NO309144B1 - Substituerte pyrrolidin-3-yl-alkyl-piperidiner som er anvendbare som tachykininantagonister - Google Patents
Substituerte pyrrolidin-3-yl-alkyl-piperidiner som er anvendbare som tachykininantagonister Download PDFInfo
- Publication number
- NO309144B1 NO309144B1 NO954400A NO954400A NO309144B1 NO 309144 B1 NO309144 B1 NO 309144B1 NO 954400 A NO954400 A NO 954400A NO 954400 A NO954400 A NO 954400A NO 309144 B1 NO309144 B1 NO 309144B1
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- ethyl
- pyrrolidin
- formula
- carboxylic acid
- Prior art date
Links
- 102000003141 Tachykinin Human genes 0.000 title abstract description 28
- 108060008037 tachykinin Proteins 0.000 title abstract description 28
- 239000005557 antagonist Substances 0.000 title description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 256
- 150000003839 salts Chemical class 0.000 claims abstract description 39
- 238000002360 preparation method Methods 0.000 claims abstract description 31
- 239000000203 mixture Substances 0.000 claims description 68
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 17
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 14
- WZMVQZJKOVPVGZ-UHFFFAOYSA-N 1-[2-[3-(3,4-dichlorophenyl)-1-(3,4,5-trimethoxybenzoyl)pyrrolidin-3-yl]ethyl]-4-phenylpiperidine-4-carboxamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)N2CC(CCN3CCC(CC3)(C(N)=O)C=3C=CC=CC=3)(CC2)C=2C=C(Cl)C(Cl)=CC=2)=C1 WZMVQZJKOVPVGZ-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 9
- 208000006673 asthma Diseases 0.000 claims description 8
- 208000002193 Pain Diseases 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 206010011224 Cough Diseases 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- JHJNEMCXXDMXAV-UHFFFAOYSA-N 1-[2-(1-benzoyl-3-naphthalen-2-ylpyrrolidin-3-yl)ethyl]-4-phenylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N)(C=2C=CC=CC=2)CCN1CCC(C1)(C=2C=C3C=CC=CC3=CC=2)CCN1C(=O)C1=CC=CC=C1 JHJNEMCXXDMXAV-UHFFFAOYSA-N 0.000 claims description 2
- IWQWJVGWWLPNNI-UHFFFAOYSA-N 1-[2-[1-[3,5-bis(trifluoromethyl)benzoyl]-3-(3,4-dichlorophenyl)pyrrolidin-3-yl]ethyl]-4-phenylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N)(C=2C=CC=CC=2)CCN1CCC(C1)(C=2C=C(Cl)C(Cl)=CC=2)CCN1C(=O)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 IWQWJVGWWLPNNI-UHFFFAOYSA-N 0.000 claims description 2
- JMIKNHGMALLEMU-UHFFFAOYSA-N 1-[2-[1-benzoyl-3-(3,4-dichlorophenyl)pyrrolidin-3-yl]ethyl]-4-phenylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N)(C=2C=CC=CC=2)CCN1CCC(C1)(C=2C=C(Cl)C(Cl)=CC=2)CCN1C(=O)C1=CC=CC=C1 JMIKNHGMALLEMU-UHFFFAOYSA-N 0.000 claims description 2
- DJQNAWVRMSVHNZ-UHFFFAOYSA-N 1-[2-[3-(3,4-dichlorophenyl)-1-(2,4-dimethoxybenzoyl)pyrrolidin-3-yl]ethyl]-4-phenylpiperidine-4-carboxamide Chemical compound COC1=CC(OC)=CC=C1C(=O)N1CC(CCN2CCC(CC2)(C(N)=O)C=2C=CC=CC=2)(C=2C=C(Cl)C(Cl)=CC=2)CC1 DJQNAWVRMSVHNZ-UHFFFAOYSA-N 0.000 claims description 2
- GFELCGJBQGNHBL-UHFFFAOYSA-N 1-[2-[3-(3,4-dichlorophenyl)-1-(2,6-dimethoxybenzoyl)pyrrolidin-3-yl]ethyl]-4-phenylpiperidine-4-carboxamide Chemical compound COC1=CC=CC(OC)=C1C(=O)N1CC(CCN2CCC(CC2)(C(N)=O)C=2C=CC=CC=2)(C=2C=C(Cl)C(Cl)=CC=2)CC1 GFELCGJBQGNHBL-UHFFFAOYSA-N 0.000 claims description 2
- VMXIXFZELDQUJS-UHFFFAOYSA-N 1-[2-[3-(3,4-dichlorophenyl)-1-(2-methoxybenzoyl)pyrrolidin-3-yl]ethyl]-4-phenylpiperidine-4-carboxamide Chemical compound COC1=CC=CC=C1C(=O)N1CC(CCN2CCC(CC2)(C(N)=O)C=2C=CC=CC=2)(C=2C=C(Cl)C(Cl)=CC=2)CC1 VMXIXFZELDQUJS-UHFFFAOYSA-N 0.000 claims description 2
- HPRPQPRCKSBECC-UHFFFAOYSA-N 1-[2-[3-(3,4-dichlorophenyl)-1-(3,4,5-trimethoxybenzoyl)pyrrolidin-3-yl]ethyl]-n-[2-(dimethylamino)ethyl]-4-phenylpiperidine-4-carboxamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)N2CC(CCN3CCC(CC3)(C(=O)NCCN(C)C)C=3C=CC=CC=3)(CC2)C=2C=C(Cl)C(Cl)=CC=2)=C1 HPRPQPRCKSBECC-UHFFFAOYSA-N 0.000 claims description 2
- GUUBAKCFURYWAZ-UHFFFAOYSA-N 1-[2-[3-(3,4-dichlorophenyl)-1-(3-methoxybenzoyl)pyrrolidin-3-yl]ethyl]-4-phenylpiperidine-4-carboxamide Chemical compound COC1=CC=CC(C(=O)N2CC(CCN3CCC(CC3)(C(N)=O)C=3C=CC=CC=3)(CC2)C=2C=C(Cl)C(Cl)=CC=2)=C1 GUUBAKCFURYWAZ-UHFFFAOYSA-N 0.000 claims description 2
- YCMAOHLEJMWCLX-UHFFFAOYSA-N 1-[2-[3-(3,4-dichlorophenyl)-1-[2-(2-methoxyphenyl)acetyl]pyrrolidin-3-yl]ethyl]-4-phenylpiperidine-4-carboxamide Chemical compound COC1=CC=CC=C1CC(=O)N1CC(CCN2CCC(CC2)(C(N)=O)C=2C=CC=CC=2)(C=2C=C(Cl)C(Cl)=CC=2)CC1 YCMAOHLEJMWCLX-UHFFFAOYSA-N 0.000 claims description 2
- UVHJSIDFUVBWQC-UHFFFAOYSA-N 4-phenyl-1-[2-[3-phenyl-1-(3,4,5-trimethoxybenzoyl)pyrrolidin-3-yl]ethyl]piperidine-4-carboxamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)N2CC(CCN3CCC(CC3)(C(N)=O)C=3C=CC=CC=3)(CC2)C=2C=CC=CC=2)=C1 UVHJSIDFUVBWQC-UHFFFAOYSA-N 0.000 claims description 2
- KGDKHLHDDRKQQP-UHFFFAOYSA-N 8-[2-[3-(3,4-dichlorophenyl)-1-(2,6-dimethoxybenzoyl)pyrrolidin-3-yl]ethyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound COC1=CC=CC(OC)=C1C(=O)N1CC(CCN2CCC3(CC2)C(NCN3C=2C=CC=CC=2)=O)(C=2C=C(Cl)C(Cl)=CC=2)CC1 KGDKHLHDDRKQQP-UHFFFAOYSA-N 0.000 claims description 2
- 230000001272 neurogenic effect Effects 0.000 claims description 2
- 208000023504 respiratory system disease Diseases 0.000 claims description 2
- NICAQILMIFKWPA-UHFFFAOYSA-N 1-[2-[1-benzyl-3-(3,4-dichlorophenyl)-5-oxopyrrolidin-3-yl]ethyl]-4-phenylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N)(C=2C=CC=CC=2)CCN1CCC(CC1=O)(C=2C=C(Cl)C(Cl)=CC=2)CN1CC1=CC=CC=C1 NICAQILMIFKWPA-UHFFFAOYSA-N 0.000 claims 1
- FMTLSROFQVSZGR-UHFFFAOYSA-N 1-[2-[3-(3,4-dimethoxyphenyl)-1-(3,4,5-trimethoxybenzoyl)pyrrolidin-3-yl]ethyl]-4-phenylpiperidine-4-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1(CCN2CCC(CC2)(C(N)=O)C=2C=CC=CC=2)CN(C(=O)C=2C=C(OC)C(OC)=C(OC)C=2)CC1 FMTLSROFQVSZGR-UHFFFAOYSA-N 0.000 claims 1
- YEHZDBDUEDGUMK-UHFFFAOYSA-N 8-[2-[1-benzoyl-3-(3,4-dichlorophenyl)pyrrolidin-3-yl]ethyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1(CCN2CCC3(CC2)C(NCN3C=2C=CC=CC=2)=O)CN(C(=O)C=2C=CC=CC=2)CC1 YEHZDBDUEDGUMK-UHFFFAOYSA-N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 71
- 230000008485 antagonism Effects 0.000 abstract description 27
- 101800000399 Neurokinin A Proteins 0.000 abstract description 24
- HEAUFJZALFKPBA-YRVBCFNBSA-N Neurokinin A Chemical compound C([C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)C(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCCN)NC(=O)[C@@H](N)CC=1NC=NC=1)C(C)O)C1=CC=CC=C1 HEAUFJZALFKPBA-YRVBCFNBSA-N 0.000 abstract description 24
- 102400000097 Neurokinin A Human genes 0.000 abstract description 24
- 201000010099 disease Diseases 0.000 abstract description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 21
- 102100024304 Protachykinin-1 Human genes 0.000 abstract description 12
- 101800003906 Substance P Proteins 0.000 abstract description 12
- QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 abstract description 11
- 208000007920 Neurogenic Inflammation Diseases 0.000 abstract description 3
- 230000000144 pharmacologic effect Effects 0.000 abstract description 3
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 513
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 366
- 238000006243 chemical reaction Methods 0.000 description 277
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 219
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 170
- 238000003786 synthesis reaction Methods 0.000 description 129
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- 239000000243 solution Substances 0.000 description 118
- -1 Polycyclic amine compounds Chemical class 0.000 description 112
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 102
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 90
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- 238000000605 extraction Methods 0.000 description 50
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- 239000002585 base Substances 0.000 description 42
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- 238000010992 reflux Methods 0.000 description 40
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- 238000004458 analytical method Methods 0.000 description 29
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 28
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 27
- 238000003756 stirring Methods 0.000 description 27
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- 108010040722 Neurokinin-2 Receptors Proteins 0.000 description 20
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- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 19
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- 229910052794 bromium Inorganic materials 0.000 description 18
- LZWFVOQSFVFPJK-UHFFFAOYSA-N 4-phenylpiperidine-4-carboxamide;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C1(C(=O)N)CCNCC1 LZWFVOQSFVFPJK-UHFFFAOYSA-N 0.000 description 17
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- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
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Classifications
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- 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
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US5860693A | 1993-05-06 | 1993-05-06 | |
US21848394A | 1994-03-28 | 1994-03-28 | |
US22537194A | 1994-04-19 | 1994-04-19 | |
PCT/US1994/004498 WO1994026735A1 (en) | 1993-05-06 | 1994-04-22 | Substituted pyrrolidin-3-yl-alkyl-piperidines useful as tachykinin antagonists |
Publications (3)
Publication Number | Publication Date |
---|---|
NO954400D0 NO954400D0 (no) | 1995-11-03 |
NO954400L NO954400L (no) | 1996-01-08 |
NO309144B1 true NO309144B1 (no) | 2000-12-18 |
Family
ID=27369482
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO954400A NO309144B1 (no) | 1993-05-06 | 1995-11-03 | Substituerte pyrrolidin-3-yl-alkyl-piperidiner som er anvendbare som tachykininantagonister |
Country Status (18)
Country | Link |
---|---|
EP (1) | EP0696280B1 (fi) |
JP (1) | JP3424174B2 (fi) |
CN (1) | CN1081635C (fi) |
AT (1) | ATE158580T1 (fi) |
AU (1) | AU678023B2 (fi) |
CA (1) | CA2160462C (fi) |
DE (1) | DE69405862T2 (fi) |
DK (1) | DK0696280T3 (fi) |
ES (1) | ES2110761T3 (fi) |
FI (1) | FI113047B (fi) |
GR (1) | GR3025475T3 (fi) |
HU (1) | HU224496B1 (fi) |
IL (1) | IL109496A (fi) |
MX (1) | MX9403386A (fi) |
NO (1) | NO309144B1 (fi) |
NZ (1) | NZ267209A (fi) |
TW (1) | TW281675B (fi) |
WO (1) | WO1994026735A1 (fi) |
Families Citing this family (76)
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FR2717802B1 (fr) * | 1994-03-25 | 1996-06-21 | Sanofi Sa | Nouveaux composés aromatiques, procédé pour leur préparation et compositions pharmaceutiques en contenant. |
EP0777666B1 (en) | 1994-08-25 | 1999-03-03 | Merrell Pharmaceuticals Inc. | Substituted piperidines useful for the treatment of allergic diseases |
CA2162786A1 (en) * | 1994-11-22 | 1996-05-23 | Philip Arthur Hipskind | Heterocyclic tachykinin receptor antagonists |
FR2729954B1 (fr) * | 1995-01-30 | 1997-08-01 | Sanofi Sa | Composes heterocycliques substitues, procede pour leur preparation et compositions pharmaceutiques les contenant |
DE69615670T2 (de) * | 1995-03-15 | 2002-08-08 | Aventis Pharmaceuticals Inc., Bridgewater | Heterocyclisch substituierte piperazonderivate als tachykinin rezeptor antagonisten |
EP0830347B1 (en) * | 1995-04-13 | 2004-09-22 | Aventis Pharmaceuticals, Inc. | Novel substituted piperazine derivatives having tachykinin receptor antagonists activity |
US5661163A (en) | 1995-06-07 | 1997-08-26 | Merck & Co., Inc. | Alpha-1a adrenergic receptor antagonists |
FR2738245B1 (fr) * | 1995-08-28 | 1997-11-21 | Sanofi Sa | Nouveaux derives de piperidine, procede pour leur obtention et compositions pharmaceutiques les contenant |
FR2738819B1 (fr) * | 1995-09-14 | 1997-12-05 | Sanofi Sa | Nouveaux composes antagonistes selectifs du recepteur nk3 humain, procede pour leur obtention et compositions pharmaceutiques les contenant |
CA2228572C (en) | 1995-10-10 | 2003-07-22 | Giovanni Piedimonte | Nk-1 receptor antagonists for prevention of neurogenic inflammation in gene therapy |
US6211199B1 (en) | 1995-11-17 | 2001-04-03 | Aventis Pharmaceuticals Inc. | Substituted 4-(1H-benzimidazol-2-yl-amino)piperidines useful for the treatment of allergic diseases |
HU224225B1 (hu) | 1995-12-01 | 2005-06-28 | Sankyo Co. Ltd. | Tachikinin receptor antagonista hatású heterociklusos vegyületek, ezek előállítási eljárása és alkalmazásuk gyógyszerkészítmények előállítására |
US6194406B1 (en) | 1995-12-20 | 2001-02-27 | Aventis Pharmaceuticals Inc. | Substituted 4-(1H-benzimidazol-2-yl)[1,4]diazepanes useful for the treatment of allergic disease |
ES2177827T3 (es) * | 1995-12-20 | 2002-12-16 | Aventis Pharma Inc | 4-(1h-bencimidazol-2-il)(1,4)diazepanes utiles para el tratamiento de enfermedades alergicas. |
US6423704B2 (en) | 1995-12-20 | 2002-07-23 | Aventis Pharmaceuticals Inc. | Substituted 4-(1H-benzimidazol-2-yl)[1,4]diazepanes useful for the treatment of allergic diseases |
GB9600235D0 (en) * | 1996-01-05 | 1996-03-06 | Pfizer Ltd | Therapeutic agents |
US5932571A (en) * | 1996-02-21 | 1999-08-03 | Hoechst Marion Roussel, Inc. | Substituted N-methyl-N-(4-(4-(1H-benzimidazol-2-yl) {1,4}diazepan-1-yl)-2-(aryl) butyl) benzamides useful for the treatment of allergic diseases |
US5922737A (en) * | 1996-02-21 | 1999-07-13 | Hoechst Marion Roussel, Inc. | Substituted N-methyl-N-(4-(4-(1H-Benzimidazol-2-YL-amino) piperidin-1-YL)-2-(arlyl) butyl) benzamides useful for the treatment of allergic diseases |
US5998439A (en) * | 1996-02-21 | 1999-12-07 | Hoescht Marion Roussel, Inc. | Substituted N-methyl-N-(4-(piperidin-1-yl)-2-(aryl)butyl)benzamides useful for the treatment of allergic diseases |
US5977139A (en) * | 1996-12-15 | 1999-11-02 | Hoechst Marion Roussel, Inc. | Carboxysubstituted cyclic carboxamide derivatives |
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AU2018333051B2 (en) | 2017-09-15 | 2024-03-21 | Azevan Pharmaceuticals, Inc. | Compositions and methods for treating brain injury |
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Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL99320A (en) * | 1990-09-05 | 1995-07-31 | Sanofi Sa | Arylalkylamines, their preparation and pharmaceutical preparations containing them |
FR2676055B1 (fr) * | 1991-05-03 | 1993-09-03 | Sanofi Elf | Composes polycycliques amines et leurs enantiomeres, procede pour leur preparation et compositions pharmaceutiques les contenant. |
-
1994
- 1994-04-22 NZ NZ267209A patent/NZ267209A/en unknown
- 1994-04-22 DK DK94917898.2T patent/DK0696280T3/da active
- 1994-04-22 WO PCT/US1994/004498 patent/WO1994026735A1/en active IP Right Grant
- 1994-04-22 HU HU9503153A patent/HU224496B1/hu not_active IP Right Cessation
- 1994-04-22 AU AU69426/94A patent/AU678023B2/en not_active Ceased
- 1994-04-22 EP EP94917898A patent/EP0696280B1/en not_active Expired - Lifetime
- 1994-04-22 CN CN94192362A patent/CN1081635C/zh not_active Expired - Fee Related
- 1994-04-22 CA CA002160462A patent/CA2160462C/en not_active Expired - Fee Related
- 1994-04-22 ES ES94917898T patent/ES2110761T3/es not_active Expired - Lifetime
- 1994-04-22 AT AT94917898T patent/ATE158580T1/de not_active IP Right Cessation
- 1994-04-22 DE DE69405862T patent/DE69405862T2/de not_active Expired - Lifetime
- 1994-04-22 JP JP52545394A patent/JP3424174B2/ja not_active Expired - Fee Related
- 1994-04-26 TW TW083103768A patent/TW281675B/zh active
- 1994-05-02 IL IL10949694A patent/IL109496A/xx not_active IP Right Cessation
- 1994-05-06 MX MX9403386A patent/MX9403386A/es unknown
-
1995
- 1995-11-02 FI FI955258A patent/FI113047B/fi not_active IP Right Cessation
- 1995-11-03 NO NO954400A patent/NO309144B1/no not_active IP Right Cessation
-
1997
- 1997-11-26 GR GR970403124T patent/GR3025475T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
CN1124961A (zh) | 1996-06-19 |
GR3025475T3 (en) | 1998-02-27 |
MX9403386A (es) | 1995-01-31 |
CN1081635C (zh) | 2002-03-27 |
AU678023B2 (en) | 1997-05-15 |
TW281675B (fi) | 1996-07-21 |
IL109496A (en) | 2000-07-26 |
EP0696280B1 (en) | 1997-09-24 |
HUT74085A (en) | 1996-11-28 |
NO954400L (no) | 1996-01-08 |
AU6942694A (en) | 1994-12-12 |
EP0696280A1 (en) | 1996-02-14 |
FI955258A0 (fi) | 1995-11-02 |
ATE158580T1 (de) | 1997-10-15 |
ES2110761T3 (es) | 1998-02-16 |
NZ267209A (en) | 1997-09-22 |
CA2160462C (en) | 1998-12-15 |
HU9503153D0 (en) | 1996-01-29 |
FI113047B (fi) | 2004-02-27 |
JP3424174B2 (ja) | 2003-07-07 |
DE69405862T2 (de) | 1998-01-15 |
NO954400D0 (no) | 1995-11-03 |
DE69405862D1 (de) | 1997-10-30 |
HU224496B1 (hu) | 2005-10-28 |
IL109496A0 (en) | 1994-08-26 |
JPH09500361A (ja) | 1997-01-14 |
DK0696280T3 (da) | 1998-01-12 |
FI955258A (fi) | 1995-11-30 |
WO1994026735A1 (en) | 1994-11-24 |
CA2160462A1 (en) | 1994-11-24 |
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