SK285618B6 - N-Substituované indol-3-glyoxylamidy s antiastmatickým, antialergickým a imunosupresívnym/imunomodulujúcim účinkom, použitie týchto zlúčenín na výrobu liečivého prípravku, liečivý prípravok obsahujúci N-substituované indol-3-glyoxylamidy, spôsob výroby liečivého prípravku a spôsob výroby N-substituovaných indol-3-glyoxylamidov - Google Patents
N-Substituované indol-3-glyoxylamidy s antiastmatickým, antialergickým a imunosupresívnym/imunomodulujúcim účinkom, použitie týchto zlúčenín na výrobu liečivého prípravku, liečivý prípravok obsahujúci N-substituované indol-3-glyoxylamidy, spôsob výroby liečivého prípravku a spôsob výroby N-substituovaných indol-3-glyoxylamidov Download PDFInfo
- Publication number
- SK285618B6 SK285618B6 SK271-99A SK27199A SK285618B6 SK 285618 B6 SK285618 B6 SK 285618B6 SK 27199 A SK27199 A SK 27199A SK 285618 B6 SK285618 B6 SK 285618B6
- Authority
- SK
- Slovakia
- Prior art keywords
- glyoxylamide
- pyridin
- alkyl
- indol
- fluorobenzyl
- Prior art date
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- -1 N-Substituted indole-3-glyoxylamides Chemical class 0.000 title claims abstract description 48
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims abstract description 8
- 230000001088 anti-asthma Effects 0.000 title claims abstract description 5
- 239000000924 antiasthmatic agent Substances 0.000 title claims abstract description 5
- 230000002519 immonomodulatory effect Effects 0.000 title claims abstract description 5
- 230000003266 anti-allergic effect Effects 0.000 title claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 230000001506 immunosuppresive effect Effects 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 230000008569 process Effects 0.000 claims abstract description 3
- 239000000243 solution Substances 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
- 239000000010 aprotic solvent Substances 0.000 claims description 9
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 8
- AMANDCZTVNQSNB-UHFFFAOYSA-N glyoxamide Chemical compound NC(=O)C=O AMANDCZTVNQSNB-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000000725 suspension Substances 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 150000003335 secondary amines Chemical class 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000002475 indoles Chemical class 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000003495 polar organic solvent Substances 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical group C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 2
- SOLIIYNRSAWTSQ-UHFFFAOYSA-N 2-[1-[(4-chlorophenyl)methyl]indol-3-yl]-2-oxo-n-pyridin-4-ylacetamide Chemical compound C1=CC(Cl)=CC=C1CN1C2=CC=CC=C2C(C(=O)C(=O)NC=2C=CN=CC=2)=C1 SOLIIYNRSAWTSQ-UHFFFAOYSA-N 0.000 claims description 2
- LCBBWDDNCWSORP-UHFFFAOYSA-N 2-oxo-n-pyridin-4-yl-2-[1-(pyridin-3-ylmethyl)indol-3-yl]acetamide Chemical compound C=1N(CC=2C=NC=CC=2)C2=CC=CC=C2C=1C(=O)C(=O)NC1=CC=NC=C1 LCBBWDDNCWSORP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000005806 3,4,5-trimethoxybenzyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1C([H])([H])* 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
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- 239000006071 cream Substances 0.000 claims description 2
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- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 239000008298 dragée Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical group N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000002674 ointment Substances 0.000 claims description 2
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
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- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000000829 suppository Substances 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
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- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- ICJFBRZPVGJKLB-UHFFFAOYSA-N 2-[1-[(2-chlorophenyl)methyl]indol-3-yl]-2-oxo-n-pyridin-3-ylacetamide Chemical compound ClC1=CC=CC=C1CN1C2=CC=CC=C2C(C(=O)C(=O)NC=2C=NC=CC=2)=C1 ICJFBRZPVGJKLB-UHFFFAOYSA-N 0.000 claims 1
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- 125000000405 phenylalanyl group Chemical group 0.000 claims 1
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Classifications
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/22—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an aralkyl radical attached to the ring nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Transplantation (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19636150A DE19636150A1 (de) | 1996-09-06 | 1996-09-06 | N-substituierte Indol-3-glyoxylamide mit antiasthmatischer, antiallergischer und immunsuppressiver/immunmodulierender Wirkung |
| PCT/EP1997/004474 WO1998009946A1 (de) | 1996-09-06 | 1997-08-16 | N-substituierte indol-3-glyoxylamide mit antiasthmatischer, antiallergischer und immunsuppressiver/immunmodulierender wirkung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK27199A3 SK27199A3 (en) | 1999-08-06 |
| SK285618B6 true SK285618B6 (sk) | 2007-05-03 |
Family
ID=7804772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK271-99A SK285618B6 (sk) | 1996-09-06 | 1997-08-16 | N-Substituované indol-3-glyoxylamidy s antiastmatickým, antialergickým a imunosupresívnym/imunomodulujúcim účinkom, použitie týchto zlúčenín na výrobu liečivého prípravku, liečivý prípravok obsahujúci N-substituované indol-3-glyoxylamidy, spôsob výroby liečivého prípravku a spôsob výroby N-substituovaných indol-3-glyoxylamidov |
Country Status (26)
| Country | Link |
|---|---|
| US (4) | US6008231A (cs) |
| EP (1) | EP0931063B3 (cs) |
| JP (1) | JP3296437B2 (cs) |
| KR (1) | KR100516321B1 (cs) |
| CN (3) | CN100376554C (cs) |
| AR (1) | AR008630A1 (cs) |
| AT (1) | ATE342889T1 (cs) |
| AU (1) | AU726521B2 (cs) |
| BR (1) | BR9712808B1 (cs) |
| CA (1) | CA2215013C (cs) |
| CZ (1) | CZ302301B6 (cs) |
| DE (2) | DE19636150A1 (cs) |
| DK (1) | DK0931063T5 (cs) |
| ES (1) | ES2276433T7 (cs) |
| HU (1) | HU227797B1 (cs) |
| IL (1) | IL127798A (cs) |
| NO (2) | NO314725B3 (cs) |
| NZ (1) | NZ334476A (cs) |
| PT (1) | PT931063E (cs) |
| RU (1) | RU2237661C2 (cs) |
| SK (1) | SK285618B6 (cs) |
| TR (1) | TR199900469T2 (cs) |
| TW (1) | TW550256B (cs) |
| UA (1) | UA60312C2 (cs) |
| WO (1) | WO1998009946A1 (cs) |
| ZA (1) | ZA977475B (cs) |
Families Citing this family (52)
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| DE19636150A1 (de) * | 1996-09-06 | 1998-03-12 | Asta Medica Ag | N-substituierte Indol-3-glyoxylamide mit antiasthmatischer, antiallergischer und immunsuppressiver/immunmodulierender Wirkung |
| EE200000573A (et) * | 1998-03-31 | 2002-04-15 | The Institutes For Pharmaceutical Discovery, Llc | Asendatud indoolalkaanhapped |
| DE19814838C2 (de) * | 1998-04-02 | 2001-01-18 | Asta Medica Ag | Indolyl-3-glyoxylsäure-Derivate mit Antitumorwirkung |
| DE19946301A1 (de) * | 1998-04-02 | 2001-04-19 | Asta Medica Ag | Indolyl-3-glyoxylsäure-Derivate mit therapeutisch wertvollen Eigenschaften |
| CZ302588B6 (cs) * | 1998-04-02 | 2011-07-27 | Ziopharm Oncology, Inc. | Použití N-substituovaného indol-3-glyoxylamidu pro výrobu léciva |
| DE19917504A1 (de) * | 1999-04-17 | 2000-10-19 | Dresden Arzneimittel | Verwendung von Hydroxyindolen, die Inhibitoren der Phosphodiesterase 4 sind, zur Therapie chronisch obstruktiver Lungenerkrankungen |
| TR200003130T2 (tr) | 1998-04-28 | 2001-01-22 | Arzneimittelwerk Dresden Gmbh | Yeni hidroksiindoller, bunların fosfodiesteraz 4 inhibitörleri olarak kullanımları ve hazırlanmaları için işlemler |
| DE19818964A1 (de) * | 1998-04-28 | 1999-11-04 | Dresden Arzneimittel | Neue Hydroxyindole, deren Verwendung als Inhibitoren der Phospodiesterase 4 und Verfahren zu deren Herstellung |
| IL147688A0 (en) | 1999-08-21 | 2002-08-14 | Byk Gulden Lomberg Chem Fab | Synergistic combination |
| TWI269654B (en) * | 1999-09-28 | 2007-01-01 | Baxter Healthcare Sa | N-substituted indole-3-glyoxylamide compounds having anti-tumor action |
| DE19962300A1 (de) * | 1999-12-23 | 2001-06-28 | Asta Medica Ag | Substituierte N-Benzyl-Indol-3-yl-glyoxylsäure-Derivate mit Antitumorwirkung |
| DE10022925A1 (de) * | 2000-05-11 | 2001-11-15 | Basf Ag | Substituierte Indole als PARP-Inhibitoren |
| DE10037310A1 (de) * | 2000-07-28 | 2002-02-07 | Asta Medica Ag | Neue Indolderivate und deren Verwendung als Arzneimittel |
| CA2460347A1 (en) * | 2001-09-13 | 2003-03-20 | Synta Pharmaceuticals Corp. | 3-glyoxlylamideindoles for treating cancer |
| RU2337906C2 (ru) * | 2001-12-03 | 2008-11-10 | Уайт | Ингибиторы цитозольной фосфолипазы а2 |
| US6903104B2 (en) * | 2001-12-06 | 2005-06-07 | National Health Research Institutes | Indol-3-YL-2-oxoacetamide compounds and methods of use thereof |
| MXPA05001011A (es) * | 2002-07-26 | 2005-06-08 | Inst For Pharm Discovery Inc | Derivado de acidos indolalcanoicos substituidos y formulaciones que lo contienen para uso en tratamiento de complicaciones diabeticas. |
| HRP20050201A2 (en) * | 2002-08-01 | 2005-04-30 | Elbion Ag | Method for producing highly pure hydroxy indolyl glyoxylic acid amideslyoxylic acid amides |
| DE10253426B4 (de) * | 2002-11-15 | 2005-09-22 | Elbion Ag | Neue Hydroxyindole, deren Verwendung als Inhibitoren der Phosphodiesterase 4 und Verfahren zu deren Herstellung |
| WO2004087211A2 (en) | 2003-04-01 | 2004-10-14 | Applied Research Systems Ars Holding N.V. | Inhibitors of phosphodiesterases in infertility |
| DE10318610A1 (de) * | 2003-04-24 | 2004-11-11 | Elbion Ag | 7-Azaindole und deren Verwendung als Therapeutika |
| DE10318611A1 (de) * | 2003-04-24 | 2004-11-11 | Elbion Ag | 4-, 6- oder 7-Hydroxyindole mit N-Oxidgruppen und deren Verwendung als Therapeutika |
| DE10318609A1 (de) * | 2003-04-24 | 2004-11-11 | Elbion Ag | 5-Hydroxyindole mit N-Oxidgruppen und deren Verwendung als Therapeutika |
| US20050075364A1 (en) * | 2003-07-01 | 2005-04-07 | Kap-Sun Yeung | Indole, azaindole and related heterocyclic N-substituted piperazine derivatives |
| DE10334040A1 (de) * | 2003-07-25 | 2005-03-10 | Zentaris Gmbh | Neue N-substituierte Indolyl-3-glyoxylsäureamide, deren Verwendung als Arzneimittel und Verfahren zu deren Herstellung |
| MXPA06002853A (es) | 2003-09-11 | 2006-06-14 | Kemia Inc | Inhibidores citoquina. |
| WO2006115509A2 (en) | 2004-06-24 | 2006-11-02 | Novartis Vaccines And Diagnostics Inc. | Small molecule immunopotentiators and assays for their detection |
| DE102004031538A1 (de) * | 2004-06-29 | 2006-02-09 | Baxter International Inc., Deerfield | Pharmazeutische Darreichungsform zur oralen Verabreichung eines schwerlöslichen Wirkstoffs, Verfahren zu deren Herstellung und Kit |
| JP2008519036A (ja) * | 2004-11-08 | 2008-06-05 | バクスター・インターナショナル・インコーポレイテッド | チューブリン阻害化合物のナノ粒子組成物 |
| US20060100209A1 (en) * | 2004-11-09 | 2006-05-11 | Chong-Hui Gu | Formulations of 1-(4-benzoyl-piperazin-1-yl)-2-[4-methoxy-7-(3-methyl-[1,2,4]triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-ethane-1,2-dione |
| US20060100432A1 (en) * | 2004-11-09 | 2006-05-11 | Matiskella John D | Crystalline materials of 1-(4-benzoyl-piperazin-1-yl)-2-[4-methoxy-7-(3-methyl-[1,2,4]triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-ethane-1,2-dione |
| WO2006073973A2 (en) | 2004-12-31 | 2006-07-13 | Reddy Us Therapeutics, Inc. | Novel benzylamine derivatives as cetp inhibitors |
| US8604055B2 (en) | 2004-12-31 | 2013-12-10 | Dr. Reddy's Laboratories Ltd. | Substituted benzylamino quinolines as cholesterol ester-transfer protein inhibitors |
| JP2006247963A (ja) * | 2005-03-09 | 2006-09-21 | Oji Paper Co Ltd | インクジェット記録用シート |
| EP2363128B1 (en) * | 2005-03-11 | 2016-02-17 | Vertex Pharmaceuticals Incorporated | Indole modulators of ATP-binding cassette transporters |
| KR20080025366A (ko) | 2005-04-29 | 2008-03-20 | 텐딕스 디벨롭먼트, 엘엘씨 | 래디얼 임펄스 엔진, 펌프 및 압축기 시스템과 관련 동작방법 |
| US20060280787A1 (en) * | 2005-06-14 | 2006-12-14 | Baxter International Inc. | Pharmaceutical formulation of the tubulin inhibitor indibulin for oral administration with improved pharmacokinetic properties, and process for the manufacture thereof |
| US7598380B2 (en) * | 2005-08-03 | 2009-10-06 | Bristol-Myers Squibb Company | Method of preparation of azaindole derivatives |
| ITMI20051999A1 (it) * | 2005-10-21 | 2007-04-22 | Eratech S R L | Formulazioni inalatorie di farmaci in fora di polvere secca per somministrazione come tale o con nebulizzatore e dotate di elevata erogabilita' respirabilita' e stabilita' |
| US7851476B2 (en) * | 2005-12-14 | 2010-12-14 | Bristol-Myers Squibb Company | Crystalline forms of 1-benzoyl-4-[2-[4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-YL)-1-[(phosphonooxy)methyl]-1H-pyrrolo[2,3-C]pyridin-3-YL]-1,2-dioxoethyl]-piperazine |
| US7807671B2 (en) | 2006-04-25 | 2010-10-05 | Bristol-Myers Squibb Company | Diketo-piperazine and piperidine derivatives as antiviral agents |
| SI2359826T1 (sl) | 2006-07-05 | 2014-02-28 | Takeda Gmbh | Kombinacija HMG-CoA reduktaznega inhibitorja rosuvastatina s fosfodiesteraznim 4 inhibitorjem, kot je roflumilast, roflumilast-N-oksid, za zdravljenje vnetnih pljučnih bolezni |
| MX2009001327A (es) * | 2006-08-07 | 2009-06-05 | Ironwood Pharmaceuticals Inc | Compuestos de indol. |
| JP2010509237A (ja) * | 2006-11-02 | 2010-03-25 | アレテ セラピューティクス， インコーポレイテッド | 可溶性エポキシドヒドロラーゼ阻害剤 |
| US20080241274A1 (en) * | 2006-11-28 | 2008-10-02 | Ziopharm Oncology, Inc. | Indibulin therapy |
| MX2011011517A (es) | 2009-04-29 | 2012-06-19 | Amarin Corp Plc | Composiciones farmaceuticas que comprenden epa y un agente cardiovascular y metodos para utilizar el mismo. |
| AR084433A1 (es) | 2010-12-22 | 2013-05-15 | Ironwood Pharmaceuticals Inc | Inhibidores de la faah y composiciones farmaceuticas que los contienen |
| US9199967B2 (en) | 2011-08-18 | 2015-12-01 | Dr. Reddy's Laboratories Ltd. | Substituted heterocyclic amine compounds as cholestryl ester-transfer protein (CETP) inhibitors |
| CN103958511A (zh) | 2011-09-27 | 2014-07-30 | 雷迪博士实验室有限公司 | 作为胆固醇酯转移蛋白(CETP)抑制剂用于治疗动脉粥样硬化的5-苄基氨基甲基-6-氨基吡唑并[3,4-b]吡啶衍生物 |
| EP3165224A1 (en) | 2015-11-09 | 2017-05-10 | Albert-Ludwigs-Universität Freiburg | Use of pde4 inhibitors for the prophylaxis and/or therapy of dyslipoproteinaemia and related disorders |
| WO2017089347A1 (en) | 2015-11-25 | 2017-06-01 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Methods and pharmaceutical compositions for the treatment of braf inhibitor resistant melanomas |
| CN109000634B (zh) * | 2018-06-04 | 2022-06-03 | 上海智蕙林医疗科技有限公司 | 一种导航对象行进路线的提醒方法和系统 |
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| GB1089071A (en) * | 1964-02-28 | 1967-11-01 | Merck & Co Inc | Indole derivatives |
| US3686213A (en) * | 1970-08-28 | 1972-08-22 | American Cyanamid Co | Substituted aminoethyl indoles |
| SU457698A1 (ru) * | 1972-10-20 | 1975-01-25 | Всесоюзный научно-исследовательский химико-фармацевтический институт им. Серго Орджоникидзе | Способ получени производных индолил-2-уксусной кислоты |
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| ATE540923T1 (de) * | 1994-04-01 | 2012-01-15 | Lilly Co Eli | Ää3-(2-amino-1,2-dioxoethyl)-2-ethyl-1- (phenylmethyl)-11h-indol-4-ylüoxyüessigsäure methyl ester als spla2 inhibitor |
| DE19636150A1 (de) * | 1996-09-06 | 1998-03-12 | Asta Medica Ag | N-substituierte Indol-3-glyoxylamide mit antiasthmatischer, antiallergischer und immunsuppressiver/immunmodulierender Wirkung |
| DE19946301A1 (de) * | 1998-04-02 | 2001-04-19 | Asta Medica Ag | Indolyl-3-glyoxylsäure-Derivate mit therapeutisch wertvollen Eigenschaften |
| US7205299B2 (en) * | 2003-06-05 | 2007-04-17 | Zentaris Gmbh | Indole derivatives having an apoptosis-inducing effect |
-
1996
- 1996-09-06 DE DE19636150A patent/DE19636150A1/de not_active Ceased
-
1997
- 1997-08-16 AT AT97937586T patent/ATE342889T1/de active
- 1997-08-16 KR KR10-1999-7001909A patent/KR100516321B1/ko not_active Expired - Fee Related
- 1997-08-16 JP JP51216798A patent/JP3296437B2/ja not_active Expired - Fee Related
- 1997-08-16 ES ES97937586T patent/ES2276433T7/es active Active
- 1997-08-16 PT PT97937586T patent/PT931063E/pt unknown
- 1997-08-16 EP EP97937586A patent/EP0931063B3/de not_active Expired - Lifetime
- 1997-08-16 TR TR1999/00469T patent/TR199900469T2/xx unknown
- 1997-08-16 RU RU99106782A patent/RU2237661C2/ru not_active IP Right Cessation
- 1997-08-16 UA UA99041907A patent/UA60312C2/uk unknown
- 1997-08-16 CN CNB971971285A patent/CN100376554C/zh not_active Expired - Fee Related
- 1997-08-16 CN CN2008100087226A patent/CN101219985B/zh not_active Expired - Fee Related
- 1997-08-16 CN CNB021320616A patent/CN100488948C/zh not_active Expired - Fee Related
- 1997-08-16 HU HU9903741A patent/HU227797B1/hu not_active IP Right Cessation
- 1997-08-16 WO PCT/EP1997/004474 patent/WO1998009946A1/de active IP Right Grant
- 1997-08-16 CZ CZ0061699A patent/CZ302301B6/cs not_active IP Right Cessation
- 1997-08-16 DE DE59712752T patent/DE59712752D1/de not_active Expired - Lifetime
- 1997-08-16 SK SK271-99A patent/SK285618B6/sk not_active IP Right Cessation
- 1997-08-16 NZ NZ334476A patent/NZ334476A/xx not_active IP Right Cessation
- 1997-08-16 IL IL12779897A patent/IL127798A/xx not_active IP Right Cessation
- 1997-08-16 DK DK97937586T patent/DK0931063T5/da active
- 1997-08-16 BR BRPI9712808-2A patent/BR9712808B1/pt not_active IP Right Cessation
- 1997-08-16 AU AU40158/97A patent/AU726521B2/en not_active Ceased
- 1997-08-20 ZA ZA9707475A patent/ZA977475B/xx unknown
- 1997-09-04 CA CA002215013A patent/CA2215013C/en not_active Expired - Fee Related
- 1997-09-05 AR ARP970104064A patent/AR008630A1/es active IP Right Grant
- 1997-09-08 US US08/925,326 patent/US6008231A/en not_active Expired - Lifetime
- 1997-09-30 TW TW086112985A patent/TW550256B/zh not_active IP Right Cessation
-
1999
- 1999-03-04 NO NO19991071A patent/NO314725B3/no not_active IP Right Cessation
- 1999-09-30 US US09/409,263 patent/US6344467B1/en not_active Expired - Lifetime
-
2002
- 2002-01-30 US US10/058,836 patent/US20020161025A1/en not_active Abandoned
-
2003
- 2003-01-30 NO NO20030481A patent/NO20030481D0/no not_active Application Discontinuation
- 2003-04-01 US US10/402,931 patent/US6919344B2/en not_active Expired - Fee Related
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20140816 |