NO300417B1 - Perhydroisoindolderivater som antagonister mot substans P - Google Patents
Perhydroisoindolderivater som antagonister mot substans P Download PDFInfo
- Publication number
- NO300417B1 NO300417B1 NO943692A NO943692A NO300417B1 NO 300417 B1 NO300417 B1 NO 300417B1 NO 943692 A NO943692 A NO 943692A NO 943692 A NO943692 A NO 943692A NO 300417 B1 NO300417 B1 NO 300417B1
- Authority
- NO
- Norway
- Prior art keywords
- methoxyphenyl
- diphenyl
- perhydroisoindolol
- symbol
- residue
- Prior art date
Links
- ODSNARDHJFFSRH-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-isoindole Chemical class C1CCCC2CNCC21 ODSNARDHJFFSRH-UHFFFAOYSA-N 0.000 title claims description 24
- 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 title description 21
- 102100024304 Protachykinin-1 Human genes 0.000 title description 21
- 101800003906 Substance P Proteins 0.000 title description 21
- 239000005557 antagonist Substances 0.000 title description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 34
- -1 benzyloxy, hydroxy Chemical group 0.000 claims description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
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- 125000002252 acyl group Chemical group 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
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- MZFMPHIMVMTSDO-UHFFFAOYSA-N 1-[4-hydroxy-4-(2-methoxyphenyl)-7,7-diphenyl-1,3,3a,5,6,7a-hexahydroisoindol-2-yl]-2-(2-hydroxyphenyl)propan-1-one Chemical compound COC1=CC=CC=C1C1(O)C2CN(C(=O)C(C)C=3C(=CC=CC=3)O)CC2C(C=2C=CC=CC=2)(C=2C=CC=CC=2)CC1 MZFMPHIMVMTSDO-UHFFFAOYSA-N 0.000 claims description 2
- ZDEDLFXGBIDZTJ-UHFFFAOYSA-N 1-[4-hydroxy-4-(2-methoxyphenyl)-7,7-diphenyl-1,3,3a,5,6,7a-hexahydroisoindol-2-yl]-2-(2-methoxyphenyl)ethanone Chemical compound COC1=CC=CC=C1CC(=O)N1CC(C(CCC2(O)C=3C(=CC=CC=3)OC)(C=3C=CC=CC=3)C=3C=CC=CC=3)C2C1 ZDEDLFXGBIDZTJ-UHFFFAOYSA-N 0.000 claims description 2
- CCIWVEMVBWEMCY-UHFFFAOYSA-N 1-[4-hydroxy-4-(2-methoxyphenyl)-7,7-diphenyl-1,3,3a,5,6,7a-hexahydroisoindol-2-yl]-2-(2-methoxyphenyl)propan-1-one Chemical group COC1=CC=CC=C1C(C)C(=O)N1CC(C(CCC2(O)C=3C(=CC=CC=3)OC)(C=3C=CC=CC=3)C=3C=CC=CC=3)C2C1 CCIWVEMVBWEMCY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
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- 229910052757 nitrogen Inorganic materials 0.000 description 24
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- 229910002027 silica gel Inorganic materials 0.000 description 24
- 239000011780 sodium chloride Substances 0.000 description 23
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 22
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 22
- 238000003756 stirring Methods 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 238000002360 preparation method Methods 0.000 description 20
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 19
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- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 230000026267 regulation of growth Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- PMOBWAXBGUSOPS-UHFFFAOYSA-N selenium tetrafluoride Chemical compound F[Se](F)(F)F PMOBWAXBGUSOPS-UHFFFAOYSA-N 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 230000001148 spastic effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- DOFWPVHNCPKPNB-SWFBWHSRSA-N tert-butyl (3as,4s,7as)-4-hydroxy-4,7,7-triphenyl-1,3,3a,5,6,7a-hexahydroisoindole-2-carboxylate Chemical compound C1([C@]2(O)CCC([C@@H]3[C@H]2CN(C3)C(=O)OC(C)(C)C)(C=2C=CC=CC=2)C=2C=CC=CC=2)=CC=CC=C1 DOFWPVHNCPKPNB-SWFBWHSRSA-N 0.000 description 1
- XIRDWFIDMQZDEU-UHFFFAOYSA-N tetrafluoro(phenyl)-$l^{5}-phosphane Chemical compound FP(F)(F)(F)C1=CC=CC=C1 XIRDWFIDMQZDEU-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- UFXIRMVZNARBDL-UHFFFAOYSA-N trifluoro(morpholin-4-yl)-$l^{4}-sulfane Chemical compound FS(F)(F)N1CCOCC1 UFXIRMVZNARBDL-UHFFFAOYSA-N 0.000 description 1
- AECHPKVYOLOZLF-UHFFFAOYSA-N trifluoro(phenyl)-$l^{4}-sulfane Chemical compound FS(F)(F)C1=CC=CC=C1 AECHPKVYOLOZLF-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000002348 vinylic group Chemical group 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
Classifications
-
- 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
- C07D403/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
- 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
- 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
- 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
- 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
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- 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
- A61P9/12—Antihypertensives
-
- 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
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pulmonology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR929204390A FR2689888B1 (fr) | 1992-04-10 | 1992-04-10 | Nouveaux derives de perhydroisoindole, leur preparation et les compositions pharmaceutiques qui les contiennent. |
PCT/FR1993/000352 WO1993021155A1 (fr) | 1992-04-10 | 1993-04-08 | Derives de perhydroisoindole comme antagonistes de la substance p |
Publications (3)
Publication Number | Publication Date |
---|---|
NO943692L NO943692L (no) | 1994-10-03 |
NO943692D0 NO943692D0 (no) | 1994-10-03 |
NO300417B1 true NO300417B1 (no) | 1997-05-26 |
Family
ID=9428707
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO943692A NO300417B1 (no) | 1992-04-10 | 1994-10-03 | Perhydroisoindolderivater som antagonister mot substans P |
Country Status (24)
Country | Link |
---|---|
US (1) | US5484804A (es) |
EP (1) | EP0635003B1 (es) |
JP (1) | JP3205557B2 (es) |
KR (1) | KR950700880A (es) |
AT (1) | ATE167472T1 (es) |
AU (1) | AU667214B2 (es) |
CA (1) | CA2133840A1 (es) |
CZ (1) | CZ284213B6 (es) |
DE (1) | DE69319235T2 (es) |
DK (1) | DK0635003T3 (es) |
ES (1) | ES2118232T3 (es) |
FI (1) | FI105023B (es) |
FR (1) | FR2689888B1 (es) |
HU (1) | HUT71354A (es) |
IL (1) | IL105255A (es) |
MX (1) | MX9301986A (es) |
NO (1) | NO300417B1 (es) |
NZ (1) | NZ251730A (es) |
PL (1) | PL172754B1 (es) |
RU (1) | RU2127260C1 (es) |
SK (1) | SK279032B6 (es) |
TW (1) | TW234119B (es) |
WO (1) | WO1993021155A1 (es) |
ZA (1) | ZA932527B (es) |
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FR2700472B1 (fr) | 1993-01-19 | 1995-02-17 | Rhone Poulenc Rorer Sa | Association synergisante ayant un effet antagoniste des récepteurs NK1 et NK2. |
FR2703679B1 (fr) * | 1993-04-05 | 1995-06-23 | Rhone Poulenc Rorer Sa | Nouveaux derives de perhydroisoindole, leur preparation et les compositions pharmaceutiques qui les contiennent. |
TW365603B (en) * | 1993-07-30 | 1999-08-01 | Rhone Poulenc Rorer Sa | Novel perhydroisoindole derivatives, their preparation and pharmaceutical compositions which contain them |
FR2710913B1 (fr) * | 1993-10-07 | 1995-11-24 | Rhone Poulenc Rorer Sa | Nouveaux dérivés de perhydroisoindole, leur préparation et les compositions pharmaceutiques qui les contiennent. |
FR2709752B1 (fr) * | 1993-07-30 | 1995-10-06 | Rhone Poulenc Rorer Sa | Nouveaux dérivés de perhydroisoindole, leur préparation et les compositions pharmaceutiques qui les contiennent. |
FR2710842B1 (fr) * | 1993-10-07 | 1995-11-24 | Rhone Poulenc Rorer Sa | Nouvelle application thérapeutique de dérivés de perhydroisoindole. |
FR2725900B1 (fr) * | 1994-10-21 | 1997-07-18 | Sanofi Sa | Utilisation d'antagonistes des recepteurs nk1 pour la preparation de medicaments a action cardioregulatrice |
FR2727411B1 (fr) * | 1994-11-30 | 1997-01-03 | Rhone Poulenc Rorer Sa | Nouveaux derives de perhydroisoindole, leur preparation et les compositions pharmaceutiques qui les contiennent |
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FR2737495B1 (fr) * | 1995-08-02 | 1997-08-29 | Rhone Poulenc Rorer Sa | Nouveaux derives de perhydroisoindole, leur preparation et les compositions pharmaceutiques qui les contiennent |
DE19636150A1 (de) * | 1996-09-06 | 1998-03-12 | Asta Medica Ag | N-substituierte Indol-3-glyoxylamide mit antiasthmatischer, antiallergischer und immunsuppressiver/immunmodulierender Wirkung |
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CA2298779A1 (en) * | 1997-08-04 | 1999-02-18 | Merck Sharp & Dohme Limited | Use of nk-1 receptor antagonists for treating aggressive behaviour disorders |
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FR514273A (fr) * | 1920-04-23 | 1921-03-07 | Georges Loutz | Bougie d'allumage électrique pour moteurs à explosions |
US4042707A (en) * | 1976-02-19 | 1977-08-16 | E. I. Du Pont De Nemours And Company | 3α-Arylhydroisoindoles |
FR2654725B1 (fr) * | 1989-11-23 | 1992-02-14 | Rhone Poulenc Sante | Nouveaux derives de l'isoindolone, leur preparation et les compositions pharmaceutiques qui les contiennent. |
FR2676442B1 (fr) * | 1991-05-17 | 1993-08-06 | Rhone Poulenc Rorer Sa | Nouveau derives de perhydroisoindole, leur preparation et les compositions pharmaceutiques qui les contiennent. |
FR2689889B1 (fr) * | 1992-04-10 | 1994-06-10 | Rhone Poulenc Rorer Sa | Nouveaux derives de perhydroisoindole, et leur preparation. |
-
1992
- 1992-04-10 FR FR929204390A patent/FR2689888B1/fr not_active Expired - Fee Related
-
1993
- 1993-04-01 IL IL10525593A patent/IL105255A/xx not_active IP Right Cessation
- 1993-04-06 MX MX9301986A patent/MX9301986A/es not_active Application Discontinuation
- 1993-04-08 WO PCT/FR1993/000352 patent/WO1993021155A1/fr active IP Right Grant
- 1993-04-08 US US08/313,121 patent/US5484804A/en not_active Expired - Lifetime
- 1993-04-08 ES ES93909005T patent/ES2118232T3/es not_active Expired - Lifetime
- 1993-04-08 CZ CZ942482A patent/CZ284213B6/cs unknown
- 1993-04-08 ZA ZA932527A patent/ZA932527B/xx unknown
- 1993-04-08 HU HU9402911A patent/HUT71354A/hu unknown
- 1993-04-08 AT AT93909005T patent/ATE167472T1/de active
- 1993-04-08 JP JP51804193A patent/JP3205557B2/ja not_active Expired - Lifetime
- 1993-04-08 NZ NZ251730A patent/NZ251730A/en unknown
- 1993-04-08 SK SK1220-94A patent/SK279032B6/sk unknown
- 1993-04-08 PL PL93305360A patent/PL172754B1/pl unknown
- 1993-04-08 DK DK93909005T patent/DK0635003T3/da active
- 1993-04-08 CA CA002133840A patent/CA2133840A1/fr not_active Abandoned
- 1993-04-08 AU AU39565/93A patent/AU667214B2/en not_active Ceased
- 1993-04-08 DE DE69319235T patent/DE69319235T2/de not_active Expired - Lifetime
- 1993-04-08 RU RU94045855A patent/RU2127260C1/ru active
- 1993-04-08 EP EP93909005A patent/EP0635003B1/fr not_active Expired - Lifetime
- 1993-04-09 TW TW082102664A patent/TW234119B/zh active
-
1994
- 1994-10-03 NO NO943692A patent/NO300417B1/no not_active IP Right Cessation
- 1994-10-06 KR KR1019940703538A patent/KR950700880A/ko not_active Application Discontinuation
- 1994-10-07 FI FI944729A patent/FI105023B/fi active
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