DK168564B1 - Anvendelse af N-acylerede derivater af L-tryptophan til fremstilling af et lægemiddel til lindring af human smerte, farmaceutiske præparater indeholdende dem, samt sådanne nye farmaceutisk aktive derivater - Google Patents
Anvendelse af N-acylerede derivater af L-tryptophan til fremstilling af et lægemiddel til lindring af human smerte, farmaceutiske præparater indeholdende dem, samt sådanne nye farmaceutisk aktive derivater Download PDFInfo
- Publication number
- DK168564B1 DK168564B1 DK381486A DK381486A DK168564B1 DK 168564 B1 DK168564 B1 DK 168564B1 DK 381486 A DK381486 A DK 381486A DK 381486 A DK381486 A DK 381486A DK 168564 B1 DK168564 B1 DK 168564B1
- Authority
- DK
- Denmark
- Prior art keywords
- analgesic
- tryptophan
- compounds
- derivatives
- effect
- Prior art date
Links
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical class C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 title claims abstract description 14
- 230000036407 pain Effects 0.000 title claims abstract description 13
- 239000003814 drug Substances 0.000 title claims description 20
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 49
- 230000000694 effects Effects 0.000 claims description 26
- 230000000202 analgesic effect Effects 0.000 claims description 23
- -1 4-fluorobenzyloxy, 4-bromobenzyloxy, 3,4-dichlorobenzyloxy, 3,4-dichlorophenyl Chemical group 0.000 claims description 18
- 229940079593 drug Drugs 0.000 claims description 16
- 230000009471 action Effects 0.000 claims description 5
- 230000002708 enhancing effect Effects 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 229940127557 pharmaceutical product Drugs 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 230000001575 pathological effect Effects 0.000 abstract description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract description 2
- 230000000968 intestinal effect Effects 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- 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 26
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 17
- 238000012360 testing method Methods 0.000 description 16
- 241001465754 Metazoa Species 0.000 description 14
- 101800001982 Cholecystokinin Proteins 0.000 description 13
- 102100025841 Cholecystokinin Human genes 0.000 description 13
- 229940107137 cholecystokinin Drugs 0.000 description 13
- 229960005181 morphine Drugs 0.000 description 13
- 238000002474 experimental method Methods 0.000 description 10
- 241000700159 Rattus Species 0.000 description 9
- 229960004799 tryptophan Drugs 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 229940127240 opiate Drugs 0.000 description 7
- 230000001225 therapeutic effect Effects 0.000 description 7
- 230000008602 contraction Effects 0.000 description 6
- 210000000232 gallbladder Anatomy 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000000730 antalgic agent Substances 0.000 description 5
- 238000010609 cell counting kit-8 assay Methods 0.000 description 5
- 108010087230 Sincalide Proteins 0.000 description 4
- 229940035676 analgesics Drugs 0.000 description 4
- 230000003042 antagnostic effect Effects 0.000 description 4
- 230000001663 anti-spastic effect Effects 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000003533 narcotic effect Effects 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- 241000700199 Cavia porcellus Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- 102000004196 processed proteins & peptides Human genes 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229940126639 Compound 33 Drugs 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
- 108010093625 Opioid Peptides Proteins 0.000 description 2
- 102000001490 Opioid Peptides Human genes 0.000 description 2
- 239000008896 Opium Substances 0.000 description 2
- PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000036592 analgesia Effects 0.000 description 2
- 208000022531 anorexia Diseases 0.000 description 2
- 230000002567 autonomic effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 210000001072 colon Anatomy 0.000 description 2
- 230000001595 contractor effect Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 206010061428 decreased appetite Diseases 0.000 description 2
- 238000001784 detoxification Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- XCKKIKBIPZJUET-VYKNHSEDSA-N morphine hydrochloride Chemical compound Cl.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O XCKKIKBIPZJUET-VYKNHSEDSA-N 0.000 description 2
- 229960001027 opium Drugs 0.000 description 2
- 229960003857 proglumide Drugs 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- QJERBBQXOMUURJ-INIZCTEOSA-N (2s)-2-[(4-chlorobenzoyl)amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C1=CC=C(Cl)C=C1 QJERBBQXOMUURJ-INIZCTEOSA-N 0.000 description 1
- RJEUERNNQHNSKG-CCKFTAQKSA-N (2s)-2-amino-n-[(2r)-1-[[2-[[(2s)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-2-oxoethyl]amino]-1-oxopropan-2-yl]-3-(4-hydroxyphenyl)propanamide Chemical compound C([C@H](N)C(=O)N[C@H](C)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)C1=CC=C(O)C=C1 RJEUERNNQHNSKG-CCKFTAQKSA-N 0.000 description 1
- CNDKJCOMEMJVKI-UHFFFAOYSA-N (4-fluorophenyl)methyl carbonochloridate Chemical compound FC1=CC=C(COC(Cl)=O)C=C1 CNDKJCOMEMJVKI-UHFFFAOYSA-N 0.000 description 1
- 150000004803 5-hydroxytryptophans Chemical class 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 102000004859 Cholecystokinin Receptors Human genes 0.000 description 1
- 108090001085 Cholecystokinin Receptors Proteins 0.000 description 1
- 206010052804 Drug tolerance Diseases 0.000 description 1
- 108010092674 Enkephalins Proteins 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
- 101000986989 Naja kaouthia Acidic phospholipase A2 CM-II Proteins 0.000 description 1
- 206010029333 Neurosis Diseases 0.000 description 1
- ZQTQPYJGMWHXMO-UHFFFAOYSA-N OOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOO ZQTQPYJGMWHXMO-UHFFFAOYSA-N 0.000 description 1
- 102100027069 Odontogenic ameloblast-associated protein Human genes 0.000 description 1
- 101710091533 Odontogenic ameloblast-associated protein Proteins 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241000204914 Salmonella enterica subsp. enterica serovar Give Species 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229950006062 benzotript Drugs 0.000 description 1
- 239000012867 bioactive agent Substances 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 description 1
- 229960004193 dextropropoxyphene Drugs 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 230000007515 enzymatic degradation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 210000003191 femoral vein Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- 230000026781 habituation Effects 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 208000002551 irritable bowel syndrome Diseases 0.000 description 1
- 210000003140 lateral ventricle Anatomy 0.000 description 1
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- 230000008018 melting Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229960005195 morphine hydrochloride Drugs 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 208000015238 neurotic disease Diseases 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000008058 pain sensation Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
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- 230000035939 shock Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 210000003384 transverse colon Anatomy 0.000 description 1
- 210000001364 upper extremity Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT68241/84A IT1179866B (it) | 1984-12-12 | 1984-12-12 | Derivati del triptofano farmaceuticamente attivi e composizioni farmaceutiche che li contengono |
| IT6824184 | 1984-12-12 | ||
| EP8500672 | 1985-12-05 | ||
| PCT/EP1985/000672 WO1986003489A1 (en) | 1984-12-12 | 1985-12-05 | Pharmaceutically active derivatives of tryptophan and pharmaceutical compositions containing them |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK381486D0 DK381486D0 (da) | 1986-08-11 |
| DK381486A DK381486A (da) | 1986-08-11 |
| DK168564B1 true DK168564B1 (da) | 1994-04-25 |
Family
ID=11308641
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK381486A DK168564B1 (da) | 1984-12-12 | 1986-08-11 | Anvendelse af N-acylerede derivater af L-tryptophan til fremstilling af et lægemiddel til lindring af human smerte, farmaceutiske præparater indeholdende dem, samt sådanne nye farmaceutisk aktive derivater |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4870097A (it) |
| EP (1) | EP0237522B1 (it) |
| JP (1) | JPS62501292A (it) |
| AT (1) | ATE85976T1 (it) |
| AU (1) | AU589938B2 (it) |
| CA (1) | CA1256441A (it) |
| DE (1) | DE3587122T2 (it) |
| DK (1) | DK168564B1 (it) |
| ES (1) | ES8706630A1 (it) |
| IE (1) | IE58502B1 (it) |
| IT (1) | IT1179866B (it) |
| PT (1) | PT81674B (it) |
| WO (1) | WO1986003489A1 (it) |
| ZA (1) | ZA859526B (it) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4814463A (en) * | 1985-12-31 | 1989-03-21 | Biomeasure, Inc. | CCK antagonists |
| US4880938A (en) * | 1986-06-16 | 1989-11-14 | Merck & Co., Inc. | Amino acid analogs |
| US5089638A (en) * | 1986-06-16 | 1992-02-18 | Merck & Co., Inc. | Amino acid analogs as CCK-antagonists |
| SE8901149D0 (sv) * | 1989-04-03 | 1989-04-03 | Pharmacia Ab | Medel foer inducering respektive foerhindrande av pupillkonstriktion i oegat |
| US5360814A (en) * | 1991-02-28 | 1994-11-01 | Merrell Dow Pharmaceuticals Inc. | NMDA antagonists |
| DK0501378T3 (da) * | 1991-02-28 | 1995-03-20 | Merrell Dow Pharma | NMDA-antagonister |
| US5484814A (en) * | 1991-02-28 | 1996-01-16 | Merrell Dow Pharmaceuticals Inc. | NMDA antagonists |
| US20030199523A1 (en) * | 2002-02-28 | 2003-10-23 | Snutch Terrance P. | Heterocyclic calcium in channel blockers |
| PT1549333E (pt) | 2002-09-20 | 2012-01-03 | Univ Pennsylvania | Análogos de compstatina com actividade melhorada |
| US8168584B2 (en) | 2005-10-08 | 2012-05-01 | Potentia Pharmaceuticals, Inc. | Methods of treating age-related macular degeneration by compstatin and analogs thereof |
| EP2662089A3 (en) | 2005-10-08 | 2014-02-19 | Potentia Pharmaceuticals, Inc. | Compstatin and analogs thereof for eye disorders |
| CN102977191B (zh) | 2005-11-28 | 2016-08-10 | 宾夕法尼亚州大学理事会 | 有效的c3补体抑制素类似物 |
| HUE026001T2 (en) | 2007-02-05 | 2016-04-28 | Apellis Pharmaceuticals Inc | Compstatin analogues for use in the treatment of the inflammatory condition of the respiratory system |
| CA2760839C (en) | 2009-05-01 | 2019-02-12 | The Trustees Of The University Of Pennsylvania | Modified compstatin with peptide backbone and c-terminal modifications |
| CA2813049A1 (en) | 2010-09-23 | 2012-03-29 | The Trustees Of The University Of Pennsylvania | Modified compstatin with improved stability and binding properties |
| JP2014503592A (ja) | 2011-01-26 | 2014-02-13 | ニコ ワールドワイド，インコーポレイテッド | 片頭痛の療法 |
| MX356528B (es) | 2011-05-11 | 2018-06-01 | Apellis Pharmaceuticals Inc | Analogos de compstatina de celula reactiva, de acción prolongada u objetivos y usos de los mismos. |
| EP3524258B1 (en) | 2011-06-22 | 2025-10-01 | Apellis Pharmaceuticals, Inc. | Methods of treating chronic disorders with complement inhibitors |
| CA2847862C (en) | 2011-09-07 | 2021-01-12 | The Trustees Of The University Of Pennsylvania | Compstatin analogs with improved pharmacokinetic properties |
| MX366404B (es) | 2012-11-15 | 2019-07-08 | Apellis Pharmaceuticals Inc | Analogos de compstatina de celula reactiva, de acción prolongada u objetivos y composiciones y metodos relacionados. |
| WO2014152391A1 (en) | 2013-03-15 | 2014-09-25 | Apellis Pharmaceuticals, Inc. | Cell-penetrating compstatin analogs and uses thereof |
| US10213476B2 (en) | 2014-03-17 | 2019-02-26 | The Trustees Of The University Of Pennsylvania | Compstatin analogs with improved potency and pharmacokinetic properties |
| US11903994B2 (en) | 2015-10-07 | 2024-02-20 | Apellis Pharmaceuticals, Inc. | Dosing regimens |
| EP3374027B1 (en) * | 2015-11-12 | 2021-06-23 | The Trustees of Columbia University in the City of New York | Rational drug design targeting resistant gram-negative bacterial infections to polymyxin-class antibiotics |
| IL269844B2 (en) | 2017-04-07 | 2025-01-01 | Apellis Pharmaceuticals Inc | Dosage regimens and related compositions and methods |
| AU2018260628A1 (en) | 2017-04-25 | 2019-12-12 | Temple Otorongo Llc | Pharmaceutical composition comprising tryptophan and phyllokinin derivative for use in treating psychiatric and psychological conditions |
| WO2019118938A1 (en) | 2017-12-15 | 2019-06-20 | Apellis Pharmaceuticals, Inc. | Dosing regimens and related compositions and methods |
| EP4011905A3 (en) | 2018-04-06 | 2022-06-29 | The Trustees Of The University Of Pennsylvania | Compstatin analogs with increased solubility and improved pharmacokinetic properties |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1055518B (it) * | 1971-05-18 | 1982-01-11 | Rotta Research Lab | Derivatives del triptofano |
| US4482567A (en) * | 1982-10-07 | 1984-11-13 | Research Foundation For Mental Hygiene, Inc. | N-hexanoyl to n-heptadecanoyl 5-hydroxy tryptophan-5-hydroxytryptophanamides and use as analgesics |
-
1984
- 1984-12-12 IT IT68241/84A patent/IT1179866B/it active
-
1985
- 1985-12-02 IE IE302985A patent/IE58502B1/en not_active IP Right Cessation
- 1985-12-05 DE DE8686900106T patent/DE3587122T2/de not_active Expired - Fee Related
- 1985-12-05 EP EP86900106A patent/EP0237522B1/en not_active Expired - Lifetime
- 1985-12-05 AT AT86900106T patent/ATE85976T1/de active
- 1985-12-05 WO PCT/EP1985/000672 patent/WO1986003489A1/en not_active Ceased
- 1985-12-05 AU AU52099/86A patent/AU589938B2/en not_active Ceased
- 1985-12-05 JP JP61500191A patent/JPS62501292A/ja active Pending
- 1985-12-09 CA CA000497174A patent/CA1256441A/en not_active Expired
- 1985-12-11 ES ES549822A patent/ES8706630A1/es not_active Expired
- 1985-12-12 PT PT81674A patent/PT81674B/pt not_active IP Right Cessation
- 1985-12-12 ZA ZA859526A patent/ZA859526B/xx unknown
-
1986
- 1986-08-11 DK DK381486A patent/DK168564B1/da not_active IP Right Cessation
-
1988
- 1988-07-11 US US07/217,116 patent/US4870097A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO1986003489A1 (en) | 1986-06-19 |
| DE3587122T2 (de) | 1993-07-15 |
| DK381486D0 (da) | 1986-08-11 |
| EP0237522B1 (en) | 1993-02-24 |
| IT8468241A0 (it) | 1984-12-12 |
| IT8468241A1 (it) | 1986-06-12 |
| ZA859526B (en) | 1986-08-27 |
| ES8706630A1 (es) | 1987-06-01 |
| JPS62501292A (ja) | 1987-05-21 |
| AU5209986A (en) | 1986-07-01 |
| US4870097A (en) | 1989-09-26 |
| IE58502B1 (en) | 1993-10-06 |
| EP0237522A1 (en) | 1987-09-23 |
| ES549822A0 (es) | 1987-06-01 |
| IE853029L (en) | 1986-06-12 |
| CA1256441A (en) | 1989-06-27 |
| PT81674B (pt) | 1987-10-20 |
| IT1179866B (it) | 1987-09-16 |
| DK381486A (da) | 1986-08-11 |
| AU589938B2 (en) | 1989-10-26 |
| ATE85976T1 (de) | 1993-03-15 |
| DE3587122D1 (de) | 1993-04-01 |
| PT81674A (en) | 1986-01-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Patent granted (law 1993) | ||
| PBP | Patent lapsed |