NO126864B - - Google Patents
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- Publication number
- NO126864B NO126864B NO00594/71A NO59471A NO126864B NO 126864 B NO126864 B NO 126864B NO 00594/71 A NO00594/71 A NO 00594/71A NO 59471 A NO59471 A NO 59471A NO 126864 B NO126864 B NO 126864B
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- acyl
- group
- indolyl
- general formula
- Prior art date
Links
- -1 e.g. t-butyl ester Chemical class 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000003855 acyl compounds Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 239000000047 product Substances 0.000 claims 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- 229960000583 acetic acid Drugs 0.000 claims 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims 2
- 239000012346 acetyl chloride Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- NNVGRWTYRUNMRQ-UHFFFAOYSA-N (5-methoxy-2,4-dimethyl-1h-indol-3-yl) acetate Chemical compound COC1=CC=C2NC(C)=C(OC(C)=O)C2=C1C NNVGRWTYRUNMRQ-UHFFFAOYSA-N 0.000 claims 1
- UAGJVSRUFNSIHR-UHFFFAOYSA-N Methyl levulinate Chemical compound COC(=O)CCC(C)=O UAGJVSRUFNSIHR-UHFFFAOYSA-N 0.000 claims 1
- 238000000862 absorption spectrum Methods 0.000 claims 1
- 230000021736 acetylation Effects 0.000 claims 1
- 238000006640 acetylation reaction Methods 0.000 claims 1
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 150000001262 acyl bromides Chemical class 0.000 claims 1
- 150000001263 acyl chlorides Chemical class 0.000 claims 1
- 230000000202 analgesic effect Effects 0.000 claims 1
- 230000001754 anti-pyretic effect Effects 0.000 claims 1
- 239000012141 concentrate Substances 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 239000012362 glacial acetic acid Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 238000001228 spectrum Methods 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 2-(6-amino-1h-indol-3-yl)acetonitrile Chemical compound NC1=CC=C2C(CC#N)=CNC2=C1 ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 0.000 description 1
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 description 1
- KWKVAGQCDSHWFK-VNKDHWASSA-N Methyl sorbate Chemical compound COC(=O)\C=C\C=C\C KWKVAGQCDSHWFK-VNKDHWASSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000001375 methyl (2E,4E)-hexa-2,4-dienoate Substances 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- HNBDRPTVWVGKBR-UHFFFAOYSA-N n-pentanoic acid methyl ester Natural products CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- 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
- A61K31/403—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 condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/26—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C30—CRYSTAL GROWTH
- C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
- C30B19/00—Liquid-phase epitaxial-layer growth
- C30B19/02—Liquid-phase epitaxial-layer growth using molten solvents, e.g. flux
- C30B19/04—Liquid-phase epitaxial-layer growth using molten solvents, e.g. flux the solvent being a component of the crystal composition
-
- C—CHEMISTRY; METALLURGY
- C30—CRYSTAL GROWTH
- C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
- C30B19/00—Liquid-phase epitaxial-layer growth
- C30B19/06—Reaction chambers; Boats for supporting the melt; Substrate holders
- C30B19/061—Tipping system, e.g. by rotation
-
- C—CHEMISTRY; METALLURGY
- C30—CRYSTAL GROWTH
- C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
- C30B29/00—Single crystals or homogeneous polycrystalline material with defined structure characterised by the material or by their shape
- C30B29/10—Inorganic compounds or compositions
- C30B29/40—AIIIBV compounds wherein A is B, Al, Ga, In or Tl and B is N, P, As, Sb or Bi
- C30B29/42—Gallium arsenide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Epidemiology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Inorganic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Hydraulic Turbines (AREA)
Description
Fremgangsmåte til fremstilling av l-acyl-3-indolylalifatiske syreestere.
Foreliggende oppfinnelse vedrører en ny fremgangsmåte til fremstilling av l-acyl-3-indolylalifatiske syreestere med den generelle formel:
hvor R^ er en alkylgruppe, halogensubstituert alkylgruppe eller alke-
nylgruppe med opptil. 10 karbonatorner. R- og R er like eller forskjel-5 •'
lige og er et hydrogenatom eller en lavere alkylgruppe, Br er. en lavere alkoksygruppe med opptil 4 karbonatomer, en benzyloksy- eller tetrahydropyranyloksygruppe, R^ er en laverealkyl-, laverealkoksy-eller laverealkyltiogruppe, et halogenatom eller et hydrogenatom, m er 0 eller 1, og n er 0 eller et helt tall fra 1 til 3, men m og n kan.ikke samtidig være 0. •
Syntesen av indolkomponenter med N-stilliriger substituert med acylgrupper, er f.eks. beskrevet i Elderfield: "Heterocyclic Compounds", Vol. 3 (1952), kapittel 1, sidene 1 - 247, og i W.C. Sampter og F.M Miller: "Chemistry of Heterocyclic Compounds with Indole and Carbazole Systems" (1954), sidene 1 - 69. Syntesen av N-acylindol-forbindelser ifølge foreliggende fremgangsmåte er imidlertid ikke tidligere beskrevet.
Ifølge foreliggende oppfinnelse er det tilveiebragt en ny fremgangsmåte og denne er kjennetegnet ved at et fenylhydrazonderivat med den generelle formel: hvor R^, R^, R^, R^, m og n er som angitt ovenfor, omsettes med en acylforbindelse med den generelle formel:
hvor B?~ har den samme betydning som angitt ovenfor, og Y er et halogenatom eller gruppen -O.CO.R''', hvor R"*" har den ovenfor angitte betydning.
Egnede oppløsningsmidler som kan anvendes i ovennevnte fremgangsmåte er inerte oppløsningsmidler, organiske syrer og organiske syreestere. Som inerte oppløsningsmidler kan manfieks. anvende benzen, toluen, xylen, cykloheksan, tetrahydrofuran og heksan, som organiske syrer, f.eks. eddiksyre, kloreddiksyre, propionsyre, smørsyre, kapro-insyre og heptanoinsyre, og som organiske syreestere f.eks. etylklor-acetat, metylbutyrat, metylakrylat, metylvalerat og metylsorbat.
Claims (1)
- Som acylforbindelsen med formelen'-III er det mest vanlig å anvende acylklorid. Man kan dessuten anvende acylbromid eller syre-anhydridet. Reaksjonstemperaturen varierer fra ^30° 150°C, fortrinnsvis fra 80° - 120°C. Reaksjonen vil vanligvis, være fullstendig i løpet av et par timer. Hvis man etter fullstendig reaksjon.enten konsentrerer opp-løsningsmidlet eller tilsetter eddiksyre, vann eller petroleter, så vil det ønskede produkt bli utfelt, hvoretter dette kan renses ved konsentrasjon etter ekstraksjon med eter, benzen eller kloroform. Alle fremstilte l-acyl-3-indolylålifatiske syreestere er nye forbindelser og har smertestillende og feberstillende virkninger. Noen av disse estere, som f.eks. t-butylester, benzylester og tetrahydro-pyranylester kan videre hydrolyseres ved egnet béhandling til 1-acyl-3-indolylalifatiske syrer. De frie syrer har' høyere terapeutisk akti-vitet enn esterene. Foreliggende fremgangsmåte skal illustreres ved følgende eksempler.Eksempel 1 2.5 g p-metoksyfenylhydrazonet av metylevulinat ble tilsatt 50 ml iseddik. Oppløsningen ble så dråpevis tilsatt 0.9 g acetylklorid og ble så holdt oppvarmet på 80°C i 3 timer. Blandingen ble deretter under omrøring tilsatt 50 ml kaldt vann,, hvorved man fikk dannet en oljeaktig substans. Denne ble ekstrahert med eter, og man oppnådde metyl-l-acetyl-2-metyl-5-metoksy-3-indolylacetat. Infrarødt absorb-sjonsspektrum av dette produkt var i full overensstemmelse med spektret fra et standardprodukt fremstilt ved acetylering av metyl-2-metyl-5-metoksy-3-indolylacetat.Eksempel 2 Ved å bruke 1.2 g eddiksyreanhydrid istedenfor 0.9 g acetyl--klorid i fremgangsmåten i eksempel 1,. fikk man fremstilt metyl-1-acetyl-2-metyl-5-metoksy-3-indolylacetat. Fremgangsmåte til fremstilling av 1-acy1-3-indolylalifatiske syreestere med den generelle formel:hvor R er en alkylgruppe, halogensubstituert alkylgruppe eller alke- . nylgruppe med opptil 10 karbonatomer, R og R er like eller for-skjellige og er et hydrogenatom eller en lavere alkylgruppe, R 5 er en lavere alkoksygruppe med opptil 4 karbonatomer, en benzyloksy- eller tetrahydropyranyloksygruppe, R^ er en laverealkyl-, laverealkoksy-eller laverealkyltiogruppe, et halogenatom eller et hydrogenatom, m er 0 eller 1, og n er 0 eller et helt tall fra 1 til 3, men m og n kan ikke samtidig være 0,.karakterisert ved at et fenylhydrazonderivat med den generelle formel: 2 ~Z C £hvor R , R , R , R , m og n er som angitt ovenfor, omsettes med en acylforbindelse med den generelle formel:hvor R<1> har den samme betydning som angitt ovenfor, og Y er et halogenatom eller gruppen -O.CO.R<1>, hvor R<1> har den ovenfor angitte betydning,
Applications Claiming Priority (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP199966 | 1966-01-12 | ||
| JP2730166 | 1966-04-28 | ||
| JP2730066 | 1966-04-28 | ||
| JP2812566 | 1966-05-02 | ||
| JP2840066 | 1966-05-04 | ||
| JP4059166 | 1966-06-21 | ||
| JP4472466 | 1966-07-08 | ||
| JP4472366 | 1966-07-08 | ||
| JP5467466 | 1966-08-19 | ||
| JP5467566 | 1966-08-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO126864B true NO126864B (no) | 1973-04-02 |
Family
ID=27579471
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO00166327A NO126862B (no) | 1966-01-12 | 1967-01-10 | |
| NO00595/71A NO126865B (no) | 1966-01-12 | 1971-02-18 | |
| NO00594/71A NO126864B (no) | 1966-01-12 | 1971-02-18 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO00166327A NO126862B (no) | 1966-01-12 | 1967-01-10 | |
| NO00595/71A NO126865B (no) | 1966-01-12 | 1971-02-18 |
Country Status (13)
| Country | Link |
|---|---|
| AT (4) | AT283349B (no) |
| BE (1) | BE692456A (no) |
| BR (1) | BR6786134D0 (no) |
| CS (3) | CS155156B2 (no) |
| DE (2) | DE1618933A1 (no) |
| DK (1) | DK134715B (no) |
| FI (1) | FI49162C (no) |
| FR (1) | FR7844M (no) |
| IL (1) | IL27173A (no) |
| NL (1) | NL146804B (no) |
| NO (3) | NO126862B (no) |
| SE (2) | SE307795B (no) |
| SU (1) | SU375847A3 (no) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU162374B (no) * | 1969-04-03 | 1973-02-28 | ||
| CZ300116B6 (cs) * | 2006-12-05 | 2009-02-11 | Zentiva, A. S. | Zpusob cištení hydrochloridu (S)-N-methyl-3-(1-naftyloxy)-3-(2-thienyl)propylaminu |
-
1966
- 1966-12-28 IL IL27173A patent/IL27173A/en unknown
- 1966-12-30 DE DE19661618933 patent/DE1618933A1/de active Pending
- 1966-12-30 DE DE1620441A patent/DE1620441C3/de not_active Expired
-
1967
- 1967-01-04 AT AT09712/68A patent/AT283349B/de not_active IP Right Cessation
- 1967-01-04 AT AT971468A patent/AT277996B/de not_active IP Right Cessation
- 1967-01-04 AT AT971368A patent/AT277995B/de not_active IP Right Cessation
- 1967-01-04 AT AT971168A patent/AT280991B/de not_active IP Right Cessation
- 1967-01-09 NL NL676700300A patent/NL146804B/xx unknown
- 1967-01-09 CS CS20067*#A patent/CS155156B2/cs unknown
- 1967-01-09 CS CS795569*1A patent/CS155158B2/cs unknown
- 1967-01-09 CS CS795469*1A patent/CS155157B2/cs unknown
- 1967-01-10 DK DK13967AA patent/DK134715B/da unknown
- 1967-01-10 NO NO00166327A patent/NO126862B/no unknown
- 1967-01-11 BE BE692456D patent/BE692456A/xx unknown
- 1967-01-12 SE SE14751/67*A patent/SE307795B/xx unknown
- 1967-01-12 FI FI670074A patent/FI49162C/fi active
- 1967-01-12 BR BR186134/67A patent/BR6786134D0/pt unknown
- 1967-01-12 SU SU1126031A patent/SU375847A3/ru active
- 1967-01-12 SE SE489/67A patent/SE314985B/xx unknown
- 1967-03-14 FR FR98691A patent/FR7844M/fr not_active Expired
-
1971
- 1971-02-18 NO NO00595/71A patent/NO126865B/no unknown
- 1971-02-18 NO NO00594/71A patent/NO126864B/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1620441C3 (de) | 1975-05-22 |
| CS155157B2 (no) | 1974-05-30 |
| SE307795B (no) | 1969-01-20 |
| NL146804B (nl) | 1975-08-15 |
| NL6700300A (no) | 1967-07-13 |
| AT277995B (de) | 1970-01-12 |
| SE314985B (no) | 1969-09-22 |
| IL27173A (en) | 1972-08-30 |
| AT280991B (de) | 1970-05-11 |
| AT283349B (de) | 1970-08-10 |
| DE1620441A1 (de) | 1970-08-27 |
| BE692456A (no) | 1967-06-16 |
| BR6786134D0 (pt) | 1973-12-26 |
| AT277996B (de) | 1970-01-12 |
| NO126865B (no) | 1973-04-02 |
| CS155158B2 (no) | 1974-05-30 |
| DE1643506A1 (de) | 1972-03-30 |
| CS155156B2 (no) | 1974-05-30 |
| SU375847A3 (no) | 1973-03-23 |
| DE1643506B2 (de) | 1973-01-04 |
| FI49162C (fi) | 1975-04-10 |
| DE1618933A1 (de) | 1972-03-16 |
| FR7844M (no) | 1970-06-01 |
| NO126862B (no) | 1973-04-02 |
| DK134715C (no) | 1977-05-31 |
| DE1620441B2 (de) | 1974-09-19 |
| DK134715B (da) | 1977-01-03 |
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