NO301831B1 - N-substituerte cykloalkyl- og polycykloalkyl-<alfa>-substituerte Trp-Phe- og fenetylamin-derivater - Google Patents
N-substituerte cykloalkyl- og polycykloalkyl-<alfa>-substituerte Trp-Phe- og fenetylamin-derivater Download PDFInfo
- Publication number
- NO301831B1 NO301831B1 NO915122A NO915122A NO301831B1 NO 301831 B1 NO301831 B1 NO 301831B1 NO 915122 A NO915122 A NO 915122A NO 915122 A NO915122 A NO 915122A NO 301831 B1 NO301831 B1 NO 301831B1
- Authority
- NO
- Norway
- Prior art keywords
- amino
- methyl
- oxo
- indol
- carbonyl
- Prior art date
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- 125000005592 polycycloalkyl group Polymers 0.000 title claims description 3
- IMMPMHKLUUZKAZ-WMZOPIPTSA-N Trp-Phe Chemical class C([C@H](NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)N)C(O)=O)C1=CC=CC=C1 IMMPMHKLUUZKAZ-WMZOPIPTSA-N 0.000 title abstract 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical class NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 182
- 238000000034 method Methods 0.000 claims abstract description 57
- 238000002360 preparation method Methods 0.000 claims abstract description 25
- 230000008569 process Effects 0.000 claims abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 402
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 253
- -1 2-[[2-[[[(2-methylcyclohexyl)oxy]carbonyl]amino]-3-(1H-indol-3-yl)-2-methyl-1-oxopropyl]amino]-3-phenylpropyl-butanedioate Chemical compound 0.000 claims description 152
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 149
- 229910052739 hydrogen Inorganic materials 0.000 claims description 98
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 82
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 72
- 150000001412 amines Chemical class 0.000 claims description 70
- 239000002253 acid Substances 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 150000002148 esters Chemical class 0.000 claims description 19
- 238000009833 condensation Methods 0.000 claims description 17
- 230000005494 condensation Effects 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 150000003536 tetrazoles Chemical class 0.000 claims description 11
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 239000004471 Glycine Substances 0.000 claims description 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 5
- MCYLGSAZLPPAIY-UHFFFAOYSA-N (2-chlorocyclohexyl)-[1-[(1-hydroxy-3-phenylpropan-2-yl)amino]-3-(1H-indol-3-yl)-2-methyl-1-oxopropan-2-yl]carbamic acid Chemical compound C=1NC2=CC=CC=C2C=1CC(C)(C(=O)NC(CO)CC=1C=CC=CC=1)N(C(O)=O)C1CCCCC1Cl MCYLGSAZLPPAIY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical class CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 3
- 239000012346 acetyl chloride Substances 0.000 claims description 3
- 239000013067 intermediate product Substances 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- LZMJMUDDCGVYRW-UHFFFAOYSA-N CC(CC1=CNC2=CC=CC=C21)(C(=O)NC(CC3=CC=CC=C3)CC(CC(=O)O)C(=O)O)NC(=O)OC4CCCCC4Cl Chemical compound CC(CC1=CNC2=CC=CC=C21)(C(=O)NC(CC3=CC=CC=C3)CC(CC(=O)O)C(=O)O)NC(=O)OC4CCCCC4Cl LZMJMUDDCGVYRW-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- ZRDRAFOVIKLQED-QEHQQCFTSA-N [(1R,2R)-2-chlorocyclohexyl]-[3-(1H-indol-3-yl)-2-methyl-1-oxo-1-(2-phenylethylamino)propan-2-yl]carbamic acid Chemical compound CC(CC1=CNC2=CC=CC=C21)(C(=O)NCCC3=CC=CC=C3)N([C@@H]4CCCC[C@H]4Cl)C(=O)O ZRDRAFOVIKLQED-QEHQQCFTSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
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- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- ZRDRAFOVIKLQED-UHFFFAOYSA-N (2-chlorocyclohexyl)-[3-(1H-indol-3-yl)-2-methyl-1-oxo-1-(2-phenylethylamino)propan-2-yl]carbamic acid Chemical compound C=1NC2=CC=CC=C2C=1CC(C)(C(=O)NCCC=1C=CC=CC=1)N(C(O)=O)C1CCCCC1Cl ZRDRAFOVIKLQED-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 85
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- ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-N 0.000 description 20
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- 150000003254 radicals Chemical class 0.000 description 1
- VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 1
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- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
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- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- JOEDXGQNNYPPKU-UHFFFAOYSA-N tert-butyl 3-(2-formamido-3-oxo-3-phenylmethoxypropyl)indole-1-carboxylate Chemical compound C12=CC=CC=C2N(C(=O)OC(C)(C)C)C=C1CC(NC=O)C(=O)OCC1=CC=CC=C1 JOEDXGQNNYPPKU-UHFFFAOYSA-N 0.000 description 1
- LDKDMDVMMCXTMO-UHFFFAOYSA-N tert-butyl n-(1-hydroxy-3-phenylpropan-2-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC(CO)CC1=CC=CC=C1 LDKDMDVMMCXTMO-UHFFFAOYSA-N 0.000 description 1
- ZGGRMKRCDRQBPZ-UHFFFAOYSA-N tert-butyl n-(3-hydroxy-2-oxo-1-phenylpropyl)carbamate Chemical compound CC(C)(C)OC(=O)NC(C(=O)CO)C1=CC=CC=C1 ZGGRMKRCDRQBPZ-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 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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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
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- 239000010937 tungsten Substances 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- 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
-
- 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
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- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- 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
- A61P25/20—Hypnotics; Sedatives
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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
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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
-
- 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
-
- 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
-
- 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
- C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
-
- 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)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Biophysics (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Child & Adolescent Psychology (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37432789A | 1989-06-29 | 1989-06-29 | |
| US42248689A | 1989-10-16 | 1989-10-16 | |
| US53081190A | 1990-06-05 | 1990-06-05 | |
| PCT/US1990/003553 WO1991000274A1 (fr) | 1989-06-29 | 1990-06-28 | DERIVES DE Trp-Phe ET PHENETHYLAMINE A SUBSTITUTION ALPHA DE CYCLOALKYLE ET DE POLYCYCLOALKYLE A SUBSTITUTION N |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO915122D0 NO915122D0 (no) | 1991-12-27 |
| NO915122L NO915122L (no) | 1992-02-27 |
| NO301831B1 true NO301831B1 (no) | 1997-12-15 |
Family
ID=27409174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO915122A NO301831B1 (no) | 1989-06-29 | 1991-12-27 | N-substituerte cykloalkyl- og polycykloalkyl-<alfa>-substituerte Trp-Phe- og fenetylamin-derivater |
Country Status (17)
| Country | Link |
|---|---|
| EP (2) | EP0479910A1 (fr) |
| JP (1) | JP2972331B2 (fr) |
| KR (2) | KR0167315B1 (fr) |
| CN (1) | CN1049165A (fr) |
| AT (1) | ATE275546T1 (fr) |
| AU (1) | AU644088B2 (fr) |
| CA (2) | CA2060652C (fr) |
| DE (1) | DE69034162T2 (fr) |
| DK (1) | DK0405537T3 (fr) |
| ES (1) | ES2229202T3 (fr) |
| FI (1) | FI106197B (fr) |
| IE (1) | IE902347A1 (fr) |
| IL (1) | IL94903A0 (fr) |
| NO (1) | NO301831B1 (fr) |
| NZ (1) | NZ234264A (fr) |
| PT (1) | PT94543B (fr) |
| WO (1) | WO1991000274A1 (fr) |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5162336A (en) * | 1990-06-21 | 1992-11-10 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Tetrahydro-pyrido-indoles as cholecystokinin and gastrin antagonists |
| DE69132805T2 (de) * | 1990-08-31 | 2002-10-24 | Warner-Lambert Co., Ann Arbor | Pro-medikamente für cck-antagonisten |
| NZ239595A (en) * | 1990-08-31 | 1994-06-27 | Warner Lambert Co | Cholecystokinin antagonistic compounds ; pharmaceutical compositions and use thereof |
| US5244915A (en) * | 1990-08-31 | 1993-09-14 | Warner-Lambert Company | Amico acid derivatives cyclized at the c-terminal |
| US5340825A (en) * | 1990-08-31 | 1994-08-23 | Warner-Lambert Company | Pro drugs for CCK antagonists |
| US5593967A (en) * | 1990-08-31 | 1997-01-14 | Warner-Lambert Company | Cholecystokinin antagonists, their preparation and therapeutic use |
| US5264420A (en) * | 1990-09-27 | 1993-11-23 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| WO1992019254A1 (fr) * | 1991-04-24 | 1992-11-12 | Warner-Lambert Company | POLYPEPTIDES α SUBSTITUES AYANT DES PROPRIETES THERAPEUTIQUES |
| HUT68769A (en) * | 1991-05-07 | 1995-07-28 | Merck & Co Inc | FIBRINOGéN RECEPTOR ANTAGONIST COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS COMPRISING THEM AS EFFECTIVE SUBSTANCE |
| EP0594692A1 (fr) * | 1991-07-12 | 1994-05-04 | Warner-Lambert Company | Antagonistes de cholecystokinine utiles dans le traitement de crises de panique |
| US5217957A (en) * | 1991-08-20 | 1993-06-08 | Warner-Lambert Company | Cholecystokinin antagonists useful for treating depression |
| US5153191A (en) * | 1991-08-20 | 1992-10-06 | Warner-Lambert Company | Cholecystokinin antagonists useful for treating depression |
| US5389631A (en) * | 1991-10-29 | 1995-02-14 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5272158A (en) * | 1991-10-29 | 1993-12-21 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| DE4137490A1 (de) * | 1991-11-14 | 1993-05-19 | Goedecke Ag | Synthese von tricyclo(3.3.1.13,7)dec-2.yl(r-(r*,r*))-3- (1h-indol-3-yl-methyl)-3-methyl-4,9-dioxo- 7,11-diphenyl-10-oxa-2,5,8-triaza-undecanat |
| US6492531B1 (en) | 1992-02-18 | 2002-12-10 | Warner-Lambert Company | Method of treating cognitive disorders |
| GB9316722D0 (en) * | 1993-08-12 | 1993-09-29 | Black James Foundation | Bicyclo (2.2.2)octane derivatives |
| US5514683A (en) * | 1992-02-20 | 1996-05-07 | James Black Foundation Limited | Bicyclo 2,2,2!octane derivatives |
| JPH07504184A (ja) * | 1992-02-20 | 1995-05-11 | ジェイムズ・ブラック・ファウンデーション・リミテッド | コレストシストキニン抑制剤としてのビシクロ［２，２，２］オクタン誘導体 |
| US5227490A (en) * | 1992-02-21 | 1993-07-13 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| AU4348993A (en) * | 1992-06-19 | 1994-01-24 | James Black Foundation Limited | Bicyclooctane and bicycloheptane derivatives |
| US5380872A (en) * | 1992-07-14 | 1995-01-10 | Glaxo Inc. | Modulators of cholecystokinin |
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| 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 |
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| US4814463A (en) * | 1985-12-31 | 1989-03-21 | Biomeasure, Inc. | CCK antagonists |
-
1990
- 1990-06-27 NZ NZ234264A patent/NZ234264A/xx unknown
- 1990-06-28 ES ES90112333T patent/ES2229202T3/es not_active Expired - Lifetime
- 1990-06-28 EP EP90911185A patent/EP0479910A1/fr active Pending
- 1990-06-28 CA CA002060652A patent/CA2060652C/fr not_active Expired - Fee Related
- 1990-06-28 AU AU59628/90A patent/AU644088B2/en not_active Ceased
- 1990-06-28 EP EP90112333A patent/EP0405537B1/fr not_active Expired - Lifetime
- 1990-06-28 CA CA002344707A patent/CA2344707C/fr not_active Expired - Fee Related
- 1990-06-28 JP JP2510126A patent/JP2972331B2/ja not_active Expired - Fee Related
- 1990-06-28 AT AT90112333T patent/ATE275546T1/de not_active IP Right Cessation
- 1990-06-28 DK DK90112333T patent/DK0405537T3/da active
- 1990-06-28 IL IL94903A patent/IL94903A0/xx unknown
- 1990-06-28 WO PCT/US1990/003553 patent/WO1991000274A1/fr active IP Right Grant
- 1990-06-28 IE IE234790A patent/IE902347A1/en unknown
- 1990-06-28 KR KR1019910702001A patent/KR0167315B1/ko not_active IP Right Cessation
- 1990-06-28 DE DE69034162T patent/DE69034162T2/de not_active Expired - Fee Related
- 1990-06-29 PT PT94543A patent/PT94543B/pt not_active IP Right Cessation
- 1990-06-29 CN CN90106804A patent/CN1049165A/zh active Pending
-
1991
- 1991-12-20 FI FI916060A patent/FI106197B/fi not_active IP Right Cessation
- 1991-12-27 NO NO915122A patent/NO301831B1/no not_active IP Right Cessation
-
1998
- 1998-06-26 KR KR1019980704957A patent/KR0180539B1/ko not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PT94543A (pt) | 1991-03-20 |
| KR920702678A (ko) | 1992-10-06 |
| ATE275546T1 (de) | 2004-09-15 |
| AU5962890A (en) | 1991-01-17 |
| KR0180539B1 (en) | 1999-05-01 |
| CN1049165A (zh) | 1991-02-13 |
| EP0479910A1 (fr) | 1992-04-15 |
| EP0405537B1 (fr) | 2004-09-08 |
| DK0405537T3 (da) | 2005-01-10 |
| CA2060652A1 (fr) | 1990-12-30 |
| NO915122L (no) | 1992-02-27 |
| CA2344707A1 (fr) | 1991-01-10 |
| JPH04506079A (ja) | 1992-10-22 |
| PT94543B (pt) | 1997-04-30 |
| NO915122D0 (no) | 1991-12-27 |
| JP2972331B2 (ja) | 1999-11-08 |
| CA2060652C (fr) | 2001-08-21 |
| DE69034162D1 (de) | 2004-10-14 |
| FI106197B (fi) | 2000-12-15 |
| EP0405537A1 (fr) | 1991-01-02 |
| DE69034162T2 (de) | 2005-09-22 |
| IE902347L (en) | 1990-12-29 |
| KR0167315B1 (ko) | 1999-01-15 |
| NZ234264A (en) | 1993-05-26 |
| FI916060A0 (fi) | 1991-12-20 |
| CA2344707C (fr) | 2002-07-30 |
| WO1991000274A1 (fr) | 1991-01-10 |
| IE902347A1 (en) | 1991-01-16 |
| AU644088B2 (en) | 1993-12-02 |
| ES2229202T3 (es) | 2005-04-16 |
| IL94903A0 (en) | 1991-04-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |