NO138090B - Analogifremgangsmaate til fremstilling av terapeutisk aktive spiromorfolinpiperazinderivater - Google Patents
Analogifremgangsmaate til fremstilling av terapeutisk aktive spiromorfolinpiperazinderivater Download PDFInfo
- Publication number
- NO138090B NO138090B NO353/73A NO35373A NO138090B NO 138090 B NO138090 B NO 138090B NO 353/73 A NO353/73 A NO 353/73A NO 35373 A NO35373 A NO 35373A NO 138090 B NO138090 B NO 138090B
- Authority
- NO
- Norway
- Prior art keywords
- preparation
- therapeutically active
- spiromorpholine
- analogical
- procedures
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- FOZVXADQAHVUSV-UHFFFAOYSA-N 1-bromo-2-(2-bromoethoxy)ethane Chemical compound BrCCOCCBr FOZVXADQAHVUSV-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000006268 Sarcoma 180 Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 1
- 230000036732 histological change Effects 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Anesthesiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Walker-Karzinoms, ved Erlich-Karzinom, ved "Sarkom 180" samt ved Oberling-Guerin-Guerin (OGG) Mielon som ble.frembrakt kunstig hos mus.
Dessuten innvirket i parallelle forsøk forbindelsen med den generelle formel T vesentlig på forlengelsen av levetiden på dyr med en svulst. Forsøkene ble gjennomført på albinomus med en vekt på 120 - 24 0 g.
Dessuten ble det ikke iakttatt histologiske forandringer i det indre epitel eller forandring av testiklene.
Hos "Yoshido AH 130 Hepatom" og Walker Karzinom forsvant svulsten fullstendig dersom det ble direkte kontakt mellom substansene og svulstcellen.: Fra britisk patentskrift 1.174.819 er det kjent at den ovennevnte forbindelse som cykliseres har beroligende og anti-histaminisk virkning, men den har imidlertid ikke cytostatisk virkning.
Oppfinnelsen vil i det etterfølgende bli belyst ved hjelp av eksempler.
Eksempel 1
80 g av en 40-prosentig løsning av 1-(klorbenzhydryl)-4-piperazin i m-xylen (32 g C17HigClN2, molekylvekt 282,780, eller 0,113 mol) og 335 ml 2,2'-diklor-dietyleter (440 g =
3,08 mol C4HgCL20, molvekt 143,022, overskudd 27 x) ble blandet i en kolbe og oppvarmet med tilbakekjøling. Etter 13 timer ble en utfelling av N'-(4'-klorbenzhydryl)-N 4-spiromor-folinpiperazinkloridhydroklorid avsuget og vasket med eter.
Omkrystallisasjon ble foretatt av en vandig etanol-eter-blanding. Det ble utvunnet 3 5,2 g (72%) N'-(4'-klorbenzhydryl)-N 4-spiromorfolinpiperazinklorid-hydroklorid med smeltepunkt 282-285°C.
Analyse: C21H27C13N2° Molvekt 429,834 Beregnet: C 58,68, H 6,33, N 6,52 %
Funnet: C 58,42, H 6,36, N 6,40 %
Smeltepunkt: 286-288°C
IR-spektrum (KBr) 2940 (-CH2~), 2440 (= NH<+>), 1600 (fenyl) 1450 (-CH2-), 1250 (C-O-C) cm"<1>.
Eksempel 2
Når det ble arbeidet som beskrevet i eksempel 1, men 2,2'-dibromdietyleteren anvendt istedenfor 2,2'-diklor-dietyleteren, oppnådde man med 90% utbytte N'-(4-klorbenzhydryl)-N 4-spiromor-folinpiperazinbromid-hydrobromid med smeltepunkt 268-270°C (av .etanol-eter).
.Analyse: C21H27Br2ClN20., Molvekt 518,731
Beregnet: C 48,63, H 5,24, N 5,40 %
Funnet: C 48,75, H 5,46, N 5,25 %
Eksempel 3
Det ble arbeidet som ifølge eksempel 1, men krystallene som ble utskilt etter oppvarmingen ble løst i 10 prosentig NaOH, og det vandige sjikt ble ekstrahert med kloroform. Kloro-formekstraktene ble tørket, kloroformen ble avdestillert, og den resterende olje ble innført i 600 ml etanol som var mettet med hydrogenklorid. Etter en viss tid falt krystaller av N'-(4'-klorbenzhydryl)-N 4 -spiromorfolinpiperazinklorid-hydro-kloridet ut. Utbytte 70%, smeltepunkt 285-286°C.
Eksempel 4
2,58 g N'-(4'-klorbenzhydryl)-N 4-spiromorfolinpiperazin-klorid-hydroklori<d> (<C>21<H>27C13N20, molvekt 429,834, det vil si 6 millimol) ble løst i destillert vann og nøytralisert med K2C03. Vannet ble avdampet til resten var tørr, og det ble tilsatt 150 ml aceton og 1,99 g KJ (molvekt 166,02 = 12 millimol) og omrørt med tilbakeløp i 5^ time. Utfellingen (2,9 g) ble avsuget, og acetonfiltratet ble inndampet til et lite volum. Den utskilte utfelling ble igjen avsuget (1,5 g). De kombinerte utfellinger ble oppslemmet i kaldt vann for å løse KCl som opp-sto, og overskudd av KJ. Resten ble filtrert og tørket, og det ble oppnådd 2,9 g (100%) N'-(4'-klorbenzhydryl)-N 4-spiromor-folinpiperazinjodid. Smeltepunkt 27 6-278°C. Etter omkrystallisasjon av varm etanol var smeltepunktet 27 9-280,5°C
Analyse: <C>21<H>26<JN>2° <M>olvekt 434,801 Beregnet: C 52,03, H 5,41, N 5,78 %
Funnet: C 52,32, H 5,62, N 5,52 %
Smeltepunkt: 279-280,5°C.
IR-spektrum (KBr) 2980 (-CH2-), 1600 (fenyl), 1485 (-CH2"), 1120 og 1085 (C-O-C) cm"<1>.
Eksempel 5
3,0 g 1-(p-klor-benzhydryl)-4-[ 2-(2-hydroksyetyl7 -piper-azinhydroklorid (c2iH28C12N2°2' molvekt 411,385, 7,3 millimol) ble i en kolbe løst i 30 ml varm nitrometan.(CH^NG^, kokepunkt 99-101°C, d^° = 1,134). Under kjøling i et isbad ble det dråpe-vis tilsatt en blanding av CH^NO., (7,5 ml) og fosfortribromid
(PBr3, 2,5 ml, d<18> = 2,852, molvekt 270,72, 7,1 g = 26,3 millimol, overskudd 12 x). Etter omrøring i 24 timer ved romtempera-tur ble overskuddet av fosfortribromid nedbrutt med vann. Blan-dingen ble nøytralisert med NaHCO^ og Na-acetat. Nitrometanet
og det vandige sjikt ble fraskilt. Det vandige sjikt ble ekstrahert ytterligere to ganger med nitrometan. Nitrometaneks-traktene ble forenet og tørket med natriumsulfat (brent). Nitrometanet ble avdampet. Det ble tilbake et gult produkt (2,3 g, 72%), smeltepunkt (244-247°C). Ved omkrystallisasjon av etanol-eter (1 : 2) fikk man 1,46 g N' - (4-klorbenzhydry]^-N 4-spiromor-folinpiperazinbromid. Smeltepunkt 248-251°C.
Analyse: C21H26BrClN20, Molvekt 437,813 Beregnet: C 57,62, H 5,98, N 6,40
Funnet: C 57,74, H 6,02, N 6,38
Smeltepunkt: 253-256°C.
Claims (1)
- Analogifremgangsmåte til fremstilling av terapeutisk aktive - spiromorfolinpiperazinderivater med den generelle formel: 2-hvor Y er et halogen, SO^H , S04 eller en annen anion, karakterisert ved at en forbindelse med den generelle formel:hvor A er et hydrogen eller en -CH2-CH2-0-CH2-CH2-OH-gruppe, enten, når A er hydrogen, omsettes med en forbindelse med den generelle formel:hvor X er et halogen, eller, når A er -CH2-CH2-0-CH2-CH2-OHomsettes med et halogeneringsmiddel, og at det oppnådde til-svarende halogenidhydrohalogenid nøytraliseres og cykliserer i et inert løsningsmiddel i nærvær av vannfri syre, og når det ønskes andre betydninger av Y enn halogen fremstilles disse ved kjente fremgangsmåter for fremstilling av salter.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH142072A CH571004A5 (no) | 1972-02-01 | 1972-02-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO138090B true NO138090B (no) | 1978-03-20 |
| NO138090C NO138090C (no) | 1978-06-28 |
Family
ID=4210035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO353/73A NO138090C (no) | 1972-02-01 | 1973-01-29 | Analogifremgangsmaate til fremstilling av terapeutisk aktive spiromorfolinpiperazinderivater |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5343511B2 (no) |
| AT (1) | AT331250B (no) |
| BE (1) | BE794804A (no) |
| CA (1) | CA994772A (no) |
| CH (1) | CH571004A5 (no) |
| DE (1) | DE2304708A1 (no) |
| ES (1) | ES411147A1 (no) |
| FR (1) | FR2173982B1 (no) |
| GB (1) | GB1424611A (no) |
| HU (1) | HU168740B (no) |
| IL (1) | IL41440A (no) |
| NL (1) | NL7301488A (no) |
| NO (1) | NO138090C (no) |
| ZA (2) | ZA73730B (no) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2341110A1 (de) * | 1973-08-14 | 1975-02-27 | Crc Ricerca Chim | Verfahren zur herstellung von piperazinderivaten |
| DE2938557A1 (de) * | 1979-09-24 | 1981-04-23 | Isartaler Schraubenkompressoren Gmbh, 8192 Gertsried | Verdichteranlage |
| FI75816C (fi) * | 1981-02-06 | 1988-08-08 | Ucb Sa | Foerfarande foer framstaellning av terapeutiskt aktiv 2-/4-(difenylmetyl)-1-piperazinyl/-aettiksyror eller dess amid. |
| JPS57134381U (no) * | 1981-02-17 | 1982-08-21 |
-
0
- BE BE794804D patent/BE794804A/xx unknown
-
1972
- 1972-02-01 CH CH142072A patent/CH571004A5/xx not_active IP Right Cessation
-
1973
- 1973-01-26 AT AT69973*#A patent/AT331250B/de not_active IP Right Cessation
- 1973-01-29 NO NO353/73A patent/NO138090C/no unknown
- 1973-01-30 HU HUCA342A patent/HU168740B/hu unknown
- 1973-01-31 DE DE2304708A patent/DE2304708A1/de active Pending
- 1973-01-31 IL IL41440A patent/IL41440A/en unknown
- 1973-01-31 CA CA162,943A patent/CA994772A/en not_active Expired
- 1973-01-31 ES ES411147A patent/ES411147A1/es not_active Expired
- 1973-02-01 JP JP1333973A patent/JPS5343511B2/ja not_active Expired
- 1973-02-01 ZA ZA730730A patent/ZA73730B/xx unknown
- 1973-02-01 GB GB507673A patent/GB1424611A/en not_active Expired
- 1973-02-01 FR FR7303599A patent/FR2173982B1/fr not_active Expired
- 1973-02-01 NL NL7301488A patent/NL7301488A/xx not_active Application Discontinuation
-
1974
- 1974-07-31 ZA ZA00744892A patent/ZA744892B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5343511B2 (no) | 1978-11-20 |
| FR2173982A1 (no) | 1973-10-12 |
| ZA73730B (en) | 1974-04-24 |
| NO138090C (no) | 1978-06-28 |
| CA994772A (en) | 1976-08-10 |
| BE794804A (fr) | 1973-05-16 |
| ATA69973A (de) | 1975-11-15 |
| IL41440A (en) | 1976-05-31 |
| ZA744892B (en) | 1975-08-27 |
| ES411147A1 (es) | 1975-12-01 |
| NL7301488A (no) | 1973-08-03 |
| JPS4881879A (no) | 1973-11-01 |
| GB1424611A (en) | 1976-02-11 |
| AT331250B (de) | 1976-08-10 |
| FR2173982B1 (no) | 1978-03-24 |
| CH571004A5 (no) | 1975-12-31 |
| IL41440A0 (en) | 1973-03-30 |
| HU168740B (no) | 1976-07-28 |
| DE2304708A1 (de) | 1973-08-23 |
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