NO139049B - Analogifremgangsmaate for fremstilling av terapeutisk aktive triaziner - Google Patents
Analogifremgangsmaate for fremstilling av terapeutisk aktive triaziner Download PDFInfo
- Publication number
- NO139049B NO139049B NO741044A NO741044A NO139049B NO 139049 B NO139049 B NO 139049B NO 741044 A NO741044 A NO 741044A NO 741044 A NO741044 A NO 741044A NO 139049 B NO139049 B NO 139049B
- Authority
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- Norway
- Prior art keywords
- general formula
- atoms
- preparation
- therapeutically active
- optionally substituted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 150000003918 triazines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 230000001588 bifunctional effect Effects 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- SACAEVOKRBNXPN-UHFFFAOYSA-N n-phenyl-4,5-dihydroimidazol-1-amine Chemical compound C1=NCCN1NC1=CC=CC=C1 SACAEVOKRBNXPN-UHFFFAOYSA-N 0.000 claims description 2
- 150000002905 orthoesters Chemical class 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- OXISDMSERFAPRY-UHFFFAOYSA-N imidazo[1,2-a][1,3,5]triazine Chemical class C1=NC=NC2=NC=CN21 OXISDMSERFAPRY-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- -1 1-carbamoyl-2-(2,6-dichlorophenylamino)-2-imidazoline Chemical compound 0.000 description 1
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000003501 anti-edematous effect Effects 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- HZSIRCSREATQNA-UHFFFAOYSA-N n-carbonochloridoyl-4-chlorobenzenecarboximidoyl chloride Chemical compound ClC(=O)N=C(Cl)C1=CC=C(Cl)C=C1 HZSIRCSREATQNA-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
- Peptides Or Proteins (AREA)
Description
Denne oppfinnelse-angår fremstilling- av' nye -imidazo [ 1 ,2-a]-s-triaziner med deri generelle formel- i
hvor betyr en fenylrest som eventuelt er substituert med 1-3, like eller forskjellige, substituenter valgt fra halogenatomér, fortrinnsvis fluor-, klor- eller bromatomer, metyl- og trifluor-metylgrupper, og R^-betyr-et - hydrogenatom-eller en fenylrest som eventuelt er substituert med ett eller flere halogenatomér, fortrinnsvis kloratomer,
med verdifulle terapeutiske egenskaper. '
I henhold til oppfinnelsen fremstilles forbindelsene med formel I ved at
a) et fenylamino-imidazolin med den generelle formel II
hvor R^ har den ovenfor angitte betydning, kondenseres med en bifunksjonell forbindelse med den generelle formel III, hvor R2 er som ovenfor angitt, og X og Y, som kan være like eller forskjellige, betyr et halogenatom, fortrinnsvis klor eller brom. f- Kondensasjonen utføres normalt i upolare oppløsningsmidler, men kah også utføres uten anvendelse av et oppløsningsmiddel, ved oppvarmning av begge komponenter til temperaturer mellom 60 og 180°C, ,fortrinnsvis 80-140°C. Syrebindende midler så som natrium-karbonat, natriumhydrogenkarbonat og trietylamin viser seg å være fordelaktige ved omsetningen. Mellomproduktene med formel IV som opptrer ved kondensasjonen, er normalt ikke isolerbare. De ring-sluttes meget lett til forbindelsene med den generelle formel I. b) en forbindelse med den generelle formel VII hvor har den ovenfor angitte betydning, omsettes med en orto-ester med formel VIII
hvor R2 har den ovenfor angitte betydning, og R betyr en lavere alkylgruppe med 1 til 3 karbonatomer.
Denne kondensasjon utføres fortrinnsvis termisk med eller uten anvendelse av oppløsningsmidler ved temperaturer mellom 80 og 180°C.
Utgangsforbindelser med formel II er f.eks. beskrevet i de belgiske patentskrifter 623.305, 687.656, 687.657 og 705.94.4 .., .
Forbindelser méd formel III kan fremstilles i- henhold til R. Neidlein og W. Haussmann, Tetrahedron Letters 28,, 2432 (.1965) eller S. Yanagida ét al. , Bull.. Chem. Sog .. Japan £4 , 2182 (1971).
Forbindelser med formel VII kan- fremstilles.ved om-setning åv forbindelser med formel II med karbaminsyreestere. ;
De nye forbindelser er i. besittelse av verdifulle terapeutiske egenskaper.. De har særlig , en utpreget anti- , depressiv virkning, som kan være ledsaget av en anti-sår-virkning, • anti-ødem-virkning, en diuretisk virkning eller blodtrykksénkende. eller smertestillende virkning. Forbindelsene med den generelle formel- I kan anvendes^ enteralt eller også parenteralt. Doseringen ligger fra 0,1 til 10 mg.
De følgende eksempler skal tjene til å illustrere oppfinnelsen ytterligere..
Eksempel 1
8-( 2, 6- diklorfenyl)- 7-( 4- klorfenyl)- 5- okso- 2, 3- dihydro- imidazo-[ 1, 2- a]- s- triazin ( fremgangsmåte a)
2,3 g (0,01 mol) 2-(2,6-diklorfenylamino)-2-imidazolin oppløses i 50 ml absolutt benzen, og efter tilsetning av 5 ml trietylamin settes det dråpevis til oppløsningen ved koke-temperatur 2,4 g (0,01 mol) N-(a-klor-4-klorbenzyliden)-karbamoylklorid, oppløst i 25 ml absolutt benzen, i løpet av ca. 15 minutter. Det oppvarmes videre i 15 minutter, og reaksjonsblandingen inndampes derefter til tørrhet i vakuum. Residuet behandles med fortynnet saltsyre (fjernelse av forurensninger
som går i oppløsning) og avsuges derefter. Efter vasking med vann, etanol og eter avpresses det dannede imidazo[1,2-a]-s-triazin på leirjord og omkrystalliseres fra kloroform.
Utbytte 2,25 g (svarende til 52,0% av det teoretiske).
sm.p.: 320-322°C.
Forbindelsen er uoppløselig i vann, fortynnet saltsyre, etanol og eter. Den oppløses i dimetylsulfoksyd.
Eksempel 2 8-( 2, 6- diklorfenyl)- 2, 3- dihydro- 5- okso- imidazo[ l, 2- a] s- triazin
( fremgangsmåte b)
2,73 g (0,01 mol) l-karbamoyl-2-(2,6-diklorfenylamino)-2-imidazolin, smp.: 257-259°C, oppvarmes sammen med 5 ml orto-maursyreetylester i 15 ml heksametylfosforsyretriamid (HMPT) ved tilbakeløpstemperatur i 2 timer. Reaksjonsblandingen, som inne-holder tre nye forbindelser (påvisbare i tynnskiktkromatogram) fortynnes med 200ml benzen, og HMPT-benzen-oppløsningen vaskes flere ganger med vann. Den organiske fase inndampes i vakuum, og residuet oppløses i fortynnet saltsyre. Ved fraksjonert eter-ekstraksjon ved forskjellige pH-verdier får man 0,15 g imidazo-[1,2-a]s-triazin (kontroll ved tynnskiktkromatogram) med smp. 155-157°C.
Ytterligere eksempler på forbindelser fremstilt analogt med eksempel 1, er gjengitt i den følgende tabell:
Claims (1)
- Analogifremgangsmåte for fremstilling av terapeutiskaktive forbindelser med den generelle formel Ihvor R^ betyr en fenylrest som eventuelt er substituert med 1-3,like eller forskjellige, substituenter valgt fra halogenatomér, fortrinnsvis fluor-, klor- eller bromatomer, metyl- og trifluor-metylgrupper, og R2 betyr en fenylrest som eventuelt er substituert med ett eller flere halogenatomér, fortrinnsvis kloratomer, karakterisert ved at (a) et fenylamino-imidazolin med den generelle formel IIhvor R^ har den ovenfor angitte betydning, kondenseres med en bifunksjonell forbindelse med den generelle formel IIIhvor R2 er som ovenfor angitt, og X og Y, som kan være like eller forskjellige, betyr et halogenatom, fortrinnsvis klor eller brom,eller (b) en forbindelse med den generelle formel VII hvor R-^ har den ovenfor angitte betydning, omsettes med en orto-ester med formel VIIIhvor R2 har den ovenfor angitte betydning og R betyr en lavere alkylgruppe med 1 til 3 karbonatomer.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2314488A DE2314488C3 (de) | 1973-03-23 | 1973-03-23 | 8-(2,6-Dichlorphenyl)-7-(4-chlorphenyl)-5-oxo-233,8-tetrahydro-imidazo [1,2-a] -s-triazin, Verfahren zu dessen Herstellung und dieses enthaltene Arzneimittel |
Publications (3)
Publication Number | Publication Date |
---|---|
NO741044L NO741044L (no) | 1974-09-24 |
NO139049B true NO139049B (no) | 1978-09-18 |
NO139049C NO139049C (no) | 1979-01-03 |
Family
ID=5875651
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO741044A NO139049C (no) | 1973-03-23 | 1974-03-22 | Analogifremgangsmaate for fremstilling av terapeutisk aktive triaziner |
Country Status (26)
Country | Link |
---|---|
US (1) | US3887552A (no) |
JP (1) | JPS5821634B2 (no) |
AT (1) | AT331256B (no) |
BE (1) | BE812736A (no) |
BG (2) | BG23750A3 (no) |
CA (1) | CA1017339A (no) |
CH (2) | CH584714A5 (no) |
CS (1) | CS191229B2 (no) |
DD (1) | DD112266A5 (no) |
DE (1) | DE2314488C3 (no) |
DK (1) | DK139519C (no) |
ES (2) | ES424345A1 (no) |
FI (1) | FI55664C (no) |
FR (1) | FR2222100B1 (no) |
GB (1) | GB1455356A (no) |
HU (1) | HU171082B (no) |
IE (1) | IE39965B1 (no) |
IL (1) | IL44470A (no) |
NL (1) | NL179479C (no) |
NO (1) | NO139049C (no) |
PL (2) | PL88663B1 (no) |
RO (2) | RO68650A (no) |
SE (1) | SE419087B (no) |
SU (2) | SU496734A3 (no) |
YU (2) | YU36959B (no) |
ZA (1) | ZA741864B (no) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1428269A (en) * | 1973-11-07 | 1976-03-17 | Ici Ltd | Pyrimidino-triazine compounds and their use as pesticides |
US4289778A (en) * | 1977-12-27 | 1981-09-15 | Eli Lilly And Company | 2-(Substituted imino)-N-(3-substituted phenyl)-3-thiazolidinecarbothioamides |
JPS6050207U (ja) * | 1983-09-09 | 1985-04-09 | ビ−・エス・コンクリ−ト株式会社 | 桁下の吊り足場 |
JPS61246273A (ja) * | 1985-04-25 | 1986-11-01 | Dainippon Ink & Chem Inc | 顔料ベ−スト |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE791025A (fr) * | 1971-11-19 | 1973-05-07 | Allen & Hanburys Ltd | Composes heterocycliques |
-
1973
- 1973-03-23 DE DE2314488A patent/DE2314488C3/de not_active Expired
-
1974
- 1974-03-08 AT AT193674A patent/AT331256B/de not_active IP Right Cessation
- 1974-03-12 US US450289A patent/US3887552A/en not_active Expired - Lifetime
- 1974-03-16 ES ES424345A patent/ES424345A1/es not_active Expired
- 1974-03-16 ES ES424346A patent/ES424346A1/es not_active Expired
- 1974-03-18 CS CS741939A patent/CS191229B2/cs unknown
- 1974-03-19 FI FI822/74A patent/FI55664C/fi active
- 1974-03-20 RO RO7484657A patent/RO68650A/ro unknown
- 1974-03-20 CH CH382874A patent/CH584714A5/xx not_active IP Right Cessation
- 1974-03-20 RO RO7400078112A patent/RO63042A/ro unknown
- 1974-03-20 CH CH382974A patent/CH588492A5/xx not_active IP Right Cessation
- 1974-03-21 HU HU74BO00001492A patent/HU171082B/hu unknown
- 1974-03-21 SU SU2007686A patent/SU496734A3/ru active
- 1974-03-21 BG BG030628A patent/BG23750A3/xx unknown
- 1974-03-21 SU SU2007687A patent/SU519135A3/ru active
- 1974-03-21 YU YU0790/74A patent/YU36959B/xx unknown
- 1974-03-21 BG BG026154A patent/BG23006A3/xx unknown
- 1974-03-22 FR FR7410019A patent/FR2222100B1/fr not_active Expired
- 1974-03-22 IL IL44470A patent/IL44470A/en unknown
- 1974-03-22 NO NO741044A patent/NO139049C/no unknown
- 1974-03-22 IE IE635/74A patent/IE39965B1/xx unknown
- 1974-03-22 ZA ZA00741864A patent/ZA741864B/xx unknown
- 1974-03-22 BE BE142376A patent/BE812736A/xx not_active IP Right Cessation
- 1974-03-22 PL PL1974169752A patent/PL88663B1/pl unknown
- 1974-03-22 NL NLAANVRAGE7403893,A patent/NL179479C/xx not_active IP Right Cessation
- 1974-03-22 SE SE7403942A patent/SE419087B/xx unknown
- 1974-03-22 GB GB1290574A patent/GB1455356A/en not_active Expired
- 1974-03-22 JP JP49032462A patent/JPS5821634B2/ja not_active Expired
- 1974-03-22 PL PL1974183800A patent/PL92111B1/zh unknown
- 1974-03-22 DK DK159774A patent/DK139519C/da not_active IP Right Cessation
- 1974-03-22 DD DD177384A patent/DD112266A5/xx unknown
- 1974-03-22 CA CA195,706A patent/CA1017339A/en not_active Expired
-
1980
- 1980-07-08 YU YU1763/80A patent/YU36961B/xx unknown
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