NO300133B1 - Analogifremgangsmåte for fremstilling av leukotrien antagonistiske indolderivater - Google Patents
Analogifremgangsmåte for fremstilling av leukotrien antagonistiske indolderivater Download PDFInfo
- Publication number
- NO300133B1 NO300133B1 NO912963A NO912963A NO300133B1 NO 300133 B1 NO300133 B1 NO 300133B1 NO 912963 A NO912963 A NO 912963A NO 912963 A NO912963 A NO 912963A NO 300133 B1 NO300133 B1 NO 300133B1
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- Norway
- Prior art keywords
- compound
- mmol
- hydrogen
- solution
- stirred
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 63
- 238000002360 preparation method Methods 0.000 title claims description 12
- 230000008569 process Effects 0.000 title claims description 4
- 150000002617 leukotrienes Chemical class 0.000 title description 5
- 150000002475 indoles Chemical class 0.000 title description 3
- 230000003042 antagnostic effect Effects 0.000 title 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 125
- 239000001257 hydrogen Substances 0.000 claims abstract description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 46
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 36
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 10
- 125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 66
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 50
- -1 5-tetrazolyl Chemical group 0.000 claims description 47
- 238000006243 chemical reaction Methods 0.000 claims description 39
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- 125000005843 halogen group Chemical group 0.000 claims description 12
- 239000003153 chemical reaction reagent Substances 0.000 claims description 10
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- 239000007858 starting material Substances 0.000 claims description 6
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- 150000002367 halogens Chemical class 0.000 claims description 5
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 230000002152 alkylating effect Effects 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 15
- 150000002825 nitriles Chemical class 0.000 abstract description 15
- 239000003199 leukotriene receptor blocking agent Substances 0.000 abstract description 5
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- SCZJKJJOPMUIQO-UHFFFAOYSA-N methyl 7-(cyanomethoxy)-1h-indole-4-carboxylate Chemical compound COC(=O)C1=CC=C(OCC#N)C2=C1C=CN2 SCZJKJJOPMUIQO-UHFFFAOYSA-N 0.000 description 1
- BEDCQSUWGKQSDF-UHFFFAOYSA-N methyl 7-(cyanomethoxy)-1h-indole-5-carboxylate Chemical compound COC(=O)C1=CC(OCC#N)=C2NC=CC2=C1 BEDCQSUWGKQSDF-UHFFFAOYSA-N 0.000 description 1
- IJPOSBBSSMJLPI-UHFFFAOYSA-N methyl 7-phenylmethoxy-1h-indole-4-carboxylate Chemical compound C1=2NC=CC=2C(C(=O)OC)=CC=C1OCC1=CC=CC=C1 IJPOSBBSSMJLPI-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000006187 phenyl benzyl group Chemical group 0.000 description 1
- FNPLJYOHPLBSJL-FYWRMAATSA-N phenyl-[3-[(e)-2-quinolin-2-ylethenyl]phenyl]methanol Chemical compound C=1C=CC(\C=C\C=2N=C3C=CC=CC3=CC=2)=CC=1C(O)C1=CC=CC=C1 FNPLJYOHPLBSJL-FYWRMAATSA-N 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical group OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 1
- BFICMSJXWUAPEH-UHFFFAOYSA-N quinolin-2-ylmethylphosphanium;chloride Chemical compound [Cl-].C1=CC=CC2=NC(C[PH3+])=CC=C21 BFICMSJXWUAPEH-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 108091006082 receptor inhibitors Proteins 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 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 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical group [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940033134 talc Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- HSGFGMBUKGMVRG-UHFFFAOYSA-N triphenyl(2H-tetrazol-5-ylmethyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC=1N=NNN=1 HSGFGMBUKGMVRG-UHFFFAOYSA-N 0.000 description 1
- BRHOKTBAFIQRFX-UHFFFAOYSA-M triphenyl(quinolin-2-ylmethyl)phosphanium;chloride Chemical compound [Cl-].C=1C=C2C=CC=CC2=NC=1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRHOKTBAFIQRFX-UHFFFAOYSA-M 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000007514 turning Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
- C07D401/02—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
- C07D401/08—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 alicyclic rings
-
- 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
-
- 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
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic 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
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D401/02—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
- C07D401/10—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 aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB909016790A GB9016790D0 (en) | 1990-07-31 | 1990-07-31 | Pharmaceutical compounds |
| GB919107486A GB9107486D0 (en) | 1991-04-09 | 1991-04-09 | Pharmaceutical compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO912963D0 NO912963D0 (no) | 1991-07-30 |
| NO912963L NO912963L (no) | 1992-02-03 |
| NO300133B1 true NO300133B1 (no) | 1997-04-14 |
Family
ID=26297410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO912963A NO300133B1 (no) | 1990-07-31 | 1991-07-30 | Analogifremgangsmåte for fremstilling av leukotrien antagonistiske indolderivater |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP0469833B1 (es) |
| JP (1) | JP3220191B2 (es) |
| KR (1) | KR0179985B1 (es) |
| CN (1) | CN1040108C (es) |
| AT (1) | ATE184280T1 (es) |
| AU (1) | AU654140B2 (es) |
| CA (1) | CA2048096C (es) |
| CZ (1) | CZ279932B6 (es) |
| DE (1) | DE69131592T2 (es) |
| DK (1) | DK0469833T3 (es) |
| ES (1) | ES2137158T3 (es) |
| FI (1) | FI102536B (es) |
| GR (1) | GR3032038T3 (es) |
| HU (2) | HU213604B (es) |
| IE (1) | IE912670A1 (es) |
| IL (1) | IL98990A (es) |
| MX (1) | MX9100414A (es) |
| MY (1) | MY131141A (es) |
| NO (1) | NO300133B1 (es) |
| NZ (1) | NZ239168A (es) |
| PH (1) | PH30487A (es) |
| PT (1) | PT98475B (es) |
| SK (1) | SK279197B6 (es) |
| YU (1) | YU47839B (es) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9122590D0 (en) * | 1991-10-24 | 1991-12-04 | Lilly Industries Ltd | Pharmaceutical compounds |
| US5273986A (en) * | 1992-07-02 | 1993-12-28 | Hoffmann-La Roche Inc. | Cycloalkylthiazoles |
| US5416211A (en) * | 1992-09-25 | 1995-05-16 | Eli Lilly And Company | Process for preparing 5-substituted pyrrolo-[2,3-d]pyrimidines |
| US5486612A (en) * | 1993-12-14 | 1996-01-23 | Eli Lilly And Company | N-benzyl dihydroindole LTD4 antagonists |
| EP0743064A1 (en) * | 1995-05-17 | 1996-11-20 | Eli Lilly And Company | Leukotriene antagonists for use in the treatment or prevention of alzheimer's disease |
| GB9523948D0 (en) | 1995-11-23 | 1996-01-24 | Univ East Anglia | Process for preparing n-benzyl indoles |
| US6160120A (en) | 1996-11-19 | 2000-12-12 | Eli Lilly And Company | Process for preparing n-benzyl indoles |
| AU2005295821A1 (en) * | 2004-10-12 | 2006-04-27 | Decode Genetics Ehf | Carboxylic acid peri - substituted bicyclics for occlusive artery disease |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8524157D0 (en) * | 1984-10-19 | 1985-11-06 | Ici America Inc | Heterocyclic amides |
| MY103259A (en) * | 1987-04-15 | 1993-05-29 | Ici America Inc | Aliphatic carboxamides |
| GB8728051D0 (en) * | 1987-12-01 | 1988-01-06 | Leo Pharm Prod Ltd | Chemical compounds |
| US4970207A (en) * | 1988-07-07 | 1990-11-13 | Fujisawa Pharmaceutical Company, Ltd. | Benzodiazepine derivatives |
-
1991
- 1991-07-26 AU AU81399/91A patent/AU654140B2/en not_active Ceased
- 1991-07-29 PH PH42849A patent/PH30487A/en unknown
- 1991-07-29 EP EP91306940A patent/EP0469833B1/en not_active Expired - Lifetime
- 1991-07-29 ES ES91306940T patent/ES2137158T3/es not_active Expired - Lifetime
- 1991-07-29 AT AT91306940T patent/ATE184280T1/de not_active IP Right Cessation
- 1991-07-29 MY MYPI91001362A patent/MY131141A/en unknown
- 1991-07-29 IL IL9899091A patent/IL98990A/en not_active IP Right Cessation
- 1991-07-29 CA CA002048096A patent/CA2048096C/en not_active Expired - Fee Related
- 1991-07-29 PT PT98475A patent/PT98475B/pt not_active IP Right Cessation
- 1991-07-29 DK DK91306940T patent/DK0469833T3/da active
- 1991-07-29 MX MX9100414A patent/MX9100414A/es unknown
- 1991-07-29 DE DE69131592T patent/DE69131592T2/de not_active Expired - Fee Related
- 1991-07-29 NZ NZ239168A patent/NZ239168A/xx unknown
- 1991-07-30 SK SK2380-91A patent/SK279197B6/sk unknown
- 1991-07-30 IE IE267091A patent/IE912670A1/en not_active Application Discontinuation
- 1991-07-30 KR KR1019910013080A patent/KR0179985B1/ko not_active IP Right Cessation
- 1991-07-30 CZ CS912380A patent/CZ279932B6/cs not_active IP Right Cessation
- 1991-07-30 CN CN91105940A patent/CN1040108C/zh not_active Expired - Fee Related
- 1991-07-30 FI FI913639A patent/FI102536B/fi active
- 1991-07-30 JP JP27905391A patent/JP3220191B2/ja not_active Expired - Fee Related
- 1991-07-30 YU YU132591A patent/YU47839B/sh unknown
- 1991-07-30 HU HU912535A patent/HU213604B/hu not_active IP Right Cessation
- 1991-07-30 NO NO912963A patent/NO300133B1/no unknown
-
1995
- 1995-06-30 HU HU95P/P00614P patent/HU211952A9/hu unknown
-
1999
- 1999-12-02 GR GR990403125T patent/GR3032038T3/el unknown
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