JPH06507402A - 治療活性を有するα−置換ポリペプチド - Google Patents
治療活性を有するα−置換ポリペプチドInfo
- Publication number
- JPH06507402A JPH06507402A JP4511401A JP51140192A JPH06507402A JP H06507402 A JPH06507402 A JP H06507402A JP 4511401 A JP4511401 A JP 4511401A JP 51140192 A JP51140192 A JP 51140192A JP H06507402 A JPH06507402 A JP H06507402A
- Authority
- JP
- Japan
- Prior art keywords
- array
- compound
- methyl
- carbonyl
- tryptophyl
- 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.)
- Pending
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title description 26
- 102000004196 processed proteins & peptides Human genes 0.000 title description 13
- 229920001184 polypeptide Polymers 0.000 title description 3
- 230000001225 therapeutic effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 83
- -1 L-tryptophyl-α-methyl-DL-phenylalaninamide Chemical group 0.000 claims description 44
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 42
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 19
- 150000001408 amides Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 12
- 229940024606 amino acid Drugs 0.000 claims description 9
- 150000001413 amino acids Chemical class 0.000 claims description 8
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 7
- 125000000539 amino acid group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 230000000903 blocking effect Effects 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 210000004899 c-terminal region Anatomy 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 4
- LEBDCRNSLNAHHD-SNVBAGLBSA-N (2r)-2-amino-2-methyl-3-phenylpropanamide Chemical group NC(=O)[C@@](N)(C)CC1=CC=CC=C1 LEBDCRNSLNAHHD-SNVBAGLBSA-N 0.000 claims description 3
- 239000004395 L-leucine Substances 0.000 claims description 3
- 229960003136 leucine Drugs 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
- 239000004471 Glycine Substances 0.000 claims description 2
- HYOWVAAEQCNGLE-JTQLQIEISA-N alpha-methyl-L-phenylalanine Chemical group OC(=O)[C@](N)(C)CC1=CC=CC=C1 HYOWVAAEQCNGLE-JTQLQIEISA-N 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- LEBDCRNSLNAHHD-UHFFFAOYSA-N 2-amino-2-methyl-3-phenylpropanamide Chemical group NC(=O)C(N)(C)CC1=CC=CC=C1 LEBDCRNSLNAHHD-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 2
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims 1
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- WTRKFKJRNBUDIR-FSOCYVASSA-N naphthalen-1-ylmethyl N-[3-[1-[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]-4-chlorocyclohexa-2,4-dien-1-yl]-1-[(2-amino-2-oxoethyl)amino]-2-methyl-1-oxopropan-2-yl]carbamate Chemical compound C1(=CC=CC2=CC=CC=C12)COC(=O)NC(CC1(CC=C(C=C1)Cl)C([C@@H](N)CC1=CNC2=CC=CC=C12)=O)(C(=O)NCC(=O)N)C WTRKFKJRNBUDIR-FSOCYVASSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 21
- 238000004458 analytical method Methods 0.000 description 20
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- 238000002844 melting Methods 0.000 description 17
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- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 14
- 239000008194 pharmaceutical composition Substances 0.000 description 13
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 125000002707 L-tryptophyl group Chemical group [H]C1=C([H])C([H])=C2C(C([C@](N([H])[H])(C(=O)[*])[H])([H])[H])=C([H])N([H])C2=C1[H] 0.000 description 11
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- 229920005989 resin Polymers 0.000 description 10
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
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- 235000001014 amino acid Nutrition 0.000 description 7
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- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 6
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- TZESVYIFIDOAJI-LCPHSBLTSA-N anthracen-9-ylmethyl N-[2-amino-3-[1-[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]cyclohexa-2,4-dien-1-yl]-2-methylpropanoyl]carbamate Chemical compound C1=CC=CC2=CC3=CC=CC=C3C(=C12)COC(=O)NC(C(N)(CC1(CC=CC=C1)C([C@@H](N)CC1=CNC2=CC=CC=C12)=O)C)=O TZESVYIFIDOAJI-LCPHSBLTSA-N 0.000 description 5
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- KQNBRMUBPRGXSL-UHFFFAOYSA-N 1-(bromomethyl)-4-chlorobenzene Chemical compound ClC1=CC=C(CBr)C=C1 KQNBRMUBPRGXSL-UHFFFAOYSA-N 0.000 description 3
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
- C07K14/66—Thymopoietins
-
- 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
- C07K14/665—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans derived from pro-opiomelanocortin, pro-enkephalin or pro-dynorphin
- C07K14/70—Enkephalins
-
- 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
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
- C07K5/06043—Leu-amino acid
-
- 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
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- C07K5/06156—Dipeptides with the first amino acid being heterocyclic and Trp-amino acid; Derivatives thereof
-
- 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
- C07K5/0815—Tripeptides with the first amino acid being basic
-
- 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
- C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
-
- 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
- C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
- C07K5/0825—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp and Glp-amino acid; Derivatives thereof
-
- 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
- C07K5/1016—Tetrapeptides 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
- C07K5/1021—Tetrapeptides with the first amino acid being acidic
-
- 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)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Gastroenterology & Hepatology (AREA)
- Zoology (AREA)
- Toxicology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Reproductive Health (AREA)
- Rheumatology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Child & Adolescent Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US690,755 | 1976-05-27 | ||
| US852,086 | 1977-11-16 | ||
| US69075591A | 1991-04-24 | 1991-04-24 | |
| US85208692A | 1992-03-20 | 1992-03-20 | |
| PCT/US1992/003119 WO1992019254A1 (en) | 1991-04-24 | 1992-04-15 | α-SUBSTITUTED POLYPEPTIDES HAVING THERAPEUTIC ACTIVITY |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06507402A true JPH06507402A (ja) | 1994-08-25 |
Family
ID=27104664
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4511401A Pending JPH06507402A (ja) | 1991-03-20 | 1992-04-15 | 治療活性を有するα−置換ポリペプチド |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0668770A1 (enrdf_load_stackoverflow) |
| JP (1) | JPH06507402A (enrdf_load_stackoverflow) |
| AU (1) | AU1907292A (enrdf_load_stackoverflow) |
| CA (1) | CA2106764A1 (enrdf_load_stackoverflow) |
| IE (1) | IE921321A1 (enrdf_load_stackoverflow) |
| NZ (1) | NZ242441A (enrdf_load_stackoverflow) |
| PT (1) | PT100422A (enrdf_load_stackoverflow) |
| WO (1) | WO1992019254A1 (enrdf_load_stackoverflow) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU674525B2 (en) * | 1992-06-01 | 1997-01-02 | Magainin Pharmaceuticals, Inc. | Biologically active peptides having N-terminal substitutions |
| AU5359694A (en) * | 1992-10-19 | 1994-05-09 | Warner-Lambert Company | Analogues of cholecystokinin (30-33) containing an alpha-substituted aminoacid |
| FR2700472B1 (fr) | 1993-01-19 | 1995-02-17 | Rhone Poulenc Rorer Sa | Association synergisante ayant un effet antagoniste des récepteurs NK1 et NK2. |
| WO1995012611A1 (en) * | 1993-11-01 | 1995-05-11 | Japat Ltd. | Endothelin receptor antagonists |
| US5610145A (en) * | 1994-04-15 | 1997-03-11 | Warner-Lambert Company | Tachykinin antagonists |
| US5554644A (en) * | 1994-06-08 | 1996-09-10 | Warner-Lambert Company | Tachykinin (NK2) antagonists |
| FR2735687B1 (fr) * | 1995-06-21 | 1997-08-14 | Sederma Sa | Nouvelles compositions cosmetiques amincissantes |
| EP0920445B1 (fr) * | 1996-08-23 | 2003-01-02 | Sederma S.A. | Peptides synthetiques et leur utilisation dans les compositions cosmetiques ou dermopharmaceutiques |
| IL137820A (en) | 2000-08-10 | 2009-06-15 | S I S Shulov Inst For Science | Pharmaceutical composition for topical administration comprising an analgesic peptide |
| US6593362B2 (en) | 2001-05-21 | 2003-07-15 | Guilford Pharmaceuticals Inc. | Non-peptidic cyclophilin binding compounds and their use |
| WO2006049681A2 (en) * | 2004-08-30 | 2006-05-11 | Bayer Pharmaceuticals Corporation | Selective neuropeptide y2 receptor agonists |
| RU2010114057A (ru) * | 2007-09-11 | 2011-10-20 | Мондобайотек Лабораториз Аг (Li) | Применение натрийуретического пептида с-типа индивидуально или в сочетании с нейропептидом af в качестве терапевтического средства |
| HUP0700782A3 (en) * | 2007-12-05 | 2009-11-30 | Biostatin Gyogyszerkutato Fejl | Novel peptides and amino acid derivatives, pharmaceutical compositions containing the same and use of the compounds |
| CA2830135C (en) | 2011-03-28 | 2019-12-17 | S.I.S. Shulov Innovative Science Ltd. | Method for treating disorders of the skin |
| WO2025049670A1 (en) * | 2023-08-31 | 2025-03-06 | Northwestern University | Compounds and methods for treating central nervous system disorders |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK309379A (da) * | 1978-07-24 | 1980-01-25 | Merck & Co Inc | Fremgangsmaade til fremstilling af aminosyrer og aminosyreestere |
| US4505853A (en) * | 1983-11-18 | 1985-03-19 | Ortho Pharmaceutical Corporation | Enzyme-resistant immunomodulatory peptides |
| US4689318A (en) * | 1985-08-29 | 1987-08-25 | The Salk Institute For Biological Studies | GRF analogs |
| US5098995A (en) * | 1987-05-22 | 1992-03-24 | The Salk Institute For Biological Studies | GRF Analogs VIIA |
| NZ229004A (en) * | 1988-05-19 | 1993-09-27 | Immunobiology Res Inst Inc | Tetrapeptides having t cell helper acitivity |
| NZ234264A (en) * | 1989-06-29 | 1993-05-26 | Warner Lambert Co | N-substituted cycloalkyl and polycycloalkyl alpha-substituted trp-phe- and phenethylamine derivatives, and pharmaceutical compositions |
-
1992
- 1992-04-15 JP JP4511401A patent/JPH06507402A/ja active Pending
- 1992-04-15 AU AU19072/92A patent/AU1907292A/en not_active Abandoned
- 1992-04-15 EP EP92911434A patent/EP0668770A1/en not_active Withdrawn
- 1992-04-15 CA CA002106764A patent/CA2106764A1/en not_active Abandoned
- 1992-04-15 WO PCT/US1992/003119 patent/WO1992019254A1/en not_active Application Discontinuation
- 1992-04-22 NZ NZ242441A patent/NZ242441A/en unknown
- 1992-04-23 IE IE132192A patent/IE921321A1/en not_active Application Discontinuation
- 1992-04-23 PT PT100422A patent/PT100422A/pt not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0668770A4 (enrdf_load_stackoverflow) | 1995-09-27 |
| IE921321A1 (en) | 1992-11-04 |
| WO1992019254A1 (en) | 1992-11-12 |
| CA2106764A1 (en) | 1992-10-25 |
| PT100422A (pt) | 1993-09-30 |
| EP0668770A1 (en) | 1995-08-30 |
| NZ242441A (en) | 1995-02-24 |
| AU1907292A (en) | 1992-12-21 |
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