RU2508295C2 - Синтетические пептиды с ненаркотическим типом анальгетического действия - Google Patents
Синтетические пептиды с ненаркотическим типом анальгетического действия Download PDFInfo
- Publication number
- RU2508295C2 RU2508295C2 RU2012110908/10A RU2012110908A RU2508295C2 RU 2508295 C2 RU2508295 C2 RU 2508295C2 RU 2012110908/10 A RU2012110908/10 A RU 2012110908/10A RU 2012110908 A RU2012110908 A RU 2012110908A RU 2508295 C2 RU2508295 C2 RU 2508295C2
- Authority
- RU
- Russia
- Prior art keywords
- leu
- peptide
- peptides
- gln
- lys
- Prior art date
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title claims abstract description 80
- 102000004196 processed proteins & peptides Human genes 0.000 title claims abstract description 38
- 230000000202 analgesic effect Effects 0.000 title claims abstract description 30
- 230000003533 narcotic effect Effects 0.000 title claims abstract description 15
- 150000001413 amino acids Chemical class 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims abstract description 5
- 230000002441 reversible effect Effects 0.000 claims abstract description 5
- OUYCCCASQSFEME-MRVPVSSYSA-N D-tyrosine Chemical compound OC(=O)[C@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-MRVPVSSYSA-N 0.000 claims abstract description 3
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 230000000694 effects Effects 0.000 abstract description 7
- 239000000126 substance Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract 1
- 230000036407 pain Effects 0.000 description 20
- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 description 19
- 229940024606 amino acid Drugs 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 14
- 241000700159 Rattus Species 0.000 description 13
- 102000055006 Calcitonin Human genes 0.000 description 12
- 108060001064 Calcitonin Proteins 0.000 description 12
- 229960004015 calcitonin Drugs 0.000 description 12
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 9
- 239000012634 fragment Substances 0.000 description 8
- 108010068072 salmon calcitonin Proteins 0.000 description 8
- 239000000730 antalgic agent Substances 0.000 description 7
- 229960003773 calcitonin (salmon synthetic) Drugs 0.000 description 7
- 229940035676 analgesics Drugs 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 210000002683 foot Anatomy 0.000 description 5
- 229960002885 histidine Drugs 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 230000004044 response Effects 0.000 description 5
- HNDVDQJCIGZPNO-RXMQYKEDSA-N D-histidine Chemical compound OC(=O)[C@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-RXMQYKEDSA-N 0.000 description 4
- 229930195721 D-histidine Natural products 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 230000036592 analgesia Effects 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
- GHCZTIFQWKKGSB-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;phosphoric acid Chemical compound OP(O)(O)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O GHCZTIFQWKKGSB-UHFFFAOYSA-N 0.000 description 2
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 208000010191 Osteitis Deformans Diseases 0.000 description 2
- 208000001132 Osteoporosis Diseases 0.000 description 2
- 208000027868 Paget disease Diseases 0.000 description 2
- 125000000539 amino acid group Chemical group 0.000 description 2
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 230000001900 immune effect Effects 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 208000027202 mammary Paget disease Diseases 0.000 description 2
- 229960005181 morphine Drugs 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000010532 solid phase synthesis reaction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- FZTIWOBQQYPTCJ-UHFFFAOYSA-N 4-[4-(4-carboxyphenyl)phenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(O)=O)C=C1 FZTIWOBQQYPTCJ-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 108010001789 Calcitonin Receptors Proteins 0.000 description 1
- 102100038520 Calcitonin receptor Human genes 0.000 description 1
- 101500007657 Crotalus durissus terrificus Crotoxin chain gamma Proteins 0.000 description 1
- 150000008574 D-amino acids Chemical class 0.000 description 1
- 206010012335 Dependence Diseases 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 108010049140 Endorphins Proteins 0.000 description 1
- 102000009025 Endorphins Human genes 0.000 description 1
- 108010092674 Enkephalins Proteins 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 101000741445 Homo sapiens Calcitonin Proteins 0.000 description 1
- 150000008575 L-amino acids Chemical class 0.000 description 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
- URLZCHNOLZSCCA-VABKMULXSA-N Leu-enkephalin Chemical class C([C@@H](C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=CC=C1 URLZCHNOLZSCCA-VABKMULXSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 208000030136 Marchiafava-Bignami Disease Diseases 0.000 description 1
- 208000029725 Metabolic bone disease Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 102000003797 Neuropeptides Human genes 0.000 description 1
- 108090000189 Neuropeptides Proteins 0.000 description 1
- 108010093625 Opioid Peptides Proteins 0.000 description 1
- 102000001490 Opioid Peptides Human genes 0.000 description 1
- 102000003840 Opioid Receptors Human genes 0.000 description 1
- 108090000137 Opioid Receptors Proteins 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 102000015731 Peptide Hormones Human genes 0.000 description 1
- 108010038988 Peptide Hormones Proteins 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 230000003913 calcium metabolism Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000035606 childbirth Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000668 effect on calcium Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- SLXXEMSPHFYCLE-UHFFFAOYSA-N ethane-1,1-dithiol;hydrate Chemical compound O.CC(S)S SLXXEMSPHFYCLE-UHFFFAOYSA-N 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 230000003370 grooming effect Effects 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 229940045644 human calcitonin Drugs 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 239000003399 opiate peptide Substances 0.000 description 1
- 239000000014 opioid analgesic Substances 0.000 description 1
- 229940005483 opioid analgesics Drugs 0.000 description 1
- 229940000673 orphan drug Drugs 0.000 description 1
- 239000002859 orphan drug Substances 0.000 description 1
- 239000000813 peptide hormone Substances 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000019833 protease Nutrition 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 230000000862 serotonergic effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- -1 t-butyloxycarbonyl Chemical group 0.000 description 1
- 230000003390 teratogenic effect Effects 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Images
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
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
-
- 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)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Rheumatology (AREA)
- Anesthesiology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU2012110908/10A RU2508295C2 (ru) | 2012-03-22 | 2012-03-22 | Синтетические пептиды с ненаркотическим типом анальгетического действия |
| US14/386,675 US9260482B2 (en) | 2012-03-22 | 2012-12-07 | Synthetic peptides with a non-narcotic type of analgesic effect |
| EP12871733.7A EP2848629B1 (en) | 2012-03-22 | 2012-12-07 | Synthetic peptides wtih a non-narcotic type of analgesic effect |
| PCT/RU2012/001036 WO2013141750A1 (ru) | 2012-03-22 | 2012-12-07 | Синтетические пептиды с ненаркотическим типом анальгетического действия |
| ES12871733.7T ES2651265T3 (es) | 2012-03-22 | 2012-12-07 | Péptidos sintéticos con un efecto analgésico de tipo no narcótico |
| CA2867994A CA2867994C (en) | 2012-03-22 | 2012-12-07 | Synthetic peptides with a non-narcotic type of analgesic effect |
| JP2015501616A JP6118392B2 (ja) | 2012-03-22 | 2012-12-07 | 非麻薬性鎮痛作用を有する合成ペプチド |
| IN2080MUN2014 IN2014MN02080A (cg-RX-API-DMAC10.html) | 2012-03-22 | 2012-12-07 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU2012110908/10A RU2508295C2 (ru) | 2012-03-22 | 2012-03-22 | Синтетические пептиды с ненаркотическим типом анальгетического действия |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2012110908A RU2012110908A (ru) | 2013-09-27 |
| RU2508295C2 true RU2508295C2 (ru) | 2014-02-27 |
Family
ID=49223070
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2012110908/10A RU2508295C2 (ru) | 2012-03-22 | 2012-03-22 | Синтетические пептиды с ненаркотическим типом анальгетического действия |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9260482B2 (cg-RX-API-DMAC10.html) |
| EP (1) | EP2848629B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JP6118392B2 (cg-RX-API-DMAC10.html) |
| CA (1) | CA2867994C (cg-RX-API-DMAC10.html) |
| ES (1) | ES2651265T3 (cg-RX-API-DMAC10.html) |
| IN (1) | IN2014MN02080A (cg-RX-API-DMAC10.html) |
| RU (1) | RU2508295C2 (cg-RX-API-DMAC10.html) |
| WO (1) | WO2013141750A1 (cg-RX-API-DMAC10.html) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2651491C1 (ru) * | 2017-04-07 | 2018-04-19 | Общество с ограниченной ответственностью "Биофармокс" | Специфические пептидные ингибиторы клатрина |
| RU2759722C2 (ru) * | 2016-12-23 | 2021-11-17 | Форшунгсцентрум Юлих Гмбх | D-энантиомерные пептиды для терапии хронической и невропатической боли |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015093515A1 (ja) * | 2013-12-19 | 2015-06-25 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | １－インダンスルファミド誘導体を含む疼痛の治療および／または予防剤 |
| US20210228677A1 (en) * | 2020-01-28 | 2021-07-29 | Pharmbiotech OY | Pharmaceutical composition and a method for its manufacture |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1229658B (it) | 1989-04-21 | 1991-09-06 | Eniricerche Spa | Analoghi della timopentina retro-inversi ad uno o piu' legami, il metodo per la loro sintesi ed il loro impiego per la preparazione di composizioni farmaceutiche. |
| US5175146A (en) * | 1989-12-05 | 1992-12-29 | Vical, Inc. | Synthetic calcitonin peptides |
-
2012
- 2012-03-22 RU RU2012110908/10A patent/RU2508295C2/ru active IP Right Revival
- 2012-12-07 JP JP2015501616A patent/JP6118392B2/ja active Active
- 2012-12-07 ES ES12871733.7T patent/ES2651265T3/es active Active
- 2012-12-07 CA CA2867994A patent/CA2867994C/en active Active
- 2012-12-07 US US14/386,675 patent/US9260482B2/en active Active
- 2012-12-07 IN IN2080MUN2014 patent/IN2014MN02080A/en unknown
- 2012-12-07 WO PCT/RU2012/001036 patent/WO2013141750A1/ru not_active Ceased
- 2012-12-07 EP EP12871733.7A patent/EP2848629B1/en active Active
Non-Patent Citations (5)
| Title |
|---|
| ANDREEV N.A. et al, Synthesis and study of the biological activity of fragments salmon calcitonin II, 1993, J. Chemistry of Natural Compounds, v.29, i.1, p.107-112. * |
| ANDREEV N.A. et al, Synthesis and study of the biological activity of fragments salmon calcitonin II, 1993, J. Chemistry of Natural Compounds, v.29, i.1, p.107-112. ROGACHEVSKII I.V. et al., Synthesis and steric structure of H-Leu-His-Lys-Leu-Gln-Thr-NH2 and H-Ala-D-Ala-Lys-Leu-Ala-Thr-NH2 Peptides, Russian Journal of General Chemistry, 2005, v.75, n.5, p.815-824. AZIRA M., Possible Mechanisms of the Analgesis Action of calcitonin, 2002, Bone v.30, n.5, p.80S-83S. ЕРШОВА О.Б. и др. Возможные перспективы комплексного использования кальцитонина лосося при остеопорозе, 2005. * |
| AZIRA M., Possible Mechanisms of the Analgesis Action of calcitonin, 2002, Bone v.30, n.5, p.80S-83S. * |
| ROGACHEVSKII I.V. et al., Synthesis and steric structure of H-Leu-His-Lys-Leu-Gln-Thr-NH2 and H-Ala-D-Ala-Lys-Leu-Ala-Thr-NH2 Peptides, Russian Journal of General Chemistry, 2005, v.75, n.5, p.815-824. * |
| ЕРШОВА О.Б. и др. Возможные перспективы комплексного использования кальцитонина лосося при остеопорозе, 2005. * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2759722C2 (ru) * | 2016-12-23 | 2021-11-17 | Форшунгсцентрум Юлих Гмбх | D-энантиомерные пептиды для терапии хронической и невропатической боли |
| US11224632B2 (en) | 2016-12-23 | 2022-01-18 | Forschungszentrum Juelich Gmbh | Methods of treating chronic and neuropathic pain mediated by N-type neuronal calcium channels using D-enantiomeric peptides |
| RU2651491C1 (ru) * | 2017-04-07 | 2018-04-19 | Общество с ограниченной ответственностью "Биофармокс" | Специфические пептидные ингибиторы клатрина |
| WO2018186770A1 (ru) | 2017-04-07 | 2018-10-11 | Олег Аркадьевич КОТИН | Специфические пептидные ингибиторы клатрина |
Also Published As
| Publication number | Publication date |
|---|---|
| JP6118392B2 (ja) | 2017-04-19 |
| RU2012110908A (ru) | 2013-09-27 |
| IN2014MN02080A (cg-RX-API-DMAC10.html) | 2015-08-21 |
| EP2848629A4 (en) | 2016-03-02 |
| CA2867994A1 (en) | 2013-09-26 |
| US9260482B2 (en) | 2016-02-16 |
| US20150073123A1 (en) | 2015-03-12 |
| JP2015512385A (ja) | 2015-04-27 |
| EP2848629A1 (en) | 2015-03-18 |
| ES2651265T3 (es) | 2018-01-25 |
| CA2867994C (en) | 2017-05-16 |
| WO2013141750A1 (ru) | 2013-09-26 |
| EP2848629B1 (en) | 2017-09-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI92326C (fi) | LHRH:n nonapeptidi- ja dekapeptidianalogeja, jotka ovat käyttökelpoisia LHRH:n antagonisteina | |
| KR100543190B1 (ko) | 향상된생물학적효능을갖는키메라성지방체-프로-지알에프유사체 | |
| TWI221845B (en) | Peptide analogues | |
| JP2000516579A (ja) | 腸栄養性ｇｌｐ―２ペプチドのアンタゴニスト | |
| CN106661088B (zh) | 鱼类繁殖中的神经激肽b拮抗剂 | |
| TW585873B (en) | Antagonistic analogs of GH-RH inhibiting IGF-I and -II | |
| AU2018362018A1 (en) | Peptide conjugate CGRP receptor antagonists and methods of preparation and uses thereof | |
| KR102117216B1 (ko) | 강력한 작용제 효과를 지닌 신규한 ｇｈ-ｒｈ 유사체 | |
| CA2069943A1 (en) | Synthetic calcitonin peptides | |
| JP2007526900A (ja) | Ｇｈ−ｒｈのアンタゴニスト誘導体（２００３） | |
| EP2848629B1 (en) | Synthetic peptides wtih a non-narcotic type of analgesic effect | |
| KR20250140094A (ko) | Gip/glp1/gcg 삼중-수용체 효능제 및 그의 용도 | |
| US11975050B2 (en) | Parathyroid hormone polypeptide conjugates and methods of their use | |
| Theobald et al. | Novel gonadotropin-releasing hormone antagonists: peptides incorporating modified N. omega.-cyanoguanidino moieties | |
| CZ91497A3 (en) | Peptides and pharmaceutical preparations containing thereof | |
| EP0592512A1 (en) | NON-DESENSITIZING ANALOGS OF GnRH AND OTHER BIOLOGICALLY ACTIVE LIGANDS | |
| WO2017073764A1 (ja) | 新規ｎｋ３受容体アゴニスト | |
| DE68923572T2 (de) | Peptide. | |
| JPH0770178A (ja) | 胃腸運動刺激活性を有するモチリン類似ポリペプチド | |
| JP7395149B2 (ja) | 神経障害性疼痛における使用のための新規のハイブリッドペプチド模倣物 | |
| EP2842965A1 (en) | Neuromedin U analogs comprising serum albumin binding amino acid residue | |
| JPH06509571A (ja) | タキキニン拮抗薬としての環状ヘキサペプチドの製法およびその薬学的化合物 | |
| WO1996030405A1 (en) | Peptides with growth promotion properties | |
| CZ6764U1 (cs) | Peptldové analogy kuřecího GnRH II a lososího GnRH | |
| HUP0900305A2 (en) | Peptide derivatives, process for their preparation and their therapeutical use |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20150323 |
|
| NF4A | Reinstatement of patent |
Effective date: 20160210 |
|
| PC41 | Official registration of the transfer of exclusive right |
Effective date: 20160311 |