NO318338B1 - Anvendelse av farnesyl proteintransferaseinhibitorer for fremstilling av farmasoytiske sammensetninger for behandling av artropatier - Google Patents
Anvendelse av farnesyl proteintransferaseinhibitorer for fremstilling av farmasoytiske sammensetninger for behandling av artropatier Download PDFInfo
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- NO318338B1 NO318338B1 NO20010053A NO20010053A NO318338B1 NO 318338 B1 NO318338 B1 NO 318338B1 NO 20010053 A NO20010053 A NO 20010053A NO 20010053 A NO20010053 A NO 20010053A NO 318338 B1 NO318338 B1 NO 318338B1
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- Prior art keywords
- alkyl
- 6alkyl
- hydrogen
- methyl
- formula
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- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
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- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4704—2-Quinolinones, e.g. carbostyril
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Enzymes And Modification Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98202258 | 1998-07-06 | ||
| PCT/EP1999/004546 WO2000001386A1 (fr) | 1998-07-06 | 1999-06-30 | Inhibiteurs de farnesyl proteine transferase pour le traitement des arthropathies |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20010053D0 NO20010053D0 (no) | 2001-01-04 |
| NO20010053L NO20010053L (no) | 2001-03-02 |
| NO318338B1 true NO318338B1 (no) | 2005-03-07 |
Family
ID=8233891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20010053A NO318338B1 (no) | 1998-07-06 | 2001-01-04 | Anvendelse av farnesyl proteintransferaseinhibitorer for fremstilling av farmasoytiske sammensetninger for behandling av artropatier |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US6451812B1 (fr) |
| EP (1) | EP1094815B1 (fr) |
| JP (1) | JP4491136B2 (fr) |
| KR (1) | KR100674122B1 (fr) |
| CN (1) | CN1170538C (fr) |
| AP (1) | AP1597A (fr) |
| AT (1) | ATE253914T1 (fr) |
| AU (1) | AU762470B2 (fr) |
| BG (1) | BG64939B1 (fr) |
| BR (1) | BR9911869A (fr) |
| CA (1) | CA2337800C (fr) |
| CZ (1) | CZ302269B6 (fr) |
| DE (1) | DE69912790T2 (fr) |
| DK (1) | DK1094815T3 (fr) |
| EA (1) | EA003510B1 (fr) |
| EE (1) | EE04579B1 (fr) |
| ES (1) | ES2212580T3 (fr) |
| HK (1) | HK1034450A1 (fr) |
| HR (1) | HRP20000904A2 (fr) |
| HU (1) | HU229358B1 (fr) |
| ID (1) | ID27199A (fr) |
| IL (2) | IL140720A0 (fr) |
| MY (1) | MY122189A (fr) |
| NO (1) | NO318338B1 (fr) |
| NZ (1) | NZ509647A (fr) |
| PL (1) | PL193296B1 (fr) |
| PT (1) | PT1094815E (fr) |
| SI (1) | SI1094815T1 (fr) |
| SK (1) | SK285231B6 (fr) |
| TR (1) | TR200003882T2 (fr) |
| TW (1) | TW557212B (fr) |
| UA (1) | UA64797C2 (fr) |
| WO (1) | WO2000001386A1 (fr) |
| ZA (1) | ZA200100152B (fr) |
Families Citing this family (70)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9911869A (pt) | 1998-07-06 | 2001-03-27 | Janssen Pharmaceutica Nv | Inibidores da transferase da proteìna farnesil para o tratamento das artropatias |
| DE60008206T2 (de) | 1999-11-30 | 2004-12-02 | Pfizer Products Inc., Groton | Chinolinderivate verwendbar zur Hemmung der Farnesyl-Protein Transferase |
| JO2361B1 (en) | 2000-06-22 | 2006-12-12 | جانسين فارماسيوتيكا ان. في | Enaniumer 1,2-anylated quinoline inhibitor for the transporter - farnesyl |
| AU2001293829A1 (en) | 2000-09-25 | 2002-04-02 | Janssen Pharmaceutica N.V. | Farnesyl transferase inhibiting 6-((substituted phenyl)methyl)-quinoline and quinazoline derivatives |
| ATE409189T1 (de) | 2000-09-25 | 2008-10-15 | Janssen Pharmaceutica Nv | Farnesyl transferase-hemmende 6- heterocyclylmethyl-chinolin und chinazol-derivate |
| US7067531B2 (en) | 2000-09-25 | 2006-06-27 | Angibaud Patrick Rene | Farnesyl transferase inhibiting 6-heterocyclylmethyl quinolinone derivatives |
| WO2002024682A1 (fr) | 2000-09-25 | 2002-03-28 | Janssen Pharmaceutica N.V. | Derives de quinoline et de quinazoline inhibant la farnesyl transferase comme inhibiteurs de farnesyl transferase |
| AU2002214056A1 (en) | 2000-11-21 | 2002-06-03 | Janssen Pharmaceutica N.V. | Farnesyl transferase inhibiting benzoheterocyclic derivatives |
| US7129356B2 (en) | 2000-12-27 | 2006-10-31 | Janssen Pharmaceutica N.V. | Farnesyl transferase inhibiting 4-substituted quinoline and quinazoline derivatives |
| DE60119383T2 (de) * | 2000-12-27 | 2007-04-19 | Janssen Pharmaceutica N.V. | Farnesyltransferasehemmende 4-heterocyclylchinolin- und chinazolinderivate |
| WO2002098370A2 (fr) * | 2001-03-02 | 2002-12-12 | Medimmune, Inc. | Methodes d'administration/dosage d'antagonistes de cd2 pour la prevention et le traitement des maladies auto-immunes ou inflammatoires |
| US6706699B2 (en) * | 2001-06-21 | 2004-03-16 | Ariad Pharmaceuticals, Inc. | Quinolines and uses thereof |
| US6713462B2 (en) | 2001-06-21 | 2004-03-30 | Ariad Pharmaceuticals, Inc. | Quinolinones and uses thereof |
| ES2323265T3 (es) | 2001-12-19 | 2009-07-10 | Janssen Pharmaceutica Nv | Derivados de quinolina condensados en 1,8 sustituidos con triazoles unidos por el carbono como inhibidores de la farnesil-transferasa. |
| AU2003223970B2 (en) | 2002-03-22 | 2008-03-06 | Janssen Pharmaceutica N.V. | Benzylimidazolyl substituted 2-quinoline and quinazoline derivatives for use as farnesyl transferase inhibitors |
| CA2481480C (fr) | 2002-04-15 | 2011-04-12 | Janssen Pharmaceutica N.V. | Derives de quinazoline tricylique inhibant la farnesyl transferase substitues avec des imidazoles ou des triazoles a liaison carbone |
| US7425618B2 (en) | 2002-06-14 | 2008-09-16 | Medimmune, Inc. | Stabilized anti-respiratory syncytial virus (RSV) antibody formulations |
| US7132100B2 (en) | 2002-06-14 | 2006-11-07 | Medimmune, Inc. | Stabilized liquid anti-RSV antibody formulations |
| US7563810B2 (en) | 2002-11-06 | 2009-07-21 | Celgene Corporation | Methods of using 3-(4-amino-1-oxo-1,3-dihydroisoindol-2-yl)-piperidine-2,6-dione for the treatment and management of myeloproliferative diseases |
| US8034831B2 (en) | 2002-11-06 | 2011-10-11 | Celgene Corporation | Methods for the treatment and management of myeloproliferative diseases using 4-(amino)-2-(2,6-Dioxo(3-piperidyl)-isoindoline-1,3-dione in combination with other therapies |
| KR20120035234A (ko) | 2003-04-11 | 2012-04-13 | 메디뮨 엘엘씨 | 재조합 ｉｌ?９ 항체 및 그의 용도 |
| WO2005042743A2 (fr) | 2003-08-18 | 2005-05-12 | Medimmune, Inc. | Humanisation d'anticorps |
| EP1691812A4 (fr) | 2003-11-20 | 2010-01-13 | Childrens Hosp Medical Center | Inhibiteurs de gtpase et procedes d'utilisation correspondants |
| US20050272068A1 (en) * | 2004-03-18 | 2005-12-08 | The Brigham And Women's Hospital, Inc. | UCH-L1 expression and cancer therapy |
| JP2007538004A (ja) * | 2004-03-18 | 2007-12-27 | ザ ブライハム アンド ウイメンズ ホスピタル， インコーポレイテッド | シヌクレイノパチーを治療する方法 |
| AU2005299355A1 (en) | 2004-10-27 | 2006-05-04 | Medimmune, Llc | Modulation of antibody specificity by tailoring the affinity to cognate antigens |
| PT1815247E (pt) | 2004-11-05 | 2013-04-23 | Janssen Pharmaceutica Nv | Uso terapêutico de inibidores de farnesiltransferase e métodos para monitorizar a eficácia do mesmo |
| US20060194821A1 (en) * | 2005-02-18 | 2006-08-31 | The Brigham And Women's Hospital, Inc. | Compounds inhibiting the aggregation of superoxide dismutase-1 |
| JP5153613B2 (ja) | 2005-03-18 | 2013-02-27 | メディミューン，エルエルシー | 抗体のフレームワーク・シャッフル |
| CA2613512A1 (fr) | 2005-06-23 | 2007-01-04 | Medimmune, Inc. | Formulations d'anticorps possedant des profils d'agregation et de fragmentation optimises |
| US7826982B2 (en) | 2005-07-29 | 2010-11-02 | Children's Hospital Medical Center | Method of identifying inhibitors using a 3-D structure of RAC-1 GTPASE |
| EP1968591A4 (fr) | 2005-12-23 | 2010-02-17 | Link Medicine Corp | Traitement de formes de synucleinopathie |
| MY162024A (en) | 2006-08-28 | 2017-05-31 | La Jolla Inst Allergy & Immunology | Antagonistic human light-specific human monoclonal antibodies |
| EP2068923A4 (fr) | 2007-03-30 | 2010-11-24 | Medimmune Llc | Anticorps presentant des profils de desamidation reduits |
| WO2008147788A1 (fr) * | 2007-05-23 | 2008-12-04 | Allergan, Inc. | Composés thérapeutiques de ((phényl)imidazolyl)méthylquinoléinyle |
| US8232402B2 (en) | 2008-03-12 | 2012-07-31 | Link Medicine Corporation | Quinolinone farnesyl transferase inhibitors for the treatment of synucleinopathies and other indications |
| BRPI0920927A2 (pt) | 2008-11-13 | 2019-09-24 | Link Medicine Corp | derivados de azaquinolinona e usos dos mesmos |
| FR2967353B1 (fr) * | 2010-11-16 | 2013-08-16 | Centre Nat Rech Scient | Derives de quinolinone |
| EP2668210B1 (fr) | 2011-01-26 | 2020-06-17 | Celldex Therapeutics, Inc. | Anticorps anti-kit et leurs utilisations |
| WO2013166043A1 (fr) | 2012-05-02 | 2013-11-07 | Children's Hospital Medical Center | Rajeunissement de cellules précurseurs |
| BR112015001459B1 (pt) | 2012-07-25 | 2023-02-14 | Celldex Therapeutics, Inc | Anticorpo isolado ou fragmento do mesmo, conjugado, usos dos mesmos, composição farmacêutica, polinucleotídeo, vetor, célula hospedeira, célula isolada, kit, método in vitro para inibir atividade da kit, método para produzir um anticorpo |
| WO2014059028A1 (fr) | 2012-10-09 | 2014-04-17 | Igenica, Inc. | Anticorps anti-c16orf54 et leurs méthodes d'utilisation |
| WO2014062667A1 (fr) | 2012-10-16 | 2014-04-24 | Janssen Pharmaceutica Nv | Modulateurs de ror-gamma-t de type quinolinyle à liaison phényle |
| KR20150070348A (ko) | 2012-10-16 | 2015-06-24 | 얀센 파마슈티카 엔.브이. | RoRγt의 헤테로아릴 결합 퀴놀리닐 조절제 |
| PE20150778A1 (es) | 2012-10-16 | 2015-05-23 | Janssen Pharmaceutica Nv | Moduladores de quinolinilo unidos a metileno de ror-gamma-t |
| EP3003390B1 (fr) | 2013-06-06 | 2021-07-07 | Pierre Fabre Médicament | Anticorps anti-c10orf54 et leurs utilisations |
| RU2699289C2 (ru) | 2013-08-26 | 2019-09-04 | Байонтек Рисерч Энд Дивелопмент, Инк. | НУКЛЕИНОВЫЕ КИСЛОТЫ, КОДИРУЮЩИЕ АНТИТЕЛА ПРОТИВ СИАЛИРОВАННОГО АНТИГЕНА ЛЬЮИСАа ЧЕЛОВЕКА |
| WO2015057203A1 (fr) * | 2013-10-15 | 2015-04-23 | Janssen Pharmaceutica Nv | Modulateurs quinolinyles à liaison phényle de rar-gamma-t |
| ES2742843T3 (es) | 2013-10-15 | 2020-02-17 | Janssen Pharmaceutica Nv | Moduladores de quinolinilo de ROR(gamma)t |
| AU2014334619A1 (en) | 2013-10-15 | 2016-04-21 | Janssen Pharmaceutica Nv | Alkyl linked quinolinyl modulators of RORyt |
| US10555941B2 (en) | 2013-10-15 | 2020-02-11 | Janssen Pharmaceutica Nv | Alkyl linked quinolinyl modulators of RORγt |
| US9403816B2 (en) * | 2013-10-15 | 2016-08-02 | Janssen Pharmaceutica Nv | Phenyl linked quinolinyl modulators of RORγt |
| US9328095B2 (en) | 2013-10-15 | 2016-05-03 | Janssen Pharmaceutica Nv | Heteroaryl linked quinolinyl modulators of RORgammat |
| US9284308B2 (en) | 2013-10-15 | 2016-03-15 | Janssen Pharmaceutica Nv | Methylene linked quinolinyl modulators of RORγt |
| US9221804B2 (en) | 2013-10-15 | 2015-12-29 | Janssen Pharmaceutica Nv | Secondary alcohol quinolinyl modulators of RORγt |
| GB201403775D0 (en) | 2014-03-04 | 2014-04-16 | Kymab Ltd | Antibodies, uses & methods |
| AU2015271685B2 (en) | 2014-06-04 | 2021-02-18 | Biontech Research And Development, Inc. | Human monoclonal antibodies to ganglioside GD2 |
| US10028503B2 (en) | 2014-06-18 | 2018-07-24 | Children's Hospital Medical Center | Platelet storage methods and compositions for same |
| US10766959B2 (en) | 2014-12-11 | 2020-09-08 | Pierre Fabre Medicament | Anti-C10ORF54 antibodies and uses thereof |
| CN114504652A (zh) | 2015-03-03 | 2022-05-17 | 科马布有限公司 | 抗体、用途和方法 |
| PT3277842T (pt) | 2015-08-17 | 2019-09-05 | Kura Oncology Inc | Métodos de tratamento de doentes com cancro usando inibidores da farnesiltransferase |
| EP3383908A1 (fr) | 2015-12-02 | 2018-10-10 | Stsciences, Inc. | Anticorps spécifiques au btla glycosylé (atténuateur de lymphocytes b et t) |
| EP3909983A1 (fr) | 2015-12-02 | 2021-11-17 | STCube & Co. Inc. | Anticorps et molécules se liant de manière immunospécifique à btn1a1 et leurs utilisations thérapeutiques |
| EP3838275A1 (fr) | 2016-11-03 | 2021-06-23 | Kura Oncology, Inc. | Inhibiteurs de farnésyltransférase pour utilisation dans le traitement de cancer |
| WO2018083248A1 (fr) | 2016-11-03 | 2018-05-11 | Kymab Limited | Anticorps, combinaisons comprenant des anticorps, biomarqueurs, utilisations et procédés |
| JP2020522512A (ja) | 2017-05-31 | 2020-07-30 | ストキューブ アンド シーオー．， インコーポレイテッド | Ｂｔｎ１ａ１に免疫特異的に結合する抗体及び分子を用いて癌を治療する方法 |
| JP7369038B2 (ja) | 2017-05-31 | 2023-10-25 | ストキューブ アンド シーオー．， インコーポレイテッド | Ｂｔｎ１ａ１に免疫特異的に結合する抗体及び分子並びにその治療的使用 |
| JP2020522562A (ja) | 2017-06-06 | 2020-07-30 | ストキューブ アンド シーオー．， インコーポレイテッド | Ｂｔｎ１ａ１又はｂｔｎ１ａ１リガンドに結合する抗体及び分子を用いて癌を治療する方法 |
| US11707522B2 (en) | 2017-10-13 | 2023-07-25 | Boehringer Ingelheim International Gmbh | Human antibodies to Tn antigen |
| AU2019306165A1 (en) | 2018-07-20 | 2021-02-25 | Pierre Fabre Medicament | Receptor for vista |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5602184A (en) | 1993-03-03 | 1997-02-11 | The United States Of America As Represented By Department Of Health And Human Services | Monoterpenes, sesquiterpenes and diterpenes as cancer therapy |
| US5574025A (en) * | 1994-10-26 | 1996-11-12 | Merck & Co., Inc. | Inhibitors of prenyl-protein transferases |
| US5831004A (en) * | 1994-10-27 | 1998-11-03 | Affymax Technologies N.V. | Inhibitors of metalloproteases, pharmaceutical compositions comprising same and methods of their use |
| FR2729390A1 (fr) * | 1995-01-18 | 1996-07-19 | Rhone Poulenc Rorer Sa | Nouveaux inhibiteurs de farnesyl transferase, leur preparation et les compositions pharmaceutiques qui les contiennent |
| TW349948B (en) | 1995-10-31 | 1999-01-11 | Janssen Pharmaceutica Nv | Farnesyl transferase inhibiting 2-quinolone derivatives |
| SI1162201T1 (sl) * | 1995-12-08 | 2006-08-31 | Janssen Pharmaceutica Nv | (Imidazol-5-il)metil-2-kinolinonski derivati kot inhibitorji farnezil protein transferaze |
| CA2251716A1 (fr) | 1996-04-15 | 1997-10-23 | W. Gillies Mckenna | Sensibilisation de cellules a la radiotherapie et a la chimiotherapie |
| WO1998002436A1 (fr) * | 1996-07-15 | 1998-01-22 | Bristol-Myers Squibb Company | Thiadioxobenzodiazepines utilises comme inhibiteurs de la farnesyle proteine transferase |
| TW591030B (en) * | 1997-03-10 | 2004-06-11 | Janssen Pharmaceutica Nv | Farnesyl transferase inhibiting 1,8-annelated quinolinone derivatives substituted with N- or C-linked imidazoles |
| GB2323783A (en) * | 1997-04-02 | 1998-10-07 | Ferring Bv Group Holdings | Inhibitors of farnesyl protein transferase |
| CA2288140C (fr) | 1997-04-25 | 2007-04-03 | Janssen Pharmaceutica N.V. | Quinazolinones inhibant la farnesyltransferase |
| JP4209472B2 (ja) | 1997-06-02 | 2009-01-14 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 平滑筋細胞増殖のインヒビターとしての（イミダゾール−５−イル）メチル−２−キノリノン誘導体 |
| TR200003580T2 (tr) | 1997-06-17 | 2002-10-21 | Schering Corporation | Farnesil protein transferazı'nın önlenmesine mahsus benzo(5,6)siklohepta(1,2-B)piridin türevleri |
| CA2336624C (fr) | 1998-07-06 | 2008-10-21 | Janssen Pharmaceutica N.V. | Inhibiteurs de farnesyl proteine transferase a proprietes de radiosensibilisation in vivo |
| BR9911869A (pt) | 1998-07-06 | 2001-03-27 | Janssen Pharmaceutica Nv | Inibidores da transferase da proteìna farnesil para o tratamento das artropatias |
| JP3495706B2 (ja) * | 1998-08-27 | 2004-02-09 | ファイザー・プロダクツ・インク | 抗癌薬として有用なアルキニル置換キノリン−２−オン誘導体 |
| JP5574025B1 (ja) * | 2013-06-25 | 2014-08-20 | 大日本印刷株式会社 | 飲料供給系配管の殺菌方法及び装置 |
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