GB1449810A - Benzo-or naphtho-dipyran-di-n-tetrazolyl- -carboxamide derivative methods for their production and compositions containing them - Google Patents
Benzo-or naphtho-dipyran-di-n-tetrazolyl- -carboxamide derivative methods for their production and compositions containing themInfo
- Publication number
- GB1449810A GB1449810A GB3904673*[A GB3904673A GB1449810A GB 1449810 A GB1449810 A GB 1449810A GB 3904673 A GB3904673 A GB 3904673A GB 1449810 A GB1449810 A GB 1449810A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- hydrogen
- pairs
- further substituted
- attached
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000203 mixture Substances 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 14
- 150000001875 compounds Chemical class 0.000 abstract 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 7
- 239000001257 hydrogen Substances 0.000 abstract 7
- 229910052739 hydrogen Inorganic materials 0.000 abstract 7
- 150000002790 naphthalenes Chemical class 0.000 abstract 6
- 150000001555 benzenes Chemical class 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000002431 hydrogen Chemical class 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 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 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- -1 methoxy, ethoxy Chemical group 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 abstract 1
- 229960004418 trolamine Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
1449810 Benzo- or naphtho-dipyran-dicarboxamide derivatives FISONS Ltd 16 Nov 1973 [5 Dec 1972 17 Aug 1973 (2)] 55997/72 39046/73 and 39047/73 Heading C2C [Also in Division A5] Novel compounds I and their salts in which two chains of Formula XX (in which each pair of R 9 and R 10 may be different and each R 9 and R 10 are selected from hydrogen, C 1-6 alkyl C 2-6 alkenyl, phenyl, phenyl C 1-6 alkyl, C 2-6 alkanoyl or C 2-6 alkoxycarbonyl) are attached to two pairs of ortho positions on a benzene or naphthalene nucleus which may be further substituted are prepared by (1) replacing a group R 12 with hydrogen (by using a hydrogen halide, catalytic hydrogenation, sodium in liquid ammonia, basic conditions or reactive diamination) in a compound in which two chains of Formula XXd are attached respectively to two pairs of ortho positions on a benzene or naphthalene nucleus which may be further substituted or removing both groups R 12 from a corresponding compound in which R 10 = R 12 to form a compound I (R 10 = H) (2) cyclizing a compound in which two chains of Formula XXe are attached to two pairs of ortho positions of an optionally further substituted benzene or naphthalene nucleus (3) reacting a compound in which two chains are attached to two pairs of ortho positions of an optionally further substituted benzene or naphthelene nucleus or an acid halide, ester or mixed anhydride thereof with a compound of Formula IV to form a compound I (R 9 =H when R 10 =H) (4) cyclizing a compound in which two pairs of groups -OH and (in which Y is -OH or NL 1 L 2 in which L 1 and L 2 are hydrogen phenyl or C 1-6 alkyl or together form a saturated or unsaturated 4 or 5 membered alkylene chain) are attached to two pairs of ortho positions on an optionally further substituted benzene or naphthalene nucleus or (5) selectively dehydrogenating a compound in which two chains of Formula XXf are attached to two pairs of ortho positions on an optionally further substituted benzene or naphthalene nucleus and, if desired, converting a compound I to a salt thereof compounds I prepared are those of Formulµ In, Io and Ip in which R 9 is hydrogen or methyl, R 10 is hydrogen, methyl, allyl carbethoxy, acetyl or benzyl and Pa and Qa are selected from hydrogen, C 1-5 alkyl, allyl, hydroxyl, chlorine, bromine, methoxy, ethoxy, allyloxy benzyloxy, nitro and ethoxymethyl, salts of a compound In (in which Qa, R 9 and R 10 are hydrogen and Pa is methoxy) with lithium, sodium, potassium, calcium, diethanolamine, tri-ethanolamine, tris-hydroxy methyl-methylamine, morpholine and N-methyl glucamine are also prepared. Compounds I inhibit antigen-antibody reactions.
Priority Applications (21)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3904673*[A GB1449810A (en) | 1972-12-05 | 1973-08-17 | Benzo-or naphtho-dipyran-di-n-tetrazolyl- -carboxamide derivative methods for their production and compositions containing them |
| IE2129/73A IE38544B1 (en) | 1972-12-05 | 1973-11-23 | Benzo-or naphtho dipyran-di(n-tetrazolyl)-carboxamide derivatives methods for their production and compositions containing them |
| MW68/73*UA MW6873A1 (en) | 1972-12-05 | 1973-11-27 | Compounds |
| IL43709A IL43709A (en) | 1972-12-05 | 1973-11-27 | Dioxo benzodipyran-di-carboxamido tetrazole derivatives their production and pharmaceutical compositions containing them |
| CA186,982A CA1023366A (en) | 1972-12-05 | 1973-11-29 | Benzo- and naphtho-dipyran derivatives |
| AU63050/73A AU483221B2 (en) | 1972-12-05 | 1973-11-29 | Benzo-di-pyran derivatives |
| FR7342955A FR2208670B1 (en) | 1972-12-05 | 1973-12-03 | |
| HU73FI00000554A HU171578B (en) | 1972-12-05 | 1973-12-03 | Process for producing new n,n-comma above-ditetrazolyl derivatives of benzodipyrane-dicarboxamides |
| ES421132A ES421132A1 (en) | 1972-12-05 | 1973-12-04 | Benzo-or naphtho-dipyran-di-n-tetrazolyl- -carboxamide derivative methods for their production and compositions containing them |
| DE2360331A DE2360331A1 (en) | 1972-12-05 | 1973-12-04 | BENZO AND NAPHTHODIPYRAN DERIVATIVES AND PROCESS FOR THEIR PRODUCTION |
| PL1973167040A PL102530B1 (en) | 1972-12-05 | 1973-12-04 | METHOD OF MAKING NEW BENZODUPIRANOCARBOXYAMIDOTETRAZOL |
| CH1694773A CH593277A5 (en) | 1972-12-05 | 1973-12-04 | |
| LU68934A LU68934A1 (en) | 1972-12-05 | 1973-12-04 | |
| SE7316373A SE409205B (en) | 1972-12-05 | 1973-12-04 | PROCEDURE FOR THE PREPARATION OF CERTAIN STATED BENZOPYRANE CARBOXAMIDOTETRAZOLE COMPOUNDS |
| SU1977568A SU553934A3 (en) | 1972-12-05 | 1973-12-04 | Method for preparing benzodipyran derivatives or their salts |
| NO4629/73A NO141517C (en) | 1972-12-05 | 1973-12-04 | ANALOGUE PROCEDURE FOR THE PREPARATION OF THERAPEUTIC PREVENTING BENZODIPYRANE-CARBOXAMIDO-TETRAZOLE COMPOUNDS |
| NL7316658A NL7316658A (en) | 1972-12-05 | 1973-12-05 | |
| DD175118A DD109387A5 (en) | 1972-12-05 | 1973-12-05 | |
| JP48135465A JPS4993366A (en) | 1972-12-05 | 1973-12-05 | |
| US05/674,732 US4085115A (en) | 1972-12-05 | 1976-04-06 | Carboxamido tetrazoles |
| AR251356A AR210310A1 (en) | 1972-12-05 | 1976-12-04 | PROCEDURE FOR THE PRODUCTION OF BENZODIPYRAN CARBOXAMIDE TETRAZOLES |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5599772 | 1972-12-05 | ||
| GB3904673*[A GB1449810A (en) | 1972-12-05 | 1973-08-17 | Benzo-or naphtho-dipyran-di-n-tetrazolyl- -carboxamide derivative methods for their production and compositions containing them |
| GB3904773 | 1973-08-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1449810A true GB1449810A (en) | 1976-09-15 |
Family
ID=27259543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3904673*[A Expired GB1449810A (en) | 1972-12-05 | 1973-08-17 | Benzo-or naphtho-dipyran-di-n-tetrazolyl- -carboxamide derivative methods for their production and compositions containing them |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS4993366A (en) |
| AR (1) | AR210310A1 (en) |
| CH (1) | CH593277A5 (en) |
| DD (1) | DD109387A5 (en) |
| DE (1) | DE2360331A1 (en) |
| ES (1) | ES421132A1 (en) |
| FR (1) | FR2208670B1 (en) |
| GB (1) | GB1449810A (en) |
| IE (1) | IE38544B1 (en) |
| IL (1) | IL43709A (en) |
| LU (1) | LU68934A1 (en) |
| MW (1) | MW6873A1 (en) |
| NL (1) | NL7316658A (en) |
| NO (1) | NO141517C (en) |
| PL (1) | PL102530B1 (en) |
| SE (1) | SE409205B (en) |
| SU (1) | SU553934A3 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4792547A (en) * | 1985-12-26 | 1988-12-20 | Hokuriku Pharmaceutical Co., Ltd. | Pyrazine-2-carboxamide derivatives useful in treating allergic disease |
| CA2482711A1 (en) * | 2002-04-23 | 2003-11-06 | L'oreal | Cosmetic composition for promoting hair growth and/or preventing or delaying hair loss |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1354477A (en) * | 1970-04-02 | 1974-06-05 | Fisons Ltd | Benzo di and tri-pyrones |
| GB1321879A (en) * | 1970-12-30 | 1973-07-04 | Fisons Ltd | Di-carboxybenzopyrano-benzopyrans |
| BE789822A (en) * | 1971-10-08 | 1973-04-06 | Allen & Hanburys Ltd | NEW HETEROCYCLIC COMPOUNDS |
-
1973
- 1973-08-17 GB GB3904673*[A patent/GB1449810A/en not_active Expired
- 1973-11-23 IE IE2129/73A patent/IE38544B1/en unknown
- 1973-11-27 MW MW68/73*UA patent/MW6873A1/en unknown
- 1973-11-27 IL IL43709A patent/IL43709A/en unknown
- 1973-12-03 FR FR7342955A patent/FR2208670B1/fr not_active Expired
- 1973-12-04 DE DE2360331A patent/DE2360331A1/en not_active Withdrawn
- 1973-12-04 NO NO4629/73A patent/NO141517C/en unknown
- 1973-12-04 PL PL1973167040A patent/PL102530B1/en unknown
- 1973-12-04 ES ES421132A patent/ES421132A1/en not_active Expired
- 1973-12-04 LU LU68934A patent/LU68934A1/xx unknown
- 1973-12-04 SU SU1977568A patent/SU553934A3/en active
- 1973-12-04 CH CH1694773A patent/CH593277A5/xx not_active IP Right Cessation
- 1973-12-04 SE SE7316373A patent/SE409205B/en unknown
- 1973-12-05 JP JP48135465A patent/JPS4993366A/ja active Pending
- 1973-12-05 NL NL7316658A patent/NL7316658A/xx not_active Application Discontinuation
- 1973-12-05 DD DD175118A patent/DD109387A5/xx unknown
-
1976
- 1976-12-04 AR AR251356A patent/AR210310A1/en active
Also Published As
| Publication number | Publication date |
|---|---|
| IE38544L (en) | 1974-06-05 |
| AU6305073A (en) | 1975-05-29 |
| FR2208670B1 (en) | 1978-01-13 |
| PL102530B1 (en) | 1979-04-30 |
| IL43709A0 (en) | 1974-03-14 |
| SU553934A3 (en) | 1977-04-05 |
| LU68934A1 (en) | 1974-07-05 |
| IL43709A (en) | 1977-04-29 |
| DE2360331A1 (en) | 1974-06-06 |
| CH593277A5 (en) | 1977-11-30 |
| JPS4993366A (en) | 1974-09-05 |
| AR210310A1 (en) | 1977-07-29 |
| DD109387A5 (en) | 1974-11-05 |
| SE409205B (en) | 1979-08-06 |
| FR2208670A1 (en) | 1974-06-28 |
| NL7316658A (en) | 1974-06-07 |
| MW6873A1 (en) | 1974-07-10 |
| ES421132A1 (en) | 1976-04-16 |
| NO141517C (en) | 1980-03-26 |
| NO141517B (en) | 1979-12-17 |
| IE38544B1 (en) | 1978-04-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |