AU658377B2 - Alpha-substituted tryptophane dipeptoid derivatives - Google Patents
Alpha-substituted tryptophane dipeptoid derivativesInfo
- Publication number
- AU658377B2 AU658377B2 AU88661/91A AU8866191A AU658377B2 AU 658377 B2 AU658377 B2 AU 658377B2 AU 88661/91 A AU88661/91 A AU 88661/91A AU 8866191 A AU8866191 A AU 8866191A AU 658377 B2 AU658377 B2 AU 658377B2
- Authority
- AU
- Australia
- Prior art keywords
- amino
- methyl
- compound according
- indol
- oxo
- 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
- 229960004799 tryptophan Drugs 0.000 title description 5
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 title description 4
- 239000006035 Tryptophane Substances 0.000 title description 2
- 125000000430 tryptophan group Chemical class [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 104
- -1 hydroxy, phenyl Chemical group 0.000 claims description 67
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 32
- 241000124008 Mammalia Species 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- YXXKMTIGKAVJTA-UHFFFAOYSA-N ac1l3htk Chemical group C1C(C2)CC3[CH]C1CC2C3 YXXKMTIGKAVJTA-UHFFFAOYSA-N 0.000 claims description 23
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 22
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 22
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
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- 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 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
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- 230000000903 blocking effect Effects 0.000 claims description 6
- AOXOCDRNSPFDPE-UKEONUMOSA-N chembl413654 Chemical compound C([C@H](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](C)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@@H](N)CCC(O)=O)C1=CC=C(O)C=C1 AOXOCDRNSPFDPE-UKEONUMOSA-N 0.000 claims description 6
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- ZTTWHZHBPDYSQB-LBPRGKRZSA-N (2s)-2-amino-3-(1h-indol-3-yl)-2-methylpropanoic acid Chemical class C1=CC=C2C(C[C@@](N)(C)C(O)=O)=CNC2=C1 ZTTWHZHBPDYSQB-LBPRGKRZSA-N 0.000 claims description 5
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- 229910052736 halogen Inorganic materials 0.000 claims description 4
- AWIISLRCVKJMSB-UHFFFAOYSA-N methyl 3-[[2-[[2-(2-adamantyloxycarbonylamino)-3-(1h-indol-3-yl)-2-methylpropanoyl]amino]-1,2,3,4-tetrahydronaphthalen-1-yl]amino]-3-oxopropanoate Chemical compound C1C(CC2C3)CC3CC1C2OC(=O)NC(C)(CC=1C2=CC=CC=C2NC=1)C(=O)NC1C(NC(=O)CC(=O)OC)C2=CC=CC=C2CC1 AWIISLRCVKJMSB-UHFFFAOYSA-N 0.000 claims description 4
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- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
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- 125000002950 monocyclic group Chemical group 0.000 claims description 2
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- 125000003367 polycyclic group Chemical group 0.000 claims description 2
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- 230000002285 radioactive effect Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
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- 239000000243 solution Substances 0.000 description 33
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 32
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- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
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- 238000004519 manufacturing process Methods 0.000 description 1
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- HNANPFCWIYUTQW-IEKLRMFZSA-N methyl (2r)-2-(2-adamantyloxycarbonylamino)-3-(1h-indol-3-yl)-2-methylpropanoate Chemical compound C1C(CC2C3)CC3CC1C2OC(=O)N[C@@](C)(C(=O)OC)CC1=CNC2=CC=CC=C12 HNANPFCWIYUTQW-IEKLRMFZSA-N 0.000 description 1
- RCUNGDZWHFRBBP-CYBMUJFWSA-N methyl (2r)-2-amino-3-(1h-indol-3-yl)-2-methylpropanoate Chemical compound C1=CC=C2C(C[C@@](C)(N)C(=O)OC)=CNC2=C1 RCUNGDZWHFRBBP-CYBMUJFWSA-N 0.000 description 1
- RCUNGDZWHFRBBP-ZDUSSCGKSA-N methyl (2s)-2-amino-3-(1h-indol-3-yl)-2-methylpropanoate Chemical compound C1=CC=C2C(C[C@](C)(N)C(=O)OC)=CNC2=C1 RCUNGDZWHFRBBP-ZDUSSCGKSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
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- IDRKSQOOQMTISM-UHFFFAOYSA-N n-(2-benzylphenyl)-2-[(3-methylphenyl)carbamoylamino]acetamide Chemical compound CC1=CC=CC(NC(=O)NCC(=O)NC=2C(=CC=CC=2)CC=2C=CC=CC=2)=C1 IDRKSQOOQMTISM-UHFFFAOYSA-N 0.000 description 1
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- 230000002265 prevention Effects 0.000 description 1
- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
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- 150000003254 radicals Chemical class 0.000 description 1
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- 210000002460 smooth muscle Anatomy 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
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- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
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- 229940034208 thyroxine Drugs 0.000 description 1
- XUIIKFGFIJCVMT-UHFFFAOYSA-N thyroxine-binding globulin Natural products IC1=CC(CC([NH3+])C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
-
- 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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57629690A | 1990-08-31 | 1990-08-31 | |
| US576296 | 1990-08-31 | ||
| US726654 | 1991-07-12 | ||
| US07/726,654 US5244915A (en) | 1990-08-31 | 1991-07-12 | Amico acid derivatives cyclized at the c-terminal |
| PCT/US1991/006177 WO1992004322A1 (en) | 1990-08-31 | 1991-08-29 | Alpha-substituted tryptophane dipeptoid derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU8866191A AU8866191A (en) | 1992-03-30 |
| AU658377B2 true AU658377B2 (en) | 1995-04-13 |
Family
ID=27076919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU88661/91A Ceased AU658377B2 (en) | 1990-08-31 | 1991-08-29 | Alpha-substituted tryptophane dipeptoid derivatives |
Country Status (11)
| Country | Link |
|---|---|
| US (3) | US5244915A (enExample) |
| EP (1) | EP0546123A1 (enExample) |
| JP (1) | JPH06502850A (enExample) |
| KR (1) | KR930702296A (enExample) |
| AU (1) | AU658377B2 (enExample) |
| CA (1) | CA2088996A1 (enExample) |
| FI (1) | FI930878L (enExample) |
| IE (1) | IE913078A1 (enExample) |
| NZ (1) | NZ239612A (enExample) |
| PT (1) | PT98828A (enExample) |
| WO (1) | WO1992004322A1 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5631281A (en) * | 1989-06-29 | 1997-05-20 | Warner-Lambert Company | N-substituted cycloalkyl and polycycloalkyl α-substituted Trp-Phe- and phenethylamine derivatives |
| EP0547178A4 (en) * | 1990-08-31 | 1994-07-06 | Warner Lambert Co | Novel cholecystokinin antagonists, their preparation and therapeutic use |
| US5593967A (en) * | 1990-08-31 | 1997-01-14 | Warner-Lambert Company | Cholecystokinin antagonists, their preparation and therapeutic use |
| WO1993000897A1 (en) * | 1991-07-12 | 1993-01-21 | Warner-Lambert Company | Cholecystokinin antagonists useful in the treatment of panic attacks |
| US5217957A (en) * | 1991-08-20 | 1993-06-08 | Warner-Lambert Company | Cholecystokinin antagonists useful for treating depression |
| US5380872A (en) * | 1992-07-14 | 1995-01-10 | Glaxo Inc. | Modulators of cholecystokinin |
| FR2700540B1 (fr) * | 1993-01-15 | 1995-02-17 | Irj | alpha-méthyl-(R)-tryptophyl-arylcycloalkylalkylamides ligands aux récepteurs des gastrines, leur préparation et leur utilisation en thérapeutique. |
| US7077822B1 (en) | 1994-02-09 | 2006-07-18 | The University Of Iowa Research Foundation | Stereotactic hypothalamic obesity probe |
| US6129685A (en) * | 1994-02-09 | 2000-10-10 | The University Of Iowa Research Foundation | Stereotactic hypothalamic obesity probe |
| WO1995024389A1 (en) * | 1994-03-10 | 1995-09-14 | Warner-Lambert Company | Indole derivatives as cck receptor antagonists |
| US5420353A (en) * | 1994-03-11 | 1995-05-30 | Merck & Co., Inc. | Regiospecific process to make cis-1-amino-2-alkanol from epoxide |
| EP0885017A2 (en) * | 1996-02-27 | 1998-12-23 | Mallinckrodt Medical, Inc. | Use of labelled cck-b receptor ligands for the detection and localization of malignant human tumours |
| AU2001268731A1 (en) * | 2000-09-27 | 2002-04-08 | Sarfaraz K. Niazi | A combination of appetite controlling agents which create a synergy and produce a satiating result |
| US20060062864A1 (en) * | 2000-12-28 | 2006-03-23 | Mccleary Edward L | Weight loss composition and method |
| EP1562594A4 (en) * | 2002-10-15 | 2008-12-17 | Univ Tennessee Res Foundation | SELECTIVE ANDROGEN RECEPTOR MODULATORS WITH METHYLENE BRIDGES AND METHOD OF USE THEREOF |
| BRPI0416434A (pt) * | 2003-11-25 | 2007-02-21 | Sinai School Medicine | métodos para aumentar a atividade de uma proteìna de ácido esfingomielinase (asm), para estender a meia-vida e prolongar a atividade de uma proteìna asm purificada, para aumentar a produção de uma proteìna asm recombinante através de uma célula hospedeira, e usos de uma composição de asm tipo alelo-selvagem, purificada e um composto análogo de ceramida ou esfingomielina, e de um composto análogo de ceramida ou de esfingomielina |
| EP1720839A1 (en) * | 2004-02-10 | 2006-11-15 | Janssen Pharmaceutica N.V. | Pyridazinones as antagonists of a4 integrins |
| US7880001B2 (en) * | 2004-04-29 | 2011-02-01 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase Type 1 enzyme |
| US20050245534A1 (en) * | 2004-04-29 | 2005-11-03 | Link James T | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase Type 1 enzyme |
| US8415354B2 (en) | 2004-04-29 | 2013-04-09 | Abbott Laboratories | Methods of use of inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| US20050261302A1 (en) * | 2004-04-29 | 2005-11-24 | Hoff Ethan D | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase Type 1 enzyme and their therapeutic application |
| US20100222316A1 (en) | 2004-04-29 | 2010-09-02 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| US8198331B2 (en) * | 2005-01-05 | 2012-06-12 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| CA2594116A1 (en) | 2005-01-05 | 2006-07-13 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| US20090192198A1 (en) | 2005-01-05 | 2009-07-30 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| MX2007008238A (es) | 2005-01-05 | 2007-08-17 | Abbott Lab | Derivados de adamantilo como inhibidores de la enzima 11-beta-hidroxiesteroide deshidrogenasa tipo 1. |
| JP5736098B2 (ja) | 2007-08-21 | 2015-06-17 | アッヴィ・インコーポレイテッド | 中枢神経系障害を治療するための医薬組成物 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4814463A (en) * | 1985-12-31 | 1989-03-21 | Biomeasure, Inc. | CCK antagonists |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4757151A (en) * | 1985-11-14 | 1988-07-12 | Warner-Lambert Company | 2-substituted-[2-substituted-amino]-N-arylalkyl-3-[indol-3-yl] |
| JPH0761992B2 (ja) * | 1987-02-06 | 1995-07-05 | 武田薬品工業株式会社 | 置換アミン誘導体 |
| US4888427A (en) * | 1987-04-07 | 1989-12-19 | University Of Florida | Amino acids containing dihydropyridine ring systems for site-specific delivery of peptides to the brain |
| US4877785A (en) * | 1987-10-01 | 1989-10-31 | G. D. Searle & Co. | Non-peptidyl beta-succinamidoacyl aminodiols as anti-hypertensive agents |
| EP0442878A4 (en) * | 1988-04-05 | 1991-10-23 | Abbott Laboratories | Derivatives of tryptophan as cck antagonists |
| 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 |
| FR2700540B1 (fr) * | 1993-01-15 | 1995-02-17 | Irj | alpha-méthyl-(R)-tryptophyl-arylcycloalkylalkylamides ligands aux récepteurs des gastrines, leur préparation et leur utilisation en thérapeutique. |
-
1991
- 1991-07-12 US US07/726,654 patent/US5244915A/en not_active Expired - Lifetime
- 1991-08-29 EP EP91919909A patent/EP0546123A1/en not_active Ceased
- 1991-08-29 KR KR1019930700602A patent/KR930702296A/ko not_active Withdrawn
- 1991-08-29 CA CA002088996A patent/CA2088996A1/en not_active Abandoned
- 1991-08-29 WO PCT/US1991/006177 patent/WO1992004322A1/en not_active Ceased
- 1991-08-29 FI FI930878A patent/FI930878L/fi unknown
- 1991-08-29 AU AU88661/91A patent/AU658377B2/en not_active Ceased
- 1991-08-29 JP JP3518049A patent/JPH06502850A/ja active Pending
- 1991-08-30 NZ NZ239612A patent/NZ239612A/en unknown
- 1991-08-30 PT PT98828A patent/PT98828A/pt not_active Application Discontinuation
- 1991-08-30 IE IE307891A patent/IE913078A1/en unknown
-
1993
- 1993-04-20 US US08/049,721 patent/US5397788A/en not_active Expired - Fee Related
-
1994
- 1994-12-05 US US08/347,999 patent/US5523306A/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4814463A (en) * | 1985-12-31 | 1989-03-21 | Biomeasure, Inc. | CCK antagonists |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2088996A1 (en) | 1992-03-01 |
| US5244915A (en) | 1993-09-14 |
| JPH06502850A (ja) | 1994-03-31 |
| EP0546123A1 (en) | 1993-06-16 |
| EP0546123A4 (enExample) | 1994-04-27 |
| WO1992004322A1 (en) | 1992-03-19 |
| PT98828A (pt) | 1992-07-31 |
| FI930878A7 (fi) | 1993-04-16 |
| FI930878L (fi) | 1993-04-16 |
| KR930702296A (ko) | 1993-09-08 |
| FI930878A0 (fi) | 1993-02-26 |
| AU8866191A (en) | 1992-03-30 |
| US5523306A (en) | 1996-06-04 |
| US5397788A (en) | 1995-03-14 |
| NZ239612A (en) | 1994-02-25 |
| IE913078A1 (en) | 1992-03-11 |
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| US5726200A (en) | Pro-drugs for CCK antagonists | |
| US5593967A (en) | Cholecystokinin antagonists, their preparation and therapeutic use | |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |