NO314725B3 - N-substituerte indol-3-glyoksylamider, deres fremstilling, anvendelse for fremstilling av medikamenter, legemidler inneholdende disse samt en fremgangsmate for fremstilling av et legemiddel - Google Patents
N-substituerte indol-3-glyoksylamider, deres fremstilling, anvendelse for fremstilling av medikamenter, legemidler inneholdende disse samt en fremgangsmate for fremstilling av et legemiddel Download PDFInfo
- Publication number
- NO314725B3 NO314725B3 NO19991071A NO991071A NO314725B3 NO 314725 B3 NO314725 B3 NO 314725B3 NO 19991071 A NO19991071 A NO 19991071A NO 991071 A NO991071 A NO 991071A NO 314725 B3 NO314725 B3 NO 314725B3
- Authority
- NO
- Norway
- Prior art keywords
- substituted
- alkyl
- group
- glyoxylamide
- indol
- Prior art date
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- -1 N-substituted indole-3-glyoxylamides Chemical class 0.000 title claims abstract description 54
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 title claims abstract description 12
- 239000003814 drug Substances 0.000 title claims description 15
- 229940079593 drug Drugs 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- 230000008569 process Effects 0.000 claims abstract description 7
- 230000001088 anti-asthma Effects 0.000 claims abstract description 5
- 239000000924 antiasthmatic agent Substances 0.000 claims abstract description 5
- 230000002519 immonomodulatory effect Effects 0.000 claims abstract description 5
- 230000003266 anti-allergic effect Effects 0.000 claims abstract description 4
- 230000001506 immunosuppresive effect Effects 0.000 claims abstract description 4
- 150000003254 radicals Chemical class 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- 229910052736 halogen Inorganic materials 0.000 claims description 52
- 150000002367 halogens Chemical class 0.000 claims description 46
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000000243 solution Substances 0.000 claims description 22
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 239000000010 aprotic solvent Substances 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 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 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 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 8
- 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 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000002883 imidazolyl group Chemical group 0.000 claims description 8
- 239000011630 iodine Substances 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 8
- 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 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 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 8
- 125000004193 piperazinyl group Chemical group 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000005493 quinolyl group Chemical group 0.000 claims description 8
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 7
- 229940126601 medicinal product Drugs 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000002475 indoles Chemical class 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 6
- 238000010790 dilution Methods 0.000 claims description 5
- 239000012895 dilution Substances 0.000 claims description 5
- SOLIIYNRSAWTSQ-UHFFFAOYSA-N 2-[1-[(4-chlorophenyl)methyl]indol-3-yl]-2-oxo-n-pyridin-4-ylacetamide Chemical group 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 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 208000025747 Rheumatic disease Diseases 0.000 claims description 3
- 239000000969 carrier Substances 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
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000008024 pharmaceutical diluent Substances 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- 238000002054 transplantation Methods 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 2
- 230000001684 chronic effect Effects 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- OMGXNZSBCBCSCC-UHFFFAOYSA-N ethyl n-[1-[(4-fluorophenyl)methyl]-2-methyl-3-[2-oxo-2-(pyridin-4-ylamino)acetyl]indol-5-yl]carbamate Chemical compound CC1=C(C(=O)C(=O)NC=2C=CN=CC=2)C2=CC(NC(=O)OCC)=CC=C2N1CC1=CC=C(F)C=C1 OMGXNZSBCBCSCC-UHFFFAOYSA-N 0.000 claims description 2
- 239000002674 ointment Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000000829 suppository Substances 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- PXZNKAFWRZAUAS-UHFFFAOYSA-N 2-[1-[(4-fluorophenyl)methyl]indol-3-yl]-2-oxo-n-pyridin-4-ylacetamide Chemical compound C1=CC(F)=CC=C1CN1C2=CC=CC=C2C(C(=O)C(=O)NC=2C=CN=CC=2)=C1 PXZNKAFWRZAUAS-UHFFFAOYSA-N 0.000 claims 1
- OKNVBEWJVIKFGW-UHFFFAOYSA-N N1=CC=C(C=C1)NC(C(=O)C1=CN(C2=CC=C(C=C12)O)CC1=CC=C(C=C1)F)=O.N1=CC=C(C=C1)NC(C(=O)C1=CN(C2=CC=C(C=C12)OC)CC1=CC=C(C=C1)F)=O Chemical compound N1=CC=C(C=C1)NC(C(=O)C1=CN(C2=CC=C(C=C12)O)CC1=CC=C(C=C1)F)=O.N1=CC=C(C=C1)NC(C(=O)C1=CN(C2=CC=C(C=C12)OC)CC1=CC=C(C=C1)F)=O OKNVBEWJVIKFGW-UHFFFAOYSA-N 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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- 230000015572 biosynthetic process Effects 0.000 description 6
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
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- AWMLDBKLOPNOAR-UHFFFAOYSA-N 2-(1h-indol-3-yl)-2-oxoacetamide Chemical compound C1=CC=C2C(C(=O)C(=O)N)=CNC2=C1 AWMLDBKLOPNOAR-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
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- 239000013078 crystal Substances 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
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- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 4
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Classifications
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- 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
- 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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- 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
- A61K31/40—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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- C—CHEMISTRY; METALLURGY
- 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
-
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- 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)
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- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
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- Immunology (AREA)
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- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (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 (4)
| Publication Number | Publication Date |
|---|---|
| NO991071L NO991071L (no) | 1999-03-04 |
| NO991071D0 NO991071D0 (no) | 1999-03-04 |
| NO314725B1 NO314725B1 (no) | 2003-05-12 |
| NO314725B3 true NO314725B3 (no) | 2009-03-09 |
Family
ID=7804772
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19991071A NO314725B3 (no) | 1996-09-06 | 1999-03-04 | N-substituerte indol-3-glyoksylamider, deres fremstilling, anvendelse for fremstilling av medikamenter, legemidler inneholdende disse samt en fremgangsmate for fremstilling av et legemiddel |
| NO20030481A NO20030481D0 (no) | 1996-09-06 | 2003-01-30 | N-substituerte indol-3-glyoksylamider med antiastmatisk, antiallergisk og immunundertrykkende/immunmodulerende virkning |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20030481A NO20030481D0 (no) | 1996-09-06 | 2003-01-30 | N-substituerte indol-3-glyoksylamider med antiastmatisk, antiallergisk og immunundertrykkende/immunmodulerende virkning |
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 |
| WO2001013953A2 (en) | 1999-08-21 | 2001-03-01 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Synergistic combination of pde inhibitors and beta 2 adrenoceptor agonist |
| KR100584650B1 (ko) * | 1998-03-31 | 2006-05-30 | 디 인스티튜트스 포 파마슈티컬 디스커버리, 엘엘씨 | 치환된 인돌알칸산 |
| CZ302588B6 (cs) * | 1998-04-02 | 2011-07-27 | Ziopharm Oncology, Inc. | Použití N-substituovaného indol-3-glyoxylamidu pro výrobu léciva |
| 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 |
| UA59443C2 (uk) * | 1998-04-28 | 2003-09-15 | Арцнайміттельверк Дрезден Гмбх | Гідроксііндол, спосіб його одержання, лікарська форма на його основі та спосіб її одержання |
| DE19818964A1 (de) * | 1998-04-28 | 1999-11-04 | Dresden Arzneimittel | Neue Hydroxyindole, deren Verwendung als Inhibitoren der Phospodiesterase 4 und Verfahren zu deren Herstellung |
| DE19917504A1 (de) * | 1999-04-17 | 2000-10-19 | Dresden Arzneimittel | Verwendung von Hydroxyindolen, die Inhibitoren der Phosphodiesterase 4 sind, zur Therapie chronisch obstruktiver Lungenerkrankungen |
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| DE10253426B4 (de) * | 2002-11-15 | 2005-09-22 | Elbion Ag | Neue Hydroxyindole, deren Verwendung als Inhibitoren der Phosphodiesterase 4 und Verfahren zu deren Herstellung |
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| DE10318610A1 (de) * | 2003-04-24 | 2004-11-11 | Elbion Ag | 7-Azaindole 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 |
| DE10318611A1 (de) * | 2003-04-24 | 2004-11-11 | Elbion Ag | 4-, 6- oder 7-Hydroxyindole mit N-Oxidgruppen und deren Verwendung als Therapeutika |
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| 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 |
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| EA032476B1 (ru) | 2006-07-05 | 2019-06-28 | Астразенека Аб | ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ, СПОСОБ ЕЁ ПОЛУЧЕНИЯ И ЛЕКАРСТВЕННОЕ СРЕДСТВО, СОДЕРЖАЩЕЕ ИНГИБИТОРЫ HMG-CoA-РЕДУКТАЗЫ И ФОСФОДИЭСТЕРАЗЫ 4, ИХ ПРИМЕНЕНИЕ ДЛЯ ЛЕЧЕНИЯ ВОСПАЛИТЕЛЬНЫХ ЗАБОЛЕВАНИЙ ЛЕГКИХ |
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| RU2624506C2 (ru) | 2009-04-29 | 2017-07-04 | АМАРИН КОРПОРЕЙШН ПиЭлСи | Фармацевтические композиции, содержащие ера и сердечно-сосудистое средство, и способы их применения |
| AR084433A1 (es) | 2010-12-22 | 2013-05-15 | Ironwood Pharmaceuticals Inc | Inhibidores de la faah y composiciones farmaceuticas que los contienen |
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| 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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-
1996
- 1996-09-06 DE DE19636150A patent/DE19636150A1/de not_active Ceased
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1997
- 1997-08-16 CN CNB971971285A patent/CN100376554C/zh not_active Expired - Fee Related
- 1997-08-16 JP JP51216798A patent/JP3296437B2/ja not_active Expired - Fee Related
- 1997-08-16 DE DE59712752T patent/DE59712752D1/de not_active Expired - Lifetime
- 1997-08-16 UA UA99041907A patent/UA60312C2/uk unknown
- 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 PT PT97937586T patent/PT931063E/pt unknown
- 1997-08-16 CZ CZ0061699A patent/CZ302301B6/cs not_active IP Right Cessation
- 1997-08-16 AT AT97937586T patent/ATE342889T1/de active
- 1997-08-16 BR BRPI9712808-2A patent/BR9712808B1/pt not_active IP Right Cessation
- 1997-08-16 WO PCT/EP1997/004474 patent/WO1998009946A1/de active IP Right Grant
- 1997-08-16 CN CNB021320616A patent/CN100488948C/zh not_active Expired - Fee Related
- 1997-08-16 EP EP97937586A patent/EP0931063B3/de not_active Expired - Lifetime
- 1997-08-16 CN CN2008100087226A patent/CN101219985B/zh not_active Expired - Fee Related
- 1997-08-16 KR KR10-1999-7001909A patent/KR100516321B1/ko not_active Expired - Fee Related
- 1997-08-16 ES ES97937586T patent/ES2276433T7/es active Active
- 1997-08-16 TR TR1999/00469T patent/TR199900469T2/xx unknown
- 1997-08-16 DK DK97937586T patent/DK0931063T5/da active
- 1997-08-16 HU HU9903741A patent/HU227797B1/hu not_active IP Right Cessation
- 1997-08-16 AU AU40158/97A patent/AU726521B2/en not_active Ceased
- 1997-08-16 RU RU99106782A patent/RU2237661C2/ru not_active IP Right Cessation
- 1997-08-16 SK SK271-99A patent/SK285618B6/sk not_active IP Right Cessation
- 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
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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
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2002
- 2002-01-30 US US10/058,836 patent/US20020161025A1/en not_active Abandoned
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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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