AU711104B2 - Compounds with growth hormone releasing properties - Google Patents
Compounds with growth hormone releasing properties Download PDFInfo
- Publication number
- AU711104B2 AU711104B2 AU61882/96A AU6188296A AU711104B2 AU 711104 B2 AU711104 B2 AU 711104B2 AU 61882/96 A AU61882/96 A AU 61882/96A AU 6188296 A AU6188296 A AU 6188296A AU 711104 B2 AU711104 B2 AU 711104B2
- Authority
- AU
- Australia
- Prior art keywords
- phe
- 2nal
- acid
- aib
- compound according
- Prior art date
- 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.)
- Ceased
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- 150000001875 compounds Chemical class 0.000 title claims description 77
- 102000018997 Growth Hormone Human genes 0.000 title claims description 46
- 108010051696 Growth Hormone Proteins 0.000 title claims description 46
- 239000000122 growth hormone Substances 0.000 title claims description 46
- 230000003578 releasing effect Effects 0.000 title claims description 6
- -1 guanidino, piperazino, morpholino, piperidino Chemical group 0.000 claims description 74
- 239000000203 mixture Substances 0.000 claims description 55
- 238000000034 method Methods 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 230000001817 pituitary effect Effects 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 241001465754 Metazoa Species 0.000 claims description 10
- FUOOLUPWFVMBKG-UHFFFAOYSA-N 2-Aminoisobutyric acid Chemical compound CC(C)(N)C(O)=O FUOOLUPWFVMBKG-UHFFFAOYSA-N 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical group 0.000 claims description 9
- JPZXHKDZASGCLU-GFCCVEGCSA-N 3-(2-Naphthyl)-D-Alanine Chemical compound C1=CC=CC2=CC(C[C@@H](N)C(O)=O)=CC=C21 JPZXHKDZASGCLU-GFCCVEGCSA-N 0.000 claims description 8
- COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical compound OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
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- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
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- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 claims description 6
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- 150000001413 amino acids Chemical class 0.000 claims description 4
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
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- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- GSWYUZQBLVUEPH-UHFFFAOYSA-N 3-(azaniumylmethyl)benzoate Chemical compound NCC1=CC=CC(C(O)=O)=C1 GSWYUZQBLVUEPH-UHFFFAOYSA-N 0.000 claims description 3
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- WTKYBFQVZPCGAO-LURJTMIESA-N (2s)-2-(pyridin-3-ylamino)propanoic acid Chemical compound OC(=O)[C@H](C)NC1=CC=CN=C1 WTKYBFQVZPCGAO-LURJTMIESA-N 0.000 claims description 2
- BWKMGYQJPOAASG-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid Chemical compound C1=CC=C2CNC(C(=O)O)CC2=C1 BWKMGYQJPOAASG-UHFFFAOYSA-N 0.000 claims description 2
- KGSVNOLLROCJQM-UHFFFAOYSA-N 2-(benzylamino)acetic acid Chemical compound OC(=O)CNCC1=CC=CC=C1 KGSVNOLLROCJQM-UHFFFAOYSA-N 0.000 claims description 2
- ATAFDSCDEDHMOK-UHFFFAOYSA-N 3,3-diaminopropanoic acid Chemical compound NC(N)CC(O)=O ATAFDSCDEDHMOK-UHFFFAOYSA-N 0.000 claims description 2
- NFQAIWOMJQWGSS-UHFFFAOYSA-N 3-amino-3-methylbutanoic acid Chemical compound CC(C)(N)CC(O)=O NFQAIWOMJQWGSS-UHFFFAOYSA-N 0.000 claims description 2
- OWSRLHPWDZOHCR-UHFFFAOYSA-N 4,4-diaminobutanoic acid Chemical compound NC(N)CCC(O)=O OWSRLHPWDZOHCR-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002541 furyl group Chemical group 0.000 claims description 2
- NMILGIZTAZXMTM-UHFFFAOYSA-N 4-propylmorpholine Chemical compound CCCN1CCOCC1 NMILGIZTAZXMTM-UHFFFAOYSA-N 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 2
- 125000003163 2-(2-naphthyl)ethyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(C([H])=C([H])C2=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
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- OBSIQMZKFXFYLV-QMMMGPOBSA-N L-phenylalanine amide Chemical compound NC(=O)[C@@H](N)CC1=CC=CC=C1 OBSIQMZKFXFYLV-QMMMGPOBSA-N 0.000 claims 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 106
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 61
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 40
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 36
- 230000014759 maintenance of location Effects 0.000 description 36
- 239000003921 oil Substances 0.000 description 36
- 235000019198 oils Nutrition 0.000 description 36
- 238000004007 reversed phase HPLC Methods 0.000 description 36
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 25
- 108090000765 processed proteins & peptides Proteins 0.000 description 25
- 235000019439 ethyl acetate Nutrition 0.000 description 24
- 239000012074 organic phase Substances 0.000 description 23
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- 235000017557 sodium bicarbonate Nutrition 0.000 description 20
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 20
- 238000010828 elution Methods 0.000 description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 239000012467 final product Substances 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- KJOZJSGOIJQCGA-UHFFFAOYSA-N dichloromethane;2,2,2-trifluoroacetic acid Chemical compound ClCCl.OC(=O)C(F)(F)F KJOZJSGOIJQCGA-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000011894 semi-preparative HPLC Methods 0.000 description 9
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
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- 239000007787 solid Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 7
- 229940080818 propionamide Drugs 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 6
- MQNHKLMHRZYTBZ-UHFFFAOYSA-N 3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]benzoic acid Chemical compound CC(C)(C)OC(=O)NCC1=CC=CC(C(O)=O)=C1 MQNHKLMHRZYTBZ-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
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- 125000003118 aryl group Chemical group 0.000 description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/60—Growth hormone-releasing factor [GH-RF], i.e. somatoliberin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/06—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0812—Tripeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
- C07K5/101—Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/02—Linear peptides containing at least one abnormal peptide link
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Endocrinology (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Zoology (AREA)
- Toxicology (AREA)
- Gastroenterology & Hepatology (AREA)
- Urology & Nephrology (AREA)
- Reproductive Health (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK719/95 | 1995-06-22 | ||
| DK71995 | 1995-06-22 | ||
| DK1371/95 | 1995-12-04 | ||
| DK137195 | 1995-12-04 | ||
| PCT/DK1996/000266 WO1997000894A1 (en) | 1995-06-22 | 1996-06-19 | Compounds with growth hormone releasing properties |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU6188296A AU6188296A (en) | 1997-01-22 |
| AU711104B2 true AU711104B2 (en) | 1999-10-07 |
Family
ID=26064522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU61882/96A Ceased AU711104B2 (en) | 1995-06-22 | 1996-06-19 | Compounds with growth hormone releasing properties |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0833845A1 (hu) |
| KR (1) | KR19990028303A (hu) |
| AU (1) | AU711104B2 (hu) |
| BR (1) | BR9608909A (hu) |
| CA (1) | CA2224434A1 (hu) |
| CZ (1) | CZ287948B6 (hu) |
| HU (1) | HUP9802821A3 (hu) |
| IL (1) | IL122371A0 (hu) |
| NO (1) | NO975992L (hu) |
| PL (1) | PL186520B1 (hu) |
| TW (1) | TW458958B (hu) |
| WO (1) | WO1997000894A1 (hu) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998008492A1 (en) * | 1996-08-29 | 1998-03-05 | Novo Nordisk A/S | Transdermal delivery of peptides |
| JP4116097B2 (ja) | 1997-06-20 | 2008-07-09 | ノボ ノルディスク アクティーゼルスカブ | 成長ホルモン放出特性をもつ化合物 |
| US6127341A (en) * | 1997-06-20 | 2000-10-03 | Novo Nordisk A/S | Compounds with growth hormone releasing properties |
| CA2301566A1 (en) | 1997-08-22 | 1999-03-04 | Kaken Pharmaceutical Co., Ltd. | N-acylated lipophilic amino acid derivatives |
| EP1047709B1 (en) | 1998-01-16 | 2004-11-03 | Novo Nordisk A/S | Compounds with growth hormone releasing properties |
| US6528529B1 (en) | 1998-03-31 | 2003-03-04 | Acadia Pharmaceuticals Inc. | Compounds with activity on muscarinic receptors |
| EA003860B1 (ru) * | 1998-05-12 | 2003-10-30 | Варнер-Ламберт Компани | КОМБИНАЦИИ ИНГИБИТОРОВ ПРОТЕИН ФАРНЕЗИЛТРАНСФЕРАЗЫ И HMG KoA РЕДУКТАЗЫ И ИХ ПРИМЕНЕНИЕ ДЛЯ ЛЕЧЕНИЯ РАКА |
| US6919315B1 (en) | 1998-06-30 | 2005-07-19 | Novo Nordisk A/S | Compounds with growth hormone releasing properties |
| AU771644B2 (en) * | 1998-06-30 | 2004-04-01 | Helsinn Healthcare Sa | Compounds with growth hormone releasing properties |
| WO2000009537A2 (en) | 1998-08-14 | 2000-02-24 | Administrators Of The Tulane Educational Fund | Compounds having growth hormone releasing activity |
| WO2000048623A1 (en) | 1999-02-18 | 2000-08-24 | Kaken Pharmaceutical Co., Ltd. | Novel amide derivatives as growth hormone secretagogues |
| DE60140285D1 (de) | 2000-05-31 | 2009-12-10 | Pfizer Prod Inc | Verwendung von Wachstumshormonsekretagoga zur Förderung der Beweglichkeit des Verdauungstrakts |
| EP1343751A2 (en) | 2000-12-20 | 2003-09-17 | Bristol-Myers Squibb Company | Cyclic derivatives as modulators of chemokine receptor activity |
| HUP0303540A2 (hu) | 2000-12-20 | 2004-01-28 | Bristol-Myers Squibb Pharma Co. | Diaminok mint kemokin receptor aktivitás modulátorai, ezeket tartalmazó gyógyszerkészítmények és alkalmazásuk |
| TWI331922B (en) | 2002-08-09 | 2010-10-21 | Ipsen Pharma Sas | Growth hormone releasing peptides |
| US7476653B2 (en) | 2003-06-18 | 2009-01-13 | Tranzyme Pharma, Inc. | Macrocyclic modulators of the ghrelin receptor |
| EP2258359A3 (en) | 2005-08-26 | 2011-04-06 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation with sabcomelin |
| EP2275095A3 (en) | 2005-08-26 | 2011-08-17 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| CU23558A1 (es) | 2006-02-28 | 2010-07-20 | Ct Ingenieria Genetica Biotech | Compuestos análogos a los secretagogos peptidicos de la hormona de crecimiento |
| EA200901077A1 (ru) | 2007-02-09 | 2010-04-30 | Транзим Фарма, Инк. | Макроциклические модуляторы грелинового рецептора и их применение |
| WO2009079797A1 (en) | 2007-12-26 | 2009-07-02 | Critical Outcome Technologies, Inc. | Compounds and method for treatment of cancer |
| WO2010006438A1 (en) | 2008-07-17 | 2010-01-21 | Critical Outcome Technologies Inc. | Thiosemicarbazone inhibitor compounds and cancer treatment methods |
| US8987272B2 (en) | 2010-04-01 | 2015-03-24 | Critical Outcome Technologies Inc. | Compounds and method for treatment of HIV |
| WO2013190520A2 (en) | 2012-06-22 | 2013-12-27 | The General Hospital Corporation | Gh-releasing agents in the treatment of vascular stenosis and associated conditions |
| US9119832B2 (en) | 2014-02-05 | 2015-09-01 | The Regents Of The University Of California | Methods of treating mild brain injury |
| US20170121385A1 (en) | 2015-10-28 | 2017-05-04 | Oxeia Biopharmaceuticals, Inc. | Methods of treating neurodegenerative conditions |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU1272495A (en) * | 1993-12-23 | 1995-07-10 | Novo Nordisk A/S | Compounds with growth hormone releasing properties |
| AU4164496A (en) * | 1994-11-16 | 1996-06-06 | Genentech Inc. | Low molecular weight peptidomimetic growth hormone secretagogues |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5663146A (en) * | 1991-08-22 | 1997-09-02 | Administrators Of The Tulane Educational Fund | Polypeptide analogues having growth hormone releasing activity |
-
1996
- 1996-06-19 PL PL96324200A patent/PL186520B1/pl unknown
- 1996-06-19 KR KR1019970709617A patent/KR19990028303A/ko not_active Application Discontinuation
- 1996-06-19 HU HU9802821A patent/HUP9802821A3/hu unknown
- 1996-06-19 WO PCT/DK1996/000266 patent/WO1997000894A1/en not_active Application Discontinuation
- 1996-06-19 AU AU61882/96A patent/AU711104B2/en not_active Ceased
- 1996-06-19 BR BR9608909A patent/BR9608909A/pt not_active Application Discontinuation
- 1996-06-19 CA CA002224434A patent/CA2224434A1/en not_active Abandoned
- 1996-06-19 IL IL12237196A patent/IL122371A0/xx not_active IP Right Cessation
- 1996-06-19 EP EP96920742A patent/EP0833845A1/en not_active Withdrawn
- 1996-06-19 CZ CZ19974081A patent/CZ287948B6/cs not_active IP Right Cessation
- 1996-06-28 TW TW085107813A patent/TW458958B/zh not_active IP Right Cessation
-
1997
- 1997-12-19 NO NO975992A patent/NO975992L/no not_active Application Discontinuation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU1272495A (en) * | 1993-12-23 | 1995-07-10 | Novo Nordisk A/S | Compounds with growth hormone releasing properties |
| AU4164496A (en) * | 1994-11-16 | 1996-06-06 | Genentech Inc. | Low molecular weight peptidomimetic growth hormone secretagogues |
Also Published As
| Publication number | Publication date |
|---|---|
| KR19990028303A (ko) | 1999-04-15 |
| PL186520B1 (pl) | 2004-01-30 |
| IL122371A0 (en) | 1998-06-15 |
| JPH11507928A (ja) | 1999-07-13 |
| JP4173541B2 (ja) | 2008-10-29 |
| PL324200A1 (en) | 1998-05-11 |
| BR9608909A (pt) | 1999-03-02 |
| AU6188296A (en) | 1997-01-22 |
| NO975992L (no) | 1998-02-20 |
| TW458958B (en) | 2001-10-11 |
| MX9710377A (es) | 1998-03-29 |
| CA2224434A1 (en) | 1997-01-09 |
| HUP9802821A3 (en) | 2000-03-28 |
| NO975992D0 (no) | 1997-12-19 |
| HUP9802821A2 (hu) | 1999-03-29 |
| CZ287948B6 (cs) | 2001-03-14 |
| CZ408197A3 (cs) | 1998-05-13 |
| EP0833845A1 (en) | 1998-04-08 |
| WO1997000894A1 (en) | 1997-01-09 |
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