CH618977A5 - - Google Patents

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Publication number: CH618977A5
Authority: CH; Switzerland
Prior art keywords: radical; carbon atoms; compound; formula; chain
Prior art date: 1974-11-30

Application number

CH168779A

Other languages

English (en)

French (fr)

Inventor

Roger Charles Brown

Richard Hazard

John Mann

Original Assignee

Fisons Ltd

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.)

1974-11-30

Filing date

1979-02-21

Publication date

1980-08-29

1974-11-30 Priority claimed from GB51944/74A external-priority patent/GB1517153A/en

1979-02-21 Application filed by Fisons Ltd filed Critical Fisons Ltd

1980-08-29 Publication of CH618977A5 publication Critical patent/CH618977A5/fr

Links

-1 alkyl radical Chemical class 0.000 claims description 57
150000001875 compounds Chemical class 0.000 claims description 53
125000004432 carbon atom Chemical group C* 0.000 claims description 32
150000003254 radicals Chemical class 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 14
125000005843 halogen group Chemical group 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
230000007062 hydrolysis Effects 0.000 claims description 7
238000006460 hydrolysis reaction Methods 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
239000000427 antigen Substances 0.000 claims description 6
102000036639 antigens Human genes 0.000 claims description 6
108091007433 antigens Proteins 0.000 claims description 6
208000006673 asthma Diseases 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
238000000034 method Methods 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
230000000144 pharmacologic effect Effects 0.000 claims description 4
238000012360 testing method Methods 0.000 claims description 4
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 claims description 3
201000009961 allergic asthma Diseases 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
210000003238 esophagus Anatomy 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
239000000843 powder Substances 0.000 claims description 2
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 claims 1
125000004990 dihydroxyalkyl group Chemical group 0.000 claims 1
239000002085 irritant Substances 0.000 claims 1
231100000021 irritant Toxicity 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
239000007787 solid Substances 0.000 description 17
239000000243 solution Substances 0.000 description 17
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
239000002253 acid Substances 0.000 description 15
239000000203 mixture Substances 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
239000002904 solvent Substances 0.000 description 10
239000000047 product Substances 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
238000010992 reflux Methods 0.000 description 7
238000007363 ring formation reaction Methods 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000002609 medium Substances 0.000 description 5
239000012071 phase Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
238000003756 stirring Methods 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
QFZTUWOWMRNMAH-UHFFFAOYSA-N 2h-pyran-2-carboxylic acid Chemical compound OC(=O)C1OC=CC=C1 QFZTUWOWMRNMAH-UHFFFAOYSA-N 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
150000003973 alkyl amines Chemical class 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
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 description 3
LZMUYDQAVFZRSL-UHFFFAOYSA-N 1-(3-hydroxy-4-propyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethanone Chemical compound C1CCCC2=C1C=C(C(C)=O)C(O)=C2CCC LZMUYDQAVFZRSL-UHFFFAOYSA-N 0.000 description 2
VFFTVZUIDYJUQS-UHFFFAOYSA-N 5-hydroxy-4-oxo-10-propyl-6,7,8,9-tetrahydrobenzo[g]chromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C(CCC)=C1CCCCC1=C2O VFFTVZUIDYJUQS-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
JMPLHIMPUGYSDQ-UHFFFAOYSA-M O1C(C=CC=C1)C(=O)[O-].[Na+] Chemical compound O1C(C=CC=C1)C(=O)[O-].[Na+] JMPLHIMPUGYSDQ-UHFFFAOYSA-M 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
125000003282 alkyl amino group Chemical group 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000011575 calcium Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
BFSWYEYFSYLMCV-UHFFFAOYSA-N ethyl 2H-pyran-2-carboxylate Chemical compound CCOC(=O)C1OC=CC=C1 BFSWYEYFSYLMCV-UHFFFAOYSA-N 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229910000042 hydrogen bromide Inorganic materials 0.000 description 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000000725 suspension Substances 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
LNZONKXKXBWZDQ-UHFFFAOYSA-N 1-(3-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)ethanone Chemical compound C1CCCC2=C1C=C(C(=O)C)C(O)=C2 LNZONKXKXBWZDQ-UHFFFAOYSA-N 0.000 description 1
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
DLKZWVIRKURGIR-UHFFFAOYSA-N 4-oxo-10-propyl-6,7,8,9-tetrahydrobenzo[g]chromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C(CCC)=C1CCCCC1=C2 DLKZWVIRKURGIR-UHFFFAOYSA-N 0.000 description 1
ASCHDAQPKVWZJM-UHFFFAOYSA-N 4H-benzo[g]chromene-2-carboxylic acid Chemical compound O1C2=C(CC=C1C(=O)O)C=C1C=CC=CC1=C2 ASCHDAQPKVWZJM-UHFFFAOYSA-N 0.000 description 1
SUMJHPMMFLYYPL-UHFFFAOYSA-N 5-hydroxy-4-oxo-10-propylbenzo[g]chromene-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C(CCC)=C1C=CC=CC1=C2O SUMJHPMMFLYYPL-UHFFFAOYSA-N 0.000 description 1
208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
206010003645 Atopy Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 1
208000004262 Food Hypersensitivity Diseases 0.000 description 1
206010016946 Food allergy Diseases 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
238000006898 Intramolecular Friedel-Crafts reaction Methods 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
208000009793 Milk Hypersensitivity Diseases 0.000 description 1
201000010859 Milk allergy Diseases 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
208000024780 Urticaria Diseases 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical class [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000004657 aryl sulfonyl amino group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000037396 body weight Effects 0.000 description 1
YTIVTFGABIZHHX-UHFFFAOYSA-N butynedioic acid Chemical compound OC(=O)C#CC(O)=O YTIVTFGABIZHHX-UHFFFAOYSA-N 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
PRDFCAIILADHDB-UHFFFAOYSA-N ethyl 4-oxo-10-propylbenzo[g]chromene-2-carboxylate Chemical compound O1C(C(=O)OCC)=CC(=O)C2=C1C(CCC)=C1C=CC=CC1=C2 PRDFCAIILADHDB-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
208000030533 eye disease Diseases 0.000 description 1
235000020932 food allergy Nutrition 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
201000005298 gastrointestinal allergy Diseases 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
238000000265 homogenisation 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
BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
201000001371 inclusion conjunctivitis Diseases 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
201000010659 intrinsic asthma Diseases 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000003901 oxalic acid esters Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
206010044325 trachoma Diseases 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/74—Benzo[b]pyrans, hydrogenated in the carbocyclic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrane Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CH168779A 1974-11-30 1979-02-21 CH618977A5 (de)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB51944/74A GB1517153A (en)	1974-11-30	1974-11-30	Naphthopyran-and benzodipyran-2-carboxylic acids and derivatives thereof
GB5370474		1974-12-12
GB2104475		1975-05-16
GB2104375		1975-05-16

Publications (1)

Publication Number	Publication Date
CH618977A5 true CH618977A5 (de)	1980-08-29

Family

ID=27448513

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH1551875A CH615171A5 (de)	1974-11-30	1975-11-28
CH168779A CH618977A5 (de)	1974-11-30	1979-02-21

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
CH1551875A CH615171A5 (de)	1974-11-30	1975-11-28

Country Status (23)

Country	Link
US (1)	US4238606A (de)
JP (1)	JPS5176277A (de)
AR (2)	AR215120A1 (de)
AT (1)	AT351530B (de)
BR (1)	BR7507936A (de)
CA (1)	CA1065329A (de)
CH (2)	CH615171A5 (de)
DD (1)	DD124735A5 (de)
DE (1)	DE2553688A1 (de)
DK (1)	DK535175A (de)
ES (1)	ES443093A1 (de)
FI (1)	FI753369A (de)
FR (1)	FR2292468A1 (de)
HU (1)	HU175915B (de)
IE (1)	IE42068B1 (de)
IL (2)	IL48566A0 (de)
IT (1)	IT1059533B (de)
MX (1)	MX3391E (de)
NL (1)	NL7513918A (de)
NO (1)	NO145982C (de)
NZ (1)	NZ179392A (de)
SE (1)	SE420835B (de)
ZM (1)	ZM16775A1 (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1570993A (en) *	1976-05-21	1980-07-09	Fisons Ltd	Pharmaceutical tablet formulation
DE2819859A1 (de) *	1977-05-06	1978-11-09	Fisons Ltd	Tiermedizinisches behandlungsmittel und inhalationsvorrichtung fuer tiere
JPS5424895A (en) *	1977-07-28	1979-02-24	Eisai Co Ltd	Pyranochromone derivatives and remedies for allergic disorder
US4269854A (en) *	1978-09-12	1981-05-26	Fisons Limited	6,7,8,9-Tetrahydro-4H-naphtho-[2,3-b]pyran-2-carboxylic acids

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1023373A (en) *	1962-03-07	1966-03-23	Benger Lab Ltd	Chromone derivatives
US3291811A (en) *	1962-03-30	1966-12-13	Benger Lab Ltd	Cyclohexano [g] chromones substituted in 2-position by carboxyl or carboxymethyl-aminocarbonyl
GB1029213A (en) *	1966-04-02	1966-05-11	Benger Lab Ltd	Chromone derivatives
GB1024645A (en) *	1962-07-10	1966-03-30	Benger Lab Ltd	Chromone compounds
GB1049289A (en) *	1962-08-18	1966-11-23	Benger Lab Ltd	Chromone derivatives and pharmaceutical compositions containing them
GB1116562A (en) *	1964-09-05	1968-06-06	Fisons Pharmaceuticals Ltd	A pyranochromone carboxylic acid and derivatives
FR1481033A (fr) *	1964-09-25	1967-05-19	Fisons Pharmaceuticals Ltd	Procédé de préparation d'un nouveau dérivé de la chromone
GB1147976A (en) *	1965-12-21	1969-04-10	Fisons Pharmaceuticals Ltd	Chromone derivatives
GB1223690A (en) *	1967-10-17	1971-03-03	Fisons Pharmaceuticals Ltd	Substituted chromon-2-carboxylic acids
GB1291864A (en) *	1969-02-12	1972-10-04	Fisons Pharmaceuticals Ltd	Mono thiachromone-2-carboxylic acids
GB1389227A (en) *	1971-09-16	1975-04-03	Fisons Ltd	Chromone-2-carboxylic acid derivatives methods for their preparation and compositions containing them

1975
- 1975-11-27 AT AT900675A patent/AT351530B/de not_active IP Right Cessation
- 1975-11-27 DK DK535175A patent/DK535175A/da not_active Application Discontinuation
- 1975-11-27 CA CA240,751A patent/CA1065329A/en not_active Expired
- 1975-11-27 HU HU75FI608A patent/HU175915B/hu unknown
- 1975-11-27 FR FR7536301A patent/FR2292468A1/fr active Granted
- 1975-11-28 BR BR7507936A patent/BR7507936A/pt unknown
- 1975-11-28 NL NL7513918A patent/NL7513918A/xx not_active Application Discontinuation
- 1975-11-28 IE IE2592/75A patent/IE42068B1/en unknown
- 1975-11-28 AR AR261386A patent/AR215120A1/es active
- 1975-11-28 IT IT2980275A patent/IT1059533B/it active
- 1975-11-28 FI FI753369A patent/FI753369A/fi not_active Application Discontinuation
- 1975-11-28 SE SE7513446A patent/SE420835B/xx unknown
- 1975-11-28 IL IL48566A patent/IL48566A0/xx unknown
- 1975-11-28 CH CH1551875A patent/CH615171A5/fr not_active IP Right Cessation
- 1975-11-28 DE DE19752553688 patent/DE2553688A1/de not_active Ceased
- 1975-11-28 NZ NZ179392A patent/NZ179392A/xx unknown
- 1975-11-28 ZM ZM167/75A patent/ZM16775A1/xx unknown
- 1975-11-29 JP JP50141857A patent/JPS5176277A/ja active Pending
- 1975-11-29 ES ES75443093A patent/ES443093A1/es not_active Expired
- 1975-12-01 NO NO754040A patent/NO145982C/no unknown
- 1975-12-01 DD DD190622A patent/DD124735A5/xx unknown
- 1975-12-01 MX MX10005475U patent/MX3391E/es unknown
1976
- 1976-07-30 AR AR264144A patent/AR219058A1/es active
1979
- 1979-02-21 CH CH168779A patent/CH618977A5/fr not_active IP Right Cessation
- 1979-05-03 US US06/035,739 patent/US4238606A/en not_active Expired - Lifetime
1980
- 1980-08-12 IL IL60824A patent/IL60824A0/xx unknown

Also Published As

Publication number	Publication date
IE42068B1 (en)	1980-05-21
CH615171A5 (de)	1980-01-15
NO145982C (no)	1982-07-07
HU175915B (en)	1980-11-28
MX3391E (es)	1980-10-27
US4238606A (en)	1980-12-09
NL7513918A (nl)	1976-06-01
NZ179392A (en)	1978-04-03
BR7507936A (pt)	1976-08-31
NO754040L (de)	1976-06-01
IT1059533B (it)	1982-06-21
FR2292468B1 (de)	1978-12-01
IL60824A0 (en)	1980-10-26
AT351530B (de)	1979-07-25
ZM16775A1 (en)	1976-11-22
IE42068L (en)	1976-05-30
NO145982B (no)	1982-03-29
ATA900675A (de)	1979-01-15
IL48566A0 (en)	1976-01-30
DD124735A5 (de)	1977-03-09
JPS5176277A (de)	1976-07-01
FI753369A (de)	1976-05-31
CA1065329A (en)	1979-10-30
ES443093A1 (es)	1977-10-16
DE2553688A1 (de)	1976-06-10
AR219058A1 (es)	1980-07-31
AR215120A1 (es)	1979-09-14
SE420835B (sv)	1981-11-02
FR2292468A1 (fr)	1976-06-25
DK535175A (da)	1976-05-31
SE7513446L (sv)	1976-05-31

Publication	Publication Date	Title
EP0202164B1 (de)	1989-02-08	(Benzoyl-4-piperidino)-2-phenyl-1-alkanolderivate, ihre Herstellung und ihre Verwendung als Heilmittel
EP0506532A1 (de)	1992-09-30	Indolderivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
EP0463945A1 (de)	1992-01-02	Chalkonderivate, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen, die sie enthalten
FR2658513A1 (fr)	1991-08-23	Procede de preparation de l'acide cis-beta-phenylglycidique-(2r,3r).
EP0021940B1 (de)	1983-01-19	Aminoderivate von Benzothiazol, Verfahren zu ihrer Herstellung und ihre Anwendung in der Heilkunde
EP0239436B1 (de)	1990-06-20	Tricyclisches Derivat, nämlich 5-(3-Chloro-6-methyl-5,5-dioxo-6,11-dihydro-dibenzo[c,f] [1,2]-thiazepin-11-yl amino)-pentansäure, Verfahren zu seiner Herstellung und dieses enthaltende Arzneimittel
EP0533827B1 (de)	1994-08-24	Oxazolederivate, ihre herstellung und diese enthaltende pharmazeutischen zubereitungen
EP0366511A1 (de)	1990-05-02	Benzoxazolinon-Derivate, Verfahren zu deren Herstellung und pharmazeutische Zusammensetzungen, die sie enthalten
LU81676A1 (fr)	1981-04-17	Nouveaux derives d'aurones,leur procede de preparation et leur utilisation comme produits pharmaceutiques
FR2559488A1 (fr)	1985-08-16	Composes d'organogermanium a la fois hydrophiles et lipophiles et procede pour leur production
EP0418933A1 (de)	1991-03-27	Alkadienderivate, ihre Herstellungen und sie enthaltende Arzneimittel und Zwischenprodukte
CH618977A5 (de)	1980-08-29
CH630606A5 (en)	1982-06-30	Phenylamidine derivatives useful especially in therapeutics
EP0385848A1 (de)	1990-09-05	Benzoxazolinon-Derivate, Verfahren zu deren Herstellung und pharmazeutische Zusammensetzungen, die sie enthalten
EP0017543B1 (de)	1983-09-28	Benzothiazolderivate, Verfahren zu ihrer Herstellung und ihre therapeutischen Anwendungen
FR2637596A1 (fr)	1990-04-13	Methyl-4 ((aryl-4 piperazinyl-1)-2 ethyl)-5 thiazole et ses derives, leur procede de preparation et les medicaments en contenant
EP0487423A1 (de)	1992-05-27	Benzoselenazolinonderivate, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen die sie enthalten
CH622795A5 (de)	1981-04-30
CA2045849A1 (fr)	1991-12-30	Derives d'oxazolo pyridines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
CH615673A5 (de)	1980-02-15
CH644603A5 (en)	1984-08-15	Aurone derivatives and process for their preparation
BE897473A (fr)	1984-02-06	Nouveaux alcaloides de l'ergot de seigle leur preparation et leur utilisation comme medicaments
CH634071A5 (en)	1983-01-14	Therapeutically active pyranoquinolones
WO1992021664A1 (fr)	1992-12-10	Nouveaux derives de l'oxazole, leur preparation et les compositions qui les contiennent
FR2595359A1 (fr)	1987-09-11	Nouveaux derives du benzo(4, 5)cyclohepta(1,2-b)thiophene, leur preparation et leur utilisation comme medicaments

Legal Events

Date	Code	Title	Description
1983-07-29	PL	Patent ceased
2024-10-31	PL	Patent ceased