FI114636B - Menetelmä uusien terapeuttisesti käyttökelpoisten bentsyyliaminokinuklidiinijohdannaisten valmistamiseksi - Google Patents
Menetelmä uusien terapeuttisesti käyttökelpoisten bentsyyliaminokinuklidiinijohdannaisten valmistamiseksi Download PDFInfo
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- FI114636B FI114636B FI934626A FI934626A FI114636B FI 114636 B FI114636 B FI 114636B FI 934626 A FI934626 A FI 934626A FI 934626 A FI934626 A FI 934626A FI 114636 B FI114636 B FI 114636B
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- Prior art keywords
- carbon atoms
- alkyl
- compounds
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- compound
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- 238000000034 method Methods 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 10
- 230000008569 process Effects 0.000 title claims description 6
- DTJXCCUWIKIZEX-UHFFFAOYSA-N n-benzyl-1-azabicyclo[2.2.2]octan-2-amine Chemical class C1C(CC2)CCN2C1NCC1=CC=CC=C1 DTJXCCUWIKIZEX-UHFFFAOYSA-N 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 81
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 29
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 abstract description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 12
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- 208000015114 central nervous system disease Diseases 0.000 abstract description 4
- -1 β-phenylethylamino Chemical group 0.000 description 22
- 239000000243 solution Substances 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 12
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- 239000002253 acid Substances 0.000 description 12
- 150000008584 quinuclidines Chemical class 0.000 description 11
- QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
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- 101800003906 Substance P Proteins 0.000 description 9
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- JASMWYNKLTULAN-UHFFFAOYSA-N octan-3-amine Chemical compound CCCCCC(N)CC JASMWYNKLTULAN-UHFFFAOYSA-N 0.000 description 5
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- 239000000126 substance Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- UGXSYMCJVMCLDN-UHFFFAOYSA-N 5-methoxy-1-methyl-2,3-dihydro-1h-indene Chemical compound COC1=CC=C2C(C)CCC2=C1 UGXSYMCJVMCLDN-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
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- 238000004587 chromatography analysis Methods 0.000 description 4
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
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- 238000006772 olefination reaction Methods 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
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- 238000012360 testing method Methods 0.000 description 4
- IJIBRSFAXRFPPN-UHFFFAOYSA-N 5-bromo-2-methoxybenzaldehyde Chemical compound COC1=CC=C(Br)C=C1C=O IJIBRSFAXRFPPN-UHFFFAOYSA-N 0.000 description 3
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- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
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- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
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- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
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- 239000007858 starting material Substances 0.000 description 3
- REUAXQZIRFXQML-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-amine Chemical class C1CC2C(N)CN1CC2 REUAXQZIRFXQML-UHFFFAOYSA-N 0.000 description 2
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 2
- MECDCHFRZHLREI-UHFFFAOYSA-N 2-benzhydryl-1-azabicyclo[2.2.2]octan-3-amine Chemical class NC1C(CC2)CCN2C1C(C=1C=CC=CC=1)C1=CC=CC=C1 MECDCHFRZHLREI-UHFFFAOYSA-N 0.000 description 2
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- CQIROPLNTVMMRB-UHFFFAOYSA-N 2-methoxy-5-prop-1-en-2-ylbenzaldehyde Chemical compound COC1=CC=C(C(C)=C)C=C1C=O CQIROPLNTVMMRB-UHFFFAOYSA-N 0.000 description 2
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 108060008037 tachykinin Proteins 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 210000000626 ureter Anatomy 0.000 description 1
- 230000002455 vasospastic effect Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- 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
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biochemistry (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4283135A JP2656699B2 (ja) | 1992-10-21 | 1992-10-21 | 置換ベンジルアミノキヌクリジン |
JP28313592 | 1992-10-21 |
Publications (3)
Publication Number | Publication Date |
---|---|
FI934626A0 FI934626A0 (fi) | 1993-10-20 |
FI934626A FI934626A (fi) | 1994-04-22 |
FI114636B true FI114636B (fi) | 2004-11-30 |
Family
ID=17661684
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI934626A FI114636B (fi) | 1992-10-21 | 1993-10-20 | Menetelmä uusien terapeuttisesti käyttökelpoisten bentsyyliaminokinuklidiinijohdannaisten valmistamiseksi |
Country Status (16)
Country | Link |
---|---|
EP (1) | EP0665844B1 (pt) |
JP (1) | JP2656699B2 (pt) |
AT (1) | ATE196140T1 (pt) |
AU (1) | AU5165393A (pt) |
CA (1) | CA2146259C (pt) |
DE (1) | DE69329386T2 (pt) |
DK (1) | DK0665844T3 (pt) |
ES (1) | ES2149215T3 (pt) |
FI (1) | FI114636B (pt) |
GR (1) | GR3034498T3 (pt) |
HU (1) | HUT65133A (pt) |
IL (1) | IL107292A0 (pt) |
MX (1) | MX9306527A (pt) |
PT (1) | PT665844E (pt) |
WO (1) | WO1994008997A1 (pt) |
ZA (1) | ZA937780B (pt) |
Families Citing this family (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH10508837A (ja) * | 1994-11-10 | 1998-09-02 | ファイザー・インコーポレーテッド | 眼の疾患を治療するためのnk−1レセプターアンタゴニスト |
FR2728166A1 (fr) | 1994-12-19 | 1996-06-21 | Oreal | Composition topique contenant un antagoniste de substance p |
TW458774B (en) | 1995-10-20 | 2001-10-11 | Pfizer | Antiemetic pharmaceutical compositions |
FR2741262B1 (fr) | 1995-11-20 | 1999-03-05 | Oreal | Utilisation d'un antagoniste de tnf-alpha pour le traitement des rougeurs cutanees d'origine neurogene |
US6861526B2 (en) | 2002-10-16 | 2005-03-01 | Pfizer Inc. | Process for the preparation of (S,S)-cis-2-benzhydryl-3-benzylaminoquinuclidine |
CA2573271C (en) | 2004-07-15 | 2015-10-06 | Amr Technology, Inc. | Aryl-and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
EP1888050B1 (en) | 2005-05-17 | 2012-03-21 | Merck Sharp & Dohme Ltd. | cis-4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)cyclohexanepropanoic acid for the treatment of cancer |
JP5258561B2 (ja) | 2005-07-15 | 2013-08-07 | アルバニー モレキュラー リサーチ, インコーポレイテッド | アリール置換およびヘテロアリール置換テトラヒドロベンズアゼピンならびにノルエピネフリン、ドーパミンおよびセロトニンの再取り込みを遮断するためのその使用 |
KR20080048502A (ko) | 2005-09-29 | 2008-06-02 | 머크 앤드 캄파니 인코포레이티드 | 멜라노코르틴-4 수용체 조절제로서의 아실화스피로피페리딘 유도체 |
GB0603041D0 (en) | 2006-02-15 | 2006-03-29 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
WO2008039327A2 (en) | 2006-09-22 | 2008-04-03 | Merck & Co., Inc. | Method of treatment using fatty acid synthesis inhibitors |
US20110218176A1 (en) | 2006-11-01 | 2011-09-08 | Barbara Brooke Jennings-Spring | Compounds, methods, and treatments for abnormal signaling pathways for prenatal and postnatal development |
MX2009007200A (es) | 2007-01-10 | 2009-07-15 | Angeletti P Ist Richerche Bio | Indazoles sustituidos con amida como inhibidores de poli(adp-ribosa)polimerasa (parp). |
JP5319518B2 (ja) | 2007-04-02 | 2013-10-16 | Msd株式会社 | インドールジオン誘導体 |
AU2008269154B2 (en) | 2007-06-27 | 2014-06-12 | Merck Sharp & Dohme Llc | 4-carboxybenzylamino derivatives as histone deacetylase inhibitors |
JP2011515343A (ja) | 2008-03-03 | 2011-05-19 | タイガー ファーマテック | チロシンキナーゼ阻害薬 |
US9156812B2 (en) | 2008-06-04 | 2015-10-13 | Bristol-Myers Squibb Company | Crystalline form of 6-[(4S)-2-methyl-4-(2-naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine |
UA105182C2 (ru) | 2008-07-03 | 2014-04-25 | Ньюрексон, Інк. | Бензоксазины, бензотиазины и родственные соединения, которые имеют ингибирующую nos активность |
WO2010114780A1 (en) | 2009-04-01 | 2010-10-07 | Merck Sharp & Dohme Corp. | Inhibitors of akt activity |
KR20120023072A (ko) | 2009-05-12 | 2012-03-12 | 브리스톨-마이어스 스큅 컴퍼니 | (S)-7-(〔1,2,4〕트리아졸〔1,5-a〕피리딘-6-일)-4-(3,4-디클로로페닐)-1,2,3,4-테트라하이드로이소퀴놀린의 결정형 및 이의 용도 |
WO2010132437A1 (en) | 2009-05-12 | 2010-11-18 | Albany Molecular Research, Inc. | Aryl, heteroaryl, and heterocycle substituted tetrahydroisoquinolines and use thereof |
AU2010247763B2 (en) | 2009-05-12 | 2015-12-24 | Albany Molecular Research, Inc. | 7-([1,2,4,]triazolo[1,5,-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4- tetrahydroisoquinoline and use thereof |
EA023838B1 (ru) | 2009-10-14 | 2016-07-29 | Мерк Шарп Энд Домэ Корп. | ЗАМЕЩЕННЫЕ ПИПЕРИДИНЫ, КОТОРЫЕ ПОВЫШАЮТ АКТИВНОСТЬ p53, И ИХ ПРИМЕНЕНИЕ |
EP2584903B1 (en) | 2010-06-24 | 2018-10-24 | Merck Sharp & Dohme Corp. | Novel heterocyclic compounds as erk inhibitors |
WO2012018754A2 (en) | 2010-08-02 | 2012-02-09 | Merck Sharp & Dohme Corp. | RNA INTERFERENCE MEDIATED INHIBITION OF CATENIN (CADHERIN-ASSOCIATED PROTEIN), BETA 1 (CTNNB1) GENE EXPRESSION USING SHORT INTERFERING NUCLEIC ACID (siNA) |
CA2807307C (en) | 2010-08-17 | 2021-02-09 | Merck Sharp & Dohme Corp. | Rna interference mediated inhibition of hepatitis b virus (hbv) gene expression using short interfering nucleic acid (sina) |
EP2608669B1 (en) | 2010-08-23 | 2016-06-22 | Merck Sharp & Dohme Corp. | NOVEL PYRAZOLO[1,5-a]PYRIMIDINE DERIVATIVES AS mTOR INHIBITORS |
US8946216B2 (en) | 2010-09-01 | 2015-02-03 | Merck Sharp & Dohme Corp. | Indazole derivatives useful as ERK inhibitors |
EP2615916B1 (en) | 2010-09-16 | 2017-01-04 | Merck Sharp & Dohme Corp. | Fused pyrazole derivatives as novel erk inhibitors |
US9260471B2 (en) | 2010-10-29 | 2016-02-16 | Sirna Therapeutics, Inc. | RNA interference mediated inhibition of gene expression using short interfering nucleic acids (siNA) |
EP2654748B1 (en) | 2010-12-21 | 2016-07-27 | Merck Sharp & Dohme Corp. | Indazole derivatives useful as erk inhibitors |
AU2012245971A1 (en) | 2011-04-21 | 2013-10-17 | Piramal Enterprises Limited | A crystalline form of a salt of a morpholino sulfonyl indole derivative and a process for its preparation |
US9023865B2 (en) | 2011-10-27 | 2015-05-05 | Merck Sharp & Dohme Corp. | Compounds that are ERK inhibitors |
EP3453762B1 (en) | 2012-05-02 | 2021-04-21 | Sirna Therapeutics, Inc. | Short interfering nucleic acid (sina) compositions |
JP6280554B2 (ja) | 2012-09-28 | 2018-02-14 | メルク・シャープ・アンド・ドーム・コーポレーションMerck Sharp & Dohme Corp. | Erk阻害剤である新規化合物 |
ME02925B (me) | 2012-11-28 | 2018-04-20 | Merck Sharp & Dohme | Kompozicije i postupci za liječenje kancera |
TW201429969A (zh) | 2012-12-20 | 2014-08-01 | Merck Sharp & Dohme | 作爲hdm2抑制劑之經取代咪唑吡啶 |
EP2951180B1 (en) | 2013-01-30 | 2018-05-02 | Merck Sharp & Dohme Corp. | 2,6,7,8 substituted purines as hdm2 inhibitors |
US20160194368A1 (en) | 2013-09-03 | 2016-07-07 | Moderna Therapeutics, Inc. | Circular polynucleotides |
WO2019094311A1 (en) | 2017-11-08 | 2019-05-16 | Merck Sharp & Dohme Corp. | Prmt5 inhibitors |
US11993602B2 (en) | 2018-08-07 | 2024-05-28 | Merck Sharp & Dohme Llc | PRMT5 inhibitors |
EP3833667B1 (en) | 2018-08-07 | 2024-03-13 | Merck Sharp & Dohme LLC | Prmt5 inhibitors |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1990005525A1 (en) * | 1988-11-23 | 1990-05-31 | Pfizer Inc. | Quinuclidine derivatives as substance p antagonists |
CA2109415C (en) * | 1991-05-22 | 1998-12-29 | Fumitaka Ito | Substituted 3-aminoquinuclidines |
-
1992
- 1992-10-21 JP JP4283135A patent/JP2656699B2/ja not_active Expired - Fee Related
-
1993
- 1993-09-30 DE DE69329386T patent/DE69329386T2/de not_active Expired - Fee Related
- 1993-09-30 CA CA002146259A patent/CA2146259C/en not_active Expired - Fee Related
- 1993-09-30 WO PCT/US1993/009168 patent/WO1994008997A1/en active IP Right Grant
- 1993-09-30 ES ES93922754T patent/ES2149215T3/es not_active Expired - Lifetime
- 1993-09-30 AT AT93922754T patent/ATE196140T1/de not_active IP Right Cessation
- 1993-09-30 AU AU51653/93A patent/AU5165393A/en not_active Abandoned
- 1993-09-30 EP EP93922754A patent/EP0665844B1/en not_active Expired - Lifetime
- 1993-09-30 DK DK93922754T patent/DK0665844T3/da active
- 1993-09-30 PT PT93922754T patent/PT665844E/pt unknown
- 1993-10-14 IL IL107292A patent/IL107292A0/xx not_active IP Right Cessation
- 1993-10-20 ZA ZA937780A patent/ZA937780B/xx unknown
- 1993-10-20 HU HU9302965A patent/HUT65133A/hu unknown
- 1993-10-20 MX MX9306527A patent/MX9306527A/es unknown
- 1993-10-20 FI FI934626A patent/FI114636B/fi active IP Right Grant
-
2000
- 2000-09-28 GR GR20000402187T patent/GR3034498T3/el not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
HU9302965D0 (en) | 1993-12-28 |
IL107292A0 (en) | 1994-01-25 |
WO1994008997A1 (en) | 1994-04-28 |
JPH06135963A (ja) | 1994-05-17 |
CA2146259C (en) | 1998-04-07 |
DE69329386T2 (de) | 2001-01-04 |
EP0665844B1 (en) | 2000-09-06 |
ATE196140T1 (de) | 2000-09-15 |
ZA937780B (en) | 1995-04-20 |
JP2656699B2 (ja) | 1997-09-24 |
PT665844E (pt) | 2001-01-31 |
EP0665844A1 (en) | 1995-08-09 |
CA2146259A1 (en) | 1994-04-28 |
AU5165393A (en) | 1994-05-09 |
DE69329386D1 (de) | 2000-10-12 |
MX9306527A (es) | 1994-07-29 |
FI934626A (fi) | 1994-04-22 |
FI934626A0 (fi) | 1993-10-20 |
ES2149215T3 (es) | 2000-11-01 |
GR3034498T3 (en) | 2000-12-29 |
HUT65133A (en) | 1994-04-28 |
DK0665844T3 (da) | 2000-10-16 |
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