EP0804463A1 - Neurokinin (tachykinin)-antagonisten - Google Patents
Neurokinin (tachykinin)-antagonistenInfo
- Publication number
- EP0804463A1 EP0804463A1 EP95919392A EP95919392A EP0804463A1 EP 0804463 A1 EP0804463 A1 EP 0804463A1 EP 95919392 A EP95919392 A EP 95919392A EP 95919392 A EP95919392 A EP 95919392A EP 0804463 A1 EP0804463 A1 EP 0804463A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- alkyl
- phenyl
- pro
- compound according
- 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.)
- Withdrawn
Links
- 239000005557 antagonist Substances 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 86
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 150000003862 amino acid derivatives Chemical class 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 75
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 125000003545 alkoxy group Chemical group 0.000 claims description 41
- -1 cyano, hydroxy Chemical group 0.000 claims description 37
- 229940024606 amino acid Drugs 0.000 claims description 28
- 235000001014 amino acid Nutrition 0.000 claims description 28
- 150000001413 amino acids Chemical class 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 25
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 18
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims description 17
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 17
- 229960003767 alanine Drugs 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 16
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 claims description 15
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 14
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
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- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 12
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 11
- 125000006239 protecting group Chemical group 0.000 claims description 11
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 9
- 229960002591 hydroxyproline Drugs 0.000 claims description 9
- IADUEWIQBXOCDZ-VKHMYHEASA-N (S)-azetidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCN1 IADUEWIQBXOCDZ-VKHMYHEASA-N 0.000 claims description 8
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- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 8
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims description 8
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 8
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 8
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 8
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Chemical compound CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 108090000765 processed proteins & peptides Chemical class 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- BJBUEDPLEOHJGE-UHFFFAOYSA-N (2R,3S)-3-Hydroxy-2-pyrolidinecarboxylic acid Natural products OC1CCNC1C(O)=O BJBUEDPLEOHJGE-UHFFFAOYSA-N 0.000 claims description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 6
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- BJBUEDPLEOHJGE-IUYQGCFVSA-N cis-3-hydroxy-D-proline zwitterion Chemical compound O[C@H]1CCN[C@H]1C(O)=O BJBUEDPLEOHJGE-IUYQGCFVSA-N 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims description 5
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
- 229960004452 methionine Drugs 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229960005190 phenylalanine Drugs 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 claims description 4
- IADUEWIQBXOCDZ-UHFFFAOYSA-N (2S)-azetidine-2-carboxylic acid Natural products OC(=O)C1CCN1 IADUEWIQBXOCDZ-UHFFFAOYSA-N 0.000 claims description 4
- XLEKQZHPKBRJNB-BKLSDQPFSA-N (2r)-3-sulfanylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@H]1NCCC1S XLEKQZHPKBRJNB-BKLSDQPFSA-N 0.000 claims description 4
- VJLXSTXGGXYQCT-BKLSDQPFSA-N (2s)-3-aminopyrrolidine-2-carboxylic acid Chemical compound NC1CCN[C@@H]1C(O)=O VJLXSTXGGXYQCT-BKLSDQPFSA-N 0.000 claims description 4
- SHINASQYHDCLEU-BKLSDQPFSA-N (2s)-4-aminopyrrolidine-2-carboxylic acid Chemical compound NC1CN[C@H](C(O)=O)C1 SHINASQYHDCLEU-BKLSDQPFSA-N 0.000 claims description 4
- OYNANFOWNSGDJL-BKLSDQPFSA-N (2s)-4-sulfanylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CC(S)CN1 OYNANFOWNSGDJL-BKLSDQPFSA-N 0.000 claims description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- OMGHIGVFLOPEHJ-UHFFFAOYSA-N 2,5-dihydro-1h-pyrrol-1-ium-2-carboxylate Chemical compound OC(=O)C1NCC=C1 OMGHIGVFLOPEHJ-UHFFFAOYSA-N 0.000 claims description 4
- FUOOLUPWFVMBKG-UHFFFAOYSA-N 2-Aminoisobutyric acid Chemical compound CC(C)(N)C(O)=O FUOOLUPWFVMBKG-UHFFFAOYSA-N 0.000 claims description 4
- PECYZEOJVXMISF-REOHCLBHSA-N 3-amino-L-alanine Chemical compound [NH3+]C[C@H](N)C([O-])=O PECYZEOJVXMISF-REOHCLBHSA-N 0.000 claims description 4
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 claims description 4
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims description 4
- OGNSCSPNOLGXSM-VKHMYHEASA-N L-2,4-diaminobutyric acid Chemical compound NCC[C@H](N)C(O)=O OGNSCSPNOLGXSM-VKHMYHEASA-N 0.000 claims description 4
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 claims description 4
- CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 claims description 4
- 235000019766 L-Lysine Nutrition 0.000 claims description 4
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- 125000000393 L-methionino group Chemical group [H]OC(=O)[C@@]([H])(N([H])[*])C([H])([H])C(SC([H])([H])[H])([H])[H] 0.000 claims description 4
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- ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 claims description 4
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- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- ORQXBVXKBGUSBA-QMMMGPOBSA-N β-cyclohexyl-alanine Chemical compound OC(=O)[C@@H](N)CC1CCCCC1 ORQXBVXKBGUSBA-QMMMGPOBSA-N 0.000 description 1
Classifications
-
- 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
- C07K5/06165—Dipeptides with the first amino acid being heterocyclic and Pro-amino acid; Derivatives thereof
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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
- A61P35/00—Antineoplastic 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
- 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
-
- 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
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4416255 | 1994-05-07 | ||
| DE4416255 | 1994-05-07 | ||
| DE4445939 | 1994-12-22 | ||
| DE4445939A DE4445939A1 (de) | 1994-05-07 | 1994-12-22 | Neue Aminosäurederivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen (II) |
| PCT/EP1995/001691 WO1995030687A1 (de) | 1994-05-07 | 1995-05-04 | Neurokinin (tachykinin)-antagonisten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0804463A1 true EP0804463A1 (de) | 1997-11-05 |
Family
ID=25936418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP95919392A Withdrawn EP0804463A1 (de) | 1994-05-07 | 1995-05-04 | Neurokinin (tachykinin)-antagonisten |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US5712273A (ja) |
| EP (1) | EP0804463A1 (ja) |
| JP (1) | JPH09512806A (ja) |
| CN (1) | CN1147260A (ja) |
| AU (1) | AU690275B2 (ja) |
| BG (1) | BG100946A (ja) |
| CA (1) | CA2189764A1 (ja) |
| CZ (1) | CZ325496A3 (ja) |
| EE (1) | EE9600186A (ja) |
| FI (1) | FI964473A0 (ja) |
| HR (1) | HRP950276A2 (ja) |
| HU (1) | HUT75708A (ja) |
| IL (1) | IL113625A0 (ja) |
| MX (1) | MX9605128A (ja) |
| NO (1) | NO964700D0 (ja) |
| NZ (1) | NZ285750A (ja) |
| PL (1) | PL317127A1 (ja) |
| RO (1) | RO115355B1 (ja) |
| SK (1) | SK142696A3 (ja) |
| WO (1) | WO1995030687A1 (ja) |
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SK65094A3 (en) * | 1992-09-03 | 1995-03-08 | Boehringer Ingelheim Kg | Aminoacid derivatives, process for producing the same and pharmaceutical compositions containing these derivatives |
| DE19541283A1 (de) | 1995-11-06 | 1997-05-07 | Boehringer Ingelheim Kg | Neue Aminosäurederivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen |
| DE19623950A1 (de) * | 1996-06-15 | 1997-12-18 | Boehringer Ingelheim Kg | Pharmazeutische Zubereitung in Form von Liposomen |
| US6329342B1 (en) | 1997-08-19 | 2001-12-11 | Eli Lilly And Company | Treatment of congestive heart failure with growth hormone secretagogues |
| US6639076B1 (en) * | 1998-08-18 | 2003-10-28 | Eli Lilly And Company | Growth hormone secretagogues |
| GB9819860D0 (en) | 1998-09-12 | 1998-11-04 | Zeneca Ltd | Chemical compounds |
| EP1930021A3 (en) | 1999-02-18 | 2008-06-18 | Kaken Pharmaceutical Co., Ltd. | Novel amide derivatives as growth hormone secretagogues |
| US6828331B1 (en) * | 1999-02-19 | 2004-12-07 | Eli Lilly And Company | Growth hormone secretagogues |
| US6514965B1 (en) | 1999-11-18 | 2003-02-04 | Antex Pharma Inc. | Substituted 1-benzazepines and derivatives thereof |
| US7125840B2 (en) * | 2001-10-09 | 2006-10-24 | Eli Lilly And Company | Substituted dipeptides as growth hormone secretagogues |
| ES2266798T3 (es) * | 2002-04-09 | 2007-03-01 | Eli Lilly And Company | Secretagodos de hormona de crecimiento. |
| US20060167268A1 (en) * | 2002-04-09 | 2006-07-27 | Eli Lilly And Company, Patent Division, | Growth hormone secretagogues |
| MX2007000428A (es) | 2004-07-15 | 2008-03-05 | Amr Technology Inc | Tetrahidroisoquinolinas sustituidas con arilo y heteroarilo y uso de las mismas para bloquear la captacion de norepinefrina, dopamina y serotonina. |
| US7238560B2 (en) * | 2004-07-23 | 2007-07-03 | Cree, Inc. | Methods of fabricating nitride-based transistors with a cap layer and a recessed gate |
| ATE550019T1 (de) | 2005-05-17 | 2012-04-15 | Merck Sharp & Dohme | Cis-4-ä(4-chlorophenyl)sulfonylü-4-(2,5- difluorophenyl)cyclohexanepropansäure zur behandlug von krebs |
| CA2615403C (en) | 2005-07-15 | 2015-06-16 | Amr Technology, Inc. | Aryl-and heteroaryl-substituted tetrahydrobenzazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| AU2006297443B2 (en) | 2005-09-29 | 2010-08-12 | Merck Sharp & Dohme Corp. | Acylated spiropiperidine derivatives as melanocortin-4 receptor modulators |
| GB0603041D0 (en) | 2006-02-15 | 2006-03-29 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| CA2664113C (en) | 2006-09-22 | 2013-05-28 | Merck & Co., Inc. | Use of platencin and platensimycin as fatty acid synthesis inhibitors to treat obesity, diabetes and cancer |
| US20110218176A1 (en) | 2006-11-01 | 2011-09-08 | Barbara Brooke Jennings-Spring | Compounds, methods, and treatments for abnormal signaling pathways for prenatal and postnatal development |
| EP2109608B1 (en) | 2007-01-10 | 2011-03-23 | Istituto di Richerche di Biologia Molecolare P. Angeletti S.p.A. | Amide substituted indazoles as poly(adp-ribose)polymerase (parp) inhibitors |
| US8106086B2 (en) | 2007-04-02 | 2012-01-31 | Msd K.K. | Indoledione derivative |
| JP5501227B2 (ja) | 2007-06-27 | 2014-05-21 | メルク・シャープ・アンド・ドーム・コーポレーション | ヒストンデアセチラーゼ阻害剤としての４−カルボキシベンジルアミノ誘導体 |
| AU2009222122A1 (en) | 2008-03-03 | 2009-09-11 | Tiger Pharmatech | Tyrosine kinase inhibitors |
| US9156812B2 (en) | 2008-06-04 | 2015-10-13 | Bristol-Myers Squibb Company | Crystalline form of 6-[(4S)-2-methyl-4-(2-naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine |
| EP2413932A4 (en) | 2009-04-01 | 2012-09-19 | Merck Sharp & Dohme | INHIBITORS OF AKT ACTIVITY |
| ES2662072T3 (es) | 2009-05-12 | 2018-04-05 | Albany Molecular Research, Inc. | 7-([1,2,4]triazolo[1,5-a]piridin-6-il)-4-(3,4-diclorofenil)-1,2,3,4-tetrahidroisoquinolina y uso de la misma |
| KR20120034644A (ko) | 2009-05-12 | 2012-04-12 | 알바니 몰레큘라 리써치, 인크. | 아릴, 헤테로아릴, 및 헤테로사이클 치환된 테트라하이드로이소퀴놀린 및 이의 용도 |
| EP2429293B1 (en) | 2009-05-12 | 2014-10-29 | Bristol-Myers Squibb Company | CRYSTALLINE FORMS OF (S)-7-([1,2,4]TRIAZOLO[1,5-a]PYRIDIN-6-YL)-4-(3,4-DICHLOROHPHENYL)-1,2,3,4-TETRAHYDROISOQUINOLINE AND USE THEREOF |
| KR101485645B1 (ko) | 2009-10-14 | 2015-01-22 | 머크 샤프 앤드 돔 코포레이션 | ｐ53 활성을 증가시키는 치환된 피페리딘 및 그의 용도 |
| WO2011163330A1 (en) | 2010-06-24 | 2011-12-29 | Merck Sharp & Dohme Corp. | Novel heterocyclic compounds as erk inhibitors |
| CN107090456B (zh) | 2010-08-02 | 2022-01-18 | 瑟纳治疗公司 | 使用短干扰核酸的RNA干扰介导的联蛋白（钙粘蛋白关联蛋白质），β1基因表达的抑制 |
| HUE044815T2 (hu) | 2010-08-17 | 2019-11-28 | Sirna Therapeutics Inc | Hepatitisz B vírus (HBV) génexpressziójának RNS-interferencia közvetített gátlása, rövid interferáló nukleinsav (SINS) alkalmazásával |
| US8883801B2 (en) | 2010-08-23 | 2014-11-11 | Merck Sharp & Dohme Corp. | Substituted pyrazolo[1,5-a]pyrimidines as mTOR inhibitors |
| WO2012030685A2 (en) | 2010-09-01 | 2012-03-08 | Schering Corporation | Indazole derivatives useful as erk inhibitors |
| US9242981B2 (en) | 2010-09-16 | 2016-01-26 | Merck Sharp & Dohme Corp. | Fused pyrazole derivatives as novel ERK inhibitors |
| WO2012058210A1 (en) | 2010-10-29 | 2012-05-03 | Merck Sharp & Dohme Corp. | RNA INTERFERENCE MEDIATED INHIBITION OF GENE EXPRESSION USING SHORT INTERFERING NUCLEIC ACIDS (siNA) |
| US9351965B2 (en) | 2010-12-21 | 2016-05-31 | Merck Sharp & Dohme Corp. | Indazole derivatives useful as ERK inhibitors |
| CN103732592A (zh) | 2011-04-21 | 2014-04-16 | 默沙东公司 | 胰岛素样生长因子-1受体抑制剂 |
| US9023865B2 (en) | 2011-10-27 | 2015-05-05 | Merck Sharp & Dohme Corp. | Compounds that are ERK inhibitors |
| EP3919620A1 (en) | 2012-05-02 | 2021-12-08 | Sirna Therapeutics, Inc. | Short interfering nucleic acid (sina) compositions |
| CA2882950A1 (en) | 2012-09-28 | 2014-04-03 | Merck Sharp & Dohme Corp. | Novel compounds that are erk inhibitors |
| LT2925888T (lt) | 2012-11-28 | 2018-01-10 | Merck Sharp & Dohme Corp. | Vėžio gydymo kompozicijos ir būdai |
| BR112015013611A2 (pt) | 2012-12-20 | 2017-11-14 | Merck Sharp & Dohme | composto, e, composição farmacêutica |
| WO2014120748A1 (en) | 2013-01-30 | 2014-08-07 | Merck Sharp & Dohme Corp. | 2,6,7,8 substituted purines as hdm2 inhibitors |
| US20160194368A1 (en) | 2013-09-03 | 2016-07-07 | Moderna Therapeutics, Inc. | Circular polynucleotides |
| MY196648A (en) | 2016-02-05 | 2023-04-27 | Denali Therapeutics Inc | Inhibitors of Receptor-Interacting Protein Kinase 1 |
| PT3552017T (pt) | 2016-12-09 | 2022-05-04 | Denali Therapeutics Inc | Compostos úteis como inibidores de ripk1 |
| US10947234B2 (en) | 2017-11-08 | 2021-03-16 | Merck Sharp & Dohme Corp. | PRMT5 inhibitors |
| US20210277009A1 (en) | 2018-08-07 | 2021-09-09 | Merck Sharp & Dohme Corp. | Prmt5 inhibitors |
| US20210309688A1 (en) | 2018-08-07 | 2021-10-07 | Merck Sharp & Dohme Corp. | Prmt5 inhibitors |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8929070D0 (en) * | 1989-12-22 | 1990-02-28 | Fujisawa Pharmaceutical Co | Peptide compounds,processes for preparation thereof and pharmaceutical composition comprising the same |
| GB9023116D0 (en) * | 1990-10-24 | 1990-12-05 | Fujisawa Pharmaceutical Co | Peptide compounds,processes for preparation thereof and pharmaceutical composition comprising the same |
| SK65094A3 (en) * | 1992-09-03 | 1995-03-08 | Boehringer Ingelheim Kg | Aminoacid derivatives, process for producing the same and pharmaceutical compositions containing these derivatives |
-
1995
- 1995-05-04 CZ CZ963254A patent/CZ325496A3/cs unknown
- 1995-05-04 EP EP95919392A patent/EP0804463A1/de not_active Withdrawn
- 1995-05-04 CN CN95192859A patent/CN1147260A/zh active Pending
- 1995-05-04 AU AU25249/95A patent/AU690275B2/en not_active Ceased
- 1995-05-04 EE EE9600186A patent/EE9600186A/xx unknown
- 1995-05-04 PL PL95317127A patent/PL317127A1/xx unknown
- 1995-05-04 MX MX9605128A patent/MX9605128A/es unknown
- 1995-05-04 JP JP7528677A patent/JPH09512806A/ja not_active Ceased
- 1995-05-04 RO RO96-02085A patent/RO115355B1/ro unknown
- 1995-05-04 CA CA002189764A patent/CA2189764A1/en not_active Abandoned
- 1995-05-04 SK SK1426-96A patent/SK142696A3/sk unknown
- 1995-05-04 US US08/434,613 patent/US5712273A/en not_active Expired - Fee Related
- 1995-05-04 NZ NZ285750A patent/NZ285750A/en unknown
- 1995-05-04 HU HU9603082A patent/HUT75708A/hu unknown
- 1995-05-04 WO PCT/EP1995/001691 patent/WO1995030687A1/de not_active Application Discontinuation
- 1995-05-05 IL IL11362595A patent/IL113625A0/xx unknown
- 1995-05-05 HR HRP4445939.4A patent/HRP950276A2/hr not_active Application Discontinuation
- 1995-06-07 US US08/475,278 patent/US5700827A/en not_active Expired - Fee Related
-
1996
- 1996-10-29 BG BG100946A patent/BG100946A/xx unknown
- 1996-11-06 NO NO964700A patent/NO964700D0/no not_active Application Discontinuation
- 1996-11-07 FI FI964473A patent/FI964473A0/fi unknown
Non-Patent Citations (1)
| Title |
|---|
| See references of WO9530687A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| IL113625A0 (en) | 1995-08-31 |
| BG100946A (en) | 1997-07-31 |
| AU2524995A (en) | 1995-11-29 |
| PL317127A1 (en) | 1997-03-17 |
| FI964473A (fi) | 1996-11-07 |
| EE9600186A (et) | 1997-08-15 |
| HUT75708A (en) | 1997-05-28 |
| NO964700L (no) | 1996-11-06 |
| HRP950276A2 (en) | 1997-04-30 |
| HU9603082D0 (en) | 1997-01-28 |
| MX9605128A (es) | 1997-08-30 |
| US5700827A (en) | 1997-12-23 |
| NO964700D0 (no) | 1996-11-06 |
| US5712273A (en) | 1998-01-27 |
| WO1995030687A1 (de) | 1995-11-16 |
| CA2189764A1 (en) | 1995-11-16 |
| RO115355B1 (ro) | 2000-01-28 |
| FI964473A0 (fi) | 1996-11-07 |
| CN1147260A (zh) | 1997-04-09 |
| JPH09512806A (ja) | 1997-12-22 |
| NZ285750A (en) | 1998-08-26 |
| SK142696A3 (en) | 1997-06-04 |
| AU690275B2 (en) | 1998-04-23 |
| CZ325496A3 (en) | 1997-09-17 |
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