AU653544B2 - Bombesin antagonists - Google Patents
Bombesin antagonists Download PDFInfo
- Publication number
- AU653544B2 AU653544B2 AU83111/91A AU8311191A AU653544B2 AU 653544 B2 AU653544 B2 AU 653544B2 AU 83111/91 A AU83111/91 A AU 83111/91A AU 8311191 A AU8311191 A AU 8311191A AU 653544 B2 AU653544 B2 AU 653544B2
- Authority
- AU
- Australia
- Prior art keywords
- ala
- pro
- phe
- phenyl
- polypeptide
- 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
Links
- 239000002790 bombesin antagonist Substances 0.000 title description 6
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 107
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 72
- 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 claims description 68
- -1 amino, hydroxy Chemical group 0.000 claims description 62
- 229920001184 polypeptide Polymers 0.000 claims description 61
- 238000000034 method Methods 0.000 claims description 45
- 150000001413 amino acids Chemical class 0.000 claims description 32
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 30
- 230000008569 process Effects 0.000 claims description 27
- 238000011282 treatment Methods 0.000 claims description 25
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 23
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 108090001053 Gastrin releasing peptide Proteins 0.000 claims description 13
- 102100036519 Gastrin-releasing peptide Human genes 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 12
- COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical compound OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 claims description 11
- 206010041067 Small cell lung cancer Diseases 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 208000000587 small cell lung carcinoma Diseases 0.000 claims description 11
- ONIBWKKTOPOVIA-SCSAIBSYSA-N D-Proline Chemical compound OC(=O)[C@H]1CCCN1 ONIBWKKTOPOVIA-SCSAIBSYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- PUBCCFNQJQKCNC-XKNFJVFFSA-N gastrin-releasingpeptide Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)CNC(=O)[C@H](C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(C)C)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)C(C)C)[C@@H](C)O)C(C)C)[C@@H](C)O)C(C)C)C1=CNC=N1 PUBCCFNQJQKCNC-XKNFJVFFSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 claims description 8
- QNAYBMKLOCPYGJ-UWTATZPHSA-N D-alanine Chemical compound C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 claims description 7
- ODKSFYDXXFIFQN-SCSAIBSYSA-N D-arginine Chemical compound OC(=O)[C@H](N)CCCNC(N)=N ODKSFYDXXFIFQN-SCSAIBSYSA-N 0.000 claims description 7
- VNYDHJARLHNEGA-RYUDHWBXSA-N Tyr-Pro Chemical compound C([C@H](N)C(=O)N1[C@@H](CCC1)C(O)=O)C1=CC=C(O)C=C1 VNYDHJARLHNEGA-RYUDHWBXSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
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- 125000001711 D-phenylalanine group Chemical group [H]N([H])[C@@]([H])(C(=O)[*])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 229940043230 sarcosine Drugs 0.000 claims description 5
- 101000993347 Gallus gallus Ciliary neurotrophic factor Proteins 0.000 claims description 4
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical group OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 4
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- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000002775 capsule Substances 0.000 claims description 4
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- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000003974 aralkylamines Chemical class 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
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- 230000002209 hydrophobic effect Effects 0.000 claims description 3
- OCLLVJCYGMCLJG-ZDUSSCGKSA-N (2s)-2-azaniumyl-2-naphthalen-1-ylpropanoate Chemical compound C1=CC=C2C([C@](N)(C(O)=O)C)=CC=CC2=C1 OCLLVJCYGMCLJG-ZDUSSCGKSA-N 0.000 claims description 2
- KRNSHCKTGFAMPQ-SFOWXEAESA-N (2s)-2-azaniumyl-4,4,4-trifluoro-3-(trifluoromethyl)butanoate Chemical group [O-]C(=O)[C@@H]([NH3+])C(C(F)(F)F)C(F)(F)F KRNSHCKTGFAMPQ-SFOWXEAESA-N 0.000 claims description 2
- 125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 2
- KFHRMMHGGBCRIV-UHFFFAOYSA-N 2-azaniumyl-4-methoxybutanoate Chemical compound COCCC(N)C(O)=O KFHRMMHGGBCRIV-UHFFFAOYSA-N 0.000 claims description 2
- 108010073466 Bombesin Receptors Proteins 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- VEVRNHHLCPGNDU-MUGJNUQGSA-O desmosine Chemical compound OC(=O)[C@@H](N)CCCC[N+]1=CC(CC[C@H](N)C(O)=O)=C(CCC[C@H](N)C(O)=O)C(CC[C@H](N)C(O)=O)=C1 VEVRNHHLCPGNDU-MUGJNUQGSA-O 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229940124597 therapeutic agent Drugs 0.000 claims description 2
- 125000000267 glycino group Chemical group [H]N([*])C([H])([H])C(=O)O[H] 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000000030 D-alanine group Chemical group [H]N([H])[C@](C([H])([H])[H])(C(=O)[*])[H] 0.000 claims 1
- 125000000180 D-prolyl group Chemical group N1[C@@H](C(=O)*)CCC1 0.000 claims 1
- 241001102334 Janua Species 0.000 claims 1
- 102000007079 Peptide Fragments Human genes 0.000 claims 1
- 108010033276 Peptide Fragments Proteins 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
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- 229940024606 amino acid Drugs 0.000 description 35
- 235000001014 amino acid Nutrition 0.000 description 34
- 239000000203 mixture Substances 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
- 238000005859 coupling reaction Methods 0.000 description 21
- 230000008878 coupling Effects 0.000 description 18
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- 125000006239 protecting group Chemical group 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
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- DNDCVAGJPBKION-DOPDSADYSA-N bombesin Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC=1NC2=CC=CC=C2C=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1NC(=O)CC1)C(C)C)C1=CN=CN1 DNDCVAGJPBKION-DOPDSADYSA-N 0.000 description 9
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- 102000004862 Gastrin releasing peptide Human genes 0.000 description 8
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- 229940079322 interferon Drugs 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 210000004153 islets of langerhan Anatomy 0.000 description 1
- 239000008263 liquid aerosol Substances 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 210000004962 mammalian cell Anatomy 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000006140 methanolysis reaction Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- QVDXUKJJGUSGLS-LURJTMIESA-N methyl L-leucinate Chemical compound COC(=O)[C@@H](N)CC(C)C QVDXUKJJGUSGLS-LURJTMIESA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 230000002297 mitogenic effect Effects 0.000 description 1
- 230000000394 mitotic effect Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000007923 nasal drop Substances 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 229940097496 nasal spray Drugs 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 201000002094 pancreatic adenocarcinoma Diseases 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 208000021255 pancreatic insulinoma Diseases 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 238000005897 peptide coupling reaction Methods 0.000 description 1
- 239000000813 peptide hormone Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 210000003635 pituitary gland Anatomy 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940097325 prolactin Drugs 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000017619 regulation of gastric acid secretion Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LQTMEOSBXTVYRM-VIFPVBQESA-N tert-butyl n-[(2s)-1-hydroxy-4-methylpentan-2-yl]carbamate Chemical compound CC(C)C[C@@H](CO)NC(=O)OC(C)(C)C LQTMEOSBXTVYRM-VIFPVBQESA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
- 238000000954 titration curve Methods 0.000 description 1
- 229940044693 topoisomerase inhibitor Drugs 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 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
- C07K7/08—Linear peptides containing only normal peptide links having 12 to 20 amino acids
- C07K7/086—Bombesin; Related peptides
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9016810 | 1990-07-31 | ||
| GB909016810A GB9016810D0 (en) | 1990-07-31 | 1990-07-31 | Peptides |
| PCT/GB1991/001289 WO1992002545A1 (en) | 1990-07-31 | 1991-07-30 | Bombesin antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU8311191A AU8311191A (en) | 1992-03-02 |
| AU653544B2 true AU653544B2 (en) | 1994-10-06 |
Family
ID=10679953
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU83111/91A Ceased AU653544B2 (en) | 1990-07-31 | 1991-07-30 | Bombesin antagonists |
Country Status (20)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5877277A (en) | 1987-09-24 | 1999-03-02 | Biomeasure, Inc. | Octapeptide bombesin analogs |
| US5723578A (en) * | 1987-09-24 | 1998-03-03 | The Administrators Of Tulane Educational Fund | Peptide analogs of bombesin |
| US5436137A (en) * | 1992-07-27 | 1995-07-25 | Oregon Regional Primate Research Center | DNA sequence which encodes a peptide capable of promoting acrosome reaction |
| US5620955A (en) * | 1993-06-18 | 1997-04-15 | Peptide Technologies Corporation | Bombesin receptor antagonists and uses thereof |
| JP4954983B2 (ja) * | 2005-05-18 | 2012-06-20 | ファーマサイエンス・インコーポレイテッド | Ｂｉｒドメイン結合化合物 |
| BRPI0617751A2 (pt) | 2005-10-25 | 2011-08-02 | Aegera Therapeutics Inc | compostos de ligação do domìnio iap bir |
| US9284350B2 (en) | 2010-02-12 | 2016-03-15 | Pharmascience Inc. | IAP BIR domain binding compounds |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0315367A2 (en) * | 1987-11-02 | 1989-05-10 | Imperial Chemical Industries Plc | Polypeptides |
-
1990
- 1990-07-31 GB GB909016810A patent/GB9016810D0/en active Pending
-
1991
- 1991-07-30 CA CA002088166A patent/CA2088166A1/en not_active Abandoned
- 1991-07-30 EP EP91914148A patent/EP0541654A1/en not_active Withdrawn
- 1991-07-30 PT PT98498A patent/PT98498A/pt not_active Application Discontinuation
- 1991-07-30 IL IL99009A patent/IL99009A0/xx unknown
- 1991-07-30 IE IE267191A patent/IE912671A1/en unknown
- 1991-07-30 WO PCT/GB1991/001289 patent/WO1992002545A1/en not_active Application Discontinuation
- 1991-07-30 NZ NZ239183A patent/NZ239183A/xx unknown
- 1991-07-30 MC MC912312D patent/MC2312A1/xx unknown
- 1991-07-30 JP JP3513218A patent/JPH05509100A/ja active Pending
- 1991-07-30 MY MYPI91001370A patent/MY107031A/en unknown
- 1991-07-30 PL PL91297652A patent/PL167322B1/pl unknown
- 1991-07-30 AU AU83111/91A patent/AU653544B2/en not_active Ceased
- 1991-07-30 TW TW080105951A patent/TW234130B/zh active
- 1991-07-30 CZ CS9380A patent/CZ8093A3/cs unknown
- 1991-07-30 ZA ZA915978A patent/ZA915978B/xx unknown
- 1991-07-30 HU HU93239A patent/HUT63178A/hu unknown
- 1991-09-30 SK SK3893A patent/SK3893A3/sk unknown
-
1993
- 1993-01-26 NO NO930262A patent/NO930262D0/no unknown
- 1993-01-29 FI FI930411A patent/FI930411A7/fi not_active Application Discontinuation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0315367A2 (en) * | 1987-11-02 | 1989-05-10 | Imperial Chemical Industries Plc | Polypeptides |
Also Published As
| Publication number | Publication date |
|---|---|
| FI930411A0 (fi) | 1993-01-29 |
| EP0541654A1 (en) | 1993-05-19 |
| PL297652A1 (enrdf_load_stackoverflow) | 1992-07-13 |
| PL167322B1 (pl) | 1995-08-31 |
| SK3893A3 (en) | 1993-07-07 |
| AU8311191A (en) | 1992-03-02 |
| CA2088166A1 (en) | 1992-02-01 |
| MY107031A (en) | 1995-08-30 |
| NO930262L (no) | 1993-01-26 |
| HU9300239D0 (en) | 1993-04-28 |
| NO930262D0 (no) | 1993-01-26 |
| PT98498A (pt) | 1992-05-29 |
| HUT63178A (en) | 1993-07-28 |
| FI930411A7 (fi) | 1993-01-29 |
| WO1992002545A1 (en) | 1992-02-20 |
| ZA915978B (en) | 1993-04-28 |
| IL99009A0 (en) | 1992-07-15 |
| IE912671A1 (en) | 1992-02-12 |
| MC2312A1 (fr) | 1993-09-27 |
| CZ8093A3 (en) | 1994-01-19 |
| GB9016810D0 (en) | 1990-09-12 |
| TW234130B (enrdf_load_stackoverflow) | 1994-11-11 |
| NZ239183A (en) | 1993-07-27 |
| JPH05509100A (ja) | 1993-12-16 |
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