AU717247B2 - Use of inhibitors of the cellular Na+/H+ exchanger (NHE) for the production of a medicament for respiratory stimulation - Google Patents
Use of inhibitors of the cellular Na+/H+ exchanger (NHE) for the production of a medicament for respiratory stimulation Download PDFInfo
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- AU717247B2 AU717247B2 AU13720/97A AU1372097A AU717247B2 AU 717247 B2 AU717247 B2 AU 717247B2 AU 13720/97 A AU13720/97 A AU 13720/97A AU 1372097 A AU1372097 A AU 1372097A AU 717247 B2 AU717247 B2 AU 717247B2
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- 239000003112 inhibitor Substances 0.000 title claims description 25
- 239000003814 drug Substances 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 239000003169 respiratory stimulant agent Substances 0.000 title description 3
- 230000001413 cellular effect Effects 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 788
- 239000001257 hydrogen Substances 0.000 claims description 723
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 525
- 125000001424 substituent group Chemical group 0.000 claims description 514
- 229910052731 fluorine Inorganic materials 0.000 claims description 492
- 125000004432 carbon atom Chemical group C* 0.000 claims description 439
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 406
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 386
- 125000000217 alkyl group Chemical group 0.000 claims description 348
- -1 chorine Chemical group 0.000 claims description 347
- 229910052760 oxygen Inorganic materials 0.000 claims description 301
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 297
- 239000001301 oxygen Substances 0.000 claims description 279
- 239000000460 chlorine Chemical group 0.000 claims description 274
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 273
- 229910052801 chlorine Inorganic materials 0.000 claims description 267
- 150000002431 hydrogen Chemical class 0.000 claims description 192
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 165
- 229910052717 sulfur Inorganic materials 0.000 claims description 157
- 229910052794 bromium Inorganic materials 0.000 claims description 136
- 150000003839 salts Chemical class 0.000 claims description 100
- 229910052799 carbon Inorganic materials 0.000 claims description 99
- 229910052740 iodine Inorganic materials 0.000 claims description 97
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 95
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 84
- 229910052757 nitrogen Inorganic materials 0.000 claims description 83
- 125000001624 naphthyl group Chemical group 0.000 claims description 79
- 150000003254 radicals Chemical class 0.000 claims description 73
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 66
- AJDQRQQNNLZLPM-UHFFFAOYSA-N n-(diaminomethylidene)benzamide Chemical class NC(N)=NC(=O)C1=CC=CC=C1 AJDQRQQNNLZLPM-UHFFFAOYSA-N 0.000 claims description 60
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 58
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 53
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 51
- 125000003342 alkenyl group Chemical group 0.000 claims description 48
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
- 235000001508 sulfur Nutrition 0.000 claims description 36
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 35
- 239000011593 sulfur Substances 0.000 claims description 35
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 34
- 150000001721 carbon Chemical group 0.000 claims description 34
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical group 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
- 125000004076 pyridyl group Chemical group 0.000 claims description 22
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 21
- 241001484259 Lacuna Species 0.000 claims description 20
- 125000002883 imidazolyl group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 239000011737 fluorine Substances 0.000 claims description 17
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 16
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 16
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 16
- 150000001409 amidines Chemical group 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 14
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 13
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 13
- 125000005493 quinolyl group Chemical group 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 12
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 11
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 11
- 125000004434 sulfur atom Chemical group 0.000 claims description 11
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 10
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 10
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 8
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 8
- 101100219382 Caenorhabditis elegans cah-2 gene Proteins 0.000 claims description 7
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 5
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 101001053263 Homo sapiens Insulin gene enhancer protein ISL-1 Proteins 0.000 claims description 3
- 102100024392 Insulin gene enhancer protein ISL-1 Human genes 0.000 claims description 3
- 125000005024 alkenyl aryl group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000005025 alkynylaryl group Chemical group 0.000 claims description 3
- FZOCFRPFPKJHHP-UHFFFAOYSA-N benzyl n-(diaminomethylidene)carbamate Chemical class NC(N)=NC(=O)OCC1=CC=CC=C1 FZOCFRPFPKJHHP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 229930016911 cinnamic acid Natural products 0.000 claims description 3
- 235000013985 cinnamic acid Nutrition 0.000 claims description 3
- 150000001851 cinnamic acid derivatives Chemical class 0.000 claims description 3
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 3
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 3
- 150000002357 guanidines Chemical class 0.000 claims description 3
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- WBCXYMNAMCHKSU-UHFFFAOYSA-N n-(diaminomethylidene)-1h-indene-1-carboxamide Chemical class C1=CC=C2C(C(=O)NC(=N)N)C=CC2=C1 WBCXYMNAMCHKSU-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
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- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 235000006629 Prosopis spicigera Nutrition 0.000 claims description 2
- 240000000037 Prosopis spicigera Species 0.000 claims description 2
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 2
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
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- XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical group COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 2
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- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
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- 238000009423 ventilation Methods 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
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- 235000013204 Crataegus X haemacarpa Nutrition 0.000 claims 1
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- LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
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- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 1
- XEHVFKKSDRMODV-UHFFFAOYSA-N ethynyl Chemical compound C#[C] XEHVFKKSDRMODV-UHFFFAOYSA-N 0.000 claims 1
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- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- QAKJXJZBXCVFLX-UHFFFAOYSA-N n-(diaminomethylidene)-1h-indole-2-carboxamide Chemical class C1=CC=C2NC(C(=O)N=C(N)N)=CC2=C1 QAKJXJZBXCVFLX-UHFFFAOYSA-N 0.000 claims 1
- 125000004957 naphthylene group Chemical group 0.000 claims 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
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- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
Classifications
-
- 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
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
-
- 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
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- 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
-
- 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
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60L—PROPULSION OF ELECTRICALLY-PROPELLED VEHICLES; SUPPLYING ELECTRIC POWER FOR AUXILIARY EQUIPMENT OF ELECTRICALLY-PROPELLED VEHICLES; ELECTRODYNAMIC BRAKE SYSTEMS FOR VEHICLES IN GENERAL; MAGNETIC SUSPENSION OR LEVITATION FOR VEHICLES; MONITORING OPERATING VARIABLES OF ELECTRICALLY-PROPELLED VEHICLES; ELECTRIC SAFETY DEVICES FOR ELECTRICALLY-PROPELLED VEHICLES
- B60L50/00—Electric propulsion with power supplied within the vehicle
- B60L50/50—Electric propulsion with power supplied within the vehicle using propulsion power supplied by batteries or fuel cells
- B60L50/60—Electric propulsion with power supplied within the vehicle using propulsion power supplied by batteries or fuel cells using power supplied by batteries
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60L—PROPULSION OF ELECTRICALLY-PROPELLED VEHICLES; SUPPLYING ELECTRIC POWER FOR AUXILIARY EQUIPMENT OF ELECTRICALLY-PROPELLED VEHICLES; ELECTRODYNAMIC BRAKE SYSTEMS FOR VEHICLES IN GENERAL; MAGNETIC SUSPENSION OR LEVITATION FOR VEHICLES; MONITORING OPERATING VARIABLES OF ELECTRICALLY-PROPELLED VEHICLES; ELECTRIC SAFETY DEVICES FOR ELECTRICALLY-PROPELLED VEHICLES
- B60L7/00—Electrodynamic brake systems for vehicles in general
- B60L7/10—Dynamic electric regenerative braking
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60L—PROPULSION OF ELECTRICALLY-PROPELLED VEHICLES; SUPPLYING ELECTRIC POWER FOR AUXILIARY EQUIPMENT OF ELECTRICALLY-PROPELLED VEHICLES; ELECTRODYNAMIC BRAKE SYSTEMS FOR VEHICLES IN GENERAL; MAGNETIC SUSPENSION OR LEVITATION FOR VEHICLES; MONITORING OPERATING VARIABLES OF ELECTRICALLY-PROPELLED VEHICLES; ELECTRIC SAFETY DEVICES FOR ELECTRICALLY-PROPELLED VEHICLES
- B60L7/00—Electrodynamic brake systems for vehicles in general
- B60L7/10—Dynamic electric regenerative braking
- B60L7/16—Dynamic electric regenerative braking for vehicles comprising converters between the power source and the motor
-
- E—FIXED CONSTRUCTIONS
- E01—CONSTRUCTION OF ROADS, RAILWAYS, OR BRIDGES
- E01C—CONSTRUCTION OF, OR SURFACES FOR, ROADS, SPORTS GROUNDS, OR THE LIKE; MACHINES OR AUXILIARY TOOLS FOR CONSTRUCTION OR REPAIR
- E01C19/00—Machines, tools or auxiliary devices for preparing or distributing paving materials, for working the placed materials, or for forming, consolidating, or finishing the paving
- E01C19/22—Machines, tools or auxiliary devices for preparing or distributing paving materials, for working the placed materials, or for forming, consolidating, or finishing the paving for consolidating or finishing laid-down unset materials
- E01C19/23—Rollers therefor; Such rollers usable also for compacting soil
- E01C19/26—Rollers therefor; Such rollers usable also for compacting soil self-propelled or fitted to road vehicles
-
- E—FIXED CONSTRUCTIONS
- E01—CONSTRUCTION OF ROADS, RAILWAYS, OR BRIDGES
- E01C—CONSTRUCTION OF, OR SURFACES FOR, ROADS, SPORTS GROUNDS, OR THE LIKE; MACHINES OR AUXILIARY TOOLS FOR CONSTRUCTION OR REPAIR
- E01C19/00—Machines, tools or auxiliary devices for preparing or distributing paving materials, for working the placed materials, or for forming, consolidating, or finishing the paving
- E01C19/22—Machines, tools or auxiliary devices for preparing or distributing paving materials, for working the placed materials, or for forming, consolidating, or finishing the paving for consolidating or finishing laid-down unset materials
- E01C19/23—Rollers therefor; Such rollers usable also for compacting soil
- E01C19/28—Vibrated rollers or rollers subjected to impacts, e.g. hammering blows
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Mechanical Engineering (AREA)
- Transportation (AREA)
- Power Engineering (AREA)
- Civil Engineering (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Sustainable Energy (AREA)
- Sustainable Development (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19548812A DE19548812A1 (de) | 1995-12-27 | 1995-12-27 | Verwendung von Inhibitoren des zellulären Na·+·/H·+·-Exchangers (NHE) zur Herstellung eines Medikaments zur Atemstimulation |
| DE19548812 | 1995-12-27 | ||
| PCT/EP1996/005614 WO1997024113A1 (de) | 1995-12-27 | 1996-12-13 | VERWENDUNG VON INHIBITOREN DES ZELLULÄREN Na+/H+-EXCHANGERS (NHE) ZUR HERSTELLUNG EINES MEDIKAMENTS ZUR ATEMSTIMULATION |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU1372097A AU1372097A (en) | 1997-07-28 |
| AU717247B2 true AU717247B2 (en) | 2000-03-23 |
Family
ID=7781474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU13720/97A Ceased AU717247B2 (en) | 1995-12-27 | 1996-12-13 | Use of inhibitors of the cellular Na+/H+ exchanger (NHE) for the production of a medicament for respiratory stimulation |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0869779A1 (cs) |
| KR (1) | KR19990076802A (cs) |
| CN (1) | CN1207676A (cs) |
| AU (1) | AU717247B2 (cs) |
| BR (1) | BR9612287A (cs) |
| CA (1) | CA2241531A1 (cs) |
| CZ (1) | CZ202198DA3 (cs) |
| DE (1) | DE19548812A1 (cs) |
| HU (1) | HUP9900807A3 (cs) |
| IL (1) | IL125114A0 (cs) |
| MX (1) | MX9805141A (cs) |
| NO (1) | NO982989L (cs) |
| PL (1) | PL327693A1 (cs) |
| SK (1) | SK88398A3 (cs) |
| TR (1) | TR199801235T2 (cs) |
| WO (1) | WO1997024113A1 (cs) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9504537D0 (sv) * | 1995-12-19 | 1995-12-19 | Jan Hedner | Sätt att behandla och diagnosticera andningsstörningar under sömn och medel för utförande av sättet |
| DE19945302A1 (de) * | 1999-09-22 | 2001-03-29 | Merck Patent Gmbh | Biphenylderivate als NHE-3-Inhibitoren |
| DE10060292A1 (de) | 2000-12-05 | 2002-06-20 | Aventis Pharma Gmbh | Verwendung substituierter Benzimidazole zur Herstellung eines Medikaments zur Behandlung von Krankheiten, welche durch Inhibierung des Na+/H+-Austauschers beeinflusst werden können und sie enthaltendes Medikament |
| DE10163239A1 (de) * | 2001-12-21 | 2003-07-10 | Aventis Pharma Gmbh | Substituierte Imidazolidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie enthaltendes Medikament |
| MX2011007024A (es) | 2008-12-31 | 2011-09-27 | Aedelyx Inc | Compuestos y metodos para inhibir el antiporte mediado por intercambiador de iones de sodio/iones de hidrogeno (nhe) en el tratamiento de trastornos asociados con retencion de fluido o sobrecarga de sal y trastornos del tracto gastrointestinal. |
| WO2018129556A1 (en) | 2017-01-09 | 2018-07-12 | Ardelyx, Inc. | Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| US10376481B2 (en) | 2012-08-21 | 2019-08-13 | Ardelyx, Inc. | Compounds and methods for inhibiting NHE-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| MX366293B (es) | 2012-08-21 | 2019-07-04 | Ardelyx Inc | Compuestos y metodos para inhibir al antipuerto mediado por nhe en el tratamiento de trastornos asociados con la retencion de fluidos o la sobrecarga de sal y trastornos del tracto gastrointestinal. |
| KR20250026881A (ko) | 2013-04-12 | 2025-02-25 | 알데릭스, 인코포레이티드 | Nhe3-결합 화합물 및 포스페이트 수송을 저해하는 방법 |
| KR102386666B1 (ko) | 2014-07-25 | 2022-04-15 | 다이쇼 세이야꾸 가부시끼가이샤 | 헤테로아릴로 치환된 페닐테트라히드로이소퀴놀린 화합물 |
| MA47203A (fr) | 2017-01-09 | 2019-11-13 | Ardelyx Inc | Inhibiteurs d'antiport à médiation par nhe |
| MX395405B (es) | 2017-01-09 | 2025-03-25 | Ardelyx Inc | Compuestos útiles para tratar trastornos del tracto gastrointestinal. |
| BR112020002322A2 (pt) | 2017-08-04 | 2020-09-01 | Ardelyx, Inc. | derivados de ácido glicirretinínico para o tratamento de hipercalemia |
| TWI861053B (zh) | 2019-02-07 | 2024-11-11 | 美商阿德利克斯公司 | 用於治療高鉀血症之化合物及方法 |
| EP3972599A1 (en) | 2019-05-21 | 2022-03-30 | Ardelyx, Inc. | Combination for lowering serum phosphate in a patient |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4325822A1 (de) * | 1993-07-31 | 1995-02-02 | Hoechst Ag | Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| EP0639573A1 (de) * | 1993-08-03 | 1995-02-22 | Hoechst Aktiengesellschaft | Benzokondensierte 5-Ringheterocyclen, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, ihre Verwendung als Diagnostikum, sowie sie enthaltendes Medikament |
| DE4337609A1 (de) * | 1993-11-04 | 1995-05-11 | Boehringer Ingelheim Kg | Neue Pyrazincarboxamidderivate, ihre Herstellung und ihre Verwendung in Arzneimitteln |
| DE4415873A1 (de) * | 1994-05-05 | 1995-11-09 | Hoechst Ag | Substituierte bizyklische Heteroaroylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
-
1995
- 1995-12-27 DE DE19548812A patent/DE19548812A1/de not_active Withdrawn
-
1996
- 1996-12-13 BR BR9612287-0A patent/BR9612287A/pt unknown
- 1996-12-13 SK SK883-98A patent/SK88398A3/sk unknown
- 1996-12-13 PL PL96327693A patent/PL327693A1/xx unknown
- 1996-12-13 IL IL12511496A patent/IL125114A0/xx unknown
- 1996-12-13 CA CA002241531A patent/CA2241531A1/en not_active Abandoned
- 1996-12-13 KR KR1019980704927A patent/KR19990076802A/ko not_active Withdrawn
- 1996-12-13 EP EP96943956A patent/EP0869779A1/de not_active Withdrawn
- 1996-12-13 AU AU13720/97A patent/AU717247B2/en not_active Ceased
- 1996-12-13 WO PCT/EP1996/005614 patent/WO1997024113A1/de not_active Application Discontinuation
- 1996-12-13 TR TR1998/01235T patent/TR199801235T2/xx unknown
- 1996-12-13 CN CN96199403A patent/CN1207676A/zh active Pending
- 1996-12-13 HU HU9900807A patent/HUP9900807A3/hu unknown
-
1998
- 1998-06-24 MX MX9805141A patent/MX9805141A/es unknown
- 1998-06-26 NO NO982989A patent/NO982989L/no not_active Application Discontinuation
-
2021
- 2021-03-03 CZ CZ982021A patent/CZ202198DA3/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SK88398A3 (en) | 1999-03-12 |
| IL125114A0 (en) | 1999-01-26 |
| CA2241531A1 (en) | 1997-07-10 |
| TR199801235T2 (xx) | 1998-10-21 |
| MX9805141A (es) | 1998-10-31 |
| CZ202198DA3 (cs) | 1998-11-11 |
| NO982989L (no) | 1998-08-06 |
| BR9612287A (pt) | 2005-05-24 |
| WO1997024113A1 (de) | 1997-07-10 |
| DE19548812A1 (de) | 1997-07-03 |
| AU1372097A (en) | 1997-07-28 |
| CN1207676A (zh) | 1999-02-10 |
| EP0869779A1 (de) | 1998-10-14 |
| HUP9900807A2 (hu) | 1999-07-28 |
| NO982989D0 (no) | 1998-06-26 |
| KR19990076802A (ko) | 1999-10-15 |
| HUP9900807A3 (en) | 2000-11-28 |
| PL327693A1 (en) | 1998-12-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |