TWI369351B - 2,4-diamino-pyrimidines as aurora inhibitors - Google Patents
2,4-diamino-pyrimidines as aurora inhibitorsInfo
- Publication number
- TWI369351B TWI369351B TW095123919A TW95123919A TWI369351B TW I369351 B TWI369351 B TW I369351B TW 095123919 A TW095123919 A TW 095123919A TW 95123919 A TW95123919 A TW 95123919A TW I369351 B TWI369351 B TW I369351B
- Authority
- TW
- Taiwan
- Prior art keywords
- pyrimidines
- diamino
- aurora inhibitors
- aurora
- inhibitors
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- 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
-
- 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
-
- 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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05106007 | 2005-07-01 |
Publications (2)
Publication Number | Publication Date |
---|---|
TW200726753A TW200726753A (en) | 2007-07-16 |
TWI369351B true TWI369351B (en) | 2012-08-01 |
Family
ID=35431858
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
TW095123919A TWI369351B (en) | 2005-07-01 | 2006-06-30 | 2,4-diamino-pyrimidines as aurora inhibitors |
Country Status (30)
Country | Link |
---|---|
US (3) | US20070032514A1 (zh) |
EP (1) | EP1902037B1 (zh) |
JP (1) | JP5179357B2 (zh) |
KR (1) | KR20080031362A (zh) |
CN (1) | CN101213179A (zh) |
AR (1) | AR057423A1 (zh) |
AT (1) | ATE441639T1 (zh) |
AU (1) | AU2006264958B2 (zh) |
BR (1) | BRPI0613096A2 (zh) |
CA (1) | CA2613664A1 (zh) |
CY (1) | CY1109644T1 (zh) |
DE (1) | DE502006004750D1 (zh) |
DK (1) | DK1902037T3 (zh) |
EA (1) | EA016358B1 (zh) |
EC (1) | ECSP078060A (zh) |
ES (1) | ES2330045T3 (zh) |
IL (1) | IL188452A (zh) |
MX (1) | MX2007015992A (zh) |
MY (1) | MY142496A (zh) |
NO (1) | NO20076059L (zh) |
NZ (1) | NZ565475A (zh) |
PE (1) | PE20070121A1 (zh) |
PL (1) | PL1902037T3 (zh) |
PT (1) | PT1902037E (zh) |
SI (1) | SI1902037T1 (zh) |
TW (1) | TWI369351B (zh) |
UA (1) | UA92355C2 (zh) |
UY (1) | UY29636A1 (zh) |
WO (1) | WO2007003596A1 (zh) |
ZA (1) | ZA200709763B (zh) |
Families Citing this family (36)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4812763B2 (ja) * | 2004-05-18 | 2011-11-09 | ライジェル ファーマシューティカルズ, インコーポレイテッド | シクロアルキル置換ピリミジンジアミン化合物およびそれらの用途 |
GB2420559B (en) * | 2004-11-15 | 2008-08-06 | Rigel Pharmaceuticals Inc | Stereoisomerically enriched 3-aminocarbonyl bicycloheptene pyrimidinediamine compounds and their uses |
PE20080068A1 (es) * | 2006-05-15 | 2008-03-17 | Boehringer Ingelheim Int | Compuestos derivados de pirimidina como inhibidores de la quinasa aurora |
ES2555803T3 (es) | 2006-10-23 | 2016-01-08 | Cephalon, Inc. | Fusión de derivados bicíclicos 2,4-diaminopirimidina como utilizar inhibidores ALK y c-Met |
US20100144706A1 (en) * | 2006-12-22 | 2010-06-10 | Boehringer Ingelheim International Gmbh | Compounds |
US20100056524A1 (en) * | 2008-04-02 | 2010-03-04 | Mciver Edward Giles | Compound |
LT2300013T (lt) | 2008-05-21 | 2017-12-27 | Ariad Pharmaceuticals, Inc. | Fosforo dariniai kaip kinazių inhibitoriai |
US9273077B2 (en) | 2008-05-21 | 2016-03-01 | Ariad Pharmaceuticals, Inc. | Phosphorus derivatives as kinase inhibitors |
WO2010022125A1 (en) * | 2008-08-20 | 2010-02-25 | Schering Corporation | Ethynyl-substituted pyridine and pyrimidine derivatives and their use in treating viral infections |
ES2439009T3 (es) | 2008-08-20 | 2014-01-21 | Merck Sharp & Dohme Corp. | Derivados de piridina y pirimidina sustituidos con etenilo y su uso en el tratamiento de infecciones virales |
CA2734486A1 (en) * | 2008-08-20 | 2010-02-25 | Southern Research Institute | Substituted pyridine and pyrimidine derivatives and their use in treating viral infections |
TW201019939A (en) | 2008-08-20 | 2010-06-01 | Schering Corp | Azo-substituted pyridine and pyrimidine derivatives and their use in treating viral infections |
EP2161259A1 (de) | 2008-09-03 | 2010-03-10 | Bayer CropScience AG | 4-Halogenalkylsubstituierte Diaminopyrimidine als Fungizide |
CN102143750B (zh) * | 2008-09-08 | 2014-04-02 | 默克专利有限公司 | 用作蛋白激酶抑制剂的大环嘧啶 |
AR074210A1 (es) | 2008-11-24 | 2010-12-29 | Boehringer Ingelheim Int | Derivados de pirimidina como inhibidores de ptk2-quinasa |
TW201024281A (en) | 2008-11-24 | 2010-07-01 | Boehringer Ingelheim Int | New compounds |
US20110071158A1 (en) * | 2009-03-18 | 2011-03-24 | Boehringer Ingelheim International Gmbh | New compounds |
US8410126B2 (en) * | 2009-05-29 | 2013-04-02 | Boehringer Ingelheim International Gmbh | Pyrimidine inhibitors of PKTK2 |
CA2764983A1 (en) | 2009-06-10 | 2010-12-16 | Abbott Laboratories | 2- ( lh-pyrazol-4 -ylamino ) -pyrimidine as kinase inhibitors |
JP2012197231A (ja) * | 2009-08-06 | 2012-10-18 | Oncotherapy Science Ltd | Ttk阻害作用を有するピリジンおよびピリミジン誘導体 |
JP5539518B2 (ja) | 2009-08-14 | 2014-07-02 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 2−アミノ−5−トリフルオロメチルピリミジン誘導体の位置選択的調製 |
US8933227B2 (en) | 2009-08-14 | 2015-01-13 | Boehringer Ingelheim International Gmbh | Selective synthesis of functionalized pyrimidines |
US8466155B2 (en) * | 2009-10-02 | 2013-06-18 | Boehringer Ingelheim International Gmbh | Pyrimidines |
US20120107304A1 (en) | 2010-04-27 | 2012-05-03 | Boehringer Ingelheim International Gmbh | Combination therapy in treatment of oncological and fibrotic diseases |
MX2012014158A (es) | 2010-06-04 | 2013-02-07 | Hoffmann La Roche | Derivados de aminopirimidina como moduladores de proteina cinasa rica repeticiones leucina 2 (lrrk2). |
HUE037844T2 (hu) | 2010-11-10 | 2018-09-28 | Genentech Inc | Pirazol-aminopirimidin-származékok mint LRRK2 modulátorok |
BR112013019942B1 (pt) * | 2011-02-25 | 2022-01-11 | Yuhan Corporation | Uso de composto ou de seu sal farmaceuticamente aceitável, composição farmacêutica, compostos ou seus sais farmaceuticamente aceitáveis e respectivos processos de preparação |
WO2012151561A1 (en) | 2011-05-04 | 2012-11-08 | Ariad Pharmaceuticals, Inc. | Compounds for inhibiting cell proliferation in egfr-driven cancers |
JP6469567B2 (ja) | 2012-05-05 | 2019-02-13 | アリアド・ファーマシューティカルズ・インコーポレイテッド | Egfr発動性がんの細胞増殖阻害用化合物 |
WO2014151871A2 (en) | 2013-03-14 | 2014-09-25 | Tolero Pharmaceuticals, Inc. | Jak2 and alk2 inhibitors and methods for their use |
US9611283B1 (en) | 2013-04-10 | 2017-04-04 | Ariad Pharmaceuticals, Inc. | Methods for inhibiting cell proliferation in ALK-driven cancers |
CA2934061A1 (en) * | 2013-12-20 | 2015-06-25 | Signal Pharmaceuticals, Llc | Substituted diaminopyrimidyl compounds, compositions thereof, and methods of treatment therewith |
JP6637880B2 (ja) | 2014-05-08 | 2020-01-29 | 東ソー・ファインケム株式会社 | 5−(トリフルオロメチル)ピリミジン誘導体及びその製造方法 |
ES2940911T3 (es) * | 2016-06-27 | 2023-05-12 | Rigel Pharmaceuticals Inc | Compuestos de 2,4-diamino-pirimidina y su uso como inhibidores de IRAK4 |
SG11202009443RA (en) | 2018-04-05 | 2020-10-29 | Sumitomo Dainippon Pharma Oncology Inc | Axl kinase inhibitors and use of the same |
WO2020023910A1 (en) | 2018-07-26 | 2020-01-30 | Tolero Pharmaceuticals, Inc. | Methods for treating diseases associated with abnormal acvr1 expression and acvr1 inhibitors for use in the same |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
MXPA03010810A (es) * | 2001-05-29 | 2004-03-22 | Schering Ag | Pirimidinas inhibidoras de cdk, su obtencion y su uso como medicamentos. |
US7169836B2 (en) * | 2001-06-27 | 2007-01-30 | Polyplastics Co., Ltd | Flame-retardant resin composition |
WO2003032997A1 (de) * | 2001-10-17 | 2003-04-24 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Pyrimidinderivate, arzneimittel enthaltend diese verbindungen, deren verwendung und verfahren zu ihrer herstellung |
IL166241A (en) * | 2002-07-29 | 2011-12-29 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds for use in the treatment of autoimmune diseases |
UA80767C2 (en) * | 2002-12-20 | 2007-10-25 | Pfizer Prod Inc | Pyrimidine derivatives for the treatment of abnormal cell growth |
JP2007514775A (ja) * | 2003-12-19 | 2007-06-07 | ライジェル ファーマシューティカルズ, インコーポレイテッド | 1−(2,4−ピリミジンジアミノ)−2−シクロペンタンカルボキサイミド合成中間体の立体異性体および立体異性体混合物 |
CN1976905A (zh) * | 2004-03-30 | 2007-06-06 | 大正制药株式会社 | 嘧啶衍生物以及与其应用有关的治疗方法 |
KR100886990B1 (ko) * | 2004-05-14 | 2009-03-04 | 화이자 프로덕츠 인크. | 비정상적인 세포성장의 치료를 위한 피리미딘 유도체 |
JP4812763B2 (ja) * | 2004-05-18 | 2011-11-09 | ライジェル ファーマシューティカルズ, インコーポレイテッド | シクロアルキル置換ピリミジンジアミン化合物およびそれらの用途 |
GB2420559B (en) * | 2004-11-15 | 2008-08-06 | Rigel Pharmaceuticals Inc | Stereoisomerically enriched 3-aminocarbonyl bicycloheptene pyrimidinediamine compounds and their uses |
EP1831181A2 (en) * | 2004-12-14 | 2007-09-12 | Vertex Pharmaceuticals Incorporated | Pyrimidine inhibitors of erk protein kinase and uses thereof |
CA2634646C (en) * | 2005-12-21 | 2012-04-10 | Pfizer Products Inc. | Pyrimidine derivatives for the treatment of abnormal cell growth |
-
2006
- 2006-06-27 US US11/475,468 patent/US20070032514A1/en not_active Abandoned
- 2006-06-28 PE PE2006000752A patent/PE20070121A1/es not_active Application Discontinuation
- 2006-06-28 MY MYPI20063091A patent/MY142496A/en unknown
- 2006-06-29 UY UY29636A patent/UY29636A1/es not_active Application Discontinuation
- 2006-06-30 KR KR1020087002717A patent/KR20080031362A/ko not_active Application Discontinuation
- 2006-06-30 AR ARP060102827A patent/AR057423A1/es unknown
- 2006-06-30 PT PT06763989T patent/PT1902037E/pt unknown
- 2006-06-30 ES ES06763989T patent/ES2330045T3/es active Active
- 2006-06-30 DE DE502006004750T patent/DE502006004750D1/de active Active
- 2006-06-30 TW TW095123919A patent/TWI369351B/zh not_active IP Right Cessation
- 2006-06-30 UA UAA200800924A patent/UA92355C2/ru unknown
- 2006-06-30 NZ NZ565475A patent/NZ565475A/en not_active IP Right Cessation
- 2006-06-30 EP EP06763989A patent/EP1902037B1/de not_active Not-in-force
- 2006-06-30 SI SI200630479T patent/SI1902037T1/sl unknown
- 2006-06-30 PL PL06763989T patent/PL1902037T3/pl unknown
- 2006-06-30 EA EA200800172A patent/EA016358B1/ru not_active IP Right Cessation
- 2006-06-30 JP JP2008518857A patent/JP5179357B2/ja not_active Expired - Fee Related
- 2006-06-30 AU AU2006264958A patent/AU2006264958B2/en not_active Ceased
- 2006-06-30 BR BRPI0613096-8A patent/BRPI0613096A2/pt not_active IP Right Cessation
- 2006-06-30 AT AT06763989T patent/ATE441639T1/de active
- 2006-06-30 MX MX2007015992A patent/MX2007015992A/es active IP Right Grant
- 2006-06-30 CN CNA2006800240865A patent/CN101213179A/zh active Pending
- 2006-06-30 DK DK06763989T patent/DK1902037T3/da active
- 2006-06-30 WO PCT/EP2006/063736 patent/WO2007003596A1/de active Application Filing
- 2006-06-30 CA CA002613664A patent/CA2613664A1/en not_active Abandoned
-
2007
- 2007-11-13 ZA ZA200709763A patent/ZA200709763B/xx unknown
- 2007-11-26 NO NO20076059A patent/NO20076059L/no not_active Application Discontinuation
- 2007-12-27 EC EC2007008060A patent/ECSP078060A/es unknown
- 2007-12-27 IL IL188452A patent/IL188452A/en not_active IP Right Cessation
-
2009
- 2009-11-25 CY CY20091101222T patent/CY1109644T1/el unknown
-
2011
- 2011-06-14 US US13/159,787 patent/US20110251174A1/en not_active Abandoned
-
2013
- 2013-03-26 US US13/850,711 patent/US20130281429A1/en not_active Abandoned
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MM4A | Annulment or lapse of patent due to non-payment of fees |