ES365089A1 - Phenyl-thiazole-malonic acid derivatives - Google Patents
Phenyl-thiazole-malonic acid derivativesInfo
- Publication number
- ES365089A1 ES365089A1 ES365089A ES365089A ES365089A1 ES 365089 A1 ES365089 A1 ES 365089A1 ES 365089 A ES365089 A ES 365089A ES 365089 A ES365089 A ES 365089A ES 365089 A1 ES365089 A1 ES 365089A1
- Authority
- ES
- Spain
- Prior art keywords
- agent
- compositions
- alkyl group
- hydrogen atom
- group
- 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
- KIKQNYBKAAVDGW-UHFFFAOYSA-N 2-(4-phenyl-1,3-thiazol-2-yl)propanedioic acid Chemical class C1(=CC=CC=C1)C=1N=C(SC1)C(C(=O)O)C(=O)O KIKQNYBKAAVDGW-UHFFFAOYSA-N 0.000 title 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 abstract 2
- 239000003242 anti bacterial agent Substances 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 abstract 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 abstract 2
- YNBADRVTZLEFNH-UHFFFAOYSA-N methyl nicotinate Chemical compound COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 abstract 2
- 239000012457 nonaqueous media Substances 0.000 abstract 2
- 231100000252 nontoxic Toxicity 0.000 abstract 2
- 230000003000 nontoxic effect Effects 0.000 abstract 2
- -1 piperidinomethyl Chemical group 0.000 abstract 2
- 239000000725 suspension Substances 0.000 abstract 2
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 abstract 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 abstract 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 abstract 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- PWWVAXIEGOYWEE-UHFFFAOYSA-N Isophenergan Chemical compound C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 PWWVAXIEGOYWEE-UHFFFAOYSA-N 0.000 abstract 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 abstract 1
- 229930193140 Neomycin Natural products 0.000 abstract 1
- 241000400688 Symmetrischema capsicum Species 0.000 abstract 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- 229940116731 Uricosuric agent Drugs 0.000 abstract 1
- 229960001138 acetylsalicylic acid Drugs 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 229910052783 alkali metal Chemical group 0.000 abstract 1
- 150000001340 alkali metals Chemical group 0.000 abstract 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 abstract 1
- 229910021502 aluminium hydroxide Inorganic materials 0.000 abstract 1
- 230000003444 anaesthetic effect Effects 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 229940069428 antacid Drugs 0.000 abstract 1
- 239000003159 antacid agent Substances 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 230000001458 anti-acid effect Effects 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 229940121375 antifungal agent Drugs 0.000 abstract 1
- 239000003429 antifungal agent Substances 0.000 abstract 1
- 229940125715 antihistaminic agent Drugs 0.000 abstract 1
- 239000000739 antihistaminic agent Substances 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- FUFVKLQESJNNAN-RIMUKSHESA-M chembl1200851 Chemical compound [Br-].O([C@H]1C[C@H]2CC[C@@H](C1)[N+]2(C)C)C(=O)C(O)C1=CC=CC=C1 FUFVKLQESJNNAN-RIMUKSHESA-M 0.000 abstract 1
- 229960003677 chloroquine Drugs 0.000 abstract 1
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 abstract 1
- 239000000812 cholinergic antagonist Substances 0.000 abstract 1
- 229960004126 codeine Drugs 0.000 abstract 1
- 239000006071 cream Substances 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- LPEPZBJOKDYZAD-UHFFFAOYSA-N flufenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 LPEPZBJOKDYZAD-UHFFFAOYSA-N 0.000 abstract 1
- 229960004369 flufenamic acid Drugs 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229960003246 homatropine methylbromide Drugs 0.000 abstract 1
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- CYWFCPPBTWOZSF-UHFFFAOYSA-N ibufenac Chemical compound CC(C)CC1=CC=C(CC(O)=O)C=C1 CYWFCPPBTWOZSF-UHFFFAOYSA-N 0.000 abstract 1
- 229950009183 ibufenac Drugs 0.000 abstract 1
- 229960000905 indomethacin Drugs 0.000 abstract 1
- 239000002085 irritant Substances 0.000 abstract 1
- 239000006210 lotion Substances 0.000 abstract 1
- 229960003464 mefenamic acid Drugs 0.000 abstract 1
- HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 abstract 1
- 229960001238 methylnicotinate Drugs 0.000 abstract 1
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 abstract 1
- 229960004927 neomycin Drugs 0.000 abstract 1
- 239000002674 ointment Substances 0.000 abstract 1
- 229960000649 oxyphenbutazone Drugs 0.000 abstract 1
- HFHZKZSRXITVMK-UHFFFAOYSA-N oxyphenbutazone Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=C(O)C=C1 HFHZKZSRXITVMK-UHFFFAOYSA-N 0.000 abstract 1
- 229960005489 paracetamol Drugs 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
- 229960002895 phenylbutazone Drugs 0.000 abstract 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 abstract 1
- 239000006187 pill Substances 0.000 abstract 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 abstract 1
- 229960005205 prednisolone Drugs 0.000 abstract 1
- DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 abstract 1
- 229960003081 probenecid Drugs 0.000 abstract 1
- 229960003910 promethazine Drugs 0.000 abstract 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 abstract 1
- 239000003542 rubefacient Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 150000003431 steroids Chemical class 0.000 abstract 1
- 150000003456 sulfonamides Chemical class 0.000 abstract 1
- 239000000829 suppository Substances 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 abstract 1
- 229960002372 tetracaine Drugs 0.000 abstract 1
- JIVZKJJQOZQXQB-UHFFFAOYSA-N tolazoline Chemical compound C=1C=CC=CC=1CC1=NCCN1 JIVZKJJQOZQXQB-UHFFFAOYSA-N 0.000 abstract 1
- 229960002312 tolazoline Drugs 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
- 239000003383 uricosuric agent Substances 0.000 abstract 1
- 239000005526 vasoconstrictor agent Substances 0.000 abstract 1
- 239000003071 vasodilator agent Substances 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
- C07D277/20—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
- C07D277/22—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
-
- 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
-
- 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
- C07D277/22—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
Pharmaceutical compositions having antiinflammatory, analgesic and anti-pyretic activity comprise, as active ingredient, at least one [alpha]-thiazolyl-malonic acid derivative of the general formula wherein Y or Z is linked to the 2-position of the thiazole nucleus, X is a hydrogen atom or a C 1-3 alkyl group, Y is a phenyl group optionally substituted by 'up to two halogen atoms selected from fluorine, chlorine or bromine, and Z is a group of the formula wherein R1 is a hydrogen or alkali metal atom, a C 1-3 alkyl group, a dialkylaminomethyl group of up to 5 carbon atoms, a piperidinomethyl or morpholinomethyl group, or a chlorine or bromine atom, and R2 and R3 are each a hydrogen atom or a C 1-3 alkyl group, provided that, when R2 and R3 are each a hydrogen atom, R1 is a hydrogen atom or a C 1-3 alkyl group, a tautomer thereof or a non-toxic, pharmaceutically-acceptable salt thereof, togothler with a non-toxic, pharmaceuticallyacceptable diluent or carrier. The compositions may be administered orally, parenterally, topically or rectally in the form of tablets, pills, capsules, suppositories, non-sterile aqueous or non-aqueous solutions or suspensions, sterile injectable aqueous or non-aqueous solutions or suspensions, creams, lotions or ointments. The compositions may additionally contain at least one known anti-inflammatory or analgesic agent, e.g. aspirin, paracetamol, codeine, chloroquine, phenylbutazone, oxyphenbutazone, indomethacin, mefenamic acid, flufenamic acid or ibufenac, or an anti-inflammatory . steroid, such as prednisolone. Compositions intended for oral administration may additionally contain an anti-cholinergic agent, e.g. homatropine methyl bromide, and/or an antacid, e.g. aluminium hydroxide, or a uricosuric agent, e.g. probenecid. Compositions suitable for topical application may additionally contain a vasodilating agent, eg. tolazoline, or a vasoconstricting agent, e.g. adrenaline a local anaesthetic, e.g. amethocaine, a counter-irritant, e.g. capsicum, and/or at least one agent chosen from 'antibacterial agents, such as sulphonamides and antibiotics having antibacterial action, e.g. neomycin anti-fungal agents, e.g. hydroxyquinoline .antihistaminic agents, e.g. promethazine, and rubefacient agents, e.g. methyl nicotinate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB03989/68A GB1192701A (en) | 1968-03-22 | 1968-03-22 | Novel Thiazole Derivatives, the preparation thereof and Compositions containing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES365089A1 true ES365089A1 (en) | 1971-01-01 |
Family
ID=10033003
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES365089A Expired ES365089A1 (en) | 1968-03-22 | 1969-03-22 | Phenyl-thiazole-malonic acid derivatives |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3661920A (en) |
| AT (1) | AT284841B (en) |
| BE (1) | BE730284A (en) |
| BR (1) | BR6807374D0 (en) |
| CA (1) | CA948199A (en) |
| CH (2) | CH513907A (en) |
| CS (3) | CS154266B2 (en) |
| DE (1) | DE1913472A1 (en) |
| DK (3) | DK125251B (en) |
| ES (1) | ES365089A1 (en) |
| FR (1) | FR2004544A1 (en) |
| GB (1) | GB1192701A (en) |
| IE (1) | IE32967B1 (en) |
| IL (1) | IL31679A (en) |
| NL (1) | NL6903963A (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2703542C2 (en) * | 1977-01-26 | 1985-09-26 | Schering AG, 1000 Berlin und 4709 Bergkamen | Thiazolyl cinnamonitriles, insect control agents containing these compounds and processes for their preparation |
| US4153703A (en) * | 1977-06-30 | 1979-05-08 | Uniroyal, Inc. | Method of controlling insects and acarids with certain aryl-substituted thiazoles |
| US4197306A (en) * | 1977-06-30 | 1980-04-08 | Uniroyal, Inc. | Aryl-substituted thiazoles |
| DE2801794A1 (en) | 1978-01-17 | 1979-07-19 | Basf Ag | PROCESS FOR MANUFACTURING THIAZOLE DERIVATIVES AND NEW THIAZOLES |
| DE2920183A1 (en) * | 1979-05-17 | 1981-04-30 | Schering Ag Berlin Und Bergkamen, 1000 Berlin | THIAZOLYLIDEN-OXO-PROPIONITRILE, INSECTICIDAL AGENT CONTAINING THESE COMPOUNDS AND METHOD FOR THE PRODUCTION THEREOF |
| US4346094A (en) * | 1980-09-22 | 1982-08-24 | Eli Lilly And Company | 3-Aryl-5-isothiazolecarboxylic acids and related compounds used to lower uric acid levels |
| US5077305A (en) * | 1990-02-13 | 1991-12-31 | Bristol-Myers Squibb Co. | Thiazole carboxylic acids and esters |
| EP0442448A3 (en) | 1990-02-13 | 1992-08-12 | Bristol-Myers Squibb Company | Heterocyclic carboxylic acids and esters |
| DE10331675A1 (en) * | 2003-07-14 | 2005-02-10 | Bayer Cropscience Ag | Hetaryl-substituted pyrazolidinedione derivatives |
| WO2009052454A2 (en) * | 2007-10-19 | 2009-04-23 | University Of California | Compositions and methods for ameliorating cns inflammation, psychosis, delirium, ptsd or ptss |
-
1968
- 1968-03-22 GB GB03989/68A patent/GB1192701A/en not_active Expired
- 1968-03-23 BR BR207374/68A patent/BR6807374D0/en unknown
-
1969
- 1969-02-17 US US799963A patent/US3661920A/en not_active Expired - Lifetime
- 1969-02-18 IE IE209/69A patent/IE32967B1/en unknown
- 1969-02-23 IL IL31679A patent/IL31679A/en unknown
- 1969-02-24 CA CA043,831A patent/CA948199A/en not_active Expired
- 1969-03-14 NL NL6903963A patent/NL6903963A/xx unknown
- 1969-03-14 AT AT251269A patent/AT284841B/en not_active IP Right Cessation
- 1969-03-17 DE DE19691913472 patent/DE1913472A1/en active Pending
- 1969-03-18 CS CS193669A patent/CS154266B2/cs unknown
- 1969-03-18 CS CS810072*1A patent/CS154268B2/cs unknown
- 1969-03-18 CS CS809972*1A patent/CS154267B2/cs unknown
- 1969-03-21 DK DK157569AA patent/DK125251B/en unknown
- 1969-03-21 CH CH434369A patent/CH513907A/en not_active IP Right Cessation
- 1969-03-21 BE BE730284D patent/BE730284A/xx unknown
- 1969-03-21 FR FR6908408A patent/FR2004544A1/fr not_active Withdrawn
- 1969-03-21 CH CH806371A patent/CH553209A/en not_active IP Right Cessation
- 1969-03-22 ES ES365089A patent/ES365089A1/en not_active Expired
-
1970
- 1970-09-30 DK DK498870AA patent/DK125326B/en unknown
- 1970-09-30 DK DK498970AA patent/DK122393B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6903963A (en) | 1969-09-24 |
| BE730284A (en) | 1969-09-22 |
| CA948199A (en) | 1974-05-28 |
| IE32967L (en) | 1969-09-22 |
| CH553209A (en) | 1974-08-30 |
| DE1913472A1 (en) | 1969-11-06 |
| CS154268B2 (en) | 1974-03-29 |
| DK125251B (en) | 1973-01-22 |
| US3661920A (en) | 1972-05-09 |
| GB1192701A (en) | 1970-05-20 |
| AT284841B (en) | 1970-09-25 |
| BR6807374D0 (en) | 1973-02-08 |
| DK125326B (en) | 1973-02-05 |
| CH513907A (en) | 1971-10-15 |
| IL31679A (en) | 1972-08-30 |
| CS154267B2 (en) | 1974-03-29 |
| DK122393B (en) | 1972-02-28 |
| IE32967B1 (en) | 1974-02-06 |
| FR2004544A1 (en) | 1969-11-28 |
| CS154266B2 (en) | 1974-03-29 |
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