NO325605B1 - 1-aryl-2-acylaminoetanforbindelser, fremgangsmate for fremstilling derav og farmasoytiske sammensetninger omfattende forbindelsene. - Google Patents
1-aryl-2-acylaminoetanforbindelser, fremgangsmate for fremstilling derav og farmasoytiske sammensetninger omfattende forbindelsene. Download PDFInfo
- Publication number
- NO325605B1 NO325605B1 NO19973857A NO973857A NO325605B1 NO 325605 B1 NO325605 B1 NO 325605B1 NO 19973857 A NO19973857 A NO 19973857A NO 973857 A NO973857 A NO 973857A NO 325605 B1 NO325605 B1 NO 325605B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- amino
- acid
- amide
- benzoyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 219
- 238000000034 method Methods 0.000 title claims description 44
- 230000008569 process Effects 0.000 title claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 9
- 239000000203 mixture Substances 0.000 claims description 85
- -1 1,3,4,5-tetrahydrobenzazepin-2-on-3-yl Chemical group 0.000 claims description 59
- 150000003839 salts Chemical class 0.000 claims description 51
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 24
- 150000001412 amines Chemical class 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
- 238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 3
- 230000006181 N-acylation Effects 0.000 claims description 3
- 238000007239 Wittig reaction Methods 0.000 claims description 3
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- GRRIMVWABNHKBX-UHFFFAOYSA-N (3-methoxyphenyl)methanamine Chemical compound COC1=CC=CC(CN)=C1 GRRIMVWABNHKBX-UHFFFAOYSA-N 0.000 claims description 2
- CIYGMJGTASKTFX-UHFFFAOYSA-N 4-[[3,5-bis(trifluoromethyl)benzoyl]-methylamino]-5-(4-chlorophenyl)pent-2-enoic acid Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(=O)N(C)C(C=CC(O)=O)CC1=CC=C(Cl)C=C1 CIYGMJGTASKTFX-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
- GDDPOYBFSLCTID-UHFFFAOYSA-N n-[1-(4-chlorophenyl)-5-oxo-5-(2-pyridin-2-ylethylamino)pent-3-en-2-yl]-n-methyl-3,5-bis(trifluoromethyl)benzamide Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(=O)N(C)C(C=CC(=O)NCCC=1N=CC=CC=1)CC1=CC=C(Cl)C=C1 GDDPOYBFSLCTID-UHFFFAOYSA-N 0.000 claims description 2
- CCEUGCAPAWIBBW-UHFFFAOYSA-N n-[4-[cyclohexyl(propan-2-yl)amino]-1-(1h-indol-3-yl)-4-oxobutan-2-yl]-n-methyl-3,5-bis(trifluoromethyl)benzamide Chemical compound C=1NC2=CC=CC=C2C=1CC(N(C)C(=O)C=1C=C(C=C(C=1)C(F)(F)F)C(F)(F)F)CC(=O)N(C(C)C)C1CCCCC1 CCEUGCAPAWIBBW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- DETMYIWTAMGCKF-UHFFFAOYSA-N n-[1-(4-chlorophenyl)-5-(cyclohexylamino)-4-methyl-5-oxopent-3-en-2-yl]-n-methyl-3,5-bis(trifluoromethyl)benzamide Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(=O)N(C)C(C=C(C)C(=O)NC1CCCCC1)CC1=CC=C(Cl)C=C1 DETMYIWTAMGCKF-UHFFFAOYSA-N 0.000 claims 1
- FBHWMUMISOSVDJ-UHFFFAOYSA-N n-[5-(cyclohexylamino)-1-naphthalen-2-yl-5-oxopent-3-en-2-yl]-n-methyl-3,5-bis(trifluoromethyl)benzamide Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(=O)N(C)C(CC=1C=C2C=CC=CC2=CC=1)C=CC(=O)NC1CCCCC1 FBHWMUMISOSVDJ-UHFFFAOYSA-N 0.000 claims 1
- RUSINKGINZUDCH-UHFFFAOYSA-N n-methyl-n-[1-(1-methylindol-3-yl)-5-(naphthalen-1-ylmethylamino)-5-oxopentan-2-yl]-3,5-bis(trifluoromethyl)benzamide Chemical compound C=1C=CC2=CC=CC=C2C=1CNC(=O)CCC(CC=1C2=CC=CC=C2N(C)C=1)N(C)C(=O)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 RUSINKGINZUDCH-UHFFFAOYSA-N 0.000 claims 1
- 239000005557 antagonist Substances 0.000 abstract description 4
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 261
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 186
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- 230000008020 evaporation Effects 0.000 description 115
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 90
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 90
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 78
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 67
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 67
- 238000004809 thin layer chromatography Methods 0.000 description 67
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 65
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 55
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- 239000012267 brine Substances 0.000 description 19
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 19
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- 229910052786 argon Inorganic materials 0.000 description 18
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 16
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 15
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- PXJACNDVRNAFHD-UHFFFAOYSA-N (2-methoxyphenyl)methanamine Chemical compound COC1=CC=CC=C1CN PXJACNDVRNAFHD-UHFFFAOYSA-N 0.000 description 14
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 14
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Immunology (AREA)
- Psychiatry (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP95810117 | 1995-02-22 | ||
PCT/EP1996/000555 WO1996026183A1 (en) | 1995-02-22 | 1996-02-09 | 1-aryl-2-acylamino-ethane compounds and their use as neurokinin especially neurokinin 1 antagonists |
Publications (3)
Publication Number | Publication Date |
---|---|
NO973857D0 NO973857D0 (no) | 1997-08-21 |
NO973857L NO973857L (no) | 1997-10-01 |
NO325605B1 true NO325605B1 (no) | 2008-06-23 |
Family
ID=8221705
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19973857A NO325605B1 (no) | 1995-02-22 | 1997-08-21 | 1-aryl-2-acylaminoetanforbindelser, fremgangsmate for fremstilling derav og farmasoytiske sammensetninger omfattende forbindelsene. |
Country Status (27)
Country | Link |
---|---|
US (1) | US5929067A (xx) |
EP (1) | EP0810991B1 (xx) |
JP (1) | JP3506714B2 (xx) |
KR (1) | KR100389253B1 (xx) |
CN (1) | CN1081625C (xx) |
AT (1) | ATE178886T1 (xx) |
AU (1) | AU701560B2 (xx) |
BR (1) | BR9607335A (xx) |
CA (1) | CA2213080C (xx) |
CY (1) | CY2198B1 (xx) |
CZ (1) | CZ288345B6 (xx) |
DE (1) | DE69602087T2 (xx) |
DK (1) | DK0810991T3 (xx) |
EA (1) | EA002348B1 (xx) |
ES (1) | ES2132882T3 (xx) |
FI (1) | FI120304B (xx) |
GR (1) | GR3030626T3 (xx) |
HU (1) | HU226562B1 (xx) |
IL (1) | IL117209A (xx) |
MX (1) | MX9706394A (xx) |
NO (1) | NO325605B1 (xx) |
NZ (1) | NZ300942A (xx) |
PL (1) | PL184226B1 (xx) |
SK (1) | SK282237B6 (xx) |
TR (1) | TR199700834T1 (xx) |
WO (1) | WO1996026183A1 (xx) |
ZA (1) | ZA961364B (xx) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
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WO1997044035A1 (en) * | 1996-05-24 | 1997-11-27 | Eli Lilly And Company | Methods of treating hypertension |
MY132550A (en) | 1996-08-22 | 2007-10-31 | Novartis Ag | Acylaminoalkenylene-amide derivatives as nk1 and nk2 antogonists |
GB0010958D0 (en) * | 2000-05-05 | 2000-06-28 | Novartis Ag | Organic compounds |
GB0203061D0 (en) * | 2002-02-08 | 2002-03-27 | Novartis Ag | Organic compounds |
GB0224788D0 (en) * | 2002-10-24 | 2002-12-04 | Novartis Ag | Organic compounds |
GB2394417A (en) * | 2002-10-24 | 2004-04-28 | Novartis Ag | Solid dispersion comprising a piperidine substance P antagonist and a carrier |
CA2547651C (en) * | 2003-12-01 | 2015-06-23 | Cambridge University Technical Services Limited | Anti-inflammatory agents |
US20090156465A1 (en) | 2005-12-30 | 2009-06-18 | Sattigeri Jitendra A | Derivatives of beta-amino acid as dipeptidyl peptidase-iv inhibitors |
JO2630B1 (en) * | 2006-04-13 | 2012-06-17 | نوفارتيس ايه جي | Organic compounds |
GB0607532D0 (en) * | 2006-04-13 | 2006-05-24 | Novartis Ag | Organic compounds |
JP4983616B2 (ja) | 2008-01-16 | 2012-07-25 | ソニー株式会社 | 熱転写記録媒体 |
WO2013004766A1 (en) | 2011-07-04 | 2013-01-10 | Ferrari Giulio | Nk-1 receptor antagonists for treating corneal neovascularisation |
AU2015219955A1 (en) * | 2014-02-18 | 2016-08-11 | Daiichi Sankyo Company,Limited | Aminopyrazolone derivative |
CA3091944A1 (en) | 2018-02-26 | 2019-08-29 | Ospedale San Raffaele S.R.L. | Nk-1 antagonists for use in the treatment of ocular pain |
RU2697414C1 (ru) * | 2018-05-11 | 2019-08-14 | Общество с ограниченной ответственностью "АЙ БИ ДИ Терапевтикс" | Новый антагонист тахикининовых рецепторов и его применение |
US11575807B2 (en) | 2020-01-20 | 2023-02-07 | Monomer Software LLC | Optical device field of view cleaning apparatus |
US20230134843A1 (en) | 2020-03-11 | 2023-05-04 | Ospedale San Raffaele S.R.L. | Treatment of stem cell deficiency |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE69129110T2 (de) * | 1990-05-10 | 1998-12-10 | Bechgaard International Research And Development A/S, Hellerup | Pharmazeutische zubereitung enthaltend n-glykofurole und n-äthylenglykole |
WO1993001169A2 (en) * | 1991-07-05 | 1993-01-21 | Merck Sharp & Dohme Limited | Aromatic compounds, pharmaceutical compositions containing them and their use in therapy |
MY110227A (en) * | 1991-08-12 | 1998-03-31 | Ciba Geigy Ag | 1-acylpiperindine compounds. |
US5217996A (en) * | 1992-01-22 | 1993-06-08 | Ciba-Geigy Corporation | Biaryl substituted 4-amino-butyric acid amides |
-
1996
- 1996-02-09 EA EA199900385A patent/EA002348B1/ru not_active IP Right Cessation
- 1996-02-09 CA CA002213080A patent/CA2213080C/en not_active Expired - Fee Related
- 1996-02-09 AU AU46233/96A patent/AU701560B2/en not_active Ceased
- 1996-02-09 SK SK1139-97A patent/SK282237B6/sk not_active IP Right Cessation
- 1996-02-09 EP EP96901800A patent/EP0810991B1/en not_active Expired - Lifetime
- 1996-02-09 BR BR9607335A patent/BR9607335A/pt not_active IP Right Cessation
- 1996-02-09 NZ NZ300942A patent/NZ300942A/xx not_active IP Right Cessation
- 1996-02-09 CZ CZ19972662A patent/CZ288345B6/cs not_active IP Right Cessation
- 1996-02-09 MX MX9706394A patent/MX9706394A/es unknown
- 1996-02-09 AT AT96901800T patent/ATE178886T1/de active
- 1996-02-09 US US08/913,352 patent/US5929067A/en not_active Expired - Lifetime
- 1996-02-09 KR KR1019970705790A patent/KR100389253B1/ko not_active IP Right Cessation
- 1996-02-09 DE DE69602087T patent/DE69602087T2/de not_active Expired - Lifetime
- 1996-02-09 DK DK96901800T patent/DK0810991T3/da active
- 1996-02-09 TR TR97/00834T patent/TR199700834T1/xx unknown
- 1996-02-09 PL PL96322001A patent/PL184226B1/pl unknown
- 1996-02-09 CN CN96192094A patent/CN1081625C/zh not_active Expired - Fee Related
- 1996-02-09 HU HU9800051A patent/HU226562B1/hu not_active IP Right Cessation
- 1996-02-09 WO PCT/EP1996/000555 patent/WO1996026183A1/en active IP Right Grant
- 1996-02-09 ES ES96901800T patent/ES2132882T3/es not_active Expired - Lifetime
- 1996-02-09 JP JP52534896A patent/JP3506714B2/ja not_active Expired - Fee Related
- 1996-02-21 IL IL11720996A patent/IL117209A/xx not_active IP Right Cessation
- 1996-02-21 ZA ZA961364A patent/ZA961364B/xx unknown
-
1997
- 1997-08-04 FI FI973221A patent/FI120304B/fi not_active IP Right Cessation
- 1997-08-21 NO NO19973857A patent/NO325605B1/no not_active IP Right Cessation
-
1999
- 1999-06-30 GR GR990401712T patent/GR3030626T3/el unknown
-
2000
- 2000-10-10 CY CY0000049A patent/CY2198B1/xx unknown
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