DD274028A5 - Verfahren zur herstellung von thiazolderivaten mit einer wirkung auf das cholinergische system - Google Patents

Verfahren zur herstellung von thiazolderivaten mit einer wirkung auf das cholinergische system Download PDF

Info

Publication number: DD274028A5
Authority: DD; German Democratic Republic
Prior art keywords: group; carbon atoms; hydrogen; formula; alkyl group
Prior art date: 1987-03-12

Application number

DD88313502A

Other languages

German (de)

English (en)

Inventor

Kathleen Biziere

Dominique Olliero

Paul Worms

Original Assignee

K

Priority date (The priority date 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 date listed.)

1987-03-12

Filing date

1988-03-08

Publication date

1989-12-06

1988-03-08 Application filed by K filed Critical K

1989-12-06 Publication of DD274028A5 publication Critical patent/DD274028A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 31
230000008569 process Effects 0.000 title claims abstract description 15
238000002360 preparation method Methods 0.000 title claims abstract description 8
230000000694 effects Effects 0.000 title claims abstract description 7
230000001713 cholinergic effect Effects 0.000 title claims abstract 3
QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical class CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 20
UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims abstract description 13
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 9
150000003585 thioureas Chemical class 0.000 claims abstract description 9
150000003839 salts Chemical class 0.000 claims abstract description 7
150000007979 thiazole derivatives Chemical class 0.000 claims abstract description 6
239000002253 acid Substances 0.000 claims abstract description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 26
239000001257 hydrogen Substances 0.000 claims description 25
125000004432 carbon atom Chemical group C* 0.000 claims description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 16
239000000460 chlorine Substances 0.000 claims description 13
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
150000001412 amines Chemical group 0.000 claims description 7
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
230000002378 acidificating effect Effects 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000006267 biphenyl group Chemical group 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
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125000001624 naphthyl group Chemical group 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000006239 protecting group Chemical group 0.000 claims description 3
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
150000007513 acids Chemical class 0.000 claims description 2
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
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YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 2
125000000753 cycloalkyl group Chemical group 0.000 claims 2
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
238000010438 heat treatment Methods 0.000 abstract description 2
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RMHMFHUVIITRHF-UHFFFAOYSA-N pirenzepine Chemical compound C1CN(C)CCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=CC=C21 RMHMFHUVIITRHF-UHFFFAOYSA-N 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
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239000004480 active ingredient Substances 0.000 description 7
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230000003551 muscarinic effect Effects 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
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UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 description 3
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QCHFTSOMWOSFHM-UHFFFAOYSA-N SJ000285536 Natural products C1OC(=O)C(CC)C1CC1=CN=CN1C QCHFTSOMWOSFHM-UHFFFAOYSA-N 0.000 description 1
206010039424 Salivary hypersecretion Diseases 0.000 description 1
206010039897 Sedation Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
206010044565 Tremor Diseases 0.000 description 1
101150046432 Tril gene Proteins 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
229960004373 acetylcholine Drugs 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000000556 agonist Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
230000027455 binding Effects 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
210000003710 cerebral cortex Anatomy 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000003412 degenerative effect Effects 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
AINBZKYUNWUTRE-UHFFFAOYSA-N ethanol;propan-2-ol Chemical compound CCO.CC(C)O AINBZKYUNWUTRE-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000011049 filling Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000004927 fusion Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
210000004907 gland Anatomy 0.000 description 1
210000001320 hippocampus Anatomy 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
230000002631 hypothermal effect Effects 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000003446 ligand Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
LZCOQTDXKCNBEE-IKIFYQGPSA-N methscopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)C)=CC=CC=C1 LZCOQTDXKCNBEE-IKIFYQGPSA-N 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
239000003094 microcapsule Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 1
230000003387 muscular Effects 0.000 description 1
UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
JELZEJSUONHTAJ-UHFFFAOYSA-N n-(2-morpholin-4-ylethyl)-4,5-dihydrobenzo[e][1,3]benzothiazol-2-amine;dihydrochloride Chemical compound Cl.Cl.N=1C(C2=CC=CC=C2CC2)=C2SC=1NCCN1CCOCC1 JELZEJSUONHTAJ-UHFFFAOYSA-N 0.000 description 1
LDVDAVKCUWMTKN-UHFFFAOYSA-N n-[2-(diethylamino)ethylcarbamothioyl]benzamide Chemical compound CCN(CC)CCNC(=S)NC(=O)C1=CC=CC=C1 LDVDAVKCUWMTKN-UHFFFAOYSA-N 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
244000052769 pathogen Species 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
229960001416 pilocarpine Drugs 0.000 description 1
230000005371 pilomotor reflex Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
FWLKYEAOOIPJRL-UHFFFAOYSA-N prop-1-yn-1-ol Chemical compound CC#CO FWLKYEAOOIPJRL-UHFFFAOYSA-N 0.000 description 1
229940052881 quinhydrone Drugs 0.000 description 1
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
208000026451 salivation Diseases 0.000 description 1
230000009291 secondary effect Effects 0.000 description 1
230000036280 sedation Effects 0.000 description 1
230000009758 senescence Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000829 suppository Substances 0.000 description 1
210000000331 sympathetic ganglia Anatomy 0.000 description 1
230000016978 synaptic transmission, cholinergic Effects 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
WLDDGNNOSXNBRD-UHFFFAOYSA-N tert-butyl n-[3-(benzoylcarbamothioylamino)propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC(=S)NC(=O)C1=CC=CC=C1 WLDDGNNOSXNBRD-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 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
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/38—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- 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
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/84—Naphthothiazoles

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Pyridine Compounds (AREA)

DD88313502A 1987-03-12 1988-03-08 Verfahren zur herstellung von thiazolderivaten mit einer wirkung auf das cholinergische system DD274028A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8703398A FR2612187B1 (fr)	1987-03-12	1987-03-12	Derives du thiazole actifs sur le systeme cholinergique, leur procede de preparation et compositions pharmaceutiques en contenant

Publications (1)

Publication Number	Publication Date
DD274028A5 true DD274028A5 (de)	1989-12-06

Family

ID=9348897

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88313502A DD274028A5 (de)	1987-03-12	1988-03-08	Verfahren zur herstellung von thiazolderivaten mit einer wirkung auf das cholinergische system

Country Status (27)

Country	Link
EP (1)	EP0283390B1 (da)
JP (1)	JPS63243080A (da)
KR (1)	KR880011135A (da)
AR (1)	AR243515A1 (da)
AT (1)	ATE86249T1 (da)
AU (1)	AU612350B2 (da)
DD (1)	DD274028A5 (da)
DE (1)	DE3878708T2 (da)
DK (1)	DK170162B1 (da)
ES (1)	ES2053778T3 (da)
FI (1)	FI881152A7 (da)
FR (1)	FR2612187B1 (da)
HU (1)	HU198916B (da)
IE (1)	IE60173B1 (da)
IL (1)	IL85704A (da)
MA (1)	MA21207A1 (da)
MY (1)	MY103233A (da)
NO (1)	NO170081C (da)
NZ (1)	NZ223845A (da)
OA (1)	OA08871A (da)
PH (1)	PH25389A (da)
PL (1)	PL151889B1 (da)
PT (1)	PT86952B (da)
SU (1)	SU1604157A3 (da)
TN (1)	TNSN88020A1 (da)
YU (1)	YU49688A (da)
ZA (1)	ZA881764B (da)

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JPS6440474A (en) *	1987-08-04	1989-02-10	Hisamitsu Pharmaceutical Co	Novel 2-substituted aminothiazole derivative
JPH0753666B2 (ja) *	1987-09-14	1995-06-07	久光製薬株式会社	置換ジフェニルチアゾール誘導体からなる抗炎症剤
FR2656610B1 (fr) *	1989-12-29	1992-05-07	Sanofi Sa	Derives d'amino-2 phenyl-4 thiazole, leur procede de preparation et leur application therapeutique.
WO1991018882A1 (fr) *	1990-05-29	1991-12-12	Nippon Soda Co., Ltd.	Derive d'amidine heterocyclique n-substitue
WO1992021666A1 (fr) *	1991-05-31	1992-12-10	Laboratoires Upsa	Derives de thiazole antagonistes de recepteurs a l'angiotensine ii
FR2677021B1 (fr) *	1991-05-31	1993-10-01	Upsa Laboratoires	Nouveaux derives de thiazole antagonistes des recepteurs a l'angiotensine ii; leurs procedes de preparation, compositions pharmaceutiques les contenant.
FR2692893B1 (fr) *	1992-06-24	1994-09-02	Sanofi Elf	Dérivés alkylamino ramifiés du thiazole, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent.
AU4982293A (en) *	1993-03-02	1994-09-26	Fujisawa Pharmaceutical Co., Ltd.	Novel heterocyclic compound
FR2714059B1 (fr) *	1993-12-21	1996-03-08	Sanofi Elf	Dérivés amino ramifiés du thiazole, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent.
FR2735777B1 (fr) *	1995-06-21	1997-09-12	Sanofi Sa	Derives de 4-phenylaminothiazole, leur procede de preparation et les compositions pharmaceutiques les contenant
FR2754258B1 (fr) *	1996-10-08	1998-12-31	Sanofi Sa	Derives d'aminothiazole, leur procede de preparation et les compositions pharmaceutiques les contenant
GB9705428D0 (en) *	1997-03-15	1997-04-30	Knoll Ag	Therapeutic agents
EP1087951B9 (en) *	1998-06-18	2006-09-13	Bristol-Myers Squibb Company	Carbon substituted aminothiazole inhibitors of cyclin dependent kinases
DE19831878C2 (de) *	1998-07-17	2001-05-17	Aventis Pharma Gmbh	Polycyclische Thiazolidin-2-yliden Amine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
US6340683B1 (en)	1999-04-22	2002-01-22	Synaptic Pharmaceutical Corporation	Selective NPY (Y5) antagonists (triazines)
US6218408B1 (en)	1999-06-30	2001-04-17	Synaptic Pharmaceutical Corporation	Selective NPY (Y5) antagonists (bicyclics)
AU775166B2 (en)	1999-04-22	2004-07-22	H. Lundbeck A/S	Selective NPY (Y5) antagonists
US6989379B1 (en)	1999-04-22	2006-01-24	H. Lundbick A/S	Selective NPY (Y5) antagonists
US6214853B1 (en)	1999-06-30	2001-04-10	Synaptic Pharmaceutical Corporation	Selective NPY (Y5) antagonists (bicyclics)
US6225330B1 (en)	1999-06-30	2001-05-01	Synaptic Pharmaceutical Corporation	Selective NPY (Y5) antagonists (tricyclics)
US6222040B1 (en)	1999-06-30	2001-04-24	Synaptic Pharmaceutical Corporation	Selective NPY (Y5) antagonists (tricyclics)
US7273880B2 (en)	1999-06-30	2007-09-25	H. Lunbeck A/S	Selective NPY (Y5) antagonists
AU2002314744A1 (en)	2001-04-17	2002-10-28	Sepracor, Inc.	Thiazole and other heterocyclic ligands and use thereof
AU2003207589B2 (en) *	2002-01-16	2006-07-13	University Of Virginia Patent Foundation	2-Aminothiazole Allosteric Enhancers of A1 Adenosine Receptors
DE10251513A1 (de) *	2002-11-04	2004-05-19	Basf Ag	Übergangsmetallkatalysatoren für (Co)Polymerisation von olefinischen Monomeren
JP2007261945A (ja) *	2004-04-07	2007-10-11	Taisho Pharmaceut Co Ltd	チアゾール誘導体
JP5388574B2 (ja) *	2005-05-31	2014-01-15	バーテックスファーマシューティカルズインコーポレイテッド	イオンチャネルのモジュレーターとして有用なヘテロ環式類
KR20110137941A (ko) *	2010-06-18	2011-12-26	(주) 에빅스젠	신규한 티오우레아 또는 우레아 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 ａｉｄｓ 예방 또는 치료용 약학 조성물
RU2456284C1 (ru) *	2011-04-12	2012-07-20	Федеральное государственное автономное образовательное учреждение высшего профессионального образования "Уральский федеральный университет имени первого Президента России Б.Н. Ельцина"	2-аминопропилморфолино-5-арил-6н-1,3,4-тиадиазины, дигидробромиды и 2-аминопропилморфолино-4-арилтиазолы, гидробромиды, обладающие антиагрегантным действием
EP3218373B1 (en) *	2014-11-10	2020-07-22	Evrys Bio, LLC	Anti-hcmv compositions and methods
CN115160207B (zh) *	2022-04-21	2023-09-26	烟台大学	苯甲酰硫脲类化合物及其制备方法和赤潮藻杀藻剂的应用

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US2975182A (en) *	1959-11-16	1961-03-14	Paul A J Janssen	1-(aroylalkyl)-4-(heterocyclyl) piperazines
FR2092714B1 (da) *	1970-06-11	1974-03-22	Melle Bezons
CH583232A5 (da) *	1973-02-02	1976-12-31	Wander Ag Dr A
DE3135250A1 (de) *	1981-09-05	1983-03-17	Basf Ag, 6700 Ludwigshafen	Tricyclische thiazolyloxamate, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel
US4552886A (en) *	1982-06-07	1985-11-12	Eli Lilly And Company	Fungicidal pyridylmethyl-amines
FR2581063B1 (fr) *	1985-04-30	1987-07-17	Chauvin Blache Lab	Amino-2 thiazoles n-substitues, leur procede de preparation et leur application en therapeutique
NL8601494A (nl) *	1985-06-22	1987-01-16	Sandoz Ag	Thiazolen, hun bereiding en farmaceutische preparaten die ze bevatten.

1987
- 1987-03-12 FR FR8703398A patent/FR2612187B1/fr not_active Expired
1988
- 1988-03-03 AU AU12662/88A patent/AU612350B2/en not_active Ceased
- 1988-03-08 MA MA21448A patent/MA21207A1/fr unknown
- 1988-03-08 DD DD88313502A patent/DD274028A5/de not_active IP Right Cessation
- 1988-03-09 DK DK128688A patent/DK170162B1/da not_active IP Right Cessation
- 1988-03-09 PH PH36616A patent/PH25389A/en unknown
- 1988-03-10 NZ NZ223845A patent/NZ223845A/en unknown
- 1988-03-10 AR AR88310267A patent/AR243515A1/es active
- 1988-03-11 DE DE8888400572T patent/DE3878708T2/de not_active Expired - Fee Related
- 1988-03-11 PT PT86952A patent/PT86952B/pt not_active IP Right Cessation
- 1988-03-11 TN TNTNSN88020A patent/TNSN88020A1/fr unknown
- 1988-03-11 AT AT88400572T patent/ATE86249T1/de not_active IP Right Cessation
- 1988-03-11 ZA ZA881764A patent/ZA881764B/xx unknown
- 1988-03-11 HU HU881190A patent/HU198916B/hu not_active IP Right Cessation
- 1988-03-11 OA OA59299A patent/OA08871A/xx unknown
- 1988-03-11 SU SU884355377A patent/SU1604157A3/ru active
- 1988-03-11 YU YU00496/88A patent/YU49688A/xx unknown
- 1988-03-11 ES ES88400572T patent/ES2053778T3/es not_active Expired - Lifetime
- 1988-03-11 NO NO881093A patent/NO170081C/no unknown
- 1988-03-11 EP EP88400572A patent/EP0283390B1/fr not_active Expired - Lifetime
- 1988-03-11 MY MYPI88000258A patent/MY103233A/en unknown
- 1988-03-11 FI FI881152A patent/FI881152A7/fi not_active Application Discontinuation
- 1988-03-11 IE IE72188A patent/IE60173B1/en not_active IP Right Cessation
- 1988-03-11 PL PL1988271132A patent/PL151889B1/pl unknown
- 1988-03-11 IL IL85704A patent/IL85704A/xx unknown
- 1988-03-12 KR KR1019880002614A patent/KR880011135A/ko not_active Withdrawn
- 1988-03-12 JP JP63059223A patent/JPS63243080A/ja active Pending

Also Published As

Publication number	Publication date
DK170162B1 (da)	1995-06-06
AU1266288A (en)	1988-09-15
PL151889B1 (en)	1990-10-31
PH25389A (en)	1991-06-03
ATE86249T1 (de)	1993-03-15
ES2053778T3 (es)	1994-08-01
EP0283390A2 (fr)	1988-09-21
OA08871A (fr)	1989-10-31
FR2612187B1 (fr)	1989-07-21
MY103233A (en)	1993-05-29
FI881152A7 (fi)	1988-09-13
NZ223845A (en)	1990-11-27
DE3878708T2 (de)	1993-09-02
IE60173B1 (en)	1994-06-15
JPS63243080A (ja)	1988-10-07
PL271132A1 (en)	1988-11-24
SU1604157A3 (ru)	1990-10-30
AR243515A1 (es)	1993-08-31
MA21207A1 (fr)	1988-10-01
NO881093L (no)	1988-09-13
NO881093D0 (no)	1988-03-11
PT86952A (pt)	1988-04-01
IL85704A0 (en)	1988-08-31
DE3878708D1 (de)	1993-04-08
DK128688D0 (da)	1988-03-09
HUT47261A (en)	1989-02-28
FI881152A0 (fi)	1988-03-11
YU49688A (en)	1989-10-31
IL85704A (en)	1992-11-15
NO170081C (no)	1992-09-09
HU198916B (en)	1989-12-28
DK128688A (da)	1988-09-13
EP0283390B1 (fr)	1993-03-03
IE880721L (en)	1988-09-12
TNSN88020A1 (fr)	1990-07-10
PT86952B (pt)	1992-05-29
ZA881764B (en)	1988-08-31
KR880011135A (ko)	1988-10-26
AU612350B2 (en)	1991-07-11
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Legal Events

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1996-05-23	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD274028A5 (de)	1989-12-06	Verfahren zur herstellung von thiazolderivaten mit einer wirkung auf das cholinergische system
DE69111077T2 (de)	1995-11-02	Chinazolinderivate um die antitumorwirkung zu verbessern.
DE69225500T2 (de)	1998-09-10	Chinazolinone als mittel gegen angina
DE3433327C2 (de)	1998-07-16	1-Heteroaryl-4-[(2,5-pyrrolidindion-1-yl)alkyl]piperazinderivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Mittel
DE69120100T2 (de)	1996-11-14	Annelierte Thiophen-Derivate, ihre Herstellung und Verwendung
DE69613240T2 (de)	2002-04-25	N-aminoalkylfluorencarboxamide, neue klasse von dopaminerezeptor subtype spezifische liganden
DE69200895T2 (de)	1995-06-29	3-Aminopyridazinderivaten mit einer Wirkung auf das zentrale Nervensystem.
DD200371A5 (de)	1983-04-20	Verfahren zur herstellung von 2,4-disubstituierten thiazolen
EP0736525A1 (de)	1996-10-09	Benzonitrile und -fluoride als 5-HT Agonisten und Antagonisten
DD215544A5 (de)	1984-11-14	Verfahren zur herstellung von dihydropyridinen
DD235256A5 (de)	1986-04-30	Verfahren zur herstellung neuer substituierter pyrrolidinone
DE69612037T2 (de)	2001-10-25	Thiopyran Derivate
AT414125B (de)	2006-09-15	Neue derivate des 4a,5,9,10,11,12-hexahydro- benzofuro(3a,3,2)(2) benzazepin, verfahren zu deren herstellung sowie deren verwendung zur herstellung von arzneimitteln
DE3216843C2 (de)	1986-10-23	3-Thiomethyl-pyridin-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2315148A1 (de)	1973-10-18	Neue chinolinderivate, verfahren zu ihrer herstellung und ihre verwendung
EP1194426B1 (de)	2004-08-18	Benzofuranderivate
EP0266308B1 (de)	1991-07-24	Indolo-pyrazino-benzodiazepin-Derivate
DE69121894T2 (de)	1997-02-06	Heterocyclische verbindungen, herstellung und verwendung
DE1076691B (de)	1960-03-03	Verfahren zur Herstellung von Phenthiazinderivaten
US4983603A (en)	1991-01-08	Tricyclic cholinergic receptor agonists
DE69012451T2 (de)	1995-02-02	Cyanoguanidin-Derivate.
DE69104155T2 (de)	1995-05-04	6-Alkylpyridazinderivate, Verfahren zu deren Herstellung und diese enthaltende Zusammensetzungen.
DE2656227C2 (de)	1985-07-04	Basisch alkylierte Diphenyldisulfid-2,2'-biscarbonsäureamide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel
DE69905191T2 (de)	2003-10-16	Kondensierte pyridazinonverbindungen
AT384809B (de)	1988-01-11	Verfahren zur herstellung von neuen imidazopyridin-derivaten