IL93485A - Tetrahydropyridines process for their preparation intermediates therefor compositions containing them and process for use of such compositions - Google Patents

Tetrahydropyridines process for their preparation intermediates therefor compositions containing them and process for use of such compositions

Info

Publication number: IL93485A
Authority: IL; Israel
Prior art keywords: alkyl; formula; compound; group; alkoxy
Prior art date: 1989-02-23

Application number

IL9348590A

Other languages

English (en)

Original Assignee

Ici Australia Operations

Australian Inst Marine Science

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.)

1989-02-23

Filing date

1990-02-21

Publication date

1996-01-19

1990-02-21 Application filed by Ici Australia Operations, Australian Inst Marine Science filed Critical Ici Australia Operations

1996-01-19 Publication of IL93485A publication Critical patent/IL93485A/en

Links

239000000203 mixture Substances 0.000 title claims abstract description 45
238000000034 method Methods 0.000 title claims abstract description 27
238000002360 preparation method Methods 0.000 title claims description 11
239000000543 intermediate Substances 0.000 title description 5
125000004853 tetrahydropyridinyl group Chemical class N1(CCCC=C1)* 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 86
125000000217 alkyl group Chemical group 0.000 claims abstract description 34
125000003545 alkoxy group Chemical group 0.000 claims abstract description 27
239000001257 hydrogen Substances 0.000 claims abstract description 24
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
-1 hydroxy, amino Chemical group 0.000 claims abstract description 20
125000003342 alkenyl group Chemical group 0.000 claims abstract description 12
239000000516 sunscreening agent Substances 0.000 claims abstract description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 9
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
230000000475 sunscreen effect Effects 0.000 claims abstract description 9
125000001589 carboacyl group Chemical group 0.000 claims abstract description 8
125000001424 substituent group Chemical group 0.000 claims abstract description 6
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
125000002837 carbocyclic group Chemical group 0.000 claims abstract 4
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
239000003795 chemical substances by application Substances 0.000 claims description 9
150000001412 amines Chemical class 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 8
150000002431 hydrogen Chemical group 0.000 claims description 8
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 7
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Chemical class CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
239000004033 plastic Substances 0.000 claims description 6
229920003023 plastic Polymers 0.000 claims description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
239000003973 paint Substances 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
239000008199 coating composition Substances 0.000 claims description 2
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 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
125000000547 substituted alkyl group Chemical group 0.000 abstract 2
125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
239000003921 oil Substances 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
239000012044 organic layer Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 6
239000000047 product Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
230000000699 topical effect Effects 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 4
239000007788 liquid Substances 0.000 description 4
HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000007789 gas Substances 0.000 description 3
239000013067 intermediate product Substances 0.000 description 3
239000010410 layer Substances 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
230000005855 radiation Effects 0.000 description 3
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
238000002835 absorbance Methods 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
239000000654 additive Substances 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000003480 eluent Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000000499 gel Substances 0.000 description 2
229910000042 hydrogen bromide Inorganic materials 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000000463 material Substances 0.000 description 2
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
238000005192 partition Methods 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
238000012216 screening Methods 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000002211 ultraviolet spectrum Methods 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 1
JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 1
WYUYEJNGHIOFOC-VVTVMFAVSA-N 2-[(z)-1-(4-methylphenyl)-3-pyrrolidin-1-ylprop-1-enyl]pyridine;hydrochloride Chemical compound Cl.C1=CC(C)=CC=C1C(\C=1N=CC=CC=1)=C\CN1CCCC1 WYUYEJNGHIOFOC-VVTVMFAVSA-N 0.000 description 1
125000006040 2-hexenyl group Chemical group 0.000 description 1
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
239000004150 EU approved colour Substances 0.000 description 1
206010015150 Erythema Diseases 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
229940123973 Oxygen scavenger Drugs 0.000 description 1
239000006096 absorbing agent Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
229920000180 alkyd Polymers 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000012505 colouration Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000010219 correlation analysis Methods 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
LTLCGIKWGSDBMN-UHFFFAOYSA-L dimercury diacetate Chemical compound CC(=O)O[Hg][Hg]OC(C)=O LTLCGIKWGSDBMN-UHFFFAOYSA-L 0.000 description 1
230000000694 effects Effects 0.000 description 1
231100000321 erythema Toxicity 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000007654 immersion Methods 0.000 description 1
239000003999 initiator Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
239000004816 latex Substances 0.000 description 1
229920000126 latex Polymers 0.000 description 1
125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
239000002304 perfume Substances 0.000 description 1
239000000049 pigment Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000006254 rheological additive Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Dermatology (AREA)
Epidemiology (AREA)
Birds (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Cosmetics (AREA)
Hydrogenated Pyridines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Compositions Of Macromolecular Compounds (AREA)
Paints Or Removers (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

IL9348590A 1989-02-23 1990-02-21 Tetrahydropyridines process for their preparation intermediates therefor compositions containing them and process for use of such compositions IL93485A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
AUPJ289189		1989-02-23
AUPJ289289		1989-02-23

Publications (1)

Publication Number	Publication Date
IL93485A true IL93485A (en)	1996-01-19

Family

ID=25643635

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9348590A IL93485A (en)	1989-02-23	1990-02-21	Tetrahydropyridines process for their preparation intermediates therefor compositions containing them and process for use of such compositions

Country Status (14)

Country	Link
EP (1)	EP0462123B1 (de)
JP (1)	JP2975106B2 (de)
AR (1)	AR246735A1 (de)
AT (1)	ATE158575T1 (de)
AU (1)	AU653495B2 (de)
CA (1)	CA2027542C (de)
DE (1)	DE69031493T2 (de)
DK (1)	DK0462123T3 (de)
ES (1)	ES2108691T3 (de)
GR (1)	GR900100129A (de)
IL (1)	IL93485A (de)
NZ (1)	NZ232660A (de)
WO (1)	WO1990009995A1 (de)
ZA (1)	ZA901410B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2295389B (en) *	1994-11-25	1998-01-21	Zeneca Ltd	Halogenated acids and esters useful as intermediates for insecticides
IL115833A (en) *	1994-11-25	1998-10-27	Zeneca Ltd	6,6-Dihalo-3,3-dimethyl-5-hydroxy-7,7,7-trifluoroheptanoic acids and their alkyl esters useful as intermediates for insecticides and their preparation
US10519111B2 (en)	2013-07-15	2019-12-31	Coral Sunscreen Pty Ltd	UV absorbing compounds, compositions comprising same and uses thereof
CA2918065C (en) *	2013-07-15	2021-09-14	Coral Sunscreen Pty Ltd	Uv absorbing 1,2,3,4-tetrahydropyridine compounds, compositions comprising same and uses thereof
AU2016329044B2 (en) *	2015-11-27	2021-06-03	Commonwealth Scientific And Industrial Research Organisation	Photostable compounds, absorbing compounds and uses thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1988002251A1 (en) *	1986-09-26	1988-04-07	Ici Australia Operations Proprietary Limited	Sunscreen compositions and compounds for use therein

1990
- 1990-02-20 GR GR900100129A patent/GR900100129A/el not_active IP Right Cessation
- 1990-02-21 IL IL9348590A patent/IL93485A/en not_active IP Right Cessation
- 1990-02-22 AR AR90316223A patent/AR246735A1/es active
- 1990-02-23 EP EP90903716A patent/EP0462123B1/de not_active Expired - Lifetime
- 1990-02-23 ZA ZA901410A patent/ZA901410B/xx unknown
- 1990-02-23 WO PCT/AU1990/000078 patent/WO1990009995A1/en not_active Ceased
- 1990-02-23 AU AU51745/90A patent/AU653495B2/en not_active Ceased
- 1990-02-23 ES ES90903716T patent/ES2108691T3/es not_active Expired - Lifetime
- 1990-02-23 JP JP2503847A patent/JP2975106B2/ja not_active Expired - Fee Related
- 1990-02-23 DE DE69031493T patent/DE69031493T2/de not_active Expired - Fee Related
- 1990-02-23 CA CA002027542A patent/CA2027542C/en not_active Expired - Lifetime
- 1990-02-23 DK DK90903716.0T patent/DK0462123T3/da not_active Application Discontinuation
- 1990-02-23 AT AT90903716T patent/ATE158575T1/de not_active IP Right Cessation
- 1990-02-23 NZ NZ232660A patent/NZ232660A/xx unknown

Also Published As

Publication number	Publication date
AU653495B2 (en)	1994-10-06
NZ232660A (en)	1993-03-26
EP0462123A1 (de)	1991-12-27
WO1990009995A1 (en)	1990-09-07
ES2108691T3 (es)	1998-01-01
CA2027542A1 (en)	1990-08-24
GR900100129A (el)	1991-06-28
AR246735A1 (es)	1994-09-30
JP2975106B2 (ja)	1999-11-10
CA2027542C (en)	1999-12-14
DE69031493D1 (de)	1997-10-30
ZA901410B (en)	1990-12-28
AU5174590A (en)	1990-09-26
EP0462123B1 (de)	1997-09-24
EP0462123A4 (de)	1991-11-06
DK0462123T3 (da)	1998-03-30
JPH04505611A (ja)	1992-10-01
DE69031493T2 (de)	1998-03-19
ATE158575T1 (de)	1997-10-15

Legal Events

Date	Code	Title
1996-06-18	FF	Patent granted
1996-10-16	KB	Patent renewed
2004-03-28	KB	Patent renewed
2008-03-23	KB	Patent renewed
2010-12-30	EXP	Patent expired

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