MD1418G2 - Analogi ai acilfulvenei şi compoziţie farmaceutică pe baza lor - Google Patents

Analogi ai acilfulvenei şi compoziţie farmaceutică pe baza lor

Info

Publication number
MD1418G2
MD1418G2 MD96-0212A MD960212A MD1418G2 MD 1418 G2 MD1418 G2 MD 1418G2 MD 960212 A MD960212 A MD 960212A MD 1418 G2 MD1418 G2 MD 1418G2
Authority
MD
Moldova
Prior art keywords
acylfulven
analogues
pharmaceutical composition
base
alkyl
Prior art date
Application number
MD96-0212A
Other languages
English (en)
Russian (ru)
Other versions
MD1418F2 (ro
MD960212A (ro
Inventor
Michael J Kelner
Trevor C Mcmorris
Raymond Taetle
Original Assignee
The Regents Of The University Of California
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by The Regents Of The University Of California filed Critical The Regents Of The University Of California
Publication of MD960212A publication Critical patent/MD960212A/ro
Publication of MD1418F2 publication Critical patent/MD1418F2/ro
Publication of MD1418G2 publication Critical patent/MD1418G2/ro

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • 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
    • A61K31/12—Ketones
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
    • 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
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
    • C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
    • C07C49/67—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having two rings, e.g. tetralones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
    • C07C49/683—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/723—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic
    • C07C49/727—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system
    • C07C49/737—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system having three rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • C07C49/755—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups a keto group being part of a condensed ring system with two or three rings, at least one ring being a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/93—Spiro compounds
    • C07C2603/94—Spiro compounds containing "free" spiro atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Emergency Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oncology (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Saccharide Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)

Abstract

Se revendică analogi ai acilfulvenei cu formula:,în care R se selectează din grupa constituită din:,unde R1 reprezintă alchil, aril, NH2, NH(alchil) sau N(alchil)2şi o compoziţie farmaceutică pentru inhibarea proliferării celulelor tumorale, utilizată în tratamentul tumorii mieloide, epidermoide, leucemiei T- celulare sau carcinomului pulmonar, ovarian sau mamar.Rezultatul constă în reducerea toxicităţii remediului medicamentos.
MD96-0212A 1993-02-09 1994-02-02 Analogi ai acilfulvenei şi compoziţie farmaceutică pe baza lor MD1418G2 (ro)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/015,179 US5439936A (en) 1989-10-03 1993-02-09 Method of treating certain tumors using illudin analogs
PCT/US1994/001232 WO1994018151A1 (en) 1993-02-09 1994-02-02 Acylfulvene analogues as antitumor agents

Publications (3)

Publication Number Publication Date
MD960212A MD960212A (ro) 1999-01-31
MD1418F2 MD1418F2 (ro) 2000-02-29
MD1418G2 true MD1418G2 (ro) 2000-10-31

Family

ID=21769946

Family Applications (1)

Application Number Title Priority Date Filing Date
MD96-0212A MD1418G2 (ro) 1993-02-09 1994-02-02 Analogi ai acilfulvenei şi compoziţie farmaceutică pe baza lor

Country Status (22)

Country Link
US (3) US5439936A (ro)
EP (1) EP0683762B1 (ro)
JP (1) JP3908270B2 (ro)
KR (1) KR100311327B1 (ro)
CN (1) CN1046934C (ro)
AT (1) ATE174894T1 (ro)
AU (1) AU676889B2 (ro)
BR (1) BR9405689A (ro)
CA (1) CA2155329C (ro)
CZ (1) CZ288596B6 (ro)
DE (1) DE69415507T2 (ro)
DK (1) DK0683762T3 (ro)
ES (1) ES2125441T3 (ro)
GR (1) GR3029736T3 (ro)
HU (1) HU220059B (ro)
MD (1) MD1418G2 (ro)
NO (1) NO318648B1 (ro)
NZ (1) NZ262282A (ro)
PL (1) PL175024B1 (ro)
RU (1) RU2145849C1 (ro)
TJ (1) TJ266B (ro)
WO (1) WO1994018151A1 (ro)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5932553A (en) * 1996-07-18 1999-08-03 The Regents Of The University Of California Illudin analogs useful as antitumor agents
US5723632A (en) * 1996-08-08 1998-03-03 Mgi Pharma, Inc. Total synthesis of antitumor acylfulvenes
US7141603B2 (en) * 1999-02-19 2006-11-28 The Regents Of The University California Antitumor agents
US6025328A (en) 1998-02-20 2000-02-15 The Regents Of The University Of California Antitumor agents
US7015247B2 (en) * 2000-10-12 2006-03-21 Alvin Guttag Ibuprofen-aspirin, hydroxymethylacylfulvene analogs and L-sugar illudin analogs
US6436916B1 (en) 2000-10-12 2002-08-20 Alvin Guttag Ibuprofen-aspirin and hydroxymethylacylfulvene analogs
EP2277595A3 (en) 2004-06-24 2011-09-28 Novartis Vaccines and Diagnostics, Inc. Compounds for immunopotentiation
EP1909783B1 (en) * 2005-08-03 2011-10-12 The Regents of the University of California Illudin analogs useful as anticancer agents
NZ594236A (en) * 2009-01-26 2014-08-29 Univ Taipei Medical Use of pterosin compounds for treating diabetes and obesity
EP3129357B1 (en) 2014-04-10 2023-08-23 AF Chemicals LLC Affinity medicant conjugates
US11135182B2 (en) 2014-04-10 2021-10-05 Af Chemicals, Llc Affinity medicant conjugates
US10285955B2 (en) 2014-04-10 2019-05-14 Af Chemicals, Llc Affinity medicant conjugate
CN106083953A (zh) * 2016-06-15 2016-11-09 成都医学院 一种从蕨菜中提取原蕨苷以及制备高纯度原蕨苷的方法
WO2018170230A1 (en) * 2017-03-15 2018-09-20 Memorial Sloan Kettering Cancer Center Diagnosis & treatment of ercc3-mutant cancer
CA3111772A1 (en) * 2018-09-04 2020-03-12 Lantern Pharma Inc. Illudin analogs, uses thereof, and methods for synthesizing the same
US11160807B1 (en) 2018-12-11 2021-11-02 Af Chemicals, Llc Methods, compositions and devices for treating cancer with illudofulvenes
RU2738848C1 (ru) * 2019-10-24 2020-12-17 Общество с ограниченной ответственностью "Научно-исследовательский институт ХимРар" (ООО "НИИ ХимРар") Ингибитор вируса гепатита В (ВГВ), представляющий собой производные N-{ 3-[6-(диалкиламино)пиридазин-3-ил]фенил} арилсульфонамида и производные N-{ 4-[6-(диалкиламино)пиридазин-3-ил]фенил} арилсульфонамида
US11591295B2 (en) 2019-11-25 2023-02-28 Af Chemicals Llc Affinity illudofulvene conjugates
EP4035684A1 (en) 2019-11-25 2022-08-03 AF Chemical LLC Affinity illudofulvene conjugates
CN112972443A (zh) * 2021-03-29 2021-06-18 杭州添帆生物科技有限公司 一种抗癌药物及其应用
WO2023239821A2 (en) * 2022-06-07 2023-12-14 Lantern Pharma Inc. Treating cancers with combinations of acylfulvenes with ibrutinib or bortezomib
WO2024016014A2 (en) * 2022-07-15 2024-01-18 Lantern Pharma Inc. Method for treating breast cancers and parp resistant breast cancers

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0565519B1 (en) * 1989-10-03 1996-08-28 The Regents Of The University Of California Illudin analogs as anti-tumor agents
GB9017024D0 (en) * 1990-08-03 1990-09-19 Erba Carlo Spa New linker for bioactive agents
FI85318C (fi) * 1990-08-14 1992-03-25 Tecnomen Oy Kompensering av felet i en klockas gaong.
JPH06223404A (ja) * 1993-01-25 1994-08-12 Mitsubishi Kasei Corp 光学的情報記録用媒体

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Kelner M. et al., Cancer Res., 1987, vol. 47, p. 3186 *

Also Published As

Publication number Publication date
MD1418F2 (ro) 2000-02-29
EP0683762A1 (en) 1995-11-29
US5439936A (en) 1995-08-08
AU676889B2 (en) 1997-03-27
CN1119854A (zh) 1996-04-03
CA2155329C (en) 2006-08-15
CZ288596B6 (cs) 2001-07-11
KR100311327B1 (ko) 2001-12-28
PL310159A1 (en) 1995-11-27
CA2155329A1 (en) 1994-08-18
JPH08506812A (ja) 1996-07-23
DE69415507D1 (de) 1999-02-04
GR3029736T3 (en) 1999-06-30
US5563176A (en) 1996-10-08
PL175024B1 (pl) 1998-10-30
AU6170094A (en) 1994-08-29
DE69415507T2 (de) 1999-08-12
BR9405689A (pt) 1995-11-21
NO953099D0 (no) 1995-08-07
CN1046934C (zh) 1999-12-01
WO1994018151A1 (en) 1994-08-18
HU9502358D0 (en) 1995-10-30
NO318648B1 (no) 2005-04-25
HU220059B (hu) 2001-10-28
HUT72450A (en) 1996-04-29
RU2145849C1 (ru) 2000-02-27
DK0683762T3 (da) 1999-08-23
NZ262282A (en) 1997-06-24
US5523490A (en) 1996-06-04
ATE174894T1 (de) 1999-01-15
CZ198695A3 (en) 1996-01-17
MD960212A (ro) 1999-01-31
EP0683762B1 (en) 1998-12-23
ES2125441T3 (es) 1999-03-01
JP3908270B2 (ja) 2007-04-25
NO953099L (no) 1995-10-09
TJ266B (en) 2000-08-07

Similar Documents

Publication Publication Date Title
MD1418G2 (ro) Analogi ai acilfulvenei şi compoziţie farmaceutică pe baza lor
GEP20074251B (en) N-oxycarbonyl substituted 5'- deoxy-5-fluorocytidines
BG104597A (en) Inhibition of raf kinase using substituted heterocyclic ureas
BG104599A (en) Inhibition of raf kinase using symmetrical and unsymmetrical substituted diphenyl ureas
PL367682A1 (en) Dolastatin 10 derivatives
MX9603052A (es) Analogos delta 12.13 iso-taxol uso antineoplastico y las composiciones farmaceuticas que los contienen.
AP9701041A0 (en) Pyridylpyrrole compounds.
WO1994004541A3 (en) Protein kinase inhibitors and related compounds combined with taxol
HU914153D0 (en) Electrically operated lock
ES8501736A1 (es) Un procedimiento para la preparacion de (-)-(r)-1-hidroxi-2--(r-1-metil-3-fenilpropril-aminoetil-salicilamida o una sal de adicion de acido respectiva.
AU2521597A (en) Piperidinylpyramidine derivatives
GR3021182T3 (en) New peptide compound and a process for the preparation thereof
DE69907419D1 (en) Antitumorwirkstoffe
GR3030472T3 (en) Novel substituted tertiary amino compound or salt thereof.
ES8608503A1 (es) Procedimiento para la fabricacion de nuevos derivados de la cumarina
PL313078A1 (en) Novel bis-naphtalimides for use in treating carcinoma
MY104829A (en) 3-phenyl-5, 6-dihydrobenz [c]acridine-7-carboxylic acids and related compounds as cancer chemotherapeutic agents.
IL108665A (en) Pharmaceutical compositions containing ureido derivatives of substituted pyrroles, certain such novel compounds and their preparation
EP0604352A3 (en) Heterocyclic compounds substituted by an aryl group.
ES2149193T3 (es) Compuestos heterociclicos sustituidos con alquilo.
DE69724472D1 (de) Selenophen-antitumormittel
GR3023427T3 (en) Heteroarylmethylbenzols aromatase inhibitors
GR3021678T3 (en) Novel platinum (ii) complex and drug for treating malignant tumor
ATE36957T1 (de) N,n-diethyl-5-methyl-2h,1-benzothiopyrano-(4,3, - cd)-indazol-2-ethanamine, diese enthaltende zubereitungen und ihre verwendung.
GB1466623A (en) Nutrient compsoitions including heterocyclic compounds and methods involving the use of such compounds

Legal Events

Date Code Title Description
PD99 Pending application
KA4A Patent for invention lapsed due to non-payment of fees (with right of restoration)
NF4A Restoration of lapsed patent for invention
KA4A Patent for invention lapsed due to non-payment of fees (with right of restoration)
MM4A Patent for invention definitely lapsed due to non-payment of fees