GB1330151A - Substituted quinoxaline-di oxides and process of preparation thereof - Google Patents
Substituted quinoxaline-di oxides and process of preparation thereofInfo
- Publication number
- GB1330151A GB1330151A GB5231270A GB5231270A GB1330151A GB 1330151 A GB1330151 A GB 1330151A GB 5231270 A GB5231270 A GB 5231270A GB 5231270 A GB5231270 A GB 5231270A GB 1330151 A GB1330151 A GB 1330151A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reaction
- compounds
- prepared
- compound
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 abstract 25
- 238000006243 chemical reaction Methods 0.000 abstract 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 abstract 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 4
- OKEAMBAZBICIFP-UHFFFAOYSA-N 3-oxido-2,1,3-benzoxadiazol-3-ium Chemical compound C1=CC=CC2=[N+]([O-])ON=C21 OKEAMBAZBICIFP-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- NGAVSCAXDJMZQP-UHFFFAOYSA-N 2-acetyloxyethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC(C)=O NGAVSCAXDJMZQP-UHFFFAOYSA-N 0.000 abstract 1
- WJAXXWSZNSFVNG-UHFFFAOYSA-N 2-bromoethanamine;hydron;bromide Chemical compound [Br-].[NH3+]CCBr WJAXXWSZNSFVNG-UHFFFAOYSA-N 0.000 abstract 1
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 abstract 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 1
- CKIHZSGJPSDCNC-UHFFFAOYSA-N Quindoxin Chemical class C1=CC=C2N([O-])C=C[N+](=O)C2=C1 CKIHZSGJPSDCNC-UHFFFAOYSA-N 0.000 abstract 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000005263 alkylenediamine group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 125000002993 cycloalkylene group Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- IWKJAXQYYBHLLO-UHFFFAOYSA-N n-(2-bromoethyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NCCBr IWKJAXQYYBHLLO-UHFFFAOYSA-N 0.000 abstract 1
- 101150009274 nhr-1 gene Proteins 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 abstract 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 abstract 1
- 229910052727 yttrium Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
- C07D241/52—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/137—Heterocyclic compounds containing two hetero atoms, of which at least one is nitrogen
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/30—Feeding-stuffs specially adapted for particular animals for swines
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/10—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Birds (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Fodder In General (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1330151 Quinoxaline-1,4-dioxides PFIZER Inc 3 Nov 1970 [18 March 1970 (2)] 52312/70 Heading C2C Novel compounds I, II and IIA in which X is a 6- or 7-position substituent and is H, Cl, Br, F, CH 3 , CH 3 O or CF 3 ; R 2 is 1-4 C alkyl, R 4 is 1-3 C alkyl; Z is Cl or Br; Z<SP>1</SP> is OH, OCOR, NH 2 , NHR 1 or NR 3 R 5 ; R is H, 1-3 C alkyl, phenyl, alkoxyphenyl or dialkylaminophenyl; R 1 is 1-4 C alkyl, benzoyl or substituted benzoyl; R 3 and R 5 are 1-2 C alkyl; Y is O, S or NR 6 ; R 6 is H or 1-4 C alkyl; and A is alkylene of 2-5 C which places at least 2 C between N and Y, N and Z or O and Z<SP>1</SP> or A is part of a 3-8 C cycloalkylene (A may be substituted by OH), are prepared (a) by reaction of an appropriate benzofuroxan with a compound III or IV: a compound H 2 N-A-Z(HZ) m (m=0 or 1) and diketene; a compound R 4 COCH 2 COOAZ<SP>1</SP>; a compound R 4 -CO-CH 2 -CO-O-A-NR 1 - COO t-alkyl followed by hydrolysis; or a compound R 4 -CH 2 -CO-CO 2 -A-Z<SP>1</SP>; or (b) by reaction of a compound IX or XI with HO-A-Z<SP>1</SP>; or (c) by reaction of an X- substituted -2-cyano-3-R 2 -quinoxaline 1,4-dioxide with H 2 N-A-SH or H 2 N-A-NHR 6 - C 7 H 7 -SO 3 H; or (d) by reaction of an X-substituted-2-amido ether HCl-3-R 2 -quinoxaline- 1,4-dioxide with an appropriate alkylene diamine or thioalkylamine; or (e) by cyclizing compounds II to give compounds I. 2 - (Acetyloxy)ethyl - acetoacetate is prepared by reaction of 2-hydroxyethyl acetate and diketene. Other compounds CH 3 COCH 2 CO 2 AZ<SP>1</SP> are similarly prepared. N - (2 - Bromoethyl)acetoacetamide is prepared by reaction of diketene with 2-bromoethylamine HBr. Compounds CH 3 CO.CH 2 CO 2 -A-NR 3 R 5 are prepared by reaction of diketene and R 3 R 5 NA-OH. Compounds XII are prepared by reaction of the appropriate benzofuroxan with Compounds are prepared by reaction of diketene with HOA-NR 1 -COOC(CH 3 ) 3 . Compounds HO-A-Z<SP>1</SP> where Z<SP>1</SP> is -O 2 CR, are prepared by reaction of HO-A-OH with an appropriate amide. Compounds HO-A-Z<SP>1</SP> where Z<SP>1</SP> is substituted amino, are prepared by reaction of HO-A-halogen with an appropriate amine. Compounds NH 2 -A-Cl.HCl are prepared by reaction of NH 2 -A-OH.HCl with SOCl 2 . Compounds R 4 COCH 2 CO 2 -A-Z<SP>1</SP> are prepared by the reaction of Dorsch et al., J. Am. Chem. Soc., 54, 2960 (1932). Compounds XIII are prepared by reaction of the appropriate 2 - methyl - 1,3 - oxazacyclic compound with R 4 COCl in the presence of n-butyl-lithium. Compounds XIV are prepared by reaction of HOANH 2 with acetic acid. Compounds XV are prepared by reaction of H 2 N-A-NHR 1 with acetic acid. Compounds XVI are prepared by reaction of Cl-A-Cl with thioacetamide. Compounds XVII are prepared by reaction of the 2-cyano compounds with ethanol. Compounds XVIII are prepared by reaction of the 2-methyl compound with R 2 COCl and n-butyl lithium. Compounds XIX are prepared by reaction of R 2 COCH 2 CN with an appropriate benzofuroxan. Pharmaceutical compositions comprise a compound I, II or IIA together with a suitable carrier and are useful as antibacterial agents.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2084170A | 1970-03-18 | 1970-03-18 | |
| US2084270A | 1970-03-18 | 1970-03-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1330151A true GB1330151A (en) | 1973-09-12 |
Family
ID=26693940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5231270A Expired GB1330151A (en) | 1970-03-18 | 1970-11-03 | Substituted quinoxaline-di oxides and process of preparation thereof |
Country Status (13)
| Country | Link |
|---|---|
| JP (3) | JPS5434756B1 (en) |
| AR (3) | AR202999A1 (en) |
| AT (1) | AT315865B (en) |
| BE (1) | BE764088A (en) |
| CH (1) | CH557356A (en) |
| DE (1) | DE2111710C3 (en) |
| DK (1) | DK131677C (en) |
| ES (1) | ES388787A1 (en) |
| FR (1) | FR2085717B1 (en) |
| GB (1) | GB1330151A (en) |
| IT (1) | IT1019008B (en) |
| NL (3) | NL7102953A (en) |
| ZA (1) | ZA711022B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4012512A (en) * | 1972-09-05 | 1977-03-15 | Ciba-Geigy Corporation | Animal feeds containing quinoxaline-di-n-oxide derivatives |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3870718A (en) * | 1971-12-13 | 1975-03-11 | Pfizer | 2-imidazolidine substituted quinoxaline-1,4-dioxides and intermediates therefor |
| CH575213A5 (en) * | 1972-09-05 | 1976-05-14 | Ciba Geigy Ag | |
| US4254120A (en) * | 1978-12-19 | 1981-03-03 | Ciba-Geigy Corporation | Growth promoting quinoxaline-di-N-oxide carboxamides |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1058665B (en) * | 1955-10-11 | 1959-06-04 | Gen Aniline & Film Corp | Drying accelerator for film formers containing drying or semi-drying oils |
| DE1670935C3 (en) * | 1967-10-04 | 1975-12-04 | Bayer Ag, 5090 Leverkusen | 2-Methyl-3-carboxamidoquinoxaline-1,4-dl-N-oxides, a process for their preparation and antibacterial agents containing these compounds |
-
1970
- 1970-11-03 GB GB5231270A patent/GB1330151A/en not_active Expired
-
1971
- 1971-02-17 ZA ZA711022A patent/ZA711022B/en unknown
- 1971-03-02 ES ES388787A patent/ES388787A1/en not_active Expired
- 1971-03-04 DK DK99971*#A patent/DK131677C/en active
- 1971-03-05 JP JP1136171A patent/JPS5434756B1/ja active Pending
- 1971-03-05 IT IT48832/71A patent/IT1019008B/en active
- 1971-03-05 AT AT191571A patent/AT315865B/en not_active IP Right Cessation
- 1971-03-05 NL NL7102953A patent/NL7102953A/xx not_active Application Discontinuation
- 1971-03-11 BE BE764088A patent/BE764088A/en unknown
- 1971-03-11 DE DE2111710A patent/DE2111710C3/en not_active Expired
- 1971-03-12 FR FR7108799A patent/FR2085717B1/fr not_active Expired
- 1971-03-12 CH CH366771A patent/CH557356A/en not_active IP Right Cessation
- 1971-12-23 AR AR239791A patent/AR202999A1/en active
-
1973
- 1973-01-01 AR AR250155A patent/AR204703A1/en active
- 1973-02-09 AR AR246512A patent/AR197977A1/en active
-
1978
- 1978-04-22 JP JP4831978A patent/JPS53127487A/en active Granted
- 1978-04-22 JP JP4831878A patent/JPS53127486A/en active Granted
- 1978-07-28 NL NL7808009A patent/NL7808009A/en not_active Application Discontinuation
- 1978-07-28 NL NL7808008A patent/NL7808008A/en not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4012512A (en) * | 1972-09-05 | 1977-03-15 | Ciba-Geigy Corporation | Animal feeds containing quinoxaline-di-n-oxide derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| DK131677C (en) | 1976-04-26 |
| JPS53127487A (en) | 1978-11-07 |
| NL7808009A (en) | 1978-11-30 |
| NL7808008A (en) | 1978-11-30 |
| ZA711022B (en) | 1971-12-29 |
| FR2085717A1 (en) | 1971-12-31 |
| IT1019008B (en) | 1977-11-10 |
| CH557356A (en) | 1974-12-31 |
| JPS554748B2 (en) | 1980-01-31 |
| DE2111710B2 (en) | 1979-01-25 |
| AR204703A1 (en) | 1976-02-27 |
| BE764088A (en) | 1971-09-13 |
| DE2111710C3 (en) | 1979-09-13 |
| AT315865B (en) | 1974-06-10 |
| JPS5434756B1 (en) | 1979-10-29 |
| ES388787A1 (en) | 1974-02-01 |
| JPS554749B2 (en) | 1980-01-31 |
| DK131677B (en) | 1975-08-18 |
| AR202999A1 (en) | 1975-08-08 |
| FR2085717B1 (en) | 1975-06-06 |
| NL7102953A (en) | 1971-09-21 |
| AR197977A1 (en) | 1974-05-24 |
| DE2111710A1 (en) | 1971-09-30 |
| JPS53127486A (en) | 1978-11-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |