ZA200100999B - New 4-amino-1-aryl-pyridine-2-ones with anticonvulsive action and method for producing same. - Google Patents
New 4-amino-1-aryl-pyridine-2-ones with anticonvulsive action and method for producing same. Download PDFInfo
- Publication number
- ZA200100999B ZA200100999B ZA200100999A ZA200100999A ZA200100999B ZA 200100999 B ZA200100999 B ZA 200100999B ZA 200100999 A ZA200100999 A ZA 200100999A ZA 200100999 A ZA200100999 A ZA 200100999A ZA 200100999 B ZA200100999 B ZA 200100999B
- Authority
- ZA
- South Africa
- Prior art keywords
- amino
- pyridin
- general formula
- compounds
- preparation
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 230000002082 anti-convulsion Effects 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- -1 morpholino, piperidino Chemical group 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 3
- 230000001037 epileptic effect Effects 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 239000001117 sulphuric acid Substances 0.000 claims description 3
- 235000011149 sulphuric acid Nutrition 0.000 claims description 3
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 claims description 2
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 claims description 2
- WSVGASGZCJRPIZ-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-(dimethylamino)pyridin-2-one Chemical compound O=C1C=C(N(C)C)C=CN1C1=CC=CC=C1Cl WSVGASGZCJRPIZ-UHFFFAOYSA-N 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 239000013543 active substance Substances 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000001961 anticonvulsive agent Substances 0.000 description 3
- 150000003230 pyrimidines Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SBQVQYPJWLJRQT-UHFFFAOYSA-N 4-amino-1h-pyridin-2-one Chemical class NC=1C=CNC(=O)C=1 SBQVQYPJWLJRQT-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 230000003556 anti-epileptic effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 206010015037 epilepsy Diseases 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 2
- ZEZJPIDPVXJEME-UHFFFAOYSA-N 2,4-Dihydroxypyridine Chemical class OC=1C=CNC(=O)C=1 ZEZJPIDPVXJEME-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- UIHGAGBMEXCYBJ-UHFFFAOYSA-N 4-amino-1-phenylpyridin-2-one Chemical compound O=C1C=C(N)C=CN1C1=CC=CC=C1 UIHGAGBMEXCYBJ-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000557626 Corvus corax Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 238000006254 arylation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 231100000189 neurotoxic Toxicity 0.000 description 1
- 230000002887 neurotoxic effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D213/60—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 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D213/60—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 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19835918A DE19835918A1 (de) | 1998-08-07 | 1998-08-07 | Neue antikonvulsiv wirkende 4-Amino-1-aryl-pyridin-2-one und Verfahren zu deren Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200100999B true ZA200100999B (en) | 2001-12-14 |
Family
ID=7876889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200100999A ZA200100999B (en) | 1998-08-07 | 2001-02-06 | New 4-amino-1-aryl-pyridine-2-ones with anticonvulsive action and method for producing same. |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6071911A (fr) |
| EP (1) | EP1102748A1 (fr) |
| JP (1) | JP2002522420A (fr) |
| KR (1) | KR20010074802A (fr) |
| CN (1) | CN1322197A (fr) |
| AR (1) | AR021186A1 (fr) |
| AU (1) | AU5507499A (fr) |
| BG (1) | BG105196A (fr) |
| BR (1) | BR9912849A (fr) |
| CA (1) | CA2279692C (fr) |
| DE (1) | DE19835918A1 (fr) |
| HU (1) | HUP0103204A3 (fr) |
| IL (1) | IL141200A0 (fr) |
| NO (1) | NO20010575L (fr) |
| NZ (1) | NZ509914A (fr) |
| PL (1) | PL346013A1 (fr) |
| RU (1) | RU2001106634A (fr) |
| SK (1) | SK2002001A3 (fr) |
| TR (1) | TR200100370T2 (fr) |
| WO (1) | WO2000007988A1 (fr) |
| ZA (1) | ZA200100999B (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2320973T3 (es) | 2000-06-12 | 2009-06-01 | EISAI R&D MANAGEMENT CO., LTD. | Compuestos de 1,2-dihidropiridina, procedimiento para su preparacion y uso de los mismos. |
| GB0129260D0 (en) | 2001-12-06 | 2002-01-23 | Eisai London Res Lab Ltd | Pharmaceutical compositions and their uses |
| MY148809A (en) | 2004-07-06 | 2013-05-31 | Eisai R&D Man Co Ltd | Crystals of 1,2-dihydropyridine compound and their production process |
| KR20210107644A (ko) | 2018-12-14 | 2021-09-01 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 1,2-디하이드로피리딘 화합물의 수성 기반 약학적 제형 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51118768A (en) * | 1975-02-19 | 1976-10-18 | Shigeo Senda | Method for preparing 4-amino-2-pyridone derivatives |
| EP0110091B1 (fr) * | 1982-10-27 | 1987-01-21 | Degussa Aktiengesellschaft | Dérivés de la 2-amino-3-acylamino-6-benzylamino-pyridine à activité antiépileptique |
-
1998
- 1998-08-07 DE DE19835918A patent/DE19835918A1/de not_active Withdrawn
-
1999
- 1999-07-28 SK SK200-2001A patent/SK2002001A3/sk unknown
- 1999-07-28 CN CN99811849A patent/CN1322197A/zh active Pending
- 1999-07-28 WO PCT/EP1999/005399 patent/WO2000007988A1/fr not_active Application Discontinuation
- 1999-07-28 BR BR9912849-7A patent/BR9912849A/pt not_active IP Right Cessation
- 1999-07-28 AU AU55074/99A patent/AU5507499A/en not_active Abandoned
- 1999-07-28 KR KR1020017001574A patent/KR20010074802A/ko not_active Application Discontinuation
- 1999-07-28 HU HU0103204A patent/HUP0103204A3/hu unknown
- 1999-07-28 PL PL99346013A patent/PL346013A1/xx unknown
- 1999-07-28 JP JP2000563622A patent/JP2002522420A/ja active Pending
- 1999-07-28 IL IL14120099A patent/IL141200A0/xx unknown
- 1999-07-28 RU RU2001106634/04A patent/RU2001106634A/ru unknown
- 1999-07-28 EP EP99941472A patent/EP1102748A1/fr not_active Withdrawn
- 1999-07-28 TR TR2001/00370T patent/TR200100370T2/xx unknown
- 1999-07-28 NZ NZ509914A patent/NZ509914A/xx unknown
- 1999-08-05 CA CA002279692A patent/CA2279692C/fr not_active Expired - Fee Related
- 1999-08-06 US US09/370,640 patent/US6071911A/en not_active Expired - Fee Related
- 1999-08-06 AR ARP990103952A patent/AR021186A1/es not_active Application Discontinuation
-
2001
- 2001-01-30 BG BG105196A patent/BG105196A/xx unknown
- 2001-02-02 NO NO20010575A patent/NO20010575L/no unknown
- 2001-02-06 ZA ZA200100999A patent/ZA200100999B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20010074802A (ko) | 2001-08-09 |
| AU5507499A (en) | 2000-02-28 |
| NO20010575L (no) | 2001-04-04 |
| JP2002522420A (ja) | 2002-07-23 |
| BR9912849A (pt) | 2001-05-08 |
| SK2002001A3 (en) | 2002-01-07 |
| CN1322197A (zh) | 2001-11-14 |
| CA2279692A1 (fr) | 2000-02-07 |
| NO20010575D0 (no) | 2001-02-02 |
| AR021186A1 (es) | 2002-07-03 |
| HUP0103204A3 (en) | 2002-06-28 |
| TR200100370T2 (tr) | 2001-08-21 |
| DE19835918A1 (de) | 2000-02-10 |
| NZ509914A (en) | 2002-11-26 |
| HUP0103204A2 (hu) | 2002-04-29 |
| PL346013A1 (en) | 2002-01-14 |
| BG105196A (en) | 2001-12-29 |
| US6071911A (en) | 2000-06-06 |
| IL141200A0 (en) | 2002-02-10 |
| EP1102748A1 (fr) | 2001-05-30 |
| RU2001106634A (ru) | 2004-02-27 |
| WO2000007988A1 (fr) | 2000-02-17 |
| CA2279692C (fr) | 2003-10-07 |
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