IT1251164B - New cyclic hexa:peptide derivs., are tachy:kinin antagonists - useful for treating arthritis, asthma, inflammation, tumours, gastrointestinal hyper motility, migraine, hypertension, etc. - Google Patents
New cyclic hexa:peptide derivs., are tachy:kinin antagonists - useful for treating arthritis, asthma, inflammation, tumours, gastrointestinal hyper motility, migraine, hypertension, etc.Info
- Publication number
- IT1251164B IT1251164B ITMI912231A IT1251164B IT 1251164 B IT1251164 B IT 1251164B IT MI912231 A ITMI912231 A IT MI912231A IT 1251164 B IT1251164 B IT 1251164B
- Authority
- IT
- Italy
- Prior art keywords
- acid
- aminoacid
- tachy
- tumours
- migraine
- Prior art date
Links
- 125000004122 cyclic group Chemical group 0.000 title abstract 2
- 206010052402 Gastrointestinal hypermotility Diseases 0.000 title 1
- 206010020772 Hypertension Diseases 0.000 title 1
- 206010061218 Inflammation Diseases 0.000 title 1
- 108010093008 Kinins Proteins 0.000 title 1
- 102000002397 Kinins Human genes 0.000 title 1
- 208000019695 Migraine disease Diseases 0.000 title 1
- 206010028980 Neoplasm Diseases 0.000 title 1
- 241001385887 Tachys Species 0.000 title 1
- 239000005557 antagonist Substances 0.000 title 1
- 206010003246 arthritis Diseases 0.000 title 1
- 208000006673 asthma Diseases 0.000 title 1
- 230000004054 inflammatory process Effects 0.000 title 1
- 206010027599 migraine Diseases 0.000 title 1
- 108090000765 processed proteins & peptides Proteins 0.000 title 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 abstract 4
- 235000001014 amino acid Nutrition 0.000 abstract 3
- 229940024606 amino acid Drugs 0.000 abstract 3
- 150000001413 amino acids Chemical class 0.000 abstract 3
- PECYZEOJVXMISF-REOHCLBHSA-N 3-amino-L-alanine Chemical compound [NH3+]C[C@H](N)C([O-])=O PECYZEOJVXMISF-REOHCLBHSA-N 0.000 abstract 2
- COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical compound OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 abstract 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 abstract 2
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 abstract 2
- BJBUEDPLEOHJGE-UHFFFAOYSA-N (2R,3S)-3-Hydroxy-2-pyrolidinecarboxylic acid Natural products OC1CCNC1C(O)=O BJBUEDPLEOHJGE-UHFFFAOYSA-N 0.000 abstract 1
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 abstract 1
- YPJJGMCMOHDOFZ-ZETCQYMHSA-N (2s)-2-(1-benzothiophen-3-ylamino)propanoic acid Chemical compound C1=CC=C2C(N[C@@H](C)C(O)=O)=CSC2=C1 YPJJGMCMOHDOFZ-ZETCQYMHSA-N 0.000 abstract 1
- CNMAQBJBWQQZFZ-LURJTMIESA-N (2s)-2-(pyridin-2-ylamino)propanoic acid Chemical compound OC(=O)[C@H](C)NC1=CC=CC=N1 CNMAQBJBWQQZFZ-LURJTMIESA-N 0.000 abstract 1
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 abstract 1
- 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 abstract 1
- WTOFYLAWDLQMBZ-UHFFFAOYSA-N 2-azaniumyl-3-thiophen-2-ylpropanoate Chemical compound OC(=O)C(N)CC1=CC=CS1 WTOFYLAWDLQMBZ-UHFFFAOYSA-N 0.000 abstract 1
- ODHCTXKNWHHXJC-GSVOUGTGSA-N 5-oxo-D-proline Chemical compound OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N 0.000 abstract 1
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 abstract 1
- 239000004475 Arginine Substances 0.000 abstract 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 abstract 1
- -1 D or L allosoleucine Chemical compound 0.000 abstract 1
- QWCKQJZIFLGMSD-GSVOUGTGSA-N D-alpha-aminobutyric acid Chemical compound CC[C@@H](N)C(O)=O QWCKQJZIFLGMSD-GSVOUGTGSA-N 0.000 abstract 1
- 125000003643 D-glutamine group Chemical group [H]N([H])[C@@]([H])(C(=O)[*])C([H])([H])C([H])([H])C(N([H])[H])=O 0.000 abstract 1
- 229930182832 D-phenylalanine Natural products 0.000 abstract 1
- QIVBCDIJIAJPQS-SECBINFHSA-N D-tryptophane Chemical compound C1=CC=C2C(C[C@@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-SECBINFHSA-N 0.000 abstract 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004471 Glycine Substances 0.000 abstract 1
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 abstract 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 abstract 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 abstract 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 abstract 1
- QWCKQJZIFLGMSD-VKHMYHEASA-N L-alpha-aminobutyric acid Chemical compound CC[C@H](N)C(O)=O QWCKQJZIFLGMSD-VKHMYHEASA-N 0.000 abstract 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 abstract 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 abstract 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 abstract 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 abstract 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 abstract 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 abstract 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 abstract 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 abstract 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 abstract 1
- LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 abstract 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 abstract 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 abstract 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 abstract 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 abstract 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 abstract 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004472 Lysine Substances 0.000 abstract 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 abstract 1
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 abstract 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 abstract 1
- 239000004473 Threonine Substances 0.000 abstract 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 abstract 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 abstract 1
- ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 abstract 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 abstract 1
- 235000004279 alanine Nutrition 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 abstract 1
- 235000009582 asparagine Nutrition 0.000 abstract 1
- 229960001230 asparagine Drugs 0.000 abstract 1
- 235000003704 aspartic acid Nutrition 0.000 abstract 1
- 229940000635 beta-alanine Drugs 0.000 abstract 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003857 carboxamides Chemical class 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 abstract 1
- 235000018417 cysteine Nutrition 0.000 abstract 1
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 abstract 1
- 235000013922 glutamic acid Nutrition 0.000 abstract 1
- 239000004220 glutamic acid Substances 0.000 abstract 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 abstract 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 abstract 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 abstract 1
- 229960000310 isoleucine Drugs 0.000 abstract 1
- 229930182817 methionine Natural products 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 abstract 1
- 230000001012 protector Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 1
- BJBUEDPLEOHJGE-IMJSIDKUSA-N trans-3-hydroxy-L-proline Chemical compound O[C@H]1CC[NH2+][C@@H]1C([O-])=O BJBUEDPLEOHJGE-IMJSIDKUSA-N 0.000 abstract 1
- PMMYEEVYMWASQN-IUYQGCFVSA-N trans-4-hydroxy-D-proline Chemical compound O[C@@H]1CN[C@@H](C(O)=O)C1 PMMYEEVYMWASQN-IUYQGCFVSA-N 0.000 abstract 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 abstract 1
- 239000004474 valine Substances 0.000 abstract 1
Abstract
Cyclic hexapeptides of the formula (I) and their salts are new. In (I), R1 is H or 1-4C alkyl; R3 is a natural or unnatural aminoacid radical with free or protected side chains or R3 is -(CH2)n-R" (where n is 1-5 and R" is cycloctyl, adamantyl, cyclohexyl or naphthyl, or additionally may be phenyl when n is other than 1, or additionally may be a substd. carboxamide gp. when n is 1 or 2); A1 is Gln or DGln; A2 is TrP or DTrp; A3 is Phe or DPhe; W is CONR1 or CH2NR1 (where R1 is H or CH3). The natural aminoacid is glycine, alanine, valine, leucine, isoleucine, proline, phenylalanine, tryptophan, methionine, serine, threonine, cysteine, tyrosine, asparagine, glutamine, aspartic acid, glutamic acid, lysine, arginine, or histidine, in L- or D-form. The unnatural aminoacid is beta-alanine, D or L 2-aminobutyric acid, D or L 2,3-diaminopropionic acid, D or L norleucine, D or L allosoleucine, D or L pyroglutamic acid, L or D 3-hydroxyproline, L or D 4-hydroxyproline, L or D phenylalanine substd. in the ortho, meta or para position, L or D thienylalanine, L or D pyridylalanine, beta (2- or 3-benzothienylalanine), or 1,2,3,4-tetrahydroisoquinolin -3-carboxylic acid. An aminoacid side chain protector is Mbs, Mtr, NO2, Z, Tos, Pmc, For, Me, Ac, 2-Br-Z, 2-Cl-Z, Bzl, 2,6-dichloro-Bzl, SO3H, Fmoc, OMe, OBzl, OFm, ONp or OSu.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT002231 IT1251164B (en) | 1991-08-08 | 1991-08-08 | New cyclic hexa:peptide derivs., are tachy:kinin antagonists - useful for treating arthritis, asthma, inflammation, tumours, gastrointestinal hyper motility, migraine, hypertension, etc. |
| AU23875/92A AU2387592A (en) | 1991-08-08 | 1992-08-03 | Cyclic hexapeptides as tachyquinin antagonists, their preparation and pharmaceutical compositions thereof |
| EP92916106A EP0606222A1 (en) | 1991-08-08 | 1992-08-03 | Cyclic hexapeptides as tachyquinin antagonists, their preparation and pharmaceutical compositions thereof |
| PCT/EP1992/001760 WO1993003059A1 (en) | 1991-08-08 | 1992-08-03 | Cyclic hexapeptides as tachyquinin antagonists, their preparation and pharmaceutical compositions thereof |
| JP5503277A JPH06509571A (en) | 1991-08-08 | 1992-08-03 | Process for producing cyclic hexapeptides as tachykinin antagonists and pharmaceutical compounds thereof |
| PT100764A PT100764A (en) | 1991-08-08 | 1992-08-07 | CYCLIC HEXAPEPTIDES OF TAQUIQUININS AND THEIR PHARMACEUTICALLY ACCEPTANT SALTS, ITS PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THESE ANALOGS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT002231 IT1251164B (en) | 1991-08-08 | 1991-08-08 | New cyclic hexa:peptide derivs., are tachy:kinin antagonists - useful for treating arthritis, asthma, inflammation, tumours, gastrointestinal hyper motility, migraine, hypertension, etc. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| ITMI912231A0 ITMI912231A0 (en) | 1991-08-08 |
| ITMI912231A1 ITMI912231A1 (en) | 1993-02-09 |
| IT1251164B true IT1251164B (en) | 1995-05-04 |
Family
ID=11360552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IT002231 IT1251164B (en) | 1991-08-08 | 1991-08-08 | New cyclic hexa:peptide derivs., are tachy:kinin antagonists - useful for treating arthritis, asthma, inflammation, tumours, gastrointestinal hyper motility, migraine, hypertension, etc. |
Country Status (1)
| Country | Link |
|---|---|
| IT (1) | IT1251164B (en) |
-
1991
- 1991-08-08 IT IT002231 patent/IT1251164B/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| ITMI912231A0 (en) | 1991-08-08 |
| ITMI912231A1 (en) | 1993-02-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 0001 | Granted | ||
| TA | Fee payment date (situation as of event date), data collected since 19931001 |
Effective date: 19970828 |