FI115135B - Substituoidut alkyylidiamiinijohdannaiset ja niiden käyttö takykiniinin antagonisteina - Google Patents
Substituoidut alkyylidiamiinijohdannaiset ja niiden käyttö takykiniinin antagonisteina Download PDFInfo
- Publication number
- FI115135B FI115135B FI965097A FI965097A FI115135B FI 115135 B FI115135 B FI 115135B FI 965097 A FI965097 A FI 965097A FI 965097 A FI965097 A FI 965097A FI 115135 B FI115135 B FI 115135B
- Authority
- FI
- Finland
- Prior art keywords
- methyl
- ethylamino
- benzyl
- indol
- butoxycarbonyl
- Prior art date
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- 102000003141 Tachykinin Human genes 0.000 title claims abstract description 31
- 108060008037 tachykinin Proteins 0.000 title claims abstract description 31
- -1 Substituted alkyl diamine Chemical class 0.000 title claims description 207
- 239000005557 antagonist Substances 0.000 title abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 48
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 43
- 201000010099 disease Diseases 0.000 claims abstract description 42
- 230000001404 mediated effect Effects 0.000 claims abstract description 18
- 238000011282 treatment Methods 0.000 claims abstract description 17
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- 206010006451 bronchitis Diseases 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 236
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 118
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 86
- 238000000034 method Methods 0.000 claims description 80
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- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-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
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical group 0.000 claims description 9
- 125000005806 3,4,5-trimethoxybenzyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1C([H])([H])* 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
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- NIRCCCPMKJFGQK-NYDCQLBNSA-N (2s)-4-[2-[[(2s)-1-[benzyl(methyl)amino]-1-oxo-3-phenylpropan-2-yl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethylamino]-2-(1h-indol-3-yl)butanoic acid Chemical group O=C([C@H](CC=1C=CC=CC=1)N(CCNCC[C@H](C(O)=O)C=1C2=CC=CC=C2NC=1)C(=O)OC(C)(C)C)N(C)CC1=CC=CC=C1 NIRCCCPMKJFGQK-NYDCQLBNSA-N 0.000 claims description 2
- VXXLTHPXDVQCQQ-VMPREFPWSA-N (3S)-3-[2-[(2S)-1-[benzyl(methyl)amino]-1-oxo-3-phenylpropan-2-yl]-2-[3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]hydrazinyl]-3-phenylpropanoic acid Chemical group C(C1=CC=CC=C1)N(C([C@H](CC1=CC=CC=C1)N(CCC(=O)OC(C)(C)C)N[C@@H](CC(=O)O)C1=CC=CC=C1)=O)C VXXLTHPXDVQCQQ-VMPREFPWSA-N 0.000 claims description 2
- UNNWGICUMGKDPP-UHFFFAOYSA-N 2-(ethylamino)-3-phenylpropanamide Chemical compound CCNC(C(N)=O)CC1=CC=CC=C1 UNNWGICUMGKDPP-UHFFFAOYSA-N 0.000 claims description 2
- DOZZSWAOPDYVLH-UHFFFAOYSA-N 2-phenylpropanamide Chemical compound NC(=O)C(C)C1=CC=CC=C1 DOZZSWAOPDYVLH-UHFFFAOYSA-N 0.000 claims description 2
- QVHDOZFUPVJIHV-HKBQPEDESA-N tert-butyl n-[(2s)-1-[benzyl(methyl)amino]-1-oxo-3-phenylpropan-2-yl]-n-[2-[2-(1h-indol-3-yl)ethylamino]ethyl]carbamate Chemical group O=C([C@H](CC=1C=CC=CC=1)N(CCNCCC=1C2=CC=CC=C2NC=1)C(=O)OC(C)(C)C)N(C)CC1=CC=CC=C1 QVHDOZFUPVJIHV-HKBQPEDESA-N 0.000 claims description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 4
- 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- 238000004809 thin layer chromatography Methods 0.000 description 39
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- 239000002904 solvent Substances 0.000 description 35
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 33
- 239000002253 acid Substances 0.000 description 32
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 31
- 150000001412 amines Chemical class 0.000 description 31
- 239000003153 chemical reaction reagent Substances 0.000 description 31
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- 150000002009 diols Chemical class 0.000 description 28
- 238000000605 extraction Methods 0.000 description 28
- 238000001953 recrystallisation Methods 0.000 description 27
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 description 23
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 16
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- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 12
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- 239000000872 buffer Substances 0.000 description 10
- XNFNGGQRDXFYMM-PPHPATTJSA-N methyl (2s)-2-amino-3-(1h-indol-3-yl)propanoate;hydrochloride Chemical compound Cl.C1=CC=C2C(C[C@H](N)C(=O)OC)=CNC2=C1 XNFNGGQRDXFYMM-PPHPATTJSA-N 0.000 description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
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- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 9
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- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 6
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- YPLWRIBGHXBPTD-YJPOWDFOSA-N tert-butyl N-[(2S)-1-[benzyl(methyl)amino]-1-oxo-3-phenylpropan-2-yl]-N-[2-(oxan-2-yloxy)propyl]carbamate Chemical compound CC(CN([C@@H](Cc1ccccc1)C(=O)N(C)Cc1ccccc1)C(=O)OC(C)(C)C)OC1CCCCO1 YPLWRIBGHXBPTD-YJPOWDFOSA-N 0.000 description 1
- NKKNGAQCRQENPV-NRFANRHFSA-N tert-butyl n-[(2s)-1-[(2-methoxyphenyl)methyl-methylamino]-1-oxo-3-phenylpropan-2-yl]-n-(2-oxoethyl)carbamate Chemical compound COC1=CC=CC=C1CN(C)C(=O)[C@@H](N(CC=O)C(=O)OC(C)(C)C)CC1=CC=CC=C1 NKKNGAQCRQENPV-NRFANRHFSA-N 0.000 description 1
- CNEFFCMAEHEWON-VWLOTQADSA-N tert-butyl n-[(2s)-1-[(3,4-dichlorophenyl)methyl-methylamino]-3-naphthalen-2-yl-1-oxopropan-2-yl]-n-(2-oxoethyl)carbamate Chemical compound O=C([C@H](CC=1C=C2C=CC=CC2=CC=1)N(CC=O)C(=O)OC(C)(C)C)N(C)CC1=CC=C(Cl)C(Cl)=C1 CNEFFCMAEHEWON-VWLOTQADSA-N 0.000 description 1
- ZRPMNXGORBDRFR-QFIPXVFZSA-N tert-butyl n-[(2s)-1-[benzyl(methyl)amino]-1-oxo-3-phenylpropan-2-yl]-n-(3-oxopropyl)carbamate Chemical compound O=C([C@H](CC=1C=CC=CC=1)N(CCC=O)C(=O)OC(C)(C)C)N(C)CC1=CC=CC=C1 ZRPMNXGORBDRFR-QFIPXVFZSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
- A61P11/08—Bronchodilators
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/78—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/52—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the nitrogen atom of at least one of the carboxamide groups further acylated
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/262,209 US5597845A (en) | 1994-06-20 | 1994-06-20 | Substituted alkyldiamine derivatives |
| US26220994 | 1994-06-20 | ||
| US9506317 | 1995-05-19 | ||
| PCT/US1995/006317 WO1995035279A1 (en) | 1994-06-20 | 1995-05-19 | Substituted alkyldiamine derivatives and their use as tachykinin antagonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI965097A0 FI965097A0 (fi) | 1996-12-18 |
| FI965097L FI965097L (fi) | 1996-12-18 |
| FI115135B true FI115135B (fi) | 2005-03-15 |
Family
ID=22996631
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI965097A FI115135B (fi) | 1994-06-20 | 1996-12-18 | Substituoidut alkyylidiamiinijohdannaiset ja niiden käyttö takykiniinin antagonisteina |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US5597845A (cs) |
| EP (1) | EP0767783B1 (cs) |
| JP (1) | JP3920916B2 (cs) |
| KR (1) | KR100371981B1 (cs) |
| CN (1) | CN1083429C (cs) |
| AT (1) | ATE169905T1 (cs) |
| AU (1) | AU691619B2 (cs) |
| CA (1) | CA2193348C (cs) |
| DE (1) | DE69504198T2 (cs) |
| DK (1) | DK0767783T3 (cs) |
| ES (1) | ES2121389T3 (cs) |
| FI (1) | FI115135B (cs) |
| HU (1) | HUT75965A (cs) |
| IL (1) | IL114185A (cs) |
| MX (1) | MX9606654A (cs) |
| NO (1) | NO307458B1 (cs) |
| NZ (1) | NZ287291A (cs) |
| TW (1) | TW442451B (cs) |
| WO (1) | WO1995035279A1 (cs) |
| ZA (1) | ZA954947B (cs) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW541295B (en) * | 1999-01-05 | 2003-07-11 | Nippon Zoki Pharmaceutical Co | A novel substituted alkylteraamine derivative for use as tachykinin antagonist |
| US7361678B2 (en) | 2002-03-05 | 2008-04-22 | Transtech Pharma, Inc. | Azole derivatives and fused bicyclic azole derivatives as therapeutic agents |
| US6613801B2 (en) * | 2000-05-30 | 2003-09-02 | Transtech Pharma, Inc. | Method for the synthesis of compounds of formula I and their uses thereof |
| CN1235583C (zh) | 2001-03-05 | 2006-01-11 | 特兰斯泰克制药公司 | 用作治疗剂的苯并咪唑衍生物 |
| EP1377295A4 (en) | 2001-03-05 | 2007-05-09 | Transtech Pharma Inc | CARBOXYL ACID DERIVATIVES THERAPEUTIC AGENTS |
| US20090263370A1 (en) * | 2006-11-30 | 2009-10-22 | Guoliang Tao | Methods for treating tachykinin-mediated diseases with cholinesterase |
| WO2011041198A1 (en) | 2009-09-30 | 2011-04-07 | Transtech Pharma, Inc. | Substituted imidazole derivatives for treatment of alzheimers disease |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5164372A (en) * | 1989-04-28 | 1992-11-17 | Fujisawa Pharmaceutical Company, Ltd. | Peptide compounds having substance p antagonism, processes for preparation thereof and pharmaceutical composition comprising the same |
| JPH06509087A (ja) * | 1991-07-05 | 1994-10-13 | メルク シヤープ エンド ドーム リミテツド | 芳香族化合物、それらを含む医薬組成物、及び治療におけるそれらの使用 |
| JP3507494B2 (ja) * | 1992-08-13 | 2004-03-15 | ワーナー−ランバート・コンパニー | タキキニン拮抗薬 |
-
1994
- 1994-06-20 US US08/262,209 patent/US5597845A/en not_active Expired - Fee Related
-
1995
- 1995-05-19 CN CN95193680A patent/CN1083429C/zh not_active Expired - Fee Related
- 1995-05-19 EP EP95920539A patent/EP0767783B1/en not_active Expired - Lifetime
- 1995-05-19 DE DE69504198T patent/DE69504198T2/de not_active Expired - Fee Related
- 1995-05-19 MX MX9606654A patent/MX9606654A/es not_active IP Right Cessation
- 1995-05-19 HU HU9603540A patent/HUT75965A/hu not_active Application Discontinuation
- 1995-05-19 ES ES95920539T patent/ES2121389T3/es not_active Expired - Lifetime
- 1995-05-19 WO PCT/US1995/006317 patent/WO1995035279A1/en active IP Right Grant
- 1995-05-19 AU AU25961/95A patent/AU691619B2/en not_active Ceased
- 1995-05-19 DK DK95920539T patent/DK0767783T3/da active
- 1995-05-19 CA CA002193348A patent/CA2193348C/en not_active Expired - Fee Related
- 1995-05-19 AT AT95920539T patent/ATE169905T1/de not_active IP Right Cessation
- 1995-05-19 NZ NZ287291A patent/NZ287291A/xx unknown
- 1995-05-19 JP JP50217396A patent/JP3920916B2/ja not_active Expired - Fee Related
- 1995-05-19 KR KR1019960707303A patent/KR100371981B1/ko not_active Expired - Fee Related
- 1995-06-14 ZA ZA954947A patent/ZA954947B/xx unknown
- 1995-06-15 TW TW084106131A patent/TW442451B/zh not_active IP Right Cessation
- 1995-06-16 IL IL11418595A patent/IL114185A/xx not_active IP Right Cessation
-
1996
- 1996-12-18 FI FI965097A patent/FI115135B/fi not_active IP Right Cessation
- 1996-12-19 NO NO965469A patent/NO307458B1/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ287291A (en) | 1998-10-28 |
| KR100371981B1 (ko) | 2003-06-12 |
| CA2193348A1 (en) | 1995-12-28 |
| IL114185A (en) | 1999-07-14 |
| NO965469D0 (no) | 1996-12-19 |
| NO307458B1 (no) | 2000-04-10 |
| CN1155883A (zh) | 1997-07-30 |
| DE69504198T2 (de) | 1999-04-29 |
| EP0767783B1 (en) | 1998-08-19 |
| DE69504198D1 (de) | 1998-09-24 |
| NO965469L (no) | 1997-02-19 |
| FI965097A0 (fi) | 1996-12-18 |
| FI965097L (fi) | 1996-12-18 |
| ES2121389T3 (es) | 1998-11-16 |
| JP3920916B2 (ja) | 2007-05-30 |
| JPH10501551A (ja) | 1998-02-10 |
| CA2193348C (en) | 1999-08-24 |
| CN1083429C (zh) | 2002-04-24 |
| TW442451B (en) | 2001-06-23 |
| US5597845A (en) | 1997-01-28 |
| AU2596195A (en) | 1996-01-15 |
| EP0767783A1 (en) | 1997-04-16 |
| MX9606654A (es) | 1997-12-31 |
| ATE169905T1 (de) | 1998-09-15 |
| IL114185A0 (cs) | 1995-10-31 |
| ZA954947B (en) | 1996-01-31 |
| DK0767783T3 (da) | 1999-05-25 |
| AU691619B2 (en) | 1998-05-21 |
| HUT75965A (en) | 1997-05-28 |
| WO1995035279A1 (en) | 1995-12-28 |
| HU9603540D0 (en) | 1997-02-28 |
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