LT4482B - Nauji 1-aril(alkil)imidazolin-2-onai, turintys dipakeistą aminogrupė 4 padėtyje, pasižymintys antispazminiu veikimu, ir jų gavimo būdas - Google Patents
Nauji 1-aril(alkil)imidazolin-2-onai, turintys dipakeistą aminogrupė 4 padėtyje, pasižymintys antispazminiu veikimu, ir jų gavimo būdas Download PDFInfo
- Publication number
- LT4482B LT4482B LT98-047A LT98047A LT4482B LT 4482 B LT4482 B LT 4482B LT 98047 A LT98047 A LT 98047A LT 4482 B LT4482 B LT 4482B
- Authority
- LT
- Lithuania
- Prior art keywords
- morpholinimidazolin
- compounds
- imidazolin
- alkyl
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims 3
- 230000002082 anti-convulsion Effects 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 208000002877 Epileptic Syndromes Diseases 0.000 claims description 3
- -1 1- (4-Chlorophenyl) -4-hexamethyleniminoimidazolin-2-one 1- (4-Chlorophenyl) -4- (4-methylpiperazino) imidazolin-2-one Chemical compound 0.000 claims description 2
- XBWXQYHHBYAPTM-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-(cyclohexylmethylamino)imidazolidin-2-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)NC(NCC2CCCCC2)C1 XBWXQYHHBYAPTM-UHFFFAOYSA-N 0.000 claims description 2
- CNRVYYCOZHBSNP-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-(dimethylamino)imidazolidin-2-one Chemical compound O=C1NC(N(C)C)CN1C1=CC=C(Cl)C=C1 CNRVYYCOZHBSNP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical class O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 230000002921 anti-spasmodic effect Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 206010029350 Neurotoxicity Diseases 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 206010044221 Toxic encephalopathy Diseases 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 2
- 230000007135 neurotoxicity Effects 0.000 description 2
- 231100000228 neurotoxicity Toxicity 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- PALSNOHDUSGTFY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-(4-methylpiperazin-1-yl)imidazolidin-2-one Chemical compound C1CN(C)CCN1C1NC(=O)N(C=2C=CC(Cl)=CC=2)C1 PALSNOHDUSGTFY-UHFFFAOYSA-N 0.000 description 1
- NSUITYVMTIPQNG-UHFFFAOYSA-N 4-(azepan-1-yl)-1-(4-chlorophenyl)imidazolidin-2-one Chemical compound ClC1=CC=C(C=C1)N1C(NC(C1)N1CCCCCC1)=O NSUITYVMTIPQNG-UHFFFAOYSA-N 0.000 description 1
- 241000557626 Corvus corax Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 238000007126 N-alkylation reaction Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 1
- 229960000623 carbamazepine Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical class NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- HGASFNYMVGEKTF-UHFFFAOYSA-N octan-1-ol;hydrate Chemical compound O.CCCCCCCCO HGASFNYMVGEKTF-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003334 secondary amides Chemical class 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- AEQFSUDEHCCHBT-UHFFFAOYSA-M sodium valproate Chemical compound [Na+].CCCC(C([O-])=O)CCC AEQFSUDEHCCHBT-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940102566 valproate Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/88—Nitrogen atoms, e.g. allantoin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19532668A DE19532668A1 (de) | 1995-09-05 | 1995-09-05 | Neue, antikonvulsiv wirkende 1-Ar(alk)yl-imidazolin-2-one, die in 4-Stellung einen disubstituierten Amin-Rest enthalten, und Verfahren zu deren Herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LT98047A LT98047A (en) | 1998-10-26 |
| LT4482B true LT4482B (lt) | 1999-03-25 |
Family
ID=7771261
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LT98-047A LT4482B (lt) | 1995-09-05 | 1998-04-03 | Nauji 1-aril(alkil)imidazolin-2-onai, turintys dipakeistą aminogrupė 4 padėtyje, pasižymintys antispazminiu veikimu, ir jų gavimo būdas |
Country Status (31)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19721580A1 (de) * | 1997-05-23 | 1998-11-26 | Dresden Arzneimittel | Verwendung von 1-Ar(alk)yl-imidazolin-2-one zur Behandlung von Angst- und Spannungszuständen |
| US20050070537A1 (en) * | 2002-10-10 | 2005-03-31 | Chris Rundfeldt | Use of dihydroimidazolones for the treatment of dogs |
| RU2354377C2 (ru) * | 2003-07-11 | 2009-05-10 | Берингер Ингельхайм Ветмедика Гмбх | Способ лечения или предупреждения заболеваний центральной нервной системы с использованием соединений, обладающих селективностью в отношении альфа-3-субъединицы бензодиазепинового рецептора |
| EP2093218A1 (en) * | 2008-02-22 | 2009-08-26 | Ruggero Fariello | Arylalkyl substituted imidazolidinones |
| AR089646A1 (es) | 2011-08-12 | 2014-09-10 | Boehringer Ingelheim Vetmed | Inhibidores de corrientes funny (if) para utilizar en un metodo de tratamiento y prevencion de la insuficiencia cardiaca en felinos |
| US9820988B2 (en) | 2014-03-24 | 2017-11-21 | Boehringer Ingelheim Vetmedica Gmbh | Treatment of epileptic disorders in feline animals |
| IT202100000782A1 (it) | 2021-01-18 | 2022-07-18 | Procos Spa | Processo per la sintesi di imepitoina |
| EP4553066A1 (en) | 2023-11-10 | 2025-05-14 | Justesa Imagen S.A.U. | Improved process for the synthesis of imepitoin |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2251354A1 (de) | 1971-10-21 | 1973-04-26 | American Cyanamid Co | Neue diuretica und mittel zur behandlung von hyperaldosteronismus |
| US4044021A (en) | 1971-10-21 | 1977-08-23 | American Cyanamid Company | Tetrasubstituted imidazolidine diuretics useful in the treatment of hyperaldosteronism |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3932452A (en) * | 1975-02-07 | 1976-01-13 | Morton-Norwich Products, Inc. | 1-Arylmethyl-2-imidazolidinones |
-
1995
- 1995-09-05 DE DE19532668A patent/DE19532668A1/de not_active Ceased
-
1996
- 1996-07-26 ES ES96927607T patent/ES2208758T3/es not_active Expired - Lifetime
- 1996-07-26 JP JP51080097A patent/JP4030578B2/ja not_active Expired - Lifetime
- 1996-07-26 CN CN96197801A patent/CN1103762C/zh not_active Expired - Lifetime
- 1996-07-26 PT PT96927607T patent/PT863880E/pt unknown
- 1996-07-26 TR TR1998/00476T patent/TR199800476T1/xx unknown
- 1996-07-26 AT AT96927607T patent/ATE254606T1/de active
- 1996-07-26 PL PL96325413A patent/PL188287B1/pl unknown
- 1996-07-26 EP EP96927607A patent/EP0863880B1/de not_active Expired - Lifetime
- 1996-07-26 BR BR9610359A patent/BR9610359A/pt active IP Right Grant
- 1996-07-26 EA EA199800271A patent/EA000535B1/ru not_active IP Right Cessation
- 1996-07-26 IL IL12333396A patent/IL123333A/en not_active IP Right Cessation
- 1996-07-26 NZ NZ315624A patent/NZ315624A/en not_active IP Right Cessation
- 1996-07-26 WO PCT/EP1996/003295 patent/WO1997009314A1/de active IP Right Grant
- 1996-07-26 UA UA98041717A patent/UA46790C2/uk unknown
- 1996-07-26 SK SK216-98A patent/SK284868B6/sk not_active IP Right Cessation
- 1996-07-26 DE DE59610827T patent/DE59610827D1/de not_active Expired - Lifetime
- 1996-07-26 EE EE9800063A patent/EE03562B1/xx unknown
- 1996-07-26 AU AU67375/96A patent/AU700602B2/en not_active Expired
- 1996-07-26 CZ CZ1998661A patent/CZ291839B6/cs not_active IP Right Cessation
- 1996-07-26 GE GEAP19964221A patent/GEP20022652B/en unknown
- 1996-07-26 DK DK96927607T patent/DK0863880T3/da active
- 1996-07-26 HU HU9802941A patent/HU225956B1/hu unknown
- 1996-08-19 ZA ZA967014A patent/ZA967014B/xx unknown
- 1996-09-03 TW TW085110749A patent/TW422838B/zh not_active IP Right Cessation
- 1996-09-04 AR ARP960104226A patent/AR003502A1/es active IP Right Grant
- 1996-09-05 CA CA002184871A patent/CA2184871C/en not_active Expired - Lifetime
-
1998
- 1998-02-27 BG BG102287A patent/BG63917B1/bg unknown
- 1998-03-02 NO NO19980906A patent/NO313829B1/no not_active IP Right Cessation
- 1998-04-03 LT LT98-047A patent/LT4482B/lt not_active IP Right Cessation
-
2013
- 2013-08-07 LU LU92263C patent/LU92263I2/fr unknown
- 2013-08-13 FR FR13C0049C patent/FR13C0049I2/fr active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2251354A1 (de) | 1971-10-21 | 1973-04-26 | American Cyanamid Co | Neue diuretica und mittel zur behandlung von hyperaldosteronismus |
| US4044021A (en) | 1971-10-21 | 1977-08-23 | American Cyanamid Company | Tetrasubstituted imidazolidine diuretics useful in the treatment of hyperaldosteronism |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5391577A (en) | N-phenylalkyl substituted α-amino carboxamide derivatives and process for their preparation | |
| FI62821B (fi) | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara hydroxamsyror | |
| US4400394A (en) | Benzylidene derivatives | |
| EP0734379B1 (fr) | Derives de 2-arylalkenyl-azacycloalkanes ligands aux recepteurs sigma, leur procede de preparation et leur application en therapeutique | |
| IE55770B1 (en) | N-formyl and n-hydroxymethyl-3-phenoxy-1-azetidinecarboxamides and their preparation and use | |
| LT4482B (lt) | Nauji 1-aril(alkil)imidazolin-2-onai, turintys dipakeistą aminogrupė 4 padėtyje, pasižymintys antispazminiu veikimu, ir jų gavimo būdas | |
| US4324787A (en) | 2-Oxo-1-pyrrolidineacetic acid compounds and their medicinal use | |
| PL194745B1 (pl) | Podstawiony 2-benzyloamino-2-fenylo-acetamid, zawierająca go kompozycja farmaceutyczna i zastosowanie | |
| IE55872B1 (en) | Derivatives of omega-amino acids,the preparation and utilisation thereof,and the compositions containing these derivatives | |
| HU178652B (en) | Process for producing pharmaceutically active 2-bracket-amino-butoxy-bracket closed stylbenes | |
| FI69836B (fi) | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 4-fenyl-1,3-bensodiazepinderivat | |
| EP0475214B1 (en) | Caffeic acid derivatives and pharmaceutical compositions containing the same | |
| KR910003711B1 (ko) | 2-(n-피롤리디노)-3-이소부톡시-n-치환된 페닐-n-벤질-프로필아민의 제조방법 | |
| HU190710B (en) | Process for preparing 2-/4-piperazinyl/-4-phenyl-quinazoline derivatives | |
| AU611978B2 (en) | Araliphatic oxo(hydroxy) amines | |
| SU906366A3 (ru) | Способ получени гидрохлорида N-алкильных производных 1-фенил-2-амино-1,3-пропандиола | |
| FI60863C (fi) | Foerfarande foer framstaellning av nya bentshydryloxialkylaminderivat med foerlaengd antihistamineffekt | |
| FR2507180A1 (fr) | Nouvelles phenylalkylamines, leur preparation et leur application comme medicaments | |
| US3963748A (en) | 1-Phenyl-3-azacarbocyclic-ureas | |
| LT4457B (lt) | Nauji pasižymintys antispazminiu aktyvumu imidazolin-2,4-dionai, turintys orto-pakeistą aril(alkil)-radikalą 1 padėtyje, ir jų gavimo būdas | |
| EP0663395A1 (de) | 3-(Phenylalkylaminoalkyloxy)-5-phenylpyrazol-Derivate, Verfahren und Zwischenprodukte zu ihrer Herstellung und ihrer Verwendung als herzfrequenzsenkendes Mittel | |
| US4026938A (en) | 1-Phenyl-3-azacarbocyclic-ureas | |
| US4052382A (en) | 1-phenyl-3-azacarbocyclic-ureas | |
| HU191585B (en) | Process for producing tetramethyl-proline-3-carboxamide derivatives and new cardiotherapeutic compositions containing them | |
| HK1015776B (en) | Novel 1-ar(alk)ylimidazolin-2-ones containing a disubstituted amine radical in the 4-position, having an anticonvulsive activity, and process for their preparation |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC9A | Transfer of patents |
Owner name: ELBION AG, DE Effective date: 20041130 |
|
| PD9A | Change of patent owner |
Owner name: ELBION GMBH, , , DE Effective date: 20071122 |
|
| TC9A | Change of representative |
Owner name: ELBION GMBH, , , DE |
|
| MK9A | Expiry of a patent |
Effective date: 20160726 |