SU685149A3 - Способ получени аминоалкилгетероциклических соединений или их солей - Google Patents
Способ получени аминоалкилгетероциклических соединений или их солейInfo
- Publication number
- SU685149A3 SU685149A3 SU772542149A SU2542149A SU685149A3 SU 685149 A3 SU685149 A3 SU 685149A3 SU 772542149 A SU772542149 A SU 772542149A SU 2542149 A SU2542149 A SU 2542149A SU 685149 A3 SU685149 A3 SU 685149A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- compounds
- salts
- aminoalheterocyclic
- obtaining
- hydrogen
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title description 6
- 150000003839 salts Chemical class 0.000 title description 5
- 238000000034 method Methods 0.000 title description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Chemical group 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 102100038902 Caspase-7 Human genes 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 101000741014 Homo sapiens Caspase-7 Proteins 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- -1 methoxy, hydroxy Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- 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
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/36—One oxygen atom with hydrocarbon radicals, substituted by nitrogen atoms, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 2
- C07D235/26—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Psychiatry (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Quinoline Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Laminated Bodies (AREA)
- Nonwoven Fabrics (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Description
Цель достигаетс синтезом соединений общей формулы (1) или их солей, основанным на известном способе. Указа1шые соединени получают восстановлением кетона общей формулы Я2п н-с1ц-со где Q, RS, Кб R п имеют указанные выше значени , комплексными гидридами металлов или в присутствии катализаторов гидрировани В качестве комплексных гидридов примен ю боргидрид натри или в качестве катализатора гидрировани - ,окйсь платины. Целевые продукты выдел ют в свободном виде или в виде их солей. Пример 1. Гидрохлорид 1-(3,4-диoкcифeнил )-l-oкcи-2 (З-метил)-бензимидазолиион- (2)-ил -этиламиноэтан. 42,5 г 3,4-дибензилоксифенш1-CJ -бромацето фенона и 29 г N-мeтил-N-(2-бeнзилaминoэтилбензимидазолинона- (2) кип т т с 25 г соды в течение 2 ч в 600 мл ацетонитрила. Неорганические примеси отфильтровывают и растворите отгон ют в вакууме. Остаток раствор ют в 900 мл метанола, добавл ют 30 мл 12%-ного хлористого водорода в эфире и 15 мл 1%-ног раствора хлорида паллади до поглощени 4 3 мол рных эквивалентов водорода и провод т гидрирование в присутствии 2 г активированного угл при температуре 60 С и давлении 5 ати. После отделени катализатора отгон ют метанол на половину и к раствору добавл ют 500 мл ацетонитрила. Выпавщие кристаллы гидрохлорида 1-(3,4-диоксифенил)-1-оксо-2- (3-метил)-бензимидазол нон-(2)-ил -этиламиноэтана фильтруют. Выход 32 г, т.пл. 250°С (из воды). 8 г полученного аминокетона раствор ют в 400 мл метанола, гидрируют в присутствии 1 г окиси платины и после поглощени 1 мол рного эквивалента водорода получают целевой продукт с выходом 88% т.пл. 180°С. П р и м е р 2. Целевое соединение примера 1 получают также восстановлением кетона боргидридом натри следующим образом. 9,45 г гидрохлорида 1-(3,4-диоксифенил)-1-оксо-2 (3-метил)-бензимидазо ЛИНОЙ- (2)-ил -этиламиноэтана (см. пример 1) раствор ют порци ми в течение 10 мин в 150 мл воды. К полученному раствору добавл ют 150 мл 1 н. раствора едкого натра, пропускают азот и при 20° С добавл ют 1,9 г боргидрида натри . Реакционную массу выдерживают при комнатной температуре, затем нагревают и после охлаждени до 50°С добавл ют сол ную кислоту до рН 4. Раствор концентрируют в вакууме. Выход цeлeвofo продукта 91%, т.пл. 185°С. ; Аналогично примерам 1 и 2 получают соединени приведенные в таблице.
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tN ОО 35 Форм ул а изобретени 1. Способ пол 1ени аминоалкилгетероци ческих соещшеиий общей формулы Q- СлН2л--Т й-СК2- СИОН где Q - один из радикалов общей формул Uv -А (Ща ипи где А -згЫН, МСНз, -OCHj - (атом кис да св зан с бензольным кольцом), -О- ил -CHj-CHj-; RI - водород или метокси; РЗ - водород или метокси; п 2-6; RS - водород, RgO-,, RgNH-, RgNCHaгидроксиметил , CN-, -CONHj, -CONHCH галоген; Яб - водород, ReO-; RS и Re вместе означают -СН СН-СН-ОСНз-СО -NH-, -CHj-CHj-CO-NH-, -0-CO-NH-; R - водород, метил, метокси, гидрокси или хлор, причем RS не может быть RgNH- или RgNCHj-, если R - хлор; Rg - водород или бензил; Рд - водород, ацетил, метилсульфонил, карбамоил , димет илсульфамонл, или их солей, отличающийс тем, что кетон общей формулы лН2л И-С112-(0 где Q, RS, Rgr R имеют указанные выше значени , восстанавливают комплексными гидридами или в присутствии катализаторов гидрировани с выделением целевого продукта в свободном виде или в виде соли. 2. Способ по п. 1,отличающийс тем, в качестве комплексного гидрида примен ют боргидрид натри или в качестве катализатора гидрировани - окись платины. Источники информащ1и, прин тые во внимание при экспертизе 1. Бюлер К., Шрсоп Д. Органические синтезы , М., 1973, т. 1, с. 222-233.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762609645 DE2609645A1 (de) | 1976-03-09 | 1976-03-09 | Aminoalkylheterocyclen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU685149A3 true SU685149A3 (ru) | 1979-09-05 |
Family
ID=5971857
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772453505A SU698530A3 (ru) | 1976-03-09 | 1977-02-22 | Способ получени аминоалкилгетероциклических соединений или их солей |
| SU772541704A SU676163A3 (ru) | 1976-03-09 | 1977-11-16 | Способ получени аминоалкилгетероциклических соединений или их солей |
| SU772543651A SU683616A3 (ru) | 1976-03-09 | 1977-11-16 | Способ получени аминоалкилгетероциклических соединений или их солей |
| SU772542149A SU685149A3 (ru) | 1976-03-09 | 1977-11-16 | Способ получени аминоалкилгетероциклических соединений или их солей |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772453505A SU698530A3 (ru) | 1976-03-09 | 1977-02-22 | Способ получени аминоалкилгетероциклических соединений или их солей |
| SU772541704A SU676163A3 (ru) | 1976-03-09 | 1977-11-16 | Способ получени аминоалкилгетероциклических соединений или их солей |
| SU772543651A SU683616A3 (ru) | 1976-03-09 | 1977-11-16 | Способ получени аминоалкилгетероциклических соединений или их солей |
Country Status (36)
| Country | Link |
|---|---|
| US (4) | US4154829A (ru) |
| JP (2) | JPS52108970A (ru) |
| AT (1) | AT360542B (ru) |
| AU (1) | AU515953B2 (ru) |
| BE (1) | BE852223A (ru) |
| BG (4) | BG27743A3 (ru) |
| CA (1) | CA1086317A (ru) |
| CH (8) | CH630358A5 (ru) |
| CS (2) | CS209435B2 (ru) |
| DD (1) | DD130037A5 (ru) |
| DE (1) | DE2609645A1 (ru) |
| DK (1) | DK102177A (ru) |
| ES (10) | ES456622A1 (ru) |
| FI (1) | FI69070C (ru) |
| FR (2) | FR2343731A1 (ru) |
| GB (1) | GB1571231A (ru) |
| GR (1) | GR64553B (ru) |
| HK (1) | HK12884A (ru) |
| HU (1) | HU177953B (ru) |
| IE (1) | IE45300B1 (ru) |
| IL (1) | IL51627A (ru) |
| LU (1) | LU76898A1 (ru) |
| MX (1) | MX4878E (ru) |
| MY (1) | MY8500079A (ru) |
| NL (1) | NL7702403A (ru) |
| NO (1) | NO147950C (ru) |
| NZ (1) | NZ183536A (ru) |
| PH (3) | PH16110A (ru) |
| PL (2) | PL111240B1 (ru) |
| PT (1) | PT66282B (ru) |
| RO (3) | RO70569A (ru) |
| SE (1) | SE435059B (ru) |
| SG (1) | SG55583G (ru) |
| SU (4) | SU698530A3 (ru) |
| YU (1) | YU62377A (ru) |
| ZA (1) | ZA771412B (ru) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2609645A1 (de) * | 1976-03-09 | 1977-09-15 | Boehringer Sohn Ingelheim | Aminoalkylheterocyclen |
| DE2644833A1 (de) * | 1976-10-05 | 1978-04-20 | Boehringer Sohn Ingelheim | Neue 1-aryloxy-2-hydroxy-3-alkylenaminopropane und verfahren zu ihrer herstellung |
| DE2833140A1 (de) * | 1978-07-28 | 1980-02-07 | Boehringer Sohn Ingelheim | Neue n-substituierte heterocyclen |
| BE883069A (fr) | 1979-05-04 | 1980-08-18 | Continental Pharma | Derives de phenylethylamine, leur preparation et utilisation ainsi que composition contenant ces derives. |
| DE3026534A1 (de) * | 1980-07-12 | 1982-03-18 | C.H. Boehringer Sohn, 6507 Ingelheim | 3,1-benzoxazin-2-one, ihre herstellung und verwendung |
| US4460581A (en) * | 1982-10-12 | 1984-07-17 | Boehringer Ingelheim Kg | (1-Hydroxy-2-amino-alkyl)-substituted benzoxazinones and benzoxazolinones |
| DE3325875A1 (de) * | 1983-07-18 | 1985-01-31 | Boehringer Ingelheim KG, 6507 Ingelheim | Neue 1-phenylimidazolidin-2-on-derivate, ihre herstellung und verwendung |
| US4743613A (en) * | 1986-04-08 | 1988-05-10 | Smithkline Beckman Corporation | Ester prodrugs of dopamine-β-hydroxylase, inhibitors, composition containing them, and method of using them to inhibit dopamine-β-hydroxylase activity |
| GB8609331D0 (en) * | 1986-04-16 | 1986-05-21 | Pfizer Ltd | Anti-arrythmia agents |
| TW203049B (ru) * | 1990-04-13 | 1993-04-01 | Yamanouchi Pharma Co Ltd | |
| ZA967892B (en) * | 1995-09-21 | 1998-03-18 | Lilly Co Eli | Selective β3 adrenergic agonists. |
| US5808080A (en) * | 1996-09-05 | 1998-09-15 | Eli Lilly And Company | Selective β3 adrenergic agonists |
| DE69711519T2 (de) | 1996-09-05 | 2002-10-31 | Eli Lilly And Co., Indianapolis | Carbazolanaloge als selektive beta3-adrenergische Agonisten |
| CO5011072A1 (es) * | 1997-12-05 | 2001-02-28 | Lilly Co Eli | Etanolaminas pirazinil substituidas como agfonistas de los receptores |
| DK1385514T5 (da) | 2001-04-18 | 2009-03-09 | Euro Celtique Sa | Spiroinden- og spiroindanforbindelser |
| BR0209129A (pt) * | 2001-04-18 | 2005-12-20 | Euro Celtique Sa | Compostos, composições farmacêuticas, métodos para tratamento de dores, métodos para modulação de uma resposta farmacológica e usos de compostos |
| DK1385515T3 (da) | 2001-04-18 | 2008-10-27 | Euro Celtique Sa | Spiropyrazole forbindelser |
| RU2265018C2 (ru) * | 2001-04-18 | 2005-11-27 | Эро-Селтик, С.А. | Производные бензимидазола и фармацевтические композиции на их основе |
| PT1975164E (pt) | 2001-04-18 | 2010-04-20 | Euro Celtique Sa | Compostos de octa-hidrobenzimidazolona utilizados como analgésicos |
| EP1997818A3 (en) * | 2001-04-18 | 2009-04-08 | Euro-Celtique S.A. | Quinolinone derivatives and their use to treat pain |
| US7056916B2 (en) * | 2002-11-15 | 2006-06-06 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Medicaments for the treatment of chronic obstructive pulmonary disease |
| AU2003297562A1 (en) * | 2002-11-27 | 2004-06-23 | Artesian Therapeutics, Inc. | COMPOUNDS WITH MIXED PDE-INHIBITORY AND Beta-ADRENERGIC ANTAGONIST OR PARTIAL AGONIST ACTIVITY FOR TREATMENT OF HEART FAILURE |
| CA2511496A1 (en) * | 2002-12-23 | 2004-07-15 | Artesian Therapeutics, Inc. | Cardiotonic compounds with inhibitory activity against .beta.-adrenergic receptors and phosphodiesterase |
| DE102004001413A1 (de) * | 2004-01-09 | 2005-08-18 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 3-Hydroxymethyl-4-Hydroxy-Phenyl-Derivate zur Behandlung von chronisch obstruktiver Lungenerkrankung |
| DE102004003428A1 (de) * | 2004-01-23 | 2005-08-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue langwirksame Beta-2-Agonisten, und deren Verwendung als Arzneimittel |
| US20050272726A1 (en) * | 2004-04-22 | 2005-12-08 | Boehringer Ingelheim International Gmbh | Novel medicaments for the treatment of respiratory diseases |
| DE102004021779A1 (de) * | 2004-04-30 | 2005-11-24 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Beta-Agonisten, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| US20050256115A1 (en) * | 2004-05-14 | 2005-11-17 | Boehringer Ingelheim International Gmbh | Aerosol formulation for the inhalation of beta-agonists |
| US20050255050A1 (en) * | 2004-05-14 | 2005-11-17 | Boehringer Ingelheim International Gmbh | Powder formulations for inhalation, comprising enantiomerically pure beta agonists |
| US7220742B2 (en) * | 2004-05-14 | 2007-05-22 | Boehringer Ingelheim International Gmbh | Enantiomerically pure beta agonists, process for the manufacture thereof and use thereof as medicaments |
| DE102004045648A1 (de) * | 2004-09-21 | 2006-03-23 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Betamimetika zur Behandlung von Atemwegserkrankungen |
| US20080255134A1 (en) * | 2004-11-30 | 2008-10-16 | Artesian Therapeutics, Inc. | Cardiotonic Compounds With Inhibitory Activity Against Beta-Adrenergic Receptors And Phosphodiesterase |
| CA2588949A1 (en) * | 2004-11-30 | 2006-06-08 | Artesian Therapeutics, Inc. | Compounds with mixed pde-inhibitory and .beta.-adrenergic antagonist or partial agonist activity for treatment of heart failure |
| DE102005007654A1 (de) * | 2005-02-19 | 2006-08-24 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue langwirksame Betamimetika zur Behandlung von Atemwegserkrankungen |
| DE102005030733A1 (de) * | 2005-07-01 | 2007-01-04 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Arzneimittelkombinationen zur Behandlung von Atemwegserkrankungen enthaltend langwirksame Beta-2-Agonisten und wenigstens einen weiteren Wirkstoff |
| KR101360803B1 (ko) * | 2005-08-15 | 2014-02-11 | 베링거 인겔하임 인터내셔날 게엠베하 | 베타모방제의 제조방법 |
| DE102005052127A1 (de) * | 2005-10-28 | 2007-05-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue indol-haltige Beta-Agonisten, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| DE102005052102A1 (de) * | 2005-10-28 | 2007-05-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Beta-Agonisten, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| DE102005052101A1 (de) * | 2005-10-28 | 2007-05-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Beta-Agonisten, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| EP1986644A1 (de) * | 2006-02-16 | 2008-11-05 | Boehringer Ingelheim International GmbH | Arzneimittelkombinationen zur behandlung von atemwegserkrankungen |
| PE20080142A1 (es) * | 2006-03-15 | 2008-04-14 | Boehringer Ingelheim Int | Beta-agonistas enantiomericamente puros y sus procedimientos de preparacion |
| US20090324510A1 (en) | 2006-08-07 | 2009-12-31 | Boehringer Ingelheim International Gmbh | Drug combinations for the treatment of respiratory tract diseases |
| US8686008B2 (en) * | 2007-08-16 | 2014-04-01 | The University Of Mississippi | Highly selective sigma receptor ligands |
| WO2009026227A2 (en) * | 2007-08-16 | 2009-02-26 | The University Of Mississippi | Highly selective sigma receptor ligands |
| US9604926B2 (en) | 2007-08-16 | 2017-03-28 | The University Of Mississippi | Highly selective sigma receptor radioligands |
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|---|---|---|---|---|
| CA631296A (en) * | 1961-11-21 | Merck And Co. | Substituted benzimidazolones | |
| CH149009A (de) * | 1929-08-10 | 1931-08-15 | Chem Ind Basel | Verfahren zur Darstellung einer N-substituierten Verbindung der Pyridonreihe. |
| US2857394A (en) * | 1957-05-10 | 1958-10-21 | Ciba Pharm Prod Inc | Heterocyclic compounds |
| NL284529A (ru) * | 1961-10-24 | |||
| FR1516714A (fr) * | 1962-11-07 | 1968-02-05 | Bayer Ag | Procédé de préparation de dérivés de l'imidazolidine |
| FR1384708A (fr) * | 1963-11-21 | 1965-01-08 | Thomson Houston Comp Francaise | Perfectionnements aux dispositifs de mise en place d'objets |
| BE659364A (ru) * | 1964-02-05 | |||
| US3355457A (en) * | 1965-05-21 | 1967-11-28 | American Cyanamid Co | Substituted 2-imidazolinones |
| FR1573739A (ru) * | 1968-07-26 | 1969-07-04 | ||
| US3984405A (en) * | 1971-06-28 | 1976-10-05 | E. R. Squibb & Sons, Inc. | Anti-inflammatory agents |
| BE787103A (fr) * | 1971-08-04 | 1973-02-02 | Pfizer | Nouveaux derives de propanolamine et composition pharmaceutiqueles contenant |
| FR2168140A1 (en) * | 1972-01-17 | 1973-08-31 | Bellon Labor Sa Roger | Dihydro-benzoxazine derivs - antidepressants |
| US3925383A (en) * | 1972-12-08 | 1975-12-09 | Janssen Pharmaceutica Nv | Bicyclic imidazoles and pyrimidines |
| US3994901A (en) * | 1974-06-13 | 1976-11-30 | Otsuka Pharmaceutical Company Limited | 5-[1-Hydroxy-2-(substituted-amino)]alkyl-8-hydroxy-3,4-dihydrocarbostyril derivatives |
| US4081447A (en) * | 1975-04-09 | 1978-03-28 | Abbott Laboratories | 5-[2-Hydroxy-3-(3,4-dimethoxy phenethylamino)]-propoxy-3,4-dihydro carbostyril and pharmaceutically acceptable salts thereof |
| DE2609645A1 (de) * | 1976-03-09 | 1977-09-15 | Boehringer Sohn Ingelheim | Aminoalkylheterocyclen |
-
1976
- 1976-03-09 DE DE19762609645 patent/DE2609645A1/de not_active Withdrawn
-
1977
- 1977-02-22 SU SU772453505A patent/SU698530A3/ru active
- 1977-02-23 FI FI770586A patent/FI69070C/fi not_active IP Right Cessation
- 1977-02-24 AT AT122377A patent/AT360542B/de not_active IP Right Cessation
- 1977-03-01 RO RO7789565A patent/RO70569A/ro unknown
- 1977-03-01 RO RO77101591A patent/RO79706A/ro unknown
- 1977-03-01 RO RO7796539A patent/RO76589A/ro unknown
- 1977-03-02 US US05/773,394 patent/US4154829A/en not_active Expired - Lifetime
- 1977-03-03 MX MX775497U patent/MX4878E/es unknown
- 1977-03-04 CS CS771476A patent/CS209435B2/cs unknown
- 1977-03-04 CS CS775352A patent/CS220320B2/cs unknown
- 1977-03-07 BG BG035601A patent/BG27743A3/xx unknown
- 1977-03-07 NL NL7702403A patent/NL7702403A/xx not_active Application Discontinuation
- 1977-03-07 BG BG036628A patent/BG28051A4/xx unknown
- 1977-03-07 BG BG036629A patent/BG28052A4/xx unknown
- 1977-03-07 CH CH281977A patent/CH630358A5/de not_active IP Right Cessation
- 1977-03-07 DD DD7700197718A patent/DD130037A5/xx unknown
- 1977-03-07 LU LU76898A patent/LU76898A1/xx unknown
- 1977-03-08 PT PT66282A patent/PT66282B/pt unknown
- 1977-03-08 HU HU77BO1653A patent/HU177953B/hu unknown
- 1977-03-08 IE IE507/77A patent/IE45300B1/en unknown
- 1977-03-08 DK DK102177A patent/DK102177A/da not_active Application Discontinuation
- 1977-03-08 PL PL1977196505A patent/PL111240B1/pl unknown
- 1977-03-08 ZA ZA00771412A patent/ZA771412B/xx unknown
- 1977-03-08 NO NO770804A patent/NO147950C/no unknown
- 1977-03-08 PL PL1977215210A patent/PL112937B1/pl unknown
- 1977-03-08 SE SE7702609A patent/SE435059B/xx not_active IP Right Cessation
- 1977-03-08 GR GR52928A patent/GR64553B/el unknown
- 1977-03-08 CA CA273,388A patent/CA1086317A/en not_active Expired
- 1977-03-08 IL IL51627A patent/IL51627A/xx unknown
- 1977-03-08 ES ES456622A patent/ES456622A1/es not_active Expired
- 1977-03-08 NZ NZ183536A patent/NZ183536A/xx unknown
- 1977-03-08 AU AU23009/77A patent/AU515953B2/en not_active Expired
- 1977-03-08 JP JP2532377A patent/JPS52108970A/ja active Pending
- 1977-03-08 BE BE175593A patent/BE852223A/xx not_active IP Right Cessation
- 1977-03-08 YU YU00623/77A patent/YU62377A/xx unknown
- 1977-03-09 FR FR7707018A patent/FR2343731A1/fr active Granted
- 1977-03-09 GB GB9952/77A patent/GB1571231A/en not_active Expired
- 1977-03-09 PH PH19550A patent/PH16110A/en unknown
- 1977-11-16 SU SU772541704A patent/SU676163A3/ru active
- 1977-11-16 SU SU772543651A patent/SU683616A3/ru active
- 1977-11-16 SU SU772542149A patent/SU685149A3/ru active
-
1978
- 1978-02-01 FR FR7802775A patent/FR2372810A1/fr active Granted
- 1978-02-03 ES ES466605A patent/ES466605A1/es not_active Expired
- 1978-02-03 ES ES466598A patent/ES466598A1/es not_active Expired
- 1978-02-03 ES ES466602A patent/ES466602A1/es not_active Expired
- 1978-02-03 ES ES466603A patent/ES466603A1/es not_active Expired
- 1978-02-03 ES ES466601A patent/ES466601A1/es not_active Expired
- 1978-02-03 ES ES466599A patent/ES466599A1/es not_active Expired
- 1978-02-03 ES ES466606A patent/ES466606A1/es not_active Expired
- 1978-02-03 ES ES466604A patent/ES466604A1/es not_active Expired
- 1978-02-03 ES ES466600A patent/ES466600A1/es not_active Expired
- 1978-06-14 BG BG036630A patent/BG28053A4/xx unknown
-
1979
- 1979-04-03 US US06/026,608 patent/US4215119A/en not_active Expired - Lifetime
- 1979-12-13 US US06/102,904 patent/US4271158A/en not_active Expired - Lifetime
-
1980
- 1980-07-11 PH PH24278A patent/PH16149A/en unknown
- 1980-12-22 US US06/218,786 patent/US4363814A/en not_active Expired - Fee Related
-
1981
- 1981-01-23 PH PH25130A patent/PH17635A/en unknown
- 1981-04-30 CH CH284981A patent/CH630362A5/de not_active IP Right Cessation
- 1981-04-30 CH CH285281A patent/CH630365A5/de not_active IP Right Cessation
- 1981-04-30 CH CH284881A patent/CH630361A5/de not_active IP Right Cessation
- 1981-04-30 CH CH285181A patent/CH630364A5/de not_active IP Right Cessation
- 1981-04-30 CH CH285081A patent/CH630363A5/de not_active IP Right Cessation
- 1981-04-30 CH CH284681A patent/CH630359A5/de not_active IP Right Cessation
- 1981-04-30 CH CH284781A patent/CH630360A5/de not_active IP Right Cessation
-
1983
- 1983-09-01 SG SG555/83A patent/SG55583G/en unknown
-
1984
- 1984-02-16 HK HK128/84A patent/HK12884A/xx unknown
-
1985
- 1985-06-12 JP JP60126401A patent/JPS6172A/ja active Pending
- 1985-12-30 MY MY79/85A patent/MY8500079A/xx unknown
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