US 7,732,412 B2Granted

Methods of treatment using novel LHRH antagonists having improved solubility properties

AssigneeZentaris AG

InventorsMichael Bernd, Bernhard Kutscher, Eckhard Gunther, Peter Romeis, Thomas Reissmann, Thomas Beckers

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Abstract

The invention relates to peptides which contain N-methylated amino acid units and have improved water solubility. The invention also relates methods for treating a hormone-dependent tumor or a non-malignant indication that is treatable by LH-RH suppression, the method comprising administering to a patient in need of the treatment a therapeutically effective amount of a compound of the invention. Hormone-dependent cancers that can be treated with the methods of the invention include prostate cancer, breast cancer, ovarian cancer, endometrial cancer, and pancreatic cancer. Non-malignant indications which can be treated by the methods of the invention include benign prostate hyperplasia (BPH), endometriosis, acne, polycystic ovarian disease, dysmenorrhea, precocious puberty, and uterine fibroids and other leiomyomas.

Claims8

Dependent claims

A method of treating a hormone-influenced non-malignant disorder that is treatable by luteinizing hormone-releasing hormone (LH-RH) suppression, the method comprising administering to a patient in need of the treatment a therapeutically effective amount of a compound of the general formula I

A-Xxx1-Xxx2-Xxx3-Xxx4-Xxx5-Xxx6-Xxx7-Xxx8-Xxx9-Xxx10-NH2 (I)
in which:
A is an acetyl or a 3-(4-fluorophenyl)propionyl group,
Xxx1 is D-Nal(1) or D-Nal(2),
Xxx2-Xxx3 is D-Cpa-D-Pal,(3) or a single bond,
Xxx4 is Ser,
Xxx5 is N-Me-Tyr,
Xxx6 is D-Cit, D-Hci or a D-amino acid group of the general formula II
in which n is the number 3 or 4, where R1 is a group having the general formula III
—(CH2)p—CO—NR2 R3 (III)
where p is an integer from 1 to 4, R2 is hydrogen or an alkyl group and R3 is an unsubstituted or substituted aryl group or heteroaryl group, or R1 is a 3-amino-1,2,4-triazole-5-carbonyl group or R1 is a ring of the general formula IV
in which q is the number 1 or 2, R4 is a hydrogen atom or an alkyl group, R5 is a hydrogen atom or an alkyl group and X is an oxygen or sulphur atom,
Xxx7 is Leu or Nle,
Xxx8 is Arg or Lys(iPr),
Xxx9 is Pro, and
Xxx10 is Ala, D-Ala, or Sar,
and their salts with pharmaceutically acceptable acids.

14 more elements

Dependencies are inferred from the claim text.

Facts

Application: 11/459,583Filed 24 Jul 2006 · continuation in part
Priority: DE 199 00 77117 Mar 1999
Published: US 2006/0281685 A114 Dec 2006
Granted: 8 Jun 2010
Term ends: Not estimatedThe source records don’t support an estimate.

Classification10 codes

A61K 38/10
Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof: peptides having 12 to 20 amino acids
A61P 5/04
Of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin: for decreasing, blocking or antagonising the activity of the hypothalamic…
A61P 5/06
Drugs for disorders of the endocrine system: of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
A61P 15/00
Drugs for genital or sexual disorders

Family

Application09/525,007Parent of this division · filed 14 Mar 2000
Application10/671,573Parent of this continuation-in-part · filed 29 Sep 2003
US 2006/0281685 A1Pre-grant publication · published 14 Dec 2006
US 7,148,195 B2Parent of this continuation-in-part
US 6,627,609 B1Parent of this division
Application10/671,573Parent of this division
US 2004/0266695 A1Published application
US 7,732,412 B2This patent

From the US filing history. Foreign family members aren’t listed.