NO159653B - Analogifremgangsmaate for fremstilling av terapeutisk aktive, sure indol-derivater. - Google Patents
Analogifremgangsmaate for fremstilling av terapeutisk aktive, sure indol-derivater. Download PDFInfo
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- NO159653B NO159653B NO854941A NO854941A NO159653B NO 159653 B NO159653 B NO 159653B NO 854941 A NO854941 A NO 854941A NO 854941 A NO854941 A NO 854941A NO 159653 B NO159653 B NO 159653B
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- carbon atoms
- radical
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- compounds
- amino group
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- 238000000034 method Methods 0.000 title abstract description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- 239000000463 material Substances 0.000 claims description 18
- 239000004065 semiconductor Substances 0.000 claims description 15
- 229910052785 arsenic Inorganic materials 0.000 claims description 8
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 8
- 229910052716 thallium Inorganic materials 0.000 claims description 7
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims description 7
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 6
- 229910052711 selenium Inorganic materials 0.000 claims description 6
- 239000011669 selenium Substances 0.000 claims description 6
- 229910052714 tellurium Inorganic materials 0.000 claims description 6
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 claims description 6
- 230000007423 decrease Effects 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 238000007499 fusion processing Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 abstract 12
- 125000003277 amino group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- BNJMRELGMDUDDB-UHFFFAOYSA-N $l^{1}-sulfanylbenzene Chemical compound [S]C1=CC=CC=C1 BNJMRELGMDUDDB-UHFFFAOYSA-N 0.000 abstract 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- -1 phenylsulphinyl radical Chemical class 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- 125000003396 thiol group Chemical class [H]S* 0.000 abstract 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical class [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 abstract 1
- BQIKRTGTPBOIMK-UHFFFAOYSA-N [O]C[O] Chemical compound [O]C[O] BQIKRTGTPBOIMK-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000013019 agitation Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000002800 charge carrier Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002772 conduction electron Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000000752 ionisation method Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- 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
-
- 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
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D403/12—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 chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Lubricants (AREA)
- Cosmetics (AREA)
Abstract
Terapeutisk aktive forbindelser med formelen. hvor (1) Rog Q uavhengig er H, alkyl, alkoksy, merkapto. alkyltio, alkylsulfinyl, alkylsulfonyl, hydroksy, Rtatt to ganger bundet til nabostilte karbonatomer slik at de to Rgrupper sammen er metyl endioksy, nitro, amino, substituert amino eller halogen; <2) Rer H, alkyl, fenyl, substituert fenyl eller benzyl; (3) Rer H, alkyl, alkoksy, merkapto, alkyltio, fenyltio, substituert fenyltio, alkylsulfinyl, fenylsul finyl, substituert fenylsulfiny1, alkylsulfonyl, fenylsul fonyl, substituert fenylsul fonyl, amino, substituert amino; og (4) Rer. og farmasøytisk godtagbare salter derav.Forbindelsene er særlig nyttige som antiallergiske midler.Fremstilling av forbindelsene er beskrevet.
Description
Halvlederkomponent.
Foreliggende oppfinnelse vedrbrer en halvlederkomponent med minst to elektroder, hvilken komponents motstand ved dkende spenning over elektrodene plutselig forandres fra en fbrste, meget stor verdi til en andre meget liten verdi og ved minskende strbmstyrke plutselig forandres fra nevnte andre verdi til nevnte fbrste verdi.
Formålet med oppfinnelsen er å tilveiebringe en halvlederkomponent eller et koblingselement som er enkel i fremstilling og har for anvendelse f.eks. innenfor telefoniområdet egnede karakteristiske data når den benyttes som koblingselement eller gnistslukningsorgan. De karakteristiske egenskaper skal være
mest mulig stabile selv efter lang og intens bruk.
En ifblge oppfinnelsen utformet halvlederkomponent kjennetegnes ved at den inneholder selen i en vektprosentgehalt innen området 1 - 50#, tallium innen området 17 - 59% og arsen innen området 3 - 22%, hvorved materialkomponentene som resultat av en sammensmeltningsprosess til sammen danner et fast, homogent smelteprodukt med stort sett amorf, glassaktig struktur.
En annen halvlederkomponent ifblge oppfinnelsen kjennetegnes ved at den dessuten inneholder 1^.5 - 65 vektprosent tellur.
Forsbk har vist at man kan tenke seg en hel del adskilte materialkombinasjoner innenfor ganske brede grenser hva den prosentuelle sammensetningen gjelder.
I det fblgende skal angis fem eksempler
1. Tellur 19- ?k vektprosent
Tallium 10-50 "
Arsen 16-30 "
la. Tellur 50-60
Tallium 12-18 "
Arsen 20-30 "
2. Selen 33-50
Tallium 3^-^6
Arsen 16-21 "
3. Selen 20-30 "
Tellur 30-62 "
Arsen 5-9 "
Germanium 12-30 "
h. Selen 1-50 "
Tellur Ut. 5-65
Tallium 17-59 "
Arsen 3-22 "
Halvlederkomponentene kan fremstilles i massiv form enten ved smelting av tilsvarende raaterialblandinger med efterfblgende hurtigkjblning, helst i hermetisk lukket smeltebeholder, eller ved presning av tilsvarende pulverblandinger til formlegemer med påfblgende sintring i syrefri atmosfære. De kan- også fremstilles i form av:tynne s^ikt, f.eks. ved vakuumfordamphing av en materialblanding, eller et stop eller et sintergods på
et hensiktsmessig metallisk eller ikke-metalli/sk underlag.
Underlaget utgjor da fortrinnsvis komponentens ene elektrode,
mens dens andre elektrode ligger an med et visst trykk mot det tynne sjiktets frie overflate.
Materialet i disse halvlederkomponenter kan betegnes som glass-artet da det bevirker visse for glass karakteristiske fenomen som a) fravær av krystallinske skarpe topper på rbnjtgen-diffraksj onsdiagraramet b) suksessiv overgang fra den faste til den flytende tilstand uten noe skarpt definert smeltepunkt som
for de krystalline materialer.
c) konkoidal bruddflate.
Ut fra struktursynspunkt kan de elementære bestanddeler i
halvlederkomponentenes materiale inndeles i to grupper med adskilte funksjoner, nemlig nettverksdannere og nettverksmodifiserere. Som nettverksdannere menes her elementer med fremherskende kovalent kjemisk binding og utpreget tilbbylig-
het til dannelse av to-eller tredimensjonale strukturnettverk til en amorf sammensetning (d.v.s. en ordnet blanding). Som nettverksmodifiserere tilsiktes her elementer, som på grunn av relativt lett polariserte valensrelektroner kan plasere seg i nettverket uten å bevirke noen egentlig krystalldannelse.
Disse glassartede materialer kjennetegnes ved at den fremherskende karakter av de kjemiske bindingene er kovalent og at inngående an;)oner har lukkede s- og p-skall slik at de kovalente bindinger danner et kontinuerlig valensnettverk som strekker seg gjennom store områder av materialet.
Den eventuelle forekomst av tomme metalliske orbitaler for-styrrer heller ikke halvledertilstanden så lenge tilsvarende atomer ikke er bundet til hverandre.
Et slikt valensnettverk kjennetegnes ved at energigapet mellom valens- og ledningsbåndet er mindre jo stbrre nettverket er. Materialet med et slikt valensnettverk er en isotrop egenhalv-leder, hvis elektriske ledningsevne ^i sin natur er elektro-nisk og er avhengig av temperaturen T og energigapet E ifblge ligningen
i
\
Ledningsevnen kan variere mellom f.eks. 10~ - 10~ /V~ * cm" .
De omhandlede halvledermaterialer fremviser ovenfor en viss verdi av spenning resp. strbm en utpreget ikke-linearitet for spenning-strbm-karakteristikken.
Denne ikke-linearitet forekommer på grunn av strukturforandring bevirket av
a) Termisk agitasjon.
Ved langsom oppvarmning får ledningselektrodene så hby energi
sammenlignet med energigapet mellom valens- og ledningsbåndet ( ^ E) at termisk agitasjon fåes ved vekselvirkning mellom lednings- og valenselektronene. Når tilstrekkelig hby energi er oppnådd fåes derved en atomisk omdiffusjon i materialet således at en ordnet nettverksstruktur (krystallisasjon) opp-nåes.
b) Stbtjonisasjon pÉ.': grunn av indre feltemisjon.
Når den elektriske feltstyrke er tilstrekkelig hby blir
bevegeligheten av elektronene så stor slik at deres energi
2
er tilstrekkelig til å jonisere valenselektronene, d.v.s.
Ladningsbærerne.s (d.v.s. elektronenes og hullenes) bevegelighet
beror på deres spredning i forskjellige baner i nettverket (gitteret) samt på deres vibrasjonsfrekvens, som igjen er av-
hengig av temperaturen. På grunn av dette sprer også ladnings-bærernes energiverdier seg sterkt. Slik bestemmes ladnings-
bærernes beveglighet av gitterets termiske egenskaper og terskelfeltstyrken for stbtjonisasjon av valenselektronenes joniseringsenergi. Terskelfeltstyrken kan også være en funksjon av tilstrekkelig termisk agitasjon for å nå strukturfaseom-
dannelse. Då hullenes bevegelighet er ganske lav og rekorabina-sjon.avhull og ledningselektroner er i likevekt med joniserings-forlbpet, kan ikke noen romladning oppstå for en viss terskel-feltstyrke er nådd.
Når den imidlertid er oppnådd dannes omkring de på halvleder-materialet pålagte elektroder en. romladning og en lavjonisering inntrer liksom ved en elektrisk gassutladning. Stbrrelsen av spenningen for å opprettholde denne utlaåning, brennspenningen er ikke avhengig av strbmbanens lengde i materialet mellom elektrodene.
Denne prosess gir seg tilkjenne forst ved minskende resistans-differensial for spenning-strbm-forholdet. Ved ytterligere
bket spenning opptrer negativ resistans, idet materialets resistansverdi synker flere tipotenser, f.eks. fra omkring 10 M/v. til omkring lOO/veller mindre. Dette innebærer at materialet går over fra en distinkt hbyohmig tilstand til en distinkt lavohmig tilstand. Terskelspenningen for denne over-
gang og spenningen for opprettholdelse av den lavohmige til-
stand er i overensstemmelse med den foregåénde kvalitative
dannelse avhengig av materialets sammensetning og struktur.
Når brennstrbmmen gjennom materialet synker under en viss verdi, f.eks. 50 ^A, går materialet tilbake til sin tidligere
hbyohmige tilstand.
Claims (2)
1. Halvlederkomponent med minst to elektroder, hvilken komponents motstand ved bkende spenning over elektrodene plutselig forandres fra en fbrste, meget stor verdi til en andre meget liten verdi og ved minskende strbmstyrke plutselig forandres fra nevnte andre verdi til nevnte fbrste verdi, karakterisert ved at den inneholder selen i en vektprosentgehalt innen området 1 - 5o£, tallium innen området 17 - 59JÉ og arsen innen området 3 - 22JÉ, hvorved raaterialkomponentene som resultat av en sammensmeltningsprosess til sammen danner et fast, homogent smelteprodukt med stort sett amorf, glassaktig struktur.
2. Halvlederkomponent som angitt i krav 1, karakterisert ved at materialkomponenten selen utgjor 33 - 50 vektprosent, tallium 3h - ^6 vektprosent og arsen 16 - 21 vektprosent.
3» Halvlederkomponent som angitt i krav 1, karakterisert ved at den dessuten inneholder l*+.5 - 65 vektprosent tellur.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68011684A | 1984-12-10 | 1984-12-10 | |
| US06/788,111 US4675332A (en) | 1984-12-10 | 1985-10-21 | Acidic tetrazolyl substituted indole compounds and their use as antiallergy agents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO854941L NO854941L (no) | 1986-06-11 |
| NO159653B true NO159653B (no) | 1988-10-17 |
| NO159653C NO159653C (no) | 1989-01-25 |
Family
ID=27102395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO854941A NO159653C (no) | 1984-12-10 | 1985-12-09 | Analogifremgangsm te for fremstilling av terapeutisk aktive, sure indol-derivater. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4675332A (no) |
| EP (1) | EP0186367B1 (no) |
| JP (1) | JPH0653736B2 (no) |
| KR (1) | KR890000292B1 (no) |
| CN (1) | CN1005974B (no) |
| AT (1) | ATE86252T1 (no) |
| AU (1) | AU576131B2 (no) |
| CA (1) | CA1259317A (no) |
| DE (1) | DE3587148T2 (no) |
| DK (1) | DK174104B1 (no) |
| ES (1) | ES8700252A1 (no) |
| FI (1) | FI84719C (no) |
| GR (1) | GR852948B (no) |
| IE (1) | IE58554B1 (no) |
| NO (1) | NO159653C (no) |
| NZ (1) | NZ214480A (no) |
| PH (1) | PH24075A (no) |
| PT (1) | PT81637B (no) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE64995B1 (en) * | 1987-07-14 | 1995-09-20 | Warner Lambert Co | Novel benzothiophenes having antiallergic activity and both novel and other selected benzothiophenes having activity for treating acute respiratory distress syndrome |
| IT1228893B (it) * | 1989-02-24 | 1991-07-09 | Valeas Spa | Derivati tetrazol ammidici di acidi alchenil eterociclici e loroimpiego come sostanze antiallergiche |
| LU87611A1 (fr) * | 1989-10-20 | 1991-05-07 | Oreal | Composition tinctoriale pour fibres keratiniques contenant des precurseurs de colorants par oxydation et des coupleurs amino indoliques,procedes de teinture mettant en oeuvre ces compositions et composes nouveaux |
| US5051442A (en) * | 1990-04-25 | 1991-09-24 | Merrell Dow Pharmaceuticals Inc. | 3-indolyl thioacetate derivatives and NMDA receptor antagonistic use thereof |
| US5095031A (en) * | 1990-08-20 | 1992-03-10 | Abbott Laboratories | Indole derivatives which inhibit leukotriene biosynthesis |
| CA2054339C (en) * | 1990-11-02 | 2002-12-24 | Francesco G. Salituro | 3-amidoindolyl derivatives |
| US5189054A (en) * | 1990-11-02 | 1993-02-23 | Merrell Dow Pharmaceuticals Inc. | 3-amidoindolyl derivatives and pharmaceutical compositions thereof |
| US5599774A (en) * | 1992-01-22 | 1997-02-04 | Imperial Chemical Industries Plc | N-arylindoles and their use as herbicides |
| US5395817A (en) * | 1992-01-22 | 1995-03-07 | Imperial Chemical Industries Plc | N-arylindoles and their use as herbicides |
| US5424329A (en) * | 1993-08-18 | 1995-06-13 | Warner-Lambert Company | Indole-2-carboxamides as inhibitors of cell adhesion |
| GB9716657D0 (en) | 1997-08-07 | 1997-10-15 | Zeneca Ltd | Chemical compounds |
| GB9803226D0 (en) | 1998-02-17 | 1998-04-08 | Zeneca Ltd | Chemical compounds |
| GB9902459D0 (en) * | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
| GB9902461D0 (en) * | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
| GB9902452D0 (en) | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
| GB9902455D0 (en) | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
| GB9902453D0 (en) * | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
| GB0000625D0 (en) | 2000-01-13 | 2000-03-01 | Zeneca Ltd | Chemical compounds |
| US6436965B1 (en) | 2000-03-02 | 2002-08-20 | Merck Frosst Canada & Co. | PDE IV inhibiting amides, compositions and methods of treatment |
| EP1314733A1 (en) * | 2001-11-22 | 2003-05-28 | Aventis Pharma Deutschland GmbH | Indole-2-carboxamides as factor Xa inhibitors |
| GB0217920D0 (en) * | 2002-04-23 | 2002-09-11 | Aventis Pharm Prod Inc | Interleukin-4 Gene Expression inhibitors |
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| CN100439367C (zh) | 2003-12-11 | 2008-12-03 | 安万特药物公司 | 作为酪蛋白激酶Iε抑制剂的取代的1H-吡咯并[3,2-b、3,2-c和2,3-c]吡啶-2-甲酰胺以及相关类似物 |
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| US3417096A (en) * | 1965-07-01 | 1968-12-17 | Bristol Myers Co | Certain 5(1-benzoyl-3-indolylmethyl) tetrazoles |
| US4316904A (en) * | 1978-06-05 | 1982-02-23 | Brown Richard E | Indolopyrone tetrazoles and carboxamidotetrazoles having antiallergic activity |
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| US4333943A (en) * | 1980-04-24 | 1982-06-08 | Miles Laboratories, Inc. | Ethyl 3-(3-indolyl)-3-(5-tetrazolyl) propionate compounds used as anti-hypertensive agents |
| DE3131527A1 (de) * | 1981-08-08 | 1983-02-24 | Kali-Chemie Pharma Gmbh, 3000 Hannover | 1-phenyl-2-aminocarbonylindol-verbindungen sowie verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| GB2111050B (en) * | 1981-11-19 | 1985-09-11 | Ciba Geigy Ag | N-substituted-2-pyridylindoles |
| US4567201A (en) * | 1981-11-25 | 1986-01-28 | Takeda Chemical Industries, Ltd. | Diphenoxypropane derivatives and compositions of antiasthmatic and antiinflammatory agents thereof |
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-
1985
- 1985-10-21 US US06/788,111 patent/US4675332A/en not_active Expired - Lifetime
- 1985-11-13 IE IE284185A patent/IE58554B1/en not_active IP Right Cessation
- 1985-11-29 AU AU50508/85A patent/AU576131B2/en not_active Ceased
- 1985-12-04 FI FI854821A patent/FI84719C/fi not_active IP Right Cessation
- 1985-12-06 PH PH33140A patent/PH24075A/en unknown
- 1985-12-09 GR GR852948A patent/GR852948B/el unknown
- 1985-12-09 NO NO854941A patent/NO159653C/no unknown
- 1985-12-09 JP JP60275227A patent/JPH0653736B2/ja not_active Expired - Fee Related
- 1985-12-09 DK DK198505688A patent/DK174104B1/da not_active IP Right Cessation
- 1985-12-09 NZ NZ214480A patent/NZ214480A/en unknown
- 1985-12-10 KR KR1019850009255A patent/KR890000292B1/ko not_active IP Right Cessation
- 1985-12-10 CA CA000497268A patent/CA1259317A/en not_active Expired
- 1985-12-10 DE DE8585308948T patent/DE3587148T2/de not_active Expired - Fee Related
- 1985-12-10 ES ES549768A patent/ES8700252A1/es not_active Expired
- 1985-12-10 AT AT85308948T patent/ATE86252T1/de not_active IP Right Cessation
- 1985-12-10 PT PT81637A patent/PT81637B/pt not_active IP Right Cessation
- 1985-12-10 CN CN85109061.3A patent/CN1005974B/zh not_active Expired
- 1985-12-10 EP EP85308948A patent/EP0186367B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE3587148T2 (de) | 1993-07-15 |
| PT81637A (en) | 1986-01-01 |
| PH24075A (en) | 1990-03-05 |
| DK568885D0 (da) | 1985-12-09 |
| CN1005974B (zh) | 1989-12-06 |
| AU576131B2 (en) | 1988-08-11 |
| ES549768A0 (es) | 1986-04-16 |
| EP0186367B1 (en) | 1993-03-03 |
| US4675332A (en) | 1987-06-23 |
| DK174104B1 (da) | 2002-06-17 |
| JPS61191683A (ja) | 1986-08-26 |
| FI84719B (fi) | 1991-09-30 |
| FI854821A0 (fi) | 1985-12-04 |
| JPH0653736B2 (ja) | 1994-07-20 |
| GR852948B (no) | 1986-04-11 |
| NO854941L (no) | 1986-06-11 |
| CN85109061A (zh) | 1987-01-21 |
| IE852841L (en) | 1986-06-10 |
| ES8700252A1 (es) | 1986-10-16 |
| CA1259317A (en) | 1989-09-12 |
| PT81637B (pt) | 1988-02-17 |
| NZ214480A (en) | 1988-05-30 |
| EP0186367A3 (en) | 1988-01-07 |
| FI854821A (fi) | 1986-06-11 |
| NO159653C (no) | 1989-01-25 |
| AU5050885A (en) | 1986-06-19 |
| ATE86252T1 (de) | 1993-03-15 |
| KR890000292B1 (ko) | 1989-03-13 |
| IE58554B1 (en) | 1993-10-06 |
| FI84719C (fi) | 1992-01-10 |
| KR860004882A (ko) | 1986-07-14 |
| DE3587148D1 (de) | 1993-04-08 |
| DK568885A (da) | 1986-06-11 |
| EP0186367A2 (en) | 1986-07-02 |
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