LU87122A1 - Nouveaux derives de la pilocarpine,leur preparation et leur utilisation comme medicaments - Google Patents
Nouveaux derives de la pilocarpine,leur preparation et leur utilisation comme medicaments Download PDFInfo
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- LU87122A1 LU87122A1 LU87122A LU87122A LU87122A1 LU 87122 A1 LU87122 A1 LU 87122A1 LU 87122 A LU87122 A LU 87122A LU 87122 A LU87122 A LU 87122A LU 87122 A1 LU87122 A1 LU 87122A1
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- Prior art keywords
- methyl
- formula
- acid addition
- signifies
- compound
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- 239000003814 drug Substances 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 5
- QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical class C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 58
- 239000002253 acid Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000012458 free base Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 208000010412 Glaucoma Diseases 0.000 claims description 4
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 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 claims description 4
- 206010026749 Mania Diseases 0.000 claims description 3
- 206010039966 Senile dementia Diseases 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 206010028417 myasthenia gravis Diseases 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 208000020016 psychiatric disease Diseases 0.000 claims description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- 230000009466 transformation Effects 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000008024 pharmaceutical diluent Substances 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- JEKWFJIPBJGBJT-WCBMZHEXSA-N (3r,4r)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]thiolan-2-one Chemical compound C1SC(=O)[C@H](CC)[C@H]1CC1=CN=CN1C JEKWFJIPBJGBJT-WCBMZHEXSA-N 0.000 claims 1
- JEKWFJIPBJGBJT-WPRPVWTQSA-N (3s,4r)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]thiolan-2-one Chemical compound C1SC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C JEKWFJIPBJGBJT-WPRPVWTQSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- -1 1-methyl-1H-imidazol-5-yl Chemical group 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 239000000155 melt Substances 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 230000001713 cholinergic effect Effects 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 6
- 229960004373 acetylcholine Drugs 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
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- 239000000047 product Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 230000001242 postsynaptic effect Effects 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
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- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 229930000680 A04AD01 - Scopolamine Natural products 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 description 3
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 3
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 3
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- QCHFTSOMWOSFHM-UHFFFAOYSA-N SJ000285536 Natural products C1OC(=O)C(CC)C1CC1=CN=CN1C QCHFTSOMWOSFHM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 3
- 239000003149 muscarinic antagonist Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 229960001416 pilocarpine Drugs 0.000 description 3
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 3
- 229960002646 scopolamine Drugs 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- YCCVZRIFCRPGSK-WCBMZHEXSA-N (3r,4r)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]thiolane-2-thione Chemical compound C1SC(=S)[C@H](CC)[C@H]1CC1=CN=CN1C YCCVZRIFCRPGSK-WCBMZHEXSA-N 0.000 description 2
- JYWKEVKEKOTYEX-UHFFFAOYSA-N 2,6-dibromo-4-chloroiminocyclohexa-2,5-dien-1-one Chemical compound ClN=C1C=C(Br)C(=O)C(Br)=C1 JYWKEVKEKOTYEX-UHFFFAOYSA-N 0.000 description 2
- 229940100578 Acetylcholinesterase inhibitor Drugs 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- 208000003098 Ganglion Cysts Diseases 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 208000005400 Synovial Cyst Diseases 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 230000000971 hippocampal effect Effects 0.000 description 2
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- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000472 muscarinic agonist Substances 0.000 description 2
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- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- PSRPKRDUWXFVQS-KXNXZCPBSA-N (3r,4r)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]thiolan-2-one;phosphoric acid Chemical compound OP(O)(O)=O.C1SC(=O)[C@H](CC)[C@H]1CC1=CN=CN1C PSRPKRDUWXFVQS-KXNXZCPBSA-N 0.000 description 1
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- PXFISGUPSYAFPW-UHFFFAOYSA-N 3-ethyl-3-methyl-4-[(3-methylimidazol-4-yl)methyl]thiolan-2-one Chemical compound C1SC(=O)C(CC)(C)C1CC1=CN=CN1C PXFISGUPSYAFPW-UHFFFAOYSA-N 0.000 description 1
- YHIOTRNEAPZWIZ-UHFFFAOYSA-N 4-[(3-methylimidazol-4-yl)methyl]thiolan-2-one Chemical compound CN1C=NC=C1CC1CC(=O)SC1 YHIOTRNEAPZWIZ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- QLIGUFZPUCEOSB-WCBMZHEXSA-N C(C)[C@H]1C(SC[C@@H]1CC1=CN=CN1C)=NO Chemical compound C(C)[C@H]1C(SC[C@@H]1CC1=CN=CN1C)=NO QLIGUFZPUCEOSB-WCBMZHEXSA-N 0.000 description 1
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- 235000014066 European mistletoe Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UQOFGTXDASPNLL-XHNCKOQMSA-N Muscarine Chemical compound C[C@@H]1O[C@H](C[N+](C)(C)C)C[C@H]1O UQOFGTXDASPNLL-XHNCKOQMSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- RSDOPYMFZBJHRL-UHFFFAOYSA-N Oxotremorine Chemical compound O=C1CCCN1CC#CCN1CCCC1 RSDOPYMFZBJHRL-UHFFFAOYSA-N 0.000 description 1
- PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 description 1
- 235000012300 Rhipsalis cassutha Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000221012 Viscum Species 0.000 description 1
- 230000009471 action Effects 0.000 description 1
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- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
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- 238000013475 authorization Methods 0.000 description 1
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- 230000028161 membrane depolarization Effects 0.000 description 1
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- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 210000001577 neostriatum Anatomy 0.000 description 1
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- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 239000004031 partial agonist Substances 0.000 description 1
- 229960001697 physostigmine Drugs 0.000 description 1
- PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 description 1
- RNAICSBVACLLGM-GNAZCLTHSA-N pilocarpine hydrochloride Chemical compound Cl.C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C RNAICSBVACLLGM-GNAZCLTHSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- 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
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Ophthalmology & Optometry (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3702940 | 1987-01-31 | ||
| DE3702940 | 1987-01-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU87122A1 true LU87122A1 (fr) | 1988-08-23 |
Family
ID=6319976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU87122A LU87122A1 (fr) | 1987-01-31 | 1988-01-28 | Nouveaux derives de la pilocarpine,leur preparation et leur utilisation comme medicaments |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4835174A (enExample) |
| JP (1) | JPS63201185A (enExample) |
| KR (1) | KR880009013A (enExample) |
| AT (1) | AT395852B (enExample) |
| AU (1) | AU607966B2 (enExample) |
| BE (1) | BE1001005A3 (enExample) |
| CA (1) | CA1327805C (enExample) |
| CH (1) | CH675721A5 (enExample) |
| CS (1) | CS411291A3 (enExample) |
| DK (1) | DK46288A (enExample) |
| ES (1) | ES2008421A6 (enExample) |
| FI (1) | FI90080C (enExample) |
| FR (1) | FR2610322B1 (enExample) |
| GB (1) | GB2200910B (enExample) |
| GR (1) | GR880100042A (enExample) |
| HU (1) | HU204047B (enExample) |
| IE (1) | IE61989B1 (enExample) |
| IL (1) | IL85252A (enExample) |
| IT (1) | IT1219827B (enExample) |
| LU (1) | LU87122A1 (enExample) |
| MY (1) | MY102415A (enExample) |
| NL (1) | NL8800099A (enExample) |
| NZ (1) | NZ223359A (enExample) |
| PH (1) | PH24837A (enExample) |
| PT (1) | PT86666B (enExample) |
| SE (1) | SE466150B (enExample) |
| ZA (1) | ZA88665B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4882343A (en) * | 1987-08-28 | 1989-11-21 | G. D. Searle & Co. | Biarylalkylimidazole derivatives as anti-depressants |
| US5861431A (en) * | 1995-06-07 | 1999-01-19 | Iotek, Inc. | Incontinence treatment |
| BR112020009361A2 (pt) | 2017-11-17 | 2020-10-13 | Cellix Bio Private Limited | composto de fórmula i, composição farmacêutica para tratar um distúrbio ocular ou complicações do mesmo, método de síntese de composto, método de tratamento de um distúrbio ocular ou complicações do mesmo em um indivíduo que precisa do mesmo e uso de um composto |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2457047A (en) * | 1946-02-13 | 1948-12-21 | Monsanto Chemicals | 2-(2'-thenyl)-4, 5-dihydroimidazoles and process for making the same |
| GB1601310A (en) * | 1978-05-23 | 1981-10-28 | Lilly Industries Ltd | Aryl hydantoins |
| JPS56131579A (en) * | 1980-03-17 | 1981-10-15 | Kissei Pharmaceut Co Ltd | Novel 1-substituted imidazole derivative |
| JPS58150566A (ja) * | 1982-03-03 | 1983-09-07 | Yoshitomi Pharmaceut Ind Ltd | 新規イミダゾ−ル誘導体 |
| DE3228266A1 (de) * | 1982-07-29 | 1984-02-02 | A. Nattermann & Cie GmbH, 5000 Köln | Imidazolylalkylthiophene, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| DE3329028A1 (de) * | 1983-08-11 | 1985-02-28 | Cassella Ag, 6000 Frankfurt | Substituierte (2-amino-2-imidazolin-1-yl)-essigsaeurederivate, verfahren zu ihrer herstellung, ihre verwendung und sie enthaltende pharmazeutische zubereitungen |
-
1988
- 1988-01-18 NL NL8800099A patent/NL8800099A/nl not_active Application Discontinuation
- 1988-01-18 HU HU88177A patent/HU204047B/hu not_active IP Right Cessation
- 1988-01-26 BE BE8800091A patent/BE1001005A3/fr not_active IP Right Cessation
- 1988-01-27 FR FR888801019A patent/FR2610322B1/fr not_active Expired - Lifetime
- 1988-01-27 GB GB8801804A patent/GB2200910B/en not_active Expired - Lifetime
- 1988-01-28 CH CH307/88A patent/CH675721A5/de not_active IP Right Cessation
- 1988-01-28 CA CA000557576A patent/CA1327805C/en not_active Expired - Fee Related
- 1988-01-28 LU LU87122A patent/LU87122A1/fr unknown
- 1988-01-29 IE IE24488A patent/IE61989B1/en not_active IP Right Cessation
- 1988-01-29 ES ES8800263A patent/ES2008421A6/es not_active Expired
- 1988-01-29 IT IT47578/88A patent/IT1219827B/it active
- 1988-01-29 MY MYPI88000081A patent/MY102415A/en unknown
- 1988-01-29 AT AT0018288A patent/AT395852B/de not_active IP Right Cessation
- 1988-01-29 DK DK046288A patent/DK46288A/da not_active Application Discontinuation
- 1988-01-29 GR GR880100042A patent/GR880100042A/el unknown
- 1988-01-29 AU AU10960/88A patent/AU607966B2/en not_active Ceased
- 1988-01-29 SE SE8800293A patent/SE466150B/sv not_active IP Right Cessation
- 1988-01-29 JP JP63021136A patent/JPS63201185A/ja active Pending
- 1988-01-29 ZA ZA88665A patent/ZA88665B/xx unknown
- 1988-01-29 FI FI880430A patent/FI90080C/fi not_active IP Right Cessation
- 1988-01-29 IL IL85252A patent/IL85252A/xx not_active IP Right Cessation
- 1988-01-29 PT PT86666A patent/PT86666B/pt not_active IP Right Cessation
- 1988-01-29 NZ NZ223359A patent/NZ223359A/en unknown
- 1988-01-29 PH PH36423A patent/PH24837A/en unknown
- 1988-01-29 US US07/149,812 patent/US4835174A/en not_active Expired - Fee Related
- 1988-01-30 KR KR1019880000895A patent/KR880009013A/ko not_active Ceased
-
1991
- 1991-12-27 CS CS914112A patent/CS411291A3/cs unknown
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