholinergic syndrome Diseases 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 2
108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 2
XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 description 2
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
229960001231 choline Drugs 0.000 description 2
239000000544 cholinesterase inhibitor Substances 0.000 description 2
229960003638 dopamine Drugs 0.000 description 2
231100000673 dose–response relationship Toxicity 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000010579 first pass effect Methods 0.000 description 2
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
239000008103 glucose Substances 0.000 description 2
230000002440 hepatic effect Effects 0.000 description 2
CBCIHIVRDWLAME-UHFFFAOYSA-N hexanitrodiphenylamine Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O CBCIHIVRDWLAME-UHFFFAOYSA-N 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
230000003518 presynaptic effect Effects 0.000 description 2
OPYKHUMNFAMIBL-NILKIKDOSA-L (2s)-2-[4-[4-[(2s)-2-hydroxy-4,4-dimethylmorpholin-4-ium-2-yl]phenyl]phenyl]-4,4-dimethylmorpholin-4-ium-2-ol;dibromide Chemical compound [Br-].[Br-].C1[N+](C)(C)CCO[C@@]1(O)C1=CC=C(C=2C=CC(=CC=2)[C@]2(O)OCC[N+](C)(C)C2)C=C1 OPYKHUMNFAMIBL-NILKIKDOSA-L 0.000 description 1
MYGCFWRBKKQKCG-GBWOLBBFSA-N (z,2r,3s,4r)-hex-5-ene-1,2,3,4,6-pentol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)\C=C/O MYGCFWRBKKQKCG-GBWOLBBFSA-N 0.000 description 1
NTBLZMAMTZXLBP-UHFFFAOYSA-M 2-acetylsulfanylethyl(trimethyl)azanium;iodide Chemical compound [I-].CC(=O)SCC[N+](C)(C)C NTBLZMAMTZXLBP-UHFFFAOYSA-M 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
229930003347 Atropine Natural products 0.000 description 1
QYOVMAREBTZLBT-KTKRTIGZSA-N CCCCCCCC\C=C/CCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO QYOVMAREBTZLBT-KTKRTIGZSA-N 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
102000003914 Cholinesterases Human genes 0.000 description 1
108090000322 Cholinesterases Proteins 0.000 description 1
229920003149 Eudragit® E 100 Polymers 0.000 description 1
RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
125000002066 L-histidyl group Chemical group [H]N1C([H])=NC(C([H])([H])[C@](C(=O)[*])([H])N([H])[H])=C1[H] 0.000 description 1
239000012891 Ringer solution Substances 0.000 description 1
241001247203 Syngnathidae Species 0.000 description 1
229920004890 Triton X-100 Polymers 0.000 description 1
239000013504 Triton X-100 Substances 0.000 description 1
230000037374 absorbed through the skin Effects 0.000 description 1
239000000556 agonist Substances 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 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
230000009435 amidation Effects 0.000 description 1
238000007112 amidation reaction Methods 0.000 description 1
239000012491 analyte Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
229960000396 atropine Drugs 0.000 description 1
238000013475 authorization Methods 0.000 description 1
230000008901 benefit Effects 0.000 description 1
NEDGUIRITORSKL-UHFFFAOYSA-N butyl 2-methylprop-2-enoate;2-(dimethylamino)ethyl 2-methylprop-2-enoate;methyl 2-methylprop-2-enoate Chemical compound COC(=O)C(C)=C.CCCCOC(=O)C(C)=C.CN(C)CCOC(=O)C(C)=C NEDGUIRITORSKL-UHFFFAOYSA-N 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
230000001713 cholinergic effect Effects 0.000 description 1
229940048961 cholinesterase Drugs 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
229940079919 digestives enzyme preparation Drugs 0.000 description 1
230000003291 dopaminomimetic effect Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
KMJTTWREVXZPTK-UHFFFAOYSA-N ethyl(methyl)carbamic acid Chemical compound CCN(C)C(O)=O KMJTTWREVXZPTK-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011888 foil Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
210000001753 habenula Anatomy 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
238000000265 homogenisation Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
239000000472 muscarinic agonist Substances 0.000 description 1
230000003551 muscarinic effect Effects 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
239000002985 plastic film Substances 0.000 description 1
229920006255 plastic film Polymers 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
238000005070 sampling Methods 0.000 description 1
RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
238000002798 spectrophotometry method Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
210000001103 thalamus Anatomy 0.000 description 1
VUOALROPAIMXGN-UHFFFAOYSA-N trimethyl(2-propoxyethyl)azanium Chemical class CCCOCC[N+](C)(C)C VUOALROPAIMXGN-UHFFFAOYSA-N 0.000 description 1
230000000007 visual effect Effects 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/325—Carbamic acids; Thiocarbamic acids; Anhydrides or salts thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
- C07C271/42—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/44—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- 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

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Epidemiology (AREA)
Psychiatry (AREA)
Emergency Medicine (AREA)
Dermatology (AREA)
Pain & Pain Management (AREA)
Hospice & Palliative Care (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)

LU87150A 1987-03-04 1988-03-02 Nouveau carbamate de phenyle,sa preparation et son utilisation comme medicament LU87150A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3706914		1987-03-04
DE3706914		1987-03-04

Publications (1)

Publication Number	Publication Date
LU87150A1 true LU87150A1 (fr)	1988-11-17

Family

ID=6322236

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
LU87150A LU87150A1 (fr)	1987-03-04	1988-03-02	Nouveau carbamate de phenyle,sa preparation et son utilisation comme medicament
LU90297C LU90297I2 (fr)	1987-03-04	1998-10-07	Rivastigmine ses sels et dérivés pharmaceutiquement acceptables en particulier la rivastigmine sous forme d'hydrogénotartrate

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
LU90297C LU90297I2 (fr)	1987-03-04	1998-10-07	Rivastigmine ses sels et dérivés pharmaceutiquement acceptables en particulier la rivastigmine sous forme d'hydrogénotartrate

Country Status (29)

Country	Link
US (1)	US5602176A (de)
JP (3)	JP2625478B2 (de)
KR (1)	KR0133686B1 (de)
AT (1)	AT394190B (de)
AU (1)	AU618949B2 (de)
BE (1)	BE1001467A3 (de)
CA (1)	CA1307003C (de)
CH (1)	CH675720A5 (de)
CS (1)	CS411091A3 (de)
CY (1)	CY1735A (de)
DK (1)	DK175762B1 (de)
ES (1)	ES2010527A6 (de)
FI (1)	FI89165C (de)
FR (1)	FR2611707B1 (de)
GB (1)	GB2203040C (de)
GR (1)	GR1000023B (de)
HK (1)	HK110093A (de)
HU (1)	HU201906B (de)
IE (1)	IE61714B1 (de)
IL (1)	IL85609A (de)
IT (1)	IT1219853B (de)
LU (2)	LU87150A1 (de)
MY (1)	MY103225A (de)
NL (1)	NL195004C (de)
NZ (1)	NZ223714A (de)
PT (1)	PT86875B (de)
SA (1)	SA93140384B1 (de)
SE (1)	SE8800731L (de)
ZA (1)	ZA881584B (de)

Families Citing this family (89)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU201906B (en) *	1987-03-04	1991-01-28	Sandoz Ag	Process for producing phenyl-carbamate derivative and acid additional salts and pharmaceutical compositions containing them
AU2224195A (en) *	1994-04-15	1995-11-10	Masaomi Iyo	Medicinal composition for treating tardive dyskinesia and utilization thereof
US6251938B1 (en)	1996-12-18	2001-06-26	Teva Pharmaceutical Industries, Ltd.,	Phenylethylamine derivatives
WO1998026775A1 (en) *	1996-12-18	1998-06-25	Teva Pharmaceutical Industries, Ltd.	Phenylethylamine derivatives
ES2241064T3 (es)	1996-12-18	2005-10-16	Teva Pharmaceutical Industries, Ltd.	Derivados de aminoindano.
GB9800526D0 (en)	1998-01-12	1998-03-11	Ciba Geigy Ag	Organic compounds
US6316023B1 (en) *	1998-01-12	2001-11-13	Novartis Ag	TTS containing an antioxidant
US6218383B1 (en)	1998-08-07	2001-04-17	Targacept, Inc.	Pharmaceutical compositions for the prevention and treatment of central nervous system disorders
BR9914251A (pt)	1998-10-01	2001-06-19	Novartis Ag	Formulações orais de liberação sustentada
US20040209849A1 (en) *	1998-11-27	2004-10-21	Sanochemia Pharmazeutika Aktiengesellschaft	Use of effectors of the central cholinergic nervous system for treatment of delirium
JP2002531502A (ja) *	1998-12-11	2002-09-24	デイビス、ボニー	視床下部−下垂体−生殖腺軸変調に於けるアセチルコリンエステラーゼ阻害剤の使用
GB9923045D0 (en) *	1999-09-29	1999-12-01	Novartis Ag	New oral formulations
US6534541B1 (en) *	1999-10-19	2003-03-18	Novartis Ag	Treatment of ocular disorders
AU5702201A (en) *	2000-04-13	2001-10-30	Mayo Foundation	Abeta<sub>42</sub> lowering agents
US20040010038A1 (en) *	2002-02-27	2004-01-15	Eran Blaugrund	Propargylamino indan derivatives and propargylamino tetralin derivatives as brain-selective MAO inhibitors
CZ20023555A3 (cs)	2002-10-24	2004-01-14	Léčiva, A.S.	Způsob výroby (-)-(S)-3-[1-(dimethylamino)ethyl]fenyl-N-ethyl-N-methylkarbamátu
KR100777904B1 (ko) *	2002-10-24	2007-11-28	메르츠 파마 게엠베하 운트 코. 카가아	1-아미노시클로헥산 유도체 및 아세틸콜린에스테라제 저해제를 포함하는 약학적 제품 및 이를 이용한 복합 치료
WO2004071431A2 (en) *	2003-02-05	2004-08-26	Myriad Genetics, Inc.	Method and composition for treating neurodegenerative disorders
US7521481B2 (en)	2003-02-27	2009-04-21	Mclaurin Joanne	Methods of preventing, treating and diagnosing disorders of protein aggregation
KR20060040676A (ko) *	2003-07-11	2006-05-10	미리어드 제네틱스, 인크.	알츠하이머병을 치료하기 위한 약제학적 방법, 투약 방법및 제형
US7795307B2 (en) *	2003-10-21	2010-09-14	Colucid Pharmaceuticals, Inc.	Carbamoyl esters that inhibit cholinesterase and release pharmacologically active agents
GB2409453A (en) *	2003-12-24	2005-06-29	Generics	Process for the preparation of aminoalkyl phenylcarbamates
WO2006001877A2 (en) *	2004-04-13	2006-01-05	Myriad Genetics, Inc.	Combination treatment for neurodegenerative disorders comprising r-flurbiprofen
AU2005241023A1 (en) *	2004-04-29	2005-11-17	Keystone Retaining Wall Systems, Inc.	Veneers for walls, retaining walls and the like
EP1779867A4 (de) *	2004-07-01	2009-12-02	Eisai R&D Man Co Ltd	Mittel zur förderung der nervenreveneration
WO2006020853A2 (en) *	2004-08-11	2006-02-23	Myriad Genetics, Inc.	Pharmaceutical composition and method for treating neurodegenerative disorders
WO2006020850A2 (en) *	2004-08-11	2006-02-23	Myriad Genetics, Inc.	Pharmaceutical composition and method for treating neurodegenerative disorders
WO2006020852A2 (en) *	2004-08-11	2006-02-23	Myriad Genetics, Inc.	Pharmaceutical composition and method for treating neurodegenerative disorders
RU2393148C2 (ru) *	2004-11-08	2010-06-27	Эмкюр Фармасьютикалз Лимитед	Способ получения (s)-3-[(1-диметиламино)этил]-фенил-n-этил-n-метил-карбамата
GB0507298D0 (en)	2005-04-11	2005-05-18	Novartis Ag	Organic compounds
KR20080039876A (ko) *	2005-07-22	2008-05-07	미리어드 제네틱스, 인크.	높은 약물 충진 제형 및 투여형
ES2267399B1 (es)	2005-08-04	2008-02-01	Ragactives, S.L.	Procedimiento para la obtencion de carbamatos de fenilo.
JP5116679B2 (ja)	2005-09-15	2013-01-09	株式会社ソニー・コンピュータエンタテインメント	強度のコンピュータ画像および音声処理、ならびにコンピュータプログラムとインタフェースするための入力装置
TWI389709B (zh) *	2005-12-01	2013-03-21	Novartis Ag	經皮治療系統
ES2632638T3 (es) *	2005-12-09	2017-09-14	Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd.	Ladostigilo de baja dosis para el tratamiento de la deficiencia cognitiva
TW200744576A (en) *	2006-02-24	2007-12-16	Teva Pharma	Propargylated aminoindans, processes for preparation, and uses thereof
US7767843B2 (en) *	2006-03-02	2010-08-03	Apotex Pharmachem Inc.	Process for the preparation of phenylcarbamates
EP2046119A2 (de) *	2006-07-07	2009-04-15	Myriad Genetics, Inc.	Behandlung von psychiatrischen störungen
CA2661009A1 (en) *	2006-08-17	2008-02-21	Alembic Limited	Improved process for the preparation of rivastigmine
WO2008037433A1 (en)	2006-09-29	2008-04-03	Synthon B.V.	Process for making aminoalkylphenyl carbamates and intermediates therefor
AU2007309390A1 (en)	2006-10-27	2008-05-02	Medivation Neurology, Inc.	Methods and combination therapies for treating Alzheimer's disease
EP1942100A1 (de) *	2007-01-04	2008-07-09	Krka Tovarna Zdravil, D.D., Novo Mesto	Amorphe und kristalline Formen von Rivastigminhydrogentartrat
AU2008214380A1 (en) *	2007-02-02	2008-08-14	Colucid Pharmaceuticals, Inc.	Compounds that inhibit cholinesterase
US8013181B2 (en) *	2007-04-10	2011-09-06	Dr. Reddy's Laboratories Limited	Preparation of rivastigmine and its salts
WO2008124969A1 (en) *	2007-04-16	2008-10-23	Topharman Shanghai Co., Ltd.	Preparation method of rivastigmine and its intermediates
US7884121B2 (en) *	2007-06-11	2011-02-08	Apotex Pharmachem Inc.	Process for the preparation of phenylcarbamates
JP2010533717A (ja) *	2007-07-18	2010-10-28	コルシド・ファーマシューティカルズ・インコーポレイテッド	覚醒を促進する方法
US8593728B2 (en) *	2009-02-19	2013-11-26	Toyota Motor Engineering & Manufacturing North America, Inc.	Multilayer photonic structures
US20090082436A1 (en) *	2007-09-26	2009-03-26	Protia, Llc	Deuterium-enriched rivastigmine
CN101910110B (zh) *	2008-01-10	2013-05-22	上海医药工业研究院	利凡斯的明的制备方法、其中间体以及中间体的制备方法
US8420846B2 (en)	2008-08-25	2013-04-16	Jubilant Life Sciences Limited	Process for producing (S)-3-[(1-dimethylamino)ethyl] phenyl-N-ethyl-N-methyl-carbamate via novel intermediates
US20100087768A1 (en) *	2008-10-02	2010-04-08	Forlano Paula	Transdermal drug delivery system for liquid active ingredient
GB0823554D0 (en)	2008-12-24	2009-01-28	Novartis Ag	Process for the preparation of optically active compounds using transfer hydrogenation
CN101823970B (zh) *	2009-03-03	2013-05-08	江苏恩华药业股份有限公司	卡巴拉汀及其中间体的合成方法
ES2670227T3 (es)	2009-12-22	2018-05-29	Luye Pharma Ag	Sistema terapéutico transdérmico para la administración de rivastigmina o sus derivados
US10076502B2 (en)	2009-12-22	2018-09-18	Luye Pharma Ag	Transdermal therapeutic system for administering rivastigmine or derivatives thereof
ES2363395B1 (es) *	2010-01-20	2012-02-23	Farmalider, S.A.	Composición farmacéutica l�?quida de rivastigmina o de una de sus sales de adición de �?cido para la administración por v�?a oral.
EA202092673A3 (ru) *	2010-02-09	2021-05-31	Дзе Джонс Хопкинс Юниверсити	Способы и композиции для улучшения когнитивной функции
BR112012024708A2 (pt)	2010-03-29	2016-06-07	Novartis Ag	composição de compostos orgânicos
WO2011151669A1 (en)	2010-06-02	2011-12-08	Jubilant Life Sciences Limited	Process for producing enantiomerically enriched isomer of 3-(1-aminoethyl) phenyl derivative and employing the same to produce rivastigmine or its pharmaceutically acceptable salt
WO2011151359A1 (en)	2010-06-02	2011-12-08	Noscira, S.A.	Combined treatment with a cholinesterase inhibitor and a thiadiazolidinedione derivative
DK2582799T3 (en)	2010-06-17	2018-02-12	Codexis Inc	BIOCATALATORS AND PROCEDURES FOR THE SYNTHESIS OF (S) -3- (1-AMINOETHYL) -PHENOL
EP3034079B1 (de)	2010-11-15	2018-01-10	Agenebio, Inc.	Pyridazinderivate, zusammensetzungen und verfahren zur behandlung von kognitiven störungen
DK2468274T3 (en)	2010-12-14	2015-08-31	Acino Ag	Transdermal therapeutic system for administration of an active substance
CN102786441B (zh) *	2011-05-18	2013-11-13	浙江海正药业股份有限公司	利凡斯的明的制备方法、其中间体以及中间体的制备方法
BR112013029945A2 (pt)	2011-05-20	2017-01-31	Sk Chemicals Co Ltd	emplastro contendo rivastigmina
AR082640A1 (es) *	2011-08-25	2012-12-19	Amarin Technologies S A	Un dispositivo para la administracion transdermal de compuestos alcalinos susceptibles a la degradacion en su forma no salificada
JP6102739B2 (ja)	2011-08-31	2017-03-29	東洋インキＳｃホールディングス株式会社	貼付剤
CN103073456B (zh) *	2011-10-26	2014-03-19	连云港润众制药有限公司	重酒石酸卡巴拉汀中间体的制备方法
EP2594261A1 (de)	2011-11-18	2013-05-22	Labtec GmbH	Zusammensetzung zur transdermalen Verabreichung von Rivastigmin
WO2013142339A1 (en)	2012-03-23	2013-09-26	Novartis Ag	Transdermal therapeutic system and method
ES2449215B1 (es) *	2012-09-17	2014-07-14	Galenicum Health S.L.	Solución oral de (S)-3-[1-(dimetilamino)etil]fenil N-etil-N-metilcarbamato
KR20140038237A (ko)	2012-09-20	2014-03-28	에스케이케미칼주식회사	리바스티그민의 안정성이 개선된 의약품
US20140206667A1 (en)	2012-11-14	2014-07-24	Michela Gallagher	Methods and compositions for treating schizophrenia
CN103896787A (zh) *	2012-12-26	2014-07-02	江苏康倍得药业有限公司	一种卡巴拉汀前体[1-(3-甲氧基苯基)乙基]二甲胺的制备方法
WO2014111790A2 (en)	2013-01-15	2014-07-24	Zydus Technologies Limited	Stable transdermal pharmaceutical drug delivery system comprising rivastigmine
AU2014228512A1 (en)	2013-03-15	2015-10-01	Agenebio, Inc.	Methods and compositions for improving cognitive function
WO2014144663A1 (en)	2013-03-15	2014-09-18	The Johns Hopkins University	Methods and compositions for improving cognitive function
CN103319374B (zh) *	2013-06-09	2015-04-22	无锡佰翱得生物科学有限公司	一种(s)-卡巴拉汀的不对称合成方法
AU2014307803A1 (en)	2013-08-16	2016-03-10	Universiteit Maastricht	Treatment of cognitive impairment with PDE4 inhibitor
EP3083569B1 (de)	2013-12-20	2022-01-26	Agenebio, Inc.	Benzodiazepinderivate, zusammensetzungen und verfahren zur behandlung von kognitiven störungen
CA2986598C (en)	2015-05-22	2023-09-26	Agenebio, Inc.	Extended release pharmaceutical compositions of levetiracetam
JP6987384B2 (ja)	2015-06-19	2021-12-22	エージンバイオ，インコーポレイテッド	ベンゾジアゼピン誘導体、組成物、および認知障害を処置するための方法
US11505555B2 (en)	2016-12-19	2022-11-22	Agenebio, Inc.	Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment
US20180170941A1 (en)	2016-12-19	2018-06-21	Agenebio, Inc.	Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment
US11414425B2 (en)	2018-06-19	2022-08-16	Agenebio, Inc.	Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment
KR20200035359A (ko)	2018-09-26	2020-04-03	캐딜라 파마슈티클즈 리미티드	리바스티그민 제조용 중간체의 합성
WO2024039886A1 (en)	2022-08-19	2024-02-22	Agenebio, Inc.	Benzazepine derivatives, compositions, and methods for treating cognitive impairment
WO2025038382A1 (en)	2023-08-11	2025-02-20	Momentive Performance Materials Inc.	Pharmaceutical adhesive compositions

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4469700A (en) *	1981-06-19	1984-09-04	Lowell M. Somers	Benzoylecgonine or benzoylnorecgonine as active agents for the treatment of rheumatoid arthritis
IL74497A (en) *	1985-03-05	1990-02-09	Proterra Ag	Pharmaceutical compositions containing phenyl carbamate derivatives and certain phenyl carbamate derivatives
HU201906B (en) *	1987-03-04	1991-01-28	Sandoz Ag	Process for producing phenyl-carbamate derivative and acid additional salts and pharmaceutical compositions containing them

1988
- 1988-02-22 HU HU88827A patent/HU201906B/hu unknown
- 1988-02-22 NL NL8800436A patent/NL195004C/nl not_active IP Right Cessation
- 1988-02-29 BE BE8800230A patent/BE1001467A3/fr not_active IP Right Cessation
- 1988-02-29 FR FR888802597A patent/FR2611707B1/fr not_active Expired - Lifetime
- 1988-03-01 CH CH774/88A patent/CH675720A5/de not_active IP Right Cessation
- 1988-03-01 GB GB8804888A patent/GB2203040C/en not_active Expired - Lifetime
- 1988-03-02 AU AU12554/88A patent/AU618949B2/en not_active Expired
- 1988-03-02 NZ NZ223714A patent/NZ223714A/en unknown
- 1988-03-02 SE SE8800731A patent/SE8800731L/xx not_active Application Discontinuation
- 1988-03-02 LU LU87150A patent/LU87150A1/fr active Protection Beyond IP Right Term
- 1988-03-02 IL IL85609A patent/IL85609A/xx not_active IP Right Cessation
- 1988-03-02 IE IE58388A patent/IE61714B1/en not_active IP Right Cessation
- 1988-03-02 PT PT86875A patent/PT86875B/pt active IP Right Grant
- 1988-03-02 FI FI880972A patent/FI89165C/fi active Protection Beyond IP Right Term
- 1988-03-02 DK DK198801125A patent/DK175762B1/da not_active IP Right Cessation
- 1988-03-03 KR KR1019880002187A patent/KR0133686B1/ko not_active Expired - Lifetime
- 1988-03-03 CA CA000560457A patent/CA1307003C/en not_active Expired - Lifetime
- 1988-03-03 JP JP63052478A patent/JP2625478B2/ja not_active Expired - Lifetime
- 1988-03-03 GR GR880100125A patent/GR1000023B/el not_active IP Right Cessation
- 1988-03-03 AT AT0055188A patent/AT394190B/de not_active IP Right Cessation
- 1988-03-03 MY MYPI88000215A patent/MY103225A/en unknown
- 1988-03-04 ES ES8800651A patent/ES2010527A6/es not_active Expired
- 1988-03-04 ZA ZA881584A patent/ZA881584B/xx unknown
- 1988-03-04 IT IT47693/88A patent/IT1219853B/it active Protection Beyond IP Right Term
1991
- 1991-12-27 CS CS914110A patent/CS411091A3/cs unknown
1993
- 1993-10-21 HK HK1100/93A patent/HK110093A/xx not_active IP Right Cessation
- 1993-11-29 SA SA93140384A patent/SA93140384B1/ar unknown
1994
- 1994-06-03 CY CY173594A patent/CY1735A/en unknown
1995
- 1995-06-06 US US08/466,502 patent/US5602176A/en not_active Expired - Lifetime
1996
- 1996-09-12 JP JP8241702A patent/JPH09118617A/ja active Pending
- 1996-11-01 JP JP8291560A patent/JP2859225B2/ja not_active Expired - Lifetime
1998
- 1998-10-07 LU LU90297C patent/LU90297I2/fr unknown

Also Published As

Publication number	Publication date
KR880011088A (ko)	1988-10-26
IL85609A (en)	1992-07-15
SA93140384B1 (ar)	2006-04-04
CA1307003C (en)	1992-09-01
NL195004C (nl)	2003-11-04
GB2203040C (en)	2014-07-30
HU201906B (en)	1991-01-28
JPH09165362A (ja)	1997-06-24
AT394190B (de)	1992-02-10
FI880972A0 (fi)	1988-03-02
ATA55188A (de)	1991-08-15
DK112588D0 (da)	1988-03-02
JP2625478B2 (ja)	1997-07-02
JP2859225B2 (ja)	1999-02-17
IL85609A0 (en)	1988-08-31
FI880972L (fi)	1988-09-05
GB2203040B (en)	1990-10-24
FR2611707B1 (fr)	1990-04-20
AU618949B2 (en)	1992-01-16
JPS63238054A (ja)	1988-10-04
FI89165B (fi)	1993-05-14
GB8804888D0 (en)	1988-03-30
NL8800436A (nl)	1988-10-03
IT1219853B (it)	1990-05-24
HK110093A (en)	1993-10-29
SE8800731A0 (sv)	1988-09-05
US5602176A (en)	1997-02-11
PT86875B (pt)	1992-05-29
HUT49325A (en)	1989-09-28
GR880100125A (en)	1989-01-31
SE8800731D0 (sv)	1988-03-02
DK175762B1 (da)	2005-02-14
KR0133686B1 (ko)	1998-04-21
IT8847693A0 (it)	1988-03-04
CY1735A (en)	1994-06-03
FI89165C (fi)	1993-08-25
IE61714B1 (en)	1994-11-30
DK112588A (da)	1988-09-05
BE1001467A3 (fr)	1989-11-07
JPH09118617A (ja)	1997-05-06
PT86875A (pt)	1988-04-01
LU90297I2 (fr)	1998-12-07
NZ223714A (en)	1994-05-26
CH675720A5 (de)	1990-10-31
IE880583L (en)	1988-09-04
AU1255488A (en)	1988-09-08
ZA881584B (en)	1989-11-29
GB2203040A (en)	1988-10-12
FR2611707A1 (fr)	1988-09-09
NL195004B (nl)	2003-07-01
ES2010527A6 (es)	1989-11-16
CS411091A3 (en)	1992-12-16
SE8800731L (sv)	1988-09-05
GR1000023B (el)	1990-01-31
MY103225A (en)	1993-05-29

Legal Events

Date	Code	Title	Description
1998-12-07	CCP	Supplementary protection certificate	Free format text: 90297, EXPIRES: 20130302

Publication	Publication Date	Title
LU87150A1 (fr)	1988-11-17	Nouveau carbamate de phenyle,sa preparation et son utilisation comme medicament
US5691365A (en)	1997-11-25	Nicotinic receptor antagonists in the treatment of neuropharmacological disorders
Manoury et al.	1987	Synthesis of a series of compounds related to betaxolol, a new. beta. 1-adrenoceptor antagonist with a pharmacological and pharmacokinetic profile optimized for the treatment of chronic cardiovascular diseases
SK10912000A3 (sk)	2001-04-09	Farmaceuticky prijateľné soli a solváty (+)-(2s,3s)-2-(3-chlórfenyl)-3,5,5-trimetyl-2-morfolinolu, farmaceutický prostriedok s ich obsahom a ich použitie
EP1908461A1 (de)	2008-04-09	Verwendung des Enantiomers (1S, 2R) von Milnacipran zur Herstellung eines Arzneimittels
HUE035105T2 (en)	2018-05-02	A composition comprising nicotine and opipramole and its use
PT867179E (pt)	2000-12-29	Composicao de esteres de l-dopa
JP2012246297A (ja)	2012-12-13	ニコチン様物質受容体のモジュレーターとしてのガランタミンおよびリコラミンの類似物
CH630068A5 (en)	1982-05-28	Process for the preparation of 4-hydroxyphenylalkanolamine derivatives
CH641759A5 (fr)	1984-03-15	Phenethanolamines et composition pharmaceutique antineoplastique les contenant.
CH683427A5 (fr)	1994-03-15	Composé d'isoquinoléine comme agents de blocage neuromusculaire.
EP0429360B1 (de)	1993-10-13	Verhinderung von Entzugserscheinungen
US6734213B2 (en)	2004-05-11	Pharmaceutically active morpholinol
BE1003959A5 (fr)	1992-07-22	Agent therapeutique pour le traitement de troubles associes a l'ischemie cerebrale.
NL195081C (nl)	2003-09-22	Fenylcarbamaat.
US20090176835A1 (en)	2009-07-09	Pharmaceutical composition for suppression of the expression of atp citrate lyase and use thereof
EP1547614B1 (de)	2011-01-19	Medizinische zusammensetzungen zur hemmung der expression von atp-citrat-lyase und ihre verwendung
EP0489640B1 (de)	1996-10-02	Verwendung von Phenyläthanolaminotetralinen zur Herstellung eines antidepressiven und Antistress-Arzneimittels
FR2744364A1 (fr)	1997-08-08	Application d'ureidoacetamides a la preparation de medicaments destines au traitement de l'abus de drogues ou de substances donnant lieu a des pharmacomanies ou a un usage excessif
EP1406627B1 (de)	2006-11-08	Pyridin-2-yl-methylamin-derivate zur behandlung von opiatsucht
Musson	1979	Chemical and Biological Studies on 3-(2, 4, 5-trihydroxyphenyl)-2-methylalanine (6-hydroxy-[alpha]-methyldopa)
WO1997033582A1 (fr)	1997-09-18	Compositions d'antagonistes de site polyamine
FR2741804A1 (fr)	1997-06-06	Application de 2-iminobenzothiazolines dans le traitement de la maladie de parkinson et des syndromes parkinsoniens
BE889046A (fr)	1981-12-02	Nouveaux medicaments a base de 4-aryl-2 (h)-quinazolinones pour le traitement de la dysmenorrhee