NO327755B1 - Svovelsubstituerte sulfonylaminokarboksylsyre N-arylamider, deres fremstilling og anvendelse samt farmasoytiske preparater inneholdende forbindelsene - Google Patents
Svovelsubstituerte sulfonylaminokarboksylsyre N-arylamider, deres fremstilling og anvendelse samt farmasoytiske preparater inneholdende forbindelsene Download PDFInfo
- Publication number
- NO327755B1 NO327755B1 NO20010013A NO20010013A NO327755B1 NO 327755 B1 NO327755 B1 NO 327755B1 NO 20010013 A NO20010013 A NO 20010013A NO 20010013 A NO20010013 A NO 20010013A NO 327755 B1 NO327755 B1 NO 327755B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- chloro
- phenyl
- formula
- benzamide
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 115
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 10
- -1 Sulfur-substituted sulfonylaminocarboxylic acid Chemical class 0.000 title description 45
- 125000001424 substituent group Chemical group 0.000 claims description 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 238000002560 therapeutic procedure Methods 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
- 238000011321 prophylaxis Methods 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 7
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- 206010002383 Angina Pectoris Diseases 0.000 claims description 4
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- 206010020772 Hypertension Diseases 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 230000009467 reduction Effects 0.000 claims description 4
- WZHRJGWXUCLILI-UHFFFAOYSA-N sulfonylcarbamic acid Chemical compound OC(=O)N=S(=O)=O WZHRJGWXUCLILI-UHFFFAOYSA-N 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 3
- YFJKHTZXXMBJEW-UHFFFAOYSA-N 2-[(4-chlorophenyl)sulfonylamino]-4,5-dimethoxy-n-(4-thiomorpholin-4-ylsulfonylphenyl)benzamide Chemical group C=1C=C(S(=O)(=O)N2CCSCC2)C=CC=1NC(=O)C=1C=C(OC)C(OC)=CC=1NS(=O)(=O)C1=CC=C(Cl)C=C1 YFJKHTZXXMBJEW-UHFFFAOYSA-N 0.000 claims description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
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- 125000000524 functional group Chemical group 0.000 claims description 3
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- 239000002243 precursor Substances 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims description 2
- NDUZZUGMFXHNMT-UHFFFAOYSA-N 5-chloro-2-[(5-chlorothiophen-2-yl)sulfonylamino]-n-(4-morpholin-4-ylsulfonylphenyl)benzamide;sodium Chemical group [Na].S1C(Cl)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1C(=O)NC1=CC=C(S(=O)(=O)N2CCOCC2)C=C1 NDUZZUGMFXHNMT-UHFFFAOYSA-N 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
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- KRLMQTYZKFWKMJ-GASCZTMLSA-N 5-chloro-n-[4-[(2r,6s)-2,6-dimethylmorpholin-4-yl]sulfonylphenyl]-2-[(3,5-dimethyl-1,2-oxazol-4-yl)sulfonylamino]benzamide Chemical compound C1[C@@H](C)O[C@@H](C)CN1S(=O)(=O)C(C=C1)=CC=C1NC(=O)C1=CC(Cl)=CC=C1NS(=O)(=O)C1=C(C)ON=C1C KRLMQTYZKFWKMJ-GASCZTMLSA-N 0.000 claims 1
- 230000000747 cardiac effect Effects 0.000 claims 1
- FAQOZARUOBFXBH-UHFFFAOYSA-N nitroformamide Chemical compound NC(=O)[N+]([O-])=O FAQOZARUOBFXBH-UHFFFAOYSA-N 0.000 claims 1
- 159000000000 sodium salts Chemical group 0.000 claims 1
- 238000002844 melting Methods 0.000 description 147
- 230000008018 melting Effects 0.000 description 147
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- ZOOGRGPOEVQQDX-KHLHZJAASA-N cyclic guanosine monophosphate Chemical compound C([C@H]1O2)O[P@](O)(=O)O[C@@H]1[C@H](O)[C@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-KHLHZJAASA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- 102000007637 Soluble Guanylyl Cyclase Human genes 0.000 description 20
- 108010007205 Soluble Guanylyl Cyclase Proteins 0.000 description 20
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 16
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical group O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
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- 230000004913 activation Effects 0.000 description 11
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Classifications
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- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
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- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
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- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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DE19830430A DE19830430A1 (de) | 1998-07-08 | 1998-07-08 | Schwefelsubstituierte Sulfonylamino-carbonsäure-N-arylamide, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
DE19903126A DE19903126A1 (de) | 1999-01-27 | 1999-01-27 | Schwefelsubstituierte Sulfonylamino-carbonsäure-N-arylamide, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
PCT/EP1999/004426 WO2000002851A1 (en) | 1998-07-08 | 1999-06-25 | Sulfur substituted sulfonylaminocarboxylic acid n-arylamides, their preparation, their use and pharmaceutical preparations comprising them |
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NO20010013D0 NO20010013D0 (no) | 2001-01-02 |
NO20010013L NO20010013L (no) | 2001-03-01 |
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NO20010013A NO327755B1 (no) | 1998-07-08 | 2001-01-02 | Svovelsubstituerte sulfonylaminokarboksylsyre N-arylamider, deres fremstilling og anvendelse samt farmasoytiske preparater inneholdende forbindelsene |
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