SK282646B6 - Arylacetamidy, spôsob ich výroby, použite a farmaceutický prípravok na ich báze - Google Patents

Arylacetamidy, spôsob ich výroby, použite a farmaceutický prípravok na ich báze Download PDF

Info

Publication number: SK282646B6
Authority: SK; Slovakia
Prior art keywords: methyl; hydroxypyrrolidino; ethyl; formula; phenyl
Prior art date: 1992-05-09

Application number

SK468-93A

Other languages

English (en)

Slovak (sk)

Other versions

SK46893A3 (en

Inventor

Rudolf Gottschlich

Karl-August Ackermann

Helmut Pr�cher

Christoph Seyfried

Hartmut Greiner

Gerd Bartoszyk

Frank Mauler

Manfred Stohrer

Andrew Barber

Original Assignee

Merck Patent Gesellschaft Mit Beschr�Nkter Haftung

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1992-05-09

Filing date

1993-05-12

Publication date

2002-10-08

1993-05-12 Application filed by Merck Patent Gesellschaft Mit Beschr�Nkter Haftung filed Critical Merck Patent Gesellschaft Mit Beschr�Nkter Haftung

1994-04-06 Publication of SK46893A3 publication Critical patent/SK46893A3/sk

2002-10-08 Publication of SK282646B6 publication Critical patent/SK282646B6/sk

Links

238000004519 manufacturing process Methods 0.000 title claims abstract description 8
-1 methylenedioxy Chemical group 0.000 claims abstract description 153
150000003839 salts Chemical class 0.000 claims abstract description 20
229910052801 chlorine Inorganic materials 0.000 claims abstract description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
229910052731 fluorine Inorganic materials 0.000 claims abstract description 13
238000011282 treatment Methods 0.000 claims abstract description 13
229910052794 bromium Inorganic materials 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
239000003814 drug Substances 0.000 claims abstract description 9
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 5
208000004454 Hyperalgesia Diseases 0.000 claims abstract description 4
208000035154 Hyperesthesia Diseases 0.000 claims abstract description 4
206010061218 Inflammation Diseases 0.000 claims abstract description 3
230000004054 inflammatory process Effects 0.000 claims abstract description 3
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 54
150000001875 compounds Chemical class 0.000 claims description 50
239000002253 acid Substances 0.000 claims description 13
239000000460 chlorine Substances 0.000 claims description 12
238000000034 method Methods 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
125000001153 fluoro group Chemical group F* 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
YUZJQTWISZUWFU-UHFFFAOYSA-N 2,2-diphenyl-1-[1-(pyrrolidin-1-ylmethyl)-3,4-dihydro-1h-isoquinolin-2-yl]propan-1-one Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C)C(=O)N1CCC2=CC=CC=C2C1CN1CCCC1 YUZJQTWISZUWFU-UHFFFAOYSA-N 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims description 2
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
150000007514 bases Chemical class 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims description 2
201000010099 disease Diseases 0.000 claims description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
CJLIKNVWZCCTKX-ZCYQVOJMSA-N (3S)-4-[(3S)-3-hydroxypyrrolidin-1-yl]-3-(4-methoxyphenyl)-2,2-diphenylbutanamide Chemical compound COC1=CC=C(C=C1)[C@H](CN1C[C@H](CC1)O)C(C(=O)N)(C1=CC=CC=C1)C1=CC=CC=C1 CJLIKNVWZCCTKX-ZCYQVOJMSA-N 0.000 claims 1
AZGVFPJKXURBKA-NBGIEHNGSA-N n-[(1s)-2-[(3s)-3-hydroxypyrrolidin-1-yl]-1-phenylethyl]-n-methyl-9h-fluorene-9-carboxamide Chemical compound C([C@@H](N(C)C(=O)C1C2=CC=CC=C2C2=CC=CC=C21)C=1C=CC=CC=1)N1CC[C@H](O)C1 AZGVFPJKXURBKA-NBGIEHNGSA-N 0.000 claims 1
JHLHNYVMZCADTC-UHFFFAOYSA-N n-[2-(3-hydroxypyrrolidin-1-yl)-1-phenylethyl]-n-methyl-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)C(=O)N(C)C(C=1C=CC=CC=1)CN1CCC(O)C1 JHLHNYVMZCADTC-UHFFFAOYSA-N 0.000 claims 1
ICZKKXVUKDFBAQ-UHFFFAOYSA-N n-methyl-n-(4-methyl-1-pyrrolidin-1-ylpentan-2-yl)-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)C(=O)N(C)C(CC(C)C)CN1CCCC1 ICZKKXVUKDFBAQ-UHFFFAOYSA-N 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 abstract description 3
125000002947 alkylene group Chemical group 0.000 abstract 1
125000004429 atom Chemical group 0.000 abstract 1
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
125000000719 pyrrolidinyl group Chemical group 0.000 abstract 1
125000004434 sulfur atom Chemical group 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
150000001412 amines Chemical class 0.000 description 26
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 13
239000000243 solution Substances 0.000 description 13
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
ORIBHZDPRQDTTL-GXTWGEPZSA-N (3s)-1-[(2s)-2-(4-methoxyphenyl)-2-(methylamino)ethyl]pyrrolidin-3-ol Chemical compound C([C@@H](NC)C=1C=CC(OC)=CC=1)N1CC[C@H](O)C1 ORIBHZDPRQDTTL-GXTWGEPZSA-N 0.000 description 11
IDBNECMSCRAUNU-LURJTMIESA-N (3s)-1-ethylpyrrolidin-3-ol Chemical compound CCN1CC[C@H](O)C1 IDBNECMSCRAUNU-LURJTMIESA-N 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
JHEFOJNPLXSWNZ-UHFFFAOYSA-N n-(4-fluorophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(F)C=C1 JHEFOJNPLXSWNZ-UHFFFAOYSA-N 0.000 description 10
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
FFHGCIYKPNISDY-UHFFFAOYSA-N n-(4-chlorophenyl)propanamide Chemical compound CCC(=O)NC1=CC=C(Cl)C=C1 FFHGCIYKPNISDY-UHFFFAOYSA-N 0.000 description 9
150000003254 radicals Chemical class 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
FKLLYUGYCHIPBQ-CYBMUJFWSA-N (1s)-1-(4-chlorophenyl)-n-methyl-2-pyrrolidin-1-ylethanamine Chemical compound C([C@@H](NC)C=1C=CC(Cl)=CC=1)N1CCCC1 FKLLYUGYCHIPBQ-CYBMUJFWSA-N 0.000 description 6
ZINZYRWMDNKTBY-CYBMUJFWSA-N (1s)-n-methyl-1-phenyl-2-pyrrolidin-1-ylethanamine Chemical compound C([C@@H](NC)C=1C=CC=CC=1)N1CCCC1 ZINZYRWMDNKTBY-CYBMUJFWSA-N 0.000 description 6
WJKIMUCPDVHFDR-NBFOIZRFSA-N (3s)-1-(1,2,3,4-tetrahydroisoquinolin-1-ylmethyl)pyrrolidin-3-ol Chemical compound C1[C@@H](O)CCN1CC1C2=CC=CC=C2CCN1 WJKIMUCPDVHFDR-NBFOIZRFSA-N 0.000 description 6
KQDZLZOJQFRMFI-GXFFZTMASA-N (3s)-1-[(2s)-2-(2,4-difluorophenyl)-2-(methylamino)ethyl]pyrrolidin-3-ol Chemical compound C([C@@H](NC)C=1C(=CC(F)=CC=1)F)N1CC[C@H](O)C1 KQDZLZOJQFRMFI-GXFFZTMASA-N 0.000 description 6
MQJRYOCYVSQUQQ-QWHCGFSZSA-N (3s)-1-[(2s)-2-(4-fluorophenyl)-2-(methylamino)ethyl]pyrrolidin-3-ol Chemical compound C([C@@H](NC)C=1C=CC(F)=CC=1)N1CC[C@H](O)C1 MQJRYOCYVSQUQQ-QWHCGFSZSA-N 0.000 description 6
YYFOXLMZCAEDSP-QWHCGFSZSA-N (3s)-1-[(2s)-2-(4-hydroxyphenyl)-2-(methylamino)ethyl]pyrrolidin-3-ol Chemical compound C([C@@H](NC)C=1C=CC(O)=CC=1)N1CC[C@H](O)C1 YYFOXLMZCAEDSP-QWHCGFSZSA-N 0.000 description 6
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125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
OQWYVBRBNXETBN-CQSZACIVSA-N (1s)-1-(2,4-dimethoxyphenyl)-n-methyl-2-pyrrolidin-1-ylethanamine Chemical compound C([C@@H](NC)C=1C(=CC(OC)=CC=1)OC)N1CCCC1 OQWYVBRBNXETBN-CQSZACIVSA-N 0.000 description 5
PBJVNKGUYVIHJW-UHFFFAOYSA-N 1-(pyrrolidin-1-ylmethyl)-1,2,3,4-tetrahydroisoquinoline Chemical compound N1CCC2=CC=CC=C2C1CN1CCCC1 PBJVNKGUYVIHJW-UHFFFAOYSA-N 0.000 description 5
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000003826 tablet Substances 0.000 description 4
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OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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230000000202 analgesic effect Effects 0.000 description 3
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238000002844 melting Methods 0.000 description 3
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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YLBWRMSQRFEIEB-VIFPVBQESA-N 1-[[(2s)-pyrrolidin-2-yl]methyl]pyrrolidine Chemical compound C1CCCN1C[C@@H]1CCCN1 YLBWRMSQRFEIEB-VIFPVBQESA-N 0.000 description 2
IDBNECMSCRAUNU-UHFFFAOYSA-N 1-ethylpyrrolidin-3-ol Chemical compound CCN1CCC(O)C1 IDBNECMSCRAUNU-UHFFFAOYSA-N 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- 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
- C07D207/08—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 hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- 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
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes 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 in position 9
- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Pain & Pain Management (AREA)
Pulmonology (AREA)
Hematology (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Rheumatology (AREA)
Diabetes (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)
Plural Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Pyrrole Compounds (AREA)
Peptides Or Proteins (AREA)

SK468-93A 1992-05-09 1993-05-12 Arylacetamidy, spôsob ich výroby, použite a farmaceutický prípravok na ich báze SK282646B6 (sk)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE4215213A DE4215213A1 (de)	1992-05-09	1992-05-09	Arylacetamide

Publications (2)

Publication Number	Publication Date
SK46893A3 SK46893A3 (en)	1994-04-06
SK282646B6 true SK282646B6 (sk)	2002-10-08

Family

ID=6458428

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK468-93A SK282646B6 (sk)	1992-05-09	1993-05-12	Arylacetamidy, spôsob ich výroby, použite a farmaceutický prípravok na ich báze

Country Status (21)

Country	Link
US (1)	US5532266A (cs)
EP (1)	EP0569802B1 (cs)
JP (1)	JP3210771B2 (cs)
KR (1)	KR100241637B1 (cs)
CN (1)	CN1041087C (cs)
AT (1)	ATE168368T1 (cs)
AU (1)	AU662051B2 (cs)
BR (1)	BR1100581A (cs)
CA (1)	CA2095797C (cs)
CZ (1)	CZ289961B6 (cs)
DE (2)	DE4215213A1 (cs)
DK (1)	DK0569802T3 (cs)
ES (1)	ES2121030T3 (cs)
HU (1)	HU214578B (cs)
NO (1)	NO179789C (cs)
PL (1)	PL173779B1 (cs)
RU (1)	RU2125041C1 (cs)
SK (1)	SK282646B6 (cs)
TW (1)	TW372961B (cs)
UA (1)	UA32543C2 (cs)
ZA (1)	ZA933222B (cs)

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CA2288828A1 (en) *	1997-07-14	1999-01-28	Adolor Corporation	Kappa agonist anti-pruritic pharmaceutical formulations and method of treating pruritus therewith
DE19827633A1 (de) *	1998-04-20	1999-10-21	Merck Patent Gmbh	Verfahren zur Herstellung von enantiomerenreinem N-Methyl-N-[(1S)-1-phenyl-2-((3S)-3-hydroxypyrrolidin-1-yl)ethyl]-2,2-diphenylacetamid
TW593241B (en) *	1999-04-20	2004-06-21	Hoffmann La Roche	Carbamic acid derivatives
DE10116978A1 (de) *	2001-04-05	2002-10-10	Merck Patent Gmbh	Kappa-Opiatagonisten für die Behandlung von Erkrankungen der Blase
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CN100411618C (zh)	2002-05-17	2008-08-20	迪欧加药品公司	有效的选择性阿片受体调制剂化合物的用途
DE10259245A1 (de)	2002-12-17	2004-07-01	Merck Patent Gmbh	Derivate des Asimadolins mit kovalent gebundenen Säuren
US6852713B2 (en) *	2003-04-16	2005-02-08	Adolor Corporation	Lactam derivatives and methods of their use
US6992193B2 (en)	2003-06-10	2006-01-31	Adolor Corporation	Sulfonylamino phenylacetamide derivatives and methods of their use
US7034051B2 (en) *	2003-08-28	2006-04-25	Adolor Corporation	Fused bicyclic carboxamide derivatives and methods of their use
CA2544245A1 (en) *	2003-10-30	2005-05-26	Tioga Pharmaceuticals, Inc.	Use of selective opiate receptor modulators in the treatment of neuropathy
US7160902B2 (en) *	2003-11-14	2007-01-09	Adolor Corporation	Amide derivatives and methods of their use
JP2007528898A (ja) *	2004-03-12	2007-10-18	イーライリリーアンドカンパニー	オピオイド受容体拮抗物質
EP2636407A3 (en)	2007-03-30	2013-11-06	Tioga Pharmaceuticals, Inc.	Kappa-opiate agonists for the treatment of diarrhea-predominant and alternating irritable bowel syndrome
JP5776554B2 (ja) *	2009-11-18	2015-09-09	日本ゼオン株式会社	フルオレン化合物、当該フルオレン化合物を含有する合成ポリマーの安定化剤、及び当該フルオレン化合物を含有する組成物
CN103664727A (zh) *	2013-12-19	2014-03-26	无锡万全医药技术有限公司	一种一锅法制备1-[(3s)-3-羟基吡咯烷-1-基]-(2s)-2-甲氨基-2-苯基乙烷的工艺
CN103772257A (zh) *	2013-12-31	2014-05-07	无锡万全医药技术有限公司	一种制备2-((3s)-3-羟基吡咯烷-1-基)-(1s)-1-苯乙基氨基甲酸酯的方法
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FR2421891A1 (fr) *	1977-10-17	1979-11-02	Fabre Sa Pierre	Obtention industrielle d'amides de la pyrrolidine ethyl amine
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1992
- 1992-05-09 DE DE4215213A patent/DE4215213A1/de not_active Withdrawn
1993
- 1993-04-08 UA UA94010169A patent/UA32543C2/uk unknown
- 1993-05-01 DK DK93107103T patent/DK0569802T3/da active
- 1993-05-01 EP EP93107103A patent/EP0569802B1/de not_active Expired - Lifetime
- 1993-05-01 AT AT93107103T patent/ATE168368T1/de active
- 1993-05-01 ES ES93107103T patent/ES2121030T3/es not_active Expired - Lifetime
- 1993-05-01 DE DE59308763T patent/DE59308763D1/de not_active Expired - Lifetime
- 1993-05-03 AU AU38341/93A patent/AU662051B2/en not_active Expired
- 1993-05-05 CZ CZ1993823A patent/CZ289961B6/cs not_active IP Right Cessation
- 1993-05-06 RU RU93004806/04A patent/RU2125041C1/ru active
- 1993-05-07 PL PL93298845A patent/PL173779B1/pl unknown
- 1993-05-07 ZA ZA933222A patent/ZA933222B/xx unknown
- 1993-05-07 CA CA002095797A patent/CA2095797C/en not_active Expired - Lifetime
- 1993-05-07 NO NO931681A patent/NO179789C/no not_active IP Right Cessation
- 1993-05-07 HU HU9301325A patent/HU214578B/hu unknown
- 1993-05-07 TW TW082103568A patent/TW372961B/zh not_active IP Right Cessation
- 1993-05-08 CN CN93105673A patent/CN1041087C/zh not_active Expired - Lifetime
- 1993-05-08 KR KR1019930007899A patent/KR100241637B1/ko not_active Expired - Lifetime
- 1993-05-10 JP JP10844493A patent/JP3210771B2/ja not_active Expired - Lifetime
- 1993-05-12 SK SK468-93A patent/SK282646B6/sk not_active IP Right Cessation
1995
- 1995-05-30 US US08/453,811 patent/US5532266A/en not_active Expired - Lifetime
1997
- 1997-05-13 BR BR1100581-5A patent/BR1100581A/pt active IP Right Grant

Also Published As

Publication number	Publication date
ZA933222B (en)	1993-12-08
CZ82393A3 (en)	1994-02-16
PL173779B1 (pl)	1998-04-30
KR100241637B1 (ko)	2000-03-02
NO931681D0 (no)	1993-05-07
CN1079219A (zh)	1993-12-08
AU3834193A (en)	1993-11-11
HUT70172A (en)	1995-09-28
CZ289961B6 (cs)	2002-05-15
NO179789B (no)	1996-09-09
DE59308763D1 (de)	1998-08-20
KR930023340A (ko)	1993-12-18
EP0569802B1 (de)	1998-07-15
TW372961B (en)	1999-11-01
SK46893A3 (en)	1994-04-06
EP0569802A1 (de)	1993-11-18
ATE168368T1 (de)	1998-08-15
RU2125041C1 (ru)	1999-01-20
NO931681L (no)	1993-11-10
PL298845A1 (en)	1994-01-10
JPH0649022A (ja)	1994-02-22
HK1011990A1 (en)	1999-07-23
CA2095797C (en)	2007-09-18
JP3210771B2 (ja)	2001-09-17
BR1100581A (pt)	2000-08-01
DK0569802T3 (da)	1999-04-19
UA32543C2 (uk)	2001-02-15
ES2121030T3 (es)	1998-11-16
HU9301325D0 (en)	1993-09-28
HU214578B (hu)	1998-04-28
AU662051B2 (en)	1995-08-17
CA2095797A1 (en)	1993-11-10
CN1041087C (zh)	1998-12-09
DE4215213A1 (de)	1993-11-11
US5532266A (en)	1996-07-02
NO179789C (no)	1996-12-18

Legal Events

Date	Code	Title	Description
2013-07-02	MK4A	Patent expired	Expiry date: 20130512

Publication	Publication Date	Title
SK46893A3 (en)	1994-04-06	Process for preparing arylacetamides, and their pharmaceutical compositions
KR100523366B1 (ko)	2005-10-20	티에닐아졸일알콕시에탄아민, 이의 제조방법 및 이의 용도
SK26995A3 (en)	1995-10-11	Single acetamides for suppressing of diseases method of their production and their using for production of medicines pharmaceutical agents on their base and method of their production
US6281243B1 (en)	2001-08-28	Derivatives of azetidine and pyrrolidine
SK10802002A3 (sk)	2003-01-09	1,3-Disubstituované pyrolidíny, spôsob ich prípravy, ich použitie a farmaceutický prostriedok, ktorý ich obsahuje
EP0483580A2 (de)	1992-05-06	1-(2-Arylethyl)-Pyrrolidine
DE60316683T2 (de)	2008-07-17	Phenylcyclohexylpropanolaminderivate, deren herstellung und therapeutsche anwendung
KR19980703476A (ko)	1998-11-05	피롤리딘일 하이드록삼산 화합물 및 그의 제조 방법
JPH07507814A (ja)	1995-08-31	置換（アリールアルコキシベンジル）アミノプロパンアミド誘導体及びその製造方法
US5130309A (en)	1992-07-14	Aryloxy and aryloxyalklazetidines as antiarrhythmic and anticonvulsant agents
HU184806B (en)	1984-10-29	Process for preparing 3-methylene-azetidine derivatives
CZ257794A3 (en)	1995-11-15	Cyclic amino derivatives
JP3786983B2 (ja)	2006-06-21	ピロリジノン誘導体
DD153691A5 (de)	1982-01-27	Verfahren zur herstellung von hexahydro-trans-4a,9b-1(h)pyridoindol-derivaten
US5371088A (en)	1994-12-06	1-aryl-4-piperazinylcyclohexanecarbonitriles, the preparation and use thereof
CA2028798A1 (en)	1991-05-01	Benzylpyrrolidine derivatives as dopamine agonists
HK1011990B (en)	2000-03-24	Arylacetamides
DD301713A9 (de)	1993-07-29	Verfahren zur herstellung von bis (benzylpyrrolidin)-derivaten