SK129897A3 - Pyrrolidinyl hydroxamic acid derivatives, method and intermediate products for their production and pharmaceutical compositions process - Google Patents

Pyrrolidinyl hydroxamic acid derivatives, method and intermediate products for their production and pharmaceutical compositions process Download PDF

Info

Publication number: SK129897A3
Authority: SK; Slovakia
Prior art keywords: hydroxy; formula; acetamide; phenyl; phenylethyl
Prior art date: 1995-03-31

Application number

SK1298-97A

Other languages

English (en)

Slovak (sk)

Inventor

Fumitaka Ito

Original Assignee

Pfizer

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.)

1995-03-31

Filing date

1996-03-28

Publication date

1998-11-04

1996-03-28 Application filed by Pfizer filed Critical Pfizer

1998-11-04 Publication of SK129897A3 publication Critical patent/SK129897A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 102
-1 Pyrrolidinyl hydroxamic Chemical compound 0.000 title claims abstract description 75
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 8
239000002253 acid Substances 0.000 title claims description 18
238000004519 manufacturing process Methods 0.000 title description 2
239000013067 intermediate product Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 150
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 92
239000001257 hydrogen Substances 0.000 claims abstract description 72
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 40
125000006239 protecting group Chemical group 0.000 claims abstract description 22
150000003839 salts Chemical class 0.000 claims abstract description 18
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 11
239000000730 antalgic agent Substances 0.000 claims abstract description 9
125000001424 substituent group Chemical group 0.000 claims abstract description 9
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 8
239000003795 chemical substances by application Substances 0.000 claims abstract description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
208000004998 Abdominal Pain Diseases 0.000 claims abstract description 6
230000003444 anaesthetic effect Effects 0.000 claims abstract description 6
239000002260 anti-inflammatory agent Substances 0.000 claims abstract description 6
230000003110 anti-inflammatory effect Effects 0.000 claims abstract description 6
239000002934 diuretic Substances 0.000 claims abstract description 6
230000001882 diuretic effect Effects 0.000 claims abstract description 6
239000003193 general anesthetic agent Substances 0.000 claims abstract description 6
239000004090 neuroprotective agent Substances 0.000 claims abstract description 6
230000000202 analgesic effect Effects 0.000 claims abstract description 5
125000001544 thienyl group Chemical group 0.000 claims abstract description 4
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 3
125000002541 furyl group Chemical group 0.000 claims abstract description 3
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract description 3
125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
239000000203 mixture Substances 0.000 claims description 45
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 30
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 12
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 11
230000000694 effects Effects 0.000 claims description 11
241000124008 Mammalia Species 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical group 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 5
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 5
208000035475 disorder Diseases 0.000 claims description 5
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 5
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 4
HOGIAGOSNJXVGR-LJQANCHMSA-N 2-(3,4-dichlorophenyl)-n-hydroxy-n-[(1s)-1-phenyl-2-pyrrolidin-1-ylethyl]acetamide Chemical compound C([C@@H](N(O)C(=O)CC=1C=C(Cl)C(Cl)=CC=1)C=1C=CC=CC=1)N1CCCC1 HOGIAGOSNJXVGR-LJQANCHMSA-N 0.000 claims description 4
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
239000012359 Methanesulfonyl chloride Substances 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
229940121954 Opioid receptor agonist Drugs 0.000 claims 1
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 1
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims 1
239000003402 opiate agonist Substances 0.000 claims 1
NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 abstract description 5
241000282414 Homo sapiens Species 0.000 abstract description 4
201000010099 disease Diseases 0.000 abstract description 2
125000003545 alkoxy group Chemical group 0.000 abstract 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 2
125000001475 halogen functional group Chemical group 0.000 abstract 2
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
125000005530 alkylenedioxy group Chemical group 0.000 abstract 1
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 abstract 1
239000004305 biphenyl Chemical group 0.000 abstract 1
235000010290 biphenyl Nutrition 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
238000005481 NMR spectroscopy Methods 0.000 description 74
150000002431 hydrogen Chemical group 0.000 description 57
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 46
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
238000004458 analytical method Methods 0.000 description 43
239000003921 oil Substances 0.000 description 38
235000019198 oils Nutrition 0.000 description 38
239000007787 solid Substances 0.000 description 32
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 26
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
229910052938 sodium sulfate Inorganic materials 0.000 description 22
235000011152 sodium sulphate Nutrition 0.000 description 22
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 20
229910000041 hydrogen chloride Inorganic materials 0.000 description 20
JVWZVGMSJISZQR-PYNWJHIZSA-N (2r)-2-[(3s)-3-(oxan-2-yloxy)pyrrolidin-1-yl]-2-phenylethanol Chemical compound O([C@H]1CCN(C1)[C@@H](CO)C=1C=CC=CC=1)C1CCCCO1 JVWZVGMSJISZQR-PYNWJHIZSA-N 0.000 description 19
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 18
150000001412 amines Chemical class 0.000 description 17
230000008018 melting Effects 0.000 description 16
238000002844 melting Methods 0.000 description 16
239000002904 solvent Substances 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
239000000126 substance Substances 0.000 description 14
239000000047 product Substances 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
239000012267 brine Substances 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
CNONYXFNOHXTLC-KBPBESRZSA-N (2r)-2-[(3s)-3-(methoxymethoxy)pyrrolidin-1-yl]-2-phenylethanol Chemical compound C1[C@@H](OCOC)CCN1[C@@H](CO)C1=CC=CC=C1 CNONYXFNOHXTLC-KBPBESRZSA-N 0.000 description 11
239000000284 extract Substances 0.000 description 11
238000001914 filtration Methods 0.000 description 11
229920006395 saturated elastomer Polymers 0.000 description 11
238000004440 column chromatography Methods 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
235000017557 sodium bicarbonate Nutrition 0.000 description 10
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
239000000556 agonist Substances 0.000 description 8
239000000843 powder Substances 0.000 description 8
239000000543 intermediate Substances 0.000 description 7
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
MWGPNRQVCPJJBW-LURJTMIESA-N (3s)-3-(methoxymethoxy)pyrrolidine Chemical compound COCO[C@H]1CCNC1 MWGPNRQVCPJJBW-LURJTMIESA-N 0.000 description 5
ZOUPGSMSNQLUNW-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(Cl)C(Cl)=C1 ZOUPGSMSNQLUNW-UHFFFAOYSA-N 0.000 description 5
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 5
241000282412 Homo Species 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000002632 kappa opiate receptor agonist Substances 0.000 description 5
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 5
238000010561 standard procedure Methods 0.000 description 5
238000012360 testing method Methods 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
JCZDMBKPCOKANB-VEDVMXKPSA-N (3r)-3-(oxan-2-yloxy)pyrrolidine Chemical compound C1NCC[C@H]1OC1OCCCC1 JCZDMBKPCOKANB-VEDVMXKPSA-N 0.000 description 4
206010010904 Convulsion Diseases 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
239000012230 colorless oil Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000000746 purification Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
102000003840 Opioid Receptors Human genes 0.000 description 3
108090000137 Opioid Receptors Proteins 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
230000029936 alkylation Effects 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
229940035676 analgesics Drugs 0.000 description 3
238000003556 assay Methods 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000007789 gas Substances 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 3
239000002674 ointment Substances 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
229940044601 receptor agonist Drugs 0.000 description 3
239000000018 receptor agonist Substances 0.000 description 3
238000010898 silica gel chromatography Methods 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
125000001412 tetrahydropyranyl group Chemical group 0.000 description 3
WPVZJYFBUIBTRC-SECBINFHSA-N (1s)-1-(3-methylphenyl)ethane-1,2-diol Chemical compound CC1=CC=CC([C@H](O)CO)=C1 WPVZJYFBUIBTRC-SECBINFHSA-N 0.000 description 2
CYRLHHDBZGNKEA-SNVBAGLBSA-N (1s)-1-[3-(methoxymethoxy)phenyl]ethane-1,2-diol Chemical compound COCOC1=CC=CC([C@H](O)CO)=C1 CYRLHHDBZGNKEA-SNVBAGLBSA-N 0.000 description 2
UZCBDOLPPICICR-YNPPLXCJSA-N (1s)-2-[(3r)-3-(oxan-2-yloxy)pyrrolidin-1-yl]-1-phenylethanol Chemical compound O([C@@H]1CCN(C1)C[C@@H](O)C=1C=CC=CC=1)C1CCCCO1 UZCBDOLPPICICR-YNPPLXCJSA-N 0.000 description 2
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CDLHNMKWIQZIOI-LSDHHAIUSA-N (1s)-2-[(3s)-3-(methoxymethoxy)pyrrolidin-1-yl]-1-(4-methylphenyl)ethanol Chemical compound C1[C@@H](OCOC)CCN1C[C@@H](O)C1=CC=C(C)C=C1 CDLHNMKWIQZIOI-LSDHHAIUSA-N 0.000 description 2
JHAQDLQRDPXVQL-GJZGRUSLSA-N (2r)-2-[(3s)-3-(methoxymethoxy)pyrrolidin-1-yl]-2-(4-methylphenyl)ethanol Chemical compound C1[C@@H](OCOC)CCN1[C@@H](CO)C1=CC=C(C)C=C1 JHAQDLQRDPXVQL-GJZGRUSLSA-N 0.000 description 2
QAWJAMQTRGCJMH-SECBINFHSA-N (2s)-2-(4-methylphenyl)oxirane Chemical compound C1=CC(C)=CC=C1[C@@H]1OC1 QAWJAMQTRGCJMH-SECBINFHSA-N 0.000 description 2
GLZXZTWPGUEGPE-AAFJCEBUSA-N (3r)-1-benzyl-3-(oxan-2-yloxy)pyrrolidine Chemical compound O([C@@H]1CCN(C1)CC=1C=CC=CC=1)C1CCCCO1 GLZXZTWPGUEGPE-AAFJCEBUSA-N 0.000 description 2
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Classifications

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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- A61P7/10—Antioedematous agents; Diuretics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- 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
- C07D405/12—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 chain containing hetero atoms as chain links
- 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
- C07D409/12—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 chain containing hetero atoms as chain links
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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

SK1298-97A 1995-03-31 1996-03-28 Pyrrolidinyl hydroxamic acid derivatives, method and intermediate products for their production and pharmaceutical compositions process SK129897A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP9500631		1995-03-31
PCT/JP1996/000820 WO1996030339A1 (fr)	1995-03-31	1996-03-28	Composes d'acide pyrrolidinyl-hydroxamique et leur procede de production

Publications (1)

Publication Number	Publication Date
SK129897A3 true SK129897A3 (en)	1998-11-04

Family

ID=14125824

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1298-97A SK129897A3 (en)	1995-03-31	1996-03-28	Pyrrolidinyl hydroxamic acid derivatives, method and intermediate products for their production and pharmaceutical compositions process

Country Status (35)

Country	Link
US (2)	US5952369A (fr)
EP (1)	EP0817772B1 (fr)
JP (1)	JP3035356B2 (fr)
KR (1)	KR100258657B1 (fr)
AP (1)	AP625A (fr)
AR (1)	AR002729A1 (fr)
AT (1)	ATE231840T1 (fr)
AU (1)	AU693336B2 (fr)
BG (1)	BG62611B1 (fr)
BR (1)	BR9607750A (fr)
CA (1)	CA2213815C (fr)
CZ (1)	CZ306497A3 (fr)
DE (1)	DE69626009T2 (fr)
DK (1)	DK0817772T3 (fr)
ES (1)	ES2188743T3 (fr)
HR (1)	HRP960141A2 (fr)
HU (1)	HUP9900767A3 (fr)
IL (2)	IL117440A0 (fr)
IS (1)	IS4547A (fr)
LV (1)	LV11971B (fr)
MA (1)	MA23832A1 (fr)
NO (1)	NO974513L (fr)
NZ (1)	NZ304113A (fr)
OA (1)	OA10518A (fr)
PE (1)	PE43397A1 (fr)
PL (1)	PL322652A1 (fr)
RU (1)	RU2144917C1 (fr)
SI (1)	SI9620039A (fr)
SK (1)	SK129897A3 (fr)
TN (1)	TNSN96045A1 (fr)
TR (1)	TR199701082T1 (fr)
TW (1)	TW408111B (fr)
WO (1)	WO1996030339A1 (fr)
YU (1)	YU18696A (fr)
ZA (1)	ZA962476B (fr)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MX9701042A (es) *	1996-02-07	1998-05-31	Pfizer	Compuestos del acido hidroxamico.
TNSN97092A1 (ar)	1996-09-18	1999-12-31	Agouron Pharma	مثبطات انزيم بروتيني فلزي وتركيبات صيدلانية تحتوي على تلك المثبتطات واستخدامها الصيدلاني وطرق ومركبات وسيطة مفيدة لتحضير التركيبات المذكورة.
ATE235903T1 (de) *	1996-12-02	2003-04-15	Kyorin Seiyaku Kk	Neue derivate von n-substituierten pyrrolidin derivaten und deren herstellungsverfahren
EP0973737A4 (fr) *	1997-01-10	2000-04-26	Merck & Co Inc	Synthese efficace d'un mediateur chiral
IL130429A0 (en) *	1998-08-24	2000-06-01	Pfizer Prod Inc	Process for preparing pyrrolidinyl hydroxamic acid compounds
KR100295740B1 (ko) *	1998-09-17	2001-11-05	박영구	N-치환된-하이드록시고리화알킬아민유도체의제조방법
US6444829B1 (en) *	2000-07-19	2002-09-03	Hoffmann-La Roche Inc.	Pyrrolidine compounds
EP1461317A2 (fr)	2001-04-30	2004-09-29	Pfizer Products Inc.	Procede de preparation de composes d'ethylamine d'hydroxypyrrolidinyle utilises comme agonistes de kappa
US7091357B2 (en) *	2001-12-26	2006-08-15	University Of Kentucky Research Foundation	Chain-modified pyridino-N substituted nicotine compounds for use in the treatment of CNS pathologies
GB0202873D0 (en) *	2002-02-07	2002-03-27	Novartis Ag	Organic compounds
WO2004039785A1 (fr) *	2002-11-01	2004-05-13	Pfizer Products Inc.	Procede servant a preparer des composes de pyrolidinyle ethylamine par l'intermediaire d'une arylamination provoquee par du cuivre
JP2006523670A (ja) *	2003-04-14	2006-10-19	ワーナー−ランバートカンパニーリミティドライアビリティーカンパニー	５−（４−フルオロフェニル）−１−［２−（（２ｒ，４ｒ）−４−ヒドロキシ−６−オキソ−テトラヒドロ−ピラン−２−イル）エチル］−２−イソプロピル−４−フェニル−１ｈ−ピロール−３−カルボン酸フェニルアミドの調製方法
UA89035C2 (ru) *	2003-12-03	2009-12-25	Лео Фарма А/С	Эфиры гидроксамовых кислот и их фармацевтическое применение
GB0821010D0 (en) *	2008-11-17	2008-12-24	Univ Warwick	Plant development control composition
US9493451B2 (en)	2011-05-16	2016-11-15	Bionomics Limited	Amine derivatives as potassium channel blockers
US9487510B2 (en)	2012-03-05	2016-11-08	Dr. Reddy's Laboratories Ltd.	Substituted heterocyclic acetamides as kappa opioid receptor (KOR) agonists
GB201210395D0 (en) *	2012-06-11	2012-07-25	Syngenta Participations Ag	Crop enhancement compositions

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3268539A (en) *	1963-05-20	1966-08-23	Universal Oil Prod Co	Tertiary-aminoalkyl derivatives of diaryl substituted acetohydroxamic acid esters

1996
- 1996-03-11 IL IL11744096A patent/IL117440A0/xx unknown
- 1996-03-14 AP APAP/P/1996/000791A patent/AP625A/en active
- 1996-03-15 TW TW085103136A patent/TW408111B/zh active
- 1996-03-25 MA MA24191A patent/MA23832A1/fr unknown
- 1996-03-25 PE PE1996000208A patent/PE43397A1/es not_active Application Discontinuation
- 1996-03-26 HR HRPCT/JP95/631A patent/HRP960141A2/hr not_active Application Discontinuation
- 1996-03-27 YU YU18696A patent/YU18696A/sh unknown
- 1996-03-28 RU RU97117590A patent/RU2144917C1/ru active
- 1996-03-28 CA CA002213815A patent/CA2213815C/fr not_active Expired - Fee Related
- 1996-03-28 DK DK96907686T patent/DK0817772T3/da active
- 1996-03-28 US US08/913,823 patent/US5952369A/en not_active Expired - Fee Related
- 1996-03-28 ZA ZA9602476A patent/ZA962476B/xx unknown
- 1996-03-28 SI SI9620039A patent/SI9620039A/sl not_active IP Right Cessation
- 1996-03-28 EP EP96907686A patent/EP0817772B1/fr not_active Expired - Lifetime
- 1996-03-28 SK SK1298-97A patent/SK129897A3/sk unknown
- 1996-03-28 WO PCT/JP1996/000820 patent/WO1996030339A1/fr not_active Ceased
- 1996-03-28 AU AU51211/96A patent/AU693336B2/en not_active Ceased
- 1996-03-28 TR TR97/01082T patent/TR199701082T1/xx unknown
- 1996-03-28 AT AT96907686T patent/ATE231840T1/de not_active IP Right Cessation
- 1996-03-28 PL PL96322652A patent/PL322652A1/xx unknown
- 1996-03-28 NZ NZ304113A patent/NZ304113A/xx unknown
- 1996-03-28 BR BR9607750A patent/BR9607750A/pt active Search and Examination
- 1996-03-28 DE DE69626009T patent/DE69626009T2/de not_active Expired - Fee Related
- 1996-03-28 JP JP08529174A patent/JP3035356B2/ja not_active Expired - Fee Related
- 1996-03-28 HU HU9900767A patent/HUP9900767A3/hu unknown
- 1996-03-28 KR KR1019970706880A patent/KR100258657B1/ko not_active Expired - Fee Related
- 1996-03-28 ES ES96907686T patent/ES2188743T3/es not_active Expired - Lifetime
- 1996-03-28 CZ CZ973064A patent/CZ306497A3/cs unknown
- 1996-03-29 TN TNTNSN96045A patent/TNSN96045A1/fr unknown
- 1996-03-29 AR ARP960101993A patent/AR002729A1/es unknown
1997
- 1997-08-19 IS IS4547A patent/IS4547A/is unknown
- 1997-09-17 BG BG101896A patent/BG62611B1/bg unknown
- 1997-09-29 NO NO974513A patent/NO974513L/no not_active Application Discontinuation
- 1997-09-30 OA OA70091A patent/OA10518A/en unknown
- 1997-10-21 LV LVP-97-203A patent/LV11971B/en unknown
1999
- 1999-04-15 IL IL12947999A patent/IL129479A0/xx unknown
- 1999-04-29 US US09/302,097 patent/US6110947A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
DE69626009T2 (de)	2003-08-14
IL129479A0 (en)	2000-02-29
JPH11501048A (ja)	1999-01-26
HRP960141A2 (en)	1997-10-31
YU18696A (sh)	1999-06-15
IL117440A0 (en)	1996-07-23
EP0817772B1 (fr)	2003-01-29
LV11971A (lv)	1998-02-20
HUP9900767A3 (en)	2001-01-29
AP9600791A0 (en)	1996-04-30
TW408111B (en)	2000-10-11
PE43397A1 (es)	1997-10-13
AU5121196A (en)	1996-10-16
ES2188743T3 (es)	2003-07-01
KR100258657B1 (ko)	2000-07-01
JP3035356B2 (ja)	2000-04-24
AP625A (en)	1997-12-24
TR199701082T1 (xx)	1998-02-21
US5952369A (en)	1999-09-14
IS4547A (is)	1997-08-19
NO974513D0 (no)	1997-09-29
KR19980703476A (ko)	1998-11-05
WO1996030339A1 (fr)	1996-10-03
ATE231840T1 (de)	2003-02-15
CA2213815A1 (fr)	1996-10-03
US6110947A (en)	2000-08-29
SI9620039A (sl)	1998-08-31
NO974513L (no)	1997-09-29
AR002729A1 (es)	1998-04-29
DE69626009D1 (de)	2003-03-06
HUP9900767A2 (hu)	1999-07-28
EP0817772A1 (fr)	1998-01-14
BG62611B1 (bg)	2000-03-31
LV11971B (en)	1998-06-20
CZ306497A3 (cs)	1998-07-15
TNSN96045A1 (fr)	2005-03-15
AU693336B2 (en)	1998-06-25
BR9607750A (pt)	1998-06-30
DK0817772T3 (da)	2003-05-19
ZA962476B (en)	1997-09-29
OA10518A (en)	2002-04-22
CA2213815C (fr)	2001-12-18
BG101896A (en)	1999-01-29
PL322652A1 (en)	1998-02-16
NZ304113A (en)	1999-01-28
MX9707454A (es)	1998-07-31
MA23832A1 (fr)	1996-10-01
RU2144917C1 (ru)	2000-01-27

Publication	Publication Date	Title
SK129897A3 (en)	1998-11-04	Pyrrolidinyl hydroxamic acid derivatives, method and intermediate products for their production and pharmaceutical compositions process
RU2125041C1 (ru)	1999-01-20	Арилацетамиды, способ их получения, фармацевтическая композиция и способ ее получения
SK278434B6 (en)	1997-05-07	3-substituted pyrolidine derivative, preparation method thereof, intermediate products of this method, pharmaceutical composition containing this derivative
EP0629190A1 (fr)	1994-12-21	Composes utilises comme antagonistes des canaux calciques
US6294557B1 (en)	2001-09-25	Pyrrolidinyl and pyrrolinyl ethylamine compounds as kappa agonists
WO1992022527A2 (fr)	1992-12-23	Derives de pyrrolidine 3-substitues comme antagonistes du calcium
JP2935899B2 (ja)	1999-08-16	▲下ｋ▼レセプターアゴニストとしてのｎ−（２−（ピロリジニル−１）−１−フェニルエチル）アセトアミド
GB2068373A (en)	1981-08-12	Cyclohexene derivatives
Liu et al.	2017	Divergent syntheses of L-733, 060 and CP-122721 from functionalized pieridinones made by one-pot tandem cyclization
Hussaini et al.	2006	2, 5-Disubstituted pyrrolidines: synthesis by enamine reduction and subsequent regioselective and diastereoselective alkylations
US5387688A (en)	1995-02-07	Intermediates for making analgesic N-phenyl-N-(3-OR1 -3-Me-4-piperidinyl)amides
JP3245578B2 (ja)	2002-01-15	ピロリジニルヒドロキサム酸化合物の製造方法
NZ233002A (en)	1992-07-28	3-(aminoalkyl)benzothiopyran derivatives and pharmaceutical compositions
EP0789021B1 (fr)	2000-10-11	Dérivés d'acide hydroxamique et leur utilisation comme agonistes du récepteur opioid kappa
US5716936A (en)	1998-02-10	Pyrrolidine derivatives for the treatment of cholecystokinine and gastrine-related disorders
MXPA97007454A (en)	1998-11-09	Hydroxamic pirrolidinil acid compounds and their product procedure
US5130321A (en)	1992-07-14	Analgesic n-phenyl-n-(3-or 1-3-me-4-piperidinyl)amides
WO2002088082A2 (fr)	2002-11-07	Procede de preparation de composes d'ethylamine d'hydroxypyrrolidinyle utilises comme agonistes de kappa
PT789021E (pt)	2001-02-28	Compostos de acido pirrolidinil hidroxamico e o processo para a sua producao
CZ9902390A3 (cs)	2000-10-11	Způsob výroby derivátů pyrrolidinylhydroxamové kyseliny