IL40338A - 2-(4-aminophenylimino)thiazines and thiazolidines,their preparation and veterinary and pharmaceutical compositions containing them - Google Patents
2-(4-aminophenylimino)thiazines and thiazolidines,their preparation and veterinary and pharmaceutical compositions containing themInfo
- Publication number
- IL40338A IL40338A IL40338A IL4033872A IL40338A IL 40338 A IL40338 A IL 40338A IL 40338 A IL40338 A IL 40338A IL 4033872 A IL4033872 A IL 4033872A IL 40338 A IL40338 A IL 40338A
- Authority
- IL
- Israel
- Prior art keywords
- general formula
- compound
- group
- process according
- reacted
- Prior art date
Links
- 150000003548 thiazolidines Chemical class 0.000 title claims abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 title claims 2
- 150000004897 thiazines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 21
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims abstract 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims 17
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 9
- 125000003342 alkenyl group Chemical group 0.000 claims 8
- -1 2-(Aminophenylimino)-thiazolines Chemical class 0.000 claims 7
- 150000001412 amines Chemical class 0.000 claims 5
- 239000003085 diluting agent Substances 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 244000045947 parasite Species 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 150000003254 radicals Chemical group 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229940100198 alkylating agent Drugs 0.000 claims 2
- 239000002168 alkylating agent Substances 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 229910000510 noble metal Inorganic materials 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- HCNHXCQEPYZVPT-UHFFFAOYSA-N Cl.CC1=C(C(=O)NC2=CC=C(C=C2)N=C2SCCN2C)C=CC=C1 Chemical compound Cl.CC1=C(C(=O)NC2=CC=C(C=C2)N=C2SCCN2C)C=CC=C1 HCNHXCQEPYZVPT-UHFFFAOYSA-N 0.000 claims 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 108010034145 Helminth Proteins Proteins 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 241000357437 Mola Species 0.000 claims 1
- FULZLIGZKMKICU-UHFFFAOYSA-N N-phenylthiourea Chemical compound NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 claims 1
- 241000244206 Nematoda Species 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000003172 aldehyde group Chemical group 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 150000003934 aromatic aldehydes Chemical class 0.000 claims 1
- 230000037396 body weight Effects 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000008298 dragée Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 244000000013 helminth Species 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000003701 inert diluent Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000005394 methallyl group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- 239000000829 suppository Substances 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- CISSMTSOBLGEAJ-UHFFFAOYSA-N 4-[(3-methyl-1,3-thiazolidin-2-ylidene)amino]aniline Chemical compound CN1CCSC1=NC1=CC=C(N)C=C1 CISSMTSOBLGEAJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 229940124339 anthelmintic agent Drugs 0.000 abstract 1
- 239000000921 anthelmintic agent Substances 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 229940124530 sulfonamide Drugs 0.000 abstract 1
- 150000003456 sulfonamides Chemical class 0.000 abstract 1
Classifications
-
- 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
- C07D277/12—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/18—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/20—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
2-(4-Aminophenylimino) derivatives of thiazolidine and -4H-5,6-dihydro-1,3-thiazines, the corresponding amide and sulfonamide derivatives, and the salts thereof are anthelmintic agents. The compounds, of which 2-(4-aminophenylimino)-N-methylthiazolidine is a typical embodiment, are prepared through cyclization of a thiourea, optionally with subsequent hydrolysis, alkylation or acetylation.
[US3860590A]
Claims (9)
1. CLAIMS 1. 2-(Aminophenylimino)-thiazolines and thiazolid-ines of the following general formula or their salts: in which R is a straight-chain or branched alkyl or alkenyl group ~ and R1 is a hydrogen atom or a straight-chain or 6 7 branched alkyl or alkenyl group, or a -COR or. -S02R group; in which R is a hydrogen atom or a straight-chain or branched alkyl, alkenyl, alkoxy, alkoxyalkyl, phenoxy-alkyl, furyl or. phenyl optionally substituted with riitro, chlorine, bromine ; fluorine, alkyl, alkoxy or trifluoro- 7 methyl; R is a straight-chain or branched alkyl group; 2 3 R and R can be identical or different and are each a hydrogen atom or a straight-chain or branched alkyl, alkenyl or alkoxy group, or a halogen, atom or trifluoro-methyl radical; R^ and ^ are each a hydrogen atom and n is 2 or 3. 2. Compounds according to Claim 1 in which R is an alkyl group with 1 or 2 carbon atoms or an ally! or meth-allyl or crotyl group; R1 is an alkyl group with 1 to 3 6 7 carbon atoms, or an allyl, -COR or -S02 group; in 6 which R is a hydrogen atom or a straight .chain or branched alkyl or alkenyl group with up to 3 carbon atoms or the furyl, or phenyl radical, or an alkoxy radical with up to 7 4 carbon atoms; R is an alkyl group^ with 1 or 2 carbon 2 3 atoms;. R is a hydrogen atom; R is a hydrogen or chlorine 4 5 i · - 55 - 40338/2 13. 2-[4-(4-nltrobenzoylamino)-phenylimino]~N-methyl-thiazolidine. 14. 2-(4-Isobutylaminophenylimino)-N-methyi-thiazolidine. 1 . 2-[ 4-( 4-chlorobenzoylaraino)-phenylimino]-N-methy1-thiazolidine hydrochloride. 16. 2-[4-(3-Chlorohenzoylamino)-pheriylimino]-N-methyl-thiazolidine hydrochloride. , 17. 2-[ 4-( 2-Chlorobenzoylamino)-phenyl-imino]-N-methy1-thiazolidine hydrochloride. 18. 2-[ 4-( 4-me h l-benzoylaraino)-phenylimino]-N-methyl-thiazolidine hydrochloride. 19. 2-[ 4-(3-methylbenzoylamino)-phenylimino]-N-methy1-thiazolidine hydrochloride. 20. 2-[4-( 2-methylbenzoylamino)-phenylimino]-N-methyl-thiazolidine hydrochloride. 21. 2-[4-(2f6-dichlorobenzoylamino)-phenylimino]-N-methyl-thiazolidine hydrochloride. 22. The compound according to claim 1 that is set forth in Example 7a. 23.. Compounds according to claim 1 , 2 or 3 that are hereinbefore specifically mentioned, other than those claimed in any of claims 4 to 22. 24. process for the production of a compound according to any of claims 1 to 23 in which: -(A) a phenylthiourea of the general formula:- . (in which R, R1 , R2, 5, R^, R5 and n are as defined in claim 1 or 2 and X is a halogen, sulphonyloxy, or hydroxyl is cycl sed under the influence of a hydroxylic solvent or under the influence of an acid; or (B) a phe is cyclized by reaction with a compound of the general formula:- (in which general formulae. R, R1 , R2, R^, R4, R5, X and n are as defined in (A) and Y" is X or an KH2 group); or (C) a 2-(aminophenylimino)-3-aza-1 -thia-cycloalkane of the general formula is reacted with an alkylating agent of the general formula:- B - R (VI) (in which general formulae (V) and (VI) R, R1 , R2, R5, R4, R5 and n are as defined in claim 1 or 2 and B is a radical which is eliminated as HB); or (D) a 2-(4-nitrophenylimino)-3-aza-1 -thia-cycloalkane of -..'J - 57 - 40338/2 is reduced to produce an amine of the general formula:- (in which general formulae R, R2, R5, R4", R5 and n are as defined in claim 1 or 2) and, when a compound of any preceding claim is required in which R1 is not hydrogen, this amine is then either (aa) [when a compound of any preceding claim in which is a straight or branched-chain alkyl or alkenyl. group is required] reacted with an alkylating agent of the general formula B - R10 (IX) [in which B is as defined in (C) and R10 is a straight-chain or branched alkyl or alkenyl group ] ; or (bb) [when a compound of any preceding claim in which R1 is an alkyl group is required] reacted with ah oxo compound, of the general formula:- - 58 - 40338/2 (i which R is a hydrogen atom or an alkyl group and I is an alkyl group) to produce a Schiff *s, base which is then reduced to produce the required compound of any preceding claim; or (cc) [whe a compound of any preceding claim in which R 6 7 ie a -COR or -CO group is required] reacted with an acylating or sulphonylating agent of the general formula:- Y - 2 (XI) 6 7 ( in which Z is a -COR or -S02 ' , group as required and Y is a group which is eliminated as HY) ; or (dd) [when a compound Of any preceding claim in which R1 is a straight-chain or branched alkyl,or alkenyl group —; '—— :— is required] reacted with an aliphatic or aromatic aldehyde to give a Schiff's base, which is then quaternised with a compound of the general formula:- B - R10 (IX) [in which B and are as defined in (aa)] and thereafter the aldehyde group is split off hydrolytically to give the required compound of any preceding claim; [when a compound of any preceding claim in which R quired] a compound of the general formula (i which R, R2, .R^, ^, ^, ^ and n are as defined in claim 1 or 2) is hydrolysed. 25. A process according to claim 24(A) or 24(B) in which the thiourea of general formula (II) or (III) is cyclized by' heating in an inert diluent at the boiling point of the diluent. 26. A process according to claim 24(A), 24(B), or 25, in which X is chlorine, bromine, or tosyloxy. 27. A process according to claim 24(C) in which the alkylating agen of general formula (VI) and the compound of general formula (V) are reacted at 20 to 80¾ in the presence of an inert organic diluent. 28. A process according to claim 24(C) or 27 in which B is a halogen, ar lsulphonyloxy, or alk ls lphonyloxy radical. 29. A process according to claim 28 in which B is a chlorine, bromine, benzenesulphonyloxy or methanesulphonyloxy radical· 30. . A process according to claim 24(D) in which the compou of general formula (VII) is reduced with hydrogen in the presence of a noble metal catalyst at 20 to 80°C and 60 to 80 atmospheres gauge. 31 i A. process according to claim 24(D) in which the compou of general formula (VII) is reduced with zinc/hydrochloric , ; • 5 . . '■" 1 0 , -'. " ' radical. .1 5 3β . A process according to claim .24(D-^) or any of claims 3Q to 33 in which the amine of general formula (VIII) and the oxo compound of general formula X are reacted in ..... substantially mola amounts in the presence of an organic ■':.' ·■■ solvent. 20 : 37. A process according to claim 24(1^) or any of claims 30 to 33 and 36 , in which the Schiff's base is reduced. by ', hydrogen with a. noble metal catalyst at about 20°C and about v.- ■ . 1 to 80 atmospheres gauge in the presence of a solvent. 38. A process according to claim 24(D _) or any of claims 25 30 to 33 in which the acylating or sulphonating agent of the general formula (XI) and the amine of general formula (X) are reacted in substantially molar amounts at 20 to 90°C in an - inert organic solvent, • 39. A process according to claim 2 (D^d) or any of claims 30 30 to .33 in which the aldehyde and the amine of general ' . . formula; (VIII ) are reacted in substantially molar amounts at ' 20 to 40°G in an inert organic solvent to produce the 23 or 46 in the form of a sterile or isotonic aqueous ' solution. , , ' 49. A composition according to claim 47 or 48 containing . from 0.5 to 90 of active ingredient by weight. 50. Pharmaceutical compositions substantially as hereinbefore described or specifically .exemplified. 51. , A medicament in dosage unit form comprising a compound according to any of claims .1 to 21 , .23 or 46 either alone or in admixture with a diluent. 5.
2. A medicament in the form of tablets, pills, dragees, capsul.es, ampoules or suppositories comprising, a compound according to any of claims 1 to 21 , 2 or 46 , either alone or in admixture with a diluent. , 5
3. A medicament in dosage unit form according to claim 51 or 52, adapted for a daily dose of 50 to 9/000 mg. 5
4. A medicament in dosage uni form, substantially as ■hereinbefore described or specifically exemplified. 5
5. A method of combatting parasites in human and non-human animals which comprises administering to the animals an active compound according to any of claims 1 to 21, 23 or 46 either alone or- in admixture with a diluent or in the form of a medicament according to. an of claims 51 to 54. 5
6. A method according to claim 55 in which the parasite is - ' a helminth. 5
7. A method according to claim 56 in which the parasite is a nematode. · .5
8. A method according to claim 55, 56 or 57 in which the active compound is administered in an amount of 1 to 100 mg per body weight per day. ; . 5
9. A method of combatting parasites substantially as hereinbefore described or specifically exemplified.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2145807A DE2145807A1 (en) | 1971-09-14 | 1971-09-14 | 2- (AMINOPHENYLIMINO) -3-AZA-1-THIACYCLOALKANE, METHOD OF MANUFACTURING AND USE AS A MEDICINAL PRODUCT |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL40338A0 IL40338A0 (en) | 1972-11-28 |
| IL40338A true IL40338A (en) | 1976-01-30 |
Family
ID=5819465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL40338A IL40338A (en) | 1971-09-14 | 1972-09-12 | 2-(4-aminophenylimino)thiazines and thiazolidines,their preparation and veterinary and pharmaceutical compositions containing them |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US3860590A (en) |
| JP (2) | JPS4836169A (en) |
| AT (1) | AT322548B (en) |
| AU (1) | AU464649B2 (en) |
| BE (1) | BE788743A (en) |
| CA (1) | CA1007638A (en) |
| CH (2) | CH569724A5 (en) |
| DD (2) | DD103898A5 (en) |
| DE (1) | DE2145807A1 (en) |
| EG (1) | EG11037A (en) |
| ES (4) | ES406622A1 (en) |
| FR (1) | FR2154512B1 (en) |
| GB (1) | GB1377265A (en) |
| HU (1) | HU167410B (en) |
| IE (1) | IE36698B1 (en) |
| IL (1) | IL40338A (en) |
| NL (1) | NL7212419A (en) |
| PL (4) | PL89701B1 (en) |
| RO (4) | RO68389A (en) |
| SE (1) | SE412756B (en) |
| SU (3) | SU556728A3 (en) |
| ZA (1) | ZA726271B (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU167761B (en) * | 1973-07-12 | 1975-12-25 | ||
| IL52927A (en) * | 1976-09-17 | 1980-01-31 | Ciba Geigy Ag | 2-(n-methylcarbamoyloxyphenyl imino)-4-thiazoline derivatives their production and their use as pesticides |
| US4140784A (en) * | 1976-09-17 | 1979-02-20 | Ciba-Geigy Corporation | Novel thiazolidines |
| DE2758005A1 (en) | 1977-12-24 | 1979-06-28 | Bayer Ag | PHOSPHONYLUREIDOBENZOL DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS |
| DE3632042A1 (en) * | 1986-03-08 | 1987-09-10 | Bayer Ag | DIARYLSULFID DERIVATIVES |
| US6353006B1 (en) | 1999-01-14 | 2002-03-05 | Bayer Corporation | Substituted 2-arylimino heterocycles and compositions containing them, for use as progesterone receptor binding agents |
| WO2001019807A1 (en) | 1999-09-14 | 2001-03-22 | Shionogi & Co., Ltd. | 2-imino-1,3-thiazine derivatives |
| DE102008030764A1 (en) * | 2008-06-28 | 2009-12-31 | Bayer Animal Health Gmbh | Combination of amidine derivatives with cyclic depsipeptides |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US327708A (en) * | 1885-10-06 | Wet-ore concentrator | ||
| US2877232A (en) * | 1957-12-31 | 1959-03-10 | Ciba Pharm Prod Inc | 2-(4-isopentyloxyphenyl)-imino, 3 (4-isopentyloxyphenyl)-thiazolidine and therapeutically useful salts |
| US3297708A (en) * | 1965-10-06 | 1967-01-10 | American Cyanamid Co | Method of preparing thiazolidines |
| FR1516854A (en) * | 1966-12-20 | 1968-02-05 | Aquitaine Petrole | Process for the production of imino-thiazolidines |
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0
- BE BE788743D patent/BE788743A/en unknown
-
1971
- 1971-09-14 DE DE2145807A patent/DE2145807A1/en active Pending
-
1972
- 1972-08-30 RO RO7280698A patent/RO68389A/en unknown
- 1972-08-30 RO RO80696A patent/RO84247B/en unknown
- 1972-08-30 RO RO80697A patent/RO84248B/en unknown
- 1972-08-30 RO RO7280695A patent/RO68372A/en unknown
- 1972-09-12 DD DD165616A patent/DD103898A5/xx unknown
- 1972-09-12 IL IL40338A patent/IL40338A/en unknown
- 1972-09-12 SU SU1827228A patent/SU556728A3/en active
- 1972-09-12 DD DD173372*A patent/DD105990A5/xx unknown
- 1972-09-12 EG EG371/72A patent/EG11037A/en active
- 1972-09-12 CH CH1338372A patent/CH569724A5/xx not_active IP Right Cessation
- 1972-09-12 SU SU1827231A patent/SU455544A3/en active
- 1972-09-12 CH CH1020475A patent/CH587258A5/xx not_active IP Right Cessation
- 1972-09-12 SU SU1827229A patent/SU505363A3/en active
- 1972-09-13 SE SE7211813A patent/SE412756B/en unknown
- 1972-09-13 ES ES406622A patent/ES406622A1/en not_active Expired
- 1972-09-13 JP JP47091344A patent/JPS4836169A/ja active Pending
- 1972-09-13 NL NL7212419A patent/NL7212419A/xx not_active Application Discontinuation
- 1972-09-13 CA CA151,607A patent/CA1007638A/en not_active Expired
- 1972-09-13 HU HU72BA2802A patent/HU167410B/en unknown
- 1972-09-13 PL PL1972157720A patent/PL89701B1/pl unknown
- 1972-09-13 JP JP47091343A patent/JPS4836168A/ja active Pending
- 1972-09-13 PL PL1972182586A patent/PL93669B1/pl unknown
- 1972-09-13 PL PL1972182585A patent/PL93588B1/pl unknown
- 1972-09-13 PL PL1972182587A patent/PL93690B1/pl unknown
- 1972-09-13 ZA ZA726271A patent/ZA726271B/en unknown
- 1972-09-13 AU AU46604/72A patent/AU464649B2/en not_active Expired
- 1972-09-13 GB GB4255272A patent/GB1377265A/en not_active Expired
- 1972-09-13 IE IE1249/72A patent/IE36698B1/en unknown
- 1972-09-14 AT AT789772A patent/AT322548B/en not_active IP Right Cessation
- 1972-09-14 FR FR7232634A patent/FR2154512B1/fr not_active Expired
- 1972-09-14 US US289092A patent/US3860590A/en not_active Expired - Lifetime
-
1975
- 1975-04-01 ES ES436200A patent/ES436200A1/en not_active Expired
- 1975-04-01 ES ES436202A patent/ES436202A1/en not_active Expired
- 1975-04-01 ES ES436201A patent/ES436201A1/en not_active Expired
Also Published As
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