ES394830A1 - A PROCEDURE FOR THE PREPARATION OF 5-SULFAMYL-BENZOIC ACIDS REPLACED IN POSITION 2. - Google Patents
A PROCEDURE FOR THE PREPARATION OF 5-SULFAMYL-BENZOIC ACIDS REPLACED IN POSITION 2.Info
- Publication number
- ES394830A1 ES394830A1 ES394830A ES394830A ES394830A1 ES 394830 A1 ES394830 A1 ES 394830A1 ES 394830 A ES394830 A ES 394830A ES 394830 A ES394830 A ES 394830A ES 394830 A1 ES394830 A1 ES 394830A1
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- formula
- carbon atoms
- benzyl
- hydrogen
- 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
- 238000000034 method Methods 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 8
- -1 trifluomethyl Chemical group 0.000 abstract 7
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 2
- 125000001246 bromo group Chemical group Br* 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 125000003944 tolyl group Chemical group 0.000 abstract 2
- NAETXYOXMDYNLE-UHFFFAOYSA-N 3-sulfamoylbenzoic acid Chemical group NS(=O)(=O)C1=CC=CC(C(O)=O)=C1 NAETXYOXMDYNLE-UHFFFAOYSA-N 0.000 abstract 1
- JTSFIVQMXUDGAB-UHFFFAOYSA-N 4-thiomorpholin-4-ylmorpholine Chemical group C1COCCN1N1CCSCC1 JTSFIVQMXUDGAB-UHFFFAOYSA-N 0.000 abstract 1
- 238000007126 N-alkylation reaction Methods 0.000 abstract 1
- JDTPCYGRCOGGAB-UHFFFAOYSA-N O[Br]Cl Chemical compound O[Br]Cl JDTPCYGRCOGGAB-UHFFFAOYSA-N 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000004193 piperazinyl group Chemical group 0.000 abstract 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000005942 tetrahydropyridyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/96—Sulfur atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyrrole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A procedure for the preparation of 5-sulfamyl benzoic acids substituted in position 2, of the formula: ** (See formula) ** amides, lower alkyl esters and pharmaceutically acceptable salts thereof, in which formula A is hydrogen, lower alkyl, cycloalkyl of 5 to 8 carbon atoms, benzyl or phenyl; B is ** (See formula) ** where n has the value from 0 to 3; R2 and R3 are each hydrogen, chloro, bromo, alkyl or alkoxy of 1 to 4 carbon atoms, carboxy, trifluomethyl, phenyl, benzyl or benzyloxy; and W is fluorine; and when A is hydrogen or lower alkyl, B is also lower alkyl or cycloalkyl of 5 to 8 carbon atoms; and A and B, when taken together with the nitrogen atom to which they are attached, form a heterocyclic ring selected from the group consisting of morpholino, thiomorpholine, piperazinyl, hexamethylenimino, heptamethyleneimino, octamethyleneimino, 3-azabicyclo [3,2,2 ] nonanyl, tetrahydropyridyl or mono- and di-substituted derivatives of said heterocyclic rings; the aforementioned substituents being alkyl, alkyloxy or alkyloxyalkyl of 1 to 4 carbon atoms in each alkyl, hydroxy, chloro, bromo, trifluomethyl, phenyl, tolyl, benzyl, benzyloxy, chloromethyl hydroxymethyl group; or the heterocyclic ring is unsubstituted piperidino or mono- or di-substituted piperidino, the substituents being alkyl, alkyloxy or alkyloxyalkyl of 1 to 4 carbon atoms in each alkyl, hydroxy, chloro, bromine, trifluomethyl, oxo, phenyl tolyl group, benzyl, benzyloxy, benzyloxymethyl, chloromethyl or hydroxymethyl, characterized by reacting an amine of the formula ** (See formula) ** where A and B are as defined above, with a compound of the formula ** (See formula) ** where Hal is halogen and W is as defined above; and, if desired, a compound of formula I wherein A is hydrogen is converted to N-alkyl by N-alkylation. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7215670A | 1970-09-14 | 1970-09-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES394830A1 true ES394830A1 (en) | 1974-12-01 |
Family
ID=22105942
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES394830A Expired ES394830A1 (en) | 1970-09-14 | 1971-09-06 | A PROCEDURE FOR THE PREPARATION OF 5-SULFAMYL-BENZOIC ACIDS REPLACED IN POSITION 2. |
| ES421977A Expired ES421977A1 (en) | 1970-09-14 | 1974-01-02 | Substituted 5-sulphamylbenzoic acids |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES421977A Expired ES421977A1 (en) | 1970-09-14 | 1974-01-02 | Substituted 5-sulphamylbenzoic acids |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5512422B1 (en) |
| AT (1) | AT323187B (en) |
| AU (1) | AU468590B2 (en) |
| BE (1) | BE772381A (en) |
| CA (1) | CA983489A (en) |
| CH (2) | CH552575A (en) |
| ES (2) | ES394830A1 (en) |
| FR (1) | FR2106514B1 (en) |
| GB (1) | GB1353357A (en) |
| KE (1) | KE2573A (en) |
| MY (1) | MY7500253A (en) |
| NL (1) | NL173400C (en) |
| SE (1) | SE401673B (en) |
| ZA (1) | ZA715851B (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3929803A (en) * | 1974-05-28 | 1975-12-30 | Pfizer | Aryl carboxylic acids |
| EP0068408A1 (en) * | 1980-11-10 | 1983-01-05 | Mochida Pharmaceutical Co., Ltd. | Antiviral compositions and a method for treating virus diseases |
| AU533742B2 (en) * | 1981-06-22 | 1983-12-08 | Mochida Pharmaceutical Co., Ltd. | Antiviral compositions |
| EP0068407A1 (en) * | 1981-06-22 | 1983-01-05 | Hodogaya Chemical Co., Ltd. | Aminosulfonylbenzoic acid derivatives |
| JPS58192863A (en) * | 1982-05-06 | 1983-11-10 | Hodogaya Chem Co Ltd | Novel aminosulfonylbenzoic acid ester derivative |
| JPS6323210U (en) * | 1986-07-31 | 1988-02-16 | ||
| DE3732374A1 (en) * | 1987-09-25 | 1989-04-06 | Basf Lacke & Farben | ZINC, LEAD AND / OR CALCIUM SALTS OF CARBONIC ACIDS AND THE USE THEREOF AS A CORROSION PROTECT |
| JPH0248510U (en) * | 1988-09-28 | 1990-04-04 | ||
| IL148148A0 (en) * | 1999-09-01 | 2002-09-12 | Aventis Pharma Gmbh | Sulfonyl carboxamide derivatives, method for their production and their use as medicaments |
| DE19941559A1 (en) * | 1999-09-01 | 2001-03-15 | Aventis Pharma Gmbh | Use of bissulfonamides for the preparation of medicaments for the prophylaxis or treatment of hyperlipidemia |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH433378A (en) * | 1962-03-09 | 1967-04-15 | Ciba Geigy | Process for the production of new anthranilic acid derivatives |
| FR1525352A (en) * | 1967-04-06 | 1968-05-17 | Ile De France | Process for preparing 2-alkoxy-5-sulfamido-benzoic acids |
-
1971
- 1971-04-19 GB GB2654071*A patent/GB1353357A/en not_active Expired
- 1971-08-31 CA CA121,776A patent/CA983489A/en not_active Expired
- 1971-09-01 ZA ZA715851A patent/ZA715851B/en unknown
- 1971-09-03 AU AU33084/71A patent/AU468590B2/en not_active Expired
- 1971-09-06 ES ES394830A patent/ES394830A1/en not_active Expired
- 1971-09-09 BE BE772381A patent/BE772381A/en not_active IP Right Cessation
- 1971-09-13 CH CH1338771A patent/CH552575A/en not_active IP Right Cessation
- 1971-09-13 AT AT793171A patent/AT323187B/en not_active IP Right Cessation
- 1971-09-13 CH CH128873A patent/CH569706A5/xx not_active IP Right Cessation
- 1971-09-13 SE SE7111587A patent/SE401673B/en unknown
- 1971-09-14 JP JP7163471A patent/JPS5512422B1/ja active Pending
- 1971-09-14 NL NLAANVRAGE7112598,A patent/NL173400C/en not_active IP Right Cessation
- 1971-09-14 FR FR7133085A patent/FR2106514B1/fr not_active Expired
-
1973
- 1973-10-15 KE KE2573*UA patent/KE2573A/en unknown
-
1974
- 1974-01-02 ES ES421977A patent/ES421977A1/en not_active Expired
-
1975
- 1975-12-30 MY MY253/75A patent/MY7500253A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2106514B1 (en) | 1975-08-01 |
| NL173400C (en) | 1984-01-16 |
| ZA715851B (en) | 1972-05-31 |
| AU468590B2 (en) | 1976-01-15 |
| CH552575A (en) | 1974-08-15 |
| NL173400B (en) | 1983-08-16 |
| AT323187B (en) | 1975-06-25 |
| BE772381A (en) | 1972-03-09 |
| MY7500253A (en) | 1975-12-31 |
| DE2145686A1 (en) | 1972-04-20 |
| JPS5512422B1 (en) | 1980-04-02 |
| NL7112598A (en) | 1972-03-16 |
| ES421977A1 (en) | 1976-05-01 |
| CA983489A (en) | 1976-02-10 |
| GB1353357A (en) | 1974-05-15 |
| CH569706A5 (en) | 1975-11-28 |
| DE2145686B2 (en) | 1977-07-07 |
| SE401673B (en) | 1978-05-22 |
| AU3308471A (en) | 1973-03-08 |
| KE2573A (en) | 1975-10-31 |
| FR2106514A1 (en) | 1972-05-05 |
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