GB1189719A - Aromatic Sulfamoyl Compounds - Google Patents
Aromatic Sulfamoyl CompoundsInfo
- Publication number
- GB1189719A GB1189719A GB5408567D GB5408567D GB1189719A GB 1189719 A GB1189719 A GB 1189719A GB 5408567 D GB5408567 D GB 5408567D GB 5408567 D GB5408567 D GB 5408567D GB 1189719 A GB1189719 A GB 1189719A
- Authority
- GB
- United Kingdom
- Prior art keywords
- resulting
- phenylsulphamoyl
- anthranilate
- chloro
- methyl
- 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
- 150000001875 compounds Chemical class 0.000 abstract 5
- 150000003839 salts Chemical class 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 4
- 125000001931 aliphatic group Chemical group 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 239000002934 diuretic Substances 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- AYHVYTXUGHRVMA-UHFFFAOYSA-N methyl 2-amino-4-chloro-5-(phenylsulfamoyl)benzoate Chemical compound ClC=1C=C(C(C(=O)OC)=CC1S(NC1=CC=CC=C1)(=O)=O)N AYHVYTXUGHRVMA-UHFFFAOYSA-N 0.000 abstract 2
- KTWCBPNVALETHA-UHFFFAOYSA-N 2,4-dichloro-5-(phenylsulfamoyl)benzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC(S(=O)(=O)NC=2C=CC=CC=2)=C1Cl KTWCBPNVALETHA-UHFFFAOYSA-N 0.000 abstract 1
- JRGAUAWPCLQHTF-UHFFFAOYSA-N 2-amino-5-sulfamoylbenzoic acid Chemical class NC1=CC=C(S(N)(=O)=O)C=C1C(O)=O JRGAUAWPCLQHTF-UHFFFAOYSA-N 0.000 abstract 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- 230000001882 diuretic effect Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- UXEXFEJDWBONPT-UHFFFAOYSA-N methyl 2-(2-benzylidenehydrazinyl)-4-chloro-5-(phenylsulfamoyl)benzoate Chemical compound C(C1=CC=CC=C1)=NNC=1C(C(=O)OC)=CC(=C(C1)Cl)S(NC1=CC=CC=C1)(=O)=O UXEXFEJDWBONPT-UHFFFAOYSA-N 0.000 abstract 1
- MZLITMFVGQBUQV-UHFFFAOYSA-N methyl 2-[benzyl(sulfamoyl)amino]-4-chloro-5-phenylbenzoate Chemical class C(C1=CC=CC=C1)N(C=1C(C(=O)OC)=CC(=C(C1)Cl)C1=CC=CC=C1)S(N)(=O)=O MZLITMFVGQBUQV-UHFFFAOYSA-N 0.000 abstract 1
- 230000001452 natriuretic effect Effects 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/42—Halides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,189,719. 5-Sulphamoylanthranilic acid derivatives. CIBA Ltd. 28 Nov., 1967 [5 Dec., 1966; 16 Oct., 1967], No. 54085/67. Heading C2C. Novel compounds I (including salts, esters and acyl derivatives thereof) wherein R 1 , R 2 and R 4 each signify a residue of aliphatic characteristics, an araliphatic residue or an aliphatic residue substituted by a heterocyclic group of aromatic characteristics, each of R 2 and R 4 also signify H and R 1 and R 2 when taken together also signify a bivalent residue of aliphatic characteristics, R 3 signifies Cl or Br and R 5 signifies an aromatic radical or a heterocyclic group of aromatic characteristics, and obtained by reacting a compound II (X signifies halogen) or an ester, an acid halide, an amide, a hydrazide or a salt thereof with an amine R 1 R 2 .NH and if desired converting any resulting amide or hydrazide into the free acid by hydrolysis, acylating a resulting compound having a hydroxy group or a primary or secondary amino group, hydrolysing a resulting acyl derivative or ester, and/or converting a resulting free acid into a salt or converting a resulting salt into the free acid or into another salt. Methyl N - benzylideneamino - 4 - chloro - 5 - phenylsulphamoyl-anthranilate, obtained by the interaction of methyl-4-chloro-5-phenylsulphamoyl-anthranilate (obtained by reacting 2,4- dichloro-5-phenylsulphamoyl-benzoic acid with ammonia) and benzaldehyde, is converted to a compound I by hydrogenation; this compound, methyl N - benzyl - 4 - chloro - 5 - phenyl - sulphamoyl-anthranilate, is also prepared by reacting benzyl chloride with methyl 4-chloro- 5-phenylsulphamoyl-anthranilate. Pharmaceutical preparations showing, in particular, diuretic, natriuretic and chloriuretic effects contain as active ingredient compounds I; administration is, e.g. orally and parenterally.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59898066A | 1966-12-05 | 1966-12-05 | |
| US67533067A | 1967-10-16 | 1967-10-16 | |
| DEF0054085 | 1967-11-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1189719A true GB1189719A (en) | 1970-04-29 |
Family
ID=27210549
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5408567D Expired GB1189719A (en) | 1966-12-05 | 1967-11-28 | Aromatic Sulfamoyl Compounds |
| GB3017469A Expired GB1189720A (en) | 1966-12-05 | 1967-11-28 | Aromatic Sulfamoyl Compounds |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3017469A Expired GB1189720A (en) | 1966-12-05 | 1967-11-28 | Aromatic Sulfamoyl Compounds |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT290499B (en) |
| BE (1) | BE707524A (en) |
| CH (1) | CH504416A (en) |
| DE (1) | DE1643279A1 (en) |
| FR (3) | FR1575550A (en) |
| GB (2) | GB1189719A (en) |
| NL (1) | NL6716492A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000027820A1 (en) * | 1998-11-10 | 2000-05-18 | Novartis Ag | N-aryl(thio)anthranilic acid amide derivatives, their preparation and their use as vegf receptor tyrosine kinase inhibitors |
| US8481564B2 (en) | 2006-04-20 | 2013-07-09 | Janssen Pharmaceutica, N.V. | Inhibitors of c-fms kinase |
| US8497376B2 (en) | 2007-10-17 | 2013-07-30 | Janssen Pharmaceutica N.V. | Inhibitors of c-fms kinase |
| US8557847B2 (en) | 2005-06-10 | 2013-10-15 | Janssen Pharmaceutica, N.V. | Synergistic modulation of FLT3 kinase using a FLT3 inhibitor and a farnesyl transferase inhibitor |
| US8697716B2 (en) | 2006-04-20 | 2014-04-15 | Janssen Pharmaceutica Nv | Method of inhibiting C-KIT kinase |
| US8722718B2 (en) | 2006-04-20 | 2014-05-13 | Janssen Pharmaceutica Nv | Inhibitors of C-FMS kinase |
| US9029352B2 (en) | 2012-08-07 | 2015-05-12 | Janssen Pharmaceutica Nv | Process for the preparation of C-FMS kinase inhibitors |
| US9303046B2 (en) | 2012-08-07 | 2016-04-05 | Janssen Pharmaceutica Nv | Process for the preparation of heterocyclic ester derivatives |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6284923B1 (en) * | 1997-08-22 | 2001-09-04 | Tularik Inc | Substituted benzene compounds as antiproliferative and cholesterol lowering action |
| ATE248845T1 (en) | 1998-06-25 | 2003-09-15 | Tularik Inc | ARYLSULFONANILIDE PHOSPHATES |
| US6153585A (en) | 1998-07-20 | 2000-11-28 | Tularik Inc. | Arylsulfonanilide derivatives |
| PL198394B1 (en) | 1998-09-23 | 2008-06-30 | Amgen Inc | Arylsulfonanilide ureas |
| AU2002234165A1 (en) | 2000-11-03 | 2002-05-27 | Tularik, Inc. | Combination therapy using pentafluorobenzenesulfonamides and antineoplastic agents |
| DE10112040A1 (en) * | 2001-03-14 | 2002-10-02 | Aventis Pharma Gmbh | Improved process for the preparation of sulfonylcarboxamide derivatives |
-
1967
- 1967-11-20 CH CH1621767A patent/CH504416A/en not_active IP Right Cessation
- 1967-11-28 GB GB5408567D patent/GB1189719A/en not_active Expired
- 1967-11-28 GB GB3017469A patent/GB1189720A/en not_active Expired
- 1967-11-30 DE DE19671643279 patent/DE1643279A1/en active Pending
- 1967-12-04 BE BE707524D patent/BE707524A/xx unknown
- 1967-12-04 AT AT1095767A patent/AT290499B/en not_active IP Right Cessation
- 1967-12-04 FR FR1575550D patent/FR1575550A/fr not_active Expired
- 1967-12-04 NL NL6716492A patent/NL6716492A/xx unknown
-
1968
- 1968-02-29 FR FR141757A patent/FR7837M/fr not_active Expired
- 1968-02-29 FR FR141758A patent/FR7838M/fr not_active Expired
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6448277B2 (en) | 1998-11-10 | 2002-09-10 | Novartis Ag | VEGF receptor tyrosine kinase inhibitors |
| US6878720B2 (en) | 1998-11-10 | 2005-04-12 | Novartis Ag | VEGF receptor tyrosine kinase inhibitors |
| US7002022B2 (en) | 1998-11-10 | 2006-02-21 | Novartis Ag | N-Aryl (thio) anthranilic acid amide derivatives, their preparation and their use as VEGF |
| CZ299829B6 (en) * | 1998-11-10 | 2008-12-10 | Novartis Ag | Derivatives of N-aryl(thio)anthranilic acid amides, process of their preparation and pharmaceutical compositions in which the derivatives are comprised |
| WO2000027820A1 (en) * | 1998-11-10 | 2000-05-18 | Novartis Ag | N-aryl(thio)anthranilic acid amide derivatives, their preparation and their use as vegf receptor tyrosine kinase inhibitors |
| US8557847B2 (en) | 2005-06-10 | 2013-10-15 | Janssen Pharmaceutica, N.V. | Synergistic modulation of FLT3 kinase using a FLT3 inhibitor and a farnesyl transferase inhibitor |
| US8759347B2 (en) | 2006-04-20 | 2014-06-24 | Janssen Pharmaceutica Nv | Inhibitors of C-FMS kinase |
| US8895584B2 (en) | 2006-04-20 | 2014-11-25 | Janssen Pharmaceutica Nv | Inhibitors of c-fms kinase |
| US8697716B2 (en) | 2006-04-20 | 2014-04-15 | Janssen Pharmaceutica Nv | Method of inhibiting C-KIT kinase |
| US8722718B2 (en) | 2006-04-20 | 2014-05-13 | Janssen Pharmaceutica Nv | Inhibitors of C-FMS kinase |
| US8481564B2 (en) | 2006-04-20 | 2013-07-09 | Janssen Pharmaceutica, N.V. | Inhibitors of c-fms kinase |
| US8815867B2 (en) | 2006-04-20 | 2014-08-26 | Janssen Pharmaceutica Nv | Inhibitors of c-fms kinase |
| US8859602B2 (en) | 2006-04-20 | 2014-10-14 | Janssen Pharmaceutica Nv | Inhibitors of c-fms kinase |
| US9526731B2 (en) | 2006-04-20 | 2016-12-27 | Janssen Pharmaceutica Nv | Method of inhibiting C-KIT kinase |
| US8933091B2 (en) | 2006-04-20 | 2015-01-13 | Janssen Pharmaceutica Nv | Method of inhibiting C-KIT kinase |
| US9403804B2 (en) | 2006-04-20 | 2016-08-02 | Janssen Pharmaceutica Nv | Inhibitors of c-fms kinase |
| US9266866B2 (en) | 2006-04-20 | 2016-02-23 | Janssen Pharmaceutica Nv | Inhibitors of C-FMS kinase |
| US9296726B2 (en) | 2006-04-20 | 2016-03-29 | Janssen Pharmaceutica Nv | Inhibitors of c-fms kinase |
| US9394289B2 (en) | 2006-04-20 | 2016-07-19 | Janssen Pharmaceutica Nv | Inhibitors of c-fms kinase |
| US8497376B2 (en) | 2007-10-17 | 2013-07-30 | Janssen Pharmaceutica N.V. | Inhibitors of c-fms kinase |
| US9303046B2 (en) | 2012-08-07 | 2016-04-05 | Janssen Pharmaceutica Nv | Process for the preparation of heterocyclic ester derivatives |
| US9029352B2 (en) | 2012-08-07 | 2015-05-12 | Janssen Pharmaceutica Nv | Process for the preparation of C-FMS kinase inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6716492A (en) | 1968-06-06 |
| BE707524A (en) | 1968-06-04 |
| CH504416A (en) | 1971-03-15 |
| FR7838M (en) | 1970-05-25 |
| FR7837M (en) | 1970-05-25 |
| DE1643279A1 (en) | 1971-06-09 |
| AT290499B (en) | 1971-06-11 |
| FR1575550A (en) | 1969-07-25 |
| GB1189720A (en) | 1970-04-29 |
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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 |