CH626613A5 - Process for the preparation of polycyclic compounds containing at least one tetrazole ring - Google Patents

Process for the preparation of polycyclic compounds containing at least one tetrazole ring Download PDF

Info

Publication number: CH626613A5
Authority: CH; Switzerland
Prior art keywords: group; formula; tetrazolyl; compounds; preparation
Prior art date: 1972-09-06

Application number

CH1282573A

Other languages

German (de)

English (en)

Inventor

Harold Francis Hodson

John Frederick Batchelor

John Henry Gorvin

Original Assignee

Wellcome Found

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.)

1972-09-06

Filing date

1973-09-06

Publication date

1981-11-30

1973-09-06 Application filed by Wellcome Found filed Critical Wellcome Found

1981-11-30 Publication of CH626613A5 publication Critical patent/CH626613A5/de

Links

238000002360 preparation method Methods 0.000 title description 54
238000000034 method Methods 0.000 title description 36
125000003831 tetrazolyl group Chemical group 0.000 title description 22
125000003367 polycyclic group Chemical group 0.000 title description 4
150000001875 compounds Chemical class 0.000 description 64
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 54
-1 5-tetrazolyl group Chemical group 0.000 description 31
125000004432 carbon atom Chemical group C* 0.000 description 28
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
125000000217 alkyl group Chemical group 0.000 description 26
150000003839 salts Chemical class 0.000 description 26
239000000203 mixture Substances 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 23
229910052739 hydrogen Inorganic materials 0.000 description 19
239000001257 hydrogen Substances 0.000 description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 description 19
238000002844 melting Methods 0.000 description 18
230000008018 melting Effects 0.000 description 18
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 18
239000004480 active ingredient Substances 0.000 description 17
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 17
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 14
150000001408 amides Chemical class 0.000 description 13
239000007787 solid Substances 0.000 description 13
239000002253 acid Substances 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
208000006673 asthma Diseases 0.000 description 8
239000000843 powder Substances 0.000 description 8
GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 description 7
FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 7
235000019270 ammonium chloride Nutrition 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
239000007788 liquid Substances 0.000 description 7
239000002245 particle Substances 0.000 description 7
IODRBNIMEDITMK-UHFFFAOYSA-N 2,7-bis(2h-tetrazol-5-yl)fluoren-1-one Chemical compound O=C1C2=CC3=CC(C4=NNN=N4)=CC=C3C2=CC=C1C=1N=NNN=1 IODRBNIMEDITMK-UHFFFAOYSA-N 0.000 description 6
125000003277 amino group Chemical group 0.000 description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
229910052760 oxygen Inorganic materials 0.000 description 6
239000001301 oxygen Substances 0.000 description 6
150000003536 tetrazoles Chemical group 0.000 description 6
UHWCYQDITWHFGT-UHFFFAOYSA-N 2,6-bis(2h-tetrazol-5-yl)anthracene-9,10-dione Chemical compound C1=C2C(=O)C3=CC=C(C=4NN=NN=4)C=C3C(=O)C2=CC=C1C1=NN=NN1 UHWCYQDITWHFGT-UHFFFAOYSA-N 0.000 description 5
125000003545 alkoxy group Chemical group 0.000 description 5
230000032050 esterification Effects 0.000 description 5
238000005886 esterification reaction Methods 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
150000002367 halogens Chemical class 0.000 description 5
239000000825 pharmaceutical preparation Substances 0.000 description 5
238000011282 treatment Methods 0.000 description 5
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 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
241000124008 Mammalia Species 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000000427 antigen Substances 0.000 description 4
102000036639 antigens Human genes 0.000 description 4
108091007433 antigens Proteins 0.000 description 4
230000037396 body weight Effects 0.000 description 4
150000001768 cations Chemical class 0.000 description 4
238000002955 isolation Methods 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
230000002685 pulmonary effect Effects 0.000 description 4
238000003756 stirring Methods 0.000 description 4
DGKVMJQDSWOYHS-UHFFFAOYSA-N 1-oxofluorene-2,7-dicarbonitrile Chemical compound N#CC1=CC=C2C3=CC=C(C#N)C(=O)C3=CC2=C1 DGKVMJQDSWOYHS-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
239000004604 Blowing Agent Substances 0.000 description 3
206010020751 Hypersensitivity Diseases 0.000 description 3
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 3
238000000297 Sandmeyer reaction Methods 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
201000009961 allergic asthma Diseases 0.000 description 3
230000009435 amidation Effects 0.000 description 3
238000007112 amidation reaction Methods 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
208000010668 atopic eczema Diseases 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000005457 ice water Substances 0.000 description 3
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
210000000214 mouth Anatomy 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
239000002243 precursor Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
238000010992 reflux Methods 0.000 description 3
210000003491 skin Anatomy 0.000 description 3
239000000725 suspension Substances 0.000 description 3
YHLYBBOFJOIABI-UHFFFAOYSA-N 9,10-dioxoanthracene-2,6-dicarbonitrile Chemical compound C1=C(C#N)C=C2C(=O)C3=CC=C(C#N)C=C3C(=O)C2=C1 YHLYBBOFJOIABI-UHFFFAOYSA-N 0.000 description 2
GPYFZBLFFXRVPB-UHFFFAOYSA-N 9,10-dioxoanthracene-2,6-dicarboxamide Chemical compound NC(=O)C1=CC=C2C(=O)C3=CC(C(=O)N)=CC=C3C(=O)C2=C1 GPYFZBLFFXRVPB-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
229920000084 Gum arabic Polymers 0.000 description 2
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 2
229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
HGVNXEVNBBVJGZ-UHFFFAOYSA-N O1C2=C(N(C3=CC=CC=C13)C1=CC=C(C3=CC(C#N)=C(C#N)C=C3C3=CC=C(N4C5=CC=CC=C5OC5=C4C=CC=C5)C=C3)C=C1)C=CC=C2 Chemical compound O1C2=C(N(C3=CC=CC=C13)C1=CC=C(C3=CC(C#N)=C(C#N)C=C3C3=CC=C(N4C5=CC=CC=C5OC5=C4C=CC=C5)C=C3)C=C1)C=CC=C2 HGVNXEVNBBVJGZ-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
206010039085 Rhinitis allergic Diseases 0.000 description 2
241000978776 Senegalia senegal Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
235000010489 acacia gum Nutrition 0.000 description 2
239000000205 acacia gum Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000013543 active substance Substances 0.000 description 2
UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
230000000172 allergic effect Effects 0.000 description 2
201000010105 allergic rhinitis Diseases 0.000 description 2
150000001409 amidines Chemical class 0.000 description 2
150000001411 amidrazones Chemical class 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229940124630 bronchodilator Drugs 0.000 description 2
239000002775 capsule Substances 0.000 description 2
125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000006184 cosolvent Substances 0.000 description 2
239000006071 cream Substances 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000006196 drop Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229960001340 histamine Drugs 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
239000007937 lozenge Substances 0.000 description 2
210000004072 lung Anatomy 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000009935 nitrosation Effects 0.000 description 2
238000007034 nitrosation reaction Methods 0.000 description 2
239000002674 ointment Substances 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
230000035945 sensitivity Effects 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
235000000346 sugar Nutrition 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 1
XNRNLOWBGVLOHG-UHFFFAOYSA-N 2,6-diaminoxanthen-9-one Chemical compound C1=C(N)C=C2C(=O)C3=CC=C(N)C=C3OC2=C1 XNRNLOWBGVLOHG-UHFFFAOYSA-N 0.000 description 1
FYEFHYMUEWRCRF-UHFFFAOYSA-N 2,7-dibromofluoren-1-one Chemical compound BrC1=CC=C2C3=CC=C(Br)C(=O)C3=CC2=C1 FYEFHYMUEWRCRF-UHFFFAOYSA-N 0.000 description 1
HQARDVLSJLCFBA-UHFFFAOYSA-N 4-[(4-aminophenyl)carbamoyl]-1h-imidazole-5-carboxylic acid Chemical compound C1=CC(N)=CC=C1NC(=O)C1=C(C(O)=O)NC=N1 HQARDVLSJLCFBA-UHFFFAOYSA-N 0.000 description 1
ZUTFCPOKQHJATC-UHFFFAOYSA-N 9,10-dioxoanthracene-2,6-dicarboxylic acid Chemical compound OC(=O)C1=CC=C2C(=O)C3=CC(C(=O)O)=CC=C3C(=O)C2=C1 ZUTFCPOKQHJATC-UHFFFAOYSA-N 0.000 description 1
XMIFYVJZYNTBTI-UHFFFAOYSA-N 9-oxofluorene-2,7-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=C2C(=O)C3=CC(C(=O)O)=CC=C3C2=C1 XMIFYVJZYNTBTI-UHFFFAOYSA-N 0.000 description 1
208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
206010027654 Allergic conditions Diseases 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
206010002198 Anaphylactic reaction Diseases 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 description 1
206010010741 Conjunctivitis Diseases 0.000 description 1
201000004624 Dermatitis Diseases 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
SOWBFZRMHSNYGE-UHFFFAOYSA-N Monoamide-Oxalic acid Natural products NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
206010040914 Skin reaction Diseases 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
208000024780 Urticaria Diseases 0.000 description 1
MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
MPLYYBPLRCQZDH-UHFFFAOYSA-N [Na].[Na].C1=CC=CC=2NC3=CC=CC=C3C(C12)=O Chemical compound [Na].[Na].C1=CC=CC=2NC3=CC=CC=C3C(C12)=O MPLYYBPLRCQZDH-UHFFFAOYSA-N 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
125000005599 alkyl carboxylate group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
230000007815 allergy Effects 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
230000002052 anaphylactic effect Effects 0.000 description 1
230000036783 anaphylactic response Effects 0.000 description 1
208000003455 anaphylaxis Diseases 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
230000003266 anti-allergic effect Effects 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000007860 aryl ester derivatives Chemical class 0.000 description 1
230000003385 bacteriostatic effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
206010006451 bronchitis Diseases 0.000 description 1
239000000168 bronchodilator agent Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
150000007942 carboxylates Chemical group 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 1
210000000038 chest Anatomy 0.000 description 1
239000000470 constituent Substances 0.000 description 1
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
208000024711 extrinsic asthma Diseases 0.000 description 1
239000003889 eye drop Substances 0.000 description 1
229940012356 eye drops Drugs 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
230000001408 fungistatic effect Effects 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
239000008241 heterogeneous mixture Substances 0.000 description 1
210000003630 histaminocyte Anatomy 0.000 description 1
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
150000002463 imidates Chemical class 0.000 description 1
150000002464 imidothioesters Chemical class 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
230000003993 interaction Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
201000010659 intrinsic asthma Diseases 0.000 description 1
229960001317 isoprenaline Drugs 0.000 description 1
239000006210 lotion Substances 0.000 description 1
MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
LMOINURANNBYCM-UHFFFAOYSA-N metaproterenol Chemical compound CC(C)NCC(O)C1=CC(O)=CC(O)=C1 LMOINURANNBYCM-UHFFFAOYSA-N 0.000 description 1
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
229940100662 nasal drops Drugs 0.000 description 1
239000006199 nebulizer Substances 0.000 description 1
239000007764 o/w emulsion Substances 0.000 description 1
229960002657 orciprenaline Drugs 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000001294 propane Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000035483 skin reaction Effects 0.000 description 1
231100000430 skin reaction Toxicity 0.000 description 1
229910001023 sodium amalgam Inorganic materials 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000004001 thioalkyl group Chemical group 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
239000007762 w/o emulsion Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
- C07D219/06—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
- C07D219/08—Nitrogen atoms
- 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
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes 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 in position 9
- C07D311/86—Oxygen atoms, e.g. xanthones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pulmonology (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrane Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

CH1282573A 1972-09-06 1973-09-06 Process for the preparation of polycyclic compounds containing at least one tetrazole ring CH626613A5 (en)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
GB4143172		1972-09-06
GB4143072		1972-09-06
GB4143272		1972-09-06
GB820073*[A GB1452891A (en)	1972-09-06	1973-02-20	Tricyclic tetrazole derivatives their synthesis and compositions containing them
GB829273		1973-02-20

Publications (1)

Publication Number	Publication Date
CH626613A5 true CH626613A5 (en)	1981-11-30

Family

ID=27515847

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1282573A CH626613A5 (en)	1972-09-06	1973-09-06	Process for the preparation of polycyclic compounds containing at least one tetrazole ring

Country Status (8)

Country	Link
JP (1)	JPS5849549B2 (2)
CH (1)	CH626613A5 (2)
DE (1)	DE2344814A1 (2)
FR (1)	FR2197606B1 (2)
GB (1)	GB1452891A (2)
IE (1)	IE38234B1 (2)
IL (1)	IL43160A (2)
NL (1)	NL7312282A (2)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4598155A (en) *	1981-11-18	1986-07-01	Ciba-Geigy Corporation	3(5-tetrazolyl)1,4-diaminoanthraquinones
US4714669A (en) *	1985-04-11	1987-12-22	Ciba-Geigy Corporation	Radiation-sensitive polycondensates, their preparation, material coated therewith and the use thereof
EP1444980A1 (en) *	2001-11-13	2004-08-11	Kyowa Hakko Kogyo Co., Ltd.	Preventive or remedy for pruritus

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE759292A (fr) *	1969-11-27	1971-05-24	Allen & Hanburys Ltd	Derives de xanthone, leur preparation et leur emploi
GB1339010A (en) *	1970-11-27	1973-11-28	Allen & Hanburys Ltd	Tetrazolyl-anthraquinone derivatives

1973
- 1973-02-20 GB GB820073*[A patent/GB1452891A/en not_active Expired
- 1973-09-05 IL IL43160A patent/IL43160A/en unknown
- 1973-09-05 DE DE19732344814 patent/DE2344814A1/de not_active Ceased
- 1973-09-05 JP JP48099387A patent/JPS5849549B2/ja not_active Expired
- 1973-09-06 CH CH1282573A patent/CH626613A5/de not_active IP Right Cessation
- 1973-09-06 IE IE1589/73A patent/IE38234B1/xx unknown
- 1973-09-06 NL NL7312282A patent/NL7312282A/xx not_active Application Discontinuation
- 1973-09-06 FR FR7332117A patent/FR2197606B1/fr not_active Expired

Also Published As

Publication number	Publication date
IL43160A0 (en)	1973-11-28
AU6003873A (en)	1975-03-06
JPS4985069A (2)	1974-08-15
DE2344814A1 (de)	1974-03-14
NL7312282A (2)	1974-03-08
JPS5849549B2 (ja)	1983-11-05
IL43160A (en)	1977-02-28
IE38234B1 (en)	1978-02-01
FR2197606A1 (2)	1974-03-29
IE38234L (en)	1974-03-06
FR2197606B1 (2)	1976-05-14
GB1452891A (en)	1976-10-20

Legal Events

Date	Code	Title	Description
1986-05-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE69522947T2 (de)	2002-04-11	Phenylxanthin-derivate
DE2557425C2 (de)	1987-03-19	11-Oxo-11-H-pyrido[2,1-b]-chinazolin-2-carbonsäure und ihre Salze, Verfahren zu ihrer Herstellung und Arzneimittel
EP0149242B1 (de)	1990-10-31	1-(2-Hydroxyaryl)-alkan-1-on-oxime, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln
DE2058295C3 (de)	1980-06-19	Xanthen-9-on-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
CH615152A5 (en)	1980-01-15	Process for the preparation of carboxylic acid amides and the carboxylic acid amides thus prepared
CH616423A5 (2)	1980-03-31
DE1795792A1 (de)	1975-06-19	Die serumlipoidkonzentration vermindernde arzneimittel
DE2164058C3 (de)	1981-08-13	Basisch substituierte Benzylphthalazinon-Derivate, ihre Salze, Verfahren zu ihrer Herstellung und diese Produkte enthaltende pharmazeutische Präparate
DE1645971B2 (de)	1974-08-22	(Indazol-3-y l)-oxy essigsäurederivate, Verfahren zu ihrer Herstellung und Mittel mit entzündungshemmender Wirkung
DE2931418A1 (de)	1980-02-28	Neue imidazochinoxaline und deren salze, verfahren zu deren herstellung, deren verwendung als arzneimittel und die sie enthaltenden pharmazeutischen zusammensetzungen
DE2536003C2 (de)	1985-11-14	Pyrazol-Derivate, ihre Herstellung und diese enthaltende pharmazeutische Derivate
AT371461B (de)	1983-06-27	Verfahren zur herstellung neuer benzopyranderivate und deren salze
DE2344799A1 (de)	1974-03-21	Schwefelhaltige tricyclische verbindungen und diese enthaltende arzneimittel
CH631973A5 (de)	1982-09-15	Verfahren zur herstellung von benzimidazolderivaten.
DE2319834C3 (de)	1983-02-03	Derivate von 2-Carboxy-pyrazin-4-oxiden, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen
CH630885A5 (en)	1982-07-15	Process for preparing tricyclic compounds, and the use of these compounds.
DE1960910A1 (de)	1970-07-09	Neue Benzylidenamino-oxyalkylcarbonsaeuren und Carbonsaeurederivate
DD140351A5 (de)	1980-02-27	Verfahren zur herstellung neuer 2-pyridyl-und 2-pyrimidylaminobenzoesaeuren
DE2253914A1 (de)	1973-05-10	Neue chromonderivate und verfahren zu ihrer herstellung
EP0643045B1 (de)	2000-03-08	Chinolin-Verbindungen als Leukotriene Antagonisten
AT390615B (de)	1990-06-11	Verfahren zur herstellung von neuen, 3-substituierten 2-oxo-hexahydro-pyrimido (1,2-a)azepinen sowie von deren pharmazeutisch geeigneten salzen
CH617432A5 (en)	1980-05-30	Process for the preparation of sulphur-containing heterotricyclic compounds
DE2344814A1 (de)	1974-03-14	Stickstoffhaltige heterocyclische verbindungen
AT374462B (de)	1984-04-25	Verfahren zur herstellung neuer benz-acylbenzimidazol-2-derivate und deren salze
DE2221281A1 (de)	1972-11-16	Pyrazolderivate und Verfahren zu ihrer Herstellung