AU709539B2 - Targeted cytotoxic anthracycline analogs - Google Patents

Targeted cytotoxic anthracycline analogs Download PDF

Info

Publication number: AU709539B2
Authority: AU; Australia
Prior art keywords: compound; trp; formula; leu; treatment
Prior art date: 1995-11-27
Legal status (The legal status 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 status listed.): Expired

Application number

AU75722/96A

Other languages

English (en)

Other versions

AU7572296A (en

Inventor

Ren Zhi Cai

Attila A. Nagy

Andrew V. Schally

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Tulane University

Original Assignee

Asta Medica GmbH

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.)

1995-11-27

Filing date

1996-11-14

Publication date

1999-09-02

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=24247176&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=AU709539(B2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1996-11-14 Application filed by Asta Medica GmbH filed Critical Asta Medica GmbH

1997-06-19 Publication of AU7572296A publication Critical patent/AU7572296A/en

1999-09-02 Application granted granted Critical

1999-09-02 Publication of AU709539B2 publication Critical patent/AU709539B2/en

2001-12-06 Assigned to ZENTARIS AKTIENGESELLSCHAFT reassignment ZENTARIS AKTIENGESELLSCHAFT Alteration of Name(s) in Register under S187 Assignors: ASTA MEDICA AKTIENGESELLSCHAFT

2003-05-22 Assigned to ADMINISTRATORS OF THE TULANE EDUCATIONAL FUND, THE reassignment ADMINISTRATORS OF THE TULANE EDUCATIONAL FUND, THE Alteration of Name(s) in Register under S187 Assignors: ZENTARIS AKTIENGESELLSCHAFT

2016-11-14 Anticipated expiration legal-status Critical

Status Expired legal-status Critical Current

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239000011368 organic material Substances 0.000 description 1
210000001672 ovary Anatomy 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
201000010210 papillary cystadenocarcinoma Diseases 0.000 description 1
230000010412 perfusion Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
230000035479 physiological effects, processes and functions Effects 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
230000036515 potency Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
XNSAINXGIQZQOO-SRVKXCTJSA-N protirelin Chemical compound NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@H]1NC(=O)CC1)CC1=CN=CN1 XNSAINXGIQZQOO-SRVKXCTJSA-N 0.000 description 1
QGKLPGKXAVVPOJ-UHFFFAOYSA-N pyrrolidin-3-one Chemical compound O=C1CCNC1 QGKLPGKXAVVPOJ-UHFFFAOYSA-N 0.000 description 1
238000011002 quantification Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000005932 reductive alkylation reaction Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
229960001153 serine Drugs 0.000 description 1
239000011734 sodium Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000010186 staining Methods 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
201000011549 stomach cancer Diseases 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
238000011285 therapeutic regimen Methods 0.000 description 1
DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical compound OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 description 1
229940034199 thyrotropin-releasing hormone Drugs 0.000 description 1
231100000816 toxic dose Toxicity 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
108700012359 toxins Proteins 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
VXKHXGOKWPXYNA-PGBVPBMZSA-N triptorelin 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](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)NCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 VXKHXGOKWPXYNA-PGBVPBMZSA-N 0.000 description 1
239000012588 trypsin Substances 0.000 description 1
125000000430 tryptophan group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
230000002476 tumorcidal effect Effects 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
230000004580 weight loss Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/23—Luteinising hormone-releasing hormone [LHRH]; Related peptides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/62—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
- 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
- A61P35/04—Antineoplastic agents specific for metastasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Genetics & Genomics (AREA)
Endocrinology (AREA)
Biochemistry (AREA)
Biophysics (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Epidemiology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Oncology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)
Saccharide Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicinal Preparation (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Plural Heterocyclic Compounds (AREA)

AU75722/96A 1995-11-27 1996-11-14 Targeted cytotoxic anthracycline analogs Expired AU709539B2 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US08/562652		1995-11-27
US08/562,652 US5843903A (en)	1995-11-27	1995-11-27	Targeted cytotoxic anthracycline analogs
PCT/EP1996/005029 WO1997019954A1 (en)	1995-11-27	1996-11-14	Targeted cytotoxic anthracycline analogs

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
AU57092/99A Division AU748507B2 (en)	1995-11-27	1999-10-28	Novel synthetic reaction and targeted cytotoxic anthracycline analogs obtained thereby

Publications (2)

Publication Number	Publication Date
AU7572296A AU7572296A (en)	1997-06-19
AU709539B2 true AU709539B2 (en)	1999-09-02

Family

ID=24247176

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU75722/96A Expired AU709539B2 (en)	1995-11-27	1996-11-14	Targeted cytotoxic anthracycline analogs

Country Status (27)

Country	Link
US (2)	US5843903A (2)
EP (2)	EP0863917B1 (2)
JP (2)	JP3987575B2 (2)
KR (2)	KR100467899B1 (2)
CN (2)	CN1166597C (2)
AT (2)	ATE401305T1 (2)
AU (1)	AU709539B2 (2)
BR (1)	BR9611647B1 (2)
CA (2)	CA2238574C (2)
CZ (1)	CZ297297B6 (2)
DE (2)	DE69630233T2 (2)
DK (2)	DK1384710T3 (2)
EA (1)	EA001372B1 (2)
ES (2)	ES2310222T3 (2)
HK (1)	HK1052920B (2)
HU (1)	HU229870B1 (2)
IL (3)	IL119691A (2)
IS (2)	IS2178B (2)
MX (1)	MX9804119A (2)
NO (2)	NO324035B1 (2)
NZ (1)	NZ322054A (2)
PL (3)	PL191781B1 (2)
PT (2)	PT863917E (2)
SK (2)	SK284672B6 (2)
UA (1)	UA67722C2 (2)
WO (1)	WO1997019954A1 (2)
ZA (1)	ZA969709B (2)

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1995
- 1995-11-27 US US08/562,652 patent/US5843903A/en not_active Expired - Lifetime
1996
- 1996-11-14 AT AT03010988T patent/ATE401305T1/de active
- 1996-11-14 CN CNB021439192A patent/CN1166597C/zh not_active Expired - Lifetime
- 1996-11-14 CA CA002238574A patent/CA2238574C/en not_active Expired - Lifetime
- 1996-11-14 PL PL358737A patent/PL191781B1/pl unknown
- 1996-11-14 SK SK341-2004A patent/SK284672B6/sk not_active IP Right Cessation
- 1996-11-14 ES ES03010988T patent/ES2310222T3/es not_active Expired - Lifetime
- 1996-11-14 DK DK03010988T patent/DK1384710T3/da active
- 1996-11-14 NZ NZ322054A patent/NZ322054A/en not_active IP Right Cessation
- 1996-11-14 CZ CZ0135798A patent/CZ297297B6/cs not_active IP Right Cessation
- 1996-11-14 BR BRPI9611647-1A patent/BR9611647B1/pt not_active IP Right Cessation
- 1996-11-14 WO PCT/EP1996/005029 patent/WO1997019954A1/en not_active Ceased
- 1996-11-14 HU HU9903771A patent/HU229870B1/hu unknown
- 1996-11-14 KR KR10-2004-7004548A patent/KR100467899B1/ko not_active Expired - Lifetime
- 1996-11-14 CA CA002471775A patent/CA2471775C/en not_active Expired - Lifetime
- 1996-11-14 AT AT96938216T patent/ATE251179T1/de active
- 1996-11-14 EA EA199800492A patent/EA001372B1/ru not_active IP Right Cessation
- 1996-11-14 UA UA98063318A patent/UA67722C2/uk unknown
- 1996-11-14 AU AU75722/96A patent/AU709539B2/en not_active Expired
- 1996-11-14 PT PT96938216T patent/PT863917E/pt unknown
- 1996-11-14 EP EP96938216A patent/EP0863917B1/en not_active Expired - Lifetime
- 1996-11-14 DK DK96938216T patent/DK0863917T3/da active
- 1996-11-14 PT PT03010988T patent/PT1384710E/pt unknown
- 1996-11-14 PL PL96358646A patent/PL188786B1/pl unknown
- 1996-11-14 JP JP52012397A patent/JP3987575B2/ja not_active Expired - Lifetime
- 1996-11-14 EP EP03010988A patent/EP1384710B1/en not_active Expired - Lifetime
- 1996-11-14 PL PL96326865A patent/PL187230B1/pl unknown
- 1996-11-14 DE DE69630233T patent/DE69630233T2/de not_active Expired - Lifetime
- 1996-11-14 SK SK628-98A patent/SK284392B6/sk unknown
- 1996-11-14 DE DE69637604T patent/DE69637604D1/de not_active Expired - Lifetime
- 1996-11-14 CN CNB961986050A patent/CN1137136C/zh not_active Expired - Lifetime
- 1996-11-14 ES ES96938216T patent/ES2205067T3/es not_active Expired - Lifetime
- 1996-11-14 KR KR10-1998-0703948A patent/KR100445754B1/ko not_active Expired - Lifetime
- 1996-11-20 ZA ZA9609709A patent/ZA969709B/xx unknown
- 1996-11-26 IL IL11969196A patent/IL119691A/en not_active IP Right Cessation
- 1996-11-26 IL IL13468596A patent/IL134685A/en not_active IP Right Cessation
1998
- 1998-05-05 IS IS4734A patent/IS2178B/is unknown
- 1998-05-15 NO NO19982252A patent/NO324035B1/no not_active IP Right Cessation
- 1998-05-25 MX MX9804119A patent/MX9804119A/es unknown
- 1998-07-15 US US09/116,125 patent/US6184374B1/en not_active Expired - Lifetime
2000
- 2000-02-23 IL IL13468500A patent/IL134685A0/xx unknown
2003
- 2003-07-09 HK HK03104934.8A patent/HK1052920B/zh not_active IP Right Cessation
2005
- 2005-03-01 NO NO20051111A patent/NO20051111L/no not_active Application Discontinuation
2006
- 2006-11-09 IS IS8567A patent/IS2634B/is unknown
- 2006-11-15 JP JP2006309698A patent/JP4778405B2/ja not_active Expired - Lifetime

Patent Citations (2)

* Cited by examiner, † Cited by third party
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GB2124224A (en) *	1982-07-20	1984-02-15	Stanford Res Inst Int	Derivatives of daunorubicin and doxorubicin
EP0434960A1 (en) *	1989-12-19	1991-07-03	PHARMACIA S.p.A.	Chiral 1,5-diiodo-2-methoxy or benzyloxy intermediates

Also Published As

Publication number	Publication date
EA199800492A1 (ru)	1998-12-24
BR9611647A (pt)	1999-02-23
CA2471775C (en)	2008-01-29
US5843903A (en)	1998-12-01
ZA969709B (en)	1997-08-25
PT863917E (pt)	2004-02-27
CA2238574A1 (en)	1997-06-05
EA001372B1 (ru)	2001-02-26
NO20051111L (no)	2005-03-01
ATE401305T1 (de)	2008-08-15
KR100445754B1 (ko)	2004-12-08
NO982252L (no)	1998-05-15
EP1384710B1 (en)	2008-07-16
SK284392B6 (sk)	2005-03-04
EP0863917A1 (en)	1998-09-16
IL134685A (en)	2002-12-01
DE69637604D1 (de)	2008-08-28
PL187230B1 (pl)	2004-06-30
JP2007045845A (ja)	2007-02-22
IS2178B (is)	2006-12-15
HK1017363A1 (en)	1999-11-19
CA2238574C (en)	2004-10-19
PL191781B1 (pl)	2006-07-31
CA2471775A1 (en)	1997-06-05
WO1997019954A1 (en)	1997-06-05
DK0863917T3 (da)	2004-01-19
IL134685A0 (en)	2001-04-30
ES2310222T3 (es)	2009-01-01
PL326865A1 (en)	1998-10-26
JP2000502055A (ja)	2000-02-22
DE69630233D1 (de)	2003-11-06
HK1052920B (zh)	2005-03-04
HUP9903771A3 (en)	2000-07-28
KR19990071672A (ko)	1999-09-27
PT1384710E (pt)	2008-10-08
NO982252D0 (no)	1998-05-15
EP1384710A1 (en)	2004-01-28
IL119691A0 (en)	1997-02-18
CZ297297B6 (cs)	2006-11-15
CN1137136C (zh)	2004-02-04
IL119691A (en)	2002-02-10
IS2634B (is)	2010-06-15
IS4734A (is)	1998-05-05
KR20040037176A (ko)	2004-05-04
US6184374B1 (en)	2001-02-06
ES2205067T3 (es)	2004-05-01
HU229870B1 (en)	2014-10-28
CN1166597C (zh)	2004-09-15
CN1202903A (zh)	1998-12-23
ATE251179T1 (de)	2003-10-15
CZ135798A3 (cs)	1998-10-14
CN1405127A (zh)	2003-03-26
PL188786B1 (pl)	2005-04-29
HUP9903771A2 (hu)	2000-02-28
HK1052920A1 (en)	2003-10-03
BR9611647B1 (pt)	2010-03-09
SK284672B6 (sk)	2005-08-04
JP4778405B2 (ja)	2011-09-21
NO324035B1 (no)	2007-07-30
SK62898A3 (en)	1999-06-11
JP3987575B2 (ja)	2007-10-10
EP0863917B1 (en)	2003-10-01
KR100467899B1 (ko)	2005-01-24
MX9804119A (es)	1998-09-30
UA67722C2 (en)	2004-07-15
DK1384710T3 (da)	2008-11-17
NZ322054A (en)	1999-04-29
DE69630233T2 (de)	2004-08-05
IS8567A (is)	2006-11-09
AU7572296A (en)	1997-06-19

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2003-05-22

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